%! # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CNpip_in_acetone #TrackingRef 'web_deposit_cif_file_0_AurelienCrochet_1363102931.CNpip.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 4-((4-hydroxy-3-(piperidin-1-ylmethyl)naphthalen-1-yl)diazenyl)benzonitrile _chemical_name_common ? _chemical_formula_moiety 'C23 H22 N4 O' _chemical_formula_sum 'C23 H22 N4 O' _exptl_crystal_recrystallization_method acetone _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour red _diffrn_ambient_temperature 200(2) _chemical_formula_weight 370.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.0932(6) _cell_length_b 11.5499(14) _cell_length_c 16.654(2) _cell_angle_alpha 92.331(10) _cell_angle_beta 93.567(10) _cell_angle_gamma 101.183(10) _cell_volume 957.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 11349 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 66.90 _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5954 _exptl_absorpt_correction_T_max 0.9211 _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54186 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7121 _diffrn_reflns_av_R_equivalents 0.0753 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 65.67 _reflns_number_total 2964 _reflns_number_gt 2196 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0938P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.063(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2964 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0813(3) 0.47851(13) 0.13929(8) 0.0324(4) Uani 1 1 d . . . C8 C 0.5816(4) 0.33756(17) 0.29819(11) 0.0259(5) Uani 1 1 d . . . N2 N 0.7457(3) 0.28309(15) 0.35017(9) 0.0277(4) Uani 1 1 d . . . C12 C 0.1929(3) 0.31015(17) 0.19983(11) 0.0240(5) Uani 1 1 d . . . C10 C 0.4571(4) 0.50854(17) 0.23647(11) 0.0260(5) Uani 1 1 d . . . N1 N 0.9092(3) 0.35402(15) 0.39771(10) 0.0305(4) Uani 1 1 d . . . C11 C 0.2454(3) 0.43448(17) 0.19196(11) 0.0249(5) Uani 1 1 d . . . C16 C 0.3109(4) 0.13566(17) 0.25862(12) 0.0304(5) Uani 1 1 d . . . H16 H 0.4241 0.1002 0.2933 0.036 Uiso 1 1 calc R . . N4 N 0.4471(3) 0.67579(14) 0.14780(9) 0.0262(4) Uani 1 1 d . . . C1 C 1.0817(4) 0.29802(18) 0.44721(11) 0.0277(5) Uani 1 1 d . . . C17 C 0.3657(3) 0.26030(17) 0.25264(11) 0.0239(5) Uani 1 1 d . . . C9 C 0.6243(4) 0.45769(17) 0.28846(11) 0.0272(5) Uani 1 1 d . . . H9 H 0.7719 0.5076 0.3180 0.033 Uiso 1 1 calc R . . C23 C 0.6541(4) 0.64892(18) 0.09630(12) 0.0296(5) Uani 1 1 d . . . H23A H 0.6558 0.5634 0.0964 0.035 Uiso 1 1 calc R . . H23B H 0.8324 0.6926 0.1184 0.035 Uiso 1 1 calc R . . C15 C 0.0976(4) 0.06612(18) 0.21511(13) 0.0345(5) Uani 1 1 d . . . H15 H 0.0645 -0.0171 0.2198 0.041 Uiso 1 1 calc R . . C14 C -0.0736(4) 0.11645(18) 0.16343(13) 0.0353(6) Uani 1 1 d . . . H14 H -0.2226 0.0673 0.1340 0.042 Uiso 1 1 calc R . . C20 C 0.3819(4) 0.84039(18) 0.06316(12) 0.0322(5) Uani 1 1 d . . . H20A H 0.2016 0.7988 0.0413 0.039 Uiso 1 1 calc R . . H20B H 0.3841 0.9264 0.0649 0.039 Uiso 1 1 calc R . . C13 C -0.0261(4) 0.23569(18) 0.15550(11) 0.0297(5) Uani 1 1 d . . . H13 H -0.1409 0.2690 0.1200 0.036 Uiso 1 1 calc R . . C18 C 0.4971(4) 0.64063(18) 0.23080(12) 0.0329(5) Uani 1 1 d . . . H18A H 0.3745 0.6716 0.2662 0.039 Uiso 1 1 calc R . . H18B H 0.6834 0.6769 0.2506 0.039 Uiso 1 1 calc R . . C7 C 1.6378(4) 0.1679(2) 0.59930(13) 0.0369(5) Uani 1 1 d . . . C22 C 0.6033(4) 0.68270(19) 0.01073(12) 0.0354(5) Uani 1 1 d . . . H22A H 0.4318 0.6344 -0.0129 0.043 Uiso 1 1 calc R . . H22B H 0.7487 0.6659 -0.0220 0.043 Uiso 1 1 calc R . . C6 C 1.2501(4) 0.37350(18) 0.50427(12) 0.0322(5) Uani 1 1 d . . . H6 H 1.2390 0.4546 0.5093 0.039 Uiso 1 1 calc R . . C21 C 0.5910(4) 0.81286(18) 0.00803(12) 0.0341(6) Uani 1 1 d . . . H21A H 0.5432 0.8316 -0.0478 0.041 Uiso 1 1 calc R . . H21B H 0.7687 0.8618 0.0257 0.041 Uiso 1 1 calc R . . C19 C 0.4363(4) 0.80232(17) 0.14822(12) 0.0318(5) Uani 1 1 d . . . H19A H 0.6090 0.8495 0.1720 0.038 Uiso 1 1 calc R . . H19B H 0.2928 0.8179 0.1822 0.038 Uiso 1 1 calc R . . C2 C 1.0934(4) 0.17869(18) 0.44074(12) 0.0322(5) Uani 1 1 d . . . H2 H 0.9777 0.1271 0.4021 0.039 Uiso 1 1 calc R . . C5 C 1.4339(4) 0.33042(19) 0.55365(12) 0.0338(5) Uani 1 1 d . . . H5 H 1.5517 0.3822 0.5917 0.041 Uiso 1 1 calc R . . N3 N 1.7903(4) 0.13597(19) 0.64203(12) 0.0533(6) Uani 1 1 d . . . C4 C 1.4453(4) 0.21160(18) 0.54738(11) 0.0299(5) Uani 1 1 d . . . C3 C 1.2741(4) 0.13567(19) 0.49083(12) 0.0338(5) Uani 1 1 d . . . H3 H 1.2820 0.0542 0.4868 0.041 Uiso 1 1 calc R . . H1 H 0.167(5) 0.558(2) 0.1338(14) 0.051 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0296(7) 0.0282(8) 0.0394(8) 0.0105(7) -0.0061(6) 0.0067(6) C8 0.0288(10) 0.0279(11) 0.0220(10) 0.0030(8) 0.0016(8) 0.0076(8) N2 0.0280(8) 0.0305(10) 0.0247(9) 0.0031(7) -0.0009(7) 0.0062(7) C12 0.0239(9) 0.0271(11) 0.0220(10) 0.0035(8) 0.0053(8) 0.0060(8) C10 0.0309(10) 0.0259(11) 0.0218(9) 0.0033(8) 0.0031(8) 0.0064(8) N1 0.0335(9) 0.0296(9) 0.0279(9) 0.0026(8) -0.0059(8) 0.0071(7) C11 0.0239(9) 0.0296(11) 0.0230(10) 0.0055(9) 0.0037(8) 0.0083(8) C16 0.0329(10) 0.0272(11) 0.0319(11) 0.0050(9) -0.0012(9) 0.0082(8) N4 0.0290(8) 0.0222(9) 0.0275(9) 0.0038(7) -0.0006(7) 0.0054(6) C1 0.0301(10) 0.0302(11) 0.0234(10) 0.0047(9) -0.0005(8) 0.0069(8) C17 0.0232(9) 0.0264(11) 0.0226(10) 0.0036(8) 0.0037(8) 0.0054(8) C9 0.0287(10) 0.0285(11) 0.0236(10) 0.0006(9) 0.0008(8) 0.0038(8) C23 0.0258(10) 0.0261(11) 0.0383(12) 0.0038(9) 0.0032(9) 0.0080(8) C15 0.0375(11) 0.0233(11) 0.0414(12) 0.0032(9) 0.0008(10) 0.0030(9) C14 0.0306(10) 0.0305(12) 0.0411(12) 0.0039(10) -0.0047(9) -0.0010(8) C20 0.0268(10) 0.0249(11) 0.0447(12) 0.0095(10) -0.0017(9) 0.0044(8) C13 0.0258(9) 0.0340(12) 0.0287(11) 0.0057(9) -0.0014(8) 0.0045(8) C18 0.0438(12) 0.0258(11) 0.0280(11) 0.0032(9) -0.0038(9) 0.0060(9) C7 0.0486(13) 0.0380(13) 0.0280(11) 0.0013(10) 0.0004(10) 0.0188(10) C22 0.0350(11) 0.0360(13) 0.0354(12) 0.0059(10) 0.0042(9) 0.0061(9) C6 0.0375(11) 0.0271(11) 0.0318(11) 0.0031(9) -0.0048(9) 0.0076(9) C21 0.0302(10) 0.0320(12) 0.0384(12) 0.0136(10) -0.0016(9) 0.0007(8) C19 0.0366(11) 0.0211(11) 0.0383(12) 0.0034(9) -0.0001(9) 0.0076(8) C2 0.0369(11) 0.0299(12) 0.0289(11) -0.0012(9) -0.0039(9) 0.0070(9) C5 0.0392(11) 0.0331(12) 0.0281(11) 0.0008(9) -0.0073(9) 0.0077(9) N3 0.0654(13) 0.0580(14) 0.0424(12) 0.0048(10) -0.0113(11) 0.0312(11) C4 0.0359(11) 0.0337(12) 0.0222(10) 0.0033(9) 0.0001(9) 0.0125(9) C3 0.0424(12) 0.0275(11) 0.0334(11) 0.0016(9) -0.0003(10) 0.0128(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.355(2) . ? O1 H1 0.94(3) . ? C8 C9 1.380(3) . ? C8 N2 1.415(2) . ? C8 C17 1.429(3) . ? N2 N1 1.262(2) . ? C12 C13 1.415(3) . ? C12 C11 1.422(3) . ? C12 C17 1.422(2) . ? C10 C11 1.391(3) . ? C10 C9 1.401(3) . ? C10 C18 1.507(3) . ? N1 C1 1.429(2) . ? C16 C15 1.366(3) . ? C16 C17 1.421(3) . ? C16 H16 0.9500 . ? N4 C23 1.470(3) . ? N4 C19 1.473(2) . ? N4 C18 1.477(2) . ? C1 C2 1.391(3) . ? C1 C6 1.393(3) . ? C9 H9 0.9500 . ? C23 C22 1.513(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C15 C14 1.408(3) . ? C15 H15 0.9500 . ? C14 C13 1.365(3) . ? C14 H14 0.9500 . ? C20 C21 1.519(3) . ? C20 C19 1.525(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C13 H13 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C7 N3 1.145(3) . ? C7 C4 1.444(3) . ? C22 C21 1.519(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C6 C5 1.385(3) . ? C6 H6 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C5 C4 1.385(3) . ? C5 H5 0.9500 . ? C4 C3 1.397(3) . ? C3 H3 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 H1 105.2(15) . . ? C9 C8 N2 123.81(17) . . ? C9 C8 C17 119.94(17) . . ? N2 C8 C17 116.22(17) . . ? N1 N2 C8 114.49(17) . . ? C13 C12 C11 121.10(16) . . ? C13 C12 C17 119.76(17) . . ? C11 C12 C17 119.14(16) . . ? C11 C10 C9 118.48(17) . . ? C11 C10 C18 120.26(17) . . ? C9 C10 C18 121.22(17) . . ? N2 N1 C1 113.76(17) . . ? O1 C11 C10 121.02(17) . . ? O1 C11 C12 117.51(16) . . ? C10 C11 C12 121.46(16) . . ? C15 C16 C17 120.84(17) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C23 N4 C19 110.89(14) . . ? C23 N4 C18 110.66(15) . . ? C19 N4 C18 110.22(16) . . ? C2 C1 C6 120.17(17) . . ? C2 C1 N1 125.11(18) . . ? C6 C1 N1 114.71(18) . . ? C16 C17 C12 118.03(17) . . ? C16 C17 C8 123.24(17) . . ? C12 C17 C8 118.71(17) . . ? C8 C9 C10 122.21(18) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? N4 C23 C22 111.31(16) . . ? N4 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? N4 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C16 C15 C14 120.70(19) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C13 C14 C15 120.17(18) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C21 C20 C19 111.10(16) . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20B 109.4 . . ? C19 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C14 C13 C12 120.50(17) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? N4 C18 C10 112.74(17) . . ? N4 C18 H18A 109.0 . . ? C10 C18 H18A 109.0 . . ? N4 C18 H18B 109.0 . . ? C10 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? N3 C7 C4 178.0(3) . . ? C23 C22 C21 111.14(18) . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? C23 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C5 C6 C1 120.05(19) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C22 C21 C20 109.31(15) . . ? C22 C21 H21A 109.8 . . ? C20 C21 H21A 109.8 . . ? C22 C21 H21B 109.8 . . ? C20 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? N4 C19 C20 111.15(17) . . ? N4 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N4 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C3 C2 C1 119.63(19) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C5 C6 119.81(19) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C4 C3 120.10(18) . . ? C5 C4 C7 119.21(18) . . ? C3 C4 C7 120.69(19) . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C8 N2 N1 11.4(3) . . . . ? C17 C8 N2 N1 -170.32(16) . . . . ? C8 N2 N1 C1 -177.28(15) . . . . ? C9 C10 C11 O1 -178.37(17) . . . . ? C18 C10 C11 O1 4.0(3) . . . . ? C9 C10 C11 C12 1.6(3) . . . . ? C18 C10 C11 C12 -176.09(18) . . . . ? C13 C12 C11 O1 -1.3(3) . . . . ? C17 C12 C11 O1 178.09(16) . . . . ? C13 C12 C11 C10 178.72(18) . . . . ? C17 C12 C11 C10 -1.9(3) . . . . ? N2 N1 C1 C2 5.8(3) . . . . ? N2 N1 C1 C6 -175.46(17) . . . . ? C15 C16 C17 C12 -0.3(3) . . . . ? C15 C16 C17 C8 178.37(19) . . . . ? C13 C12 C17 C16 0.2(3) . . . . ? C11 C12 C17 C16 -179.20(17) . . . . ? C13 C12 C17 C8 -178.52(17) . . . . ? C11 C12 C17 C8 2.1(3) . . . . ? C9 C8 C17 C16 179.25(19) . . . . ? N2 C8 C17 C16 0.9(3) . . . . ? C9 C8 C17 C12 -2.1(3) . . . . ? N2 C8 C17 C12 179.55(16) . . . . ? N2 C8 C9 C10 -179.89(17) . . . . ? C17 C8 C9 C10 1.9(3) . . . . ? C11 C10 C9 C8 -1.6(3) . . . . ? C18 C10 C9 C8 176.06(19) . . . . ? C19 N4 C23 C22 -58.3(2) . . . . ? C18 N4 C23 C22 179.12(16) . . . . ? C17 C16 C15 C14 -0.2(3) . . . . ? C16 C15 C14 C13 0.8(3) . . . . ? C15 C14 C13 C12 -0.9(3) . . . . ? C11 C12 C13 C14 179.79(19) . . . . ? C17 C12 C13 C14 0.4(3) . . . . ? C23 N4 C18 C10 -68.2(2) . . . . ? C19 N4 C18 C10 168.79(16) . . . . ? C11 C10 C18 N4 -40.0(3) . . . . ? C9 C10 C18 N4 142.42(18) . . . . ? N4 C23 C22 C21 57.4(2) . . . . ? C2 C1 C6 C5 1.3(3) . . . . ? N1 C1 C6 C5 -177.47(17) . . . . ? C23 C22 C21 C20 -54.9(2) . . . . ? C19 C20 C21 C22 54.5(2) . . . . ? C23 N4 C19 C20 57.7(2) . . . . ? C18 N4 C19 C20 -179.41(15) . . . . ? C21 C20 C19 N4 -56.5(2) . . . . ? C6 C1 C2 C3 -0.4(3) . . . . ? N1 C1 C2 C3 178.27(18) . . . . ? C1 C6 C5 C4 -1.5(3) . . . . ? C6 C5 C4 C3 0.7(3) . . . . ? C6 C5 C4 C7 -179.95(19) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C5 C4 C3 C2 0.2(3) . . . . ? C7 C4 C3 C2 -179.12(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N4 0.94(3) 1.77(3) 2.642(2) 152(2) . _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 65.67 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.334 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.125 _iucr_refine_instructions_details ; TITL CNpip in acetone CELL 1.54186 5.0932 11.5499 16.6536 92.331 93.567 101.183 ZERR 2.00 0.0006 0.0014 0.0020 0.010 0.010 0.010 LATT 1 SFAC C H N O UNIT 46 44 8 2 MERG 2 HTAB O1 N4 FMAP 2 PLAN 20 SIZE 0.13 0.40 0.90 ACTA BOND $H CONF LIST 3 L.S. 20 TEMP -73.00 WGHT 0.093800 EXTI 0.063370 FVAR 1.98949 O1 4 0.081283 0.478507 0.139286 11.00000 0.02964 0.02816 = 0.03935 0.01048 -0.00607 0.00669 C8 1 0.581633 0.337557 0.298194 11.00000 0.02883 0.02787 = 0.02203 0.00297 0.00158 0.00764 N2 3 0.745655 0.283094 0.350167 11.00000 0.02803 0.03047 = 0.02468 0.00312 -0.00095 0.00621 C12 1 0.192940 0.310152 0.199827 11.00000 0.02390 0.02715 = 0.02200 0.00351 0.00527 0.00598 C10 1 0.457058 0.508541 0.236468 11.00000 0.03088 0.02586 = 0.02181 0.00326 0.00306 0.00639 N1 3 0.909166 0.354022 0.397712 11.00000 0.03348 0.02962 = 0.02788 0.00259 -0.00590 0.00710 C11 1 0.245371 0.434485 0.191958 11.00000 0.02394 0.02960 = 0.02302 0.00552 0.00367 0.00827 C16 1 0.310938 0.135664 0.258624 11.00000 0.03288 0.02717 = 0.03189 0.00503 -0.00115 0.00816 AFIX 43 H16 2 0.424095 0.100247 0.293315 11.00000 -1.20000 AFIX 0 N4 3 0.447098 0.675794 0.147798 11.00000 0.02898 0.02216 = 0.02746 0.00379 -0.00063 0.00536 C1 1 1.081673 0.298022 0.447205 11.00000 0.03007 0.03015 = 0.02339 0.00473 -0.00045 0.00694 C17 1 0.365686 0.260303 0.252644 11.00000 0.02321 0.02644 = 0.02262 0.00359 0.00373 0.00540 C9 1 0.624263 0.457689 0.288461 11.00000 0.02872 0.02847 = 0.02359 0.00060 0.00078 0.00383 AFIX 43 H9 2 0.771919 0.507587 0.318000 11.00000 -1.20000 AFIX 0 C23 1 0.654131 0.648918 0.096301 11.00000 0.02582 0.02611 = 0.03826 0.00378 0.00318 0.00800 AFIX 23 H23A 2 0.655754 0.563350 0.096391 11.00000 -1.20000 H23B 2 0.832383 0.692595 0.118428 11.00000 -1.20000 AFIX 0 C15 1 0.097621 0.066116 0.215113 11.00000 0.03747 0.02332 = 0.04136 0.00321 0.00077 0.00303 AFIX 43 H15 2 0.064469 -0.017074 0.219774 11.00000 -1.20000 AFIX 0 C14 1 -0.073643 0.116447 0.163426 11.00000 0.03060 0.03054 = 0.04109 0.00395 -0.00475 -0.00099 AFIX 43 H14 2 -0.222632 0.067261 0.134005 11.00000 -1.20000 AFIX 0 C20 1 0.381943 0.840395 0.063158 11.00000 0.02675 0.02492 = 0.04474 0.00955 -0.00170 0.00445 AFIX 23 H20A 2 0.201588 0.798752 0.041333 11.00000 -1.20000 H20B 2 0.384071 0.926355 0.064949 11.00000 -1.20000 AFIX 0 C13 1 -0.026098 0.235692 0.155502 11.00000 0.02578 0.03404 = 0.02872 0.00570 -0.00139 0.00452 AFIX 43 H13 2 -0.140900 0.268970 0.119964 11.00000 -1.20000 AFIX 0 C18 1 0.497106 0.640627 0.230803 11.00000 0.04380 0.02579 = 0.02804 0.00316 -0.00377 0.00599 AFIX 23 H18A 2 0.374494 0.671582 0.266177 11.00000 -1.20000 H18B 2 0.683352 0.676904 0.250640 11.00000 -1.20000 AFIX 0 C7 1 1.637769 0.167887 0.599303 11.00000 0.04862 0.03803 = 0.02796 0.00132 0.00039 0.01884 C22 1 0.603345 0.682704 0.010730 11.00000 0.03503 0.03600 = 0.03544 0.00588 0.00418 0.00608 AFIX 23 H22A 2 0.431826 0.634367 -0.012922 11.00000 -1.20000 H22B 2 0.748675 0.665861 -0.021991 11.00000 -1.20000 AFIX 0 C6 1 1.250148 0.373504 0.504271 11.00000 0.03751 0.02706 = 0.03184 0.00310 -0.00483 0.00765 AFIX 43 H6 2 1.238994 0.454603 0.509317 11.00000 -1.20000 AFIX 0 C21 1 0.591011 0.812860 0.008029 11.00000 0.03019 0.03200 = 0.03844 0.01360 -0.00159 0.00065 AFIX 23 H21A 2 0.543224 0.831642 -0.047820 11.00000 -1.20000 H21B 2 0.768684 0.861821 0.025699 11.00000 -1.20000 AFIX 0 C19 1 0.436324 0.802323 0.148218 11.00000 0.03657 0.02111 = 0.03831 0.00342 -0.00006 0.00756 AFIX 23 H19A 2 0.609004 0.849486 0.171974 11.00000 -1.20000 H19B 2 0.292814 0.817884 0.182156 11.00000 -1.20000 AFIX 0 C2 1 1.093397 0.178687 0.440741 11.00000 0.03692 0.02994 = 0.02892 -0.00121 -0.00388 0.00699 AFIX 43 H2 2 0.977682 0.127095 0.402071 11.00000 -1.20000 AFIX 0 C5 1 1.433863 0.330423 0.553646 11.00000 0.03915 0.03307 = 0.02810 0.00080 -0.00731 0.00770 AFIX 43 H5 2 1.551695 0.382226 0.591709 11.00000 -1.20000 AFIX 0 N3 3 1.790349 0.135966 0.642034 11.00000 0.06539 0.05798 = 0.04238 0.00482 -0.01134 0.03117 C4 1 1.445336 0.211598 0.547381 11.00000 0.03588 0.03371 = 0.02221 0.00334 0.00011 0.01253 C3 1 1.274095 0.135672 0.490828 11.00000 0.04235 0.02754 = 0.03343 0.00161 -0.00033 0.01280 AFIX 43 H3 2 1.282013 0.054154 0.486820 11.00000 -1.20000 AFIX 0 H1 2 0.167437 0.557620 0.133848 11.00000 -1.50000 HKLF 4 REM CNpip in acetone REM R1 = 0.0511 for 2196 Fo > 4sig(Fo) and 0.0736 for all 2964 data REM 257 parameters refined using 0 restraints END WGHT 0.0965 0.0000 REM Highest difference peak 0.334, deepest hole -0.401, 1-sigma level 0.125 Q1 1 0.9355 0.6688 0.3180 11.00000 0.05 0.33 Q2 1 1.0104 0.4096 0.5378 11.00000 0.05 0.33 Q3 1 1.9984 0.2069 0.6955 11.00000 0.05 0.32 Q4 1 2.0369 0.2856 0.6167 11.00000 0.05 0.32 Q5 1 1.0078 0.4654 0.3775 11.00000 0.05 0.31 Q6 1 1.9153 0.2624 0.6349 11.00000 0.05 0.30 Q7 1 1.2217 0.2233 0.6034 11.00000 0.05 0.29 Q8 1 -0.1174 0.0457 0.0985 11.00000 0.05 0.29 Q9 1 1.0139 0.6620 0.2031 11.00000 0.05 0.29 Q10 1 0.0329 0.0458 0.0738 11.00000 0.05 0.28 Q11 1 2.0687 0.2430 0.5889 11.00000 0.05 0.28 Q12 1 0.2002 0.7596 0.0235 11.00000 0.05 0.28 Q13 1 1.0061 0.5970 0.3024 11.00000 0.05 0.27 Q14 1 1.0213 0.5312 0.3948 11.00000 0.05 0.27 Q15 1 0.9477 0.4432 0.5819 11.00000 0.05 0.27 Q16 1 -0.2939 0.1452 0.1996 11.00000 0.05 0.27 Q17 1 0.0877 0.9102 -0.0197 11.00000 0.05 0.27 Q18 1 -0.0575 -0.0393 0.2401 11.00000 0.05 0.27 Q19 1 0.5439 0.7032 -0.1243 11.00000 0.05 0.27 Q20 1 1.1327 0.5432 0.4398 11.00000 0.05 0.27 ; _database_code_depnum_ccdc_archive 'CCDC 928932' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CNpipH_ClO4 #TrackingRef '18491_web_deposit_cif_file_1_AurelienCrochet_1363102931.CNpip ClO4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ;1-((4-(2-(4-cyanophenyl)hydrazono)-1-oxo-1, 4-dihydronaphthalen-2-yl)methyl)piperidin-1-ium perchlorate ; _chemical_name_common '1-cyanophenylazo-4-naphthol-piperidinium perchlorate' _chemical_formula_moiety 'C23 H23 N4 O, Cl O4' _chemical_formula_sum 'C23 H23 Cl N4 O5' _exptl_crystal_recrystallization_method 'ethanol, cyclohexane' _chemical_melting_point ? _exptl_crystal_description rectangle _exptl_crystal_colour red-orange _diffrn_ambient_temperature 200(2) _chemical_formula_weight 470.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.6608(9) _cell_length_b 12.6110(5) _cell_length_c 11.6097(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.592(4) _cell_angle_gamma 90.00 _cell_volume 2173.