# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Organic & Biomolecular Chemistry' _journal_coden_Cambridge ? _publ_contact_author ; Maria Gdaniec Faculty of Chemistry A. Mickiewicz Unversity 60-780 Poznan Poland ; _publ_contact_author_email magdan@amu.edu.pl loop_ _publ_author_name _publ_author_address I.Bensemann ; Department of Chemistry Technical University 80-952 Gda\'nsk Poland ; M.Gdaniec ; Faculty of Chemistry A.Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; K.Lakomecka ; Faculty of Chemistry A.Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; M.J.Milewska ; Department of Chemistry Technical University 80-952 Gda\'nsk Poland ; T.Polonski ; Department of Chemistry Technical University 80-952 Gda\'nsk Poland ; data_1iso _database_code_CSD 191434 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene 1,3-benzenedicarboxylic acid ; _chemical_melting_point 211-212 _chemical_formula_moiety 'C16 H14 N4, C8H6O4' _chemical_formula_sum 'C24 H20 N4 O4' _chemical_formula_weight 428.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y-1/2, z' _cell_length_a 9.1922(11) _cell_length_b 7.1341(11) _cell_length_c 31.750(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2082.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 10774 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1867 _reflns_number_gt 1766 _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^)+(0.0616P)^2^+1.3617P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0054(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1867 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1534 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 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 1.1603(2) 0.0050(3) 0.62749(6) 0.0447(5) Uani 1 1 d . . . N7 N 0.9793(2) 0.0944(3) 0.67283(6) 0.0437(5) Uani 1 1 d . . . H7 H 0.9183 0.0706 0.6489 0.073(9) Uiso 1 1 d R . . C2 C 1.1248(2) 0.0956(3) 0.66313(7) 0.0400(5) Uani 1 1 d . . . C3 C 1.2324(3) 0.1869(3) 0.68681(7) 0.0450(6) Uani 1 1 d . . . H3 H 1.2069 0.2579 0.7114 0.057(8) Uiso 1 1 d R . . C4 C 1.3741(3) 0.1781(4) 0.67372(8) 0.0524(7) Uani 1 1 d . . . H4 H 1.4454 0.2476 0.6894 0.066(8) Uiso 1 1 d R . . C5 C 1.4113(3) 0.0784(4) 0.63769(8) 0.0567(7) Uani 1 1 d . . . H5 H 1.5094 0.0748 0.6274 0.070(9) Uiso 1 1 d R . . C6 C 1.3000(3) -0.0015(4) 0.61548(8) 0.0514(7) Uani 1 1 d . . . H6 H 1.3155 -0.0628 0.5890 0.060(8) Uiso 1 1 d R . . C8 C 0.9137(2) 0.1329(3) 0.71198(6) 0.0383(5) Uani 1 1 d . . . C9 C 0.7703(3) 0.1954(3) 0.71202(7) 0.0443(6) Uani 1 1 d . . . H9 H 0.7197 0.2173 0.6860 0.054(7) Uiso 1 1 d R . . C10 C 0.7005(4) 0.2247(6) 0.7500 0.0491(9) Uani 1 2 d S . . H10 H 0.6016 0.2683 0.7500 0.037(8) Uiso 1 2 d SR . . C11 C 0.9845(3) 0.0961(4) 0.7500 0.0367(7) Uani 1 2 d S . . H11 H 1.0818 0.0471 0.7500 0.039(9) Uiso 1 2 d SR . . O2A O 0.7922(2) -0.0082(3) 0.59909(5) 0.0601(6) Uani 1 1 d . . . O1A O 0.9906(2) -0.1305(3) 0.56933(6) 0.0655(6) Uani 1 1 d . . . H1OA H 1.044(4) -0.074(5) 0.5955(11) 0.080(10) Uiso 1 1 d . . . C1A C 0.7707(3) -0.1731(3) 0.53387(7) 0.0454(6) Uani 1 1 d . . . C2A C 0.8453(4) -0.2500 0.5000 0.0479(8) Uani 1 2 d S . . H2A H 0.9497 -0.2500 0.5000 0.052(10) Uiso 1 2 d SR . . C3A C 0.5434(4) -0.2500 0.5000 0.0585(10) Uani 1 2 d S . . H3A H 0.4389 -0.2500 0.5000 0.057(10) Uiso 1 2 d SR . . C4A C 0.6191(3) -0.1726(4) 0.53342(8) 0.0533(7) Uani 1 1 d . . . H4A H 0.5729 -0.1147 0.5572 0.056(7) Uiso 1 1 d R . . C5A C 0.8509(3) -0.0946(4) 0.57065(7) 0.0498(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0444(11) 0.0581(12) 0.0315(10) -0.0044(8) 0.0037(8) 0.0026(10) N7 0.0401(11) 0.0609(12) 0.0302(9) -0.0065(8) 0.0011(8) -0.0011(9) C2 0.0415(12) 0.0483(12) 0.0303(10) 0.0019(9) 0.0007(9) 0.0020(10) C3 0.0463(13) 0.0542(14) 0.0347(12) 0.0004(10) -0.0005(10) -0.0021(11) C4 0.0437(14) 0.0694(17) 0.0440(13) 0.0051(12) -0.0038(11) -0.0079(12) C5 0.0434(14) 0.0781(19) 0.0484(14) 0.0013(13) 0.0078(11) 0.0011(13) C6 0.0477(14) 0.0687(16) 0.0380(13) -0.0033(12) 0.0051(10) 0.0059(12) C8 0.0395(12) 0.0439(12) 0.0316(11) -0.0041(9) 0.0018(9) -0.0028(10) C9 0.0390(12) 0.0593(15) 0.0346(12) 0.0029(10) -0.0015(9) -0.0012(11) C10 0.0367(17) 0.071(2) 0.0395(17) 0.000 0.000 0.0055(16) C11 0.0369(16) 0.0400(16) 0.0333(15) 0.000 0.000 0.0015(13) O2A 0.0573(11) 0.0826(13) 0.0404(9) -0.0192(9) 0.0060(8) 0.0008(10) O1A 0.0489(11) 0.0987(16) 0.0490(11) -0.0286(10) -0.0041(9) 0.0033(10) C1A 0.0491(13) 0.0547(14) 0.0323(12) -0.0028(10) 0.0009(10) -0.0027(11) C2A 0.0462(19) 0.063(2) 0.0349(16) -0.0050(15) 0.000 0.000 C3A 0.0433(19) 0.083(3) 0.049(2) -0.0085(19) 0.000 0.000 C4A 0.0495(14) 0.0697(17) 0.0409(13) -0.0060(12) 0.0054(11) 0.0055(12) C5A 0.0513(14) 0.0613(15) 0.0367(12) -0.0046(11) 0.0032(11) -0.0009(12) _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 1.341(3) . ? N1 C2 1.343(3) . ? N7 C2 1.373(3) . ? N7 C8 1.409(3) . ? N7 H7 0.9600 . ? C2 C3 1.403(3) . ? C3 C4 1.368(3) . ? C3 H3 0.9601 . ? C4 C5 1.390(4) . ? C4 H4 0.9600 . ? C5 C6 1.366(4) . ? C5 H5 0.9600 . ? C6 H6 0.9599 . ? C8 C9 1.392(3) . ? C8 C11 1.396(3) . ? C9 C10 1.382(3) . ? C9 H9 0.9600 . ? C10 C9 1.382(3) 6_557 ? C10 H10 0.9600 . ? C11 C8 1.396(3) 6_557 ? C11 H11 0.9600 . ? O2A C5A 1.219(3) . ? O1A C5A 1.310(3) . ? O1A H1OA 1.05(4) . ? C1A C2A 1.388(3) . ? C1A C4A 1.394(4) . ? C1A C5A 1.490(3) . ? C2A C1A 1.388(3) 4_546 ? C2A H2A 0.9600 . ? C3A C4A 1.384(3) . ? C3A C4A 1.384(3) 4_546 ? C3A H3A 0.9600 . ? C4A H4A 0.9600 . ? 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 119.2(2) . . ? C2 N7 C8 127.88(19) . . ? C2 N7 H7 113.1 . . ? C8 N7 H7 118.9 . . ? N1 C2 N7 115.0(2) . . ? N1 C2 C3 120.3(2) . . ? N7 C2 C3 124.7(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 117.9 . . ? C5 C4 H4 121.5 . . ? C6 C5 C4 117.0(2) . . ? C6 C5 H5 121.0 . . ? C4 C5 H5 121.7 . . ? N1 C6 C5 123.8(2) . . ? N1 C6 H6 114.0 . . ? C5 C6 H6 122.1 . . ? C9 C8 C11 120.1(2) . . ? C9 C8 N7 117.97(19) . . ? C11 C8 N7 121.8(2) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.7 . . ? C9 C10 C9 121.5(3) 6_557 . ? C9 C10 H10 119.2 6_557 . ? C9 C10 H10 119.2 . . ? C8 C11 C8 119.7(3) 6_557 . ? C8 C11 H11 120.2 6_557 . ? C8 C11 H11 120.2 . . ? C5A O1A H1OA 111.1(18) . . ? C2A C1A C4A 119.1(2) . . ? C2A C1A C5A 120.8(2) . . ? C4A C1A C5A 120.1(2) . . ? C1A C2A C1A 120.8(3) 4_546 . ? C1A C2A H2A 119.6 4_546 . ? C1A C2A H2A 119.6 . . ? C4A C3A C4A 119.6(3) . 4_546 ? C4A C3A H3A 120.2 . . ? C4A C3A H3A 120.2 4_546 . ? C3A C4A C1A 120.7(2) . . ? C3A C4A H4A 123.5 . . ? C1A C4A H4A 115.8 . . ? O2A C5A O1A 123.8(2) . . ? O2A C5A C1A 123.5(2) . . ? O1A C5A C1A 112.7(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.222 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.049 #===END data_1obe _database_code_CSD 191435 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene 4,4'-oxybisbenzoic acid ; _chemical_name_common ? _chemical_melting_point 158-200 _chemical_formula_moiety 'C16H14N4, C14H10O5' _chemical_formula_sum 'C30 H24 N4 O5' _chemical_formula_weight 520.53 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 orthorhombic _symmetry_space_group_name_H-M Ama2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 35.743(7) _cell_length_b 9.285(2) _cell_length_c 7.3380(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2435.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 3651 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1135 _reflns_number_gt 909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0494P)^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 and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 1135 _refine_ls_number_parameters 196 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.35603(7) 0.1951(3) 0.6846(4) 0.0210(7) Uani 1 1 d . . . C2 C 0.32609(8) 0.1615(4) 0.7862(4) 0.0190(8) Uani 1 1 d . . . C3 C 0.30585(9) 0.2671(4) 0.8791(5) 0.0225(9) Uani 1 1 d . . . H3 H 0.2841 0.2458 0.9554 0.022(9) Uiso 1 1 d R . . C4 C 0.31518(9) 0.4095(4) 0.8541(5) 0.0240(9) Uani 1 1 d . . . H4 H 0.3010 0.4913 0.9241 0.037(10) Uiso 1 1 d R . . C5 C 0.34495(9) 0.4461(4) 0.7387(5) 0.0246(9) Uani 1 1 d . . . H5 H 0.3537 0.5520 0.7080 0.030(10) Uiso 1 1 d R . . C6 C 0.36455(8) 0.3357(4) 0.6619(4) 0.0225(8) Uani 1 1 d . . . H6 H 0.3859 0.3547 0.5793 0.040(11) Uiso 1 1 d R . . N7 N 0.31838(7) 0.0166(3) 0.7964(4) 0.0211(7) Uani 1 1 d . . . H7 H 0.3376 -0.0383 0.7846 0.027(10) Uiso 1 1 d R . . C8 C 0.28377(8) -0.0489(4) 0.8260(4) 0.0187(8) Uani 1 1 d . . . C9 C 0.28361(8) -0.1966(4) 0.8675(5) 0.0221(9) Uani 1 1 d . . . H9 H 0.3067 -0.2446 0.8787 0.010(8) Uiso 1 1 d R . . C10 C 0.2500 -0.2669(6) 0.8855(7) 0.0230(12) Uani 1 2 d S . . H10 H 0.2500 -0.3719 0.9038 0.027(14) Uiso 1 2 d SR . . C11 C 0.2500 0.0234(5) 0.8027(7) 0.0192(11) Uani 1 2 d S . . H11 H 0.2500 0.1328 0.7652 0.010(11) Uiso 1 2 d SR . . O1A O 0.40711(6) 0.0211(3) 0.5444(3) 0.0226(6) Uani 1 1 d . . . H1OA H 0.3838(9) 0.085(4) 0.598(5) 0.030(10) Uiso 1 1 d . . . O2A O 0.38230(6) -0.1573(3) 0.7106(4) 0.0283(6) Uani 1 1 d . . . C1A C 0.43165(8) -0.2134(4) 0.5069(4) 0.0178(8) Uani 1 1 d . . . C2A C 0.43115(8) -0.3590(4) 0.5518(5) 0.0235(9) Uani 1 1 d . . . H2A H 0.4145 -0.3840 0.6398 0.038(11) Uiso 1 1 d R . . C3A C 0.45421(8) -0.4551(4) 0.4627(5) 0.0226(8) Uani 1 1 d . . . H3A H 0.4555 -0.5591 0.4915 0.020(9) Uiso 1 1 d R . . C4A C 0.47817(8) -0.4045(4) 0.3290(5) 0.0214(8) Uani 1 1 d . . . C5A C 0.47971(8) -0.2599(4) 0.2842(5) 0.0244(9) Uani 1 1 d . . . H5A H 0.4984 -0.2287 0.1932 0.041(10) Uiso 1 1 d R . . C6A C 0.45644(8) -0.1639(4) 0.3736(5) 0.0209(8) Uani 1 1 d . . . H6A H 0.4573 -0.0577 0.3416 0.011(8) Uiso 1 1 d R . . C7A C 0.40494(9) -0.1150(4) 0.5978(5) 0.0227(8) Uani 1 1 d . . . O3A O 0.5000 -0.5000 0.2301(5) 0.0249(8) 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 0.0190(13) 0.0206(18) 0.0235(15) 0.0025(15) -0.0013(13) -0.0007(13) C2 0.0178(14) 0.020(2) 0.0193(17) 0.0011(17) -0.0026(15) -0.0010(14) C3 0.0212(16) 0.027(2) 0.0198(18) -0.0025(18) 0.0015(16) 0.0017(15) C4 0.0234(16) 0.023(2) 0.025(2) -0.0066(19) -0.0065(16) 0.0021(16) C5 0.0249(16) 0.022(2) 0.0272(19) -0.0044(18) -0.0042(15) -0.0010(16) C6 0.0199(16) 0.025(2) 0.0221(18) 0.0025(19) -0.0024(14) -0.0021(16) N7 0.0201(13) 0.0163(18) 0.0270(15) 0.0000(15) 0.0018(13) 0.0025(12) C8 0.0183(15) 0.024(2) 0.0144(17) -0.0024(16) 0.0001(14) 0.0000(14) C9 0.0200(16) 0.022(2) 0.0244(19) -0.0028(19) -0.0015(14) 0.0040(15) C10 0.028(2) 0.021(3) 0.020(2) 0.001(3) 0.000 0.000 C11 0.025(2) 0.014(3) 0.018(2) 0.001(2) 0.000 0.000 O1A 0.0223(11) 0.0190(16) 0.0266(13) 0.0006(12) 0.0028(11) 0.0018(10) O2A 0.0249(11) 0.0272(16) 0.0328(14) 0.0032(13) 0.0090(12) 0.0039(11) C1A 0.0153(14) 0.021(2) 0.0166(18) 0.0003(16) -0.0009(14) 0.0031(14) C2A 0.0168(15) 0.032(3) 0.022(2) 0.0026(18) 0.0013(15) -0.0024(16) C3A 0.0238(17) 0.019(2) 0.0255(19) 0.0005(18) -0.0014(15) 0.0011(16) C4A 0.0194(15) 0.024(2) 0.0203(18) -0.0024(17) -0.0030(15) 0.0043(15) C5A 0.0227(16) 0.029(3) 0.0218(19) 0.0058(18) 0.0024(16) 0.0045(15) C6A 0.0238(16) 0.015(2) 0.0234(18) 0.0037(17) 0.0002(15) 0.0008(14) C7A 0.0173(15) 0.027(2) 0.0238(18) 0.0020(18) -0.0032(15) -0.0004(15) O3A 0.0287(16) 0.024(2) 0.0216(18) 0.000 0.000 0.0084(15) _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 1.341(4) . ? N1 C6 1.350(4) . ? C2 N7 1.375(4) . ? C2 C3 1.396(5) . ? C3 C4 1.376(5) . ? C3 H3 0.9790 . ? C4 C5 1.402(5) . ? C4 H4 1.0479 . ? C5 C6 1.363(5) . ? C5 H5 1.0563 . ? C6 H6 0.9891 . ? N7 C8 1.396(4) . ? N7 H7 0.8608 . ? C8 C11 1.391(4) . ? C8 C9 1.405(5) . ? C9 C10 1.374(4) . ? C9 H9 0.9399 . ? C10 C9 1.374(4) 4 ? C10 H10 0.9842 . ? C11 C8 1.391(4) 4 ? C11 H11 1.0528 . ? O1A C7A 1.325(4) . ? O1A H1OA 1.09(4) . ? O2A C7A 1.223(4) . ? C1A C2A 1.392(5) . ? C1A C6A 1.398(4) . ? C1A C7A 1.480(5) . ? C2A C3A 1.379(5) . ? C2A H2A 0.9070 . ? C3A C4A 1.384(5) . ? C3A H3A 0.9897 . ? C4A C5A 1.383(5) . ? C4A O3A 1.386(4) . ? C5A C6A 1.384(5) . ? C5A H5A 0.9882 . ? C6A H6A 1.0139 . ? O3A C4A 1.386(4) 2_645 ? 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 118.3(3) . . ? N1 C2 N7 114.7(3) . . ? N1 C2 C3 121.4(3) . . ? N7 C2 C3 123.8(3) . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 117.6 . . ? C2 C3 H3 123.3 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 117.2(3) . . ? C6 C5 H5 117.4 . . ? C4 C5 H5 125.4 . . ? N1 C6 C5 124.0(3) . . ? N1 C6 H6 114.9 . . ? C5 C6 H6 121.0 . . ? C2 N7 C8 127.7(3) . . ? C2 N7 H7 114.4 . . ? C8 N7 H7 117.8 . . ? C11 C8 N7 122.7(3) . . ? C11 C8 C9 119.6(3) . . ? N7 C8 C9 117.5(3) . . ? C10 C9 C8 119.2(3) . . ? C10 C9 H9 122.2 . . ? C8 C9 H9 118.6 . . ? C9 C10 C9 122.0(5) 4 . ? C9 C10 H10 118.9 4 . ? C9 C10 H10 118.9 . . ? C8 C11 C8 120.3(4) 4 . ? C8 C11 H11 119.8 4 . ? C8 C11 H11 119.8 . . ? C7A O1A H1OA 111.4(19) . . ? C2A C1A C6A 119.6(3) . . ? C2A C1A C7A 119.0(3) . . ? C6A C1A C7A 121.4(3) . . ? C3A C2A C1A 120.5(3) . . ? C3A C2A H2A 124.3 . . ? C1A C2A H2A 115.2 . . ? C2A C3A C4A 119.1(4) . . ? C2A C3A H3A 123.9 . . ? C4A C3A H3A 116.9 . . ? C5A C4A C3A 121.5(3) . . ? C5A C4A O3A 118.3(3) . . ? C3A C4A O3A 120.2(3) . . ? C4A C5A C6A 119.3(3) . . ? C4A C5A H5A 118.2 . . ? C6A C5A H5A 122.5 . . ? C5A C6A C1A 120.0(3) . . ? C5A C6A H6A 119.9 . . ? C1A C6A H6A 120.0 . . ? O2A C7A O1A 123.0(3) . . ? O2A C7A C1A 122.2(3) . . ? O1A C7A C1A 114.7(3) . . ? C4A O3A C4A 116.9(4) . 2_645 ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.200 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.049 #===END data_1oxa _database_code_CSD 191436 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene oxalic acid ; _chemical_name_common ? _chemical_melting_point 198-199 _chemical_formula_moiety 'C16 H14 N4, C2H2O4' _chemical_formula_sum 'C18 H16 N4 O4' _chemical_formula_weight 352.35 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 orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.281(3) _cell_length_b 24.097(6) _cell_length_c 8.919(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1564.