# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:complex1 #TrackingRef 'structures_Chemistry_2013.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H40 Cl2 Cu N8 O8' _chemical_formula_sum 'C24 H40 Cl2 Cu N8 O8' _chemical_formula_weight 703.08 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 tetragonal _symmetry_space_group_name_H-M 'I 41cd' _symmetry_space_group_name_Hall 'I 4bw -2c' _symmetry_Int_Tables_number 110 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-y, -x+1/2, z+3/4' 'y+1/2, -x, z+3/4' '-y, x+1/2, z+1/4' 'y+1/2, x, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' '-x+1, -y+1, z+1' 'x+1, -y+1, z+1/2' '-y+1/2, -x+1, z+5/4' 'y+1, -x+1/2, z+5/4' '-y+1/2, x+1, z+3/4' 'y+1, x+1/2, z+3/4' _cell_length_a 15.795(2) _cell_length_b 15.795(2) _cell_length_c 27.870(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6953.1(19) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6834 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.00 _exptl_crystal_description cube _exptl_crystal_colour violet _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2936 _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; A crystal was mounted at 173K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using MoK\a graphite monochromated radiation. Image plate distance 70mm, \f oscillation scans 0 - 200\%, step \D\f = 1.0\%, 5 minutes per frame. ; _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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12254 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 26.05 _reflns_number_total 3050 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe & Cie, 2000)' _computing_cell_refinement 'CELL (Stoe & Cie, 2000)' _computing_data_reduction 'INTEGRATE (Stoe & Cie, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-32 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0501P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 3050 _refine_ls_number_parameters 201 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.855 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1481(3) 0.4374(2) -0.01146(17) 0.0489(10) Uani 1 1 d . . . C2 C 0.1576(3) 0.4040(3) -0.05710(17) 0.0596(12) Uani 1 1 d . . . C3 C 0.0783(3) 0.3875(3) -0.07393(16) 0.0573(11) Uani 1 1 d . . . C4 C 0.1024(3) 0.4492(3) 0.14283(16) 0.0541(11) Uani 1 1 d . . . C5 C 0.1300(3) 0.3723(3) 0.16334(16) 0.0555(11) Uani 1 1 d . . . C6 C 0.1092(3) 0.3107(3) 0.13098(18) 0.0579(12) Uani 1 1 d . . . C7 C 0.2157(3) 0.4645(3) 0.02208(19) 0.0751(14) Uani 1 1 d . . . H7A H 0.1946 0.5089 0.0424 0.113 Uiso 1 1 calc R . . H7B H 0.2633 0.4851 0.0041 0.113 Uiso 1 1 calc R . . H7C H 0.2329 0.4173 0.0414 0.113 Uiso 1 1 calc R . . C8 C 0.2407(3) 0.3879(4) -0.0830(2) 0.100(2) Uani 1 1 d . . . H8A H 0.2714 0.4401 -0.0860 0.150 Uiso 1 1 calc R . . H8B H 0.2294 0.3653 -0.1143 0.150 Uiso 1 1 calc R . . H8C H 0.2739 0.3481 -0.0650 0.150 Uiso 1 1 calc R . . C9 C 0.0477(4) 0.3513(4) -0.12009(19) 0.0917(18) Uani 1 1 d . . . H9A H -0.0005 0.3159 -0.1142 0.138 Uiso 1 1 calc R . . H9B H 0.0920 0.3183 -0.1345 0.138 Uiso 1 1 calc R . . H9C H 0.0320 0.3965 -0.1414 0.138 Uiso 1 1 calc R . . C10 C 0.1125(3) 0.5360(3) 0.16196(18) 0.0716(13) Uani 1 1 d . . . H10A H 0.1023 0.5763 0.1368 0.107 Uiso 1 1 calc R . . H10B H 0.1690 0.5431 0.1740 0.107 Uiso 1 1 calc R . . H10C H 0.0726 0.5450 0.1875 0.107 Uiso 1 1 calc R . . C11 C 0.1734(4) 0.3623(3) 0.2112(2) 0.0834(16) Uani 1 1 d . . . H11A H 0.1327 0.3687 0.2365 0.125 Uiso 1 1 calc R . . H11B H 0.2166 0.4047 0.2144 0.125 Uiso 1 1 calc R . . H11C H 0.1986 0.3071 0.2131 0.125 Uiso 1 1 calc R . . C12 C 0.1234(4) 0.2162(3) 0.1298(2) 0.0848(17) Uani 1 1 d . . . H12A H 0.1033 0.1916 0.1592 0.127 Uiso 1 1 calc R . . H12B H 0.1827 0.2048 0.1263 0.127 Uiso 1 1 calc R . . H12C H 0.0931 0.1922 0.1032 0.127 Uiso 1 1 calc R . . N1 N 0.0652(2) 0.4402(2) -0.00021(13) 0.0507(10) Uani 1 1 d . . . N2 N 0.0248(2) 0.4095(2) -0.03932(13) 0.0544(9) Uani 1 1 d . . . H2 H -0.0293 0.4048 -0.0415 0.065 Uiso 1 1 calc R . . N3 N 0.0632(2) 0.4341(2) 0.10040(14) 0.0542(10) Uani 1 1 d . . . N4 N 0.0703(2) 0.3495(2) 0.09408(14) 0.0567(9) Uani 1 1 d . . . H4 H 0.0518 0.3232 0.0691 0.068 Uiso 1 1 calc R . . O1 O -0.1293(2) 0.3012(3) -0.02396(14) 0.1183(15) Uani 1 1 d . . . O2 O -0.0456(2) 0.2369(2) 0.03441(17) 0.1115(15) Uani 1 1 d . . . O3 O -0.1931(3) 0.2464(3) 0.04408(17) 0.1234(17) Uani 1 1 d . . . O4 O -0.1063(2) 0.3651(2) 0.04926(19) 0.1002(12) Uani 1 1 d . . . Cl1 Cl -0.12013(8) 0.28550(7) 0.02589(4) 0.0676(3) Uani 1 1 d . . . Cu1 Cu 0.0000 0.5000 0.05182(4) 0.04997(16) 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 C1 0.049(2) 0.048(2) 0.050(3) 0.0017(19) 0.004(2) 0.0055(18) C2 0.064(3) 0.063(3) 0.053(3) -0.001(2) 0.012(2) 0.009(2) C3 0.074(3) 0.055(3) 0.042(3) -0.006(2) 0.008(2) 0.007(2) C4 0.063(3) 0.056(3) 0.044(3) -0.001(2) -0.005(2) 0.000(2) C5 0.062(3) 0.057(3) 0.047(3) 0.008(2) -0.013(2) 0.004(2) C6 0.060(3) 0.051(2) 0.062(3) 0.011(2) -0.015(2) 0.004(2) C7 0.058(3) 0.085(3) 0.082(4) -0.008(3) -0.013(3) 0.008(2) C8 0.078(4) 0.125(4) 0.098(5) -0.013(4) 0.037(3) 0.009(3) C9 0.122(4) 0.096(4) 0.057(3) -0.025(3) -0.003(3) 0.000(3) C10 0.089(3) 