# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Zhu, Lei' 'Shatruk, Michael' _publ_contact_author_name 'Zhu, Lei' _publ_contact_author_email lzhu@chem.fsu.edu _publ_section_title ; Tridentate Complexes of 2,6-Bis(4-substituted-1,2,3-triazol-1-ylmethyl)pyridine and its Organic Azide Precursors - an Application of the Copper(II) Acetate-Accelerated Azide-Alkyne Cycloaddition ; data_zhu37 _database_code_depnum_ccdc_archive 'CCDC 762781' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl4 Cu2 N8' _chemical_formula_sum 'C12 H12 Cl4 Cu2 N8' _chemical_formula_weight 537.18 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8184(3) _cell_length_b 8.0206(3) _cell_length_c 9.7388(3) _cell_angle_alpha 68.0600(10) _cell_angle_beta 71.7100(10) _cell_angle_gamma 89.3780(10) _cell_volume 465.63(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5967 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 33.06 _exptl_crystal_description irregular _exptl_crystal_colour green _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 266 _exptl_absorpt_coefficient_mu 2.872 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.457 _exptl_absorpt_correction_T_max 0.563 _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_reflns_number 6699 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.25 _reflns_number_total 2249 _reflns_number_gt 2171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 2249 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0504 _refine_ls_wR_factor_gt 0.0503 _refine_ls_goodness_of_fit_ref 2.709 _refine_ls_restrained_S_all 2.709 _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 Cu1 Cu 0.79596(3) 0.08118(3) 0.43876(2) 0.01678(7) Uani 1 1 d . . . N1 N 0.7650(2) 0.14757(19) 0.22496(16) 0.0168(3) Uani 1 1 d . . . N2 N 0.6936(2) -0.16228(19) 0.45064(16) 0.0211(3) Uani 1 1 d . . . N3 N 0.6593(2) -0.3104(2) 0.56641(17) 0.0194(3) Uani 1 1 d . . . N4 N 0.6255(3) -0.4349(2) 0.67614(18) 0.0270(4) Uani 1 1 d . . . C1 C 0.7881(3) 0.3196(2) 0.1184(2) 0.0229(4) Uani 1 1 d . . . H1 H 0.8067 0.4168 0.1482 0.027 Uiso 1 1 calc R . . C2 C 0.7858(3) 0.3588(3) -0.0307(2) 0.0262(4) Uani 1 1 d . . . H2 H 0.8010 0.4810 -0.1021 0.031 Uiso 1 1 calc R . . C3 C 0.7609(3) 0.2182(3) -0.0760(2) 0.0246(4) Uani 1 1 d . . . H3 H 0.7599 0.2422 -0.1790 0.030 Uiso 1 1 calc R . . C4 C 0.7374(3) 0.0425(2) 0.0316(2) 0.0222(4) Uani 1 1 d . . . H4 H 0.7218 -0.0564 0.0031 0.027 Uiso 1 1 calc R . . C5 C 0.7367(3) 0.0115(2) 0.1817(2) 0.0175(3) Uani 1 1 d . . . C6 C 0.7041(3) -0.1778(2) 0.30229(19) 0.0220(4) Uani 1 1 d . . . H6A H 0.5731 -0.2431 0.3149 0.026 Uiso 1 1 calc R . . H6B H 0.8208 -0.2448 0.2703 0.026 Uiso 1 1 calc R . . Cl1 Cl 0.82604(7) 0.36269(6) 0.42883(5) 0.02384(11) Uani 1 1 d . . . Cl2 Cl 0.79679(7) -0.04836(6) 0.68895(5) 0.02113(11) 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 Cu1 0.01959(13) 0.01670(12) 0.01639(12) -0.00723(9) -0.00809(9) 0.00158(9) N1 0.0156(8) 0.0179(7) 0.0168(7) -0.0057(6) -0.0064(6) 0.0007(6) N2 0.0316(9) 0.0151(8) 0.0149(7) -0.0028(6) -0.0092(7) -0.0025(7) N3 0.0195(8) 0.0206(8) 0.0218(8) -0.0107(7) -0.0089(7) 0.0028(6) N4 0.0349(10) 0.0216(9) 0.0237(8) -0.0047(7) -0.0137(8) 0.0025(7) C1 0.0237(10) 0.0205(10) 0.0244(10) -0.0070(8) -0.0100(8) -0.0003(8) C2 0.0308(11) 0.0218(10) 0.0207(9) -0.0002(8) -0.0114(8) 0.0012(8) C3 0.0244(10) 0.0319(11) 0.0180(9) -0.0081(8) -0.0094(8) 0.0036(8) C4 0.0230(10) 0.0274(10) 0.0195(9) -0.0120(8) -0.0083(8) 0.0037(8) C5 0.0143(9) 0.0208(9) 0.0179(8) -0.0083(7) -0.0051(7) 0.0026(7) C6 0.0288(11) 0.0214(9) 0.0173(9) -0.0096(8) -0.0069(8) 0.0014(8) Cl1 0.0286(3) 0.0193(2) 0.0281(2) -0.01271(19) -0.0111(2) 0.00330(19) Cl2 0.0222(2) 0.0275(2) 0.0163(2) -0.01043(18) -0.00764(18) 0.00451(18) _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 Cu1 N1 2.0270(13) . ? Cu1 N2 2.0305(14) . ? Cu1 Cl1 2.2325(4) . ? Cu1 Cl2 2.2656(4) . ? Cu1 Cl2 2.7181(5) 2_756 ? N1 C5 1.344(2) . ? N1 C1 1.355(2) . ? N2 N3 1.256(2) . ? N2 C6 1.476(2) . ? N3 N4 1.116(2) . ? C1 C2 1.372(2) . ? C1 H1 0.9500 . ? C2 C3 1.385(2) . ? C2 H2 0.9500 . ? C3 C4 1.381(2) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C6 1.498(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? Cl2 Cu1 2.7181(5) 2_756 ? 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 Cu1 N2 77.98(5) . . ? N1 Cu1 Cl1 96.94(4) . . ? N2 Cu1 Cl1 165.46(5) . . ? N1 Cu1 Cl2 168.33(4) . . ? N2 Cu1 Cl2 90.52(4) . . ? Cl1 Cu1 Cl2 93.770(17) . . ? N1 Cu1 Cl2 88.91(4) . 2_756 ? N2 Cu1 Cl2 93.69(5) . 2_756 ? Cl1 Cu1 Cl2 99.879(17) . 2_756 ? Cl2 Cu1 Cl2 93.801(15) . 2_756 ? C5 N1 C1 118.04(14) . . ? C5 N1 Cu1 117.51(11) . . ? C1 N1 Cu1 124.21(11) . . ? N3 N2 C6 114.82(14) . . ? N3 N2 Cu1 126.00(10) . . ? C6 N2 Cu1 117.71(11) . . ? N4 N3 N2 174.81(16) . . ? N1 C1 C2 122.57(16) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.26(17) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 118.59(16) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 119.47(16) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 122.03(16) . . ? N1 C5 C6 117.48(14) . . ? C4 C5 C6 120.49(15) . . ? N2 C6 C5 106.63(13) . . ? N2 C6 H6A 110.4 . . ? C5 C6 H6A 110.4 . . ? N2 C6 H6B 110.4 . . ? C5 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? Cu1 Cl2 Cu1 86.199(15) . 2_756 ? 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 N2 Cu1 N1 C5 -12.31(12) . . . . ? Cl1 Cu1 N1 C5 -178.48(12) . . . . ? Cl2 Cu1 N1 C5 -21.9(3) . . . . ? Cl2 Cu1 N1 C5 81.70(12) 2_756 . . . ? N2 Cu1 N1 C1 173.40(15) . . . . ? Cl1 Cu1 N1 C1 7.22(14) . . . . ? Cl2 Cu1 N1 C1 163.78(15) . . . . ? Cl2 Cu1 N1 C1 -92.60(14) 2_756 . . . ? N1 Cu1 N2 N3 -179.18(16) . . . . ? Cl1 Cu1 N2 N3 -108.37(18) . . . . ? Cl2 Cu1 N2 N3 -1.12(15) . . . . ? Cl2 Cu1 N2 N3 92.72(15) 2_756 . . . ? N1 Cu1 N2 C6 15.43(12) . . . . ? Cl1 Cu1 N2 C6 86.2(2) . . . . ? Cl2 Cu1 N2 C6 -166.50(12) . . . . ? Cl2 Cu1 N2 C6 -72.66(13) 2_756 . . . ? C5 N1 C1 C2 -0.7(3) . . . . ? Cu1 N1 C1 C2 173.59(13) . . . . ? N1 C1 C2 C3 -0.6(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C1 N1 C5 C4 2.1(2) . . . . ? Cu1 N1 C5 C4 -172.55(13) . . . . ? C1 N1 C5 C6 -177.97(15) . . . . ? Cu1 N1 C5 C6 7.4(2) . . . . ? C3 C4 C5 N1 -2.2(3) . . . . ? C3 C4 C5 C6 177.87(16) . . . . ? N3 N2 C6 C5 177.66(14) . . . . ? Cu1 N2 C6 C5 -15.34(19) . . . . ? N1 C5 C6 N2 4.9(2) . . . . ? C4 C5 C6 N2 -175.13(15) . . . . ? N1 Cu1 Cl2 Cu1 103.1(2) . . . 2_756 ? N2 Cu1 Cl2 Cu1 93.73(4) . . . 2_756 ? Cl1 Cu1 Cl2 Cu1 -100.177(16) . . . 2_756 ? Cl2 Cu1 Cl2 Cu1 0.0 2_756 . . 2_756 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.279 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.085 data_zhu7 _database_code_depnum_ccdc_archive 'CCDC 762783' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 Cl Cu N6, Cl O4' _chemical_formula_sum 'C22 H22 Cl2 Cu N6 O4' _chemical_formula_weight 568.90 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.8646(15) _cell_length_b 7.5283(7) _cell_length_c 18.9900(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.990(2) _cell_angle_gamma 90.00 _cell_volume 2339.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6018 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.27 _exptl_crystal_description tetragonal _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 1.205 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.7137 _exptl_absorpt_correction_T_max 0.9312 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27253 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4787 _reflns_number_gt 4194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+2.1237P] 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 4787 _refine_ls_number_parameters 353 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.167 _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 Cu1 Cu 0.876657(19) 0.91818(4) -0.050946(17) 0.01425(11) Uani 1 1 d . . . C1 C 0.93702(17) 0.7096(4) 0.08594(16) 0.0199(6) Uani 1 1 d . . . H1 H 0.9489 0.6178 0.0557 0.024 Uiso 1 1 calc R . . C2 C 0.95372(18) 0.6817(4) 0.15967(16) 0.0239(6) Uani 1 1 d . . . H2 H 0.9762 0.5721 0.1799 0.029 Uiso 1 1 calc R . . C3 C 0.93723(19) 0.8158(4) 0.20375(17) 0.0271(7) Uani 1 1 d . . . H3 H 0.9490 0.8002 0.2549 0.033 Uiso 1 1 calc R . . C4 C 0.90328(18) 0.9731(4) 0.17259(16) 0.0259(7) Uani 1 1 d . . . H4 H 0.8917 1.0671 0.2020 0.031 Uiso 1 1 calc R . . C5 C 0.88634(16) 0.9913(4) 0.09759(15) 0.0180(6) Uani 1 1 d . . . C6 C 0.84922(19) 1.1599(4) 0.06104(15) 0.0201(6) Uani 1 1 d . . . H6A H 0.8013 1.1924 0.0798 0.024 Uiso 1 1 calc R . . H6B H 0.8897 1.2572 0.0735 0.024 Uiso 1 1 calc R . . C7 C 0.85141(17) 1.2926(4) -0.05739(15) 0.0180(6) Uani 1 1 d . . . H7A H 0.9077 1.3268 -0.0319 0.022 Uiso 1 1 calc R . . H7B H 0.8153 1.3966 -0.0581 0.022 Uiso 1 1 calc R . . C8 C 0.84922(16) 1.2352(4) -0.13389(15) 0.0177(6) Uani 1 1 d . . . C9 C 0.83444(18) 1.3509(4) -0.19200(16) 0.0241(6) Uani 1 1 d . . . H9 H 0.8226 1.4724 -0.1857 0.029 Uiso 1 1 calc R . . C10 C 0.8372(2) 1.2869(4) -0.25950(17) 0.0288(7) Uani 1 1 d . . . H10 H 0.8269 1.3641 -0.3003 0.035 Uiso 1 1 calc R . . C11 C 0.85482(19) 1.1098(4) -0.26739(17) 0.0272(7) Uani 1 1 d . . . H11 H 0.8576 1.0640 -0.3133 0.033 Uiso 1 1 calc R . . C12 C 0.86838(18) 1.0007(4) -0.20721(16) 0.0220(6) Uani 1 1 d . . . H12 H 0.8803 0.8788 -0.2125 0.026 Uiso 1 1 calc R . . C13 C 0.73256(17) 1.1253(4) -0.04487(16) 0.0191(6) Uani 1 1 d . . . H13A H 0.7057 1.2086 -0.0175 0.023 Uiso 1 1 calc R . . H13B H 0.7153 1.1566 -0.0970 0.023 Uiso 1 1 calc R . . C14 C 0.70703(16) 0.9399(4) -0.03400(15) 0.0164(6) Uani 1 1 d . . . C15 C 0.64670(17) 0.8686(4) -0.00549(15) 0.0181(6) Uani 1 1 d . . . H15 H 0.6086 0.9297 0.0153 0.022 Uiso 1 1 calc R . . C16 C 0.60756(17) 0.5512(4) 0.01107(16) 0.0212(6) Uani 1 1 d . . . H16A H 0.5890 0.4645 -0.0287 0.025 Uiso 1 1 calc R . . H16B H 0.5584 0.6033 0.0229 0.025 Uiso 1 1 calc R . . C17 C 0.65719(17) 0.4556(4) 0.07703(15) 0.0178(6) Uani 1 1 d . . . C18 C 0.62787(19) 0.2941(4) 0.09624(17) 0.0233(6) Uani 1 1 d . . . H18 H 0.5786 0.2460 0.0673 0.028 Uiso 1 1 calc R . . C19 C 0.6702(2) 0.2029(4) 0.15746(17) 0.0271(7) Uani 1 1 d . . . H19 H 0.6496 0.0933 0.1704 0.033 Uiso 1 1 calc R . . C20 C 0.74227(19) 0.2714(4) 0.19958(16) 0.0254(7) Uani 1 1 d . . . H20 H 0.7712 0.2094 0.2415 0.031 Uiso 1 1 calc R . . C21 C 0.77206(19) 0.4314(4) 0.18018(16) 0.0240(6) Uani 1 1 d . . . H21 H 0.8218 0.4784 0.2086 0.029 Uiso 1 1 calc R . . C22 C 0.72943(18) 0.5227(4) 0.11954(16) 0.0214(6) Uani 1 1 d . . . H22 H 0.7500 0.6326 0.1069 0.026 Uiso 1 1 calc R . . N1 N 0.90431(14) 0.8631(3) 0.05494(12) 0.0165(5) Uani 1 1 d . . . N2 N 0.86521(14) 1.0613(3) -0.14145(13) 0.0175(5) Uani 1 1 d . . . N3 N 0.82328(13) 1.1420(3) -0.01915(12) 0.0152(5) Uani 1 1 d . . . N4 N 0.74719(14) 0.8043(3) -0.05739(12) 0.0168(5) Uani 1 1 d . . . N5 N 0.71478(14) 0.6517(3) -0.04448(13) 0.0179(5) Uani 1 1 d . . . N6 N 0.65387(14) 0.6917(3) -0.01365(13) 0.0168(5) Uani 1 1 d . . . Cl1 Cl 0.94718(4) 0.69545(9) -0.08479(4) 0.02098(17) Uani 1 1 d . . . Cl2 Cl 0.50782(5) 0.17913(13) 0.84842(4) 0.0369(2) Uani 1 1 d D . . O1A O 0.5174(10) 0.162(2) 0.9244(5) 0.042(3) Uani 0.650(13) 1 d PD A 1 O2A O 0.4279(5) 0.2161(16) 0.8132(5) 0.069(3) Uani 0.650(13) 1 d PD A 1 O3A O 0.5254(5) -0.0056(10) 0.8284(3) 0.092(3) Uani 0.650(13) 1 d PD A 1 O4A O 0.5705(5) 0.2827(16) 0.8406(4) 0.105(4) Uani 0.650(13) 1 d PD A 1 O1B O 0.4996(19) 0.135(5) 0.9188(9) 0.041(6) Uani 0.350(13) 1 d PD A 2 O2B O 0.4380(8) 0.164(3) 0.7917(8) 0.057(5) Uani 0.350(13) 1 d PD A 2 O3B O 0.5758(7) 0.147(3) 0.8192(6) 0.087(7) Uani 0.350(13) 1 d PD A 2 O4B O 0.5149(10) 0.3857(12) 0.8467(5) 0.070(5) Uani 0.350(13) 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01652(18) 0.00900(17) 0.01780(19) 0.00039(12) 0.00525(13) 0.00204(12) C1 0.0177(14) 0.0158(14) 0.0263(15) 0.0036(11) 0.0052(12) 0.0019(11) C2 0.0199(15) 0.0232(16) 0.0285(16) 0.0098(12) 0.0059(12) 0.0023(12) C3 0.0249(16) 0.0341(18) 0.0218(15) 0.0067(13) 0.0048(12) 0.0011(13) C4 0.0264(16) 0.0293(17) 0.0226(15) -0.0018(13) 0.0070(13) 0.0006(13) C5 0.0151(13) 0.0174(14) 0.0220(14) -0.0016(11) 0.0054(11) -0.0010(11) C6 0.0272(15) 0.0133(13) 0.0219(14) -0.0026(11) 0.0097(12) 0.0005(11) C7 0.0185(14) 0.0097(13) 0.0266(15) 0.0022(11) 0.0071(11) 0.0001(10) C8 0.0145(13) 0.0154(13) 0.0229(14) 0.0002(11) 0.0038(11) -0.0021(11) C9 0.0238(15) 0.0172(14) 0.0291(16) 0.0064(12) 0.0022(13) -0.0007(12) C10 0.0304(17) 0.0297(17) 0.0228(16) 0.0092(13) -0.0003(13) -0.0010(14) C11 0.0286(17) 0.0321(18) 0.0203(15) 0.0010(13) 0.0045(13) -0.0034(13) C12 0.0228(15) 0.0201(15) 0.0226(15) -0.0012(12) 0.0049(12) 0.0009(12) C13 0.0156(14) 0.0126(13) 0.0297(15) 0.0019(11) 0.0069(12) 0.0028(10) C14 0.0146(13) 0.0138(13) 0.0202(14) 0.0013(10) 0.0028(11) 0.0022(10) C15 0.0152(13) 0.0150(13) 0.0239(14) -0.0005(11) 0.0044(11) 0.0033(11) C16 0.0158(13) 0.0155(14) 0.0316(16) 0.0003(12) 0.0047(12) -0.0029(11) C17 0.0186(14) 0.0143(13) 0.0227(14) -0.0034(11) 0.0092(11) 0.0012(11) C18 0.0220(15) 0.0210(15) 0.0282(16) -0.0012(12) 0.0083(12) -0.0055(12) C19 0.0319(17) 0.0234(16) 0.0291(16) 0.0028(13) 0.0134(14) -0.0041(13) C20 0.0291(16) 0.0290(17) 0.0205(15) 0.0026(13) 0.0104(13) 0.0026(13) C21 0.0241(15) 0.0250(16) 0.0233(15) -0.0064(12) 0.0064(12) -0.0013(12) C22 0.0238(15) 0.0151(14) 0.0264(15) -0.0039(12) 0.0087(12) -0.0014(12) N1 0.0159(11) 0.0133(11) 0.0203(12) 0.0021(9) 0.0045(9) 0.0006(9) N2 0.0174(12) 0.0152(12) 0.0206(12) 0.0024(9) 0.0056(9) -0.0005(9) N3 0.0160(11) 0.0100(10) 0.0207(12) 0.0004(9) 0.0069(9) -0.0005(9) N4 0.0154(11) 0.0141(12) 0.0196(12) -0.0005(9) 0.0016(9) 0.0010(9) N5 0.0169(12) 0.0141(11) 0.0222(12) -0.0021(9) 0.0036(10) 0.0002(9) N6 0.0139(11) 0.0144(11) 0.0222(12) 0.0009(9) 0.0048(9) -0.0007(9) Cl1 0.0247(4) 0.0131(3) 0.0269(4) -0.0006(3) 0.0098(3) 0.0057(3) Cl2 0.0227(4) 0.0598(6) 0.0256(4) -0.0080(4) 0.0007(3) -0.0047(4) O1A 0.045(8) 0.040(5) 0.039(4) 0.000(3) 0.004(3) 0.016(5) O2A 0.037(3) 0.095(7) 0.061(5) 0.030(5) -0.014(3) 0.008(3) O3A 0.115(6) 0.082(5) 0.067(4) -0.045(4) 0.002(4) 0.034(5) O4A 0.060(5) 0.166(11) 0.083(5) 0.039(6) 0.004(4) -0.069(7) O1B 0.032(10) 0.059(12) 0.034(7) 0.019(7) 0.010(6) -0.002(7) O2B 0.043(7) 0.072(10) 0.051(8) 0.007(6) 0.000(5) -0.032(7) O3B 0.067(9) 0.146(17) 0.050(6) -0.020(8) 0.019(5) 0.046(11) O4B 0.114(12) 0.043(6) 0.047(6) -0.003(4) 0.005(6) -0.045(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 Cu1 N1 1.995(2) . ? Cu1 N2 1.998(2) . ? Cu1 N3 2.068(2) . ? Cu1 Cl1 2.2380(7) . ? Cu1 N4 2.321(2) . ? C1 N1 1.352(4) . ? C1 C2 1.376(4) . ? C1 H1 0.9500 . ? C2 C3 1.382(5) . ? C2 H2 0.9500 . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 N1 1.341(4) . ? C5 C6 1.508(4) . ? C6 N3 1.485(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3 1.485(3) . ? C7 C8 1.508(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N2 1.351(4) . ? C8 C9 1.380(4) . ? C9 C10 1.380(4) . ? C9 H9 0.9500 . ? C10 C11 1.382(5) . ? C10 H10 0.9500 . ? C11 C12 1.381(4) . ? C11 H11 0.9500 . ? C12 N2 1.343(4) . ? C12 H12 0.9500 . ? C13 C14 1.490(4) . ? C13 N3 1.495(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.358(3) . ? C14 C15 1.372(4) . ? C15 N6 1.349(4) . ? C15 H15 0.9500 . ? C16 N6 1.458(4) . ? C16 C17 1.510(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.384(4) . ? C17 C18 1.394(4) . ? C18 C19 1.390(4) . ? C18 H18 0.9500 . ? C19 C20 1.384(5) . ? C19 H19 0.9500 . ? C20 C21 1.389(4) . ? C20 H20 0.9500 . ? C21 C22 1.384(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N4 N5 1.320(3) . ? N5 N6 1.334(3) . ? Cl2 O4A 1.350(5) . ? Cl2 O2A 1.381(7) . ? Cl2 O2B 1.396(12) . ? Cl2 O3B 1.409(9) . ? Cl2 O1B 1.417(13) . ? Cl2 O1A 1.417(9) . ? Cl2 O3A 1.490(6) . ? Cl2 O4B 1.561(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 N1 Cu1 N2 158.38(10) . . ? N1 Cu1 N3 83.52(9) . . ? N2 Cu1 N3 81.57(9) . . ? N1 Cu1 Cl1 97.06(7) . . ? N2 Cu1 Cl1 96.00(7) . . ? N3 Cu1 Cl1 173.38(7) . . ? N1 Cu1 N4 87.94(9) . . ? N2 Cu1 N4 105.06(9) . . ? N3 Cu1 N4 81.15(8) . . ? Cl1 Cu1 N4 105.45(6) . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.9(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.3(3) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 121.8(3) . . ? N1 C5 C6 117.2(2) . . ? C4 C5 C6 120.9(3) . . ? N3 C6 C5 112.5(2) . . ? N3 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? N3 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? N3 C7 C8 108.4(2) . . ? N3 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? N3 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? N2 C8 C9 121.9(3) . . ? N2 C8 C7 114.9(2) . . ? C9 C8 C7 123.2(3) . . ? C8 C9 C10 118.8(3) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 118.8(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N2 C12 C11 122.1(3) . . ? N2 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C14 C13 N3 109.9(2) . . ? C14 C13 H13A 109.7 . . ? N3 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? N3 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N4 C14 C15 108.1(2) . . ? N4 C14 C13 118.4(2) . . ? C15 C14 C13 133.5(3) . . ? N6 C15 C14 104.2(2) . . ? N6 C15 H15 127.9 . . ? C14 C15 H15 127.9 . . ? N6 C16 C17 112.3(2) . . ? N6 C16 H16A 109.1 . . ? C17 C16 H16A 109.1 . . ? N6 C16 H16B 109.1 . . ? C17 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? C22 C17 C18 118.9(3) . . ? C22 C17 C16 122.9(3) . . ? C18 C17 C16 118.2(3) . