# 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_exp_1136 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 Cd0.50 I N7' _chemical_formula_weight 396.32 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.3342(6) _cell_length_b 7.6172(2) _cell_length_c 16.7658(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2341.44(14) _cell_formula_units_Z 8 _cell_measurement_temperature 116(1) _cell_measurement_reflns_used 2557 _cell_measurement_theta_min 2.5272 _cell_measurement_theta_max 28.4403 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1496 _exptl_absorpt_coefficient_mu 3.610 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8691 _exptl_absorpt_correction_T_max 0.9313 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 116(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14669 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2058 _reflns_number_gt 1554 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0200P)^2^+3.5931P] 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_number_reflns 2058 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0714 _refine_ls_wR_factor_gt 0.0611 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.5000 0.55486(7) 0.7500 0.01460(16) Uani 1 2 d S . . I1 I 0.59442(2) 0.79723(5) 0.83523(3) 0.01903(13) Uani 1 1 d . . . N1 N 0.5768(3) 0.3294(6) 0.8145(3) 0.0180(12) Uani 1 1 d . . . N2 N 0.6506(3) 0.3048(7) 0.7933(3) 0.0254(14) Uani 1 1 d . . . N3 N 0.6326(2) 0.2137(6) 0.9175(3) 0.0156(11) Uani 1 1 d . . . N4 N 0.7156(3) 0.1039(6) 1.0066(3) 0.0161(12) Uani 1 1 d . . . N5 N 0.8077(3) 0.0101(6) 1.0888(3) 0.0152(11) Uani 1 1 d . . . N6 N 0.9262(3) 0.0464(6) 1.0714(3) 0.0215(13) Uani 1 1 d . . . N7 N 0.9134(3) -0.0267(6) 1.1469(3) 0.0186(12) Uani 1 1 d . . . C1 C 0.5683(3) 0.2773(7) 0.8865(4) 0.0207(16) Uani 1 1 d . . . H1 H 0.5244 0.2817 0.9142 0.025 Uiso 1 1 calc R . . C2 C 0.6810(4) 0.2343(8) 0.8553(4) 0.0226(16) Uani 1 1 d . . . H2 H 0.7298 0.2015 0.8576 0.027 Uiso 1 1 calc R . . C3 C 0.6460(4) 0.1337(7) 0.9921(4) 0.0181(15) Uani 1 1 d . . . C4 C 0.5895(3) 0.0949(8) 1.0447(4) 0.0197(15) Uani 1 1 d . . . H4 H 0.5412 0.1212 1.0324 0.024 Uiso 1 1 calc R . . C5 C 0.6082(3) 0.0154(8) 1.1164(4) 0.0204(15) Uani 1 1 d . . . H5 H 0.5723 -0.0133 1.1533 0.024 Uiso 1 1 calc R . . C6 C 0.6811(3) -0.0213(8) 1.1327(4) 0.0208(15) Uani 1 1 d . . . H6 H 0.6951 -0.0781 1.1794 0.025 Uiso 1 1 calc R . . C7 C 0.7312(3) 0.0304(7) 1.0767(4) 0.0176(14) Uani 1 1 d . . . C8 C 0.8436(3) -0.0446(7) 1.1562(4) 0.0171(14) Uani 1 1 d . . . H8 H 0.8211 -0.0882 1.2018 0.020 Uiso 1 1 calc R . . C9 C 0.8625(3) 0.0662(8) 1.0390(4) 0.0197(15) Uani 1 1 d . . . H9 H 0.8549 0.1126 0.9884 0.024 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 Cd1 0.0127(3) 0.0170(3) 0.0141(4) 0.000 0.0001(3) 0.000 I1 0.0190(2) 0.0194(2) 0.0186(2) -0.00259(19) -0.00141(19) -0.00228(17) N1 0.020(3) 0.015(3) 0.019(3) -0.002(2) -0.004(2) 0.002(2) N2 0.026(3) 0.025(3) 0.026(4) 0.001(3) -0.002(3) 0.005(3) N3 0.013(3) 0.016(3) 0.018(3) -0.002(2) -0.003(2) 0.001(2) N4 0.016(3) 0.016(3) 0.016(3) 0.000(2) -0.002(2) 0.002(2) N5 0.016(3) 0.014(3) 0.016(3) 0.003(2) 0.000(3) 0.000(2) N6 0.020(3) 0.020(3) 0.025(4) 0.003(3) -0.006(3) 0.002(2) N7 0.020(3) 0.019(3) 0.017(3) 0.003(2) -0.002(2) 0.004(2) C1 0.012(3) 0.018(3) 0.032(5) 0.002(3) -0.004(3) 0.003(3) C2 0.014(3) 0.030(4) 0.024(5) 0.000(3) -0.001(3) 0.003(3) C3 0.028(4) 0.013(3) 0.012(4) -0.005(3) -0.009(3) 0.002(3) C4 0.013(3) 0.023(3) 0.022(4) -0.008(3) 0.001(3) 0.001(3) C5 0.017(4) 0.024(4) 0.020(4) -0.002(3) 0.004(3) -0.003(3) C6 0.019(4) 0.021(3) 0.022(4) 0.001(3) 0.000(3) 0.001(3) C7 0.016(3) 0.017(3) 0.020(4) -0.001(3) 0.003(3) 0.005(3) C8 0.023(4) 0.019(3) 0.009(4) -0.001(3) -0.002(3) 0.003(3) C9 0.021(4) 0.022(4) 0.016(4) -0.001(3) -0.001(3) 0.000(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 N7 2.356(5) 4_457 ? Cd1 N7 2.356(5) 2_654 ? Cd1 N1 2.470(5) 3_656 ? Cd1 N1 2.470(5) . ? Cd1 I1 2.9063(5) . ? Cd1 I1 2.9063(5) 3_656 ? N1 C1 1.281(8) . ? N1 N2 1.411(7) . ? N2 C2 1.296(8) . ? N3 C1 1.377(7) . ? N3 C2 1.377(8) . ? N3 C3 1.413(8) . ? N4 C3 1.319(7) . ? N4 C7 1.332(8) . ? N5 C8 1.372(8) . ? N5 C9 1.375(8) . ? N5 C7 1.426(7) . ? N6 C9 1.295(8) . ? N6 N7 1.404(7) . ? N7 C8 1.297(7) . ? N7 Cd1 2.356(5) 2_655 ? C3 C4 1.392(9) . ? C4 C5 1.389(9) . ? C5 C6 1.391(8) . ? C6 C7 1.372(8) . ? 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 N7 Cd1 N7 169.6(2) 4_457 2_654 ? N7 Cd1 N1 82.72(17) 4_457 3_656 ? N7 Cd1 N1 90.01(18) 2_654 3_656 ? N7 Cd1 N1 90.01(17) 4_457 . ? N7 Cd1 N1 82.72(17) 2_654 . ? N1 Cd1 N1 91.9(2) 3_656 . ? N7 Cd1 I1 95.66(12) 4_457 . ? N7 Cd1 I1 90.98(12) 2_654 . ? N1 Cd1 I1 175.14(11) 3_656 . ? N1 Cd1 I1 83.51(11) . . ? N7 Cd1 I1 90.98(12) 4_457 3_656 ? N7 Cd1 I1 95.66(12) 2_654 3_656 ? N1 Cd1 I1 83.51(11) 3_656 3_656 ? N1 Cd1 I1 175.14(11) . 3_656 ? I1 Cd1 I1 101.13(2) . 3_656 ? C1 N1 N2 108.3(5) . . ? C1 N1 Cd1 123.9(4) . . ? N2 N1 Cd1 122.0(4) . . ? C2 N2 N1 105.4(5) . . ? C1 N3 C2 103.1(5) . . ? C1 N3 C3 129.4(5) . . ? C2 N3 C3 127.4(5) . . ? C3 N4 C7 116.2(5) . . ? C8 N5 C9 104.1(5) . . ? C8 N5 C7 128.4(5) . . ? C9 N5 C7 126.8(6) . . ? C9 N6 N7 105.9(5) . . ? C8 N7 N6 108.3(5) . . ? C8 N7 Cd1 124.6(4) . 2_655 ? N6 N7 Cd1 125.9(4) . 2_655 ? N1 C1 N3 111.1(6) . . ? N2 C2 N3 112.2(6) . . ? N4 C3 C4 124.5(6) . . ? N4 C3 N3 113.9(6) . . ? C4 C3 N3 121.6(6) . . ? C5 C4 C3 117.1(6) . . ? C6 C5 C4 119.7(6) . . ? C7 C6 C5 116.8(6) . . ? N4 C7 C6 125.5(6) . . ? N4 C7 N5 112.4(5) . . ? C6 C7 N5 122.0(6) . . ? N7 C8 N5 110.0(6) . . ? N6 C9 N5 111.6(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.980 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 910903' ####################################################################### # # 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_n120331a #TrackingRef 'N120331A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 Cd F6 N12 O4 Si' _chemical_formula_weight 751.00 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' Si Si 0.0817 0.0704 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5550(5) _cell_length_b 9.5468(6) _cell_length_c 10.3006(6) _cell_angle_alpha 113.6790(10) _cell_angle_beta 91.9870(10) _cell_angle_gamma 104.3270(10) _cell_volume 651.67(7) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2295 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 28.30 _exptl_crystal_description BLOCK _exptl_crystal_colour PALE-YELLOW _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.984 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8665 _exptl_absorpt_correction_T_max 0.8828 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3342 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2268 _reflns_number_gt 2112 _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, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0169P)^2^+2.1104P] 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_number_reflns 2268 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 -0.5000 0.0000 0.03655(16) Uani 1 2 d S . . Si1 Si 0.0000 0.0000 0.5000 0.0148(3) Uani 1 2 d S . . F1 F 0.1913(3) -0.0430(2) 0.4393(2) 0.0310(5) Uani 1 1 d . . . F2 F 0.1296(3) 0.1876(2) 0.6096(2) 0.0344(5) Uani 1 1 d . . . F3 F 0.0334(3) -0.0608(3) 0.6275(3) 0.0468(7) Uani 1 1 d . . . O1 O 0.1830(4) -0.6672(3) -0.1021(3) 0.0363(7) Uani 1 1 d . . . H1A H 0.1692 -0.7088 -0.1921 0.054 Uiso 1 1 d R . . H1B H 0.1696 -0.7418 -0.0763 0.054 Uiso 1 1 d R . . O2 O 0.1262(4) 1.0333(3) 0.9139(3) 0.0411(7) Uani 1 1 d . . . H2A H 0.1040 0.9842 0.8240 0.062 Uiso 1 1 d R . . H2B H 0.0490 0.9801 0.9464 0.062 Uiso 1 1 d R . . N1 N 0.4392(4) -0.0342(3) 0.2071(3) 0.0211(6) Uani 1 1 d . . . N2 N 0.2598(4) -0.2779(4) 0.0971(3) 0.0308(7) Uani 1 1 d . . . N3 N 0.4143(4) -0.2821(3) 0.1715(3) 0.0279(7) Uani 1 1 d . . . N4 N 0.8007(4) 0.4721(3) 0.5799(3) 0.0271(7) Uani 1 1 d . . . N5 N 0.9474(4) 0.5292(4) 0.7896(4) 0.0368(8) Uani 1 1 d . . . N6 N 0.9498(5) 0.6716(4) 0.7825(5) 0.0580(13) Uani 1 1 d . . . C1 C 0.2788(6) -0.1312(4) 0.1205(4) 0.0333(9) Uani 1 1 d . . . H1 H 0.1917 -0.0960 0.0819 0.040 Uiso 1 1 calc R . . C2 C 0.5174(5) -0.1344(4) 0.2362(4) 0.0237(7) Uani 1 1 d . . . H2 H 0.6322 -0.1012 0.2960 0.028 Uiso 1 1 calc R . . C3 C 0.5107(5) 0.1351(4) 0.2587(4) 0.0228(7) Uani 1 1 d . . . C4 C 0.6155(5) 0.2204(4) 0.3930(4) 0.0203(7) Uani 1 1 d . . . H4 H 0.6364 0.1680 0.4509 0.024 Uiso 1 1 calc R . . C5 C 0.6897(5) 0.3839(4) 0.4419(4) 0.0244(8) Uani 1 1 d . . . C6 C 0.6547(7) 0.4619(4) 0.3597(4) 0.0394(11) Uani 1 1 d . . . H6 H 0.7037 0.5743 0.3945 0.047 Uiso 1 1 calc R . . C7 C 0.5478(8) 0.3738(5) 0.2270(5) 0.0531(14) Uani 1 1 d . . . H7 H 0.5229 0.4266 0.1705 0.064 Uiso 1 1 calc R . . C8 C 0.4758(7) 0.2101(5) 0.1739(4) 0.0416(11) Uani 1 1 d . . . H8 H 0.4039 0.1502 0.0814 0.050 Uiso 1 1 calc R . . C9 C 0.8593(5) 0.4135(4) 0.6677(4) 0.0263(8) Uani 1 1 d . . . H9 H 0.8392 0.3033 0.6439 0.032 Uiso 1 1 calc R . . C10 C 0.8625(6) 0.6341(5) 0.6579(6) 0.0506(13) Uani 1 1 d . . . H10 H 0.8435 0.7094 0.6245 0.061 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 Cd1 0.0195(2) 0.0262(2) 0.0339(2) -0.01682(17) -0.01087(16) 0.00834(16) Si1 0.0175(6) 0.0103(6) 0.0138(6) 0.0035(5) -0.0007(5) 0.0022(5) F1 0.0230(11) 0.0208(10) 0.0398(13) 0.0036(9) 0.0078(9) 