# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name _publ_author_address 'Bensemann, Igor' ; Department of Chemistry Technical University 80-952 Gdansk Poland ; 'Gdaniec, Maria' ; Faculty of Chemistry A.Mickiewicz University Grunwaldzka 6 60-780 Poznan Poland ; 'Polonski, Tadeusz' ; Department of Chemistry Technical University 80-952 Gdansk Poland ; _publ_contact_author_name 'Dr Maria Gdaniec' _publ_contact_author_address ; Faculty of Chemistry A. Mickieiwcz University ul. Grunwaldzka 6 Poznan 60-780 POLAND ; _publ_contact_author_email 'MAGDAN@AMU.EDU.PL' _publ_section_title ; Supramolecular structures formed by 2-aminopyridine derivatives. I. Hydrogen bonding networks via N-H···N interaction and conformational polymorphism of N,N'-bis(2-pyridyl)aryldiamines ; data_1 _database_code_CSD 174152 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,3-diaminobenzene ; _chemical_melting_point 165-166 _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 19.917(4) _cell_length_b 7.627(2) _cell_length_c 8.677(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1318.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 57 _cell_measurement_theta_min 5 _cell_measurement_theta_max 11 _exptl_crystal_description needle _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <2% _diffrn_reflns_number 1173 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1173 _reflns_number_gt 699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0616P)^2^+0.0192P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1173 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.003 _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 N1 N 0.37525(9) -0.1758(2) 0.26113(18) 0.0439(5) Uani 1 1 d . . . C2 C 0.37322(9) -0.1097(3) 0.4032(2) 0.0370(5) Uani 1 1 d . . . C3 C 0.33293(11) -0.1844(3) 0.5180(2) 0.0450(5) Uani 1 1 d . . . C4 C 0.29455(11) -0.3258(3) 0.4834(2) 0.0480(6) Uani 1 1 d . . . C5 C 0.29687(13) -0.3975(3) 0.3376(2) 0.0549(6) Uani 1 1 d . . . C6 C 0.33801(12) -0.3183(3) 0.2330(3) 0.0516(6) Uani 1 1 d . . . N7 N 0.40831(9) 0.0387(2) 0.4358(2) 0.0456(5) Uani 1 1 d . . . C8 C 0.45483(10) 0.1264(3) 0.3412(2) 0.0405(5) Uani 1 1 d . . . C9 C 0.5000 0.0361(4) 0.2500 0.0393(7) Uani 1 2 d S . . C10 C 0.45549(14) 0.3077(3) 0.3431(3) 0.0630(7) Uani 1 1 d . . . C11 C 0.5000 0.3963(5) 0.2500 0.0782(13) Uani 1 2 d S . . H7N H 0.4036(12) 0.080(3) 0.526(3) 0.068(8) Uiso 1 1 d . . . H3 H 0.3340(11) -0.129(2) 0.621(3) 0.047(6) Uiso 1 1 d . . . H4 H 0.2664(12) -0.371(3) 0.563(3) 0.056(6) Uiso 1 1 d . . . H5 H 0.2673(13) -0.506(3) 0.306(3) 0.079(7) Uiso 1 1 d . . . H6 H 0.3390(16) -0.361(3) 0.133(4) 0.082(9) Uiso 1 1 d . . . H9 H 0.5000 -0.096(4) 0.2500 0.037(7) Uiso 1 2 d S . . H10 H 0.4235(14) 0.370(3) 0.406(3) 0.080(8) Uiso 1 1 d . . . H11 H 0.5000 0.519(5) 0.2500 0.086(13) Uiso 1 2 d S . . 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 N1 0.0483(11) 0.0530(10) 0.0305(8) -0.0004(7) 0.0031(7) -0.0068(9) C2 0.0349(10) 0.0446(10) 0.0313(9) 0.0023(9) 0.0005(8) 0.0066(9) C3 0.0523(12) 0.0520(12) 0.0306(10) 0.0034(10) 0.0045(9) 0.0068(11) C4 0.0503(12) 0.0518(12) 0.0419(11) 0.0128(10) 0.0100(10) -0.0018(11) C5 0.0630(14) 0.0560(13) 0.0458(11) 0.0019(11) 0.0041(11) -0.0126(12) C6 0.0564(13) 0.0600(14) 0.0385(11) -0.0037(11) 0.0048(10) -0.0123(12) N7 0.0475(10) 0.0576(11) 0.0318(9) -0.0082(8) 0.0056(8) -0.0035(9) C8 0.0387(10) 0.0490(11) 0.0340(9) -0.0023(9) 0.0008(9) -0.0024(9) C9 0.0349(14) 0.0482(17) 0.0347(14) 0.000 -0.0001(12) 0.000 C10 0.0621(15) 0.0515(13) 0.0756(16) -0.0111(13) 0.0204(13) 0.0018(12) C11 0.078(3) 0.044(2) 0.113(3) 0.000 0.036(3) 0.000 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 N1 C2 1.333(2) . y N1 C6 1.338(3) . y C2 N7 1.359(3) . y C2 C3 1.400(3) . y C3 C4 1.355(3) . y C3 H3 0.99(2) . y C4 C5 1.379(3) . y C4 H4 0.95(2) . y C5 C6 1.364(3) . y C5 H5 1.05(3) . y C6 H6 0.92(3) . y N7 C8 1.407(3) . y N7 H7N 0.85(3) . y C8 C9 1.382(2) . y C8 C10 1.383(3) . y C9 C8 1.382(2) 3_655 y C9 H9 1.01(3) . y C10 C11 1.376(3) . y C10 H10 0.96(3) . y C11 C10 1.376(3) 3_655 y C11 H11 0.94(4) . y 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 N1 C6 117.34(17) . . y N1 C2 N7 119.45(16) . . y N1 C2 C3 121.41(19) . . y N7 C2 C3 119.05(18) . . y C4 C3 C2 119.32(19) . . y C4 C3 H3 123.7(12) . . y C2 C3 H3 117.0(13) . . y C3 C4 C5 120.0(2) . . y C3 C4 H4 117.5(13) . . y C5 C4 H4 122.5(13) . . y C6 C5 C4 117.1(2) . . y C6 C5 H5 120.5(15) . . y C4 C5 H5 122.4(15) . . y N1 C6 C5 124.8(2) . . y N1 C6 H6 116.4(18) . . y C5 C6 H6 118.7(18) . . y C2 N7 C8 127.81(17) . . y C2 N7 H7N 116.2(17) . . y C8 N7 H7N 115.8(17) . . y C9 C8 C10 119.9(2) . . y C9 C8 N7 121.69(19) . . y C10 C8 N7 118.36(19) . . y C8 C9 C8 120.2(3) 3_655 . y C8 C9 H9 119.91(14) 3_655 . y C8 C9 H9 119.91(14) . . y C11 C10 C8 119.3(3) . . y C11 C10 H10 121.0(16) . . y C8 C10 H10 119.6(16) . . y C10 C11 C10 121.2(4) 3_655 . y C10 C11 H11 119.39(17) 3_655 . y C10 C11 H11 119.39(18) . . y 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 C2 N7 C8 -8.2(3) . . . . y C3 C2 N7 C8 175.1(2) . . . . y C2 N7 C8 C9 -39.1(3) . . . . y C2 N7 C8 C10 142.1(2) . . . . y _refine_diff_density_max 0.172 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.041 #===END data_2 _database_code_CSD 174153 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,3-diamino-2-methylbenzene ; _chemical_melting_point 153-154 _chemical_formula_sum 'C17 H16 N4' _chemical_formula_weight 276.34 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 11.352(5) _cell_length_b 7.702(2) _cell_length_c 16.435(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.36(3) _cell_angle_gamma 90.00 _cell_volume 1436.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 6 _cell_measurement_theta_max 24 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.621 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Twinned crystal has been used for data collection. Depending on the crystallization batch many reflections were showing double peaks indicating crystal twinning. In these cases the beta angle was 91.25(2) deg. Crystallization from acetonitrile yielded crystals with unit-cell beta angle 90.36(3). The reflections were broad and their intensity dropped very fast with the increase of the diffraction angle. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <1.5 _diffrn_reflns_number 2286 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.74 _diffrn_reflns_theta_max 58.90 _reflns_number_total 2046 _reflns_number_gt 1057 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; The crystal has been refined as pseudumerohedral twinn with the twin matrix 1 0 0 0 -1 0 0 0 -1. The BASF parameter for a second twin component refined at 0.276. Despite this the highest peaks on the difference Fourier map formed mirror image of the molecule with mirror plane perpendicular to the z axis at 0.2500. The mirror image of the molecule (molecule A) has been generated and its occupancy refined. This 'mirror image molecule A' has been refined as rigid model with AFIX 6 instruction with one common isotropic temperature factor for all atoms. The occupancy of the molecule A equals 0.180(7). ; _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^)+(0.1418P)^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 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2046 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1730 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.2205 _refine_ls_wR_factor_gt 0.1883 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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 N1 N 0.1421(4) 0.0772(5) -0.0343(3) 0.0685(16) Uani 0.820(7) 1 d PG A 2 C2 C 0.1137(3) 0.0149(5) -0.1064(3) 0.0733(19) Uani 0.820(7) 1 d PG A 2 C3 C 0.1993(3) -0.0184(6) -0.1656(3) 0.082(2) Uani 0.820(7) 1 d PG A 2 H3 H 0.1776 -0.0676 -0.2172 0.098 Uiso 0.820(7) 1 d PR A 2 C4 C 0.3133(7) 0.0177(12) -0.1466(6) 0.099(3) Uani 0.820(7) 1 d P A 2 H4 H 0.3716 0.0012 -0.1880 0.119 Uiso 0.820(7) 1 d PR A 2 C5 C 0.3458(7) 0.0809(12) -0.0732(6) 0.094(3) Uani 0.820(7) 1 d P A 2 H5 H 0.4276 0.1007 -0.0611 0.113 Uiso 0.820(7) 1 d PR A 2 C6 C 0.2566(7) 0.1105(11) -0.0189(6) 0.093(2) Uani 0.820(7) 1 d P A 2 H6 H 0.2767 0.1596 0.0330 0.112 Uiso 0.820(7) 1 d PR A 2 N7 N -0.0053(5) -0.0164(7) -0.1191(4) 0.0767(16) Uani 0.820(7) 1 d P A 2 H7 H -0.0548 0.0205 -0.0802 0.092 Uiso 0.820(7) 1 d PR A 2 C8 C -0.0514(6) -0.1090(11) -0.1887(4) 0.073(2) Uani 0.820(7) 1 d P A 2 C9 C -0.0524(5) -0.0457(9) -0.2651(4) 0.0708(18) Uani 0.820(7) 1 d P A 2 C10 C -0.0949(5) -0.1498(10) -0.3301(4) 0.0698(19) Uani 0.820(7) 1 d P A 2 C11 C -0.1399(6) -0.3134(10) -0.3117(5) 0.080(2) Uani 0.820(7) 1 d P A 2 H11 H -0.1649 -0.3892 -0.3548 0.096 Uiso 0.820(7) 1 d PR A 2 C12 C -0.1489(7) -0.3673(12) -0.2342(5) 0.086(2) Uani 0.820(7) 1 d P A 2 H12 H -0.1865 -0.4759 -0.2223 0.103 Uiso 0.820(7) 1 d PR A 2 C13 C -0.1044(6) -0.2666(11) -0.1711(4) 0.077(2) Uani 0.820(7) 1 d P A 2 H13A H -0.1073 -0.3075 -0.1160 0.092 Uiso 0.820(7) 1 d PR A 2 N14 N -0.0904(5) -0.0887(8) -0.4095(3) 0.0791(17) Uani 0.820(7) 1 d P A 2 H14 H -0.0224 -0.0376 -0.4241 0.095 Uiso 0.820(7) 1 d PR A 2 C15 C -0.1784(5) -0.0893(8) -0.4662(4) 0.0617(17) Uani 0.820(7) 1 d P A 2 N16 N -0.1490(5) -0.0288(8) -0.5392(4) 0.0790(17) Uani 0.820(7) 1 d P A 2 C17 C -0.2326(6) -0.0124(10) -0.5953(4) 0.078(2) Uani 0.820(7) 1 d P A 2 H17 H -0.2122 0.0435 -0.6455 0.093 Uiso 0.820(7) 1 d PR A 2 C18 C -0.3476(7) -0.0619(13) -0.5846(5) 0.090(2) Uani 0.820(7) 1 d P A 2 H18 H -0.4052 -0.0555 -0.6275 0.108 Uiso 0.820(7) 1 d PR A 2 C19 C -0.3782(6) -0.1289(10) -0.5099(5) 0.075(2) Uani 0.820(7) 1 d P A 2 H19A H -0.4575 -0.1657 -0.4992 0.091 Uiso 0.820(7) 1 d PR A 2 C20 C -0.2938(6) -0.1434(8) -0.4513(4) 0.0669(18) Uani 0.820(7) 1 d P A 2 H20 H -0.3141 -0.1861 -0.3983 0.080 Uiso 0.820(7) 1 d PR A 2 C21 C -0.0175(7) 0.1410(10) -0.2791(4) 0.088(2) Uani 0.820(7) 1 d P A 2 H21C H 0.0064 0.1919 -0.2283 0.106 Uiso 0.820(7) 1 d PR A 2 H21B H -0.0834 0.2041 -0.3010 0.106 Uiso 0.820(7) 1 d PR A 2 H21A H 0.0468 0.1458 -0.3168 0.106 Uiso 0.820(7) 1 d PR A 2 N1A N -0.1394(7) -0.0603(17) -0.5360(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C2A C -0.1117(8) -0.0046(16) -0.6092(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C3A C -0.1977(9) 0.021(2) -0.6697(4) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C4A C -0.3113(8) -0.021(3) -0.6492(4) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C5A C -0.3424(8) -0.075(3) -0.5781(4) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C6A C -0.2520(7) -0.097(2) -0.5213(4) 0.107(5) Uiso 0.180(7) 1 d PG A 1 N7A N 0.0072(8) 0.0339(12) -0.6219(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C8A C 0.0529(9) 0.1220(12) -0.6920(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C9A C 0.0536(10) 0.0449(14) -0.7602(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C10A C 0.0909(11) 0.1428(15) -0.8333(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C11A C 0.1367(13) 0.3235(15) -0.8178(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C12A C 0.1420(13) 0.3794(13) -0.7434(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C13A C 0.1024(11) 0.2837(12) -0.6788(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 N14A N 0.0910(12) 0.0793(17) -0.9125(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C15A C 0.1798(13) 0.0792(19) -0.9686(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 N16A N 0.1491(14) 0.012(2) -1.0397(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C17A C 0.2355(15) -0.009(2) -1.0968(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C18A C 0.3552(15) 0.052(3) -1.0846(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C19A C 0.3770(14) 0.124(3) -1.0113(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C20A C 0.2925(13) 0.138(2) -0.9532(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 C21A C 0.0215(11) -0.1379(14) -0.7770(3) 0.107(5) Uiso 0.180(7) 1 d PG A 1 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 N1 0.048(3) 0.073(4) 0.085(4) 0.007(3) 0.003(3) -0.015(3) C2 0.071(5) 0.066(5) 0.083(5) 0.012(4) 0.009(4) -0.002(4) C3 0.053(4) 0.096(6) 0.097(5) 0.001(4) 0.016(4) -0.005(4) C4 0.066(5) 0.113(7) 0.119(7) 0.009(5) 0.019(5) -0.008(5) C5 0.054(4) 0.097(6) 0.131(7) 0.004(5) 0.018(5) -0.005(4) C6 0.081(6) 0.075(5) 0.124(7) 0.009(5) -0.007(5) -0.010(4) N7 0.052(3) 0.091(4) 0.087(4) -0.010(3) 0.008(3) -0.005(3) C8 0.057(4) 0.092(6) 0.068(4) 