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 8 _cell_measurement_theta_max 30 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.904 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 296(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 2182 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 62.58 _reflns_number_total 1274 _reflns_number_gt 838 _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^)+(0.0482P)^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 and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1274 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 0.1045(2) 0.41126(6) 0.89322(16) 0.0328(4) Uani 1 1 d . . . H1N H 0.038(6) 0.4466(14) 0.788(3) 0.146(13) Uiso 1 1 d . . . N7 N 0.1959(2) 0.35142(6) 0.70766(15) 0.0327(4) Uani 1 1 d . . . H7 H 0.1808 0.3822 0.6403 0.056(7) Uiso 1 1 d R . . C2 C 0.1968(3) 0.36478(7) 0.85713(19) 0.0276(4) Uani 1 1 d . . . C3 C 0.2909(3) 0.33502(8) 0.96704(19) 0.0333(5) Uani 1 1 d . . . H3 H 0.3585 0.3023 0.9400 0.046(6) Uiso 1 1 d R . . C4 C 0.2878(3) 0.35399(8) 1.1116(2) 0.0393(5) Uani 1 1 d . . . H4 H 0.3609 0.3342 1.1835 0.049(6) Uiso 1 1 d R . . C5 C 0.1894(3) 0.40100(8) 1.1497(2) 0.0436(6) Uani 1 1 d . . . H5 H 0.1863 0.4162 1.2492 0.047(6) Uiso 1 1 d R . . C6 C 0.1011(3) 0.42846(8) 1.0374(2) 0.0398(6) Uani 1 1 d . . . H6 H 0.0246 0.4603 1.0552 0.050(6) Uiso 1 1 d R . . C8 C 0.2397(3) 0.29985(7) 0.64454(19) 0.0277(5) Uani 1 1 d . . . C9 C 0.3139(3) 0.29983(8) 0.5009(2) 0.0374(5) Uani 1 1 d . . . H9 H 0.3336 0.3355 0.4558 0.050(6) Uiso 1 1 d R . . C10 C 0.3492(5) 0.2500 0.4310(3) 0.0436(8) Uani 1 2 d S . . H10 H 0.3999 0.2500 0.3317 0.058(10) Uiso 1 2 d SR . . C11 C 0.1995(4) 0.2500 0.7142(3) 0.0273(6) Uani 1 2 d S . . H11 H 0.1316 0.2500 0.8065 0.041(8) Uiso 1 2 d SR . . C1A C 0.0346(3) 0.47757(7) 0.5557(2) 0.0335(5) Uani 1 1 d . . . O1A O -0.0304(2) 0.48123(6) 0.68753(15) 0.0475(4) Uani 1 1 d . . . O2A O 0.1447(2) 0.44235(6) 0.51267(14) 0.0481(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0470(10) 0.0219(8) 0.0296(9) -0.0019(7) 0.0012(8) 0.0011(8) N7 0.0529(11) 0.0228(8) 0.0225(8) 0.0007(6) -0.0007(8) 0.0055(8) C2 0.0358(11) 0.0210(9) 0.0260(9) 0.0000(7) 0.0027(9) -0.0014(9) C3 0.0417(12) 0.0269(10) 0.0312(10) 0.0010(8) -0.0011(10) 0.0038(10) C4 0.0530(14) 0.0361(11) 0.0288(11) 0.0046(9) -0.0062(11) 0.0020(11) C5 0.0678(16) 0.0357(11) 0.0272(11) -0.0031(9) 0.0016(11) 0.0010(11) C6 0.0581(15) 0.0293(11) 0.0320(12) -0.0042(9) 0.0074(11) 0.0053(10) C8 0.0347(11) 0.0243(10) 0.0243(9) -0.0003(7) -0.0036(9) 0.0021(8) C9 0.0576(15) 0.0282(10) 0.0265(10) 0.0034(8) 0.0045(10) -0.0030(10) C10 0.075(2) 0.0325(15) 0.0231(14) 0.000 0.0104(15) 0.000 C11 0.0309(15) 0.0280(13) 0.0229(14) 0.000 0.0009(13) 0.000 C1A 0.0437(12) 0.0274(10) 0.0294(12) -0.0030(9) -0.0033(10) 0.0032(10) O1A 0.0651(10) 0.0469(9) 0.0305(8) 0.0034(7) 0.0064(8) 0.0199(8) O2A 0.0675(11) 0.0416(9) 0.0351(8) 0.0048(7) 0.0058(8) 0.0231(8) 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 1.345(2) . ? N1 C6 1.352(2) . ? N7 C2 1.371(2) . ? N7 C8 1.401(2) . ? C2 C3 1.395(2) . ? C3 C4 1.368(3) . ? C4 C5 1.383(3) . ? C5 C6 1.362(3) . ? C8 C11 1.384(2) . ? C8 C9 1.390(3) . ? C9 C10 1.377(2) . ? C10 C9 1.377(2) 7_565 ? C11 C8 1.384(2) 7_565 ? C1A O2A 1.229(2) . ? C1A O1A 1.270(2) . ? C1A C1A 1.553(4) 5_566 ? 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 119.50(16) . . ? C2 N7 C8 126.70(15) . . ? N1 C2 N7 115.20(16) . . ? N1 C2 C3 120.36(16) . . ? N7 C2 C3 124.39(17) . . ? C4 C3 C2 118.85(18) . . ? C3 C4 C5 120.91(19) . . ? C6 C5 C4 117.54(18) . . ? N1 C6 C5 122.81(19) . . ? C11 C8 C9 119.72(19) . . ? C11 C8 N7 122.78(16) . . ? C9 C8 N7 117.32(17) . . ? C10 C9 C8 119.3(2) . . ? C9 C10 C9 121.4(3) . 7_565 ? C8 C11 C8 120.5(2) 7_565 . ? O2A C1A O1A 125.47(17) . . ? O2A C1A C1A 119.5(2) . 5_566 ? O1A C1A C1A 115.0(2) . 5_566 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 62.58 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.168 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.045 #===END data_1seb _database_code_CSD 191437 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene sebacic acid ; _chemical_name_common ? _chemical_melting_point 138 _chemical_formula_moiety 'C16H14N4, C10H18O4' _chemical_formula_sum 'C26 H32 N4 O4' _chemical_formula_weight 464.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.4920(10) _cell_length_b 34.585(2) _cell_length_c 6.3180(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.810(10) _cell_angle_gamma 90.00 _cell_volume 1170.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 6765 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2024 _reflns_number_gt 1561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0468P)^2^+0.6292P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2024 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1293 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 0.4209(4) 0.13853(5) 0.1426(3) 0.0240(5) Uani 1 1 d . . . C2 C 0.3444(4) 0.17062(7) 0.0255(4) 0.0228(6) Uani 1 1 d . . . C3 C 0.1396(4) 0.19205(7) 0.0589(4) 0.0250(6) Uani 1 1 d . . . H3 H 0.0794 0.2134 -0.0357 0.029(7) Uiso 1 1 d R . . C4 C 0.0248(4) 0.18098(7) 0.2232(4) 0.0288(6) Uani 1 1 d . . . H4 H -0.1177 0.1948 0.2485 0.035(7) Uiso 1 1 d R . . C5 C 0.1086(5) 0.14897(7) 0.3497(4) 0.0297(6) Uani 1 1 d . . . H5 H 0.0348 0.1409 0.4668 0.035(7) Uiso 1 1 d R . . C6 C 0.3036(5) 0.12852(7) 0.3009(4) 0.0277(6) Uani 1 1 d . . . H6 H 0.3673 0.1054 0.3780 0.030(7) Uiso 1 1 d R . . N7 N 0.4753(4) 0.17876(6) -0.1324(3) 0.0254(5) Uani 1 1 d . . . H7 H 0.5731 0.1576 -0.1662 0.038(7) Uiso 1 1 d R . . C8 C 0.5100(4) 0.21503(7) -0.2226(4) 0.0226(6) Uani 1 1 d . . . C9 C 0.6083(5) 0.21510(7) -0.4082(4) 0.0276(6) Uani 1 1 d . . . H9 H 0.6395 0.1913 -0.4757 0.035(7) Uiso 1 1 d R . . C10 C 0.6588(7) 0.2500 -0.4966(6) 0.0321(9) Uani 1 2 d S . . H10 H 0.7342 0.2500 -0.6200 0.047(11) Uiso 1 2 d SR . . C11 C 0.4676(6) 0.2500 -0.1275(5) 0.0207(7) Uani 1 2 d S . . H11 H 0.4129 0.2500 0.0067 0.018(8) Uiso 1 2 d SR . . O1A O 0.7291(3) 0.08318(5) 0.0764(3) 0.0294(5) Uani 1 1 d . . . H1O H 0.624(6) 0.1054(11) 0.097(5) 0.078(11) Uiso 1 1 d . . . O2A O 0.7918(3) 0.11415(5) -0.2185(3) 0.0318(5) Uani 1 1 d . . . C1A C 0.8354(4) 0.08723(7) -0.0918(4) 0.0233(5) Uani 1 1 d . . . C2A C 1.0130(5) 0.05489(7) -0.1062(4) 0.0259(6) Uani 1 1 d . . . H2AA H 0.9169 0.0316 -0.1100 0.036(7) Uiso 1 1 d R . . H2AB H 1.1340 0.0545 0.0292 0.028(7) Uiso 1 1 d R . . C3A C 1.1407(5) 0.05623(7) -0.2970(4) 0.0256(6) Uani 1 1 d . . . H3AA H 1.2411 0.0792 -0.2831 0.024(6) Uiso 1 1 d R . . H3AB H 1.0177 0.0588 -0.4303 0.031(7) Uiso 1 1 d R . . C4A C 1.3000(4) 0.02029(7) -0.3040(4) 0.0249(6) Uani 1 1 d . . . H4AA H 1.2039 -0.0029 -0.3059 0.024(6) Uiso 1 1 d R . . H4AB H 1.4257 0.0188 -0.1717 0.025(6) Uiso 1 1 d R . . C5A C 1.4264(4) 0.01858(7) -0.4957(4) 0.0244(6) Uani 1 1 d . . . H5AB H 1.5353 0.0404 -0.4910 0.017(6) Uiso 1 1 d R . . H5AA H 1.2998 0.0206 -0.6271 0.028(7) 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 0.0323(11) 0.0185(11) 0.0237(11) 0.0021(9) 0.0113(9) 0.0010(9) C2 0.0266(13) 0.0180(12) 0.0246(13) -0.0015(10) 0.0075(11) -0.0034(10) C3 0.0261(13) 0.0194(13) 0.0293(14) 0.0007(11) 0.0054(11) -0.0007(10) C4 0.0292(14) 0.0234(13) 0.0371(15) -0.0042(12) 0.0141(12) -0.0005(11) C5 0.0373(15) 0.0268(14) 0.0294(14) -0.0013(11) 0.0167(12) -0.0045(11) C6 0.0355(14) 0.0216(13) 0.0279(15) 0.0048(11) 0.0112(12) 0.0015(11) N7 0.0350(12) 0.0185(11) 0.0275(12) 0.0027(9) 0.0171(10) 0.0047(9) C8 0.0257(13) 0.0203(13) 0.0221(13) 0.0012(10) 0.0058(11) 0.0016(10) C9 0.0399(15) 0.0185(13) 0.0270(14) -0.0022(11) 0.0132(12) 0.0017(11) C10 0.046(2) 0.026(2) 0.030(2) 0.000 0.0208(19) 0.000 C11 0.0266(18) 0.0226(18) 0.0137(17) 0.000 0.0056(14) 0.000 O1A 0.0394(10) 0.0228(10) 0.0309(10) 0.0028(8) 0.0182(8) 0.0059(8) O2A 0.0434(11) 0.0261(10) 0.0299(10) 0.0065(8) 0.0170(9) 0.0108(8) C1A 0.0255(13) 0.0202(13) 0.0249(13) -0.0024(11) 0.0069(11) -0.0024(10) C2A 0.0335(14) 0.0201(13) 0.0250(15) 0.0015(10) 0.0082(12) 0.0056(11) C3A 0.0311(14) 0.0227(14) 0.0236(14) 0.0002(11) 0.0070(12) 0.0034(11) C4A 0.0299(13) 0.0207(13) 0.0254(14) 0.0006(11) 0.0086(12) 0.0023(11) C5A 0.0289(13) 0.0209(13) 0.0240(14) 0.0012(10) 0.0073(11) 0.0040(11) _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 1.348(3) . ? N1 C6 1.350(3) . ? C2 N7 1.382(3) . ? C2 C3 1.402(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9602 . ? C4 C5 1.383(3) . ? C4 H4 0.9600 . ? C5 C6 1.374(3) . ? C5 H5 0.9599 . ? C6 H6 0.9598 . ? N7 C8 1.408(3) . ? N7 H7 0.9599 . ? C8 C11 1.393(3) . ? C8 C9 1.396(3) . ? C9 C10 1.384(3) . ? C9 H9 0.9600 . ? C10 C9 1.384(3) 4_565 ? C10 H10 0.9600 . ? C11 C8 1.393(3) 4_565 ? C11 H11 0.9600 . ? O1A C1A 1.329(3) . ? O1A H1O 0.99(4) . ? O2A C1A 1.216(3) . ? C1A C2A 1.500(3) . ? C2A C3A 1.524(3) . ? C2A H2AA 0.9600 . ? C2A H2AB 0.9600 . ? C3A C4A 1.526(3) . ? C3A H3AA 0.9599 . ? C3A H3AB 0.9600 . ? C4A C5A 1.525(3) . ? C4A H4AA 0.9601 . ? C4A H4AB 0.9600 . ? C5A C5A 1.525(4) 3_854 ? C5A H5AB 0.9598 . ? C5A H5AA 0.9600 . ? 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 118.41(19) . . ? N1 C2 N7 114.52(19) . . ? N1 C2 C3 121.1(2) . . ? N7 C2 C3 124.4(2) . . ? C4 C3 C2 118.8(2) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 120.4(2) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 118.8 . . ? C6 C5 C4 117.3(2) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 122.3 . . ? N1 C6 C5 123.9(2) . . ? N1 C6 H6 114.2 . . ? C5 C6 H6 121.9 . . ? C2 N7 C8 127.76(19) . . ? C2 N7 H7 114.3 . . ? C8 N7 H7 117.2 . . ? C11 C8 C9 119.6(2) . . ? C11 C8 N7 123.3(2) . . ? C9 C8 N7 117.0(2) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 120.8 . . ? C9 C10 C9 121.5(3) 4_565 . ? C9 C10 H10 119.3 4_565 . ? C9 C10 H10 119.3 . . ? C8 C11 C8 120.5(3) 4_565 . ? C8 C11 H11 119.7 4_565 . ? C8 C11 H11 119.7 . . ? C1A O1A H1O 113(2) . . ? O2A C1A O1A 123.4(2) . . ? O2A C1A C2A 124.5(2) . . ? O1A C1A C2A 112.1(2) . . ? C1A C2A C3A 116.4(2) . . ? C1A C2A H2AA 105.4 . . ? C3A C2A H2AA 110.6 . . ? C1A C2A H2AB 106.7 . . ? C3A C2A H2AB 110.9 . . ? H2AA C2A H2AB 106.2 . . ? C2A C3A C4A 111.44(19) . . ? C2A C3A H3AA 108.0 . . ? C4A C3A H3AA 110.8 . . ? C2A C3A H3AB 109.8 . . ? C4A C3A H3AB 110.3 . . ? H3AA C3A H3AB 106.4 . . ? C5A C4A C3A 114.81(19) . . ? C5A C4A H4AA 107.6 . . ? C3A C4A H4AA 111.4 . . ? C5A C4A H4AB 108.9 . . ? C3A C4A H4AB 109.0 . . ? H4AA C4A H4AB 104.6 . . ? C4A C5A C5A 113.5(2) . 3_854 ? C4A C5A H5AB 109.5 . . ? C5A C5A H5AB 109.4 3_854 . ? C4A C5A H5AA 108.3 . . ? C5A C5A H5AA 108.6 3_854 . ? H5AB C5A H5AA 107.2 . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.184 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.052 #===END data_1sq _database_code_CSD 191438 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene squaric acid ; _chemical_name_common ? _chemical_melting_point 287-288 _chemical_formula_moiety 'C16H14N4, C4H2O4' _chemical_formula_sum 'C20 H16 N4 O4' _chemical_formula_weight 376.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.251(4) _cell_length_b 24.325(5) _cell_length_c 9.185(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1620.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 7085 _diffrn_reflns_av_R_equivalents 0.1576 _diffrn_reflns_av_sigmaI/netI 0.1029 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 23.81 _reflns_number_total 1281 _reflns_number_gt 893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0815P)^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 and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1281 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1333 _refine_ls_R_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.2047 _refine_ls_wR_factor_gt 0.1717 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _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 0.1296(6) 0.40775(16) 0.8971(4) 0.0236(11) Uani 1 1 d . . . H1N H 0.063(7) 0.433(2) 0.828(6) 0.041(16) Uiso 1 1 d . . . N7 N 0.2167(6) 0.35085(17) 0.7086(4) 0.0240(11) Uani 1 1 d . . . H7 H 0.2013 0.3798 0.6385 0.021(13) Uiso 1 1 d R . . C2 C 0.2206(7) 0.3618(2) 0.8527(5) 0.0216(12) Uani 1 1 d . . . C3 C 0.3168(7) 0.3312(2) 0.9574(5) 0.0243(13) Uani 1 1 d . . . H3 H 0.3829 0.2987 0.9298 0.022(13) Uiso 1 1 d R . . C4 C 0.3153(7) 0.3479(2) 1.1000(5) 0.0268(13) Uani 1 1 d . . . H4 H 0.3807 0.3268 1.1716 0.055(18) Uiso 1 1 d R . . C5 C 0.2184(7) 0.3947(2) 1.1441(6) 0.0280(13) Uani 1 1 d . . . H5 H 0.2164 0.4061 1.2441 0.029(14) Uiso 1 1 d R . . C6 C 0.1298(7) 0.4239(2) 1.0381(5) 0.0244(13) Uani 1 1 d . . . H6 H 0.0653 0.4568 1.0648 0.011(12) Uiso 1 1 d R . . C8 C 0.2621(6) 0.29989(19) 0.6434(5) 0.0188(12) Uani 1 1 d . . . C9 C 0.3397(6) 0.2998(2) 0.5054(5) 0.0227(12) Uani 1 1 d . . . H9 H 0.3530 0.3361 0.4657 0.036(15) Uiso 1 1 d R . . C10 C 0.3747(10) 0.2500 0.4377(8) 0.0274(19) Uani 1 2 d S . . H10 H 0.4496 0.2500 0.3517 0.020(18) Uiso 1 2 d SR . . C11 C 0.2184(10) 0.2500 0.7119(8) 0.0257(18) Uani 1 2 d S . . H11 H 0.1700 0.2500 0.8091 0.05(3) Uiso 1 2 d SR . . O2A O 0.1937(5) 0.42588(14) 0.4878(4) 0.0296(10) Uani 1 1 d . . . O1A O -0.0554(5) 0.47900(13) 0.7401(3) 0.0270(10) Uani 1 1 d . . . C2A C -0.0238(7) 0.4908(2) 0.6082(5) 0.0237(13) Uani 1 1 d . . . C1A C 0.0884(7) 0.4665(2) 0.4929(5) 0.0235(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.040(3) 0.013(2) 0.018(2) 0.0032(18) -0.001(2) 0.002(2) N7 0.039(3) 0.017(2) 0.015(2) 0.0002(18) -0.006(2) 0.003(2) C2 0.031(3) 0.021(3) 0.014(3) 0.002(2) 0.003(2) -0.005(2) C3 0.032(3) 0.022(3) 0.018(3) -0.002(2) 0.002(2) 0.001(3) C4 0.029(3) 0.030(3) 0.022(3) 0.006(2) 0.000(3) -0.002(2) C5 0.040(3) 0.025(3) 0.019(3) -0.002(2) 0.006(3) -0.005(3) C6 0.035(3) 0.020(3) 0.018(3) 0.000(2) 0.004(2) -0.003(2) C8 0.029(3) 0.014(3) 0.014(3) -0.003(2) 0.000(2) -0.002(2) C9 0.035(3) 0.011(3) 0.021(3) 0.001(2) -0.002(2) -0.002(2) C10 0.039(5) 0.030(4) 0.014(4) 0.000 0.006(3) 0.000 C11 0.032(4) 0.025(4) 0.021(4) 0.000 -0.006(3) 0.000 O2A 0.044(2) 0.022(2) 0.023(2) 0.0017(15) -0.0034(18) 0.0076(18) O1A 0.047(2) 0.021(2) 0.0129(19) 0.0013(15) 0.0015(16) 0.0011(17) C2A 0.032(3) 0.020(3) 0.019(3) -0.003(2) 0.002(2) -0.004(2) C1A 0.033(3) 0.015(3) 0.022(3) 0.001(2) -0.002(2) -0.004(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 C6 1.354(6) . ? N1 C2 1.360(6) . ? N1 H1N 1.00(5) . ? N7 C2 1.351(6) . ? N7 C8 1.415(6) . ? N7 H7 0.9595 . ? C2 C3 1.402(7) . ? C3 C4 1.372(7) . ? C3 H3 0.9588 . ? C4 C5 1.399(7) . ? C4 H4 0.9589 . ? C5 C6 1.366(7) . ? C5 H5 0.9597 . ? C6 H6 0.9589 . ? C8 C9 1.386(6) . ? C8 C11 1.403(6) . ? C9 C10 1.385(6) . ? C9 H9 0.9594 . ? C10 C9 1.385(6) 7_565 ? C10 H10 0.9587 . ? C11 C8 1.403(6) 7_565 ? C11 H11 0.9592 . ? O2A C1A 1.250(6) . ? O1A C2A 1.266(5) . ? C2A C1A 1.460(7) . ? C2A C1A 1.470(7) 5_566 ? C1A C2A 1.470(7) 5_566 ? 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 121.7(4) . . ? C6 N1 H1N 115(3) . . ? C2 N1 H1N 123(3) . . ? C2 N7 C8 125.7(4) . . ? C2 N7 H7 121.0 . . ? C8 N7 H7 112.7 . . ? N7 C2 N1 116.5(4) . . ? N7 C2 C3 125.2(5) . . ? N1 C2 C3 118.2(4) . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.4(5) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.0 . . ? C6 C5 C4 117.0(5) . . ? C6 C5 H5 121.7 . . ? C4 C5 H5 121.3 . . ? N1 C6 C5 122.1(5) . . ? N1 C6 H6 119.1 . . ? C5 C6 H6 118.8 . . ? C9 C8 C11 120.0(5) . . ? C9 C8 N7 118.8(4) . . ? C11 C8 N7 121.0(5) . . ? C10 C9 C8 119.1(5) . . ? C10 C9 H9 127.9 . . ? C8 C9 H9 112.8 . . ? C9 C10 C9 122.0(7) . 7_565 ? C9 C10 H10 118.3 . . ? C9 C10 H10 118.3 7_565 . ? C8 C11 C8 119.7(7) 7_565 . ? C8 C11 H11 120.0 7_565 . ? C8 C11 H11 120.0 . . ? O1A C2A C1A 134.7(5) . . ? O1A C2A C1A 135.0(5) . 5_566 ? C1A C2A C1A 90.2(4) . 5_566 ? O2A C1A C2A 133.4(5) . . ? O2A C1A C2A 136.8(5) . 5_566 ? C2A C1A C2A 89.8(4) . 5_566 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.81 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.281 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.082 #===END data_1suc _database_code_CSD 191439 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene succinic acid ; _chemical_name_common ? _chemical_melting_point 187-188 _chemical_formula_moiety 'C16H14N4, C4H6O4' _chemical_formula_sum 'C20 H20 N4 O4' _chemical_formula_weight 380.