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 23270 _cell_measurement_theta_min 1.37 _cell_measurement_theta_max 26.07 _exptl_crystal_size_max 0.660 _exptl_crystal_size_mid 0.290 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41433 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3826 _reflns_number_gt 2701 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3826 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.33244(9) -0.64880(12) 0.63637(13) 0.0528(4) Uani 1 1 d . . . N1 N -0.01006(12) -0.63020(13) 0.42699(16) 0.0412(4) Uani 1 1 d . . . N2 N -0.01681(10) -0.62875(12) 0.53805(14) 0.0392(4) Uani 1 1 d . . . N3 N 0.39910(15) -0.7253(2) 0.3760(3) 0.0858(8) Uani 1 1 d . . . N4 N -0.39318(11) -0.60479(13) 0.31575(14) 0.0392(4) Uani 1 1 d . . . C1 C 0.07496(13) -0.64222(14) 0.41521(18) 0.0384(4) Uani 1 1 d . . . C6 C 0.08349(14) -0.64609(16) 0.29934(19) 0.0455(5) Uani 1 1 d . . . H6 H 0.0333 -0.6364 0.2309 0.055 Uiso 1 1 calc R . . C5 C 0.16691(15) -0.66444(17) 0.2871(2) 0.0512(5) Uani 1 1 d . . . H5 H 0.1730 -0.6667 0.2101 0.061 Uiso 1 1 calc R . . C4 C 0.24185(14) -0.67952(17) 0.3888(2) 0.0499(5) Uani 1 1 d . . . C3 C 0.23304(14) -0.67257(18) 0.5042(2) 0.0532(5) Uani 1 1 d . . . H3 H 0.2833 -0.6811 0.5727 0.064 Uiso 1 1 calc R . . C2 C 0.15013(14) -0.65317(17) 0.51713(19) 0.0469(5) Uani 1 1 d . . . H2 H 0.1446 -0.6474 0.5943 0.056 Uiso 1 1 calc R . . C8 C -0.09541(12) -0.63384(14) 0.55602(17) 0.0374(4) Uani 1 1 d . . . C17 C -0.09308(13) -0.62473(14) 0.68299(17) 0.0375(4) Uani 1 1 d . . . C16 C -0.01231(13) -0.61343(14) 0.77790(18) 0.0416(4) Uani 1 1 d . . . H16 H 0.0420 -0.6115 0.7613 0.050 Uiso 1 1 calc R . . C15 C -0.01250(15) -0.60514(16) 0.89610(19) 0.0472(5) Uani 1 1 d . . . H15 H 0.0419 -0.6010 0.9590 0.057 Uiso 1 1 calc R . . C14 C -0.09279(15) -0.60287(16) 0.92236(19) 0.0491(5) Uani 1 1 d . . . H14 H -0.0924 -0.5948 1.0022 0.059 Uiso 1 1 calc R . . C13 C -0.17282(14) -0.61252(15) 0.83013(18) 0.0452(5) Uani 1 1 d . . . H13 H -0.2267 -0.6098 0.8476 0.054 Uiso 1 1 calc R . . C12 C -0.17437(13) -0.62640(14) 0.70984(17) 0.0385(4) Uani 1 1 d . . . C11 C -0.26070(13) -0.64459(15) 0.61379(18) 0.0411(4) Uani 1 1 d . . . C10 C -0.25867(12) -0.66066(14) 0.48895(17) 0.0378(4) Uani 1 1 d . . . C9 C -0.18030(12) -0.65249(14) 0.46408(17) 0.0381(4) Uani 1 1 d . . . H9 H -0.1815 -0.6593 0.3838 0.046 Uiso 1 1 calc R . . C7 C 0.32880(16) -0.70500(19) 0.3795(2) 0.0634(6) Uani 1 1 d . . . C18 C -0.34345(13) -0.69408(15) 0.39270(18) 0.0414(4) Uani 1 1 d . . . H18B H -0.3285 -0.7462 0.3407 0.050 Uiso 1 1 calc R . . H18A H -0.3828 -0.7280 0.4313 0.050 Uiso 1 1 calc R . . C23 C -0.42788(14) -0.52614(16) 0.38672(19) 0.0464(5) Uani 1 1 d . . . H23B H -0.3777 -0.4969 0.4514 0.056 Uiso 1 1 calc R . . H23A H -0.4676 -0.5618 0.4236 0.056 Uiso 1 1 calc R . . C22 C -0.47829(16) -0.43771(18) 0.3067(2) 0.0594(6) Uani 1 1 d . . . H22B H -0.4371 -0.3978 0.2761 0.071 Uiso 1 1 calc R . . H22A H -0.5023 -0.3899 0.3542 0.071 Uiso 1 1 calc R . . C21 C -0.55481(17) -0.4802(2) 0.2006(2) 0.0665(7) Uani 1 1 d . . . H21B H -0.5838 -0.4223 0.1476 0.080 Uiso 1 1 calc R . . H21A H -0.5993 -0.5140 0.2304 0.080 Uiso 1 1 calc R . . C20 C -0.51808(17) -0.5599(2) 0.1304(2) 0.0635(6) Uani 1 1 d . . . H20A H -0.5676 -0.5894 0.0650 0.076 Uiso 1 1 calc R . . H20B H -0.4780 -0.5240 0.0945 0.076 Uiso 1 1 calc R . . C19 C -0.46804(13) -0.64805(17) 0.21031(18) 0.0479(5) Uani 1 1 d . . . H19B H -0.4433 -0.6955 0.1634 0.057 Uiso 1 1 calc R . . H19A H -0.5093 -0.6884 0.2403 0.057 Uiso 1 1 calc R . . Cl1 Cl -0.23706(3) -0.53155(4) 0.14051(4) 0.04507(15) Uani 1 1 d . . . O2 O -0.26267(12) -0.48143(14) 0.23548(15) 0.0701(5) Uani 1 1 d . . . O3 O -0.15277(11) -0.58563(17) 0.19088(15) 0.0764(6) Uani 1 1 d . . . O4 O -0.30341(13) -0.60772(16) 0.0860(2) 0.0925(7) Uani 1 1 d . . . O5 O -0.23048(14) -0.45749(16) 0.05383(17) 0.0845(6) Uani 1 1 d . . . H1 H -0.0562(17) -0.6243(19) 0.362(2) 0.062(7) Uiso 1 1 d . . . H4 H -0.3555(17) -0.570(2) 0.287(2) 0.075 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0486(8) 0.0643(10) 0.0555(9) -0.0024(7) 0.0308(7) -0.0039(7) N1 0.0424(9) 0.0437(10) 0.0435(10) 0.0002(8) 0.0221(8) -0.0001(8) N2 0.0437(9) 0.0361(9) 0.0444(9) -0.0014(7) 0.0236(7) 0.0001(7) N3 0.0709(14) 0.0901(17) 0.122(2) 0.0064(15) 0.0675(15) 0.0014(13) N4 0.0406(9) 0.0417(9) 0.0409(9) -0.0008(7) 0.0209(7) -0.0027(7) C1 0.0438(10) 0.0305(10) 0.0478(11) -0.0019(8) 0.0245(9) -0.0044(8) C6 0.0550(12) 0.0415(11) 0.0469(11) -0.0015(9) 0.0261(10) -0.0035(9) C5 0.0668(14) 0.0456(12) 0.0565(13) -0.0065(10) 0.0411(12) -0.0083(10) C4 0.0506(12) 0.0442(12) 0.0686(15) -0.0028(10) 0.0384(12) -0.0077(10) C3 0.0439(11) 0.0601(14) 0.0610(14) 0.0015(11) 0.0241(10) -0.0048(10) C2 0.0468(11) 0.0574(13) 0.0445(11) -0.0009(9) 0.0260(9) -0.0054(9) C8 0.0431(10) 0.0314(10) 0.0439(11) -0.0016(8) 0.0226(9) 0.0003(8) C17 0.0474(11) 0.0271(9) 0.0448(10) -0.0007(8) 0.0244(9) -0.0007(8) C16 0.0452(11) 0.0349(10) 0.0482(11) -0.0020(8) 0.0199(9) 0.0004(8) C15 0.0569(13) 0.0402(11) 0.0454(11) -0.0031(9) 0.0173(10) -0.0013(9) C14 0.0687(14) 0.0441(11) 0.0404(11) -0.0044(9) 0.0257(11) -0.0086(10) C13 0.0596(13) 0.0370(11) 0.0506(12) -0.0038(9) 0.0340(11) -0.0061(9) C12 0.0464(11) 0.0309(10) 0.0449(10) -0.0013(8) 0.0240(9) -0.0038(8) C11 0.0472(11) 0.0353(10) 0.0501(11) 0.0005(9) 0.0285(9) 0.0006(8) C10 0.0426(10) 0.0304(10) 0.0462(11) 0.0003(8) 0.0224(9) 0.0020(8) C9 0.0457(11) 0.0329(10) 0.0418(10) -0.0010(8) 0.0224(9) 0.0025(8) C7 0.0629(15) 0.0590(15) 0.0862(18) 0.0005(13) 0.0489(14) -0.0063(12) C18 0.0431(10) 0.0364(10) 0.0499(11) -0.0018(9) 0.0222(9) 0.0005(9) C23 0.0534(12) 0.0436(11) 0.0477(11) -0.0019(9) 0.0241(9) 0.0064(10) C22 0.0643(14) 0.0473(13) 0.0706(15) 0.0042(11) 0.0274(12) 0.0100(11) C21 0.0626(15) 0.0648(16) 0.0690(15) 0.0130(13) 0.0167(13) 0.0176(12) C20 0.0626(14) 0.0774(17) 0.0473(13) 0.0064(12) 0.0131(11) -0.0002(13) C19 0.0455(11) 0.0575(13) 0.0449(11) -0.0058(10) 0.0204(9) -0.0023(10) Cl1 0.0461(3) 0.0515(3) 0.0420(3) -0.0002(2) 0.0203(2) -0.0034(2) O2 0.0881(12) 0.0752(12) 0.0622(10) -0.0150(9) 0.0455(9) -0.0056(9) O3 0.0500(9) 0.1253(16) 0.0587(10) 0.0226(10) 0.0243(8) 0.0220(10) O4 0.0694(12) 0.0783(13) 0.1260(18) -0.0400(12) 0.0260(11) -0.0230(10) O5 0.1127(15) 0.0827(13) 0.0805(13) 0.0313(10) 0.0623(12) 0.0188(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.234(2) . ? N1 N2 1.327(2) . ? N1 C1 1.389(2) . ? N1 H1 0.87(3) . ? N2 C8 1.314(2) . ? N3 C7 1.143(3) . ? N4 C18 1.493(2) . ? N4 C23 1.498(2) . ? N4 C19 1.502(3) . ? N4 H4 0.88(3) . ? C1 C2 1.384(3) . ? C1 C6 1.394(3) . ? C6 C5 1.378(3) . ? C6 H6 0.9300 . ? C5 C4 1.387(3) . ? C5 H5 0.9300 . ? C4 C3 1.393(3) . ? C4 C7 1.436(3) . ? C3 C2 1.376(3) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C8 C9 1.434(3) . ? C8 C17 1.467(3) . ? C17 C16 1.395(3) . ? C17 C12 1.404(3) . ? C16 C15 1.377(3) . ? C16 H16 0.9300 . ? C15 C14 1.385(3) . ? C15 H15 0.9300 . ? C14 C13 1.370(3) . ? C14 H14 0.9300 . ? C13 C12 1.400(3) . ? C13 H13 0.9300 . ? C12 C11 1.471(3) . ? C11 C10 1.474(3) . ? C10 C9 1.351(3) . ? C10 C18 1.498(3) . ? C9 H9 0.9300 . ? C18 H18B 0.9700 . ? C18 H18A 0.9700 . ? C23 C22 1.504(3) . ? C23 H23B 0.9700 . ? C23 H23A 0.9700 . ? C22 C21 1.516(3) . ? C22 H22B 0.9700 . ? C22 H22A 0.9700 . ? C21 C20 1.518(4) . ? C21 H21B 0.9700 . ? C21 H21A 0.9700 . ? C20 C19 1.499(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C19 H19B 0.9700 . ? C19 H19A 0.9700 . ? Cl1 O5 1.4006(17) . ? Cl1 O4 1.4085(18) . ? Cl1 O3 1.4343(17) . ? Cl1 O2 1.4346(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 118.22(17) . . ? N2 N1 H1 123.2(16) . . ? C1 N1 H1 118.6(16) . . ? C8 N2 N1 121.50(17) . . ? C18 N4 C23 112.45(15) . . ? C18 N4 C19 109.66(15) . . ? C23 N4 C19 111.29(15) . . ? C18 N4 H4 108.5(17) . . ? C23 N4 H4 106.3(17) . . ? C19 N4 H4 108.5(17) . . ? C2 C1 N1 120.47(17) . . ? C2 C1 C6 120.27(18) . . ? N1 C1 C6 119.23(19) . . ? C5 C6 C1 119.4(2) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C4 C3 119.57(19) . . ? C5 C4 C7 122.2(2) . . ? C3 C4 C7 118.2(2) . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C2 C1 119.96(19) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? N2 C8 C9 125.65(17) . . ? N2 C8 C17 115.54(17) . . ? C9 C8 C17 118.73(16) . . ? C16 C17 C12 118.96(18) . . ? C16 C17 C8 121.83(17) . . ? C12 C17 C8 119.21(17) . . ? C15 C16 C17 120.36(18) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C13 C14 C15 119.64(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C13 C12 120.76(19) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C12 C17 119.41(18) . . ? C13 C12 C11 119.68(17) . . ? C17 C12 C11 120.90(17) . . ? O1 C11 C12 121.67(18) . . ? O1 C11 C10 120.64(18) . . ? C12 C11 C10 117.66(16) . . ? C9 C10 C11 120.36(18) . . ? C9 C10 C18 120.76(17) . . ? C11 C10 C18 118.72(16) . . ? C10 C9 C8 122.89(17) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? N3 C7 C4 177.8(3) . . ? N4 C18 C10 113.79(16) . . ? N4 C18 H18B 108.8 . . ? C10 C18 H18B 108.8 . . ? N4 C18 H18A 108.8 . . ? C10 C18 H18A 108.8 . . ? H18B C18 H18A 107.7 . . ? N4 C23 C22 111.24(17) . . ? N4 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? N4 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? H23B C23 H23A 108.0 . . ? C23 C22 C21 111.27(19) . . ? C23 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? H22B C22 H22A 108.0 . . ? C22 C21 C20 109.5(2) . . ? C22 C21 H21B 109.8 . . ? C20 C21 H21B 109.8 . . ? C22 C21 H21A 109.8 . . ? C20 C21 H21A 109.8 . . ? H21B C21 H21A 108.2 . . ? C19 C20 C21 111.81(19) . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? C19 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C20 C19 N4 110.68(18) . . ? C20 C19 H19B 109.5 . . ? N4 C19 H19B 109.5 . . ? C20 C19 H19A 109.5 . . ? N4 C19 H19A 109.5 . . ? H19B C19 H19A 108.1 . . ? O5 Cl1 O4 110.15(15) . . ? O5 Cl1 O3 109.95(11) . . ? O4 Cl1 O3 108.07(13) . . ? O5 Cl1 O2 111.16(12) . . ? O4 Cl1 O2 107.40(12) . . ? O3 Cl1 O2 110.04(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C8 -169.55(17) . . . . ? N2 N1 C1 C2 0.5(3) . . . . ? N2 N1 C1 C6 178.73(16) . . . . ? C2 C1 C6 C5 2.2(3) . . . . ? N1 C1 C6 C5 -176.08(18) . . . . ? C1 C6 C5 C4 0.3(3) . . . . ? C6 C5 C4 C3 -2.1(3) . . . . ? C6 C5 C4 C7 176.3(2) . . . . ? C5 C4 C3 C2 1.4(3) . . . . ? C7 C4 C3 C2 -177.0(2) . . . . ? C4 C3 C2 C1 1.0(3) . . . . ? N1 C1 C2 C3 175.37(19) . . . . ? C6 C1 C2 C3 -2.8(3) . . . . ? N1 N2 C8 C9 7.0(3) . . . . ? N1 N2 C8 C17 -176.32(15) . . . . ? N2 C8 C17 C16 -1.1(3) . . . . ? C9 C8 C17 C16 175.81(17) . . . . ? N2 C8 C17 C12 178.24(17) . . . . ? C9 C8 C17 C12 -4.8(3) . . . . ? C12 C17 C16 C15 0.7(3) . . . . ? C8 C17 C16 C15 -179.97(18) . . . . ? C17 C16 C15 C14 -3.0(3) . . . . ? C16 C15 C14 C13 2.2(3) . . . . ? C15 C14 C13 C12 1.0(3) . . . . ? C14 C13 C12 C17 -3.4(3) . . . . ? C14 C13 C12 C11 175.41(18) . . . . ? C16 C17 C12 C13 2.5(3) . . . . ? C8 C17 C12 C13 -176.89(16) . . . . ? C16 C17 C12 C11 -176.28(17) . . . . ? C8 C17 C12 C11 4.3(3) . . . . ? C13 C12 C11 O1 -0.5(3) . . . . ? C17 C12 C11 O1 178.24(18) . . . . ? C13 C12 C11 C10 -178.92(17) . . . . ? C17 C12 C11 C10 -0.1(3) . . . . ? O1 C11 C10 C9 177.81(18) . . . . ? C12 C11 C10 C9 -3.8(3) . . . . ? O1 C11 C10 C18 -6.7(3) . . . . ? C12 C11 C10 C18 171.67(16) . . . . ? C11 C10 C9 C8 3.4(3) . . . . ? C18 C10 C9 C8 -171.99(17) . . . . ? N2 C8 C9 C10 177.54(18) . . . . ? C17 C8 C9 C10 0.9(3) . . . . ? C5 C4 C7 N3 179(100) . . . . ? C3 C4 C7 N3 -3(7) . . . . ? C23 N4 C18 C10 -64.8(2) . . . . ? C19 N4 C18 C10 170.81(15) . . . . ? C9 C10 C18 N4 -85.9(2) . . . . ? C11 C10 C18 N4 98.61(19) . . . . ? C18 N4 C23 C22 -179.52(17) . . . . ? C19 N4 C23 C22 -56.0(2) . . . . ? N4 C23 C22 C21 56.4(3) . . . . ? C23 C22 C21 C20 -55.8(3) . . . . ? C22 C21 C20 C19 56.2(3) . . . . ? C21 C20 C19 N4 -56.6(3) . . . . ? C18 N4 C19 C20 -179.05(17) . . . . ? C23 N4 C19 C20 55.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.87(3) 2.13(3) 2.986(2) 168(2) . N4 H4 O2 0.88(3) 2.07(3) 2.946(2) 175(2) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.333 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.038 _iucr_refine_instructions_details ; TITL 07.02.12-9.3 New: P21/c CELL 0.71073 15.6608 12.6110 11.6097 90.000 108.592 90.000 ZERR 4.00 0.0009 0.0005 0.0007 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CL N O UNIT 92 92 4 16 20 MERG 2 OMIT 0.00 50.00 HTAB N1 O3 HTAB N4 O2 FMAP 2 PLAN 20 ACTA 50.00 BOND $H CONF L.S. 20 WGHT 0.062200 FVAR 0.38934 O1 5 -0.332439 -0.648797 0.636375 11.00000 0.04860 0.06429 = 0.05554 -0.00237 0.03076 -0.00393 N1 4 -0.010061 -0.630200 0.426988 11.00000 0.04239 0.04372 = 0.04347 0.00016 0.02209 -0.00014 N2 4 -0.016810 -0.628754 0.538052 11.00000 0.04375 0.03613 = 0.04443 -0.00145 0.02363 0.00011 N3 4 0.399103 -0.725250 0.376046 11.00000 0.07090 0.09010 = 0.12245 0.00635 0.06748 0.00142 N4 4 -0.393180 -0.604789 0.315751 11.00000 0.04056 0.04169 = 0.04093 -0.00076 0.02090 -0.00272 C1 1 0.074957 -0.642219 0.415206 11.00000 0.04381 0.03051 = 0.04776 -0.00187 0.02449 -0.00439 C6 1 0.083486 -0.646089 0.299335 11.00000 0.05499 0.04150 = 0.04693 -0.00147 0.02606 -0.00349 AFIX 43 H6 2 0.033332 -0.636374 0.230929 11.00000 -1.20000 AFIX 0 C5 1 0.166915 -0.664440 0.287125 11.00000 0.06683 0.04557 = 0.05653 -0.00652 0.04111 -0.00833 AFIX 43 H5 2 0.173012 -0.666730 0.210061 11.00000 -1.20000 AFIX 0 C4 1 0.241847 -0.679521 0.388753 11.00000 0.05059 0.04420 = 0.06858 -0.00279 0.03842 -0.00769 C3 1 0.233039 -0.672573 0.504198 11.00000 0.04389 0.06006 = 0.06097 0.00153 0.02410 -0.00476 AFIX 43 H3 2 0.283334 -0.681072 0.572696 11.00000 -1.20000 AFIX 0 C2 1 0.150126 -0.653173 0.517125 11.00000 0.04684 0.05742 = 0.04452 -0.00093 0.02601 -0.00538 AFIX 43 H2 2 0.144574 -0.647419 0.594283 11.00000 -1.20000 AFIX 0 C8 1 -0.095405 -0.633836 0.556020 11.00000 0.04309 0.03138 = 0.04394 -0.00155 0.02259 0.00029 C17 1 -0.093078 -0.624732 0.682994 11.00000 0.04744 0.02712 = 0.04478 -0.00074 0.02444 -0.00071 C16 1 -0.012314 -0.613425 0.777903 11.00000 0.04521 0.03492 = 0.04822 -0.00203 0.01987 0.00036 AFIX 43 H16 2 0.041957 -0.611474 0.761271 11.00000 -1.20000 AFIX 0 C15 1 -0.012497 -0.605136 0.896096 11.00000 0.05686 0.04020 = 0.04539 -0.00313 0.01734 -0.00128 AFIX 43 H15 2 0.041893 -0.601015 0.958999 11.00000 -1.20000 AFIX 0 C14 1 -0.092789 -0.602866 0.922359 11.00000 0.06866 0.04414 = 0.04043 -0.00439 0.02574 -0.00863 AFIX 43 H14 2 -0.092356 -0.594830 1.002171 11.00000 -1.20000 AFIX 0 C13 1 -0.172819 -0.612522 0.830127 11.00000 0.05963 0.03703 = 0.05057 -0.00381 0.03398 -0.00611 AFIX 43 H13 2 -0.226742 -0.609830 0.847620 11.00000 -1.20000 AFIX 0 C12 1 -0.174367 -0.626397 0.709838 11.00000 0.04640 0.03089 = 0.04492 -0.00134 0.02404 -0.00377 C11 1 -0.260696 -0.644587 0.613795 11.00000 0.04720 0.03529 = 0.05007 0.00050 0.02849 0.00064 C10 1 -0.258671 -0.660658 0.488955 11.00000 0.04260 0.03037 = 0.04622 0.00028 0.02239 0.00203 C9 1 -0.180299 -0.652494 0.464082 11.00000 0.04571 0.03288 = 0.04182 -0.00098 0.02240 0.00253 AFIX 43 H9 2 -0.181462 -0.659271 0.383830 11.00000 -1.20000 AFIX 0 C7 1 0.328800 -0.704998 0.379486 11.00000 0.06287 0.05896 = 0.08620 0.00046 0.04886 -0.00627 C18 1 -0.343445 -0.694084 0.392699 11.00000 0.04312 0.03644 = 0.04991 -0.00185 0.02223 0.00050 AFIX 23 H18B 2 -0.328482 -0.746197 0.340737 11.00000 -1.20000 H18A 2 -0.382819 -0.728038 0.431319 11.00000 -1.20000 AFIX 0 C23 1 -0.427877 -0.526135 0.386715 11.00000 0.05341 0.04363 = 0.04774 -0.00192 0.02412 0.00641 AFIX 23 H23B 2 -0.377738 -0.496854 0.451403 11.00000 -1.20000 H23A 2 -0.467564 -0.561756 0.423581 11.00000 -1.20000 AFIX 0 C22 1 -0.478287 -0.437712 0.306703 11.00000 0.06434 0.04729 = 0.07063 0.00420 0.02740 0.01000 AFIX 23 H22B 2 -0.437131 -0.397776 0.276134 11.00000 -1.20000 H22A 2 -0.502318 -0.389943 0.354198 11.00000 -1.20000 AFIX 0 C21 1 -0.554806 -0.480212 0.200647 11.00000 0.06258 0.06477 = 0.06902 0.01298 0.01666 0.01764 AFIX 23 H21B 2 -0.583806 -0.422290 0.147586 11.00000 -1.20000 H21A 2 -0.599341 -0.514036 0.230368 11.00000 -1.20000 AFIX 0 C20 1 -0.518085 -0.559911 0.130425 11.00000 0.06259 0.07740 = 0.04728 0.00636 0.01313 -0.00019 AFIX 23 H20A 2 -0.567572 -0.589416 0.064980 11.00000 -1.20000 H20B 2 -0.477961 -0.523984 0.094521 11.00000 -1.20000 AFIX 0 C19 1 -0.468043 -0.648055 0.210309 11.00000 0.04549 0.05747 = 0.04495 -0.00580 0.02042 -0.00228 AFIX 23 H19B 2 -0.443260 -0.695522 0.163364 11.00000 -1.20000 H19A 2 -0.509312 -0.688351 0.240317 11.00000 -1.20000 AFIX 0 CL1 3 -0.237055 -0.531549 0.140513 11.00000 0.04612 0.05150 = 0.04202 -0.00020 0.02029 -0.00342 O2 5 -0.262667 -0.481429 0.235480 11.00000 0.08813 0.07523 = 0.06223 -0.01500 0.04553 -0.00560 O3 5 -0.152770 -0.585633 0.190879 11.00000 0.05003 0.12527 = 0.05872 0.02265 0.02427 0.02199 O4 5 -0.303407 -0.607716 0.085971 11.00000 0.06943 0.07832 = 0.12602 -0.03998 0.02596 -0.02304 O5 5 -0.230483 -0.457486 0.053832 11.00000 0.11273 0.08273 = 0.08052 0.03131 0.06228 0.01878 H1 2 -0.056170 -0.624322 0.361511 11.00000 0.06238 H4 2 -0.355515 -0.569935 0.287251 11.00000 -1.20000 HKLF 4 1.0 -1.00 0.00 0.00 0.00 -1.00 0.00 0.00 0.00 1.00 REM 07.02.12-9.3 New: P21/c REM R1 = 0.0368 for 2701 Fo > 4sig(Fo) and 0.0588 for all 3826 data REM 305 parameters refined using 0 restraints END WGHT 0.0621 0.0000 REM Highest difference peak 0.333, deepest hole -0.287, 1-sigma level 0.038 Q1 1 -0.1541 -0.5178 0.2210 11.00000 0.05 0.33 Q2 1 -0.2029 -0.4524 0.2351 11.00000 0.05 0.24 Q3 1 -0.2093 -0.6239 0.6668 11.00000 0.05 0.20 Q4 1 -0.1244 -0.6055 0.2028 11.00000 0.05 0.19 Q5 1 -0.2694 -0.6329 0.1684 11.00000 0.05 0.17 Q6 1 -0.2750 -0.5838 0.0375 11.00000 0.05 0.17 Q7 1 -0.1942 -0.4439 0.1155 11.00000 0.05 0.16 Q8 1 -0.3229 -0.5506 0.1455 11.00000 0.05 0.16 Q9 1 0.3586 -0.7380 0.2972 11.00000 0.05 0.16 Q10 1 -0.2220 -0.6306 0.4812 11.00000 0.05 0.15 Q11 1 -0.3926 -0.6183 0.5571 11.00000 0.05 0.15 Q12 1 -0.0639 -0.6156 0.7217 11.00000 0.05 0.15 Q13 1 -0.0996 -0.6139 0.6319 11.00000 0.05 0.15 Q14 1 -0.1348 -0.6296 0.6970 11.00000 0.05 0.15 Q15 1 0.0539 -0.6318 0.6063 11.00000 0.05 0.15 Q16 1 -0.3382 -0.6194 0.0642 11.00000 0.05 0.14 Q17 1 -0.2648 -0.6243 0.5577 11.00000 0.05 0.14 Q18 1 0.2396 -0.6885 0.4437 11.00000 0.05 0.14 Q19 1 -0.3588 -0.5968 0.5773 11.00000 0.05 0.14 Q20 1 -0.1283 -0.6354 0.5248 11.00000 0.05 0.14 ; _database_code_depnum_ccdc_archive 'CCDC 928933' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cnpiph2so4 #TrackingRef '18492_web_deposit_cif_file_2_AurelienCrochet_1363102931.cnpiph2so4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ;1-((4-(2-(4-cyanophenyl)hydrazono)-1-oxo-1,4 -dihydronaphthalen-2-yl)methyl)piperidin-1-ium hydrogensulfate methanol solvate ; _chemical_name_common ? _chemical_formula_moiety 'C23 H23 N4 O, H O4 S, C H4 O' _chemical_formula_sum 'C24 H28 N4 O6 S' _exptl_crystal_recrystallization_method methanol _chemical_melting_point ? _exptl_crystal_description rectangle _exptl_crystal_colour red _diffrn_ambient_temperature 200(2) _chemical_formula_weight 500.