# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound1 #TrackingRef 'web_deposit_cif_file_0_Jian-ZhenLiao_1357890106.compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 Cd F2 N10 O2' _chemical_formula_sum 'C16 H10 Cd F2 N10 O2' _chemical_formula_weight 524.74 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.6882(15) _cell_length_b 10.6882(15) _cell_length_c 16.036(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1831.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6947 _cell_measurement_theta_min 3.1762 _cell_measurement_theta_max 27.4662 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.252 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8345 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15338 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2096 _reflns_number_gt 2090 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007) (Rigaku, 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0135P)^2^+1.4692P] 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 constr _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 0.00(3) _refine_ls_number_reflns 2096 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0489 _refine_ls_wR_factor_gt 0.0488 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.700607(16) 0.700607(16) 0.0000 0.02198(7) Uani 1 2 d S . . C3 C 0.7987(3) 0.8707(3) 0.35895(17) 0.0322(6) Uani 1 1 d . . . N5 N 0.85032(19) 0.7929(2) 0.22043(13) 0.0289(5) Uani 1 1 d . . . H5 H 0.7707 0.7901 0.2130 0.035 Uiso 1 1 calc R . . C1 C 0.9262(2) 0.7580(2) 0.15439(16) 0.0252(5) Uani 1 1 d . . . N1 N 0.8785(2) 0.7335(2) 0.07923(14) 0.0298(5) Uani 1 1 d . . . C2 C 0.8929(3) 0.8313(3) 0.29649(18) 0.0340(7) Uani 1 1 d . . . C6 C 0.6452(3) 0.9370(3) 0.4880(2) 0.0476(8) Uani 1 1 d . . . C4 C 0.6842(3) 0.8136(3) 0.36813(18) 0.0404(7) Uani 1 1 d . . . H1 H 0.6593 0.7525 0.3303 0.049 Uiso 1 1 calc R . . C7 C 0.7567(4) 0.9960(3) 0.4802(2) 0.0520(9) Uani 1 1 d . . . H3 H 0.7805 1.0575 0.5180 0.062 Uiso 1 1 calc R . . C8 C 0.8339(3) 0.9632(3) 0.4154(2) 0.0455(8) Uani 1 1 d . . . H4 H 0.9106 1.0033 0.4092 0.055 Uiso 1 1 calc R . . C5 C 0.6052(3) 0.8467(4) 0.4337(2) 0.0521(9) Uani 1 1 d . . . H2 H 0.5276 0.8086 0.4403 0.063 Uiso 1 1 calc R . . N4 N 1.0499(2) 0.7481(2) 0.15467(14) 0.0262(5) Uani 1 1 d . . . N3 N 1.0799(2) 0.7176(3) 0.07521(14) 0.0331(5) Uani 1 1 d . . . O1 O 1.0044(2) 0.8367(3) 0.31340(13) 0.0535(7) Uani 1 1 d . . . N2 N 0.9798(2) 0.7089(3) 0.03061(14) 0.0390(6) Uani 1 1 d . . . F1 F 0.5713(2) 0.9675(3) 0.55315(14) 0.0801(8) 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 Cd1 0.02277(8) 0.02277(8) 0.02039(12) -0.00081(8) 0.00081(8) -0.00033(10) C3 0.0280(12) 0.0439(16) 0.0247(13) -0.0017(11) 0.0020(12) 0.0029(12) N5 0.0198(9) 0.0427(12) 0.0242(10) -0.0040(10) -0.0001(8) 0.0021(10) C1 0.0236(13) 0.0289(13) 0.0230(13) -0.0016(10) -0.0009(10) 0.0008(10) N1 0.0214(11) 0.0446(15) 0.0233(11) -0.0044(10) -0.0005(9) -0.0007(9) C2 0.0261(13) 0.0461(18) 0.0298(15) -0.0022(12) 0.0006(11) -0.0044(12) C6 0.0503(18) 0.058(2) 0.0341(18) -0.0026(16) 0.0166(16) 0.0140(15) C4 0.0336(15) 0.0563(19) 0.0315(15) -0.0091(14) 0.0042(12) -0.0059(15) C7 0.061(2) 0.051(2) 0.045(2) -0.0151(16) 0.0093(16) 0.0058(17) C8 0.0413(18) 0.050(2) 0.0451(19) -0.0107(16) 0.0083(14) -0.0058(14) C5 0.0368(17) 0.074(3) 0.0456(19) -0.0043(18) 0.0128(15) -0.0031(18) N4 0.0225(11) 0.0316(11) 0.0245(11) -0.0024(10) -0.0020(9) -0.0001(9) N3 0.0244(11) 0.0473(15) 0.0275(11) -0.0091(11) 0.0004(9) -0.0015(10) O1 0.0230(10) 0.103(2) 0.0342(11) -0.0248(12) 0.0017(9) -0.0032(12) N2 0.0222(11) 0.0648(17) 0.0300(12) -0.0112(14) -0.0004(9) 0.0000(13) F1 0.0731(17) 0.105(2) 0.0625(14) -0.0240(14) 0.0369(13) 0.0086(14) _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 Cd1 N4 2.288(2) 2_644 ? Cd1 N4 2.288(2) 5_465 ? Cd1 N1 2.314(2) . ? Cd1 N1 2.314(2) 7 ? Cd1 O1 2.364(2) 5_465 ? Cd1 O1 2.364(2) 2_644 ? C3 C4 1.375(4) . ? C3 C8 1.393(4) . ? C3 C2 1.481(4) . ? N5 C2 1.365(3) . ? N5 C1 1.385(3) . ? C1 N4 1.326(3) . ? C1 N1 1.334(3) . ? N1 N2 1.359(3) . ? C2 O1 1.224(4) . ? C6 F1 1.349(3) . ? C6 C7 1.354(5) . ? C6 C5 1.369(5) . ? C4 C5 1.394(4) . ? C7 C8 1.372(4) . ? N4 N3 1.354(3) . ? N4 Cd1 2.288(2) 4_565 ? N3 N2 1.291(3) . ? O1 Cd1 2.364(2) 4_565 ? 