0.0060(8) F2 0.0243(11) 0.0149(10) 0.0421(13) -0.0053(9) 0.0008(9) -0.0012(8) F3 0.0308(13) 0.0748(18) 0.0533(16) 0.0549(15) -0.0036(11) 0.0001(12) O1 0.0314(15) 0.0206(13) 0.0428(16) -0.0020(12) -0.0059(12) 0.0118(11) O2 0.0344(16) 0.0380(16) 0.0507(19) 0.0192(14) 0.0069(13) 0.0095(13) N1 0.0248(15) 0.0174(14) 0.0172(14) 0.0034(11) -0.0037(12) 0.0072(12) N2 0.0256(16) 0.0214(16) 0.0301(17) -0.0042(13) -0.0102(13) 0.0085(13) N3 0.0216(16) 0.0193(15) 0.0339(17) 0.0041(13) -0.0061(13) 0.0048(12) N4 0.0208(15) 0.0117(14) 0.0392(18) 0.0034(13) 0.0042(13) 0.0010(11) N5 0.0221(16) 0.0203(16) 0.044(2) -0.0099(14) -0.0082(14) 0.0065(13) N6 0.038(2) 0.0142(17) 0.086(3) -0.0093(18) -0.026(2) 0.0048(15) C1 0.037(2) 0.0250(19) 0.026(2) -0.0025(16) -0.0169(16) 0.0144(17) C2 0.0195(17) 0.0177(17) 0.0288(19) 0.0059(15) -0.0035(14) 0.0046(14) C3 0.034(2) 0.0158(16) 0.0195(17) 0.0069(14) 0.0053(15) 0.0098(14) C4 0.0222(17) 0.0159(16) 0.0234(17) 0.0102(14) 0.0041(14) 0.0031(13) C5 0.0274(19) 0.0160(16) 0.0271(19) 0.0069(14) 0.0104(15) 0.0048(14) C6 0.071(3) 0.0173(18) 0.038(2) 0.0176(17) 0.027(2) 0.0148(19) C7 0.117(5) 0.033(2) 0.029(2) 0.022(2) 0.025(3) 0.038(3) C8 0.082(3) 0.031(2) 0.0178(19) 0.0102(17) 0.006(2) 0.027(2) C9 0.0183(17) 0.0171(17) 0.030(2) -0.0012(15) 0.0028(15) 0.0024(14) C10 0.035(2) 0.0128(19) 0.078(4) 0.001(2) -0.016(2) -0.0013(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 O1 2.326(2) . ? Cd1 O1 2.326(2) 2_545 ? Cd1 N5 2.327(4) 1_444 ? Cd1 N5 2.327(4) 2_656 ? Cd1 N2 2.334(3) . ? Cd1 N2 2.334(3) 2_545 ? Si1 F3 1.670(2) 2_556 ? Si1 F3 1.670(2) . ? Si1 F1 1.673(2) . ? Si1 F1 1.673(2) 2_556 ? Si1 F2 1.6948(19) . ? Si1 F2 1.6948(19) 2_556 ? O1 H1A 0.8400 . ? O1 H1B 0.8401 . ? O2 H2A 0.8401 . ? O2 H2B 0.8453 . ? N1 C1 1.352(5) . ? N1 C2 1.361(4) . ? N1 C3 1.430(4) . ? N2 C1 1.292(5) . ? N2 N3 1.392(4) . ? N3 C2 1.305(4) . ? N4 C9 1.351(5) . ? N4 C10 1.369(5) . ? N4 C5 1.429(5) . ? N5 C9 1.305(5) . ? N5 N6 1.387(5) . ? N5 Cd1 2.327(4) 1_666 ? N6 C10 1.290(7) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C4 1.380(5) . ? C3 C8 1.387(5) . ? C4 C5 1.386(5) . ? C4 H4 0.9500 . ? C5 C6 1.389(5) . ? C6 C7 1.375(7) . ? C6 H6 0.9500 . ? C7 C8 1.382(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 O1 180.0 . 2_545 ? O1 Cd1 N5 91.58(11) . 1_444 ? O1 Cd1 N5 88.42(11) 2_545 1_444 ? O1 Cd1 N5 88.42(11) . 2_656 ? O1 Cd1 N5 91.58(11) 2_545 2_656 ? N5 Cd1 N5 180.000(1) 1_444 2_656 ? O1 Cd1 N2 91.19(10) . . ? O1 Cd1 N2 88.81(10) 2_545 . ? N5 Cd1 N2 94.10(11) 1_444 . ? N5 Cd1 N2 85.90(11) 2_656 . ? O1 Cd1 N2 88.81(10) . 2_545 ? O1 Cd1 N2 91.19(10) 2_545 2_545 ? N5 Cd1 N2 85.90(11) 1_444 2_545 ? N5 Cd1 N2 94.10(11) 2_656 2_545 ? N2 Cd1 N2 180.0 . 2_545 ? F3 Si1 F3 180.000(1) 2_556 . ? F3 Si1 F1 90.54(12) 2_556 . ? F3 Si1 F1 89.46(12) . . ? F3 Si1 F1 89.46(12) 2_556 2_556 ? F3 Si1 F1 90.54(12) . 2_556 ? F1 Si1 F1 179.999(1) . 2_556 ? F3 Si1 F2 89.66(12) 2_556 . ? F3 Si1 F2 90.34(12) . . ? F1 Si1 F2 89.33(10) . . ? F1 Si1 F2 90.67(10) 2_556 . ? F3 Si1 F2 90.34(12) 2_556 2_556 ? F3 Si1 F2 89.66(12) . 2_556 ? F1 Si1 F2 90.67(10) . 2_556 ? F1 Si1 F2 89.33(10) 2_556 2_556 ? F2 Si1 F2 180.0 . 2_556 ? Cd1 O1 H1A 115.4 . . ? Cd1 O1 H1B 113.4 . . ? H1A O1 H1B 106.9 . . ? H2A O2 H2B 106.8 . . ? C1 N1 C2 104.1(3) . . ? C1 N1 C3 128.4(3) . . ? C2 N1 C3 127.4(3) . . ? C1 N2 N3 107.7(3) . . ? C1 N2 Cd1 130.3(2) . . ? N3 N2 Cd1 120.5(2) . . ? C2 N3 N2 105.8(3) . . ? C9 N4 C10 103.9(3) . . ? C9 N4 C5 127.5(3) . . ? C10 N4 C5 128.5(4) . . ? C9 N5 N6 107.4(4) . . ? C9 N5 Cd1 124.7(3) . 1_666 ? N6 N5 Cd1 125.1(3) . 1_666 ? C10 N6 N5 106.5(3) . . ? N2 C1 N1 111.0(3) . . ? N2 C1 H1 124.5 . . ? N1 C1 H1 124.5 . . ? N3 C2 N1 111.3(3) . . ? N3 C2 H2 124.3 . . ? N1 C2 H2 124.3 . . ? C4 C3 C8 121.4(3) . . ? C4 C3 N1 118.5(3) . . ? C8 C3 N1 120.1(3) . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 120.9(4) . . ? C4 C5 N4 118.9(3) . . ? C6 C5 N4 120.3(3) . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 121.5(4) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C3 118.6(4) . . ? C7 C8 H8 120.7 . . ? C3 C8 H8 120.7 . . ? N5 C9 N4 110.7(3) . . ? N5 C9 H9 124.6 . . ? N4 C9 H9 124.6 . . ? N6 C10 N4 111.5(4) . . ? N6 C10 H10 124.2 . . ? N4 C10 H10 124.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cd1 N2 C1 147.5(4) . . . . ? O1 Cd1 N2 C1 -32.5(4) 2_545 . . . ? N5 Cd1 N2 C1 55.8(4) 1_444 . . . ? N5 Cd1 N2 C1 -124.2(4) 2_656 . . . ? N2 Cd1 N2 C1 44(13) 2_545 . . . ? O1 Cd1 N2 N3 -48.1(3) . . . . ? O1 Cd1 N2 N3 131.9(3) 2_545 . . . ? N5 Cd1 N2 N3 -139.8(3) 1_444 . . . ? N5 Cd1 N2 N3 40.2(3) 2_656 . . . ? N2 Cd1 N2 N3 -151(13) 2_545 . . . ? C1 N2 N3 C2 0.3(4) . . . . ? Cd1 N2 N3 C2 -167.3(2) . . . . ? C9 N5 N6 C10 0.4(5) . . . . ? Cd1 N5 N6 C10 -161.1(3) 1_666 . . . ? N3 N2 C1 N1 0.1(5) . . . . ? Cd1 N2 C1 N1 166.0(3) . . . . ? C2 N1 C1 N2 -0.4(4) . . . . ? C3 N1 C1 N2 -179.7(3) . . . . ? N2 N3 C2 N1 -0.5(4) . . . . ? C1 N1 C2 N3 0.6(4) . . . . ? C3 N1 C2 N3 179.9(3) . . . . ? C1 N1 C3 C4 147.3(4) . . . . ? C2 N1 C3 C4 -31.9(5) . . . . ? C1 N1 C3 C8 -33.3(6) . . . . ? C2 N1 C3 C8 147.6(4) . . . . ? C8 C3 C4 C5 -1.3(5) . . . . ? N1 C3 C4 C5 178.2(3) . . . . ? C3 C4 C5 C6 2.1(5) . . . . ? C3 C4 C5 N4 -179.0(3) . . . . ? C9 N4 C5 C4 6.7(5) . . . . ? C10 N4 C5 C4 -168.7(4) . . . . ? C9 N4 C5 C6 -174.4(4) . . . . ? C10 N4 C5 C6 10.2(6) . . . . ? C4 C5 C6 C7 -1.3(6) . . . . ? N4 C5 C6 C7 179.8(4) . . . . ? C5 C6 C7 C8 -0.3(7) . . . . ? C6 C7 C8 C3 1.1(7) . . . . ? C4 C3 C8 C7 -0.3(6) . . . . ? N1 C3 C8 C7 -179.7(4) . . . . ? N6 N5 C9 N4 -0.7(4) . . . . ? Cd1 N5 C9 N4 160.9(2) 1_666 . . . ? C10 N4 C9 N5 0.7(4) . . . . ? C5 N4 C9 N5 -175.6(3) . . . . ? N5 N6 C10 N4 0.0(6) . . . . ? C9 N4 C10 N6 -0.4(5) . . . . ? C5 N4 C10 N6 175.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.524 _refine_diff_density_min -2.073 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 917442' ####################################################################### # # 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_1 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 Br2 N6 Zn, H2 O' _chemical_formula_sum 'C10 H10 Br2 N6 O Zn' _chemical_formula_weight 455.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.135(3) _cell_length_b 13.562(4) _cell_length_c 20.655(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2839.2(15) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 950 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 21.05 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 7.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3854 _exptl_absorpt_correction_T_max 0.6267 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11548 _diffrn_reflns_av_R_equivalents 0.1004 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2442 _reflns_number_gt 1546 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1058P)^2^+1.8722P] 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_number_reflns 2442 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1206 _refine_ls_R_factor_gt 0.0717 _refine_ls_wR_factor_ref 0.1937 _refine_ls_wR_factor_gt 0.1684 _refine_ls_goodness_of_fit_ref 1.067 _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 Br1 Br 0.47826(11) 0.61643(9) 0.42900(6) 0.0333(4) Uani 1 1 d . . . Br2 Br 0.32846(13) 0.37679(10) 0.34678(6) 0.0419(4) Uani 1 1 d . . . C1 C 0.9423(11) 0.3720(8) 0.4937(5) 0.025(3) Uani 1 1 d . . . C2 C 0.8970(11) 0.3861(9) 0.5569(5) 0.029(3) Uani 1 1 d . . . H2 H 0.8064 0.3986 0.5651 0.035 Uiso 1 1 calc R . . C3 C 0.9865(11) 0.3817(8) 0.6068(5) 0.026(3) Uani 1 1 d . . . C4 C 1.1193(10) 0.3614(7) 0.5955(5) 0.020(2) Uani 1 1 d . . . H4 H 1.1794 0.3554 0.6306 0.025 Uiso 1 1 calc R . . C5 C 1.1619(12) 0.3500(9) 0.5328(6) 0.032(3) Uani 1 1 d . . . H5 H 1.2531 0.3394 0.5247 0.038 Uiso 1 1 calc R . . C6 C 1.0752(11) 0.3539(8) 0.4815(6) 0.025(3) Uani 1 1 d . . . H6 H 1.1056 0.3444 0.4384 0.031 Uiso 1 1 calc R . . C7 C 0.8643(13) 0.3416(10) 0.3793(6) 0.041(3) Uani 1 1 d . . . H7 H 0.9402 0.3085 0.3633 0.049 Uiso 1 1 calc R . . C8 C 0.7342(11) 0.4237(9) 0.4423(5) 0.028(3) Uani 1 1 d . . . H8 H 0.6988 0.4580 0.4785 0.034 Uiso 1 1 calc R . . C9 C 0.8249(12) 0.3801(9) 0.6995(6) 0.038(3) Uani 1 1 d . . . H9 H 0.7554 0.3447 0.6792 0.045 Uiso 1 1 calc R . . C10 C 1.0119(12) 0.4559(9) 0.7166(5) 0.032(3) Uani 1 1 d . . . H10 H 1.0977 0.4826 0.7109 0.039 Uiso 1 1 calc R . . N1 N 0.6766(9) 0.4153(7) 0.3854(4) 0.027(2) Uani 1 1 d . . . N2 N 0.7552(11) 0.3611(8) 0.3446(4) 0.038(3) Uani 1 1 d . . . N3 N 0.8502(9) 0.3766(7) 0.4413(4) 0.025(2) Uani 1 1 d . . . N4 N 0.9414(9) 0.4613(7) 0.7700(5) 0.028(2) Uani 1 1 d . . . N5 N 0.8239(10) 0.4124(8) 0.7598(5) 0.037(3) Uani 1 1 d . . . N6 N 0.9421(9) 0.4057(7) 0.6707(5) 0.030(2) Uani 1 1 d . . . O1 O 0.0641(9) 0.2734(8) 0.2600(5) 0.061(3) Uani 1 1 d . . . H1A H 0.0992 0.2899 0.2243 0.074 Uiso 1 1 d R . . H1B H 0.1151 0.2921 0.2903 0.074 Uiso 1 1 d R . . Zn1 Zn 0.50903(12) 0.48354(10) 0.35666(6) 0.0261(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0310(7) 0.0338(7) 0.0353(7) -0.0033(6) 0.0073(5) 0.0018(6) Br2 0.0359(7) 0.0461(9) 0.0437(8) -0.0052(7) 0.0003(6) -0.0086(6) C1 0.036(7) 0.020(6) 0.018(6) -0.001(5) -0.007(5) 0.003(5) C2 0.019(6) 0.039(7) 0.031(7) -0.001(6) -0.006(5) 0.002(5) C3 0.034(6) 