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.448(5) _cell_length_b 6.722(5) _cell_length_c 23.296(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 110.275(5) _cell_angle_gamma 90.000(5) _cell_volume 2416(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9666 _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 24.19 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29512 _diffrn_reflns_av_R_equivalents 0.1449 _diffrn_reflns_av_sigmaI/netI 0.0900 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4194 _reflns_number_gt 2043 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0948P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0088(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4194 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1405 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1708 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5344(3) 0.2623(6) 0.02863(19) 0.0383(10) Uani 1 1 d . . . C2 C 0.5980(3) 0.2795(7) 0.0862(2) 0.0444(11) Uani 1 1 d . . . H2 H 0.5834 0.2652 0.1212 0.053 Uiso 1 1 calc R . . C3 C 0.6831(3) 0.3180(7) 0.0915(2) 0.0453(11) Uani 1 1 d . . . H3 H 0.7257 0.3294 0.1300 0.054 Uiso 1 1 calc R . . C4 C 0.7043(3) 0.3394(6) 0.0395(2) 0.0427(10) Uani 1 1 d . . . C5 C 0.6408(3) 0.3223(6) -0.0182(2) 0.0431(10) Uani 1 1 d . . . H5 H 0.6554 0.3372 -0.0531 0.052 Uiso 1 1 calc R . . C6 C 0.5561(3) 0.2832(6) -0.0237(2) 0.0432(11) Uani 1 1 d . . . H6 H 0.5137 0.2710 -0.0622 0.052 Uiso 1 1 calc R . . C7 C 0.3083(2) 0.1645(6) -0.03511(18) 0.0373(9) Uani 1 1 d . . . C8 C 0.2463(2) 0.1609(7) -0.09760(18) 0.0398(10) Uani 1 1 d . . . C9 C 0.2727(3) 0.1936(7) -0.1474(2) 0.0487(11) Uani 1 1 d . . . H9 H 0.3307 0.2198 -0.1411 0.058 Uiso 1 1 calc R . . C10 C 0.2129(3) 0.1873(8) -0.2064(2) 0.0595(13) Uani 1 1 d . . . H10 H 0.2313 0.2061 -0.2396 0.071 Uiso 1 1 calc R . . C11 C 0.1263(3) 0.1531(9) -0.2163(2) 0.0617(13) Uani 1 1 d . . . H11 H 0.0866 0.1511 -0.2560 0.074 Uiso 1 1 calc R . . C12 C 0.0986(3) 0.1222(8) -0.1677(2) 0.0540(13) Uani 1 1 d . . . H12 H 0.0403 0.0986 -0.1746 0.065 Uiso 1 1 calc R . . C13 C 0.1582(3) 0.1263(6) -0.10767(18) 0.0408(10) Uani 1 1 d . . . C14 C 0.1274(3) 0.0930(6) -0.0561(2) 0.0407(10) Uani 1 1 d . . . C15 C 0.1919(2) 0.0853(6) 0.00538(18) 0.0370(9) Uani 1 1 d . . . C16 C 0.2771(3) 0.1198(6) 0.01376(19) 0.0395(10) Uani 1 1 d . . . H16 H 0.3171 0.1140 0.0534 0.047 Uiso 1 1 calc R . . C17 C 0.1640(3) 0.0286(7) 0.0576(2) 0.0451(11) Uani 1 1 d . . . H17A H 0.2052 -0.0659 0.0833 0.054 Uiso 1 1 calc R . . H17B H 0.1081 -0.0369 0.0418 0.054 Uiso 1 1 calc R . . C18 C 0.0833(3) 0.3399(7) 0.06311(19) 0.0455(11) Uani 1 1 d . . . H18A H 0.0287 0.2699 0.0541 0.055 Uiso 1 1 calc R . . H18B H 0.0884 0.3820 0.0247 0.055 Uiso 1 1 calc R . . C19 C 0.0843(3) 0.5197(8) 0.1021(2) 0.0559(13) Uani 1 1 d . . . H19A H 0.0353 0.6043 0.0809 0.067 Uiso 1 1 calc R . . H19B H 0.1368 0.5952 0.1081 0.067 Uiso 1 1 calc R . . C20 C 0.0800(3) 0.4618(9) 0.1638(2) 0.0658(15) Uani 1 1 d . . . H20A H 0.0246 0.3999 0.1584 0.079 Uiso 1 1 calc R . . H20B H 0.0852 0.5797 0.1889 0.079 Uiso 1 1 calc R . . C21 C 0.1530(3) 0.3176(8) 0.1956(2) 0.0590(13) Uani 1 1 d . . . H21A H 0.1479 0.2752 0.2340 0.071 Uiso 1 1 calc R . . H21B H 0.2082 0.3848 0.2047 0.071 Uiso 1 1 calc R . . C22 C 0.1506(3) 0.1358(8) 0.15595(19) 0.0520(12) Uani 1 1 d . . . H22A H 0.1985 0.0479 0.1768 0.062 Uiso 1 1 calc R . . H22B H 0.0969 0.0634 0.1486 0.062 Uiso 1 1 calc R . . C23 C 0.7924(3) 0.3755(7) 0.0440(2) 0.0470(11) Uani 1 1 d . . . C24 C 0.5427(5) 0.8593(12) 0.2131(5) 0.127(3) Uani 1 1 d . . . H24A H 0.5532 0.9588 0.1870 0.190 Uiso 1 1 calc R . . H24B H 0.5745 0.7409 0.2116 0.190 Uiso 1 1 calc R . . H24C H 0.5613 0.9081 0.2544 0.190 Uiso 1 1 calc R . . N1 N 0.4501(2) 0.2190(6) 0.02517(17) 0.0402(9) Uani 1 1 d . . . N2 N 0.3889(2) 0.2026(5) -0.02963(15) 0.0377(8) Uani 1 1 d . . . N3 N 0.8626(3) 0.4020(6) 0.0470(2) 0.0611(11) Uani 1 1 d . . . N4 N 0.1571(2) 0.2026(5) 0.09596(15) 0.0399(9) Uani 1 1 d . . . O1 O 0.04957(18) 0.0706(5) -0.06422(14) 0.0492(8) Uani 1 1 d . . . O2 O 0.4481(2) 0.3158(7) 0.14267(15) 0.0749(12) Uani 1 1 d . . . O3 O 0.30489(17) 0.4401(5) 0.12483(13) 0.0493(8) Uani 1 1 d . . . O4 O 0.3568(2) 0.1568(6) 0.18854(18) 0.0724(10) Uani 1 1 d . . . O5 O 0.4132(2) 0.4691(6) 0.22483(14) 0.0694(11) Uani 1 1 d . . . O6 O 0.4550(3) 0.8163(7) 0.1937(2) 0.0949(14) Uani 1 1 d . . . S1 S 0.38103(7) 0.34579(19) 0.16678(5) 0.0467(3) Uani 1 1 d . . . H1 H 0.442(3) 0.208(7) 0.058(2) 0.056 Uiso 1 1 d . . . H4 H 0.209(3) 0.276(7) 0.107(2) 0.056 Uiso 1 1 d . . . H6B H 0.3963 -0.0234 0.1663 0.070 Uiso 1 1 d . . . H6A H 0.4194 0.6501 0.1964 0.070 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.032(2) 0.037(2) 0.043(2) -0.0012(19) 0.0093(18) 0.0011(17) C2 0.041(2) 0.047(3) 0.044(2) -0.003(2) 0.015(2) 0.001(2) C3 0.034(2) 0.045(3) 0.052(3) -0.003(2) 0.010(2) -0.001(2) C4 0.040(2) 0.030(2) 0.061(3) 0.002(2) 0.022(2) -0.0013(19) C5 0.036(2) 0.042(3) 0.052(3) 0.004(2) 0.016(2) 0.0033(19) C6 0.047(2) 0.039(3) 0.043(2) 0.0032(19) 0.015(2) 0.0027(19) C7 0.033(2) 0.037(2) 0.042(2) -0.006(2) 0.0123(18) 0.0010(18) C8 0.036(2) 0.044(2) 0.035(2) -0.004(2) 0.0065(17) -0.0048(19) C9 0.043(2) 0.060(3) 0.041(2) -0.002(2) 0.012(2) 0.000(2) C10 0.059(3) 0.076(4) 0.040(3) 0.005(3) 0.013(2) -0.003(3) C11 0.052(3) 0.088(4) 0.036(3) -0.003(3) 0.003(2) -0.004(3) C12 0.041(2) 0.070(3) 0.040(3) -0.004(2) 0.001(2) -0.007(2) C13 0.039(2) 0.043(3) 0.037(2) -0.005(2) 0.0087(18) -0.002(2) C14 0.033(2) 0.036(2) 0.048(3) -0.0032(19) 0.0071(19) 0.0018(18) C15 0.034(2) 0.037(2) 0.039(2) 0.0007(18) 0.0109(18) 0.0005(17) C16 0.038(2) 0.038(2) 0.037(2) -0.0013(18) 0.0064(18) 0.0009(18) C17 0.043(2) 0.046(3) 0.045(2) 0.000(2) 0.014(2) -0.003(2) C18 0.038(2) 0.054(3) 0.042(2) -0.003(2) 0.0098(19) 0.000(2) C19 0.048(3) 0.060(3) 0.053(3) -0.005(2) 0.009(2) 0.011(2) C20 0.061(3) 0.080(4) 0.057(3) -0.010(3) 0.023(3) 0.004(3) C21 0.061(3) 0.076(4) 0.044(3) -0.006(3) 0.024(2) -0.007(3) C22 0.049(3) 0.068(3) 0.039(2) 0.013(2) 0.015(2) -0.001(2) C23 0.038(2) 0.042(3) 0.060(3) 0.001(2) 0.016(2) 0.001(2) C24 0.106(6) 0.083(5) 0.221(10) 0.017(6) 0.093(6) -0.004(4) N1 0.0336(18) 0.049(2) 0.037(2) 0.0012(17) 0.0101(16) -0.0016(15) N2 0.0346(18) 0.036(2) 0.0379(19) -0.0023(15) 0.0071(15) 0.0033(15) N3 0.046(2) 0.056(3) 0.080(3) 0.003(2) 0.020(2) -0.003(2) N4 0.0328(18) 0.047(2) 0.038(2) 0.0012(16) 0.0103(15) 0.0016(16) O1 0.0330(16) 0.058(2) 0.0521(18) -0.0047(15) 0.0092(13) -0.0009(14) O2 0.0447(18) 0.129(4) 0.053(2) -0.011(2) 0.0195(16) 0.012(2) O3 0.0351(15) 0.059(2) 0.0437(17) 0.0102(15) 0.0013(13) -0.0023(14) O4 0.072(2) 0.056(2) 0.090(3) 0.016(2) 0.029(2) 0.0003(19) O5 0.055(2) 0.103(3) 0.0396(18) -0.0198(19) 0.0035(15) 0.012(2) O6 0.085(3) 0.073(3) 0.136(4) 0.004(3) 0.050(3) -0.010(2) S1 0.0431(6) 0.0560(7) 0.0378(6) 0.0014(6) 0.0100(5) 0.0034(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.390(6) . ? C1 C2 1.391(6) . ? C1 N1 1.393(5) . ? C2 C3 1.386(6) . ? C2 H2 0.9300 . ? C3 C4 1.379(6) . ? C3 H3 0.9300 . ? C4 C5 1.393(6) . ? C4 C23 1.437(6) . ? C5 C6 1.379(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N2 1.312(5) . ? C7 C16 1.433(6) . ? C7 C8 1.460(6) . ? C8 C9 1.391(6) . ? C8 C13 1.404(5) . ? C9 C10 1.387(6) . ? C9 H9 0.9300 . ? C10 C11 1.381(7) . ? C10 H10 0.9300 . ? C11 C12 1.376(7) . ? C11 H11 0.9300 . ? C12 C13 1.402(6) . ? C12 H12 0.9300 . ? C13 C14 1.473(6) . ? C14 O1 1.237(5) . ? C14 C15 1.458(6) . ? C15 C16 1.367(5) . ? C15 C17 1.491(6) . ? C16 H16 0.9300 . ? C17 N4 1.499(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N4 1.506(5) . ? C18 C19 1.508(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.516(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.521(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.524(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N4 1.507(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N3 1.145(5) . ? C24 O6 1.385(8) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N1 N2 1.328(5) . ? N1 H1 0.83(5) . ? N4 H4 0.94(5) . ? O2 S1 1.414(3) . ? O3 S1 1.441(3) . ? O4 S1 1.473(4) . ? O5 S1 1.517(3) . ? O5 H6A 1.405(4) . ? O6 H6A 1.273(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.1(4) . . ? C6 C1 N1 121.6(4) . . ? C2 C1 N1 118.3(4) . . ? C3 C2 C1 119.9(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.3(4) . . ? C3 C4 C23 120.7(4) . . ? C5 C4 C23 119.0(4) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 119.7(4) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N2 C7 C16 126.2(4) . . ? N2 C7 C8 115.7(4) . . ? C16 C7 C8 118.1(3) . . ? C9 C8 C13 119.3(4) . . ? C9 C8 C7 121.1(4) . . ? C13 C8 C7 119.5(4) . . ? C10 C9 C8 120.2(4) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 120.5(5) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 119.6(4) . . ? C12 C13 C14 119.4(4) . . ? C8 C13 C14 121.0(4) . . ? O1 C14 C15 120.5(4) . . ? O1 C14 C13 121.6(4) . . ? C15 C14 C13 117.9(3) . . ? C16 C15 C14 119.6(4) . . ? C16 C15 C17 121.2(4) . . ? C14 C15 C17 119.1(3) . . ? C15 C16 C7 123.6(4) . . ? C15 C16 H16 118.2 . . ? C7 C16 H16 118.2 . . ? C15 C17 N4 113.3(4) . . ? C15 C17 H17A 108.9 . . ? N4 C17 H17A 108.9 . . ? C15 C17 H17B 108.9 . . ? N4 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? N4 C18 C19 110.3(3) . . ? N4 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? N4 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C18 C19 C20 111.8(4) . . ? C18 C19 H19A 109.3 . . ? C20 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C20 C19 H19B 109.3 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 109.7(4) . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C20 C21 C22 111.5(4) . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? N4 C22 C21 109.2(4) . . ? N4 C22 H22A 109.8 . . ? C21 C22 H22A 109.8 . . ? N4 C22 H22B 109.8 . . ? C21 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? N3 C23 C4 179.0(5) . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 N1 C1 118.7(4) . . ? N2 N1 H1 125(3) . . ? C1 N1 H1 116(3) . . ? C7 N2 N1 120.9(3) . . ? C17 N4 C18 112.9(3) . . ? C17 N4 C22 111.4(4) . . ? C18 N4 C22 110.5(3) . . ? C17 N4 H4 109(3) . . ? C18 N4 H4 109(3) . . ? C22 N4 H4 104(3) . . ? S1 O5 H6A 96.5(2) . . ? C24 O6 H6A 127.7(5) . . ? O2 S1 O3 114.0(2) . . ? O2 S1 O4 110.8(3) . . ? O3 S1 O4 109.7(2) . . ? O2 S1 O5 110.6(2) . . ? O3 S1 O5 108.5(2) . . ? O4 S1 O5 102.5(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(6) . . . . ? N1 C1 C2 C3 178.5(4) . . . . ? C1 C2 C3 C4 0.1(7) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? C2 C3 C4 C23 -178.8(4) . . . . ? C3 C4 C5 C6 -0.2(7) . . . . ? C23 C4 C5 C6 178.6(4) . . . . ? C4 C5 C6 C1 0.4(6) . . . . ? C2 C1 C6 C5 -0.4(6) . . . . ? N1 C1 C6 C5 -178.7(4) . . . . ? N2 C7 C8 C9 0.8(6) . . . . ? C16 C7 C8 C9 -177.0(4) . . . . ? N2 C7 C8 C13 -178.4(4) . . . . ? C16 C7 C8 C13 3.8(6) . . . . ? C13 C8 C9 C10 -1.5(7) . . . . ? C7 C8 C9 C10 179.2(4) . . . . ? C8 C9 C10 C11 1.5(8) . . . . ? C9 C10 C11 C12 -0.9(9) . . . . ? C10 C11 C12 C13 0.4(8) . . . . ? C11 C12 C13 C8 -0.4(7) . . . . ? C11 C12 C13 C14 180.0(5) . . . . ? C9 C8 C13 C12 1.0(7) . . . . ? C7 C8 C13 C12 -179.8(4) . . . . ? C9 C8 C13 C14 -179.4(4) . . . . ? C7 C8 C13 C14 -0.2(6) . . . . ? C12 C13 C14 O1 -3.4(7) . . . . ? C8 C13 C14 O1 176.9(4) . . . . ? C12 C13 C14 C15 176.1(4) . . . . ? C8 C13 C14 C15 -3.6(6) . . . . ? O1 C14 C15 C16 -176.9(4) . . . . ? C13 C14 C15 C16 3.6(6) . . . . ? O1 C14 C15 C17 6.5(6) . . . . ? C13 C14 C15 C17 -173.0(4) . . . . ? C14 C15 C16 C7 0.1(6) . . . . ? C17 C15 C16 C7 176.7(4) . . . . ? N2 C7 C16 C15 178.6(4) . . . . ? C8 C7 C16 C15 -3.9(6) . . . . ? C16 C15 C17 N4 80.0(5) . . . . ? C14 C15 C17 N4 -103.4(4) . . . . ? N4 C18 C19 C20 -57.1(5) . . . . ? C18 C19 C20 C21 55.0(6) . . . . ? C19 C20 C21 C22 -55.7(6) . . . . ? C20 C21 C22 N4 58.2(5) . . . . ? C3 C4 C23 N3 126(36) . . . . ? C5 C4 C23 N3 -53(36) . . . . ? C6 C1 N1 N2 -1.8(6) . . . . ? C2 C1 N1 N2 179.9(4) . . . . ? C16 C7 N2 N1 -5.6(6) . . . . ? C8 C7 N2 N1 176.8(4) . . . . ? C1 N1 N2 C7 -179.1(4) . . . . ? C15 C17 N4 C18 69.0(4) . . . . ? C15 C17 N4 C22 -166.0(3) . . . . ? C19 C18 N4 C17 -175.4(4) . . . . ? C19 C18 N4 C22 59.1(5) . . . . ? C21 C22 N4 C17 174.4(4) . . . . ? C21 C22 N4 C18 -59.3(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.83(5) 2.07(5) 2.825(5) 152(5) . N4 H4 O3 0.94(5) 1.85(5) 2.788(5) 174(4) . N4 H4 O4 0.94(5) 2.63(5) 3.259(5) 124(4) . O6 H6A O4 1.273(4) 3.458(4) 4.706(6) 166.5(2) . O6 H6A O2 1.273(4) 2.692(4) 3.557(7) 123.5(2) . O6 H6A O5 1.273(4) 1.405(4) 2.606(6) 153.2(3) . O6 H6A O5 1.273(4) 1.405(4) 2.606(6) 153.2(3) . O6 H6A O3 1.273(4) 2.479(3) 3.510(6) 136.2(2) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.789 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.065 _iucr_refine_instructions_details ; TITL CNpip H2SO4 in MeOH CELL 0.71073 16.4480 6.7220 23.2960 90.000 110.275 90.000 ZERR 4.00 0.0050 0.0050 0.0050 0.005 0.005 0.005 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 96 112 16 24 4 MERG 2 OMIT 0.00 50.00 OMIT -5 1 11 OMIT 8 2 2 OMIT -7 1 1 OMIT -8 2 4 OMIT 17 1 1 OMIT -3 2 4 OMIT 1 6 3 OMIT 4 0 6 OMIT -2 1 2 OMIT 0 7 10 OMIT 8 6 9 OMIT 1 1 18 OMIT -10 5 3 OMIT -1 2 5 OMIT 10 4 4 OMIT 5 7 7 OMIT -4 2 1 OMIT -6 1 5 OMIT -8 2 1 OMIT 11 2 7 OMIT 0 7 9 OMIT 5 0 15 OMIT -2 5 10 OMIT -18 3 7 OMIT -5 1 20 OMIT -7 0 11 OMIT -10 1 2 OMIT 6 2 10 OMIT -8 1 7 OMIT -11 3 22 OMIT -3 2 10 OMIT 5 5 1 OMIT -3 3 6 OMIT 11 0 3 HTAB N1 O2 HTAB N4 O3 HTAB N4 O4 HTAB O6 O4 HTAB O6 O2 HTAB O6 O5 HTAB O6 O5 HTAB O6 O3 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 3 L.S. 6 WGHT 0.094800 EXTI 0.008819 FVAR 0.43299 C1 1 0.534438 0.262329 0.028632 11.00000 0.03215 0.03672 = 0.04307 -0.00115 0.00931 0.00105 C2 1 0.597995 0.279540 0.086237 11.00000 0.04106 0.04743 = 0.04437 -0.00259 0.01453 0.00147 AFIX 43 H2 2 0.583421 0.265236 0.121187 11.00000 -1.20000 AFIX 0 C3 1 0.683060 0.318027 0.091499 11.00000 0.03397 0.04546 = 0.05238 -0.00346 0.00970 -0.00137 AFIX 43 H3 2 0.725677 0.329435 0.129965 11.00000 -1.20000 AFIX 0 C4 1 0.704346 0.339366 0.039530 11.00000 0.04038 0.03045 = 0.06090 0.00223 0.02206 -0.00126 C5 1 0.640776 0.322270 -0.018189 11.00000 0.03612 0.04207 = 0.05173 0.00366 0.01600 0.00326 AFIX 43 H5 2 0.655449 0.337192 -0.053079 11.00000 -1.20000 AFIX 0 C6 1 0.556087 0.283232 -0.023655 11.00000 0.04704 0.03946 = 0.04250 0.00321 0.01457 0.00272 AFIX 43 H6 2 0.513658 0.270954 -0.062169 11.00000 -1.20000 AFIX 0 C7 1 0.308277 0.164473 -0.035111 11.00000 0.03260 0.03737 = 0.04162 -0.00552 0.01229 0.00096 C8 1 0.246285 0.160911 -0.097598 11.00000 0.03605 0.04359 = 0.03516 -0.00353 0.00649 -0.00478 C9 1 0.272747 0.193611 -0.147415 11.00000 0.04321 0.05966 = 0.04138 -0.00171 0.01242 -0.00031 AFIX 43 H9 2 0.330723 0.219805 -0.141119 11.00000 -1.20000 AFIX 0 C10 1 0.212943 0.187269 -0.206433 11.00000 0.05892 0.07570 = 0.04043 0.00463 0.01277 -0.00313 AFIX 43 H10 2 0.231273 0.206125 -0.239588 11.00000 -1.20000 AFIX 0 C11 1 0.126343 0.153145 -0.216321 11.00000 0.05169 0.08779 = 0.03621 -0.00289 0.00331 -0.00378 AFIX 43 H11 2 0.086572 0.151055 -0.256044 11.00000 -1.20000 AFIX 0 C12 1 0.098626 0.122218 -0.167669 11.00000 0.04116 0.07019 = 0.04025 -0.00386 0.00087 -0.00734 AFIX 43 H12 2 0.040283 0.098574 -0.174593 11.00000 -1.20000 AFIX 0 C13 1 0.158243 0.126312 -0.107672 11.00000 0.03906 0.04287 = 0.03698 -0.00517 0.00872 -0.00168 C14 1 0.127438 0.092993 -0.056118 11.00000 0.03305 0.03577 = 0.04773 -0.00322 0.00713 0.00185 C15 1 0.191865 0.085253 0.005380 11.00000 0.03361 0.03653 = 0.03935 0.00067 0.01091 0.00052 C16 1 0.277139 0.119794 0.013757 11.00000 0.03849 0.03789 = 0.03674 -0.00129 0.00636 0.00087 AFIX 43 H16 2 0.317134 0.113962 0.053362 11.00000 -1.20000 AFIX 0 C17 1 0.163978 0.028641 0.057626 11.00000 0.04314 0.04631 = 0.04499 -0.00024 0.01433 -0.00288 AFIX 23 H17A 2 0.205192 -0.065933 0.083328 11.00000 -1.20000 H17B 2 0.108073 -0.036938 0.041768 11.00000 -1.20000 AFIX 0 C18 1 0.083282 0.339920 0.063111 11.00000 0.03758 0.05383 = 0.04202 -0.00304 0.00975 0.00016 AFIX 23 H18A 2 0.028703 0.269899 0.054103 11.00000 -1.20000 H18B 2 0.088368 0.381994 0.024670 11.00000 -1.20000 AFIX 0 C19 1 0.084293 0.519694 0.102065 11.00000 0.04792 0.06044 = 0.05281 -0.00544 0.00923 0.01141 AFIX 23 H19A 2 0.035308 0.604336 0.080876 11.00000 -1.20000 H19B 2 0.136850 0.595240 0.108073 11.00000 -1.20000 AFIX 0 C20 1 0.079989 0.461826 0.163837 11.00000 0.06136 0.08029 = 0.05746 -0.01004 0.02281 0.00381 AFIX 23 H20A 2 0.024552 0.399891 0.158417 11.00000 -1.20000 H20B 2 0.085221 0.579722 0.188875 11.00000 -1.20000 AFIX 0 C21 1 0.152970 0.317606 0.195605 11.00000 0.06137 0.07583 = 0.04419 -0.00559 0.02391 -0.00678 AFIX 23 H21A 2 0.147922 0.275155 0.234025 11.00000 -1.20000 H21B 2 0.208205 0.384803 0.204701 11.00000 -1.20000 AFIX 0 C22 1 0.150596 0.135834 0.155949 11.00000 0.04885 0.06772 = 0.03899 0.01257 0.01473 -0.00138 AFIX 23 H22A 2 0.198487 0.047860 0.176794 11.00000 -1.20000 H22B 2 0.096934 0.063404 0.148633 11.00000 -1.20000 AFIX 0 C23 1 0.792436 0.375483 0.043997 11.00000 0.03810 0.04249 = 0.05962 0.00149 0.01607 0.00085 C24 1 0.542724 0.859325 0.213147 11.00000 0.10590 0.08251 = 0.22106 0.01735 0.09345 -0.00408 AFIX 137 H24A 2 0.553207 0.958812 0.186973 11.00000 -1.50000 H24B 2 0.574480 0.740876 0.211553 11.00000 -1.50000 H24C 2 0.561302 0.908094 0.254418 11.00000 -1.50000 AFIX 0 N1 3 0.450070 0.218964 0.025175 11.00000 0.03364 0.04851 = 0.03677 0.00117 0.01011 -0.00162 N2 3 0.388870 0.202615 -0.029633 11.00000 0.03460 0.03611 = 0.03794 -0.00232 0.00711 0.00329 N3 3 0.862599 0.401964 0.047029 11.00000 0.04635 0.05635 = 0.07955 0.00350 0.02041 -0.00267 N4 3 0.157119 0.202619 0.095962 11.00000 0.03277 0.04683 = 0.03850 0.00121 0.01031 0.00163 O1 4 0.049575 0.070633 -0.064219 11.00000 0.03296 0.05815 = 0.05210 -0.00469 0.00918 -0.00091 O2 4 0.448050 0.315813 0.142672 11.00000 0.04468 0.12862 = 0.05335 -0.01129 0.01952 0.01229 O3 4 0.304888 0.440076 0.124833 11.00000 0.03510 0.05943 = 0.04371 0.01016 0.00126 -0.00229 O4 4 0.356782 0.156789 0.188544 11.00000 0.07196 0.05597 = 0.08958 0.01638 0.02853 0.00031 O5 4 0.413223 0.469140 0.224826 11.00000 0.05522 0.10326 = 0.03956 -0.01982 0.00352 0.01166 O6 4 0.454991 0.816327 0.193667 11.00000 0.08512 0.07340 = 0.13572 0.00375 0.05042 -0.01014 S1 5 0.381027 0.345790 0.166778 11.00000 0.04310 0.05598 = 0.03783 0.00144 0.01005 0.00345 H1 2 0.442050 0.207968 0.058201 11.00000 -1.20000 H4 2 0.209308 0.275834 0.107355 11.00000 -1.20000 H6B 2 10.396300 9.976582 10.166306 11.00000 -1.50000 H6A 2 10.419394 10.650105 10.196400 11.00000 -1.50000 HKLF 4 REM CNpip H2SO4 in MeOH REM R1 = 0.0637 for 2043 Fo > 4sig(Fo) and 0.1405 for all 4194 data REM 324 parameters refined using 0 restraints END WGHT 0.0947 0.0000 REM Highest difference peak 0.789, deepest hole -0.355, 1-sigma level 0.065 Q1 1 0.4203 0.1661 0.1502 11.00000 0.05 0.79 Q2 1 0.4600 0.5334 0.1616 11.00000 0.05 0.77 Q3 1 0.3879 0.3263 0.2317 11.00000 0.05 0.35 Q4 1 0.3639 0.5706 0.1522 11.00000 0.05 0.24 Q5 1 0.1076 0.0066 0.1141 11.00000 0.05 0.24 Q6 1 0.5562 0.2876 0.0108 11.00000 0.05 0.21 Q7 1 0.2935 0.0433 0.1470 11.00000 0.05 0.21 Q8 1 0.4843 0.4128 0.2026 11.00000 0.05 0.20 Q9 1 0.4777 0.1604 0.1279 11.00000 0.05 0.20 Q10 1 0.2612 0.2035 -0.2520 11.00000 0.05 0.20 ; _database_code_depnum_ccdc_archive 'CCDC 928934' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_no2pip_in_ACN #TrackingRef 'web_deposit_cif_file_3_AurelienCrochet_1363102931.NO2pip in ACN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic 4-((4-nitrophenyl)diazenyl)-2-(piperidin-1-ylmethyl)naphthalen-1-ol _chemical_name_common ? _chemical_formula_moiety 'C22 H22 N4 O3' _chemical_formula_sum 'C22 H22 N4 O3' _exptl_crystal_recrystallization_method Acetonitrile _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour red _diffrn_ambient_temperature 200(2) _chemical_formula_weight 390.