0.001(4) 0.008(4) 0.016(4) C9 0.053(3) 0.076(5) 0.084(5) 0.012(4) 0.008(4) 0.005(3) C10 0.053(4) 0.088(6) 0.069(5) -0.006(4) -0.004(3) 0.003(4) C11 0.052(4) 0.083(6) 0.106(6) -0.012(5) 0.003(4) 0.006(4) C12 0.064(4) 0.105(6) 0.089(5) 0.017(5) 0.005(4) 0.005(4) C13 0.059(4) 0.094(6) 0.078(5) 0.012(5) -0.001(4) 0.005(4) N14 0.053(3) 0.108(5) 0.076(4) -0.004(4) -0.010(3) -0.015(3) C15 0.057(4) 0.058(4) 0.069(4) -0.007(4) -0.004(3) -0.006(3) N16 0.058(3) 0.091(4) 0.088(4) -0.002(4) -0.003(3) -0.020(3) C17 0.060(4) 0.095(6) 0.078(5) -0.004(4) -0.008(4) -0.001(4) C18 0.059(4) 0.109(6) 0.103(6) -0.017(5) -0.011(4) -0.008(4) C19 0.050(4) 0.080(5) 0.097(5) -0.019(4) -0.002(4) -0.001(4) C20 0.053(4) 0.064(4) 0.084(5) -0.007(4) 0.004(4) -0.004(3) C21 0.090(5) 0.088(5) 0.087(5) 0.004(4) 0.009(4) -0.001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1 C2 1.3171 . y N1 C6 1.347(9) . y C2 N7 1.386(6) . y C2 C3 1.4032 . y C3 C4 1.358(9) . y C4 C5 1.350(10) . y C5 C6 1.373(11) . y N7 C8 1.443(9) . y C8 C9 1.347(9) . y C8 C13 1.386(10) . y C9 C10 1.419(9) . y C9 C21 1.509(10) . y C10 N14 1.388(8) . y C10 C11 1.394(10) . y C11 C12 1.343(9) . y C12 C13 1.388(10) . y N14 C15 1.362(8) . y C15 N16 1.332(8) . y C15 C20 1.398(9) . y N16 C17 1.325(9) . y C17 C18 1.373(10) . y C18 C19 1.378(10) . y C19 C20 1.360(9) . y N1A C2A 1.3171 . y N1A C6A 1.3336 . y C2A N7A 1.3980 . y C2A C3A 1.4031 . y C3A C4A 1.3727 . y C4A C5A 1.2930 . y C5A C6A 1.3930 . y N7A C8A 1.4368 . y C8A C9A 1.2691 . y C8A C13A 1.3825 . y C9A C21A 1.4799 . y C9A C10A 1.4822 . y C10A N14A 1.3904 . y C10A C11A 1.5069 . y C11A C12A 1.2963 . y C12A C13A 1.3708 . y N14A C15A 1.3700 . y C15A N16A 1.3219 . y C15A C20A 1.3805 . y N16A C17A 1.3717 . y C17A C18A 1.4504 . y C18A C19A 1.3482 . y C19A C20A 1.3622 . y 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 N1 C6 117.9(5) . . y N1 C2 N7 115.6(3) . . y N1 C2 C3 121.6 . . y N7 C2 C3 122.9(3) . . y C4 C3 C2 117.8(5) . . y C5 C4 C3 122.2(7) . . y C4 C5 C6 116.2(8) . . y N1 C6 C5 124.2(8) . . y C2 N7 C8 123.6(5) . . y C9 C8 C13 120.6(7) . . y C9 C8 N7 124.1(7) . . y C13 C8 N7 115.1(6) . . y C8 C9 C10 119.9(7) . . y C8 C9 C21 119.1(7) . . y C10 C9 C21 120.7(6) . . y N14 C10 C11 121.8(7) . . y N14 C10 C9 120.1(7) . . y C11 C10 C9 118.1(7) . . y C12 C11 C10 121.1(8) . . y C11 C12 C13 120.4(8) . . y C8 C13 C12 119.4(7) . . y C15 N14 C10 127.6(6) . . y N16 C15 N14 115.4(6) . . y N16 C15 C20 120.2(6) . . y N14 C15 C20 124.4(6) . . y C17 N16 C15 118.5(6) . . y N16 C17 C18 124.2(8) . . y C17 C18 C19 117.6(7) . . y C20 C19 C18 118.8(7) . . y C19 C20 C15 120.6(6) . . y C2A N1A C6A 118.0 . . y N1A C2A N7A 116.2 . . y N1A C2A C3A 121.6 . . y N7A C2A C3A 122.2 . . y C4A C3A C2A 116.4 . . y C5A C4A C3A 124.1 . . y C4A C5A C6A 116.1 . . y N1A C6A C5A 123.8 . . y C2A N7A C8A 125.0 . . y C9A C8A C13A 123.7 . . y C9A C8A N7A 119.5 . . y C13A C8A N7A 116.7 . . y C8A C9A C21A 127.3 . . y C8A C9A C10A 118.8 . . y C21A C9A C10A 113.9 . . y N14A C10A C9A 125.6 . . y N14A C10A C11A 118.8 . . y C9A C10A C11A 115.6 . . y C12A C11A C10A 118.8 . . y C11A C12A C13A 122.5 . . y C12A C13A C8A 119.9 . . y C15A N14A C10A 129.4 . . y N16A C15A N14A 113.8 . . y N16A C15A C20A 122.0 . . y N14A C15A C20A 124.2 . . y C15A N16A C17A 117.8 . . y N16A C17A C18A 122.7 . . y C19A C18A C17A 115.0 . . y C18A C19A C20A 122.3 . . y C19A C20A C15A 120.1 . . y _refine_diff_density_max 0.235 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.048 #===END data_3a _database_code_CSD 174154 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,4-diaminobenzene, polymorph alpha ; _chemical_melting_point 205-206 _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.778(2) _cell_length_b 9.003(2) _cell_length_c 10.240(2) _cell_angle_alpha 101.77(3) _cell_angle_beta 97.54(3) _cell_angle_gamma 105.52(3) _cell_volume 663.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 5 _cell_measurement_theta_max 12.5 _exptl_crystal_description prism _exptl_crystal_colour 'light-brown' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; metastable form - transforms into stable polymorph at temperatures 140-190C depending on crystal specimen ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <1.5 _diffrn_reflns_number 2080 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0594 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 24.05 _reflns_number_total 2080 _reflns_number_gt 1289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0737P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.032(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2080 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1126 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 N1A N 0.2206(3) 0.0184(2) 0.41059(18) 0.0449(5) Uani 1 1 d . . . C2A C 0.3281(3) 0.0825(3) 0.3311(2) 0.0435(6) Uani 1 1 d . . . C3A C 0.4702(4) 0.2242(3) 0.3830(3) 0.0584(8) Uani 1 1 d . . . H3A H 0.537(4) 0.264(3) 0.319(3) 0.069(8) Uiso 1 1 d . . . C4A C 0.5059(4) 0.2939(4) 0.5188(3) 0.0638(8) Uani 1 1 d . . . H4A H 0.616(4) 0.393(4) 0.554(3) 0.088(10) Uiso 1 1 d . . . C5A C 0.3992(4) 0.2268(4) 0.6017(3) 0.0615(8) Uani 1 1 d . . . H5A H 0.423(4) 0.282(3) 0.700(3) 0.073(9) Uiso 1 1 d . . . C6A C 0.2587(4) 0.0917(3) 0.5430(2) 0.0497(7) Uani 1 1 d . . . H6A H 0.176(3) 0.048(3) 0.598(2) 0.045(6) Uiso 1 1 d . . . N7A N 0.2787(3) 0.0031(3) 0.1963(2) 0.0549(6) Uani 1 1 d . . . H7NA H 0.171(4) -0.072(4) 0.171(3) 0.067(9) Uiso 1 1 d . . . C8A C 0.3937(4) 0.0062(3) 0.1004(2) 0.0450(6) Uani 1 1 d . . . C9A C 0.5780(4) 0.0326(3) 0.1348(2) 0.0483(7) Uani 1 1 d . . . H9A H 0.651(3) 0.051(3) 0.227(3) 0.059(7) Uiso 1 1 d . . . C10A C 0.3161(4) -0.0269(3) -0.0354(3) 0.0489(7) Uani 1 1 d . . . H10A H 0.194(3) -0.041(3) -0.059(2) 0.052(7) Uiso 1 1 d . . . N1B N 0.0662(3) 0.2649(2) 0.90147(18) 0.0440(5) Uani 1 1 d . . . C2B C 0.0991(3) 0.3761(3) 0.8315(2) 0.0395(6) Uani 1 1 d . . . C3B C 0.2252(4) 0.5266(3) 0.8905(3) 0.0524(7) Uani 1 1 d . . . H3B H 0.247(4) 0.592(3) 0.837(3) 0.061(8) Uiso 1 1 d . . . C4B C 0.3118(4) 0.5609(3) 1.0218(3) 0.0571(7) Uani 1 1 d . . . H4B H 0.400(4) 0.671(4) 1.068(3) 0.084(9) Uiso 1 1 d . . . C5B C 0.2758(4) 0.4460(3) 1.0952(3) 0.0562(7) Uani 1 1 d . . . H5B H 0.343(4) 0.467(3) 1.197(3) 0.066(8) Uiso 1 1 d . . . C6B C 0.1550(3) 0.3023(3) 1.0297(2) 0.0476(6) Uani 1 1 d . . . H6B H 0.121(3) 0.210(3) 1.075(2) 0.056(7) Uiso 1 1 d . . . N7B N 0.0043(3) 0.3287(2) 0.7006(2) 0.0481(6) Uani 1 1 d . . . H7NB H -0.057(3) 0.221(3) 0.670(2) 0.054(7) Uiso 1 1 d . . . C8B C 0.0069(3) 0.4186(3) 0.6027(2) 0.0400(6) Uani 1 1 d . . . C9B C 0.0043(3) 0.5747(3) 0.6320(2) 0.0447(6) Uani 1 1 d . . . H9B H 0.015(3) 0.633(3) 0.728(2) 0.052(7) Uiso 1 1 d . . . C10B C 0.0011(3) 0.3449(3) 0.4684(2) 0.0447(6) Uani 1 1 d . . . H10B H 0.000(3) 0.232(3) 0.447(2) 0.052(7) 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 N1A 0.0531(13) 0.0433(11) 0.0348(11) 0.0089(9) 0.0120(9) 0.0079(10) C2A 0.0474(14) 0.0375(13) 0.0426(14) 0.0077(11) 0.0133(11) 0.0077(11) C3A 0.0627(18) 0.0472(15) 0.0566(18) 0.0054(13) 0.0241(14) 0.0018(13) C4A 0.0531(17) 0.0543(17) 0.063(2) -0.0091(14) 0.0117(14) -0.0013(14) C5A 0.0639(19) 0.0652(19) 0.0420(16) -0.0019(14) 0.0047(13) 0.0122(15) C6A 0.0552(16) 0.0529(16) 0.0370(14) 0.0101(12) 0.0085(12) 0.0109(13) N7A 0.0590(14) 0.0534(14) 0.0387(12) 0.0050(10) 0.0180(10) -0.0048(12) C8A 0.0584(17) 0.0327(13) 0.0425(14) 0.0098(10) 0.0192(12) 0.0069(11) C9A 0.0621(18) 0.0456(14) 0.0360(14) 0.0116(11) 0.0128(12) 0.0117(12) C10A 0.0537(17) 0.0462(15) 0.0452(16) 0.0115(11) 0.0127(12) 0.0110(13) N1B 0.0515(12) 0.0416(12) 0.0374(11) 0.0118(9) 0.0108(9) 0.0090(9) C2B 0.0420(13) 0.0418(13) 0.0360(13) 0.0117(10) 0.0098(10) 0.0123(11) C3B 0.0521(16) 0.0432(15) 0.0567(17) 0.0207(13) 0.0050(13) 0.0022(12) C4B 0.0549(16) 0.0472(16) 0.0527(17) 0.0027(13) -0.0017(13) 0.0015(13) C5B 0.0550(16) 0.0634(18) 0.0423(15) 0.0086(13) 0.0005(12) 0.0129(14) C6B 0.0544(16) 0.0528(16) 0.0359(14) 0.0154(12) 0.0096(11) 0.0134(13) N7B 0.0617(13) 0.0369(12) 0.0389(12) 0.0139(9) 0.0054(10) 0.0027(10) C8B 0.0426(14) 0.0380(14) 0.0387(13) 0.0150(11) 0.0106(10) 0.0055(11) C9B 0.0551(15) 0.0458(14) 0.0334(13) 0.0082(11) 0.0121(11) 0.0152(12) C10B 0.0567(16) 0.0343(13) 0.0419(14) 0.0097(11) 0.0103(11) 0.0115(11) 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 N1A C6A 1.337(3) . y N1A C2A 1.344(3) . y C2A N7A 1.370(3) . y C2A C3A 1.395(4) . y C3A C4A 1.361(4) . y C3A H3A 0.96(3) . y C4A C5A 1.378(4) . y C4A H4A 1.02(3) . y C5A C6A 1.361(4) . y C5A H5A 1.00(3) . y C6A H6A 0.97(2) . y N7A C8A 1.412(3) . y N7A H7NA 0.89(3) . y C8A C9A 1.373(4) . y C8A C10A 1.379(3) . y C9A C10A 1.393(4) 2_655 y C9A H9A 0.99(3) . y C10A C9A 1.393(4) 2_655 y C10A H10A 0.92(2) . y N1B C6B 1.331(3) . y N1B C2B 1.336(3) . y C2B N7B 1.365(3) . y C2B C3B 1.401(3) . y C3B C4B 1.356(4) . y C3B H3B 0.88(3) . y C4B C5B 1.389(4) . y C4B H4B 1.02(3) . y C5B C6B 1.355(4) . y C5B H5B 1.06(3) . y C6B H6B 1.02(3) . y N7B C8B 1.411(3) . y N7B H7NB 0.93(3) . y C8B C9B 1.381(3) . y C8B C10B 1.389(3) . y C9B C10B 1.376(3) 2_566 y C9B H9B 1.00(2) . y C10B C9B 1.376(3) 2_566 y C10B H10B 0.99(3) . y 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 C6A N1A C2A 117.7(2) . . y N1A C2A N7A 114.5(2) . . y N1A C2A C3A 121.5(2) . . y N7A C2A C3A 123.8(2) . . y C4A C3A C2A 118.8(3) . . y C4A C3A H3A 125.0(17) . . y C2A C3A H3A 116.1(17) . . y C3A C4A C5A 120.0(3) . . y C3A C4A H4A 116.7(17) . . y C5A C4A H4A 123.3(17) . . y C6A C5A C4A 117.9(3) . . y C6A C5A H5A 122.9(16) . . y C4A C5A H5A 119.1(16) . . y N1A C6A C5A 123.9(2) . . y N1A C6A H6A 117.0(14) . . y C5A C6A H6A 119.0(14) . . y C2A N7A C8A 126.2(2) . . y C2A N7A H7NA 116.1(18) . . y C8A N7A H7NA 116.4(18) . . y C9A C8A C10A 118.2(2) . . y C9A C8A N7A 123.3(2) . . y C10A C8A N7A 118.4(2) . . y C8A C9A C10A 121.0(2) . 2_655 y C8A C9A H9A 127.0(15) . . y C10A C9A H9A 111.9(15) 2_655 . y C8A C10A C9A 120.8(3) . 2_655 y C8A C10A H10A 118.8(15) . . y C9A C10A H10A 120.4(15) 2_655 . y C6B N1B C2B 117.9(2) . . y N1B C2B N7B 114.6(2) . . y N1B C2B C3B 121.1(2) . . y N7B C2B C3B 124.3(2) . . y C4B C3B C2B 119.3(2) . . y C4B C3B H3B 123.9(18) . . y C2B C3B H3B 116.7(18) . . y C3B C4B C5B 119.7(3) . . y C3B C4B H4B 120.4(17) . . y C5B C4B H4B 119.9(17) . . y C6B C5B C4B 117.4(2) . . y C6B C5B H5B 120.8(15) . . y C4B C5B H5B 121.8(15) . . y N1B C6B C5B 124.6(2) . . y N1B C6B H6B 112.3(14) . . y C5B C6B H6B 123.0(14) . . y C2B N7B C8B 128.0(2) . . y C2B N7B H7NB 115.2(15) . . y C8B N7B H7NB 116.3(15) . . y C9B C8B C10B 117.9(2) . . y C9B C8B N7B 123.2(2) . . y C10B C8B N7B 118.7(2) . . y C10B C9B C8B 121.0(2) 2_566 . y C10B C9B H9B 119.1(14) 2_566 . y C8B C9B H9B 119.8(14) . . y C9B C10B C8B 121.1(2) 2_566 . y C9B C10B H10B 121.3(14) 2_566 . y C8B C10B H10B 117.7(13) . . y 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 C9A C8A N7A C10A -176.6(4) . . . . y C9B C8B N7B C2B -42.7(4) . . . . y C10A C8A N7A C2A -155.7(3) . . . . y C10B C8B N7B C2B 141.2(2) . . . . y C8A N7A C2A N1A -156.5(2) . . . . y C8B N7B C2B N1B 178.8(2) . . . . y C8A N7A C2A C3A 27.5(4) . . . . y C8B N7B C2B C3B -2.8(4) . . . . y _refine_diff_density_max 0.172 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.041 #===END data_3b _database_code_CSD 174155 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,4-diaminobenzene, polymorph beta ; _chemical_melting_point 205-206 _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.454(1) _cell_length_b 8.991(2) _cell_length_c 19.477(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1305.