0.061(3) 0.065(3) -0.009(2) -0.017(3) 0.001(2) C11 0.097(4) 0.084(3) 0.070(4) 0.019(3) -0.039(3) -0.011(3) C12 0.106(4) 0.053(3) 0.096(5) 0.006(3) -0.029(3) 0.011(3) N1 0.053(2) 0.057(2) 0.042(2) -0.0073(17) -0.0057(18) 0.0088(18) N2 0.057(2) 0.063(2) 0.043(2) -0.0052(18) -0.0039(18) 0.0054(16) N3 0.065(2) 0.050(2) 0.048(3) -0.0074(17) -0.0049(19) 0.0088(17) N4 0.074(2) 0.048(2) 0.048(2) -0.0034(17) -0.0160(19) 0.0074(17) O1 0.095(3) 0.201(5) 0.059(3) 0.025(3) -0.022(2) -0.024(3) O2 0.109(3) 0.104(3) 0.121(4) -0.025(2) -0.041(3) 0.046(2) O3 0.110(3) 0.151(4) 0.109(4) 0.031(3) 0.001(3) -0.063(3) O4 0.102(2) 0.073(2) 0.125(3) -0.030(2) -0.007(3) 0.0026(19) Cl1 0.0730(7) 0.0720(7) 0.0578(7) 0.0050(6) -0.0135(6) -0.0054(6) Cu1 0.0574(4) 0.0571(4) 0.0354(3) 0.000 0.000 0.0159(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.346(5) . ? C1 C2 1.385(6) . ? C1 C7 1.483(6) . ? C2 C3 1.363(7) . ? C2 C8 1.518(7) . ? C3 N2 1.329(5) . ? C3 C9 1.488(7) . ? C4 N3 1.356(6) . ? C4 C5 1.411(6) . ? C4 C10 1.479(6) . ? C5 C6 1.366(6) . ? C5 C11 1.508(6) . ? C6 N4 1.346(5) . ? C6 C12 1.509(6) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N1 N2 1.353(5) . ? N1 Cu1 2.014(4) . ? N2 H2 0.8600 . ? N3 N4 1.353(5) . ? N3 Cu1 1.978(4) . ? N4 H4 0.8600 . ? O1 Cl1 1.419(4) . ? O2 Cl1 1.426(3) . ? O3 Cl1 1.402(4) . ? O4 Cl1 1.432(3) . ? Cu1 N3 1.978(4) 11_454 ? Cu1 N1 2.014(4) 11_454 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 109.4(4) . . ? N1 C1 C7 122.9(4) . . ? C2 C1 C7 127.6(4) . . ? C3 C2 C1 106.8(4) . . ? C3 C2 C8 126.8(4) . . ? C1 C2 C8 126.4(5) . . ? N2 C3 C2 106.5(4) . . ? N2 C3 C9 121.5(5) . . ? C2 C3 C9 132.0(4) . . ? N3 C4 C5 110.1(4) . . ? N3 C4 C10 121.7(4) . . ? C5 C4 C10 128.2(4) . . ? C6 C5 C4 105.7(4) . . ? C6 C5 C11 128.2(4) . . ? C4 C5 C11 126.1(4) . . ? N4 C6 C5 106.9(4) . . ? N4 C6 C12 120.1(4) . . ? C5 C6 C12 133.0(4) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 N1 N2 105.0(4) . . ? C1 N1 Cu1 132.9(3) . . ? N2 N1 Cu1 120.4(3) . . ? C3 N2 N1 112.3(3) . . ? C3 N2 H2 123.9 . . ? N1 N2 H2 123.9 . . ? N4 N3 C4 104.4(3) . . ? N4 N3 Cu1 118.2(3) . . ? C4 N3 Cu1 137.3(3) . . ? C6 N4 N3 112.8(4) . . ? C6 N4 H4 123.6 . . ? N3 N4 H4 123.6 . . ? O3 Cl1 O1 110.3(3) . . ? O3 Cl1 O2 112.4(3) . . ? O1 Cl1 O2 110.0(3) . . ? O3 Cl1 O4 110.3(3) . . ? O1 Cl1 O4 107.9(3) . . ? O2 Cl1 O4 105.7(2) . . ? N3 Cu1 N3 93.6(2) . 11_454 ? N3 Cu1 N1 89.30(12) . . ? N3 Cu1 N1 176.14(16) 11_454 . ? N3 Cu1 N1 176.14(16) . 11_454 ? N3 Cu1 N1 89.30(12) 11_454 11_454 ? N1 Cu1 N1 87.9(2) . 11_454 ? 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 0.9(5) . . . . ? C7 C1 C2 C3 179.2(4) . . . . ? N1 C1 C2 C8 -178.3(4) . . . . ? C7 C1 C2 C8 0.0(8) . . . . ? C1 C2 C3 N2 -0.6(5) . . . . ? C8 C2 C3 N2 178.6(5) . . . . ? C1 C2 C3 C9 -179.7(5) . . . . ? C8 C2 C3 C9 -0.6(8) . . . . ? N3 C4 C5 C6 2.4(5) . . . . ? C10 C4 C5 C6 -177.2(5) . . . . ? N3 C4 C5 C11 -177.7(5) . . . . ? C10 C4 C5 C11 2.7(8) . . . . ? C4 C5 C6 N4 -1.1(5) . . . . ? C11 C5 C6 N4 179.0(5) . . . . ? C4 C5 C6 C12 177.5(6) . . . . ? C11 C5 C6 C12 -2.4(9) . . . . ? C2 C1 N1 N2 -0.8(5) . . . . ? C7 C1 N1 N2 -179.2(4) . . . . ? C2 C1 N1 Cu1 -165.5(3) . . . . ? C7 C1 N1 Cu1 16.1(6) . . . . ? C2 C3 N2 N1 0.1(5) . . . . ? C9 C3 N2 N1 179.4(4) . . . . ? C1 N1 N2 C3 0.4(4) . . . . ? Cu1 N1 N2 C3 167.5(3) . . . . ? C5 C4 N3 N4 -2.7(5) . . . . ? C10 C4 N3 N4 177.0(4) . . . . ? C5 C4 N3 Cu1 174.2(4) . . . . ? C10 C4 N3 Cu1 -6.2(7) . . . . ? C5 C6 N4 N3 -0.6(5) . . . . ? C12 C6 N4 N3 -179.4(4) . . . . ? C4 N3 N4 C6 2.1(5) . . . . ? Cu1 N3 N4 C6 -175.6(3) . . . . ? N4 N3 Cu1 N3 134.9(4) . . . 11_454 ? C4 N3 Cu1 N3 -41.7(4) . . . 11_454 ? N4 N3 Cu1 N1 -47.7(3) . . . . ? C4 N3 Cu1 N1 135.8(4) . . . . ? C1 N1 Cu1 N3 -62.3(4) . . . . ? N2 N1 Cu1 N3 134.8(3) . . . . ? C1 N1 Cu1 N1 120.3(5) . . . 11_454 ? N2 N1 Cu1 N1 -42.5(2) . . . 11_454 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.271 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 930623' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:complex2 #TrackingRef 'structures_Chemistry_2013.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H46 Cl2 Cu2 N8 O10' _chemical_formula_sum 'C26 H46 Cl2 Cu2 N8 O10' _chemical_formula_weight 828.69 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7851(17) _cell_length_b 10.375(2) _cell_length_c 10.915(2) _cell_angle_alpha 85.01(2) _cell_angle_beta 76.37(2) _cell_angle_gamma 72.47(2) _cell_volume 921.