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2175(7) _cell_length_b 10.7215(16) _cell_length_c 17.295(3) _cell_angle_alpha 82.197(12) _cell_angle_beta 81.572(12) _cell_angle_gamma 89.056(12) _cell_volume 948.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4213 _cell_measurement_theta_min 1.20 _cell_measurement_theta_max 24.38 _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.303 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12143 _diffrn_reflns_av_R_equivalents 0.1473 _diffrn_reflns_av_sigmaI/netI 0.1233 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3343 _reflns_number_gt 1433 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3343 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1476 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1832 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.7527(7) 0.6878(4) 0.0332(2) 0.0463(10) Uani 1 1 d . . . C2 C 1.8738(8) 0.7952(4) 0.0439(2) 0.0528(11) Uani 1 1 d . . . H2 H 1.8091 0.8389 0.0855 0.063 Uiso 1 1 calc R . . C3 C 2.0932(8) 0.8389(4) -0.0074(2) 0.0534(11) Uani 1 1 d . . . H3 H 2.1821 0.9095 0.0004 0.064 Uiso 1 1 calc R . . C4 C 2.1752(7) 0.7751(4) -0.0698(2) 0.0463(10) Uani 1 1 d . . . C5 C 2.0552(8) 0.6684(4) -0.0827(2) 0.0540(11) Uani 1 1 d . . . H5 H 2.1174 0.6269 -0.1255 0.065 Uiso 1 1 calc R . . C6 C 1.8383(8) 0.6241(4) -0.0302(2) 0.0524(11) Uani 1 1 d . . . H6 H 1.7516 0.5525 -0.0375 0.063 Uiso 1 1 calc R . . C7 C 1.2291(7) 0.6498(4) 0.1913(2) 0.0447(10) Uani 1 1 d . . . C8 C 1.0573(7) 0.7367(4) 0.2264(2) 0.0439(9) Uani 1 1 d . . . C9 C 1.0856(8) 0.8687(4) 0.2087(2) 0.0510(11) Uani 1 1 d . . . H9 H 1.2293 0.9021 0.1742 0.061 Uiso 1 1 calc R . . C10 C 0.9069(9) 0.9485(4) 0.2410(2) 0.0572(11) Uani 1 1 d . . . H10 H 0.9313 1.0352 0.2296 0.069 Uiso 1 1 calc R . . C11 C 0.6845(8) 0.8988(4) 0.2919(3) 0.0566(12) Uani 1 1 d . . . H11 H 0.5580 0.9530 0.3116 0.068 Uiso 1 1 calc R . . C12 C 0.6545(8) 0.7730(4) 0.3122(2) 0.0491(10) Uani 1 1 d . . . H12 H 0.5103 0.7418 0.3472 0.059 Uiso 1 1 calc R . . C13 C 0.8392(7) 0.6881(4) 0.2808(2) 0.0462(10) Uani 1 1 d . . . C14 C 0.8157(7) 0.5575(4) 0.3040(2) 0.0467(10) Uani 1 1 d . . . C15 C 0.9939(7) 0.4738(4) 0.2720(2) 0.0474(10) Uani 1 1 d . . . C16 C 1.1987(8) 0.5232(4) 0.2145(2) 0.0483(10) Uani 1 1 d . . . H16 H 1.3168 0.4682 0.1915 0.058 Uiso 1 1 calc R . . C17 C 0.9650(9) 0.3343(4) 0.2982(2) 0.0532(11) Uani 1 1 d . . . H17A H 0.8349 0.3010 0.2717 0.064 Uiso 1 1 calc R . . H17B H 1.1279 0.2931 0.2831 0.064 Uiso 1 1 calc R . . C18 C 0.8191(8) 0.1739(4) 0.4081(2) 0.0515(10) Uani 1 1 d . . . H18A H 0.9667 0.1217 0.3929 0.062 Uiso 1 1 calc R . . H18B H 0.6790 0.1528 0.3809 0.062 Uiso 1 1 calc R . . C19 C 0.7357(8) 0.1463(4) 0.4960(2) 0.0538(11) Uani 1 1 d . . . H19A H 0.6999 0.0570 0.5102 0.065 Uiso 1 1 calc R . . H19B H 0.5767 0.1914 0.5101 0.065 Uiso 1 1 calc R . . C20 C 0.9410(8) 0.1843(4) 0.5425(2) 0.0513(11) Uani 1 1 d . . . H20A H 0.8735 0.1741 0.5983 0.062 Uiso 1 1 calc R . . H20B H 1.0921 0.1309 0.5349 0.062 Uiso 1 1 calc R . . C21 C 1.0161(8) 0.3206(4) 0.5141(2) 0.0527(11) Uani 1 1 d . . . H21A H 0.8697 0.3744 0.5278 0.063 Uiso 1 1 calc R . . H21B H 1.1572 0.3435 0.5403 0.063 Uiso 1 1 calc R . . C22 C 1.0982(7) 0.3412(4) 0.4263(2) 0.0499(10) Uani 1 1 d . . . H22A H 1.1436 0.4290 0.4095 0.060 Uiso 1 1 calc R . . H22B H 1.2507 0.2910 0.4130 0.060 Uiso 1 1 calc R . . N1 N 1.5360(6) 0.6300(3) 0.08699(19) 0.0514(9) Uani 1 1 d . . . N2 N 1.4343(6) 0.7039(3) 0.13416(19) 0.0509(9) Uani 1 1 d . . . N3 N 2.4130(7) 0.8208(4) -0.1237(2) 0.0583(10) Uani 1 1 d . . . N4 N 0.8890(6) 0.3061(3) 0.38409(18) 0.0449(8) Uani 1 1 d . . . O1 O 0.6186(5) 0.5146(3) 0.36107(17) 0.0540(8) Uani 1 1 d . . . O2 O 2.4731(6) 0.7695(3) -0.18328(19) 0.0712(9) Uani 1 1 d . . . O3 O 2.5323(6) 0.9081(3) -0.1071(2) 0.0760(10) Uani 1 1 d . . . H1 H 0.671(12) 0.419(6) 0.384(3) 0.114 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.041(2) 0.053(3) 0.041(2) -0.0018(19) 0.0024(19) 0.001(2) C2 0.046(2) 0.059(3) 0.053(2) -0.013(2) 0.000(2) -0.001(2) C3 0.041(2) 0.059(3) 0.058(3) -0.004(2) -0.003(2) -0.004(2) C4 0.036(2) 0.051(3) 0.048(2) -0.0018(19) 0.0005(19) 0.0008(19) C5 0.053(3) 0.060(3) 0.046(2) -0.007(2) 0.003(2) 0.004(2) C6 0.045(2) 0.061(3) 0.050(2) -0.011(2) 0.000(2) -0.003(2) C7 0.041(2) 0.050(3) 0.039(2) -0.0026(19) 0.0033(18) -0.0031(19) C8 0.038(2) 0.050(3) 0.043(2) -0.0031(18) -0.0034(18) -0.0005(18) C9 0.039(2) 0.058(3) 0.055(2) -0.008(2) -0.002(2) -0.001(2) C10 0.062(3) 0.048(3) 0.063(3) -0.010(2) -0.011(2) 0.004(2) C11 0.042(2) 0.064(3) 0.065(3) -0.016(2) -0.005(2) 0.009(2) C12 0.039(2) 0.051(3) 0.058(2) -0.010(2) -0.0064(19) 0.0025(19) C13 0.039(2) 0.055(3) 0.045(2) -0.011(2) -0.0021(19) 0.0026(19) C14 0.035(2) 0.060(3) 0.043(2) -0.0060(19) 0.0027(18) -0.0051(19) C15 0.043(2) 0.052(3) 0.046(2) -0.009(2) 0.0002(19) -0.001(2) C16 0.041(2) 0.054(3) 0.047(2) -0.008(2) -0.0002(19) 0.0011(19) C17 0.055(3) 0.052(3) 0.050(2) -0.009(2) 0.004(2) 0.002(2) C18 0.045(2) 0.046(2) 0.062(3) -0.006(2) -0.003(2) -0.0023(19) C19 0.045(2) 0.051(3) 0.062(3) -0.003(2) -0.001(2) -0.001(2) C20 0.039(2) 0.060(3) 0.053(2) -0.007(2) -0.0001(19) 0.006(2) C21 0.045(2) 0.060(3) 0.055(3) -0.012(2) -0.010(2) 0.004(2) C22 0.034(2) 0.052(3) 0.064(3) -0.011(2) -0.007(2) -0.0004(19) N1 0.046(2) 0.054(2) 0.051(2) -0.0068(17) 0.0024(17) -0.0011(17) N2 0.0417(19) 0.062(2) 0.0478(19) -0.0069(17) -0.0023(16) 0.0044(17) N3 0.038(2) 0.069(3) 0.062(2) -0.001(2) 0.0025(19) 0.003(2) N4 0.0377(17) 0.048(2) 0.0483(18) -0.0066(15) -0.0022(15) -0.0002(15) O1 0.0364(15) 0.0600(19) 0.0617(18) -0.0058(15) 0.0041(14) -0.0016(14) O2 0.0509(19) 0.091(3) 0.067(2) -0.0154(19) 0.0137(16) -0.0001(17) O3 0.055(2) 0.075(2) 0.092(3) -0.007(2) 0.0056(18) -0.0146(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.370(6) . ? C1 C6 1.385(5) . ? C1 N1 1.444(5) . ? C2 C3 1.387(6) . ? C2 H2 0.9300 . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 C5 1.373(6) . ? C4 N3 1.486(5) . ? C5 C6 1.390(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C16 1.368(6) . ? C7 C8 1.416(5) . ? C7 N2 1.419(5) . ? C8 C9 1.413(6) . ? C8 C13 1.423(5) . ? C9 C10 1.366(5) . ? C9 H9 0.9300 . ? C10 C11 1.414(6) . ? C10 H10 0.9300 . ? C11 C12 1.353(6) . ? C11 H11 0.9300 . ? C12 C13 1.415(5) . ? C12 H12 0.9300 . ? C13 C14 1.405(6) . ? C14 O1 1.356(4) . ? C14 C15 1.390(5) . ? C15 C16 1.406(5) . ? C15 C17 1.506(5) . ? C16 H16 0.9300 . ? C17 N4 1.471(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N4 1.458(5) . ? C18 C19 1.509(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.522(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.516(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.504(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N4 1.479(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? N1 N2 1.269(4) . ? N3 O3 1.221(5) . ? N3 O2 1.231(4) . ? O1 H1 1.09(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.2(4) . . ? C2 C1 N1 123.8(4) . . ? C6 C1 N1 115.0(4) . . ? C1 C2 C3 119.9(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 118.1(4) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C3 C4 C5 123.3(4) . . ? C3 C4 N3 117.9(4) . . ? C5 C4 N3 118.8(4) . . ? C4 C5 C6 118.1(4) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C1 C6 C5 119.3(4) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C16 C7 C8 120.7(4) . . ? C16 C7 N2 123.8(4) . . ? C8 C7 N2 115.5(4) . . ? C9 C8 C7 123.8(4) . . ? C9 C8 C13 118.1(4) . . ? C7 C8 C13 118.0(4) . . ? C10 C9 C8 121.5(4) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.0(4) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 121.5(4) . . ? C14 C13 C8 119.4(3) . . ? C12 C13 C8 119.1(4) . . ? O1 C14 C15 120.2(4) . . ? O1 C14 C13 118.2(3) . . ? C15 C14 C13 121.6(3) . . ? C14 C15 C16 118.1(4) . . ? C14 C15 C17 120.5(3) . . ? C16 C15 C17 121.4(3) . . ? C7 C16 C15 121.8(4) . . ? C7 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? N4 C17 C15 111.6(3) . . ? N4 C17 H17A 109.3 . . ? C15 C17 H17A 109.3 . . ? N4 C17 H17B 109.3 . . ? C15 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? N4 C18 C19 111.4(3) . . ? N4 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? N4 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 C19 C20 112.2(3) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C21 C20 C19 109.0(3) . . ? C21 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? C21 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C22 C21 C20 110.9(3) . . ? C22 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.0 . . ? N4 C22 C21 111.2(3) . . ? N4 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? N4 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? N2 N1 C1 111.9(3) . . ? N1 N2 C7 114.4(4) . . ? O3 N3 O2 124.4(4) . . ? O3 N3 C4 118.1(4) . . ? O2 N3 C4 117.5(4) . . ? C18 N4 C17 111.7(3) . . ? C18 N4 C22 110.3(3) . . ? C17 N4 C22 110.8(3) . . ? C14 O1 H1 106(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.8(6) . . . . ? N1 C1 C2 C3 175.0(4) . . . . ? C1 C2 C3 C4 2.8(6) . . . . ? C2 C3 C4 C5 -1.8(6) . . . . ? C2 C3 C4 N3 -178.9(4) . . . . ? C3 C4 C5 C6 0.6(6) . . . . ? N3 C4 C5 C6 177.7(4) . . . . ? C2 C1 C6 C5 1.7(6) . . . . ? N1 C1 C6 C5 -176.3(4) . . . . ? C4 C5 C6 C1 -0.5(6) . . . . ? C16 C7 C8 C9 176.2(4) . . . . ? N2 C7 C8 C9 -1.5(6) . . . . ? C16 C7 C8 C13 -5.7(6) . . . . ? N2 C7 C8 C13 176.5(3) . . . . ? C7 C8 C9 C10 176.4(4) . . . . ? C13 C8 C9 C10 -1.6(6) . . . . ? C8 C9 C10 C11 -1.6(6) . . . . ? C9 C10 C11 C12 3.6(7) . . . . ? C10 C11 C12 C13 -2.4(6) . . . . ? C11 C12 C13 C14 177.3(4) . . . . ? C11 C12 C13 C8 -0.9(6) . . . . ? C9 C8 C13 C14 -175.4(4) . . . . ? C7 C8 C13 C14 6.5(6) . . . . ? C9 C8 C13 C12 2.8(6) . . . . ? C7 C8 C13 C12 -175.3(4) . . . . ? C12 C13 C14 O1 -3.9(6) . . . . ? C8 C13 C14 O1 174.3(3) . . . . ? C12 C13 C14 C15 178.6(4) . . . . ? C8 C13 C14 C15 -3.2(6) . . . . ? O1 C14 C15 C16 -178.3(3) . . . . ? C13 C14 C15 C16 -0.9(6) . . . . ? O1 C14 C15 C17 2.2(6) . . . . ? C13 C14 C15 C17 179.7(4) . . . . ? C8 C7 C16 C15 1.7(6) . . . . ? N2 C7 C16 C15 179.3(4) . . . . ? C14 C15 C16 C7 1.7(6) . . . . ? C17 C15 C16 C7 -178.8(4) . . . . ? C14 C15 C17 N4 -41.7(5) . . . . ? C16 C15 C17 N4 138.8(4) . . . . ? N4 C18 C19 C20 -55.7(4) . . . . ? C18 C19 C20 C21 53.1(4) . . . . ? C19 C20 C21 C22 -54.3(4) . . . . ? C20 C21 C22 N4 58.5(4) . . . . ? C2 C1 N1 N2 15.2(5) . . . . ? C6 C1 N1 N2 -166.9(3) . . . . ? C1 N1 N2 C7 -176.7(3) . . . . ? C16 C7 N2 N1 22.8(6) . . . . ? C8 C7 N2 N1 -159.5(3) . . . . ? C3 C4 N3 O3 4.4(5) . . . . ? C5 C4 N3 O3 -172.9(4) . . . . ? C3 C4 N3 O2 -174.0(4) . . . . ? C5 C4 N3 O2 8.8(5) . . . . ? C19 C18 N4 C17 -178.7(3) . . . . ? C19 C18 N4 C22 57.6(4) . . . . ? C15 C17 N4 C18 170.5(3) . . . . ? C15 C17 N4 C22 -66.1(4) . . . . ? C21 C22 N4 C18 -59.5(4) . . . . ? C21 C22 N4 C17 176.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N4 1.09(6) 1.65(6) 2.639(4) 148(5) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.234 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.062 _iucr_refine_instructions_details ; TITL NO2pip in ACN CELL 0.71073 5.2175 10.7215 17.2946 82.197 81.572 89.056 ZERR 2.00 0.0007 0.0016 0.0026 0.012 0.012 0.012 LATT 1 SFAC C H N O UNIT 44 44 8 6 MERG 2 OMIT 0.00 50.00 HTAB O1 N4 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 5 WGHT 0.083600 FVAR 0.65329 C1 1 1.752673 0.687817 0.033235 11.00000 0.04057 0.05340 = 0.04101 -0.00178 0.00239 0.00059 C2 1 1.873813 0.795242 0.043917 11.00000 0.04591 0.05911 = 0.05281 -0.01262 -0.00028 -0.00145 AFIX 43 H2 2 1.809064 0.838853 0.085502 11.00000 -1.20000 AFIX 0 C3 1 2.093232 0.838873 -0.007397 11.00000 0.04133 0.05897 = 0.05770 -0.00428 -0.00264 -0.00414 AFIX 43 H3 2 2.182102 0.909547 0.000391 11.00000 -1.20000 AFIX 0 C4 1 2.175180 0.775050 -0.069751 11.00000 0.03622 0.05089 = 0.04835 -0.00180 0.00053 0.00075 C5 1 2.055232 0.668360 -0.082747 11.00000 0.05287 0.05957 = 0.04639 -0.00718 0.00281 0.00396 AFIX 43 H5 2 2.117387 0.626864 -0.125532 11.00000 -1.20000 AFIX 0 C6 1 1.838287 0.624113 -0.030158 11.00000 0.04532 0.06072 = 0.04998 -0.01057 0.00039 -0.00308 AFIX 43 H6 2 1.751564 0.552494 -0.037468 11.00000 -1.20000 AFIX 0 C7 1 1.229106 0.649841 0.191311 11.00000 0.04121 0.05025 = 0.03897 -0.00264 0.00326 -0.00307 C8 1 1.057293 0.736677 0.226393 11.00000 0.03756 0.04965 = 0.04300 -0.00309 -0.00342 -0.00054 C9 1 1.085616 0.868711 0.208677 11.00000 0.03867 0.05825 = 0.05457 -0.00795 -0.00181 -0.00094 AFIX 43 H9 2 1.229299 0.902052 0.174222 11.00000 -1.20000 AFIX 0 C10 1 0.906857 0.948522 0.240982 11.00000 0.06248 0.04760 = 0.06250 -0.00965 -0.01067 0.00362 AFIX 43 H10 2 0.931278 1.035165 0.229551 11.00000 -1.20000 AFIX 0 C11 1 0.684527 0.898807 0.291879 11.00000 0.04161 0.06384 = 0.06520 -0.01552 -0.00544 0.00919 AFIX 43 H11 2 0.557954 0.953011 0.311562 11.00000 -1.20000 AFIX 0 C12 1 0.654493 0.772972 0.312172 11.00000 0.03856 0.05113 = 0.05818 -0.00993 -0.00638 0.00251 AFIX 43 H12 2 0.510313 0.741796 0.347237 11.00000 -1.20000 AFIX 0 C13 1 0.839180 0.688064 0.280841 11.00000 0.03854 0.05472 = 0.04516 -0.01115 -0.00214 0.00262 C14 1 0.815723 0.557540 0.303974 11.00000 0.03510 0.05975 = 0.04272 -0.00605 0.00267 -0.00508 C15 1 0.993853 0.473811 0.272022 11.00000 0.04304 0.05212 = 0.04570 -0.00935 0.00025 -0.00058 C16 1 1.198712 0.523177 0.214467 11.00000 0.04129 0.05432 = 0.04745 -0.00762 -0.00020 0.00115 AFIX 43 H16 2 1.316808 0.468178 0.191510 11.00000 -1.20000 AFIX 0 C17 1 0.964956 0.334291 0.298222 11.00000 0.05530 0.05177 = 0.04962 -0.00900 0.00387 0.00169 AFIX 23 H17A 2 0.834933 0.300975 0.271747 11.00000 -1.20000 H17B 2 1.127942 0.293058 0.283084 11.00000 -1.20000 AFIX 0 C18 1 0.819107 0.173887 0.408067 11.00000 0.04542 0.04553 = 0.06188 -0.00643 -0.00281 -0.00232 AFIX 23 H18A 2 0.966659 0.121705 0.392906 11.00000 -1.20000 H18B 2 0.679018 0.152820 0.380901 11.00000 -1.20000 AFIX 0 C19 1 0.735687 0.146319 0.495959 11.00000 0.04501 0.05102 = 0.06189 -0.00298 -0.00080 -0.00077 AFIX 23 H19A 2 0.699945 0.056992 0.510151 11.00000 -1.20000 H19B 2 0.576727 0.191408 0.510117 11.00000 -1.20000 AFIX 0 C20 1 0.941048 0.184288 0.542502 11.00000 0.03899 0.05957 = 0.05308 -0.00715 -0.00005 0.00621 AFIX 23 H20A 2 0.873538 0.174125 0.598321 11.00000 -1.20000 H20B 2 1.092059 0.130911 0.534867 11.00000 -1.20000 AFIX 0 C21 1 1.016062 0.320620 0.514136 11.00000 0.04529 0.05980 = 0.05479 -0.01163 -0.01013 0.00429 AFIX 23 H21A 2 0.869742 0.374387 0.527845 11.00000 -1.20000 H21B 2 1.157204 0.343462 0.540307 11.00000 -1.20000 AFIX 0 C22 1 1.098212 0.341171 0.426312 11.00000 0.03443 0.05230 = 0.06385 -0.01144 -0.00666 -0.00040 AFIX 23 H22A 2 1.143565 0.429042 0.409500 11.00000 -1.20000 H22B 2 1.250722 0.291048 0.412981 11.00000 -1.20000 AFIX 0 N1 3 1.536016 0.630006 0.086986 11.00000 0.04645 0.05368 = 0.05101 -0.00676 0.00244 -0.00107 N2 3 1.434251 0.703913 0.134159 11.00000 0.04165 0.06172 = 0.04778 -0.00692 -0.00227 0.00436 N3 3 2.413049 0.820752 -0.123699 11.00000 0.03830 0.06918 = 0.06207 -0.00092 0.00252 0.00349 N4 3 0.888989 0.306057 0.384086 11.00000 0.03773 0.04753 = 0.04827 -0.00661 -0.00223 -0.00021 O1 4 0.618610 0.514595 0.361074 11.00000 0.03638 0.05997 = 0.06169 -0.00580 0.00408 -0.00160 O2 4 2.473149 0.769506 -0.183280 11.00000 0.05091 0.09057 = 0.06666 -0.01541 0.01375 -0.00006 O3 4 2.532307 0.908097 -0.107102 11.00000 0.05548 0.07464 = 0.09211 -0.00678 0.00564 -0.01456 H1 2 0.670679 0.419348 0.383815 11.00000 -1.50000 HKLF 4 REM NO2pip REM R1 = 0.0605 for 1433 Fo > 4sig(Fo) and 0.1476 for all 3343 data REM 265 parameters refined using 0 restraints END WGHT 0.0834 0.0000 REM Highest difference peak 0.234, deepest hole -0.234, 1-sigma level 0.062 Q1 1 1.0060 0.3769 0.5399 11.00000 0.05 0.23 Q2 1 0.9022 0.1872 0.2953 11.00000 0.05 0.22 Q3 1 0.9642 0.2621 0.5660 11.00000 0.05 0.22 Q4 1 2.4470 0.7339 -0.2425 11.00000 0.05 0.22 Q5 1 0.8763 0.9762 0.3234 11.00000 0.05 0.20 Q6 1 2.5000 1.0000 0.0000 10.50000 0.05 0.19 Q7 1 1.0060 1.0904 0.2249 11.00000 0.05 0.19 Q8 1 0.9603 0.2960 0.4988 11.00000 0.05 0.19 Q9 1 0.9215 0.3782 0.3395 11.00000 0.05 0.18 Q10 1 1.4931 0.8440 0.1158 11.00000 0.05 0.18 Q11 1 2.5194 0.9004 -0.0124 11.00000 0.05 0.18 Q12 1 1.0290 0.3076 0.5430 11.00000 0.05 0.18 Q13 1 0.9711 0.4135 0.2626 11.00000 0.05 0.18 Q14 1 0.9249 0.7213 0.2334 11.00000 0.05 0.18 Q15 1 0.9070 0.9149 0.2006 11.00000 0.05 0.18 Q16 1 0.9526 0.3414 0.3582 11.00000 0.05 0.17 Q17 1 0.7879 0.7617 0.3180 11.00000 0.05 0.17 Q18 1 1.2262 0.4829 0.1403 11.00000 0.05 0.17 Q19 1 1.0143 0.9084 0.1378 11.00000 0.05 0.17 Q20 1 0.9047 0.3300 0.4199 11.00000 0.05 0.17 ; _database_code_depnum_ccdc_archive 'CCDC 928935' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_NO2pipH_ClO4 #TrackingRef '18493_web_deposit_cif_file_4_AurelienCrochet_1363102931.NO2pipH ClO4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-1-((4-(2-(4-nitrophenyl)hydrazono)-1-oxo-1, 4-dihydronaphthalen-2-yl)methyl)piperidin-1-ium perchlorate ; _chemical_name_common '1-nitrophenylazo-4-naphthol-piperidinium perchlorate' _chemical_formula_moiety 'C22 H23 N4 O3, Cl O4' _chemical_formula_sum 'C22 H23 Cl N4 O7' _exptl_crystal_recrystallization_method 'Methanol, 1,3-dioxolane' _chemical_melting_point ? _exptl_crystal_description square _exptl_crystal_colour red _diffrn_ambient_temperature 200(2) _chemical_formula_weight 490.