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 5 _cell_measurement_theta_max 24 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 1.5 _diffrn_reflns_number 1027 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 24.04 _reflns_number_total 1027 _reflns_number_gt 595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0674P)^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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1027 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1205 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 N1 N 0.0878(3) -0.00725(19) 0.37531(10) 0.0417(6) Uani 1 1 d . . . N2 N 0.2859(3) 0.1752(2) 0.41359(11) 0.0476(6) Uani 1 1 d . . . H2N H 0.320(4) 0.268(3) 0.4067(14) 0.052(8) Uiso 1 1 d . . . C2 C 0.1401(3) 0.1353(2) 0.37640(11) 0.0368(6) Uani 1 1 d . . . C3 C 0.0525(3) 0.2443(3) 0.33708(13) 0.0439(6) Uani 1 1 d . . . H3 H 0.081(4) 0.345(4) 0.3435(14) 0.071(9) Uiso 1 1 d . . . C4 C -0.0871(3) 0.2030(3) 0.29617(14) 0.0473(7) Uani 1 1 d . . . H4 H -0.147(3) 0.277(3) 0.2632(14) 0.052(7) Uiso 1 1 d . . . C5 C -0.1426(4) 0.0580(3) 0.29494(14) 0.0511(7) Uani 1 1 d . . . H5 H -0.256(4) 0.035(3) 0.2682(15) 0.073(9) Uiso 1 1 d . . . C6 C -0.0517(4) -0.0404(3) 0.33527(14) 0.0484(7) Uani 1 1 d . . . H6 H -0.084(3) -0.148(3) 0.3338(12) 0.060(8) Uiso 1 1 d . . . C7 C 0.3914(3) 0.0853(2) 0.45716(12) 0.0394(6) Uani 1 1 d . . . C8 C 0.5755(3) 0.1004(3) 0.45593(13) 0.0496(7) Uani 1 1 d . . . H8 H 0.625(4) 0.186(4) 0.4211(16) 0.078(9) Uiso 1 1 d . . . C9 C 0.3171(3) -0.0160(3) 0.50174(14) 0.0477(7) Uani 1 1 d . . . H9 H 0.185(4) -0.027(3) 0.5034(15) 0.058(7) 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 N1 0.0507(13) 0.0278(10) 0.0465(12) 0.0034(8) -0.0063(10) 0.0006(9) N2 0.0545(13) 0.0294(11) 0.0587(12) 0.0081(11) -0.0140(11) -0.0039(11) C2 0.0378(13) 0.0333(13) 0.0394(12) -0.0010(10) 0.0004(11) 0.0010(10) C3 0.0471(14) 0.0264(12) 0.0583(15) 0.0037(12) -0.0019(14) 0.0068(13) C4 0.0461(15) 0.0404(14) 0.0553(15) 0.0055(12) -0.0053(13) 0.0078(12) C5 0.0526(16) 0.0458(15) 0.0550(16) 0.0047(13) -0.0135(13) -0.0043(14) C6 0.0574(16) 0.0331(14) 0.0547(14) 0.0023(12) -0.0113(14) -0.0066(14) C7 0.0429(13) 0.0318(12) 0.0434(13) 0.0001(11) -0.0031(12) -0.0010(11) C8 0.0520(15) 0.0488(16) 0.0481(15) 0.0137(12) -0.0075(13) -0.0111(13) C9 0.0376(14) 0.0573(16) 0.0482(14) 0.0108(13) -0.0008(11) -0.0035(12) 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 N1 C6 1.334(3) . y N1 C2 1.340(3) . y N2 C2 1.354(3) . y N2 C7 1.411(3) . y C2 C3 1.404(3) . y C3 C4 1.362(4) . y C4 C5 1.368(4) . y C5 C6 1.363(4) . y C7 C9 1.375(3) . y C7 C8 1.379(4) . y C8 C9 1.377(4) 5_656 y C9 C8 1.377(4) 5_656 y 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 N1 C2 116.72(19) . . y C2 N2 C7 128.1(2) . . y N1 C2 N2 119.7(2) . . y N1 C2 C3 121.6(2) . . y N2 C2 C3 118.7(2) . . y C4 C3 C2 119.0(2) . . y C3 C4 C5 120.1(2) . . y C6 C5 C4 117.2(3) . . y N1 C6 C5 125.4(2) . . y C9 C7 C8 118.5(2) . . y C9 C7 N2 122.3(2) . . y C8 C7 N2 119.2(2) . . y C9 C8 C7 120.9(2) 5_656 . y C7 C9 C8 120.6(2) . 5_656 y _refine_diff_density_max 0.172 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.051 #===END data_4 _database_code_CSD 174156 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-1,5-diaminonaphthalene ; _chemical_melting_point 258-260 _chemical_formula_sum 'C20 H16 N4' _chemical_formula_weight 312.37 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.118(2) _cell_length_b 9.361(2) _cell_length_c 11.803(2) _cell_angle_alpha 100.62(3) _cell_angle_beta 101.57(3) _cell_angle_gamma 114.20(3) _cell_volume 765.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2450 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30 _exptl_crystal_description plate _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <1 _diffrn_reflns_number 5718 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 24.40 _reflns_number_total 2499 _reflns_number_gt 1387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.157a, 1999' _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1240P)^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 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2499 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.2022 _refine_ls_wR_factor_gt 0.1689 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 N1A N 0.2993(4) 0.5212(3) -0.0782(2) 0.0439(7) Uani 1 1 d . . . C2A C 0.4190(5) 0.6662(4) -0.0825(3) 0.0448(9) Uani 1 1 d . . . C3A C 0.3578(5) 0.7740(4) -0.1197(3) 0.0523(10) Uani 1 1 d . . . H3A H 0.4484 0.8807 -0.1178 0.063 Uiso 1 1 d R . . C4A C 0.1682(5) 0.7260(5) -0.1584(3) 0.0568(10) Uani 1 1 d . . . H4A H 0.1241 0.7978 -0.1865 0.068 Uiso 1 1 d R . . C5A C 0.0398(5) 0.5739(5) -0.1580(3) 0.0569(10) Uani 1 1 d . . . H5A H -0.0945 0.5373 -0.1853 0.068 Uiso 1 1 d R . . C6A C 0.1107(5) 0.4777(5) -0.1168(3) 0.0555(10) Uani 1 1 d . . . H6A H 0.0223 0.3724 -0.1150 0.067 Uiso 1 1 d R . . N7A N 0.6089(4) 0.7075(3) -0.0437(3) 0.0515(8) Uani 1 1 d . . . H7A H 0.6442 0.6549 0.0051 0.062 Uiso 1 1 d R . . C8A C 0.7539(5) 0.8282(4) -0.0760(3) 0.0463(9) Uani 1 1 d . . . C9A C 0.7293(5) 0.8374(4) -0.1906(3) 0.0486(9) Uani 1 1 d . . . H9A H 0.6126 0.7612 -0.2530 0.058 Uiso 1 1 d R . . C10A C 0.9273(4) 0.9388(4) 0.0142(3) 0.0419(8) Uani 1 1 d . . . C11A C 0.9600(5) 0.9350(4) 0.1378(3) 0.0481(9) Uani 1 1 d . . . H11A H 0.8633 0.8559 0.1609 0.058 Uiso 1 1 d R . . C12A C 1.1318(5) 1.0460(4) 0.2223(3) 0.0487(9) Uani 1 1 d . . . H12A H 1.1559 1.0452 0.3051 0.058 Uiso 1 1 d R . . N1B N 0.7733(4) 0.8607(3) 0.3941(2) 0.0414(7) Uani 1 1 d . . . C2B C 0.7350(4) 0.9868(4) 0.3918(3) 0.0391(8) Uani 1 1 d . . . C3B C 0.5756(5) 0.9695(4) 0.3083(3) 0.0459(9) Uani 1 1 d . . . H3B H 0.5499 1.0610 0.3093 0.055 Uiso 1 1 d R . . C4B C 0.4559(5) 0.8195(4) 0.2242(3) 0.0480(9) Uani 1 1 d . . . H4B H 0.3447 0.8050 0.1659 0.058 Uiso 1 1 d R . . C5B C 0.4956(5) 0.6891(4) 0.2236(3) 0.0472(9) Uani 1 1 d . . . H5B H 0.4143 0.5835 0.1650 0.057 Uiso 1 1 d R . . C6B C 0.6546(5) 0.7168(4) 0.3099(3) 0.0451(9) Uani 1 1 d . . . H6B H 0.6827 0.6267 0.3098 0.054 Uiso 1 1 d R . . N7B N 0.8658(4) 1.1336(3) 0.4766(2) 0.0458(8) Uani 1 1 d . . . H7B H 0.9680 1.1354 0.5250 0.055 Uiso 1 1 d R . . C8B C 0.8531(4) 1.2812(4) 0.4945(3) 0.0390(8) Uani 1 1 d . . . C9B C 0.6994(5) 1.2889(4) 0.5185(3) 0.0477(9) Uani 1 1 d . . . H9B H 0.5968 1.1921 0.5216 0.057 Uiso 1 1 d R . . C10B C 1.0056(4) 1.4251(4) 0.4900(3) 0.0361(8) Uani 1 1 d . . . C11B C 1.1686(4) 1.4240(4) 0.4649(3) 0.0418(8) Uani 1 1 d . . . H11B H 1.1776 1.3235 0.4499 0.050 Uiso 1 1 d R . . C12B C 1.3126(5) 1.5629(4) 0.4618(3) 0.0443(9) Uani 1 1 d . . . H12B H 1.4221 1.5601 0.4447 0.053 Uiso 1 1 d R . . 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 N1A 0.0446(17) 0.0399(16) 0.0484(17) 0.0151(13) 0.0125(13) 0.0207(14) C2A 0.0365(19) 0.048(2) 0.042(2) 0.0127(16) 0.0060(15) 0.0146(17) C3A 0.055(2) 0.041(2) 0.057(2) 0.0157(18) 0.0174(18) 0.0176(18) C4A 0.059(2) 0.070(3) 0.062(2) 0.030(2) 0.022(2) 0.042(2) C5A 0.042(2) 0.063(3) 0.066(3) 0.024(2) 0.0136(18) 0.024(2) C6A 0.050(2) 0.048(2) 0.058(2) 0.0150(19) 0.0145(18) 0.0143(18) N7A 0.0398(17) 0.0415(17) 0.065(2) 0.0258(15) 0.0083(14) 0.0109(14) C8A 0.046(2) 0.0335(18) 0.056(2) 0.0175(17) 0.0091(17) 0.0167(16) C9A 0.048(2) 0.043(2) 0.050(2) 0.0117(17) 0.0091(17) 0.0193(17) C10A 0.0384(19) 0.0286(17) 0.056(2) 0.0128(16) 0.0137(16) 0.0136(15) C11A 0.047(2) 0.044(2) 0.055(2) 0.0178(18) 0.0181(17) 0.0200(17) C12A 0.051(2) 0.044(2) 0.051(2) 0.0121(17) 0.0144(18) 0.0227(18) N1B 0.0413(16) 0.0308(15) 0.0473(17) 0.0154(13) 0.0095(13) 0.0128(13) C2B 0.0373(18) 0.0334(18) 0.048(2) 0.0164(15) 0.0138(16) 0.0157(15) C3B 0.048(2) 0.046(2) 0.050(2) 0.0207(17) 0.0112(17) 0.0264(17) C4B 0.042(2) 0.050(2) 0.043(2) 0.0151(17) 0.0076(16) 0.0151(17) C5B 0.046(2) 0.0383(19) 0.042(2) 0.0078(16) 0.0075(16) 0.0106(17) C6B 0.049(2) 0.039(2) 0.047(2) 0.0167(17) 0.0152(17) 0.0181(17) N7B 0.0414(16) 0.0298(15) 0.0577(19) 0.0127(13) 0.0013(13) 0.0153(13) C8B 0.0399(19) 0.0306(17) 0.050(2) 0.0178(15) 0.0120(15) 0.0182(15) C9B 0.041(2) 0.041(2) 0.063(2) 0.0239(17) 0.0175(17) 0.0174(17) C10B 0.0350(17) 0.0360(18) 0.0391(18) 0.0151(15) 0.0085(14) 0.0179(15) C11B 0.048(2) 0.0355(18) 0.051(2) 0.0176(16) 0.0164(16) 0.0247(17) C12B 0.042(2) 0.046(2) 0.054(2) 0.0176(17) 0.0202(16) 0.0252(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1A C2A 1.324(4) . y N1A C6A 1.363(4) . y C2A N7A 1.378(4) . y C2A C3A 1.395(5) . y C3A C4A 1.361(5) . y C4A C5A 1.379(5) . y C5A C6A 1.362(5) . y N7A C8A 1.434(4) . y C8A C9A 1.351(5) . y C8A C10A 1.409(4) . y C9A C12A 1.383(5) 2_775 y C10A C10A 1.418(6) 2_775 y C10A C11A 1.439(5) . y C11A C12A 1.376(5) . y C12A C9A 1.383(5) 2_775 y N1B C6B 1.338(4) . y N1B C2B 1.342(4) . y C2B N7B 1.374(4) . y C2B C3B 1.389(4) . y C3B C4B 1.372(5) . y C4B C5B 1.383(5) . y C5B C6B 1.368(5) . y N7B C8B 1.408(4) . y C8B C9B 1.360(4) . y C8B C10B 1.427(4) . y C9B C12B 1.410(4) 2_786 y C10B C11B 1.417(4) . y C10B C10B 1.421(6) 2_786 y C11B C12B 1.359(4) . y C12B C9B 1.410(4) 2_786 y 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 C2A N1A C6A 117.0(3) . . y N1A C2A N7A 116.1(3) . . y N1A C2A C3A 122.2(3) . . y N7A C2A C3A 121.6(3) . . y C4A C3A C2A 119.1(3) . . y C3A C4A C5A 120.0(3) . . y C6A C5A C4A 117.4(3) . . y C5A C6A N1A 124.2(4) . . y C2A N7A C8A 124.5(3) . . y C9A C8A C10A 119.3(3) . . y C9A C8A N7A 121.8(3) . . y C10A C8A N7A 118.9(3) . . y C8A C9A C12A 122.1(3) . 2_775 y C8A C10A C10A 120.4(4) . 2_775 y C8A C10A C11A 121.5(3) . . y C10A C10A C11A 118.1(4) 2_775 . y C12A C11A C10A 119.1(3) . . y C11A C12A C9A 121.0(3) . 2_775 y C6B N1B C2B 117.4(3) . . y N1B C2B N7B 115.1(3) . . y N1B C2B C3B 122.0(3) . . y N7B C2B C3B 122.8(3) . . y C4B C3B C2B 118.9(3) . . y C3B C4B C5B 119.8(3) . . y C6B C5B C4B 117.4(3) . . y N1B C6B C5B 124.5(3) . . y C2B N7B C8B 125.5(3) . . y C9B C8B N7B 120.8(3) . . y C9B C8B C10B 119.8(3) . . y N7B C8B C10B 119.4(3) . . y C8B C9B C12B 121.0(3) . 2_786 y C11B C10B C10B 118.4(4) . 2_786 y C11B C10B C8B 122.1(3) . . y C10B C10B C8B 119.5(4) 2_786 . y C12B C11B C10B 121.1(3) . . y C11B C12B C9B 120.3(3) . 2_786 y 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 N1A C2A N7A C8A 158.9(3) . . . . y C3A C2A N7A C8A -23.4(5) . . . . y C2A N7A C8A C9A -43.5(5) . . . . y C2A N7A C8A C10A 137.2(3) . . . . y N1B C2B N7B C8B -177.7(3) . . . . y C3B C2B N7B C8B 3.1(5) . . . . y C2B N7B C8B C9B 56.4(5) . . . . y C2B N7B C8B C10B -125.0(3) . . . . y _refine_diff_density_max 0.460 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.056 #===END data_5 _database_code_CSD 174157 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-4,4'-diaminobiphenyl ; _chemical_melting_point 232-234 _chemical_formula_sum 'C22 H18 N4' _chemical_formula_weight 338.40 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.761(3) _cell_length_b 13.162(3) _cell_length_c 18.341(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.70(3) _cell_angle_gamma 90.00 _cell_volume 3446.7(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 5 _cell_measurement_theta_max 14 _exptl_crystal_description plate _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <2% _diffrn_reflns_number 2810 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.1042 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.04 _reflns_number_total 2720 _reflns_number_gt 1415 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0671P)^2^+0.0054P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2720 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1665 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 N1A N 0.76292(19) 0.1254(2) 0.54559(15) 0.0486(8) Uani 1 1 d . . . C2A C 0.8194(2) 0.0971(3) 0.50244(17) 0.0427(8) Uani 1 1 d . . . C3A C 0.8685(3) 0.0060(3) 0.51305(19) 0.0486(9) Uani 1 1 d . . . C4A C 0.8575(3) -0.0571(3) 0.5693(2) 0.0554(10) Uani 1 1 d . . . C5A C 0.7991(3) -0.0308(3) 0.6136(2) 0.0581(10) Uani 1 1 d . . . C6A C 0.7554(3) 0.0605(3) 0.60071(19) 0.0561(10) Uani 1 1 d . . . N7A N 0.8257(2) 0.1674(2) 0.44850(16) 0.0533(8) Uani 1 1 d . . . C8A C 0.8768(2) 0.1605(3) 0.39362(17) 0.0415(8) Uani 1 1 d . . . C9A C 0.9200(2) 0.2466(3) 0.37588(18) 0.0430(8) Uani 1 1 d . . . C10A C 0.9662(2) 0.2463(3) 0.31995(17) 0.0411(8) Uani 1 1 d . . . C11A C 0.9739(2) 0.1584(2) 0.27914(16) 0.0386(7) Uani 1 1 d . . . C12A C 0.9306(2) 0.0715(3) 0.29793(18) 0.0452(8) Uani 1 1 d . . . C13A C 0.8817(2) 0.0727(3) 0.35315(18) 0.0472(9) Uani 1 1 d . . . N1B N 0.65859(18) -0.1516(2) 0.45415(14) 0.0513(8) Uani 1 1 d . . . C2B C 0.7004(2) -0.1525(3) 0.39751(17) 0.0453(8) Uani 1 1 d . . . C3B C 0.6758(3) -0.0841(3) 0.3376(2) 0.0534(9) Uani 1 1 d . . . C4B C 0.6088(3) -0.0126(3) 0.3385(2) 0.0618(10) Uani 1 1 d . . . C5B C 0.5667(3) -0.0089(3) 0.3972(2) 0.0688(12) Uani 1 1 d . . . C6B C 0.5933(3) -0.0800(3) 0.4524(2) 0.0644(11) Uani 1 1 d . . . N7B N 0.7696(2) -0.2232(2) 0.40513(17) 0.0519(8) Uani 1 1 d . . . C8B C 0.8338(2) -0.2297(2) 0.35975(17) 0.0438(8) Uani 1 1 d . . . C9B C 0.8057(2) -0.2486(3) 0.28362(18) 0.0517(9) Uani 1 1 d . . . C10B C 0.8707(2) -0.2532(3) 0.24134(19) 0.0469(9) Uani 1 1 d . . . C11B C 0.9654(2) -0.2395(2) 0.27308(17) 0.0413(7) Uani 1 1 d . . . C12B C 0.9929(3) -0.2244(3) 0.35023(19) 0.0510(9) Uani 1 1 d . . . C13B C 0.9286(2) -0.2188(3) 0.39307(19) 