# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Qiu-Yun Chen' _publ_contact_author_address ; School of chemistry and chemical engineering Jiangsu University 212013 China ; _publ_contact_author_email chenqy@ujs.edu.cn loop_ _publ_author_name 'Yun Chen.' 'Haijian Fu.' 'Weihua Zhu.' 'Yan Qi.' 'Zhengping Ma.' 'Kaidi Zhao.' ; Jing Gao ; data_s _database_code_depnum_ccdc_archive 'CCDC 766526' #TrackingRef '- CIF-DIPY deposit.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H31 Cl Cu N5 O4, Cl O4' _chemical_formula_sum 'C31 H31 Cl2 Cu N5 O10' _chemical_formula_weight 768.05 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2186(16) _cell_length_b 18.370(4) _cell_length_c 21.523(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.39(3) _cell_angle_gamma 90.00 _cell_volume 3240.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12432 _cell_measurement_theta_min 2.4120 _cell_measurement_theta_max 29.2015 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1580 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8089 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15849 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0583 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.38 _reflns_number_total 6479 _reflns_number_gt 5304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.1298P)^2^+3.8458P] 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 SHELXS _refine_ls_extinction_coef ? _refine_ls_number_reflns 6479 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.2572 _refine_ls_wR_factor_gt 0.2406 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.008 _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 0.18840(7) 0.72560(3) 0.14835(3) 0.0411(2) Uani 1 1 d . . . N3 N 0.3631(5) 0.7685(2) 0.2083(2) 0.0426(10) Uani 1 1 d . . . N2 N 0.3189(5) 0.6310(2) 0.1530(2) 0.0423(10) Uani 1 1 d . . . N4 N 0.0522(5) 0.8153(2) 0.1356(2) 0.0409(9) Uani 1 1 d . . . N5 N 0.0152(5) 0.6869(2) 0.0863(2) 0.0443(10) Uani 1 1 d . . . C26 C -0.1038(6) 0.7344(3) 0.0682(2) 0.0384(11) Uani 1 1 d . . . C25 C -0.0815(6) 0.8085(3) 0.0954(2) 0.0396(11) Uani 1 1 d . . . N1 N 0.1087(5) 0.6773(2) 0.2406(2) 0.0421(10) Uani 1 1 d . . . C9 C 0.4975(7) 0.7659(3) 0.3102(3) 0.0526(14) Uani 1 1 d . . . H9A H 0.4993 0.7496 0.3526 0.063 Uiso 1 1 d R . . C27 C -0.2353(7) 0.7144(3) 0.0272(3) 0.0510(13) Uani 1 1 d . . . H27 H -0.3167 0.7481 0.0159 0.061 Uiso 1 1 d R . . C2 C 0.2747(7) 0.5825(3) 0.1949(2) 0.0444(12) Uani 1 1 d . . . C8 C 0.3683(6) 0.7470(3) 0.2681(2) 0.0401(11) Uani 1 1 d . . . C24 C -0.1842(7) 0.8657(3) 0.0803(3) 0.0459(12) Uani 1 1 d . . . H24 H -0.2760 0.8585 0.0529 0.055 Uiso 1 1 d R . . C28 C -0.2451(8) 0.6452(4) 0.0034(3) 0.0550(14) Uani 1 1 d . . . C31 C 0.0036(8) 0.6183(3) 0.0629(3) 0.0556(14) Uani 1 1 d . . . H31 H 0.0844 0.5846 0.0751 0.067 Uiso 1 1 d R . . C12 C 0.4874(7) 0.8098(3) 0.1897(3) 0.0504(13) Uani 1 1 d . . . H12 H 0.4850 0.8246 0.1483 0.060 Uiso 1 1 d R . . C14 C -0.1388(6) 0.6538(3) 0.3017(3) 0.0476(13) Uani 1 1 d . . . C13 C -0.0613(7) 0.6970(3) 0.2523(3) 0.0515(13) Uani 1 1 d . . . H13A H -0.1286 0.6918 0.2135 0.062 Uiso 1 1 d R . . H13B H -0.0631 0.7480 0.2640 0.062 Uiso 1 1 d R . . C22 C -0.1515(7) 0.9350(3) 0.1059(3) 0.0487(13) Uani 1 1 d . . . C6 C 0.4466(7) 0.6170(3) 0.1198(3) 0.0480(13) Uani 1 1 d . . . H6 H 0.4780 0.6515 0.0915 0.058 Uiso 1 1 d R . . C3 C 0.3583(7) 0.5176(3) 0.2037(3) 0.0561(14) Uani 1 1 d . . . H3 H 0.3266 0.4843 0.2329 0.067 Uiso 1 1 d R . . C20 C 0.0822(7) 0.8811(3) 0.1613(3) 0.0529(14) Uani 1 1 d . . . H20 H 0.1722 0.8864 0.1898 0.064 Uiso 1 1 d R . . C7 C 0.2285(8) 0.7049(4) 0.2901(3) 0.0544(14) Uani 1 1 d . . . H7A H 0.2718 0.6637 0.3143 0.065 Uiso 1 1 d R . . H7B H 0.1713 0.7356 0.3179 0.065 Uiso 1 1 d R . . C11 C 0.6166(7) 0.8302(3) 0.2301(3) 0.0555(15) Uani 1 1 d . . . H11 H 0.6993 0.8592 0.2163 0.067 Uiso 1 1 d R . . C10 C 0.6228(7) 0.8073(3) 0.2914(3) 0.0546(14) Uani 1 1 d . . . H10 H 0.7103 0.8199 0.3193 0.065 Uiso 1 1 d R . . C21 C -0.0150(8) 0.9411(3) 0.1471(3) 0.0548(14) Uani 1 1 d . . . H21 H 0.0117 0.9858 0.1655 