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 119.6(3) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.8(3) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? C5 N1 C1 118.7(2) . . ? C5 N1 Cu1 115.32(19) . . ? C1 N1 Cu1 126.0(2) . . ? C12 N2 C8 118.8(2) . . ? C12 N2 Cu1 126.9(2) . . ? C8 N2 Cu1 114.29(19) . . ? C7 N3 C6 112.5(2) . . ? C7 N3 C13 109.1(2) . . ? C6 N3 C13 111.5(2) . . ? C7 N3 Cu1 105.45(16) . . ? C6 N3 Cu1 109.38(16) . . ? C13 N3 Cu1 108.63(16) . . ? N5 N4 C14 109.4(2) . . ? N5 N4 Cu1 137.56(17) . . ? C14 N4 Cu1 104.01(17) . . ? N4 N5 N6 106.4(2) . . ? N5 N6 C15 111.9(2) . . ? N5 N6 C16 120.4(2) . . ? C15 N6 C16 127.5(2) . . ? O4A Cl2 O2A 121.9(6) . . ? O4A Cl2 O2B 120.0(8) . . ? O4A Cl2 O3B 47.5(7) . . ? O2A Cl2 O3B 129.5(7) . . ? O2B Cl2 O3B 107.3(9) . . ? O4A Cl2 O1B 119.9(13) . . ? O2A Cl2 O1B 101.4(14) . . ? O2B Cl2 O1B 116.8(14) . . ? O3B Cl2 O1B 127.2(15) . . ? O4A Cl2 O1A 105.3(8) . . ? O2A Cl2 O1A 111.6(8) . . ? O2B Cl2 O1A 130.2(9) . . ? O3B Cl2 O1A 118.8(8) . . ? O4A Cl2 O3A 107.6(6) . . ? O2A Cl2 O3A 107.2(5) . . ? O2B Cl2 O3A 84.8(8) . . ? O3B Cl2 O3A 60.5(7) . . ? O1B Cl2 O3A 95.2(15) . . ? O1A Cl2 O3A 101.3(7) . . ? O4A Cl2 O4B 49.9(6) . . ? O2A Cl2 O4B 81.9(7) . . ? O2B Cl2 O4B 96.9(9) . . ? O3B Cl2 O4B 95.2(9) . . ? O1B Cl2 O4B 106.3(15) . . ? O1A Cl2 O4B 96.9(8) . . ? O3A Cl2 O4B 154.6(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.6(4) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C3 C4 C5 N1 -2.1(4) . . . . ? C3 C4 C5 C6 179.9(3) . . . . ? N1 C5 C6 N3 11.5(4) . . . . ? C4 C5 C6 N3 -170.5(2) . . . . ? N3 C7 C8 N2 -32.5(3) . . . . ? N3 C7 C8 C9 149.3(3) . . . . ? N2 C8 C9 C10 -0.8(4) . . . . ? C7 C8 C9 C10 177.2(3) . . . . ? C8 C9 C10 C11 -0.3(5) . . . . ? C9 C10 C11 C12 0.8(5) . . . . ? C10 C11 C12 N2 -0.2(5) . . . . ? N3 C13 C14 N4 -48.9(3) . . . . ? N3 C13 C14 C15 133.3(3) . . . . ? N4 C14 C15 N6 -0.2(3) . . . . ? C13 C14 C15 N6 177.8(3) . . . . ? N6 C16 C17 C22 15.7(4) . . . . ? N6 C16 C17 C18 -165.4(2) . . . . ? C22 C17 C18 C19 0.6(4) . . . . ? C16 C17 C18 C19 -178.4(3) . . . . ? C17 C18 C19 C20 -0.5(5) . . . . ? C18 C19 C20 C21 -0.2(5) . . . . ? C19 C20 C21 C22 0.7(4) . . . . ? C20 C21 C22 C17 -0.6(4) . . . . ? C18 C17 C22 C21 0.0(4) . . . . ? C16 C17 C22 C21 178.9(3) . . . . ? C4 C5 N1 C1 2.5(4) . . . . ? C6 C5 N1 C1 -179.4(2) . . . . ? C4 C5 N1 Cu1 -179.0(2) . . . . ? C6 C5 N1 Cu1 -0.9(3) . . . . ? C2 C1 N1 C5 -1.1(4) . . . . ? C2 C1 N1 Cu1 -179.5(2) . . . . ? N2 Cu1 N1 C5 40.1(4) . . . . ? N3 Cu1 N1 C5 -6.52(19) . . . . ? Cl1 Cu1 N1 C5 166.84(18) . . . . ? N4 Cu1 N1 C5 -87.8(2) . . . . ? N2 Cu1 N1 C1 -141.5(3) . . . . ? N3 Cu1 N1 C1 171.9(2) . . . . ? Cl1 Cu1 N1 C1 -14.8(2) . . . . ? N4 Cu1 N1 C1 90.6(2) . . . . ? C11 C12 N2 C8 -0.8(4) . . . . ? C11 C12 N2 Cu1 176.0(2) . . . . ? C9 C8 N2 C12 1.4(4) . . . . ? C7 C8 N2 C12 -176.8(2) . . . . ? C9 C8 N2 Cu1 -175.9(2) . . . . ? C7 C8 N2 Cu1 5.9(3) . . . . ? N1 Cu1 N2 C12 150.8(3) . . . . ? N3 Cu1 N2 C12 -162.3(2) . . . . ? Cl1 Cu1 N2 C12 23.9(2) . . . . ? N4 Cu1 N2 C12 -83.9(2) . . . . ? N1 Cu1 N2 C8 -32.2(4) . . . . ? N3 Cu1 N2 C8 14.68(19) . . . . ? Cl1 Cu1 N2 C8 -159.11(18) . . . . ? N4 Cu1 N2 C8 93.1(2) . . . . ? C8 C7 N3 C6 160.3(2) . . . . ? C8 C7 N3 C13 -75.3(3) . . . . ? C8 C7 N3 Cu1 41.2(2) . . . . ? C5 C6 N3 C7 -132.4(2) . . . . ? C5 C6 N3 C13 104.6(3) . . . . ? C5 C6 N3 Cu1 -15.5(3) . . . . ? C14 C13 N3 C7 155.6(2) . . . . ? C14 C13 N3 C6 -79.5(3) . . . . ? C14 C13 N3 Cu1 41.1(3) . . . . ? N1 Cu1 N3 C7 133.34(17) . . . . ? N2 Cu1 N3 C7 -30.96(17) . . . . ? N4 Cu1 N3 C7 -137.75(17) . . . . ? N1 Cu1 N3 C6 12.14(17) . . . . ? N2 Cu1 N3 C6 -152.16(18) . . . . ? N4 Cu1 N3 C6 101.05(17) . . . . ? N1 Cu1 N3 C13 -109.82(18) . . . . ? N2 Cu1 N3 C13 85.89(18) . . . . ? N4 Cu1 N3 C13 -20.90(17) . . . . ? C15 C14 N4 N5 -0.2(3) . . . . ? C13 C14 N4 N5 -178.6(2) . . . . ? C15 C14 N4 Cu1 -153.62(19) . . . . ? C13 C14 N4 Cu1 28.0(3) . . . . ? N1 Cu1 N4 N5 -60.2(3) . . . . ? N2 Cu1 N4 N5 137.3(3) . . . . ? N3 Cu1 N4 N5 -144.0(3) . . . . ? Cl1 Cu1 N4 N5 36.6(3) . . . . ? N1 Cu1 N4 C14 81.02(18) . . . . ? N2 Cu1 N4 C14 -81.46(18) . . . . ? N3 Cu1 N4 C14 -2.74(17) . . . . ? Cl1 Cu1 N4 C14 177.78(15) . . . . ? C14 N4 N5 N6 0.6(3) . . . . ? Cu1 N4 N5 N6 140.5(2) . . . . ? N4 N5 N6 C15 -0.7(3) . . . . ? N4 N5 N6 C16 -176.8(2) . . . . ? C14 C15 N6 N5 0.6(3) . . . . ? C14 C15 N6 C16 176.3(3) . . . . ? C17 C16 N6 N5 70.4(3) . . . . ? C17 C16 N6 C15 -105.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.842 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.092 # Attachment 'fig-2A---zhu47final.cif' data_zhu47 _database_code_depnum_ccdc_archive 'CCDC 811002' #TrackingRef 'fig-2A---zhu47final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H38 Cu N14, C2 H3 N, 2(Cl O4)' _chemical_formula_sum 'C48 H41 Cl2 Cu N15 O8' _chemical_formula_weight 1090.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6858(7) _cell_length_b 12.5597(8) _cell_length_c 17.8088(11) _cell_angle_alpha 70.0930(10) _cell_angle_beta 78.6670(10) _cell_angle_gamma 79.7420(10) _cell_volume 2392.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8228 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.90 _exptl_crystal_description polyhedral _exptl_crystal_colour green _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1122 _exptl_absorpt_coefficient_mu 0.641 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8459 _exptl_absorpt_correction_T_max 0.8613 _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_reflns_number 26975 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.10 _reflns_number_total 10453 _reflns_number_gt 8465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+3.2271P] 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 10453 _refine_ls_number_parameters 668 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 Cu1 Cu 0.07975(3) 0.69401(2) 0.221658(18) 0.02662(9) Uani 1 1 d . . . N1 N -0.19448(19) 0.78226(18) 0.17803(13) 0.0332(5) Uani 1 1 d . . . N2 N -0.11546(19) 0.69147(17) 0.19581(13) 0.0319(5) Uani 1 1 d . . . N3 N -0.16255(18) 0.61580(16) 0.26376(12) 0.0278(4) Uani 1 1 d . . . N4 N 0.06300(17) 0.56774(16) 0.33318(12) 0.0259(4) Uani 1 1 d . . . N5 N 0.30446(19) 0.65504(18) 0.29581(13) 0.0322(5) Uani 1 1 d . . . N6 N 0.26945(19) 0.72609(18) 0.22651(14) 0.0348(5) Uani 1 1 d . . . N7 N 0.3563(2) 0.72374(19) 0.16765(14) 0.0363(5) Uani 1 1 d . . . C1 C -0.4815(2) 0.8436(3) 0.29840(18) 0.0415(6) Uani 1 1 d . . . H1 H -0.4681 0.7886 0.3488 0.050 Uiso 1 1 calc R . . C2 C -0.5828(3) 0.9202(3) 0.2937(2) 0.0513(8) Uani 1 1 d . . . H2 H -0.6388 0.9171 0.3407 0.062 Uiso 1 1 calc R . . C3 C -0.6029(3) 1.0012(3) 0.2209(2) 0.0534(8) Uani 1 1 d . . . H3 H -0.6714 1.0552 0.2181 0.064 Uiso 1 1 calc R . . C4 C -0.5229(3) 1.0033(3) 0.1521(2) 0.0540(8) Uani 1 1 d . . . H4 H -0.5373 1.0581 0.1018 0.065 Uiso 1 1 calc R . . C5 C -0.4216(2) 0.9258(2) 0.15605(19) 0.0428(7) Uani 1 1 d . . . H5 H -0.3677 0.9268 0.1084 0.051 Uiso 1 1 calc R . . C6 C -0.3991(2) 0.8465(2) 0.22997(16) 0.0322(5) Uani 1 1 d . . . C7 C -0.2924(2) 0.7635(2) 0.23459(15) 0.0294(5) Uani 1 1 d . . . C8 C -0.2715(2) 0.6566(2) 0.28940(15) 0.0282(5) Uani 1 1 d . . . H8 H -0.3234 0.6197 0.3355 0.034 Uiso 1 1 calc R . . C9 C -0.0964(2) 0.5030(2) 0.29166(15) 0.0298(5) Uani 1 1 d . . . H9A H -0.0503 0.4840 0.2440 0.036 Uiso 1 1 calc R . . H9B H -0.1530 0.4464 0.3179 0.036 Uiso 1 1 calc R . . C10 C -0.0134(2) 0.4908(2) 0.35016(14) 0.0276(5) Uani 1 1 d . . . C11 C -0.0133(2) 0.3945(2) 0.41804(15) 0.0330(6) Uani 1 1 d . . . H11 H -0.0696 0.3430 0.4295 0.040 Uiso 1 1 calc R . . C12 C 0.0692(3) 0.3742(2) 0.46891(16) 0.0392(6) Uani 1 1 d . . . H12 H 0.0723 0.3076 0.5147 0.047 Uiso 1 1 calc R . . C13 C 0.1466(2) 0.4527(2) 0.45168(16) 0.0366(6) Uani 1 1 d . . . H13 H 0.2039 0.4407 0.4858 0.044 Uiso 1 1 calc R . . C14 C 0.1413(2) 0.5497(2) 0.38452(15) 0.0296(5) Uani 1 1 d . . . C15 C 0.2217(2) 0.6386(2) 0.37059(16) 0.0350(6) Uani 1 1 d . . . H15A H 0.1732 0.7121 0.3694 0.042 Uiso 1 1 calc R . . H15B H 0.2665 0.6157 0.4165 0.042 Uiso 1 1 calc R . . C16 C 0.4149(2) 0.6063(2) 0.28173(17) 0.0350(6) Uani 1 1 d . . . H16 H 0.4604 0.5530 0.3201 0.042 Uiso 1 1 calc R . . C17 C 0.4479(2) 0.6504(2) 0.19960(17) 0.0341(6) Uani 1 1 d . . . C18 C 0.5600(2) 0.6299(3) 0.14942(18) 0.0393(6) Uani 1 1 d . . . C19 C 0.6395(3) 0.5338(3) 0.1789(2) 0.0469(7) Uani 1 1 d . . . H19 H 0.6198 0.4804 0.2306 0.056 Uiso 1 1 calc R . . C20 C 0.7472(3) 0.5166(3) 0.1326(2) 0.0578(10) Uani 1 1 d . . . H20 H 0.8007 0.4509 0.1526 0.069 Uiso 1 1 calc R . . C21 C 0.7770(3) 0.5940(4) 0.0579(2) 0.0633(10) Uani 1 1 d . . . H21 H 0.8516 0.5827 0.0270 0.076 Uiso 1 1 calc R . . C22 C 0.6983(3) 0.6880(4) 0.0280(2) 0.0613(10) Uani 1 1 d . . . H22 H 0.7183 0.7407 -0.0240 0.074 Uiso 1 1 calc R . . C23 C 0.5901(3) 0.7064(3) 0.07327(19) 0.0489(7) Uani 1 1 d . . . H23 H 0.5364 0.7713 0.0521 0.059 Uiso 1 1 calc R . . N31 N -0.08810(18) 0.80141(17) 0.32881(13) 0.0306(5) Uani 1 1 d . . . N32 N -0.00044(18) 0.81291(17) 0.26897(13) 0.0304(5) Uani 1 1 d . . . N33 N 0.01062(19) 0.92419(17) 0.23300(13) 0.0320(5) Uani 1 1 d . . . N34 N 0.10320(17) 0.81656(17) 0.10649(13) 0.0291(4) Uani 1 1 d . . . N35 N 0.18159(18) 0.58565(17) 0.09813(12) 0.0283(4) Uani 1 1 d . . . N36 N 0.16325(18) 0.57044(16) 0.17748(12) 0.0284(4) Uani 1 1 d . . . N37 N 0.24543(18) 0.49257(17) 0.21146(13) 0.0293(4) Uani 1 1 d . . . C24 C -0.2900(2) 0.8336(2) 0.44609(17) 0.0373(6) Uani 1 1 d . . . H24 H -0.2809 0.7660 0.4317 0.045 Uiso 1 1 calc R . . C25 C -0.3672(3) 0.8424(3) 0.51395(19) 0.0457(7) Uani 1 1 d . . . H25 H -0.4098 0.7807 0.5466 0.055 Uiso 1 1 calc R . . C26 C -0.3821(3) 0.9422(3) 0.5341(2) 0.0517(8) Uani 1 1 d . . . H26 H -0.4339 0.9481 0.5812 0.062 Uiso 1 1 calc R . . C27 C -0.3218(3) 1.0327(3) 0.4859(2) 0.0486(7) Uani 1 1 d . . . H27 H -0.3341 1.1014 0.4992 0.058 Uiso 1 1 calc R . . C28 C -0.2435(2) 1.0236(2) 0.41828(18) 0.0398(6) Uani 1 1 d . . . H28 H -0.2020 1.0859 0.3854 0.048 Uiso 1 1 calc R . . C29 C -0.2256(2) 0.9226(2) 0.39862(16) 0.0326(5) Uani 1 1 d . . . C30 C -0.1337(2) 0.9077(2) 0.33240(16) 0.0307(5) Uani 1 1 d . . . C31 C -0.0712(2) 0.9859(2) 0.27096(17) 0.0339(6) Uani 1 1 d . . . H31 H -0.0833 1.0666 0.2581 0.041 Uiso 1 1 calc R . . C32 C 0.1113(2) 0.9598(2) 0.17140(17) 0.0365(6) Uani 1 1 d . . . H32A H 0.1843 0.9267 0.1954 0.044 Uiso 1 1 calc R . . H32B H 0.1075 1.0439 0.1547 0.044 Uiso 1 1 calc R . . C33 C 0.1177(2) 0.9251(2) 0.09787(17) 0.0334(6) Uani 1 1 d . . . C34 C 0.1429(2) 1.0046(2) 0.02235(19) 0.0411(7) Uani 1 1 d . . . H34 H 0.1535 1.0799 0.0179 0.049 Uiso 1 1 calc R . . C35 C 0.1524(2) 0.9738(2) -0.04646(18) 0.0428(7) Uani 1 1 d . . . H35 H 0.1692 1.0274 -0.0985 0.051 Uiso 1 1 calc R . . C36 C 0.1371(2) 0.8640(2) -0.03799(16) 0.0367(6) Uani 1 1 d . . . H36 H 0.1429 0.8409 -0.0843 0.044 Uiso 1 1 calc R . . C37 C 0.1131(2) 0.7874(2) 0.03867(16) 0.0310(5) Uani 1 1 d . . . C38 C 0.0991(2) 0.6661(2) 0.04809(15) 0.0320(5) Uani 1 1 d . . . H38A H 0.0177 0.6508 0.0731 0.038 Uiso 1 1 calc R . . H38B H 0.1130 0.6556 -0.0058 0.038 Uiso 1 1 calc R . . C39 C 0.2761(2) 0.5163(2) 0.07969(15) 0.0310(5) Uani 1 1 d . . . H39 H 0.3083 0.5096 0.0280 0.037 Uiso 1 1 calc R . . C40 C 0.3166(2) 0.4566(2) 0.15247(15) 0.0296(5) Uani 1 1 d . . . C41 C 0.4191(2) 0.3702(2) 0.16927(16) 0.0330(6) Uani 1 1 d . . . C42 C 0.4921(3) 0.3395(3) 0.10607(19) 0.0425(7) Uani 1 1 d . . . H42 H 0.4745 0.3732 0.0525 0.051 Uiso 1 1 calc R . . C43 C 0.5902(3) 0.2600(3) 0.1213(2) 0.0545(8) Uani 1 1 d . . . H43 H 0.6395 0.2389 0.0782 0.065 Uiso 1 1 calc R . . C44 C 0.6169(3) 0.2114(3) 0.1988(2) 0.0568(9) Uani 1 1 d . . . H44 H 0.6845 0.1571 0.2088 0.068 Uiso 1 1 calc R . . C45 C 0.5455(3) 0.2415(3) 0.2619(2) 0.0534(8) Uani 1 1 d . . . H45 H 0.5643 0.2084 0.3152 0.064 Uiso 1 1 calc R . . C46 C 0.4463(3) 0.3201(3) 0.24722(18) 0.0439(7) Uani 1 1 d . . . H46 H 0.3966 0.3399 0.2907 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.63091(9) 0.36465(7) 0.44836(5) 0.0589(2) Uani 1 1 d . . . O1 O 0.6064(2) 0.28993(19) 0.52664(13) 0.0618(6) Uani 1 1 d . . . O2 O 0.6723(3) 0.4639(2) 0.45141(15) 0.0887(10) Uani 1 1 d . . . O3 O 0.7264(3) 0.3034(3) 0.4038(2) 0.1088(12) Uani 1 1 d . . . O4 O 0.5373(4) 0.3937(3) 0.4063(2) 0.1247(16) Uani 1 1 d . . . Cl2 Cl 0.04061(6) 0.28632(5) 0.16489(4) 0.03897(16) Uani 1 1 d . . . O5 O -0.0461(3) 0.2608(2) 0.2350(2) 0.1000(12) Uani 1 1 d . . . O6 O 0.0206(4) 0.2356(2) 0.1104(2) 0.1067(13) Uani 1 1 d . . . O7 O 0.0362(2) 0.40622(17) 0.12700(16) 0.0610(7) Uani 1 1 d . . . O8 O 0.1523(3) 0.2361(3) 0.1877(2) 0.0884(9) Uani 1 1 d . . . C61 C 0.0952(5) 0.1132(4) 0.3988(3) 0.0974(16) Uani 1 1 d . . . H61A H 0.1633 0.1473 0.3629 0.146 Uiso 1 1 calc R . . H61B H 0.0949 0.1154 0.4534 0.146 Uiso 1 1 calc R . . H61C H 0.0228 0.1561 0.3787 0.146 Uiso 1 1 calc R . . C62 C 0.1021(4) -0.0044(5) 0.4010(3) 0.0829(14) Uani 1 1 d . . . N61 N 0.1056(3) -0.0946(4) 0.4022(3) 0.1148(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 Cu1 0.02904(16) 0.01870(14) 0.02964(16) -0.00443(12) -0.00660(12) -0.00040(11) N1 0.0319(11) 0.0261(10) 0.0369(12) -0.0029(9) -0.0077(9) -0.0025(9) N2 0.0326(11) 0.0255(10) 0.0333(11) -0.0033(9) -0.0048(9) -0.0050(9) N3 0.0303(11) 0.0229(10) 0.0286(10) -0.0032(8) -0.0076(8) -0.0051(8) N4 0.0294(10) 0.0205(9) 0.0269(10) -0.0081(8) -0.0059(8) 0.0024(8) N5 0.0338(11) 0.0290(11) 0.0378(12) -0.0130(9) -0.0125(9) -0.0015(9) N6 0.0342(12) 0.0311(11) 0.0398(12) -0.0109(10) -0.0116(10) 0.0002(9) N7 0.0337(12) 0.0350(12) 0.0414(13) -0.0122(10) -0.0100(10) -0.0022(9) C1 0.0360(15) 0.0448(16) 0.0447(16) -0.0152(13) -0.0088(12) -0.0017(12) C2 0.0348(16) 0.061(2) 0.064(2) -0.0316(17) -0.0063(14) 0.0019(14) C3 0.0341(16) 0.0433(17) 0.087(3) -0.0259(18) -0.0186(16) 0.0053(13) C4 0.0418(17) 0.0368(16) 0.073(2) 0.0003(15) -0.0212(16) 0.0001(13) C5 0.0328(14) 0.0373(15) 0.0490(17) -0.0008(13) -0.0081(12) -0.0039(12) C6 0.0276(13) 0.0261(12) 0.0425(15) -0.0073(11) -0.0091(11) -0.0052(10) C7 0.0285(12) 0.0274(12) 0.0315(13) -0.0051(10) -0.0078(10) -0.0062(10) C8 0.0274(12) 0.0273(12) 0.0291(12) -0.0071(10) -0.0036(10) -0.0059(10) C9 0.0345(13) 0.0204(11) 0.0332(13) -0.0063(10) -0.0073(10) -0.0020(10) C10 0.0308(13) 0.0224(11) 0.0276(12) -0.0085(10) -0.0037(10) 0.0023(9) C11 0.0376(14) 0.0232(12) 0.0337(13) -0.0056(10) -0.0039(11) -0.0005(10) C12 0.0459(16) 0.0298(13) 0.0319(14) -0.0007(11) -0.0081(12) 0.0055(12) C13 0.0420(15) 0.0356(14) 0.0300(13) -0.0094(11) -0.0121(11) 0.0065(12) C14 0.0312(13) 0.0296(12) 0.0293(12) -0.0142(10) -0.0064(10) 0.0049(10) C15 0.0379(14) 0.0369(14) 0.0364(14) -0.0181(12) -0.0120(11) 0.0000(11) C16 0.0316(13) 0.0328(13) 0.0460(16) -0.0153(12) -0.0162(12) -0.0006(11) C17 0.0321(13) 0.0321(13) 0.0454(15) -0.0175(12) -0.0143(11) -0.0022(11) C18 0.0324(14) 0.0483(16) 0.0502(17) -0.0287(14) -0.0096(12) -0.0076(12) C19 0.0370(16) 0.0578(19) 0.0603(19) -0.0344(16) -0.0173(14) 0.0003(14) C20 0.0350(16) 0.082(3) 0.081(3) -0.059(2) -0.0203(16) 0.0081(16) C21 0.0369(17) 0.102(3) 0.077(3) -0.064(2) -0.0019(17) -0.0123(19) C22 0.057(2) 0.087(3) 0.056(2) -0.040(2) 0.0029(17) -0.027(2) C23 0.0479(18) 0.0578(19) 0.0498(18) -0.0259(16) -0.0059(14) -0.0126(15) N31 0.0320(11) 0.0261(10) 0.0351(11) -0.0104(9) -0.0098(9) -0.0002(8) N32 0.0323(11) 0.0206(10) 0.0371(12) -0.0075(9) -0.0070(9) -0.0013(8) N33 0.0341(11) 0.0197(10) 0.0423(12) -0.0085(9) -0.0090(9) -0.0025(8) N34 0.0246(10) 0.0220(10) 0.0358(11) -0.0038(9) -0.0050(8) -0.0006(8) N35 0.0342(11) 0.0247(10) 0.0258(10) -0.0064(8) -0.0063(8) -0.0040(8) N36 0.0345(11) 0.0222(10) 0.0273(10) -0.0066(8) -0.0077(8) 0.0003(8) N37 0.0327(11) 0.0226(10) 0.0329(11) -0.0088(9) -0.0095(9) 0.0013(8) C24 0.0365(14) 0.0329(14) 0.0450(16) -0.0149(12) -0.0128(12) 0.0024(11) C25 0.0408(16) 0.0453(17) 0.0493(18) -0.0143(14) -0.0041(13) -0.0053(13) C26 0.0447(18) 0.060(2) 0.0535(19) -0.0286(17) -0.0013(14) 0.0007(15) C27 0.0468(17) 0.0451(17) 0.060(2) -0.0293(16) -0.0094(15) 0.0053(14) C28 0.0377(15) 0.0326(14) 0.0514(17) -0.0178(13) -0.0092(13) 0.0022(11) C29 0.0300(13) 0.0311(13) 0.0397(14) -0.0148(11) -0.0129(11) 0.0043(10) C30 0.0314(13) 0.0253(12) 0.0377(14) -0.0117(11) -0.0123(11) 0.0021(10) C31 0.0352(14) 0.0220(12) 0.0464(15) -0.0128(11) -0.0116(12) 0.0024(10) C32 0.0313(13) 0.0217(12) 0.0537(17) -0.0088(12) -0.0052(12) -0.0039(10) C33 0.0221(12) 0.0247(12) 0.0464(15) -0.0039(11) -0.0048(11) -0.0004(9) C34 0.0300(14) 0.0240(13) 0.0572(18) 0.0006(12) -0.0028(12) -0.0031(10) C35 0.0318(14) 0.0353(15) 0.0444(16) 0.0069(13) -0.0019(12) -0.0043(11) C36 0.0284(13) 0.0384(15) 0.0331(14) -0.0004(11) -0.0024(11) -0.0023(11) C37 0.0228(12) 0.0282(12) 0.0355(13) -0.0028(11) -0.0053(10) 0.0002(10) C38 0.0326(13) 0.0312(13) 0.0304(13) -0.0059(11) -0.0086(10) -0.0021(10) C39 0.0333(13) 0.0293(13) 0.0313(13) -0.0125(11) -0.0024(10) -0.0026(10) C40 0.0320(13) 0.0246(12) 0.0336(13) -0.0104(10) -0.0055(10) -0.0035(10) C41 0.0327(13) 0.0268(12) 0.0418(15) -0.0142(11) -0.0080(11) -0.0005(10) C42 0.0391(15) 0.0441(16) 0.0474(17) -0.0224(14) -0.0078(13) 0.0043(12) C43 0.0419(17) 0.059(2) 0.063(2) -0.0302(17) -0.0073(15) 0.0151(15) C44 0.0405(17) 0.0510(19) 0.076(2) -0.0227(18) -0.0171(16) 0.0182(14) C45 0.0489(18) 0.0499(19) 0.0550(19) -0.0115(16) -0.0173(15) 0.0107(15) C46 0.0433(16) 0.0416(16) 0.0438(16) -0.0138(13) -0.0100(13) 0.0072(13) Cl1 0.0875(6) 0.0531(5) 0.0377(4) 0.0100(3) -0.0263(4) -0.0427(4) O1 0.0905(19) 0.0465(13) 0.0431(13) 0.0027(10) -0.0131(12) -0.0247(12) O2 0.156(3) 0.0680(17) 0.0511(15) 0.0079(13) -0.0317(17) -0.0709(19) O3 0.123(3) 0.115(3) 0.096(2) -0.052(2) 0.044(2) -0.063(2) O4 0.178(4) 0.078(2) 0.134(3) 0.006(2) -0.124(3) -0.021(2) Cl2 0.0368(3) 0.0267(3) 0.0545(4) -0.0147(3) -0.0074(3) -0.0023(3) O5 0.081(2) 0.0460(15) 0.126(3) -0.0012(16) 0.0422(19) -0.0033(14) O6 0.202(4) 0.0407(14) 0.104(2) -0.0206(15) -0.097(3) -0.0041(19) O7 0.0587(14) 0.0271(10) 0.0869(18) -0.0164(11) 0.0163(13) -0.0125(10) O8 0.0613(17) 0.093(2) 0.105(2) -0.0216(18) -0.0342(17) 0.0101(15) C61 0.133(4) 0.081(3) 0.094(3) -0.038(3) -0.062(3) 0.018(3) C62 0.061(2) 0.108(4) 0.112(4) -0.075(3) -0.048(2) 0.029(2) N61 0.073(3) 0.126(4) 0.202(5) -0.121(4) -0.075(3) 0.038(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N32 1.966(2) . ? Cu1 N36 1.993(2) . ? Cu1 N4 2.076(2) . ? Cu1 N34 2.105(2) . ? Cu1 N6 2.345(2) . ? Cu1 N2 2.422(2) . ? N1 N2 1.322(3) . ? N1 C7 1.364(3) . ? N2 N3 1.346(3) . ? N3 C8 1.338(3) . ? N3 C9 1.460(3) . ? N4 C10 1.350(3) . ? N4 C14 1.356(3) . ? N5 C16 1.341(3) . ? N5 N6 1.344(3) . ? N5 C15 1.459(3) . ? N6 N7 1.312(3) . ? N7 C17 1.360(3) . ? C1 C6 1.391(4) . ? C1 C2 1.382(4) . ? C1 H1 0.9500 . ? C2 C3 1.381(5) . ? C2 H2 0.9500 . ? C3 C4 1.382(5) . ? C3 H3 0.9500 . ? C4 C5 1.390(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(4) . ? C5 H5 0.9500 . ? C6 C7 1.471(3) . ? C7 C8 1.379(3) . ? C8 H8 0.9500 . ? C9 C10 1.512(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.389(3) . ? C11 C12 1.384(4) . ? C11 H11 0.9500 . ? C12 C13 1.374(4) . ? C12 H12 0.9500 . ? C13 C14 1.388(4) . ? C13 H13 0.9500 . ? C14 C15 1.512(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.377(4) . ? C16 H16 0.9500 . ? C17 C18 1.469(4) . ? C18 C23 1.389(4) . ? C18 C19 1.398(4) . ? C19 C20 1.389(4) . ? C19 H19 0.9500 . ? C20 C21 1.375(6) . ? C20 H20 0.9500 . ? C21 C22 1.380(6) . ? C21 H21 0.9500 . ? C22 C23 1.387(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N31 N32 1.313(3) . ? N31 C30 1.364(3) . ? N32 N33 1.343(3) . ? N33 C31 1.346(3) . ? N33 C32 1.461(3) . ? N34 C33 1.357(3) . ? N34 C37 1.355(3) . ? N35 C39 1.340(3) . ? N35 N36 1.338(3) . ? N35 C38 1.456(3) . ? N36 N37 1.317(3) . ? N37 C40 1.358(3) . ? C24 C25 1.383(4) . ? C24 C29 1.392(4) . ? C24 H24 0.9500 . ? C25 C26 1.391(4) . ? C25 H25 0.9500 . ? C26 C27 1.380(5) . ? C26 H26 0.9500 . ? C27 C28 1.388(4) . ? C27 H27 0.9500 . ? C28 C29 1.398(4) . ? C28 H28 0.9500 . ? C29 C30 1.470(4) . ? C30 C31 1.381(4) . ? C31 H31 0.9500 . ? C32 C33 1.500(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.388(4) . ? C34 C35 1.385(4) . ? C34 H34 0.9500 . ? C35 C36 1.375(4) . ? C35 H35 0.9500 . ? C36 C37 1.385(3) . ? C36 H36 0.9500 . ? C37 C38 1.510(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.385(4) . ? C39 H39 0.9500 . ? C40 C41 1.469(3) . ? C41 C42 1.395(4) . ? C41 C46 1.390(4) . ? C42 C43 1.384(4) . ? C42 H42 0.9500 . ? C43 C44 1.379(5) . ? C43 H43 0.9500 . ? C44 C45 1.382(5) . ? C44 H44 0.9500 . ? C45 C46 1.387(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? Cl1 O4 1.373(3) . ? Cl1 O1 1.398(2) . ? Cl1 O2 1.436(3) . ? Cl1 O3 1.492(4) . ? Cl2 O6 1.401(3) . ? Cl2 O8 1.417(3) . ? Cl2 O5 1.426(3) . ? Cl2 O7 1.421(2) . ? C61 C62 1.452(6) . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? C62 N61 1.119(6) . ? 