0.028(6) 0.015(6) -0.006(5) -0.007(5) 0.004(6) C4 0.016(5) 0.017(6) 0.028(6) 0.004(5) -0.008(5) -0.009(4) C5 0.026(6) 0.035(8) 0.035(7) -0.002(6) -0.002(5) 0.003(5) C6 0.024(6) 0.025(7) 0.028(7) -0.007(5) 0.006(5) -0.006(5) C7 0.047(8) 0.055(9) 0.021(7) -0.001(6) -0.003(6) 0.023(7) C8 0.028(6) 0.036(7) 0.021(6) 0.010(5) 0.005(5) 0.000(6) C9 0.037(7) 0.034(7) 0.043(8) -0.006(7) -0.008(6) 0.010(6) C10 0.024(6) 0.046(8) 0.027(7) -0.007(6) -0.008(5) -0.001(6) N1 0.034(5) 0.028(6) 0.019(5) -0.003(4) -0.002(4) 0.002(5) N2 0.044(6) 0.050(7) 0.018(5) -0.012(5) -0.003(5) 0.018(5) N3 0.026(5) 0.031(6) 0.019(5) -0.003(4) -0.008(4) 0.010(4) N4 0.026(5) 0.026(6) 0.030(6) 0.003(4) -0.008(4) 0.007(4) N5 0.042(6) 0.041(7) 0.027(6) -0.005(5) 0.000(5) -0.017(5) N6 0.017(5) 0.042(7) 0.030(6) 0.005(5) -0.006(4) -0.008(4) O1 0.054(6) 0.069(7) 0.061(7) 0.005(6) -0.007(5) -0.018(6) Zn1 0.0240(7) 0.0308(8) 0.0234(7) 0.0037(6) 0.0005(6) 0.0007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Zn1 2.3618(19) . ? Br2 Zn1 2.3424(19) . ? C1 C6 1.392(16) . ? C1 C2 1.395(16) . ? C1 N3 1.432(13) . ? C2 C3 1.375(15) . ? C2 H2 0.9500 . ? C3 C4 1.394(15) . ? C3 N6 1.431(14) . ? C4 C5 1.373(16) . ? C4 H4 0.9500 . ? C5 C6 1.379(16) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.344(15) . ? C7 N3 1.372(15) . ? C7 H7 0.9500 . ? C8 N1 1.317(14) . ? C8 N3 1.338(14) . ? C8 H8 0.9500 . ? C9 N5 1.321(15) . ? C9 N6 1.373(15) . ? C9 H9 0.9500 . ? C10 N4 1.317(14) . ? C10 N6 1.364(14) . ? C10 H10 0.9500 . ? N1 N2 1.373(13) . ? N1 Zn1 2.024(9) . ? N4 N5 1.380(13) . ? N4 Zn1 2.004(10) 2_665 ? O1 H1A 0.8501 . ? O1 H1B 0.8499 . ? Zn1 N4 2.004(10) 2_664 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.8(10) . . ? C6 C1 N3 120.0(10) . . ? C2 C1 N3 119.2(10) . . ? C3 C2 C1 118.6(11) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.2(10) . . ? C2 C3 N6 118.4(10) . . ? C4 C3 N6 120.2(9) . . ? C5 C4 C3 119.0(10) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.3(11) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.9(10) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? N2 C7 N3 110.1(11) . . ? N2 C7 H7 125.0 . . ? N3 C7 H7 125.0 . . ? N1 C8 N3 109.5(10) . . ? N1 C8 H8 125.3 . . ? N3 C8 H8 125.3 . . ? N5 C9 N6 109.4(11) . . ? N5 C9 H9 125.3 . . ? N6 C9 H9 125.3 . . ? N4 C10 N6 109.2(10) . . ? N4 C10 H10 125.4 . . ? N6 C10 H10 125.4 . . ? C8 N1 N2 109.7(9) . . ? C8 N1 Zn1 126.4(8) . . ? N2 N1 Zn1 123.5(7) . . ? C7 N2 N1 104.8(9) . . ? C8 N3 C7 105.8(9) . . ? C8 N3 C1 125.5(9) . . ? C7 N3 C1 128.5(10) . . ? C10 N4 N5 108.3(9) . . ? C10 N4 Zn1 129.3(8) . 2_665 ? N5 N4 Zn1 122.1(7) . 2_665 ? C9 N5 N4 107.2(10) . . ? C10 N6 C9 105.9(10) . . ? C10 N6 C3 126.2(9) . . ? C9 N6 C3 127.8(10) . . ? H1A O1 H1B 107.8 . . ? N4 Zn1 N1 102.8(4) 2_664 . ? N4 Zn1 Br2 110.4(3) 2_664 . ? N1 Zn1 Br2 113.5(3) . . ? N4 Zn1 Br1 108.3(3) 2_664 . ? N1 Zn1 Br1 105.9(3) . . ? Br2 Zn1 Br1 115.06(7) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 2.418 _refine_diff_density_min -0.934 _refine_diff_density_rms 0.220 _database_code_depnum_ccdc_archive 'CCDC 929121' ####################################################################### # # 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_1 #TrackingRef '1-ok.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 Cd N14 S2, 2(H2 O)' _chemical_formula_sum 'C22 H20 Cd N14 O2 S2' _chemical_formula_weight 689.04 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.905(3) _cell_length_b 11.572(4) _cell_length_c 14.981(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.870(14) _cell_angle_gamma 90.00 _cell_volume 1325.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 838 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 19.55 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7821 _exptl_absorpt_correction_T_max 0.8199 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8503 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0889 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2555 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0409P)^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 2555 _refine_ls_number_parameters 193 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2560(7) 0.5365(4) -0.2575(4) 0.0257(12) Uani 1 1 d . . . C2 C 0.5288(6) 0.9766(4) 0.1383(4) 0.0219(11) Uani 1 1 d . . . C3 C 0.6944(6) 0.9759(4) 0.2273(4) 0.0228(12) Uani 1 1 d . . . H3 H 0.7641 0.9079 0.2483 0.027 Uiso 1 1 calc R . . C4 C 0.7552(6) 1.0774(4) 0.2849(4) 0.0233(11) Uani 1 1 d . . . C5 C 0.6536(6) 1.1753(4) 0.2579(4) 0.0259(12) Uani 1 1 d . . . H5 H 0.6962 1.2430 0.2995 0.031 Uiso 1 1 calc R . . C6 C 0.4887(7) 1.1741(4) 0.1697(4) 0.0264(12) Uani 1 1 d . . . H6 H 0.4183 1.2417 0.1507 0.032 Uiso 1 1 calc R . . C7 C 0.4247(6) 1.0766(4) 0.1088(4) 0.0244(12) Uani 1 1 d . . . H7 H 0.3119 1.0769 0.0478 0.029 Uiso 1 1 calc R . . C8 C 0.3004(6) 0.8556(4) -0.0074(4) 0.0265(12) Uani 1 1 d . . . H8 H 0.2109 0.9126 -0.0364 0.032 Uiso 1 1 calc R . . C9 C 0.5457(6) 0.7701(4) 0.0914(4) 0.0264(12) Uani 1 1 d . . . H9 H 0.6623 0.7539 0.1450 0.032 Uiso 1 1 calc R . . C10 C 1.0009(7) 1.1398(4) 0.4616(4) 0.0276(12) Uani 1 1 d . . . H10 H 0.9354 1.1857 0.4822 0.033 Uiso 1 1 calc R . . C11 C 1.0712(7) 1.0289(4) 0.3739(4) 0.0273(12) Uani 1 1 d . . . H11 H 1.0644 0.9815 0.3202 0.033 Uiso 1 1 calc R . . Cd1 Cd 0.5000 0.5000 0.0000 0.02101(19) Uani 1 2 d S . . N1 N 0.3765(6) 0.5252(4) -0.1750(4) 0.0318(11) Uani 1 1 d . . . N2 N 0.4411(5) 0.6965(3) 0.0199(3) 0.0258(10) Uani 1 1 d . . . N3 N 0.2833(5) 0.7517(4) -0.0438(3) 0.0262(10) Uani 1 1 d . . . N4 N 0.4625(5) 0.8730(3) 0.0775(3) 0.0230(9) Uani 1 1 d . . . N5 N 1.2170(5) 1.0540(4) 0.4605(3) 0.0259(10) Uani 1 1 d . . . N6 N 1.1720(6) 1.1260(4) 0.5169(3) 0.0307(11) Uani 1 1 d . . . N7 N 0.9311(5) 1.0796(3) 0.3712(3) 0.0231(9) Uani 1 1 d . . . O1 O 0.9612(6) 0.7379(5) 0.7515(4) 0.0746(17) Uani 1 1 d D . . H1A H 0.914(8) 0.771(7) 0.785(5) 0.089 Uiso 1 1 d D . . H1B H 1.069(3) 0.725(6) 0.793(4) 0.089 Uiso 1 1 d D . . S1 S 0.08462(19) 0.55252(13) -0.37544(11) 0.0349(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(3) 0.023(3) 0.025(3) -0.002(2) 0.012(3) -0.006(2) C2 0.021(3) 0.023(3) 0.024(3) -0.001(2) 0.012(2) -0.001(2) C3 0.017(3) 0.025(3) 0.026(3) 0.003(2) 0.011(2) 0.002(2) C4 0.016(3) 0.029(3) 0.023(3) 0.003(2) 0.009(2) -0.001(2) C5 0.021(3) 0.021(3) 0.032(3) -0.003(2) 0.011(3) -0.003(2) C6 0.024(3) 0.024(3) 0.031(3) 0.005(2) 0.014(3) 0.003(2) C7 0.014(3) 0.028(3) 0.028(3) 0.003(2) 0.008(2) 0.003(2) C8 0.017(3) 0.029(3) 0.026(3) -0.007(2) 0.006(2) 0.005(2) C9 0.017(3) 0.032(3) 0.026(3) 0.001(2) 0.008(2) 0.004(2) C10 0.025(3) 0.028(3) 0.027(3) -0.002(2) 0.012(3) 0.000(2) C11 0.021(3) 0.033(3) 0.027(3) -0.003(2) 0.011(3) 0.000(2) Cd1 0.0159(3) 0.0219(3) 0.0214(3) -0.0005(2) 0.0069(2) 0.0003(2) N1 0.031(3) 0.037(3) 0.028(3) 0.002(2) 0.016(2) 0.002(2) N2 0.019(2) 0.027(2) 0.027(2) -0.002(2) 0.009(2) -0.0010(19) N3 0.019(2) 0.032(2) 0.024(2) -0.005(2) 0.009(2) 0.0006(19) N4 0.017(2) 0.024(2) 0.026(2) -0.0027(19) 0.009(2) -0.0030(18) N5 0.019(2) 0.022(2) 0.032(3) -0.003(2) 0.010(2) -0.0003(19) N6 0.027(3) 0.029(2) 0.030(3) -0.005(2) 0.010(2) 0.000(2) N7 0.020(2) 0.021(2) 0.025(2) -0.0014(18) 0.010(2) -0.0019(18) O1 0.037(3) 0.072(4) 0.076(4) 0.028(3) 0.001(3) -0.013(3) S1 0.0259(8) 0.0430(9) 0.0264(8) 0.0001(7) 0.0068(6) -0.0066(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.156(7) . ? C1 S1 1.649(6) . ? C2 C3 1.391(7) . ? C2 C7 1.404(7) . ? C2 N4 1.437(6) . ? C3 C4 1.391(7) . ? C3 H3 0.9500 . ? C4 C5 1.375(6) . ? C4 N7 1.431(6) . ? C5 C6 1.383(7) . ? C5 H5 0.9500 . ? C6 C7 1.377(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N3 1.296(6) . ? C8 N4 1.363(6) . ? C8 H8 0.9500 . ? C9 N2 1.310(6) . ? C9 N4 1.361(6) . ? C9 H9 0.9500 . ? C10 N6 1.318(6) . ? C10 N7 1.357(6) . ? C10 H10 0.9500 . ? C11 N5 1.313(6) . ? C11 N7 1.360(6) . ? C11 H11 0.9500 . ? Cd1 N1 2.282(5) 3_665 ? Cd1 N1 2.282(5) . ? Cd1 N5 2.358(4) 4_475 ? Cd1 N5 2.358(4) 2_745 ? Cd1 N2 2.387(4) . ? Cd1 N2 2.387(4) 3_665 ? N2 N3 1.384(5) . ? N5 N6 1.384(6) . ? N5 Cd1 2.358(4) 2_755 ? O1 H1A 0.89(2) . ? O1 H1B 0.85(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 S1 179.8(5) . . ? C3 C2 C7 120.7(4) . . ? C3 C2 N4 119.4(4) . . ? C7 C2 N4 119.9(4) . . ? C2 C3 C4 118.2(4) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 121.7(5) . . ? C5 C4 N7 120.0(4) . . ? C3 C4 N7 118.2(4) . . ? C4 C5 C6 119.2(5) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C7 C6 C5 121.1(5) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C2 119.0(5) . . ? C6 C7 H7 120.5 . . ? C2 C7 H7 120.5 . . ? N3 C8 N4 111.6(4) . . ? N3 C8 H8 124.2 . . ? N4 C8 H8 124.2 . . ? N2 C9 N4 109.9(4) . . ? N2 C9 H9 125.0 . . ? N4 C9 H9 125.0 . . ? N6 C10 N7 110.8(5) . . ? N6 C10 H10 124.6 . . ? N7 C10 H10 124.6 . . ? N5 C11 N7 111.2(5) . . ? N5 C11 H11 124.4 . . ? N7 C11 H11 124.4 . . ? N1 Cd1 N1 180.0 3_665 . ? N1 Cd1 N5 94.45(15) 3_665 4_475 ? N1 Cd1 N5 85.55(15) . 4_475 ? N1 Cd1 N5 85.55(15) 3_665 2_745 ? N1 Cd1 N5 94.45(15) . 2_745 ? N5 Cd1 N5 180.00(19) 4_475 2_745 ? N1 Cd1 N2 89.19(15) 3_665 . ? N1 Cd1 N2 90.81(15) . . ? N5 Cd1 N2 90.51(14) 4_475 . ? N5 Cd1 N2 89.49(14) 2_745 . ? N1 Cd1 N2 90.81(15) 3_665 3_665 ? N1 Cd1 N2 89.19(15) . 