0.066 Uiso 1 1 d R . . C30 C -0.1227(8) 0.5973(3) 0.0221(3) 0.0620(16) Uani 1 1 d . . . H30 H -0.1260 0.5500 0.0067 0.074 Uiso 1 1 d R . . C18 C -0.1715(9) 0.6253(5) 0.4086(3) 0.084(2) Uani 1 1 d . . . H18 H -0.1414 0.6325 0.4507 0.101 Uiso 1 1 d R . . C4 C 0.4874(7) 0.5022(3) 0.1695(3) 0.0556(15) Uani 1 1 d . . . H4 H 0.5439 0.4585 0.1750 0.067 Uiso 1 1 d R . . C15 C -0.2547(8) 0.6005(4) 0.2857(3) 0.0624(16) Uani 1 1 d . . . H15 H -0.2836 0.5913 0.2438 0.075 Uiso 1 1 d R . . C5 C 0.5323(7) 0.5530(3) 0.1266(3) 0.0538(14) Uani 1 1 d . . . H5 H 0.6194 0.5439 0.1026 0.065 Uiso 1 1 d R . . C19 C -0.0995(8) 0.6660(4) 0.3652(3) 0.0640(17) Uani 1 1 d . . . H19 H -0.0243 0.7018 0.3779 0.077 Uiso 1 1 d R . . C23 C -0.2594(10) 0.9982(4) 0.0880(4) 0.078(2) Uani 1 1 d . . . H23A H -0.2191 1.0409 0.1098 0.116 Uiso 1 1 d R . . H23B H -0.3683 0.9881 0.0989 0.116 Uiso 1 1 d R . . H23C H -0.2604 1.0063 0.0439 0.116 Uiso 1 1 d R . . C17 C -0.2876(9) 0.5738(5) 0.3912(3) 0.079(2) Uani 1 1 d . . . H17 H -0.3386 0.5477 0.4212 0.094 Uiso 1 1 d R . . C16 C -0.3270(8) 0.5614(4) 0.3298(3) 0.0733(19) Uani 1 1 d . . . H16 H -0.4039 0.5259 0.3177 0.088 Uiso 1 1 d R . . C1 C 0.1281(7) 0.5992(3) 0.2291(3) 0.0537(14) Uani 1 1 d . . . H1A H 0.0316 0.5813 0.2051 0.064 Uiso 1 1 d R . . H1B H 0.1367 0.5737 0.2686 0.064 Uiso 1 1 d R . . C29 C -0.3878(10) 0.6223(4) -0.0408(3) 0.079(2) Uani 1 1 d . . . H29A H -0.4603 0.6629 -0.0484 0.118 Uiso 1 1 d R . . H29B H -0.4453 0.5832 -0.0226 0.118 Uiso 1 1 d R . . H29C H -0.3486 0.6065 -0.0794 0.118 Uiso 1 1 d R . . Cl1 Cl 0.32859(17) 0.82191(9) 0.00900(7) 0.0579(4) Uani 1 1 d . . . O1 O 0.3513(6) 0.7618(2) 0.0515(2) 0.0720(13) Uani 1 1 d . . . O4 O 0.3888(13) 0.8842(4) 0.0422(4) 0.155(4) Uani 1 1 d . . . O3 O 0.1670(6) 0.8323(5) -0.0069(3) 0.129(3) Uani 1 1 d . . . O2 O 0.4221(10) 0.8136(5) -0.0405(4) 0.152(4) Uani 1 1 d . . . Cl2 Cl 0.9249(2) 0.41162(10) 0.14814(11) 0.0744(5) Uani 1 1 d . . . O8 O 0.853(2) 0.4346(16) 0.1926(6) 0.393(17) Uani 1 1 d . . . O5 O 0.7964(15) 0.3995(12) 0.1109(13) 0.400(18) Uani 1 1 d . . . O9 O 1.0152(15) 0.3607(10) 0.1533(13) 0.429(18) Uani 1 1 d . . . O10 O 0.998(3) 0.4617(7) 0.1216(6) 0.310(10) 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 0.0421(4) 0.0373(4) 0.0436(4) 0.0002(2) 0.0005(3) 0.0033(3) N3 0.042(2) 0.042(2) 0.044(2) 0.0022(18) 0.0056(19) -0.0003(19) N2 0.043(2) 0.040(2) 0.044(2) 0.0027(18) 0.0053(19) 0.0019(19) N4 0.040(2) 0.040(2) 0.043(2) -0.0002(18) 0.0020(18) 0.0012(19) N5 0.046(2) 0.040(2) 0.047(3) -0.0030(19) 0.0021(19) 0.002(2) C26 0.038(3) 0.041(3) 0.036(3) 0.005(2) 0.005(2) 0.002(2) C25 0.044(3) 0.045(3) 0.030(2) 0.004(2) 0.009(2) 0.007(2) N1 0.041(2) 0.041(2) 0.045(2) 0.0005(18) 0.0060(18) -0.0015(19) C9 0.049(3) 0.064(4) 0.044(3) -0.008(3) -0.001(2) 0.001(3) C27 0.052(3) 0.052(3) 0.048(3) 0.001(2) -0.003(3) -0.002(3) C2 0.047(3) 0.038(3) 0.047(3) 0.005(2) 0.000(2) 0.001(2) C8 0.041(3) 0.040(3) 0.040(3) -0.001(2) 0.005(2) 0.004(2) C24 0.046(3) 0.051(3) 0.042(3) 0.004(2) 0.009(2) 0.005(2) C28 0.063(4) 0.066(4) 0.035(3) -0.003(3) 0.002(3) -0.007(3) C31 0.060(3) 0.039(3) 0.066(4) -0.009(3) -0.003(3) 0.011(3) C12 0.053(3) 0.046(3) 0.052(3) 0.000(2) 0.002(3) -0.009(3) C14 0.034(3) 0.060(3) 0.050(3) -0.002(3) 0.009(2) 0.004(2) C13 0.045(3) 0.055(3) 0.056(3) 0.005(3) 0.012(2) 0.008(3) C22 0.050(3) 0.043(3) 0.054(3) 0.007(2) 0.014(2) 0.012(3) C6 0.051(3) 0.048(3) 0.046(3) 0.002(2) 0.014(2) 0.002(3) C3 0.061(4) 0.049(3) 0.059(4) 0.005(3) 0.009(3) 0.003(3) C20 0.053(3) 0.048(3) 0.058(3) -0.008(3) -0.001(3) 0.007(3) C7 0.061(4) 0.065(4) 0.036(3) 0.003(3) 0.003(2) -0.016(3) C11 0.047(3) 0.053(3) 0.067(4) -0.010(3) 0.012(3) -0.010(3) C10 0.039(3) 0.066(4) 0.059(4) -0.020(3) 0.006(2) -0.007(3) C21 0.062(4) 0.041(3) 0.063(4) -0.009(3) 0.008(3) 0.004(3) C30 0.073(4) 0.046(3) 0.066(4) -0.015(3) 0.000(3) 0.000(3) C18 0.074(5) 0.133(7) 0.049(4) -0.009(4) 0.026(3) -0.023(5) C4 0.053(3) 0.046(3) 0.067(4) -0.001(3) 0.000(3) 0.013(3) C15 0.055(3) 0.089(5) 0.044(3) -0.001(3) 0.003(3) -0.003(3) C5 0.049(3) 0.055(3) 0.058(3) -0.008(3) 