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 N32 Cu1 N36 177.92(9) . . ? N32 Cu1 N4 92.00(8) . . ? N36 Cu1 N4 86.22(8) . . ? N32 Cu1 N34 90.68(8) . . ? N36 Cu1 N34 91.09(8) . . ? N4 Cu1 N34 177.19(8) . . ? N32 Cu1 N6 94.60(8) . . ? N36 Cu1 N6 84.51(8) . . ? N4 Cu1 N6 95.35(8) . . ? N34 Cu1 N6 83.57(8) . . ? N32 Cu1 N2 83.19(8) . . ? N36 Cu1 N2 98.01(8) . . ? N4 Cu1 N2 94.76(7) . . ? N34 Cu1 N2 86.41(7) . . ? N6 Cu1 N2 169.72(7) . . ? N2 N1 C7 108.8(2) . . ? N1 N2 N3 107.2(2) . . ? N1 N2 Cu1 124.39(16) . . ? N3 N2 Cu1 103.50(14) . . ? C8 N3 N2 110.9(2) . . ? C8 N3 C9 130.9(2) . . ? N2 N3 C9 117.8(2) . . ? C10 N4 C14 118.4(2) . . ? C10 N4 Cu1 120.36(16) . . ? C14 N4 Cu1 120.32(17) . . ? C16 N5 N6 110.4(2) . . ? C16 N5 C15 130.5(2) . . ? N6 N5 C15 119.0(2) . . ? N7 N6 N5 108.1(2) . . ? N7 N6 Cu1 121.84(17) . . ? N5 N6 Cu1 108.86(16) . . ? N6 N7 C17 108.3(2) . . ? C6 C1 C2 120.6(3) . . ? C6 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 C7 120.6(2) . . ? C5 C6 C7 120.3(2) . . ? N1 C7 C8 107.8(2) . . ? N1 C7 C6 122.3(2) . . ? C8 C7 C6 129.8(2) . . ? N3 C8 C7 105.3(2) . . ? N3 C8 H8 127.3 . . ? C7 C8 H8 127.3 . . ? N3 C9 C10 115.3(2) . . ? N3 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? N3 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? N4 C10 C11 121.9(2) . . ? N4 C10 C9 120.3(2) . . ? C11 C10 C9 117.7(2) . . ? C12 C11 C10 119.5(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 118.4(2) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? N4 C14 C13 121.4(2) . . ? N4 C14 C15 119.7(2) . . ? C13 C14 C15 118.9(2) . . ? N5 C15 C14 113.5(2) . . ? N5 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? N5 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? N5 C16 C17 105.0(2) . . ? N5 C16 H16 127.5 . . ? C17 C16 H16 127.5 . . ? N7 C17 C16 108.2(2) . . ? N7 C17 C18 121.9(3) . . ? C16 C17 C18 129.9(2) . . ? C23 C18 C19 119.1(3) . . ? C23 C18 C17 120.9(3) . . ? C19 C18 C17 120.0(3) . . ? C20 C19 C18 120.0(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 120.5(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 119.8(3) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C23 120.5(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 120.2(3) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? N32 N31 C30 107.8(2) . . ? N31 N32 N33 109.23(19) . . ? N31 N32 Cu1 126.29(16) . . ? N33 N32 Cu1 123.11(17) . . ? C31 N33 N32 109.3(2) . . ? C31 N33 C32 129.7(2) . . ? N32 N33 C32 120.3(2) . . ? C33 N34 C37 118.0(2) . . ? C33 N34 Cu1 120.83(18) . . ? C37 N34 Cu1 121.01(16) . . ? C39 N35 N36 110.1(2) . . ? C39 N35 C38 131.1(2) . . ? N36 N35 C38 118.8(2) . . ? N37 N36 N35 108.93(19) . . ? N37 N36 Cu1 123.62(16) . . ? N35 N36 Cu1 121.41(15) . . ? N36 N37 C40 107.6(2) . . ? C25 C24 C29 120.7(3) . . ? C25 C24 H24 119.6 . . ? C29 C24 H24 119.6 . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 120.3(3) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 120.3(3) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C29 119.9(3) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C24 C29 C28 119.2(3) . . ? C24 C29 C30 120.5(2) . . ? C28 C29 C30 120.2(2) . . ? N31 C30 C31 107.9(2) . . ? N31 C30 C29 120.8(2) . . ? C31 C30 C29 130.9(2) . . ? N33 C31 C30 105.7(2) . . ? N33 C31 H31 127.2 . . ? C30 C31 H31 127.2 . . ? N33 C32 C33 113.9(2) . . ? N33 C32 H32A 108.8 . . ? C33 C32 H32A 108.8 . . ? N33 C32 H32B 108.8 . . ? C33 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? N34 C33 C34 121.7(3) . . ? N34 C33 C32 119.7(2) . . ? C34 C33 C32 118.6(2) . . ? C33 C34 C35 119.8(3) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C36 C35 C34 118.7(3) . . ? C36 C35 H35 120.6 . . ? C34 C35 H35 120.6 . . ? C35 C36 C37 119.4(3) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? N34 C37 C36 122.4(2) . . ? N34 C37 C38 118.1(2) . . ? C36 C37 C38 119.4(2) . . ? N35 C38 C37 110.8(2) . . ? N35 C38 H38A 109.5 . . ? C37 C38 H38A 109.5 . . ? N35 C38 H38B 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 108.1 . . ? N35 C39 C40 105.0(2) . . ? N35 C39 H39 127.5 . . ? C40 C39 H39 127.5 . . ? N37 C40 C39 108.4(2) . . ? N37 C40 C41 122.0(2) . . ? C39 C40 C41 129.5(2) . . ? C42 C41 C46 119.1(3) . . ? C42 C41 C40 119.8(2) . . ? C46 C41 C40 121.0(2) . . ? C43 C42 C41 120.0(3) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C44 C43 C42 120.3(3) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C45 120.2(3) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? C44 C45 C46 119.8(3) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C41 C46 C45 120.5(3) . . ? C41 C46 H46 119.8 . . ? C45 C46 H46 119.8 . . ? O4 Cl1 O1 113.1(2) . . ? O4 Cl1 O2 111.4(2) . . ? O1 Cl1 O2 109.59(15) . . ? O4 Cl1 O3 106.5(3) . . ? O1 Cl1 O3 107.06(19) . . ? O2 Cl1 O3 108.9(2) . . ? O6 Cl2 O8 106.6(2) . . ? O6 Cl2 O5 109.6(2) . . ? O8 Cl2 O5 108.7(2) . . ? O6 Cl2 O7 109.34(17) . . ? O8 Cl2 O7 112.12(18) . . ? O5 Cl2 O7 110.39(15) . . ? C62 C61 H61A 109.5 . . ? C62 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C62 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? N61 C62 C61 178.7(5) . . ? 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 C7 N1 N2 N3 -0.5(3) . . . . ? C7 N1 N2 Cu1 -121.10(19) . . . . ? N32 Cu1 N2 N1 34.1(2) . . . . ? N36 Cu1 N2 N1 -147.59(19) . . . . ? N4 Cu1 N2 N1 125.57(19) . . . . ? N34 Cu1 N2 N1 -57.0(2) . . . . ? N6 Cu1 N2 N1 -44.0(5) . . . . ? N32 Cu1 N2 N3 -88.12(15) . . . . ? N36 Cu1 N2 N3 90.17(15) . . . . ? N4 Cu1 N2 N3 3.33(15) . . . . ? N34 Cu1 N2 N3 -179.23(15) . . . . ? N6 Cu1 N2 N3 -166.2(4) . . . . ? N1 N2 N3 C8 0.6(3) . . . . ? Cu1 N2 N3 C8 133.66(17) . . . . ? N1 N2 N3 C9 174.1(2) . . . . ? Cu1 N2 N3 C9 -52.9(2) . . . . ? N32 Cu1 N4 C10 108.00(18) . . . . ? N36 Cu1 N4 C10 -73.07(18) . . . . ? N6 Cu1 N4 C10 -157.19(17) . . . . ? N2 Cu1 N4 C10 24.67(18) . . . . ? N32 Cu1 N4 C14 -82.89(18) . . . . ? N36 Cu1 N4 C14 96.04(18) . . . . ? N6 Cu1 N4 C14 11.92(18) . . . . ? N2 Cu1 N4 C14 -166.22(17) . . . . ? C16 N5 N6 N7 0.0(3) . . . . ? C15 N5 N6 N7 -177.6(2) . . . . ? C16 N5 N6 Cu1 134.33(17) . . . . ? C15 N5 N6 Cu1 -43.3(2) . . . . ? N32 Cu1 N6 N7 -140.05(19) . . . . ? N36 Cu1 N6 N7 41.84(19) . . . . ? N4 Cu1 N6 N7 127.51(19) . . . . ? N34 Cu1 N6 N7 -49.89(19) . . . . ? N2 Cu1 N6 N7 -62.9(5) . . . . ? N32 Cu1 N6 N5 93.18(16) . . . . ? N36 Cu1 N6 N5 -84.93(16) . . . . ? N4 Cu1 N6 N5 0.74(16) . . . . ? N34 Cu1 N6 N5 -176.66(16) . . . . ? N2 Cu1 N6 N5 170.3(4) . . . . ? N5 N6 N7 C17 0.0(3) . . . . ? Cu1 N6 N7 C17 -127.13(19) . . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? C1 C2 C3 C4 1.9(5) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C3 C4 C5 C6 -1.2(5) . . . . ? C2 C1 C6 C5 -1.7(4) . . . . ? C2 C1 C6 C7 -178.7(3) . . . . ? C4 C5 C6 C1 2.6(4) . . . . ? C4 C5 C6 C7 179.5(3) . . . . ? N2 N1 C7 C8 0.3(3) . . . . ? N2 N1 C7 C6 -177.1(2) . . . . ? C1 C6 C7 N1 -159.7(3) . . . . ? C5 C6 C7 N1 23.3(4) . . . . ? C1 C6 C7 C8 23.5(4) . . . . ? C5 C6 C7 C8 -153.4(3) . . . . ? N2 N3 C8 C7 -0.4(3) . . . . ? C9 N3 C8 C7 -172.8(2) . . . . ? N1 C7 C8 N3 0.1(3) . . . . ? C6 C7 C8 N3 177.2(2) . . . . ? C8 N3 C9 C10 -96.8(3) . . . . ? N2 N3 C9 C10 91.3(3) . . . . ? C14 N4 C10 C11 -0.2(3) . . . . ? Cu1 N4 C10 C11 169.08(18) . . . . ? C14 N4 C10 C9 -175.7(2) . . . . ? Cu1 N4 C10 C9 -6.3(3) . . . . ? N3 C9 C10 N4 -49.7(3) . . . . ? N3 C9 C10 C11 134.6(2) . . . . ? N4 C10 C11 C12 -1.9(4) . . . . ? C9 C10 C11 C12 173.6(2) . . . . ? C10 C11 C12 C13 2.1(4) . . . . ? C11 C12 C13 C14 -0.2(4) . . . . ? C10 N4 C14 C13 2.2(3) . . . . ? Cu1 N4 C14 C13 -167.08(19) . . . . ? C10 N4 C14 C15 -175.4(2) . . . . ? Cu1 N4 C14 C15 15.3(3) . . . . ? C12 C13 C14 N4 -2.1(4) . . . . ? C12 C13 C14 C15 175.6(2) . . . . ? C16 N5 C15 C14 -92.7(3) . . . . ? N6 N5 C15 C14 84.4(3) . . . . ? N4 C14 C15 N5 -64.7(3) . . . . ? C13 C14 C15 N5 117.6(3) . . . . ? N6 N5 C16 C17 -0.1(3) . . . . ? C15 N5 C16 C17 177.2(2) . . . . ? N6 N7 C17 C16 0.0(3) . . . . ? N6 N7 C17 C18 -178.9(2) . . . . ? N5 C16 C17 N7 0.0(3) . . . . ? N5 C16 C17 C18 178.8(3) . . . . ? N7 C17 C18 C23 18.8(4) . . . . ? C16 C17 C18 C23 -159.9(3) . . . . ? N7 C17 C18 C19 -162.7(2) . . . . ? C16 C17 C18 C19 18.6(4) . . . . ? C23 C18 C19 C20 0.7(4) . . . . ? C17 C18 C19 C20 -177.8(3) . . . . ? C18 C19 C20 C21 0.5(4) . . . . ? C19 C20 C21 C22 -1.5(5) . . . . ? C20 C21 C22 C23 1.2(5) . . . . ? C21 C22 C23 C18 0.1(5) . . . . ? C19 C18 C23 C22 -1.0(4) . . . . ? C17 C18 C23 C22 177.4(3) . . . . ? C30 N31 N32 N33 -0.9(3) . . . . ? C30 N31 N32 Cu1 -167.77(17) . . . . ? N4 Cu1 N32 N31 -35.7(2) . . . . ? N34 Cu1 N32 N31 145.1(2) . . . . ? N6 Cu1 N32 N31 -131.3(2) . . . . ? N2 Cu1 N32 N31 58.8(2) . . . . ? N4 Cu1 N32 N33 159.11(19) . . . . ? N34 Cu1 N32 N33 -20.03(19) . . . . ? N6 Cu1 N32 N33 63.58(19) . . . . ? N2 Cu1 N32 N33 -106.33(19) . . . . ? N31 N32 N33 C31 0.5(3) . . . . ? Cu1 N32 N33 C31 167.91(17) . . . . ? N31 N32 N33 C32 171.9(2) . . . . ? Cu1 N32 N33 C32 -20.8(3) . . . . ? N32 Cu1 N34 C33 31.59(19) . . . . ? N36 Cu1 N34 C33 -147.31(19) . . . . ? N6 Cu1 N34 C33 -62.96(18) . . . . ? N2 Cu1 N34 C33 114.73(18) . . . . ? N32 Cu1 N34 C37 -153.39(19) . . . . ? N36 Cu1 N34 C37 27.71(19) . . . . ? N6 Cu1 N34 C37 112.06(19) . . . . ? N2 Cu1 N34 C37 -70.25(18) . . . . ? C39 N35 N36 N37 0.6(3) . . . . ? C38 N35 N36 N37 178.3(2) . . . . ? C39 N35 N36 Cu1 154.15(17) . . . . ? C38 N35 N36 Cu1 -28.2(3) . . . . ? N4 Cu1 N36 N37 -45.57(19) . . . . ? N34 Cu1 N36 N37 133.62(19) . . . . ? N6 Cu1 N36 N37 50.18(19) . . . . ? N2 Cu1 N36 N37 -139.85(19) . . . . ? N4 Cu1 N36 N35 164.84(19) . . . . ? N34 Cu1 N36 N35 -15.98(19) . . . . ? N6 Cu1 N36 N35 -99.41(19) . . . . ? N2 Cu1 N36 N35 70.56(19) . . . . ? N35 N36 N37 C40 -0.8(3) . . . . ? Cu1 N36 N37 C40 -153.61(17) . . . . ? C29 C24 C25 C26 1.2(4) . . . . ? C24 C25 C26 C27 1.2(5) . . . . ? C25 C26 C27 C28 -1.9(5) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? C25 C24 C29 C28 -2.8(4) . . . . ? C25 C24 C29 C30 172.7(3) . . . . ? C27 C28 C29 C24 2.1(4) . . . . ? C27 C28 C29 C30 -173.4(3) . . . . ? N32 N31 C30 C31 0.9(3) . . . . ? N32 N31 C30 C29 -173.7(2) . . . . ? C24 C29 C30 N31 -17.4(4) . . . . ? C28 C29 C30 N31 158.0(2) . . . . ? C24 C29 C30 C31 169.4(3) . . . . ? C28 C29 C30 C31 -15.2(4) . . . . ? N32 N33 C31 C30 0.0(3) . . . . ? C32 N33 C31 C30 -170.2(2) . . . . ? N31 C30 C31 N33 -0.6(3) . . . . ? C29 C30 C31 N33 173.2(3) . . . . ? C31 N33 C32 C33 -128.2(3) . . . . ? N32 N33 C32 C33 62.5(3) . . . . ? C37 N34 C33 C34 -0.5(3) . . . . ? Cu1 N34 C33 C34 174.62(19) . . . . ? C37 N34 C33 C32 -178.1(2) . . . . ? Cu1 N34 C33 C32 -2.9(3) . . . . ? N33 C32 C33 N34 -47.2(3) . . . . ? N33 C32 C33 C34 135.2(2) . . . . ? N34 C33 C34 C35 0.7(4) . . . . ? C32 C33 C34 C35 178.3(2) . . . . ? C33 C34 C35 C36 -0.3(4) . . . . ? C34 C35 C36 C37 -0.2(4) . . . . ? C33 N34 C37 C36 0.0(3) . . . . ? Cu1 N34 C37 C36 -175.17(18) . . . . ? C33 N34 C37 C38 178.9(2) . . . . ? Cu1 N34 C37 C38 3.8(3) . . . . ? C35 C36 C37 N34 0.4(4) . . . . ? C35 C36 C37 C38 -178.6(2) . . . . ? C39 N35 C38 C37 -111.0(3) . . . . ? N36 N35 C38 C37 71.9(3) . . . . ? N34 C37 C38 N35 -55.8(3) . . . . ? C36 C37 C38 N35 123.2(2) . . . . ? N36 N35 C39 C40 -0.2(3) . . . . ? C38 N35 C39 C40 -177.5(2) . . . . ? N36 N37 C40 C39 0.7(3) . . . . ? N36 N37 C40 C41 179.2(2) . . . . ? N35 C39 C40 N37 -0.3(3) . . . . ? N35 C39 C40 C41 -178.7(2) . . . . ? N37 C40 C41 C42 -177.4(2) . . . . ? C39 C40 C41 C42 0.8(4) . . . . ? N37 C40 C41 C46 1.1(4) . . . . ? C39 C40 C41 C46 179.3(3) . . . . ? C46 C41 C42 C43 0.1(4) . . . . ? C40 C41 C42 C43 178.6(3) . . . . ? C41 C42 C43 C44 -0.5(5) . . . . ? C42 C43 C44 C45 0.2(6) . . . . ? C43 C44 C45 C46 0.5(5) . . . . ? C42 C41 C46 C45 0.7(4) . . . . ? C40 C41 C46 C45 -177.8(3) . . . . ? C44 C45 C46 C41 -1.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.201 _refine_diff_density_min -0.911 _refine_diff_density_rms 0.063 # Attachment 'fig-2B---zhu48final.cif' data_zhu48 _database_code_depnum_ccdc_archive 'CCDC 811003' #TrackingRef 'fig-2B---zhu48final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H38 Fe N14, C4 H10 O, C2 H3 N, 2(Cl O4)' _chemical_formula_sum 'C52 H51 Cl2 Fe N15 O9' _chemical_formula_weight 1156.83 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4446(9) _cell_length_b 14.6888(10) _cell_length_c 17.0173(12) _cell_angle_alpha 114.1500(10) _cell_angle_beta 101.2550(10) _cell_angle_gamma 96.1870(10) _cell_volume 2722.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7893 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 24.54 _exptl_crystal_description polyhedral _exptl_crystal_colour purple _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.445 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8350 _exptl_absorpt_correction_T_max 0.9526 _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_reflns_number 19804 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 23.82 _reflns_number_total 8347 _reflns_number_gt 6226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^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 8347 _refine_ls_number_parameters 715 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 2.003 _refine_ls_restrained_S_all 2.003 _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 Fe1 Fe 0.75164(4) 0.80079(4) 0.55692(3) 0.02664(15) Uani 1 1 d . . . C1 C 0.7578(3) 1.1921(3) 0.8332(3) 0.0464(11) Uani 1 1 d . . . H1 H 0.8048 1.1777 0.7937 0.056 Uiso 1 1 calc R . . C2 C 0.7860(4) 1.2837(3) 0.9097(3) 0.0553(12) Uani 1 1 d . . . H2 H 0.8515 1.3322 0.9217 0.066 Uiso 1 1 calc R . . C3 C 0.7205(4) 1.3050(3) 0.9681(3) 0.0566(12) Uani 1 1 d . . . H3 H 0.7416 1.3671 1.0215 0.068 Uiso 1 1 calc R . . C4 C 0.6242(4) 1.2362(3) 0.9494(3) 0.0561(12) Uani 1 1 d . . . H4 H 0.5776 1.2514 0.9892 0.067 Uiso 1 1 calc R . . C5 C 0.5946(3) 1.1444(3) 0.8722(3) 0.0461(11) Uani 1 1 d . . . H5 H 0.5277 1.0974 0.8596 0.055 Uiso 1 1 calc R . . C6 C 0.6613(3) 1.1208(3) 0.8136(2) 0.0347(9) Uani 1 1 d . . . C7 C 0.6350(3) 1.0207(3) 0.7366(2) 0.0305(9) Uani 1 1 d . . . C8 C 0.5421(3) 0.9427(3) 0.7005(2) 0.0352(9) Uani 1 1 d . . . H8 H 0.4738 0.9437 0.7175 0.042 Uiso 1 1 calc R . . C9 C 0.5055(3) 0.7602(2) 0.5798(2) 0.0325(9) Uani 1 1 d . . . H9A H 0.4874 0.7483 0.5166 0.039 Uiso 1 1 calc R . . H9B H 0.4341 0.7508 0.5956 0.039 Uiso 1 1 calc R . . C10 C 0.5701(3) 0.6834(2) 0.5899(2) 0.0283(9) Uani 1 1 d . . . C11 C 0.5225(3) 0.6131(3) 0.6144(2) 0.0407(10) Uani 1 1 d . . . H11 H 0.4527 0.6172 0.6288 0.049 Uiso 1 1 calc R . . C12 C 0.5764(3) 0.5373(3) 0.6178(3) 0.0467(11) Uani 1 1 d . . . H12 H 0.5444 0.4885 0.6345 0.056 Uiso 1 1 calc R . . C13 C 0.6771(3) 0.5338(3) 0.5967(2) 0.0395(10) Uani 1 1 d . . . H13 H 0.7149 0.4810 0.5970 0.047 Uiso 1 1 calc R . . C14 C 0.7234(3) 0.6072(3) 0.5749(2) 0.0286(9) Uani 1 1 d . . . C15 C 0.8371(3) 0.6029(3) 0.5563(2) 0.0324(9) Uani 1 1 d . . . H15A H 0.8948 0.6548 0.6095 0.039 Uiso 1 1 calc R . . H15B H 0.8534 0.5350 0.5461 0.039 Uiso 1 1 calc R . . C16 C 0.8705(3) 0.5616(3) 0.4038(3) 0.0381(10) Uani 1 1 d . . . H16 H 0.8842 0.4946 0.3865 0.046 Uiso 1 1 calc R . . C17 C 0.8726(3) 0.6190(3) 0.3572(2) 0.0350(10) Uani 1 1 d . . . C18 C 0.8942(3) 0.5968(3) 0.2695(3) 0.0463(11) Uani 1 1 d . . . C19 C 0.9488(4) 0.5198(4) 0.2315(3) 0.0686(14) Uani 1 1 d . . . H19 H 0.9731 0.4805 0.2615 0.082 Uiso 1 1 calc R . . C20 C 0.9682(4) 0.4997(4) 0.1468(4) 0.0911(19) Uani 1 1 d . . . H20 H 1.0062 0.4472 0.1199 0.109 Uiso 1 1 calc R . . C21 C 0.9317(5) 0.5565(5) 0.1048(4) 0.099(2) Uani 1 1 d . . . H21 H 0.9440 0.5426 0.0480 0.119 Uiso 1 1 calc R . . C22 C 0.8776(5) 0.6333(4) 0.1426(3) 0.0869(18) Uani 1 1 d . . . H22 H 0.8527 0.6721 0.1124 0.104 Uiso 1 1 calc R . . C23 C 0.8597(4) 0.6536(3) 0.2253(3) 0.0616(13) Uani 1 1 d . . . H23 H 0.8232 0.7074 0.2521 0.074 Uiso 1 1 calc R . . N1 N 0.7138(2) 0.9873(2) 0.69210(18) 0.0300(7) Uani 1 1 d . . . N2 N 0.6719(2) 0.8924(2) 0.63129(18) 0.0285(7) Uani 1 1 d . . . N3 N 0.5679(2) 0.8648(2) 0.63614(19) 0.0300(7) Uani 1 1 d . . . N4 N 0.6719(2) 0.68343(19) 0.57166(17) 0.0254(7) Uani 1 1 d . . . N5 N 0.8450(2) 0.6206(2) 0.4791(2) 0.0302(7) Uani 1 1 d . . . N6 N 0.8316(2) 0.7103(2) 0.48060(18) 0.0273(7) Uani 1 1 d . . . N7 N 0.8481(2) 0.7103(2) 0.40601(19) 0.0305(7) Uani 1 1 d . . . C24 C 1.0553(4) 0.8942(3) 0.9532(3) 0.0646(14) Uani 1 1 d . . . H24 H 1.1152 0.9323 0.9449 0.077 Uiso 1 1 calc R . . C25 C 1.0663(4) 0.8894(4) 1.0339(3) 0.0789(16) Uani 1 1 d . . . H25 H 1.1337 0.9230 1.0802 0.095 Uiso 1 1 calc R . . C26 C 0.9800(5) 0.8366(4) 1.0466(3) 0.0851(17) Uani 1 1 d . . . H26 H 0.9863 0.8355 1.1028 0.102 Uiso 1 1 calc R . . C27 C 0.8848(4) 0.7851(5) 0.9795(4) 0.106(2) Uani 1 1 d . . . H27 H 0.8259 0.7462 0.9880 0.127 Uiso 1 1 calc R . . C28 C 0.8741(4) 0.7897(4) 0.8980(3) 0.0819(17) Uani 1 1 d . . . H28 H 0.8073 0.7544 0.8514 0.098 Uiso 1 1 calc R . . C29 C 0.9589(3) 0.8446(3) 0.8847(3) 0.0477(11) Uani 1 1 d . . . C30 C 0.9463(3) 0.8519(3) 0.7998(2) 0.0373(10) Uani 1 1 d . . . C31 C 1.0252(3) 0.8934(3) 0.7703(2) 0.0401(10) Uani 1 1 d . . . H31 H 1.1016 0.9246 0.8010 0.048 Uiso 1 1 calc R . . C32 C 1.0112(3) 0.9051(2) 0.6239(2) 0.0296(9) Uani 1 1 d . . . H32A H 1.0101 0.8412 0.5718 0.036 Uiso 1 1 calc R . . H32B H 1.0898 0.9437 0.6510 0.036 Uiso 1 1 calc R . . C33 C 0.9412(3) 0.9673(3) 0.5931(2) 0.0267(9) Uani 1 1 d . . . C34 C 0.9904(3) 1.0633(3) 0.6076(2) 0.0311(9) Uani 1 1 d . . . H34 H 1.0660 1.0924 0.6419 0.037 Uiso 1 1 calc R . . C35 C 0.9294(3) 1.1168(3) 0.5720(2) 0.0345(9) Uani 1 1 d . . . H35 H 0.9612 1.1841 0.5831 0.041 Uiso 1 1 calc R . . C36 C 0.8218(3) 1.0708(2) 0.5202(2) 0.0324(9) Uani 1 1 d . . . H36 H 0.7802 1.1035 0.4907 0.039 Uiso 1 1 calc R . . C37 C 0.7746(3) 0.9765(2) 0.5114(2) 0.0268(9) Uani 1 1 d . . . C38 C 0.6526(3) 0.9338(2) 0.4602(2) 0.0310(9) Uani 1 1 d . . . H38A H 0.6062 0.9498 0.5033 0.037 Uiso 1 1 calc R . . H38B H 0.6320 0.9683 0.4219 0.037 Uiso 1 1 calc R . . C39 C 0.5791(3) 0.7705(3) 0.3166(2) 0.0311(9) Uani 1 1 d . . . H39 H 0.5603 0.7965 0.2741 0.037 Uiso 1 1 calc R . . C40 C 0.5636(3) 0.6701(3) 0.3010(2) 0.0274(9) Uani 1 1 d . . . C41 C 0.5154(3) 0.5780(3) 0.2176(2) 0.0328(9) Uani 1 1 d . . . C42 C 0.4495(3) 0.5829(3) 0.1452(3) 0.0542(12) Uani 1 1 d . . . H42 H 0.4359 0.6470 0.1496 0.065 Uiso 1 1 calc R . . C43 C 0.4021(4) 0.4950(3) 0.0655(3) 0.0665(14) Uani 1 1 d . . . H43 H 0.3576 0.4998 0.0157 0.080 Uiso 1 1 calc R . . C44 C 0.4194(4) 0.4023(3) 0.0587(3) 0.0594(13) Uani 1 1 d . . . H44 H 0.3847 0.3420 0.0052 0.071 Uiso 1 1 calc R . . C45 C 0.4878(4) 0.3971(3) 0.1303(3) 0.0529(12) Uani 1 1 d . . . H45 H 0.5024 0.3331 0.1256 0.063 Uiso 1 1 calc R . . C46 C 0.5358(3) 0.4850(3) 0.2096(2) 0.0412(10) Uani 1 1 d . . . H46 H 0.5829 0.4806 0.2585 0.049 Uiso 1 1 calc R . . N8 N 0.8472(2) 0.8165(2) 0.73631(19) 0.0350(8) Uani 1 1 d . . . N9 N 0.8634(2) 0.8330(2) 0.66785(18) 0.0283(7) Uani 1 1 d . . . N10 N 0.9709(2) 0.8801(2) 0.68880(18) 0.0315(7) Uani 1 1 d . . . N11 N 0.8308(2) 0.92370(19) 0.54829(17) 0.0251(7) Uani 1 1 d . . . N12 N 0.6265(2) 0.8242(2) 0.40460(18) 0.0269(7) Uani 1 1 d . . . N13 N 0.6410(2) 0.7613(2) 0.44302(18) 0.0266(7) Uani 1 1 d . . . N14 N 0.6019(2) 0.6659(2) 0.37971(18) 0.0280(7) Uani 1 1 d . . . Cl1 Cl 0.18398(8) 0.69874(7) 0.55974(7) 0.0421(3) Uani 1 1 d . . . O1 O 0.0883(2) 0.6801(2) 0.5893(2) 0.0762(10) Uani 1 1 d . . . O2 O 0.1502(3) 0.6727(3) 0.4680(2) 0.1146(14) Uani 1 1 d . . . O3 O 0.2420(2) 0.80278(18) 0.6097(2) 0.0662(9) Uani 1 1 d . . . O4 O 0.2570(2) 0.63515(18) 0.5743(2) 0.0665(9) Uani 1 1 d . . . Cl2 Cl 0.27585(9) 0.10531(8) 0.80352(7) 0.0537(3) Uani 1 1 d . . . O5 