0.0501(9) Uani 1 1 d . . . H7A H 0.797(2) 0.227(3) 0.450(2) 0.064(12) Uiso 1 1 d . . . H3A H 0.912(2) -0.019(2) 0.4866(17) 0.046(9) Uiso 1 1 d . . . H4A H 0.888(2) -0.123(3) 0.5763(18) 0.060(11) Uiso 1 1 d . . . H5A H 0.797(2) -0.075(3) 0.655(2) 0.074(12) Uiso 1 1 d . . . H6A H 0.710(2) 0.087(2) 0.6305(17) 0.051(9) Uiso 1 1 d . . . H9A H 0.9229(19) 0.306(2) 0.4071(16) 0.037(8) Uiso 1 1 d . . . H10A H 0.998(2) 0.307(2) 0.3106(16) 0.044(9) Uiso 1 1 d . . . H12A H 0.9316(19) 0.013(2) 0.2672(16) 0.036(8) Uiso 1 1 d . . . H13A H 0.852(2) 0.008(2) 0.3638(16) 0.046(9) Uiso 1 1 d . . . H7B H 0.793(2) -0.265(3) 0.452(2) 0.075(12) Uiso 1 1 d . . . H3B H 0.701(2) -0.090(2) 0.2952(18) 0.052(9) Uiso 1 1 d . . . H4B H 0.595(2) 0.035(3) 0.298(2) 0.063(11) Uiso 1 1 d . . . H5B H 0.512(3) 0.039(4) 0.397(2) 0.112(16) Uiso 1 1 d . . . H6B H 0.560(3) -0.078(3) 0.490(2) 0.080(12) Uiso 1 1 d . . . H9B H 0.743(2) -0.258(2) 0.2599(17) 0.052(9) Uiso 1 1 d . . . H10B H 0.852(2) -0.267(2) 0.191(2) 0.056(10) Uiso 1 1 d . . . H12B H 1.0545(19) -0.220(2) 0.3759(14) 0.024(7) Uiso 1 1 d . . . H13B H 0.951(2) -0.210(2) 0.447(2) 0.059(10) 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 N1A 0.0594(18) 0.0487(17) 0.0443(15) 0.0029(14) 0.0252(15) -0.0001(14) C2A 0.0415(19) 0.045(2) 0.0429(18) 0.0032(16) 0.0125(16) -0.0036(16) C3A 0.051(2) 0.046(2) 0.050(2) 0.0021(17) 0.0142(17) 0.0039(18) C4A 0.061(2) 0.050(2) 0.049(2) 0.0011(18) 0.0033(19) 0.006(2) C5A 0.075(3) 0.053(3) 0.044(2) 0.0110(19) 0.010(2) -0.007(2) C6A 0.071(3) 0.061(3) 0.0426(19) 0.0052(18) 0.0259(19) -0.004(2) N7A 0.062(2) 0.0498(19) 0.0596(18) 0.0105(16) 0.0358(16) 0.0094(16) C8A 0.0409(19) 0.045(2) 0.0433(18) 0.0037(16) 0.0189(15) -0.0011(16) C9A 0.0421(19) 0.040(2) 0.0476(19) -0.0058(17) 0.0122(16) 0.0019(16) C10A 0.0416(19) 0.039(2) 0.0458(19) -0.0001(16) 0.0177(15) -0.0079(16) C11A 0.0362(16) 0.0415(18) 0.0387(15) -0.0013(16) 0.0106(13) 0.0011(16) C12A 0.051(2) 0.041(2) 0.0448(19) -0.0023(17) 0.0149(17) -0.0056(17) C13A 0.050(2) 0.044(2) 0.051(2) 0.0032(17) 0.0194(17) -0.0078(17) N1B 0.0444(17) 0.065(2) 0.0472(16) -0.0034(15) 0.0161(14) -0.0010(16) C2B 0.0381(19) 0.054(2) 0.0466(19) -0.0054(17) 0.0151(16) -0.0059(17) C3B 0.051(2) 0.053(2) 0.058(2) 0.0043(19) 0.0174(19) -0.0052(19) C4B 0.065(3) 0.047(2) 0.071(3) 0.006(2) 0.013(2) -0.003(2) C5B 0.063(3) 0.066(3) 0.076(3) -0.003(2) 0.015(2) 0.015(2) C6B 0.057(2) 0.079(3) 0.062(2) -0.020(2) 0.024(2) 0.005(2) N7B 0.0485(17) 0.065(2) 0.0500(18) 0.0118(15) 0.0264(15) 0.0097(16) C8B 0.044(2) 0.049(2) 0.0421(19) 0.0060(16) 0.0179(16) -0.0027(17) C9B 0.039(2) 0.077(3) 0.042(2) -0.0037(19) 0.0149(17) -0.0062(19) C10B 0.048(2) 0.058(2) 0.0371(19) -0.0038(17) 0.0147(17) -0.0049(17) C11B 0.0421(18) 0.0436(18) 0.0408(17) -0.0017(16) 0.0152(14) -0.0045(17) C12B 0.034(2) 0.069(3) 0.048(2) -0.0078(18) 0.0091(17) -0.0032(18) C13B 0.053(2) 0.067(3) 0.0354(19) -0.0056(17) 0.0207(18) 0.0011(19) 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 N1A C2A 1.339(4) . y N1A C6A 1.349(4) . y C2A N7A 1.375(4) . y C2A C3A 1.389(5) . y C3A C4A 1.366(5) . y C3A H3A 0.96(3) . y C4A C5A 1.370(5) . y C4A H4A 0.97(3) . y C5A C6A 1.356(5) . y C5A H5A 0.97(4) . y C6A H6A 1.03(3) . y N7A C8A 1.406(4) . y N7A H7A 0.90(4) . y C8A C9A 1.379(4) . y C8A C13A 1.386(5) . y C9A C10A 1.368(4) . y C9A H9A 0.96(3) . y C10A C11A 1.398(4) . y C10A H10A 0.96(3) . y C11A C12A 1.394(4) . y C11A C11A 1.468(6) 2_755 y C12A C13A 1.386(4) . y C12A H12A 0.96(3) . y C13A H13A 1.00(3) . y N1B C2B 1.337(4) . y N1B C6B 1.342(5) . y C2B N7B 1.361(4) . y C2B C3B 1.396(5) . y C3B C4B 1.369(5) . y C3B H3B 0.94(3) . y C4B C5B 1.373(6) . y C4B H4B 0.96(3) . y C5B C6B 1.362(6) . y C5B H5B 1.02(5) . y C6B H6B 0.95(4) . y N7B C8B 1.414(4) . y N7B H7B 1.00(4) . y C8B C9B 1.374(4) . y C8B C13B 1.386(5) . y C9B C10B 1.380(5) . y C9B H9B 0.93(3) . y C10B C11B 1.383(4) . y C10B H10B 0.92(3) . y C11B C12B 1.384(4) . y C11B C11B 1.482(6) 2_755 y C12B C13B 1.379(4) . y C12B H12B 0.91(3) . y C13B H13B 0.97(3) . y 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 C2A N1A C6A 116.7(3) . . y N1A C2A N7A 113.8(3) . . y N1A C2A C3A 122.6(3) . . y N7A C2A C3A 123.6(3) . . y C4A C3A C2A 118.2(3) . . y C4A C3A H3A 113.4(19) . . y C2A C3A H3A 128.4(19) . . y C3A C4A C5A 120.4(4) . . y C3A C4A H4A 120(2) . . y C5A C4A H4A 119(2) . . y C6A C5A C4A 117.7(4) . . y C6A C5A H5A 124(2) . . y C4A C5A H5A 118(2) . . y N1A C6A C5A 124.4(3) . . y N1A C6A H6A 111.9(18) . . y C5A C6A H6A 123.6(18) . . y C2A N7A C8A 128.2(3) . . y C2A N7A H7A 116(2) . . y C8A N7A H7A 115(2) . . y C9A C8A C13A 118.0(3) . . y C9A C8A N7A 118.7(3) . . y C13A C8A N7A 123.2(3) . . y C10A C9A C8A 121.5(3) . . y C10A C9A H9A 119.8(17) . . y C8A C9A H9A 118.4(17) . . y C9A C10A C11A 121.9(3) . . y C9A C10A H10A 119.2(18) . . y C11A C10A H10A 118.8(17) . . y C12A C11A C10A 116.2(3) . . y C12A C11A C11A 122.5(2) . 2_755 y C10A C11A C11A 121.25(19) . 2_755 y C13A C12A C11A 121.9(4) . . y C13A C12A H12A 121.9(17) . . y C11A C12A H12A 116.0(16) . . y C12A C13A C8A 120.5(3) . . y C12A C13A H13A 118.0(17) . . y C8A C13A H13A 121.4(17) . . y C2B N1B C6B 117.3(3) . . y N1B C2B N7B 114.1(3) . . y N1B C2B C3B 121.8(3) . . y N7B C2B C3B 124.1(3) . . y C4B C3B C2B 118.6(4) . . y C4B C3B H3B 120(2) . . y C2B C3B H3B 121(2) . . y C3B C4B C5B 120.4(4) . . y C3B C4B H4B 117(2) . . y C5B C4B H4B 123(2) . . y C6B C5B C4B 117.1(4) . . y C6B C5B H5B 121(3) . . y C4B C5B H5B 122(3) . . y N1B C6B C5B 124.8(4) . . y N1B C6B H6B 120(2) . . y C5B C6B H6B 115(2) . . y C2B N7B C8B 125.3(3) . . y C2B N7B H7B 124(2) . . y C8B N7B H7B 109(2) . . y C9B C8B C13B 118.5(3) . . y C9B C8B N7B 122.4(3) . . y C13B C8B N7B 119.2(3) . . y C8B C9B C10B 120.4(3) . . y C8B C9B H9B 120.5(19) . . y C10B C9B H9B 119.1(19) . . y C9B C10B C11B 122.0(3) . . y C9B C10B H10B 120(2) . . y C11B C10B H10B 118(2) . . y C10B C11B C12B 116.8(3) . . y C10B C11B C11B 121.9(4) . 2_755 y C12B C11B C11B 121.3(4) . 2_755 y C13B C12B C11B 121.7(3) . . y C13B C12B H12B 116.2(16) . . y C11B C12B H12B 122.1(15) . . y C12B C13B C8B 120.5(3) . . y C12B C13B H13B 119(2) . . y C8B C13B H13B 120.3(19) . . y 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 N1A C2A N7A C8A -178.6(3) . . . . y C3A C2A N7A C8A 3.0(6) . . . . y C2A N7A C8A C9A -142.3(4) . . . . y C2A N7A C8A C13A 41.5(5) . . . . y N1B C2B N7B C8B -169.8(3) . . . . y C3B C2B N7B C8B 8.4(5) . . . . y C2B N7B C8B C9B -62.8(5) . . . . y C2B N7B C8B C13B 118.5(4) . . . . y _refine_diff_density_max 0.156 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.042 #===END data_6a _database_code_CSD 174158 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl) -4,4'-oxybis(aminobenzene), polymorph alphafrom ethyl acetate ; _chemical_melting_point 143-144 _chemical_formula_sum 'C22 H18 N4 O' _chemical_formula_weight 354.40 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6437(5) _cell_length_b 11.8742(6) _cell_length_c 17.1611(8) _cell_angle_alpha 79.732(4) _cell_angle_beta 89.713(4) _cell_angle_gamma 72.535(5) _cell_volume 1842.06(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3899 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 15254 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7401 _reflns_number_gt 5285 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.157a, 1999' _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0856P)^2^+0.0374P] 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 'C-H riding model, N-H refall' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7401 _refine_ls_number_parameters 503 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 N1A N 1.18438(16) 0.15727(13) 0.41450(10) 0.0597(4) Uani 1 1 d . . . C2A C 1.10109(17) 0.27254(15) 0.40480(10) 0.0478(4) Uani 1 1 d . . . C3A C 1.1257(2) 0.35042(17) 0.45109(11) 0.0592(5) Uani 1 1 d . . . H3A H 1.0639 0.4321 0.4437 0.071 Uiso 1 1 d R . . C4A C 1.2393(3) 0.3092(2) 0.50670(13) 0.0756(6) Uani 1 1 d . . . H4A H 1.2574 0.3614 0.5395 0.091 Uiso 1 1 d R . . C5A C 1.3253(3) 0.1912(2) 0.51663(15) 0.0881(7) Uani 1 1 d . . . H5A H 1.4079 0.1606 0.5538 0.106 Uiso 1 1 d R . . C6A C 1.2923(2) 0.1200(2) 0.47021(14) 0.0769(6) Uani 1 1 d . . . H6A H 1.3501 0.0371 0.4785 0.092 Uiso 1 1 d R . . N7A N 0.98925(15) 0.30209(13) 0.34862(9) 0.0515(4) Uani 1 1 d . . . H7A H 0.963(2) 0.2382(18) 0.3341(12) 0.062(5) Uiso 1 1 d . . . C8A C 0.90374(16) 0.41617(14) 0.31095(10) 0.0443(4) Uani 1 1 d . . . C9A C 0.76489(19) 0.42938(17) 0.28131(12) 0.0610(5) Uani 1 1 d . . . H9A H 0.7275 0.3621 0.2915 0.073 Uiso 1 1 d R . . C10A C 0.68043(18) 0.53692(17) 0.23777(12) 0.0612(5) Uani 1 1 d . . . H10A H 0.5856 0.5440 0.2166 0.073 Uiso 1 1 d R . . C11A C 0.73217(17) 0.63386(15) 0.22459(10) 0.0480(4) Uani 1 1 d . . . C12A C 0.86950(19) 0.62270(15) 0.25280(11) 0.0552(4) Uani 1 1 d . . . H12A H 0.9063 0.6903 0.2425 0.066 Uiso 1 1 d R . . C13A C 0.95546(18) 0.51424(15) 0.29552(11) 0.0512(4) Uani 1 1 d . . . H13A H 1.0514 0.5068 0.3152 0.061 Uiso 1 1 d R . . O14A O 0.65070(12) 0.74193(10) 0.17709(7) 0.0563(3) Uani 1 1 d . . . C15A C 0.52424(17) 0.80686(14) 0.20740(9) 0.0445(4) Uani 1 1 d . . . C16A C 0.4127(2) 0.87414(16) 0.15291(10) 0.0601(5) Uani 1 1 d . . . H16A H 0.4235 0.8707 0.0977 0.072 Uiso 1 1 d R . . C17A C 0.2860(2) 0.94712(17) 0.17766(11) 0.0651(5) Uani 1 1 d . . . H17A H 0.2093 0.9949 0.1394 0.078 Uiso 1 1 d R . . C18A C 0.26877(18) 0.95127(14) 0.25723(10) 0.0474(4) Uani 1 1 d . . . C19A C 0.38118(17) 0.88155(15) 0.31130(10) 0.0482(4) Uani 1 1 d . . . H19A H 0.3693 0.8825 0.3668 0.058 Uiso 1 1 d R . . C20A C 0.50868(17) 0.80959(15) 0.28686(10) 0.0504(4) Uani 1 1 d . . . H20A H 0.5863 0.7630 0.3250 0.061 Uiso 1 1 d R . . N21A N 0.14119(15) 1.02647(14) 0.28444(10) 0.0549(4) Uani 1 1 d . . . H21A H 0.156(2) 1.0673(17) 0.3223(12) 0.062(5) Uiso 1 1 d . . . C22A C 0.00242(18) 1.02406(14) 0.27114(10) 0.0470(4) Uani 1 1 d . . . N23A N -0.10002(15) 1.10335(13) 0.30342(9) 0.0563(4) Uani 1 1 d . . . C24A C -0.2383(2) 1.10226(19) 0.29541(13) 0.0691(6) Uani 1 1 d . . . H24A H -0.3111 1.1598 0.3185 0.083 Uiso 1 1 d R . . C25A C -0.2818(2) 1.02736(19) 0.25689(13) 0.0699(5) Uani 1 1 d . . . H25A H -0.3819 1.0294 0.2536 0.084 Uiso 1 1 d R . . C26A C -0.1764(2) 0.94860(17) 0.22293(13) 0.0691(6) Uani 1 1 d . . . H26A H -0.2019 0.8951 0.1939 0.083 Uiso 1 1 d R . . C27A C -0.0337(2) 0.94541(16) 0.22915(12) 0.0612(5) Uani 1 1 d . . . H27A H 0.0407 0.8897 0.2058 0.073 Uiso 1 1 d R . . N1B N 1.37627(16) 0.65079(13) 0.48978(8) 0.0556(4) Uani 1 1 d . . . C2B C 1.30060(17) 0.63476(14) 0.42942(9) 0.0455(4) Uani 1 1 d . . . C3B C 1.15960(18) 0.70832(16) 0.40593(10) 0.0517(4) Uani 1 1 d . . . H3B H 1.1060 0.6910 0.3650 0.062 Uiso 1 1 d R . . C4B C 1.0991(2) 0.80380(17) 0.44249(11) 0.0591(5) Uani 1 1 d . . . H4B H 1.0030 0.8568 0.4263 0.071 Uiso 1 1 d R . . C5B C 1.1771(2) 0.82446(18) 0.50220(11) 0.0654(5) Uani 1 1 d . . . H5B H 1.1388 0.8922 0.5277 0.078 Uiso 1 1 d R . . C6B C 1.3124(2) 0.74501(18) 0.52412(11) 0.0659(5) Uani 1 1 d . . . H6B H 1.3653 0.7572 0.5675 0.079 Uiso 1 1 d R . . N7B N 1.37135(17) 0.53837(13) 0.39470(9) 0.0526(4) Uani 1 1 d . . . H7B H 1.445(2) 0.4876(17) 0.4231(12) 0.065(6) Uiso 1 1 d . . . C8B C 1.33937(16) 0.52124(14) 0.31871(10) 0.0442(4) Uani 1 1 d . . . C9B C 1.36607(17) 0.40565(15) 0.30342(10) 0.0498(4) Uani 1 1 d . . . H9B H 1.4038 0.3381 0.3457 0.060 Uiso 1 1 d R . . C10B C 1.33931(19) 0.38647(15) 0.22832(11) 0.0530(4) Uani 1 1 d . . . H10B H 1.3618 0.3063 0.2179 0.064 Uiso 1 1 d R . . C11B C 1.28017(17) 0.48340(15) 0.16770(9) 0.0464(4) Uani 1 1 d . . . C12B C 1.25440(17) 0.59879(14) 0.18131(10) 0.0457(4) Uani 1 1 d . . . H12B H 1.2144 0.6658 0.1390 0.055 Uiso 1 1 d R . . C13B C 1.28538(17) 0.61767(14) 0.25589(10) 0.0458(4) Uani 1 1 d . . . H13B H 1.2702 0.6980 0.2648 0.055 Uiso 1 1 d R . . O14B O 1.25629(14) 0.47105(11) 0.09022(7) 0.0571(3) Uani 1 1 d . . . C15B C 1.17944(17) 0.39424(14) 0.07488(9) 0.0452(4) Uani 1 1 d . . . C16B C 1.19826(19) 0.35908(16) 0.00223(10) 0.0524(4) Uani 1 1 d . . . H16B H 1.2629 0.3862 -0.0339 0.063 Uiso 1 1 d R . . C17B C 1.12366(19) 0.28604(16) -0.01874(10) 0.0536(4) Uani 1 1 d . . . H17B H 1.1364 0.2616 -0.0694 0.064 Uiso 1 1 d R . . C18B C 1.03060(17) 0.24503(14) 0.03261(10) 0.0457(4) Uani 1 1 d . . . C19B C 1.0132(2) 0.28108(16) 0.10552(10) 0.0546(4) Uani 1 1 d . . . H19B H 0.9491 0.2537 0.1419 0.066 Uiso 1 1 d R . . C20B C 1.0854(2) 0.35660(17) 0.12616(10) 0.0559(4) Uani 1 1 d . . . H20B H 1.0713 0.3821 0.1764 0.067 Uiso 1 1 d R . . N21B N 0.96388(17) 0.16276(14) 0.01086(10) 0.0566(4) Uani 1 1 d . . . H21B H 1.025(2) 0.0970(19) -0.0027(12) 0.067(6) Uiso 1 1 d . . . C22B C 0.82744(18) 0.15767(15) 0.02960(9) 0.0473(4) Uani 1 1 d . . . N23B N 0.80418(15) 0.05226(13) 0.02918(8) 0.0515(4) Uani 1 1 d . . . C24B C 0.6706(2) 0.04396(18) 0.04626(11) 0.0588(5) Uani 1 1 d . . . H24B H 0.6540 -0.0316 0.0453 0.071 Uiso 1 1 d R . . C25B C 0.5577(2) 0.1363(2) 0.06340(12) 0.0647(5) Uani 1 1 d . . . H25B H 0.4651 0.1253 0.0762 0.078 Uiso 1 1 d R . . C26B C 0.5822(2) 0.2457(2) 0.06187(12) 0.0673(5) Uani 1 1 d . . . H26B H 0.5053 0.3130 0.0729 0.081 Uiso 1 1 d R . . C27B C 0.7166(2) 0.25758(17) 0.04499(12) 0.0599(5) Uani 1 1 d . . . H27B H 0.7354 0.3329 0.0435 0.072 Uiso 1 1 d R . . 