0.007(3) 0.007(3) C19 0.059(4) 0.087(5) 0.048(3) -0.015(3) 0.014(3) -0.015(3) C23 0.086(5) 0.054(4) 0.092(5) -0.003(4) -0.005(4) 0.023(4) C17 0.067(4) 0.109(6) 0.062(4) 0.008(4) 0.019(3) -0.019(4) C16 0.058(4) 0.095(5) 0.068(4) 0.003(4) 0.006(3) -0.021(4) C1 0.056(3) 0.040(3) 0.067(4) 0.004(3) 0.017(3) -0.002(3) C29 0.087(5) 0.087(5) 0.058(4) -0.006(4) -0.023(4) -0.012(4) Cl1 0.0496(8) 0.0696(10) 0.0551(8) 0.0182(7) 0.0064(6) 0.0070(7) O1 0.083(3) 0.066(3) 0.069(3) 0.028(2) 0.016(2) 0.017(2) O4 0.227(9) 0.079(4) 0.147(7) 0.020(4) -0.062(6) -0.033(5) O3 0.052(3) 0.196(8) 0.136(6) 0.086(5) -0.008(3) 0.015(4) O2 0.169(7) 0.187(8) 0.113(5) 0.071(5) 0.090(5) 0.070(6) Cl2 0.0625(10) 0.0604(10) 0.1017(14) 0.0072(9) 0.0149(10) 0.0052(8) O8 0.282(17) 0.77(5) 0.131(10) 0.013(17) 0.044(11) 0.28(3) O5 0.124(9) 0.41(2) 0.65(4) -0.36(3) -0.084(15) 0.043(12) O9 0.148(10) 0.312(19) 0.83(5) 0.35(3) 0.057(17) 0.124(12) O10 0.58(3) 0.157(10) 0.191(12) 0.048(9) 0.028(16) -0.141(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 2.000(4) . ? Cu1 N5 2.006(4) . ? Cu1 N3 2.016(4) . ? Cu1 N2 2.040(4) . ? Cu1 N1 2.314(4) . ? N3 C8 1.343(7) . ? N3 C12 1.356(7) . ? N2 C2 1.338(7) . ? N2 C6 1.339(6) . ? N4 C20 1.343(7) . ? N4 C25 1.351(7) . ? N5 C26 1.346(7) . ? N5 C31 1.356(7) . ? C26 C27 1.391(8) . ? C26 C25 1.487(7) . ? C25 C24 1.371(7) . ? N1 C1 1.467(7) . ? N1 C13 1.483(7) . ? N1 C7 1.484(7) . ? C9 C10 1.366(8) . ? C9 C8 1.387(8) . ? C9 H9A 0.9602 . ? C27 C28 1.372(8) . ? C27 H27 0.9300 . ? C2 C3 1.382(8) . ? C2 C1 1.491(8) . ? C8 C7 1.493(8) . ? C24 C22 1.406(8) . ? C24 H24 0.9301 . ? C28 C30 1.372(9) . ? C28 C29 1.512(8) . ? C31 C30 1.364(9) . ? C31 H31 0.9301 . ? C12 C11 1.372(8) . ? C12 H12 0.9301 . ? C14 C15 1.392(9) . ? C14 C19 1.399(8) . ? C14 C13 1.505(8) . ? C13 H13A 0.9701 . ? C13 H13B 0.9700 . ? C22 C21 1.381(8) . ? C22 C23 1.493(8) . ? C6 C5 1.373(8) . ? C6 H6 0.9301 . ? C3 C4 1.366(8) . ? C3 H3 0.9301 . ? C20 C21 1.382(8) . ? C20 H20 0.9300 . ? C7 H7A 0.9699 . ? C7 H7B 0.9701 . ? C11 C10 1.383(9) . ? C11 H11 0.9300 . ? C10 H10 0.9299 . ? C21 H21 0.9299 . ? C30 H30 0.9300 . ? C18 C19 1.366(10) . ? C18 C17 1.376(11) . ? C18 H18 0.9301 . ? C4 C5 1.382(9) . ? C4 H4 0.9298 . ? C15 C16 1.363(9) . ? C15 H15 0.9302 . ? C5 H5 0.9301 . ? C19 H19 0.9299 . ? C23 H23A 0.9600 . ? C23 H23B 0.9599 . ? C23 H23C 0.9601 . ? C17 C16 1.355(10) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? C1 H1A 0.9701 . ? C1 H1B 0.9698 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9599 . ? Cl1 O3 1.359(5) . ? Cl1 O2 1.369(6) . ? Cl1 O4 1.418(7) . ? Cl1 O1 1.438(4) . ? Cl2 O9 1.194(13) . ? Cl2 O8 1.237(13) . ? Cl2 O10 1.257(12) . ? Cl2 O5 1.295(14) . ? 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 80.79(17) . . ? N4 Cu1 N3 97.42(17) . . ? N5 Cu1 N3 177.44(17) . . ? N4 Cu1 N2 174.51(17) . . ? N5 Cu1 N2 94.26(17) . . ? N3 Cu1 N2 87.45(17) . . ? N4 Cu1 N1 103.98(16) . . ? N5 Cu1 N1 101.66(17) . . ? N3 Cu1 N1 80.53(17) . . ? N2 Cu1 N1 79.25(16) . . ? C8 N3 C12 118.5(5) . . ? C8 N3 Cu1 117.8(3) . . ? C12 N3 Cu1 123.1(4) . . ? C2 N2 C6 119.7(5) . . ? C2 N2 Cu1 115.6(3) . . ? C6 N2 Cu1 124.6(4) . . ? C20 N4 C25 117.5(5) . . ? C20 N4 Cu1 127.0(4) . . ? C25 N4 Cu1 115.5(3) . . ? C26 N5 C31 117.7(5) . . ? C26 N5 Cu1 115.2(3) . . ? C31 N5 Cu1 127.1(4) . . ? N5 C26 C27 121.6(5) . . ? N5 C26 C25 114.5(4) . . ? C27 C26 C25 123.9(5) . . ? N4 C25 C24 122.4(5) . . ? N4 C25 C26 114.0(4) . . ? C24 C25 C26 123.6(5) . . ? C1 N1 C13 112.5(4) . . ? C1 N1 C7 112.3(5) . . ? C13 N1 C7 112.1(4) . . ? C1 N1 Cu1 100.9(3) . . ? C13 N1 Cu1 112.7(3) . . ? C7 N1 Cu1 105.7(3) . . ? C10 C9 C8 120.2(6) . . ? C10 C9 H9A 119.9 . . ? C8 C9 H9A 119.9 . . ? C28 C27 C26 120.1(6) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? N2 C2 C3 120.6(5) . . ? N2 C2 C1 117.8(5) . . ? C3 C2 C1 121.5(5) . . ? N3 C8 C9 121.2(5) . . ? N3 C8 C7 119.3(5) . . ? C9 C8 C7 119.4(5) . . ? C25 C24 C22 120.4(5) . . ? C25 C24 H24 119.8 . . ? C22 C24 H24 119.8 . . ? C27 C28 C30 117.7(6) . . ? C27 C28 C29 120.8(6) . . ? C30 C28 C29 121.5(6) . . ? N5 