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3569 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.75 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 1.359 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; A crystal was mounted at 173K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using MoK\a graphite monochromated radiation. Image plate distance 70mm, \f oscillation scans 0 - 200\%, step \D\f = 1.5\%, 3 minutes per frame. ; _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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7252 _diffrn_reflns_av_R_equivalents 0.1051 _diffrn_reflns_av_sigmaI/netI 0.1290 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _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 2.73 _diffrn_reflns_theta_max 26.12 _reflns_number_total 3380 _reflns_number_gt 1881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe & Cie, 2000)' _computing_cell_refinement 'CELL (Stoe & Cie, 2000)' _computing_data_reduction 'INTEGRATE (Stoe & Cie, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-32 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0977P)^2^] 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 3380 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1075 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.849 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2287(9) 0.5546(7) 0.4339(7) 0.0735(19) Uani 1 1 d . . . H1A H 0.1413 0.6363 0.4557 0.110 Uiso 1 1 calc R . . H1B H 0.1881 0.4780 0.4596 0.110 Uiso 1 1 calc R . . H1C H 0.2709 0.5531 0.3444 0.110 Uiso 1 1 calc R . . C2 C 0.0073(8) 0.4640(7) 0.8114(6) 0.0670(17) Uani 1 1 d . . . C3 C 0.0327(9) 0.3283(7) 0.8149(7) 0.0686(18) Uani 1 1 d . . . C4 C 0.1808(9) 0.2743(6) 0.7310(6) 0.0645(17) Uani 1 1 d . . . C5 C 0.5919(7) 0.1874(5) 0.7772(5) 0.0526(15) Uani 1 1 d . . . C6 C 0.6955(8) 0.0570(5) 0.7806(6) 0.0557(15) Uani 1 1 d . . . C7 C 0.7528(8) 0.0183(6) 0.6569(6) 0.0630(17) Uani 1 1 d . . . C8 C -0.1306(11) 0.5762(10) 0.8766(9) 0.101(3) Uani 1 1 d . . . H8A H -0.0887 0.6454 0.8963 0.152 Uiso 1 1 calc R . . H8B H -0.1865 0.5422 0.9530 0.152 Uiso 1 1 calc R . . H8C H -0.2056 0.6133 0.8225 0.152 Uiso 1 1 calc R . . C9 C -0.0776(13) 0.2507(11) 0.8915(9) 0.122(4) Uani 1 1 d . . . H9A H -0.1645 0.3104 0.9495 0.184 Uiso 1 1 calc R . . H9B H -0.0158 0.1791 0.9377 0.184 Uiso 1 1 calc R . . H9C H -0.1231 0.2131 0.8364 0.184 Uiso 1 1 calc R . . C10 C 0.2668(12) 0.1301(7) 0.6994(9) 0.098(3) Uani 1 1 d . . . H10A H 0.3443 0.1250 0.6203 0.146 Uiso 1 1 calc R . . H10B H 0.1883 0.0848 0.6933 0.146 Uiso 1 1 calc R . . H10C H 0.3231 0.0873 0.7643 0.146 Uiso 1 1 calc R . . C11 C 0.4927(9) 0.2777(6) 0.8821(6) 0.0700(19) Uani 1 1 d . . . H11A H 0.4891 0.3695 0.8574 0.105 Uiso 1 1 calc R . . H11B H 0.5408 0.2530 0.9543 0.105 Uiso 1 1 calc R . . H11C H 0.3836 0.2694 0.9030 0.105 Uiso 1 1 calc R . . C12 C 0.7333(11) -0.0261(7) 0.8938(7) 0.080(2) Uani 1 1 d . . . H12A H 0.6706 -0.0896 0.9119 0.120 Uiso 1 1 calc R . . H12B H 0.7059 0.0318 0.9645 0.120 Uiso 1 1 calc R . . H12C H 0.8479 -0.0741 0.8778 0.120 Uiso 1 1 calc R . . C13 C 0.8647(12) -0.1133(8) 0.6005(8) 0.096(3) Uani 1 1 d . . . H13A H 0.8135 -0.1838 0.6275 0.143 Uiso 1 1 calc R . . H13B H 0.9658 -0.1350 0.6277 0.143 Uiso 1 1 calc R . . H13C H 0.8860 -0.1052 0.5102 0.143 Uiso 1 1 calc R . . Cl1 Cl 0.6201(3) 0.25704(14) 0.26487(14) 0.0687(5) Uani 1 1 d . . . Cu1 Cu 0.45870(10) 0.39024(7) 0.58291(7) 0.0562(3) Uani 1 1 d . . . N1 N 0.2474(6) 0.3750(5) 0.6810(5) 0.0594(13) Uani 1 1 d . . . N2 N 0.5882(6) 0.2270(5) 0.6573(5) 0.0610(13) Uani 1 1 d . . . N3 N 0.1353(7) 0.4898(5) 0.7315(5) 0.0666(15) Uani 1 1 d . . . H3 H 0.1457 0.5696 0.7140 0.080 Uiso 1 1 calc R . . N4 N 0.6885(7) 0.1228(5) 0.5860(5) 0.0743(17) Uani 1 1 d . . . H4 H 0.7088 0.1233 0.5050 0.089 Uiso 1 1 calc R . . O1 O 0.3538(5) 0.5493(4) 0.4954(4) 0.0541(10) Uani 1 1 d . . . O2 O 0.5116(8) 0.2413(5) 0.3826(5) 0.0931(17) Uani 1 1 d . . . O3 O 0.7804(9) 0.2148(7) 0.2856(7) 0.124(2) Uani 1 1 d . . . O4 O 0.6023(10) 0.1806(6) 0.1715(5) 0.110(2) Uani 1 1 d . . . O5 O 0.5823(8) 0.3952(4) 0.2311(5) 0.0945(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 C1 0.067(5) 0.072(4) 0.076(4) 0.011(3) -0.020(4) -0.010(3) C2 0.053(4) 0.080(4) 0.061(4) 0.002(3) -0.007(3) -0.015(3) C3 0.063(5) 0.081(4) 0.069(4) 0.014(3) -0.015(3) -0.036(4) C4 0.072(5) 0.057(3) 0.070(4) 0.018(3) -0.024(4) -0.026(3) C5 0.061(4) 0.041(3) 0.047(3) 0.019(2) -0.012(3) -0.009(3) C6 0.065(4) 0.041(3) 0.059(3) 0.015(2) -0.018(3) -0.013(3) C7 0.066(4) 0.044(3) 0.065(4) 0.013(3) -0.023(3) 0.007(3) C8 0.071(6) 0.122(7) 0.092(6) -0.016(5) 0.004(5) -0.011(5) C9 0.120(8) 0.159(9) 0.113(7) 0.045(7) -0.017(6) -0.096(8) C10 0.123(8) 0.047(4) 0.123(7) 0.013(4) -0.040(6) -0.020(4) C11 0.088(5) 0.057(3) 0.051(3) 0.008(3) -0.004(3) -0.012(3) C12 0.107(6) 0.053(3) 0.074(4) 0.034(3) -0.032(4) -0.013(4) C13 0.107(7) 0.070(5) 0.088(5) -0.005(4) -0.033(5) 0.017(4) Cl1 0.1023(15) 0.0478(8) 0.0553(9) 0.0076(6) -0.0270(9) -0.0158(8) Cu1 0.0586(5) 0.0461(4) 0.0525(4) 0.0172(3) -0.0091(3) -0.0060(3) N1 0.056(3) 0.043(2) 0.071(3) 0.015(2) -0.017(3) -0.005(2) N2 0.057(3) 0.058(3) 0.050(3) 0.011(2) -0.005(2) 0.001(2) N3 0.066(4) 0.048(3) 0.076(3) 0.009(2) -0.003(3) -0.014(3) N4 0.084(4) 0.069(3) 0.048(3) 0.013(2) -0.007(3) 0.001(3) O1 0.057(3) 0.052(2) 0.048(2) 0.0068(17) -0.0138(19) -0.0081(18) O2 0.139(5) 0.083(3) 0.063(3) 0.006(2) -0.008(3) -0.053(3) O3 0.095(5) 0.126(5) 0.132(6) -0.035(4) -0.039(4) 0.015(4) O4 0.203(7) 0.075(3) 0.069(3) 0.000(3) -0.058(4) -0.042(4) O5 0.149(5) 0.046(2) 0.083(3) 0.025(2) -0.030(3) -0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.402(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N3 1.332(8) . ? C2 C3 1.356(10) . ? C2 C8 1.490(10) . ? C3 C4 1.391(10) . ? C3 C9 1.503(9) . ? C4 N1 1.360(7) . ? C4 C10 1.488(10) . ? C5 N2 1.341(7) . ? C5 C6 1.388(8) . ? C5 C11 1.475(8) . ? C6 