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 N1A 0.0518(8) 0.0552(9) 0.0670(10) -0.0189(7) -0.0131(7) -0.0041(7) C2A 0.0434(9) 0.0512(9) 0.0508(10) -0.0120(7) 0.0022(7) -0.0162(7) C3A 0.0694(12) 0.0575(11) 0.0544(11) -0.0182(9) 0.0002(9) -0.0204(9) C4A 0.0883(15) 0.0853(15) 0.0607(12) -0.0272(11) -0.0096(11) -0.0296(12) C5A 0.0807(15) 0.0965(17) 0.0797(16) -0.0260(13) -0.0338(12) -0.0095(13) C6A 0.0669(13) 0.0726(13) 0.0805(15) -0.0222(11) -0.0249(11) -0.0002(10) N7A 0.0473(8) 0.0428(8) 0.0655(9) -0.0137(7) -0.0094(7) -0.0127(6) C8A 0.0368(8) 0.0441(8) 0.0525(9) -0.0137(7) 0.0040(7) -0.0104(7) C9A 0.0447(9) 0.0550(10) 0.0837(14) -0.0033(9) -0.0022(9) -0.0212(8) C10A 0.0374(9) 0.0657(11) 0.0777(13) -0.0046(10) -0.0041(8) -0.0166(8) C11A 0.0400(8) 0.0496(9) 0.0486(9) -0.0088(7) 0.0068(7) -0.0050(7) C12A 0.0489(10) 0.0488(10) 0.0690(12) -0.0084(8) 0.0013(8) -0.0179(8) C13A 0.0395(8) 0.0502(9) 0.0644(11) -0.0112(8) -0.0046(7) -0.0138(7) O14A 0.0461(6) 0.0608(7) 0.0494(7) -0.0012(5) 0.0081(5) -0.0026(5) C15A 0.0418(8) 0.0436(8) 0.0451(9) -0.0047(7) 0.0038(7) -0.0106(7) C16A 0.0641(11) 0.0648(11) 0.0368(9) -0.0036(8) -0.0018(8) -0.0011(9) C17A 0.0615(11) 0.0640(12) 0.0466(10) -0.0007(8) -0.0074(8) 0.0100(9) C18A 0.0489(9) 0.0412(8) 0.0482(9) -0.0104(7) -0.0030(7) -0.0065(7) C19A 0.0477(9) 0.0572(10) 0.0402(8) -0.0138(7) -0.0030(7) -0.0140(8) C20A 0.0417(9) 0.0620(10) 0.0431(9) -0.0082(7) -0.0066(7) -0.0099(8) N21A 0.0478(8) 0.0523(8) 0.0633(10) -0.0249(7) -0.0036(7) -0.0050(6) C22A 0.0510(9) 0.0403(8) 0.0447(9) -0.0068(7) -0.0065(7) -0.0071(7) N23A 0.0508(8) 0.0589(9) 0.0642(10) -0.0263(7) 0.0026(7) -0.0153(7) C24A 0.0545(11) 0.0787(14) 0.0810(14) -0.0321(11) 0.0048(10) -0.0206(10) C25A 0.0658(12) 0.0716(13) 0.0796(14) -0.0159(11) -0.0073(10) -0.0307(11) C26A 0.0819(14) 0.0491(11) 0.0778(14) -0.0131(10) -0.0245(11) -0.0208(10) C27A 0.0693(12) 0.0459(10) 0.0643(12) -0.0187(8) -0.0142(9) -0.0061(8) N1B 0.0617(9) 0.0560(9) 0.0472(8) -0.0159(7) -0.0075(7) -0.0114(7) C2B 0.0511(9) 0.0481(9) 0.0392(8) -0.0077(7) -0.0005(7) -0.0181(7) C3B 0.0477(9) 0.0606(10) 0.0468(9) -0.0109(8) 0.0001(7) -0.0157(8) C4B 0.0535(10) 0.0643(11) 0.0511(10) -0.0074(9) 0.0099(8) -0.0074(9) C5B 0.0776(13) 0.0609(12) 0.0533(11) -0.0188(9) 0.0113(10) -0.0099(10) C6B 0.0805(13) 0.0670(12) 0.0501(11) -0.0231(9) -0.0064(9) -0.0149(10) N7B 0.0535(8) 0.0506(8) 0.0508(8) -0.0159(7) -0.0134(7) -0.0073(7) C8B 0.0376(8) 0.0494(9) 0.0489(9) -0.0154(7) -0.0021(7) -0.0147(7) C9B 0.0488(9) 0.0448(9) 0.0540(10) -0.0127(7) -0.0030(7) -0.0092(7) C10B 0.0580(10) 0.0451(9) 0.0585(11) -0.0202(8) 0.0034(8) -0.0137(8) C11B 0.0473(9) 0.0566(10) 0.0439(9) -0.0194(7) 0.0043(7) -0.0230(8) C12B 0.0471(9) 0.0476(9) 0.0457(9) -0.0092(7) 0.0010(7) -0.0191(7) C13B 0.0469(9) 0.0433(9) 0.0521(10) -0.0150(7) 0.0012(7) -0.0176(7) O14B 0.0761(8) 0.0656(8) 0.0449(7) -0.0203(6) 0.0090(6) -0.0387(7) C15B 0.0499(9) 0.0474(9) 0.0431(9) -0.0147(7) 0.0024(7) -0.0183(7) C16B 0.0570(10) 0.0661(11) 0.0437(9) -0.0174(8) 0.0102(8) -0.0288(9) C17B 0.0576(10) 0.0675(11) 0.0445(9) -0.0254(8) 0.0079(8) -0.0236(9) C18B 0.0463(9) 0.0450(9) 0.0489(9) -0.0167(7) 0.0024(7) -0.0141(7) C19B 0.0639(11) 0.0607(11) 0.0486(10) -0.0159(8) 0.0130(8) -0.0297(9) C20B 0.0679(11) 0.0684(11) 0.0439(9) -0.0258(8) 0.0127(8) -0.0305(9) N21B 0.0528(9) 0.0529(9) 0.0746(10) -0.0313(8) 0.0134(7) -0.0208(7) C22B 0.0495(9) 0.0535(10) 0.0411(9) -0.0135(7) -0.0001(7) -0.0162(8) N23B 0.0533(8) 0.0562(9) 0.0489(8) -0.0132(6) -0.0029(6) -0.0204(7) C24B 0.0589(11) 0.0687(12) 0.0541(11) -0.0105(9) -0.0043(8) -0.0276(9) C25B 0.0504(11) 0.0877(15) 0.0599(12) -0.0151(10) 0.0035(9) -0.0259(10) C26B 0.0522(11) 0.0784(14) 0.0685(13) -0.0241(10) 0.0035(9) -0.0096(10) C27B 0.0561(11) 0.0562(10) 0.0690(12) -0.0209(9) 0.0044(9) -0.0143(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1A C6A 1.333(2) . y N1A C2A 1.344(2) . y C2A N7A 1.371(2) . y C2A C3A 1.392(2) . y C3A C4A 1.368(3) . y C4A C5A 1.378(3) . y C5A C6A 1.362(3) . y N7A C8A 1.398(2) . y C8A C13A 1.383(2) . y C8A C9A 1.389(2) . y C9A C10A 1.376(3) . y C10A C11A 1.370(2) . y C11A C12A 1.373(2) . y C11A O14A 1.3989(19) . y C12A C13A 1.383(2) . y O14A C15A 1.3873(18) . y C15A C20A 1.376(2) . y C15A C16A 1.378(2) . y C16A C17A 1.383(2) . y C17A C18A 1.383(2) . y C18A C19A 1.385(2) . y C18A N21A 1.419(2) . y C19A C20A 1.382(2) . y N21A C22A 1.368(2) . y C22A N23A 1.338(2) . y C22A C27A 1.397(2) . y N23A C24A 1.346(2) . y C24A C25A 1.356(3) . y C25A C26A 1.366(3) . y C26A C27A 1.369(3) . y N1B C6B 1.340(2) . y N1B C2B 1.343(2) . y C2B N7B 1.379(2) . y C2B C3B 1.393(2) . y C3B C4B 1.368(2) . y C4B C5B 1.373(3) . y C5B C6B 1.369(3) . y N7B C8B 1.405(2) . y C8B C9B 1.391(2) . y C8B C13B 1.397(2) . y C9B C10B 1.387(2) . y C10B C11B 1.385(2) . y C11B C12B 1.379(2) . y C11B O14B 1.3912(19) . y C12B C13B 1.387(2) . y O14B C15B 1.3940(19) . y C15B C20B 1.376(2) . y C15B C16B 1.378(2) . y C16B C17B 1.374(2) . y C17B C18B 1.386(2) . y C18B C19B 1.387(2) . y C18B N21B 1.420(2) . y C19B C20B 1.380(2) . y N21B C22B 1.369(2) . y C22B N23B 1.337(2) . y C22B C27B 1.403(2) . y N23B C24B 1.348(2) . y C24B C25B 1.367(3) . y C25B C26B 1.384(3) . y C26B C27B 1.369(3) . y 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 C6A N1A C2A 117.43(16) . . y N1A C2A N7A 113.63(15) . . y N1A C2A C3A 121.59(16) . . y N7A C2A C3A 124.72(16) . . y C4A C3A C2A 119.17(18) . . y C3A C4A C5A 119.4(2) . . y C6A C5A C4A 117.9(2) . . y N1A C6A C5A 124.5(2) . . y C2A N7A C8A 128.64(15) . . y C13A C8A C9A 118.20(15) . . y C13A C8A N7A 123.00(14) . . y C9A C8A N7A 118.54(15) . . y C10A C9A C8A 121.19(16) . . y C11A C10A C9A 119.79(16) . . y C10A C11A C12A 120.04(15) . . y C10A C11A O14A 120.42(15) . . y C12A C11A O14A 119.35(15) . . y C11A C12A C13A 120.28(16) . . y C12A C13A C8A 120.47(15) . . y C15A O14A C11A 117.03(12) . . y C20A C15A C16A 120.15(15) . . y C20A C15A O14A 123.45(14) . . y C16A C15A O14A 116.36(14) . . y C15A C16A C17A 120.10(16) . . y C18A C17A C16A 120.50(15) . . y C17A C18A C19A 118.58(15) . . y C17A C18A N21A 121.89(14) . . y C19A C18A N21A 119.51(15) . . y C20A C19A C18A 121.20(15) . . y C15A C20A C19A 119.45(14) . . y C22A N21A C18A 125.45(15) . . y N23A C22A N21A 114.35(15) . . y N23A C22A C27A 121.13(16) . . y N21A C22A C27A 124.51(16) . . y C22A N23A C24A 117.40(16) . . y N23A C24A C25A 125.00(19) . . y C24A C25A C26A 116.89(19) . . y C25A C26A C27A 120.77(18) . . y C26A C27A C22A 118.79(18) . . y C6B N1B C2B 116.73(15) . . y N1B C2B N7B 114.88(14) . . y N1B C2B C3B 121.98(15) . . y N7B C2B C3B 123.10(15) . . y C4B C3B C2B 119.14(17) . . y C3B C4B C5B 119.62(17) . . y C6B C5B C4B 117.62(18) . . y N1B C6B C5B 124.78(18) . . y C2B N7B C8B 126.35(14) . . y C9B C8B C13B 117.94(15) . . y C9B C8B N7B 120.13(15) . . y C13B C8B N7B 121.90(14) . . y C10B C9B C8B 121.15(15) . . y C11B C10B C9B 119.95(15) . . y C12B C11B C10B 119.81(15) . . y C12B C11B O14B 116.88(15) . . y C10B C11B O14B 123.06(15) . . y C11B C12B C13B 120.07(15) . . y C12B C13B C8B 120.99(15) . . y C11B O14B C15B 120.30(12) . . y C20B C15B C16B 119.91(15) . . y C20B C15B O14B 123.98(14) . . y C16B C15B O14B 116.07(14) . . y C17B C16B C15B 120.00(16) . . y C16B C17B C18B 121.08(15) . . y C17B C18B C19B 118.15(15) . . y C17B C18B N21B 119.16(15) . . y C19B C18B N21B 122.59(15) . . y C20B C19B C18B 121.00(16) . . y C15B C20B C19B 119.83(15) . . y C22B N21B C18B 125.61(15) . . y N23B C22B N21B 115.72(15) . . y N23B C22B C27B 121.72(16) . . y N21B C22B C27B 122.50(16) . . y C22B N23B C24B 117.59(15) . . y N23B C24B C25B 124.24(18) . . y C24B C25B C26B 117.58(18) . . y C27B C26B C25B 119.88(18) . . y C26B C27B C22B 118.95(18) . . y 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 C2A N7A C8A C9A -154.67(18) . . . . y C2A N7A C8A C13A 31.3(3) . . . . y C3A C2A N7A C8A 18.6(3) . . . . y N1A C2A N7A C8A -164.13(16) . . . . y N23A C22A N21A C18A 179.53(15) . . . . y C27A C22A N21A C18A 0.8(3) . . . . y C22A N21A C18A C19A -124.06(19) . . . . y C22A N21A C18A C17A 57.3(3) . . . . y C2B N7B C8B C9B -150.32(17) . . . . y C2B N7B C8B C13B 32.0(3) . . . . y C3B C2B N7B C8B 22.0(3) . . . . y N1B C2B N7B C8B -159.93(16) . . . . y N23B C22B N21B C18B -157.15(16) . . . . y C27B C22B N21B C18B 25.5(3) . . . . y C22B N21B C18B C19B 37.7(3) . . . . y C22B N21B C18B C17B -146.18(18) . . . . y C10A C11A O14A C15A 69.8(2) . . . . y C12A C11A O14A C15A -115.30(18) . . . . y C11A O14A C15A C16A -149.05(16) . . . . y C11A O14A C15A C20A 33.2(2) . . . . y C10B C11B O14B C15B 51.8(2) . . . . y C12B C11B O14B C15B -133.95(16) . . . . y C11B O14B C15B C16B -160.85(15) . . . . y C11B O14B C15B C20B 21.3(2) . . . . y _refine_diff_density_max 0.177 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.037 #===END data_6b _database_code_CSD 174159 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl) -4,4'-oxybis(aminobenzene),polymorph beta from methanol ; _chemical_melting_point 138-140 _chemical_formula_sum 'C22 H18 N4 O' _chemical_formula_weight 354.40 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 monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' 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 11.162(1) _cell_length_b 18.893(1) _cell_length_c 17.247(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.89(1) _cell_angle_gamma 90.00 _cell_volume 3571.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3560 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2 _diffrn_reflns_number 17631 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6281 _reflns_number_gt 4284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.157a, 1999' _computing_cell_refinement 'KM4RED, Version 1.157a, 1999' _computing_data_reduction 'KM4RED, Version 1.157a, 1999' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0782P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6281 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1299 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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 N1B N 0.99610(16) 0.13287(8) 0.16974(10) 0.0491(4) Uani 1 1 d . . . C2B C 1.01416(17) 0.20240(10) 0.18101(11) 0.0411(5) Uani 1 1 d . . . C3B C 1.0768(2) 0.24290(11) 0.13315(12) 0.0514(5) Uani 1 1 d . . . H3B H 1.0885 0.2927 0.1426 0.062 Uiso 1 1 d R . . C4B C 1.1210(2) 0.21092(12) 0.07381(12) 0.0553(6) Uani 1 1 d . . . H4B H 1.1645 0.2380 0.0410 0.066 Uiso 1 1 d R . . C5B C 1.1027(2) 0.13876(12) 0.06110(12) 0.0558(6) Uani 1 1 d . . . H5B H 1.1326 0.1150 0.0194 0.067 Uiso 1 1 d R . . C6B C 1.0406(2) 0.10345(11) 0.11014(13) 0.0558(6) Uani 1 1 d . . . H6B H 1.0272 0.0537 0.1010 0.067 Uiso 1 1 d R . . N7B N 0.97346(16) 0.23531(9) 0.24157(9) 0.0503(4) Uani 1 1 d . . . H7B H 0.9820 0.2827 0.2442 0.060 Uiso 1 1 d R . . C8B C 0.92017(18) 0.20320(10) 0.30081(11) 0.0435(5) Uani 1 1 d . . . C9B C 0.82866(19) 0.15270(11) 0.28469(12) 0.0492(5) Uani 1 1 d . . . H9B H 0.8016 0.1372 0.2312 0.059 Uiso 1 1 d R . . C10B C 0.77805(19) 0.12420(11) 0.34507(12) 0.0487(5) Uani 1 1 d . . . H10B H 0.7164 0.0882 0.3338 0.058 Uiso 1 1 d R . . C11B C 0.81667(18) 0.14704(11) 0.42142(12) 0.0464(5) Uani 1 1 d . . . C12B C 0.9052(2) 0.19853(12) 0.43779(12) 0.0537(6) Uani 1 1 d . . . H12B H 0.9300 0.2151 0.4910 0.064 Uiso 1 1 d R . . C13B C 0.95804(19) 0.22570(11) 0.37826(12) 0.0525(6) Uani 1 1 d . . . H13B H 1.0218 0.2603 0.3902 0.063 Uiso 1 1 d R . . O14B O 0.76036(12) 0.12034(8) 0.48085(8) 0.0557(4) Uani 1 1 d . . . C15B C 0.83442(18) 0.09573(10) 0.54968(11) 0.0438(5) Uani 1 1 d . . . C16B C 0.95199(19) 0.07210(11) 0.55285(12) 0.0526(6) Uani 1 1 d . . . H16B