C31 C30 122.0(5) . . ? N5 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? N3 C12 C11 122.0(5) . . ? N3 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C15 C14 C19 117.2(5) . . ? C15 C14 C13 121.0(5) . . ? C19 C14 C13 121.8(5) . . ? N1 C13 C14 116.5(5) . . ? N1 C13 H13A 108.2 . . ? C14 C13 H13A 108.2 . . ? N1 C13 H13B 108.2 . . ? C14 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? C21 C22 C24 116.5(5) . . ? C21 C22 C23 122.7(6) . . ? C24 C22 C23 120.8(6) . . ? N2 C6 C5 121.7(5) . . ? N2 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C4 C3 C2 120.3(6) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N4 C20 C21 122.8(6) . . ? N4 C20 H20 118.6 . . ? C21 C20 H20 118.6 . . ? N1 C7 C8 115.6(4) . . ? N1 C7 H7A 108.4 . . ? C8 C7 H7A 108.4 . . ? N1 C7 H7B 108.4 . . ? C8 C7 H7B 108.4 . . ? H7A C7 H7B 107.4 . . ? C12 C11 C10 119.4(5) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C9 C10 C11 118.6(5) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C22 C21 C20 120.3(5) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C31 C30 C28 120.8(5) . . ? C31 C30 H30 119.6 . . ? C28 C30 H30 119.6 . . ? C19 C18 C17 121.2(7) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C3 C4 C5 118.5(5) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.7 . . ? C16 C15 C14 121.7(6) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C6 C5 C4 119.2(5) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C18 C19 C14 120.1(6) . . ? C18 C19 H19 120.0 . . ? C14 C19 H19 119.9 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C16 C17 C18 119.4(7) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C16 C15 120.4(7) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? N1 C1 C2 112.8(4) . . ? N1 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? N1 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O3 Cl1 O2 114.5(5) . . ? O3 Cl1 O4 108.1(6) . . ? O2 Cl1 O4 106.7(6) . . ? O3 Cl1 O1 110.2(4) . . ? O2 Cl1 O1 110.9(4) . . ? O4 Cl1 O1 106.0(4) . . ? O9 Cl2 O8 121.8(16) . . ? O9 Cl2 O10 107.6(13) . . ? O8 Cl2 O10 112.0(16) . . ? O9 Cl2 O5 113.2(15) . . ? O8 Cl2 O5 96.9(11) . . ? O10 Cl2 O5 103.8(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 N4 Cu1 N3 C8 109.3(4) . . . . ? N5 Cu1 N3 C8 155(4) . . . . ? N2 Cu1 N3 C8 -73.2(4) . . . . ? N1 Cu1 N3 C8 6.3(4) . . . . ? N4 Cu1 N3 C12 -79.9(4) . . . . ? N5 Cu1 N3 C12 -34(4) . . . . ? N2 Cu1 N3 C12 97.5(4) . . . . ? N1 Cu1 N3 C12 177.1(4) . . . . ? N4 Cu1 N2 C2 -113.2(17) . . . . ? N5 Cu1 N2 C2 -87.8(4) . . . . ? N3 Cu1 N2 C2 94.2(4) . . . . ? N1 Cu1 N2 C2 13.3(4) . . . . ? N4 Cu1 N2 C6 70.1(19) . . . . ? N5 Cu1 N2 C6 95.5(5) . . . . ? N3 Cu1 N2 C6 -82.5(4) . . . . ? N1 Cu1 N2 C6 -163.4(5) . . . . ? N5 Cu1 N4 C20 -177.5(5) . . . . ? N3 Cu1 N4 C20 0.6(5) . . . . ? N2 Cu1 N4 C20 -151.8(16) . . . . ? N1 Cu1 N4 C20 82.7(5) . . . . ? N5 Cu1 N4 C25 0.7(3) . . . . ? N3 Cu1 N4 C25 178.8(3) . . . . ? N2 Cu1 N4 C25 26(2) . . . . ? N1 Cu1 N4 C25 -99.1(4) . . . . ? N4 Cu1 N5 C26 -1.9(4) . . . . ? N3 Cu1 N5 C26 -48(4) . . . . ? N2 Cu1 N5 C26 -179.5(4) . . . . ? N1 Cu1 N5 C26 100.6(4) . . . . ? N4 Cu1 N5 C31 -179.6(5) . . . . ? N3 Cu1 N5 C31 135(4) . . . . ? N2 Cu1 N5 C31 2.8(5) . . . . ? N1 Cu1 N5 C31 -77.1(5) . . . . ? C31 N5 C26 C27 0.4(8) . . . . ? Cu1 N5 C26 C27 -177.5(4) . . . . ? C31 N5 C26 C25 -179.5(5) . . . . ? Cu1 N5 C26 C25 2.6(5) . . . . ? C20 N4 C25 C24 0.5(7) . . . . ? Cu1 N4 C25 C24 -177.9(4) . . . . ? C20 N4 C25 C26 178.9(5) . . . . ? Cu1 N4 C25 C26 0.5(5) . . . . ? N5 C26 C25 N4 -2.0(6) . . . . ? C27 C26 C25 N4 178.1(5) . . . . ? N5 C26 C25 C24 176.3(5) . . . . ? C27 C26 C25 C24 -3.6(8) . . . . ? N4 Cu1 N1 C1 147.6(3) . . . . ? N5 Cu1 N1 C1 64.3(3) . . . . ? N3 Cu1 N1 C1 -117.0(3) . . . . ? N2 Cu1 N1 C1 -27.9(3) . . . . ? N4 Cu1 N1 C13 27.4(4) . . . . ? N5 Cu1 N1 C13 -55.8(4) . . . . ? N3 Cu1 N1 C13 122.8(4) . . . . ? N2 Cu1 N1 C13 -148.0(4) . . . . ? N4 Cu1 N1 C7 -95.3(4) . . . . ? N5 Cu1 N1 C7 -178.6(4) . . . . ? N3 Cu1 N1 C7 0.1(4) . . . . ? N2 Cu1 N1 C7 89.2(4) . . . . ? N5 C26 C27 C28 -0.9(8) . . . . ? C25 C26 C27 C28 