O 0.1614(2) 0.1122(2) 0.79793(19) 0.0753(9) Uani 1 1 d . . . O6 O 0.2888(3) 0.0580(2) 0.7156(2) 0.0981(13) Uani 1 1 d . . . O7 O 0.3456(2) 0.2046(2) 0.84879(18) 0.0761(10) Uani 1 1 d . . . O8 O 0.3029(3) 0.0462(3) 0.8490(3) 0.1322(16) Uani 1 1 d . . . C51 C 0.3219(4) 0.7589(4) 0.3647(3) 0.0565(13) Uani 1 1 d . . . C52 C 0.2383(4) 0.6687(4) 0.2984(3) 0.0868(17) Uani 1 1 d . . . H52A H 0.2160 0.6259 0.3264 0.130 Uiso 1 1 calc R . . H52B H 0.2701 0.6299 0.2497 0.130 Uiso 1 1 calc R . . H52C H 0.1725 0.6899 0.2746 0.130 Uiso 1 1 calc R . . N51 N 0.3860(3) 0.8281(3) 0.4157(3) 0.0694(12) Uani 1 1 d . . . O61 O 0.5681(6) 0.1902(4) 0.1441(4) 0.188(2) Uani 1 1 d . . . C64 C 0.7705(9) 0.2885(6) 0.1998(5) 0.235(6) Uani 1 1 d . . . H64A H 0.7660 0.3126 0.1536 0.352 Uiso 1 1 calc R . . H64B H 0.8459 0.2767 0.2163 0.352 Uiso 1 1 calc R . . H64C H 0.7547 0.3400 0.2525 0.352 Uiso 1 1 calc R . . C63 C 0.6966(8) 0.2028(7) 0.1689(6) 0.167(4) Uani 1 1 d . . . H63A H 0.7141 0.1758 0.2135 0.200 Uiso 1 1 calc R . . H63B H 0.7146 0.1550 0.1146 0.200 Uiso 1 1 calc R . . C62 C 0.4726(9) 0.1153(7) 0.1117(8) 0.245(7) Uani 1 1 d . . . H62A H 0.4903 0.0602 0.0615 0.294 Uiso 1 1 calc R . . H62B H 0.4793 0.0919 0.1590 0.294 Uiso 1 1 calc R . . C61 C 0.3695(7) 0.1021(9) 0.0844(9) 0.251(7) Uani 1 1 d . . . H61A H 0.3399 0.1450 0.1331 0.376 Uiso 1 1 calc R . . H61B H 0.3352 0.0303 0.0638 0.376 Uiso 1 1 calc R . . H61C H 0.3519 0.1207 0.0349 0.376 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 Fe1 0.0232(3) 0.0281(3) 0.0265(3) 0.0115(3) 0.0063(2) -0.0007(2) C1 0.050(3) 0.044(3) 0.041(3) 0.013(2) 0.017(2) 0.012(2) C2 0.055(3) 0.042(3) 0.049(3) 0.006(2) 0.009(3) 0.002(2) C3 0.075(4) 0.042(3) 0.036(3) 0.006(2) 0.004(3) 0.015(3) C4 0.078(4) 0.055(3) 0.039(3) 0.015(3) 0.030(3) 0.026(3) C5 0.051(3) 0.046(3) 0.041(3) 0.016(2) 0.019(2) 0.011(2) C6 0.038(2) 0.037(3) 0.030(2) 0.015(2) 0.007(2) 0.012(2) C7 0.030(2) 0.033(2) 0.031(2) 0.016(2) 0.0084(19) 0.0061(19) C8 0.031(2) 0.042(3) 0.038(2) 0.019(2) 0.015(2) 0.012(2) C9 0.020(2) 0.036(2) 0.038(2) 0.014(2) 0.0101(18) -0.0018(18) C10 0.023(2) 0.030(2) 0.029(2) 0.0105(18) 0.0072(17) -0.0004(17) C11 0.030(2) 0.042(3) 0.052(3) 0.021(2) 0.019(2) 0.000(2) C12 0.052(3) 0.041(3) 0.061(3) 0.031(2) 0.028(2) 0.005(2) C13 0.047(3) 0.034(2) 0.046(3) 0.025(2) 0.017(2) 0.006(2) C14 0.026(2) 0.029(2) 0.029(2) 0.0125(19) 0.0058(17) 0.0006(17) C15 0.028(2) 0.030(2) 0.043(2) 0.019(2) 0.0097(18) 0.0050(17) C16 0.032(2) 0.028(2) 0.043(3) 0.004(2) 0.015(2) 0.0007(18) C17 0.030(2) 0.030(2) 0.034(2) 0.004(2) 0.0121(19) -0.0045(18) C18 0.039(3) 0.040(3) 0.036(3) -0.003(2) 0.015(2) -0.013(2) C19 0.051(3) 0.070(4) 0.054(3) -0.003(3) 0.020(3) -0.001(3) C20 0.070(4) 0.096(5) 0.057(4) -0.016(3) 0.032(3) -0.001(3) C21 0.095(5) 0.110(6) 0.051(4) 0.000(4) 0.037(4) -0.030(4) C22 0.114(5) 0.081(4) 0.041(3) 0.007(3) 0.032(3) -0.017(4) C23 0.080(4) 0.052(3) 0.039(3) 0.007(3) 0.028(3) -0.009(3) N1 0.0308(18) 0.0283(19) 0.0264(18) 0.0080(15) 0.0081(15) 0.0036(15) N2 0.0257(18) 0.0302(19) 0.0299(18) 0.0131(16) 0.0099(15) 0.0026(14) N3 0.0230(17) 0.034(2) 0.0343(19) 0.0153(17) 0.0099(15) 0.0037(15) N4 0.0231(17) 0.0252(17) 0.0239(17) 0.0084(14) 0.0051(14) 0.0009(14) N5 0.0227(17) 0.0296(19) 0.036(2) 0.0134(17) 0.0082(15) 0.0020(14) N6 0.0243(17) 0.0266(18) 0.0293(19) 0.0112(15) 0.0083(14) 0.0011(14) N7 0.0268(18) 0.0328(19) 0.0284(18) 0.0101(16) 0.0118(15) -0.0023(14) C24 0.060(3) 0.093(4) 0.040(3) 0.038(3) 0.000(2) -0.001(3) C25 0.073(4) 0.120(5) 0.050(3) 0.052(3) -0.001(3) 0.019(3) C26 0.077(4) 0.161(6) 0.056(4) 0.075(4) 0.030(3) 0.046(4) C27 0.062(4) 0.207(7) 0.092(4) 0.112(5) 0.023(3) 0.011(4) C28 0.054(3) 0.145(5) 0.061(3) 0.069(4) 0.003(3) -0.003(3) C29 0.042(3) 0.069(3) 0.038(3) 0.029(2) 0.012(2) 0.008(2) C30 0.034(2) 0.050(3) 0.027(2) 0.018(2) 0.0060(19) 0.003(2) C31 0.031(2) 0.055(3) 0.029(2) 0.020(2) -0.0006(19) -0.001(2) C32 0.020(2) 0.037(2) 0.027(2) 0.0114(19) 0.0059(17) -0.0033(17) C33 0.025(2) 0.033(2) 0.021(2) 0.0105(18) 0.0085(17) 0.0003(17) C34 0.025(2) 0.035(2) 0.030(2) 0.0123(19) 0.0093(17) -0.0044(18) C35 0.038(2) 0.028(2) 0.033(2) 0.0095(19) 0.013(2) -0.0020(19) C36 0.036(2) 0.029(2) 0.030(2) 0.0126(19) 0.0095(19) 0.0019(18) C37 0.027(2) 0.024(2) 0.027(2) 0.0089(18) 0.0101(17) 0.0008(17) C38 0.034(2) 0.027(2) 0.031(2) 0.0131(19) 0.0071(18) 0.0049(17) C39 0.032(2) 0.034(2) 0.027(2) 0.016(2) 0.0035(18) 0.0008(18) C40 0.025(2) 0.034(2) 0.023(2) 0.0136(19) 0.0053(17) 0.0017(17) C41 0.036(2) 0.030(2) 0.026(2) 0.009(2) 0.0071(18) -0.0005(18) C42 0.066(3) 0.037(3) 0.039(3) 0.009(2) -0.008(2) 0.004(2) C43 0.085(4) 0.052(3) 0.038(3) 0.010(3) -0.011(3) 0.007(3) C44 0.065(3) 0.044(3) 0.036(3) -0.004(2) 0.001(2) -0.004(2) C45 0.073(3) 0.036(3) 0.045(3) 0.012(2) 0.019(3) 0.012(2) C46 0.047(3) 0.039(3) 0.028(2) 0.007(2) 0.007(2) 0.006(2) N8 0.0348(19) 0.041(2) 0.0304(19) 0.0180(16) 0.0087(16) 0.0036(15) N9 0.0214(17) 0.0350(19) 0.0304(18) 0.0165(15) 0.0089(14) 0.0008(14) N10 0.0243(18) 0.0385(19) 0.0263(18) 0.0128(16) 0.0036(15) -0.0027(14) N11 0.0235(17) 0.0286(18) 0.0216(17) 0.0098(15) 0.0077(14) 0.0011(14) N12 0.0265(17) 0.0250(18) 0.0284(18) 0.0124(16) 0.0061(14) 0.0021(14) N13 0.0251(17) 0.0273(18) 0.0277(18) 0.0140(16) 0.0060(14) 0.0014(14) N14 0.0231(17) 0.0250(18) 0.0288(18) 0.0082(15) 0.0046(14) -0.0033(13) Cl1 0.0336(6) 0.0420(7) 0.0537(7) 0.0231(6) 0.0133(5) 0.0087(5) O1 0.0322(17) 0.094(2) 0.106(3) 0.042(2) 0.0342(18) 0.0088(16) O2 0.136(3) 0.140(3) 0.052(2) 0.047(2) 0.003(2) -0.009(3) O3 0.0552(19) 0.0309(17) 0.101(3) 0.0248(17) 0.0075(18) 0.0026(14) O4 0.0398(18) 0.0398(18) 0.120(3) 0.0352(18) 0.0172(18) 0.0145(14) Cl2 0.0474(7) 0.0562(8) 0.0472(7) 0.0202(6) 0.0077(6) -0.0098(6) O5 0.046(2) 0.094(2) 0.063(2) 0.0159(19) 0.0134(17) -0.0028(17) O6 0.118(3) 0.064(2) 0.071(2) -0.0138(19) 0.061(2) -0.032(2) O7 0.072(2) 0.057(2) 0.055(2) -0.0045(17) 0.0088(17) -0.0281(17) O8 0.109(3) 0.158(4) 0.177(4) 0.138(4) 0.001(3) 0.013(3) C51 0.047(3) 0.079(4) 0.050(3) 0.032(3) 0.019(3) 0.015(3) C52 0.098(4) 0.096(4) 0.058(3) 0.038(3) 0.010(3) -0.010(3) N51 0.042(3) 0.086(3) 0.072(3) 0.025(3) 0.017(2) 0.018(2) O61 0.183(6) 0.127(5) 0.307(8) 0.145(5) 0.053(6) 0.059(4) C64 0.461(18) 0.115(7) 0.134(8) 0.049(6) 0.137(9) -0.003(9) C63 0.177(9) 0.186(9) 0.166(8) 0.101(8) 0.017(7) 0.103(8) C62 0.261(13) 0.172(9) 0.329(13) 0.218(10) -0.042(13) -0.072(10) C61 0.130(8) 0.337(15) 0.48(2) 0.318(16) 0.136(12) 0.122(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 N2 1.945(3) . ? Fe1 N6 1.954(3) . ? Fe1 N9 1.955(3) . ? Fe1 N13 1.964(3) . ? Fe1 N4 2.025(3) . ? Fe1 N11 2.035(2) . ? C1 C2 1.384(5) . ? C1 C6 1.391(5) . ? C1 H1 0.9500 . ? C2 C3 1.367(5) . ? C2 H2 0.9500 . ? C3 C4 1.373(5) . ? C3 H3 0.9500 . ? C4 C5 1.391(5) . ? C4 H4 0.9500 . ? C5 C6 1.381(5) . ? C5 H5 0.9500 . ? C6 C7 1.463(5) . ? C7 N1 1.366(4) . ? C7 C8 1.374(4) . ? C8 N3 1.342(4) . ? C8 H8 0.9500 . ? C9 N3 1.459(4) . ? C9 C10 1.500(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N4 1.361(4) . ? C10 C11 1.381(4) . ? C11 C12 1.375(5) . ? C11 H11 0.9500 . ? C12 C13 1.370(5) . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C13 H13 0.9500 . ? C14 N4 1.364(4) . ? C14 C15 1.511(4) . ? C15 N5 1.460(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N5 1.343(4) . ? C16 C17 1.374(5) . ? C16 H16 0.9500 . ? C17 N7 1.362(4) . ? C17 C18 1.479(5) . ? C18 C19 1.378(5) . ? C18 C23 1.382(5) . ? C19 C20 1.423(6) . ? C19 H19 0.9500 . ? C20 C21 1.365(7) . ? C20 H20 0.9500 . ? C21 C22 1.370(7) . ? C21 H21 0.9500 . ? C22 C23 1.382(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 N2 1.318(3) . ? N2 N3 1.343(3) . ? N5 N6 1.336(3) . ? N6 N7 1.325(3) . ? C24 C29 1.379(5) . ? C24 C25 1.385(5) . ? C24 H24 0.9500 . ? C25 C26 1.361(6) . ? C25 H25 0.9500 . ? C26 C27 1.361(6) . ? C26 H26 0.9500 . ? C27 C28 1.396(6) . ? C27 H27 0.9500 . ? C28 C29 1.370(5) . ? C28 H28 0.9500 . ? C29 C30 1.470(5) . ? C30 N8 1.357(4) . ? C30 C31 1.379(4) . ? C31 N10 1.343(4) . ? C31 H31 0.9500 . ? C32 N10 1.453(4) . ? C32 C33 1.502(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N11 1.371(4) . ? C33 C34 1.375(4) . ? C34 C35 1.379(4) . ? C34 H34 0.9500 . ? C35 C36 1.372(4) . ? C35 H35 0.9500 . ? C36 C37 1.381(4) . ? C36 H36 0.9500 . ? C37 N11 1.352(4) . ? C37 C38 1.513(4) . ? C38 N12 1.453(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 N12 1.342(4) . ? C39 C40 1.371(4) . ? C39 H39 0.9500 . ? C40 N14 1.360(4) . ? C40 C41 1.459(4) . ? C41 C46 1.372(4) . ? C41 C42 1.373(5) . ? C42 C43 1.395(5) . ? C42 H42 0.9500 . ? C43 C44 1.363(5) . ? C43 H43 0.9500 . ? C44 C45 1.380(5) . ? C44 H44 0.9500 . ? C45 C46 1.391(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N8 N9 1.330(3) . ? N9 N10 1.345(3) . ? N12 N13 1.341(3) . ? N13 N14 1.332(3) . ? Cl1 O2 1.408(3) . ? Cl1 O1 1.421(3) . ? Cl1 O3 1.428(2) . ? Cl1 O4 1.429(2) . ? Cl2 O8 1.406(3) . ? Cl2 O6 1.419(3) . ? Cl2 O7 1.421(2) . ? Cl2 O5 1.426(3) . ? C51 N51 1.121(5) . ? C51 C52 1.460(6) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? O61 C62 1.376(8) . ? O61 C63 1.542(8) . ? C64 C63 1.314(9) . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C62 C61 1.240(10) . ? C62 H62A 0.9900 . ? C62 H62B 0.9900 . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? 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 N2 Fe1 N6 178.74(12) . . ? N2 Fe1 N9 86.49(11) . . ? N6 Fe1 N9 94.28(11) . . ? N2 Fe1 N13 95.96(11) . . ? N6 Fe1 N13 83.29(11) . . ? N9 Fe1 N13 177.06(12) . . ? N2 Fe1 N4 90.15(11) . . ? N6 Fe1 N4 90.87(11) . . ? N9 Fe1 N4 87.61(11) . . ? N13 Fe1 N4 90.76(11) . . ? N2 Fe1 N11 87.22(11) . . ? N6 Fe1 N11 91.78(11) . . ? N9 Fe1 N11 90.89(11) . . ? N13 Fe1 N11 90.85(11) . . ? N4 Fe1 N11 177.05(11) . . ? C2 C1 C6 120.7(4) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C3 C2 C1 120.5(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.8(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.2(4) . . ? C5 C6 C7 120.6(3) . . ? C1 C6 C7 121.1(4) . . ? N1 C7 C8 108.0(3) . . ? N1 C7 C6 120.5(3) . . ? C8 C7 C6 131.3(4) . . ? N3 C8 C7 105.7(3) . . ? N3 C8 H8 127.1 . . ? C7 C8 H8 127.1 . . ? N3 C9 C10 112.2(3) . . ? N3 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N3 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N4 C10 C11 122.5(3) . . ? N4 C10 C9 118.7(3) . . ? C11 C10 C9 118.8(3) . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 118.6(4) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 119.7(4) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? N4 C14 C13 122.7(3) . . ? N4 C14 C15 119.6(3) . . ? C13 C14 C15 117.7(3) . . ? N5 C15 C14 113.2(3) . . ? N5 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? N5 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.8 . . ? N5 C16 C17 105.1(3) . . ? N5 C16 H16 127.4 . . ? C17 C16 H16 127.4 . . ? N7 C17 C16 108.3(3) . . ? N7 C17 C18 120.1(4) . . ? C16 C17 C18 131.7(4) . . ? C19 C18 C23 119.8(4) . . ? C19 C18 C17 120.3(4) . . ? C23 C18 C17 119.9(4) . . ? C18 C19 C20 119.2(5) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C21 C20 C19 119.3(6) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 121.4(6) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C21 C22 C23 119.3(6) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C18 C23 C22 120.9(5) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? N2 N1 C7 108.0(3) . . ? N1 N2 N3 108.4(3) . . ? N1 N2 Fe1 126.4(2) . . ? N3 N2 Fe1 124.7(2) . . ? C8 N3 N2 109.8(3) . . ? C8 N3 C9 130.6(3) . . ? N2 N3 C9 119.4(3) . . ? C10 N4 C14 116.6(3) . . ? C10 N4 Fe1 121.5(2) . . ? C14 N4 Fe1 121.4(2) . . ? N6 N5 C16 110.7(3) . . ? N6 N5 C15 119.0(3) . . ? C16 N5 C15 130.2(3) . . ? N7 N6 N5 107.9(3) . . ? N7 N6 Fe1 125.2(2) . . ? N5 N6 Fe1 123.7(2) . . ? N6 N7 C17 108.0(3) . . ? C29 C24 C25 121.0(4) . . ? C29 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C26 C25 C24 119.7(5) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C27 C26 C25 120.5(5) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 119.6(5) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C29 C28 C27 120.7(4) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C24 118.4(4) . . ? C28 C29 C30 120.7(4) . . ? C24 C29 C30 120.9(4) . . ? N8 C30 C31 108.7(3) . . ? N8 C30 C29 122.2(3) . . ? C31 C30 C29 129.1(3) . . ? N10 C31 C30 105.2(3) . . ? N10 C31 H31 127.4 . . ? C30 C31 H31 127.4 . . ? N10 C32 C33 112.0(3) . . ? N10 C32 H32A 109.2 . . ? C33 C32 H32A 109.2 . . ? N10 C32 H32B 109.2 . . ? C33 C32 H32B 109.2 . . ? H32A C32 H32B 107.9 . . ? N11 C33 C34 122.7(3) . . ? N11 C33 C32 117.9(3) . . ? C34 C33 C32 119.3(3) . . ? C33 C34 C35 119.6(3) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C36 C35 C34 118.6(3) . . ? C36 C35 H35 120.7 . . ? C34 C35 H35 120.7 . . ? C35 C36 C37 119.4(3) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? N11 C37 C36 123.3(3) . . ? N11 C37 C38 119.7(3) . . ? C36 C37 C38 117.0(3) . . ? N12 C38 C37 113.9(3) . . ? N12 C38 H38A 108.8 . . ? C37 C38 H38A 108.8 . . ? N12 C38 H38B 108.8 . . ? C37 C38 H38B 108.8 . . ? H38A C38 H38B 107.7 . . ? N12 C39 C40 105.4(3) . . ? N12 C39 H39 127.3 . . ? C40 C39 H39 127.3 . . ? N14 C40 C39 108.6(3) . . ? N14 C40 C41 121.7(3) . . ? C39 C40 C41 129.7(3) . . ? C46 C41 C42 118.8(3) . . ? C46 C41 C40 120.8(3) . . ? C42 C41 C40 120.4(3) . . ? C41 C42 C43 120.8(4) . . ? C41 C42 H42 119.6 . . ? C43 C42 H42 119.6 . . ? C44 C43 C42 120.3(4) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C45 119.1(4) . . ? C43 C44 H44 120.4 . . ? C45 C44 H44 120.4 . . ? C44 C45 C46 120.4(4) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? C41 C46 C45 120.5(4) . . ? C41 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? N9 N8 C30 107.7(3) . . ? N8 N9 N10 108.2(3) . . ? N8 N9 Fe1 127.1(2) . . ? N10 N9 Fe1 124.7(2) . . ? C31 N10 N9 110.2(3) . . ? C31 N10 C32 130.6(3) . . ? N9 N10 C32 119.2(3) . . ? C37 N11 C33 116.1(3) . . ? C37 N11 Fe1 122.2(2) . . ? C33 N11 Fe1 120.8(2) . . ? N13 N12 C39 110.4(3) . . ? N13 N12 C38 119.4(3) . . ? C39 N12 C38 130.0(3) . . ? N14 N13 N12 107.9(2) . . ? N14 N13 Fe1 124.8(2) . . ? N12 N13 Fe1 123.1(2) . . ? N13 N14 C40 107.7(3) . . ? O2 Cl1 O1 109.2(2) . . ? O2 Cl1 O3 110.9(2) . . ? O1 Cl1 O3 110.96(18) . . ? O2 Cl1 O4 109.7(2) . . ? O1 Cl1 O4 107.33(18) . . ? O3 Cl1 O4 108.67(16) . . ? O8 Cl2 O6 110.5(3) . . ? O8 Cl2 O7 111.1(2) . . ? O6 Cl2 O7 108.67(18) . . ? O8 Cl2 O5 108.1(2) . . ? O6 Cl2 O5 108.5(2) . . ? O7 Cl2 O5 109.94(19) . . ? N51 C51 C52 179.9(6) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C62 O61 C63 139.9(7) . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C64 C63 O61 126.1(8) . . ? C64 C63 H63A 105.8 . . ? O61 C63 H63A 105.8 . . ? C64 C63 H63B 105.8 . . ? O61 C63 H63B 105.8 . . ? H63A C63 H63B 106.2 . . ? C61 C62 O61 140.6(10) . . ? C61 C62 H62A 101.9 . . ? O61 C62 H62A 101.9 . . ? C61 C62 H62B 101.9 . . ? O61 C62 H62B 101.9 . . ? H62A C62 H62B 104.7 . . ? C62 C61 H61A 109.5 . . ? C62 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C62 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? 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 C6 C1 C2 C3 1.1(6) . . . . ? C1 C2 C3 C4 -2.0(7) . . . . ? C2 C3 C4 C5 1.3(6) . . . . ? C3 C4 C5 C6 0.2(6) . . . . ? C4 C5 C6 C1 -1.1(6) . . . . ? C4 C5 C6 C7 174.7(3) . . . . ? C2 C1 C6 C5 0.4(6) . . . . ? C2 C1 C6 C7 -175.4(3) . . . . ? C5 C6 C7 N1 -163.2(3) . . . . ? C1 C6 C7 N1 12.5(5) . . . . ? C5 C6 C7 C8 10.4(6) . . . . ? C1 C6 C7 C8 -173.9(4) . . . . ? N1 C7 C8 N3 0.5(4) . . . . ? C6 C7 C8 N3 -173.7(3) . . . . ? N3 C9 C10 N4 -58.6(4) . . . . ? N3 C9 C10 C11 123.5(3) . . . . ? N4 C10 C11 C12 -2.5(5) . . . . ? C9 C10 C11 C12 175.3(3) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 1.7(6) . . . . ? C12 C13 C14 N4 -1.3(5) . . . . ? C12 C13 C14 C15 177.2(3) . . . . ? N4 C14 C15 N5 -44.3(4) . . . . ? C13 C14 C15 N5 137.1(3) . . . . ? N5 C16 C17 N7 -0.1(4) . . . . ? N5 C16 C17 C18 -179.2(4) . . . . ? N7 C17 C18 C19 161.7(3) . . . . ? C16 C17 C18 C19 -19.2(6) . . . . ? N7 C17 C18 C23 -18.2(5) . . . . ? C16 C17 C18 C23 160.8(4) . . . . ? C23 C18 C19 C20 -0.3(6) . . . . ? C17 C18 C19 C20 179.8(4) . . . . ? C18 C19 C20 C21 -0.5(7) . . . . ? C19 C20 C21 C22 0.6(9) . . . . ? C20 C21 C22 C23 0.1(8) . . . . ? C19 C18 C23 C22 1.0(6) . . . . ? C17 C18 C23 C22 -179.1(4) . . . . ? C21 C22 C23 C18 -0.9(7) . . . . ? C8 C7 N1 N2 -0.3(4) . . . . ? C6 C7 N1 N2 174.6(3) . . . . ? C7 N1 N2 N3 0.1(3) . . . . ? C7 N1 N2 Fe1 -172.7(2) . . . . ? N9 Fe1 N2 N1 52.5(3) . . . . ? N13 Fe1 N2 N1 -129.1(3) . . . . ? N4 Fe1 N2 N1 140.1(3) . . . . ? N11 Fe1 N2 N1 -38.6(3) . . . . ? N9 Fe1 N2 N3 -119.2(3) . . . . ? N13 Fe1 N2 N3 59.2(3) . . . . ? N4 Fe1 N2 N3 -31.6(3) . . . . ? N11 Fe1 N2 N3 149.8(3) . . . . ? C7 C8 N3 N2 -0.4(4) . . . . ? C7 C8 N3 C9 174.9(3) . . . . ? N1 N2 N3 C8 0.2(4) . . . . ? Fe1 N2 N3 C8 173.2(2) . . . . ? N1 N2 N3 C9 -175.7(3) . . . . ? Fe1 N2 N3 C9 -2.8(4) . . . . ? C10 C9 N3 C8 -121.5(4) . . . . ? C10 C9 N3 N2 53.4(4) . . . . ? C11 C10 N4 C14 2.8(5) . . . . ? C9 C10 N4 C14 -175.0(3) . . . . ? C11 C10 N4 Fe1 -169.2(3) . . . . ? C9 C10 N4 Fe1 13.0(4) . . . . ? C13 C14 N4 C10 -0.9(5) . . . . ? C15 C14 N4 C10 -179.4(3) . . . . ? C13 C14 N4 Fe1 171.1(3) . . . . ? C15 C14 N4 Fe1 -7.4(4) . . . . ? N2 Fe1 N4 C10 25.5(3) . . . . ? N6 Fe1 N4 C10 -153.8(2) . . . . ? N9 Fe1 N4 C10 111.9(3) . . . . ? N13 Fe1 N4 C10 -70.5(3) . . . . ? N2 Fe1 N4 C14 -146.2(3) . . . . ? N6 Fe1 N4 C14 34.5(3) . . . . ? N9 Fe1 N4 C14 -59.7(3) . . . . ? N13 Fe1 N4 C14 117.8(3) . . . . ? C17 C16 N5 N6 0.0(4) . . . . ? C17 C16 N5 C15 -176.2(3) . . . . ? C14 C15 N5 N6 62.0(4) . . . . ? C14 C15 N5 C16 -122.1(4) . . . . ? C16 N5 N6 N7 0.1(3) . . . . ? C15 N5 N6 N7 176.8(3) . . . . ? C16 N5 N6 Fe1 160.8(2) . . . . ? C15 N5 N6 Fe1 -22.6(4) . . . . ? N9 Fe1 N6 N7 -135.0(2) . . . . ? N13 Fe1 N6 N7 46.6(2) . . . . ? N4 Fe1 N6 N7 137.3(2) . . . . ? N11 Fe1 N6 N7 -44.0(2) . . . . ? N9 Fe1 N6 N5 67.7(2) . . . . ? N13 Fe1 N6 N5 -110.7(2) . . . . ? N4 Fe1 N6 N5 -20.0(2) . . . . ? N11 Fe1 N6 N5 158.7(2) . . . . ? N5 N6 N7 C17 -0.2(3) . . . . ? Fe1 N6 N7 C17 -160.5(2) . . . . ? C16 C17 N7 N6 0.2(4) . . . . ? C18 C17 N7 N6 179.4(3) . . . . ? C29 C24 C25 C26 -1.2(8) . . . . ? C24 C25 C26 C27 2.6(8) . . . . ? C25 C26 C27 C28 -2.3(9) . . . . ? C26 C27 C28 C29 0.7(8) . . . . ? C27 C28 C29 C24 0.7(7) . . . . ? C27 C28 C29 C30 -178.2(5) . . . . ? C25 C24 C29 C28 -0.4(7) . . . . ? C25 C24 C29 C30 178.5(4) . . . . ? C28 C29 C30 N8 8.6(6) . . . . ? C24 C29 C30 N8 -170.3(4) . . . . ? C28 C29 C30 C31 -172.1(4) . . . . ? C24 C29 C30 C31 9.0(7) . . . . ? N8 C30 C31 N10 -0.9(4) . . . . ? C29 C30 C31 N10 179.7(4) . . . . ? N10 C32 C33 N11 -63.2(4) . . . . ? N10 C32 C33 C34 119.4(3) . . . . ? N11 C33 C34 C35 -3.6(5) . . . . ? C32 C33 C34 C35 173.8(3) . . . . ? C33 C34 C35 C36 -2.3(5) . . . . ? C34 C35 C36 C37 5.5(5) . . . . ? C35 C36 C37 N11 -3.1(5) . . . . ? C35 C36 C37 C38 174.8(3) . . . . ? N11 C37 C38 N12 -40.0(4) . . . . ? C36 C37 C38 N12 142.1(3) . . . . ? N12 C39 C40 N14 0.0(4) . . . . ? N12 C39 C40 C41 179.9(3) . . . . ? N14 C40 C41 C46 -19.3(5) . . . . ? C39 C40 C41 C46 160.9(4) . . . . ? N14 C40 C41 C42 161.3(4) . . . . ? C39 C40 C41 C42 -18.5(6) . . . . ? C46 C41 C42 C43 1.2(6) . . . . ? C40 C41 C42 C43 -179.4(4) . . . . ? C41 C42 C43 C44 1.0(7) . . . . ? C42 C43 C44 C45 -2.6(7) . . . . ? C43 C44 C45 C46 2.0(7) . . . . ? C42 C41 C46 C45 -1.8(6) . . . . ? C40 C41 C46 C45 178.8(3) . . . . ? C44 C45 C46 C41 0.2(6) . . . . ? C31 C30 N8 N9 1.3(4) . . . . ? C29 C30 N8 N9 -179.3(3) . . . . ? C30 N8 N9 N10 -1.2(4) . . . . ? C30 N8 N9 Fe1 -179.0(2) . . . . ? N2 Fe1 N9 N8 60.5(3) . . . . ? N6 Fe1 N9 N8 -120.5(3) . . . . ? N4 Fe1 N9 N8 -29.8(3) . . . . ? N11 Fe1 N9 N8 147.6(3) . . . . ? N2 Fe1 N9 N10 -116.9(3) . . . . ? N6 Fe1 N9 N10 62.1(3) . . . . ? N4 Fe1 N9 N10 152.8(3) . . . . ? N11 Fe1 N9 N10 -29.8(3) . . . . ? C30 C31 N10 N9 0.1(4) . . . . ? C30 C31 N10 C32 -177.6(3) . . . . ? N8 N9 N10 C31 0.7(4) . . . . ? Fe1 N9 N10 C31 178.5(2) . . . . ? N8 N9 N10 C32 178.7(3) . . . . ? Fe1 N9 N10 C32 -3.5(4) . . . . ? C33 C32 N10 C31 -127.6(4) . . . . ? C33 C32 N10 N9 54.8(4) . . . . ? C36 C37 N11 C33 -2.6(5) . . . . ? C38 C37 N11 C33 179.7(3) . . . . ? C36 C37 N11 Fe1 166.7(3) . . . . ? C38 C37 N11 Fe1 -11.0(4) . . . . ? C34 C33 N11 C37 5.9(5) . . . . ? C32 C33 N11 C37 -171.5(3) . . . . ? C34 C33 N11 Fe1 -163.6(3) . . . . ? C32 C33 N11 Fe1 19.1(4) . . . . ? N2 Fe1 N11 C37 -61.7(3) . . . . ? N6 Fe1 N11 C37 117.6(3) . . . . ? N9 Fe1 N11 C37 -148.1(3) . . . . ? N13 Fe1 N11 C37 34.3(3) . . . . ? N2 Fe1 N11 C33 107.1(3) . . . . ? N6 Fe1 N11 C33 -73.6(3) . . . . ? N9 Fe1 N11 C33 20.7(3) . . . . ? N13 Fe1 N11 C33 -156.9(3) . . . . ? C40 C39 N12 N13 0.3(4) . . . . ? C40 C39 N12 C38 -173.8(3) . . . . ? C37 C38 N12 N13 62.7(4) . . . . ? C37 C38 N12 C39 -123.6(4) . . . . ? C39 N12 N13 N14 -0.5(3) . . . . ? C38 N12 N13 N14 174.3(3) . . . . ? C39 N12 N13 Fe1 157.4(2) . . . . ? C38 N12 N13 Fe1 -27.8(4) . . . . ? N2 Fe1 N13 N14 -133.7(2) . . . . ? N6 Fe1 N13 N14 47.3(2) . . . . ? N4 Fe1 N13 N14 -43.5(2) . . . . ? N11 Fe1 N13 N14 139.0(2) . . . . ? N2 Fe1 N13 N12 72.1(3) . . . . ? N6 Fe1 N13 N12 -106.9(3) . . . . ? N4 Fe1 N13 N12 162.3(3) . . . . ? N11 Fe1 N13 N12 -15.2(3) . . . . ? N12 N13 N14 C40 0.5(3) . . . . ? Fe1 N13 N14 C40 -157.0(2) . . . . ? C39 C40 N14 N13 -0.3(4) . . . . ? C41 C40 N14 N13 179.8(3) . . . . ? C62 O61 C63 C64 179.9(11) . . . . ? C63 O61 C62 C61 -171.8(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.82 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.891 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.063 # Attachment 'fig-2C---zhu49.cif' data_zhu49 _database_code_depnum_ccdc_archive 'CCDC 811004' #TrackingRef 'fig-2C---zhu49.