# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name C.Aakeroy _publ_contact_author_email aakeroy@ksu.edu _publ_author_name C.Aakeroy data_3,3'azpy:SA _database_code_depnum_ccdc_archive 'CCDC 892700' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-AzoPy-SA (3-pyridyl)-N=N-(3-pyridyl), HOOC-(CH2)2-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C4 H6 O4) ; _chemical_formula_sum 'C14 H14 N4 O4' _chemical_formula_weight 302.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9092(7) _cell_length_b 5.2342(3) _cell_length_c 11.3589(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.198(3) _cell_angle_gamma 90.00 _cell_volume 707.90(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3462 _cell_measurement_theta_min 3.59 _cell_measurement_theta_max 31.45 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9626 _exptl_absorpt_correction_T_max 0.9936 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8074 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 31.49 _reflns_number_total 2256 _reflns_number_gt 1785 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0600P)^2^+0.1000P] 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 2256 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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 N11 N 0.22353(8) 0.21628(18) 0.18515(8) 0.0213(2) Uani 1 1 d . . . C12 C 0.30171(9) 0.2240(2) 0.10285(10) 0.0201(2) Uani 1 1 d . . . H12 H 0.2976 0.3551 0.0451 0.024 Uiso 1 1 calc R . . C13 C 0.38879(8) 0.0485(2) 0.09804(9) 0.0192(2) Uani 1 1 d . . . N13 N 0.46146(7) 0.08056(18) 0.00152(8) 0.0219(2) Uani 1 1 d . . . C14 C 0.39716(9) -0.1416(2) 0.18373(10) 0.0225(2) Uani 1 1 d . . . H14 H 0.4563 -0.2633 0.1830 0.027 Uiso 1 1 calc R . . C15 C 0.31687(9) -0.1474(2) 0.26965(10) 0.0229(2) Uani 1 1 d . . . H15 H 0.3203 -0.2726 0.3302 0.027 Uiso 1 1 calc R . . C16 C 0.23103(9) 0.0321(2) 0.26643(10) 0.0216(2) Uani 1 1 d . . . H16 H 0.1750 0.0236 0.3247 0.026 Uiso 1 1 calc R . . C21 C 0.07886(8) 0.71690(19) 0.07027(9) 0.0171(2) Uani 1 1 d . . . O21 O 0.05586(6) 0.55739(15) 0.15732(7) 0.0221(2) Uani 1 1 d . . . H21 H 0.1165(12) 0.443(3) 0.1686(12) 0.027 Uiso 1 1 d . . . O22 O 0.16323(6) 0.70311(15) 0.01271(7) 0.02153(19) Uani 1 1 d . . . C22 C -0.01114(8) 0.9151(2) 0.05220(9) 0.0182(2) Uani 1 1 d . . . H22A H -0.0158 1.0216 0.1239 0.022 Uiso 1 1 calc R . . H22B H -0.0845 0.8288 0.0401 0.022 Uiso 1 1 calc 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 N11 0.0202(4) 0.0208(5) 0.0231(5) 0.0006(3) 0.0035(3) 0.0032(3) C12 0.0191(5) 0.0189(5) 0.0224(5) 0.0020(4) 0.0032(4) 0.0026(4) C13 0.0168(4) 0.0201(5) 0.0206(5) 0.0002(4) 0.0018(4) 0.0008(4) N13 0.0183(4) 0.0226(5) 0.0248(5) 0.0013(4) 0.0033(3) 0.0032(3) C14 0.0203(5) 0.0223(5) 0.0249(5) 0.0014(4) 0.0006(4) 0.0047(4) C15 0.0240(5) 0.0225(5) 0.0221(5) 0.0040(4) 0.0013(4) 0.0023(4) C16 0.0222(5) 0.0225(5) 0.0203(5) -0.0002(4) 0.0039(4) 0.0014(4) C21 0.0188(5) 0.0154(5) 0.0170(5) -0.0014(3) 0.0017(4) 0.0007(3) O21 0.0217(4) 0.0217(4) 0.0234(4) 0.0066(3) 0.0063(3) 0.0051(3) O22 0.0203(4) 0.0231(4) 0.0214(4) 0.0019(3) 0.0053(3) 0.0042(3) C22 0.0180(4) 0.0180(5) 0.0188(5) 0.0019(4) 0.0039(4) 0.0031(4) _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 N11 C12 1.3337(13) . ? N11 C16 1.3367(14) . ? C12 C13 1.3871(14) . ? C12 H12 0.9500 . ? C13 C14 1.3940(15) . ? C13 N13 1.4209(14) . ? N13 N13 1.2475(18) 3_655 ? C14 C15 1.3809(15) . ? C14 H14 0.9500 . ? C15 C16 1.3883(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O22 1.2124(12) . ? C21 O21 1.3270(12) . ? C21 C22 1.5025(14) . ? O21 H21 0.946(15) . ? C22 C22 1.510(2) 3_575 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 C12 N11 C16 117.93(9) . . ? N11 C12 C13 122.76(10) . . ? N11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C12 C13 C14 119.18(10) . . ? C12 C13 N13 114.85(9) . . ? C14 C13 N13 125.95(9) . . ? N13 N13 C13 113.70(12) 3_655 . ? C15 C14 C13 117.96(10) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? C14 C15 C16 119.12(10) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N11 C16 C15 123.01(10) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? O22 C21 O21 123.41(9) . . ? O22 C21 C22 124.36(9) . . ? O21 C21 C22 112.23(8) . . ? C21 O21 H21 109.4(8) . . ? C21 C22 C22 112.16(10) . 