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 monoclinic _symmetry_space_group_name_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.7015(5) _cell_length_b 26.821(3) _cell_length_c 6.1015(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.708(8) _cell_angle_gamma 90.00 _cell_volume 902.47(16) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 28 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 294(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 2346 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 65.07 _reflns_number_total 1533 _reflns_number_gt 1330 _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^)+(0.0633P)^2^+0.2080P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0089(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1533 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1064 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.6231(2) 0.60458(4) 0.1531(2) 0.0394(3) Uani 1 1 d . . . C2 C 0.6890(3) 0.64708(5) 0.2683(2) 0.0349(4) Uani 1 1 d . . . C3 C 0.8841(3) 0.67539(6) 0.2369(3) 0.0414(4) Uani 1 1 d . . . H3 H 0.9361 0.7050 0.3238 0.049(5) Uiso 1 1 d R . . C4 C 0.9972(3) 0.66070(6) 0.0747(3) 0.0474(4) Uani 1 1 d . . . H4 H 1.1307 0.6802 0.0532 0.058(5) Uiso 1 1 d R . . C5 C 0.9233(3) 0.61814(6) -0.0515(3) 0.0485(4) Uani 1 1 d . . . H5 H 1.0035 0.6073 -0.1638 0.060(5) Uiso 1 1 d R . . C6 C 0.7400(3) 0.59074(6) -0.0022(3) 0.0449(4) Uani 1 1 d . . . H6 H 0.6893 0.5592 -0.0724 0.056(5) Uiso 1 1 d R . . N7 N 0.5564(2) 0.65849(5) 0.4212(2) 0.0417(4) Uani 1 1 d . . . H7 H 0.4640 0.6308 0.4541 0.057(5) Uiso 1 1 d R . . C8 C 0.5191(3) 0.70488(5) 0.5119(2) 0.0338(3) Uani 1 1 d . . . C9 C 0.4183(3) 0.70507(6) 0.6967(3) 0.0422(4) Uani 1 1 d . . . H9 H 0.3848 0.6740 0.7604 0.052(5) Uiso 1 1 d R . . C10 C 0.3659(5) 0.7500 0.7832(4) 0.0455(6) Uani 1 2 d S . . H10 H 0.3007 0.7500 0.9137 0.054(7) Uiso 1 2 d SR . . C11 C 0.5640(4) 0.7500 0.4167(3) 0.0342(5) Uani 1 2 d S . . H11 H 0.6136 0.7500 0.2776 0.049(7) Uiso 1 2 d SR . . O1A O 0.3357(2) 0.53192(4) 0.2214(2) 0.0536(4) Uani 1 1 d . . . H1O H 0.426(5) 0.5635(10) 0.205(4) 0.091(8) Uiso 1 1 d . . . O2A O 0.2608(2) 0.57491(4) 0.5083(2) 0.0548(4) Uani 1 1 d . . . C1A C 0.2292(3) 0.53846(5) 0.3873(3) 0.0410(4) Uani 1 1 d . . . C2A C 0.0657(3) 0.49604(6) 0.4085(3) 0.0442(4) Uani 1 1 d . . . H22A H -0.0465 0.4914 0.2634 0.062(6) Uiso 1 1 d R . . H21A H 0.1638 0.4665 0.4391 0.062(6) 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 0.0494(7) 0.0275(7) 0.0466(7) -0.0035(5) 0.0223(6) -0.0034(5) C2 0.0418(8) 0.0252(7) 0.0399(8) 0.0012(6) 0.0144(6) 0.0010(6) C3 0.0416(8) 0.0291(8) 0.0563(9) -0.0034(6) 0.0179(7) -0.0024(6) C4 0.0458(9) 0.0370(9) 0.0664(11) 0.0047(7) 0.0273(8) 0.0002(7) C5 0.0566(10) 0.0421(9) 0.0559(10) -0.0016(8) 0.0312(8) 0.0026(7) C6 0.0562(10) 0.0336(9) 0.0509(9) -0.0068(7) 0.0248(8) -0.0024(7) N7 0.0564(8) 0.0256(7) 0.0518(8) -0.0048(5) 0.0300(7) -0.0067(5) C8 0.0391(7) 0.0275(7) 0.0364(7) -0.0019(6) 0.0123(6) -0.0013(6) C9 0.0591(10) 0.0317(8) 0.0412(8) 0.0033(6) 0.0227(7) -0.0016(7) C10 0.0654(15) 0.0399(12) 0.0393(12) 0.000 0.0281(11) 0.000 C11 0.0431(11) 0.0297(11) 0.0328(10) 0.000 0.0152(9) 0.000 O1A 0.0700(8) 0.0347(6) 0.0696(8) -0.0106(5) 0.0429(7) -0.0128(5) O2A 0.0775(9) 0.0373(7) 0.0598(7) -0.0116(5) 0.0362(7) -0.0208(6) C1A 0.0487(9) 0.0280(8) 0.0499(9) 0.0008(6) 0.0194(7) -0.0032(6) C2A 0.0548(10) 0.0306(8) 0.0531(10) -0.0043(7) 0.0243(8) -0.0080(7) _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 1.3416(19) . ? N1 C2 1.3416(19) . ? C2 N7 1.3761(18) . ? C2 C3 1.400(2) . ? C3 C4 1.369(2) . ? C3 H3 0.9600 . ? C4 C5 1.381(2) . ? C4 H4 0.9600 . ? C5 C6 1.372(2) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.3996(18) . ? N7 H7 0.9600 . ? C8 C9 1.390(2) . ? C8 C11 1.3938(17) . ? C9 C10 1.3785(19) . ? C9 H9 0.9599 . ? C10 C9 1.3785(19) 4_575 ? C10 H10 0.9601 . ? C11 C8 1.3938(17) 4_575 ? C11 H11 0.9600 . ? O1A C1A 1.3175(19) . ? O1A H1O 1.01(3) . ? O2A C1A 1.2106(18) . ? C1A C2A 1.497(2) . ? C2A C2A 1.509(3) 3_566 ? C2A H22A 0.9599 . ? C2A H21A 0.9600 . ? 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 118.83(13) . . ? N1 C2 N7 114.55(12) . . ? N1 C2 C3 121.03(13) . . ? N7 C2 C3 124.37(13) . . ? C4 C3 C2 118.64(14) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 121.3 . . ? C3 C4 C5 120.51(15) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 117.50(15) . . ? C6 C5 H5 121.5 . . ? C4 C5 H5 120.9 . . ? N1 C6 C5 123.31(15) . . ? N1 C6 H6 114.3 . . ? C5 C6 H6 122.3 . . ? C2 N7 C8 129.06(12) . . ? C2 N7 H7 113.3 . . ? C8 N7 H7 117.3 . . ? C9 C8 C11 119.50(13) . . ? C9 C8 N7 117.35(12) . . ? C11 C8 N7 123.02(14) . . ? C10 C9 C8 119.25(14) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 119.4 . . ? C9 C10 C9 121.9(2) . 4_575 ? C9 C10 H10 119.0 . . ? C9 C10 H10 119.0 4_575 . ? C8 C11 C8 120.51(18) . 4_575 ? C8 C11 H11 119.6 . . ? C8 C11 H11 119.6 4_575 . ? C1A O1A H1O 108.1(14) . . ? O2A C1A O1A 123.36(14) . . ? O2A C1A C2A 124.07(14) . . ? O1A C1A C2A 112.57(13) . . ? C1A C2A C2A 113.21(16) . 3_566 ? C1A C2A H22A 107.7 . . ? C2A C2A H22A 111.1 3_566 . ? C1A C2A H21A 107.4 . . ? C2A C2A H21A 110.3 3_566 . ? H22A C2A H21A 106.9 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 65.07 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.166 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.039 #===END data_1tere _database_code_CSD 191440 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,3-diaminobenzene 1,4-benzeneicarboxylic acid 2:1 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 N4, C4H3O2' _chemical_formula_sum 'C20 H17 N4 O2' _chemical_formula_weight 345.38 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 P21/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 10.268(2) _cell_length_b 15.529(3) _cell_length_c 11.158(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.47(3) _cell_angle_gamma 90.00 _cell_volume 1714.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 294(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 12805 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3016 _reflns_number_gt 2463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0825P)^2^+0.0970P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap, geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3016 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.89699(11) 0.21848(7) 0.85277(11) 0.0403(3) Uani 1 1 d . . . H1 H 0.920(2) 0.2677(13) 0.8084(18) 0.079(6) Uiso 1 1 d . . . C2 C 0.76688(13) 0.19871(8) 0.84376(13) 0.0399(3) Uani 1 1 d . . . C3 C 0.74041(15) 0.13407(10) 0.92272(15) 0.0511(4) Uani 1 1 d . . . H3 H 0.6474 0.1205 0.9153 0.061(5) Uiso 1 1 d R . . C4 C 0.84603(15) 0.09261(11) 1.00119(16) 0.0588(4) Uani 1 1 d . . . H4 H 0.8313 0.0499 1.0584 0.080(6) Uiso 1 1 d R . . C5 C 0.97959(15) 0.11311(10) 1.00524(15) 0.0520(4) Uani 1 1 d . . . H5 H 1.0565 0.0851 1.0591 0.059(4) Uiso 1 1 d R . . C6 C 1.00140(14) 0.17684(9) 0.93074(13) 0.0442(3) Uani 1 1 d . . . H6 H 1.0892 0.1968 0.9286 0.045(4) Uiso 1 1 d R . . N7 N 0.67252(11) 0.24230(8) 0.75990(12) 0.0511(3) Uani 1 1 d . . . H7 H 0.7000 0.2774 0.7002 0.070(5) Uiso 1 1 d R . . C8 C 0.52970(13) 0.23474(9) 0.74615(13) 0.0444(4) Uani 1 1 d . . . C9 C 0.47165(14) 0.28585(9) 0.82038(13) 0.0447(4) Uani 1 1 d . . . H9 H 0.5258 0.3222 0.8841 0.056(4) Uiso 1 1 d R . . C10 C 0.33202(13) 0.28610(9) 0.80015(13) 0.0421(3) Uani 1 1 d . . . C11 C 0.25378(14) 0.23393(9) 0.70652(14) 0.0481(4) Uani 1 1 d . . . H11 H 0.1570 0.2346 0.6887 0.052(4) Uiso 1 1 d R . . C12 C 0.31370(15) 0.18222(10) 0.63626(15) 0.0542(4) Uani 1 1 d . . . H12 H 0.2561 0.1475 0.5725 0.065(5) Uiso 1 1 d R . . C13 C 0.45244(15) 0.18206(10) 0.65531(15) 0.0523(4) Uani 1 1 d . . . H13 H 0.4942 0.1456 0.6067 0.064(5) Uiso 1 1 d R . . N14 N 0.26197(12) 0.33828(8) 0.86407(12) 0.0522(3) Uani 1 1 d . . . H14 H 0.1677 0.3440 0.8221 0.065(5) Uiso 1 1 d R . . C15 C 0.30797(15) 0.38809(9) 0.96940(14) 0.0492(4) Uani 1 1 d . . . N16 N 0.43727(14) 0.38486(9) 1.03400(13) 0.0626(4) Uani 1 1 d . . . C17 C 0.4749(2) 0.43557(13) 1.13446(16) 0.0757(6) Uani 1 1 d . . . H17 H 0.5694 0.4344 1.1770 0.094(7) Uiso 1 1 d R . . C18 C 0.3895(2) 0.48819(13) 1.17525(18) 0.0799(6) Uani 1 1 d . . . H18 H 0.4256 0.5220 1.2486 0.095(7) Uiso 1 1 d R . . C19 C 0.2551(2) 0.49051(12) 1.10903(18) 0.0769(6) Uani 1 1 d . . . H19 H 0.1867 0.5246 1.1307 0.094(7) Uiso 1 1 d R . . C20 C 0.21242(19) 0.44031(11) 1.00473(16) 0.0620(4) Uani 1 1 d . . . H20 H 0.1200 0.4416 0.9559 0.077(6) Uiso 1 1 d R . . O1A O 0.97557(10) 0.35588(7) 0.75380(10) 0.0535(3) Uani 1 1 d . . . O2A O 0.78607(10) 0.34445(9) 0.60324(11) 0.0697(4) Uani 1 1 d . . . C1A C 0.90024(12) 0.37460(9) 0.64719(13) 0.0421(3) Uani 1 1 d . . . C2A C 0.95336(12) 0.43898(8) 0.57079(12) 0.0368(3) Uani 1 1 d . . . C3A C 1.06059(13) 0.49334(8) 0.62635(13) 0.0395(3) Uani 1 1 d . . . H3A H 1.0999 0.4901 0.7145 0.049(4) Uiso 1 1 d R . . C4A C 0.89381(13) 0.44609(8) 0.44426(13) 0.0400(3) Uani 1 1 d . . . H4A H 0.8224 0.4075 0.4043 0.053(4) 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 0.0329(6) 0.0438(6) 0.0442(7) 0.0067(5) 0.0105(5) -0.0021(5) C2 0.0334(7) 0.0423(7) 0.0447(8) 0.0027(6) 0.0118(6) -0.0014(5) C3 0.0361(7) 0.0564(9) 0.0610(9) 0.0136(7) 0.0132(7) -0.0080(6) C4 0.0491(9) 0.0593(9) 0.0648(10) 0.0239(8) 0.0096(8) -0.0081(7) C5 0.0407(8) 0.0527(9) 0.0574(9) 0.0156(7) 0.0042(7) -0.0013(6) C6 0.0348(7) 0.0478(8) 0.0483(8) 0.0046(6) 0.0083(6) -0.0012(6) N7 0.0337(6) 0.0614(8) 0.0595(8) 0.0211(6) 0.0145(6) 0.0035(5) C8 0.0339(7) 0.0490(8) 0.0497(8) 0.0137(6) 0.0098(6) 0.0021(6) C9 0.0354(7) 0.0507(8) 0.0450(8) 0.0040(6) 0.0056(6) -0.0035(6) C10 0.0354(7) 0.0462(8) 0.0434(8) 0.0046(6) 0.0083(6) 0.0010(6) C11 0.0333(7) 0.0540(8) 0.0539(9) 0.0002(7) 0.0061(6) -0.0017(6) C12 0.0456(8) 0.0582(9) 0.0550(9) -0.0087(7) 0.0069(7) -0.0047(7) C13 0.0483(9) 0.0546(9) 0.0558(9) -0.0002(7) 0.0172(7) 0.0041(7) N14 0.0360(7) 0.0656(8) 0.0530(7) -0.0076(6) 0.0085(6) 0.0020(6) C15 0.0514(9) 0.0497(8) 0.0473(8) 0.0030(6) 0.0146(7) -0.0020(7) N16 0.0559(9) 0.0713(9) 0.0540(8) -0.0082(7) 0.0034(7) -0.0014(7) C17 0.0826(14) 0.0810(13) 0.0547(11) -0.0107(9) 0.0031(10) -0.0066(10) C18 0.1113(18) 0.0737(13) 0.0521(11) -0.0122(9) 0.0171(11) -0.0063(12) C19 0.1032(16) 0.0706(12) 0.0663(12) -0.0045(9) 0.0387(12) 0.0086(11) C20 0.0674(11) 0.0642(10) 0.0595(10) 0.0011(8) 0.0256(9) 0.0066(8) O1A 0.0372(6) 0.0643(7) 0.0558(6) 0.0230(5) 0.0069(5) -0.0068(4) O2A 0.0369(6) 0.0951(9) 0.0702(8) 0.0352(7) 0.0024(5) -0.0200(5) C1A 0.0286(7) 0.0465(7) 0.0513(8) 0.0129(6) 0.0111(6) 0.0026(5) C2A 0.0286(6) 0.0377(7) 0.0460(8) 0.0066(6) 0.0135(5) 0.0048(5) C3A 0.0341(7) 0.0446(7) 0.0393(7) 0.0057(6) 0.0092(5) 0.0019(5) C4A 0.0323(7) 0.0402(7) 0.0469(8) 0.0027(6) 0.0094(6) -0.0016(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 1.3483(16) . ? N1 C6 1.3515(17) . ? C2 N7 1.3376(18) . ? C2 C3 1.4090(19) . ? C3 C4 1.360(2) . ? C4 C5 1.397(2) . ? C5 C6 1.349(2) . ? N7 C8 1.4380(17) . ? C8 C13 1.377(2) . ? C8 C9 1.391(2) . ? C9 C10 1.3906(19) . ? C10 C11 1.395(2) . ? C10 N14 1.3987(18) . ? C11 C12 1.377(2) . ? C12 C13 1.383(2) . ? N14 C15 1.3808(19) . ? C15 N16 1.332(2) . ? C15 C20 1.408(2) . ? N16 C17 1.340(2) . ? C17 C18 1.362(3) . ? C18 C19 1.382(3) . ? C19 C20 1.372(3) . ? O1A C1A 1.2677(17) . ? O2A C1A 1.2358(17) . ? C1A C2A 1.5072(18) . ? C2A C4A 1.3853(19) . ? C2A C3A 1.3947(19) . ? C3A C4A 1.3862(18) 3_766 ? C4A C3A 1.3862(18) 3_766 ? 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 122.62(12) . . ? N7 C2 N1 117.09(12) . . ? N7 C2 C3 125.00(12) . . ? N1 C2 C3 117.92(13) . . ? C4 C3 C2 119.08(13) . . ? C3 C4 C5 121.34(14) . . ? C6 C5 C4 118.05(14) . . ? C5 C6 N1 120.93(13) . . ? C2 N7 C8 124.13(11) . . ? C13 C8 C9 121.53(13) . . ? C13 C8 N7 119.86(13) . . ? C9 C8 N7 118.47(13) . . ? C10 C9 C8 119.47(13) . . ? C9 C10 C11 118.88(13) . . ? C9 C10 N14 124.54(13) . . ? C11 C10 N14 116.52(12) . . ? C12 C11 C10 120.64(13) . . ? C11 C12 C13 120.79(14) . . ? C8 C13 C12 118.65(14) . . ? C15 N14 C10 130.76(13) . . ? N16 C15 N14 120.31(14) . . ? N16 C15 C20 122.60(15) . . ? N14 C15 C20 117.08(14) . . ? C15 N16 C17 116.99(16) . . ? N16 C17 C18 124.4(2) . . ? C17 C18 C19 118.49(18) . . ? C20 C19 C18 119.09(19) . . ? C19 C20 C15 118.44(18) . . ? O2A C1A O1A 124.21(12) . . ? O2A C1A C2A 118.36(12) . . ? O1A C1A C2A 117.42(11) . . ? C4A C2A C3A 119.10(12) . . ? C4A C2A C1A 120.09(12) . . ? C3A C2A C1A 120.79(12) . . ? C4A C3A C2A 120.29(13) 3_766 . ? C2A C4A C3A 120.61(12) . 3_766 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.191 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.035 #===END data_2diph _database_code_CSD 191441 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,4-diaminobenzene 2,2'-biphenyldicarboxylic acid co-crystal ; _chemical_name_common ? _chemical_melting_point 216 _chemical_formula_moiety 'C16H14N4, C14H10O4' _chemical_formula_sum 'C30 H24 N4 O4' _chemical_formula_weight 504.53 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 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 9.117(2) _cell_length_b 14.433(4) _cell_length_c 19.312(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2541.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 7 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 296(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 2258 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.06 _reflns_number_total 2258 _reflns_number_gt 1208 _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^)+(0.0586P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens dimap,geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0095(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2258 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1369 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _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 -0.80616(18) -0.23704(12) 0.37850(10) 0.0550(5) Uani 1 1 d . . . C2 C -0.7815(2) -0.16667(15) 0.42167(12) 0.0540(6) Uani 1 1 d . . . C3 C -0.8981(2) -0.11778(17) 0.45110(14) 0.0679(7) Uani 1 1 d . . . H3 H -0.8774 -0.0684 0.4829 0.098(9) Uiso 1 1 d R . . C4 C -1.0374(3) -0.13947(18) 0.43109(16) 0.0788(8) Uani 1 1 d . . . H4 H -1.1206 -0.1060 0.4485 0.115(10) Uiso 1 1 d R . . C5 C -1.0625(3) -0.20971(17) 0.38504(16) 0.0793(8) Uani 1 1 d . . . H5 H -1.1541 -0.2304 0.3660 0.086(8) Uiso 1 1 d R . . C6 C -0.9453(3) -0.25735(17) 0.36129(14) 0.0684(7) Uani 1 1 d . . . H6 H -0.9480 -0.3070 0.3283 0.089(9) Uiso 1 1 d R . . C8 C -0.5737(2) -0.07363(14) 0.46874(11) 0.0475(5) Uani 1 1 d . . . C10 C -0.6281(2) 0.01551(14) 0.46422(11) 0.0537(6) Uani 1 1 d . . . H10 H -0.7146 0.0273 0.4373 0.077(7) Uiso 1 1 d R . . C9 C -0.4442(2) -0.08785(15) 0.50460(10) 0.0508(5) Uani 1 1 d . . . H9 H -0.4061 -0.1498 0.5069 0.045(5) Uiso 1 1 d R . . N7 N -0.63698(17) -0.15036(12) 0.43526(10) 0.0605(5) Uani 1 1 d . . . H7 H -0.5680 -0.1980 0.4233 0.072(7) Uiso 1 1 d R . . O1A O -0.6227(2) -0.3623(3) 0.3370(2) 0.0784(13) Uani 0.898(10) 1 d P . . H1OA H -0.681(3) -0.2970(19) 0.3504(14) 0.110(9) Uiso 1 1 d . . . O2A O -0.4334(3) -0.2834(3) 0.3772(3) 0.0923(13) Uani 0.898(10) 1 d P . . O1A' O -0.587(2) -0.3232(14) 0.3093(8) 0.038(6) Uiso 0.102(10) 1 d P . . O2A' O -0.470(3) -0.3195(16) 0.4023(10) 0.057(7) Uiso 0.102(10) 1 d P . . C1A C -0.42737(19) -0.48587(13) 0.26712(11) 0.0460(5) Uani 1 1 d . . . C2A C -0.3860(2) -0.42437(13) 0.31985(11) 0.0475(5) Uani 1 1 d . . . C3A C -0.2470(2) -0.43313(16) 0.34883(12) 0.0604(6) Uani 1 1 d . . . H3A H -0.2237 -0.3913 0.3859 0.063(7) Uiso 1 1 d R . . C4A C -0.1522(2) -0.50041(17) 0.32819(14) 0.0714(7) Uani 1 1 d . . . H4A H -0.0528 -0.5045 0.3443 0.079(7) Uiso 1 1 d R . . C5A C -0.1930(2) -0.56164(17) 0.27790(14) 0.0699(7) Uani 1 1 d . . . H5A H -0.1296 -0.6104 0.2622 0.088(8) Uiso 1 1 d R . . C6A C -0.3303(2) -0.55421(15) 0.24826(13) 0.0605(6) Uani 1 1 d . . . H6A H -0.3596 -0.5980 0.2135 0.079(8) Uiso 1 1 d R . . C7A C -0.4818(2) -0.35039(16) 0.34668(12) 0.0555(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0450(10) 0.0503(10) 0.0698(12) 0.0014(9) -0.0078(9) -0.0052(8) C2 0.0450(13) 0.0515(12) 0.0655(14) 0.0061(12) 0.0002(10) -0.0022(10) C3 0.0431(13) 0.0683(15) 0.0922(19) -0.0065(14) 0.0081(12) -0.0018(11) C4 0.0476(14) 0.0702(17) 0.119(2) 0.0051(17) 0.0086(14) 0.0007(13) C5 0.0436(14) 0.0666(16) 0.128(2) 0.0141(17) -0.0182(15) -0.0089(13) C6 0.0542(15) 0.0599(15) 0.0910(19) 0.0060(14) -0.0163(13) -0.0112(12) C8 0.0395(11) 0.0515(13) 0.0516(12) -0.0055(10) 0.0046(10) 0.0011(10) C10 0.0408(11) 0.0632(14) 0.0570(13) -0.0019(11) -0.0025(10) 0.0054(11) C9 0.0429(10) 0.0493(13) 0.0601(14) -0.0026(11) 0.0043(10) 0.0033(9) N7 0.0372(10) 0.0596(11) 0.0848(14) -0.0191(11) -0.0048(9) -0.0004(9) O1A 0.0420(11) 0.074(2) 0.120(3) -0.038(2) -0.0038(12) -0.0055(11) O2A 0.0526(13) 0.083(2) 0.141(3) -0.053(2) -0.0044(15) -0.0118(12) C1A 0.0374(10) 0.0463(10) 0.0544(12) 0.0052(10) -0.0066(10) -0.0013(9) C2A 0.0411(11) 0.0496(12) 0.0520(12) 0.0026(10) -0.0073(9) -0.0043(9) C3A 0.0500(12) 0.0654(14) 0.0659(15) -0.0001(13) -0.0179(11) -0.0052(12) C4A 0.0406(12) 0.0824(17) 0.0912(19) 0.0104(15) -0.0230(13) 0.0018(13) C5A 0.0420(12) 0.0697(15) 0.098(2) -0.0030(15) -0.0072(13) 0.0083(13) C6A 0.0429(11) 0.0579(13) 0.0806(15) -0.0084(13) -0.0062(11) 0.0077(11) C7A 0.0497(13) 0.0579(14) 0.0588(14) -0.0076(12) -0.0069(11) -0.0059(12) _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 1.333(3) . ? N1 C6 1.344(3) . ? C2 N7 1.364(2) . ? C2 C3 1.397(3) . ? C3 C4 1.364(3) . ? C4 C5 1.368(4) . ? C5 C6 1.351(3) . ? C8 C10 1.382(3) . ? C8 C9 1.384(3) . ? C8 N7 1.406(3) . ? C10 C9 1.374(3) 5_456 ? C9 C10 1.374(3) 5_456 ? O1A O1A' 0.84(2) . ? O1A C7A 1.310(3) . ? O2A O2A' 0.78(2) . ? O2A C7A 1.215(3) . ? O1A' C7A 1.266(14) . ? O2A' C7A 1.17(2) . ? C1A C6A 1.374(3) . ? C1A C2A 1.402(3) . ? C1A C1A 1.480(4) 3_455 ? C2A C3A 1.391(3) . ? C2A C7A 1.473(3) . ? C3A C4A 1.359(3) . ? C4A C5A 1.365(3) . ? C5A C6A 1.380(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 118.7(2) . . ? N1 C2 N7 114.52(19) . . ? N1 C2 C3 120.72(19) . . ? N7 C2 C3 124.7(2) . . ? C4 C3 C2 118.5(2) . . ? C3 C4 C5 120.7(2) . . ? C6 C5 C4 117.8(2) . . ? N1 C6 C5 123.5(2) . . ? C10 C8 C9 118.41(19) . . ? C10 C8 N7 123.86(19) . . ? C9 C8 N7 117.59(18) . . ? C9 C10 C8 120.5(2) 5_456 . ? C10 C9 C8 121.1(2) 5_456 . ? C2 N7 C8 128.36(18) . . ? O1A' O1A C7A 68.1(10) . . ? O2A' O2A C7A 67.6(16) . . ? O1A O1A' C7A 73.8(11) . . ? O2A O2A' C7A 74.0(15) . . ? C6A C1A C2A 118.27(18) . . ? C6A C1A C1A 117.23(18) . 3_455 ? C2A C1A C1A 124.39(17) . 3_455 ? C3A C2A C1A 118.65(19) . . ? C3A C2A C7A 117.65(19) . . ? C1A C2A C7A 123.70(17) . . ? C4A C3A C2A 121.7(2) . . ? C3A C4A C5A 119.9(2) . . ? C4A C5A C6A 119.5(2) . . ? C1A C6A C5A 122.0(2) . . ? O2A' C7A O2A 38.4(11) . . ? O2A' C7A O1A' 118.5(11) . . ? O2A C7A O1A' 107.8(8) . . ? O2A' C7A O1A 105.8(12) . . ? O2A C7A O1A 121.9(2) . . ? O1A' C7A O1A 38.1(10) . . ? O2A' C7A C2A 123.0(9) . . ? O2A C7A C2A 122.2(2) . . ? O1A' C7A C2A 118.3(6) . . ? O1A C7A C2A 115.9(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.142 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.037 #===END data_2mal _database_code_CSD 191442 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,4-diaminobenzene malonic acid co-crystal ; _chemical_name_common ? _chemical_melting_point 198-199 _chemical_formula_moiety 'C16 H14 N4, C3H4O4' _chemical_formula_sum 'C19 H18 N4 O4' _chemical_formula_weight 366.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 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 17.290(2) _cell_length_b 4.0427(5) _cell_length_c 24.720(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.121(11) _cell_angle_gamma 90.00 _cell_volume 1725.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 8 _cell_measurement_theta_max 25 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.841 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 2040 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 64.97 _reflns_number_total 1374 _reflns_number_gt 987 _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^)+(0.0485P)^2^+0.8756P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1374 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.69105(9) 0.2358(5) 0.65532(6) 0.0430(5) Uani 1 1 d . . . H1N H 0.6538(17) 0.375(8) 0.6835(12) 0.104(10) Uiso 1 1 d . . . C2 C 0.66350(10) 0.1159(5) 0.60696(7) 0.0386(5) Uani 1 1 d . . . C3 C 0.71266(11) -0.0657(6) 0.57507(8) 0.0465(5) Uani 1 1 d . . . H3 H 0.6935 -0.1594 0.5413 0.064(7) Uiso 1 1 d R . . C4 C 0.78782(12) -0.1184(6) 0.59354(9) 0.0542(6) Uani 1 1 d . . . H4 H 0.8191 -0.2441 0.5700 0.062(7) Uiso 1 1 d R . . C5 C 0.81508(12) 0.0074(7) 0.64317(10) 0.0584(7) Uani 1 1 d . . . H5 H 0.8674 -0.0259 0.6572 0.073(7) Uiso 1 1 d R . . C6 C 0.76508(11) 0.1792(6) 0.67268(9) 0.0524(6) Uani 1 1 d . . . H6 H 0.7781 0.2796 0.7072 0.062(7) Uiso 1 1 d R . . N7 N 0.58814(8) 0.1822(5) 0.59411(6) 0.0458(5) Uani 1 1 d . . . H7 H 0.5598 0.2748 0.6228 0.061(7) Uiso 1 1 d R . . C8 C 0.54527(10) 0.0841(5) 0.54616(7) 0.0377(5) Uani 1 1 d . . . C9 C 0.47462(10) -0.0695(5) 0.55073(7) 0.0406(5) Uani 1 1 d . . . H9 H 0.4584 -0.1185 0.5864 0.049(6) Uiso 1 1 d R . . C10 C 0.57036(10) 0.1539(5) 0.49513(7) 0.0414(5) Uani 1 1 d . . . H10 H 0.6183 0.2689 0.4913 0.051(6) Uiso 1 1 d R . . C1A C 0.54187(11) 0.6301(5) 0.71090(7) 0.0408(5) Uani 1 1 d . . . C2A C 0.5000 0.8433(8) 0.7500 0.0463(7) Uani 1 2 d S . . O2A O 0.50602(8) 0.5051(4) 0.67170(6) 0.0562(5) Uani 1 1 d . . . O1A O 0.61439(8) 0.5904(5) 0.72114(6) 0.0614(5) Uani 1 1 d . . . H2A H 0.4614 0.9671 0.7292 0.061(7) 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 0.0343(8) 0.0600(11) 0.0340(9) 0.0015(8) -0.0031(6) -0.0017(8) C2 0.0314(9) 0.0509(13) 0.0331(10) 0.0051(9) -0.0012(8) -0.0031(9) C3 0.0382(11) 0.0581(14) 0.0434(11) -0.0004(11) 0.0019(9) 0.0054(10) C4 0.0412(11) 0.0645(15) 0.0571(14) 0.0071(12) 0.0069(10) 0.0091(11) C5 0.0334(11) 0.0768(17) 0.0641(15) 0.0118(13) -0.0063(10) 0.0028(11) C6 0.0379(11) 0.0714(16) 0.0466(13) 0.0062(12) -0.0091(9) -0.0045(11) N7 0.0310(8) 0.0729(13) 0.0328(9) -0.0113(9) -0.0039(6) 0.0060(8) C8 0.0295(9) 0.0489(12) 0.0345(10) -0.0047(9) -0.0020(7) 0.0068(8) C9 0.0354(10) 0.0566(13) 0.0298(10) 0.0034(9) 0.0029(8) 0.0046(9) C10 0.0299(10) 0.0543(13) 0.0401(11) 0.0008(10) 0.0018(8) -0.0033(9) C1A 0.0414(11) 0.0496(12) 0.0313(10) 0.0058(9) 0.0007(8) -0.0070(9) C2A 0.0537(17) 0.0435(17) 0.0420(16) 0.000 0.0040(13) 0.000 O2A 0.0395(8) 0.0856(12) 0.0432(8) -0.0143(8) -0.0010(6) 0.0025(8) O1A 0.0404(8) 0.0912(13) 0.0517(9) -0.0172(9) -0.0070(6) 0.0015(8) _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 1.347(2) . ? N1 C2 1.352(2) . ? N1 H1N 1.12(3) . ? C2 N7 1.351(2) . ? C2 C3 1.398(3) . ? C3 C4 1.370(3) . ? C3 H3 0.9599 . ? C4 C5 1.387(3) . ? C4 H4 0.9599 . ? C5 C6 1.353(3) . ? C5 H5 0.9596 . ? C6 H6 0.9598 . ? N7 C8 1.420(2) . ? N7 H7 0.9599 . ? C8 C9 1.381(3) . ? C8 C10 1.385(3) . ? C9 C10 1.382(2) 5_656 ? C9 H9 0.9599 . ? C10 C9 1.382(2) 5_656 ? C10 H10 0.9599 . ? C1A O2A 1.230(2) . ? C1A O1A 1.276(2) . ? C1A C2A 1.509(3) . ? C2A C1A 1.509(3) 2_656 ? C2A H2A 0.9606 . ? O1A H1N 1.47(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 120.23(19) . . ? C6 N1 H1N 117.0(14) . . ? C2 N1 H1N 122.7(14) . . ? N7 C2 N1 115.18(17) . . ? N7 C2 C3 125.43(17) . . ? N1 C2 C3 119.39(17) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4 115.8 . . ? C5 C4 H4 123.6 . . ? C6 C5 C4 117.97(19) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 122.4 . . ? N1 C6 C5 122.6(2) . . ? N1 C6 H6 112.6 . . ? C5 C6 H6 124.7 . . ? C2 N7 C8 126.42(17) . . ? C2 N7 H7 115.4 . . ? C8 N7 H7 117.5 . . ? C9 C8 C10 119.24(17) . . ? C9 C8 N7 118.78(17) . . ? C10 C8 N7 121.89(17) . . ? C8 C9 C10 120.32(18) . 5_656 ? C8 C9 H9 118.1 . . ? C10 C9 H9 121.5 5_656 . ? C9 C10 C8 120.44(18) 5_656 . ? C9 C10 H10 119.3 5_656 . ? C8 C10 H10 120.2 . . ? O2A C1A O1A 123.53(19) . . ? O2A C1A C2A 120.02(15) . . ? O1A C1A C2A 116.45(15) . . ? C1A C2A C1A 110.3(2) 2_656 . ? C1A C2A H2A 107.3 2_656 . ? C1A C2A H2A 107.3 . . ? C1A O1A H1N 115.7(11) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 64.97 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.169 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.044 #===END data_2seb _database_code_CSD 191443 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,4-diaminobenzene sebacic acid ; _chemical_name_common ? _chemical_melting_point 185-186 _chemical_formula_moiety 'C16H14N4, C10H18O4' _chemical_formula_sum 'C26 H32 N4 O4' _chemical_formula_weight 464.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.4312(9) _cell_length_b 10.1438(12) _cell_length_c 15.0064(15) _cell_angle_alpha 85.842(9) _cell_angle_beta 73.025(9) _cell_angle_gamma 78.006(9) _cell_volume 1200.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 9211 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.1268 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4194 _reflns_number_gt 1591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0465P)^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, geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4194 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1829 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4820(3) 0.2565(3) -0.66383(19) 0.0750(9) Uani 1 1 d . . . H1O H 0.463(5) 0.328(5) -0.711(3) 0.139(18) Uiso 1 1 d . . . O2 O 0.7585(3) 0.2264(2) -0.72865(16) 0.0631(8) Uani 1 1 d . . . O3 O 1.5058(3) -0.7673(3) -0.34991(17) 0.0691(8) Uani 1 1 d . . . H3O H 1.511(5) -0.849(5) -0.294(3) 0.141(17) Uiso 1 1 d . . . O4 O 1.2364(3) -0.7112(2) -0.26785(16) 0.0622(7) Uani 1 1 d . . . C1 C 0.6390(5) 0.1933(3) -0.6724(2) 0.0469(9) Uani 1 1 d . . . C2 C 0.6479(4) 0.0796(3) -0.6030(2) 0.0521(10) Uani 1 1 d . . . H2A H 0.6041 0.1168 -0.5416 0.063 Uiso 1 1 d R . . H2B H 0.5757 0.0209 -0.6088 0.063 Uiso 1 1 d R . . C3 C 0.8228(4) -0.0036(3) -0.6122(2) 0.0454(9) Uani 1 1 d . . . H3A H 0.8636 -0.0477 -0.6714 0.054 Uiso 1 1 d R . . H3B H 0.8977 0.0552 -0.6109 0.054 Uiso 1 1 d R . . C4 C 0.8236(4) -0.1078(3) -0.5343(2) 0.0473(9) Uani 1 1 d . . . H4A H 0.7488 -0.1663 -0.5364 0.057 Uiso 1 1 d R . . H4B H 0.7799 -0.0629 -0.4754 0.057 Uiso 1 1 d R . . C5 C 0.9960(4) -0.1939(3) -0.5391(2) 0.0470(9) Uani 1 1 d . . . H5A H 1.0398 -0.2393 -0.5978 0.056 Uiso 1 1 d R . . H5B H 1.0712 -0.1356 -0.5370 0.056 Uiso 1 1 d R . . C6 C 0.9956(4) -0.2973(3) -0.4608(2) 0.0473(9) Uani 1 1 d . . . H6A H 0.9553 -0.2520 -0.4021 0.057 Uiso 1 1 d R . . H6B H 0.9183 -0.3543 -0.4618 0.057 Uiso 1 1 d R . . C7 C 1.1680(4) -0.3847(3) -0.4676(2) 0.0483(9) Uani 1 1 d . . . H7A H 1.2080 -0.4295 -0.5265 0.058 Uiso 1 1 d R . . H7B H 1.2449 -0.3273 -0.4669 0.058 Uiso 1 1 d R . . C8 C 1.1711(4) -0.4912(3) -0.3910(2) 0.0481(9) Uani 1 1 d . . . H8A H 1.1317 -0.4469 -0.3319 0.058 Uiso 1 1 d R . . H8B H 1.0946 -0.5491 -0.3916 0.058 Uiso 1 1 d R . . C9 C 1.3452(4) -0.5758(3) -0.4004(2) 0.0520(10) Uani 1 1 d . . . H9A H 1.3882 -0.6112 -0.4624 0.062 Uiso 1 1 d R . . H9B H 1.4180 -0.5178 -0.3944 0.062 Uiso 1 1 d R . . C10 C 1.3562(5) -0.6911(3) -0.3330(2) 0.0483(9) Uani 1 1 d . . . N1A N 1.5561(3) -0.9638(3) -0.23232(18) 0.0463(7) Uani 1 1 d . . . C2A C 1.4513(4) -1.0077(3) -0.1559(2) 0.0443(9) Uani 1 1 d . . . C3A C 1.5144(5) -1.1015(3) -0.0959(2) 0.0654(11) Uani 1 1 d . . . H3AA H 1.4394 -1.1321 -0.0406 0.079 Uiso 1 1 d R . . C4A C 1.6835(5) -1.1479(4) -0.1171(3) 0.0752(12) Uani 1 1 d . . . H4AA H 1.7269 -1.2133 -0.0762 0.090 Uiso 1 1 d R . . C5A C 1.7937(5) -1.1061(4) -0.1962(3) 0.0676(11) Uani 1 1 d . . . H5AA H 1.9135 -1.1391 -0.2110 0.081 Uiso 1 1 d R . . C6A C 1.7224(5) -1.0138(3) -0.2502(2) 0.0593(10) Uani 1 1 d . . . H6AA H 1.7957 -0.9827 -0.3060 0.071 Uiso 1 1 d R . . N7A N 1.2839(3) -0.9481(3) -0.14201(18) 0.0526(8) Uani 1 1 d . . . H7AN H 1.2596 -0.8671 -0.1768 0.063 Uiso 1 1 d R . . C8A C 1.1442(4) -0.9767(3) -0.0697(2) 0.0427(9) Uani 1 1 d . . . C9A C 1.0181(4) -0.8704(3) -0.0274(2) 0.0484(9) Uani 1 1 d . . . H9A' H 1.0465 -0.7839 -0.0465 0.058 Uiso 1 1 d R . . C10A C 1.1236(4) -1.1064(3) -0.0422(2) 0.0517(9) Uani 1 1 d . . . H10A H 1.2049 -1.1853 -0.0678 0.062 Uiso 1 1 d R . . N1B N 0.4368(4) 0.4654(3) -0.77645(19) 0.0489(7) Uani 1 1 d . . . C2B C 0.5497(4) 0.5220(3) -0.8414(2) 0.0397(8) Uani 1 1 d . . . C3B C 0.5007(4) 0.6456(3) -0.8828(2) 0.0546(10) Uani 1 1 d . . . H3BA H 0.5828 0.6878 -0.9275 0.066 Uiso 1 1 d R . . C4B C 0.3325(4) 0.7061(3) -0.8577(2) 0.0577(10) Uani 1 1 d . . . H4BA H 0.2962 0.7905 -0.8860 0.069 Uiso 1 1 d R . . C5B C 0.2149(4) 0.6454(4) -0.7926(2) 0.0567(10) Uani 1 1 d . . . H5BA H 0.0972 0.6867 -0.7747 0.068 Uiso 1 1 d R . . C6B C 0.2728(5) 0.5273(4) -0.7537(2) 0.0563(10) Uani 1 1 d . . . H6BA H 0.1924 0.4839 -0.7088 0.068 Uiso 1 1 d R . . N7B N 0.7133(3) 0.4527(2) -0.85924(17) 0.0487(8) Uani 1 1 d . . . H7BN H 0.7304 0.3751 -0.8201 0.058 Uiso 1 1 d R . . C8B C 0.8540(4) 0.4804(3) -0.9302(2) 0.0401(9) Uani 1 1 d . . . C9B C 1.0071(4) 0.4684(3) -0.9109(2) 0.0483(9) Uani 1 1 d . . . H9B' H 1.0110 0.4475 -0.8481 0.058 Uiso 1 1 d R . . C10B C 0.8491(4) 0.5124(3) -1.0208(2) 0.0475(9) Uani 1 1 d . . . H10B H 0.7420 0.5256 -1.0339 0.057 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 O1 0.0422(18) 0.0825(19) 0.084(2) 0.0467(17) -0.0103(15) -0.0038(14) O2 0.0469(17) 0.0681(17) 0.0594(16) 0.0309(13) -0.0034(14) -0.0057(13) O3 0.0415(17) 0.0773(18) 0.0646(18) 0.0328(15) 0.0014(13) 0.0061(14) O4 0.0506(17) 0.0640(17) 0.0582(16) 0.0235(13) -0.0072(14) -0.0008(13) C1 0.047(3) 0.045(2) 0.046(2) 0.0089(18) -0.015(2) -0.004(2) C2 0.043(2) 0.056(2) 0.053(2) 0.0221(19) -0.0139(19) -0.0101(18) C3 0.047(2) 0.045(2) 0.044(2) 0.0124(17) -0.0154(18) -0.0077(17) C4 0.046(2) 0.050(2) 0.045(2) 0.0112(17) -0.0156(18) -0.0093(17) C5 0.048(2) 0.049(2) 0.044(2) 0.0149(19) -0.0163(18) -0.0095(17) C6 0.049(2) 0.044(2) 0.048(2) 0.0108(18) -0.0180(19) -0.0060(17) C7 0.041(2) 0.051(2) 0.048(2) 0.0170(17) -0.0118(17) -0.0066(17) C8 0.045(2) 0.050(2) 0.047(2) 0.0144(17) -0.0162(18) -0.0049(17) C9 0.050(2) 0.051(2) 0.051(2) 0.0194(18) -0.0114(19) -0.0116(18) C10 0.045(3) 0.057(2) 0.040(2) 0.0107(19) -0.009(2) -0.011(2) N1A 0.0383(19) 0.0492(17) 0.0415(18) 0.0134(14) -0.0044(15) -0.0013(15) C2A 0.037(2) 0.050(2) 0.043(2) 0.0096(18) -0.0113(19) -0.0039(17) C3A 0.052(3) 0.075(3) 0.057(3) 0.038(2) -0.013(2) -0.003(2) C4A 0.050(3) 0.089(3) 0.075(3) 0.036(2) -0.021(2) 0.003(2) C5A 0.039(2) 0.078(3) 0.070(3) 0.023(2) -0.010(2) 0.005(2) C6A 0.040(3) 0.071(3) 0.051(2) 0.013(2) -0.002(2) 0.004(2) N7A 0.0360(19) 0.0542(18) 0.0543(19) 0.0247(14) -0.0046(16) 0.0001(15) C8A 0.034(2) 0.047(2) 0.041(2) 0.0142(18) -0.0079(18) -0.0048(17) C9A 0.044(2) 0.045(2) 0.051(2) 0.0094(17) -0.0094(18) -0.0050(17) C10A 0.047(2) 0.042(2) 0.059(2) 0.0081(18) -0.0113(19) 0.0021(16) N1B 0.037(2) 0.0573(18) 0.0468(19) 0.0141(15) -0.0079(16) -0.0077(15) C2B 0.040(2) 0.040(2) 0.035(2) 0.0085(17) -0.0084(18) -0.0046(17) C3B 0.042(2) 0.060(2) 0.049(2) 0.0136(19) -0.0027(18) -0.0035(18) C4B 0.057(3) 0.058(2) 0.050(2) 0.0083(19) -0.015(2) 0.005(2) C5B 0.040(2) 0.072(3) 0.046(2) 0.006(2) -0.0079(19) 0.0065(19) C6B 0.038(2) 0.077(3) 0.047(2) 0.014(2) -0.0056(19) -0.010(2) N7B 0.0348(18) 0.0494(17) 0.0481(18) 0.0228(14) -0.0022(15) 0.0005(14) C8B 0.037(2) 0.038(2) 0.037(2) 0.0108(16) -0.0026(18) -0.0042(16) C9B 0.046(2) 0.056(2) 0.038(2) 0.0101(16) -0.0099(18) -0.0044(17) C10B 0.037(2) 0.054(2) 0.045(2) 0.0087(17) -0.0096(18) -0.0018(16) _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 O1 C1 1.319(4) . ? O1 H1O 0.99(5) . ? O2 C1 1.201(4) . ? O3 C10 1.300(4) . ? O3 H3O 1.14(5) . ? O4 C10 1.224(4) . ? C1 C2 1.502(4) . ? C2 C3 1.512(4) . ? C2 H2A 0.9601 . ? C2 H2B 0.9600 . ? C3 C4 1.519(4) . ? C3 H3A 0.9599 . ? C3 H3B 0.9600 . ? C4 C5 1.517(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C5 C6 1.517(4) . ? C5 H5A 0.9601 . ? C5 H5B 0.9601 . ? C6 C7 1.516(4) . ? C6 H6A 0.9601 . ? C6 H6B 0.9600 . ? C7 C8 1.522(4) . ? C7 H7A 0.9599 . ? C7 H7B 0.9601 . ? C8 C9 1.512(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9601 . ? C9 C10 1.496(4) . ? C9 H9A 0.9601 . ? C9 H9B 0.9600 . ? N1A C2A 1.339(4) . ? N1A C6A 1.341(4) . ? N1A H3O 1.49(5) . ? C2A N7A 1.375(4) . ? C2A C3A 1.394(4) . ? C3A C4A 1.354(4) . ? C3A H3AA 0.9601 . ? C4A C5A 1.377(5) . ? C4A H4AA 0.9601 . ? C5A C6A 1.356(4) . ? C5A H5AA 0.9600 . ? C6A H6AA 0.9600 . ? N7A C8A 1.413(4) . ? N7A H7AN 0.9599 . ? C8A C10A 1.381(4) . ? C8A C9A 1.387(4) . ? C9A C10A 1.388(4) 2_735 ? C9A H9A' 0.9600 . ? C10A C9A 1.388(4) 2_735 ? C10A H10A 0.9599 . ? N1B C2B 1.338(4) . ? N1B C6B 1.348(4) . ? C2B N7B 1.370(4) . ? C2B C3B 1.396(4) . ? C3B C4B 1.375(4) . ? C3B H3BA 0.9601 . ? C4B C5B 1.384(4) . ? C4B H4BA 0.9600 . ? C5B C6B 1.355(4) . ? C5B H5BA 0.9600 . ? C6B H6BA 0.9601 . ? N7B C8B 1.406(4) . ? N7B H7BN 0.9600 . ? C8B C9B 1.383(4) . ? C8B C10B 1.386(4) . ? C9B C10B 1.379(4) 2_763 ? C9B H9B' 0.9600 . ? C10B C9B 1.379(4) 2_763 ? C10B H10B 0.9599 . ? 