3_665 ? N5 Cd1 N2 89.49(14) 4_475 3_665 ? N5 Cd1 N2 90.51(14) 2_745 3_665 ? N2 Cd1 N2 180.0 . 3_665 ? C1 N1 Cd1 151.5(4) . . ? C9 N2 N3 107.9(4) . . ? C9 N2 Cd1 127.7(3) . . ? N3 N2 Cd1 124.3(3) . . ? C8 N3 N2 106.3(4) . . ? C9 N4 C8 104.2(4) . . ? C9 N4 C2 128.3(4) . . ? C8 N4 C2 127.5(4) . . ? C11 N5 N6 106.6(4) . . ? C11 N5 Cd1 125.3(3) . 2_755 ? N6 N5 Cd1 127.8(3) . 2_755 ? C10 N6 N5 107.0(4) . . ? C10 N7 C11 104.3(4) . . ? C10 N7 C4 129.8(4) . . ? C11 N7 C4 125.5(4) . . ? H1A O1 H1B 111(5) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.068 _refine_diff_density_min -0.929 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 917437' ####################################################################### # # 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_1z #TrackingRef '1-ok.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 Cd N12, 2(B F4)' _chemical_formula_sum 'C20 H16 B2 Cd F8 N12' _chemical_formula_weight 710.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.287(11) _cell_length_b 22.046(16) _cell_length_c 8.268(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.563(10) _cell_angle_gamma 90.00 _cell_volume 2575(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1139 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 20.53 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8336 _exptl_absorpt_correction_T_max 0.9283 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11671 _diffrn_reflns_av_R_equivalents 0.1077 _diffrn_reflns_av_sigmaI/netI 0.1618 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4504 _reflns_number_gt 2288 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1363P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0057(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4504 _refine_ls_number_parameters 369 _refine_ls_number_restraints 381 _refine_ls_R_factor_all 0.1698 _refine_ls_R_factor_gt 0.0910 _refine_ls_wR_factor_ref 0.2697 _refine_ls_wR_factor_gt 0.2301 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.135 _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 B1 B 0.8658(9) 0.4845(6) 0.7016(15) 0.054(6) Uiso 1 1 d D . . F4 F 0.9071(8) 0.4288(4) 0.7169(13) 0.083(4) Uiso 1 1 d D A . F1 F 0.9216(16) 0.5228(8) 0.806(3) 0.096(11) Uiso 0.46(3) 1 d PD A 1 F2 F 0.8513(18) 0.5058(9) 0.5492(18) 0.081(10) Uiso 0.46(3) 1 d PD A 1 F3 F 0.7800(12) 0.4807(9) 0.759(3) 0.093(11) Uiso 0.46(3) 1 d PD A 1 F1' F 0.7770(12) 0.4775(9) 0.614(3) 0.125(12) Uiso 0.54(3) 1 d PD A 2 F2' F 0.9160(16) 0.5193(8) 0.605(3) 0.111(11) Uiso 0.54(3) 1 d PD A 2 F3' F 0.8652(17) 0.5113(8) 0.8448(18) 0.096(9) Uiso 0.54(3) 1 d PD A 2 B2 B 0.5413(9) 0.3392(6) 0.1293(15) 0.050(5) Uiso 1 1 d D . . F5 F 0.6399(9) 0.3420(9) 0.145(2) 0.070(8) Uiso 0.52(2) 1 d PD B 3 F6 F 0.5060(13) 0.3224(9) -0.0258(17) 0.080(8) Uiso 0.52(2) 1 d PD B 3 F7 F 0.5253(16) 0.2910(8) 0.229(2) 0.102(10) Uiso 0.52(2) 1 d PD B 3 F8 F 0.5096(16) 0.3907(7) 0.179(3) 0.098(9) Uiso 0.52(2) 1 d PD B 3 F5' F 0.4541(12) 0.3179(10) 0.145(3) 0.093(10) Uiso 0.48(2) 1 d PD B 4 F6' F 0.6079(13) 0.2979(9) 0.151(2) 0.074(8) Uiso 0.48(2) 1 d PD B 4 F7' F 0.5355(18) 0.3673(12) -0.022(2) 0.134(13) Uiso 0.48(2) 1 d PD B 4 F8' F 0.5608(17) 0.3866(8) 0.241(3) 0.095(10) Uiso 0.48(2) 1 d PD B 4 C1 C -0.1727(11) 0.9080(6) -0.326(2) 0.043(4) Uani 1 1 d . . . C2 C -0.1399(10) 0.9666(6) -0.2938(18) 0.033(4) Uani 1 1 d . . . H2 H -0.0767 0.9748 -0.2449 0.039 Uiso 1 1 calc R . . C3 C -0.2050(12) 1.0121(6) -0.337(2) 0.045(4) Uani 1 1 d . . . C4 C -0.2934(12) 1.0030(7) -0.413(2) 0.047(4) Uani 1 1 d . . . H4 H -0.3332 1.0369 -0.4442 0.056 Uiso 1 1 calc R . . C5 C -0.3276(13) 0.9442(8) -0.447(2) 0.054(5) Uani 1 1 d . . . H5 H -0.3909 0.9377 -0.4979 0.065 Uiso 1 1 calc R . . C6 C -0.2667(11) 0.8951(8) -0.404(2) 0.050(5) Uani 1 1 d . . . H6 H -0.2872 0.8545 -0.4264 0.060 Uiso 1 1 calc R . . C7 C -0.0634(10) 0.8376(7) -0.1457(18) 0.033(4) Uani 1 1 d . . . H7 H -0.0792 0.8500 -0.0431 0.040 Uiso 1 1 calc R . . C8 C -0.0651(10) 0.8290(7) -0.4035(18) 0.032(4) Uani 1 1 d . . . H8 H -0.0822 0.8334 -0.5184 0.038 Uiso 1 1 calc R . . C9 C -0.1526(12) 1.1083(6) -0.176(2) 0.043(4) Uani 1 1 d . . . H9 H -0.1632 1.0945 -0.0709 0.052 Uiso 1 1 calc R . . C10 C -0.1435(11) 1.1103(6) -0.430(2) 0.041(4) Uani 1 1 d . . . H10 H -0.1463 1.0987 -0.5417 0.049 Uiso 1 1 calc R . . C11 C 0.4449(10) 0.6309(7) 0.3684(18) 0.035(4) Uani 1 1 d . . . C12 C 0.5237(13) 0.6588(9) 0.446(2) 0.055(5) Uani 1 1 d . . . H12 H 0.5205 0.7001 0.4781 0.065 Uiso 1 1 calc R . . C13 C 0.6088(12) 0.6278(8) 0.479(2) 0.052(5) Uani 1 1 d . . . C14 C 0.6158(12) 0.5691(7) 0.432(2) 0.049(5) Uani 1 1 d . . . H14 H 0.6746 0.5482 0.4506 0.058 Uiso 1 1 calc R . . C15 C 0.5326(11) 0.5402(7) 0.356(2) 0.056(5) Uani 1 1 d . . . H15 H 0.5357 0.4989 0.3247 0.067 Uiso 1 1 calc R . . C16 C 0.4481(12) 0.5697(7) 0.326(2) 0.051(5) Uani 1 1 d . . . H16 H 0.3925 0.5490 0.2776 0.061 Uiso 1 1 calc R . . C17 C 0.3070(10) 0.6804(7) 0.4595(19) 0.037(4) Uani 1 1 d . . . H17 H 0.3256 0.6736 0.5732 0.044 Uiso 1 1 calc R . . C18 C 0.3095(11) 0.6798(6) 0.2012(18) 0.034(4) Uani 1 1 d . . . H18 H 0.3286 0.6731 0.0974 0.041 Uiso 1 1 calc R . . C19 C 0.7082(16) 0.7193(10) 0.561(3) 0.096(9) Uani 1 1 d . . . H19 H 0.6686 0.7482 0.4989 0.116 Uiso 1 1 calc R . . C20 C 0.7619(13) 0.6365(8) 0.667(2) 0.055(5) Uani 1 1 d . . . H20 H 0.7679 0.5953 0.7013 0.067 Uiso 1 1 calc R . . Cd1 Cd 0.11109(6) 0.75295(4) 0.03095(11) 0.0200(4) Uani 1 1 d . . . N1 N 0.0000(9) 0.7924(5) -0.3336(15) 0.034(3) Uani 1 1 d . . . N2 N -0.0006(9) 0.7980(5) -0.1665(15) 0.035(3) Uani 1 1 d . . . N3 N -0.1038(9) 0.8590(5) -0.2942(16) 0.038(3) Uani 1 1 d . . . N4 N -0.1178(9) 1.1636(5) -0.3704(16) 0.036(3) Uani 1 1 d . . . N5 N -0.1237(9) 1.1630(5) -0.2043(14) 0.033(3) Uani 1 1 d . . . N6 N -0.1653(9) 1.0744(5) -0.3096(16) 0.037(3) Uani 1 1 d . . . N7 N 0.2303(9) 0.7084(5) 0.2272(15) 0.035(3) Uani 1 1 d . . . N8 N 0.2310(9) 0.7080(5) 0.3977(15) 0.037(3) Uani 1 1 d . . . N9 N 0.3564(8) 0.6625(6) 0.3432(13) 0.030(3) Uani 1 1 d . . . N10 N 0.8227(11) 0.6787(7) 0.716(2) 0.068(5) Uani 1 1 d . . . N11 N 0.7877(12) 0.7319(7) 0.655(3) 0.090(7) Uani 1 1 d . . . N12 N 0.6904(10) 0.6585(7) 0.5648(19) 0.057(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(10) 0.020(8) 0.074(12) -0.002(8) 0.006(9) -0.006(7) C2 0.023(8) 0.031(9) 0.044(10) 0.007(7) 0.005(7) 0.005(7) C3 0.056(12) 0.018(8) 0.060(12) -0.005(8) 0.008(9) -0.001(8) C4 0.041(11) 0.040(10) 0.057(12) 0.000(8) 0.002(9) 0.006(8) C5 0.048(12) 0.055(12) 0.054(12) -0.003(9) -0.007(9) -0.011(10) C6 0.035(10) 0.038(10) 0.074(13) -0.002(9) 0.000(9) 0.003(8) C7 0.033(9) 0.040(9) 0.026(8) -0.004(7) 0.000(7) 0.017(8) C8 0.025(8) 0.042(9) 0.027(8) -0.001(7) -0.001(7) 0.003(7) C9 0.076(13) 0.015(8) 0.043(10) -0.005(7) 0.020(9) -0.001(8) C10 0.040(10) 0.024(8) 0.058(11) -0.003(8) 0.003(8) 0.000(7) C11 0.025(9) 0.050(10) 0.030(9) -0.007(7) 0.000(7) 0.011(8) C12 0.054(13) 0.062(12) 0.053(11) 0.001(10) 0.025(10) 0.013(10) C13 0.046(11) 0.038(10) 0.069(12) 0.000(9) -0.003(10) 0.005(9) C14 0.033(10) 0.033(9) 0.077(13) -0.009(9) 0.000(9) 0.004(8) C15 0.035(10) 0.028(9) 0.101(16) -0.022(9) -0.004(10) -0.002(8) C16 0.039(11) 0.034(9) 0.079(14) -0.016(9) 0.008(9) 0.005(8) C17 0.015(8) 0.060(11) 0.031(9) 0.005(8) -0.010(7) 0.004(8) C18 0.047(10) 0.030(8) 0.025(8) 0.006(7) 0.004(7) 0.002(7) C19 0.078(17) 0.061(14) 0.13(2) 0.031(14) -0.043(15) -0.041(13) C20 0.052(12) 0.037(10) 0.072(13) -0.009(9) -0.011(10) 0.013(9) Cd1 0.0205(6) 0.0161(6) 0.0224(6) 0.0012(5) 0.0000(3) -0.0006(5) N1 0.040(8) 0.030(7) 0.031(7) 0.004(6) 0.000(6) -0.004(6) N2 0.043(8) 0.028(7) 0.031(7) -0.004(6) -0.006(6) 0.015(6) N3 0.040(8) 0.018(7) 0.056(9) -0.002(6) 0.008(7) -0.001(6) N4 0.042(8) 0.020(7) 0.047(9) 0.006(6) 0.010(6) -0.003(6) N5 0.046(8) 0.025(7) 0.026(7) -0.008(5) 0.001(6) 0.005(6) N6 0.042(9) 0.015(6) 0.056(9) 0.006(6) 0.014(7) 0.002(6) N7 0.037(8) 0.026(7) 0.042(8) -0.007(6) 0.001(6) 0.004(6) N8 0.032(8) 0.041(8) 0.036(8) -0.008(6) 0.004(6) -0.004(6) N9 0.026(7) 0.047(8) 0.016(6) 0.000(6) 0.002(5) 0.005(6) N10 0.041(10) 0.062(11) 0.094(13) -0.011(10) -0.008(9) -0.008(8) N11 0.053(11) 0.044(10) 0.16(2) 0.029(11) -0.023(12) -0.007(8) N12 0.048(10) 0.058(10) 0.063(10) 0.011(8) 0.004(8) -0.009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F3' 1.324(13) . ? B1 F2 1.332(13) . ? B1 F4 1.360(12) . ? B1 F1' 1.372(13) . ? B1 F1 1.373(13) . ? B1 F3 1.382(13) . ? B1 F2' 1.384(13) . ? B2 F6' 1.310(13) . ? B2 F8 1.311(13) . ? B2 F5' 1.355(13) . ? B2 F6 1.358(13) . ? B2 F7 1.387(13) . ? B2 F7' 1.388(13) . ? B2 F8' 1.393(13) . ? B2 F5 1.397(13) . ? C1 C2 1.386(19) . ? C1 C6 1.43(2) . ? C1 N3 1.458(19) . ? C2 C3 1.38(2) . ? C2 H2 0.9500 . ? C3 C4 1.34(2) . ? C3 N6 1.490(18) . ? C4 C5 1.40(2) . ? C4 H4 0.9500 . ? C5 C6 1.40(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.280(17) . ? C7 N3 1.362(17) . ? C7 H7 0.9500 . ? C8 N1 1.300(17) . ? C8 N3 1.307(18) . ? C8 H8 0.9500 . ? C9 N5 1.308(18) . ? C9 N6 1.327(18) . ? C9 H9 0.9500 . ? C10 N4 1.308(17) . ? C10 N6 1.347(19) . ? C10 H10 0.9500 . ? C11 C12 1.36(2) . ? C11 C16 1.40(2) . ? C11 N9 1.432(17) . ? C12 C13 1.39(2) . ? C12 H12 0.9500 . ? C13 C14 1.36(2) . ? C13 N12 1.44(2) . ? C14 C15 1.41(2) . ? C14 H14 0.9500 . ? C15 C16 1.36(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N8 