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.4219(7) _cell_length_b 12.5442(5) _cell_length_c 11.5782(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.116(3) _cell_angle_gamma 90.00 _cell_volume 2140.66(16) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 30506 _cell_measurement_theta_min 1.38 _cell_measurement_theta_max 26.04 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26857 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3766 _reflns_number_gt 2866 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1063P)^2^+0.2014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3766 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1602 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O6 O 0.39167(14) 0.2996(2) -0.0855(2) 0.0923(7) Uani 1 1 d . . . O7 O 0.32329(13) 0.2856(2) -0.2756(2) 0.0871(7) Uani 1 1 d . . . O1 O -0.33298(13) 0.35631(18) 0.13656(18) 0.0767(6) Uani 1 1 d . . . N1 N -0.01084(15) 0.36895(17) -0.0881(2) 0.0547(5) Uani 1 1 d . . . N2 N -0.01594(14) 0.37131(16) 0.02501(18) 0.0557(5) Uani 1 1 d . . . N3 N 0.32323(16) 0.3018(2) -0.1709(2) 0.0699(6) Uani 1 1 d . . . N4 N -0.39273(15) 0.39051(18) -0.1850(2) 0.0625(6) Uani 1 1 d . . . C1 C 0.07371(16) 0.35809(18) -0.1062(2) 0.0526(5) Uani 1 1 d . . . C2 C 0.15184(17) 0.3504(2) -0.0104(2) 0.0602(6) Uani 1 1 d . . . H2 H 0.1489 0.3572 0.0700 0.072 Uiso 1 1 calc R . . C3 C 0.23440(18) 0.3327(2) -0.0313(2) 0.0619(6) Uani 1 1 d . . . H3 H 0.2884 0.3260 0.0341 0.074 Uiso 1 1 calc R . . C4 C 0.23661(16) 0.3249(2) -0.1496(2) 0.0588(6) Uani 1 1 d . . . C5 C 0.16011(17) 0.3353(2) -0.2464(2) 0.0578(6) Uani 1 1 d . . . H5 H 0.1640 0.3308 -0.3266 0.069 Uiso 1 1 calc R . . C6 C 0.07714(17) 0.35245(19) -0.2257(2) 0.0552(6) Uani 1 1 d . . . H6 H 0.0235 0.3603 -0.2914 0.066 Uiso 1 1 calc R . . C7 C -0.09519(17) 0.36609(19) 0.0459(2) 0.0547(6) Uani 1 1 d . . . C8 C -0.09212(17) 0.37689(18) 0.1736(2) 0.0557(6) Uani 1 1 d . . . C9 C -0.01144(18) 0.38769(19) 0.2654(2) 0.0574(6) Uani 1 1 d . . . H9 H 0.0443 0.3885 0.2462 0.069 Uiso 1 1 calc R . . C10 C -0.01080(19) 0.3973(2) 0.3840(2) 0.0635(6) Uani 1 1 d . . . H10 H 0.0453 0.4022 0.4460 0.076 Uiso 1 1 calc R . . C11 C -0.0920(2) 0.4000(2) 0.4139(3) 0.0660(7) Uani 1 1 d . . . H11 H -0.0914 0.4080 0.4957 0.079 Uiso 1 1 calc R . . C12 C -0.17174(19) 0.3912(2) 0.3250(2) 0.0638(7) Uani 1 1 d . . . H12 H -0.2271 0.3951 0.3452 0.077 Uiso 1 1 calc R . . C13 C -0.17440(17) 0.37631(19) 0.2036(2) 0.0568(6) Uani 1 1 d . . . C14 C -0.26049(18) 0.3586(2) 0.1121(2) 0.0618(6) Uani 1 1 d . . . C15 C -0.25883(17) 0.3391(2) -0.0131(2) 0.0596(6) Uani 1 1 d . . . C16 C -0.18003(17) 0.3464(2) -0.0417(2) 0.0578(6) Uani 1 1 d . . . H16 H -0.1815 0.3380 -0.1238 0.069 Uiso 1 1 calc R . . C17 C -0.34392(17) 0.3027(2) -0.1050(2) 0.0638(7) Uani 1 1 d . . . H17A H -0.3285 0.2464 -0.1556 0.077 Uiso 1 1 calc R . . H17B H -0.3849 0.2710 -0.0627 0.077 Uiso 1 1 calc R . . C18 C -0.46813(18) 0.3451(2) -0.2869(3) 0.0701(7) Uani 1 1 d . . . H18A H -0.4426 0.2931 -0.3324 0.084 Uiso 1 1 calc R . . H18B H -0.5114 0.3068 -0.2533 0.084 Uiso 1 1 calc R . . C19 C -0.5175(2) 0.4303(3) -0.3709(3) 0.0837(9) Uani 1 1 d . . . H19A H -0.5692 0.3981 -0.4330 0.100 Uiso 1 1 calc R . . H19B H -0.4762 0.4621 -0.4126 0.100 Uiso 1 1 calc R . . C20 C -0.5524(2) 0.5172(3) -0.3055(3) 0.0873(9) Uani 1 1 d . . . H20A H -0.6005 0.4881 -0.2737 0.105 Uiso 1 1 calc R . . H20B H -0.5791 0.5754 -0.3626 0.105 Uiso 1 1 calc R . . C21 C -0.4754(2) 0.5611(3) -0.2016(3) 0.0824(8) Uani 1 1 d . . . H21A H -0.4314 0.5986 -0.2346 0.099 Uiso 1 1 calc R . . H21B H -0.5002 0.6134 -0.1556 0.099 Uiso 1 1 calc R . . C22 C -0.4275(2) 0.4737(2) -0.1182(3) 0.0707(7) Uani 1 1 d . . . H22A H -0.3763 0.5044 -0.0539 0.085 Uiso 1 1 calc R . . H22B H -0.4701 0.4407 -0.0792 0.085 Uiso 1 1 calc R . . Cl1 Cl -0.23515(4) 0.46856(6) -0.36042(6) 0.0684(3) Uani 1 1 d . . . O4 O -0.30493(17) 0.3931(2) -0.4075(3) 0.1194(10) Uani 1 1 d . . . O5 O -0.23015(19) 0.5414(2) -0.4490(2) 0.1084(9) Uani 1 1 d . . . O3 O -0.15208(15) 0.4107(2) -0.31804(19) 0.0930(7) Uani 1 1 d . . . O2 O -0.25600(18) 0.5205(2) -0.2621(2) 0.0972(7) Uani 1 1 d . . . H1 H -0.0552(15) 0.3721(17) -0.147(2) 0.037(6) Uiso 1 1 d . . . H4 H -0.3577(17) 0.412(2) -0.225(2) 0.050(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O6 0.0595(12) 0.134(2) 0.0897(15) 0.0027(14) 0.0316(11) 0.0021(12) O7 0.0723(12) 0.1185(18) 0.0852(14) -0.0195(12) 0.0460(11) -0.0023(12) O1 0.0684(11) 0.0956(15) 0.0807(12) -0.0058(11) 0.0447(10) -0.0088(10) N1 0.0562(12) 0.0589(12) 0.0557(12) -0.0022(9) 0.0267(10) -0.0022(10) N2 0.0637(12) 0.0521(12) 0.0612(11) -0.0023(9) 0.0336(10) -0.0022(9) N3 0.0589(13) 0.0789(16) 0.0808(15) -0.0021(12) 0.0343(12) -0.0021(11) N4 0.0595(12) 0.0641(13) 0.0744(14) 0.0002(10) 0.0362(11) -0.0011(10) C1 0.0603(13) 0.0440(12) 0.0627(13) -0.0007(10) 0.0325(11) -0.0025(10) C2 0.0669(15) 0.0620(15) 0.0597(14) -0.0005(11) 0.0312(12) -0.0071(12) C3 0.0596(14) 0.0671(16) 0.0637(14) 0.0023(12) 0.0257(12) -0.0066(12) C4 0.0590(14) 0.0571(14) 0.0708(15) -0.0016(11) 0.0353(12) -0.0034(11) C5 0.0688(15) 0.0542(14) 0.0612(14) -0.0023(11) 0.0358(12) -0.0029(11) C6 0.0595(13) 0.0517(13) 0.0611(13) -0.0018(10) 0.0281(11) -0.0038(11) C7 0.0615(14) 0.0481(13) 0.0635(13) -0.0023(10) 0.0325(11) -0.0025(10) C8 0.0689(15) 0.0436(12) 0.0658(14) 0.0000(10) 0.0371(12) 0.0009(11) C9 0.0658(14) 0.0500(13) 0.0643(14) -0.0016(11) 0.0314(12) 0.0015(11) C10 0.0759(16) 0.0565(15) 0.0629(15) 0.0004(11) 0.0277(13) 0.0035(12) C11 0.0858(18) 0.0612(15) 0.0606(14) 0.0008(12) 0.0365(14) -0.0001(13) C12 0.0787(17) 0.0571(14) 0.0707(16) -0.0020(12) 0.0455(14) -0.0042(12) C13 0.0675(15) 0.0511(13) 0.0627(14) -0.0004(11) 0.0360(12) -0.0035(11) C14 0.0672(15) 0.0581(15) 0.0724(15) -0.0013(12) 0.0397(13) -0.0043(12) C15 0.0633(14) 0.0584(15) 0.0660(14) -0.0029(11) 0.0325(12) -0.0049(11) C16 0.0654(15) 0.0563(14) 0.0618(14) -0.0019(11) 0.0344(12) -0.0023(11) C17 0.0646(15) 0.0607(15) 0.0753(16) -0.0012(12) 0.0347(13) -0.0011(12) C18 0.0636(15) 0.0757(18) 0.0751(17) -0.0098(14) 0.0269(13) 0.0010(13) C19 0.0807(19) 0.093(2) 0.0797(19) 0.0006(17) 0.0276(16) 0.0062(17) C20 0.0764(19) 0.087(2) 0.101(2) 0.0088(18) 0.0294(17) 0.0135(16) C21 0.084(2) 0.0693(18) 0.102(2) -0.0016(16) 0.0402(18) 0.0065(16) C22 0.0772(17) 0.0624(16) 0.0814(17) -0.0085(13) 0.0372(14) 0.0025(13) Cl1 0.0644(4) 0.0803(5) 0.0687(4) -0.0002(3) 0.0323(3) -0.0025(3) O4 0.0840(16) 0.111(2) 0.165(3) -0.0405(19) 0.0404(16) -0.0221(15) O5 0.129(2) 0.1097(19) 0.1081(18) 0.0371(15) 0.0680(16) 0.0217(16) O3 0.0777(13) 0.132(2) 0.0777(13) 0.0175(13) 0.0354(11) 0.0224(13) O2 0.1167(19) 0.1017(18) 0.0907(15) -0.0174(13) 0.0577(14) 0.0020(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O6 N3 1.216(3) . ? O7 N3 1.230(3) . ? O1 C14 1.232(3) . ? N1 N2 1.335(3) . ? N1 C1 1.387(3) . ? N1 H1 0.81(2) . ? N2 C7 1.316(3) . ? N3 C4 1.457(3) . ? N4 C22 1.490(3) . ? N4 C17 1.492(4) . ? N4 C18 1.503(4) . ? N4 H4 0.86(3) . ? C1 C2 1.380(4) . ? C1 C6 1.402(3) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.384(4) . ? C3 H3 0.9500 . ? C4 C5 1.374(4) . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C16 1.422(4) . ? C7 C8 1.472(3) . ? C8 C9 1.385(4) . ? C8 C13 1.410(3) . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 C11 1.394(4) . ? C10 H10 0.9500 . ? C11 C12 1.356(4) . ? C11 H11 0.9500 . ? C12 C13 1.407(3) . ? C12 H12 0.9500 . ? C13 C14 1.451(4) . ? C14 C15 1.478(3) . ? C15 C16 1.353(3) . ? C15 C17 1.497(4) . ? C16 H16 0.9500 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.494(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.514(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.522(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.504(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? Cl1 O5 1.393(2) . ? Cl1 O4 1.416(3) . ? Cl1 O2 1.428(2) . ? Cl1 O3 1.428(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C1 118.7(2) . . ? N2 N1 H1 122.9(16) . . ? C1 N1 H1 118.4(16) . . ? C7 N2 N1 120.4(2) . . ? O6 N3 O7 123.1(2) . . ? O6 N3 C4 119.1(2) . . ? O7 N3 C4 117.8(2) . . ? C22 N4 C17 112.8(2) . . ? C22 N4 C18 111.0(2) . . ? C17 N4 C18 109.9(2) . . ? C22 N4 H4 116.2(17) . . ? C17 N4 H4 106.8(17) . . ? C18 N4 H4 99.3(16) . . ? C2 C1 N1 121.5(2) . . ? C2 C1 C6 120.8(2) . . ? N1 C1 C6 117.7(2) . . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 118.5(2) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 122.4(2) . . ? C5 C4 N3 119.4(2) . . ? C3 C4 N3 118.2(2) . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C1 118.9(2) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? N2 C7 C16 125.9(2) . . ? N2 C7 C8 115.0(2) . . ? C16 C7 C8 118.9(2) . . ? C9 C8 C13 118.8(2) . . ? C9 C8 C7 122.4(2) . . ? C13 C8 C7 118.8(2) . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.4(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 121.5(2) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C12 C13 C8 118.8(2) . . ? C12 C13 C14 120.1(2) . . ? C8 C13 C14 121.2(2) . . ? O1 C14 C13 122.2(2) . . ? O1 C14 C15 120.0(3) . . ? C13 C14 C15 117.7(2) . . ? C16 C15 C14 120.3(2) . . ? C16 C15 C17 120.6(2) . . ? C14 C15 C17 118.9(2) . . ? C15 C16 C7 122.8(2) . . ? C15 C16 H16 118.6 . . ? C7 C16 H16 118.6 . . ? N4 C17 C15 113.2(2) . . ? N4 C17 H17A 108.9 . . ? C15 C17 H17A 108.9 . . ? N4 C17 H17B 108.9 . . ? C15 C17 H17B 108.9 . . ? H17A C17 H17B 107.8 . . ? C19 C18 N4 111.6(3) . . ? C19 C18 H18A 109.3 . . ? N4 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? N4 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 C19 C20 112.2(3) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 110.3(3) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C20 111.4(3) . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? N4 C22 C21 111.1(2) . . ? N4 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? N4 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? O5 Cl1 O4 110.9(2) . . ? O5 Cl1 O2 111.21(18) . . ? O4 Cl1 O2 106.71(17) . . ? O5 Cl1 O3 110.37(15) . . ? O4 Cl1 O3 107.20(18) . . ? O2 Cl1 O3 110.34(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C7 -170.2(2) . . . . ? N2 N1 C1 C2 -0.4(3) . . . . ? N2 N1 C1 C6 178.0(2) . . . . ? N1 C1 C2 C3 175.8(2) . . . . ? C6 C1 C2 C3 -2.6(4) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C2 C3 C4 N3 -177.5(2) . . . . ? O6 N3 C4 C5 175.2(3) . . . . ? O7 N3 C4 C5 -4.6(4) . . . . ? O6 N3 C4 C3 -6.5(4) . . . . ? O7 N3 C4 C3 173.7(3) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? N3 C4 C5 C6 177.1(2) . . . . ? C4 C5 C6 C1 -0.4(4) . . . . ? C2 C1 C6 C5 2.2(4) . . . . ? N1 C1 C6 C5 -176.2(2) . . . . ? N1 N2 C7 C16 7.2(4) . . . . ? N1 N2 C7 C8 -175.96(19) . . . . ? N2 C7 C8 C9 -2.3(3) . . . . ? C16 C7 C8 C9 174.8(2) . . . . ? N2 C7 C8 C13 177.6(2) . . . . ? C16 C7 C8 C13 -5.3(3) . . . . ? C13 C8 C9 C10 0.2(4) . . . . ? C7 C8 C9 C10 -179.8(2) . . . . ? C8 C9 C10 C11 -2.2(4) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 C13 1.8(4) . . . . ? C11 C12 C13 C8 -3.7(4) . . . . ? C11 C12 C13 C14 175.1(2) . . . . ? C9 C8 C13 C12 2.6(3) . . . . ? C7 C8 C13 C12 -177.3(2) . . . . ? C9 C8 C13 C14 -176.2(2) . . . . ? C7 C8 C13 C14 3.9(3) . . . . ? C12 C13 C14 O1 0.2(4) . . . . ? C8 C13 C14 O1 178.9(2) . . . . ? C12 C13 C14 C15 -177.5(2) . . . . ? C8 C13 C14 C15 1.2(4) . . . . ? O1 C14 C15 C16 176.9(3) . . . . ? C13 C14 C15 C16 -5.3(4) . . . . ? O1 C14 C15 C17 -7.9(4) . . . . ? C13 C14 C15 C17 169.9(2) . . . . ? C14 C15 C16 C7 4.0(4) . . . . ? C17 C15 C16 C7 -171.1(2) . . . . ? N2 C7 C16 C15 178.1(2) . . . . ? C8 C7 C16 C15 1.3(4) . . . . ? C22 N4 C17 C15 -64.8(3) . . . . ? C18 N4 C17 C15 170.7(2) . . . . ? C16 C15 C17 N4 -84.4(3) . . . . ? C14 C15 C17 N4 100.4(3) . . . . ? C22 N4 C18 C19 55.8(3) . . . . ? C17 N4 C18 C19 -178.7(2) . . . . ? N4 C18 C19 C20 -54.7(3) . . . . ? C18 C19 C20 C21 53.6(4) . . . . ? C19 C20 C21 C22 -54.3(4) . . . . ? C17 N4 C22 C21 179.5(2) . . . . ? C18 N4 C22 C21 -56.7(3) . . . . ? C20 C21 C22 N4 56.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.81(2) 2.16(2) 2.949(3) 165(2) . N4 H4 O2 0.86(3) 2.21(3) 3.001(3) 154(2) . N4 H4 O4 0.86(3) 2.49(3) 3.243(4) 148(2) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.359 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.060 _iucr_refine_instructions_details ; TITL NO2pipH New: P21/c CELL 0.71073 15.4219 12.5442 11.5782 90.000 107.116 90.000 ZERR 4.00 0.0007 0.0005 0.0005 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CL N O UNIT 88 92 4 16 28 MERG 2 OMIT 0.00 50.00 HTAB N1 O3 HTAB N4 O2 HTAB N4 O4 FMAP 2 PLAN 20 SIZE 0.15 0.30 0.42 ACTA BOND $H CONF LIST 3 L.S. 5 TEMP -73.00 WGHT 0.106300 0.201400 FVAR 0.39571 O6 5 0.391667 0.299604 -0.085465 11.00000 0.05946 0.13413 = 0.08968 0.00273 0.03165 0.00206 O7 5 0.323295 0.285614 -0.275640 11.00000 0.07230 0.11853 = 0.08525 -0.01947 0.04601 -0.00234 O1 5 -0.332977 0.356314 0.136559 11.00000 0.06840 0.09558 = 0.08074 -0.00584 0.04473 -0.00876 N1 4 -0.010839 0.368952 -0.088098 11.00000 0.05618 0.05894 = 0.05571 -0.00225 0.02669 -0.00219 N2 4 -0.015938 0.371305 0.025007 11.00000 0.06370 0.05211 = 0.06116 -0.00233 0.03361 -0.00217 N3 4 0.323232 0.301809 -0.170922 11.00000 0.05889 0.07885 = 0.08075 -0.00209 0.03430 -0.00209 N4 4 -0.392733 0.390506 -0.185050 11.00000 0.05954 0.06408 = 0.07445 0.00023 0.03619 -0.00114 C1 1 0.073706 0.358089 -0.106209 11.00000 0.06029 0.04401 = 0.06273 -0.00073 0.03251 -0.00245 C2 1 0.151842 0.350368 -0.010430 11.00000 0.06694 0.06196 = 0.05971 -0.00046 0.03119 -0.00712 AFIX 43 H2 2 0.148861 0.357231 0.070027 11.00000 -1.20000 AFIX 0 C3 1 0.234396 0.332682 -0.031271 11.00000 0.05957 0.06710 = 0.06373 0.00227 0.02565 -0.00658 AFIX 43 H3 2 0.288392 0.326027 0.034119 11.00000 -1.20000 AFIX 0 C4 1 0.236607 0.324886 -0.149585 11.00000 0.05902 0.05710 = 0.07081 -0.00155 0.03534 -0.00343 C5 1 0.160106 0.335289 -0.246391 11.00000 0.06885 0.05419 = 0.06120 -0.00229 0.03585 -0.00293 AFIX 43 H5 2 0.164016 0.330776 -0.326612 11.00000 -1.20000 AFIX 0 C6 1 0.077137 0.352448 -0.225697 11.00000 0.05947 0.05174 = 0.06112 -0.00180 0.02815 -0.00383 AFIX 43 H6 2 0.023486 0.360256 -0.291409 11.00000 -1.20000 AFIX 0 C7 1 -0.095186 0.366087 0.045910 11.00000 0.06151 0.04813 = 0.06349 -0.00233 0.03248 -0.00252 C8 1 -0.092119 0.376886 0.173629 11.00000 0.06888 0.04363 = 0.06580 0.00000 0.03712 0.00087 C9 1 -0.011435 0.387692 0.265398 11.00000 0.06585 0.05003 = 0.06430 -0.00158 0.03143 0.00146 AFIX 43 H9 2 0.044343 0.388450 0.246156 11.00000 -1.20000 AFIX 0 C10 1 -0.010795 0.397348 0.384022 11.00000 0.07588 0.05653 = 0.06289 0.00037 0.02768 0.00346 AFIX 43 H10 2 0.045348 0.402216 0.445988 11.00000 -1.20000 AFIX 0 C11 1 -0.091961 0.400034 0.413868 11.00000 0.08585 0.06119 = 0.06059 0.00079 0.03652 -0.00011 AFIX 43 H11 2 -0.091412 0.408002 0.495676 11.00000 -1.20000 AFIX 0 C12 1 -0.171744 0.391166 0.325028 11.00000 0.07873 0.05707 = 0.07067 -0.00195 0.04546 -0.00419 AFIX 43 H12 2 -0.227061 0.395070 0.345245 11.00000 -1.20000 AFIX 0 C13 1 -0.174399 0.376312 0.203573 11.00000 0.06753 0.05107 = 0.06274 -0.00037 0.03598 -0.00348 C14 1 -0.260486 0.358650 0.112095 11.00000 0.06723 0.05806 = 0.07236 -0.00126 0.03972 -0.00430 C15 1 -0.258826 0.339100 -0.013116 11.00000 0.06325 0.05838 = 0.06595 -0.00290 0.03250 -0.00493 C16 1 -0.180035 0.346399 -0.041736 11.00000 0.06540 0.05630 = 0.06177 -0.00193 0.03442 -0.00226 AFIX 43 H16 2 -0.181483 0.338015 -0.123829 11.00000 -1.20000 AFIX 0 C17 1 -0.343918 0.302749 -0.105026 11.00000 0.06457 0.06074 = 0.07526 -0.00118 0.03473 -0.00111 AFIX 23 H17A 2 -0.328493 0.246419 -0.155556 11.00000 -1.20000 H17B 2 -0.384916 0.271031 -0.062732 11.00000 -1.20000 AFIX 0 C18 1 -0.468129 0.345118 -0.286885 11.00000 0.06363 0.07567 = 0.07506 -0.00981 0.02688 0.00101 AFIX 23 H18A 2 -0.442634 0.293132 -0.332438 11.00000 -1.20000 H18B 2 -0.511354 0.306765 -0.253264 11.00000 -1.20000 AFIX 0 C19 1 -0.517491 0.430313 -0.370886 11.00000 0.08068 0.09332 = 0.07968 0.00059 0.02760 0.00615 AFIX 23 H19A 2 -0.569249 0.398088 -0.433022 11.00000 -1.20000 H19B 2 -0.476174 0.462137 -0.412621 11.00000 -1.20000 AFIX 0 C20 1 -0.552382 0.517230 -0.305470 11.00000 0.07639 0.08687 = 0.10089 0.00883 0.02944 0.01348 AFIX 23 H20A 2 -0.600502 0.488087 -0.273718 11.00000 -1.20000 H20B 2 -0.579057 0.575427 -0.362643 11.00000 -1.20000 AFIX 0 C21 1 -0.475449 0.561096 -0.201637 11.00000 0.08401 0.06931 = 0.10225 -0.00162 0.04022 0.00646 AFIX 23 H21A 2 -0.431432 0.598620 -0.234568 11.00000 -1.20000 H21B 2 -0.500154 0.613408 -0.155555 11.00000 -1.20000 AFIX 0 C22 1 -0.427540 0.473700 -0.118183 11.00000 0.07716 0.06240 = 0.08135 -0.00846 0.03718 0.00246 AFIX 23 H22A 2 -0.376276 0.504360 -0.053939 11.00000 -1.20000 H22B 2 -0.470052 0.440674 -0.079150 11.00000 -1.20000 AFIX 0 CL1 3 -0.235151 0.468558 -0.360416 11.00000 0.06436 0.08032 = 0.06868 -0.00021 0.03225 -0.00249 O4 5 -0.304926 0.393065 -0.407452 11.00000 0.08403 0.11130 = 0.16541 -0.04052 0.04043 -0.02213 O5 5 -0.230154 0.541446 -0.448964 11.00000 0.12887 0.10973 = 0.10810 0.03711 0.06802 0.02170 O3 5 -0.152083 0.410725 -0.318042 11.00000 0.07766 0.13173 = 0.07769 0.01747 0.03541 0.02235 O2 5 -0.255997 0.520458 -0.262113 11.00000 0.11670 0.10166 = 0.09071 -0.01736 0.05769 0.00197 H1 2 -0.055192 0.372110 -0.146916 11.00000 0.03672 H4 2 -0.357667 0.412273 -0.225251 11.00000 0.05021 HKLF 4 1.0 -1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 -1.00 REM NO2pipH New: P21/c REM R1 = 0.0541 for 2866 Fo > 4sig(Fo) and 0.0661 for all 3766 data REM 315 parameters refined using 0 restraints END WGHT 0.1064 0.2015 REM Highest difference peak 0.359, deepest hole -0.416, 1-sigma level 0.060 Q1 1 -0.1678 0.4772 -0.2804 11.00000 0.05 0.36 Q2 1 0.2140 0.3414 -0.1636 11.00000 0.05 0.31 Q3 1 -0.2933 0.4625 -0.4566 11.00000 0.05 0.30 Q4 1 -0.2136 0.3801 0.1482 11.00000 0.05 0.30 Q5 1 0.1984 0.3276 -0.1868 11.00000 0.05 0.30 Q6 1 -0.1378 0.3659 0.0004 11.00000 0.05 0.29 Q7 1 0.1136 0.3505 -0.0492 11.00000 0.05 0.28 Q8 1 -0.0595 0.3823 0.2074 11.00000 0.05 0.27 Q9 1 -0.3751 0.3989 0.0690 11.00000 0.05 0.26 Q10 1 -0.3599 0.4231 0.0894 11.00000 0.05 0.26 Q11 1 -0.1930 0.5469 -0.2662 11.00000 0.05 0.25 Q12 1 -0.2969 0.3877 -0.0635 11.00000 0.05 0.25 Q13 1 -0.1012 0.3802 0.1412 11.00000 0.05 0.24 Q14 1 -0.1281 0.3996 0.3744 11.00000 0.05 0.20 Q15 1 0.0259 0.3756 0.0758 11.00000 0.05 0.20 Q16 1 0.0388 0.3395 -0.2682 11.00000 0.05 0.20 Q17 1 0.3159 0.3500 -0.2802 11.00000 0.05 0.19 Q18 1 0.4174 0.3000 -0.0370 11.00000 0.05 0.19 Q19 1 -0.2791 0.3842 0.0523 11.00000 0.05 0.19 Q20 1 0.0840 0.3307 -0.2102 11.00000 0.05 0.19 ; _database_code_depnum_ccdc_archive 'CCDC 928936' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_no2piph2so4 #TrackingRef '18494_web_deposit_cif_file_5_AurelienCrochet_1363102931.no2piph2so4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-((4-(2-(4-nitrophenyl)hydrazono)-1-oxo-1,4-dihydronaphthalen-2-yl) methyl)piperidin-1-ium hydrogensulfate' ; _chemical_name_common ? _chemical_formula_moiety 'C22 H23 N4 O3, H O4 S' _chemical_formula_sum 'C22 H24 N4 O7 S' _exptl_crystal_recrystallization_method 'MeOH, H2SO4' _chemical_melting_point ? _exptl_crystal_description rectangle _exptl_crystal_colour red _diffrn_ambient_temperature 200(2) _chemical_formula_weight 488.