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 C1 O1 H1O 117(2) . . ? C10 O3 H3O 111(2) . . ? O2 C1 O1 122.8(3) . . ? O2 C1 C2 125.3(3) . . ? O1 C1 C2 111.9(3) . . ? C1 C2 C3 115.2(3) . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 111.9(3) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 114.5(3) . . ? C5 C4 H4A 108.3 . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 114.1(2) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 108.3 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 113.6(2) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 114.8(3) . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 113.0(3) . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 116.3(3) . . ? C10 C9 H9A 108.2 . . ? C8 C9 H9A 107.9 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.2 . . ? H9A C9 H9B 107.3 . . ? O4 C10 O3 123.2(3) . . ? O4 C10 C9 123.4(3) . . ? O3 C10 C9 113.4(3) . . ? C2A N1A C6A 118.3(3) . . ? C2A N1A H3O 126.3(16) . . ? C6A N1A H3O 114.7(15) . . ? N1A C2A N7A 114.1(3) . . ? N1A C2A C3A 120.6(3) . . ? N7A C2A C3A 125.2(3) . . ? C4A C3A C2A 118.6(3) . . ? C4A C3A H3AA 120.8 . . ? C2A C3A H3AA 120.6 . . ? C3A C4A C5A 122.0(3) . . ? C3A C4A H4AA 118.6 . . ? C5A C4A H4AA 119.4 . . ? C6A C5A C4A 115.8(3) . . ? C6A C5A H5AA 122.4 . . ? C4A C5A H5AA 121.8 . . ? N1A C6A C5A 124.8(3) . . ? N1A C6A H6AA 117.4 . . ? C5A C6A H6AA 117.9 . . ? C2A N7A C8A 127.2(3) . . ? C2A N7A H7AN 117.2 . . ? C8A N7A H7AN 114.5 . . ? C10A C8A C9A 118.3(3) . . ? C10A C8A N7A 122.8(3) . . ? C9A C8A N7A 118.9(3) . . ? C8A C9A C10A 121.0(3) . 2_735 ? C8A C9A H9A' 113.0 . . ? C10A C9A H9A' 125.7 2_735 . ? C8A C10A C9A 120.7(3) . 2_735 ? C8A C10A H10A 123.5 . . ? C9A C10A H10A 115.7 2_735 . ? C2B N1B C6B 118.9(3) . . ? N1B C2B N7B 114.7(3) . . ? N1B C2B C3B 121.0(3) . . ? N7B C2B C3B 124.2(3) . . ? C4B C3B C2B 118.5(3) . . ? C4B C3B H3BA 120.7 . . ? C2B C3B H3BA 120.7 . . ? C3B C4B C5B 120.5(3) . . ? C3B C4B H4BA 119.7 . . ? C5B C4B H4BA 119.8 . . ? C6B C5B C4B 117.5(3) . . ? C6B C5B H5BA 121.3 . . ? C4B C5B H5BA 121.1 . . ? N1B C6B C5B 123.6(3) . . ? N1B C6B H6BA 118.0 . . ? C5B C6B H6BA 118.4 . . ? C2B N7B C8B 126.9(3) . . ? C2B N7B H7BN 115.2 . . ? C8B N7B H7BN 117.8 . . ? C9B C8B C10B 117.8(3) . . ? C9B C8B N7B 119.2(3) . . ? C10B C8B N7B 122.8(3) . . ? C10B C9B C8B 121.5(3) 2_763 . ? C10B C9B H9B' 120.3 2_763 . ? C8B C9B H9B' 118.2 . . ? C9B C10B C8B 120.7(3) 2_763 . ? C9B C10B H10B 121.1 2_763 . ? C8B C10B H10B 118.2 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.179 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.040 #===END data_2sq _database_code_CSD 191444 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,4-diaminobenzene squaric acid co-crystal ; _chemical_name_common ? _chemical_melting_point 284-285 _chemical_formula_moiety 'C16H14N4, C4H2O4' _chemical_formula_sum 'C20 H16 N4 O4' _chemical_formula_weight 376.37 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' 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 3.8420(10) _cell_length_b 9.062(2) _cell_length_c 12.098(2) _cell_angle_alpha 87.23(3) _cell_angle_beta 81.25(3) _cell_angle_gamma 78.18(3) _cell_volume 407.41(15) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 3082 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1442 _reflns_number_gt 1154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0250P)^2^+0.4316P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1442 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 0.1283(5) 0.6425(2) 0.18366(16) 0.0174(5) Uani 1 1 d . . . H1 H -0.019(9) 0.706(4) 0.125(3) 0.049(9) Uiso 1 1 d . . . C2 C 0.1701(6) 0.6981(3) 0.28216(19) 0.0161(5) Uani 1 1 d . . . C3 C 0.3773(6) 0.6006(3) 0.3539(2) 0.0196(5) Uani 1 1 d . . . H3 H 0.4233 0.6411 0.4209 0.012(6) Uiso 1 1 d R . . C4 C 0.5269(6) 0.4551(3) 0.3229(2) 0.0213(6) Uani 1 1 d . . . H4 H 0.6696 0.3902 0.3713 0.033(8) Uiso 1 1 d R . . C5 C 0.4757(6) 0.4004(3) 0.2212(2) 0.0212(6) Uani 1 1 d . . . H5 H 0.5836 0.2990 0.1991 0.022(7) Uiso 1 1 d R . . C6 C 0.2771(7) 0.4982(3) 0.1536(2) 0.0211(6) Uani 1 1 d . . . H6 H 0.2203 0.4707 0.0838 0.012(6) Uiso 1 1 d R . . N7 N 0.0129(5) 0.8434(2) 0.30282(16) 0.0185(5) Uani 1 1 d . . . H7 H -0.1021 0.9046 0.2465 0.038(8) Uiso 1 1 d R . . C8 C 0.0121(6) 0.9186(3) 0.40398(19) 0.0161(5) Uani 1 1 d . . . C9 C 0.1027(6) 1.0613(3) 0.3951(2) 0.0182(5) Uani 1 1 d . . . H9 H 0.1726 1.1004 0.3217 0.032(8) Uiso 1 1 d R . . C10 C -0.0908(6) 0.8592(3) 0.50871(19) 0.0186(5) Uani 1 1 d . . . H10 H -0.1583 0.7626 0.5121 0.038(8) Uiso 1 1 d R . . O1A O -0.2319(5) 0.75152(18) 0.02221(14) 0.0232(4) Uani 1 1 d . . . O2A O -0.3227(4) 1.04898(18) 0.16546(13) 0.0211(4) Uani 1 1 d . . . C1A C -0.3802(6) 0.8886(3) 0.00897(19) 0.0180(5) Uani 1 1 d . . . C2A C -0.4218(6) 1.0232(3) 0.07447(19) 0.0182(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0208(10) 0.0154(10) 0.0166(11) -0.0009(8) -0.0032(9) -0.0045(8) C2 0.0165(11) 0.0175(12) 0.0140(12) -0.0017(10) -0.0009(9) -0.0037(10) C3 0.0204(12) 0.0224(13) 0.0167(12) -0.0023(10) -0.0039(10) -0.0044(10) C4 0.0221(13) 0.0183(13) 0.0224(13) 0.0016(10) -0.0033(11) -0.0021(10) C5 0.0230(13) 0.0162(12) 0.0226(13) -0.0024(10) 0.0003(10) -0.0021(10) C6 0.0249(13) 0.0222(13) 0.0171(13) -0.0028(10) -0.0026(10) -0.0066(11) N7 0.0241(11) 0.0160(10) 0.0150(10) -0.0020(8) -0.0067(9) 0.0003(8) C8 0.0181(12) 0.0166(12) 0.0132(12) -0.0011(9) -0.0052(9) 0.0001(9) C9 0.0196(12) 0.0186(12) 0.0154(12) 0.0009(10) -0.0028(10) -0.0014(10) C10 0.0178(12) 0.0197(13) 0.0180(13) -0.0016(10) -0.0037(10) -0.0020(10) O1A 0.0316(10) 0.0176(9) 0.0201(9) -0.0006(7) -0.0088(8) -0.0006(7) O2A 0.0275(9) 0.0202(9) 0.0154(9) -0.0014(7) -0.0051(7) -0.0024(7) C1A 0.0201(12) 0.0175(12) 0.0161(12) -0.0019(10) 0.0007(10) -0.0051(10) C2A 0.0190(12) 0.0207(13) 0.0153(12) 0.0003(10) -0.0014(10) -0.0060(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 N1 C6 1.358(3) . ? N1 C2 1.360(3) . ? N1 H1 1.05(3) . ? C2 N7 1.349(3) . ? C2 C3 1.420(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9600 . ? C4 C5 1.404(3) . ? C4 H4 0.9600 . ? C5 C6 1.371(3) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.428(3) . ? N7 H7 0.9600 . ? C8 C10 1.386(3) . ? C8 C9 1.401(3) . ? C9 C10 1.389(3) 2_576 ? C9 H9 0.9600 . ? C10 C9 1.389(3) 2_576 ? C10 H10 0.9600 . ? O1A C1A 1.270(3) . ? O2A C2A 1.265(3) . ? C1A C2A 1.455(3) . ? C1A C2A 1.464(3) 2_475 ? C2A C1A 1.464(3) 2_475 ? 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 121.8(2) . . ? C6 N1 H1 114.7(17) . . ? C2 N1 H1 123.5(17) . . ? N7 C2 N1 116.7(2) . . ? N7 C2 C3 125.3(2) . . ? N1 C2 C3 118.0(2) . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 118.5 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 117.6(2) . . ? C6 C5 H5 121.5 . . ? C4 C5 H5 120.8 . . ? N1 C6 C5 121.9(2) . . ? N1 C6 H6 114.2 . . ? C5 C6 H6 123.9 . . ? C2 N7 C8 124.57(19) . . ? C2 N7 H7 120.1 . . ? C8 N7 H7 115.3 . . ? C10 C8 C9 119.5(2) . . ? C10 C8 N7 122.6(2) . . ? C9 C8 N7 117.8(2) . . ? C10 C9 C8 119.6(2) 2_576 . ? C10 C9 H9 122.2 2_576 . ? C8 C9 H9 118.2 . . ? C8 C10 C9 120.8(2) . 2_576 ? C8 C10 H10 117.7 . . ? C9 C10 H10 121.5 2_576 . ? O1A C1A C2A 133.4(2) . . ? O1A C1A C2A 136.1(2) . 2_475 ? C2A C1A C2A 90.43(19) . 2_475 ? O2A C2A C1A 133.9(2) . . ? O2A C2A C1A 136.5(2) . 2_475 ? C1A C2A C1A 89.57(19) . 2_475 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.232 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.057 #===END data_2tere _database_code_CSD 191445 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-1,4-diaminobenzene 1,4-benzenedicarboxylic acid ; _chemical_name_common ? _chemical_melting_point 259 _chemical_formula_moiety 'C16H14N4, C8H6O4' _chemical_formula_sum 'C24 H20 N4 O4' _chemical_formula_weight 428.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7670(13) _cell_length_b 8.8044(17) _cell_length_c 9.1959(17) _cell_angle_alpha 62.048(19) _cell_angle_beta 71.921(17) _cell_angle_gamma 70.707(16) _cell_volume 515.10(16) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 8 _cell_measurement_theta_max 27 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.792 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 1621 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.54 _diffrn_reflns_theta_max 65.07 _reflns_number_total 1621 _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^)+(0.0918P)^2^+0.0634P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1621 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.2296(2) -0.17270(18) 1.01075(16) 0.0412(4) Uani 1 1 d . . . H1N H 0.294(4) -0.053(3) 0.916(3) 0.090(8) Uiso 1 1 d . . . N7 N 0.1487(2) -0.05094(18) 1.20070(16) 0.0412(4) Uani 1 1 d . . . H7 H 0.2232 0.0304 1.1167 0.071(6) Uiso 1 1 d R . . C2 C 0.1460(2) -0.1840(2) 1.16658(19) 0.0365(4) Uani 1 1 d . . . C3 C 0.06823(19) -0.33187(16) 1.27861(16) 0.0458(4) Uani 1 1 d . . . H3 H 0.0078 -0.3345 1.3878 0.065 Uiso 1 1 d R . . C4 C 0.08228(19) -0.45841(16) 1.22709(16) 0.0523(5) Uani 1 1 d R . . H4 H 0.0261 -0.5577 1.2982 0.066(6) Uiso 1 1 d R . . C5 C 0.1730(3) -0.4457(2) 1.0668(2) 0.0556(5) Uani 1 1 d . . . H5 H 0.1912 -0.5302 1.0223 0.070(6) Uiso 1 1 d R . . C6 C 0.2429(3) -0.2993(2) 0.9634(2) 0.0516(5) Uani 1 1 d . . . H6 H 0.3127 -0.2819 0.8526 0.070(6) Uiso 1 1 d R . . C8 C 0.0721(2) -0.02897(19) 1.35276(19) 0.0357(4) Uani 1 1 d . . . C9 C -0.1046(2) -0.0550(2) 1.4433(2) 0.0403(4) Uani 1 1 d . . . H9 H -0.1785 -0.0880 1.4010 0.052(5) Uiso 1 1 d R . . C10 C 0.1741(2) 0.0270(2) 1.4108(2) 0.0407(4) Uani 1 1 d . . . H10 H 0.2979 0.0403 1.3525 0.059(5) Uiso 1 1 d R . . O1A O 0.36807(16) 0.07816(14) 0.76824(13) 0.0452(4) Uani 1 1 d . . . O2A O 0.34087(18) 0.20881(15) 0.93421(14) 0.0511(4) Uani 1 1 d . . . C1A C 0.4429(2) 0.35727(18) 0.64104(18) 0.0353(4) Uani 1 1 d . . . C2A C 0.4770(2) 0.4920(2) 0.6583(2) 0.0424(4) Uani 1 1 d . . . H2A H 0.4645 0.4847 0.7685 0.059(6) Uiso 1 1 d R . . C3A C 0.4669(2) 0.3649(2) 0.4821(2) 0.0425(4) Uani 1 1 d . . . H3A H 0.4415 0.2744 0.4666 0.054(5) Uiso 1 1 d R . . C4A C 0.3788(2) 0.2043(2) 0.79538(19) 0.0366(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0569(8) 0.0407(7) 0.0258(8) -0.0144(6) 0.0035(6) -0.0196(6) N7 0.0608(8) 0.0397(7) 0.0252(8) -0.0152(6) 0.0065(6) -0.0238(6) C2 0.0455(8) 0.0370(8) 0.0253(9) -0.0120(7) -0.0004(6) -0.0136(6) C3 0.0608(10) 0.0413(9) 0.0299(9) -0.0125(7) 0.0066(7) -0.0215(8) C4 0.0694(11) 0.0401(9) 0.0442(11) -0.0130(8) 0.0017(8) -0.0260(8) C5 0.0781(13) 0.0490(11) 0.0483(12) -0.0274(9) 0.0030(9) -0.0267(9) C6 0.0760(12) 0.0482(10) 0.0331(10) -0.0217(8) 0.0066(8) -0.0245(9) C8 0.0497(9) 0.0303(7) 0.0240(8) -0.0100(6) 0.0007(6) -0.0136(6) C9 0.0496(9) 0.0458(9) 0.0321(9) -0.0196(7) 0.0002(7) -0.0199(7) C10 0.0450(9) 0.0438(9) 0.0358(9) -0.0200(7) 0.0041(6) -0.0180(7) O1A 0.0664(8) 0.0421(7) 0.0285(7) -0.0120(5) 0.0042(5) -0.0296(5) O2A 0.0833(9) 0.0471(7) 0.0239(7) -0.0119(5) 0.0053(6) -0.0337(6) C1A 0.0413(8) 0.0341(8) 0.0259(9) -0.0086(7) -0.0005(6) -0.0136(6) C2A 0.0614(10) 0.0422(9) 0.0229(9) -0.0104(7) 0.0006(7) -0.0229(7) C3A 0.0633(10) 0.0379(9) 0.0283(9) -0.0117(7) 0.0003(7) -0.0245(7) C4A 0.0442(8) 0.0358(8) 0.0271(9) -0.0107(7) -0.0011(6) -0.0143(6) _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 1.339(2) . ? N1 C2 1.348(2) . ? N1 H1N 1.16(3) . ? N7 C2 1.355(2) . ? N7 C8 1.417(2) . ? N7 H7 0.9600 . ? C2 C3 1.413(2) . ? C3 C4 1.3638 . ? C3 H3 0.9600 . ? C4 C5 1.391(2) . ? C4 H4 0.9600 . ? C5 C6 1.361(3) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? C8 C10 1.387(2) . ? C8 C9 1.396(2) . ? C9 C10 1.387(2) 2_558 ? C9 H9 0.9600 . ? C10 C9 1.387(2) 2_558 ? C10 H10 0.9600 . ? O1A C4A 1.2790(18) . ? O1A H1N 1.41(3) . ? O2A C4A 1.2349(19) . ? C1A C2A 1.383(2) . ? C1A C3A 1.387(2) . ? C1A C4A 1.513(2) . ? C2A C3A 1.390(2) 2_666 ? C2A H2A 0.9600 . ? C3A C2A 1.390(2) 2_666 ? C3A H3A 0.9601 . ? 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 121.37(14) . . ? C6 N1 H1N 118.8(13) . . ? C2 N1 H1N 119.9(13) . . ? C2 N7 C8 127.59(13) . . ? C2 N7 H7 116.0 . . ? C8 N7 H7 116.0 . . ? N1 C2 N7 115.51(14) . . ? N1 C2 C3 118.11(13) . . ? N7 C2 C3 126.37(13) . . ? C4 C3 C2 119.43(8) . . ? C4 C3 H3 124.7 . . ? C2 C3 H3 115.9 . . ? C3 C4 C5 121.33(9) . . ? C3 C4 H4 121.5 . . ? C5 C4 H4 117.1 . . ? C6 C5 C4 116.74(15) . . ? C6 C5 H5 117.0 . . ? C4 C5 H5 126.3 . . ? N1 C6 C5 122.99(16) . . ? N1 C6 H6 114.3 . . ? C5 C6 H6 122.6 . . ? C10 C8 C9 118.60(14) . . ? C10 C8 N7 118.59(14) . . ? C9 C8 N7 122.76(14) . . ? C10 C9 C8 120.14(15) 2_558 . ? C10 C9 H9 120.7 2_558 . ? C8 C9 H9 119.1 . . ? C8 C10 C9 121.26(15) . 2_558 ? C8 C10 H10 119.4 . . ? C9 C10 H10 119.2 2_558 . ? C4A O1A H1N 111.9(10) . . ? C2A C1A C3A 119.44(14) . . ? C2A C1A C4A 119.71(14) . . ? C3A C1A C4A 120.85(13) . . ? C1A C2A C3A 120.59(15) . 2_666 ? C1A C2A H2A 119.4 . . ? C3A C2A H2A 120.0 2_666 . ? C1A C3A C2A 119.97(15) . 2_666 ? C1A C3A H3A 121.1 . . ? C2A C3A H3A 118.9 2_666 . ? O2A C4A O1A 125.21(13) . . ? O2A C4A C1A 119.60(13) . . ? O1A C4A C1A 115.19(13) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 65.07 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.192 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.064 #===END data_3tere _database_code_CSD 191446 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-4,4'-methylenebis(aminobenzene) 1,4-benzenedicarboxylic acid ethanol 2:1:2 ; _chemical_name_common ? _chemical_melting_point 'clouds at 76C, begins to melt at 176C' _chemical_formula_moiety 'C23H20N4, 0.5(C8H6O4), C2H6O' _chemical_formula_sum 'C29 H29 N4 O3' _chemical_formula_weight 481.