3_575 ? C21 C22 H22A 109.2 . . ? C22 C22 H22A 109.2 3_575 . ? C21 C22 H22B 109.2 . . ? C22 C22 H22B 109.2 3_575 . ? H22A C22 H22B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.59(16) . . . . ? N11 C12 C13 C14 -1.34(17) . . . . ? N11 C12 C13 N13 177.59(10) . . . . ? C12 C13 N13 N13 -179.44(12) . . . 3_655 ? C14 C13 N13 N13 -0.60(19) . . . 3_655 ? C12 C13 C14 C15 0.55(16) . . . . ? N13 C13 C14 C15 -178.25(10) . . . . ? C13 C14 C15 C16 0.88(17) . . . . ? C12 N11 C16 C15 0.95(17) . . . . ? C14 C15 C16 N11 -1.70(18) . . . . ? O22 C21 C22 C22 4.21(17) . . . 3_575 ? O21 C21 C22 C22 -176.02(11) . . . 3_575 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 N11 0.946(15) 1.748(15) 2.6924(12) 176.5(13) . _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.315 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051 #END data_3,3'-azpy:AA _database_code_depnum_ccdc_archive 'CCDC 892701' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-pyridyl)-N=N-(3-pyridyl), HOOC-(CH2)4-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C6 H10 O4) ; _chemical_formula_sum 'C16 H18 N4 O4' _chemical_formula_weight 330.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 5.2025(4) _cell_length_b 7.0703(6) _cell_length_c 11.4579(10) _cell_angle_alpha 99.247(5) _cell_angle_beta 102.957(6) _cell_angle_gamma 101.395(5) _cell_volume 393.25(6) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3389 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 32.20 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9100 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 32.40 _reflns_number_total 2738 _reflns_number_gt 2187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0800P)^2^+0.0500P] 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 2738 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1451 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 N11 N 0.45190(18) 0.32391(12) 0.26933(8) 0.0203(2) Uani 1 1 d . . . C12 C 0.3220(2) 0.44091(13) 0.32443(9) 0.0192(2) Uani 1 1 d . . . H12 H 0.3261 0.5675 0.3058 0.023 Uiso 1 1 calc R . . C13 C 0.18080(19) 0.38467(13) 0.40807(9) 0.0184(2) Uani 1 1 d . . . N13 N 0.06191(18) 0.52845(12) 0.46214(8) 0.01982(19) Uani 1 1 d . . . C14 C 0.1719(2) 0.19811(15) 0.43484(11) 0.0253(2) Uani 1 1 d . . . H14 H 0.0786 0.1562 0.4921 0.030 Uiso 1 1 calc R . . C15 C 0.3022(2) 0.07577(14) 0.37593(11) 0.0257(2) Uani 1 1 d . . . H15 H 0.2966 -0.0532 0.3908 0.031 Uiso 1 1 calc R . . C16 C 0.4419(2) 0.14387(14) 0.29455(10) 0.0217(2) Uani 1 1 d . . . H16 H 0.5335 0.0599 0.2554 0.026 Uiso 1 1 calc R . . C21 C 0.7562(2) 0.66816(14) 0.13255(10) 0.0195(2) Uani 1 1 d . . . O21 O 0.74580(17) 0.47749(11) 0.12650(8) 0.0264(2) Uani 1 1 d . . . H21 H 0.652(3) 0.428(2) 0.1777(15) 0.032 Uiso 1 1 d . . . C22 C 0.9301(2) 0.75491(14) 0.05597(10) 0.0206(2) Uani 1 1 d . . . H22A H 0.8838 0.6625 -0.0245 0.025 Uiso 1 1 calc R . . H22B H 1.1230 0.7654 0.0968 0.025 Uiso 1 1 calc R . . O22 O 0.64141(18) 0.75943(11) 0.19448(8) 0.0288(2) Uani 1 1 d . . . C23 C 0.9001(2) 0.95725(14) 0.03435(10) 0.0192(2) Uani 1 1 d . . . H23A H 0.9323 1.0484 0.1142 0.023 Uiso 1 1 calc R . . H23B H 0.7120 0.9459 -0.0137 0.023 Uiso 1 1 calc 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 N11 0.0240(4) 0.0190(4) 0.0201(4) 0.0042(3) 0.0093(3) 0.0058(3) C12 0.0229(4) 0.0171(4) 0.0198(5) 0.0052(3) 0.0086(4) 0.0055(3) C13 0.0209(4) 0.0155(4) 0.0192(5) 0.0034(3) 0.0076(4) 0.0034(3) N13 0.0234(4) 0.0174(3) 0.0208(4) 0.0040(3) 0.0103(3) 0.0047(3) C14 0.0330(5) 0.0180(4) 0.0306(6) 0.0091(4) 0.0178(5) 0.0054(4) C15 0.0339(6) 0.0173(4) 0.0305(6) 0.0078(4) 0.0141(5) 0.0084(4) C16 0.0240(5) 0.0186(4) 0.0238(5) 0.0033(4) 0.0085(4) 0.0067(3) C21 0.0211(4) 0.0183(4) 0.0224(5) 0.0056(4) 0.0096(4) 0.0068(3) O21 0.0371(4) 0.0190(3) 0.0346(5) 0.0109(3) 0.0245(4) 0.0120(3) C22 0.0221(4) 0.0194(4) 0.0259(5) 0.0080(4) 0.0135(4) 0.0075(3) O22 0.0384(5) 0.0219(3) 0.0369(5) 0.0082(3) 0.0264(4) 0.0120(3) C23 0.0190(4) 0.0190(4) 0.0235(5) 0.0069(4) 0.0102(4) 0.0063(3) _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 N11 C12 1.3358(13) . ? N11 C16 1.3437(12) . ? C12 C13 1.3923(13) . ? C12 H12 0.9500 . ? C13 C14 1.3958(13) . ? C13 N13 1.4205(13) . ? N13 N13 1.2609(16) 2_566 ? C14 C15 1.3832(15) . ? C14 H14 0.9500 . ? C15 C16 1.3925(14) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O22 1.2133(12) . ? C21 O21 1.3283(12) . ? C21 C22 1.5079(13) . ? O21 H21 0.913(17) . ? C22 C23 1.5222(13) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C23 1.5289(18) 2_775 ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? 