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H50 Cl2 Co N15 O9' _chemical_formula_weight 1158.90 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.3100(8) _cell_length_b 14.6560(9) _cell_length_c 17.4106(11) _cell_angle_alpha 114.7030(10) _cell_angle_beta 101.9890(10) _cell_angle_gamma 94.2900(10) _cell_volume 2744.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8501 _exptl_absorpt_correction_T_max 0.9359 _exptl_absorpt_process_details ? _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 32788 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.28 _reflns_number_total 13224 _reflns_number_gt 10562 _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^)+(0.0000P)^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 13224 _refine_ls_number_parameters 704 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 2.373 _refine_ls_restrained_S_all 2.381 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.245447(19) 0.200803(18) 0.445248(16) 0.02733(7) Uani 1 1 d . A . C1 C 0.55269(14) 0.41977(9) 0.85410(8) 0.0767(11) Uani 0.811(2) 1 d PG A 1 H1 H 0.5649 0.3552 0.8509 0.092 Uiso 0.811(2) 1 calc PR A 1 C2 C 0.60562(18) 0.50867(11) 0.92944(8) 0.1074(16) Uani 0.811(2) 1 d PG A 1 H2 H 0.6540 0.5049 0.9778 0.129 Uiso 0.811(2) 1 calc PR A 1 C3 C 0.58769(16) 0.60313(9) 0.93405(9) 0.0746(11) Uani 0.811(2) 1 d PG A 1 H3 H 0.6239 0.6639 0.9855 0.090 Uiso 0.811(2) 1 calc PR A 1 C4 C 0.51683(15) 0.60870(7) 0.86333(10) 0.0611(9) Uani 0.811(2) 1 d PG A 1 H4 H 0.5046 0.6733 0.8665 0.073 Uiso 0.811(2) 1 calc PR A 1 C5 C 0.46390(13) 0.51981(8) 0.78799(9) 0.0452(7) Uani 0.811(2) 1 d PG A 1 H5 H 0.4155 0.5236 0.7397 0.054 Uiso 0.811(2) 1 calc PR A 1 C6 C 0.48183(8) 0.42534(7) 0.78338(6) 0.0389(7) Uani 0.811(2) 1 d PG A 1 C1A C 0.49391(16) 0.43828(9) 0.87331(6) 0.050(4) Uiso 0.189(2) 1 d PG A 2 C2A C 0.5549(2) 0.52246(11) 0.94770(6) 0.059(4) Uiso 0.189(2) 1 d PG A 2 C3A C 0.63290(16) 0.59170(11) 0.94464(10) 0.051(4) Uiso 0.189(2) 1 d PG A 2 C4A C 0.66074(12) 0.57353(10) 0.87254(13) 0.074(4) Uiso 0.189(2) 1 d PG A 2 C5A C 0.60083(11) 0.48692(9) 0.79215(11) 0.063(4) Uiso 0.189(2) 1 d PG A 2 C6A C 0.50914(8) 0.42136(7) 0.79109(6) 0.025(3) Uiso 0.189(2) 1 d PG A 2 C7 C 0.43467(9) 0.33144(8) 0.70356(6) 0.0331(4) Uani 1 1 d G . . C8 C 0.41214(12) 0.23124(7) 0.68964(8) 0.0342(5) Uani 1 1 d G A . H8 H 0.4252 0.2060 0.7323 0.041 Uiso 1 1 calc R . . C9 C 0.34276(14) 0.06683(13) 0.54992(12) 0.0330(4) Uani 1 1 d . . . H9A H 0.3629 0.0341 0.5892 0.040 Uiso 1 1 calc R . . H9B H 0.3921 0.0488 0.5095 0.040 Uiso 1 1 calc R . . C10 C 0.22170(14) 0.02164(13) 0.49624(12) 0.0272(4) Uani 1 1 d . A . C11 C 0.17798(15) -0.07307(13) 0.48697(12) 0.0315(4) Uani 1 1 d . . . H11 H 0.2207 -0.1042 0.5181 0.038 Uiso 1 1 calc R . . C12 C 0.07186(15) -0.12214(14) 0.43210(12) 0.0340(5) Uani 1 1 d . . . H12 H 0.0419 -0.1888 0.4224 0.041 Uiso 1 1 calc R . . C13 C 0.01039(15) -0.07212(13) 0.39166(12) 0.0307(4) Uani 1 1 d . . . H13 H -0.0632 -0.1038 0.3540 0.037 Uiso 1 1 calc R . . C14 C 0.05660(14) 0.02418(13) 0.40627(11) 0.0258(4) Uani 1 1 d . A . C15 C -0.01645(14) 0.08431(13) 0.37150(12) 0.0284(4) Uani 1 1 d . . . H15A H -0.0946 0.0451 0.3450 0.034 Uiso 1 1 calc R . . H15B H -0.0181 0.1493 0.4213 0.034 Uiso 1 1 calc R . . C16 C -0.03507(16) 0.08960(14) 0.22520(12) 0.0337(4) Uani 1 1 d . . . H16 H -0.1093 0.0521 0.1939 0.040 Uiso 1 1 calc R . . C17 C 0.03783(15) 0.13762(14) 0.19709(12) 0.0319(4) Uani 1 1 d . . . C18 C 0.02174(17) 0.14394(15) 0.11353(13) 0.0370(5) Uani 1 1 d . . . C19 C 0.10664(19) 0.19716(17) 0.09890(14) 0.0528(6) Uani 1 1 d . . . H19 H 0.1744 0.2323 0.1440 0.063 Uiso 1 1 calc R . . C20 C 0.0928(2) 0.19928(19) 0.01847(16) 0.0633(7) Uani 1 1 d . . . H20 H 0.1517 0.2352 0.0085 0.076 Uiso 1 1 calc R . . C21 C -0.0051(2) 0.14999(19) -0.04660(16) 0.0586(7) Uani 1 1 d . . . H21 H -0.0141 0.1516 -0.1015 0.070 Uiso 1 1 calc R . . C22 C -0.0900(2) 0.09831(19) -0.03212(15) 0.0582(6) Uani 1 1 d . . . H22 H -0.1584 0.0649 -0.0769 0.070 Uiso 1 1 calc R . . C23 C -0.07658(18) 0.09458(17) 0.04740(14) 0.0480(6) Uani 1 1 d . . . H23 H -0.1354 0.0578 0.0566 0.058 Uiso 1 1 calc R . . N1 N 0.40373(12) 0.33415(11) 0.62518(10) 0.0327(4) Uani 1 1 d . A . N2 N 0.36388(12) 0.23951(11) 0.56407(10) 0.0301(4) Uani 1 1 d . . . N3 N 0.36786(12) 0.17723(11) 0.60310(10) 0.0296(4) Uani 1 1 d . A . N4 N 0.16342(11) 0.07057(10) 0.45580(9) 0.0256(3) Uani 1 1 d . . . N5 N 0.02150(12) 0.10743(11) 0.30603(10) 0.0277(3) Uani 1 1 d . A . N6 N 0.12383(12) 0.16407(11) 0.32861(10) 0.0297(4) Uani 1 1 d . . . N7 N 0.13488(12) 0.18236(11) 0.26202(10) 0.0329(4) Uani 1 1 d . A . C31 C 0.25791(19) -0.19014(17) 0.16434(15) 0.0529(6) Uani 1 1 d . . . H31 H 0.2102 -0.1758 0.2028 0.064 Uiso 1 1 calc R . . C32 C 0.2316(2) -0.28125(19) 0.08867(17) 0.0719(8) Uani 1 1 d . . . H32 H 0.1658 -0.3291 0.0752 0.086 Uiso 1 1 calc R . . C33 C 0.3003(3) -0.3027(2) 0.03308(18) 0.0827(9) Uani 1 1 d . . . H33 H 0.2809 -0.3645 -0.0197 0.099 Uiso 1 1 calc R . . C34 C 0.3969(3) -0.2352(2) 0.05358(18) 0.0789(8) Uani 1 1 d . . . H34 H 0.4458 -0.2513 0.0160 0.095 Uiso 1 1 calc R . . C35 C 0.4237(2) -0.14338(18) 0.12890(15) 0.0585(6) Uani 1 1 d . . . H35 H 0.4907 -0.0967 0.1424 0.070 Uiso 1 1 calc R . . C36 C 0.35399(18) -0.11928(15) 0.18440(13) 0.0402(5) Uani 1 1 d . . . C37 C 0.37617(15) -0.01872(15) 0.26094(12) 0.0337(4) Uani 1 1 d . . . C38 C 0.46228(16) 0.06383(15) 0.29198(13) 0.0376(5) Uani 1 1 d . . . H38 H 0.5264 0.0674 0.2703 0.045 Uiso 1 1 calc R . . C39 C 0.49471(14) 0.24290(14) 0.41614(13) 0.0353(5) Uani 1 1 d . . . H39A H 0.5676 0.2529 0.4026 0.042 Uiso 1 1 calc R . . H39B H 0.5115 0.2537 0.4778 0.042 Uiso 1 1 calc R . . C40 C 0.42805(14) 0.32247(14) 0.40712(12) 0.0301(4) Uani 1 1 d . A . C41 C 0.47408(17) 0.39173(15) 0.38249(14) 0.0433(5) Uani 1 1 d . . . H41 H 0.5430 0.3853 0.3660 0.052 Uiso 1 1 calc R . . C42 C 0.41928(19) 0.46993(16) 0.38214(15) 0.0526(6) Uani 1 1 d . . . H42 H 0.4503 0.5188 0.3663 0.063 Uiso 1 1 calc R . . C43 C 0.31847(17) 0.47617(15) 0.40514(13) 0.0407(5) Uani 1 1 d . . . H43 H 0.2793 0.5298 0.4058 0.049 Uiso 1 1 calc R . . C44 C 0.27502(14) 0.40324(13) 0.42723(11) 0.0284(4) Uani 1 1 d . A . C45 C 0.15980(14) 0.40764(14) 0.44499(12) 0.0293(4) Uani 1 1 d . . . H45A H 0.1398 0.4743 0.4520 0.035 Uiso 1 1 calc R . . H45B H 0.1036 0.3537 0.3932 0.035 Uiso 1 1 calc R . . C46 C 0.12721(15) 0.45821(14) 0.59562(12) 0.0326(4) Uani 1 1 d . . . H46 H 0.1177 0.5270 0.6121 0.039 Uiso 1 1 calc R . . C47 C 0.11929(14) 0.40274(14) 0.64215(12) 0.0315(4) Uani 1 1 d . . . C48 C 0.09195(17) 0.43185(15) 0.72673(13) 0.0424(5) Uani 1 1 d . . . C49 C 0.1160(2) 0.37438(18) 0.77265(14) 0.0581(6) Uani 1 1 d . . . H49 H 0.1515 0.3170 0.7500 0.070 Uiso 1 1 calc R . . C50 C 0.0880(3) 0.4010(2) 0.85144(17) 0.0860(9) Uani 1 1 d . . . H50 H 0.1032 0.3613 0.8825 0.103 Uiso 1 1 calc R . . C51 C 0.0382(3) 0.4849(3) 0.88454(18) 0.0995(12) Uani 1 1 d . . . H51 H 0.0196 0.5031 0.9387 0.119 Uiso 1 1 calc R . . C52 C 0.0151(3) 0.5426(2) 0.84068(19) 0.0936(10) Uani 1 1 d . . . H52 H -0.0190 0.6007 0.8643 0.112 Uiso 1 1 calc R . . C53 C 0.0417(2) 0.51603(18) 0.76189(16) 0.0636(7) Uani 1 1 d . . . H53 H 0.0254 0.5560 0.7312 0.076 Uiso 1 1 calc R . . N31 N 0.30228(12) 0.00838(12) 0.31086(10) 0.0348(4) Uani 1 1 d . A . N32 N 0.33956(12) 0.10353(12) 0.37053(10) 0.0334(4) Uani 1 1 d . . . N33 N 0.43630(12) 0.13788(11) 0.35913(10) 0.0314(4) Uani 1 1 d . A . N34 N 0.32806(11) 0.32679(11) 0.42835(9) 0.0267(3) Uani 1 1 d . . . N35 N 0.15108(11) 0.39471(11) 0.52233(10) 0.0277(3) Uani 1 1 d . A . N36 N 0.15666(11) 0.30306(11) 0.52191(10) 0.0284(3) Uani 1 1 d . . . N37 N 0.13823(12) 0.30753(11) 0.59518(10) 0.0304(4) Uani 1 1 d . A . Cl1 Cl 0.74142(5) 0.86633(5) 0.18366(4) 0.05635(16) Uani 1 1 d . . . O1 O 0.67489(15) 0.76738(13) 0.14929(10) 0.0824(6) Uani 1 1 d . . . O2 O 0.71074(15) 0.91056(17) 0.12544(14) 0.1011(7) Uani 1 1 d . . . O3 O 0.72427(14) 0.92831(12) 0.26770(10) 0.0734(5) Uani 1 1 d . . . O4 O 0.85889(13) 0.86039(13) 0.19442(10) 0.0688(5) Uani 1 1 d . . . Cl2 Cl 0.81370(4) 0.29329(4) 0.43095(4) 0.03780(12) Uani 1 1 d . . . O5 O 0.75569(11) 0.18935(10) 0.38310(10) 0.0524(4) Uani 1 1 d . . . O6 O 0.73839(10) 0.36010(9) 0.42042(9) 0.0449(4) Uani 1 1 d . . . O7 O 0.90839(11) 0.30760(11) 0.39876(11) 0.0574(4) Uani 1 1 d . . . O8 O 0.85195(15) 0.31910(13) 0.52245(11) 0.0741(5) Uani 1 1 d . . . C61 C 0.6786(2) 0.2396(2) 0.6338(2) 0.0623(7) Uani 1 1 d . . . C62 C 0.7686(3) 0.3221(2) 0.69957(19) 0.0995(10) Uani 1 1 d . . . H62A H 0.8228 0.2946 0.7300 0.149 Uiso 1 1 calc R . . H62B H 0.7365 0.3728 0.7420 0.149 Uiso 1 1 calc R . . H62C H 0.8072 0.3546 0.6711 0.149 Uiso 1 1 calc R . . N61 N 0.60979(18) 0.17574(19) 0.58211(16) 0.0743(7) Uani 1 1 d . . . C71 C 0.3661(3) 0.1153(3) 0.1003(3) 0.1583(19) Uani 1 1 d D . . H71A H 0.3664 0.1675 0.1585 0.237 Uiso 1 1 calc R . . H71B H 0.3266 0.0492 0.0905 0.237 Uiso 1 1 calc R . . H71C H 0.3273 0.1343 0.0555 0.237 Uiso 1 1 calc R . . C72 C 0.4815(4) 0.1079(4) 0.0951(3) 0.176(2) Uani 1 1 d D . . H72A H 0.4952 0.0398 0.0889 0.212 Uiso 1 1 calc R . . H72B H 0.4901 0.1128 0.0416 0.212 Uiso 1 1 calc R . . C73 C 0.6724(3) 0.1710(3) 0.1564(3) 0.1591(19) Uani 1 1 d D . . H73A H 0.7057 0.1346 0.1896 0.191 Uiso 1 1 calc R . . H73B H 0.6707 0.1301 0.0942 0.191 Uiso 1 1 calc R . . C74 C 0.7401(3) 0.2652(3) 0.1878(2) 0.1167(12) Uani 1 1 d D . . H74A H 0.7443 0.2806 0.1388 0.175 Uiso 1 1 calc R . . H74B H 0.8161 0.2641 0.2184 0.175 Uiso 1 1 calc R . . H74C H 0.7079 0.3178 0.2287 0.175 Uiso 1 1 calc R . . O71 O 0.5595(2) 0.1785(2) 0.1633(2) 0.1640(13) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02363(13) 0.02651(14) 0.03378(15) 0.01502(12) 0.00935(11) 0.00069(10) C1 0.100(3) 0.049(2) 0.048(2) 0.0113(16) -0.0203(19) 0.0029(19) C2 0.140(4) 0.068(3) 0.056(2) 0.007(2) -0.041(2) 0.006(3) C3 0.073(2) 0.051(2) 0.055(2) -0.0091(17) -0.0002(18) 0.0066(18) C4 0.084(2) 0.0397(18) 0.0460(19) 0.0048(15) 0.0201(17) 0.0099(16) C5 0.0602(18) 0.0364(16) 0.0350(15) 0.0109(13) 0.0140(13) 0.0108(13) C6 0.0354(14) 0.0450(18) 0.0348(16) 0.0162(14) 0.0108(12) 0.0034(12) C7 0.0312(10) 0.0346(11) 0.0347(12) 0.0156(10) 0.0120(9) 0.0022(9) C8 0.0334(11) 0.0388(12) 0.0356(12) 0.0221(10) 0.0083(9) 0.0044(9) C9 0.0281(10) 0.0270(11) 0.0446(12) 0.0181(9) 0.0065(9) 0.0043(8) C10 0.0254(9) 0.0258(10) 0.0328(11) 0.0137(9) 0.0116(8) 0.0044(8) C11 0.0313(10) 0.0297(11) 0.0401(12) 0.0200(9) 0.0129(9) 0.0059(8) C12 0.0374(11) 0.0248(10) 0.0408(12) 0.0149(9) 0.0141(10) -0.0010(9) C13 0.0277(10) 0.0298(11) 0.0318(11) 0.0120(9) 0.0087(8) -0.0016(8) C14 0.0241(9) 0.0268(10) 0.0279(10) 0.0114(8) 0.0119(8) 0.0028(8) C15 0.0229(9) 0.0310(10) 0.0335(11) 0.0157(9) 0.0104(8) 0.0013(8) C16 0.0283(10) 0.0365(12) 0.0349(12) 0.0181(10) 0.0023(9) 0.0018(9) C17 0.0319(11) 0.0307(11) 0.0336(11) 0.0145(9) 0.0092(9) 0.0055(9) C18 0.0440(12) 0.0377(12) 0.0350(12) 0.0190(10) 0.0141(10) 0.0112(10) C19 0.0552(14) 0.0643(16) 0.0445(14) 0.0302(13) 0.0152(11) 0.0012(12) C20 0.0736(18) 0.0782(19) 0.0547(17) 0.0411(15) 0.0281(14) 0.0073(15) C21 0.0751(18) 0.0766(18) 0.0427(15) 0.0379(14) 0.0230(14) 0.0288(15) C22 0.0580(16) 0.0749(18) 0.0461(15) 0.0332(14) 0.0072(12) 0.0165(13) C23 0.0475(14) 0.0601(15) 0.0434(14) 0.0304(12) 0.0095(11) 0.0108(11) N1 0.0329(9) 0.0296(9) 0.0353(10) 0.0152(8) 0.0093(7) -0.0006(7) N2 0.0282(8) 0.0276(9) 0.0372(10) 0.0172(8) 0.0095(7) 0.0002(7) N3 0.0247(8) 0.0294(9) 0.0380(10) 0.0193(8) 0.0066(7) 0.0020(7) N4 0.0221(8) 0.0244(8) 0.0314(9) 0.0125(7) 0.0098(7) 0.0025(6) N5 0.0229(8) 0.0280(9) 0.0328(9) 0.0153(7) 0.0062(7) 0.0005(7) N6 0.0263(8) 0.0310(9) 0.0331(9) 0.0159(7) 0.0089(7) -0.0007(7) N7 0.0339(9) 0.0347(9) 0.0318(9) 0.0159(8) 0.0111(8) 0.0019(7) C31 0.0594(15) 0.0442(14) 0.0480(15) 0.0136(12) 0.0135(12) 0.0120(12) C32 0.084(2) 0.0470(16) 0.0620(18) 0.0082(14) 0.0108(16) 0.0067(14) C33 0.124(3) 0.0543(19) 0.0505(18) 0.0068(15) 0.0173(19) 0.0259(19) C34 0.113(3) 0.068(2) 0.0601(19) 0.0184(16) 0.0456(18) 0.0346(18) C35 0.0714(17) 0.0562(16) 0.0520(16) 0.0204(13) 0.0288(13) 0.0218(13) C36 0.0487(13) 0.0402(13) 0.0360(12) 0.0192(10) 0.0113(10) 0.0192(11) C37 0.0337(11) 0.0388(12) 0.0339(11) 0.0195(10) 0.0109(9) 0.0119(9) C38 0.0325(11) 0.0463(13) 0.0434(13) 0.0236(11) 0.0187(10) 0.0132(10) C39 0.0215(10) 0.0416(12) 0.0431(12) 0.0212(10) 0.0070(9) -0.0023(9) C40 0.0241(10) 0.0313(11) 0.0321(11) 0.0136(9) 0.0055(8) -0.0027(8) C41 0.0346(11) 0.0462(13) 0.0587(15) 0.0285(12) 0.0225(11) 0.0016(10) C42 0.0567(14) 0.0490(14) 0.0772(17) 0.0431(13) 0.0365(13) 0.0087(12) C43 0.0449(12) 0.0377(12) 0.0523(14) 0.0283(11) 0.0209(11) 0.0079(10) C44 0.0269(10) 0.0287(10) 0.0285(10) 0.0136(9) 0.0053(8) -0.0016(8) C45 0.0293(10) 0.0283(10) 0.0340(11) 0.0178(9) 0.0077(8) 0.0034(8) C46 0.0312(10) 0.0248(10) 0.0390(12) 0.0108(9) 0.0124(9) 0.0015(8) C47 0.0277(10) 0.0294(11) 0.0332(11) 0.0112(9) 0.0085(9) -0.0031(8) C48 0.0488(13) 0.0353(12) 0.0343(12) 0.0084(10) 0.0141(10) -0.0086(10) C49 0.0797(18) 0.0515(15) 0.0390(14) 0.0180(12) 0.0178(13) -0.0045(13) C50 0.134(3) 0.075(2) 0.0435(17) 0.0229(16) 0.0292(18) -0.0122(19) C51 0.149(3) 0.085(2) 0.0464(18) 0.0061(17) 0.052(2) -0.021(2) C52 0.133(3) 0.068(2) 0.075(2) 0.0097(17) 0.070(2) 0.0074(19) C53 0.0839(19) 0.0503(15) 0.0586(17) 0.0168(13) 0.0404(15) 0.0079(14) N31 0.0330(9) 0.0305(9) 0.0405(10) 0.0144(8) 0.0119(8) 0.0055(7) N32 0.0259(8) 0.0329(9) 0.0427(10) 0.0163(8) 0.0138(7) 0.0015(7) N33 0.0227(8) 0.0360(10) 0.0392(10) 0.0194(8) 0.0101(7) 0.0036(7) N34 0.0218(8) 0.0291(9) 0.0279(9) 0.0141(7) 0.0034(7) -0.0025(7) N35 0.0258(8) 0.0259(8) 0.0331(9) 0.0147(7) 0.0089(7) 0.0011(7) N36 0.0263(8) 0.0261(8) 0.0353(9) 0.0156(7) 0.0103(7) 0.0020(7) N37 0.0275(8) 0.0320(9) 0.0335(9) 0.0160(8) 0.0104(7) 0.0000(7) Cl1 0.0543(4) 0.0628(4) 0.0434(4) 0.0246(3) 0.0036(3) -0.0177(3) O1 0.0911(13) 0.0673(12) 0.0498(11) 0.0036(9) 0.0081(9) -0.0428(10) O2 0.0756(13) 0.154(2) 0.1176(17) 0.1089(16) 0.0127(12) 0.0098(13) O3 0.0756(12) 0.0584(11) 0.0582(11) 0.0020(9) 0.0250(9) -0.0230(9) O4 0.0564(11) 0.0864(13) 0.0570(11) 0.0307(10) 0.0096(9) -0.0030(9) Cl2 0.0273(2) 0.0333(3) 0.0585(4) 0.0257(3) 0.0114(2) 0.0051(2) O5 0.0415(8) 0.0273(8) 0.0853(12) 0.0247(8) 0.0128(8) 0.0022(6) O6 0.0290(7) 0.0332(8) 0.0774(11) 0.0273(8) 0.0168(7) 0.0097(6) O7 0.0330(8) 0.0551(10) 0.1026(13) 0.0446(9) 0.0324(9) 0.0144(7) O8 0.0847(13) 0.0803(13) 0.0559(11) 0.0387(10) 0.0008(9) 0.0058(10) C61 0.0551(17) 0.083(2) 0.069(2) 0.0451(18) 0.0296(15) 0.0229(15) C62 0.107(3) 0.109(3) 0.079(2) 0.050(2) 0.011(2) -0.014(2) N61 0.0433(13) 0.097(2) 0.0859(18) 0.0382(16) 0.0258(13) 0.0255(13) C71 0.071(3) 0.225(5) 0.228(5) 0.171(4) 0.000(3) -0.006(3) C72 0.140(4) 0.240(6) 0.181(5) 0.146(5) 0.009(4) -0.015(4) C73 0.078(3) 0.134(4) 0.225(5) 0.056(4) 0.016(3) -0.002(3) C74 0.091(3) 0.159(4) 0.101(3) 0.068(3) 0.011(2) 0.009(3) O71 0.0648(17) 0.136(2) 0.223(3) 0.040(2) -0.007(2) 0.0026(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N6 2.0875(15) . ? Co1 N2 2.0903(15) . ? Co1 N32 2.0952(15) . ? Co1 N36 2.0979(14) . ? Co1 N4 2.1859(13) . ? Co1 N34 2.1972(14) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 H1 0.9500 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 H4 0.9500 . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 C7 1.4522 . ? C1A C2A 1.3729 . ? C1A C6A 1.4026 . ? C2A C3A 1.3698 . ? C3A C4A 1.2950 . ? C4A C5A 1.4354 . ? C5A C6A 1.4185 . ? C6A C7 1.5684 . ? C7 N1 1.3567(17) . ? C7 C8 1.3805 . ? C8 N3 1.3383(18) . ? C8 H8 0.9500 . ? C9 N3 1.458(2) . ? C9 C10 1.513(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N4 1.347(2) . ? C10 C11 1.381(2) . ? C11 C12 1.379(2) . ? C11 H11 0.9500 . ? C12 C13 1.378(2) . ? C12 H12 0.9500 . ? C13 C14 1.378(2) . ? C13 H13 0.9500 . ? C14 N4 1.356(2) . ? C14 C15 1.513(2) . ? C15 N5 1.467(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N5 1.339(2) . ? C16 C17 1.384(2) . ? C16 H16 0.9500 . ? C17 N7 1.355(2) . ? C17 C18 1.470(2) . ? C18 C23 1.381(3) . ? C18 C19 1.386(3) . ? C19 C20 1.389(3) . ? C19 H19 0.9500 . ? C20 C21 1.370(3) . ? C20 H20 0.9500 . ? C21 C22 1.372(3) . ? C21 H21 0.9500 . ? C22 C23 1.384(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 N2 1.3208(19) . ? N2 N3 1.3449(18) . ? N5 N6 1.3399(18) . ? N6 N7 1.3244(18) . ? C31 C32 1.382(3) . ? C31 C36 1.393(3) . ? C31 H31 0.9500 . ? C32 C33 1.370(4) . ? C32 H32 0.9500 . ? C33 C34 1.369(4) . ? C33 H33 0.9500 . ? C34 C35 1.385(3) . ? C34 H34 0.9500 . ? C35 C36 1.379(3) . ? C35 H35 0.9500 . ? C36 C37 1.473(3) . ? C37 N31 1.354(2) . ? C37 C38 1.380(3) . ? C38 N33 1.339(2) . ? C38 H38 0.9500 . ? C39 N33 1.460(2) . ? C39 C40 1.517(2) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 N34 1.355(2) . ? C40 C41 1.383(2) . ? C41 C42 1.374(3) . ? C41 H41 0.9500 . ? C42 C43 1.379(3) . ? C42 H42 0.9500 . ? C43 C44 1.386(2) . ? C43 H43 0.9500 . ? C44 N34 1.343(2) . ? C44 C45 1.514(2) . ? C45 N35 1.460(2) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 N35 1.336(2) . ? C46 C47 1.378(2) . ? C46 H46 0.9500 . ? C47 N37 1.358(2) . ? C47 C48 1.472(3) . ? C48 C53 1.385(3) . ? C48 C49 1.392(3) . ? C49 C50 1.386(3) . ? C49 H49 0.9500 . ? C50 C51 1.375(4) . ? C50 H50 0.9500 . ? C51 C52 1.365(4) . ? C51 H51 0.9500 . ? C52 C53 1.378(3) . ? C52 H52 0.9500 . ? C53 H53 0.9500 . ? N31 N32 1.315(2) . ? N32 N33 1.3428(18) . ? N35 N36 1.3473(18) . ? N36 N37 1.3174(18) . ? Cl1 O2 1.4203(17) . ? Cl1 O1 1.4231(15) . ? Cl1 O4 1.4331(16) . ? Cl1 O3 1.4341(16) . ? Cl2 O7 1.4317(13) . ? Cl2 O5 1.4332(13) . ? Cl2 O8 1.4356(16) . ? Cl2 O6 1.4377(13) . ? C61 N61 1.124(3) . ? C61 C62 1.455(4) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C71 C72 1.452(5) . ? C71 H71A 0.9800 . ? C71 H71B 0.9800 . ? C71 H71C 0.9800 . ? C72 O71 1.324(5) . ? C72 H72A 0.9900 . ? C72 H72B 0.9900 . ? C73 C74 1.381(4) . ? C73 O71 1.428(4) . ? C73 H73A 0.9900 . ? C73 H73B 0.9900 . ? C74 H74A 0.9800 . ? C74 H74B 0.9800 . ? C74 H74C 0.9800 . ? 