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.7830(11) _cell_length_b 10.6035(11) _cell_length_c 13.8087(15) _cell_angle_alpha 88.060(9) _cell_angle_beta 87.645(9) _cell_angle_gamma 86.861(9) _cell_volume 1282.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _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 ; ? ; _diffrn_ambient_temperature 294(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 9437 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 24.41 _reflns_number_total 4179 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0887P)^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,geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4179 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1515 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.1934 _refine_ls_wR_factor_gt 0.1562 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5055(3) 0.5987(3) 0.3991(2) 0.0626(8) Uani 1 1 d . . . H1N H 0.420(4) 0.670(4) 0.425(3) 0.097(12) Uiso 1 1 d . . . C2 C 0.4653(4) 0.4962(3) 0.3526(2) 0.0574(9) Uani 1 1 d . . . C3 C 0.5807(4) 0.4071(3) 0.3259(3) 0.0782(11) Uani 1 1 d . . . H3 H 0.5540 0.3341 0.2925 0.099(13) Uiso 1 1 d R . . C4 C 0.7280(5) 0.4264(4) 0.3472(3) 0.0918(13) Uani 1 1 d . . . H4 H 0.8073 0.3641 0.3304 0.115(15) Uiso 1 1 d R . . C5 C 0.7656(5) 0.5328(4) 0.3946(3) 0.0873(12) Uani 1 1 d . . . H5 H 0.8687 0.5486 0.4090 0.096(12) Uiso 1 1 d R . . C6 C 0.6502(4) 0.6172(4) 0.4187(3) 0.0763(11) Uani 1 1 d . . . H6 H 0.6755 0.6917 0.4508 0.091(12) Uiso 1 1 d R . . N7 N 0.3158(3) 0.4878(2) 0.3383(2) 0.0644(8) Uani 1 1 d . . . H7 H 0.2439 0.5496 0.3655 0.074(10) Uiso 1 1 d R . . C8 C 0.2542(4) 0.3888(3) 0.2869(3) 0.0565(9) Uani 1 1 d . . . C9 C 0.2943(4) 0.3721(3) 0.1906(3) 0.0781(11) Uani 1 1 d . . . H9 H 0.3648 0.4271 0.1584 0.087(11) Uiso 1 1 d R . . C10 C 0.2326(5) 0.2781(3) 0.1412(3) 0.0790(11) Uani 1 1 d . . . H10 H 0.2623 0.2663 0.0743 0.090(12) Uiso 1 1 d R . . C11 C 0.1297(4) 0.1979(3) 0.1852(3) 0.0614(9) Uani 1 1 d . . . C12 C 0.0905(4) 0.2168(3) 0.2815(3) 0.0680(10) Uani 1 1 d . . . H12 H 0.0185 0.1622 0.3127 0.094(12) Uiso 1 1 d R . . C13 C 0.1516(4) 0.3115(3) 0.3326(3) 0.0651(10) Uani 1 1 d . . . H13 H 0.1225 0.3232 0.3996 0.061(10) Uiso 1 1 d R . . C14 C 0.0639(4) 0.0954(3) 0.1298(3) 0.0830(12) Uani 1 1 d . . . H14B H 0.0399 0.1293 0.0666 0.087(13) Uiso 1 1 d R . . H14A H -0.0287 0.0689 0.1617 0.093(13) Uiso 1 1 d R . . C15 C 0.1694(4) -0.0201(3) 0.1162(3) 0.0619(9) Uani 1 1 d . . . C16 C 0.2571(6) -0.0364(4) 0.0344(3) 0.1065(15) Uani 1 1 d . . . H16 H 0.2563 0.0290 -0.0154 0.151(19) Uiso 1 1 d R . . C17 C 0.3535(6) -0.1433(4) 0.0209(3) 0.1073(16) Uani 1 1 d . . . H17 H 0.4125 -0.1516 -0.0389 0.117(15) Uiso 1 1 d R . . C18 C 0.3634(4) -0.2370(3) 0.0894(3) 0.0650(10) Uani 1 1 d . . . C19 C 0.2771(6) -0.2221(4) 0.1726(4) 0.1088(16) Uani 1 1 d . . . H19 H 0.2802 -0.2871 0.2227 0.128(16) Uiso 1 1 d R . . C20 C 0.1809(6) -0.1143(4) 0.1851(4) 0.1092(16) Uani 1 1 d . . . H20 H 0.1217 -0.1072 0.2449 0.107(14) Uiso 1 1 d R . . N21 N 0.4562(4) -0.3497(3) 0.0725(2) 0.0789(9) Uani 1 1 d . . . H21 H 0.4098 -0.4157 0.0403 0.138(17) Uiso 1 1 d R . . C22 C 0.6036(4) -0.3706(3) 0.0994(3) 0.0690(10) Uani 1 1 d G . . N23 N 0.6708(4) -0.4777(2) 0.0665(2) 0.0812(9) Uani 1 1 d G . . C24 C 0.8168(4) -0.5005(4) 0.0876(3) 0.1032(14) Uani 1 1 d G . . H24 H 0.8644 -0.5771 0.0630 0.112(14) Uiso 1 1 d R . . C25 C 0.9001(6) -0.4261(5) 0.1394(4) 0.1225(18) Uani 1 1 d . . . H25 H 1.0053 -0.4470 0.1518 0.145(19) Uiso 1 1 d R . . C26 C 0.8271(6) -0.3157(5) 0.1738(4) 0.1140(16) Uani 1 1 d . . . H26 H 0.8825 -0.2599 0.2109 0.119(15) Uiso 1 1 d R . . C27 C 0.6774(5) -0.2881(4) 0.1549(3) 0.0873(12) Uani 1 1 d . . . H27 H 0.6244 -0.2135 0.1795 0.099(13) Uiso 1 1 d R . . C4A C 0.0848(4) 0.8922(3) 0.4714(2) 0.0556(9) Uani 1 1 d . . . C2A C -0.0686(4) 0.9056(3) 0.4550(3) 0.0628(9) Uani 1 1 d . . . H2A H -0.1121 0.8346 0.4274 0.071(10) Uiso 1 1 d R . . C3A C 0.1539(4) 0.9882(3) 0.5162(3) 0.0630(9) Uani 1 1 d . . . H3A H 0.2561 0.9802 0.5386 0.059(9) Uiso 1 1 d R . . C1A C 0.1774(4) 0.7754(3) 0.4425(3) 0.0632(9) Uani 1 1 d . . . O1A O 0.3213(3) 0.7793(2) 0.4491(2) 0.0876(9) Uani 1 1 d . . . O2A O 0.1140(3) 0.6834(2) 0.4132(2) 0.0837(8) Uani 1 1 d . . . O1E O 0.5459(4) -0.0734(3) 0.3639(3) 0.1439(14) Uani 1 1 d . . . H1E H 0.4566 -0.1132 0.3894 0.173 Uiso 1 1 d R . . C2E C 0.5032(7) 0.0399(5) 0.3172(6) 0.145(2) Uani 1 1 d . . . H2EA H 0.4950 0.1059 0.3632 0.174 Uiso 1 1 d R . . H2EB H 0.4073 0.0333 0.2873 0.174 Uiso 1 1 d R . . C3E C 0.6198(11) 0.0701(6) 0.2459(5) 0.194(3) Uani 1 1 d . . . H3EA H 0.5965 0.1490 0.2121 0.233 Uiso 1 1 d R . . H3EB H 0.7150 0.0764 0.2767 0.233 Uiso 1 1 d R . . H3EC H 0.6267 0.0034 0.2004 0.233 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 0.0541(18) 0.0541(17) 0.081(2) -0.0135(15) -0.0021(15) -0.0046(15) C2 0.056(2) 0.0481(19) 0.067(2) -0.0028(17) 0.0006(17) 0.0001(17) C3 0.071(3) 0.063(2) 0.101(3) -0.016(2) -0.004(2) 0.005(2) C4 0.065(3) 0.084(3) 0.125(4) -0.009(3) -0.003(2) 0.017(2) C5 0.060(3) 0.091(3) 0.112(4) -0.007(3) -0.009(2) -0.004(2) C6 0.067(3) 0.073(3) 0.091(3) -0.009(2) -0.009(2) -0.012(2) N7 0.0546(18) 0.0493(16) 0.090(2) -0.0209(15) 0.0025(15) -0.0010(14) C8 0.053(2) 0.0428(18) 0.074(3) -0.0123(18) -0.0006(18) 0.0023(16) C9 0.093(3) 0.062(2) 0.080(3) -0.011(2) 0.014(2) -0.023(2) C10 0.094(3) 0.077(3) 0.066(3) -0.018(2) 0.012(2) -0.009(2) C11 0.050(2) 0.053(2) 0.081(3) -0.0179(19) -0.0051(18) 0.0067(16) C12 0.055(2) 0.064(2) 0.086(3) -0.008(2) 0.000(2) -0.0107(18) C13 0.060(2) 0.065(2) 0.070(3) -0.0137(19) 0.0024(19) -0.0059(19) C14 0.069(3) 0.073(2) 0.109(4) -0.036(2) -0.020(2) 0.004(2) C15 0.059(2) 0.055(2) 0.074(3) -0.022(2) -0.0087(19) -0.0017(17) C16 0.157(4) 0.085(3) 0.070(3) 0.006(3) 0.010(3) 0.039(3) C17 0.154(4) 0.088(3) 0.071(3) 0.003(3) 0.035(3) 0.042(3) C18 0.077(2) 0.052(2) 0.067(3) -0.015(2) -0.003(2) -0.0010(18) C19 0.159(5) 0.066(3) 0.094(4) 0.012(3) 0.040(3) 0.015(3) C20 0.137(4) 0.070(3) 0.113(4) -0.008(3) 0.062(3) 0.010(3) N21 0.086(2) 0.0520(17) 0.100(3) -0.0253(17) -0.0083(19) 0.0053(17) C22 0.078(3) 0.061(2) 0.067(3) -0.0127(19) 0.003(2) 0.004(2) N23 0.089(2) 0.074(2) 0.080(2) -0.0167(18) -0.0033(18) 0.0168(18) C24 0.101(4) 0.118(4) 0.089(4) -0.032(3) -0.009(3) 0.027(3) C25 0.091(4) 0.151(5) 0.125(5) -0.047(4) -0.020(3) 0.029(4) C26 0.098(4) 0.133(4) 0.115(4) -0.042(3) -0.021(3) -0.005(3) C27 0.093(3) 0.076(3) 0.095(3) -0.025(2) -0.004(2) -0.002(2) C4A 0.058(2) 0.0451(18) 0.064(2) -0.0081(16) 0.0097(17) -0.0050(16) C2A 0.063(2) 0.050(2) 0.076(3) -0.0177(18) 0.0070(18) -0.0127(18) C3A 0.056(2) 0.058(2) 0.076(3) -0.0144(19) -0.0046(18) -0.0060(18) C1A 0.061(2) 0.053(2) 0.076(3) -0.0071(18) 0.0070(19) -0.0088(18) O1A 0.0611(17) 0.0634(15) 0.140(3) -0.0309(15) 0.0057(15) -0.0051(13) O2A 0.0707(16) 0.0550(14) 0.127(2) -0.0318(15) 0.0047(14) -0.0080(12) O1E 0.100(2) 0.114(3) 0.219(4) 0.028(3) -0.023(2) -0.023(2) C2E 0.135(5) 0.082(3) 0.219(7) 0.039(4) -0.046(5) -0.002(3) C3E 0.336(11) 0.117(5) 0.127(6) -0.005(4) 0.044(6) -0.020(6) _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 1.337(4) . ? N1 C2 1.351(4) . ? N1 H1N 1.09(4) . ? C2 N7 1.344(4) . ? C2 C3 1.394(5) . ? C3 C4 1.366(5) . ? C3 H3 0.9600 . ? C4 C5 1.385(5) . ? C4 H4 0.9601 . ? C5 C6 1.353(5) . ? C5 H5 0.9600 . ? C6 H6 0.9601 . ? N7 C8 1.430(4) . ? N7 H7 0.9600 . ? C8 C13 1.371(4) . ? C8 C9 1.376(5) . ? C9 C10 1.374(5) . ? C9 H9 0.9600 . ? C10 C11 1.383(5) . ? C10 H10 0.9599 . ? C11 C12 1.378(5) . ? C11 C14 1.505(4) . ? C12 C13 1.390(4) . ? C12 H12 0.9599 . ? C13 H13 0.9599 . ? C14 C15 1.507(4) . ? C14 H14B 0.9600 . ? C14 H14A 0.9600 . ? C15 C16 1.351(5) . ? C15 C20 1.358(5) . ? C16 C17 1.391(5) . ? C16 H16 0.9600 . ? C17 C18 1.350(5) . ? C17 H17 0.9601 . ? C18 C19 1.359(5) . ? C18 N21 1.429(4) . ? C19 C20 1.396(6) . ? C19 H19 0.9599 . ? C20 H20 0.9601 . ? N21 C22 1.365(4) . ? N21 H21 0.9600 . ? C22 N23 1.3353 . ? C22 C27 1.387(5) . ? N23 C24 1.3336 . ? C24 C25 1.346(6) . ? C24 H24 0.9599 . ? C25 C26 1.392(6) . ? C25 H25 0.9599 . ? C26 C27 1.365(6) . ? C26 H26 0.9600 . ? C27 H27 0.9600 . ? C4A C2A 1.374(4) . ? C4A C3A 1.388(4) . ? C4A C1A 1.500(4) . ? C2A C3A 1.379(4) 2_576 ? C2A H2A 0.9601 . ? C3A C2A 1.379(4) 2_576 ? C3A H3A 0.9600 . ? C1A O2A 1.237(4) . ? C1A O1A 1.274(4) . ? O1A H1N 1.45(4) . ? O1E C2E 1.384(5) . ? O1E H1E 0.9600 . ? C2E C3E 1.432(8) . ? C2E H2EA 0.9599 . ? C2E H2EB 0.9600 . ? C3E H3EA 0.9600 . ? C3E H3EB 0.9600 . ? C3E H3EC 0.9599 . ? 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 122.3(3) . . ? C6 N1 H1N 116.4(18) . . ? C2 N1 H1N 121.2(18) . . ? N7 C2 N1 116.6(3) . . ? N7 C2 C3 125.6(3) . . ? N1 C2 C3 117.7(3) . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 118.7 . . ? C3 C4 C5 121.5(4) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.0 . . ? C6 C5 C4 117.2(4) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 122.6 . . ? N1 C6 C5 121.8(4) . . ? N1 C6 H6 120.5 . . ? C5 C6 H6 117.7 . . ? C2 N7 C8 124.0(3) . . ? C2 N7 H7 119.3 . . ? C8 N7 H7 116.7 . . ? C13 C8 C9 119.4(3) . . ? C13 C8 N7 120.2(3) . . ? C9 C8 N7 120.4(3) . . ? C10 C9 C8 120.1(4) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 122.0(4) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 118.4 . . ? C12 C11 C10 116.9(3) . . ? C12 C11 C14 121.9(4) . . ? C10 C11 C14 121.2(4) . . ? C11 C12 C13 121.8(3) . . ? C11 C12 H12 117.7 . . ? C13 C12 H12 120.4 . . ? C8 C13 C12 119.7(4) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 120.4 . . ? C11 C14 C15 114.4(3) . . ? C11 C14 H14B 108.1 . . ? C15 C14 H14B 107.7 . . ? C11 C14 H14A 110.3 . . ? C15 C14 H14A 107.9 . . ? H14B C14 H14A 108.2 . . ? C16 C15 C20 116.2(4) . . ? C16 C15 C14 121.9(4) . . ? C20 C15 C14 121.9(4) . . ? C15 C16 C17 122.2(4) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 118.3 . . ? C18 C17 C16 121.2(4) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 117.5(4) . . ? C17 C18 N21 120.8(4) . . ? C19 C18 N21 121.6(4) . . ? C18 C19 C20 120.6(4) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 119.4 . . ? C15 C20 C19 122.2(4) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 118.1 . . ? C22 N21 C18 125.3(3) . . ? C22 N21 H21 118.0 . . ? C18 N21 H21 116.7 . . ? N23 C22 N21 113.8(3) . . ? N23 C22 C27 122.9(3) . . ? N21 C22 C27 123.3(3) . . ? C24 N23 C22 116.2 . . ? N23 C24 C25 125.8(3) . . ? N23 C24 H24 115.6 . . ? C25 C24 H24 118.6 . . ? C24 C25 C26 116.9(5) . . ? C24 C25 H25 122.1 . . ? C26 C25 H25 120.9 . . ? C27 C26 C25 119.8(5) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C22 118.3(4) . . ? C26 C27 H27 120.9 . . ? C22 C27 H27 120.7 . . ? C2A C4A C3A 119.1(3) . . ? C2A C4A C1A 121.0(3) . . ? C3A C4A C1A 119.9(3) . . ? C4A C2A C3A 120.7(3) . 2_576 ? C4A C2A H2A 115.8 . . ? C3A C2A H2A 123.2 2_576 . ? C2A C3A C4A 120.1(3) 2_576 . ? C2A C3A H3A 115.5 2_576 . ? C4A C3A H3A 123.6 . . ? O2A C1A O1A 123.8(3) . . ? O2A C1A C4A 120.3(3) . . ? O1A C1A C4A 115.9(3) . . ? C1A O1A H1N 119.8(14) . . ? C2E O1E H1E 109.6 . . ? O1E C2E C3E 108.8(6) . . ? O1E C2E H2EA 109.4 . . ? C3E C2E H2EA 108.0 . . ? O1E C2E H2EB 110.1 . . ? C3E C2E H2EB 110.6 . . ? H2EA C2E H2EB 109.9 . . ? C2E C3E H3EA 112.1 . . ? C2E C3E H3EB 109.7 . . ? H3EA C3E H3EB 108.0 . . ? C2E C3E H3EC 107.1 . . ? H3EA C3E H3EC 109.2 . . ? H3EB C3E H3EC 110.8 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.41 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.140 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.033 #===END data_4tere _database_code_CSD 191447 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-4,4'-oxybis(aminobenzene) 1,4-benzenedicarboxylic acid hydrate 1:1:1 ; _chemical_name_common ? _chemical_melting_point 176 _chemical_formula_moiety 'C22H18N4O, C8H6O4, H2O' _chemical_formula_sum 'C30 H26 N4 O6' _chemical_formula_weight 538.55 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 10.3442(7) _cell_length_b 11.7028(9) _cell_length_c 12.6687(9) _cell_angle_alpha 78.461(6) _cell_angle_beta 65.910(6) _cell_angle_gamma 73.925(6) _cell_volume 1338.68(17) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 294(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 10143 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4640 _reflns_number_gt 3523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.163, 2000' _computing_cell_refinement 'KM4RED, Version 1.163, 2000' _computing_data_reduction 'KM4RED, Version 1.163, 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^)+(0.0879P)^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,geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4689 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.28595(14) 0.17859(12) 0.47572(11) 0.0450(3) Uani 1 1 d . . . H1 H 0.2654(19) 0.2649(18) 0.4441(16) 0.067(5) Uiso 1 1 d . . . C2 C 0.30355(15) 0.14868(13) 0.57853(13) 0.0386(3) Uani 1 1 d . . . C3 C 0.32488(16) 0.02713(13) 0.62099(14) 0.0445(4) Uani 1 1 d . . . H3 H 0.3408 0.0050 0.6940 0.055(5) Uiso 1 1 d R . . C4 C 0.32899(18) -0.05630(15) 0.55746(15) 0.0519(4) Uani 1 1 d . . . H4 H 0.3433 -0.1404 0.5918 0.058(5) Uiso 1 1 d R . . C5 C 0.31253(19) -0.02215(16) 0.45099(16) 0.0562(5) Uani 1 1 d . . . H5 H 0.3209 -0.0780 0.4041 0.069(6) Uiso 1 1 d R . . C6 C 0.28975(19) 0.09547(16) 0.41302(15) 0.0532(4) Uani 1 1 d . . . H6 H 0.2764 0.1292 0.3394 0.061(5) Uiso 1 1 d R . . N7 N 0.30196(16) 0.23924(12) 0.63028(11) 0.0474(3) Uani 1 1 d . . . H7 H 0.2937 0.3198 0.5860 0.068(5) Uiso 1 1 d R . . C8 C 0.31592(17) 0.22595(13) 0.73970(13) 0.0408(4) Uani 1 1 d . . . C9 C 0.21810(16) 0.17858(13) 0.84010(13) 0.0418(4) Uani 1 1 d . . . H9 H 0.1451 0.1474 0.8343 0.057(5) Uiso 1 1 d R . . C10 C 0.23077(16) 0.17157(13) 0.94585(13) 0.0400(4) Uani 1 1 d . . . H10 H 0.1637 0.1369 1.0181 0.048(4) Uiso 1 1 d R . . C11 C 0.34022(16) 0.21353(14) 0.95173(13) 0.0417(4) Uani 1 1 d . . . C12 C 0.43815(17) 0.26194(15) 0.85233(14) 0.0485(4) Uani 1 1 d . . . H12 H 0.5115 0.2938 0.8568 0.071(6) Uiso 1 1 d R . . C13 C 0.42554(17) 0.26756(14) 0.74641(14) 0.0467(4) Uani 1 1 d . . . H13 H 0.4964 0.3001 0.6756 0.060(5) Uiso 1 1 d R . . O14 O 0.33910(12) 0.20799(12) 1.06209(9) 0.0573(3) Uani 1 1 d . . . C15 C 0.46392(17) 0.21176(15) 1.07688(13) 0.0437(4) Uani 1 1 d . . . C16 C 0.59270(18) 0.12957(15) 1.03295(14) 0.0502(4) Uani 1 1 d . . . H16 H 0.5991 0.0737 0.9869 0.071(6) Uiso 1 1 d R . . C17 C 0.71034(17) 0.13120(13) 1.05732(13) 0.0444(4) Uani 1 1 d . . . H17 H 0.7990 0.0771 1.0249 0.057(5) Uiso 1 1 d R . . C18 C 0.70040(16) 0.21257(13) 1.12736(13) 0.0399(4) Uani 1 1 d . . . C19 C 0.56895(18) 0.29216(15) 1.17399(15) 0.0514(4) Uani 1 1 d . . . H19 H 0.5615 0.3443 1.2241 0.057(5) Uiso 1 1 d R . . C20 C 0.45235(18) 0.29297(15) 1.14674(14) 0.0511(4) Uani 1 1 d . . . H20 H 0.3636 0.3486 1.1753 0.067(5) Uiso 1 1 d R . . N21 N 0.82080(14) 0.20568(11) 1.15588(12) 0.0460(3) Uani 1 1 d . . . H21 H 0.8855 0.1293 1.1598 0.068(5) Uiso 1 1 d R . . C22 C 0.86560(16) 0.29929(13) 