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 N4 Cd1 N4 141.65(11) 2_644 5_465 ? N4 Cd1 N1 106.07(8) 2_644 . ? N4 Cd1 N1 100.11(8) 5_465 . ? N4 Cd1 N1 100.11(8) 2_644 7 ? N4 Cd1 N1 106.07(8) 5_465 7 ? N1 Cd1 N1 92.99(12) . 7 ? N4 Cd1 O1 78.84(8) 2_644 5_465 ? N4 Cd1 O1 72.73(8) 5_465 5_465 ? N1 Cd1 O1 172.16(8) . 5_465 ? N1 Cd1 O1 92.12(9) 7 5_465 ? N4 Cd1 O1 72.73(8) 2_644 2_644 ? N4 Cd1 O1 78.84(8) 5_465 2_644 ? N1 Cd1 O1 92.12(9) . 2_644 ? N1 Cd1 O1 172.16(8) 7 2_644 ? O1 Cd1 O1 83.44(14) 5_465 2_644 ? C4 C3 C8 119.0(3) . . ? C4 C3 C2 123.5(3) . . ? C8 C3 C2 117.3(3) . . ? C2 N5 C1 124.7(2) . . ? N4 C1 N1 111.6(2) . . ? N4 C1 N5 127.1(2) . . ? N1 C1 N5 121.4(2) . . ? C1 N1 N2 104.6(2) . . ? C1 N1 Cd1 147.07(18) . . ? N2 N1 Cd1 108.05(16) . . ? O1 C2 N5 122.5(3) . . ? O1 C2 C3 119.9(3) . . ? N5 C2 C3 117.6(2) . . ? F1 C6 C7 118.3(3) . . ? F1 C6 C5 118.7(3) . . ? C7 C6 C5 122.9(3) . . ? C3 C4 C5 120.5(3) . . ? C6 C7 C8 118.7(3) . . ? C7 C8 C3 120.8(3) . . ? C6 C5 C4 118.0(3) . . ? C1 N4 N3 104.6(2) . . ? C1 N4 Cd1 133.24(19) . 4_565 ? N3 N4 Cd1 121.29(16) . 4_565 ? N2 N3 N4 110.0(2) . . ? C2 O1 Cd1 139.5(2) . 4_565 ? N3 N2 N1 109.2(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 N5 H5 N3 0.86 2.13 2.983(3) 171.2 5_465 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.318 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 919195' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound2 #TrackingRef 'web_deposit_cif_file_2_Jian-ZhenLiao_1357890106.compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H30 Cd3 N36 O18' _chemical_formula_sum 'C48 H30 Cd3 N36 O18' _chemical_formula_weight 1736.28 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' Cd Cd -0.8075 1.2024 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 18.118(3) _cell_length_b 18.118(3) _cell_length_c 17.507(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 4976.9(14) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5215 _cell_measurement_theta_min 3.4874 _cell_measurement_theta_max 27.4932 _exptl_crystal_description cube _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1400 _exptl_crystal_size_min 0.1200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2574 _exptl_absorpt_coefficient_mu 1.049 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8391 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details Higashi,T.(1995). _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Saturn724 (2x2 bin mode)' _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14003 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2538 _reflns_number_gt 2507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007) (Rigaku, 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0099P)^2^+20.5152P] 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 2538 _refine_ls_number_parameters 162 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0769 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.304 _refine_ls_restrained_S_all 1.304 _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 Cd1 Cd 0.0000 0.0000 0.5000 0.02503(13) Uani 1 6 d S . . Cd2 Cd 0.0000 0.0000 0.26556(2) 0.02612(11) Uani 1 3 d S . . O1 O 0.05754(17) 0.11367(14) 0.18214(13) 0.0430(6) Uani 1 