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 C12 N11 C16 118.45(8) . . ? N11 C12 C13 122.59(8) . . ? N11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C14 118.95(9) . . ? C12 C13 N13 115.80(8) . . ? C14 C13 N13 125.23(9) . . ? N13 N13 C13 113.54(10) 2_566 . ? C15 C14 C13 118.36(9) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C16 119.20(9) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N11 C16 C15 122.44(9) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? O22 C21 O21 123.04(9) . . ? O22 C21 C22 125.04(9) . . ? O21 C21 C22 111.91(8) . . ? C21 O21 H21 111.6(10) . . ? C21 C22 C23 114.79(8) . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.5 . . ? C22 C23 C23 111.63(10) . 2_775 ? C22 C23 H23A 109.3 . . ? C23 C23 H23A 109.3 2_775 . ? C22 C23 H23B 109.3 . . ? C23 C23 H23B 109.3 2_775 . ? H23A C23 H23B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 1.02(15) . . . . ? N11 C12 C13 C14 -0.63(16) . . . . ? N11 C12 C13 N13 177.75(9) . . . . ? C12 C13 N13 N13 -179.49(11) . . . 2_566 ? C14 C13 N13 N13 -1.23(18) . . . 2_566 ? C12 C13 C14 C15 -0.60(17) . . . . ? N13 C13 C14 C15 -178.81(10) . . . . ? C13 C14 C15 C16 1.37(17) . . . . ? C12 N11 C16 C15 -0.19(16) . . . . ? C14 C15 C16 N11 -1.01(18) . . . . ? O22 C21 C22 C23 -14.62(16) . . . . ? O21 C21 C22 C23 166.49(9) . . . . ? C21 C22 C23 C23 175.10(11) . . . 2_775 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 N11 0.913(17) 1.778(17) 2.6893(11) 176.5(15) . _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.393 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.064 #END data_3,3'azpy:SuA _database_code_depnum_ccdc_archive 'CCDC 892702' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 03-04BD (3-pyridyl)-N=N-(3-pyridyl), HOOC-(CH2)6-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C8 H14 O4) ; _chemical_formula_sum 'C18 H22 N4 O4' _chemical_formula_weight 358.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4680(6) _cell_length_b 7.0381(7) _cell_length_c 11.9358(12) _cell_angle_alpha 98.867(6) _cell_angle_beta 93.592(6) _cell_angle_gamma 102.392(6) _cell_volume 441.09(8) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4276 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 32.59 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 190 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10333 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 32.03 _reflns_number_total 3043 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0850P)^2^+0.0200P] 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 3043 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 N11 N 0.37397(15) 0.52122(11) 0.29688(7) 0.02243(19) Uani 1 1 d . . . C12 C 0.54561(17) 0.44109(13) 0.34451(7) 0.02070(19) Uani 1 1 d . . . H12 H 0.5264 0.3020 0.3279 0.025 Uiso 1 1 calc R . . C13 C 0.75152(16) 0.55357(12) 0.41749(8) 0.02044(19) Uani 1 1 d . . . N13 N 0.91051(14) 0.44590(11) 0.46573(7) 0.02158(18) Uani 1 1 d . . . C14 C 0.78275(19) 0.75813(14) 0.44055(9) 0.0275(2) Uani 1 1 d . . . H14 H 0.9210 0.8385 0.4905 0.033 Uiso 1 1 calc R . . C15 C 0.60798(19) 0.84131(13) 0.38914(9) 0.0277(2) Uani 1 1 d . . . H15 H 0.6262 0.9805 0.4019 0.033 Uiso 1 1 calc R . . C16 C 0.40497(18) 0.71841(14) 0.31848(8) 0.0240(2) Uani 1 1 d . . . H16 H 0.2839 0.7761 0.2843 0.029 Uiso 1 1 calc R . . C21 C -0.02751(17) 0.08676(13) 0.17296(8) 0.0215(2) Uani 1 1 d . . . O21 O -0.03708(13) 0.27499(10) 0.18041(7) 0.02851(19) Uani 1 1 d . . . H21 H 0.108(3) 0.358(2) 0.2191(12) 0.034 Uiso 1 1 d . . . O22 O 0.14520(14) 0.03384(11) 0.21804(8) 0.0359(2) Uani 1 1 d . . . C22 C -0.25302(16) -0.04841(13) 0.10173(8) 0.0220(2) Uani 1 1 d . . . H22A H -0.2669 -0.0057 0.0268 0.026 Uiso 1 1 calc R . . H22B H -0.4054 -0.0315 0.1391 0.026 Uiso 1 1 calc R . . C23 C -0.25240(17) -0.26768(13) 