1.16726(13) 0.0389(3) Uani 1 1 d . . . N23 N 0.96147(13) 0.27254(12) 1.22018(11) 0.0424(3) Uani 1 1 d . . . H23 H 0.997(2) 0.174(2) 1.2563(17) 0.082(6) Uiso 1 1 d . . . C24 C 1.01467(18) 0.35906(16) 1.23457(15) 0.0530(4) Uani 1 1 d . . . H24 H 1.0826 0.3283 1.2739 0.066(5) Uiso 1 1 d R . . C25 C 0.9737(2) 0.47540(16) 1.19716(18) 0.0638(5) Uani 1 1 d . . . H25 H 1.0107 0.5338 1.2120 0.082(6) Uiso 1 1 d R . . C26 C 0.87861(19) 0.50388(15) 1.13975(17) 0.0589(5) Uani 1 1 d . . . H26 H 0.8496 0.5868 1.1081 0.080(6) Uiso 1 1 d R . . C27 C 0.82348(18) 0.41784(14) 1.12501(15) 0.0505(4) Uani 1 1 d . . . H27 H 0.7573 0.4343 1.0849 0.065(5) Uiso 1 1 d R . . O1A O 0.22610(14) 0.40338(10) 0.38886(10) 0.0605(4) Uani 1 1 d . . . O2A O 0.28452(14) 0.46957(10) 0.51298(11) 0.0602(4) Uani 1 1 d . . . O3A O 0.03997(14) 1.05681(10) 0.30815(10) 0.0559(3) Uani 1 1 d . . . O4A O 0.00957(12) 0.98855(9) 0.16949(9) 0.0489(3) Uani 1 1 d . . . C1A C 0.18449(16) 0.61244(13) 0.38898(13) 0.0403(4) Uani 1 1 d . . . C2A C 0.17869(18) 0.63719(14) 0.27916(14) 0.0457(4) Uani 1 1 d . . . H2A H 0.2058 0.5773 0.2311 0.057(5) Uiso 1 1 d R . . C3A C 0.13171(18) 0.75283(14) 0.23718(14) 0.0457(4) Uani 1 1 d . . . H3A H 0.1284 0.7686 0.1599 0.063(5) Uiso 1 1 d R . . C4A C 0.09000(15) 0.84709(13) 0.30425(13) 0.0390(4) Uani 1 1 d . . . C5A C 0.09478(17) 0.82267(14) 0.41456(13) 0.0435(4) Uani 1 1 d . . . H5A H 0.0652 0.8841 0.4614 0.053(5) Uiso 1 1 d R . . C6A C 0.14235(18) 0.70691(14) 0.45591(14) 0.0474(4) Uani 1 1 d . . . H6A H 0.1479 0.6912 0.5325 0.062(5) Uiso 1 1 d R . . C7A C 0.23485(18) 0.48606(14) 0.43395(14) 0.0454(4) Uani 1 1 d . . . C8A C 0.04325(16) 0.97253(13) 0.25631(13) 0.0406(4) Uani 1 1 d . . . O1W O 0.39947(18) 0.63030(14) 0.58228(14) 0.0873(5) Uani 1 1 d . . . H1WB H 0.3599 0.5762 0.5640 0.142(11) Uiso 1 1 d R . . H1WA H 0.4978 0.5881 0.5584 0.151(12) 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 0.0525(8) 0.0399(8) 0.0480(8) -0.0031(6) -0.0255(6) -0.0089(6) C2 0.0384(8) 0.0366(8) 0.0429(8) -0.0012(6) -0.0174(6) -0.0097(6) C3 0.0466(9) 0.0377(9) 0.0469(9) 0.0000(7) -0.0156(7) -0.0114(7) C4 0.0495(9) 0.0384(9) 0.0616(11) -0.0062(8) -0.0117(8) -0.0135(7) C5 0.0566(11) 0.0523(11) 0.0654(11) -0.0197(9) -0.0192(9) -0.0163(8) C6 0.0572(10) 0.0580(11) 0.0540(10) -0.0111(8) -0.0275(8) -0.0129(8) N7 0.0703(9) 0.0334(7) 0.0481(8) 0.0018(6) -0.0330(7) -0.0135(6) C8 0.0525(9) 0.0301(8) 0.0449(8) -0.0015(6) -0.0260(7) -0.0062(7) C9 0.0472(9) 0.0330(8) 0.0523(9) -0.0037(7) -0.0248(7) -0.0104(7) C10 0.0418(8) 0.0322(8) 0.0462(9) -0.0034(6) -0.0171(7) -0.0076(6) C11 0.0419(8) 0.0425(9) 0.0436(8) -0.0070(7) -0.0209(7) -0.0044(7) C12 0.0456(9) 0.0557(10) 0.0529(9) -0.0040(8) -0.0235(7) -0.0179(8) C13 0.0469(9) 0.0468(9) 0.0486(9) -0.0010(7) -0.0187(7) -0.0150(7) O14 0.0464(7) 0.0888(9) 0.0441(6) -0.0108(6) -0.0194(5) -0.0194(6) C15 0.0440(9) 0.0520(9) 0.0397(8) -0.0028(7) -0.0197(7) -0.0125(7) C16 0.0579(10) 0.0477(9) 0.0532(10) -0.0149(8) -0.0275(8) -0.0066(8) C17 0.0474(9) 0.0365(8) 0.0503(9) -0.0075(7) -0.0219(7) -0.0025(7) C18 0.0461(9) 0.0335(8) 0.0432(8) 0.0008(6) -0.0228(7) -0.0077(6) C19 0.0515(10) 0.0526(10) 0.0565(10) -0.0224(8) -0.0231(8) -0.0050(8) C20 0.0427(9) 0.0572(10) 0.0532(10) -0.0175(8) -0.0183(8) -0.0018(8) N21 0.0492(8) 0.0327(7) 0.0637(9) -0.0044(6) -0.0325(7) -0.0035(6) C22 0.0381(8) 0.0343(8) 0.0426(8) -0.0052(6) -0.0151(6) -0.0039(6) N23 0.0423(7) 0.0402(7) 0.0473(7) -0.0056(6) -0.0198(6) -0.0076(6) C24 0.0474(9) 0.0558(11) 0.0624(10) -0.0125(8) -0.0234(8) -0.0125(8) C25 0.0613(11) 0.0450(10) 0.0897(14) -0.0162(9) -0.0249(10) -0.0170(9) C26 0.0576(11) 0.0360(9) 0.0783(12) -0.0057(8) -0.0223(9) -0.0078(8) C27 0.0532(10) 0.0376(9) 0.0609(10) -0.0021(7) -0.0255(8) -0.0056(7) O1A 0.0929(10) 0.0363(6) 0.0612(7) -0.0045(5) -0.0431(7) -0.0060(6) O2A 0.0867(9) 0.0403(7) 0.0694(8) 0.0049(6) -0.0512(7) -0.0114(6) O3A 0.0794(9) 0.0359(6) 0.0697(8) -0.0018(5) -0.0477(7) -0.0108(6) O4A 0.0590(7) 0.0404(6) 0.0495(6) -0.0021(5) -0.0292(6) -0.0021(5) C1A 0.0423(8) 0.0358(8) 0.0445(8) 0.0003(7) -0.0205(7) -0.0076(6) C2A 0.0576(10) 0.0369(8) 0.0482(9) -0.0067(7) -0.0262(8) -0.0074(7) C3A 0.0569(10) 0.0428(9) 0.0431(9) 0.0003(7) -0.0276(7) -0.0093(7) C4A 0.0372(8) 0.0361(8) 0.0466(9) -0.0011(7) -0.0198(7) -0.0083(6) C5A 0.0491(9) 0.0370(8) 0.0458(9) -0.0069(7) -0.0209(7) -0.0045(7) C6A 0.0589(10) 0.0430(9) 0.0409(9) -0.0009(7) -0.0245(7) -0.0054(7) C7A 0.0536(9) 0.0376(9) 0.0451(9) -0.0008(7) -0.0214(7) -0.0076(7) C8A 0.0387(8) 0.0389(8) 0.0462(9) -0.0007(7) -0.0197(7) -0.0078(6) O1W 0.0812(11) 0.0754(10) 0.1146(12) -0.0374(9) -0.0373(9) -0.0105(8) _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 1.3520(19) . ? N1 C6 1.357(2) . ? N1 H1 1.01(2) . ? C2 N7 1.3464(19) . ? C2 C3 1.407(2) . ? C3 C4 1.366(2) . ? C3 H3 0.9767 . ? C4 C5 1.394(2) . ? C4 H4 0.9898 . ? C5 C6 1.353(2) . ? C5 H5 0.9322 . ? C6 H6 0.9856 . ? N7 C8 1.4252(18) . ? N7 H7 0.9967 . ? C8 C9 1.388(2) . ? C8 C13 1.390(2) . ? C9 C10 1.383(2) . ? C9 H9 0.9582 . ? C10 C11 1.386(2) . ? C10 H10 0.9858 . ? C11 O14 1.3821(18) . ? C11 C12 1.387(2) . ? C12 C13 1.387(2) . ? C12 H12 0.9585 . ? C13 H13 0.9839 . ? O14 C15 1.3915(18) . ? C15 C20 1.374(2) . ? C15 C16 1.382(2) . ? C16 C17 1.378(2) . ? C16 H16 0.9325 . ? C17 C18 1.384(2) . ? C17 H17 0.9413 . ? C18 C19 1.389(2) . ? C18 N21 1.4100(19) . ? C19 C20 1.381(2) . ? C19 H19 0.9322 . ? C20 H20 0.9432 . ? N21 C22 1.3545(19) . ? N21 H21 0.9631 . ? C22 N23 1.3482(18) . ? C22 C27 1.400(2) . ? N23 C24 1.351(2) . ? N23 H23 1.17(2) . ? C24 C25 1.358(3) . ? C24 H24 0.9727 . ? C25 C26 1.383(3) . ? C25 H25 0.9510 . ? C26 C27 1.362(2) . ? C26 H26 0.9871 . ? C27 H27 0.9669 . ? O1A C7A 1.2580(18) . ? O2A C7A 1.2615(18) . ? O3A C8A 1.2758(17) . ? O4A C8A 1.2491(17) . ? C1A C2A 1.386(2) . ? C1A C6A 1.392(2) . ? C1A C7A 1.504(2) . ? C2A C3A 1.382(2) . ? C2A H2A 0.9293 . ? C3A C4A 1.392(2) . ? C3A H3A 0.9727 . ? C4A C5A 1.388(2) . ? C4A C8A 1.499(2) . ? C5A C6A 1.382(2) . ? C5A H5A 0.9294 . ? C6A H6A 0.9725 . ? O1W H1WB 0.9496 . ? O1W H1WA 0.9493 . ? 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 122.14(14) . . ? C2 N1 H1 120.6(10) . . ? C6 N1 H1 117.2(10) . . ? N7 C2 N1 116.25(13) . . ? N7 C2 C3 125.67(14) . . ? N1 C2 C3 118.06(14) . . ? C4 C3 C2 119.62(15) . . ? C4 C3 H3 122.1 . . ? C2 C3 H3 118.2 . . ? C3 C4 C5 120.65(16) . . ? C3 C4 H4 116.2 . . ? C5 C4 H4 123.1 . . ? C6 C5 C4 118.57(16) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 122.0 . . ? C5 C6 N1 120.96(16) . . ? C5 C6 H6 125.2 . . ? N1 C6 H6 113.9 . . ? C2 N7 C8 124.52(13) . . ? C2 N7 H7 116.1 . . ? C8 N7 H7 119.4 . . ? C9 C8 C13 119.56(14) . . ? C9 C8 N7 121.51(13) . . ? C13 C8 N7 118.85(14) . . ? C10 C9 C8 120.19(14) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 119.0 . . ? C9 C10 C11 119.84(14) . . ? C9 C10 H10 121.6 . . ? C11 C10 H10 118.5 . . ? O14 C11 C10 115.33(14) . . ? O14 C11 C12 123.94(14) . . ? C10 C11 C12 120.67(14) . . ? C11 C12 C13 119.12(14) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.2 . . ? C12 C13 C8 120.62(15) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 120.2 . . ? C11 O14 C15 120.18(12) . . ? C20 C15 C16 120.07(14) . . ? C20 C15 O14 117.82(14) . . ? C16 C15 O14 121.81(14) . . ? C17 C16 C15 119.72(14) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.84(14) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C17 C18 C19 118.83(14) . . ? C17 C18 N21 118.70(13) . . ? C19 C18 N21 122.29(14) . . ? C20 C19 C18 120.32(14) . . ? C20 C19 H19 121.2 . . ? C18 C19 H19 118.5 . . ? C15 C20 C19 120.14(15) . . ? C15 C20 H20 118.6 . . ? C19 C20 H20 121.3 . . ? C22 N21 C18 126.15(13) . . ? C22 N21 H21 114.4 . . ? C18 N21 H21 119.1 . . ? N23 C22 N21 115.87(13) . . ? N23 C22 C27 119.27(14) . . ? N21 C22 C27 124.81(14) . . ? C22 N23 C24 120.70(14) . . ? C22 N23 H23 120.1(10) . . ? C24 N23 H23 119.2(10) . . ? N23 C24 C25 121.67(16) . . ? N23 C24 H24 112.7 . . ? C25 C24 H24 125.6 . . ? C24 C25 C26 118.34(16) . . ? C24 C25 H25 118.9 . . ? C26 C25 H25 122.8 . . ? C27 C26 C25 120.69(16) . . ? C27 C26 H26 118.4 . . ? C25 C26 H26 120.9 . . ? C26 C27 C22 119.28(16) . . ? C26 C27 H27 123.0 . . ? C22 C27 H27 117.7 . . ? C2A C1A C6A 118.43(13) . . ? C2A C1A C7A 120.28(13) . . ? C6A C1A C7A 121.28(13) . . ? C3A C2A C1A 120.82(14) . . ? C3A C2A H2A 117.4 . . ? C1A C2A H2A 121.8 . . ? C2A C3A C4A 120.58(14) . . ? C2A C3A H3A 119.7 . . ? C4A C3A H3A 119.7 . . ? C5A C4A C3A 118.81(13) . . ? C5A C4A C8A 121.17(13) . . ? C3A C4A C8A 120.01(13) . . ? C6A C5A C4A 120.34(14) . . ? C6A C5A H5A 119.5 . . ? C4A C5A H5A 120.2 . . ? C5A C6A C1A 121.01(14) . . ? C5A C6A H6A 119.6 . . ? C1A C6A H6A 119.4 . . ? O1A C7A O2A 124.25(14) . . ? O1A C7A C1A 117.45(14) . . ? O2A C7A C1A 118.30(13) . . ? O4A C8A O3A 124.08(14) . . ? O4A C8A C4A 118.82(13) . . ? O3A C8A C4A 117.10(13) . . ? H1WB O1W H1WA 99.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.239 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.038 #===END data_5fum _database_code_CSD 191448 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-2,2'-oxybis(aminobenzene) fumaric acid co-crystal ; _chemical_name_common ? _chemical_melting_point 160-161 _chemical_formula_moiety 'C22H18N4O, 0.5(C4H4O4)' _chemical_formula_sum 'C24 H20 N4 O3' _chemical_formula_weight 412.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 28.8097(18) _cell_length_b 7.8866(6) _cell_length_c 18.5925(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.004(5) _cell_angle_gamma 90.00 _cell_volume 4183.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 9500 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3656 _reflns_number_gt 2935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.168, 2001' _computing_cell_refinement 'KM4RED, Version 1.168, 2001' _computing_data_reduction 'KM4RED, Version 1.168, 2001' _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^)+(0.0775P)^2^+1.6715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3656 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1452 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.004 _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 0.05008(5) 0.9582(2) 0.19885(9) 0.0513(4) Uani 1 1 d . . . H1N H 0.0332(10) 0.862(4) 0.1534(16) 0.103(9) Uiso 1 1 d . . . C2 C 0.07640(6) 0.8992(2) 0.25890(9) 0.0436(4) Uani 1 1 d . . . C3 C 0.09325(7) 1.0121(2) 0.31460(11) 0.0511(5) Uani 1 1 d . . . H3 H 0.1123 0.9667 0.3566 0.063(6) Uiso 1 1 d R . . C4 C 0.08428(8) 1.1818(3) 0.30500(13) 0.0627(6) Uani 1 1 d . . . H4 H 0.0962 1.2628 0.3415 0.082(8) Uiso 1 1 d R . . C5 C 0.05860(8) 1.2406(3) 0.24221(14) 0.0677(6) Uani 1 1 d . . . H5 H 0.0524 1.3589 0.2331 0.092(8) Uiso 1 1 d R . . C6 C 0.04177(7) 1.1259(3) 0.19058(13) 0.0621(6) Uani 1 1 d . . . H6 H 0.0230 1.1553 0.1456 0.065(6) Uiso 1 1 d R . . N7 N 0.08522(5) 0.7289(2) 0.25988(8) 0.0502(4) Uani 1 1 d . . . H7 H 0.0775 0.6766 0.2131 0.082(7) Uiso 1 1 d R . . C8 C 0.11667(6) 0.6463(2) 0.31351(10) 0.0442(4) Uani 1 1 d . . . C9 C 0.15484(6) 0.5606(2) 0.29238(10) 0.0441(4) Uani 1 1 d . . . C10 C 0.18600(7) 0.4748(2) 0.34261(11) 0.0533(5) Uani 1 1 d . . . H10 H 0.2113 0.4136 0.3262 0.077(7) Uiso 1 1 d R . . C11 C 0.17947(8) 0.4753(3) 0.41493(12) 0.0619(6) Uani 1 1 d . . . H11 H 0.2031 0.4203 0.4485 0.079(7) Uiso 1 1 d R . . C12 C 0.14188(8) 0.5588(3) 0.43683(11) 0.0614(6) Uani 1 1 d . . . H12 H 0.1383 0.5588 0.4874 0.065(6) Uiso 1 1 d R . . C13 C 0.11019(7) 0.6424(3) 0.38610(11) 0.0548(5) Uani 1 1 d . . . H13 H 0.0835 0.7005 0.3999 0.062(6) Uiso 1 1 d R . . O14 O 0.15734(5) 0.56612(19) 0.21886(7) 0.0576(4) Uani 1 1 d . . . C15 C 0.19749(6) 0.5108(2) 0.19229(10) 0.0473(5) Uani 1 1 d . . . C16 C 0.19131(6) 0.3827(2) 0.14026(10) 0.0464(4) Uani 1 1 d . . . C17 C 0.23021(7) 0.3387(3) 0.10713(11) 0.0573(5) Uani 1 1 d . . . H17 H 0.2258 0.2553 0.0692 0.073(7) Uiso 1 1 d R . . C18 C 0.27305(7) 0.4151(3) 0.12719(13) 0.0643(6) Uani 1 1 d . . . H18 H 0.2982 0.3847 0.1009 0.083(7) Uiso 1 1 d R . . C19 C 0.27829(8) 0.5395(3) 0.17956(14) 0.0680(6) Uani 1 1 d . . . H19 H 0.3088 0.5875 0.1935 0.083(8) Uiso 1 1 d R . . C20 C 0.23987(7) 0.5898(3) 0.21125(12) 0.0614(6) Uani 1 1 d . . . H20 H 0.2433 0.6797 0.2464 0.070(7) Uiso 1 1 d R . . N21 N 0.14713(6) 0.3104(2) 0.12226(9) 0.0552(4) Uani 1 1 d . . . H21 H 0.1211 0.3836 0.1267 0.062(6) Uiso 1 1 d R . . C22 C 0.13739(7) 0.1544(3) 0.08876(10) 0.0533(5) Uani 1 1 d . . . N23 N 0.09610(6) 0.1452(2) 0.04679(9) 0.0553(4) Uani 1 1 d . . . C24 C 0.08405(9) -0.0019(3) 0.01398(12) 0.0636(6) Uani 1 1 d . . . H24 H 0.0532 -0.0019 -0.0133 0.049(5) Uiso 1 1 d R . . C25 C 0.11205(10) -0.1435(3) 0.02061(14) 0.0759(7) Uani 1 1 d . . . H25 H 0.1009 -0.2471 -0.0028 0.097(9) Uiso 1 1 d R . . C26 C 0.15398(10) -0.1343(3) 0.06483(16) 0.0847(8) Uani 1 1 d . . . H26 H 0.1745 -0.2308 0.0710 0.114(10) Uiso 1 1 d R . . C27 C 0.16714(9) 0.0150(3) 0.10030(15) 0.0772(7) Uani 1 1 d . . . H27 H 0.1956 0.0223 0.1338 0.101(9) Uiso 1 1 d R . . O1A O 0.00698(6) 0.7755(3) 0.09673(10) 0.0866(6) Uani 1 1 d . . . O2A O 0.05795(8) 0.5657(2) 0.12150(10) 0.0895(6) Uani 1 1 d . . . C1A C 0.02336(12) 0.6348(5) 0.08294(13) 0.0860(9) Uani 1 1 d . . . C2A C 0.01607(19) 0.4820(11) 0.0229(4) 0.0679(13) Uani 0.50 1 d P . . C2'A C -0.00585(18) 0.5764(5) 0.0148(3) 0.0365(8) Uani 0.50 1 d P . . H2A H -0.0324 0.6353 -0.0107 0.077(7) 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 0.0469(8) 0.0630(11) 0.0442(9) -0.0016(8) 0.0069(7) 0.0033(7) C2 0.0375(9) 0.0513(11) 0.0429(10) -0.0051(8) 0.0095(7) -0.0010(8) C3 0.0483(10) 0.0501(12) 0.0540(11) -0.0071(9) 0.0042(9) -0.0035(8) C4 0.0624(13) 0.0514(12) 0.0758(15) -0.0090(11) 0.0150(11) -0.0083(10) C5 0.0706(14) 0.0519(13) 0.0836(17) 0.0058(12) 0.0211(12) 0.0017(11) C6 0.0571(12) 0.0702(15) 0.0612(13) 0.0155(11) 0.0164(10) 0.0112(11) N7 0.0569(9) 0.0493(9) 0.0422(9) -0.0134(7) -0.0005(7) 0.0057(7) C8 0.0504(10) 0.0388(10) 0.0431(10) -0.0090(7) 0.0052(8) -0.0039(8) C9 0.0486(10) 0.0409(10) 0.0427(10) -0.0089(8) 0.0055(8) -0.0063(8) C10 0.0565(11) 0.0453(11) 0.0579(12) -0.0047(9) 0.0067(9) 0.0005(9) C11 0.0726(14) 0.0527(12) 0.0576(13) 0.0074(10) -0.0012(11) -0.0001(10) C12 0.0857(15) 0.0561(13) 0.0437(12) 0.0013(9) 0.0131(10) -0.0042(11) C13 0.0649(12) 0.0526(12) 0.0489(11) -0.0077(9) 0.0149(9) -0.0003(10) O14 0.0504(8) 0.0799(10) 0.0423(7) -0.0145(7) 0.0063(6) 0.0094(7) C15 0.0462(10) 0.0523(11) 0.0439(10) -0.0038(8) 0.0078(8) 0.0038(8) C16 0.0487(10) 0.0489(11) 0.0412(10) 0.0002(8) 0.0045(8) 0.0042(8) C17 0.0581(12) 0.0630(13) 0.0523(12) -0.0075(10) 0.0130(9) 0.0073(10) C18 0.0539(12) 0.0686(14) 0.0743(15) 0.0059(12) 0.0226(10) 0.0069(10) C19 0.0487(12) 0.0633(14) 0.0931(18) -0.0016(13) 0.0135(11) -0.0063(10) C20 0.0568(12) 0.0548(13) 0.0721(14) -0.0146(11) 0.0072(10) -0.0022(10) N21 0.0476(9) 0.0579(10) 0.0591(10) -0.0195(8) 0.0038(7) 0.0012(8) C22 0.0571(11) 0.0563(12) 0.0467(11) -0.0011(9) 0.0076(9) 0.0012(9) N23 0.0557(10) 0.0569(10) 0.0526(10) -0.0048(8) 0.0053(8) -0.0032(8) C24 0.0698(14) 0.0614(14) 0.0588(13) -0.0048(10) 0.0063(11) -0.0109(11) C25 0.0956(18) 0.0530(14) 0.0784(17) -0.0078(12) 0.0100(14) -0.0067(13) C26 0.0975(19) 0.0496(14) 0.103(2) 0.0018(13) 0.0012(16) 0.0145(13) C27 0.0789(16) 0.0611(15) 0.0846(17) 0.0001(12) -0.0130(14) 0.0141(12) O1A 0.0757(11) 0.1160(16) 0.0620(11) -0.0170(11) -0.0122(8) -0.0158(11) O2A 0.1349(17) 0.0640(11) 0.0711(12) -0.0291(9) 0.0192(12) -0.0138(11) C1A 0.099(2) 0.119(3) 0.0388(13) -0.0120(14) 0.0059(13) -0.059(2) C2A 0.063(3) 0.074(4) 0.067(4) 0.001(4) 0.010(3) -0.002(4) C2'A 0.038(2) 0.034(2) 0.034(2) -0.0089(18) -0.0089(17) 0.0111(19) _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 1.342(2) . ? N1 C6 1.349(3) . ? N1 H1N 1.19(3) . ? C2 N7 1.367(2) . ? C2 C3 1.400(3) . ? C3 C4 1.370(3) . ? C3 H3 0.9600 . ? C4 C5 1.373(3) . ? C4 H4 0.9601 . ? C5 C6 1.358(3) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.410(2) . ? N7 H7 0.9600 . ? C8 C13 1.388(3) . ? C8 C9 1.393(3) . ? C9 C10 1.379(3) . ? C9 O14 1.380(2) . ? C10 C11 1.383(3) . ? C10 H10 0.9602 . ? C11 C12 1.377(3) . ? C11 H11 0.9600 . ? C12 C13 1.385(3) . ? C12 H12 0.9600 . ? C13 H13 0.9600 . ? O14 C15 1.390(2) . ? C15 C20 1.372(3) . ? C15 C16 1.393(3) . ? C16 N21 1.392(2) . ? C16 C17 1.396(3) . ? C17 C18 1.377(3) . ? C17 H17 0.9601 . ? C18 C19 1.376(3) . ? C18 H18 0.9598 . ? C19 C20 1.382(3) . ? C19 H19 0.9601 . ? C20 H20 0.9601 . ? N21 C22 1.390(3) . ? N21 H21 0.9600 . ? C22 N23 1.331(3) . ? C22 C27 1.393(3) . ? N23 C24 1.334(3) . ? C24 C25 1.373(3) . ? C24 H24 0.9600 . ? C25 C26 1.365(4) . ? C25 H25 0.9600 . ? C26 C27 1.377(4) . ? C26 H26 0.9601 . ? C27 H27 0.9600 . ? O1A C1A 1.247(4) . ? O1A H1N 1.39(3) . ? O2A C1A 1.267(4) . ? C1A C2'A 1.493(6) . ? C1A C2A 1.636(10) . ? C2A C2'A 0.855(6) 5_565 ? C2A C2'A 0.975(6) . ? C2A C2A 1.201(11) 5_565 ? C2'A C2A 0.855(6) 5_565 ? C2'A C2'A 1.385(8) 5_565 ? C2'A H2A 0.9601 . ? 