1.282(17) . ? C17 N9 1.335(18) . ? C17 H17 0.9500 . ? C18 N9 1.319(17) . ? C18 N7 1.341(18) . ? C18 H18 0.9500 . ? C19 N11 1.31(2) . ? C19 N12 1.36(2) . ? C19 H19 0.9500 . ? C20 N10 1.29(2) . ? C20 N12 1.32(2) . ? C20 H20 0.9500 . ? Cd1 N1 2.302(13) 4_576 ? Cd1 N2 2.329(11) . ? Cd1 N5 2.333(11) 3_575 ? Cd1 N8 2.335(13) 4_575 ? Cd1 N7 2.382(12) . ? Cd1 N4 2.385(11) 2_544 ? N1 N2 1.389(16) . ? N1 Cd1 2.302(13) 4_575 ? N4 N5 1.389(16) . ? N4 Cd1 2.385(11) 2_554 ? N5 Cd1 2.333(11) 3_575 ? N7 N8 1.408(17) . ? N8 Cd1 2.335(13) 4_576 ? N10 N11 1.34(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F3' B1 F2 131.9(15) . . ? F3' B1 F4 112.3(11) . . ? F2 B1 F4 114.2(11) . . ? F3' B1 F1' 113.2(12) . . ? F2 B1 F1' 62.6(12) . . ? F4 B1 F1' 107.5(11) . . ? F3' B1 F1 41.0(11) . . ? F2 B1 F1 111.7(12) . . ? F4 B1 F1 107.1(11) . . ? F1' B1 F1 143.6(14) . . ? F3' B1 F3 66.1(12) . . ? F2 B1 F3 109.1(11) . . ? F4 B1 F3 107.9(11) . . ? F1' B1 F3 51.5(12) . . ? F1 B1 F3 106.4(11) . . ? F3' B1 F2' 110.1(11) . . ? F2 B1 F2' 43.8(11) . . ? F4 B1 F2' 107.4(11) . . ? F1' B1 F2' 106.0(11) . . ? F1 B1 F2' 73.7(12) . . ? F3 B1 F2' 142.8(14) . . ? F6' B2 F8 146.8(14) . . ? F6' B2 F5' 113.9(11) . . ? F8 B2 F5' 84.6(13) . . ? F6' B2 F6 95.7(13) . . ? F8 B2 F6 115.9(12) . . ? F5' B2 F6 77.2(13) . . ? F6' B2 F7 64.3(11) . . ? F8 B2 F7 112.5(12) . . ? F5' B2 F7 56.1(11) . . ? F6 B2 F7 106.5(11) . . ? F6' B2 F7' 112.2(12) . . ? F8 B2 F7' 85.4(14) . . ? F5' B2 F7' 108.0(11) . . ? F6 B2 F7' 46.1(12) . . ? F7 B2 F7' 152.5(14) . . ? F6' B2 F8' 111.1(11) . . ? F8 B2 F8' 35.7(11) . . ? F5' B2 F8' 107.1(11) . . ? F6 B2 F8' 147.0(13) . . ? F7 B2 F8' 102.4(14) . . ? F7' B2 F8' 103.9(11) . . ? F6' B2 F5 46.8(10) . . ? F8 B2 F5 108.8(11) . . ? F5' B2 F5 159.1(13) . . ? F6 B2 F5 109.2(11) . . ? F7 B2 F5 103.3(10) . . ? F7' B2 F5 89.4(13) . . ? F8' B2 F5 78.7(12) . . ? C2 C1 C6 122.7(15) . . ? C2 C1 N3 117.1(13) . . ? C6 C1 N3 119.8(13) . . ? C3 C2 C1 115.6(14) . . ? C3 C2 H2 122.2 . . ? C1 C2 H2 122.2 . . ? C4 C3 C2 124.5(15) . . ? C4 C3 N6 121.3(14) . . ? C2 C3 N6 113.9(14) . . ? C3 C4 C5 120.6(16) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 118.7(16) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C1 117.8(15) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? N2 C7 N3 109.1(13) . . ? N2 C7 H7 125.5 . . ? N3 C7 H7 125.5 . . ? N1 C8 N3 110.8(13) . . ? N1 C8 H8 124.6 . . ? N3 C8 H8 124.6 . . ? N5 C9 N6 112.0(14) . . ? N5 C9 H9 124.0 . . ? N6 C9 H9 124.0 . . ? N4 C10 N6 109.2(15) . . ? N4 C10 H10 125.4 . . ? N6 C10 H10 125.4 . . ? C12 C11 C16 120.1(15) . . ? C12 C11 N9 120.0(14) . . ? C16 C11 N9 119.7(14) . . ? C11 C12 C13 120.6(17) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 121.0(17) . . ? C14 C13 N12 119.9(15) . . ? C12 C13 N12 119.1(16) . . ? C13 C14 C15 117.5(15) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C16 C15 C14 122.2(15) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C15 C16 C11 118.4(15) . . ? C15 C16 H16 120.8 . . ? C11 C16 H16 120.8 . . ? N8 C17 N9 111.1(14) . . ? N8 C17 H17 124.4 . . ? N9 C17 H17 124.4 . . ? N9 C18 N7 108.8(13) . . ? N9 C18 H18 125.6 . . ? N7 C18 H18 125.6 . . ? N11 C19 N12 110.0(19) . . ? N11 C19 H19 125.0 . . ? N12 C19 H19 125.0 . . ? N10 C20 N12 110.7(16) . . ? N10 C20 H20 124.7 . . ? N12 C20 H20 124.7 . . ? N1 Cd1 N2 94.4(4) 4_576 . ? N1 Cd1 N5 92.4(4) 4_576 3_575 ? N2 Cd1 N5 94.2(4) . 3_575 ? N1 Cd1 N8 175.4(4) 4_576 4_575 ? N2 Cd1 N8 89.2(4) . 4_575 ? N5 Cd1 N8 90.1(4) 3_575 4_575 ? N1 Cd1 N7 88.0(4) 4_576 . ? N2 Cd1 N7 177.7(5) . . ? N5 Cd1 N7 85.8(4) 3_575 . ? N8 Cd1 N7 88.5(4) 4_575 . ? N1 Cd1 N4 90.0(4) 4_576 2_544 ? N2 Cd1 N4 92.4(4) . 2_544 ? N5 Cd1 N4 172.7(4) 3_575 2_544 ? N8 Cd1 N4 87.0(4) 4_575 2_544 ? N7 Cd1 N4 87.4(4) . 2_544 ? C8 N1 N2 106.0(12) . . ? C8 N1 Cd1 123.6(10) . 4_575 ? N2 N1 Cd1 129.0(9) . 4_575 ? C7 N2 N1 107.6(11) . . ? C7 N2 Cd1 128.1(10) . . ? N1 N2 Cd1 123.6(9) . . ? C8 N3 C7 106.3(12) . . ? C8 N3 C1 126.3(14) . . ? C7 N3 C1 127.2(14) . . ? C10 N4 N5 108.2(12) . . ? C10 N4 Cd1 124.3(11) . 2_554 ? N5 N4 Cd1 124.9(8) . 2_554 ? C9 N5 N4 104.9(11) . . ? C9 N5 Cd1 128.2(10) . 3_575 ? N4 N5 Cd1 126.1(8) . 3_575 ? C9 N6 C10 105.7(13) . . ? C9 N6 C3 130.3(13) . . ? C10 N6 C3 123.7(14) . . ? C18 N7 N8 106.1(12) . . ? C18 N7 Cd1 128.3(10) . . ? N8 N7 Cd1 125.6(9) . . ? C17 N8 N7 106.4(13) . . ? C17 N8 Cd1 128.6(11) . 4_576 ? N7 N8 Cd1 125.0(9) . 4_576 ? C18 N9 C17 107.6(12) . . ? C18 N9 C11 126.2(13) . . ? C17 N9 C11 126.1(12) . . ? C20 N10 N11 108.5(16) . . ? C19 N11 N10 106.2(17) . . ? C20 N12 C19 104.4(16) . . ? C20 N12 C13 129.5(16) . . ? C19 N12 C13 126.1(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.355 _refine_diff_density_min -1.379 _refine_diff_density_rms 0.222 _database_code_depnum_ccdc_archive 'CCDC 917438' ####################################################################### # # 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_1a #TrackingRef '1-ok.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 Cd N12, 2(Cl O4)' _chemical_formula_sum 'C20 H16 Cd Cl2 N12 O8' _chemical_formula_weight 735.75 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.327(3) _cell_length_b 22.105(5) _cell_length_c 8.3039(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.790(3) _cell_angle_gamma 90.00 _cell_volume 2599.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1064 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 20.45 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.880 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7301 _exptl_absorpt_correction_T_max 0.8501 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12989 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.1159 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4552 _reflns_number_gt 2697 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0556P)^2^+2.0786P] 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_number_reflns 4552 _refine_ls_number_parameters 378 _refine_ls_number_restraints 181 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.011 _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 Cl1 Cl 0.12959(18) -0.00835(12) 0.8006(3) 0.0431(7) Uani 1 1 d D . . O1 O 0.0907(5) -0.0691(3) 0.7858(8) 0.0516(19) Uiso 1 1 d D A . O2 O 0.0700(9) 0.0266(5) 0.8923(15) 0.065(5) Uiso 0.531(14) 1 d PD A 1 O3 O 0.1308(11) 0.0171(6) 0.6487(14) 0.089(6) Uiso 0.531(14) 1 d PD A 1 O4 O 0.2207(8) -0.0131(6) 0.9004(17) 0.078(6) Uiso 0.531(14) 1 d PD A 1 O2' O 0.0669(10) 0.0320(6) 0.6988(19) 0.090(8) Uiso 0.469(14) 1 d PD A 2 O3' O 0.2151(9) -0.0085(6) 0.7222(18) 0.069(6) Uiso 0.469(14) 1 d PD A 2 O4' O 0.1525(13) 0.0122(7) 0.9597(14) 0.097(8) Uiso 0.469(14) 1 d PD A 2 Cl2 Cl 0.45832(18) 0.66146(11) 0.8633(3) 0.0392(6) Uani 1 1 d D . . O5 O 0.4958(7) 0.6763(5) 1.0299(10) 0.047(4) Uiso 0.594(12) 1 d PD B 3 O6 O 0.4888(9) 0.6068(4) 0.8101(15) 0.063(4) Uiso 0.594(12) 1 d PD B 3 O7 O 0.3544(6) 0.6624(6) 0.8489(12) 0.048(4) Uiso 0.594(12) 1 d PD B 3 O8 O 0.4809(9) 0.7123(5) 0.7632(13) 0.065(5) Uiso 0.594(12) 1 d PD B 3 O5' O 0.4723(12) 0.6348(8) 1.0256(14) 0.064(6) Uiso 0.406(12) 1 d PD B 4 O6' O 0.4364(12) 0.6084(6) 0.7537(18) 0.061(6) Uiso 0.406(12) 1 d PD B 4 O7' O 0.3810(9) 0.7000(6) 0.8424(16) 0.033(5) Uiso 0.406(12) 1 d PD B 4 O8' O 0.5440(9) 0.6868(7) 0.828(2) 0.061(7) Uiso 0.406(12) 1 d PD B 4 C1 C -0.1790(6) 0.9101(4) -0.3310(10) 0.022(2) Uani 1 1 d . . . C2 C -0.1434(5) 0.9666(4) -0.2947(9) 0.0173(18) Uani 1 1 d . . . H2 H -0.0800 0.9722 -0.2436 0.021 Uiso 1 1 calc R . . C3 C -0.2022(6) 1.0151(4) -0.3346(9) 0.022(2) Uani 1 1 d . . . C4 C -0.2950(6) 1.0069(4) -0.4098(11) 0.031(2) Uani 1 1 d . . . H4 H -0.3350 1.0407 -0.4376 0.038 Uiso 1 1 calc R . . C5 C -0.3277(6) 0.9494(4) -0.4434(11) 0.032(2) Uani 1 1 d . . . H5 H -0.3910 0.9436 -0.4950 0.039 Uiso 1 1 calc R . . C6 C -0.2706(6) 0.9001(4) -0.4035(11) 0.028(2) Uani 1 1 d . . . H6 H -0.2937 0.8602 -0.4253 0.033 Uiso 1 1 calc R . . C7 C -0.0696(5) 0.8398(4) -0.1514(9) 0.0207(19) Uani 1 1 d . . . H7 H -0.0824 0.8539 -0.0489 0.025 Uiso 1 1 calc R . . C8 C -0.0738(6) 0.8282(3) -0.4062(10) 0.022(2) Uani 1 1 d . . . H8 H -0.0903 0.8324 -0.5208 0.027 Uiso 1 1 calc R . . C9 C -0.1485(6) 1.1084(4) -0.1729(10) 0.028(2) Uani 1 1 d . . . H9 H -0.1599 1.0944 -0.0695 0.033 Uiso 1 1 calc R . . C10 C -0.1366(6) 1.1123(4) -0.4259(10) 0.026(2) Uani 1 1 d . . . H10 H -0.1377 1.1012 -0.5367 0.032 Uiso 1 1 calc R . . C11 C 0.4375(6) 0.6305(4) 0.3655(9) 0.023(2) Uani 1 1 d . . . C12 C 0.5154(6) 0.6608(4) 0.4410(10) 0.025(2) Uani 1 1 d . . . H12 H 0.5118 0.7021 0.4713 0.030 Uiso 1 1 calc R . . C13 C 0.5994(6) 0.6291(4) 0.4715(10) 0.026(2) Uani 1 1 d . . . C14 C 0.6042(6) 0.5698(4) 0.4246(11) 0.034(2) Uani 1 1 d . . . H14 H 0.6627 0.5488 0.4459 0.040 Uiso 1 1 calc R . . C15 C 0.5247(6) 0.5402(4) 0.3466(12) 0.041(3) Uani 1 1 d . . . H15 H 0.5286 0.4993 0.3131 0.050 Uiso 1 1 calc R . . C16 C 0.4396(6) 0.5709(4) 0.3180(11) 0.032(2) Uani 1 1 d . . . H16 H 0.3839 0.5513 0.2668 0.038 Uiso 1 1 calc R . . C17 C 0.2983(6) 0.6816(4) 0.4547(11) 0.029(2) Uani 1 1 d . . . H17 H 0.3168 0.6753 0.5683 0.034 Uiso 1 1 calc R . . C18 C 0.2973(6) 0.6805(4) 0.1968(10) 0.023(2) Uani 1 1 d . . . H18 H 0.3145 0.6734 0.0924 0.027 Uiso 1 1 calc R . . C19 C 0.7040(8) 