H 0.9870 0.0727 0.5061 0.063 Uiso 1 1 d R . . C17B C 1.0177(2) 0.04731(11) 0.62374(13) 0.0549(6) Uani 1 1 d . . . H17B H 1.1001 0.0314 0.6265 0.066 Uiso 1 1 d R . . C18B C 0.96760(19) 0.04552(10) 0.69089(11) 0.0454(5) Uani 1 1 d . . . C19B C 0.8494(2) 0.06850(12) 0.68619(13) 0.0576(6) Uani 1 1 d . . . H19B H 0.8138 0.0672 0.7327 0.069 Uiso 1 1 d R . . C20B C 0.7827(2) 0.09315(12) 0.61558(13) 0.0570(6) Uani 1 1 d . . . H20B H 0.7003 0.1091 0.6128 0.068 Uiso 1 1 d R . . N21B N 1.03712(16) 0.01899(9) 0.76304(9) 0.0539(5) Uani 1 1 d . . . H21B H 1.0207 -0.0248 0.7786 0.065 Uiso 1 1 d R . . C22B C 1.12657(19) 0.05700(10) 0.81015(11) 0.0441(5) Uani 1 1 d . . . N23B N 1.12937(16) 0.12764(8) 0.79991(10) 0.0473(4) Uani 1 1 d . . . C24B C 1.2188(2) 0.16304(11) 0.84705(13) 0.0552(6) Uani 1 1 d . . . H24B H 1.2226 0.2133 0.8395 0.066 Uiso 1 1 d R . . C25B C 1.3051(2) 0.13314(12) 0.90455(13) 0.0589(6) Uani 1 1 d . . . H25B H 1.3670 0.1613 0.9366 0.071 Uiso 1 1 d R . . C26B C 1.3002(2) 0.06056(12) 0.91405(13) 0.0603(6) Uani 1 1 d . . . H26B H 1.3590 0.0371 0.9535 0.072 Uiso 1 1 d R . . C27B C 1.2117(2) 0.02237(11) 0.86761(11) 0.0528(6) Uani 1 1 d . . . H27B H 1.2072 -0.0280 0.8742 0.063 Uiso 1 1 d R . . N1A N 0.50291(16) -0.13614(8) 0.82580(9) 0.0496(4) Uani 1 1 d . . . C2A C 0.47818(18) -0.20351(10) 0.80646(11) 0.0434(5) Uani 1 1 d . . . C3A C 0.4104(2) -0.24652(11) 0.84837(12) 0.0571(6) Uani 1 1 d . . . H3A H 0.3930 -0.2947 0.8323 0.069 Uiso 1 1 d R . . C4A C 0.3689(2) -0.21947(13) 0.91133(13) 0.0634(6) Uani 1 1 d . . . H4A H 0.3223 -0.2482 0.9407 0.076 Uiso 1 1 d R . . C5A C 0.3947(2) -0.14963(13) 0.93288(14) 0.0641(6) Uani 1 1 d . . . H5A H 0.3672 -0.1290 0.9773 0.077 Uiso 1 1 d R . . C6A C 0.4601(2) -0.11125(12) 0.88837(14) 0.0611(6) Uani 1 1 d . . . H6A H 0.4783 -0.0630 0.9036 0.073 Uiso 1 1 d R . . N7A N 0.51732(16) -0.23130(8) 0.74263(9) 0.0514(5) Uani 1 1 d . . . H7A H 0.5053 -0.2780 0.7344 0.062 Uiso 1 1 d R . . C8A C 0.57437(19) -0.19528(10) 0.68725(11) 0.0423(5) Uani 1 1 d . . . C9A C 0.5260(2) -0.20288(11) 0.60801(12) 0.0508(5) Uani 1 1 d . . . H9A H 0.4511 -0.2285 0.5926 0.061 Uiso 1 1 d R . . C10A C 0.58236(19) -0.17385(12) 0.55080(12) 0.0526(6) Uani 1 1 d . . . H10A H 0.5479 -0.1796 0.4958 0.063 Uiso 1 1 d R . . C11A C 0.68958(18) -0.13616(11) 0.57308(12) 0.0453(5) Uani 1 1 d . . . C12A C 0.73819(18) -0.12680(11) 0.65234(12) 0.0480(5) Uani 1 1 d . . . H12A H 0.8119 -0.1000 0.6677 0.058 Uiso 1 1 d R . . C13A C 0.68108(19) -0.15639(10) 0.70920(12) 0.0474(5) Uani 1 1 d . . . H13A H 0.7143 -0.1495 0.7642 0.057 Uiso 1 1 d R . . O14A O 0.75307(13) -0.10824(9) 0.51822(8) 0.0620(4) Uani 1 1 d . . . C15A C 0.68067(18) -0.08570(11) 0.44709(12) 0.0476(5) Uani 1 1 d . . . C16A C 0.6121(2) -0.02537(12) 0.44565(12) 0.0540(6) Uani 1 1 d . . . H16A H 0.6132 0.0009 0.4934 0.065 Uiso 1 1 d R . . C17A C 0.54135(19) -0.00288(11) 0.37541(12) 0.0513(5) Uani 1 1 d . . . H17A H 0.4914 0.0386 0.3744 0.062 Uiso 1 1 d R . . C18A C 0.54098(18) -0.03980(10) 0.30609(11) 0.0425(5) Uani 1 1 d . . . C19A C 0.6145(2) -0.09872(11) 0.30800(12) 0.0525(6) Uani 1 1 d . . . H19A H 0.6187 -0.1230 0.2597 0.063 Uiso 1 1 d R . . C20A C 0.6828(2) -0.12199(12) 0.37876(13) 0.0568(6) Uani 1 1 d . . . H20A H 0.7314 -0.1640 0.3800 0.068 Uiso 1 1 d R . . N21A N 0.46875(16) -0.01439(8) 0.23521(9) 0.0508(4) Uani 1 1 d . . . H21A H 0.4804 0.0309 0.2223 0.061 Uiso 1 1 d R . . C22A C 0.38307(18) -0.05207(10) 0.18399(11) 0.0415(5) Uani 1 1 d . . . N23A N 0.37673(15) -0.12274(8) 0.19238(9) 0.0466(4) Uani 1 1 d . . . C24A C 0.2869(2) -0.15622(11) 0.14321(13) 0.0540(6) Uani 1 1 d . . . H24A H 0.2802 -0.2064 0.1496 0.065 Uiso 1 1 d R . . C25A C 0.2051(2) -0.12423(12) 0.08478(13) 0.0567(6) Uani 1 1 d . . . H25A H 0.1430 -0.1510 0.0511 0.068 Uiso 1 1 d R . . C26A C 0.2146(2) -0.05195(12) 0.07626(12) 0.0561(6) Uani 1 1 d . . . H26A H 0.1595 -0.0273 0.0358 0.067 Uiso 1 1 d R . . C27A C 0.30293(19) -0.01568(11) 0.12543(11) 0.0505(5) Uani 1 1 d . . . H27A H 0.3109 0.0346 0.1199 0.061 Uiso 1 1 d R . . 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 N1B 0.0579(11) 0.0366(10) 0.0544(11) -0.0023(8) 0.0144(9) -0.0046(8) C2B 0.0439(12) 0.0361(11) 0.0411(11) 0.0049(8) 0.0024(9) -0.0011(9) C3B 0.0643(14) 0.0379(11) 0.0533(13) 0.0062(9) 0.0145(11) -0.0044(10) C4B 0.0621(15) 0.0561(14) 0.0503(13) 0.0112(11) 0.0173(11) -0.0003(11) C5B 0.0614(15) 0.0566(14) 0.0519(13) -0.0012(11) 0.0175(11) 0.0049(11) C6B 0.0637(15) 0.0428(12) 0.0637(15) -0.0050(10) 0.0197(12) -0.0008(10) N7B 0.0673(12) 0.0357(9) 0.0508(10) 0.0000(8) 0.0191(9) -0.0050(8) C8B 0.0466(12) 0.0379(11) 0.0468(12) 0.0043(9) 0.0110(9) 0.0039(9) C9B 0.0524(13) 0.0495(12) 0.0441(12) -0.0032(9) 0.0052(10) -0.0038(10) C10B 0.0454(12) 0.0489(12) 0.0512(13) 0.0004(10) 0.0075(10) -0.0079(10) C11B 0.0419(12) 0.0493(12) 0.0475(12) 0.0077(10) 0.0065(9) 0.0027(10) C12B 0.0598(14) 0.0585(13) 0.0416(12) -0.0016(10) 0.0063(10) -0.0074(11) C13B 0.0573(14) 0.0499(13) 0.0490(13) -0.0030(10) 0.0071(10) -0.0126(10) O14B 0.0453(9) 0.0723(10) 0.0493(9) 0.0148(7) 0.0085(7) -0.0025(7) C15B 0.0447(12) 0.0433(11) 0.0438(12) -0.0004(9) 0.0094(9) -0.0015(9) C16B 0.0581(14) 0.0561(13) 0.0485(13) 0.0087(10) 0.0226(10) 0.0074(11) C17B 0.0495(13) 0.0537(13) 0.0640(14) 0.0102(11) 0.0170(11) 0.0079(11) C18B 0.0573(14) 0.0352(11) 0.0436(12) 0.0025(9) 0.0096(10) -0.0033(10) C19B 0.0659(16) 0.0648(15) 0.0477(13) 0.0048(11) 0.0256(11) 0.0072(12) C20B 0.0510(14) 0.0671(15) 0.0570(14) 0.0046(11) 0.0210(11) 0.0103(11) N21B 0.0718(13) 0.0338(9) 0.0519(10) 0.0103(8) 0.0012(9) -0.0071(9) C22B 0.0547(13) 0.0369(11) 0.0429(11) 0.0034(9) 0.0148(10) 0.0002(10) N23B 0.0544(11) 0.0337(9) 0.0545(10) 0.0047(8) 0.0119(8) 0.0002(8) C24B 0.0631(15) 0.0372(11) 0.0675(15) -0.0015(10) 0.0182(12) -0.0048(11) C25B 0.0566(15) 0.0587(15) 0.0587(14) -0.0069(11) 0.0042(11) -0.0072(12) C26B 0.0663(16) 0.0558(15) 0.0554(14) 0.0046(11) 0.0025(11) 0.0080(12) C27B 0.0718(15) 0.0377(11) 0.0475(12) 0.0047(9) 0.0072(11) 0.0036(11) N1A 0.0625(12) 0.0380(10) 0.0505(10) -0.0030(8) 0.0160(9) -0.0016(8) C2A 0.0516(13) 0.0368(11) 0.0405(11) 0.0050(9) 0.0057(9) 0.0039(9) C3A 0.0791(16) 0.0410(12) 0.0543(13) 0.0078(10) 0.0203(12) -0.0042(11) C4A 0.0769(17) 0.0621(16) 0.0561(14) 0.0147(12) 0.0247(12) 0.0011(13) C5A 0.0743(17) 0.0675(16) 0.0555(14) -0.0004(12) 0.0249(12) 0.0088(13) C6A 0.0744(17) 0.0509(14) 0.0626(15) -0.0112(11) 0.0245(13) -0.0015(12) N7A 0.0782(13) 0.0311(9) 0.0484(10) -0.0012(7) 0.0210(9) -0.0070(8) C8A 0.0515(12) 0.0337(10) 0.0423(11) 0.0011(8) 0.0103(9) 0.0023(9) C9A 0.0499(13) 0.0556(13) 0.0465(12) -0.0002(10) 0.0081(10) -0.0078(10) C10A 0.0520(13) 0.0646(14) 0.0395(12) -0.0019(10) 0.0042(10) -0.0093(11) C11A 0.0391(12) 0.0500(12) 0.0470(12) 0.0093(9) 0.0086(9) 0.0049(10) C12A 0.0414(12) 0.0491(12) 0.0510(13) 0.0042(10) 0.0024(10) -0.0008(10) C13A 0.0530(13) 0.0445(12) 0.0414(11) -0.0013(9) 0.0008(10) 0.0040(10) O14A 0.0405(8) 0.0928(12) 0.0528(9) 0.0218(8) 0.0086(7) -0.0024(8) C15A 0.0373(11) 0.0599(14) 0.0463(12) 0.0116(10) 0.0095(9) -0.0033(10) C16A 0.0598(14) 0.0571(14) 0.0461(12) -0.0057(10) 0.0128(10) -0.0052(11) C17A 0.0587(14) 0.0395(11) 0.0575(13) -0.0011(10) 0.0154(11) 0.0034(10) C18A 0.0475(12) 0.0358(11) 0.0455(12) 0.0047(9) 0.0123(9) -0.0043(9) C19A 0.0590(14) 0.0520(13) 0.0493(13) -0.0011(10) 0.0172(10) 0.0101(11) C20A 0.0571(14) 0.0552(14) 0.0615(15) 0.0089(11) 0.0199(11) 0.0170(11) N21A 0.0662(12) 0.0326(9) 0.0512(10) 0.0068(8) 0.0052(9) -0.0026(8) C22A 0.0463(12) 0.0372(11) 0.0443(11) 0.0044(9) 0.0166(9) 0.0024(9) N23A 0.0510(11) 0.0363(9) 0.0532(10) 0.0047(8) 0.0118(8) 0.0016(8) C24A 0.0559(14) 0.0398(11) 0.0667(15) 0.0000(10) 0.0123(11) -0.0019(11) C25A 0.0567(14) 0.0525(14) 0.0585(14) -0.0021(11) 0.0051(11) -0.0026(11) C26A 0.0575(14) 0.0584(14) 0.0508(13) 0.0082(11) 0.0061(11) 0.0094(11) C27A 0.0591(14) 0.0389(11) 0.0534(13) 0.0078(10) 0.0104(11) 0.0069(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1B C2B 1.338(2) . y N1B C6B 1.344(3) . y C2B N7B 1.365(2) . y C2B C3B 1.405(3) . y C3B C4B 1.359(3) . y C4B C5B 1.390(3) . y C5B C6B 1.364(3) . y N7B C8B 1.413(2) . y C8B C9B 1.387(3) . y C8B C13B 1.389(3) . y C9B C10B 1.384(3) . y C10B C11B 1.375(3) . y C11B C12B 1.378(3) . y C11B O14B 1.394(2) . y C12B C13B 1.376(3) . y O14B C15B 1.392(2) . y C15B C20B 1.370(3) . y C15B C16B 1.377(3) . y C16B C17B 1.383(3) . y C17B C18B 1.378(3) . y C18B C19B 1.376(3) . y C18B N21B 1.427(2) . y C19B C20B 1.383(3) . y N21B C22B 1.366(3) . y C22B N23B 1.347(2) . y C22B C27B 1.399(3) . y N23B C24B 1.341(3) . y C24B C25B 1.368(3) . y C25B C26B 1.383(3) . y C26B C27B 1.356(3) . y N1A C2A 1.331(2) . y N1A C6A 1.345(3) . y C2A N7A 1.364(2) . y C2A C3A 1.401(3) . y C3A C4A 1.358(3) . y C4A C5A 1.386(3) . y C5A C6A 1.363(3) . y N7A C8A 1.418(2) . y C8A C9A 1.379(3) . y C8A C13A 1.390(3) . y C9A C10A 1.380(3) . y C10A C11A 1.383(3) . y C11A C12A 1.383(3) . y C11A O14A 1.389(2) . y C12A C13A 1.384(3) . y O14A C15A 1.402(2) . y C15A C20A 1.367(3) . y C15A C16A 1.371(3) . y C16A C17A 1.382(3) . y C17A C18A 1.383(3) . y C18A C19A 1.380(3) . y C18A N21A 1.415(2) . y C19A C20A 1.383(3) . y N21A C22A 1.372(2) . y C22A N23A 1.346(2) . y C22A C27A 1.397(3) . y N23A C24A 1.343(3) . y C24A C25A 1.366(3) . y C25A C26A 1.380(3) . y C26A C27A 1.358(3) . y 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 C2B N1B C6B 116.76(17) . . y N1B C2B N7B 119.72(17) . . y N1B C2B C3B 121.84(18) . . y N7B C2B C3B 118.43(17) . . y C4B C3B C2B 119.47(19) . . y C3B C4B C5B 119.4(2) . . y C6B C5B C4B 117.3(2) . . y N1B C6B C5B 125.2(2) . . y C2B N7B C8B 127.18(16) . . y C9B C8B C13B 118.82(18) . . y C9B C8B N7B 123.04(18) . . y C13B C8B N7B 118.08(18) . . y C10B C9B C8B 120.44(19) . . y C11B C10B C9B 119.98(19) . . y C10B C11B C12B 120.05(19) . . y C10B C11B O14B 119.15(18) . . y C12B C11B O14B 120.70(18) . . y C13B C12B C11B 120.15(19) . . y C12B C13B C8B 120.52(19) . . y C15B O14B C11B 118.05(15) . . y C20B C15B C16B 120.23(19) . . y C20B C15B O14B 116.36(18) . . y C16B C15B O14B 123.36(17) . . y C15B C16B C17B 119.13(19) . . y C18B C17B C16B 121.3(2) . . y C19B C18B C17B 118.62(19) . . y C19B C18B N21B 121.29(18) . . y C17B C18B N21B 120.1(2) . . y C18B C19B C20B 120.60(19) . . y C15B C20B C19B 120.1(2) . . y C22B N21B C18B 123.35(16) . . y N23B C22B N21B 118.37(17) . . y N23B C22B C27B 121.78(19) . . y N21B C22B C27B 119.85(18) . . y C24B N23B C22B 116.59(17) . . y N23B C24B C25B 125.1(2) . . y C24B C25B C26B 117.2(2) . . y C27B C26B C25B 119.9(2) . . y C26B C27B C22B 119.4(2) . . y C2A N1A C6A 116.55(18) . . y N1A C2A N7A 119.17(17) . . y N1A C2A C3A 122.13(18) . . y N7A C2A C3A 118.68(18) . . y C4A C3A C2A 119.6(2) . . y C3A C4A C5A 119.2(2) . . y C6A C5A C4A 117.5(2) . . y N1A C6A C5A 125.1(2) . . y C2A N7A C8A 127.74(16) . . y C9A C8A C13A 118.68(18) . . y C9A C8A N7A 118.43(18) . . y C13A C8A N7A 122.76(17) . . y C8A C9A C10A 121.4(2) . . y C9A C10A C11A 119.56(19) . . y C10A C11A C12A 119.84(18) . . y C10A C11A O14A 122.16(18) . . y C12A C11A O14A 117.99(18) . . y C11A C12A C13A 120.08(19) . . y C12A C13A C8A 120.41(18) . . y C11A O14A C15A 115.31(15) . . y C20A C15A C16A 120.12(19) . . y C20A C15A O14A 120.07(19) . . y C16A C15A O14A 119.75(19) . . y C15A C16A C17A 119.74(19) . . y C16A C17A C18A 120.70(19) . . y C19A C18A C17A 118.78(18) . . y C19A C18A N21A 122.24(18) . . y C17A C18A N21A 118.93(18) . . y C18A C19A C20A 120.25(19) . . y C15A C20A C19A 120.3(2) . . y C22A N21A C18A 126.46(16) . . y N23A C22A N21A 119.33(17) . . y N23A C22A C27A 121.75(19) . . y N21A C22A C27A 118.91(18) . . y C24A N23A C22A 116.58(17) . . y N23A C24A C25A 124.9(2) . . y C24A C25A C26A 117.5(2) . . y C27A C26A C25A 119.6(2) . . y C26A C27A C22A 119.6(2) . . y 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 C2A N7A C8A C9A -127.5(2) . . . . y C2A N7A C8A C13A 56.6(3) . . . . y C3A C2A N7A C8A 172.2(2) . . . . y N1A C2A N7A C8A -6.2(3) . . . . y N23A C22A N21A C18A -11.4(3) . . . . y C27A C22A N21A C18A 167.27(18) . . . . y C22A N21A C18A C19A 55.9(3) . . . . y C22A N21A C18A C17A -126.5(2) . . . . y C2B N7B C8B C9B -46.8(3) . . . . y C2B N7B C8B C13B 136.0(2) . . . . y C3B C2B N7B C8B -173.02(19) . . . . y N1B C2B N7B C8B 5.5(3) . . . . y N23B C22B N21B C18B 17.4(3) . . . . y C27B C22B N21B C18B -163.00(19) . . . . y C22B N21B C18B C19B -103.6(2) . . . . y C22B N21B C18B C17B 77.6(3) . . . . y C10A C11A O14A C15A 