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_int_tables_number 4 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.498(5) _cell_length_b 21.404(5) _cell_length_c 13.732(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.611(5) _cell_angle_gamma 90.00 _cell_volume 2202.9(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 15514 _cell_measurement_theta_min 1.48 _cell_measurement_theta_max 26.23 _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28678 _diffrn_reflns_av_R_equivalents 0.0928 _diffrn_reflns_av_sigmaI/netI 0.0744 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7748 _reflns_number_gt 5188 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.42(11) _refine_ls_number_reflns 7748 _refine_ls_number_parameters 628 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3177(6) 0.0454(2) -0.1299(3) 0.0355(11) Uani 1 1 d . . . C2 C 0.2669(6) 0.1066(2) -0.1558(4) 0.0426(12) Uani 1 1 d . . . H2 H 0.2852 0.1401 -0.1111 0.051 Uiso 1 1 calc R . . C3 C 0.1903(6) 0.1175(2) -0.2466(4) 0.0455(13) Uani 1 1 d . . . H3 H 0.1545 0.1586 -0.2644 0.055 Uiso 1 1 calc R . . C4 C 0.1655(6) 0.0699(3) -0.3108(4) 0.0394(12) Uani 1 1 d . . . C5 C 0.2150(6) 0.0081(2) -0.2865(4) 0.0374(12) Uani 1 1 d . . . H5A H 0.1984 -0.0248 -0.3323 0.045 Uiso 1 1 calc R . . C6 C 0.2879(6) -0.0036(2) -0.1951(4) 0.0370(11) Uani 1 1 d . . . H6 H 0.3179 -0.0451 -0.1765 0.044 Uiso 1 1 calc R . . C7 C 0.5469(5) -0.0271(2) 0.0684(3) 0.0314(10) Uani 1 1 d . . . C8 C 0.5976(5) -0.0914(2) 0.0928(3) 0.0322(10) Uani 1 1 d . . . C9 C 0.5577(6) -0.1411(2) 0.0311(4) 0.0427(12) Uani 1 1 d . . . H9 H 0.4936 -0.1336 -0.0284 0.051 Uiso 1 1 calc R . . C10 C 0.6093(8) -0.2009(3) 0.0545(4) 0.0558(15) Uani 1 1 d . . . H10 H 0.5856 -0.2340 0.0100 0.067 Uiso 1 1 calc R . . C11 C 0.6959(8) -0.2129(3) 0.1430(5) 0.0608(16) Uani 1 1 d . . . H11 H 0.7305 -0.2544 0.1592 0.073 Uiso 1 1 calc R . . C12 C 0.7324(7) -0.1646(3) 0.2081(4) 0.0526(14) Uani 1 1 d . . . H12A H 0.7886 -0.1729 0.2697 0.063 Uiso 1 1 calc R . . C13 C 0.6848(6) -0.1033(2) 0.1816(4) 0.0364(11) Uani 1 1 d . . . C14 C 0.7295(5) -0.0527(2) 0.2499(3) 0.0357(11) Uani 1 1 d . . . C15 C 0.7053(6) 0.0120(2) 0.2150(3) 0.0336(11) Uani 1 1 d . . . C16 C 0.6146(5) 0.0229(2) 0.1309(3) 0.0340(10) Uani 1 1 d . . . H16 H 0.5939 0.0650 0.1115 0.041 Uiso 1 1 calc R . . C17 C 0.7940(6) 0.0635(2) 0.2726(4) 0.0373(11) Uani 1 1 d . . . H17A H 0.8428 0.0943 0.2265 0.045 Uiso 1 1 calc R . . H17B H 0.8957 0.0457 0.3107 0.045 Uiso 1 1 calc R . . C18 C 0.6140(6) 0.0562(2) 0.4223(4) 0.0409(12) Uani 1 1 d . . . H18A H 0.7182 0.0427 0.4630 0.049 Uiso 1 1 calc R . . H18B H 0.5547 0.0184 0.3952 0.049 Uiso 1 1 calc R . . C19 C 0.4837(7) 0.0928(3) 0.4844(4) 0.0506(14) Uani 1 1 d . . . H19A H 0.3766 0.1039 0.4443 0.061 Uiso 1 1 calc R . . H19B H 0.4451 0.0662 0.5390 0.061 Uiso 1 1 calc R . . C20 C 0.5686(8) 0.1509(3) 0.5239(4) 0.0573(16) Uani 1 1 d . . . H20A H 0.6684 0.1396 0.5693 0.069 Uiso 1 1 calc R . . H20B H 0.4802 0.1749 0.5607 0.069 Uiso 1 1 calc R . . C21 C 0.6383(9) 0.1910(3) 0.4420(5) 0.0633(17) Uani 1 1 d . . . H21A H 0.5370 0.2061 0.4006 0.076 Uiso 1 1 calc R . . H21B H 0.7012 0.2279 0.4698 0.076 Uiso 1 1 calc R . . C22 C 0.7647(7) 0.1540(2) 0.3806(4) 0.0438(13) Uani 1 1 d . . . H22A H 0.8056 0.1802 0.3262 0.053 Uiso 1 1 calc R . . H22B H 0.8706 0.1416 0.4208 0.053 Uiso 1 1 calc R . . C23 C -0.1375(6) 0.4145(2) -0.1359(3) 0.0342(11) Uani 1 1 d . . . C24 C -0.1828(6) 0.3543(2) -0.1642(4) 0.0407(11) Uani 1 1 d . . . H24 H -0.1597 0.3205 -0.1208 0.049 Uiso 1 1 calc R . . C25 C -0.2600(6) 0.3431(3) -0.2534(4) 0.0451(13) Uani 1 1 d . . . H25 H -0.2911 0.3018 -0.2729 0.054 Uiso 1 1 calc R . . C26 C -0.2925(6) 0.3941(2) -0.3157(4) 0.0387(11) Uani 1 1 d . . . C27 C -0.2483(6) 0.4532(2) -0.2887(4) 0.0409(12) Uani 1 1 d . . . H27 H -0.2715 0.4869 -0.3323 0.049 Uiso 1 1 calc R . . C28 C -0.1704(6) 0.4647(2) -0.1990(4) 0.0362(11) Uani 1 1 d . . . H28 H -0.1392 0.5061 -0.1800 0.043 Uiso 1 1 calc R . . C29 C 0.0937(5) 0.4873(2) 0.0631(3) 0.0306(10) Uani 1 1 d . . . C30 C 0.1430(5) 0.5517(2) 0.0870(3) 0.0353(11) Uani 1 1 d . . . C31 C 0.1005(7) 0.6017(2) 0.0234(4) 0.0440(12) Uani 1 1 d . . . H31 H 0.0357 0.5942 -0.0359 0.053 Uiso 1 1 calc R . . C32 C 0.1535(7) 0.6614(3) 0.0480(4) 0.0534(14) Uani 1 1 d . . . H32 H 0.1266 0.6950 0.0046 0.064 Uiso 1 1 calc R . . C33 C 0.2449(7) 0.6733(3) 0.1344(4) 0.0530(14) Uani 1 1 d . . . H33 H 0.2827 0.7145 0.1497 0.064 Uiso 1 1 calc R . . C34 C 0.2809(7) 0.6260(3) 0.1975(4) 0.0466(12) Uani 1 1 d . . . H34 H 0.3408 0.6347 0.2578 0.056 Uiso 1 1 calc R . . C35 C 0.2315(6) 0.5650(2) 0.1752(4) 0.0375(11) Uani 1 1 d . . . C36 C 0.2776(6) 0.5144(2) 0.2453(4) 0.0348(11) Uani 1 1 d . . . C37 C 0.2493(6) 0.4497(2) 0.2106(4) 0.0357(11) Uani 1 1 d . . . C38 C 0.1592(6) 0.4384(2) 0.1265(3) 0.0334(10) Uani 1 1 d . . . H38 H 0.1378 0.3962 0.1080 0.040 Uiso 1 1 calc R . . C39 C 0.3334(6) 0.3970(2) 0.2696(4) 0.0377(11) Uani 1 1 d . . . H39A H 0.3805 0.3653 0.2245 0.045 Uiso 1 1 calc R . . H39B H 0.4353 0.4137 0.3089 0.045 Uiso 1 1 calc R . . C40 C 0.1491(6) 0.4056(2) 0.4196(4) 0.0420(12) Uani 1 1 d . . . H40A H 0.2545 0.4159 0.4616 0.050 Uiso 1 1 calc R . . H40B H 0.0979 0.4452 0.3944 0.050 Uiso 1 1 calc R . . C41 C 0.0136(7) 0.3727(3) 0.4789(4) 0.0509(14) Uani 1 1 d . . . H41A H -0.0953 0.3651 0.4381 0.061 Uiso 1 1 calc R . . H41B H -0.0194 0.3995 0.5342 0.061 Uiso 1 1 calc R . . C42 C 0.0862(7) 0.3104(3) 0.5176(4) 0.0548(15) Uani 1 1 d . . . H42A H 0.1854 0.3182 0.5651 0.066 Uiso 1 1 calc R . . H42B H -0.0091 0.2878 0.5515 0.066 Uiso 1 1 calc R . . C43 C 0.1521(8) 0.2707(3) 0.4344(4) 0.0540(15) Uani 1 1 d . . . H43A H 0.2099 0.2326 0.4612 0.065 Uiso 1 1 calc R . . H43B H 0.0492 0.2576 0.3926 0.065 Uiso 1 1 calc R . . C44 C 0.2835(6) 0.3058(2) 0.3735(4) 0.0418(12) Uani 1 1 d . . . H44A H 0.3927 0.3146 0.4133 0.050 Uiso 1 1 calc R . . H44B H 0.3176 0.2794 0.3178 0.050 Uiso 1 1 calc R . . N1 N 0.3973(5) 0.0369(2) -0.0394(3) 0.0389(10) Uani 1 1 d . . . H1 H 0.421(6) 0.068(3) 0.004(4) 0.047 Uiso 1 1 d . . . N2 N 0.4550(5) -0.01979(18) -0.0127(3) 0.0327(9) Uani 1 1 d . . . N3 N 0.0887(5) 0.0818(3) -0.4063(3) 0.0476(11) Uani 1 1 d . . . N4 N 0.6742(5) 0.0973(2) 0.3412(3) 0.0351(10) Uani 1 1 d . . . H4 H 0.585(6) 0.100(2) 0.316(4) 0.042 Uiso 1 1 d . . . N5 N -0.0565(5) 0.4228(2) -0.0449(3) 0.0360(9) Uani 1 1 d . . . H5B H -0.062(6) 0.390(2) -0.004(4) 0.043 Uiso 1 1 d . . . N6 N 0.0010(5) 0.47948(19) -0.0192(3) 0.0344(9) Uani 1 1 d . . . N7 N -0.3772(5) 0.3808(3) -0.4111(3) 0.0506(12) Uani 1 1 d . . . N8 N 0.2062(5) 0.36615(18) 0.3359(3) 0.0331(9) Uani 1 1 d . . . H8A H 0.095(6) 0.352(2) 0.300(3) 0.040 Uiso 1 1 d . . . O1 O 0.7924(5) -0.06309(17) 0.3326(3) 0.0513(9) Uani 1 1 d . . . O2 O 0.0574(5) 0.0391(2) -0.4620(3) 0.0594(11) Uani 1 1 d . . . O3 O 0.0539(6) 0.1368(2) -0.4284(3) 0.0708(13) Uani 1 1 d . . . O4 O 0.3379(5) 0.52468(17) 0.3271(3) 0.0516(9) Uani 1 1 d . . . O5 O -0.4145(5) 0.3270(2) -0.4310(3) 0.0665(12) Uani 1 1 d . . . O6 O -0.4071(5) 0.4255(2) -0.4663(3) 0.0584(10) Uani 1 1 d . . . O7 O 0.9047(5) 0.23592(16) 0.1915(3) 0.0607(9) Uani 1 1 d . . . O8 O 0.6313(4) 0.29092(15) 0.1694(3) 0.0563(9) Uani 1 1 d . . . H8B H 0.6085 0.2525 0.1662 0.084 Uiso 1 1 calc R . . O9 O 0.8818(5) 0.34551(19) 0.2386(3) 0.0618(10) Uani 1 1 d . . . O10 O 0.8824(5) 0.31506(17) 0.0684(3) 0.0561(9) Uani 1 1 d . . . O11 O 0.3178(9) 0.1262(4) 0.2469(5) 0.148(3) Uani 1 1 d . . . O12 O 0.2382(5) 0.22410(17) 0.1681(3) 0.0729(11) Uani 1 1 d . . . H12B H 0.1301 0.2190 0.1523 0.109 Uiso 1 1 calc R . . O13 O 0.5216(6) 0.1790(2) 0.1693(6) 0.155(3) Uani 1 1 d . . . O14 O 0.3003(10) 0.1339(3) 0.0824(4) 0.165(4) Uani 1 1 d . . . S1 S 0.82564(14) 0.30041(5) 0.16581(9) 0.0387(3) Uani 1 1 d . . . S3 S 0.32953(15) 0.16460(6) 0.16587(10) 0.0410(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.038(2) 0.037(3) 0.032(3) 0.008(2) 0.000(2) -0.0028(19) C2 0.049(3) 0.037(3) 0.041(3) 0.004(2) -0.005(2) 0.001(2) C3 0.050(3) 0.033(3) 0.053(3) 0.011(2) -0.005(2) 0.000(2) C4 0.033(2) 0.053(3) 0.032(3) 0.009(2) -0.0049(19) -0.005(2) C5 0.039(2) 0.047(3) 0.026(3) -0.001(2) -0.004(2) 0.000(2) C6 0.035(2) 0.038(3) 0.037(3) 0.005(2) -0.001(2) 0.0005(19) C7 0.032(2) 0.032(2) 0.031(2) -0.001(2) 0.0043(19) 0.0013(18) C8 0.033(2) 0.032(2) 0.031(2) -0.001(2) 0.0009(18) -0.0010(18) C9 0.053(3) 0.035(3) 0.039(3) 0.000(2) 0.001(2) 0.003(2) C10 0.085(4) 0.030(3) 0.052(3) -0.010(3) -0.012(3) 0.006(3) C11 0.093(4) 0.030(3) 0.058(4) -0.004(3) -0.019(3) 0.008(3) C12 0.068(3) 0.039(3) 0.050(3) 0.001(3) -0.008(3) 0.005(2) C13 0.040(2) 0.029(2) 0.040(3) 0.001(2) -0.002(2) 0.0044(19) C14 0.034(2) 0.039(3) 0.034(3) -0.003(2) -0.004(2) 0.0045(18) C15 0.035(2) 0.035(3) 0.031(3) -0.006(2) 0.0045(19) -0.0001(19) C16 0.036(2) 0.036(3) 0.031(2) 0.002(2) 0.0032(19) 0.0026(19) C17 0.043(2) 0.035(3) 0.034(3) -0.003(2) 0.004(2) -0.004(2) C18 0.050(3) 0.037(3) 0.035(3) -0.001(2) 0.002(2) -0.006(2) C19 0.053(3) 0.063(4) 0.035(3) 0.003(3) 0.004(2) 0.011(3) C20 0.075(4) 0.060(4) 0.037(3) -0.005(3) 0.003(3) 0.017(3) C21 0.088(4) 0.047(4) 0.055(4) -0.014(3) 0.000(3) 0.020(3) C22 0.063(3) 0.035(3) 0.034(3) 0.003(2) 0.001(2) -0.001(2) C23 0.038(2) 0.037(3) 0.027(2) 0.002(2) -0.0018(18) -0.0003(19) C24 0.054(3) 0.033(3) 0.036(3) 0.003(2) -0.003(2) -0.001(2) C25 0.057(3) 0.041(3) 0.037(3) -0.009(2) -0.007(2) 0.004(2) C26 0.043(2) 0.044(3) 0.030(3) -0.006(2) -0.002(2) 0.001(2) C27 0.040(3) 0.040(3) 0.042(3) 0.001(2) 0.004(2) 0.004(2) C28 0.035(2) 0.038(3) 0.035(3) -0.002(2) -0.001(2) -0.0015(19) C29 0.033(2) 0.033(2) 0.025(2) -0.0003(19) 0.0016(18) 0.0013(18) C30 0.034(2) 0.035(3) 0.037(3) -0.002(2) 0.0031(19) -0.0002(19) C31 0.061(3) 0.040(3) 0.031(3) 0.006(2) 0.001(2) 0.002(2) C32 0.081(4) 0.035(3) 0.045(3) 0.002(3) 0.006(3) 0.002(3) C33 0.079(4) 0.028(3) 0.052(3) -0.003(3) -0.001(3) -0.009(3) C34 0.064(3) 0.038(3) 0.037(3) -0.008(2) 0.000(2) -0.009(2) C35 0.040(2) 0.040(3) 0.032(3) 0.004(2) 0.0008(19) 0.000(2) C36 0.034(2) 0.030(2) 0.039(3) -0.002(2) -0.001(2) 0.0001(18) C37 0.038(2) 0.039(3) 0.031(3) -0.006(2) 0.004(2) -0.0024(19) C38 0.040(2) 0.025(2) 0.036(3) 0.001(2) 0.010(2) -0.0005(18) C39 0.037(2) 0.038(3) 0.038(3) 0.003(2) 0.002(2) 0.0018(19) C40 0.049(3) 0.039(3) 0.038(3) -0.011(2) 0.005(2) -0.001(2) C41 0.055(3) 0.060(4) 0.037(3) -0.009(3) 0.001(2) -0.005(3) C42 0.060(3) 0.073(4) 0.031(3) 0.008(3) 0.001(2) -0.009(3) C43 0.078(4) 0.042(3) 0.041(3) 0.005(3) -0.012(3) 0.001(3) C44 0.059(3) 0.032(3) 0.034(3) 0.006(2) -0.010(2) 0.010(2) N1 0.048(2) 0.034(2) 0.034(2) 0.0010(19) -0.0038(18) 0.0041(18) N2 0.0391(19) 0.032(2) 0.027(2) 0.0030(17) 0.0011(16) 0.0058(16) N3 0.049(2) 0.056(3) 0.037(3) 0.012(2) -0.0073(19) -0.007(2) N4 0.035(2) 0.038(2) 0.032(2) -0.0053(18) -0.0053(17) 0.0004(17) N5 0.048(2) 0.032(2) 0.028(2) 0.0061(18) -0.0064(16) -0.0055(17) N6 0.0381(19) 0.035(2) 0.030(2) -0.0020(17) 0.0032(16) -0.0023(16) N7 0.051(2) 0.061(3) 0.040(3) -0.009(3) -0.003(2) 0.012(2) N8 0.042(2) 0.029(2) 0.027(2) -0.0035(17) 0.0000(17) -0.0016(16) O1 0.074(2) 0.045(2) 0.034(2) 0.0016(17) -0.0121(17) 0.0057(17) O2 0.068(2) 0.070(3) 0.039(2) 0.006(2) -0.0142(18) -0.019(2) O3 0.087(3) 0.070(3) 0.054(3) 0.018(2) -0.030(2) -0.003(2) O4 0.068(2) 0.045(2) 0.041(2) -0.0031(18) -0.0191(18) -0.0019(17) O5 0.082(3) 0.062(3) 0.054(3) -0.024(2) -0.018(2) 0.002(2) O6 0.066(2) 0.070(3) 0.038(2) -0.002(2) -0.0098(17) 0.019(2) O7 0.062(2) 0.0477(19) 0.073(2) 0.0352(18) 0.0147(18) 0.0152(16) O8 0.0368(16) 0.0413(18) 0.090(3) -0.0062(18) -0.0056(16) -0.0007(13) O9 0.061(2) 0.075(2) 0.049(2) -0.0146(18) -0.0146(17) -0.0146(18) O10 0.094(3) 0.0444(19) 0.0300(17) 0.0036(15) 0.0073(17) -0.0079(18) O11 0.155(5) 0.172(6) 0.120(5) 0.093(5) 0.054(4) 0.061(5) O12 0.057(2) 0.049(2) 0.113(3) -0.017(2) 0.012(2) 0.0097(17) O13 0.057(3) 0.056(3) 0.350(10) 0.029(4) -0.029(4) -0.015(2) O14 0.236(7) 0.144(5) 0.109(4) -0.101(4) -0.115(5) 0.133(5) S1 0.0414(6) 0.0362(8) 0.0381(8) 0.0056(6) -0.0048(5) -0.0007(5) S3 0.0429(6) 0.0382(8) 0.0418(8) -0.0064(6) -0.0027(5) -0.0004(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.376(6) . ? C1 C6 1.392(7) . ? C1 C2 1.406(7) . ? C2 C3 1.379(7) . ? C2 H2 0.9500 . ? C3 C4 1.355(8) . ? C3 H3 0.9500 . ? C4 C5 1.411(7) . ? C4 N3 1.440(6) . ? C5 C6 1.379(7) . ? C5 H5A 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.303(6) . ? C7 C16 1.454(6) . ? C7 C8 1.465(6) . ? C8 C9 1.387(7) . ? C8 C13 1.392(6) . ? C9 C10 1.372(7) . ? C9 H9 0.9500 . ? C10 C11 1.387(8) . ? C10 H10 0.9500 . ? C11 C12 1.389(8) . ? C11 H11 0.9500 . ? C12 C13 1.405(7) . ? C12 H12A 0.9500 . ? C13 C14 1.467(7) . ? C14 O1 1.238(6) . ? C14 C15 1.475(7) . ? C15 C16 1.344(6) . ? C15 C17 1.500(6) . ? C16 H16 0.9500 . ? C17 N4 1.506(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N4 1.499(7) . ? C18 C19 1.530(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.493(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.519(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.510(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N4 1.485(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N5 1.385(6) . ? C23 C24 1.385(7) . ? C23 C28 1.397(7) . ? C24 C25 1.362(7) . ? C24 H24 0.9500 . ? C25 C26 1.404(7) . ? C25 H25 0.9500 . ? C26 C27 1.358(7) . ? C26 N7 1.467(6) . ? C27 C28 1.371(7) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 N6 1.322(6) . ? C29 C38 1.438(6) . ? C29 C30 1.462(6) . ? C30 C35 1.393(7) . ? C30 C31 1.412(7) . ? C31 C32 1.378(7) . ? C31 H31 0.9500 . ? C32 C33 1.377(8) . ? C32 H32 0.9500 . ? C33 C34 1.354(8) . ? C33 H33 0.9500 . ? C34 C35 1.389(7) . ? C34 H34 0.9500 . ? C35 C36 1.484(7) . ? C36 O4 1.219(6) . ? C36 C37 1.477(6) . ? C37 C38 1.344(7) . ? C37 C39 1.516(6) . ? C38 H38 0.9500 . ? C39 N8 1.491(6) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.495(7) . ? C40 N8 1.499(6) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 C42 1.529(8) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 C43 1.518(8) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 C44 1.510(8) . ? C43 H43A 0.9900 . ? C43 H43B 0.9900 . ? C44 N8 1.502(6) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? N1 N2 1.337(5) . ? N1 H1 0.91(5) . ? N3 O2 1.211(6) . ? N3 O3 1.240(6) . ? N4 H4 0.75(5) . ? N5 N6 1.333(6) . ? N5 H5B 0.91(5) . ? N7 O5 1.216(6) . ? N7 O6 1.236(6) . ? N8 H8A 1.01(5) . ? O7 S1 1.539(3) . ? O8 S1 1.473(3) . ? O8 H8B 0.8400 . ? O9 S1 1.444(4) . ? O10 S1 1.449(4) . ? O11 S3 1.388(5) . ? O12 S3 1.447(4) . ? O12 H12B 0.8400 . ? O13 S3 1.472(5) . ? O14 S3 1.333(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C6 122.6(5) . . ? N1 C1 C2 117.3(5) . . ? C6 C1 C2 120.1(4) . . ? C3 C2 C1 119.2(5) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C4 C3 C2 120.5(5) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 121.3(4) . . ? C3 C4 N3 120.2(5) . . ? C5 C4 N3 118.5(5) . . ? C6 C5 C4 118.7(5) . . ? C6 C5 H5A 120.7 . . ? C4 C5 H5A 120.7 . . ? C5 C6 C1 120.1(5) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N2 C7 C16 125.7(4) . . ? N2 C7 C8 115.8(4) . . ? C16 C7 C8 118.3(4) . . ? C9 C8 C13 118.9(4) . . ? C9 C8 C7 122.1(4) . . ? C13 C8 C7 119.0(4) . . ? C10 C9 C8 121.2(5) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.1(5) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.3(6) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 119.0(5) . . ? C11 C12 H12A 120.5 . . ? C13 C12 H12A 120.5 . . ? C8 C13 C12 120.5(5) . . ? C8 C13 C14 121.2(4) . . ? C12 C13 C14 118.2(4) . . ? O1 C14 C13 121.8(4) . . ? O1 C14 C15 120.5(4) . . ? C13 C14 C15 117.6(4) . . ? C16 C15 C14 119.8(4) . . ? C16 C15 C17 122.1(4) . . ? C14 C15 C17 118.0(4) . . ? C15 C16 C7 122.6(4) . . ? C15 C16 H16 118.7 . . ? C7 C16 H16 118.7 . . ? C15 C17 N4 114.8(4) . . ? C15 C17 H17A 108.6 . . ? N4 C17 H17A 108.6 . . ? C15 C17 H17B 108.6 . . ? N4 C17 H17B 108.6 . . ? H17A C17 H17B 107.5 . . ? N4 C18 C19 108.9(4) . . ? N4 C18 H18A 109.9 . . ? C19 C18 H18A 109.9 . . ? N4 C18 H18B 109.9 . . ? C19 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? C20 C19 C18 110.9(5) . . ? C20 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C19 C20 C21 110.7(5) . . ? C19 C20 H20A 109.5 . . ? C21 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C20 110.5(5) . . ? C22 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? N4 C22 C21 110.2(4) . . ? N4 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? N4 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? N5 C23 C24 117.9(4) . . ? N5 C23 C28 121.8(4) . . ? C24 C23 C28 120.3(4) . . ? C25 C24 C23 120.7(5) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 118.2(5) . . ? C24 C25 H25 120.9 . . ? C26 C25 H25 120.9 . . ? C27 C26 C25 121.4(5) . . ? C27 C26 N7 121.4(5) . . ? C25 C26 N7 117.2(5) . . ? C26 C27 C28 120.5(5) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 118.8(5) . . ? C27 C28 H28 120.6 . . ? C23 C28 H28 120.6 . . ? N6 C29 C38 126.0(4) . . ? N6 C29 C30 115.8(4) . . ? C38 C29 C30 118.1(4) . . ? C35 C30 C31 118.5(5) . . ? C35 C30 C29 119.9(4) . . ? C31 C30 C29 121.6(4) . . ? C32 C31 C30 119.5(5) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C33 C32 C31 121.0(6) . . ? C33 C32 H32 119.5 . . ? C31 C32 H32 119.5 . . ? C34 C33 C32 120.0(5) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 120.9(5) . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C34 C35 C30 120.1(5) . . ? C34 C35 C36 119.2(4) . . ? C30 C35 C36 120.7(5) . . ? O4 C36 C37 120.9(4) . . ? O4 C36 C35 122.6(4) . . ? C37 C36 C35 116.5(4) . . ? C38 C37 C36 120.6(4) . . ? C38 C37 C39 121.1(4) . . ? C36 C37 C39 118.1(4) . . ? C37 C38 C29 123.0(4) . . ? C37 C38 H38 118.5 . . ? C29 C38 H38 118.5 . . ? N8 C39 C37 113.1(4) . . ? N8 C39 H39A 109.0 . . ? C37 C39 H39A 109.0 . . ? N8 C39 H39B 109.0 . . ? C37 C39 H39B 109.0 . . ? H39A C39 H39B 107.8 . . ? C41 C40 N8 111.4(4) . . ? C41 C40 H40A 109.3 . . ? N8 C40 H40A 109.3 . . ? C41 C40 H40B 109.3 . . ? N8 C40 H40B 109.3 . . ? H40A C40 H40B 108.0 . . ? C40 C41 C42 111.1(5) . . ? C40 C41 H41A 109.4 . . ? C42 C41 H41A 109.4 . . ? C40 C41 H41B 109.4 . . ? C42 C41 H41B 109.4 . . ? H41A C41 H41B 108.0 . . ? C43 C42 C41 110.3(5) . . ? C43 C42 H42A 109.6 . . ? C41 C42 H42A 109.6 . . ? C43 C42 H42B 109.6 . . ? C41 C42 H42B 109.6 . . ? H42A C42 H42B 108.1 . . ? C44 C43 C42 111.8(5) . . ? C44 C43 H43A 109.3 . . ? C42 C43 H43A 109.3 . . ? C44 C43 H43B 109.3 . . ? C42 C43 H43B 109.3 . . ? H43A C43 H43B 107.9 . . ? N8 C44 C43 111.5(4) . . ? N8 C44 H44A 109.3 . . ? C43 C44 H44A 109.3 . . ? N8 C44 H44B 109.3 . . ? C43 C44 H44B 109.3 . . ? H44A C44 H44B 108.0 . . ? N2 N1 C1 119.8(4) . . ? N2 N1 H1 115(3) . . ? C1 N1 H1 125(3) . . ? C7 N2 N1 120.2(4) . . ? O2 N3 O3 121.8(5) . . ? O2 N3 C4 120.4(5) . . ? O3 N3 C4 117.8(5) . . ? C22 N4 C18 110.7(4) . . ? C22 N4 C17 110.2(4) . . ? C18 N4 C17 112.4(4) . . ? C22 N4 H4 119(4) . . ? C18 N4 H4 96(4) . . ? C17 N4 H4 107(4) . . ? N6 N5 C23 119.0(4) . . ? N6 N5 H5B 124(3) . . ? C23 N5 H5B 116(3) . . ? C29 N6 N5 120.1(4) . . ? O5 N7 O6 124.0(5) . . ? O5 N7 C26 118.3(5) . . ? O6 N7 C26 117.7(5) . . ? C39 N8 C40 114.9(4) . . ? C39 N8 C44 110.1(4) . . ? C40 N8 C44 109.7(4) . . ? C39 N8 H8A 111(3) . . ? C40 N8 H8A 107(2) . . ? C44 N8 H8A 103(3) . . ? S1 O8 H8B 109.5 . . ? S3 O12 H12B 109.5 . . ? O9 S1 O10 114.0(2) . . ? O9 S1 O8 109.8(2) . . ? O10 S1 O8 112.1(2) . . ? O9 S1 O7 109.7(2) . . ? O10 S1 O7 106.5(2) . . ? O8 S1 O7 104.1(2) . . ? O14 S3 O11 112.7(5) . . ? O14 S3 O12 112.7(3) . . ? O11 S3 O12 117.6(4) . . ? O14 S3 O13 105.5(5) . . ? O11 S3 O13 100.5(4) . . ? O12 S3 O13 106.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 178.5(4) . . . . ? C6 C1 C2 C3 -1.0(7) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C2 C3 C4 N3 -178.8(4) . . . . ? C3 C4 C5 C6 0.8(7) . . . . ? N3 C4 C5 C6 -179.7(4) . . . . ? C4 C5 C6 C1 -2.4(6) . . . . ? N1 C1 C6 C5 -177.0(4) . . . . ? C2 C1 C6 C5 2.6(7) . . . . ? N2 C7 C8 C9 3.0(6) . . . . ? C16 C7 C8 C9 -171.9(4) . . . . ? N2 C7 C8 C13 -175.4(4) . . . . ? C16 C7 C8 C13 9.6(6) . . . . ? C13 C8 C9 C10 -2.7(7) . . . . ? C7 C8 C9 C10 178.8(5) . . . . ? C8 C9 C10 C11 2.9(9) . . . . ? C9 C10 C11 C12 -0.6(9) . . . . ? C10 C11 C12 C13 -1.8(9) . . . . ? C9 C8 C13 C12 0.3(7) . . . . ? C7 C8 C13 C12 178.8(4) . . . . ? C9 C8 C13 C14 -179.7(4) . . . . ? C7 C8 C13 C14 -1.2(6) . . . . ? C11 C12 C13 C8 2.0(8) . . . . ? C11 C12 C13 C14 -178.1(5) . . . . ? C8 C13 C14 O1 173.4(4) . . . . ? C12 C13 C14 O1 -6.6(7) . . . . ? C8 C13 C14 C15 -9.6(6) . . . . ? C12 C13 C14 C15 170.4(4) . . . . ? O1 C14 C15 C16 -170.8(4) . . . . ? C13 C14 C15 C16 12.2(6) . . . . ? O1 C14 C15 C17 13.0(6) . . . . ? C13 C14 C15 C17 -164.1(4) . . . . ? C14 C15 C16 C7 -3.8(6) . . . . ? C17 C15 C16 C7 172.2(4) . . . . ? N2 C7 C16 C15 178.4(4) . . . . ? C8 C7 C16 C15 -7.2(6) . . . . ? C16 C15 C17 N4 85.2(6) . . . . ? C14 C15 C17 N4 -98.6(5) . . . . ? N4 C18 C19 C20 -58.0(5) . . . . ? C18 C19 C20 C21 56.1(6) . . . . ? C19 C20 C21 C22 -55.5(7) . . . . ? C20 C21 C22 N4 57.2(6) . . . . ? N5 C23 C24 C25 -178.9(4) . . . . ? C28 C23 C24 C25 -0.1(7) . . . . ? C23 C24 C25 C26 -0.1(7) . . . . ? C24 C25 C26 C27 0.2(7) . . . . ? C24 C25 C26 N7 -179.5(4) . . . . ? C25 C26 C27 C28 -0.1(7) . . . . ? N7 C26 C27 C28 179.6(4) . . . . ? C26 C27 C28 C23 -0.1(7) . . . . ? N5 C23 C28 C27 178.9(4) . . . . ? C24 C23 C28 C27 0.2(7) . . . . ? N6 C29 C30 C35 176.1(4) . . . . ? C38 C29 C30 C35 -8.0(6) . . . . ? N6 C29 C30 C31 -2.7(6) . . . . ? C38 C29 C30 C31 173.2(4) . . . . ? C35 C30 C31 C32 2.7(7) . . . . ? C29 C30 C31 C32 -178.5(5) . . . . ? C30 C31 C32 C33 -1.1(8) . . . . ? C31 C32 C33 C34 -1.3(8) . . . . ? C32 C33 C34 C35 1.9(8) . . . . ? C33 C34 C35 C30 -0.2(8) . . . . ? C33 C34 C35 C36 178.4(5) . . . . ? C31 C30 C35 C34 -2.1(7) . . . . ? C29 C30 C35 C34 179.0(4) . . . . ? C31 C30 C35 C36 179.3(4) . . . . ? C29 C30 C35 C36 0.4(6) . . . . ? C34 C35 C36 O4 9.2(7) . . . . ? C30 C35 C36 O4 -172.2(4) . . . . ? C34 C35 C36 C37 -169.9(4) . . . . ? C30 C35 C36 C37 8.7(6) . . . . ? O4 C36 C37 C38 170.2(4) . . . . ? C35 C36 C37 C38 -10.7(6) . . . . ? O4 C36 C37 C39 -13.2(6) . . . . ? C35 C36 C37 C39 165.9(4) . . . . ? C36 C37 C38 C29 3.3(7) . . . . ? C39 C37 C38 C29 -173.2(4) . . . . ? N6 C29 C38 C37 -178.3(4) . . . . ? C30 C29 C38 C37 6.2(6) . . . . ? C38 C37 C39 N8 -84.8(5) . . . . ? C36 C37 C39 N8 98.7(5) . . . . ? N8 C40 C41 C42 57.9(6) . . . . ? C40 C41 C42 C43 -54.3(6) . . . . ? C41 C42 C43 C44 53.1(6) . . . . ? C42 C43 C44 N8 -55.5(6) . . . . ? C6 C1 N1 N2 2.3(7) . . . . ? C2 C1 N1 N2 -177.2(4) . . . . ? C16 C7 N2 N1 -7.8(6) . . . . ? C8 C7 N2 N1 177.7(4) . . . . ? C1 N1 N2 C7 172.8(4) . . . . ? C3 C4 N3 O2 -176.0(5) . . . . ? C5 C4 N3 O2 4.5(7) . . . . ? C3 C4 N3 O3 3.0(7) . . . . ? C5 C4 N3 O3 -176.5(4) . . . . ? C21 C22 N4 C18 -60.3(5) . . . . ? C21 C22 N4 C17 174.7(5) . . . . ? C19 C18 N4 C22 60.0(5) . . . . ? C19 C18 N4 C17 -176.3(4) . . . . ? C15 C17 N4 C22 -169.8(4) . . . . ? C15 C17 N4 C18 66.3(5) . . . . ? C24 C23 N5 N6 174.8(4) . . . . ? C28 C23 N5 N6 -4.0(6) . . . . ? C38 C29 N6 N5 7.4(7) . . . . ? C30 C29 N6 N5 -177.1(4) . . . . ? C23 N5 N6 C29 -173.5(4) . . . . ? C27 C26 N7 O5 -179.7(5) . . . . ? C25 C26 N7 O5 0.0(7) . . . . ? C27 C26 N7 O6 -0.1(7) . . . . ? C25 C26 N7 O6 179.6(4) . . . . ? C37 C39 N8 C40 -69.1(5) . . . . ? C37 C39 N8 C44 166.5(4) . . . . ? C41 C40 N8 C39 176.6(4) . . . . ? C41 C40 N8 C44 -58.8(5) . . . . ? C43 C44 N8 C39 -175.4(4) . . . . ? C43 C44 N8 C40 57.3(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O14 0.91(5) 2.00(5) 2.777(6) 141(4) . N4 H4 O11 0.75(5) 2.26(5) 3.001(8) 171(5) . N4 H4 O13 0.75(5) 2.66(5) 3.129(8) 123(4) . N5 H5B O10 0.91(5) 1.93(6) 2.826(6) 168(4) 1_455 N8 H8A O9 1.01(5) 1.79(5) 2.777(5) 166(4) 1_455 O8 H8B O13 0.84 1.70 2.533(5) 168.3 . O12 H12B O7 0.84 1.82 2.542(5) 142.4 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.437 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.055 _iucr_refine_instructions_details ; TITL NO2pipH2SO4 in MeOH New: P21 CELL 0.71073 7.4980 21.4040 13.7320 90.000 91.611 90.000 ZERR 4.00 0.0050 0.0050 0.0050 0.000 0.005 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O S UNIT 88 96 16 28 4 MERG 2 OMIT 0.00 50.00 TWIN HTAB N1 O14 HTAB N4 O11 HTAB N4 O13 EQIV $1 x-1, y, z HTAB N5 O10_$1 HTAB N8 O9_$1 HTAB O8 O13 HTAB O12 O7_$1 FMAP 2 PLAN 5 SIZE 0.03 0.27 0.74 ACTA 50.00 BOND $H CONF LIST 3 L.S. 5 TEMP -73.00 WGHT 0.077600 BASF 0.41544 FVAR 0.28023 C1 1 0.317653 0.045437 -0.129942 11.00000 0.03761 0.03715 = 0.03170 0.00778 0.00042 -0.00276 C2 1 0.266875 0.106603 -0.155778 11.00000 0.04920 0.03722 = 0.04110 0.00447 -0.00514 0.00141 AFIX 43 H2 2 0.285153 0.140058 -0.111143 11.00000 -1.20000 AFIX 0 C3 1 0.190255 0.117451 -0.246641 11.00000 0.04965 0.03317 = 0.05322 0.01117 -0.00451 -0.00039 AFIX 43 H3 2 0.154506 0.158574 -0.264418 11.00000 -1.20000 AFIX 0 C4 1 0.165520 0.069914 -0.310816 11.00000 0.03285 0.05282 = 0.03214 0.00855 -0.00493 -0.00470 C5 1 0.215017 0.008106 -0.286545 11.00000 0.03885 0.04711 = 0.02609 -0.00141 -0.00403 -0.00024 AFIX 43 H5A 2 0.198420 -0.024799 -0.332336 11.00000 -1.20000 AFIX 0 C6 1 0.287931 -0.003571 -0.195066 11.00000 0.03546 0.03840 = 0.03708 0.00471 -0.00056 0.00050 AFIX 43 H6 2 0.317919 -0.045092 -0.176450 11.00000 -1.20000 AFIX 0 C7 1 0.546918 -0.027096 0.068429 11.00000 0.03181 0.03172 = 0.03087 -0.00132 0.00428 0.00128 C8 1 0.597590 -0.091435 0.092772 11.00000 0.03305 0.03219 = 0.03143 -0.00120 0.00093 -0.00100 C9 1 0.557740 -0.141126 0.031070 11.00000 0.05343 0.03541 = 0.03913 -0.00046 0.00091 0.00281 AFIX 43 H9 2 0.493618 -0.133642 -0.028439 11.00000 -1.20000 AFIX 0 C10 1 0.609296 -0.200874 0.054474 11.00000 0.08505 0.03004 = 0.05161 -0.01045 -0.01188 0.00622 AFIX 43 H10 2 0.585638 -0.234028 0.009965 11.00000 -1.20000 AFIX 0 C11 1 0.695911 -0.212943 0.143028 11.00000 0.09277 0.02989 = 0.05844 -0.00356 -0.01917 0.00799 AFIX 43 H11 2 0.730474 -0.254443 0.159247 11.00000 -1.20000 AFIX 0 C12 1 0.732379 -0.164619 0.208146 11.00000 0.06836 0.03896 = 0.04995 0.00111 -0.00848 0.00476 AFIX 43 H12A 2 0.788595 -0.172896 0.269657 11.00000 -1.20000 AFIX 0 C13 1 0.684839 -0.103343 0.181620 11.00000 0.03963 0.02900 = 0.04044 0.00083 -0.00153 0.00445 C14 1 0.729488 -0.052657 0.249942 11.00000 0.03387 0.03921 = 0.03378 -0.00286 -0.00382 0.00451 C15 1 0.705342 0.012021 0.215032 11.00000 0.03459 0.03495 = 0.03143 -0.00640 0.00447 -0.00007 C16 1 0.614638 0.022920 0.130909 11.00000 0.03575 0.03554 = 0.03082 0.00184 0.00318 0.00261 AFIX 43 H16 2 0.593950 0.064961 0.111500 11.00000 -1.20000 AFIX 0 C17 1 0.793989 0.063516 0.272561 11.00000 0.04260 0.03530 = 0.03412 -0.00296 0.00368 -0.00409 AFIX 23 H17A 2 0.842824 0.094266 0.226516 11.00000 -1.20000 H17B 2 0.895716 0.045658 0.310728 11.00000 -1.20000 AFIX 0 C18 1 0.613986 0.056182 0.422335 11.00000 0.05035 0.03741 = 0.03507 -0.00113 0.00170 -0.00552 AFIX 23 H18A 2 0.718159 0.042744 0.462999 11.00000 -1.20000 H18B 2 0.554706 0.018437 0.395170 11.00000 -1.20000 AFIX 0 C19 1 0.483668 0.092759 0.484414 11.00000 0.05346 0.06333 = 0.03509 0.00283 0.00434 0.01077 AFIX 23 H19A 2 0.376588 0.103868 0.444274 11.00000 -1.20000 H19B 2 0.445117 0.066245 0.539021 11.00000 -1.20000 AFIX 0 C20 1 0.568643 0.150878 0.523901 11.00000 0.07509 0.05970 = 0.03723 -0.00533 0.00345 0.01661 AFIX 23 H20A 2 0.668442 0.139645 0.569297 11.00000 -1.20000 H20B 2 0.480154 0.174934 0.560738 11.00000 -1.20000 AFIX 0 C21 1 0.638349 0.190997 0.441996 11.00000 0.08842 0.04662 = 0.05482 -0.01395 0.00006 0.02011 AFIX 23 H21A 2 0.536995 0.206081 0.400634 11.00000 -1.20000 H21B 2 0.701151 0.227859 0.469819 11.00000 -1.20000 AFIX 0 C22 1 0.764707 0.153969 0.380631 11.00000 0.06269 0.03492 = 0.03363 0.00292 0.00089 -0.00058 AFIX 23 H22A 2 0.805556 0.180192 0.326214 11.00000 -1.20000 H22B 2 0.870640 0.141595 0.420762 11.00000 -1.20000 AFIX 0 C23 1 -0.137484 0.414541 -0.135924 11.00000 0.03799 0.03733 = 0.02714 0.00193 -0.00176 -0.00026 C24 1 -0.182762 0.354345 -0.164154 11.00000 0.05363 0.03258 = 0.03553 0.00300 -0.00260 -0.00141 AFIX 43 H24 2 -0.159676 0.320528 -0.120802 11.00000 -1.20000 AFIX 0 C25 1 -0.260021 0.343098 -0.253383 11.00000 0.05712 0.04076 = 0.03694 -0.00875 -0.00687 0.00376 AFIX 43 H25 2 -0.291100 0.301845 -0.272931 11.00000 -1.20000 AFIX 0 C26 1 -0.292517 0.394089 -0.315712 11.00000 0.04261 0.04362 = 0.02983 -0.00583 -0.00168 0.00060 C27 1 -0.248277 0.453250 -0.288666 11.00000 0.04047 0.04013 = 0.04217 0.00124 0.00431 0.00381 AFIX 43 H27 2 -0.271521 0.486930 -0.332257 11.00000 -1.20000 AFIX 0 C28 1 -0.170356 0.464737 -0.198970 11.00000 0.03542 0.03784 = 0.03515 -0.00189 -0.00068 -0.00148 AFIX 43 H28 2 -0.139243 0.506094 -0.179995 11.00000 -1.20000 AFIX 0 C29 1 0.093698 0.487309 0.063148 11.00000 0.03327 0.03318 = 0.02543 -0.00033 0.00162 0.00132 C30 1 0.143045 0.551723 0.087003 11.00000 0.03435 0.03507 = 0.03665 -0.00229 0.00310 -0.00021 C31 1 0.100455 0.601720 0.023388 11.00000 0.06062 0.04021 = 0.03102 0.00555 0.00057 0.00215 AFIX 43 H31 2 0.035711 0.594227 -0.035923 11.00000 -1.20000 AFIX 0 C32 1 0.153468 0.661432 0.047956 11.00000 0.08062 0.03482 = 0.04506 0.00215 0.00552 0.00242 AFIX 43 H32 2 0.126556 0.694951 0.004640 11.00000 -1.20000 AFIX 0 C33 1 0.244894 0.673256 0.134373 11.00000 0.07909 0.02815 = 0.05171 -0.00276 -0.00058 -0.00868 AFIX 43 H33 2 0.282694 0.714549 0.149711 11.00000 -1.20000 AFIX 0 C34 1 0.280896 0.625995 0.197484 11.00000 0.06442 0.03795 = 0.03736 -0.00815 -0.00019 -0.00931 AFIX 43 H34 2 0.340810 0.634683 0.257845 11.00000 -1.20000 AFIX 0 C35 1 0.231451 0.565003 0.175196 11.00000 0.04048 0.03975 = 0.03228 0.00407 0.00084 0.00045 C36 1 0.277569 0.514357 0.245315 11.00000 0.03443 0.03045 = 0.03944 -0.00207 -0.00092 0.00009 C37 1 0.249271 0.449694 0.210643 11.00000 0.03757 0.03899 = 0.03058 -0.00604 0.00402 -0.00240 C38 1 0.159213 0.438413 0.126493 11.00000 0.04005 0.02488 = 0.03579 0.00089 0.01022 -0.00054 AFIX 43 H38 2 0.137850 0.396244 0.108001 11.00000 -1.20000 AFIX 0 C39 1 0.333398 0.396988 0.269620 11.00000 0.03689 0.03848 = 0.03792 0.00260 0.00196 0.00185 AFIX 23 H39A 2 0.380516 0.365348 0.224475 11.00000 -1.20000 H39B 2 0.435317 0.413727 0.308900 11.00000 -1.20000 AFIX 0 C40 1 0.149097 0.405593 0.419623 11.00000 0.04919 0.03873 = 0.03839 -0.01147 0.00473 -0.00146 AFIX 23 H40A 2 0.254531 0.415860 0.461613 11.00000 -1.20000 H40B 2 0.097883 0.445249 0.394433 11.00000 -1.20000 AFIX 0 C41 1 0.013630 0.372677 0.478856 11.00000 0.05549 0.06049 = 0.03677 -0.00857 0.00072 -0.00523 AFIX 23 H41A 2 -0.095267 0.365057 0.438149 11.00000 -1.20000 H41B 2 -0.019351 0.399520 0.534233 11.00000 -1.20000 AFIX 0 C42 1 0.086157 0.310425 0.517602 11.00000 0.06025 0.07314 = 0.03107 0.00770 0.00104 -0.00864 AFIX 23 H42A 2 0.185416 0.318237 0.565107 11.00000 -1.20000 H42B 2 -0.009089 0.287818 0.551543 11.00000 -1.20000 AFIX 0 C43 1 0.152146 0.270736 0.434422 11.00000 0.07824 0.04205 = 0.04093 0.00528 -0.01250 0.00127 AFIX 23 H43A 2 0.209942 0.232617 0.461237 11.00000 -1.20000 H43B 2 0.049156 0.257608 0.392604 11.00000 -1.20000 AFIX 0 C44 1 0.283502 0.305773 0.373497 11.00000 0.05862 0.03235 = 0.03374 0.00562 -0.00987 0.01005 AFIX 23 H44A 2 0.392693 0.314604 0.413334 11.00000 -1.20000 H44B 2 0.317552 0.279371 0.317817 11.00000 -1.20000 AFIX 0 N1 3 0.397329 0.036928 -0.039436 11.00000 0.04770 0.03416 = 0.03445 0.00097 -0.00375 0.00407 H1 2 0.421477 0.068283 0.004234 11.00000 -1.20000 N2 3 0.454960 -0.019792 -0.012659 11.00000 0.03908 0.03238 = 0.02655 0.00296 0.00106 0.00579 N3 3 0.088659 0.081818 -0.406315 11.00000 0.04930 0.05578 = 0.03720 0.01154 -0.00726 -0.00683 N4 3 0.674170 0.097308 0.341211 11.00000 0.03502 0.03827 = 0.03167 -0.00532 -0.00534 0.00037 H4 2 0.584788 0.100346 0.316114 11.00000 -1.20000 N5 3 -0.056528 0.422760 -0.044922 11.00000 0.04756 0.03218 = 0.02786 0.00615 -0.00637 -0.00552 H5B 2 -0.061640 0.389637 -0.003631 11.00000 -1.20000 N6 3 0.000954 0.479478 -0.019211 11.00000 0.03808 0.03527 = 0.03012 -0.00203 0.00324 -0.00235 N7 3 -0.377171 0.380848 -0.411129 11.00000 0.05087 0.06075 = 0.04002 -0.00893 -0.00302 0.01171 N8 3 0.206197 0.366148 0.335882 11.00000 0.04246 0.02942 = 0.02740 -0.00348 -0.00003 -0.00159 H8A 2 0.095078 0.351953 0.299515 11.00000 -1.20000 O1 4 0.792404 -0.063088 0.332630 11.00000 0.07433 0.04460 = 0.03415 0.00155 -0.01206 0.00574 O2 4 0.057388 0.039072 -0.462017 11.00000 0.06845 0.06978 = 0.03918 0.00612 -0.01419 -0.01897 O3 4 0.053900 0.136777 -0.428355 11.00000 0.08684 0.06989 = 0.05400 0.01759 -0.02996 -0.00298 O4 4 0.337859 0.524676 0.327086 11.00000 0.06764 0.04538 = 0.04072 -0.00312 -0.01914 -0.00189 O5 4 -0.414456 0.326963 -0.431037 11.00000 0.08240 0.06182 = 0.05420 -0.02442 -0.01826 0.00217 O6 4 -0.407142 0.425525 -0.466276 11.00000 0.06606 0.07000 = 0.03844 -0.00196 -0.00985 0.01864 O7 4 0.904712 0.235922 0.191511 11.00000 0.06224 0.04771 = 0.07291 0.03523 0.01475 0.01524 O8 4 0.631290 0.290925 0.169352 11.00000 0.03676 0.04134 = 0.09043 -0.00618 -0.00558 -0.00075 AFIX 147 H8B 2 0.608459 0.252544 0.166223 11.00000 -1.50000 AFIX 0 O9 4 0.881774 0.345509 0.238606 11.00000 0.06067 0.07492 = 0.04890 -0.01459 -0.01463 -0.01461 O10 4 0.882399 0.315056 0.068415 11.00000 0.09436 0.04441 = 0.02996 0.00365 0.00730 -0.00792 O11 4 0.317781 0.126243 0.246938 11.00000 0.15492 0.17152 = 0.12050 0.09322 0.05386 0.06082 O12 4 0.238169 0.224097 0.168140 11.00000 0.05749 0.04868 = 0.11301 -0.01654 0.01249 0.00973 AFIX 147 H12B 2 0.130128 0.218974 0.152314 11.00000 -1.50000 AFIX 0 O13 4 0.521588 0.178985 0.169270 11.00000 0.05689 0.05572 = 0.34986 0.02911 -0.02877 -0.01506 O14 4 0.300275 0.133943 0.082431 11.00000 0.23596 0.14385 = 0.10897 -0.10143 -0.11483 0.13341 S1 5 0.825636 0.300406 0.165813 11.00000 0.04140 0.03619 = 0.03807 0.00556 -0.00483 -0.00067 S3 5 0.329535 0.164603 0.165871 11.00000 0.04291 0.03824 = 0.04177 -0.00643 -0.00274 -0.00039 HKLF 4 1.0 -1.00 0.00 0.00 0.00 0.00 -1.00 0.00 -1.00 0.00 REM NO2pipH2SO4 in MeOH New: P21 REM R1 = 0.0493 for 5188 Fo > 4sig(Fo) and 0.0820 for all 7748 data REM 628 parameters refined using 1 restraints END WGHT 0.0775 0.0000 REM Highest difference peak 0.437, deepest hole -0.370, 1-sigma level 0.055 Q1 1 0.1216 0.1711 0.1580 11.00000 0.05 0.44 Q2 1 1.0482 0.2937 0.1866 11.00000 0.05 0.42 Q3 1 0.9972 0.2778 0.2156 11.00000 0.05 0.39 Q4 1 0.4025 0.2313 0.1966 11.00000 0.05 0.37 Q5 1 0.2062 0.1213 0.2064 11.00000 0.05 0.35 ; _database_code_depnum_ccdc_archive 'CCDC 928937' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_no2piphcl #TrackingRef '18495_web_deposit_cif_file_6_AurelienCrochet_1363102931.no2piphcl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'diaqua 1-((4-(2-(4-nitrophenyl)hydrazono)-1-oxo-1,4-dihydronaphthalen-2-yl) methyl)piperidin-1-ium chloride' ; _chemical_name_common ? _chemical_formula_moiety 'C22 H23 N4 O3, Cl, 2(H2 O)' _chemical_formula_sum 'C22 H27 Cl N4 O5' _exptl_crystal_recrystallization_method methanol _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour red _diffrn_ambient_temperature 200(2) _chemical_formula_weight 462.