178.9(5) . . . . ? C6 N2 C2 C3 -0.8(8) . . . . ? Cu1 N2 C2 C3 -177.7(4) . . . . ? C6 N2 C2 C1 -177.8(5) . . . . ? Cu1 N2 C2 C1 5.4(6) . . . . ? C12 N3 C8 C9 -0.3(7) . . . . ? Cu1 N3 C8 C9 170.9(4) . . . . ? C12 N3 C8 C7 176.8(5) . . . . ? Cu1 N3 C8 C7 -12.0(6) . . . . ? C10 C9 C8 N3 0.2(8) . . . . ? C10 C9 C8 C7 -177.0(5) . . . . ? N4 C25 C24 C22 1.0(8) . . . . ? C26 C25 C24 C22 -177.2(5) . . . . ? C26 C27 C28 C30 0.7(9) . . . . ? C26 C27 C28 C29 179.5(6) . . . . ? C26 N5 C31 C30 0.4(9) . . . . ? Cu1 N5 C31 C30 178.0(5) . . . . ? C8 N3 C12 C11 -0.4(8) . . . . ? Cu1 N3 C12 C11 -171.0(4) . . . . ? C1 N1 C13 C14 51.9(7) . . . . ? C7 N1 C13 C14 -75.9(6) . . . . ? Cu1 N1 C13 C14 165.1(4) . . . . ? C15 C14 C13 N1 -104.5(6) . . . . ? C19 C14 C13 N1 76.3(7) . . . . ? C25 C24 C22 C21 -1.3(8) . . . . ? C25 C24 C22 C23 178.0(6) . . . . ? C2 N2 C6 C5 1.4(8) . . . . ? Cu1 N2 C6 C5 178.0(4) . . . . ? N2 C2 C3 C4 0.0(9) . . . . ? C1 C2 C3 C4 176.8(6) . . . . ? C25 N4 C20 C21 -1.6(8) . . . . ? Cu1 N4 C20 C21 176.6(4) . . . . ? C1 N1 C7 C8 103.4(6) . . . . ? C13 N1 C7 C8 -128.8(5) . . . . ? Cu1 N1 C7 C8 -5.7(6) . . . . ? N3 C8 C7 N1 11.8(8) . . . . ? C9 C8 C7 N1 -171.0(5) . . . . ? N3 C12 C11 C10 1.1(9) . . . . ? C8 C9 C10 C11 0.6(9) . . . . ? C12 C11 C10 C9 -1.2(9) . . . . ? C24 C22 C21 C20 0.3(8) . . . . ? C23 C22 C21 C20 -179.0(6) . . . . ? N4 C20 C21 C22 1.2(9) . . . . ? N5 C31 C30 C28 -0.6(10) . . . . ? C27 C28 C30 C31 0.1(10) . . . . ? C29 C28 C30 C31 -178.7(6) . . . . ? C2 C3 C4 C5 0.3(9) . . . . ? C19 C14 C15 C16 -0.2(9) . . . . ? C13 C14 C15 C16 -179.4(6) . . . . ? N2 C6 C5 C4 -1.1(9) . . . . ? C3 C4 C5 C6 0.2(9) . . . . ? C17 C18 C19 C14 -2.4(12) . . . . ? C15 C14 C19 C18 1.3(10) . . . . ? C13 C14 C19 C18 -179.5(6) . . . . ? C19 C18 C17 C16 2.4(13) . . . . ? C18 C17 C16 C15 -1.3(12) . . . . ? C14 C15 C16 C17 0.2(11) . . . . ? C13 N1 C1 C2 158.7(5) . . . . ? C7 N1 C1 C2 -73.7(6) . . . . ? Cu1 N1 C1 C2 38.4(5) . . . . ? N2 C2 C1 N1 -33.5(7) . . . . ? C3 C2 C1 N1 149.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.118 _refine_diff_density_min -0.694 _refine_diff_density_rms 0.138 # Attachment '- cif complex 3 deposit.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 782308' #TrackingRef '- cif complex 3 deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C62 H60 Cl4 Cu2 N10 O19' _chemical_formula_weight 1518.08 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6111(17) _cell_length_b 21.793(4) _cell_length_c 19.306(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.29(3) _cell_angle_gamma 90.00 _cell_volume 3601.2(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.813 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16333 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6305 _reflns_number_gt 5121 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1541P)^2^+1.8782P] 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 6305 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.2500 _refine_ls_wR_factor_gt 0.2330 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.008 _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 O10 O 0.386(4) 0.0215(10) 0.1096(14) 0.319(18) Uani 0.50 1 d P . . H10A H 0.4414 0.0492 0.0935 0.478 Uiso 0.50 1 d PR . . H10B H 0.3869 -0.0106 0.0847 0.478 Uiso 0.50 1 d PR . . Cu1 Cu 0.34417(7) 0.82822(2) 0.59228(3) 0.0499(3) Uani 1 1 d . . . Cl1 Cl 0.1289(2) 0.65642(9) 0.38742(9) 0.0882(5) Uani 1 1 d . . . Cl2 Cl 0.47421(17) 0.92988(7) 0.34267(8) 0.0731(4) Uani 1 1 d . . . C1 C 0.2030(7) 0.8202(3) 0.4409(3) 0.0642(14) Uani 1 1 d . . . H1 H 0.2826 0.7931 0.4331 0.077 Uiso 1 1 calc R . . C2 C 0.0927(8) 0.8361(3) 0.3845(3) 0.0789(18) Uani 1 1 d . . . H2 H 0.0996 0.8195 0.3406 0.095 Uiso 1 1 calc R . . C3 C -0.0244(7) 0.8761(3) 0.3946(3) 0.0789(17) Uani 1 1 d . . . H3 H -0.0971 0.8874 0.3577 0.095 Uiso 1 1 calc R . . C4 C -0.0339(6) 0.9001(2) 0.4621(3) 0.0639(13) Uani 1 1 d . . . C5 C 0.0809(5) 0.8820(2) 0.5144(3) 0.0520(11) Uani 1 1 d . . . C6 C -0.1524(7) 0.9417(3) 0.4777(4) 0.0793(17) Uani 1 1 d . . . H6 H -0.2288 0.9537 0.4426 