33.3(3) . . . . y C12A C11A O14A C15A -148.26(19) . . . . y C11A O14A C15A C16A 72.2(2) . . . . y C11A O14A C15A C20A -110.7(2) . . . . y C10B C11B O14B C15B 131.5(2) . . . . y C12B C11B O14B C15B -52.1(3) . . . . y C11B O14B C15B C16B -24.5(3) . . . . y C11B O14B C15B C20B 158.09(19) . . . . y _refine_diff_density_max 0.239 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.042 #===END data_7 _database_code_CSD 174160 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl) -4,4'-thiobis(aminobenzene) ; _chemical_melting_point 186-187 _chemical_formula_sum 'C22 H18 N4 S' _chemical_formula_weight 370.46 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' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 34.619(7) _cell_length_b 18.823(4) _cell_length_c 5.6100(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3655.7(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 40 _exptl_crystal_description plate _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 1.674 _exptl_absorpt_correction_type 'psi scan' _exptl_absorpt_correction_T_min 0.481 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <1.5 _diffrn_reflns_number 1674 _diffrn_reflns_av_R_equivalents 0.0086 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 5.11 _diffrn_reflns_theta_max 64.91 _reflns_number_total 1503 _reflns_number_gt 1483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(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^)+(0.0781P)^2^+0.2750P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00050(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(17) _refine_ls_number_reflns 1503 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 N1 N 0.15498(5) 0.00788(8) 1.6644(3) 0.0538(4) Uani 1 1 d . . . C2 C 0.15117(5) 0.07768(9) 1.6995(4) 0.0480(4) Uani 1 1 d . . . C3 C 0.17668(6) 0.11662(11) 1.8440(4) 0.0580(5) Uani 1 1 d . . . H3 H 0.1716(8) 0.1684(15) 1.853(6) 0.080(8) Uiso 1 1 d . . . C4 C 0.20588(6) 0.08156(11) 1.9572(4) 0.0652(5) Uani 1 1 d . . . H4 H 0.2228(9) 0.1043(14) 2.055(7) 0.090(8) Uiso 1 1 d . . . C5 C 0.20999(6) 0.00906(12) 1.9259(5) 0.0668(5) Uani 1 1 d . . . H5 H 0.2307(9) -0.0193(16) 2.025(7) 0.121(12) Uiso 1 1 d . . . C6 C 0.18433(6) -0.02421(11) 1.7779(4) 0.0612(5) Uani 1 1 d . . . H6 H 0.1864(8) -0.0801(15) 1.755(6) 0.079(7) Uiso 1 1 d . . . N7 N 0.12071(5) 0.11293(9) 1.5984(3) 0.0558(4) Uani 1 1 d . . . H7 H 0.1165(6) 0.1483(12) 1.641(5) 0.052(6) Uiso 1 1 d . . . C8 C 0.09261(5) 0.08358(8) 1.4458(3) 0.0473(4) Uani 1 1 d . . . C9 C 0.05388(6) 0.09982(10) 1.4840(4) 0.0557(5) Uani 1 1 d . . . H9 H 0.0467(7) 0.1299(11) 1.629(6) 0.072(7) Uiso 1 1 d . . . C10 C 0.02595(5) 0.07455(10) 1.3309(4) 0.0548(4) Uani 1 1 d . . . H10 H -0.0012(8) 0.0827(13) 1.351(6) 0.078(8) Uiso 1 1 d . . . C11 C 0.03571(5) 0.03128(8) 1.1401(3) 0.0450(4) Uani 1 1 d . . . C12 C 0.07437(5) 0.01513(10) 1.1036(4) 0.0499(4) Uani 1 1 d . . . H12 H 0.0813(7) -0.0160(12) 0.999(5) 0.057(6) Uiso 1 1 d . . . C13 C 0.10251(5) 0.04153(9) 1.2509(4) 0.0497(4) Uani 1 1 d . . . H13 H 0.1269(7) 0.0324(12) 1.225(4) 0.066(6) Uiso 1 1 d . . . S14 S 0.0000 0.0000 0.93938(10) 0.0506(2) Uani 1 2 d S . . 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 N1 0.0597(9) 0.0494(7) 0.0524(9) -0.0041(7) -0.0053(8) -0.0023(6) C2 0.0476(8) 0.0467(8) 0.0496(9) -0.0009(7) 0.0060(7) -0.0088(6) C3 0.0596(10) 0.0520(9) 0.0625(11) -0.0044(9) -0.0003(9) -0.0125(8) C4 0.0591(10) 0.0691(11) 0.0674(13) -0.0020(10) -0.0083(10) -0.0178(8) C5 0.0614(10) 0.0683(11) 0.0705(13) 0.0010(10) -0.0111(13) -0.0012(9) C6 0.0681(11) 0.0564(10) 0.0592(11) -0.0024(8) -0.0065(10) 0.0035(9) N7 0.0574(9) 0.0429(7) 0.0672(11) -0.0070(7) -0.0056(8) -0.0020(7) C8 0.0481(8) 0.0445(7) 0.0492(9) 0.0028(7) 0.0008(8) -0.0043(6) C9 0.0557(9) 0.0577(9) 0.0537(11) -0.0115(8) 0.0053(8) -0.0007(8) C10 0.0447(8) 0.0622(9) 0.0576(10) -0.0106(8) 0.0080(8) 0.0008(7) C11 0.0480(8) 0.0444(7) 0.0426(9) 0.0023(7) 0.0006(7) -0.0027(6) C12 0.0506(9) 0.0523(8) 0.0468(9) -0.0057(8) 0.0054(7) 0.0050(7) C13 0.0429(9) 0.0536(9) 0.0528(10) 0.0003(7) 0.0066(7) 0.0015(7) S14 0.0506(3) 0.0580(3) 0.0431(3) 0.000 0.000 -0.0014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1 C2 1.335(2) . y N1 C6 1.343(3) . y C2 N7 1.369(3) . y C2 C3 1.405(3) . y C3 C4 1.364(3) . y C4 C5 1.383(3) . y C5 C6 1.368(3) . y N7 C8 1.409(3) . y C8 C9 1.392(3) . y C8 C13 1.392(3) . y C9 C10 1.378(3) . y C10 C11 1.387(3) . y C11 C12 1.388(2) . y C11 S14 1.7729(17) . y C12 C13 1.371(3) . y S14 C11 1.7729(17) 2 y 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 N1 C6 116.59(17) . . y N1 C2 N7 119.48(16) . . y N1 C2 C3 122.43(18) . . y N7 C2 C3 118.06(17) . . y C4 C3 C2 118.82(18) . . y C3 C4 C5 119.64(19) . . y C6 C5 C4 117.5(2) . . y N1 C6 C5 124.99(19) . . y C2 N7 C8 126.41(16) . . y C9 C8 C13 118.88(17) . . y C9 C8 N7 119.03(17) . . y C13 C8 N7 122.02(16) . . y C10 C9 C8 120.27(18) . . y C9 C10 C11 120.85(16) . . y C10 C11 C12 118.53(17) . . y C10 C11 S14 121.03(13) . . y C12 C11 S14 120.39(14) . . y C13 C12 C11 121.12(18) . . y C12 C13 C8 120.30(16) . . y C11 S14 C11 101.13(10) . 2 y 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 C2 N7 C8 C9 134.9(2) . . . . y C2 N7 C8 C13 -48.2(3) . . . . y C3 C2 N7 C8 178.79(18) . . . . y N1 C2 N7 C8 -3.3(3) . . . . y C12 C11 S14 C11 134.77(15) . . . 2 y C10 C11 S14 C11 -47.82(13) . . . 2 y _refine_diff_density_max 0.162 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.040 #===END data_8 _database_code_CSD 174161 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl) -4,4'-methylenebis(aminobenzene) ; _chemical_melting_point 176-177 _chemical_formula_sum 'C23 H20 N4' _chemical_formula_weight 352.43 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.756(2) _cell_length_b 17.048(3) _cell_length_c 22.116(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3678.2(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 6 _cell_measurement_theta_max 24 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.603 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <1.5 _diffrn_reflns_number 2746 _diffrn_reflns_av_R_equivalents 0.0 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 62.37 _reflns_number_total 2745 _reflns_number_gt 1235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0930P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'C-H geom , N-H difmap' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2745 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1621 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1610 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _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 N1 N 0.3793(3) -0.46510(17) 0.07008(14) 0.0617(8) Uani 1 1 d . . . C2 C 0.2772(3) -0.4251(2) 0.09619(16) 0.0546(9) Uani 1 1 d . . . C3 C 0.1421(3) -0.4523(2) 0.09560(18) 0.0655(10) Uani 1 1 d . . . H3A H 0.0711 -0.4243 0.1165 0.079 Uiso 1 1 d R . . C4 C 0.1134(4) -0.5202(2) 0.06433(18) 0.0711(11) Uani 1 1 d . . . H4A H 0.0209 -0.5392 0.0621 0.085 Uiso 1 1 d R . . C5 C 0.2170(4) -0.5604(2) 0.03630(19) 0.0702(11) Uani 1 1 d . . . H5A H 0.1991 -0.6079 0.0143 0.084 Uiso 1 1 d R . . C6 C 0.3470(4) -0.5307(2) 0.04092(18) 0.0675(11) Uani 1 1 d . . . H6A H 0.4198 -0.5593 0.0217 0.081 Uiso 1 1 d R . . N7 N 0.3172(3) -0.35434(16) 0.12091(15) 0.0675(9) Uani 1 1 d . . . H7 H 0.3926 -0.3332 0.1041 0.113(17) Uiso 1 1 d R . . C8 C 0.2357(3) -0.2996(2) 0.15196(17) 0.0508(9) Uani 1 1 d . . . C9 C 0.1460(4) -0.3196(2) 0.19733(17) 0.0650(10) Uani 1 1 d . . . H9A H 0.1332 -0.3739 0.2074 0.078 Uiso 1 1 d R . . C10 C 0.0737(4) -0.2626(2) 0.22874(16) 0.0679(10) Uani 1 1 d . . . H10A H 0.0114 -0.2782 0.2601 0.081 Uiso 1 1 d R . . C11 C 0.0899(3) -0.1836(2) 0.21565(16) 0.0584(10) Uani 1 1 d . . . C12 C 0.1813(4) -0.1644(2) 0.17046(18) 0.0645(10) Uani 1 1 d . . . H12A H 0.1958 -0.1101 0.1609 0.077 Uiso 1 1 d R . . C13 C 0.2523(3) -0.2205(2) 0.13871(17) 0.0581(11) Uani 1 1 d . . . H13A H 0.3139 -0.2048 0.1071 0.070 Uiso 1 1 d R . . C14 C 0.0105(4) -0.1214(2) 0.24891(18) 0.0746(10) Uani 1 1 d . . . H14A H -0.0494 -0.1465 0.2774 0.089 Uiso 1 1 d R . . H14B H -0.0458 -0.0937 0.2204 0.089 Uiso 1 1 d R . . C15 C 0.0979(3) -0.0626(2) 0.28239(16) 0.0591(9) Uani 1 1 d . . . C16 C 0.1814(4) -0.0856(2) 0.32964(17) 0.0625(10) Uani 1 1 d . . . H16A H 0.1859 -0.1401 0.3402 0.075 Uiso 1 1 d R . . C17 C 0.2587(3) -0.0325(2) 0.36200(16) 0.0559(10) Uani 1 1 d . . . H17A H 0.3132 -0.0501 0.3955 0.067 Uiso 1 1 d R . . C18 C 0.2579(3) 0.0463(2) 0.34641(17) 0.0507(9) Uani 1 1 d . . . C19 C 0.1765(4) 0.0701(2) 0.29883(18) 0.0667(10) Uani 1 1 d . . . H19A H 0.1740 0.1244 0.2875 0.080 Uiso 1 1 d R . . C20 C 0.0978(4) 0.0158(2) 0.26717(17) 0.0685(11) Uani 1 1 d . . . H20A H 0.0422 0.0333 0.2340 0.082 Uiso 1 1 d R . . N21 N 0.3434(3) 0.09811(16) 0.37854(15) 0.0667(9) Uani 1 1 d . . . H21 H 0.4139 0.0787 0.3944 0.072(12) Uiso 1 1 d R . . C22 C 0.3069(3) 0.16966(19) 0.40299(16) 0.0544(9) Uani 1 1 d . . . N23 N 0.4095(3) 0.20558(17) 0.43173(14) 0.0649(8) Uani 1 1 d . . . C24 C 0.3799(4) 0.2723(2) 0.46082(18) 0.0727(11) Uani 1 1 d . . . H24A H 0.4525 0.2978 0.4825 0.087 Uiso 1 1 d R . . C25 C 0.2543(5) 0.3060(2) 0.46184(18) 0.0723(12) Uani 1 1 d . . . H25A H 0.2384 0.3538 0.4836 0.087 Uiso 1 1 d R . . C26 C 0.1502(4) 0.2696(2) 0.43025(19) 0.0701(11) Uani 1 1 d . . . H26A H 0.0599 0.2920 0.4296 0.084 Uiso 1 1 d R . . C27 C 0.1766(3) 0.2013(2) 0.40009(17) 0.0633(10) Uani 1 1 d . . . H27A H 0.1058 0.1757 0.3773 0.076 Uiso 1 1 d R . . 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 N1 0.0496(18) 0.0469(17) 0.089(2) -0.0006(16) 0.0061(15) 0.0008(14) C2 0.053(2) 0.047(2) 0.064(3) 0.0021(19) 0.0020(17) -0.0004(16) C3 0.049(2) 0.068(3) 0.080(3) -0.002(2) 0.0098(18) -0.0001(17) C4 0.062(2) 0.072(3) 0.080(3) -0.008(2) 0.002(2) -0.019(2) C5 0.071(3) 0.065(3) 0.075(3) -0.010(2) 0.008(2) -0.011(2) C6 0.063(2) 0.050(2) 0.090(3) -0.001(2) 0.012(2) 0.0024(18) N7 0.0498(17) 0.0491(18) 0.104(3) -0.0109(17) 0.0092(17) -0.0021(14) C8 0.0420(18) 0.048(2) 0.062(3) -0.003(2) -0.0011(16) 0.0020(15) C9 0.068(2) 0.058(2) 0.069(3) 0.005(2) 0.001(2) -0.0115(19) C10 0.063(2) 0.074(2) 0.067(3) -0.006(2) 0.006(2) -0.016(2) C11 0.0398(18) 0.073(2) 0.063(2) -0.0170(19) -0.0046(17) 0.0003(18) C12 0.069(2) 0.050(2) 0.074(3) -0.0035(19) 0.004(2) 0.0020(18) C13 0.060(2) 0.050(3) 0.065(3) -0.001(2) 0.0143(18) -0.0023(16) C14 0.051(2) 0.085(2) 0.088(3) -0.030(2) 0.002(2) 0.0043(19) C15 0.0437(18) 0.071(2) 0.062(2) -0.0137(19) 0.0020(17) 0.0024(18) C16 0.066(2) 0.053(2) 0.069(3) -0.0021(19) 0.000(2) -0.0017(18) C17 0.058(2) 0.048(3) 0.062(3) -0.002(2) -0.0102(17) 0.0018(16) C18 0.0391(17) 0.052(2) 0.061(3) -0.004(2) 0.0039(16) -0.0034(15) C19 0.069(2) 0.061(2) 0.070(3) 0.006(2) 0.003(2) 0.006(2) C20 0.066(2) 0.071(3) 0.069(3) -0.002(2) -0.004(2) 0.015(2) N21 0.0442(16) 0.0498(17) 0.106(3) -0.0054(17) -0.0071(17) 0.0023(15) C22 0.0518(19) 0.0433(19) 0.068(3) 0.0033(19) 0.0068(18) 0.0002(16) N23 0.0589(18) 0.0520(18) 0.084(2) -0.0036(17) -0.0071(16) -0.0001(15) C24 0.079(3) 0.056(2) 0.084(3) -0.006(2) -0.021(2) 0.000(2) C25 0.103(3) 0.056(3) 0.058(3) -0.006(2) 0.002(2) 0.018(2) C26 0.062(2) 0.063(3) 0.086(3) 0.009(2) 0.011(2) 0.017(2) C27 0.049(2) 0.056(2) 0.085(3) 0.001(2) -0.001(2) -0.0040(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1 C6 1.330(5) . y N1 C2 1.338(4) . y C2 N7 1.381(4) . y C2 C3 1.397(5) . y C3 C4 1.378(5) . y C4 C5 1.370(5) . y C5 C6 1.369(5) . y N7 C8 1.405(4) . y C8 C9 1.374(5) . y C8 C13 1.391(5) . y C9 C10 1.387(5) . y C10 C11 1.387(5) . y C11 C12 1.379(5) . y C11 C14 1.506(4) . y C12 C13 1.374(5) . y C14 C15 1.510(5) . y C15 C20 1.378(5) . y C15 C16 1.381(5) . y C16 C17 1.379(5) . y C17 C18 1.387(5) . y C18 C19 1.379(5) . y C18 N21 1.408(4) . y C19 C20 1.391(5) . y N21 C22 1.381(4) . y C22 N23 1.334(4) . y C22 C27 1.383(4) . y N23 C24 1.338(4) . y C24 C25 1.353(5) . y C25 C26 1.380(5) . y C26 C27 1.366(5) . y 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 N1 C2 117.5(3) . . y N1 C2 N7 113.9(3) . . y N1 C2 C3 122.0(3) . . y N7 C2 C3 124.1(3) . . y C4 C3 C2 118.4(3) . . y C5 C4 C3 119.9(4) . . y C6 C5 C4 117.7(4) . . y N1 C6 C5 124.6(4) . . y C2 N7 C8 127.8(3) . . y C9 C8 C13 117.9(3) . . y C9 C8 N7 123.6(4) . . y C13 C8 N7 118.4(3) . . y C8 C9 C10 121.1(3) . . y C11 C10 C9 121.2(3) . . y C12 C11 C10 117.1(3) . . y C12 C11 C14 121.3(4) . . y C10 C11 C14 121.6(4) . . y C13 C12 C11 122.1(3) . . y C12 C13 C8 120.6(3) . . y C11 C14 C15 114.6(3) . . y C20 C15 C16 117.4(3) . . y C20 C15 C14 121.5(4) . . y C16 C15 C14 121.0(4) . . y C17 C16 C15 121.9(3) . . y C16 C17 C18 120.2(3) . . y C19 C18 C17 118.5(3) . . y C19 C18 N21 122.8(4) . . y C17 C18 N21 118.6(3) . . y C18 C19 C20 120.4(4) . . y C15 C20 C19 121.4(4) . . y C22 N21 C18 126.8(3) . . y N23 C22 N21 113.5(3) . . y N23 C22 C27 122.2(3) . . y N21 C22 C27 124.3(3) . . y C22 N23 C24 117.2(3) . . y N23 C24 C25 124.3(4) . . y C24 C25 C26 117.9(4) . . y C27 C26 C25 119.4(4) . . y C26 C27 C22 118.9(3) . . y 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 C2 N7 C8 -179.0(3) . . . . y C3 C2 N7 C8 3.6(6) . . . . y C2 N7 C8 C9 47.3(6) . . . . y C2 N7 C8 C13 -136.7(4) . . . . y C17 C18 N21 C22 -132.3(4) . . . . y C19 C18 N21 C22 49.8(5) . . . . y C18 N21 C22 N23 179.2(3) . . . . y C18 N21 C22 C27 0.9(6) . . . . y C10 C11 C14 C15 120.1(4) . . . . y C12 C11 C14 C15 -60.4(5) . . . . y C11 C14 C15 C16 -63.5(5) . . . . y C11 C14 C15 C20 116.6(4) . . . . y _refine_diff_density_max 0.248 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.045 #===END data_9a _database_code_CSD 174162 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl)-3,3'-methylenebis(aminobenzene) ; _chemical_melting_point 152-153 _chemical_formula_sum 'C23 H20 N4' _chemical_formula_weight 352.43 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.4291(10) _cell_length_b 14.5351(13) _cell_length_c 11.9115(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.555(8) _cell_angle_gamma 90.00 _cell_volume 1886.