1 d . . . N4 N 0.0721(2) 0.11720(17) 0.41950(15) 0.0394(7) Uani 1 1 d . . . N2 N 0.1196(2) 0.23591(18) 0.25280(16) 0.0439(8) Uani 1 1 d D . . N5 N 0.1144(2) 0.19380(19) 0.44568(16) 0.0530(9) Uani 1 1 d . . . N3 N 0.06634(19) 0.11860(17) 0.34228(15) 0.0361(7) Uani 1 1 d . . . N6 N 0.1386(2) 0.24932(19) 0.38702(17) 0.0544(10) Uani 1 1 d . . . C7 C 0.0714(3) 0.2535(3) -0.0118(3) 0.0694(14) Uani 1 1 d . . . H3 H 0.0342 0.2297 -0.0528 0.083 Uiso 1 1 calc R . . C5 C 0.1974(4) 0.3698(3) 0.0420(2) 0.0742(16) Uani 1 1 d . . . H4 H 0.2449 0.4239 0.0368 0.089 Uiso 1 1 calc R . . C2 C 0.0942(2) 0.1918(2) 0.18662(18) 0.0369(8) Uani 1 1 d . . . C6 C 0.1401(3) 0.3340(3) -0.0163(2) 0.0612(12) Uani 1 1 d . . . C3 C 0.1129(2) 0.2438(2) 0.11567(19) 0.0385(8) Uani 1 1 d . . . C4 C 0.1836(3) 0.3242(3) 0.1090(2) 0.0586(12) Uani 1 1 d . . . H5 H 0.2217 0.3475 0.1494 0.070 Uiso 1 1 calc R . . C8 C 0.0585(3) 0.2084(3) 0.0551(2) 0.0575(11) Uani 1 1 d . . . H2 H 0.0124 0.1533 0.0591 0.069 Uiso 1 1 calc R . . C1 C 0.1079(2) 0.2006(2) 0.32516(18) 0.0380(8) Uani 1 1 d . . . N1 N 0.1534(4) 0.3836(3) -0.0875(2) 0.0933(17) Uani 1 1 d . . . O2 O 0.0975(4) 0.3564(4) -0.1337(2) 0.132(2) Uani 1 1 d . . . O3 O 0.2210(4) 0.4482(3) -0.0953(2) 0.149(3) Uani 1 1 d . . . H1 H 0.141(5) 0.2891(9) 0.255(5) 0.179 Uiso 1 1 d 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 Cd1 0.02830(18) 0.02830(18) 0.0185(2) 0.000 0.000 0.01415(9) Cd2 0.02759(14) 0.02759(14) 0.02317(19) 0.000 0.000 0.01380(7) O1 0.0617(17) 0.0276(12) 0.0291(12) 0.0022(10) 0.0015(11) 0.0145(12) N4 0.0568(19) 0.0262(14) 0.0233(14) 0.0032(11) 0.0025(13) 0.0118(14) N2 0.067(2) 0.0295(15) 0.0232(14) 0.0035(12) 0.0029(13) 0.0151(15) N5 0.085(3) 0.0293(16) 0.0255(15) 0.0026(12) 0.0011(15) 0.0139(17) N3 0.0477(17) 0.0297(14) 0.0238(13) 0.0012(11) 0.0002(12) 0.0141(13) N6 0.088(3) 0.0273(16) 0.0272(15) 0.0005(12) 0.0004(16) 0.0135(17) C7 0.072(3) 0.082(4) 0.045(2) 0.015(2) -0.011(2) 0.032(3) C5 0.118(4) 0.034(2) 0.035(2) 0.0046(17) 0.013(2) 0.011(2) C2 0.047(2) 0.0335(18) 0.0268(16) 0.0014(13) 0.0027(14) 0.0172(16) C6 0.101(4) 0.048(2) 0.037(2) 0.0147(18) 0.010(2) 0.040(3) C3 0.051(2) 0.0341(18) 0.0277(16) 0.0030(14) 0.0048(15) 0.0190(17) C4 0.084(3) 0.038(2) 0.032(2) 0.0005(16) 0.002(2) 0.014(2) C8 0.053(3) 0.057(3) 0.044(2) 0.0124(19) -0.0077(19) 0.014(2) C1 0.054(2) 0.0280(17) 0.0240(16) 0.0023(13) 0.0028(14) 0.0150(16) N1 0.166(6) 0.076(3) 0.044(2) 0.022(2) 0.015(3) 0.064(4) O2 0.185(5) 0.163(5) 0.062(3) 0.044(3) -0.008(3) 0.099(4) O3 0.240(7) 0.070(3) 0.061(3) 0.037(2) 0.011(3) 0.020(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 Cd1 N4 2.330(3) 11_556 ? Cd1 N4 2.330(3) 2 ? Cd1 N4 2.330(3) 12_556 ? Cd1 N4 2.330(3) . ? Cd1 N4 2.330(3) 3 ? Cd1 N4 2.330(3) 10_556 ? Cd2 N3 2.299(3) . ? Cd2 N3 2.299(3) 3 ? Cd2 N3 2.299(3) 2 ? Cd2 O1 2.305(2) 2 ? Cd2 O1 2.305(2) 3 ? Cd2 O1 2.305(2) . ? O1 C2 1.230(4) . ? N4 N5 1.288(4) . ? N4 N3 1.357(4) . ? N2 C2 1.351(4) . ? N2 C1 1.387(4) . ? N5 N6 1.348(4) . ? N3 C1 1.321(4) . ? N6 C1 1.330(4) . ? C7 C6 1.366(6) . ? C7 C8 1.379(5) . ? C5 C6 1.367(6) . ? C5 C4 1.384(5) . ? C2 C3 1.492(4) . ? C6 N1 1.484(5) . ? C3 C8 1.369(5) . ? C3 C4 1.382(5) . ? N1 O2 1.193(7) . ? N1 O3 1.207(7) . ? 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 N4 Cd1 N4 180.00(10) 11_556 2 ? N4 Cd1 N4 87.20(10) 11_556 12_556 ? N4 Cd1 N4 92.80(10) 2 12_556 ? N4 Cd1 N4 92.80(10) 11_556 . ? N4 Cd1 N4 87.20(10) 2 . ? N4 Cd1 N4 92.80(10) 12_556 . ? N4 Cd1 N4 92.80(10) 11_556 3 ? N4 Cd1 N4 87.20(10) 2 3 ? N4 Cd1 N4 180.00(10) 12_556 3 ? N4 Cd1 N4 87.20(10) . 3 ? N4 Cd1 N4 87.20(10) 11_556 10_556 ? N4 Cd1 N4 92.80(10) 2 10_556 ? N4 Cd1 N4 87.20(10) 12_556 10_556 ? N4 Cd1 N4 180.00(12) . 10_556 ? N4 Cd1 N4 92.80(10) 3 10_556 ? N3 Cd2 N3 89.30(9) . 