0.7192(5) 0.5413(14) 0.057(3) Uani 1 1 d . . . H19 H 0.6689 0.7472 0.4691 0.068 Uiso 1 1 calc R . . C20 C 0.7479(7) 0.6396(5) 0.6670(12) 0.046(3) Uani 1 1 d . . . H20 H 0.7504 0.5989 0.7037 0.055 Uiso 1 1 calc R . . Cd1 Cd 0.10155(4) 0.75333(3) 0.02740(6) 0.01729(19) Uani 1 1 d . . . N1 N -0.0098(5) 0.7915(3) -0.3361(8) 0.0217(16) Uani 1 1 d . . . N2 N -0.0071(5) 0.7987(3) -0.1690(8) 0.0194(15) Uani 1 1 d . . . N3 N -0.1141(4) 0.8599(3) -0.2962(7) 0.0186(15) Uani 1 1 d . . . N4 N -0.1094(5) 1.1647(3) -0.3660(8) 0.0241(17) Uani 1 1 d . . . N5 N -0.1164(5) 1.1620(3) -0.2000(8) 0.0249(17) Uani 1 1 d . . . N6 N -0.1632(5) 1.0753(3) -0.3109(8) 0.0225(16) Uani 1 1 d . . . N7 N 0.2207(5) 0.7086(3) 0.2234(7) 0.0229(16) Uani 1 1 d . . . N8 N 0.2216(5) 0.7091(3) 0.3899(8) 0.0210(16) Uani 1 1 d . . . N9 N 0.3479(5) 0.6631(3) 0.3389(8) 0.0256(17) Uani 1 1 d . . . N10 N 0.8107(6) 0.6802(4) 0.7243(10) 0.044(2) Uani 1 1 d . . . N11 N 0.7808(6) 0.7329(4) 0.6410(11) 0.051(2) Uani 1 1 d . . . N12 N 0.6806(5) 0.6601(3) 0.5536(8) 0.0288(18) 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 Cl1 0.0410(16) 0.0511(17) 0.0373(14) -0.0061(12) 0.0058(12) -0.0112(13) Cl2 0.0422(15) 0.0434(16) 0.0328(13) 0.0039(11) 0.0077(11) 0.0053(13) C1 0.023(5) 0.016(5) 0.028(5) -0.001(4) 0.003(4) 0.000(4) C2 0.010(4) 0.019(5) 0.023(4) 0.003(4) 0.003(3) 0.005(4) C3 0.030(5) 0.021(5) 0.015(4) -0.004(4) 0.008(4) -0.005(4) C4 0.023(5) 0.025(5) 0.045(6) 0.002(4) 0.002(4) 0.001(4) C5 0.021(5) 0.024(5) 0.047(6) -0.006(4) -0.011(4) -0.004(4) C6 0.016(5) 0.017(5) 0.050(6) -0.006(4) 0.006(4) -0.005(4) C7 0.023(5) 0.020(5) 0.019(4) -0.003(4) 0.004(4) -0.006(4) C8 0.021(5) 0.015(5) 0.031(5) 0.002(4) 0.004(4) 0.005(4) C9 0.044(6) 0.020(5) 0.022(5) -0.002(4) 0.012(4) -0.003(4) C10 0.039(6) 0.018(5) 0.024(5) 0.007(4) 0.012(4) 0.003(4) C11 0.021(5) 0.033(6) 0.018(4) 0.003(4) 0.010(4) 0.011(4) C12 0.020(5) 0.025(5) 0.029(5) 0.004(4) 0.002(4) 0.006(4) C13 0.025(5) 0.027(5) 0.030(5) 0.005(4) 0.011(4) 0.000(4) C14 0.022(5) 0.037(6) 0.042(6) -0.008(5) 0.004(4) 0.011(5) C15 0.029(6) 0.031(6) 0.064(7) -0.007(5) 0.006(5) 0.008(5) C16 0.019(5) 0.037(6) 0.039(6) -0.006(4) 0.002(4) 0.008(4) C17 0.023(5) 0.034(6) 0.029(5) -0.005(4) 0.001(4) -0.002(4) C18 0.023(5) 0.025(5) 0.022(5) 0.000(4) 0.008(4) 0.004(4) C19 0.046(7) 0.039(7) 0.078(8) 0.015(6) -0.015(6) -0.012(6) C20 0.051(7) 0.030(6) 0.051(6) 0.000(5) -0.006(6) -0.003(5) Cd1 0.0179(3) 0.0164(3) 0.0176(3) 0.0010(3) 0.0027(2) -0.0001(3) N1 0.022(4) 0.015(4) 0.027(4) -0.001(3) 0.002(3) 0.003(3) N2 0.021(4) 0.013(4) 0.025(4) -0.004(3) 0.004(3) 0.001(3) N3 0.017(4) 0.013(4) 0.024(4) 0.002(3) -0.001(3) 0.001(3) N4 0.026(4) 0.018(4) 0.029(4) -0.001(3) 0.006(3) -0.004(3) N5 0.037(5) 0.016(4) 0.021(4) -0.001(3) 0.003(3) 0.001(3) N6 0.024(4) 0.014(4) 0.029(4) 0.000(3) 0.003(3) 0.001(3) N7 0.024(4) 0.026(4) 0.017(4) -0.001(3) -0.001(3) 0.005(3) N8 0.021(4) 0.027(4) 0.016(4) 0.002(3) 0.006(3) 0.002(3) N9 0.022(4) 0.036(5) 0.019(4) -0.001(3) 0.005(3) 0.005(3) N10 0.034(5) 0.052(6) 0.041(5) -0.003(4) -0.011(4) -0.009(4) N11 0.040(5) 0.044(6) 0.062(6) -0.001(5) -0.012(5) -0.011(4) N12 0.019(4) 0.032(5) 0.033(4) 0.007(4) -0.004(3) 0.002(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 Cl1 O3 1.383(10) . ? Cl1 O4' 1.388(11) . ? Cl1 O4 1.438(10) . ? Cl1 O2' 1.444(11) . ? Cl1 O2 1.451(10) . ? Cl1 O1 1.452(6) . ? Cl1 O3' 1.473(10) . ? Cl2 O6 1.380(9) . ? Cl2 O7' 1.387(10) . ? Cl2 O8' 1.419(10) . ? Cl2 O5 1.443(8) . ? Cl2 O5' 1.456(10) . ? Cl2 O8 1.463(9) . ? Cl2 O7 1.475(9) . ? Cl2 O6' 1.489(10) . ? C1 C2 1.367(11) . ? C1 C6 1.376(11) . ? C1 N3 1.448(10) . ? C2 C3 1.372(11) . ? C2 H2 0.9500 . ? C3 C4 1.392(11) . ? C3 N6 1.444(10) . ? C4 C5 1.367(11) . ? C4 H4 0.9500 . ? C5 C6 1.374(11) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.299(10) . ? C7 N3 1.347(9) . ? C7 H7 0.9500 . ? C8 N1 1.295(10) . ? C8 N3 1.348(10) . ? C8 H8 0.9500 . ? C9 N5 1.303(10) . ? C9 N6 1.349(10) . ? C9 H9 0.9500 . ? C10 N4 1.298(10) . ? C10 N6 1.356(10) . ? C10 H10 0.9500 . ? C11 C12 1.370(11) . ? C11 C16 1.376(12) . ? C11 N9 1.459(10) . ? C12 C13 1.383(11) . ? C12 H12 0.9500 . ? C13 C14 1.372(12) . ? C13 N12 1.430(11) . ? C14 C15 1.386(12) . ? C14 H14 0.9500 . ? C15 C16 1.384(12) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N8 1.299(10) . ? C17 N9 1.344(10) . ? C17 H17 0.9500 . ? C18 N7 1.309(10) . ? C18 N9 1.343(10) . ? C18 H18 0.9500 . ? C19 N11 1.308(12) . ? C19 N12 1.355(12) . ? C19 H19 0.9500 . ? C20 N10 1.309(11) . ? C20 N12 1.321(11) . ? C20 H20 0.9500 . ? Cd1 N2 2.305(6) . ? Cd1 N1 2.316(7) 4_576 ? Cd1 N5 2.348(7) 3_575 ? Cd1 N8 2.356(7) 4_575 ? Cd1 N4 2.385(7) 2_544 ? Cd1 N7 2.386(6) . ? N1 N2 1.391(9) . ? N1 Cd1 2.316(7) 4_575 ? N4 N5 1.398(9) . ? N4 Cd1 2.386(7) 2_554 ? N5 Cd1 2.348(7) 3_575 ? N7 N8 1.381(8) . ? N8 Cd1 2.356(7) 4_576 ? N10 N11 1.389(11) . ? 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 O3 Cl1 O4' 134.5(9) . . ? O3 Cl1 O4 114.7(8) . . ? O4' Cl1 O4 54.1(8) . . ? O3 Cl1 O2' 46.2(8) . . ? O4' Cl1 O2' 113.0(8) . . ? O4 Cl1 O2' 144.2(9) . . ? O3 Cl1 O2 110.6(7) . . ? O4' Cl1 O2 53.0(8) . . ? O4 Cl1 O2 106.9(7) . . ? O2' Cl1 O2 67.3(8) . . ? O3 Cl1 O1 110.9(6) . . ? O4' Cl1 O1 114.5(7) . . ? O4 Cl1 O1 106.5(6) . . ? O2' Cl1 O1 109.0(7) . . ? O2 Cl1 O1 106.8(6) . . ? O3 Cl1 O3' 58.1(7) . . ? O4' Cl1 O3' 109.3(8) . . ? O4 Cl1 O3' 60.8(7) . . ? O2' Cl1 O3' 103.2(7) . . ? O2 Cl1 O3' 146.0(8) . . ? O1 Cl1 O3' 107.1(6) . . ? O6 Cl2 O7' 141.5(8) . . ? O6 Cl2 O8' 87.4(8) . . ? O7' Cl2 O8' 115.5(8) . . ? O6 Cl2 O5 114.6(6) . . ? O7' Cl2 O5 98.8(7) . . ? O8' Cl2 O5 84.2(8) . . ? O6 Cl2 O5' 86.4(8) . . ? O7' Cl2 O5' 111.0(7) . . ? O8' Cl2 O5' 110.4(8) . . ? O5 Cl2 O5' 39.4(7) . . ? O6 Cl2 O8 112.5(6) . . ? O7' Cl2 O8 72.5(7) . . ? O8' Cl2 O8 46.2(7) . . ? O5 Cl2 O8 106.7(6) . . ? O5' Cl2 O8 145.7(8) . . ? O6 Cl2 O7 110.6(6) . . ? O7' Cl2 O7 37.3(6) . . ? O8' Cl2 O7 150.6(8) . . ? O5 Cl2 O7 107.3(6) . . ? O5' Cl2 O7 94.3(8) . . ? O8 Cl2 O7 104.5(6) . . ? O6 Cl2 O6' 33.1(7) . . ? O7' Cl2 O6' 108.5(8) . . ? O8' Cl2 O6' 107.1(8) . . ? O5 Cl2 O6' 141.1(8) . . ? O5' Cl2 O6' 103.5(8) . . ? O8 Cl2 O6' 107.6(8) . . ? O7 Cl2 O6' 81.1(8) . . ? C2 C1 C6 122.8(8) . . ? C2 C1 N3 116.8(7) . . ? C6 C1 N3 120.3(7) . . ? C1 C2 C3 117.8(7) . . ? C1 C2 H2 121.1 . . ? C3 C2 H2 121.1 . . ? C2 C3 C4 121.1(8) . . ? C2 C3 N6 118.4(7) . . ? C4 C3 N6 120.3(8) . . ? C5 C4 C3 119.2(8) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.0(8) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.2(8) . . ? C5 C6 H6 120.9 . . ? C1 C6 H6 120.9 . . ? N2 C7 N3 111.7(7) . . ? N2 C7 H7 124.2 . . ? N3 C7 H7 124.2 . . ? N1 C8 N3 111.6(7) . . ? N1 C8 H8 124.2 . . ? N3 C8 H8 124.2 . . ? N5 C9 N6 111.1(7) . . ? N5 C9 H9 124.5 . . ? N6 C9 H9 124.5 . . ? N4 C10 N6 111.7(7) . . ? N4 C10 H10 124.2 . . ? N6 C10 H10 124.2 . . ? C12 C11 C16 123.2(8) . . ? C12 C11 N9 117.6(8) . . ? C16 C11 N9 119.2(8) . . ? C11 C12 C13 117.5(8) . . ? C11 C12 H12 121.3 . . ? C13 C12 H12 121.3 . . ? C14 C13 C12 120.8(8) . . ? C14 C13 N12 121.4(8) . . ? C12 C13 N12 117.8(8) . . ? C13 C14 C15 120.7(8) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.2(9) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C11 C16 C15 118.6(8) . . ? C11 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? N8 C17 N9 110.7(8) . . ? N8 C17 H17 124.7 . . ? N9 C17 H17 124.7 . . ? N7 C18 N9 110.0(7) . . ? N7 C18 H18 125.0 . . ? N9 C18 H18 125.0 . . ? N11 C19 N12 111.7(9) . . ? N11 C19 H19 124.1 . . ? N12 C19 H19 124.1 . . ? N10 C20 N12 114.2(9) . . ? N10 C20 H20 122.9 . . ? N12 C20 H20 122.9 . . ? N2 Cd1 N1 95.2(2) . 4_576 ? N2 Cd1 N5 94.2(2) . 3_575 ? N1 Cd1 N5 92.7(2) 4_576 3_575 ? N2 Cd1 N8 88.2(2) . 4_575 ? N1 Cd1 N8 175.1(2) 4_576 4_575 ? N5 Cd1 N8 90.6(2) 3_575 4_575 ? N2 Cd1 N4 92.6(2) . 2_544 ? N1 Cd1 N4 91.1(2) 4_576 2_544 ? N5 Cd1 N4 171.9(2) 3_575 2_544 ? N8 Cd1 N4 85.2(2) 4_575 2_544 ? N2 Cd1 N7 176.9(2) . . ? N1 Cd1 N7 87.9(2) 4_576 . ? N5 Cd1 N7 85.7(2) 3_575 . ? N8 Cd1 N7 88.7(2) 4_575 . ? N4 Cd1 N7 87.3(2) 2_544 . ? C8 N1 N2 106.6(7) . . ? C8 N1 Cd1 122.8(6) . 4_575 ? N2 N1 Cd1 128.4(5) . 4_575 ? C7 N2 N1 106.2(6) . . ? C7 N2 Cd1 128.8(5) . . ? N1 N2 Cd1 124.6(5) . . ? C7 N3 C8 103.9(7) . . ? C7 N3 C1 129.2(7) . . ? C8 N3 C1 126.3(7) . . ? C10 N4 N5 106.1(6) . . ? C10 N4 Cd1 123.7(5) . 2_554 ? N5 N4 Cd1 127.3(5) . 2_554 ? C9 N5 N4 106.9(7) . . ? C9 N5 Cd1 128.4(6) . 3_575 ? N4 N5 Cd1 123.6(5) . 3_575 ? C9 N6 C10 104.3(7) . . ? C9 N6 C3 128.5(7) . . ? C10 N6 C3 127.2(7) . . ? C18 N7 N8 107.0(6) . . ? C18 N7 Cd1 127.8(5) . . ? N8 N7 Cd1 125.2(5) . . ? C17 N8 N7 106.8(7) . . ? C17 N8 Cd1 126.7(6) . 4_576 ? N7 N8 Cd1 126.3(5) . 4_576 ? C18 N9 C17 105.5(7) . . ? C18 N9 C11 128.3(7) . . ? C17 N9 C11 126.2(7) . . ? C20 N10 N11 104.5(8) . . ? C19 N11 N10 106.7(8) . . ? C20 N12 C19 102.8(8) . . ? C20 N12 C13 128.8(8) . . ? C19 N12 C13 128.2(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.079 _refine_diff_density_min -0.699 _refine_diff_density_rms 0.144 _database_code_depnum_ccdc_archive 'CCDC 917439' ####################################################################### # # 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_1b #TrackingRef '1-ok.