0.08128(8) 0.0220(2) Uani 1 1 d . . . H23A H -0.2362 -0.3127 0.1554 0.026 Uiso 1 1 calc R . . H23B H -0.1058 -0.2884 0.0403 0.026 Uiso 1 1 calc R . . C24 C -0.49421(16) -0.38923(13) 0.01141(8) 0.0228(2) Uani 1 1 d . . . H24A H -0.5091 -0.3429 -0.0624 0.027 Uiso 1 1 calc R . . H24B H -0.6398 -0.3660 0.0524 0.027 Uiso 1 1 calc 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 N11 0.0216(4) 0.0210(4) 0.0233(4) 0.0028(3) -0.0024(3) 0.0038(3) C12 0.0209(4) 0.0169(4) 0.0224(4) 0.0020(3) -0.0021(3) 0.0023(3) C13 0.0195(4) 0.0179(4) 0.0224(4) 0.0036(3) -0.0015(3) 0.0020(3) N13 0.0202(3) 0.0189(3) 0.0233(4) 0.0033(3) -0.0037(3) 0.0011(3) C14 0.0266(4) 0.0175(4) 0.0339(5) 0.0029(3) -0.0081(4) -0.0006(3) C15 0.0312(5) 0.0169(4) 0.0334(5) 0.0038(4) -0.0038(4) 0.0046(4) C16 0.0245(4) 0.0211(4) 0.0268(4) 0.0050(3) -0.0007(3) 0.0064(3) C21 0.0193(4) 0.0199(4) 0.0243(4) 0.0034(3) -0.0026(3) 0.0038(3) O21 0.0255(3) 0.0180(3) 0.0384(4) -0.0008(3) -0.0124(3) 0.0053(3) O22 0.0271(4) 0.0222(3) 0.0541(5) 0.0045(3) -0.0190(3) 0.0039(3) C22 0.0181(4) 0.0201(4) 0.0257(4) 0.0026(3) -0.0048(3) 0.0028(3) C23 0.0196(4) 0.0196(4) 0.0252(4) 0.0020(3) -0.0029(3) 0.0037(3) C24 0.0202(4) 0.0192(4) 0.0263(4) 0.0007(3) -0.0051(3) 0.0032(3) _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 N11 C12 1.3346(11) . ? N11 C16 1.3434(12) . ? C12 C13 1.3911(12) . ? C12 H12 0.9500 . ? C13 C14 1.3943(12) . ? C13 N13 1.4199(12) . ? N13 N13 1.2628(15) 2_766 ? C14 C15 1.3819(14) . ? C14 H14 0.9500 . ? C15 C16 1.3919(13) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O22 1.2121(11) . ? C21 O21 1.3266(11) . ? C21 C22 1.5047(12) . ? O21 H21 0.925(16) . ? C22 C23 1.5256(12) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5271(13) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C24 1.5278(17) 2_445 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 C12 N11 C16 118.54(7) . . ? N11 C12 C13 122.49(8) . . ? N11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C12 C13 C14 118.96(8) . . ? C12 C13 N13 115.79(8) . . ? C14 C13 N13 125.22(8) . . ? N13 N13 C13 113.33(9) 2_766 . ? C15 C14 C13 118.48(8) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C16 119.09(8) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? N11 C16 C15 122.41(8) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? O22 C21 O21 123.01(8) . . ? O22 C21 C22 125.21(8) . . ? O21 C21 C22 111.78(8) . . ? C21 O21 H21 111.3(8) . . ? C21 C22 C23 116.02(7) . . ? C21 C22 H22A 108.3 . . ? C23 C22 H22A 108.3 . . ? C21 C22 H22B 108.3 . . ? C23 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24 110.91(7) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C24 113.45(9) . 2_445 ? C23 C24 H24A 108.9 . . ? C24 C24 H24A 108.9 2_445 . ? C23 C24 H24B 108.9 . . ? C24 C24 H24B 108.9 2_445 . ? H24A C24 H24B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 1.51(14) . . . . ? N11 C12 C13 C14 -1.07(15) . . . . ? N11 C12 C13 N13 176.99(8) . . . . ? C12 C13 N13 N13 -177.71(9) . . . 2_766 ? C14 C13 N13 N13 0.21(16) . . . 2_766 ? C12 C13 C14 C15 -0.42(15) . . . . ? N13 C13 C14 C15 -178.28(9) . . . . ? C13 C14 C15 C16 1.38(16) . . . . ? C12 N11 C16 C15 -0.48(14) . . . . ? C14 C15 C16 N11 -0.97(16) . . . . ? O22 C21 C22 C23 -3.20(15) . . . . ? O21 C21 C22 C23 176.18(8) . . . . ? C21 C22 C23 C24 178.16(8) . . . . ? C22 C23 C24 C24 -179.66(9) . . . 2_445 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 N11 0.925(16) 1.756(16) 2.6798(11) 177.0(13) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 32.03 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.353 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.056 #END data_3,3'azpy:SeA _database_code_depnum_ccdc_archive 'CCDC 892703' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 03-03BD (3-pyridyl)-N=N-(3-pyridyl), HOOC-(CH2)8-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C10 H18 O4) ; _chemical_formula_sum 'C20 H26 N4 O4' _chemical_formula_weight 386.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 7.0388(14) _cell_length_b 8.2451(18) _cell_length_c 17.490(4) _cell_angle_alpha 77.525(14) _cell_angle_beta 80.368(13) _cell_angle_gamma 85.474(14) _cell_volume 976.