3 ? N3 Cd2 N3 89.30(9) . 2 ? N3 Cd2 N3 89.30(9) 3 2 ? N3 Cd2 O1 135.80(10) . 2 ? N3 Cd2 O1 130.56(10) 3 2 ? N3 Cd2 O1 75.14(9) 2 2 ? N3 Cd2 O1 130.56(10) . 3 ? N3 Cd2 O1 75.14(9) 3 3 ? N3 Cd2 O1 135.80(10) 2 3 ? O1 Cd2 O1 84.15(9) 2 3 ? N3 Cd2 O1 75.14(9) . . ? N3 Cd2 O1 135.80(10) 3 . ? N3 Cd2 O1 130.56(10) 2 . ? O1 Cd2 O1 84.15(9) 2 . ? O1 Cd2 O1 84.15(9) 3 . ? C2 O1 Cd2 137.0(2) . . ? N5 N4 N3 110.1(3) . . ? N5 N4 Cd1 121.8(2) . . ? N3 N4 Cd1 127.3(2) . . ? C2 N2 C1 125.6(3) . . ? N4 N5 N6 109.2(3) . . ? C1 N3 N4 104.0(3) . . ? C1 N3 Cd2 131.0(2) . . ? N4 N3 Cd2 125.0(2) . . ? C1 N6 N5 104.7(3) . . ? C6 C7 C8 118.4(4) . . ? C6 C5 C4 118.7(4) . . ? O1 C2 N2 124.3(3) . . ? O1 C2 C3 119.7(3) . . ? N2 C2 C3 116.0(3) . . ? C7 C6 C5 122.3(4) . . ? C7 C6 N1 118.7(5) . . ? C5 C6 N1 119.0(5) . . ? C8 C3 C4 119.9(3) . . ? C8 C3 C2 117.8(3) . . ? C4 C3 C2 122.3(3) . . ? C3 C4 C5 119.8(4) . . ? C3 C8 C7 120.7(4) . . ? N3 C1 N6 112.0(3) . . ? N3 C1 N2 126.6(3) . . ? N6 C1 N2 121.4(3) . . ? O2 N1 O3 124.3(5) . . ? O2 N1 C6 118.2(6) . . ? O3 N1 C6 117.5(6) . . ? 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 N3 Cd2 O1 C2 -6.5(4) . . . . ? N3 Cd2 O1 C2 -79.6(4) 3 . . . ? N3 Cd2 O1 C2 69.4(4) 2 . . . ? O1 Cd2 O1 C2 134.1(4) 2 . . . ? O1 Cd2 O1 C2 -141.2(4) 3 . . . ? N4 Cd1 N4 N5 -48.2(4) 11_556 . . . ? N4 Cd1 N4 N5 131.8(4) 2 . . . ? N4 Cd1 N4 N5 39.1(4) 12_556 . . . ? N4 Cd1 N4 N5 -140.9(4) 3 . . . ? N4 Cd1 N4 N5 86(100) 10_556 . . . ? N4 Cd1 N4 N3 142.7(3) 11_556 . . . ? N4 Cd1 N4 N3 -37.3(3) 2 . . . ? N4 Cd1 N4 N3 -130.0(2) 12_556 . . . ? N4 Cd1 N4 N3 50.0(2) 3 . . . ? N4 Cd1 N4 N3 -83(100) 10_556 . . . ? N3 N4 N5 N6 -0.1(5) . . . . ? Cd1 N4 N5 N6 -170.9(3) . . . . ? N5 N4 N3 C1 0.0(4) . . . . ? Cd1 N4 N3 C1 170.2(3) . . . . ? N5 N4 N3 Cd2 178.8(3) . . . . ? Cd1 N4 N3 Cd2 -11.1(4) . . . . ? N3 Cd2 N3 C1 139.9(4) 3 . . . ? N3 Cd2 N3 C1 -130.8(4) 2 . . . ? O1 Cd2 N3 C1 -63.2(4) 2 . . . ? O1 Cd2 N3 C1 70.2(4) 3 . . . ? O1 Cd2 N3 C1 1.7(3) . . . . ? N3 Cd2 N3 N4 -38.5(2) 3 . . . ? N3 Cd2 N3 N4 50.8(2) 2 . . . ? O1 Cd2 N3 N4 118.4(3) 2 . . . ? O1 Cd2 N3 N4 -108.2(3) 3 . . . ? O1 Cd2 N3 N4 -176.7(3) . . . . ? N4 N5 N6 C1 0.1(5) . . . . ? Cd2 O1 C2 N2 7.1(6) . . . . ? Cd2 O1 C2 C3 -172.7(3) . . . . ? C1 N2 C2 O1 -0.6(7) . . . . ? C1 N2 C2 C3 179.2(4) . . . . ? C8 C7 C6 C5 2.1(8) . . . . ? C8 C7 C6 N1 -178.8(5) . . . . ? C4 C5 C6 C7 -2.5(8) . . . . ? C4 C5 C6 N1 178.4(5) . . . . ? O1 C2 C3 C8 29.7(6) . . . . ? N2 C2 C3 C8 -150.1(4) . . . . ? O1 C2 C3 C4 -148.5(4) . . . . ? N2 C2 C3 C4 31.7(6) . . . . ? C8 C3 C4 C5 2.3(7) . . . . ? C2 C3 C4 C5 -179.5(4) . . . . ? C6 C5 C4 C3 0.3(8) . . . . ? C4 C3 C8 C7 -2.8(7) . . . . ? C2 C3 C8 C7 179.0(4) . . . . ? C6 C7 C8 C3 0.6(8) . . . . ? N4 N3 C1 N6 0.0(5) . . . . ? Cd2 N3 C1 N6 -178.6(3) . . . . ? N4 N3 C1 N2 -179.4(4) . . . . ? Cd2 N3 C1 N2 1.9(6) . . . . ? N5 N6 C1 N3 -0.1(5) . . . . ? N5 N6 C1 N2 179.4(4) . . . . ? C2 N2 C1 N3 -3.8(7) . . . . ? C2 N2 C1 N6 176.8(4) . . . . ? C7 C6 N1 O2 10.5(8) . . . . ? C5 C6 N1 O2 -170.4(6) . . . . ? C7 C6 N1 O3 -168.1(6) . . . . ? C5 C6 N1 O3 11.0(8) . . . . ? 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 N2 H1 N6 0.841(10) 2.068(18) 2.899(4) 170(8) 16 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.541 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 919196' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound3 #TrackingRef 'web_deposit_cif_file_4_Jian-ZhenLiao_1357890106.compound3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cd N10 O2 S2' _chemical_formula_sum 'C12 H8 Cd N10 O2 S2' _chemical_formula_weight 500.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.877(2) _cell_length_b 10.898(2) _cell_length_c 14.101(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1671.