C7 1.375(9) . ? C6 C12 1.488(8) . ? C7 N4 1.336(7) . ? C7 C13 1.504(9) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? Cl1 O5 1.407(4) . ? Cl1 O4 1.408(5) . ? Cl1 O3 1.410(7) . ? Cl1 O2 1.437(5) . ? Cu1 O1 1.924(4) 2_666 ? Cu1 O1 1.926(4) . ? Cu1 N1 1.956(5) . ? Cu1 N2 1.964(5) . ? Cu1 Cu1 2.9409(15) 2_666 ? N1 N3 1.358(7) . ? N2 N4 1.341(7) . ? N3 H3 0.8600 . ? N4 H4 0.8600 . ? O1 Cu1 1.924(4) 2_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 C3 107.6(6) . . ? N3 C2 C8 120.6(7) . . ? C3 C2 C8 131.9(7) . . ? C2 C3 C4 106.3(5) . . ? C2 C3 C9 127.3(8) . . ? C4 C3 C9 126.4(8) . . ? N1 C4 C3 109.7(6) . . ? N1 C4 C10 121.7(7) . . ? C3 C4 C10 128.5(6) . . ? N2 C5 C6 109.9(5) . . ? N2 C5 C11 120.6(5) . . ? C6 C5 C11 129.4(5) . . ? C7 C6 C5 105.4(5) . . ? C7 C6 C12 126.8(6) . . ? C5 C6 C12 127.7(6) . . ? N4 C7 C6 107.3(5) . . ? N4 C7 C13 122.2(6) . . ? C6 C7 C13 130.6(6) . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 Cl1 O4 110.9(3) . . ? O5 Cl1 O3 108.3(4) . . ? O4 Cl1 O3 111.9(4) . . ? O5 Cl1 O2 108.4(3) . . ? O4 Cl1 O2 109.9(4) . . ? O3 Cl1 O2 107.2(4) . . ? O1 Cu1 O1 80.39(19) 2_666 . ? O1 Cu1 N1 165.29(18) 2_666 . ? O1 Cu1 N1 91.50(18) . . ? O1 Cu1 N2 93.8(2) 2_666 . ? O1 Cu1 N2 173.53(19) . . ? N1 Cu1 N2 94.8(2) . . ? O1 Cu1 Cu1 40.21(12) 2_666 2_666 ? O1 Cu1 Cu1 40.18(12) . 2_666 ? N1 Cu1 Cu1 130.55(14) . 2_666 ? N2 Cu1 Cu1 133.99(16) . 2_666 ? N3 N1 C4 104.5(5) . . ? N3 N1 Cu1 117.5(4) . . ? C4 N1 Cu1 137.3(5) . . ? C5 N2 N4 106.0(5) . . ? C5 N2 Cu1 132.3(4) . . ? N4 N2 Cu1 121.5(4) . . ? C2 N3 N1 111.9(5) . . ? C2 N3 H3 124.1 . . ? N1 N3 H3 124.1 . . ? C7 N4 N2 111.4(5) . . ? C7 N4 H4 124.3 . . ? N2 N4 H4 124.3 . . ? C1 O1 Cu1 122.8(4) . 2_666 ? C1 O1 Cu1 123.1(4) . . ? Cu1 O1 Cu1 99.61(19) 2_666 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C2 C3 C4 -1.2(8) . . . . ? C8 C2 C3 C4 177.9(9) . . . . ? N3 C2 C3 C9 179.9(7) . . . . ? C8 C2 C3 C9 -0.9(14) . . . . ? C2 C3 C4 N1 2.3(8) . . . . ? C9 C3 C4 N1 -178.8(7) . . . . ? C2 C3 C4 C10 179.5(8) . . . . ? C9 C3 C4 C10 -1.7(13) . . . . ? N2 C5 C6 C7 -0.9(8) . . . . ? C11 C5 C6 C7 178.1(7) . . . . ? N2 C5 C6 C12 -179.1(7) . . . . ? C11 C5 C6 C12 -0.1(12) . . . . ? C5 C6 C7 N4 1.5(8) . . . . ? C12 C6 C7 N4 179.8(7) . . . . ? C5 C6 C7 C13 -177.7(8) . . . . ? C12 C6 C7 C13 0.5(13) . . . . ? C3 C4 N1 N3 -2.4(7) . . . . ? C10 C4 N1 N3 -179.8(7) . . . . ? C3 C4 N1 Cu1 167.2(5) . . . . ? C10 C4 N1 Cu1 -10.2(11) . . . . ? O1 Cu1 N1 N3 11.1(11) 2_666 . . . ? O1 Cu1 N1 N3 -45.0(5) . . . . ? N2 Cu1 N1 N3 136.6(5) . . . . ? Cu1 Cu1 N1 N3 -34.6(6) 2_666 . . . ? O1 Cu1 N1 C4 -157.5(7) 2_666 . . . ? O1 Cu1 N1 C4 146.4(7) . . . . ? N2 Cu1 N1 C4 -32.0(7) . . . . ? Cu1 Cu1 N1 C4 156.8(6) 2_666 . . . ? C6 C5 N2 N4 -0.1(8) . . . . ? C11 C5 N2 N4 -179.2(6) . . . . ? C6 C5 N2 Cu1 174.8(5) . . . . ? C11 C5 N2 Cu1 -4.3(10) . . . . ? O1 Cu1 N2 C5 114.8(6) 2_666 . . . ? N1 Cu1 N2 C5 -53.2(6) . . . . ? Cu1 Cu1 N2 C5 117.5(6) 2_666 . . . ? O1 Cu1 N2 N4 -70.9(5) 2_666 . . . ? N1 Cu1 N2 N4 121.1(5) . . . . ? Cu1 Cu1 N2 N4 -68.2(6) 2_666 . . . ? C3 C2 N3 N1 -0.3(8) . . . . ? C8 C2 N3 N1 -179.5(7) . . . . ? C4 N1 N3 C2 1.6(8) . . . . ? Cu1 N1 N3 C2 -170.4(4) . . . . ? C6 C7 N4 N2 -1.7(8) . . . . ? C13 C7 N4 N2 177.6(7) . . . . ? C5 N2 N4 C7 1.1(8) . . . . ? Cu1 N2 N4 C7 -174.5(5) . . . . ? O1 Cu1 O1 C1 140.1(5) 2_666 . . . ? N1 Cu1 O1 C1 -52.3(5) . . . . ? Cu1 Cu1 O1 C1 140.1(5) 2_666 . . . ? O1 Cu1 O1 Cu1 0.0 2_666 . . 2_666 ? N1 Cu1 O1 Cu1 167.7(2) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 26.12 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.677 _refine_diff_density_min -1.170 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 930624' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:complex3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H84 Cu4 N16 O4, 4 (Cl O4)' _chemical_formula_sum 'C48 H84 Cl4 Cu4 N16 O20' _chemical_formula_weight 1601.27 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 15.9451(6) _cell_length_b 30.6995(8) _cell_length_c 20.6734(9) _cell_angle_alpha 90.00 _cell_angle_beta 122.694(3) _cell_angle_gamma 90.00 _cell_volume 8516.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.48 _cell_measurement_theta_max 28.40 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3296 _exptl_absorpt_coefficient_mu 1.174 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.088 0.000 0.412 1238 316 ' ' 2 -0.103 0.500 0.898 1238 317 ' ' 3 0.473 0.661 0.962 11 2 ' ' 4 0.473 0.839 0.462 11 2 ' ' 5 0.527 0.161 0.538 11 1 ' ' 6 0.527 0.339 0.038 11 1 ' ' _platon_squeeze_details ; Upon examination of the crystal packing of complex 3 with PLATON (Spek, 2003), two large solvent accessible voids were observed. These solvent accessible voids occupy an area of approximately 1240 \%A^3^. Chemical evidence suggests that diethylether molecules sit in these regions, however, the electron densities in these areas are quite low and it was not possible to define crystallographically the solvent molecules. Therefore, a data set corresponding to omission of the missing solvent was generated using the SQUEEZE (Spek, 2003; van der Sluis & Spek, 1990) algorithm from PLATON and the structure was