0.095 Uiso 1 1 calc R . . C7 C -0.1559(7) 0.9639(3) 0.5423(4) 0.0822(19) Uani 1 1 d . . . H7 H -0.2337 0.9916 0.5510 0.099 Uiso 1 1 calc R . . C8 C -0.0405(6) 0.9455(2) 0.5987(3) 0.0673(14) Uani 1 1 d . . . C9 C 0.0778(5) 0.9055(2) 0.5838(3) 0.0531(11) Uani 1 1 d . . . C10 C -0.0385(8) 0.9664(3) 0.6676(4) 0.0764(17) Uani 1 1 d . . . H10 H -0.1155 0.9930 0.6799 0.092 Uiso 1 1 calc R . . C11 C 0.0793(8) 0.9471(3) 0.7166(4) 0.0785(17) Uani 1 1 d . . . H11 H 0.0832 0.9606 0.7624 0.094 Uiso 1 1 calc R . . C12 C 0.1922(7) 0.9072(2) 0.6971(3) 0.0666(14) Uani 1 1 d . . . H12 H 0.2710 0.8945 0.7309 0.080 Uiso 1 1 calc R . . C13 C 0.6127(7) 0.8534(3) 0.6994(3) 0.0690(14) Uani 1 1 d . . . H13 H 0.6364 0.8846 0.6695 0.083 Uiso 1 1 calc R . . C14 C 0.7110(8) 0.8435(3) 0.7576(4) 0.0829(18) Uani 1 1 d . . . H14 H 0.8017 0.8666 0.7665 0.100 Uiso 1 1 calc R . . C15 C 0.6765(8) 0.7994(4) 0.8032(4) 0.090(2) Uani 1 1 d . . . H15 H 0.7414 0.7926 0.8443 0.107 Uiso 1 1 calc R . . C16 C 0.5433(8) 0.7648(3) 0.7873(3) 0.0813(17) Uani 1 1 d . . . H16 H 0.5178 0.7342 0.8176 0.098 Uiso 1 1 calc R . . C17 C 0.4459(6) 0.7760(2) 0.7254(3) 0.0586(12) Uani 1 1 d . . . C18 C 0.2947(6) 0.7414(3) 0.7065(3) 0.0632(13) Uani 1 1 d . . . H18A H 0.3033 0.7008 0.7270 0.076 Uiso 1 1 calc R . . H18B H 0.2102 0.7628 0.7256 0.076 Uiso 1 1 calc R . . C19 C 0.0866(6) 0.7321(2) 0.6096(3) 0.0628(13) Uani 1 1 d . . . H19A H 0.0705 0.7286 0.5592 0.075 Uiso 1 1 calc R . . H19B H 0.0401 0.7706 0.6219 0.075 Uiso 1 1 calc R . . C20 C -0.0021(6) 0.6803(2) 0.6402(3) 0.0633(14) Uani 1 1 d . . . C21 C -0.0977(7) 0.6934(3) 0.6915(3) 0.0735(15) Uani 1 1 d . . . H21 H -0.0989 0.7329 0.7095 0.088 Uiso 1 1 calc R . . C22 C -0.1899(8) 0.6494(3) 0.7161(4) 0.0839(18) Uani 1 1 d . . . H22 H -0.2539 0.6597 0.7501 0.101 Uiso 1 1 calc R . . C23 C -0.1905(7) 0.5919(3) 0.6923(4) 0.088(2) Uani 1 1 d . . . H23 H -0.2547 0.5624 0.7093 0.105 Uiso 1 1 calc R . . C24 C -0.0936(9) 0.5767(3) 0.6418(4) 0.098(2) Uani 1 1 d . . . H24 H -0.0904 0.5366 0.6257 0.118 Uiso 1 1 calc R . . C25 C -0.0022(7) 0.6212(3) 0.6155(4) 0.0767(16) Uani 1 1 d . . . H25 H 0.0600 0.6111 0.5807 0.092 Uiso 1 1 calc R . . C26 C 0.3481(7) 0.6891(3) 0.5998(3) 0.0753(17) Uani 1 1 d . . . H26A H 0.2776 0.6657 0.5672 0.090 Uiso 1 1 calc R . . H26B H 0.3898 0.6612 0.6364 0.090 Uiso 1 1 calc R . . C27 C 0.4811(5) 0.7113(2) 0.5623(2) 0.0530(11) Uani 1 1 d . . . C28 C 0.5855(7) 0.6703(2) 0.5389(3) 0.0648(14) Uani 1 1 d . . . H28 H 0.5764 0.6285 0.5476 0.078 Uiso 1 1 calc R . . C29 C 0.7031(7) 0.6917(3) 0.5027(3) 0.0704(15) Uani 1 1 d . . . H29 H 0.7741 0.6643 0.4869 0.084 Uiso 1 1 calc R . . C30 C 0.7160(7) 0.7529(3) 0.4898(3) 0.0714(15) Uani 1 1 d . . . H30 H 0.7962 0.7680 0.4661 0.086 Uiso 1 1 calc R . . C31 C 0.6061(6) 0.7916(3) 0.5131(3) 0.0655(13) Uani 1 1 d . . . H31 H 0.6122 0.8333 0.5036 0.079 Uiso 1 1 calc R . . N1 N 0.1987(5) 0.84231(18) 0.5048(2) 0.0511(9) Uani 1 1 d . . . N2 N 0.1934(5) 0.88630(18) 0.6327(2) 0.0537(10) Uani 1 1 d . . . N3 N 0.4828(5) 0.82056(18) 0.6825(2) 0.0561(10) Uani 1 1 d . . . N4 N 0.2583(5) 0.73597(17) 0.6308(2) 0.0514(9) Uani 1 1 d . . . N5 N 0.4917(4) 0.77194(17) 0.5487(2) 0.0517(9) Uani 1 1 d . . . O1 O 0.0355(12) 0.6878(4) 0.4314(4) 0.186(4) Uani 1 1 d . . . O2 O 0.2748(11) 0.6705(5) 0.4122(10) 0.298(9) Uani 1 1 d . . . O3 O 0.0974(13) 0.6856(4) 0.3199(4) 0.182(4) Uani 1 1 d . . . O4 O 0.1017(19) 0.5956(4) 0.3791(5) 0.268(7) Uani 1 1 d . . . O5 O 0.4272(8) 0.9405(4) 0.4086(3) 0.147(2) Uani 1 1 d . . . O6 O 0.5631(9) 0.8763(3) 0.3547(5) 0.184(4) Uani 1 1 d . . . O7 O 0.3458(9) 0.9184(4) 0.2943(4) 0.177(3) Uani 1 1 d . . . O8 O 0.5797(10) 0.9737(4) 0.3277(4) 0.180(3) Uani 1 1 d . . . O9 O 0.4703(5) 0.92405(19) 0.5560(2) 0.0897(13) Uani 1 1 d . . . H9A H 0.4003 0.9485 0.5379 0.135 Uiso 1 1 d R . . H9C H 0.5328 0.9154 0.5262 0.135 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O10 0.54(5) 0.136(16) 0.27(3) -0.012(16) 0.01(3) 0.07(2) Cu1 0.0580(4) 0.0473(4) 0.0452(4) 0.0026(2) 0.0091(3) 0.0050(2) Cl1 0.0900(11) 0.1040(12) 0.0706(10) -0.0192(9) 