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6272 _cell_measurement_theta_min 3.0138 _cell_measurement_theta_max 27.5165 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.990 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 1.591 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.7929 _exptl_absorpt_correction_T_max 0.8745 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13514 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3820 _reflns_number_gt 3808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007) (Rigaku, 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0296P)^2^+0.7063P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(19) _refine_ls_number_reflns 3820 _refine_ls_number_parameters 244 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0542 _refine_ls_wR_factor_gt 0.0541 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.100 _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 Cd1 Cd -0.435019(14) -0.268712(16) -0.130493(12) 0.02328(5) Uani 1 1 d . . . N1 N -0.29918(19) -0.2391(2) -0.01592(15) 0.0313(5) Uani 1 1 d . . . O1 O -0.24749(18) -0.2101(2) -0.21214(14) 0.0351(4) Uani 1 1 d . . . N2 N -0.32059(19) -0.2800(2) 0.07378(16) 0.0318(5) Uani 1 1 d . . . N3 N -0.21920(19) -0.2743(2) 0.12270(16) 0.0331(5) Uani 1 1 d . . . N5 N -0.1155(2) -0.1610(3) -0.09287(18) 0.0379(6) Uani 1 1 d D . . S1 S -0.12267(9) -0.07188(10) -0.36555(7) 0.0568(2) Uani 1 1 d . . . N9 N -0.4758(2) -0.0739(2) -0.18195(18) 0.0318(5) Uani 1 1 d . . . N10 N -0.6293(2) -0.0907(2) -0.30091(18) 0.0345(5) Uani 1 1 d D . . N8 N -0.4044(2) 0.0186(2) -0.14754(18) 0.0364(5) Uani 1 1 d . . . S2 S -0.77446(9) -0.13442(9) -0.55640(6) 0.0491(2) Uani 1 1 d . . . N7 N -0.4283(2) 0.1181(2) -0.19463(17) 0.0338(5) Uani 1 1 d . . . N4 N -0.12784(19) -0.2302(3) 0.06569(16) 0.0329(5) Uani 1 1 d . . . O2 O -0.6050(2) 0.0138(2) -0.43872(15) 0.0445(5) Uani 1 1 d . . . N6 N -0.5182(2) 0.0942(2) -0.25932(17) 0.0299(5) Uani 1 1 d . . . C1 C -0.1802(2) -0.2101(2) -0.0176(2) 0.0293(5) Uani 1 1 d . . . C2 C -0.1542(2) -0.1567(2) -0.1849(2) 0.0291(5) Uani 1 1 d . . . C3 C -0.0772(3) -0.0857(3) -0.2498(2) 0.0344(6) Uani 1 1 d . . . C4 C 0.0315(3) -0.0195(3) -0.2323(2) 0.0363(6) Uani 1 1 d . . . H4 H 0.0710 -0.0146 -0.1739 0.044 Uiso 1 1 calc R . . C5 C 0.0715(3) 0.0381(3) -0.3158(3) 0.0533(9) Uani 1 1 d . . . H5A H 0.1427 0.0852 -0.3187 0.064 Uiso 1 1 calc R . . C6 C -0.0017(4) 0.0195(4) -0.3911(3) 0.0572(10) Uani 1 1 d . . . H6 H 0.0126 0.0532 -0.4507 0.069 Uiso 1 1 calc R . . C7 C -0.5435(2) -0.0242(2) -0.24909(19) 0.0267(5) Uani 1 1 d . . . C8 C -0.6531(2) -0.0707(2) -0.3948(2) 0.0307(6) Uani 1 1 d . . . C9 C -0.7398(3) -0.1556(3) -0.4385(2) 0.0330(6) Uani 1 1 d . . . C10 C -0.8051(3) -0.2505(3) -0.4009(2) 0.0421(7) Uani 1 1 d . . . H10A H -0.7997 -0.2753 -0.3379 0.051 Uiso 1 1 calc R . . C11 C -0.8821(3) -0.3070(3) -0.4692(3) 0.0509(9) Uani 1 1 d . . . H11 H -0.9324 -0.3739 -0.4562 0.061 Uiso 1 1 calc R . . C12 C -0.8745(3) -0.2529(3) -0.5553(3) 0.0529(9) Uani 1 1 d . . . H12 H -0.9192 -0.2781 -0.6080 0.063 Uiso 1 1 calc R . . H5 H -0.0380 -0.1456 -0.0840 0.063 Uiso 1 1 d RD . . H10 H -0.6493 -0.1592 -0.2710 0.063 Uiso 1 1 d RD . . 