refined to convergence. ; _exptl_special_details ; A crystal was mounted at 173K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using MoK\a graphite monochromated radiation. Image plate distance 70mm, \f oscillation scans 0 - 200\%, step \D\f = 1.0\%, 5 minutes per frame. ; _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 'STOE IPDS' _diffrn_measurement_method 'phi oscillation' _diffrn_detector_area_resol_mean 0.81\%A _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 109282 _diffrn_reflns_av_R_equivalents 0.1237 _diffrn_reflns_av_unetI/netI 0.1306 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 29.35 _reflns_number_total 23126 _reflns_number_gt 13196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE (Stoe & Cie, 2000)' _computing_cell_refinement 'CELL (Stoe & Cie, 2000)' _computing_data_reduction 'INTEGRATE (Stoe & Cie, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-32 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0959P)^2^] 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 23126 _refine_ls_number_parameters 835 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1880 _refine_ls_R_factor_gt 0.1020 _refine_ls_wR_factor_ref 0.2306 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4076(4) 0.2340(2) 0.0808(3) 0.0244(12) Uani 1 1 d . . . C2 C 0.3566(4) 0.1955(2) 0.0764(3) 0.0274(13) Uani 1 1 d . . . C3 C 0.3386(5) 0.1993(2) 0.1350(3) 0.0262(13) Uani 1 1 d . . . C4 C 0.4418(5) 0.2481(2) 0.0288(4) 0.0358(15) Uani 1 1 d . . . H4A H 0.3853 0.2506 -0.0229 0.054 Uiso 1 1 calc R . . H4B H 0.4873 0.2268 0.0307 0.054 Uiso 1 1 calc R . . H4C H 0.4747 0.2758 0.0456 0.054 Uiso 1 1 calc R . . C5 C 0.3278(5) 0.1587(2) 0.0212(4) 0.0373(16) Uani 1 1 d . . . H5A H 0.3842 0.1399 0.0383 0.056 Uiso 1 1 calc R . . H5B H 0.3061 0.1699 -0.0288 0.056 Uiso 1 1 calc R . . H5C H 0.2746 0.1424 0.0187 0.056 Uiso 1 1 calc R . . C6 C 0.2877(5) 0.1692(2) 0.1608(4) 0.0357(15) Uani 1 1 d . . . H6A H 0.3370 0.1524 0.2040 0.054 Uiso 1 1 calc R . . H6B H 0.2441 0.1499 0.1195 0.054 Uiso 1 1 calc R . . H6C H 0.2496 0.1860 0.1753 0.054 Uiso 1 1 calc R . . C7 C 0.2938(5) 0.3695(2) 0.0537(4) 0.0393(17) Uani 1 1 d . . . C8 C 0.2005(6) 0.3806(3) 0.0410(5) 0.058(2) Uani 1 1 d . . . C9 C 0.1951(6) 0.3624(3) 0.0991(6) 0.060(2) Uani 1 1 d . . . C10 C 0.3379(6) 0.3800(3) 0.0080(4) 0.059(2) Uani 1 1 d . . . H10A H 0.3472 0.4109 0.0084 0.089 Uiso 1 1 calc R . . H10B H 0.2940 0.3703 -0.0440 0.089 Uiso 1 1 calc R . . H10C H 0.4011 0.3656 0.0301 0.089 Uiso 1 1 calc R . . C11 C 0.1219(8) 0.4091(4) -0.0256(7) 0.103(4) Uani 1 1 d . . . H11A H 0.1102 0.3982 -0.0733 0.154 Uiso 1 1 calc R . . H11B H 0.1455 0.4386 -0.0183 0.154 Uiso 1 1 calc R . . H11C H 0.0609 0.4083 -0.0268 0.154 Uiso 1 1 calc R . . C12 C 0.1154(7) 0.3619(4) 0.1179(7) 0.090(4) Uani 1 1 d . . . H12A H 0.0577 0.3468 0.0781 0.135 Uiso 1 1 calc R . . H12B H 0.0975 0.3913 0.1214 0.135 Uiso 1 1 calc R . . H12C H 0.1405 0.3474 0.1661 0.135 Uiso 1 1 calc R . . C13 C 0.3110(6) 0.4360(3) 0.2502(5) 0.0476(19) Uani 1 1 d . . . C14 C 0.3219(6) 0.4147(2) 0.3133(5) 0.0445(18) Uani 1 1 d . . . C15 C 0.4115(5) 0.3921(2) 0.3454(4) 0.0330(14) Uani 1 1 d . . . C16 C 0.2309(7) 0.4670(3) 0.1927(7) 0.080(3) Uani 1 1 d . . . H16A H 0.2437 0.4958 0.2144 0.121 Uiso 1 1 calc R . . H16B H 0.1669 0.4573 0.1809 0.121 Uiso 1 1 calc R . . H16C H 0.2316 0.4676 0.1465 0.121 Uiso 1 1 calc R . . C17 C 0.2527(7) 0.4143(3) 0.3414(6) 0.072(3) Uani 1 1 d . . . H17A H 0.2127 0.4402 0.3243 0.108 Uiso 1 1 calc R . . H17B H 0.2909 0.4133 0.3965 0.108 Uiso 1 1 calc R . . H17C H 0.2103 0.3892 0.3213 0.108 Uiso 1 1 calc R . . C18 C 0.4629(6) 0.3651(3) 0.4164(4) 0.0479(19) Uani 1 1 d . . . H18A H 0.5216 0.3524 0.4224 0.072 Uiso 1 1 calc R . . H18B H 0.4189 0.3425 0.4126 0.072 Uiso 1 1 calc R . . H18C H 0.4813 0.3832 0.4601 0.072 Uiso 1 1 calc R . . C19 C 0.7166(5) 0.4375(2) 0.4528(4) 0.0391(17) Uani 1 1 d . . . C20 C 0.7479(6) 0.4812(3) 0.4680(5) 0.049(2) Uani 1 1 d . . . C21 C 0.6981(6) 0.5018(2) 0.3976(6) 0.056(2) Uani 1 1 d . . . C22 C 0.7464(6) 0.4019(3) 0.5091(4) 0.052(2) Uani 1 1 d . . . H22A H 0.7270 0.4091 0.5445 0.078 Uiso 1 1 calc R . . H22B H 0.8173 0.3981 0.5368 0.078 Uiso 1 1 calc R . . H22C H 0.7141 0.3754 0.4828 0.078 Uiso 1 1 calc R . . C23 C 0.8195(7) 0.5013(4) 0.5438(6) 0.080(3) Uani 1 1 d . . . H23A H 0.8856 0.4910 0.5620 0.120 Uiso 1 1 calc R . . H23B H 0.8018 0.4935 0.5798 0.120 Uiso 1 1 calc R . . H23C H 0.8176 0.5324 0.5385 0.120 Uiso 1 1 calc R . . C24 C 0.6957(8) 0.5490(3) 0.3735(8) 0.089(4) Uani 1 1 d . . . H24A H 0.6610 0.5507 0.3185 0.134 Uiso 1 1 calc R . . H24B H 0.7626 0.5594 0.3959 0.134 Uiso 1 1 calc R . . H24C H 0.6620 0.5667 0.3910 0.134 Uiso 1 1 calc R . . C25 C 0.6876(5) 0.4474(2) 0.1646(4) 0.0350(15) Uani 1 1 d . . . C26 C 0.7345(6) 0.4880(2) 0.1896(5) 0.0429(18) Uani 1 1 d . . . C27 C 0.7991(6) 0.4843(3) 0.2675(4) 0.0454(18) Uani 1 1 d . . . C28 C 0.6123(6) 0.4332(3) 0.0845(4) 0.051(2) Uani 1 1 d . . . H28A H 0.5904 0.4042 0.0854 0.077 Uiso 1 1 calc R . . H28B H 0.6417 0.4336 0.0544 0.077 Uiso 1 1 calc R . . H28C H 0.5563 0.4527 0.0621 0.077 Uiso 1 1 calc R . . C29 C 0.7174(7) 0.5267(3) 0.1389(6) 0.069(3) Uani 1 1 d . . . H29A H 0.6521 0.5384 0.1195 0.104 Uiso 1 1 calc R . . H29B H 0.7225 0.5178 0.0967 0.104 Uiso 1 1 calc R . . H29C H 0.7666 0.5486 0.1683 0.104 Uiso 1 1 calc R . . C30 C 0.8718(7) 0.5165(3) 0.3249(5) 0.068(3) Uani 1 1 d . . . H30A H 0.8841 0.5100 0.3747 0.102 Uiso 1 1 calc R . . H30B H 0.8447 0.5454 0.3100 0.102 Uiso 1 1 calc R . . H30C H 0.9332 0.5149 0.3268 0.102 Uiso 1 1 calc R . . C31 C 0.8232(5) 0.3166(2) 0.1912(4) 0.0358(15) Uani 1 1 d . . . C32 C 0.9226(5) 0.3076(3) 0.2253(4) 0.0409(17) Uani 1 1 d . . . C33 C 0.9681(5) 0.3214(3) 0.3000(4) 0.0440(18) Uani 1 1 d . . . C34 C 0.7405(6) 0.3088(3) 0.1095(4) 0.0458(19) Uani 1 1 d . . . H34A H 0.7162 0.2796 0.1041 0.069 Uiso 1 1 calc R . . H34B H 0.7649 0.3129 0.0764 0.069 Uiso 1 1 calc R . . H34C H 0.6873 0.3290 0.0956 0.069 Uiso 1 1 calc R . . C35 C 0.9727(7) 0.2860(4) 0.1889(6) 0.077(3) Uani 1 1 d . . . H35A H 0.9579 0.3020 0.1440 0.115 Uiso 1 1 calc R . . H35B H 0.9484 0.2567 0.1745 0.115 Uiso 1 1 calc R . . H35C H 1.0435 0.2855 0.2251 0.115 Uiso 1 1 calc R . . C36 C 1.0757(5) 0.3218(3) 0.3662(5) 0.061(3) Uani 1 1 d . . . H36A H 1.1014 0.3509 0.3741 0.092 Uiso 1 1 calc R . . H36B H 1.1140 0.3030 0.3545 0.092 Uiso 1 1 calc R . . H36C H 1.0802 0.3117 0.4119 0.092 Uiso 1 1 calc R . . C37 C 0.8821(5) 0.2695(2) 0.4491(3) 0.0327(14) Uani 1 1 d . . . C38 C 0.9657(5) 0.2500(2) 0.4564(4) 0.0396(17) Uani 1 1 d . . . C39 C 0.9334(5) 0.2328(3) 0.3844(4) 0.0431(17) Uani 1 1 d . . . C40 C 0.8744(6) 0.2919(3) 0.5109(4) 0.049(2) Uani 1 1 d . . . H40A H 0.8948 0.3218 0.5151 0.074 Uiso 1 1 calc R . . H40B H 0.9168 0.2775 0.5591 0.074 Uiso 1 1 calc R . . H40C H 0.8067 0.2908 0.4976 0.074 Uiso 1 1 calc R . . C41 C 1.0712(6) 0.2498(3) 0.5271(5) 0.072(3) Uani 1 1 d . . . H41A H 1.1115 0.2301 0.5191 0.107 Uiso 1 1 calc R . . H41B H 1.0700 0.2406 0.5710 0.107 Uiso 1 1 calc R . . H41C H 1.0986 0.2787 0.5358 0.107 Uiso 1 1 calc R . . C42 C 0.9846(6) 0.2078(3) 0.3541(6) 0.066(3) Uani 1 1 d . . . H42A H 0.9524 0.2131 0.3000 0.099 Uiso 1 1 calc R . . H42B H 0.9814 0.1773 0.3627 0.099 Uiso 1 1 calc R . . H42C H 1.0530 0.2167 0.3801 0.099 Uiso 1 1 calc R . . C43 C 0.5732(5) 0.2118(2) 0.3662(3) 0.0322(14) Uani 1 1 d . . . C44 C 0.5429(5) 0.1688(2) 0.3435(4) 0.0382(16) Uani 1 1 d . . . C45 C 0.5619(5) 0.1597(2) 0.2872(4) 0.0342(15) Uani 1 1 d . . . C46 C 0.5710(6) 0.2379(3) 0.4261(4) 0.0419(17) Uani 1 1 d . . . H46A H 0.6224 0.2596 0.4461 0.063 Uiso 1 1 calc R . . H46B H 0.5820 0.2190 0.4671 0.063 Uiso 1 1 calc R . . H46C H 0.5073 0.2518 0.4039 0.063 Uiso 1 1 calc R . . C47 C 0.5014(6) 0.1380(3) 0.3772(5) 0.057(2) Uani 1 1 d . . . H47A H 0.4821 0.1111 0.3491 0.086 Uiso 1 1 calc R . . H47B H 0.4443 0.1511 0.3737 0.086 Uiso 1 1 calc R . . H47C H 0.5515 0.1324 0.4302 0.086 Uiso 1 1 calc R . . C48 C 0.5459(7) 0.1197(2) 0.2402(5) 0.056(2) Uani 1 1 d . . . H48A H 0.5125 0.1276 0.1869 0.085 Uiso 1 1 calc R . . H48B H 0.5059 0.0992 0.2470 0.085 Uiso 1 1 calc R . . H48C H 0.6092 0.1068 0.2565 0.085 Uiso 1 1 calc R . . Cu1 Cu 0.47715(5) 0.31878(2) 0.16906(4) 0.02288(16) Uani 1 1 d . . . Cu2 Cu 0.58157(6) 0.37787(2) 0.32355(4) 0.02447(17) Uani 1 1 d . . . Cu3 Cu 0.68132(5) 0.35929(2) 0.22619(4) 0.02454(17) Uani 1 1 d . . . Cu4 Cu 0.66423(5) 0.28690(2) 0.33098(4) 0.02396(17) Uani 1 1 d . . . N1 N 0.4217(4) 0.25904(17) 0.1383(3) 0.0251(11) Uani 1 1 d . . . N2 N 0.3788(4) 0.23700(16) 0.1711(3) 0.0264(11) Uani 1 1 d . . . H2 H 0.3780 0.2463 0.2100 0.032 Uiso 1 1 calc R . . N3 N 0.3448(4) 0.34549(19) 0.1186(3) 0.0342(13) Uani 1 1 d . . . N4 N 0.2821(4) 0.3416(2) 0.1448(4) 0.0405(14) Uani 1 1 d . . . H4 H 0.2969 0.3275 0.1856 0.049 Uiso 1 1 calc R . . N5 N 0.4523(4) 0.39883(18) 0.3041(3) 0.0311(12) Uani 1 1 d . . . N6 N 0.3897(4) 0.42645(18) 0.2464(3) 0.0365(13) Uani 1 1 d . . . H6 H 0.3996 0.4364 0.2122 0.044 Uiso 1 1 calc R . . N7 N 0.6525(4) 0.43154(18) 0.3771(3) 0.0364(13) Uani 1 1 d . . . N8 N 0.6418(5) 0.47133(18) 0.3439(4) 0.0430(15) Uani 1 1 d . . . H8 H 0.6043 0.4764 0.2954 0.052 Uiso 1 1 calc R . . N9 N 0.7195(4) 0.42071(18) 0.2248(3) 0.0291(12) Uani 1 1 d . . . N10 N 0.7886(4) 0.44401(18) 0.2870(3) 0.0347(13) Uani 1 1 d . . . H10 H 0.8214 0.4341 0.3333 0.042 Uiso 1 1 calc R . . N11 N 0.8058(4) 0.33562(19) 0.2416(3) 0.0329(12) Uani 1 1 d . . . N12 N 0.8959(4) 0.33822(19) 0.3078(3) 0.0334(12) Uani 1 1 d . . . H12 H 0.9061 0.3492 0.3497 0.040 Uiso 1 1 calc R . . N13 N 0.8033(4) 0.26500(18) 0.3780(3) 0.0315(12) Uani 1 1 d . . . N14 N 0.8363(4) 0.24274(19) 0.3396(3) 0.0354(13) Uani 1 1 d . . . H14 H 0.7992 0.2357 0.2918 0.042 Uiso 1 1 calc R . . N15 N 0.6083(4) 0.22891(17) 0.3249(3) 0.0283(11) Uani 1 1 d . . . N16 N 0.5997(4) 0.19649(17) 0.2774(3) 0.0316(12) Uani 1 1 d . . . H16 H 0.6166 0.1991 0.2445 0.038 Uiso 1 1 calc R . . O1 O 0.5471(3) 0.37512(14) 0.1980(2) 0.0278(9) Uani 1 1 d . . . H1 H 0.5146 0.4002 0.1641 0.033 Uiso 1 1 calc R . . O2 O 0.6145(3) 0.30188(13) 0.2051(2) 0.0240(9) Uani 1 1 d . . . H2A H 0.6259 0.2800 0.1761 0.029 Uiso 1 1 calc R . . O3 O 0.5376(3) 0.31674(14) 0.2981(2) 0.0266(9) Uani 1 1 d . . . H3 H 0.4951 0.3047 0.3145 0.032 Uiso 1 1 calc R . . O4 O 0.7041(3) 0.34858(13) 0.3454(2) 0.0257(9) Uani 1 1 d . . . H4D H 0.7678 