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2500 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 29.94 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9780 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6041 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.0802 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 31.00 _reflns_number_total 6041 _reflns_number_gt 2977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6041 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1782 _refine_ls_R_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.2462 _refine_ls_wR_factor_gt 0.2017 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _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 N11 N 0.0857(3) 0.5352(2) 0.72502(11) 0.0399(5) Uani 1 1 d . . . C12 C 0.2303(4) 0.4661(3) 0.68101(13) 0.0374(6) Uani 1 1 d . . . H12 H 0.3569 0.4631 0.6936 0.045 Uiso 1 1 calc R . . C13 C 0.2033(3) 0.3984(3) 0.61759(13) 0.0359(5) Uani 1 1 d . . . N13 N 0.3754(3) 0.3364(2) 0.57424(11) 0.0373(5) Uani 1 1 d . . . C14 C 0.0181(4) 0.3991(3) 0.60046(13) 0.0379(6) Uani 1 1 d . . . H14 H -0.0050 0.3530 0.5577 0.045 Uiso 1 1 calc R . . C15 C -0.1317(4) 0.4676(3) 0.64619(14) 0.0404(6) Uani 1 1 d . . . H15 H -0.2603 0.4678 0.6362 0.048 Uiso 1 1 calc R . . C16 C -0.0920(4) 0.5365(3) 0.70728(14) 0.0411(6) Uani 1 1 d . . . H16 H -0.1954 0.5866 0.7377 0.049 Uiso 1 1 calc R . . N21 N 0.6347(3) 0.0966(2) 0.36068(11) 0.0385(5) Uani 1 1 d . . . C22 C 0.4888(4) 0.1610(3) 0.40656(13) 0.0363(5) Uani 1 1 d . . . H22 H 0.3628 0.1670 0.3931 0.044 Uiso 1 1 calc R . . C23 C 0.5140(4) 0.2192(3) 0.47281(13) 0.0360(5) Uani 1 1 d . . . N23 N 0.3443(3) 0.2808(2) 0.51574(11) 0.0367(5) Uani 1 1 d . . . C24 C 0.6992(4) 0.2100(3) 0.49337(14) 0.0396(6) Uani 1 1 d . . . H24 H 0.7207 0.2457 0.5392 0.048 Uiso 1 1 calc R . . C25 C 0.8499(4) 0.1472(3) 0.44488(14) 0.0400(6) Uani 1 1 d . . . H25 H 0.9778 0.1423 0.4562 0.048 Uiso 1 1 calc R . . C26 C 0.8132(4) 0.0912(3) 0.37923(14) 0.0399(6) Uani 1 1 d . . . H26 H 0.9177 0.0477 0.3466 0.048 Uiso 1 1 calc R . . C31 C 0.3644(4) 0.6487(3) 0.84364(13) 0.0359(5) Uani 1 1 d . . . O31 O 0.1782(3) 0.6731(2) 0.83866(10) 0.0473(5) Uani 1 1 d . . . H31 H 0.146(4) 0.614(3) 0.7959(17) 0.057 Uiso 1 1 d . . . O32 O 0.4776(3) 0.5801(2) 0.80016(10) 0.0469(5) Uani 1 1 d . . . C32 C 0.4133(3) 0.7154(3) 0.91117(14) 0.0387(6) Uani 1 1 d . . . H32A H 0.3317 0.6615 0.9605 0.046 Uiso 1 1 calc R . . H32B H 0.3779 0.8359 0.9021 0.046 Uiso 1 1 calc R . . C33 C 0.6229(3) 0.6919(3) 0.92453(14) 0.0370(5) Uani 1 1 d . . . H33A H 0.7057 0.7541 0.8777 0.044 Uiso 1 1 calc R . . H33B H 0.6633 0.5726 0.9307 0.044 Uiso 1 1 calc R . . C34 C 0.6501(3) 0.7530(3) 0.99840(14) 0.0371(5) Uani 1 1 d . . . H34A H 0.6059 0.8715 0.9919 0.044 Uiso 1 1 calc R . . H34B H 0.5658 0.6902 1.0446 0.044 Uiso 1 1 calc R . . C35 C 0.8543(4) 0.7368(3) 1.01674(14) 0.0388(6) Uani 1 1 d . . . H35A H 0.9403 0.7964 0.9702 0.047 Uiso 1 1 calc R . . H35B H 0.8974 0.6179 1.0259 0.047 Uiso 1 1 calc R . . C36 C 0.8744(4) 0.8058(3) 1.08918(14) 0.0391(6) Uani 1 1 d . . . H36A H 0.8266 0.9235 1.0808 0.047 Uiso 1 1 calc R . . H36B H 0.7917 0.7434 1.1360 0.047 Uiso 1 1 calc R . . C37 C 1.0800(4) 0.7957(3) 1.10665(14) 0.0394(6) Uani 1 1 d . . . H37A H 1.1640 0.8510 1.0583 0.047 Uiso 1 1 calc R . . H37B H 1.1242 0.6772 1.1184 0.047 Uiso 1 1 calc R . . C38 C 1.1070(4) 0.8745(3) 1.17577(13) 0.0387(6) Uani 1 1 d . . . H38A H 1.0636 0.9933 1.1648 0.046 Uiso 1 1 calc R . . H38B H 1.0265 0.8183 1.2249 0.046 Uiso 1 1 calc R . . C39 C 1.3169(4) 0.8602(3) 1.18793(13) 0.0397(6) Uani 1 1 d . . . H39A H 1.3572 0.7407 1.1993 0.048 Uiso 1 1 calc R . . H39B H 1.3957 0.9123 1.1375 0.048 Uiso 1 1 calc R . . C40 C 1.3638(4) 0.9369(3) 1.25281(14) 0.0381(6) Uani 1 1 d . . . O40 O 1.5498(3) 0.9540(2) 1.24719(10) 0.0468(5) Uani 1 1 d . . . H40 H 1.578(4) 1.022(3) 1.2905(16) 0.056 Uiso 1 1 d . . . O41 O 1.2446(3) 0.9794(3) 1.30463(10) 0.0536(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 N11 0.0430(13) 0.0500(13) 0.0278(10) -0.0084(9) -0.0063(8) -0.0050(9) C12 0.0399(15) 0.0453(14) 0.0285(11) -0.0060(10) -0.0094(10) -0.0065(10) C13 0.0379(14) 0.0438(14) 0.0266(11) -0.0049(10) -0.0073(9) -0.0071(10) N13 0.0439(13) 0.0427(12) 0.0272(9) -0.0068(8) -0.0093(8) -0.0069(9) C14 