0.0087(8) -0.0102(9) Cl2 0.0714(9) 0.0771(9) 0.0728(9) -0.0155(7) 0.0169(7) -0.0001(7) C1 0.070(3) 0.069(3) 0.052(3) -0.002(2) 0.004(3) 0.005(3) C2 0.095(5) 0.087(4) 0.052(3) -0.001(3) 0.001(3) -0.009(4) C3 0.071(3) 0.085(4) 0.075(4) 0.014(3) -0.015(3) -0.003(3) C4 0.059(3) 0.063(3) 0.069(4) 0.009(3) 0.001(3) -0.003(3) C5 0.050(2) 0.054(3) 0.054(3) 0.007(2) 0.012(2) -0.004(2) C6 0.053(3) 0.075(4) 0.108(5) 0.016(4) 0.004(3) -0.001(3) C7 0.055(3) 0.069(4) 0.124(6) 0.012(4) 0.018(3) 0.008(3) C8 0.060(3) 0.052(3) 0.093(4) 0.003(3) 0.025(3) 0.001(3) C9 0.052(3) 0.043(2) 0.066(3) 0.008(2) 0.016(2) 0.002(2) C10 0.080(4) 0.063(3) 0.093(5) -0.005(3) 0.042(4) 0.005(3) C11 0.106(5) 0.062(3) 0.074(4) -0.010(3) 0.039(4) -0.006(3) C12 0.090(4) 0.053(3) 0.061(3) -0.001(2) 0.024(3) -0.002(3) C13 0.074(4) 0.062(3) 0.070(4) 0.005(3) 0.003(3) -0.013(3) C14 0.074(4) 0.099(5) 0.073(4) 0.004(4) -0.005(3) -0.014(4) C15 0.086(4) 0.108(5) 0.069(4) 0.013(4) -0.018(3) -0.012(4) C16 0.093(4) 0.090(4) 0.060(4) 0.022(3) 0.004(3) -0.001(4) C17 0.065(3) 0.061(3) 0.051(3) 0.003(2) 0.010(2) 0.005(2) C18 0.073(3) 0.064(3) 0.055(3) 0.010(2) 0.013(2) -0.003(3) C19 0.060(3) 0.064(3) 0.065(3) 0.010(2) 0.008(2) -0.006(3) C20 0.062(3) 0.066(3) 0.063(3) 0.012(3) 0.008(3) -0.008(3) C21 0.076(4) 0.083(4) 0.062(4) 0.005(3) 0.008(3) -0.008(3) C22 0.079(4) 0.095(5) 0.081(4) 0.023(4) 0.020(3) -0.005(4) C23 0.072(4) 0.092(5) 0.101(5) 0.041(4) 0.017(4) -0.007(4) C24 0.102(5) 0.064(4) 0.130(7) 0.021(4) 0.015(5) -0.006(4) C25 0.080(4) 0.058(3) 0.095(5) 0.001(3) 0.022(3) -0.005(3) C26 0.094(4) 0.048(3) 0.091(4) -0.006(3) 0.047(4) -0.001(3) C27 0.051(2) 0.058(3) 0.049(3) 0.001(2) 0.003(2) 0.003(2) C28 0.065(3) 0.054(3) 0.076(4) -0.005(2) 0.010(3) 0.011(2) C29 0.064(3) 0.081(4) 0.069(4) -0.009(3) 0.018(3) 0.020(3) C30 0.066(3) 0.082(4) 0.071(4) -0.003(3) 0.024(3) 0.002(3) C31 0.073(3) 0.062(3) 0.064(3) 0.005(2) 0.020(3) -0.001(3) N1 0.054(2) 0.050(2) 0.051(2) 0.0017(17) 0.0109(18) -0.0001(18) N2 0.066(2) 0.047(2) 0.051(2) 0.0020(17) 0.0180(19) -0.0011(19) N3 0.060(2) 0.055(2) 0.053(2) 0.0055(18) 0.0055(19) 0.002(2) N4 0.059(2) 0.050(2) 0.046(2) 0.0011(16) 0.0121(17) -0.0002(18) N5 0.055(2) 0.051(2) 0.050(2) 0.0055(17) 0.0114(18) 0.0040(18) O1 0.224(9) 0.225(8) 0.127(6) -0.041(6) 0.099(6) -0.018(7) O2 0.122(6) 0.259(13) 0.48(2) -0.140(13) -0.088(10) 0.051(7) O3 0.278(11) 0.175(7) 0.102(5) 0.017(5) 0.066(6) -0.010(7) O4 0.54(2) 0.107(6) 0.153(7) -0.025(5) 0.009(10) -0.081(9) O5 0.148(5) 0.201(7) 0.099(4) -0.025(4) 0.049(4) 0.015(5) O6 0.166(6) 0.129(6) 0.256(10) -0.059(6) 0.015(6) 0.050(5) O7 0.149(6) 0.243(9) 0.125(6) -0.005(5) -0.047(5) -0.051(6) O8 0.213(8) 0.173(7) 0.146(6) 0.040(5) -0.011(5) -0.099(6) O9 0.094(3) 0.072(3) 0.106(4) 0.002(2) 0.027(3) -0.011(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 O10 H10A 0.8501 . ? O10 H10B 0.8499 . ? Cu1 N3 2.008(4) . ? Cu1 N1 2.014(4) . ? Cu1 N5 2.015(4) . ? Cu1 N2 2.030(4) . ? Cu1 N4 2.294(4) . ? Cl1 O2 1.330(9) . ? Cl1 O4 1.353(8) . ? Cl1 O1 1.410(7) . ? Cl1 O3 1.449(8) . ? Cl2 O8 1.371(7) . ? Cl2 O7 1.390(6) . ? Cl2 O5 1.396(6) . ? Cl2 O6 1.401(7) . ? C1 N1 1.327(7) . ? C1 C2 1.409(9) . ? C1 H1 0.9300 . ? C2 C3 1.362(9) . ? C2 H2 0.9300 . ? C3 C4 1.414(8) . ? C3 H3 0.9300 . ? C4 C5 1.391(7) . ? C4 C6 1.422(8) . ? C5 N1 1.361(6) . ? C5 C9 1.437(7) . ? C6 C7 1.341(10) . ? C6 H6 0.9300 . ? C7 C8 1.449(9) . ? C7 H7 0.9300 . ? C8 C9 1.394(7) . ? C8 C10 1.404(9) . ? C9 N2 1.360(6) . ? C10 C11 1.375(10) . ? C10 H10 0.9300 . ? C11 C12 1.386(8) . ? C11 H11 0.9300 . ? C12 N2 1.326(6) . ? C12 H12 0.9300 . ? C13 N3 1.337(7) . ? C13 C14 1.348(8) . ? C13 H13 0.9300 . ? C14 C15 1.358(10) . ? C14 H14 0.9300 . ? C15 C16 1.378(9) . ? C15 H15 0.9300 . ? C16 C17 1.405(8) . ? C16 H16 0.9300 . ? C17 N3 1.336(6) . ? C17 C18 1.514(8) . ? C18 N4 1.465(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N4 1.492(6) . ? C19 C20 1.520(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C25 1.372(8) . ? C20 C21 1.385(8) . ? C21 C22 1.363(9) . ? C21 H21 0.9300 . ? C22 C23 1.334(10) . ? C22 H22 0.9300 . ? C23 C24 1.392(10) . ? C23 H23 0.9300 . ? C24 C25 1.380(9) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 N4 1.449(6) . ? C26 C27 1.501(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 N5 1.352(6) . ? C27 C28 1.378(7) . ? C28 C29 1.374(8) . ? C28 H28 0.9300 . ? C29 C30 1.364(8) . ? C29 H29 0.9300 . ? C30 C31 1.379(8) . ? C30 H30 0.9300 . ? C31 N5 1.332(6) . ? C31 H31 0.9300 . ? O9 H9A 0.8500 . ? O9 H9C 0.8500 . ? 