0.3570 0.3915 0.031 Uiso 1 1 calc R . . Cl1 Cl 0.27705(13) 0.26633(7) 0.28935(9) 0.0398(4) Uani 1 1 d . . . O5 O 0.1933(4) 0.2580(2) 0.2159(3) 0.0591(17) Uani 1 1 d . . . O6 O 0.3552(3) 0.28583(17) 0.2820(3) 0.0410(12) Uani 1 1 d . . . O7 O 0.3160(5) 0.2254(2) 0.3300(4) 0.0719(18) Uani 1 1 d . . . O8 O 0.2563(4) 0.2941(2) 0.3333(4) 0.0677(19) Uani 1 1 d . . . Cl2 Cl 0.99138(14) 0.40372(6) 0.49107(10) 0.0446(4) Uani 1 1 d . . . O9 O 0.9943(7) 0.3994(4) 0.5596(4) 0.145(5) Uani 1 1 d . . . O10 O 0.9960(8) 0.4488(3) 0.4813(6) 0.156(5) Uani 1 1 d . . . O11 O 0.8954(4) 0.38726(18) 0.4271(3) 0.0466(13) Uani 1 1 d . . . O12 O 1.0661(6) 0.3827(5) 0.4931(6) 0.180(6) Uani 1 1 d . . . Cl3 Cl 0.43934(18) 0.50244(6) 0.13222(12) 0.0558(5) Uani 1 1 d G . . O13 O 0.4574(6) 0.45804(9) 0.1543(4) 0.106(3) Uani 1 1 d G . . O14 O 0.4061(9) 0.5067(2) 0.0529(2) 0.313(14) Uani 1 1 d G . . O15 O 0.5244(4) 0.5277(2) 0.1806(5) 0.297(12) Uani 1 1 d G . . O16 O 0.3581(6) 0.5173(2) 0.1376(6) 0.171(5) Uani 1 1 d G . . Cl4 Cl 0.69895(15) 0.18278(6) 0.14441(10) 0.0496(5) Uani 1 1 d G . . O17 O 0.7222(8) 0.20006(15) 0.0924(5) 0.261(10) Uani 1 1 d G . . O18 O 0.7825(5) 0.1591(2) 0.2042(2) 0.172(6) Uani 1 1 d G . . O19 O 0.6121(3) 0.1573(2) 0.1052(5) 0.184(6) Uani 1 1 d G . . O20 O 0.6837(3) 0.21834(10) 0.1819(2) 0.0451(13) Uani 1 1 d G . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.020(3) 0.030(3) 0.019(3) -0.003(2) 0.007(2) 0.002(3) C2 0.021(3) 0.033(3) 0.022(3) -0.002(2) 0.007(2) 0.000(3) C3 0.030(3) 0.023(3) 0.026(3) 0.001(2) 0.016(3) 0.002(3) C4 0.045(4) 0.042(4) 0.025(3) -0.003(3) 0.021(3) -0.004(3) C5 0.045(4) 0.038(4) 0.033(4) -0.009(3) 0.024(3) -0.008(3) C6 0.038(4) 0.029(3) 0.049(4) -0.001(3) 0.030(3) -0.003(3) C7 0.030(4) 0.027(4) 0.038(4) 0.016(3) 0.003(3) 0.005(3) C8 0.045(5) 0.043(5) 0.062(5) 0.014(4) 0.012(4) 0.008(4) C9 0.040(5) 0.041(5) 0.090(7) 0.015(5) 0.031(5) 0.005(4) C10 0.060(5) 0.062(6) 0.036(4) 0.019(4) 0.014(4) -0.002(5) C11 0.058(6) 0.098(9) 0.097(9) 0.042(7) 0.005(6) 0.031(6) C12 0.049(6) 0.087(8) 0.145(11) 0.027(8) 0.060(7) 0.021(6) C13 0.039(4) 0.041(4) 0.061(5) 0.014(4) 0.026(4) 0.010(4) C14 0.046(4) 0.038(4) 0.066(5) 0.006(4) 0.041(4) 0.009(4) C15 0.036(4) 0.030(3) 0.038(4) -0.006(3) 0.023(3) -0.003(3) C16 0.063(6) 0.065(7) 0.108(9) 0.035(6) 0.043(6) 0.031(5) C17 0.081(7) 0.064(6) 0.104(8) 0.011(6) 0.072(7) 0.022(5) C18 0.057(5) 0.052(5) 0.045(4) -0.006(4) 0.034(4) -0.001(4) C19 0.037(4) 0.033(4) 0.044(4) -0.019(3) 0.020(3) -0.006(3) C20 0.042(4) 0.039(4) 0.066(5) -0.016(4) 0.029(4) -0.001(4) C21 0.043(5) 0.020(3) 0.111(8) -0.019(4) 0.046(5) -0.004(3) C22 0.066(5) 0.061(5) 0.027(4) -0.005(3) 0.023(4) -0.009(4) C23 0.064(6) 0.077(7) 0.089(8) -0.052(6) 0.035(6) -0.019(5) C24 0.074(7) 0.030(5) 0.150(11) 0.000(6) 0.051(7) -0.005(5) C25 0.038(4) 0.032(4) 0.035(4) 0.012(3) 0.020(3) -0.006(3) C26 0.041(4) 0.032(4) 0.056(5) 0.012(3) 0.026(4) -0.009(3) C27 0.042(4) 0.040(4) 0.048(4) -0.001(3) 0.020(4) -0.012(4) C28 0.049(5) 0.063(5) 0.035(4) -0.002(4) 0.018(4) -0.022(4) C29 0.069(6) 0.048(5) 0.076(6) 0.022(5) 0.030(5) -0.009(5) C30 0.073(6) 0.051(5) 0.067(6) -0.008(5) 0.029(5) -0.017(5) C31 0.037(4) 0.044(4) 0.032(3) -0.012(3) 0.022(3) -0.013(3) C32 0.033(4) 0.054(5) 0.040(4) -0.016(3) 0.023(3) -0.005(3) C33 0.026(3) 0.059(5) 0.049(4) -0.015(4) 0.022(3) -0.008(4) C34 0.045(4) 0.064(5) 0.028(4) -0.007(3) 0.020(3) -0.006(4) C35 0.065(6) 0.117(9) 0.065(6) -0.039(6) 0.046(5) -0.007(6) C36 0.033(4) 0.096(8) 0.045(5) -0.020(5) 0.015(4) -0.001(5) C37 0.037(4) 0.024(3) 0.023(3) 0.001(2) 0.007(3) -0.001(3) C38 0.029(4) 0.034(4) 0.035(4) 0.006(3) 0.004(3) 0.006(3) C39 0.030(4) 0.044(4) 0.044(4) -0.007(3) 0.013(3) 0.006(3) C40 0.057(5) 0.048(5) 0.031(4) 0.008(3) 0.016(4) 0.006(4) C41 0.041(5) 0.075(7) 0.061(6) 0.007(5) 0.003(4) 0.004(5) C42 0.043(5) 0.070(6) 0.078(6) -0.014(5) 0.027(5) 0.014(5) C43 0.028(3) 0.034(3) 0.026(3) 0.012(3) 0.009(3) 0.009(3) C44 0.039(4) 0.027(3) 0.043(4) 0.011(3) 0.018(3) 0.001(3) C45 0.034(4) 0.026(3) 0.033(3) 0.002(3) 0.012(3) -0.003(3) C46 0.051(4) 0.049(4) 0.026(3) 0.004(3) 0.021(3) 0.001(4) C47 0.054(5) 0.051(5) 0.062(5) 0.019(4) 0.028(4) -0.005(4) C48 0.068(6) 0.025(4) 0.070(6) -0.017(4) 0.034(5) -0.007(4) Cu1 0.0231(4) 0.0234(4) 0.0208(3) -0.0001(3) 0.0110(3) -0.0015(3) Cu2 0.0299(4) 0.0212(3) 0.0247(4) -0.0016(3) 0.0164(3) -0.0009(3) Cu3 0.0255(4) 0.0266(4) 0.0224(4) -0.0010(3) 0.0135(3) -0.0034(3) Cu4 0.0261(4) 0.0228(4) 0.0213(3) 0.0010(3) 0.0116(3) 0.0006(3) N1 0.024(3) 0.029(3) 0.024(2) -0.003(2) 0.014(2) -0.005(2) N2 0.036(3) 0.028(3) 0.028(3) -0.001(2) 0.025(2) 0.000(2) N3 0.029(3) 0.036(3) 0.038(3) 0.002(2) 0.018(3) -0.003(2) N4 0.033(3) 0.039(3) 0.051(4) 0.008(3) 0.023(3) 0.003(3) N5 0.031(3) 0.029(3) 0.032(3) -0.005(2) 0.016(2) -0.004(2) N6 0.039(3) 0.031(3) 0.049(3) 0.012(3) 0.030(3) 0.006(3) N7 0.037(3) 0.024(3) 0.044(3) 0.002(2) 0.019(3) 0.002(3) N8 0.047(4) 0.019(3) 0.064(4) 0.003(3) 0.031(3) 0.006(3) N9 0.025(3) 0.034(3) 0.020(2) -0.001(2) 0.006(2) -0.008(2) N10 0.037(3) 0.035(3) 0.029(3) 0.001(2) 0.015(3) -0.002(3) N11 0.033(3) 0.041(3) 0.027(3) -0.009(2) 0.018(2) -0.007(3) N12 0.023(3) 0.048(3) 0.023(3) -0.011(2) 