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 N6 Co1 N2 178.34(6) . . ? N6 Co1 N32 88.12(6) . . ? N2 Co1 N32 93.50(6) . . ? N6 Co1 N36 93.02(6) . . ? N2 Co1 N36 85.37(6) . . ? N32 Co1 N36 177.70(6) . . ? N6 Co1 N4 90.45(5) . . ? N2 Co1 N4 89.24(5) . . ? N32 Co1 N4 88.44(5) . . ? N36 Co1 N4 93.54(5) . . ? N6 Co1 N34 87.91(5) . . ? N2 Co1 N34 92.46(5) . . ? N32 Co1 N34 89.36(5) . . ? N36 Co1 N34 88.69(5) . . ? N4 Co1 N34 177.30(5) . . ? C2 C1 C6 120.0 . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 C7 121.5 . . ? C1 C6 C7 118.3 . . ? C2A C1A C6A 120.5 . . ? C3A C2A C1A 121.6 . . ? C4A C3A C2A 120.5 . . ? C3A C4A C5A 120.6 . . ? C6A C5A C4A 119.9 . . ? C1A C6A C5A 115.8 . . ? C1A C6A C7 122.4 . . ? C5A C6A C7 121.7 . . ? N1 C7 C8 108.50(9) . . ? N1 C7 C6 120.13(9) . . ? C8 C7 C6 131.4 . . ? N1 C7 C6A 125.48(9) . . ? C8 C7 C6A 124.6 . . ? C6 C7 C6A 12.7 . . ? N3 C8 C7 105.17(9) . . ? N3 C8 H8 127.4 . . ? C7 C8 H8 127.4 . . ? N3 C9 C10 116.00(14) . . ? N3 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? N3 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? N4 C10 C11 122.67(16) . . ? N4 C10 C9 120.19(15) . . ? C11 C10 C9 117.03(16) . . ? C12 C11 C10 119.49(17) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 118.41(17) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 119.47(17) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? N4 C14 C13 122.58(16) . . ? N4 C14 C15 118.06(15) . . ? C13 C14 C15 119.21(16) . . ? N5 C15 C14 114.24(13) . . ? N5 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? N5 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? N5 C16 C17 105.21(16) . . ? N5 C16 H16 127.4 . . ? C17 C16 H16 127.4 . . ? N7 C17 C16 108.19(16) . . ? N7 C17 C18 122.04(16) . . ? C16 C17 C18 129.78(18) . . ? C23 C18 C19 118.89(19) . . ? C23 C18 C17 120.72(18) . . ? C19 C18 C17 120.36(19) . . ? C18 C19 C20 120.1(2) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 120.4(2) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 119.7(2) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C18 C23 C22 120.5(2) . . ? C18 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? N2 N1 C7 107.84(13) . . ? N1 N2 N3 108.33(14) . . ? N1 N2 Co1 124.07(11) . . ? N3 N2 Co1 121.24(11) . . ? C8 N3 N2 110.15(14) . . ? C8 N3 C9 129.21(14) . . ? N2 N3 C9 119.88(15) . . ? C10 N4 C14 117.18(14) . . ? C10 N4 Co1 121.97(11) . . ? C14 N4 Co1 119.53(11) . . ? C16 N5 N6 110.33(14) . . ? C16 N5 C15 130.04(14) . . ? N6 N5 C15 119.26(14) . . ? N7 N6 N5 108.22(14) . . ? N7 N6 Co1 128.08(11) . . ? N5 N6 Co1 123.42(11) . . ? N6 N7 C17 108.05(14) . . ? C32 C31 C36 120.3(2) . . ? C32 C31 H31 119.8 . . ? C36 C31 H31 119.8 . . ? C33 C32 C31 120.2(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 120.0(3) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 120.3(3) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C36 C35 C34 120.4(2) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C31 118.7(2) . . ? C35 C36 C37 121.2(2) . . ? C31 C36 C37 120.02(18) . . ? N31 C37 C38 108.14(17) . . ? N31 C37 C36 121.20(17) . . ? C38 C37 C36 130.52(18) . . ? N33 C38 C37 105.41(16) . . ? N33 C38 H38 127.3 . . ? C37 C38 H38 127.3 . . ? N33 C39 C40 113.71(15) . . ? N33 C39 H39A 108.8 . . ? C40 C39 H39A 108.8 . . ? N33 C39 H39B 108.8 . . ? C40 C39 H39B 108.8 . . ? H39A C39 H39B 107.7 . . ? N34 C40 C41 122.22(17) . . ? N34 C40 C39 118.59(15) . . ? C41 C40 C39 119.08(16) . . ? C42 C41 C40 119.46(18) . . ? C42 C41 H41 120.3 . . ? C40 C41 H41 120.3 . . ? C41 C42 C43 118.82(18) . . ? C41 C42 H42 120.6 . . ? C43 C42 H42 120.6 . . ? C42 C43 C44 119.20(18) . . ? C42 C43 H43 120.4 . . ? C44 C43 H43 120.4 . . ? N34 C44 C43 122.57(16) . . ? N34 C44 C45 119.66(15) . . ? C43 C44 C45 117.65(16) . . ? N35 C45 C44 114.85(14) . . ? N35 C45 H45A 108.6 . . ? C44 C45 H45A 108.6 . . ? N35 C45 H45B 108.6 . . ? C44 C45 H45B 108.6 . . ? H45A C45 H45B 107.5 . . ? N35 C46 C47 105.39(16) . . ? N35 C46 H46 127.3 . . ? C47 C46 H46 127.3 . . ? N37 C47 C46 108.45(16) . . ? N37 C47 C48 121.50(17) . . ? C46 C47 C48 130.02(18) . . ? C53 C48 C49 118.8(2) . . ? C53 C48 C47 121.0(2) . . ? C49 C48 C47 120.2(2) . . ? C50 C49 C48 119.9(2) . . ? C50 C49 H49 120.0 . . ? C48 C49 H49 120.0 . . ? C51 C50 C49 119.8(3) . . ? C51 C50 H50 120.1 . . ? C49 C50 H50 120.1 . . ? C52 C51 C50 121.0(3) . . ? C52 C51 H51 119.5 . . ? C50 C51 H51 119.5 . . ? C51 C52 C53 119.5(3) . . ? C51 C52 H52 120.2 . . ? C53 C52 H52 120.2 . . ? C52 C53 C48 121.0(3) . . ? C52 C53 H53 119.5 . . ? C48 C53 H53 119.5 . . ? N32 N31 C37 108.16(15) . . ? N31 N32 N33 108.48(14) . . ? N31 N32 Co1 126.23(11) . . ? N33 N32 Co1 122.91(12) . . ? C38 N33 N32 109.81(15) . . ? C38 N33 C39 130.44(15) . . ? N32 N33 C39 119.74(14) . . ? C44 N34 C40 117.70(15) . . ? C44 N34 Co1 121.28(11) . . ? C40 N34 Co1 120.45(12) . . ? C46 N35 N36 109.92(14) . . ? C46 N35 C45 130.43(15) . . ? N36 N35 C45 119.34(14) . . ? N37 N36 N35 108.45(13) . . ? N37 N36 Co1 125.29(11) . . ? N35 N36 Co1 121.63(10) . . ? N36 N37 C47 107.78(14) . . ? O2 Cl1 O1 110.17(12) . . ? O2 Cl1 O4 108.13(11) . . ? O1 Cl1 O4 110.53(11) . . ? O2 Cl1 O3 110.70(13) . . ? O1 Cl1 O3 108.59(10) . . ? O4 Cl1 O3 108.71(10) . . ? O7 Cl2 O5 110.13(9) . . ? O7 Cl2 O8 109.52(10) . . ? O5 Cl2 O8 109.95(10) . . ? O7 Cl2 O6 108.75(8) . . ? O5 Cl2 O6 109.68(8) . . ? O8 Cl2 O6 108.79(10) . . ? N61 C61 C62 179.1(3) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C72 C71 H71A 109.5 . . ? C72 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C72 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 109.5 . . ? O71 C72 C71 114.7(5) . . ? O71 C72 H72A 108.6 . . ? C71 C72 H72A 108.6 . . ? O71 C72 H72B 108.6 . . ? C71 C72 H72B 108.6 . . ? H72A C72 H72B 107.6 . . ? C74 C73 O71 112.7(4) . . ? C74 C73 H73A 109.0 . . ? O71 C73 H73A 109.0 . . ? C74 C73 H73B 109.0 . . ? O71 C73 H73B 109.0 . . ? H73A C73 H73B 107.8 . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? C72 O71 C73 113.9(4) . . ? 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 C6 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C4 C5 C6 C7 -175.4 . . . . ? C2 C1 C6 C5 0.0 . . . . ? C2 C1 C6 C7 175.6 . . . . ? C6A C1A C2A C3A -0.8 . . . . ? C1A C2A C3A C4A -7.9 . . . . ? C2A C3A C4A C5A 7.6 . . . . ? C3A C4A C5A C6A 1.0 . . . . ? C2A C1A C6A C5A 8.9 . . . . ? C2A C1A C6A C7 -174.9 . . . . ? C4A C5A C6A C1A -9.0 . . . . ? C4A C5A C6A C7 174.7 . . . . ? C5 C6 C7 N1 21.17(14) . . . . ? C1 C6 C7 N1 -154.32(14) . . . . ? C5 C6 C7 C8 -158.3 . . . . ? C1 C6 C7 C8 26.2 . . . . ? C5 C6 C7 C6A 139.6 . . . . ? C1 C6 C7 C6A -35.9 . . . . ? C1A C6A C7 N1 146.81(15) . . . . ? C5A C6A C7 N1 -37.13(15) . . . . ? C1A C6A C7 C8 -48.6 . . . . ? C5A C6A C7 C8 127.5 . . . . ? C1A C6A C7 C6 77.8 . . . . ? C5A C6A C7 C6 -106.1 . . . . ? N1 C7 C8 N3 -0.25(12) . . . . ? C6 C7 C8 N3 179.29(11) . . . . ? C6A C7 C8 N3 -167.06(10) . . . . ? N3 C9 C10 N4 39.8(2) . . . . ? N3 C9 C10 C11 -143.96(16) . . . . ? N4 C10 C11 C12 2.2(3) . . . . ? C9 C10 C11 C12 -173.96(16) . . . . ? C10 C11 C12 C13 -3.3(3) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 N4 3.4(3) . . . . ? C12 C13 C14 C15 -172.05(16) . . . . ? N4 C14 C15 N5 67.3(2) . . . . ? C13 C14 C15 N5 -117.03(17) . . . . ? N5 C16 C17 N7 -0.1(2) . . . . ? N5 C16 C17 C18 179.95(17) . . . . ? N7 C17 C18 C23 177.74(18) . . . . ? C16 C17 C18 C23 -2.3(3) . . . . ? N7 C17 C18 C19 -0.3(3) . . . . ? C16 C17 C18 C19 179.6(2) . . . . ? C23 C18 C19 C20 -0.8(3) . . . . ? C17 C18 C19 C20 177.29(19) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C20 C21 C22 C23 -0.9(4) . . . . ? C19 C18 C23 C22 0.0(3) . . . . ? C17 C18 C23 C22 -178.12(19) . . . . ? C21 C22 C23 C18 0.9(3) . . . . ? C8 C7 N1 N2 -0.37(14) . . . . ? C6 C7 N1 N2 -179.96(9) . . . . ? C6A C7 N1 N2 166.29(10) . . . . ? C7 N1 N2 N3 0.84(17) . . . . ? C7 N1 N2 Co1 152.93(10) . . . . ? N6 Co1 N2 N1 -62(2) . . . . ? N32 Co1 N2 N1 131.03(13) . . . . ? N36 Co1 N2 N1 -46.97(13) . . . . ? N4 Co1 N2 N1 -140.58(13) . . . . ? N34 Co1 N2 N1 41.52(13) . . . . ? N6 Co1 N2 N3 87(2) . . . . ? N32 Co1 N2 N3 -80.29(13) . . . . ? N36 Co1 N2 N3 101.72(13) . . . . ? N4 Co1 N2 N3 8.10(13) . . . . ? N34 Co1 N2 N3 -169.80(12) . . . . ? C7 C8 N3 N2 0.77(14) . . . . ? C7 C8 N3 C9 170.61(14) . . . . ? N1 N2 N3 C8 -1.03(18) . . . . ? Co1 N2 N3 C8 -154.06(11) . . . . ? N1 N2 N3 C9 -171.95(13) . . . . ? Co1 N2 N3 C9 35.02(19) . . . . ? C10 C9 N3 C8 123.09(18) . . . . ? C10 C9 N3 N2 -67.9(2) . . . . ? C11 C10 N4 C14 1.8(2) . . . . ? C9 C10 N4 C14 177.78(15) . . . . ? C11 C10 N4 Co1 -165.08(13) . . . . ? C9 C10 N4 Co1 10.9(2) . . . . ? C13 C14 N4 C10 -4.6(2) . . . . ? C15 C14 N4 C10 170.93(14) . . . . ? C13 C14 N4 Co1 162.59(13) . . . . ? C15 C14 N4 Co1 -21.87(19) . . . . ? N6 Co1 N4 C10 151.02(13) . . . . ? N2 Co1 N4 C10 -30.61(13) . . . . ? N32 Co1 N4 C10 62.91(13) . . . . ? N36 Co1 N4 C10 -115.92(13) . . . . ? N34 Co1 N4 C10 98.4(11) . . . . ? N6 Co1 N4 C14 -15.53(12) . . . . ? N2 Co1 N4 C14 162.83(13) . . . . ? N32 Co1 N4 C14 -103.65(13) . . . . ? N36 Co1 N4 C14 77.52(13) . . . . ? N34 Co1 N4 C14 -68.1(11) . . . . ? C17 C16 N5 N6 0.52(19) . . . . ? C17 C16 N5 C15 173.25(16) . . . . ? C14 C15 N5 C16 126.59(18) . . . . ? C14 C15 N5 N6 -61.2(2) . . . . ? C16 N5 N6 N7 -0.76(19) . . . . ? C15 N5 N6 N7 -174.38(13) . . . . ? C16 N5 N6 Co1 -175.16(11) . . . . ? C15 N5 N6 Co1 11.2(2) . . . . ? N2 Co1 N6 N7 129.5(19) . . . . ? N32 Co1 N6 N7 -63.04(14) . . . . ? N36 Co1 N6 N7 114.97(14) . . . . ? N4 Co1 N6 N7 -151.47(14) . . . . ? N34 Co1 N6 N7 26.39(14) . . . . ? N2 Co1 N6 N5 -57(2) . . . . ? N32 Co1 N6 N5 110.20(13) . . . . ? N36 Co1 N6 N5 -71.79(13) . . . . ? N4 Co1 N6 N5 21.78(13) . . . . ? N34 Co1 N6 N5 -160.37(13) . . . . ? N5 N6 N7 C17 0.67(18) . . . . ? Co1 N6 N7 C17 174.74(12) . . . . ? C16 C17 N7 N6 -0.3(2) . . . . ? C18 C17 N7 N6 179.60(15) . . . . ? C36 C31 C32 C33 0.3(4) . . . . ? C31 C32 C33 C34 1.8(4) . . . . ? C32 C33 C34 C35 -2.2(4) . . . . ? C33 C34 C35 C36 0.5(4) . . . . ? C34 C35 C36 C31 1.7(3) . . . . ? C34 C35 C36 C37 -175.0(2) . . . . ? C32 C31 C36 C35 -2.1(3) . . . . ? C32 C31 C36 C37 174.6(2) . . . . ? C35 C36 C37 N31 173.95(19) . . . . ? C31 C36 C37 N31 -2.7(3) . . . . ? C35 C36 C37 C38 -1.2(3) . . . . ? C31 C36 C37 C38 -177.8(2) . . . . ? N31 C37 C38 N33 -0.5(2) . . . . ? C36 C37 C38 N33 175.13(18) . . . . ? N33 C39 C40 N34 62.7(2) . . . . ? N33 C39 C40 C41 -120.95(19) . . . . ? N34 C40 C41 C42 2.3(3) . . . . ? C39 C40 C41 C42 -173.91(19) . . . . ? C40 C41 C42 C43 -1.0(3) . . . . ? C41 C42 C43 C44 -0.5(3) . . . . ? C42 C43 C44 N34 0.9(3) . . . . ? C42 C43 C44 C45 -175.18(18) . . . . ? N34 C44 C45 N35 48.4(2) . . . . ? C43 C44 C45 N35 -135.38(17) . . . . ? N35 C46 C47 N37 -0.2(2) . . . . ? N35 C46 C47 C48 -178.27(18) . . . . ? N37 C47 C48 C53 -161.25(19) . . . . ? C46 C47 C48 C53 16.6(3) . . . . ? N37 C47 C48 C49 18.5(3) . . . . ? C46 C47 C48 C49 -163.7(2) . . . . ? C53 C48 C49 C50 1.0(3) . . . . ? C47 C48 C49 C50 -178.7(2) . . . . ? C48 C49 C50 C51 -1.0(4) . . . . ? C49 C50 C51 C52 0.4(5) . . . . ? C50 C51 C52 C53 0.3(5) . . . . ? C51 C52 C53 C48 -0.3(4) . . . . ? C49 C48 C53 C52 -0.4(4) . . . . ? C47 C48 C53 C52 179.4(2) . . . . ? C38 C37 N31 N32 0.1(2) . . . . ? C36 C37 N31 N32 -175.99(16) . . . . ? C37 N31 N32 N33 0.3(2) . . . . ? C37 N31 N32 Co1 163.05(12) . . . . ? N6 Co1 N32 N31 -51.24(15) . . . . ? N2 Co1 N32 N31 128.40(15) . . . . ? N36 Co1 N32 N31 -171.2(14) . . . . ? N4 Co1 N32 N31 39.26(15) . . . . ? N34 Co1 N32 N31 -139.17(15) . . . . ? N6 Co1 N32 N33 109.18(14) . . . . ? N2 Co1 N32 N33 -71.18(14) . . . . ? N36 Co1 N32 N33 -10.8(16) . . . . ? N4 Co1 N32 N33 -160.32(14) . . . . ? N34 Co1 N32 N33 21.25(14) . . . . ? C37 C38 N33 N32 0.7(2) . . . . ? C37 C38 N33 C39 -178.68(17) . . . . ? N31 N32 N33 C38 -0.6(2) . . . . ? Co1 N32 N33 C38 -164.06(12) . . . . ? N31 N32 N33 C39 178.81(15) . . . . ? Co1 N32 N33 C39 15.4(2) . . . . ? C40 C39 N33 C38 115.0(2) . . . . ? C40 C39 N33 N32 -64.3(2) . . . . ? C43 C44 N34 C40 0.2(3) . . . . ? C45 C44 N34 C40 176.26(15) . . . . ? C43 C44 N34 Co1 -171.16(14) . . . . ? C45 C44 N34 Co1 4.9(2) . . . . ? C41 C40 N34 C44 -1.8(3) . . . . ? C39 C40 N34 C44 174.36(16) . . . . ? C41 C40 N34 Co1 169.63(14) . . . . ? C39 C40 N34 Co1 -14.2(2) . . . . ? N6 Co1 N34 C44 61.98(13) . . . . ? N2 Co1 N34 C44 -116.40(13) . . . . ? N32 Co1 N34 C44 150.12(13) . . . . ? N36 Co1 N34 C44 -31.10(13) . . . . ? N4 Co1 N34 C44 114.6(11) . . . . ? N6 Co1 N34 C40 -109.17(13) . . . . ? N2 Co1 N34 C40 72.45(13) . . . . ? N32 Co1 N34 C40 -21.03(13) . . . . ? N36 Co1 N34 C40 157.76(13) . . . . ? N4 Co1 N34 C40 -56.5(12) . . . . ? C47 C46 N35 N36 0.72(19) . . . . ? C47 C46 N35 C45 174.15(16) . . . . ? C44 C45 N35 C46 118.23(19) . . . . ? C44 C45 N35 N36 -68.9(2) . . . . ? C46 N35 N36 N37 -0.96(18) . . . . ? C45 N35 N36 N37 -175.22(13) . . . . ? C46 N35 N36 Co1 -157.99(12) . . . . ? C45 N35 N36 Co1 27.74(19) . . . . ? N6 Co1 N36 N37 134.12(13) . . . . ? N2 Co1 N36 N37 -45.46(13) . . . . ? N32 Co1 N36 N37 -106.0(15) . . . . ? N4 Co1 N36 N37 43.49(13) . . . . ? N34 Co1 N36 N37 -138.04(13) . . . . ? N6 Co1 N36 N35 -72.84(13) . . . . ? N2 Co1 N36 N35 107.57(13) . . . . ? N32 Co1 N36 N35 47.0(15) . . . . ? N4 Co1 N36 N35 -163.48(12) . . . . ? N34 Co1 N36 N35 15.00(12) . . . . ? N35 N36 N37 C47 0.78(18) . . . . ? Co1 N36 N37 C47 156.76(12) . . . . ? C46 C47 N37 N36 -0.34(19) . . . . ? C48 C47 N37 N36 177.90(16) . . . . ? C71 C72 O71 C73 -179.1(4) . . . . ? C74 C73 O71 C72 140.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.760 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.051 # Attachment 'fig-4---zhu71final.cif' data_zhu71 _database_code_depnum_ccdc_archive 'CCDC 811005' #TrackingRef 'fig-4---zhu71final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H19 Cl2 Cu N7' _chemical_formula_sum 'C23 H19 Cl2 Cu N7' _chemical_formula_weight 527.89 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(2) _symmetry_space_group_name_Hall P62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z' 'y, -x+y, z+2/3' 'x-y, x, z+1/3' _cell_length_a 12.4784(17) _cell_length_b 12.4784(17) _cell_length_c 14.4891(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1953.8(5) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4514 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 18.20 _exptl_crystal_description hexgonal _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 807 _exptl_absorpt_coefficient_mu 1.067 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8311 _exptl_absorpt_correction_T_max 0.8737 _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_reflns_number 7902 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 18.20 _reflns_number_total 918 _reflns_number_gt 910 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+4.5684P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(5) _refine_ls_number_reflns 918 _refine_ls_number_parameters 151 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.232 _refine_ls_restrained_S_all 1.231 _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 Cu1 Cu 0.5000 0.5000 0.29037(11) 0.0723(7) Uani 1 2 d S . . Cl1 Cl 0.3495(3) 0.3223(3) 0.2217(2) 0.0864(11) Uani 1 1 d . . . C1 C 0.8686(15) 0.2632(15) 0.3094(10) 0.117(5) Uani 1 1 d . . . H1 H 0.8802 0.2871 0.3725 0.140 Uiso 1 1 calc R . . C2 C 0.9187(17) 0.1934(18) 0.2765(17) 0.161(9) Uani 1 1 d . . . H2 H 0.9625 0.1690 0.3170 0.194 Uiso 1 1 calc R . . C3 C 0.9046(17) 0.1594(17) 0.1841(16) 0.144(6) Uani 1 1 d . . . H3 H 0.9407 0.1143 0.1594 0.173 Uiso 1 1 calc R . . C4 C 0.8372(15) 0.1930(13) 0.1305(9) 0.096(4) Uani 1 1 d . . . H4 H 0.8252 0.1683 0.0676 0.115 Uiso 1 1 calc R . . C5 C 0.7873(11) 0.2579(13) 0.1606(9) 0.072(3) Uani 1 1 d . . . H5 H 0.7403 0.2773 0.1192 0.087 Uiso 1 1 calc R . . C6 C 0.8022(11) 0.2995(11) 0.2534(10) 0.075(4) Uani 1 1 d . . . C7 C 0.7468(12) 0.3698(11) 0.2892(8) 0.061(3) Uani 1 1 d . . . C8 C 0.7910(11) 0.4542(12) 0.3600(8) 0.065(3) Uani 1 1 d . . . H8 H 0.8618 0.4757 0.3970 0.078 Uiso 1 1 calc R . . C9 C 0.7195(12) 0.5912(12) 0.4291(9) 0.085(4) Uani 1 1 d . . . H9A H 0.7313 0.6636 0.3928 0.102 Uiso 1 1 calc R . . H9B H 0.7909 0.6196 0.4715 0.102 Uiso 1 1 calc R . . C10 C 0.6062(12) 0.5439(11) 0.4833(9) 0.077(4) Uani 1 1 d . . . C11 C 0.6116(14) 0.5461(13) 0.5835(9) 0.100(5) Uani 1 1 d . . . H11 H 0.6871 0.5774 0.6165 0.120 Uiso 1 1 calc R . . C12 C 0.5000 0.5000 0.6265(13) 0.113(8) Uani 1 2 d S . . H12 H 0.5000 0.5000 0.6921 0.136 Uiso 1 2 calc SR . . N1 N 0.6469(9) 0.3692(10) 0.2558(6) 0.069(3) Uani 1 1 d . . . N2 N 0.6215(9) 0.4459(9) 0.3004(7) 0.067(3) Uani 1 1 d . . . N3 N 0.7172(10) 0.4986(9) 0.3664(6) 0.070(3) Uani 1 1 d . . . N4 N 0.5000 0.5000 0.4404(9) 0.076(4) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0897(15) 0.1059(17) 0.0401(11) 0.000 0.000 0.0631(14) Cl1 0.091(2) 0.124(3) 0.061(2) -0.0188(19) -0.0095(18) 0.066(2) C1 0.160(14) 0.162(15) 0.065(10) -0.026(10) -0.016(11) 0.107(13) C2 0.21(2) 0.24(2) 0.135(18) -0.079(17) -0.083(16) 0.19(2) C3 0.178(18) 0.196(19) 0.120(17) -0.050(15) -0.024(13) 0.140(16) C4 0.134(12) 0.116(11) 0.053(9) -0.006(9) 0.006(10) 0.074(10) C5 0.100(9) 0.097(9) 0.038(10) 0.012(7) 0.014(7) 0.063(9) C6 0.082(10) 0.103(9) 0.059(13) -0.018(8) -0.034(7) 0.059(9) C7 0.065(9) 0.089(9) 0.041(8) 0.007(8) 0.006(7) 0.048(8) C8 0.081(9) 0.108(9) 0.036(8) -0.016(7) -0.016(7) 0.069(9) C9 0.100(10) 0.101(9) 0.071(9) -0.029(8) -0.024(8) 0.063(8) C10 0.093(11) 0.104(10) 0.057(12) -0.015(7) -0.007(9) 0.066(9) C11 0.152(14) 0.162(15) 0.053(12) -0.005(9) -0.013(10) 0.129(13) C12 0.20(3) 0.19(2) 0.048(15) 0.000 0.000 0.17(2) N1 0.064(7) 0.093(8) 0.051(7) 0.004(6) -0.006(5) 0.041(6) N2 0.096(7) 0.075(6) 0.043(7) -0.019(5) -0.005(6) 0.052(6) N3 0.076(7) 0.099(8) 0.053(7) -0.023(6) -0.019(6) 0.056(7) N4 0.087(12) 0.110(11) 0.050(10) 0.000 0.000 0.063(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.949(10) 4_665 ? Cu1 N2 1.949(10) . ? Cu1 N4 2.174(14) . ? Cu1 Cl1 2.295(3) . ? Cu1 Cl1 2.295(3) 4_665 ? C1 C6 1.388(16) . ? C1 C2 1.386(19) . ? C1 H1 0.9500 . ? C2 C3 1.39(2) . ? C2 H2 0.9500 . ? C3 C4 1.356(19) . ? C3 H3 0.9500 . ? C4 C5 1.318(16) . ? C4 H4 0.9500 . ? C5 C6 1.421(15) . ? C5 H5 0.9500 . ? C6 C7 1.457(15) . ? C7 N1 1.334(12) . ? C7 C8 1.373(14) . ? C8 N3 1.294(12) . ? C8 H8 0.9500 . ? C9 N3 1.459(14) . ? C9 C10 1.459(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N4 1.310(13) . ? C10 C11 1.454(16) . ? C11 C12 1.363(14) . ? C11 H11 0.9500 . ? C12 C11 1.363(14) 4_665 ? C12 H12 0.9500 . ? N1 N2 1.318(12) . ? N2 N3 1.410(11) . ? N4 C10 1.310(13) 4_665 ? 