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4200 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KumaCCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2 _diffrn_reflns_number 4987 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 26.04 _reflns_number_total 1839 _reflns_number_gt 1275 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.162, 2000' _computing_cell_refinement 'KM4RED, Version 1.162, 2000' _computing_data_reduction 'KM4RED, Version 1.162, 2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0737P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0089(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1839 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.002 _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 N1 N 0.58002(11) 0.25258(8) -0.03837(11) 0.0476(4) Uani 1 1 d . . . C2 C 0.58886(12) 0.17564(9) 0.02576(11) 0.0388(4) Uani 1 1 d . . . C3 C 0.48468(14) 0.12506(11) 0.02514(14) 0.0491(4) Uani 1 1 d . . . H3 H 0.4909(13) 0.0706(11) 0.0682(13) 0.054(4) Uiso 1 1 d . . . C4 C 0.37189(16) 0.15564(12) -0.04013(16) 0.0633(5) Uani 1 1 d . . . H4 H 0.2975(17) 0.1206(13) -0.0388(16) 0.079(5) Uiso 1 1 d . . . C5 C 0.36168(17) 0.23494(13) -0.10519(18) 0.0700(6) Uani 1 1 d . . . H5 H 0.2828(18) 0.2579(12) -0.1481(19) 0.089(6) Uiso 1 1 d . . . C6 C 0.46748(15) 0.28013(12) -0.10154(16) 0.0621(5) Uani 1 1 d . . . H6 H 0.4641(15) 0.3377(12) -0.1518(16) 0.069(5) Uiso 1 1 d . . . N7 N 0.70660(11) 0.15025(9) 0.08652(11) 0.0468(4) Uani 1 1 d . . . H7 H 0.7673(16) 0.1787(12) 0.0648(15) 0.066(5) Uiso 1 1 d . . . C8 C 0.74346(12) 0.07801(9) 0.16885(11) 0.0397(4) Uani 1 1 d . . . C9 C 0.68367(14) 0.05958(11) 0.25257(13) 0.0500(4) Uani 1 1 d . . . H9 H 0.6153(14) 0.0980(11) 0.2614(13) 0.054(4) Uiso 1 1 d . . . C10 C 0.72404(16) -0.01095(12) 0.33158(14) 0.0586(5) Uani 1 1 d . . . H10 H 0.6803(15) -0.0248(12) 0.3902(16) 0.075(5) Uiso 1 1 d . . . C11 C 0.82589(14) -0.06267(11) 0.33165(14) 0.0538(4) Uani 1 1 d . . . H11 H 0.8569(14) -0.1129(11) 0.3931(14) 0.063(5) Uiso 1 1 d . . . C12 C 0.88894(12) -0.04367(9) 0.25167(12) 0.0419(4) Uani 1 1 d . . . C13 C 0.84588(12) 0.02629(9) 0.16949(12) 0.0392(4) Uani 1 1 d . . . H13 H 0.8890(12) 0.0387(9) 0.1092(12) 0.042(4) Uiso 1 1 d . . . C14 C 1.0000 -0.10032(15) 0.2500 0.0510(6) Uani 1 2 d S . . H14 H 0.9769(16) -0.1417(11) 0.1781(16) 0.073(5) 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 N1 0.0416(7) 0.0459(7) 0.0503(7) 0.0093(6) 0.0065(5) -0.0032(5) C2 0.0387(8) 0.0370(7) 0.0394(7) 0.0002(6) 0.0101(6) -0.0012(6) C3 0.0425(9) 0.0422(8) 0.0573(9) 0.0066(7) 0.0072(7) -0.0066(7) C4 0.0422(9) 0.0582(11) 0.0785(12) 0.0085(8) 0.0019(8) -0.0136(8) C5 0.0422(10) 0.0653(11) 0.0848(13) 0.0216(10) -0.0076(9) -0.0050(8) C6 0.0498(10) 0.0546(10) 0.0693(11) 0.0193(9) -0.0009(8) -0.0039(8) N7 0.0343(7) 0.0508(8) 0.0544(8) 0.0170(6) 0.0122(6) 0.0009(5) C8 0.0371(8) 0.0406(8) 0.0382(7) 0.0031(6) 0.0066(6) -0.0042(6) C9 0.0478(9) 0.0575(9) 0.0476(9) 0.0077(7) 0.0189(7) 0.0052(8) C10 0.0626(11) 0.0696(11) 0.0494(9) 0.0160(8) 0.0256(8) 0.0046(9) C11 0.0600(10) 0.0531(10) 0.0451(9) 0.0134(7) 0.0109(8) 0.0020(8) C12 0.0391(8) 0.0389(8) 0.0418(8) 0.0001(6) 0.0036(6) -0.0046(6) C13 0.0344(7) 0.0424(8) 0.0385(7) 0.0008(6) 0.0076(6) -0.0065(6) C14 0.0447(13) 0.0401(12) 0.0616(15) 0.000 0.0060(11) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1 C6 1.3406(19) . y N1 C2 1.3407(17) . y C2 N7 1.3724(17) . y C2 C3 1.397(2) . y C3 C4 1.364(2) . y C4 C5 1.374(2) . y C5 C6 1.365(2) . y N7 C8 1.4115(17) . y C8 C13 1.3892(19) . y C8 C9 1.3944(19) . y C9 C10 1.374(2) . y C10 C11 1.385(2) . y C11 C12 1.385(2) . y C12 C13 1.3942(19) . y C12 C14 1.5181(18) . y C14 C12 1.5181(18) 2_755 y 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 N1 C2 117.62(12) . . y N1 C2 N7 114.72(12) . . y N1 C2 C3 121.21(13) . . y N7 C2 C3 124.03(13) . . y C4 C3 C2 119.27(15) . . y C3 C4 C5 120.00(16) . . y C6 C5 C4 117.50(16) . . y N1 C6 C5 124.39(16) . . y C2 N7 C8 127.31(12) . . y C13 C8 C9 119.08(13) . . y C13 C8 N7 118.74(11) . . y C9 C8 N7 122.13(13) . . y C10 C9 C8 119.84(14) . . y C9 C10 C11 120.91(15) . . y C12 C11 C10 120.19(14) . . y C11 C12 C13 118.80(13) . . y C11 C12 C14 120.76(12) . . y C13 C12 C14 120.39(12) . . y C8 C13 C12 121.13(13) . . y C12 C14 C12 114.31(17) 2_755 . y 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 C2 N7 C8 C9 -41.1(2) . . . . y C2 N7 C8 C13 141.73(14) . . . . y C3 C2 N7 C8 -8.7(2) . . . . y N1 C2 N7 C8 173.74(13) . . . . y C13 C12 C14 C12 51.11(10) . . . 2_755 y C11 C12 C14 C12 -131.35(14) . . . 2_755 y _refine_diff_density_max 0.136 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.033 #===END data_9b _database_code_CSD 174163 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-Bis(2-pyridyl) -3,3'-methylenebis(aminobenzene) 0.5 ethanol solvate ; _chemical_formula_moiety 'C23H20N4 x 0.5 C2H5OH' _chemical_formula_sum 'C24 H23 N4 O0.50' _chemical_formula_weight 375.46 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 tetragonal _symmetry_space_group_name_H-M P4nc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 15.039(2) _cell_length_b 15.039(2) _cell_length_c 8.896(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2012.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 7 _cell_measurement_theta_max 23 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 0.600 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'KM-4 four-circle diffractometer' _diffrn_measurement_method '\w/2\q scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% <1.5 _diffrn_reflns_number 1550 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 9.33 _diffrn_reflns_theta_max 65.08 _reflns_number_total 882 _reflns_number_gt 561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 sofware (Kuma Diffraction, 1991)' _computing_cell_refinement 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 software (Kuma Diffraction, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0483P)^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 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(11) _refine_ls_number_reflns 882 _refine_ls_number_parameters 132 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0926 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _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 N1 N 0.2184(2) 0.82402(17) 0.2176(3) 0.0431(7) Uani 1 1 d . . . C2 C 0.2323(2) 0.8140(2) 0.3644(4) 0.0384(8) Uani 1 1 d . . . C3 C 0.1627(3) 0.8058(3) 0.4679(5) 0.0600(12) Uani 1 1 d . . . H3 H 0.1753 0.7980 0.5729 0.072 Uiso 1 1 d R . . C4 C 0.0773(3) 0.8084(3) 0.4176(6) 0.0737(14) Uani 1 1 d . . . H4 H 0.0286 0.8026 0.4869 0.088 Uiso 1 1 d R . . C5 C 0.0620(3) 0.8194(3) 0.2644(5) 0.0732(14) Uani 1 1 d . . . H5 H 0.0026 0.8212 0.2248 0.088 Uiso 1 1 d R . . C6 C 0.1327(3) 0.8266(3) 0.1727(5) 0.0569(11) Uani 1 1 d . . . H6 H 0.1226 0.8346 0.0670 0.068 Uiso 1 1 d R . . N7 N 0.3178(2) 0.8079(2) 0.4169(3) 0.0512(8) Uani 1 1 d . . . H7 H 0.3232 0.7892 0.5126 0.061 Uiso 1 1 d R . . C8 C 0.3976(2) 0.8263(2) 0.3403(4) 0.0409(8) Uani 1 1 d . . . C9 C 0.4719(2) 0.7746(3) 0.3741(5) 0.0542(11) Uani 1 1 d . . . H9 H 0.4656 0.7244 0.4399 0.065 Uiso 1 1 d R . . C10 C 0.5527(2) 0.7941(3) 0.3101(6) 0.0622(12) Uani 1 1 d . . . H10 H 0.6041 0.7590 0.3349 0.075 Uiso 1 1 d R . . C11 C 0.5613(3) 0.8649(3) 0.2139(5) 0.0557(10) Uani 1 1 d . . . H11 H 0.6179 0.8773 0.1686 0.067 Uiso 1 1 d R . . C12 C 0.4891(2) 0.9175(2) 0.1790(4) 0.0420(8) Uani 1 1 d . . . C13 C 0.4072(2) 0.8974(2) 0.2432(4) 0.0410(8) Uani 1 1 d . . . H13 H 0.3561 0.9331 0.2198 0.049 Uiso 1 1 d R . . C14 C 0.5000 1.0000 0.0823(5) 0.0531(14) Uani 1 2 d S . . H14 H 0.4488 1.0067 0.0190 0.064 Uiso 1 1 d R . . C1A C 0.0000 1.0000 -0.055(3) 0.224(10) Uiso 1 4 d S . . O2A O 0.042(3) 1.045(3) -0.215(4) 0.246(18) Uiso 0.25 1 d P . . C3A C 0.0000 1.0000 -0.292(5) 0.290(18) Uiso 1 4 d S . . 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 N1 0.0409(17) 0.0475(18) 0.0410(17) -0.0010(15) -0.0041(14) -0.0070(14) C2 0.040(2) 0.0396(19) 0.036(2) 0.0011(16) 0.0022(17) -0.0021(16) C3 0.049(3) 0.081(4) 0.049(2) 0.007(2) 0.004(2) -0.004(2) C4 0.047(3) 0.103(4) 0.072(3) 0.013(3) 0.013(2) 0.001(3) C5 0.037(2) 0.102(4) 0.081(4) 0.018(3) -0.007(2) -0.011(2) C6 0.055(3) 0.063(3) 0.053(2) 0.003(2) -0.014(2) -0.013(2) N7 0.0428(19) 0.073(2) 0.0379(14) 0.0130(15) -0.0025(14) -0.0075(15) C8 0.037(2) 0.049(2) 0.0359(18) -0.0041(18) -0.0023(16) -0.0055(16) C9 0.051(2) 0.052(2) 0.059(3) 0.012(2) 0.000(2) -0.0008(18) C10 0.051(2) 0.066(3) 0.070(3) 0.006(3) 0.009(2) 0.009(2) C11 0.042(2) 0.066(3) 0.059(2) -0.007(2) 0.011(2) 0.0000(18) C12 0.044(2) 0.048(2) 0.0341(17) -0.0091(19) 0.0035(18) -0.0101(17) C13 0.039(2) 0.049(2) 0.0346(17) 0.0018(17) -0.0052(16) -0.0032(16) C14 0.057(4) 0.069(5) 0.033(2) 0.000 0.000 -0.023(3) 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 N1 C2 1.331(4) . y N1 C6 1.351(4) . y C2 N7 1.372(4) . y C2 C3 1.399(5) . y C3 C4 1.362(6) . y C4 C5 1.392(6) . y C5 C6 1.345(6) . y N7 C8 1.408(4) . y C8 C13 1.382(4) . y C8 C9 1.394(5) . y C9 C10 1.374(5) . y C10 C11 1.373(5) . y C11 C12 1.379(5) . y C12 C13 1.391(5) . y C12 C14 1.518(4) . y C14 C12 1.518(4) 2_675 y C1A O2A 1.70(3) 2_575 y C1A O2A 1.70(3) 3_665 y C1A O2A 1.70(3) 4_465 y C1A O2A 1.70(3) . y O2A C3A 1.15(4) . y O2A O2A 1.30(4) 3_665 y O2A O2A 1.30(4) 4_465 y C3A O2A 1.15(4) 3_665 y C3A O2A 1.15(4) 4_465 y C3A O2A 1.15(4) 2_575 y 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 N1 C6 116.3(3) . . y N1 C2 N7 119.2(3) . . y N1 C2 C3 122.6(3) . . y N7 C2 C3 118.1(3) . . y C4 C3 C2 119.1(4) . . y C3 C4 C5 118.8(4) . . y C6 C5 C4 118.2(4) . . y C5 C6 N1 124.9(4) . . y C2 N7 C8 128.4(3) . . y C13 C8 C9 118.9(3) . . y C13 C8 N7 122.9(3) . . y C9 C8 N7 118.0(3) . . y C10 C9 C8 120.0(4) . . y C11 C10 C9 120.4(4) . . y C10 C11 C12 120.8(4) . . y C11 C12 C13 118.6(3) . . y C11 C12 C14 120.8(3) . . y C13 C12 C14 120.4(3) . . y C8 C13 C12 121.1(3) . . y C12 C14 C12 111.0(4) 2_675 . y O2A C1A O2A 45.1(17) 2_575 3_665 y O2A C1A O2A 45.1(17) 2_575 4_465 y O2A C1A O2A 66(3) 3_665 4_465 y O2A C1A O2A 66(3) 2_575 . y O2A C1A O2A 45.1(17) 3_665 . y O2A C1A O2A 45.1(17) 4_465 . y C3A O2A O2A 55.4(14) . 3_665 y C3A O2A O2A 55.4(14) . 4_465 y O2A O2A O2A 90.000(9) 3_665 4_465 y C3A O2A C1A 94(3) . . y O2A O2A C1A 67.4(9) 3_665 . y O2A O2A C1A 67.4(9) 4_465 . y O2A C3A O2A 69(3) . 3_665 y O2A C3A O2A 69(3) . 4_465 y O2A C3A O2A 107(5) 3_665 4_465 y O2A C3A O2A 107(5) . 2_575 y O2A C3A O2A 69(3) 3_665 2_575 y O2A C3A O2A 69(3) 4_465 2_575 y 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 C2 N7 C8 C9 -145.6(4) . . . . y C2 N7 C8 C13 39.8(5) . . . . y C3 C2 N7 C8 -170.0(3) . . . . y N1 C2 N7 C8 12.4(6) . . . . y C13 C12 C14 C12 80.0(3) . . . 2_675 y C11 C12 C14 C12 -95.3(3) . . . 2_675 y _refine_diff_density_max 0.211 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036 #===END