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C20 H16 Cd N12), N O3' _chemical_formula_sum 'C60 H48 Cd3 N37 O3' _chemical_formula_weight 1672.58 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' 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' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M 'R -3 m' _symmetry_space_group_name_Hall '-R 3 2"' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z' '-x, -x+y, -z' 'x-y, -y, -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' 'y+2/3, x+1/3, -z+1/3' '-x+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, -y+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' 'y+1/3, x+2/3, -z+2/3' '-x+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, -y+2/3, -z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z' 'x, x-y, z' '-x+y, y, 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' '-y+2/3, -x+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-x+y+2/3, y+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' '-y+1/3, -x+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' '-x+y+1/3, y+2/3, z+2/3' _cell_length_a 20.5262(16) _cell_length_b 20.5262(16) _cell_length_c 20.152(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7353.0(15) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2557 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 22.10 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.133 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2504 _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8450 _exptl_absorpt_correction_T_max 0.8732 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9469 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1739 _reflns_number_gt 1431 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1111P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1739 _refine_ls_number_parameters 160 _refine_ls_number_restraints 175 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.102 _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 0.0000 0.02154(15) Uani 1 12 d S . . Cd2 Cd 0.0000 0.0000 0.205442(18) 0.02028(12) Uani 1 6 d S . . C1 C 0.1677(5) 0.3004(3) 0.1110(2) 0.087(2) Uani 0.50 1 d PDU . . C2 C 0.1782(6) 0.3441(2) 0.0558(2) 0.073(2) Uani 0.50 1 d PDU . . H2A H 0.1473 0.3230 0.0169 0.087 Uiso 0.50 1 d PR . . C3 C 0.2299(5) 0.4204(3) 0.0598(3) 0.096(3) Uani 0.50 1 d PDU . . C4 C 0.2708(6) 0.4533(5) 0.1162(4) 0.133(3) Uani 0.50 1 d PDU . . H4A H 0.3121 0.5044 0.1153 0.159 Uiso 0.50 1 d PR . . C5 C 0.2586(8) 0.4071(4) 0.1695(4) 0.145(3) Uani 0.50 1 d PDU . . H5A H 0.2813 0.4298 0.2114 0.174 Uiso 0.50 1 d PR . . C6 C 0.2040(7) 0.3324(4) 0.1684(3) 0.136(3) Uani 0.50 1 d PDU . . H6A H 0.2039 0.3000 0.2030 0.163 Uiso 0.50 1 d PR . . N3 N 0.1224(5) 0.2220(2) 0.10633(16) 0.0607(19) Uani 0.50 1 d PDU . . C7 C 0.1007(4) 0.1731(2) 0.15770(19) 0.046(2) Uani 0.50 1 d PDU . . H7A H 0.1116 0.1879 0.2036 0.055 Uiso 0.50 1 d PR . . N2 N 0.0629(4) 0.1051(2) 0.13646(15) 0.0388(16) Uani 0.50 1 d PDU . . N1 N 0.05380(9) 0.10759(18) 0.06787(13) 0.0368(9) Uani 1 2 d SDU . . C8 C 0.0964(7) 0.1770(2) 0.05151(19) 0.054(2) Uani 0.50 1 d PDU . . H8A H 0.1115 0.1941 0.0066 0.065 Uiso 0.50 1 d PR . . N6 N 0.2462(5) 0.4644(2) 0.0007(2) 0.081(2) Uani 0.50 1 d PDU . . C9 C 0.2487(5) 0.4392(4) -0.0624(3) 0.090(3) Uani 0.50 1 d PDU . . H9A H 0.2420 0.3903 -0.0725 0.108 Uiso 0.50 1 d PR . . N5 N 0.2713(4) 0.4924(3) -0.1061(3) 0.082(3) Uani 0.50 1 d PDU . . N4 N 0.27874(11) 0.5575(2) -0.06765(18) 0.0637(13) Uani 1 2 d SDU . . C10 C 0.26803(12) 0.5361(2) -0.0087(2) 0.0679(16) Uani 1 2 d SDU . . H10A H 0.2654 0.5672 0.0263 0.082 Uiso 0.50 1 d PR . . N7 N 0.3333 0.6667 0.1735(5) 0.057(2) Uani 0.50 6 d SPDU . . O1 O 0.3333 0.6667 0.1131(4) 0.074(3) Uani 0.50 6 d SPDU . . O2 O 0.3901(6) 0.6950(3) 0.2092(5) 0.030(3) Uani 0.17 2 d SPDU . . O3 O 0.2697(7) 0.6349(3) 0.2023(7) 0.084(4) Uani 0.17 2 d SPDU . . 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 0.0229(2) 0.0229(2) 0.0189(2) 0.000 0.000 0.01144(10) Cd2 0.02067(16) 0.02067(16) 0.01951(19) 0.000 0.000 0.01033(8) C1 0.161(4) 0.021(2) 0.0282(19) 0.0023(18) -0.010(3) 0.008(3) C2 0.146(4) 0.021(2) 0.0304(17) 0.0052(16) -0.011(4) 0.027(4) C3 0.169(5) 0.027(2) 0.038(2) 0.008(2) -0.007(3) 0.009(3) C4 0.215(5) 0.039(3) 0.050(3) 0.003(3) -0.020(4) -0.007(4) C5 0.235(6) 0.037(4) 0.054(3) 0.005(3) -0.036(4) -0.012(4) C6 0.219(6) 0.041(3) 0.050(3) 0.007(3) -0.032(4) -0.008(4) N3 0.109(4) 0.0195(18) 0.0269(15) 0.0039(14) -0.003(3) 0.012(3) C7 0.078(4) 0.021(2) 0.0230(16) 0.0057(15) 0.001(2) 0.013(3) N2 0.059(3) 0.0242(17) 0.0201(13) 0.0040(13) 0.002(2) 0.011(2) N1 0.0545(18) 0.0210(17) 0.0237(13) 0.0013(12) 0.0006(6) 0.0105(9) C8 0.086(4) 0.025(2) 0.0231(16) -0.0026(16) -0.002(4) 0.006(3) N6 0.139(4) 0.025(2) 0.051(2) 0.0162(17) -0.006(3) 0.018(3) C9 0.146(5) 0.040(3) 0.057(3) 0.011(3) 0.010(3) 0.027(3) N5 0.136(5) 0.036(2) 0.053(2) -0.001(2) 0.012(3) 0.026(3) N4 0.095(3) 0.030(2) 0.0437(18) 0.0101(16) 0.0050(8) 0.0152(10) C10 0.119(3) 0.019(2) 0.0320(18) 0.0023(17) 0.0012(8) 0.0096(11) N7 0.063(3) 0.063(3) 0.046(4) 0.000 0.000 0.0313(13) O1 0.082(4) 0.082(4) 0.059(5) 0.000 0.000 0.041(2) O2 0.048(6) 0.023(5) 0.029(5) -0.008(2) -0.017(5) 0.024(3) O3 0.071(7) 0.096(7) 0.077(7) 0.003(3) 0.007(6) 0.035(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 2.351(3) . ? Cd1 N1 2.351(3) 19 ? Cd1 N1 2.351(3) 21 ? Cd1 N1 2.351(3) 3 ? Cd1 N1 2.351(3) 2 ? Cd1 N1 2.351(3) 20 ? Cd2 N4 2.289(4) 8 ? Cd2 N4 2.289(4) 7_445 ? Cd2 N4 2.289(4) 9_455 ? Cd2 N2 2.339(3) 3 ? Cd2 N2 2.339(3) 23 ? Cd2 N2 2.339(3) 22 ? Cd2 N2 2.339(3) . ? Cd2 N2 2.339(3) 2 ? Cd2 N2 2.339(3) 24 ? C1 C1 0.72(2) 24 ? C1 C6 1.355(9) . ? C1 C2 1.376(7) . ? C1 N3 1.404(6) . ? C1 C2 1.440(8) 24 ? C1 N3 1.519(8) 24 ? C2 C2 0.25(2) 24 ? C2 C3 1.387(7) . ? C2 C1 1.440(8) 24 ? C2 C3 1.459(9) 24 ? C2 H2A 0.9638 . ? C3 C3 0.81(2) 24 ? C3 C4 1.374(9) . ? C3 N6 1.429(7) . ? C3 C2 1.459(9) 24 ? C3 N6 1.584(9) 24 ? C4 C5 1.370(10) . ? C4 H4A 0.9643 . ? C5 C6 1.374(9) . ? C5 H5A 0.9637 . ? C6 C6 1.55(3) 24 ? C6 H6A 0.9639 . ? N3 N3 0.469(19) 24 ? N3 C7 1.352(5) . ? N3 C8 1.366(5) . ? N3 C8 1.420(7) 24 ? N3 C7 1.449(7) 24 ? N3 C1 1.519(8) 24 ? C7 C7 0.580(16) 24 ? C7 N2 1.285(5) . ? C7 N2 1.377(6) 24 ? C7 N3 1.449(7) 24 ? C7 H7A 0.9635 . ? N2 N2 0.426(15) 24 ? N2 C7 1.377(6) 24 ? N2 N1 1.399(4) . ? N1 C8 1.287(5) . ? N1 C8 1.287(5) 24 ? N1 N2 1.399(4) 24 ? C8 C8 0.32(3) 24 ? C8 N3 1.420(7) 24 ? C8 H8A 0.9636 . ? N6 N6 0.577(19) 24 ? N6 C10 1.321(6) . ? N6 C9 1.384(8) . ? N6 C3 1.584(9) 24 ? N6 C9 1.614(10) 24 ? C9 C9 1.19(2) 24 ? C9 N5 1.295(8) . ? C9 N6 1.614(10) 24 ? C9 N5 1.705(10) 24 ? C9 H9A 0.9643 . ? N5 N5 1.032(15) 24 ? N5 N4 1.485(6) . ? N5 C9 1.706(10) 24 ? N4 C10 1.247(5) . ? N4 N5 1.485(6) 24 ? N4 Cd2 2.289(4) 13_554 ? C10 N6 1.321(6) 24 ? C10 H10A 0.9722 . ? N7 N7 0.27(2) 25_565 ? N7 O1 0.944(15) 25_565 ? N7 O1 1.217(13) . ? N7 O2 1.239(11) . ? N7 O2 1.239(11) 3_565 ? N7 O2 1.239(11) 2_665 ? N7 O3 1.272(12) . ? N7 O3 1.272(12) 3_565 ? N7 O3 1.272(12) 2_665 ? N7 O2 1.415(13) 25_565 ? N7 O2 1.415(13) 27 ? N7 O2 1.415(13) 26_455 ? O1 N7 0.944(15) 25_565 ? O1 O2 1.033(11) 27 ? O1 O2 1.033(11) 25_565 ? O1 O2 1.033(11) 26_455 ? O1 O3 1.188(13) 25_565 ? O1 O3 1.188(13) 27 ? O1 O3 1.188(13) 26_455 ? O2 O1 1.033(11) 25_565 ? O2 O3 1.084(8) 3_565 ? O2 O3 1.084(8) 2_665 ? O2 N7 1.415(13) 25_565 ? O2 O3 1.579(18) 25_565 ? O2 O2 1.746(19) 3_565 ? O2 O2 1.747(18) 2_665 ? O3 O2 1.084(8) 3_565 ? O3 O2 1.084(8) 2_665 ? O3 O1 1.188(13) 25_565 ? O3 N7 1.417(14) 25_565 ? O3 O2 1.579(18) 25_565 ? O3 O3 1.83(2) 27 ? O3 O3 1.83(2) 26_455 ? 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 180.0 . 19 ? N1 Cd1 N1 90.43(10) . 21 ? N1 Cd1 N1 89.57(10) 19 21 ? N1 Cd1 N1 89.57(10) . 3 ? N1 Cd1 N1 90.43(10) 19 3 ? N1 Cd1 N1 180.00(17) 21 3 ? N1 Cd1 N1 89.57(10) . 2 ? N1 Cd1 N1 90.43(10) 19 2 ? N1 Cd1 N1 90.43(10) 21 2 ? N1 Cd1 N1 89.57(10) 3 2 ? N1 Cd1 N1 90.43(10) . 20 ? N1 Cd1 N1 89.57(10) 19 20 ? N1 Cd1 N1 89.57(10) 21 20 ? N1 Cd1 N1 90.43(10) 3 20 ? N1 Cd1 N1 180.00(17) 2 20 ? N4 Cd2 N4 94.49(13) 8 7_445 ? N4 Cd2 N4 94.48(13) 8 9_455 ? N4 Cd2 N4 94.48(13) 7_445 9_455 ? N4 Cd2 N2 92.48(16) 8 3 ? N4 Cd2 N2 84.82(16) 7_445 3 ? N4 Cd2 N2 173.03(17) 9_455 3 ? N4 Cd2 N2 84.82(16) 8 23 ? N4 Cd2 N2 92.48(17) 7_445 23 ? N4 Cd2 N2 173.03(17) 9_455 23 ? N2 Cd2 N2 10.4(4) 3 23 ? N4 Cd2 N2 173.04(17) 8 22 ? N4 Cd2 N2 84.82(16) 7_445 22 ? N4 Cd2 N2 92.48(17) 9_455 22 ? N2 Cd2 N2 80.6(3) 3 22 ? N2 Cd2 N2 88.29(11) 23 22 ? N4 Cd2 N2 84.82(16) 8 . ? N4 Cd2 N2 173.04(17) 7_445 . ? N4 Cd2 N2 92.48(17) 9_455 . ? N2 Cd2 N2 88.28(11) 3 . ? N2 Cd2 N2 80.6(3) 23 . ? N2 Cd2 N2 95.0(3) 22 . ? N4 Cd2 N2 173.03(17) 8 2 ? N4 Cd2 N2 92.48(17) 7_445 2 ? N4 Cd2 N2 84.82(16) 9_455 2 ? N2 Cd2 N2 88.29(11) 3 2 ? N2 Cd2 N2 95.0(3) 23 2 ? N2 Cd2 N2 10.4(4) 22 2 ? N2 Cd2 N2 88.28(11) . 2 ? N4 Cd2 N2 92.48(17) 8 24 ? N4 Cd2 N2 173.03(17) 7_445 24 ? N4 Cd2 N2 84.82(16) 9_455 24 ? N2 Cd2 N2 95.0(3) 3 24 ? N2 Cd2 N2 88.29(11) 23 24 ? N2 Cd2 N2 88.28(11) 22 24 ? N2 Cd2 N2 10.4(4) . 24 ? N2 Cd2 N2 80.6(3) 2 24 ? C1 C1 C6 107.9(7) 24 . ? C1 C1 C2 80.2(6) 24 . ? C6 C1 C2 120.3(5) . . ? C1 C1 N3 84.9(6) 24 . ? C6 C1 N3 120.1(5) . . ? C2 C1 N3 119.5(4) . . ? C1 C1 C2 70.3(6) 24 24 ? C6 C1 C2 122.4(5) . 24 ? C2 C1 C2 10.0(9) . 24 ? N3 C1 C2 117.0(5) . 24 ? C1 C1 N3 67.0(5) 24 24 ? C6 C1 N3 123.9(5) . 