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 Cd1 0.01925(8) 0.02439(8) 0.02621(9) -0.00021(6) -0.00119(7) 0.00042(6) N1 0.0237(10) 0.0388(12) 0.0315(11) 0.0059(10) -0.0051(8) -0.0057(10) O1 0.0264(9) 0.0425(12) 0.0366(10) -0.0026(9) 0.0025(8) -0.0060(9) N2 0.0250(10) 0.0406(12) 0.0297(10) 0.0049(10) -0.0023(8) -0.0017(10) N3 0.0239(10) 0.0466(12) 0.0288(10) 0.0065(12) -0.0025(8) -0.0023(9) N5 0.0243(11) 0.0513(15) 0.0382(13) 0.0147(11) -0.0067(10) -0.0160(11) S1 0.0564(5) 0.0692(6) 0.0448(5) 0.0168(5) -0.0040(4) -0.0108(4) N9 0.0292(11) 0.0266(10) 0.0395(13) 0.0044(10) -0.0077(10) -0.0009(9) N10 0.0324(12) 0.0322(12) 0.0388(13) 0.0100(10) -0.0106(10) -0.0076(10) N8 0.0379(12) 0.0268(11) 0.0446(14) 0.0020(10) -0.0120(11) -0.0022(9) S2 0.0579(5) 0.0485(5) 0.0407(4) 0.0045(4) -0.0138(4) -0.0112(4) N7 0.0375(12) 0.0257(10) 0.0380(12) 0.0002(9) -0.0095(12) -0.0003(11) N4 0.0223(10) 0.0423(12) 0.0341(11) 0.0071(11) -0.0042(8) -0.0049(10) O2 0.0639(15) 0.0325(11) 0.0372(11) 0.0042(9) -0.0048(10) -0.0135(10) N6 0.0312(11) 0.0255(11) 0.0330(11) 0.0024(9) -0.0036(9) -0.0007(9) C1 0.0231(12) 0.0306(13) 0.0342(12) 0.0055(10) -0.0033(9) -0.0054(10) C2 0.0247(11) 0.0280(12) 0.0345(14) 0.0048(11) 0.0016(10) 0.0002(10) C3 0.0317(14) 0.0344(13) 0.0372(14) 0.0071(11) 0.0040(12) -0.0047(12) C4 0.0347(15) 0.0339(14) 0.0402(16) 0.0057(12) 0.0053(11) -0.0065(11) C5 0.0410(17) 0.0357(15) 0.083(3) 0.0160(16) 0.0168(19) -0.0055(16) C6 0.064(2) 0.053(2) 0.055(2) 0.0246(17) 0.0187(19) 0.0052(18) C7 0.0215(11) 0.0260(12) 0.0325(12) 0.0033(10) -0.0008(10) -0.0002(9) C8 0.0286(12) 0.0245(12) 0.0390(15) 0.0012(10) -0.0045(11) -0.0007(10) C9 0.0313(13) 0.0267(12) 0.0410(15) 0.0001(11) -0.0091(12) 0.0019(11) C10 0.0403(14) 0.0388(16) 0.0473(16) 0.0069(13) -0.0157(12) -0.0061(13) C11 0.0413(17) 0.0436(18) 0.068(2) 0.0051(16) -0.0198(16) -0.0136(15) C12 0.0511(18) 0.054(2) 0.0535(19) -0.0026(17) -0.0216(16) -0.0087(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.213(2) . ? Cd1 N6 2.215(2) 4_444 ? Cd1 N9 2.287(2) . ? Cd1 N4 2.288(2) 3_445 ? Cd1 O1 2.4278(19) . ? Cd1 O2 2.600(2) 4_444 ? N1 C1 1.332(3) . ? N1 N2 1.361(3) . ? O1 C2 1.231(3) . ? N2 N3 1.302(3) . ? N3 N4 1.366(3) . ? N5 C2 1.365(4) . ? N5 C1 1.381(4) . ? S1 C6 1.689(4) . ? S1 C3 1.712(3) . ? N9 C7 1.316(3) . ? N9 N8 1.362(3) . ? N10 C8 1.366(4) . ? N10 C7 1.389(3) . ? N8 N7 1.298(3) . ? S2 C12 1.688(4) . ? S2 C9 1.720(3) . ? N7 N6 1.362(3) . ? N4 C1 1.324(3) . ? N4 Cd1 2.288(2) 3_545 ? O2 C8 1.226(4) . ? O2 Cd1 2.600(2) 4_454 ? N6 C7 1.327(3) . ? N6 Cd1 2.215(2) 4_454 ? C2 C3 1.462(4) . ? C3 C4 1.407(4) . ? C4 C5 1.403(5) . ? C5 C6 1.344(6) . ? C8 C9 1.459(4) . ? C9 C10 1.362(4) . ? C10 C11 1.417(4) . ? C11 C12 1.352(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 N6 139.80(9) . 4_444 ? N1 Cd1 N9 103.05(9) . . ? N6 Cd1 N9 111.04(9) 4_444 . ? N1 Cd1 N4 108.74(8) . 3_445 ? N6 Cd1 N4 93.80(9) 4_444 3_445 ? N9 Cd1 N4 87.35(9) . 3_445 ? N1 Cd1 O1 75.34(8) . . ? N6 Cd1 O1 92.15(8) 4_444 . ? N9 Cd1 O1 76.60(8) . . ? N4 Cd1 O1 163.95(8) 3_445 . ? N1 Cd1 O2 75.34(8) . 4_444 ? N6 Cd1 O2 71.76(8) 4_444 4_444 ? N9 Cd1 O2 176.22(8) . 4_444 ? N4 Cd1 O2 89.94(9) 3_445 4_444 ? O1 Cd1 O2 106.08(8) . 4_444 ? C1 N1 N2 105.1(2) . . ? C1 N1 Cd1 132.06(18) . . ? N2 N1 Cd1 121.11(16) . . ? C2 O1 Cd1 131.96(18) . . ? N3 N2 N1 109.4(2) . . ? N2 N3 N4 108.7(2) . . ? C2 N5 C1 125.9(2) . . ? C6 S1 C3 91.75(18) . . ? C7 N9 N8 105.7(2) . . ? C7 N9 Cd1 135.96(19) . . ? N8 N9 Cd1 117.61(16) . . ? C8 N10 C7 123.6(2) . . ? N7 N8 N9 108.8(2) . . ? C12 S2 C9 91.68(16) . . ? N8 N7 N6 109.1(2) . . ? C1 N4 N3 105.5(2) . . ? C1 N4 Cd1 138.57(18) . 3_545 ? N3 N4 Cd1 115.48(16) . 3_545 ? C8 O2 Cd1 124.47(19) . 4_454 ? C7 N6 N7 105.1(2) . . ? C7 N6 Cd1 133.20(19) . 4_454 ? N7 N6 Cd1 120.39(17) . 