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 H10A O10 H10B 109.5 . . ? N3 Cu1 N1 175.36(16) . . ? N3 Cu1 N5 88.27(17) . . ? N1 Cu1 N5 96.02(16) . . ? N3 Cu1 N2 93.60(17) . . ? N1 Cu1 N2 82.07(16) . . ? N5 Cu1 N2 177.89(15) . . ? N3 Cu1 N4 80.10(16) . . ? N1 Cu1 N4 102.28(15) . . ? N5 Cu1 N4 80.92(14) . . ? N2 Cu1 N4 100.34(14) . . ? O2 Cl1 O4 114.4(8) . . ? O2 Cl1 O1 104.5(8) . . ? O4 Cl1 O1 116.4(7) . . ? O2 Cl1 O3 107.4(9) . . ? O4 Cl1 O3 108.1(6) . . ? O1 Cl1 O3 105.5(6) . . ? O8 Cl2 O7 118.7(5) . . ? O8 Cl2 O5 110.0(5) . . ? O7 Cl2 O5 110.7(5) . . ? O8 Cl2 O6 104.7(6) . . ? O7 Cl2 O6 109.9(5) . . ? O5 Cl2 O6 101.2(5) . . ? N1 C1 C2 123.0(6) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.5(6) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 117.1(5) . . ? C5 C4 C6 119.7(6) . . ? C3 C4 C6 123.2(6) . . ? N1 C5 C4 124.2(5) . . ? N1 C5 C9 116.4(4) . . ? C4 C5 C9 119.4(5) . . ? C7 C6 C4 121.2(6) . . ? C7 C6 H6 119.4 . . ? C4 C6 H6 119.4 . . ? C6 C7 C8 121.0(6) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C10 117.7(6) . . ? C9 C8 C7 118.3(6) . . ? C10 C8 C7 123.9(6) . . ? N2 C9 C8 123.0(5) . . ? N2 C9 C5 116.8(4) . . ? C8 C9 C5 120.3(5) . . ? C11 C10 C8 118.9(5) . . ? C11 C10 H10 120.6 . . ? C8 C10 H10 120.6 . . ? C10 C11 C12 119.5(6) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N2 C12 C11 123.1(6) . . ? N2 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? N3 C13 C14 123.4(6) . . ? N3 C13 H13 118.3 . . ? C14 C13 H13 118.3 . . ? C13 C14 C15 119.4(6) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 118.6(6) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C17 119.9(6) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? N3 C17 C16 119.6(5) . . ? N3 C17 C18 117.9(5) . . ? C16 C17 C18 122.4(5) . . ? N4 C18 C17 111.4(4) . . ? N4 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? N4 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? N4 C19 C20 117.4(4) . . ? N4 C19 H19A 107.9 . . ? C20 C19 H19A 107.9 . . ? N4 C19 H19B 107.9 . . ? C20 C19 H19B 107.9 . . ? H19A C19 H19B 107.2 . . ? C25 C20 C21 117.7(5) . . ? C25 C20 C19 122.9(5) . . ? C21 C20 C19 119.3(5) . . ? C22 C21 C20 121.3(7) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C23 C22 C21 121.4(7) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 118.9(6) . . ? C22 C23 H23 120.5 . . ? C24 C23 H23 120.5 . . ? C25 C24 C23 120.1(7) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C20 C25 C24 120.6(6) . . ? C20 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? N4 C26 C27 116.2(4) . . ? N4 C26 H26A 108.2 . . ? C27 C26 H26A 108.2 . . ? N4 C26 H26B 108.2 . . ? C27 C26 H26B 108.2 . . ? H26A C26 H26B 107.4 . . ? N5 C27 C28 120.6(5) . . ? N5 C27 C26 118.7(4) . . ? C28 C27 C26 120.5(5) . . ? C29 C28 C27 119.4(5) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C30 C29 C28 120.3(5) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C29 C30 C31 117.7(5) . . ? C29 C30 H30 121.1 . . ? C31 C30 H30 121.1 . . ? N5 C31 C30 123.0(5) . . ? N5 C31 H31 118.5 . . ? C30 C31 H31 118.5 . . ? C1 N1 C5 117.0(4) . . ? C1 N1 Cu1 130.2(4) . . ? C5 N1 Cu1 112.7(3) . . ? C12 N2 C9 117.7(4) . . ? C12 N2 Cu1 130.2(4) . . ? C9 N2 Cu1 112.1(3) . . ? C17 N3 C13 119.1(5) . . ? C17 N3 Cu1 116.0(4) . . ? C13 N3 Cu1 124.7(4) . . ? C26 N4 C18 113.8(4) . . ? C26 N4 C19 113.9(4) . . ? C18 N4 C19 112.0(4) . . ? C26 N4 Cu1 106.2(3) . . ? C18 N4 Cu1 102.1(3) . . ? C19 N4 Cu1 107.8(3) . . ? C31 N5 C27 118.9(4) . . ? C31 N5 Cu1 123.8(3) . . ? C27 N5 Cu1 117.0(3) . . ? H9A O9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.704 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.094