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9584(6) _cell_length_b 12.8269(11) _cell_length_c 13.1334(11) _cell_angle_alpha 76.183(7) _cell_angle_beta 85.273(7) _cell_angle_gamma 86.982(7) _cell_volume 1133.77(17) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9444 _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 25.96 _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2T' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14564 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3989 _reflns_number_gt 2738 _reflns_threshold_expression >2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2009)' _computing_cell_refinement X-Area _computing_data_reduction 'X-RED32(Stoe & Cie, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3989 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2523(3) 0.99246(14) -0.06197(13) 0.0358(4) Uani 1 1 d . . . C2 C 0.2568(3) 0.96899(15) -0.16009(14) 0.0460(5) Uani 1 1 d . . . H2 H 0.2369 0.8978 -0.1654 0.055 Uiso 1 1 calc R . . C3 C 0.2900(3) 1.04877(16) -0.24924(15) 0.0482(5) Uani 1 1 d . . . H3 H 0.2918 1.0332 -0.3165 0.058 Uiso 1 1 calc R . . C4 C 0.3206(3) 1.15124(15) -0.24114(14) 0.0400(4) Uani 1 1 d . . . C5 C 0.3199(3) 1.17583(15) -0.14435(15) 0.0428(5) Uani 1 1 d . . . H5A H 0.3435 1.2468 -0.1397 0.051 Uiso 1 1 calc R . . C6 C 0.2844(3) 1.09639(14) -0.05467(14) 0.0399(4) Uani 1 1 d . . . H6 H 0.2820 1.1126 0.0123 0.048 Uiso 1 1 calc R . . C7 C 0.1776(2) 0.85485(14) 0.20634(13) 0.0346(4) Uani 1 1 d . . . C8 C 0.1909(3) 0.88627(14) 0.30550(14) 0.0374(4) Uani 1 1 d . . . C9 C 0.2338(3) 0.99114(16) 0.30779(17) 0.0516(5) Uani 1 1 d . . . H9 H 0.2509 1.0444 0.2440 0.062 Uiso 1 1 calc R . . C10 C 0.2511(4) 1.01687(19) 0.40193(19) 0.0702(7) Uani 1 1 d . . . H10 H 0.2814 1.0879 0.4030 0.084 Uiso 1 1 calc R . . C11 C 0.2247(4) 0.9404(2) 0.49550(19) 0.0745(8) Uani 1 1 d . . . H11 H 0.2384 0.9592 0.5602 0.089 Uiso 1 1 calc R . . C12 C 0.1796(3) 0.83862(18) 0.49575(16) 0.0546(6) Uani 1 1 d . . . H12 H 0.1598 0.7869 0.5605 0.066 Uiso 1 1 calc R . . C13 C 0.1623(3) 0.81004(15) 0.40086(14) 0.0381(4) Uani 1 1 d . . . C14 C 0.1140(3) 0.69923(15) 0.40320(13) 0.0377(4) Uani 1 1 d . . . C15 C 0.1004(3) 0.67145(14) 0.30183(13) 0.0344(4) Uani 1 1 d . . . C16 C 0.1284(2) 0.74615(13) 0.21103(13) 0.0335(4) Uani 1 1 d . . . H16 H 0.1150 0.7261 0.1469 0.040 Uiso 1 1 calc R . . C17 C 0.0480(3) 0.55889(14) 0.30222(14) 0.0379(4) Uani 1 1 d . . . H17A H -0.0165 0.5253 0.3715 0.046 Uiso 1 1 calc R . . H17B H -0.0442 0.5618 0.2480 0.046 Uiso 1 1 calc R . . C18 C 0.1635(3) 0.38775(15) 0.25918(16) 0.0477(5) Uani 1 1 d . . . H18A H 0.0740 0.4035 0.2022 0.057 Uiso 1 1 calc R . . H18B H 0.0955 0.3439 0.3230 0.057 Uiso 1 1 calc R . . C19 C 0.3400(4) 0.32587(17) 0.22722(16) 0.0561(6) Uani 1 1 d . . . H19A H 0.4007 0.3675 0.1600 0.067 Uiso 1 1 calc R . . H19B H 0.3003 0.2568 0.2157 0.067 Uiso 1 1 calc R . . C20 C 0.4865(4) 0.30377(16) 0.30949(17) 0.0551(6) Uani 1 1 d . . . H20A H 0.6052 0.2703 0.2825 0.066 Uiso 1 1 calc R . . H20B H 0.4337 0.2529 0.3735 0.066 Uiso 1 1 calc R . . C21 C 0.5353(3) 0.40727(16) 0.33697(16) 0.0489(5) Uani 1 1 d . . . H21A H 0.6208 0.3904 0.3958 0.059 Uiso 1 1 calc R . . H21B H 0.6060 0.4536 0.2756 0.059 Uiso 1 1 calc R . . C22 C 0.3559(3) 0.46729(15) 0.36795(14) 0.0395(4) Uani 1 1 d . . . H22A H 0.2899 0.4235 0.4324 0.047 Uiso 1 1 calc R . . H22B H 0.3920 0.5353 0.3833 0.047 Uiso 1 1 calc R . . Cl1 Cl 0.88884(9) 0.30368(4) 0.05958(4) 0.05316(17) Uani 1 1 d . . . N1 N 0.2131(2) 0.90982(12) 0.02619(11) 0.0387(4) Uani 1 1 d . . . N2 N 0.2150(2) 0.92983(11) 0.12070(11) 0.0361(3) Uani 1 1 d . . . N3 N 0.3496(2) 1.23499(14) -0.33699(14) 0.0500(4) Uani 1 1 d . . . N4 N 0.2222(2) 0.49112(11) 0.28087(11) 0.0361(3) Uani 1 1 d . . . O1 O 0.0869(2) 0.63199(11) 0.48672(9) 0.0508(4) Uani 1 1 d . . . O2 O 0.3402(3) 1.21179(14) -0.42159(12) 0.0709(5) Uani 1 1 d . . . O3 O 0.3792(3) 1.32602(13) -0.32871(13) 0.0700(5) Uani 1 1 d . . . O4 O 0.4211(3) 0.60204(14) 0.10084(12) 0.0612(4) Uani 1 1 d . . . O5 O 0.7975(2) 0.54686(14) 0.07834(13) 0.0601(4) Uani 1 1 d . . . H1 H 0.179(4) 0.845(2) 0.017(2) 0.090 Uiso 1 1 d . . . H4A H 0.293(4) 0.531(2) 0.219(2) 0.090 Uiso 1 1 d . . . H4B H 0.355(4) 0.626(2) 0.046(2) 0.090 Uiso 1 1 d . . . H4C H 0.544(5) 0.584(2) 0.084(2) 0.090 Uiso 1 1 d . . . H5B H 0.814(4) 0.486(2) 0.068(2) 0.090 Uiso 1 1 d . . . H5C H 0.886(4) 0.589(2) 0.035(2) 0.090 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0325(10) 0.0375(10) 0.0354(10) -0.0048(8) -0.0004(8) -0.0035(8) C2 0.0599(13) 0.0396(10) 0.0388(10) -0.0099(8) 0.0020(9) -0.0102(9) C3 0.0578(13) 0.0532(12) 0.0337(10) -0.0095(9) 0.0007(9) -0.0113(10) C4 0.0331(10) 0.0451(11) 0.0371(10) 0.0000(8) -0.0008(8) -0.0061(8) C5 0.0420(11) 0.0365(10) 0.0488(11) -0.0060(8) -0.0044(9) -0.0083(9) C6 0.0449(11) 0.0386(10) 0.0365(10) -0.0083(8) -0.0037(8) -0.0060(9) C7 0.0313(10) 0.0370(9) 0.0349(9) -0.0075(8) -0.0019(7) -0.0016(8) C8 0.0331(10) 0.0416(10) 0.0385(10) -0.0114(8) -0.0002(8) -0.0039(8) C9 0.0613(14) 0.0436(11) 0.0527(12) -0.0176(10) 0.0019(10) -0.0086(10) C10 0.102(2) 0.0531(13) 0.0638(15) -0.0281(12) -0.0011(14) -0.0211(13) C11 0.115(2) 0.0682(15) 0.0524(14) -0.0336(12) -0.0085(14) -0.0175(15) C12 0.0716(16) 0.0593(13) 0.0367(11) -0.0169(9) -0.0067(10) -0.0053(11) C13 0.0361(10) 0.0444(10) 0.0362(9) -0.0139(8) -0.0036(8) -0.0010(8) C14 0.0349(10) 0.0442(10) 0.0321(9) -0.0053(8) -0.0022(8) -0.0031(8) C15 0.0306(10) 0.0380(9) 0.0342(9) -0.0072(8) -0.0034(7) -0.0037(8) C16 0.0325(10) 0.0378(9) 0.0303(9) -0.0079(7) -0.0022(7) -0.0023(8) C17 0.0378(11) 0.0402(10) 0.0349(10) -0.0049(8) -0.0033(8) -0.0101(8) C18 0.0614(14) 0.0408(10) 0.0459(11) -0.0153(9) -0.0134(10) -0.0097(10) C19 0.0799(17) 0.0461(12) 0.0469(12) -0.0180(9) -0.0112(11) -0.0010(11) C20 0.0707(15) 0.0441(11) 0.0496(12) -0.0097(9) -0.0094(11) 0.0059(10) C21 0.0489(12) 0.0491(11) 0.0475(11) -0.0076(9) -0.0101(9) 0.0018(9) C22 0.0458(11) 0.0393(10) 0.0342(9) -0.0067(8) -0.0098(8) -0.0069(9) Cl1 0.0684(4) 0.0448(3) 0.0483(3) -0.0106(2) -0.0108(2) -0.0123(2) N1 0.0464(10) 0.0358(8) 0.0326(8) -0.0055(7) 0.0013(7) -0.0086(7) N2 0.0342(8) 0.0374(8) 0.0355(8) -0.0065(7) 0.0000(6) -0.0034(7) N3 0.0383(10) 0.0558(11) 0.0472(10) 0.0052(8) -0.0010(8) -0.0077(8) N4 0.0427(9) 0.0345(8) 0.0309(7) -0.0052(6) -0.0037(7) -0.0088(7) O1 0.0671(10) 0.0519(8) 0.0304(7) -0.0024(6) -0.0021(6) -0.0108(7) O2 0.0840(12) 0.0831(11) 0.0372(8) 0.0028(8) -0.0008(8) -0.0109(9) O3 0.0782(12) 0.0504(9) 0.0708(11) 0.0099(8) -0.0021(9) -0.0235(8) O4 0.0523(10) 0.0784(11) 0.0421(8) 0.0034(7) 0.0035(7) 0.0044(8) O5 0.0568(10) 0.0579(9) 0.0673(10) -0.0211(8) 0.0077(8) -0.0053(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.389(2) . ? C1 N1 1.390(2) . ? C1 C6 1.390(2) . ? C2 C3 1.371(3) . ? C2 H2 0.9500 . ? C3 C4 1.373(3) . ? C3 H3 0.9500 . ? C4 C5 1.380(3) . ? C4 N3 1.454(2) . ? C5 C6 1.375(3) . ? C5 H5A 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.311(2) . ? C7 C16 1.439(2) . ? C7 C8 1.464(2) . ? C8 C13 1.399(3) . ? C8 C9 1.401(3) . ? C9 C10 1.369(3) . ? C9 H9 0.9500 . ? C10 C11 1.383(3) . ? C10 H10 0.9500 . ? C11 C12 1.358(3) . ? C11 H11 0.9500 . ? C12 C13 1.396(3) . ? C12 H12 0.9500 . ? C13 C14 1.470(3) . ? C14 O1 1.230(2) . ? C14 C15 1.469(2) . ? C15 C16 1.347(2) . ? C15 C17 1.506(2) . ? C16 H16 0.9500 . ? C17 N4 1.501(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N4 1.504(2) . ? C18 C19 1.512(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.514(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.518(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.510(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N4 1.499(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? N1 N2 1.327(2) . ? N1 H1 0.91(3) . ? N3 O2 1.225(2) . ? N3 O3 1.228(2) . ? N4 H4A 0.97(3) . ? O4 H4B 0.87(3) . ? O4 H4C 0.90(3) . ? O5 H5B 0.83(3) . ? O5 H5C 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 117.93(16) . . ? C2 C1 C6 119.81(16) . . ? N1 C1 C6 122.27(16) . . ? C3 C2 C1 119.84(17) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.87(18) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 121.18(17) . . ? C3 C4 N3 118.72(17) . . ? C5 C4 N3 120.09(17) . . ? C6 C5 C4 119.21(17) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? C5 C6 C1 120.09(17) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N2 C7 C16 126.19(16) . . ? N2 C7 C8 115.71(15) . . ? C16 C7 C8 118.09(15) . . ? C13 C8 C9 118.68(17) . . ? C13 C8 C7 119.67(16) . . ? C9 C8 C7 121.64(16) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.6(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.06(18) . . ? C12 C13 C14 118.93(17) . . ? C8 C13 C14 121.00(16) . . ? O1 C14 C15 121.12(16) . . ? O1 C14 C13 121.41(16) . . ? C15 C14 C13 117.47(15) . . ? C16 C15 C14 120.49(16) . . ? C16 C15 C17 121.02(16) . . ? C14 C15 C17 118.46(15) . . ? C15 C16 C7 123.22(16) . . ? C15 C16 H16 118.4 . . ? C7 C16 H16 118.4 . . ? N4 C17 C15 111.85(14) . . ? N4 C17 H17A 109.2 . . ? C15 C17 H17A 109.2 . . ? N4 C17 H17B 109.2 . . ? C15 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? N4 C18 C19 109.89(17) . . ? N4 C18 H18A 109.7 . . ? C19 C18 H18A 109.7 . . ? N4 C18 H18B 109.7 . . ? C19 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C18 C19 C20 112.07(17) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 110.49(17) . . ? C19 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C19 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C20 111.53(18) . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? N4 C22 C21 110.15(14) . . ? N4 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? N4 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? N2 N1 C1 118.75(15) . . ? N2 N1 H1 122.7(17) . . ? C1 N1 H1 118.5(17) . . ? C7 N2 N1 121.13(14) . . ? O2 N3 O3 123.33(17) . . ? O2 N3 C4 118.57(18) . . ? O3 N3 C4 118.08(18) . . ? C22 N4 C17 113.21(13) . . ? C22 N4 C18 109.72(14) . . ? C17 N4 C18 110.78(15) . . ? C22 N4 H4A 107.1(16) . . ? C17 N4 H4A 107.5(16) . . ? C18 N4 H4A 108.3(16) . . ? H4B O4 H4C 113(3) . . ? H5B O5 H5C 107(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 178.33(18) . . . . ? C6 C1 C2 C3 -1.0(3) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 N3 -178.14(19) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? N3 C4 C5 C6 177.39(17) . . . . ? C4 C5 C6 C1 0.8(3) . . . . ? C2 C1 C6 C5 0.3(3) . . . . ? N1 C1 C6 C5 -179.03(18) . . . . ? N2 C7 C8 C13 -177.00(17) . . . . ? C16 C7 C8 C13 2.1(3) . . . . ? N2 C7 C8 C9 2.3(3) . . . . ? C16 C7 C8 C9 -178.57(18) . . . . ? C13 C8 C9 C10 1.4(3) . . . . ? C7 C8 C9 C10 -178.0(2) . . . . ? C8 C9 C10 C11 -0.6(4) . . . . ? C9 C10 C11 C12 -0.6(5) . . . . ? C10 C11 C12 C13 1.0(4) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C11 C12 C13 C14 179.8(2) . . . . ? C9 C8 C13 C12 -1.0(3) . . . . ? C7 C8 C13 C12 178.36(18) . . . . ? C9 C8 C13 C14 179.08(18) . . . . ? C7 C8 C13 C14 -1.6(3) . . . . ? C12 C13 C14 O1 0.7(3) . . . . ? C8 C13 C14 O1 -179.33(18) . . . . ? C12 C13 C14 C15 -178.92(18) . . . . ? C8 C13 C14 C15 1.0(3) . . . . ? O1 C14 C15 C16 179.29(18) . . . . ? C13 C14 C15 C16 -1.1(3) . . . . ? O1 C14 C15 C17 1.3(3) . . . . ? C13 C14 C15 C17 -179.04(16) . . . . ? C14 C15 C16 C7 1.7(3) . . . . ? C17 C15 C16 C7 179.66(16) . . . . ? N2 C7 C16 C15 176.76(18) . . . . ? C8 C7 C16 C15 -2.2(3) . . . . ? C16 C15 C17 N4 81.5(2) . . . . ? C14 C15 C17 N4 -100.50(18) . . . . ? N4 C18 C19 C20 56.8(2) . . . . ? C18 C19 C20 C21 -53.1(2) . . . . ? C19 C20 C21 C22 53.3(2) . . . . ? C20 C21 C22 N4 -57.6(2) . . . . ? C2 C1 N1 N2 177.61(17) . . . . ? C6 C1 N1 N2 -3.1(3) . . . . ? C16 C7 N2 N1 -1.0(3) . . . . ? C8 C7 N2 N1 177.99(16) . . . . ? C1 N1 N2 C7 179.48(16) . . . . ? C3 C4 N3 O2 2.1(3) . . . . ? C5 C4 N3 O2 -176.46(19) . . . . ? C3 C4 N3 O3 -179.14(19) . . . . ? C5 C4 N3 O3 2.3(3) . . . . ? C21 C22 N4 C17 -175.10(15) . . . . ? C21 C22 N4 C18 60.58(19) . . . . ? C15 C17 N4 C22 68.15(18) . . . . ? C15 C17 N4 C18 -168.11(14) . . . . ? C19 C18 N4 C22 -59.9(2) . . . . ? C19 C18 N4 C17 174.34(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.91(3) 2.44(3) 3.3288(16) 164(2) 2_665 N4 H4A O4 0.97(3) 1.79(3) 2.756(2) 178(2) . O4 H4B Cl1 0.87(3) 2.29(3) 3.1322(19) 163(3) 2_665 O5 H5B Cl1 0.83(3) 2.40(3) 3.2136(18) 171(3) . O5 H5C Cl1 0.91(3) 2.23(3) 3.1384(18) 175(2) 2_765 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.195 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.036 _iucr_refine_instructions_details ; TITL NO2pipHCl CELL 0.71073 6.9584 12.8269 13.1334 76.183 85.273 86.982 ZERR 2.00 0.0006 0.0011 0.0011 0.007 0.007 0.007 LATT 1 SFAC C H CL N O UNIT 44 54 2 8 10 MERG 2 OMIT 0.00 50.00 FMAP 2 PLAN 5 SIZE 0.08 0.43 0.68 ACTA 50.00 EQIV $1 -x+1, -y+1, -z EQIV $2 -x+2, -y+1, -z HTAB N1 Cl1_$1 HTAB N4 O4 HTAB O4 Cl1_$1 HTAB O5 Cl1 HTAB O5 Cl1_$2 BOND $H CONF LIST 3 L.S. 10 TEMP -73.00 WGHT 0.052400 FVAR 0.44365 C1 1 0.252255 0.992459 -0.061973 11.00000 0.03246 0.03753 = 0.03540 -0.00476 -0.00040 -0.00351 C2 1 0.256799 0.968985 -0.160088 11.00000 0.05993 0.03959 = 0.03880 -0.00991 0.00195 -0.01019 AFIX 43 H2 2 0.236941 0.897820 -0.165400 11.00000 -1.20000 AFIX 0 C3 1 0.290015 1.048773 -0.249238 11.00000 0.05781 0.05316 = 0.03372 -0.00951 0.00072 -0.01129 AFIX 43 H3 2 0.291831 1.033174 -0.316484 11.00000 -1.20000 AFIX 0 C4 1 0.320642 1.151242 -0.241144 11.00000 0.03306 0.04513 = 0.03710 0.00001 -0.00081 -0.00612 C5 1 0.319852 1.175830 -0.144350 11.00000 0.04199 0.03649 = 0.04877 -0.00598 -0.00444 -0.00829 AFIX 43 H5A 2 0.343480 1.246774 -0.139739 11.00000 -1.20000 AFIX 0 C6 1 0.284450 1.096393 -0.054673 11.00000 0.04495 0.03858 = 0.03649 -0.00830 -0.00374 -0.00596 AFIX 43 H6 2 0.281993 1.112565 0.012350 11.00000 -1.20000 AFIX 0 C7 1 0.177566 0.854849 0.206337 11.00000 0.03135 0.03704 = 0.03488 -0.00752 -0.00189 -0.00158 C8 1 0.190893 0.886275 0.305505 11.00000 0.03313 0.04155 = 0.03850 -0.01143 -0.00021 -0.00386 C9 1 0.233805 0.991137 0.307793 11.00000 0.06130 0.04364 = 0.05266 -0.01758 0.00195 -0.00861 AFIX 43 H9 2 0.250946 1.044449 0.243986 11.00000 -1.20000 AFIX 0 C10 1 0.251066 1.016865 0.401927 11.00000 0.10207 0.05314 = 0.06382 -0.02807 -0.00105 -0.02107 AFIX 43 H10 2 0.281412 1.087938 0.402956 11.00000 -1.20000 AFIX 0 C11 1 0.224747 0.940381 0.495503 11.00000 0.11489 0.06820 = 0.05238 -0.03359 -0.00850 -0.01752 AFIX 43 H11 2 0.238371 0.959206 0.560181 11.00000 -1.20000 AFIX 0 C12 1 0.179604 0.838616 0.495753 11.00000 0.07156 0.05926 = 0.03667 -0.01687 -0.00665 -0.00526 AFIX 43 H12 2 0.159815 0.786878 0.560459 11.00000 -1.20000 AFIX 0 C13 1 0.162281 0.810044 0.400858 11.00000 0.03612 0.04435 = 0.03618 -0.01385 -0.00358 -0.00104 C14 1 0.114032 0.699228 0.403196 11.00000 0.03492 0.04419 = 0.03212 -0.00530 -0.00216 -0.00314 C15 1 0.100396 0.671450 0.301828 11.00000 0.03063 0.03801 = 0.03421 -0.00719 -0.00345 -0.00368 C16 1 0.128382 0.746146 0.211025 11.00000 0.03250 0.03785 = 0.03029 -0.00786 -0.00225 -0.00225 AFIX 43 H16 2 0.114999 0.726092 0.146923 11.00000 -1.20000 AFIX 0 C17 1 0.048035 0.558890 0.302218 11.00000 0.03778 0.04018 = 0.03491 -0.00486 -0.00325 -0.01006 AFIX 23 H17A 2 -0.016467 0.525275 0.371457 11.00000 -1.20000 H17B 2 -0.044224 0.561769 0.248037 11.00000 -1.20000 AFIX 0 C18 1 0.163486 0.387754 0.259185 11.00000 0.06137 0.04079 = 0.04595 -0.01529 -0.01344 -0.00974 AFIX 23 H18A 2 0.074032 0.403511 0.202179 11.00000 -1.20000 H18B 2 0.095480 0.343887 0.322983 11.00000 -1.20000 AFIX 0 C19 1 0.340043 0.325875 0.227218 11.00000 0.07994 0.04613 = 0.04694 -0.01802 -0.01121 -0.00100 AFIX 23 H19A 2 0.400654 0.367478 0.159959 11.00000 -1.20000 H19B 2 0.300277 0.256825 0.215749 11.00000 -1.20000 AFIX 0 C20 1 0.486505 0.303772 0.309488 11.00000 0.07071 0.04413 = 0.04963 -0.00967 -0.00938 0.00595 AFIX 23 H20A 2 0.605213 0.270280 0.282451 11.00000 -1.20000 H20B 2 0.433678 0.252865 0.373482 11.00000 -1.20000 AFIX 0 C21 1 0.535299 0.407271 0.336968 11.00000 0.04892 0.04910 = 0.04747 -0.00763 -0.01012 0.00181 AFIX 23 H21A 2 0.620786 0.390415 0.395804 11.00000 -1.20000 H21B 2 0.605963 0.453552 0.275635 11.00000 -1.20000 AFIX 0 C22 1 0.355918 0.467294 0.367954 11.00000 0.04579 0.03928 = 0.03424 -0.00670 -0.00985 -0.00687 AFIX 23 H22A 2 0.289853 0.423455 0.432423 11.00000 -1.20000 H22B 2 0.392030 0.535323 0.383251 11.00000 -1.20000 AFIX 0 CL1 3 0.888840 0.303683 0.059578 11.00000 0.06839 0.04483 = 0.04834 -0.01064 -0.01082 -0.01226 N1 4 0.213071 0.909817 0.026191 11.00000 0.04639 0.03585 = 0.03263 -0.00549 0.00134 -0.00860 N2 4 0.215000 0.929829 0.120703 11.00000 0.03416 0.03741 = 0.03552 -0.00649 -0.00003 -0.00335 N3 4 0.349626 1.234992 -0.336985 11.00000 0.03828 0.05585 = 0.04722 0.00524 -0.00096 -0.00769 N4 4 0.222160 0.491123 0.280871 11.00000 0.04265 0.03447 = 0.03088 -0.00518 -0.00373 -0.00880 O1 5 0.086929 0.631990 0.486720 11.00000 0.06708 0.05188 = 0.03035 -0.00239 -0.00207 -0.01082 O2 5 0.340164 1.211793 -0.421593 11.00000 0.08398 0.08311 = 0.03716 0.00284 -0.00082 -0.01086 O3 5 0.379182 1.326016 -0.328706 11.00000 0.07818 0.05045 = 0.07084 0.00987 -0.00214 -0.02350 O4 5 0.421134 0.602042 0.100837 11.00000 0.05227 0.07839 = 0.04215 0.00336 0.00354 0.00438 O5 5 0.797519 0.546864 0.078344 11.00000 0.05679 0.05788 = 0.06729 -0.02111 0.00773 -0.00529 H1 2 0.179130 0.845314 0.016582 11.00000 -1.50000 H4A 2 0.293370 0.531017 0.218876 11.00000 -1.50000 H4B 2 0.354513 0.626189 0.045989 11.00000 -1.50000 H4C 2 0.544240 0.583506 0.083930 11.00000 -1.50000 H5B 2 0.813941 0.486049 0.067754 11.00000 -1.50000 H5C 2 0.885615 0.589190 0.034623 11.00000 -1.50000 HKLF 4 REM NO2pipHCl REM R1 = 0.0362 for 2738 Fo > 4sig(Fo) and 0.0618 for all 3989 data REM 307 parameters refined using 0 restraints END WGHT 0.0525 0.0000 REM Highest difference peak 0.195, deepest hole -0.182, 1-sigma level 0.036 Q1 1 0.3846 0.5341 0.0778 11.00000 0.05 0.19 Q2 1 0.1913 0.8700 0.2543 11.00000 0.05 0.17 Q3 1 0.1751 0.6995 0.2603 11.00000 0.05 0.16 Q4 1 0.9291 0.3657 -0.0212 11.00000 0.05 0.15 Q5 1 0.3103 1.0453 -0.0581 11.00000 0.05 0.15 ; _database_code_depnum_ccdc_archive 'CCDC 928938'