0.0399(15) 0.0456(14) 0.0296(11) -0.0042(10) -0.0118(10) -0.0075(11) C15 0.0387(15) 0.0493(15) 0.0336(12) -0.0059(11) -0.0087(10) -0.0056(11) C16 0.0404(15) 0.0466(15) 0.0346(13) -0.0061(11) -0.0039(10) -0.0027(11) N21 0.0387(13) 0.0475(12) 0.0303(10) -0.0080(9) -0.0078(8) -0.0039(9) C22 0.0361(14) 0.0440(14) 0.0295(11) -0.0069(10) -0.0078(9) -0.0034(10) C23 0.0431(15) 0.0377(13) 0.0282(11) -0.0047(10) -0.0085(10) -0.0059(10) N23 0.0428(13) 0.0428(12) 0.0268(9) -0.0076(8) -0.0097(8) -0.0063(9) C24 0.0411(15) 0.0450(14) 0.0332(12) -0.0029(11) -0.0116(10) -0.0068(11) C25 0.0392(15) 0.0446(15) 0.0372(13) -0.0019(11) -0.0146(10) -0.0073(11) C26 0.0426(16) 0.0428(14) 0.0333(12) -0.0047(10) -0.0070(10) -0.0026(11) C31 0.0378(14) 0.0417(14) 0.0289(11) -0.0064(10) -0.0092(10) 0.0007(10) O31 0.0435(11) 0.0668(12) 0.0377(10) -0.0204(9) -0.0120(8) 0.0004(9) O32 0.0422(11) 0.0641(12) 0.0408(10) -0.0235(9) -0.0092(8) 0.0000(8) C32 0.0396(15) 0.0453(14) 0.0334(12) -0.0097(10) -0.0100(10) -0.0014(11) C33 0.0395(14) 0.0417(14) 0.0315(11) -0.0093(10) -0.0095(9) 0.0003(10) C34 0.0392(14) 0.0410(13) 0.0335(12) -0.0100(10) -0.0110(10) 0.0005(10) C35 0.0416(15) 0.0453(14) 0.0326(12) -0.0126(10) -0.0088(10) -0.0009(11) C36 0.0422(15) 0.0441(14) 0.0346(12) -0.0107(11) -0.0126(10) -0.0029(11) C37 0.0402(15) 0.0460(15) 0.0347(12) -0.0115(11) -0.0107(10) 0.0013(11) C38 0.0414(15) 0.0460(14) 0.0298(12) -0.0095(10) -0.0065(10) -0.0019(11) C39 0.0437(15) 0.0466(14) 0.0306(12) -0.0115(11) -0.0064(10) -0.0021(11) C40 0.0394(15) 0.0437(14) 0.0310(12) -0.0060(10) -0.0078(10) -0.0007(11) O40 0.0404(11) 0.0700(13) 0.0360(9) -0.0216(9) -0.0066(7) -0.0064(9) O41 0.0429(12) 0.0836(15) 0.0419(10) -0.0302(10) -0.0061(8) -0.0022(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 N11 C16 1.337(3) . ? N11 C12 1.338(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 N13 1.437(3) . ? N13 N23 1.264(3) . ? C14 C15 1.375(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C22 1.343(3) . ? N21 C26 1.344(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.401(3) . ? C23 N23 1.420(3) . ? C24 C25 1.383(3) . ? C24 H24 0.9500 . ? C25 C26 1.395(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 O32 1.202(3) . ? C31 O31 1.324(3) . ? C31 C32 1.504(3) . ? O31 H31 1.04(3) . ? C32 C33 1.523(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.530(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.514(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.527(3) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.521(3) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.535(3) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.519(3) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.505(3) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 O41 1.219(3) . ? C40 O40 1.313(3) . ? O40 H40 1.08(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 C16 N11 C12 118.0(2) . . ? N11 C12 C13 122.8(2) . . ? N11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C14 C13 C12 118.6(2) . . ? C14 C13 N13 125.8(2) . . ? C12 C13 N13 115.6(2) . . ? N23 N13 C13 113.3(2) . . ? C15 C14 C13 119.0(2) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 118.9(2) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N11 C16 C15 122.8(2) . . ? N11 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C22 N21 C26 118.3(2) . . ? N21 C22 C23 122.8(2) . . ? N21 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C24 119.0(2) . . ? C22 C23 N23 115.8(2) . . ? C24 C23 N23 125.2(2) . . ? N13 N23 C23 113.5(2) . . ? C25 C24 C23 118.0(2) . . ? C25 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? C24 C25 C26 119.7(2) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? N21 C26 C25 122.2(2) . . ? N21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? O32 C31 O31 123.9(2) . . ? O32 C31 C32 125.0(2) . . ? O31 C31 C32 111.14(19) . . ? C31 O31 H31 109.4(15) . . ? C31 C32 C33 116.4(2) . . ? C31 C32 H32A 108.2 . . ? C33 C32 H32A 108.2 . . ? C31 C32 H32B 108.2 . . ? C33 C32 H32B 108.2 . . ? H32A C32 H32B 107.3 . . ? C32 C33 C34 111.15(19) . . ? C32 C33 H33A 109.4 . . ? C34 C33 H33A 109.4 . . ? C32 C33 H33B 109.4 . . ? C34 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C35 