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 120.35(18) . . ? C2 N1 H1N 119.8(14) . . ? C6 N1 H1N 119.9(14) . . ? N1 C2 N7 115.73(16) . . ? N1 C2 C3 119.49(18) . . ? N7 C2 C3 124.77(17) . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3 123.1 . . ? C2 C3 H3 117.8 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 118.3 . . ? C6 C5 C4 118.2(2) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 122.8 . . ? N1 C6 C5 122.2(2) . . ? N1 C6 H6 113.9 . . ? C5 C6 H6 123.9 . . ? C2 N7 C8 124.30(15) . . ? C2 N7 H7 113.0 . . ? C8 N7 H7 119.1 . . ? C13 C8 C9 118.78(18) . . ? C13 C8 N7 122.52(17) . . ? C9 C8 N7 118.66(16) . . ? C10 C9 O14 124.59(17) . . ? C10 C9 C8 120.80(17) . . ? O14 C9 C8 114.59(16) . . ? C9 C10 C11 119.54(19) . . ? C9 C10 H10 118.9 . . ? C11 C10 H10 121.6 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11 122.6 . . ? C10 C11 H11 116.8 . . ? C11 C12 C13 119.83(19) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 121.1 . . ? C12 C13 C8 120.50(19) . . ? C12 C13 H13 121.5 . . ? C8 C13 H13 118.0 . . ? C9 O14 C15 120.21(14) . . ? C20 C15 O14 121.41(17) . . ? C20 C15 C16 122.05(18) . . ? O14 C15 C16 116.25(16) . . ? N21 C16 C15 119.21(16) . . ? N21 C16 C17 123.75(18) . . ? C15 C16 C17 117.00(18) . . ? C18 C17 C16 121.1(2) . . ? C18 C17 H17 121.4 . . ? C16 C17 H17 117.5 . . ? C19 C18 C17 120.6(2) . . ? C19 C18 H18 121.5 . . ? C17 C18 H18 117.7 . . ? C18 C19 C20 119.4(2) . . ? C18 C19 H19 118.5 . . ? C20 C19 H19 122.0 . . ? C15 C20 C19 119.8(2) . . ? C15 C20 H20 120.9 . . ? C19 C20 H20 119.3 . . ? C22 N21 C16 126.23(16) . . ? C22 N21 H21 117.3 . . ? C16 N21 H21 115.7 . . ? N23 C22 N21 114.83(17) . . ? N23 C22 C27 121.8(2) . . ? N21 C22 C27 123.3(2) . . ? C22 N23 C24 118.07(19) . . ? N23 C24 C25 123.6(2) . . ? N23 C24 H24 113.9 . . ? C25 C24 H24 122.5 . . ? C26 C25 C24 118.1(2) . . ? C26 C25 H25 122.1 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 119.7(2) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 119.8 . . ? C26 C27 C22 118.6(2) . . ? C26 C27 H27 121.0 . . ? C22 C27 H27 120.3 . . ? C1A O1A H1N 114.3(11) . . ? O1A C1A O2A 123.8(2) . . ? O1A C1A C2'A 105.3(3) . . ? O2A C1A C2'A 130.9(4) . . ? O1A C1A C2A 141.2(4) . . ? O2A C1A C2A 94.9(4) . . ? C2'A C1A C2A 35.93(19) . . ? C2'A C2A C2'A 98.2(7) 5_565 . ? C2'A C2A C2A 53.4(6) 5_565 5_565 ? C2'A C2A C2A 44.8(5) . 5_565 ? C2'A C2A C1A 162.2(10) 5_565 . ? C2'A C2A C1A 64.0(8) . . ? C2A C2A C1A 108.8(11) 5_565 . ? C2A C2'A C2A 81.8(7) 5_565 . ? C2A C2'A C2'A 44.1(5) 5_565 5_565 ? C2A C2'A C2'A 37.6(4) . 5_565 ? C2A C2'A C1A 161.8(10) 5_565 . ? C2A C2'A C1A 80.1(8) . . ? C2'A C2'A C1A 117.7(6) 5_565 . ? C2A C2'A H2A 72.4 5_565 . ? C2A C2'A H2A 154.1 . . ? C2'A C2'A H2A 116.5 5_565 . ? C1A C2'A H2A 125.8 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.244 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.035 #===END data_5tere _database_code_CSD 191449 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis(2-pyridyl)-2,2'-oxybis(aminobenzene) 1,4-benzenedicarboxylic acid co-crystal ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22H18N4O, 0.5(C8H6O4)' _chemical_formula_sum 'C26 H21 N4 O3' _chemical_formula_weight 437.47 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 8.2875(6) _cell_length_b 10.1511(8) _cell_length_c 13.3739(10) _cell_angle_alpha 78.828(7) _cell_angle_beta 87.705(6) _cell_angle_gamma 84.019(6) _cell_volume 1097.55(14) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 'not relevant with the CCD data' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'Kuma KM4CCD diffractometer' _diffrn_measurement_method '\o scan' _diffrn_standards_interval_count 50 _diffrn_standards_decay_% <2 _diffrn_reflns_number 7973 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3798 _reflns_number_gt 2684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD, Version 1.168, 2001' _computing_cell_refinement 'KM4RED, Version 1.168, 2001' _computing_data_reduction 'KM4RED, Version 1.168, 2001' _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^)+(0.0606P)^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, geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3798 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 -0.08881(18) 0.86793(16) 0.60671(12) 0.0471(4) Uani 1 1 d . . . H1 H 0.022(3) 0.783(3) 0.5867(18) 0.101(8) Uiso 1 1 d . . . C2 C -0.0622(2) 0.97714(19) 0.64440(13) 0.0434(5) Uani 1 1 d . . . C3 C -0.1940(2) 1.0697(2) 0.65947(16) 0.0567(6) Uani 1 1 d . . . H3 H -0.1705 1.1459 0.6871 0.070(7) Uiso 1 1 d R . . C4 C -0.3464(3) 1.0453(3) 0.63748(18) 0.0680(6) Uani 1 1 d . . . H4 H -0.4357 1.1088 0.6497 0.073(7) Uiso 1 1 d R . . C5 C -0.3718(3) 0.9310(3) 0.60220(18) 0.0677(6) Uani 1 1 d . . . H5 H -0.4769 0.9082 0.5879 0.085(7) Uiso 1 1 d R . . C6 C -0.2410(2) 0.8454(2) 0.58702(16) 0.0592(6) Uani 1 1 d . . . H6 H -0.2415 0.7634 0.5614 0.071(7) Uiso 1 1 d R . . N7 N 0.09501(18) 0.98532(16) 0.66664(13) 0.0511(4) Uani 1 1 d . . . H7 H 0.1632 0.9019 0.6724 0.083(7) Uiso 1 1 d R . . C8 C 0.1557(2) 1.09425(19) 0.69834(14) 0.0429(5) Uani 1 1 d . . . C9 C 0.2739(2) 1.06818(19) 0.77151(14) 0.0450(5) Uani 1 1 d . . . C10 C 0.3435(3) 1.1704(2) 0.80290(16) 0.0590(6) Uani 1 1 d . . . H10 H 0.4302 1.1469 0.8505 0.070(6) Uiso 1 1 d R . . C11 C 0.2928(3) 1.3028(2) 0.76176(19) 0.0683(6) Uani 1 1 d . . . H11 H 0.3458 1.3711 0.7844 0.092(8) Uiso 1 1 d R . . C12 C 0.1773(3) 1.3308(2) 0.68818(18) 0.0638(6) Uani 1 1 d . . . H12 H 0.1425 1.4221 0.6568 0.076(7) Uiso 1 1 d R . . C13 C 0.1093(2) 1.2288(2) 0.65540(16) 0.0545(5) Uani 1 1 d . . . H13 H 0.0314 1.2475 0.6020 0.056(6) Uiso 1 1 d R . . O14 O 0.33100(16) 0.93414(13) 0.80537(10) 0.0536(4) Uani 1 1 d . . . C15 C 0.3107(2) 0.87581(19) 0.90675(14) 0.0438(5) Uani 1 1 d . . . C16 C 0.3935(2) 0.74879(19) 0.93581(15) 0.0475(5) Uani 1 1 d . . . C17 C 0.3752(3) 0.6817(2) 1.03516(16) 0.0606(6) Uani 1 1 d . . . H17 H 0.4333 0.5940 1.0542 0.077(7) Uiso 1 1 d R . . C18 C 0.2796(3) 0.7408(2) 1.10457(17) 0.0661(6) Uani 1 1 d . . . H18 H 0.2757 0.6907 1.1732 0.096(8) Uiso 1 1 d R . . C19 C 0.2001(3) 0.8664(2) 1.07505(17) 0.0638(6) Uani 1 1 d . . . H19 H 0.1341 0.9108 1.1217 0.075(7) Uiso 1 1 d R . . C20 C 0.2140(2) 0.9348(2) 0.97571(15) 0.0553(5) Uani 1 1 d . . . H20 H 0.1626 1.0241 0.9522 0.060(6) Uiso 1 1 d R . . N21 N 0.49028(19) 0.68901(16) 0.86352(13) 0.0551(5) Uani 1 1 d . . . H21 H 0.4473 0.7043 0.7962 0.064(6) Uiso 1 1 d R . . C22 C 0.6590(2) 0.67073(19) 0.86711(15) 0.0492(5) Uani 1 1 d . . . N23 N 0.7299(2) 0.61778(18) 0.79107(13) 0.0622(5) Uani 1 1 d . . . C24 C 0.8919(3) 0.5970(3) 0.7913(2) 0.0770(7) Uani 1 1 d . . . H24 H 0.9397 0.5588 0.7354 0.101(9) Uiso 1 1 d R . . C25 C 0.9877(3) 0.6249(3) 0.8622(2) 0.0874(8) Uani 1 1 d . . . H25 H 1.1036 0.6067 0.8600 0.106(9) Uiso 1 1 d R . . C26 C 0.9112(3) 0.6781(3) 0.9408(2) 0.0932(9) Uani 1 1 d . . . H26 H 0.9723 0.6972 0.9950 0.108(9) Uiso 1 1 d R . . C27 C 0.7464(3) 0.7019(3) 0.94373(19) 0.0734(7) Uani 1 1 d . . . H27 H 0.6914 0.7362 0.9993 0.074(7) Uiso 1 1 d R . . O1A O 0.12251(16) 0.69318(14) 0.55286(10) 0.0570(4) Uani 1 1 d . . . O2A O 0.30530(16) 0.73778(15) 0.65442(11) 0.0634(4) Uani 1 1 d . . . C1A C 0.3509(2) 0.53813(19) 0.45616(14) 0.0472(5) Uani 1 1 d . . . H1A H 0.2478 0.5653 0.4243 0.050(5) Uiso 1 1 d R . . C2A C 0.3873(2) 0.58730(17) 0.54185(13) 0.0409(4) Uani 1 1 d . . . C3A C 0.5379(2) 0.54788(18) 0.58545(14) 0.0460(5) Uani 1 1 d . . . H3A H 0.5651 0.5777 0.6460 0.057(6) Uiso 1 1 d R . . C4A C 0.2655(2) 0.67985(18) 0.58761(14) 0.0438(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0449(9) 0.0495(10) 0.0486(10) -0.0127(8) -0.0013(7) -0.0063(7) C2 0.0447(11) 0.0476(11) 0.0370(11) -0.0085(9) -0.0008(8) 0.0002(9) C3 0.0502(12) 0.0603(14) 0.0599(14) -0.0180(11) 0.0049(10) 0.0034(10) C4 0.0469(13) 0.0793(17) 0.0731(16) -0.0111(13) 0.0094(11) 0.0057(12) C5 0.0430(13) 0.0815(17) 0.0754(17) -0.0030(14) -0.0024(11) -0.0131(12) C6 0.0537(13) 0.0643(15) 0.0615(14) -0.0106(12) -0.0030(10) -0.0166(11) N7 0.0441(9) 0.0448(10) 0.0682(12) -0.0227(9) -0.0115(8) 0.0039(8) C8 0.0436(10) 0.0434(11) 0.0427(11) -0.0129(9) 0.0004(8) -0.0001(8) C9 0.0490(11) 0.0456(11) 0.0412(11) -0.0135(9) 0.0023(8) 0.0011(9) C10 0.0590(13) 0.0648(15) 0.0592(14) -0.0267(12) -0.0070(11) -0.0037(11) C11 0.0786(16) 0.0581(15) 0.0767(17) -0.0283(13) 0.0028(13) -0.0181(12) C12 0.0795(16) 0.0445(13) 0.0653(15) -0.0083(12) 0.0078(12) -0.0038(11) C13 0.0618(13) 0.0507(13) 0.0504(13) -0.0108(10) -0.0045(10) 0.0003(10) O14 0.0664(9) 0.0511(8) 0.0423(8) -0.0156(7) -0.0067(6) 0.0134(7) C15 0.0414(10) 0.0521(12) 0.0407(11) -0.0157(9) -0.0077(8) -0.0021(9) C16 0.0509(11) 0.0472(11) 0.0474(12) -0.0181(10) -0.0072(9) 0.0016(9) C17 0.0754(15) 0.0500(13) 0.0552(14) -0.0093(11) -0.0068(11) 0.0008(11) C18 0.0767(15) 0.0732(16) 0.0482(14) -0.0100(12) 0.0019(11) -0.0100(13) C19 0.0603(13) 0.0798(16) 0.0521(14) -0.0207(13) 0.0072(10) 0.0022(12) C20 0.0523(12) 0.0618(14) 0.0515(13) -0.0184(11) -0.0037(9) 0.0112(10) N21 0.0576(10) 0.0604(11) 0.0490(11) -0.0232(9) -0.0117(8) 0.0141(8) C22 0.0584(12) 0.0390(11) 0.0491(12) -0.0087(9) -0.0045(9) 0.0022(9) N23 0.0657(12) 0.0684(12) 0.0505(11) -0.0168(9) -0.0027(8) 0.0131(9) C24 0.0703(17) 0.0857(18) 0.0706(17) -0.0149(14) 0.0072(13) 0.0089(14) C25 0.0527(15) 0.109(2) 0.099(2) -0.0185(18) -0.0019(14) -0.0013(14) C26 0.0715(18) 0.122(2) 0.095(2) -0.0348(19) -0.0211(16) -0.0156(16) C27 0.0662(15) 0.0903(18) 0.0733(17) -0.0399(14) -0.0084(12) -0.0040(13) O1A 0.0477(8) 0.0631(9) 0.0664(10) -0.0314(8) -0.0112(7) 0.0049(7) O2A 0.0549(8) 0.0747(10) 0.0718(10) -0.0465(9) -0.0096(7) 0.0051(7) C1A 0.0454(11) 0.0524(12) 0.0471(12) -0.0179(9) -0.0080(8) -0.0011(9) C2A 0.0465(10) 0.0388(10) 0.0403(11) -0.0132(8) 0.0010(8) -0.0075(8) C3A 0.0493(11) 0.0501(12) 0.0435(12) -0.0208(9) -0.0039(8) -0.0044(9) C4A 0.0495(11) 0.0413(11) 0.0429(11) -0.0134(9) -0.0013(9) -0.0053(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 N1 C2 1.345(2) . ? N1 C6 1.350(2) . ? N1 H1 1.25(2) . ? C2 N7 1.363(2) . ? C2 C3 1.400(2) . ? C3 C4 1.366(3) . ? C3 H3 0.9601 . ? C4 C5 1.373(3) . ? C4 H4 0.9600 . ? C5 C6 1.350(3) . ? C5 H5 0.9600 . ? C6 H6 0.9600 . ? N7 C8 1.404(2) . ? N7 H7 0.9599 . ? C8 C9 1.382(3) . ? C8 C13 1.396(3) . ? C9 C10 1.378(3) . ? C9 O14 1.387(2) . ? C10 C11 1.379(3) . ? C10 H10 0.9600 . ? C11 C12 1.369(3) . ? C11 H11 0.9601 . ? C12 C13 1.378(3) . ? C12 H12 0.9600 . ? C13 H13 0.9601 . ? O14 C15 1.382(2) . ? C15 C20 1.380(2) . ? C15 C16 1.388(3) . ? C16 C17 1.381(3) . ? C16 N21 1.418(2) . ? C17 C18 1.381(3) . ? C17 H17 0.9600 . ? C18 C19 1.367(3) . ? C18 H18 0.9600 . ? C19 C20 1.381(3) . ? C19 H19 0.9600 . ? C20 H20 0.9600 . ? N21 C22 1.393(2) . ? N21 H21 0.9601 . ? C22 N23 1.329(2) . ? C22 C27 1.381(3) . ? N23 C24 1.337(3) . ? C24 C25 1.350(4) . ? C24 H24 0.9600 . ? C25 C26 1.376(4) . ? C25 H25 0.9599 . ? C26 C27 1.363(3) . ? C26 H26 0.9600 . ? C27 H27 0.9599 . ? O1A C4A 1.275(2) . ? O1A H1 1.31(2) . ? O2A C4A 1.233(2) . ? C1A C3A 1.379(2) 2_666 ? C1A C2A 1.391(2) . ? C1A H1A 0.9600 . ? C2A C3A 1.386(2) . ? C2A C4A 1.501(2) . ? C3A C1A 1.379(2) 2_666 ? C3A H3A 0.9600 . ? 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 120.51(17) . . ? C2 N1 H1 123.4(11) . . ? C6 N1 H1 116.1(11) . . ? N1 C2 N7 115.28(15) . . ? N1 C2 C3 119.02(18) . . ? N7 C2 C3 125.69(18) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3 124.2 . . ? C2 C3 H3 116.6 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 118.1 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 118.0(2) . . ? C6 C5 H5 118.2 . . ? C4 C5 H5 123.8 . . ? C5 C6 N1 122.3(2) . . ? C5 C6 H6 126.5 . . ? N1 C6 H6 111.2 . . ? C2 N7 C8 126.08(15) . . ? C2 N7 H7 114.5 . . ? C8 N7 H7 118.4 . . ? C9 C8 C13 117.79(18) . . ? C9 C8 N7 118.93(17) . . ? C13 C8 N7 123.18(18) . . ? C10 C9 C8 121.88(18) . . ? C10 C9 O14 120.85(18) . . ? C8 C9 O14 116.99(17) . . ? C9 C10 C11 119.5(2) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 121.8 . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 123.4 . . ? C10 C11 H11 117.0 . . ? C11 C12 C13 121.2(2) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 117.7 . . ? C12 C13 C8 120.1(2) . . ? C12 C13 H13 121.6 . . ? C8 C13 H13 118.2 . . ? C15 O14 C9 119.63(13) . . ? C20 C15 O14 124.19(17) . . ? C20 C15 C16 120.93(18) . . ? O14 C15 C16 114.87(15) . . ? C17 C16 C15 118.47(17) . . ? C17 C16 N21 121.38(17) . . ? C15 C16 N21 120.12(18) . . ? C16 C17 C18 120.7(2) . . ? C16 C17 H17 117.6 . . ? C18 C17 H17 121.7 . . ? C19 C18 C17 120.1(2) . . ? C19 C18 H18 123.1 . . ? C17 C18 H18 116.8 . . ? C18 C19 C20 120.32(19) . . ? C18 C19 H19 122.1 . . ? C20 C19 H19 117.6 . . ? C15 C20 C19 119.43(19) . . ? C15 C20 H20 117.5 . . ? C19 C20 H20 123.1 . . ? C22 N21 C16 122.49(16) . . ? C22 N21 H21 114.7 . . ? C16 N21 H21 115.6 . . ? N23 C22 C27 122.34(19) . . ? N23 C22 N21 114.20(18) . . ? C27 C22 N21 123.45(17) . . ? C22 N23 C24 116.7(2) . . ? N23 C24 C25 125.3(2) . . ? N23 C24 H24 114.8 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 116.9(2) . . ? C24 C25 H25 122.4 . . ? C26 C25 H25 120.6 . . ? C27 C26 C25 120.0(2) . . ? C27 C26 H26 119.0 . . ? C25 C26 H26 120.9 . . ? C26 C27 C22 118.7(2) . . ? C26 C27 H27 120.8 . . ? C22 C27 H27 120.4 . . ? C4A O1A H1 114.9(10) . . ? C3A C1A C2A 120.96(17) 2_666 . ? C3A C1A H1A 119.0 2_666 . ? C2A C1A H1A 120.0 . . ? C3A C2A C1A 118.83(16) . . ? C3A C2A C4A 120.28(16) . . ? C1A C2A C4A 120.88(16) . . ? C1A C3A C2A 120.21(17) 2_666 . ? C1A C3A H3A 119.1 2_666 . ? C2A C3A H3A 120.7 . . ? O2A C4A O1A 123.71(16) . . ? O2A C4A C2A 120.58(16) . . ? O1A C4A C2A 115.71(16) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.115 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 #===END