4_454 ? N4 C1 N1 111.3(2) . . ? N4 C1 N5 121.8(2) . . ? N1 C1 N5 126.9(2) . . ? O1 C2 N5 122.3(3) . . ? O1 C2 C3 121.8(3) . . ? N5 C2 C3 115.9(2) . . ? C4 C3 C2 130.0(3) . . ? C4 C3 S1 111.4(2) . . ? C2 C3 S1 118.6(2) . . ? C5 C4 C3 110.1(3) . . ? C6 C5 C4 114.3(3) . . ? C5 C6 S1 112.5(3) . . ? N9 C7 N6 111.3(2) . . ? N9 C7 N10 122.6(2) . . ? N6 C7 N10 126.1(2) . . ? O2 C8 N10 121.9(3) . . ? O2 C8 C9 122.6(3) . . ? N10 C8 C9 115.5(2) . . ? C10 C9 C8 130.9(3) . . ? C10 C9 S2 111.4(2) . . ? C8 C9 S2 117.7(2) . . ? C9 C10 C11 111.9(3) . . ? C12 C11 C10 112.6(3) . . ? C11 C12 S2 112.4(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 N5 H5 N2 0.87 2.50 3.283(3) 149.6 3_545 N10 H10 N3 0.88 2.34 3.072(3) 140.1 3_445 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.279 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 919197' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound4 #TrackingRef 'web_deposit_cif_file_6_Jian-ZhenLiao_1357890106.compound4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cd N12 O2' _chemical_formula_sum 'C14 H10 Cd N12 O2' _chemical_formula_weight 490.74 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P41212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+1/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+3/4' 'x+1/2, -y+1/2, -z+3/4' '-x+1/2, y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.5749(15) _cell_length_b 10.5749(15) _cell_length_c 16.256(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1817.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.243 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.25 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku Mercury CCD area-detector' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '4-circle diffractometer' _diffrn_measurement_method 'scintillation counter' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17521 _diffrn_reflns_av_R_equivalents 0.0846 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2082 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius CAD4 software' _computing_cell_refinement 'Nonius CAD4 software' _computing_data_reduction 'XCAD (P.McArdle, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0537P)^2^+5.5724P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(8) _refine_ls_number_reflns 2082 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.067 _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 Cd1 Cd -0.70627(4) -0.70627(4) 0.0000 0.02253(16) Uani 1 2 d S . . N4 N -0.7320(5) -0.8861(5) 0.0792(3) 0.0280(12) Uani 1 1 d . . . N1 N -0.7427(5) -1.0544(5) 0.1575(3) 0.0255(11) Uani 1 1 d . . . N2 N -0.6887(6) -1.0841(5) 0.0839(3) 0.0353(13) Uani 1 1 d . . . N3 N -0.6822(6) -0.9833(5) 0.0379(4) 0.0403(15) Uani 1 1 d . . . N5 N -0.8346(5) -0.8591(5) 0.2078(3) 0.0324(13) Uani 1 1 d D A . O1 O -0.8390(7) -1.0042(5) 0.3112(3) 0.0526(16) Uani 1 1 d . A . C1 C -0.7698(6) -0.9308(6) 0.1511(3) 0.0245(12) Uani 1 1 d . . . C2 C -0.8644(7) -0.8995(6) 0.2858(4) 0.0355(17) Uani 1 1 d . . . C3A C -0.9407(6) -0.8115(5) 0.3385(4) 0.079(2) Uani 0.404(12) 1 d PG A 1 N6A N -1.1134(7) -0.6787(6) 0.4353(4) 0.079(2) Uani 0.404(12) 1 d PG A 1 C7A C -0.9826(7) -0.6986(6) 0.3118(3) 0.079(2) Uani 0.60 1 d PG A 1 H7A H -0.9690 -0.6669 0.2591 0.095 Uiso 0.596(12) 1 calc PR A 1 C6A C -1.0464(7) -0.6377(5) 0.3709(4) 0.079(2) Uani 0.404(12) 1 d PG A 1 H6A H -1.0436 -0.5501 0.3662 0.095 Uiso 0.404(12) 1 calc PR A 1 C5A C -1.0956(10) -0.8108(6) 0.4419(6) 0.079(2) Uani 0.404(12) 1 d PG A 1 H5A H -1.1413 -0.8534 0.4822 0.095 Uiso 0.404(12) 1 calc PR A 1 C4A C -1.0174(10) -0.8793(5) 0.3943(6) 0.079(2) Uani 0.404(12) 1 d PG A 1 H4A H -1.0141 -0.9670 0.3979 0.095 Uiso 0.404(12) 1 calc PR A 1 C3B C -0.9363(6) -0.8116(5) 0.3386(4) 0.079(2) Uani 0.60 1 d PG A 2 C5B C -1.0334(10) -0.7638(8) 0.4716(4) 0.079(2) Uani 0.60 1 d PG A 2 H5B H -1.0560 -0.7917 0.5238 0.095 Uiso 0.596(12) 1 calc PR A 2 C7B C -0.9670(7) -0.6795(5) 0.3264(3) 0.079(2) Uani 0.404(12) 1 d PG A 2 H7B H -0.9287 -0.6375 0.2827 0.095 Uiso 0.404(12) 1 calc PR A 2 N6B N -1.0637(8) -0.6594(6) 0.4490(4) 0.079(2) Uani 0.60 1 d PG A 2 C6B C -1.0541(8) -0.6081(5) 0.3781(4) 0.079(2) Uani 0.60 1 