C34 C33 115.5(2) . . ? C35 C34 H34A 108.4 . . ? C33 C34 H34A 108.4 . . ? C35 C34 H34B 108.4 . . ? C33 C34 H34B 108.4 . . ? H34A C34 H34B 107.5 . . ? C34 C35 C36 113.2(2) . . ? C34 C35 H35A 108.9 . . ? C36 C35 H35A 108.9 . . ? C34 C35 H35B 108.9 . . ? C36 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 113.8(2) . . ? C37 C36 H36A 108.8 . . ? C35 C36 H36A 108.8 . . ? C37 C36 H36B 108.8 . . ? C35 C36 H36B 108.8 . . ? H36A C36 H36B 107.7 . . ? C36 C37 C38 115.0(2) . . ? C36 C37 H37A 108.5 . . ? C38 C37 H37A 108.5 . . ? C36 C37 H37B 108.5 . . ? C38 C37 H37B 108.5 . . ? H37A C37 H37B 107.5 . . ? C39 C38 C37 111.09(19) . . ? C39 C38 H38A 109.4 . . ? C37 C38 H38A 109.4 . . ? C39 C38 H38B 109.4 . . ? C37 C38 H38B 109.4 . . ? H38A C38 H38B 108.0 . . ? C40 C39 C38 116.4(2) . . ? C40 C39 H39A 108.2 . . ? C38 C39 H39A 108.2 . . ? C40 C39 H39B 108.2 . . ? C38 C39 H39B 108.2 . . ? H39A C39 H39B 107.3 . . ? O41 C40 O40 123.3(2) . . ? O41 C40 C39 124.6(2) . . ? O40 C40 C39 112.1(2) . . ? C40 O40 H40 110.4(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.9(3) . . . . ? N11 C12 C13 C14 -1.6(4) . . . . ? N11 C12 C13 N13 177.1(2) . . . . ? C14 C13 N13 N23 0.6(3) . . . . ? C12 C13 N13 N23 -178.0(2) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? N13 C13 C14 C15 -178.0(2) . . . . ? C13 C14 C15 C16 1.1(4) . . . . ? C12 N11 C16 C15 0.8(4) . . . . ? C14 C15 C16 N11 -1.9(4) . . . . ? C26 N21 C22 C23 -1.1(3) . . . . ? N21 C22 C23 C24 -0.4(3) . . . . ? N21 C22 C23 N23 -179.0(2) . . . . ? C13 N13 N23 C23 -179.90(18) . . . . ? C22 C23 N23 N13 -178.2(2) . . . . ? C24 C23 N23 N13 3.3(3) . . . . ? C22 C23 C24 C25 1.8(3) . . . . ? N23 C23 C24 C25 -179.7(2) . . . . ? C23 C24 C25 C26 -1.9(3) . . . . ? C22 N21 C26 C25 1.1(3) . . . . ? C24 C25 C26 N21 0.4(4) . . . . ? O32 C31 C32 C33 -0.3(4) . . . . ? O31 C31 C32 C33 178.7(2) . . . . ? C31 C32 C33 C34 -175.7(2) . . . . ? C32 C33 C34 C35 -179.5(2) . . . . ? C33 C34 C35 C36 177.8(2) . . . . ? C34 C35 C36 C37 -178.0(2) . . . . ? C35 C36 C37 C38 176.1(2) . . . . ? C36 C37 C38 C39 -179.3(2) . . . . ? C37 C38 C39 C40 178.5(2) . . . . ? C38 C39 C40 O41 14.8(4) . . . . ? C38 C39 C40 O40 -164.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O31 H31 N11 1.04(3) 1.65(3) 2.682(3) 175(2) . O40 H40 N21 1.08(3) 1.61(3) 2.683(3) 171(2) 1_666 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.609 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.092 #END data_4,4'azpy:SuA _database_code_depnum_ccdc_archive 'CCDC 892704' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 05:04BD (4-pyridyl)-N=N-(4-pyridyl), HOOC-(CH2)6-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C10 H8 N4) (C8 H14 O4) ; _chemical_formula_sum 'C18 H22 N4 O4' _chemical_formula_weight 358.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8269(6) _cell_length_b 8.6817(8) _cell_length_c 9.0827(9) _cell_angle_alpha 76.314(6) _cell_angle_beta 87.963(6) _cell_angle_gamma 77.486(6) _cell_volume 435.76(7) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3758 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 32.77 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 190 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9748 _exptl_absorpt_correction_T_max 0.9863 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9736 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 33.12 _reflns_number_total 3144 _reflns_number_gt 2201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0750P)^2^+0.0200P] 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 3144 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1459 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 N11 N 0.44565(18) 0.36459(12) 0.16690(12) 0.0242(2) Uani 1 1 d . . . C12 C 0.4253(2) 0.29985(14) 0.04940(14) 0.0244(2) Uani 1 1 d . . . H12A H 0.2790 0.3296 -0.0040 0.029 Uiso 1 1 calc R . . C13 C 0.6062(2) 0.19190(14) 0.00188(14) 0.0235(2) Uani 1 1 d . . . H13A H 0.5855 0.1473 -0.0814 0.028 Uiso 1 1 calc R . . C14 C 0.81992(19) 0.15073(13) 0.08040(13) 0.0209(2) Uani 1 1 d . . . N14 N 1.02287(16) 0.04115(12) 0.04308(12) 0.0241(2) Uani 1 1 d . . . C15 C 0.8453(2) 0.21919(14) 0.19983(14) 0.0242(3) Uani 1 1 d . . . H15A H 0.9913 0.1945 0.2528 0.029 Uiso 1 1 calc