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 N2 Cu1 N2 171.5(6) 4_665 . ? N2 Cu1 N4 85.7(3) 4_665 . ? N2 Cu1 N4 85.7(3) . . ? N2 Cu1 Cl1 88.0(3) 4_665 . ? N2 Cu1 Cl1 95.7(3) . . ? N4 Cu1 Cl1 115.68(9) . . ? N2 Cu1 Cl1 95.7(3) 4_665 4_665 ? N2 Cu1 Cl1 88.0(3) . 4_665 ? N4 Cu1 Cl1 115.68(9) . 4_665 ? Cl1 Cu1 Cl1 128.65(18) . 4_665 ? C6 C1 C2 122.3(13) . . ? C6 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 119.7(14) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 117.5(14) . . ? C4 C3 H3 121.3 . . ? C2 C3 H3 121.3 . . ? C5 C4 C3 123.9(13) . . ? C5 C4 H4 118.0 . . ? C3 C4 H4 118.0 . . ? C4 C5 C6 121.4(11) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 115.2(12) . . ? C1 C6 C7 122.0(13) . . ? C5 C6 C7 122.8(13) . . ? N1 C7 C8 106.9(10) . . ? N1 C7 C6 126.3(13) . . ? C8 C7 C6 126.7(13) . . ? N3 C8 C7 106.4(10) . . ? N3 C8 H8 126.8 . . ? C7 C8 H8 126.8 . . ? N3 C9 C10 112.5(11) . . ? N3 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N3 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N4 C10 C11 120.6(12) . . ? N4 C10 C9 119.2(11) . . ? C11 C10 C9 120.3(12) . . ? C12 C11 C10 114.9(14) . . ? C12 C11 H11 122.5 . . ? C10 C11 H11 122.5 . . ? C11 C12 C11 125.5(19) . 4_665 ? C11 C12 H12 117.2 . . ? C11 C12 H12 117.2 4_665 . ? N2 N1 C7 112.5(9) . . ? N1 N2 N3 102.5(8) . . ? N1 N2 Cu1 136.6(8) . . ? N3 N2 Cu1 120.9(8) . . ? C8 N3 N2 111.7(9) . . ? C8 N3 C9 130.4(11) . . ? N2 N3 C9 117.9(10) . . ? C10 N4 C10 123.4(15) 4_665 . ? C10 N4 Cu1 118.3(8) 4_665 . ? C10 N4 Cu1 118.3(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1(3) . . . . ? C1 C2 C3 C4 -2(3) . . . . ? C2 C3 C4 C5 2(3) . . . . ? C3 C4 C5 C6 1(2) . . . . ? C2 C1 C6 C5 1(2) . . . . ? C2 C1 C6 C7 178.2(15) . . . . ? C4 C5 C6 C1 -2.1(19) . . . . ? C4 C5 C6 C7 -179.1(12) . . . . ? C1 C6 C7 N1 -152.4(12) . . . . ? C5 C6 C7 N1 24.4(17) . . . . ? C1 C6 C7 C8 31.5(18) . . . . ? C5 C6 C7 C8 -151.7(12) . . . . ? N1 C7 C8 N3 0.5(13) . . . . ? C6 C7 C8 N3 177.2(10) . . . . ? N3 C9 C10 N4 -58.0(14) . . . . ? N3 C9 C10 C11 122.3(12) . . . . ? N4 C10 C11 C12 0.0(16) . . . . ? C9 C10 C11 C12 179.7(10) . . . . ? C10 C11 C12 C11 0.0(7) . . . 4_665 ? C8 C7 N1 N2 -0.8(12) . . . . ? C6 C7 N1 N2 -177.5(10) . . . . ? C7 N1 N2 N3 0.7(11) . . . . ? C7 N1 N2 Cu1 177.1(8) . . . . ? N4 Cu1 N2 N1 142.5(11) . . . . ? Cl1 Cu1 N2 N1 27.1(11) . . . . ? Cl1 Cu1 N2 N1 -101.6(10) 4_665 . . . ? N4 Cu1 N2 N3 -41.6(7) . . . . ? Cl1 Cu1 N2 N3 -157.0(7) . . . . ? Cl1 Cu1 N2 N3 74.4(7) 4_665 . . . ? C7 C8 N3 N2 -0.1(13) . . . . ? C7 C8 N3 C9 -179.8(11) . . . . ? N1 N2 N3 C8 -0.4(12) . . . . ? Cu1 N2 N3 C8 -177.5(8) . . . . ? N1 N2 N3 C9 179.4(9) . . . . ? Cu1 N2 N3 C9 2.2(13) . . . . ? C10 C9 N3 C8 -121.8(14) . . . . ? C10 C9 N3 N2 58.5(13) . . . . ? C11 C10 N4 C10 0.0(8) . . . 4_665 ? C9 C10 N4 C10 -179.7(12) . . . 4_665 ? C11 C10 N4 Cu1 180.0(8) . . . . ? C9 C10 N4 Cu1 0.3(12) . . . . ? N2 Cu1 N4 C10 41.8(6) 4_665 . . 4_665 ? N2 Cu1 N4 C10 -138.2(6) . . . 4_665 ? Cl1 Cu1 N4 C10 -43.9(6) . . . 4_665 ? Cl1 Cu1 N4 C10 136.1(6) 4_665 . . 4_665 ? N2 Cu1 N4 C10 -138.2(6) 4_665 . . . ? N2 Cu1 N4 C10 41.8(6) . . . . ? Cl1 Cu1 N4 C10 136.1(6) . . . . ? Cl1 Cu1 N4 C10 -43.9(6) 4_665 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 18.20 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.274 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.047 # Attachment 'fig-7B---zhu69Final.cif' data_zhu69 _database_code_depnum_ccdc_archive 'CCDC 811006' #TrackingRef 'fig-7B---zhu69Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl2 Cu N8' _chemical_formula_sum 'C12 H12 Cl2 Cu N8' _chemical_formula_weight 402.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3249(8) _cell_length_b 9.4048(9) _cell_length_c 10.0280(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.6930(10) _cell_angle_gamma 90.00 _cell_volume 771.50(13) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 5099 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 28.84 _exptl_crystal_description parallelpiped _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.734 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 406 _exptl_absorpt_coefficient_mu 1.773 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6937 _exptl_absorpt_correction_T_max 0.8553 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8675 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1897 _reflns_number_gt 1748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+0.4555P] 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 1897 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Cu1 Cu 0.0000 0.0000 0.5000 0.01704(8) Uani 1 2 d S . . Cl1 Cl 0.04852(4) -0.06453(4) 0.28700(3) 0.02340(9) Uani 1 1 d . . . C1 C 0.26843(17) 0.19738(15) 0.49467(14) 0.0203(3) Uani 1 1 d . . . H1 H 0.1887 0.2441 0.4293 0.024 Uiso 1 1 calc R . . C2 C 0.42141(18) 0.25837(16) 0.53052(14) 0.0231(3) Uani 1 1 d . . . H2 H 0.4456 0.3467 0.4927 0.028 Uiso 1 1 calc R . . C3 C 0.53903(18) 0.18744(17) 0.62325(15) 0.0241(3) Uani 1 1 d . . . H3 H 0.6450 0.2271 0.6506 0.029 Uiso 1 1 calc R . . C4 C 0.49999(17) 0.05814(16) 0.67537(14) 0.0219(3) Uani 1 1 d . . . H4 H 0.5801 0.0065 0.7363 0.026 Uiso 1 1 calc R . . C5 C 0.34229(18) 0.00471(14) 0.63752(14) 0.0181(3) Uani 1 1 d . . . C6 C 0.29336(18) -0.13090(15) 0.69982(14) 0.0226(3) Uani 1 1 d . . . H6A H 0.3875 -0.1971 0.7156 0.027 Uiso 1 1 calc R . . H6B H 0.2635 -0.1093 0.7887 0.027 Uiso 1 1 calc R . . N1 N 0.22778(14) 0.07454(12) 0.54860(11) 0.0178(2) Uani 1 1 d . . . N2 N 0.15285(15) -0.20031(13) 0.61066(13) 0.0238(3) Uani 1 1 d . . . N3 N 0.18027(15) -0.31372(13) 0.55719(12) 0.0237(3) Uani 1 1 d . . . N4 N 0.1847(2) -0.41826(16) 0.50267(16) 0.0379(3) 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 Cu1 0.01618(12) 0.01611(12) 0.01861(12) -0.00033(8) 0.00263(9) -0.00052(8) Cl1 0.02226(17) 0.02689(18) 0.02144(17) -0.00485(13) 0.00505(13) -0.00116(13) C1 0.0221(7) 0.0194(7) 0.0196(6) 0.0008(5) 0.0040(5) 0.0012(5) C2 0.0263(7) 0.0208(7) 0.0241(7) -0.0005(5) 0.0097(6) -0.0031(6) C3 0.0195(6) 0.0297(7) 0.0234(7) -0.0046(6) 0.0048(5) -0.0036(6) C4 0.0197(7) 0.0265(7) 0.0192(6) -0.0023(5) 0.0026(5) 0.0023(6) C5 0.0206(7) 0.0183(6) 0.0159(6) -0.0019(5) 0.0045(5) 0.0028(5) C6 0.0261(7) 0.0187(6) 0.0216(7) 0.0024(5) 0.0008(5) 0.0006(5) N1 0.0188(5) 0.0168(5) 0.0177(5) -0.0008(4) 0.0035(4) 0.0008(4) N2 0.0246(6) 0.0174(6) 0.0289(6) 0.0007(5) 0.0037(5) 0.0009(5) N3 0.0252(6) 0.0209(6) 0.0246(6) 0.0032(5) 0.0040(5) -0.0010(5) N4 0.0439(9) 0.0282(7) 0.0391(8) -0.0078(6) 0.0012(7) 0.0027(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 Cu1 N1 1.9954(12) 3_556 ? Cu1 N1 1.9955(12) . ? Cu1 Cl1 2.3268(4) 3_556 ? Cu1 Cl1 2.3268(4) . ? Cu1 N2 2.4240(12) 3_556 ? Cu1 N2 2.4240(12) . ? C1 N1 1.3452(18) . ? C1 C2 1.382(2) . ? C1 H1 0.9500 . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 N1 1.3489(18) . ? C5 C6 1.5091(19) . ? C6 N2 1.4852(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N2 N3 1.2340(18) . ? N3 N4 1.1289(19) . ? 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 Cu1 N1 180.0 3_556 . ? N1 Cu1 Cl1 89.82(3) 3_556 3_556 ? N1 Cu1 Cl1 90.18(3) . 3_556 ? N1 Cu1 Cl1 90.18(3) 3_556 . ? N1 Cu1 Cl1 89.82(3) . . ? Cl1 Cu1 Cl1 180.0 3_556 . ? N1 Cu1 N2 76.52(4) 3_556 3_556 ? N1 Cu1 N2 103.48(4) . 3_556 ? Cl1 Cu1 N2 92.97(3) 3_556 3_556 ? Cl1 Cu1 N2 87.03(3) . 3_556 ? N1 Cu1 N2 103.48(4) 3_556 . ? N1 Cu1 N2 76.52(4) . . ? Cl1 Cu1 N2 87.03(3) 3_556 . ? Cl1 Cu1 N2 92.97(3) . . ? N2 Cu1 N2 180.0 3_556 . ? N1 C1 C2 122.70(13) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.40(13) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.23(13) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.31(13) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.33(13) . . ? N1 C5 C6 118.24(12) . . ? C4 C5 C6 120.39(13) . . ? N2 C6 C5 111.42(11) . . ? N2 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N2 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C1 N1 C5 118.96(12) . . ? C1 N1 Cu1 120.13(9) . . ? C5 N1 Cu1 120.89(9) . . ? N3 N2 C6 116.93(12) . . ? N3 N2 Cu1 126.63(10) . . ? C6 N2 Cu1 102.82(8) . . ? N4 N3 N2 171.33(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.9(2) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -2.3(2) . . . . ? C3 C4 C5 N1 1.6(2) . . . . ? C3 C4 C5 C6 -175.94(13) . . . . ? N1 C5 C6 N2 25.89(17) . . . . ? C4 C5 C6 N2 -156.48(13) . . . . ? C2 C1 N1 C5 -2.6(2) . . . . ? C2 C1 N1 Cu1 176.13(10) . . . . ? C4 C5 N1 C1 0.80(19) . . . . ? C6 C5 N1 C1 178.41(12) . . . . ? C4 C5 N1 Cu1 -177.92(10) . . . . ? C6 C5 N1 Cu1 -0.30(16) . . . . ? Cl1 Cu1 N1 C1 -106.31(10) 3_556 . . . ? Cl1 Cu1 N1 C1 73.69(10) . . . . ? N2 Cu1 N1 C1 -13.22(11) 3_556 . . . ? N2 Cu1 N1 C1 166.78(11) . . . . ? Cl1 Cu1 N1 C5 72.39(10) 3_556 . . . ? Cl1 Cu1 N1 C5 -107.61(10) . . . . ? N2 Cu1 N1 C5 165.48(10) 3_556 . . . ? N2 Cu1 N1 C5 -14.52(10) . . . . ? C5 C6 N2 N3 111.14(14) . . . . ? C5 C6 N2 Cu1 -32.17(12) . . . . ? N1 Cu1 N2 N3 67.01(13) 3_556 . . . ? N1 Cu1 N2 N3 -112.99(13) . . . . ? Cl1 Cu1 N2 N3 156.11(12) 3_556 . . . ? Cl1 Cu1 N2 N3 -23.89(12) . . . . ? N1 Cu1 N2 C6 -154.57(8) 3_556 . . . ? N1 Cu1 N2 C6 25.43(8) . . . . ? Cl1 Cu1 N2 C6 -65.47(8) 3_556 . . . ? Cl1 Cu1 N2 C6 114.53(8) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.372 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.054 # Attachment 'fig-7C---zhu70final.cif' data_zhu70 _database_code_depnum_ccdc_archive 'CCDC 811007' #TrackingRef 'fig-7C---zhu70final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cu N10 O6' _chemical_formula_sum 'C12 H12 Cu N10 O6' _chemical_formula_weight 455.86 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' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2242(6) _cell_length_b 8.0475(7) _cell_length_c 8.0930(7) _cell_angle_alpha 84.6130(10) _cell_angle_beta 67.8770(10) _cell_angle_gamma 76.5890(10) _cell_volume 423.96(6) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4330 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.99 _exptl_crystal_description irregular, _exptl_crystal_colour blue _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 231 _exptl_absorpt_coefficient_mu 1.348 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6799 _exptl_absorpt_correction_T_max 0.8442 _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_reflns_number 5082 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 29.07 _reflns_number_total 2094 _reflns_number_gt 2072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.2806P] 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 2094 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Cu1 Cu 0.0000 0.5000 0.5000 0.01797(8) Uani 1 2 d S . . C1 C -0.1893(2) 0.45026(19) 0.2553(2) 0.0229(3) Uani 1 1 d . . . H1 H -0.2941 0.5407 0.3217 0.027 Uiso 1 1 calc R . . C2 C -0.2105(2) 0.3834(2) 0.1139(2) 0.0251(3) Uani 1 1 d . . . H2 H -0.3261 0.4283 0.0818 0.030 Uiso 1 1 calc R . . C3 C -0.0589(3) 0.2492(2) 0.0201(2) 0.0262(3) Uani 1 1 d . . . H3 H -0.0696 0.2001 -0.0773 0.031 Uiso 1 1 calc R . . C4 C 0.1083(2) 0.18744(19) 0.0699(2) 0.0232(3) Uani 1 1 d . . . H4 H 0.2127 0.0947 0.0077 0.028 Uiso 1 1 calc R . . C5 C 0.1221(2) 0.26216(17) 0.21158(18) 0.0187(3) Uani 1 1 d . . . C6 C 0.3084(2) 0.20178(18) 0.26075(19) 0.0202(3) Uani 1 1 d . . . H6A H 0.3535 0.0763 0.2470 0.024 Uiso 1 1 calc R . . H6B H 0.4208 0.2541 0.1783 0.024 Uiso 1 1 calc R . . N1 N -0.02555(18) 0.39210(15) 0.30270(16) 0.0192(2) Uani 1 1 d . . . N2 N 0.2661(2) 0.24714(16) 0.44694(17) 0.0222(2) Uani 1 1 d . . . N3 N 0.27172(19) 0.12356(17) 0.55041(17) 0.0244(3) Uani 1 1 d . . . N4 N 0.2763(2) 0.0237(2) 0.6568(2) 0.0373(3) Uani 1 1 d . . . N5 N 0.28131(19) 0.73122(16) 0.29564(17) 0.0225(2) Uani 1 1 d . . . O1 O 0.24632(19) 0.57914(14) 0.31131(16) 0.0307(3) Uani 1 1 d . . . O2 O 0.1488(2) 0.84756(16) 0.3829(2) 0.0441(4) Uani 1 1 d . . . O3 O 0.4452(2) 0.75416(18) 0.1852(2) 0.0497(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 Cu1 0.01954(13) 0.01584(12) 0.01818(13) -0.00183(8) -0.00679(9) -0.00264(9) C1 0.0219(7) 0.0209(6) 0.0259(7) 0.0004(5) -0.0095(6) -0.0034(5) C2 0.0258(7) 0.0261(7) 0.0283(7) 0.0043(6) -0.0142(6) -0.0092(6) C3 0.0330(8) 0.0270(7) 0.0233(7) -0.0002(6) -0.0128(6) -0.0113(6) C4 0.0267(7) 0.0205(7) 0.0211(7) -0.0018(5) -0.0066(6) -0.0057(5) C5 0.0207(6) 0.0162(6) 0.0181(6) 0.0020(5) -0.0051(5) -0.0062(5) C6 0.0201(6) 0.0190(6) 0.0198(6) -0.0010(5) -0.0058(5) -0.0029(5) N1 0.0204(5) 0.0171(5) 0.0198(5) 0.0004(4) -0.0070(4) -0.0040(4) N2 0.0255(6) 0.0186(6) 0.0228(6) 0.0003(4) -0.0107(5) -0.0023(5) N3 0.0215(6) 0.0252(6) 0.0234(6) -0.0007(5) -0.0069(5) -0.0015(5) N4 0.0385(8) 0.0379(8) 0.0282(7) 0.0084(6) -0.0102(6) -0.0015(6) N5 0.0229(6) 0.0199(6) 0.0256(6) 0.0019(5) -0.0096(5) -0.0057(5) O1 0.0367(6) 0.0201(5) 0.0285(6) -0.0041(4) -0.0003(5) -0.0118(5) O2 0.0345(7) 0.0214(6) 0.0587(9) -0.0061(6) 0.0040(6) -0.0060(5) O3 0.0307(7) 0.0307(7) 0.0651(10) 0.0006(6) 0.0100(6) -0.0110(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9734(12) 2_566 ? Cu1 N1 1.9734(12) . ? Cu1 O1 2.0495(11) 2_566 ? Cu1 O1 2.0495(11) . ? Cu1 N2 2.3977(12) . ? Cu1 N2 2.3978(12) 2_566 ? C1 N1 1.3479(18) . ? C1 C2 1.381(2) . ? C1 H1 0.9500 . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 C4 1.385(2) . ? C3 H3 0.9500 . ? C4 C5 1.389(2) . ? C4 H4 0.9500 . ? C5 N1 1.3452(18) . ? C5 C6 1.5066(19) . ? C6 N2 1.4840(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? N2 N3 1.2419(18) . ? N3 N4 1.125(2) . ? N5 O2 1.2208(18) . ? N5 O3 1.2283(18) . ? N5 O1 1.2915(16) . ? 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 Cu1 N1 180.0 2_566 . ? N1 Cu1 O1 86.65(5) 2_566 2_566 ? N1 Cu1 O1 93.35(5) . 2_566 ? N1 Cu1 O1 93.35(5) 2_566 . ? N1 Cu1 O1 86.65(5) . . ? O1 Cu1 O1 180.0 2_566 . ? N1 Cu1 N2 102.34(5) 2_566 . ? N1 Cu1 N2 77.66(5) . . ? O1 Cu1 N2 102.91(5) 2_566 . ? O1 Cu1 N2 77.09(5) . . ? N1 Cu1 N2 77.66(5) 2_566 2_566 ? N1 Cu1 N2 102.34(5) . 2_566 ? O1 Cu1 N2 77.09(5) 2_566 2_566 ? O1 Cu1 N2 102.91(5) . 2_566 ? N2 Cu1 N2 180.00(4) . 2_566 ? N1 C1 C2 122.48(14) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 118.41(14) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.31(14) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.45(14) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.10(13) . . ? N1 C5 C6 119.04(12) . . ? C4 C5 C6 119.82(13) . . ? N2 C6 C5 111.60(11) . . ? N2 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N2 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C5 N1 C1 119.24(12) . . ? C5 N1 Cu1 120.45(10) . . ? C1 N1 Cu1 120.29(10) . . ? N3 N2 C6 114.87(12) . . ? N3 N2 Cu1 126.21(10) . . ? C6 N2 Cu1 103.52(8) . . ? N4 N3 N2 172.54(17) . . ? O2 N5 O3 122.45(13) . . ? O2 N5 O1 119.67(13) . . ? O3 N5 O1 117.77(13) . . ? N5 O1 Cu1 125.90(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.3(2) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ? C3 C4 C5 N1 0.9(2) . . . . ? C3 C4 C5 C6 -176.90(13) . . . . ? N1 C5 C6 N2 22.98(17) . . . . ? C4 C5 C6 N2 -159.21(12) . . . . ? C4 C5 N1 C1 0.0(2) . . . . ? C6 C5 N1 C1 177.82(12) . . . . ? C4 C5 N1 Cu1 -178.58(10) . . . . ? C6 C5 N1 Cu1 -0.80(17) . . . . ? C2 C1 N1 C5 -1.1(2) . . . . ? C2 C1 N1 Cu1 177.47(11) . . . . ? O1 Cu1 N1 C5 -114.94(11) 2_566 . . . ? O1 Cu1 N1 C5 65.06(11) . . . . ? N2 Cu1 N1 C5 -12.45(10) . . . . ? N2 Cu1 N1 C5 167.55(10) 2_566 . . . ? O1 Cu1 N1 C1 66.46(11) 2_566 . . . ? O1 Cu1 N1 C1 -113.54(11) . . . . ? N2 Cu1 N1 C1 168.95(12) . . . . ? N2 Cu1 N1 C1 -11.05(12) 2_566 . . . ? C5 C6 N2 N3 113.18(14) . . . . ? C5 C6 N2 Cu1 -28.18(12) . . . . ? N1 Cu1 N2 N3 66.91(13) 2_566 . . . ? N1 Cu1 N2 N3 -113.09(13) . . . . ? O1 Cu1 N2 N3 -22.44(13) 2_566 . . . ? O1 Cu1 N2 N3 157.55(13) . . . . ? N1 Cu1 N2 C6 -157.69(8) 2_566 . . . ? N1 Cu1 N2 C6 22.31(8) . . . . ? O1 Cu1 N2 C6 112.95(9) 2_566 . . . ? O1 Cu1 N2 C6 -67.05(9) . . . . ? O2 N5 O1 Cu1 -10.0(2) . . . . ? O3 N5 O1 Cu1 173.66(13) . . . . ? N1 Cu1 O1 N5 -46.69(13) 2_566 . . . ? N1 Cu1 O1 N5 133.31(13) . . . . ? N2 Cu1 O1 N5 -148.59(13) . . . . ? N2 Cu1 O1 N5 31.41(13) 2_566 . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 29.07 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.497 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.054 # Attachment 'fig-9A---zhu41final.cif' data_zhu41 _database_code_depnum_ccdc_archive 'CCDC 811008' #TrackingRef 'fig-9A---zhu41final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Cl2 Cu N7' _chemical_formula_sum 'C7 H7 Cl2 Cu N7' _chemical_formula_weight 323.64 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1364(4) _cell_length_b 9.0635(5) _cell_length_c 10.3618(5) _cell_angle_alpha 108.7560(10) _cell_angle_beta 94.2700(10) _cell_angle_gamma 107.2860(10) _cell_volume 595.15(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5977 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 32.94 _exptl_crystal_description flat _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 2.271 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6349 _exptl_absorpt_correction_T_max 0.8217 _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_reflns_number 8719 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 33.14 _reflns_number_total 3312 _reflns_number_gt 2909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.3109P] 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 3312 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0593 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 Cu1 Cu 0.69485(3) 0.70098(2) 0.76787(2) 0.02191(6) Uani 1 1 d . . . Cl1 Cl 0.63224(6) 0.78401(5) 0.99709(4) 0.02595(9) Uani 1 1 d . . . Cl2 Cl 0.55426(7) 0.83200(6) 0.66570(5) 0.03144(10) Uani 1 1 d . . . C1 C 0.7319(2) 0.3889(2) 0.75957(16) 0.0223(3) Uani 1 1 d . . . C2 C 0.8245(3) 0.2831(2) 0.78059(18) 0.0280(4) Uani 1 1 d . . . H2 H 0.7512 0.1688 0.7571 0.034 Uiso 1 1 calc R . . C3 C 1.0276(3) 0.3468(2) 0.83690(19) 0.0294(4) Uani 1 1 d . . . H3 H 1.0941 0.2765 0.8540 0.035 Uiso 1 1 calc R . . C4 C 1.1326(2) 0.5129(2) 0.86796(18) 0.0267(4) Uani 1 1 d . . . H4 H 1.2714 0.5578 0.9061 0.032 Uiso 1 1 calc R . . C5 C 1.0317(2) 0.6124(2) 0.84246(17) 0.0227(3) Uani 1 1 d . . . C6 C 0.5124(2) 0.3317(2) 0.70269(19) 0.0259(3) Uani 1 1 d . . . H6A H 0.4738 0.2297 0.6189 0.031 Uiso 1 1 calc R . . H6B H 0.4337 0.3075 0.7727 0.031 Uiso 1 1 calc R . . C7 C 1.1318(2) 0.7945(2) 0.8715(2) 0.0289(4) Uani 1 1 d . . . H7A H 1.1588 0.8580 0.9725 0.035 Uiso 1 1 calc R . . H7B H 1.2603 0.8137 0.8384 0.035 Uiso 1 1 calc R . . N1 N 0.83405(19) 0.55095(17) 0.79115(14) 0.0206(3) Uani 1 1 d . . . N2 N 0.9951(2) 0.84853(19) 0.79761(16) 0.0282(3) Uani 1 1 d . . . N3 N 1.0664(2) 0.91944(19) 0.71858(16) 0.0295(3) Uani 1 1 d . . . N4 N 1.1138(3) 0.9854(2) 0.6456(2) 0.0462(5) Uani 1 1 d . . . N5 N 0.4751(2) 0.46695(18) 0.66765(16) 0.0261(3) Uani 1 1 d . . . N6 N 0.3092(2) 0.43165(19) 0.59428(15) 0.0271(3) Uani 1 1 d . . . N7 N 0.1658(2) 0.4140(2) 0.52922(18) 0.0389(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 Cu1 0.02046(9) 0.02071(11) 0.02424(11) 0.00895(8) 0.00389(8) 0.00571(8) Cl1 0.02513(18) 0.0274(2) 0.02278(19) 0.00676(16) 0.00432(15) 0.00795(16) Cl2 0.0364(2) 0.0303(2) 0.0327(2) 0.01490(19) 0.00507(18) 0.01504(19) C1 0.0235(7) 0.0217(8) 0.0198(8) 0.0068(6) 0.0055(6) 0.0055(7) C2 0.0332(9) 0.0212(8) 0.0282(9) 0.0074(7) 0.0072(7) 0.0087(7) C3 0.0328(8) 0.0333(10) 0.0287(9) 0.0118(8) 0.0100(7) 0.0190(8) C4 0.0212(7) 0.0343(10) 0.0259(8) 0.0104(7) 0.0074(6) 0.0109(7) C5 0.0190(6) 0.0259(9) 0.0214(8) 0.0085(7) 0.0056(6) 0.0048(6) C6 0.0232(7) 0.0233(9) 0.0283(9) 0.0114(7) 0.0018(6) 0.0025(7) C7 0.0213(7) 0.0287(9) 0.0342(10) 0.0145(8) 0.0002(7) 0.0027(7) N1 0.0190(6) 0.0203(7) 0.0210(7) 0.0070(5) 0.0045(5) 0.0048(5) N2 0.0208(6) 0.0264(8) 0.0362(8) 0.0161(7) 0.0040(6) 0.0015(6) N3 0.0256(7) 0.0245(8) 0.0322(8) 0.0097(6) 0.0015(6) 0.0012(6) N4 0.0432(10) 0.0474(11) 0.0457(11) 0.0277(9) 0.0056(8) 0.0007(9) N5 0.0201(6) 0.0243(7) 0.0301(8) 0.0093(6) 0.0000(5) 0.0038(6) N6 0.0245(7) 0.0288(8) 0.0261(7) 0.0090(6) 0.0066(6) 0.0072(6) N7 0.0290(8) 0.0483(11) 0.0343(9) 0.0107(8) -0.0008(7) 0.0123(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 Cu1 N1 1.9677(14) . ? Cu1 N5 2.0978(15) . ? Cu1 N2 2.0997(14) . ? Cu1 Cl2 2.2127(5) . ? Cu1 Cl1 2.3697(5) . ? C1 N1 1.347(2) . ? C1 C2 1.377(2) . ? C1 C6 1.501(2) . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 N1 1.347(2) . ? C5 C7 1.507(2) . ? C6 N5 1.474(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N2 1.480(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N2 N3 1.244(2) . ? N3 N4 1.119(2) . ? N5 N6 1.252(2) . ? N6 N7 1.121(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 Cu1 N5 77.64(6) . . ? N1 Cu1 N2 78.48(6) . . ? N5 Cu1 N2 146.78(6) . . ? N1 Cu1 Cl2 159.62(4) . . ? N5 Cu1 Cl2 95.59(4) . . ? N2 Cu1 Cl2 98.86(4) . . ? N1 Cu1 Cl1 95.96(4) . . ? N5 Cu1 Cl1 103.72(4) . . ? N2 Cu1 Cl1 101.42(5) . . ? Cl2 Cu1 Cl1 104.345(18) . . ? N1 C1 C2 121.40(15) . . ? N1 C1 C6 116.38(15) . . ? C2 C1 C6 122.22(15) . . ? C1 C2 C3 118.65(16) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.81(17) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 118.80(16) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 121.15(15) . . ? N1 C5 C7 115.70(15) . . ? C4 C5 C7 123.14(15) . . ? N5 C6 C1 106.87(13) . . ? N5 C6 H6A 110.3 . . ? C1 C6 H6A 110.3 . . ? N5 C6 H6B 110.3 . . ? C1 C6 H6B 110.3 . . ? H6A C6 H6B 108.6 . . ? N2 C7 C5 107.67(13) . . ? N2 C7 H7A 110.2 . . ? C5 C7 H7A 110.2 . . ? N2 C7 H7B 110.2 . . ? C5 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C5 N1 C1 120.15(14) . . ? C5 N1 Cu1 119.44(11) . . ? C1 N1 Cu1 120.38(11) . . ? N3 N2 C7 116.26(14) . . ? N3 N2 Cu1 124.85(12) . . ? C7 N2 Cu1 112.10(10) . . ? N4 N3 N2 173.5(2) . . ? N6 N5 C6 116.40(14) . . ? N6 N5 Cu1 128.20(12) . . ? C6 N5 Cu1 114.95(10) . . ? N7 N6 N5 173.94(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.6(2) . . . . ? C6 C1 C2 C3 -178.44(16) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 N1 1.4(2) . . . . ? C3 C4 C5 C7 -179.60(16) . . . . ? N1 C1 C6 N5 12.3(2) . . . . ? C2 C1 C6 N5 -168.60(15) . . . . ? N1 C5 C7 N2 -16.2(2) . . . . ? C4 C5 C7 N2 164.81(15) . . . . ? C4 C5 N1 C1 -2.1(2) . . . . ? C7 C5 N1 C1 178.86(14) . . . . ? C4 C5 N1 Cu1 176.17(12) . . . . ? C7 C5 N1 Cu1 -2.87(19) . . . . ? C2 C1 N1 C5 1.1(2) . . . . ? C6 C1 N1 C5 -179.85(14) . . . . ? C2 C1 N1 Cu1 -177.19(12) . . . . ? C6 C1 N1 Cu1 1.90(19) . . . . ? N5 Cu1 N1 C5 171.10(13) . . . . ? N2 Cu1 N1 C5 14.36(12) . . . . ? Cl2 Cu1 N1 C5 98.79(16) . . . . ? Cl1 Cu1 N1 C5 -86.12(11) . . . . ? N5 Cu1 N1 C1 -10.64(12) . . . . ? N2 Cu1 N1 C1 -167.38(13) . . . . ? Cl2 Cu1 N1 C1 -82.95(16) . . . . ? Cl1 Cu1 N1 C1 92.14(12) . . . . ? C5 C7 N2 N3 -126.07(16) . . . . ? C5 C7 N2 Cu1 26.56(17) . . . . ? N1 Cu1 N2 N3 127.05(16) . . . . ? N5 Cu1 N2 N3 82.30(18) . . . . ? Cl2 Cu1 N2 N3 -32.41(16) . . . . ? Cl1 Cu1 N2 N3 -139.11(15) . . . . ? N1 Cu1 N2 C7 -22.80(12) . . . . ? N5 Cu1 N2 C7 -67.56(16) . . . . ? Cl2 Cu1 N2 C7 177.74(11) . . . . ? Cl1 Cu1 N2 C7 71.04(12) . . . . ? C1 C6 N5 N6 166.64(14) . . . . ? C1 C6 N5 Cu1 -20.42(17) . . . . ? N1 Cu1 N5 N6 -170.52(15) . . . . ? N2 Cu1 N5 N6 -125.59(15) . . . . ? Cl2 Cu1 N5 N6 -10.00(15) . . . . ? Cl1 Cu1 N5 N6 96.27(14) . . . . ? N1 Cu1 N5 C6 17.53(11) . . . . ? N2 Cu1 N5 C6 62.47(16) . . . . ? Cl2 Cu1 N5 C6 178.06(11) . . . . ? Cl1 Cu1 N5 C6 -75.68(12) . . . . ? _diffrn_measured_fraction_theta_max 0.731 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.731 _refine_diff_density_max 0.418 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.063 # Attachment 'fig-9B---zhu67final.cif' data_zhu67 _database_code_depnum_ccdc_archive 'CCDC 811009' #TrackingRef 'fig-9B---zhu67final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Cl2 Cu N7' _chemical_formula_sum 'C7 H7 Cl2 Cu N7' _chemical_formula_weight 323.64 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.1972(7) _cell_length_b 12.5443(6) _cell_length_c 14.1168(10) _cell_angle_alpha 90.00 _cell_angle_beta 119.04 _cell_angle_gamma 90.00 _cell_volume 2352.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6298 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.81 _exptl_crystal_description irregular, _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.827 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 2.298 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6961 _exptl_absorpt_correction_T_max 0.8028 _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_reflns_number 12958 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2598 _reflns_number_gt 2366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0284P)^2^+3.1320P] 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 2598 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0553 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 Cu1 Cu 0.145958(14) 0.814045(15) 0.119086(17) 0.01996(7) Uani 1 1 d . . . Cl1 Cl 0.22811(3) 0.81906(3) 0.31643(4) 0.02947(11) Uani 1 1 d . . . Cl2 Cl 0.21291(3) 0.95118(3) 0.07753(4) 0.02629(10) Uani 1 1 d . . . C1 C -0.07327(13) 0.80924(14) 0.06051(17) 0.0293(4) Uani 1 1 d . . . H1A H -0.1270 0.8119 -0.0161 0.035 Uiso 1 1 calc R . . H1B H -0.1028 0.8295 0.1069 0.035 Uiso 1 1 calc R . . C2 C -0.02939(12) 0.69876(13) 0.08881(14) 0.0235(3) Uani 1 1 d . . . C3 C 0.11222(12) 0.59247(13) 0.13328(13) 0.0220(3) Uani 1 1 d . . . C4 C 0.06291(14) 0.50221(14) 0.13978(14) 0.0270(4) Uani 1 1 d . . . H4 H 0.0956 0.4348 0.1574 0.032 Uiso 1 1 calc R . . C5 C -0.03568(14) 0.51290(15) 0.11980(15) 0.0290(4) Uani 1 1 d . . . H5 H -0.0711 0.4522 0.1239 0.035 Uiso 1 1 calc R . . C6 C -0.08281(13) 0.61176(15) 0.09381(14) 0.0279(4) Uani 1 1 d . . . H6 H -0.1503 0.6194 0.0798 0.033 Uiso 1 1 calc R . . C7 C 0.22002(13) 0.59154(13) 0.15557(16) 0.0269(4) Uani 1 1 d . . . H7A H 0.2668 0.5850 0.2343 0.032 Uiso 1 1 calc R . . H7B H 0.2315 0.5309 0.1180 0.032 Uiso 1 1 calc R . . N1 N 0.23611(11) 0.69424(11) 0.11399(13) 0.0235(3) Uani 1 1 d . . . N2 N 0.32443(11) 0.71428(11) 0.13454(12) 0.0251(3) Uani 1 1 d . . . N3 N 0.39866(12) 0.74177(14) 0.14572(16) 0.0403(4) Uani 1 1 d . . . N4 N 0.06645(10) 0.68767(10) 0.10863(12) 0.0210(3) Uani 1 1 d . . . N5 N 0.00964(11) 0.88368(12) 0.07840(13) 0.0285(3) Uani 1 1 d . . . N6 N 0.01333(11) 0.97099(13) 0.12290(13) 0.0308(3) Uani 1 1 d . . . N7 N 0.02633(15) 1.05182(16) 0.16090(17) 0.0519(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01742(11) 0.01533(11) 0.02931(12) 0.00073(8) 0.01305(9) 0.00009(7) Cl1 0.0334(2) 0.0282(2) 0.0267(2) -0.00298(16) 0.01452(19) -0.00642(17) Cl2 0.0240(2) 0.02006(19) 0.0378(2) 0.00338(16) 0.01728(18) -0.00179(15) C1 0.0184(8) 0.0281(9) 0.0428(11) 0.0038(8) 0.0158(8) 0.0003(7) C2 0.0186(8) 0.0260(9) 0.0244(8) -0.0003(7) 0.0093(7) -0.0023(6) C3 0.0217(8) 0.0206(8) 0.0224(8) -0.0011(6) 0.0097(7) -0.0020(6) C4 0.0312(9) 0.0198(8) 0.0287(9) 0.0011(7) 0.0135(8) -0.0030(7) C5 0.0293(9) 0.0276(9) 0.0299(9) 0.0002(7) 0.0142(8) -0.0102(7) C6 0.0210(8) 0.0322(9) 0.0300(9) 0.0019(7) 0.0121(7) -0.0044(7) C7 0.0235(9) 0.0176(8) 0.0393(10) 0.0045(7) 0.0151(8) 0.0015(6) N1 0.0198(7) 0.0196(7) 0.0343(8) 0.0024(6) 0.0156(6) 0.0022(5) N2 0.0240(8) 0.0196(7) 0.0305(8) 0.0034(6) 0.0121(6) 0.0037(6) N3 0.0244(8) 0.0328(9) 0.0616(12) 0.0122(8) 0.0193(8) 0.0034(7) N4 0.0189(7) 0.0192(7) 0.0246(7) 0.0001(5) 0.0104(6) -0.0012(5) N5 0.0218(7) 0.0208(7) 0.0458(9) 0.0001(6) 0.0187(7) 0.0020(6) N6 0.0241(8) 0.0316(9) 0.0350(9) -0.0013(7) 0.0130(7) 0.0063(6) N7 0.0395(11) 0.0448(12) 0.0630(13) -0.0211(10) 0.0181(10) 0.0065(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 Cu1 N4 1.9549(13) . ? Cu1 N5 2.0565(14) . ? Cu1 N1 2.0582(14) . ? Cu1 Cl2 2.2177(4) . ? Cu1 Cl1 2.4386(5) . ? C1 N5 1.488(2) . ? C1 C2 1.505(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N4 1.350(2) . ? C2 C6 1.382(2) . ? C3 N4 1.340(2) . ? C3 C4 1.385(2) . ? C3 C7 1.511(2) . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.484(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N1 N2 1.253(2) . ? N2 N3 1.115(2) . ? N5 N6 1.250(2) . ? N6 N7 1.119(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 N4 Cu1 N5 79.71(6) . . ? N4 Cu1 N1 78.63(6) . . ? N5 Cu1 N1 153.86(6) . . ? N4 Cu1 Cl2 162.78(5) . . ? N5 Cu1 Cl2 97.23(4) . . ? N1 Cu1 Cl2 99.12(4) . . ? N4 Cu1 Cl1 93.56(4) . . ? N5 Cu1 Cl1 101.29(5) . . ? N1 Cu1 Cl1 94.50(5) . . ? Cl2 Cu1 Cl1 103.648(17) . . ? N5 C1 C2 107.64(14) . . ? N5 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? N5 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N4 C2 C6 120.61(16) . . ? N4 C2 C1 116.37(14) . . ? C6 C2 C1 123.02(15) . . ? N4 C3 C4 121.08(15) . . ? N4 C3 C7 115.76(14) . . ? C4 C3 C7 123.14(15) . . ? C3 C4 C5 118.18(17) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 120.43(16) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C2 C6 C5 118.55(16) . . ? C2 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? N1 C7 C3 106.32(13) . . ? N1 C7 H7A 110.5 . . ? C3 C7 H7A 110.5 . . ? N1 C7 H7B 110.5 . . ? C3 C7 H7B 110.5 . . ? H7A C7 H7B 108.7 . . ? N2 N1 C7 116.49(14) . . ? N2 N1 Cu1 120.12(11) . . ? C7 N1 Cu1 112.32(10) . . ? N3 N2 N1 172.26(18) . . ? C3 N4 C2 121.15(14) . . ? C3 N4 Cu1 118.62(11) . . ? C2 N4 Cu1 119.81(11) . . ? N6 N5 C1 117.55(15) . . ? N6 N5 Cu1 116.00(12) . . ? C1 N5 Cu1 115.85(11) . . ? N7 N6 N5 171.5(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 N5 C1 C2 N4 -8.5(2) . . . . ? N5 C1 C2 C6 172.11(17) . . . . ? N4 C3 C4 C5 0.1(3) . . . . ? C7 C3 C4 C5 178.64(16) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? N4 C2 C6 C5 0.1(3) . . . . ? C1 C2 C6 C5 179.46(17) . . . . ? C4 C5 C6 C2 -0.3(3) . . . . ? N4 C3 C7 N1 -15.3(2) . . . . ? C4 C3 C7 N1 166.16(16) . . . . ? C3 C7 N1 N2 172.95(15) . . . . ? C3 C7 N1 Cu1 28.80(17) . . . . ? N4 Cu1 N1 N2 -168.93(15) . . . . ? N5 Cu1 N1 N2 156.50(14) . . . . ? Cl2 Cu1 N1 N2 28.42(14) . . . . ? Cl1 Cu1 N1 N2 -76.20(13) . . . . ? N4 Cu1 N1 C7 -26.24(12) . . . . ? N5 Cu1 N1 C7 -60.8(2) . . . . ? Cl2 Cu1 N1 C7 171.11(11) . . . . ? Cl1 Cu1 N1 C7 66.50(12) . . . . ? C4 C3 N4 C2 -0.3(3) . . . . ? C7 C3 N4 C2 -178.93(15) . . . . ? C4 C3 N4 Cu1 172.28(13) . . . . ? C7 C3 N4 Cu1 -6.3(2) . . . . ? C6 C2 N4 C3 0.2(3) . . . . ? C1 C2 N4 C3 -179.21(16) . . . . ? C6 C2 N4 Cu1 -172.30(13) . . . . ? C1 C2 N4 Cu1 8.3(2) . . . . ? N5 Cu1 N4 C3 -176.52(14) . . . . ? N1 Cu1 N4 C3 18.20(13) . . . . ? Cl2 Cu1 N4 C3 102.30(17) . . . . ? Cl1 Cu1 N4 C3 -75.68(13) . . . . ? N5 Cu1 N4 C2 -3.83(13) . . . . ? N1 Cu1 N4 C2 -169.11(14) . . . . ? Cl2 Cu1 N4 C2 -85.01(19) . . . . ? Cl1 Cu1 N4 C2 97.01(13) . . . . ? C2 C1 N5 N6 -137.91(17) . . . . ? C2 C1 N5 Cu1 5.45(19) . . . . ? N4 Cu1 N5 N6 142.53(15) . . . . ? N1 Cu1 N5 N6 176.96(13) . . . . ? Cl2 Cu1 N5 N6 -54.62(14) . . . . ? Cl1 Cu1 N5 N6 50.92(14) . . . . ? N4 Cu1 N5 C1 -1.40(13) . . . . ? N1 Cu1 N5 C1 33.0(2) . . . . ? Cl2 Cu1 N5 C1 161.45(13) . . . . ? Cl1 Cu1 N5 C1 -93.01(13) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.330 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.057 # Attachment 'fig-9C---zhu68newfinal.cif' data_zhu68 _database_code_depnum_ccdc_archive 'CCDC 811010' #TrackingRef 'fig-9C---zhu68newfinal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 Cu N9 O7' _chemical_formula_sum 'C7 H9 Cu N9 O7' _chemical_formula_weight 394.77 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' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall -P2n2ab 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 15.5617(12) _cell_length_b 11.3047(9) _cell_length_c 7.9984(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1407.08(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6109 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.59 _exptl_crystal_description flat _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 1.612 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7387 _exptl_absorpt_correction_T_max 0.9237 _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_reflns_number 16297 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1611 _reflns_number_gt 1440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+0.8582P] 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 1611 _refine_ls_number_parameters 134 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.15484(2) 0.2500 0.01807(10) Uani 1 2 d S . . C1 C 0.36389(10) 0.30996(13) 0.1016(2) 0.0208(3) Uani 1 1 d . A . H1A H 0.3087 0.3242 0.1599 0.025 Uiso 1 1 calc R . . H1B H 0.3567 0.3306 -0.0179 0.025 Uiso 1 1 calc R . . C2 C 0.43413(9) 0.38393(13) 0.17860(19) 0.0190(3) Uani 1 1 d . . . C3 C 0.43238(10) 0.50672(14) 0.1771(2) 0.0251(3) Uani 1 1 d . . . H3 H 0.3858 0.5480 0.1271 0.030 Uiso 1 1 calc R . . C4 C 0.5000 0.5678(2) 0.2500 0.0272(5) Uani 1 2 d S . . H4 H 0.5000 0.6519 0.2500 0.033 Uiso 1 2 calc SR . . N1 N 0.5000 0.32559(16) 0.2500 0.0176(4) Uani 1 2 d S . . N2 N 0.38951(8) 0.18406(11) 0.11873(17) 0.0214(3) Uani 1 1 d . . . N3 N 0.3291(6) 0.1132(8) 0.142(3) 0.037(3) Uani 0.37(2) 1 d PU A 1 N4 N 0.2795(4) 0.0430(6) 0.152(4) 0.081(7) Uani 0.37(2) 1 d PU A 1 N3A N 0.3348(3) 0.1104(5) 0.0689(10) 0.0267(10) Uani 0.63(2) 1 d PU A 2 N4A N 0.2917(3) 0.0371(3) 0.0287(13) 0.0516(19) Uani 0.63(2) 1 d PU A 2 N5 N 0.63162(8) 0.20740(12) -0.06754(17) 0.0227(3) Uani 1 1 d . A . O1 O 0.56912(9) 0.14439(13) -0.01556(17) 0.0407(4) Uani 1 1 d . . . O2 O 0.64816(10) 0.20928(13) -0.21769(15) 0.0390(3) Uani 1 1 d . . . O3 O 0.67321(8) 0.26601(12) 0.03452(16) 0.0354(3) Uani 1 1 d . . . O4 O 0.5000 -0.01269(17) 0.2500 0.0414(5) Uani 1 2 d S . . H4O H 0.4812(17) -0.051(2) 0.180(3) 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01919(16) 0.01403(15) 0.02099(16) 0.000 -0.00429(9) 0.000 C1 0.0192(7) 0.0176(7) 0.0257(8) 0.0025(6) -0.0031(6) 0.0011(6) C2 0.0172(7) 0.0196(7) 0.0203(7) 0.0013(6) 0.0014(6) 0.0014(5) C3 0.0221(7) 0.0204(7) 0.0329(9) 0.0030(6) -0.0019(6) 0.0032(6) C4 0.0266(12) 0.0168(10) 0.0382(14) 0.000 0.0013(9) 0.000 N1 0.0168(9) 0.0170(8) 0.0191(9) 0.000 0.0015(6) 0.000 N2 0.0167(6) 0.0178(6) 0.0296(7) -0.0013(5) -0.0042(5) -0.0010(5) N3 0.019(3) 0.022(3) 0.072(8) 0.003(4) -0.014(4) 0.0041(19) N4 0.019(3) 0.024(3) 0.20(2) 0.020(5) -0.019(5) -0.003(2) N3A 0.0185(14) 0.0193(14) 0.042(3) 0.0040(18) -0.0076(18) 0.0012(10) N4A 0.0305(18) 0.0228(14) 0.102(5) 0.0022(19) -0.026(2) -0.0026(12) N5 0.0202(6) 0.0242(7) 0.0237(7) 0.0005(5) 0.0011(5) 0.0021(5) O1 0.0341(7) 0.0562(9) 0.0318(7) -0.0182(6) 0.0124(6) -0.0248(6) O2 0.0514(9) 0.0444(8) 0.0211(6) 0.0033(5) 0.0061(6) -0.0009(7) O3 0.0320(7) 0.0408(7) 0.0334(7) -0.0078(6) 0.0006(5) -0.0145(6) O4 0.0640(14) 0.0153(8) 0.0449(12) 0.000 -0.0329(10) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.8939(19) . ? Cu1 N1 1.9303(19) . ? Cu1 N2 2.0415(13) . ? Cu1 N2 2.0415(13) 3_655 ? Cu1 O1 2.3838(13) 3_655 ? Cu1 O1 2.3838(13) . ? C1 N2 1.4845(19) . ? C1 C2 1.508(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.3460(17) . ? C2 C3 1.388(2) . ? C3 C4 1.3874(19) . ? C3 H3 0.9500 . ? C4 C3 1.3874(19) 3_655 ? C4 H4 0.9500 . ? N1 C2 1.3460(17) 3_655 ? N2 N3 1.248(10) . ? N2 N3A 1.256(6) . ? N3 N4 1.111(11) . ? N3A N4A 1.113(6) . ? N5 O2 1.2285(18) . ? N5 O3 1.2346(18) . ? N5 O1 1.2753(18) . ? O4 H4O 0.76(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 O4 Cu1 N1 180.0 . . ? O4 Cu1 N2 99.31(4) . . ? N1 Cu1 N2 80.69(4) . . ? O4 Cu1 N2 99.31(4) . 3_655 ? N1 Cu1 N2 80.69(4) . 3_655 ? N2 Cu1 N2 161.38(7) . 3_655 ? O4 Cu1 O1 87.16(3) . 3_655 ? N1 Cu1 O1 92.84(3) . 3_655 ? N2 Cu1 O1 94.95(5) . 3_655 ? N2 Cu1 O1 85.97(5) 3_655 3_655 ? O4 Cu1 O1 87.16(3) . . ? N1 Cu1 O1 92.84(3) . . ? N2 Cu1 O1 85.97(5) . . ? N2 Cu1 O1 94.95(5) 3_655 . ? O1 Cu1 O1 174.32(7) 3_655 . ? N2 C1 C2 107.41(12) . . ? N2 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? N2 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C3 120.57(15) . . ? N1 C2 C1 116.98(13) . . ? C3 C2 C1 122.45(13) . . ? C4 C3 C2 118.64(15) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C3 120.3(2) . 3_655 ? C3 C4 H4 119.9 . . ? C3 C4 H4 119.9 3_655 . ? C2 N1 C2 121.32(19) 3_655 . ? C2 N1 Cu1 119.34(9) 3_655 . ? C2 N1 Cu1 119.34(9) . . ? N3 N2 C1 115.3(4) . . ? N3A N2 C1 115.1(3) . . ? N3 N2 Cu1 117.0(6) . . ? N3A N2 Cu1 128.8(3) . . ? C1 N2 Cu1 115.39(9) . . ? N4 N3 N2 173.3(10) . . ? N4A N3A N2 173.5(5) . . ? O2 N5 O3 121.83(15) . . ? O2 N5 O1 119.22(14) . . ? O3 N5 O1 118.95(13) . . ? N5 O1 Cu1 127.37(10) . . ? Cu1 O4 H4O 124.2(19) . . ? 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 N2 C1 C2 N1 -2.83(17) . . . . ? N2 C1 C2 C3 177.04(14) . . . . ? N1 C2 C3 C4 0.2(2) . . . . ? C1 C2 C3 C4 -179.63(13) . . . . ? C2 C3 C4 C3 -0.11(11) . . . 3_655 ? C3 C2 N1 C2 -0.12(11) . . . 3_655 ? C1 C2 N1 C2 179.75(15) . . . 3_655 ? C3 C2 N1 Cu1 179.88(11) . . . . ? C1 C2 N1 Cu1 -0.25(15) . . . . ? N2 Cu1 N1 C2 -177.72(8) . . . 3_655 ? N2 Cu1 N1 C2 2.28(8) 3_655 . . 3_655 ? O1 Cu1 N1 C2 87.73(8) 3_655 . . 3_655 ? O1 Cu1 N1 C2 -92.27(8) . . . 3_655 ? N2 Cu1 N1 C2 2.28(8) . . . . ? N2 Cu1 N1 C2 -177.72(8) 3_655 . . . ? O1 Cu1 N1 C2 -92.27(8) 3_655 . . . ? O1 Cu1 N1 C2 87.73(8) . . . . ? C2 C1 N2 N3 145.8(10) . . . . ? C2 C1 N2 N3A 176.0(4) . . . . ? C2 C1 N2 Cu1 4.53(15) . . . . ? O4 Cu1 N2 N3 35.5(9) . . . . ? N1 Cu1 N2 N3 -144.5(9) . . . . ? N2 Cu1 N2 N3 -144.5(9) 3_655 . . . ? O1 Cu1 N2 N3 -52.4(9) 3_655 . . . ? O1 Cu1 N2 N3 122.0(9) . . . . ? O4 Cu1 N2 N3A 6.1(5) . . . . ? N1 Cu1 N2 N3A -173.9(5) . . . . ? N2 Cu1 N2 N3A -173.9(5) 3_655 . . . ? O1 Cu1 N2 N3A -81.8(5) 3_655 . . . ? O1 Cu1 N2 N3A 92.5(5) . . . . ? O4 Cu1 N2 C1 176.11(10) . . . . ? N1 Cu1 N2 C1 -3.89(10) . . . . ? N2 Cu1 N2 C1 -3.89(10) 3_655 . . . ? O1 Cu1 N2 C1 88.19(11) 3_655 . . . ? O1 Cu1 N2 C1 -97.43(11) . . . . ? O2 N5 O1 Cu1 -164.54(12) . . . . ? O3 N5 O1 Cu1 14.6(2) . . . . ? N1 Cu1 O1 N5 42.14(14) . . . . ? N2 Cu1 O1 N5 122.59(15) . . . . ? N2 Cu1 O1 N5 -38.75(15) 3_655 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.317 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.054