d PG A 2 H6B H -1.0967 -0.5354 0.3618 0.095 Uiso 0.596(12) 1 calc PR A 2 C4B C -0.9630(10) -0.8443(7) 0.4183(5) 0.079(2) Uani 0.60 1 d PG A 2 H4B H -0.9342 -0.9215 0.4382 0.095 Uiso 0.596(12) 1 calc PR A 2 H5 H -0.7794 -0.8064 0.2147 0.095 Uiso 1 1 d RD A 2 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 Cd1 0.0246(2) 0.0246(2) 0.0183(2) -0.00130(18) 0.00130(18) -0.0024(2) N4 0.037(3) 0.021(2) 0.026(3) -0.002(2) 0.005(2) 0.002(2) N1 0.030(3) 0.021(3) 0.025(2) 0.000(2) 0.003(2) 0.0049(19) N2 0.052(4) 0.022(3) 0.032(3) 0.007(2) 0.012(3) 0.003(2) N3 0.055(4) 0.030(3) 0.036(3) 0.000(2) 0.016(3) -0.001(3) N5 0.037(3) 0.029(3) 0.032(3) -0.003(2) 0.014(2) 0.001(2) O1 0.094(5) 0.031(3) 0.033(3) 0.004(2) 0.019(3) 0.001(3) C1 0.028(3) 0.024(3) 0.022(3) 0.004(2) 0.003(2) -0.007(2) C2 0.046(4) 0.027(4) 0.033(3) 0.000(3) 0.010(3) -0.003(3) C3A 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) N6A 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C7A 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C6A 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C5A 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C4A 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C3B 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C5B 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C7B 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) N6B 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C6B 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(3) C4B 0.121(5) 0.048(3) 0.067(3) -0.005(2) 0.052(3) 0.014(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 Cd1 N1 2.265(5) 6_355 ? Cd1 N1 2.265(5) 4_534 ? Cd1 N4 2.312(5) 7 ? Cd1 N4 2.312(5) . ? Cd1 O1 2.404(5) 4_534 ? Cd1 O1 2.404(5) 6_355 ? N4 C1 1.323(7) . ? N4 N3 1.335(8) . ? N1 C1 1.343(8) . ? N1 N2 1.361(7) . ? N1 Cd1 2.265(5) 2_345 ? N2 N3 1.304(7) . ? N5 C2 1.375(8) . ? N5 C1 1.376(8) . ? O1 C2 1.212(9) . ? O1 Cd1 2.404(5) 2_345 ? C2 C3B 1.477(8) . ? C2 C3A 1.501(8) . ? C3A C7A 1.3458 . ? C3A C4A 1.4127 . ? N6A C6A 1.3363 . ? N6A C5A 1.4140 . ? C7A C6A 1.3398 . ? C5A C4A 1.3442 . ? C3B C4B 1.3704 . ? C3B C7B 1.4471 . ? C5B N6B 1.2067 . ? C5B C4B 1.4250 . ? C7B C6B 1.4579 . ? N6B C6B 1.2780 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cd1 N1 141.1(3) 6_355 4_534 ? N1 Cd1 N4 104.89(18) 6_355 7 ? N1 Cd1 N4 100.68(18) 4_534 7 ? N1 Cd1 N4 100.68(18) 6_355 . ? N1 Cd1 N4 104.89(18) 4_534 . ? N4 Cd1 N4 96.7(3) 7 . ? N1 Cd1 O1 78.24(19) 6_355 4_534 ? N1 Cd1 O1 72.07(17) 4_534 4_534 ? N4 Cd1 O1 169.82(19) 7 4_534 ? N4 Cd1 O1 92.2(2) . 4_534 ? N1 Cd1 O1 72.07(17) 6_355 6_355 ? N1 Cd1 O1 78.24(19) 4_534 6_355 ? N4 Cd1 O1 92.2(2) 7 6_355 ? N4 Cd1 O1 169.82(19) . 6_355 ? O1 Cd1 O1 79.5(3) 4_534 6_355 ? C1 N4 N3 106.7(5) . . ? C1 N4 Cd1 145.2(4) . . ? N3 N4 Cd1 107.9(4) . . ? C1 N1 N2 104.2(5) . . ? C1 N1 Cd1 133.7(4) . 2_345 ? N2 N1 Cd1 121.3(4) . 2_345 ? N3 N2 N1 109.7(5) . . ? N2 N3 N4 108.7(5) . . ? C2 N5 C1 124.1(6) . . ? C2 O1 Cd1 135.7(5) . 2_345 ? N4 C1 N1 110.6(5) . . ? N4 C1 N5 123.0(5) . . ? N1 C1 N5 126.2(5) . . ? O1 C2 N5 123.2(7) . . ? O1 C2 C3B 119.4(6) . . ? N5 C2 C3B 117.3(6) . . ? O1 C2 C3A 119.4(6) . . ? N5 C2 C3A 117.2(6) . . ? C3B C2 C3A 1.5 . . ? C7A C3A C4A 118.0 . . ? C7A C3A C2 122.9(5) . . ? C4A C3A C2 111.2(4) . . ? C6A N6A C5A 108.0 . . ? C6A C7A C3A 111.1 . . ? N6A C6A C7A 132.4 . . ? C4A C5A N6A 124.8 . . ? C5A C4A C3A 116.7 . . ? C4B C3B C7B 109.1 . . ? C4B C3B C2 119.8(5) . . ? C7B C3B C2 130.0(5) . . ? N6B C5B C4B 120.0 . . ? C3B C7B C6B 124.2 . . ? C5B N6B C6B 129.9 . . ? N6B C6B C7B 110.5 . . ? C3B C4B C5B 122.1 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.711 _refine_diff_density_min -0.674 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 919198'