24 ? C2 C1 N3 113.7(5) . 24 ? N3 C1 N3 17.9(7) . 24 ? C2 C1 N3 108.4(6) 24 24 ? C1 C1 C6 48.7(5) 24 24 ? C6 C1 C6 59.2(10) . 24 ? C2 C1 C6 104.2(6) . 24 ? N3 C1 C6 108.4(6) . 24 ? C2 C1 C6 96.8(7) 24 24 ? N3 C1 C6 95.0(6) 24 24 ? C2 C2 C1 99.8(6) 24 . ? C2 C2 C3 101.6(6) 24 . ? C1 C2 C3 118.1(5) . . ? C2 C2 C1 70.3(6) 24 24 ? C1 C2 C1 29.5(8) . 24 ? C3 C2 C1 123.3(5) . 24 ? C2 C2 C3 68.6(7) 24 24 ? C1 C2 C3 122.8(5) . 24 ? C3 C2 C3 32.9(8) . 24 ? C1 C2 C3 109.6(7) 24 24 ? C2 C2 H2A 64.3 24 . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 121.0 . . ? C1 C2 H2A 105.8 24 . ? C3 C2 H2A 104.4 24 . ? C3 C3 C4 111.4(7) 24 . ? C3 C3 C2 78.4(6) 24 . ? C4 C3 C2 122.6(6) . . ? C3 C3 N6 85.3(5) 24 . ? C4 C3 N6 119.1(6) . . ? C2 C3 N6 118.0(5) . . ? C3 C3 C2 68.7(7) 24 24 ? C4 C3 C2 125.1(5) . 24 ? C2 C3 C2 9.8(9) . 24 ? N6 C3 C2 115.6(5) . 24 ? C3 C3 N6 64.1(5) 24 24 ? C4 C3 N6 124.9(6) . 24 ? C2 C3 N6 110.5(6) . 24 ? N6 C3 N6 21.3(7) . 24 ? C2 C3 N6 104.9(6) 24 24 ? C3 C3 C4 44.3(4) 24 24 ? C4 C3 C4 67.1(9) . 24 ? C2 C3 C4 101.8(6) . 24 ? N6 C3 C4 106.5(6) . 24 ? C2 C3 C4 94.1(7) 24 24 ? N6 C3 C4 89.8(6) 24 24 ? C5 C4 C3 116.9(7) . . ? C5 C4 C4 99.4(9) . 24 ? C3 C4 C4 68.6(7) . 24 ? C5 C4 C3 114.3(8) . 24 ? C3 C4 C3 24.3(7) . 24 ? C4 C4 C3 44.3(4) 24 24 ? C5 C4 H4A 121.7 . . ? C3 C4 H4A 120.6 . . ? C4 C4 H4A 109.5 24 . ? C3 C4 H4A 121.9 24 . ? C4 C5 C6 121.6(8) . . ? C4 C5 H5A 118.3 . . ? C6 C5 H5A 118.8 . . ? C1 C6 C5 120.0(7) . . ? C1 C6 C6 72.1(7) . 24 ? C5 C6 C6 105.0(9) . 24 ? C1 C6 C1 23.5(7) . 24 ? C5 C6 C1 120.1(8) . 24 ? C6 C6 C1 48.7(5) 24 24 ? C1 C6 H6A 118.2 . . ? C5 C6 H6A 118.5 . . ? C6 C6 H6A 110.1 24 . ? C1 C6 H6A 121.1 24 . ? N3 N3 C7 92.4(5) 24 . ? N3 N3 C8 86.9(7) 24 . ? C7 N3 C8 104.2(4) . . ? N3 N3 C1 95.1(6) 24 . ? C7 N3 C1 125.7(4) . . ? C8 N3 C1 129.8(4) . . ? N3 N3 C8 73.8(7) 24 24 ? C7 N3 C8 104.2(4) . 24 ? C8 N3 C8 13.1(12) . 24 ? C1 N3 C8 129.5(4) . 24 ? N3 N3 C7 68.8(5) 24 24 ? C7 N3 C7 23.6(6) . 24 ? C8 N3 C7 102.0(4) . 24 ? C1 N3 C7 125.4(4) . 24 ? C8 N3 C7 96.8(5) 24 24 ? N3 N3 C1 67.0(5) 24 24 ? C7 N3 C1 124.0(5) . 24 ? C8 N3 C1 124.5(6) . 24 ? C1 N3 C1 28.1(8) . 24 ? C8 N3 C1 117.1(6) 24 24 ? C7 N3 C1 111.4(6) 24 24 ? C7 C7 N2 86.6(5) 24 . ? C7 C7 N3 87.6(5) 24 . ? N2 C7 N3 110.3(3) . . ? C7 C7 N2 68.6(5) 24 24 ? N2 C7 N2 18.0(6) . 24 ? N3 C7 N2 108.1(4) . 24 ? C7 C7 N3 68.8(5) 24 24 ? N2 C7 N3 107.7(4) . 24 ? N3 C7 N3 18.8(8) . 24 ? N2 C7 N3 99.9(4) 24 24 ? C7 C7 H7A 94.2 24 . ? N2 C7 H7A 125.5 . . ? N3 C7 H7A 124.2 . . ? N2 C7 H7A 124.4 24 . ? N3 C7 H7A 123.2 24 . ? N2 N2 C7 93.4(5) 24 . ? N2 N2 C7 68.6(4) 24 24 ? C7 N2 C7 24.9(7) . 24 ? N2 N2 N1 81.3(3) 24 . ? C7 N2 N1 108.0(3) . . ? C7 N2 N1 102.9(4) 24 . ? N2 N2 Cd2 84.78(19) 24 . ? C7 N2 Cd2 124.0(3) . . ? C7 N2 Cd2 118.9(3) 24 . ? N1 N2 Cd2 126.7(3) . . ? C8 N1 C8 14.4(13) . 24 ? C8 N1 N2 105.3(3) . . ? C8 N1 N2 107.6(3) 24 . ? C8 N1 N2 107.6(3) . 24 ? C8 N1 N2 105.3(3) 24 24 ? N2 N1 N2 17.5(6) . 24 ? C8 N1 Cd1 129.1(3) . . ? C8 N1 Cd1 129.1(3) 24 . ? N2 N1 Cd1 123.3(2) . . ? N2 N1 Cd1 123.3(2) 24 . ? C8 C8 N1 82.8(7) 24 . ? C8 C8 N3 93.1(7) 24 . ? N1 C8 N3 111.1(3) . . ? C8 C8 N3 73.8(7) 24 24 ? N1 C8 N3 107.8(5) . 24 ? N3 C8 N3 19.2(8) . 24 ? C8 C8 H8A 98.1 24 . ? N1 C8 H8A 124.1 . . ? N3 C8 H8A 124.5 . . ? N3 C8 H8A 126.3 24 . ? N6 N6 C10 77.4(4) 24 . ? N6 N6 C9 102.9(6) 24 . ? C10 N6 C9 103.2(4) . . ? N6 N6 C3 94.7(5) 24 . ? C10 N6 C3 131.8(5) . . ? C9 N6 C3 124.8(5) . . ? N6 N6 C3 64.0(5) 24 24 ? C10 N6 C3 119.3(6) . 24 ? C9 N6 C3 129.0(5) . 24 ? C3 N6 C3 30.6(8) . 24 ? N6 N6 C9 56.7(4) 24 24 ? C10 N6 C9 91.9(5) . 24 ? C9 N6 C9 46.2(8) . 24 ? C3 N6 C9 123.3(5) . 24 ? C3 N6 C9 102.4(6) 24 24 ? C9 C9 N5 86.4(6) 24 . ? C9 C9 N6 77.1(6) 24 . ? N5 C9 N6 112.0(6) . . ? C9 C9 N6 56.7(4) 24 24 ? N5 C9 N6 107.4(6) . 24 ? N6 C9 N6 20.4(7) . 24 ? C9 C9 N5 49.3(4) 24 24 ? N5 C9 N5 37.1(6) . 24 ? N6 C9 N5 98.6(6) . 24 ? N6 C9 N5 84.0(6) 24 24 ? C9 C9 H9A 112.3 24 . ? N5 C9 H9A 122.5 . . ? N6 C9 H9A 124.8 . . ? N6 C9 H9A 128.7 24 . ? N5 C9 H9A 129.6 24 . ? N5 N5 C9 93.6(6) 24 . ? N5 N5 N4 69.7(3) 24 . ? C9 N5 N4 103.7(5) . . ? N5 N5 C9 49.2(4) 24 24 ? C9 N5 C9 44.4(7) . 24 ? N4 N5 C9 86.3(4) . 24 ? C10 N4 N5 105.0(4) . 24 ? C10 N4 N5 105.0(4) . . ? N5 N4 N5 40.6(6) 24 . ? C10 N4 Cd2 139.8(3) . 13_554 ? N5 N4 Cd2 112.6(3) 24 13_554 ? N5 N4 Cd2 112.6(3) . 13_554 ? N4 C10 N6 115.6(4) . . ? N4 C10 N6 115.6(4) . 24 ? N6 C10 N6 25.2(8) . 24 ? N4 C10 H10A 121.1 . . ? N6 C10 H10A 121.9 . . ? N6 C10 H10A 111.2 24 . ? N7 N7 O1 0.040(6) 25_565 . ? O1 N7 O1 180.0 25_565 . ? N7 N7 O2 125.5(7) 25_565 . ? O1 N7 O2 54.5(7) 25_565 . ? O1 N7 O2 125.5(7) . . ? N7 N7 O2 125.5(7) 25_565 3_565 ? O1 N7 O2 54.5(7) 25_565 3_565 ? O1 N7 O2 125.5(7) . 3_565 ? O2 N7 O2 89.6(9) . 3_565 ? N7 N7 O2 125.5(6) 25_565 2_665 ? O1 N7 O2 54.5(7) 25_565 2_665 ? O1 N7 O2 125.5(7) . 2_665 ? O2 N7 O2 89.6(9) . 2_665 ? O2 N7 O2 89.6(9) 3_565 2_665 ? N7 N7 O3 117.2(8) 25_565 . ? O1 N7 O3 62.8(8) 25_565 . ? O1 N7 O3 117.2(8) . . ? O2 N7 O3 117.3(11) . . ? O2 N7 O3 51.1(4) 3_565 . ? O2 N7 O3 51.1(4) 2_665 . ? N7 N7 O3 117.2(8) 25_565 3_565 ? O1 N7 O3 62.8(7) 25_565 3_565 ? O1 N7 O3 117.2(8) . 3_565 ? O2 N7 O3 51.1(4) . 3_565 ? O2 N7 O3 117.3(11) 3_565 3_565 ? O2 N7 O3 51.1(4) 2_665 3_565 ? O3 N7 O3 100.8(9) . 3_565 ? N7 N7 O3 117.2(8) 25_565 2_665 ? O1 N7 O3 62.8(7) 25_565 2_665 ? O1 N7 O3 117.2(7) . 2_665 ? O2 N7 O3 51.1(4) . 2_665 ? O2 N7 O3 51.1(4) 3_565 2_665 ? O2 N7 O3 117.3(11) 2_665 2_665 ? O3 N7 O3 100.8(9) . 2_665 ? O3 N7 O3 100.8(9) 3_565 2_665 ? N7 N7 O2 45.4(6) 25_565 25_565 ? O1 N7 O2 134.6(6) 25_565 25_565 ? O1 N7 O2 45.4(6) . 25_565 ? O2 N7 O2 170.9(7) . 25_565 ? O2 N7 O2 96.8(7) 3_565 25_565 ? O2 N7 O2 96.8(7) 2_665 25_565 ? O3 N7 O2 71.8(7) . 25_565 ? O3 N7 O2 129.6(4) 3_565 25_565 ? O3 N7 O2 129.6(4) 2_665 25_565 ? N7 N7 O2 45.4(6) 25_565 27 ? O1 N7 O2 134.6(6) 25_565 27 ? O1 N7 O2 45.4(6) . 27 ? O2 N7 O2 96.8(7) . 27 ? O2 N7 O2 171.0(7) 3_565 27 ? O2 N7 O2 96.8(7) 2_665 27 ? O3 N7 O2 129.6(4) . 27 ? O3 N7 O2 71.8(7) 3_565 27 ? O3 N7 O2 129.6(4) 2_665 27 ? O2 N7 O2 76.2(9) 25_565 27 ? N7 N7 O2 45.5(6) 25_565 26_455 ? O1 N7 O2 134.6(6) 25_565 26_455 ? O1 N7 O2 45.4(6) . 26_455 ? O2 N7 O2 96.8(7) . 26_455 ? O2 N7 O2 96.8(7) 3_565 26_455 ? O2 N7 O2 170.9(7) 2_665 26_455 ? O3 N7 O2 129.6(4) . 26_455 ? O3 N7 O2 129.6(4) 3_565 26_455 ? O3 N7 O2 71.8(7) 2_665 26_455 ? O2 N7 O2 76.2(9) 25_565 26_455 ? O2 N7 O2 76.2(9) 27 26_455 ? N7 O1 O2 77.5(8) 25_565 27 ? N7 O1 O2 77.5(8) 25_565 25_565 ? O2 O1 O2 115.4(6) 27 25_565 ? N7 O1 O2 77.5(8) 25_565 26_455 ? O2 O1 O2 115.4(6) 27 26_455 ? O2 O1 O2 115.4(6) 25_565 26_455 ? N7 O1 O3 72.2(8) 25_565 25_565 ? O2 O1 O3 57.9(2) 27 25_565 ? O2 O1 O3 149.7(14) 25_565 25_565 ? O2 O1 O3 57.9(2) 26_455 25_565 ? N7 O1 O3 72.2(8) 25_565 27 ? O2 O1 O3 149.7(14) 27 27 ? O2 O1 O3 57.9(2) 25_565 27 ? O2 O1 O3 57.9(2) 26_455 27 ? O3 O1 O3 111.1(7) 25_565 27 ? N7 O1 O3 72.2(8) 25_565 26_455 ? O2 O1 O3 57.9(2) 27 26_455 ? O2 O1 O3 57.9(2) 25_565 26_455 ? O2 O1 O3 149.7(14) 26_455 26_455 ? O3 O1 O3 111.1(7) 25_565 26_455 ? O3 O1 O3 111.1(7) 27 26_455 ? N7 O1 N7 0.012(1) 25_565 . ? O2 O1 N7 77.5(8) 27 . ? O2 O1 N7 77.5(8) 25_565 . ? O2 O1 N7 77.5(8) 26_455 . ? O3 O1 N7 72.2(8) 25_565 . ? O3 O1 N7 72.2(8) 27 . ? O3 O1 N7 72.2(8) 26_455 . ? O1 O2 O3 68.2(9) 25_565 3_565 ? O1 O2 O3 68.2(9) 25_565 2_665 ? O3 O2 O3 129.3(14) 3_565 2_665 ? O1 O2 N7 48.0(8) 25_565 . ? O3 O2 N7 66.0(7) 3_565 . ? O3 O2 N7 66.0(7) 2_665 . ? O1 O2 N7 57.1(7) 25_565 25_565 ? O3 O2 N7 67.6(7) 3_565 25_565 ? O3 O2 N7 67.6(7) 2_665 25_565 ? N7 O2 N7 9.0(7) . 25_565 ? O1 O2 O3 107.0(10) 25_565 25_565 ? O3 O2 O3 84.5(8) 3_565 25_565 ? O3 O2 O3 84.5(8) 2_665 25_565 ? N7 O2 O3 58.9(7) . 25_565 ? N7 O2 O3 49.9(6) 25_565 25_565 ? O1 O2 O2 32.3(3) 25_565 3_565 ? O3 O2 O2 95.6(8) 3_565 3_565 ? O3 O2 O2 36.3(8) 2_665 3_565 ? N7 O2 O2 45.2(5) . 3_565 ? N7 O2 O2 51.9(4) 25_565 3_565 ? O3 O2 O2 93.9(6) 25_565 3_565 ? O1 O2 O2 32.3(3) 25_565 2_665 ? O3 O2 O2 36.3(8) 3_565 2_665 ? O3 O2 O2 95.6(8) 2_665 2_665 ? N7 O2 O2 45.2(5) . 2_665 ? N7 O2 O2 51.9(4) 25_565 2_665 ? O3 O2 O2 93.9(6) 25_565 2_665 ? O2 O2 O2 59.999(3) 3_565 2_665 ? O2 O3 O2 107.3(17) 3_565 2_665 ? O2 O3 O1 53.9(9) 3_565 25_565 ? O2 O3 O1 53.8(9) 2_665 25_565 ? O2 O3 N7 62.9(7) 3_565 . ? O2 O3 N7 62.9(7) 2_665 . ? O1 O3 N7 45.0(8) 25_565 . ? O2 O3 N7 67.4(7) 3_565 25_565 ? O2 O3 N7 67.4(7) 2_665 25_565 ? O1 O3 N7 54.8(6) 25_565 25_565 ? N7 O3 N7 9.9(8) . 25_565 ? O2 O3 O2 94.7(8) 3_565 25_565 ? O2 O3 O2 94.7(8) 2_665 25_565 ? O1 O3 O2 103.3(10) 25_565 25_565 ? N7 O3 O2 58.4(7) . 25_565 ? N7 O3 O2 48.5(6) 25_565 25_565 ? O2 O3 O3 59.3(6) 3_565 27 ? O2 O3 O3 110.7(8) 2_665 27 ? O1 O3 O3 86.9(5) 25_565 27 ? N7 O3 O3 50.6(5) . 27 ? N7 O3 O3 43.9(5) 25_565 27 ? O2 O3 O3 36.2(5) 25_565 27 ? O2 O3 O3 110.7(8) 3_565 26_455 ? O2 O3 O3 59.3(6) 2_665 26_455 ? O1 O3 O3 86.9(5) 25_565 26_455 ? N7 O3 O3 50.6(5) . 26_455 ? N7 O3 O3 43.9(5) 25_565 26_455 ? O2 O3 O3 36.2(5) 25_565 26_455 ? O3 O3 O3 64.8(10) 27 26_455 ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.007 0.291 -0.008 2524 984 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.744 _refine_diff_density_min -0.790 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 917440'