R . . C16 C 0.6527(2) 0.32481(14) 0.24056(15) 0.0249(3) Uani 1 1 d . . . H16A H 0.6683 0.3706 0.3239 0.030 Uiso 1 1 calc R . . C21 C 0.0293(2) 0.63516(13) 0.32508(14) 0.0216(2) Uani 1 1 d . . . O21 O 0.04390(16) 0.56163(11) 0.21133(11) 0.0278(2) Uani 1 1 d . . . H21 H 0.191(3) 0.5071(18) 0.2090(18) 0.033 Uiso 1 1 d . . . O22 O 0.19091(15) 0.62041(11) 0.40993(11) 0.0325(2) Uani 1 1 d . . . C22 C -0.21285(19) 0.73861(13) 0.33141(14) 0.0222(2) Uani 1 1 d . . . H22A H -0.3278 0.6675 0.3494 0.027 Uiso 1 1 calc R . . H22B H -0.2513 0.8150 0.2314 0.027 Uiso 1 1 calc R . . C23 C -0.2424(2) 0.83518(13) 0.45201(14) 0.0224(2) Uani 1 1 d . . . H23A H -0.1198 0.9001 0.4402 0.027 Uiso 1 1 calc R . . H23B H -0.2205 0.7595 0.5533 0.027 Uiso 1 1 calc R . . C24 C -0.48398(19) 0.94804(13) 0.44204(13) 0.0221(2) Uani 1 1 d . . . H24A H -0.6057 0.8822 0.4575 0.027 Uiso 1 1 calc R . . H24B H -0.5079 1.0201 0.3391 0.027 Uiso 1 1 calc 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 N11 0.0243(5) 0.0206(4) 0.0270(6) -0.0085(4) 0.0048(4) -0.0009(4) C12 0.0214(5) 0.0227(5) 0.0272(6) -0.0076(4) 0.0009(4) 0.0011(4) C13 0.0216(5) 0.0240(5) 0.0252(6) -0.0108(4) 0.0009(4) 0.0003(4) C14 0.0181(5) 0.0192(5) 0.0257(6) -0.0094(4) 0.0034(4) -0.0004(4) N14 0.0193(5) 0.0252(5) 0.0289(6) -0.0136(4) 0.0012(4) 0.0005(4) C15 0.0218(6) 0.0248(5) 0.0276(7) -0.0111(4) 0.0009(4) -0.0028(4) C16 0.0268(6) 0.0233(5) 0.0273(6) -0.0122(4) 0.0048(5) -0.0046(4) C21 0.0223(5) 0.0189(5) 0.0237(6) -0.0083(4) 0.0021(4) -0.0009(4) O21 0.0235(5) 0.0301(5) 0.0302(5) -0.0175(4) 0.0014(4) 0.0048(3) O22 0.0246(5) 0.0367(5) 0.0375(6) -0.0186(4) -0.0045(4) 0.0023(4) C22 0.0191(5) 0.0220(5) 0.0253(6) -0.0106(4) 0.0002(4) 0.0016(4) C23 0.0235(5) 0.0211(5) 0.0225(6) -0.0103(4) 0.0011(4) 0.0007(4) C24 0.0213(5) 0.0206(5) 0.0244(6) -0.0101(4) 0.0025(4) 0.0004(4) _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 N11 C16 1.3378(17) . ? N11 C12 1.3382(15) . ? C12 C13 1.3810(16) . ? C12 H12A 0.9500 . ? C13 C14 1.3917(17) . ? C13 H13A 0.9500 . ? C14 C15 1.3808(16) . ? C14 N14 1.4335(14) . ? N14 N14 1.2473(19) 2_755 ? C15 C16 1.3866(17) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C21 O22 1.2042(15) . ? C21 O21 1.3283(14) . ? C21 C22 1.5066(16) . ? O21 H21 0.885(17) . ? C22 C23 1.5136(15) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5230(16) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C24 1.523(2) 2_476 ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? 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 C16 N11 C12 118.41(10) . . ? N11 C12 C13 123.27(11) . . ? N11 C12 H12A 118.4 . . ? C13 C12 H12A 118.4 . . ? C12 C13 C14 117.64(11) . . ? C12 C13 H13A 121.2 . . ? C14 C13 H13A 121.2 . . ? C15 C14 C13 119.79(10) . . ? C15 C14 N14 116.54(10) . . ? C13 C14 N14 123.66(10) . . ? N14 N14 C14 113.23(12) 2_755 . ? C14 C15 C16 118.41(11) . . ? C14 C15 H15A 120.8 . . ? C16 C15 H15A 120.8 . . ? N11 C16 C15 122.46(11) . . ? N11 C16 H16A 118.8 . . ? C15 C16 H16A 118.8 . . ? O22 C21 O21 123.56(11) . . ? O22 C21 C22 125.43(11) . . ? O21 C21 C22 111.01(10) . . ? C21 O21 H21 107.7(10) . . ? C21 C22 C23 114.83(10) . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.5 . . ? C22 C23 C24 111.74(9) . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C23 C24 C24 113.08(12) . 2_476 ? C23 C24 H24A 109.0 . . ? C24 C24 H24A 109.0 2_476 . ? C23 C24 H24B 109.0 . . ? C24 C24 H24B 109.0 2_476 . ? H24A C24 H24B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 1.09(18) . . . . ? N11 C12 C13 C14 -0.60(18) . . . . ? C12 C13 C14 C15 -0.82(17) . . . . ? C12 C13 C14 N14 -179.63(11) . . . . ? C15 C14 N14 N14 166.12(13) . . . 2_755 ? C13 C14 N14 N14 -15.0(2) . . . 2_755 ? C13 C14 C15 C16 1.67(18) . . . . ? N14 C14 C15 C16 -179.44(10) . . . . ? C12 N11 C16 C15 -0.16(18) . . . . ? C14 C15 C16 N11 -1.20(18) . . . . ? O22 C21 C22 C23 2.88(18) . . . . ? O21 C21 C22 C23 -176.57(10) . . . . ? C21 C22 C23 C24 174.79(10) . . . . ? C22 C23 C24 C24 -177.72(12) . . . 2_476 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O21 H21 N11 0.885(17) 1.809(18) 2.6633(13) 161.6(15) . _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.495 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.057 #END