0.008(2) -0.008(3) N13 0.032(3) 0.032(3) 0.028(3) -0.002(2) 0.015(2) -0.003(2) N14 0.028(3) 0.038(3) 0.033(3) -0.008(2) 0.011(2) 0.005(3) N15 0.030(3) 0.034(3) 0.020(2) -0.001(2) 0.013(2) 0.000(2) N16 0.041(3) 0.027(3) 0.031(3) -0.002(2) 0.022(3) 0.002(2) O1 0.029(2) 0.025(2) 0.027(2) 0.0050(17) 0.0138(19) -0.0008(19) O2 0.029(2) 0.029(2) 0.026(2) -0.0057(17) 0.0225(19) 0.0005(18) O3 0.030(2) 0.028(2) 0.022(2) 0.0024(17) 0.0138(18) 0.0009(19) O4 0.025(2) 0.026(2) 0.024(2) -0.0031(17) 0.0118(18) -0.0045(18) Cl1 0.0350(9) 0.0598(11) 0.0311(8) -0.0109(8) 0.0220(7) -0.0068(8) O5 0.033(3) 0.101(5) 0.035(3) -0.020(3) 0.013(2) -0.011(3) O6 0.035(3) 0.054(3) 0.042(3) -0.008(2) 0.026(2) -0.007(2) O7 0.090(5) 0.052(4) 0.074(4) 0.018(3) 0.044(4) 0.000(4) O8 0.065(4) 0.093(5) 0.069(4) -0.036(4) 0.052(3) -0.014(4) Cl2 0.0406(10) 0.0490(11) 0.0315(9) -0.0079(8) 0.0111(8) -0.0114(9) O9 0.139(8) 0.237(12) 0.041(4) -0.045(6) 0.037(5) -0.111(8) O10 0.165(9) 0.078(6) 0.118(8) -0.006(6) 0.007(7) -0.049(7) O11 0.036(3) 0.064(4) 0.030(2) -0.015(2) 0.012(2) -0.019(3) O12 0.045(4) 0.282(15) 0.141(9) -0.114(9) 0.004(5) 0.039(7) Cl3 0.0827(15) 0.0329(9) 0.0537(12) 0.0182(8) 0.0381(12) 0.0141(10) O13 0.210(9) 0.031(3) 0.164(8) 0.038(4) 0.157(8) 0.038(5) O14 0.68(4) 0.184(14) 0.224(15) 0.149(13) 0.34(2) 0.23(2) O15 0.187(14) 0.150(14) 0.52(4) -0.106(18) 0.169(19) -0.034(12) O16 0.185(11) 0.129(9) 0.270(15) 0.086(9) 0.170(12) 0.097(9) Cl4 0.0661(13) 0.0438(10) 0.0425(10) -0.0079(8) 0.0317(10) 0.0082(10) O17 0.66(3) 0.067(6) 0.322(17) 0.038(8) 0.44(2) 0.079(12) O18 0.179(10) 0.157(10) 0.107(8) -0.022(7) 0.030(7) 0.104(9) O19 0.128(8) 0.129(9) 0.228(13) -0.127(10) 0.052(9) -0.031(7) O20 0.057(3) 0.040(3) 0.041(3) -0.011(2) 0.028(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.329(7) . ? C1 C2 1.410(9) . ? C1 C4 1.507(8) . ? C2 C3 1.392(8) . ? C2 C5 1.492(9) . ? C3 N2 1.337(8) . ? C3 C6 1.505(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N3 1.350(8) . ? C7 C8 1.406(11) . ? C7 C10 1.488(11) . ? C8 C9 1.369(13) . ? C8 C11 1.539(12) . ? C9 N4 1.346(10) . ? C9 C12 1.516(12) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N6 1.331(9) . ? C13 C14 1.385(11) . ? C13 C16 1.519(11) . ? C14 C15 1.393(10) . ? C14 C17 1.499(10) . ? C15 N5 1.341(8) . ? C15 C18 1.486(10) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N7 1.341(9) . ? C19 C20 1.408(10) . ? C19 C22 1.475(11) . ? C20 C21 1.378(13) . ? C20 C23 1.485(12) . ? C21 N8 1.355(10) . ? C21 C24 1.527(12) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N9 1.340(8) . ? C25 C26 1.398(10) . ? C25 C28 1.493(10) . ? C26 C27 1.369(10) . ? C26 C29 1.510(10) . ? C27 N10 1.339(9) . ? C27 C30 1.500(11) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 N11 1.348(8) . ? C31 C32 1.370(10) . ? C31 C34 1.498(9) . ? C32 C33 1.372(10) . ? C32 C35 1.515(10) . ? C33 N12 1.347(8) . ? C33 C36 1.510(10) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 N13 1.328(8) . ? C37 C38 1.393(10) . ? C37 C40 1.513(10) . ? C38 C39 1.390(10) . ? C38 C41 1.519(10) . ? C39 N14 1.341(8) . ? C39 C42 1.483(11) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 N15 1.354(8) . ? C43 C44 1.396(10) . ? C43 C46 1.492(9) . ? C44 C45 1.382(10) . ? C44 C47 1.521(10) . ? C45 N16 1.347(8) . ? C45 C48 1.499(9) . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? Cu1 N3 1.959(6) . ? Cu1 O2 1.964(4) . ? Cu1 O1 1.968(4) . ? Cu1 N1 1.986(5) . ? Cu1 O3 2.296(4) . ? Cu2 N7 1.966(6) . ? Cu2 O4 1.968(4) . ? Cu2 O3 1.973(4) . ? Cu2 N5 1.982(5) . ? Cu2 O1 2.346(4) . ? Cu2 Cu4 3.0564(10) . ? Cu3 O1 1.952(4) . ? Cu3 N11 1.971(5) . ? Cu3 O2 1.983(4) . ? Cu3 N9 1.987(5) . ? Cu3 O4 2.312(4) . ? Cu4 N15 1.965(5) . ? Cu4 O4 1.968(4) . ? Cu4 O3 1.973(4) . ? Cu4 N13 1.997(5) . ? Cu4 O2 2.319(4) . ? N1 N2 1.373(6) . ? N2 H2 0.8600 . ? N3 N4 1.375(8) . ? N4 H4 0.8600 . ? N5 N6 1.361(7) . ? N6 H6 0.8600 . ? N7 N8 1.366(8) . ? N8 H8 0.8600 . ? N9 N10 1.360(7) . ? N10 H10 0.8600 . ? N11 N12 1.348(7) . ? N12 H12 0.8600 . ? N13 N14 1.351(7) . ? N14 H14 0.8600 . ? N15 N16 1.353(7) . ? N16 H16 0.8600 . ? O1 H1 0.9800 . ? O2 H2A 0.9800 . ? O3 H3 0.9800 . ? O4 H4D 0.9800 . ? Cl1 O5 1.401(5) . ? Cl1 O8 1.409(5) . ? Cl1 O7 1.452(6) . ? Cl1 O6 1.464(5) . ? Cl2 O12 1.336(8) . ? Cl2 O9 1.398(8) . ? Cl2 O10 1.407(9) . ? Cl2 O11 1.469(5) . ? Cl3 O15 1.4052 . ? Cl3 O13 1.4168 . ? Cl3 O14 1.4320 . ? Cl3 O16 1.4338 . ? Cl4 O19 1.4052 . ? Cl4 O17 1.4168 . ? Cl4 O18 1.4320 . ? Cl4 O20 1.4339 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 110.8(5) . . ? N1 C1 C4 121.3(6) . . ? C2 C1 C4 127.8(5) . . ? C3 C2 C1 104.9(5) . . ? C3 C2 C5 127.3(6) . . ? C1 C2 C5 127.8(6) . . ? N2 C3 C2 107.2(5) . . ? N2 C3 C6 121.5(5) . . ? C2 C3 C6 131.3(6) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 C8 109.1(7) . . ? N3 C7 C10 120.8(6) . . ? C8 C7 C10 130.1(7) . . ? C9 C8 C7 107.4(7) . . ? C9 C8 C11 127.6(9) . . ? C7 C8 C11 125.0(9) . . ? N4 C9 C8 106.2(7) . . ? N4 C9 C12 120.3(8) . . ? C8 C9 C12 133.5(8) . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N6 C13 C14 107.9(6) . . ? N6 C13 C16 120.9(8) . . ? C14 C13 C16 131.1(8) . . ? C13 C14 C15 105.1(6) . . ? C13 C14 C17 128.7(7) . . ? C15 C14 C17 126.2(7) . . ? N5 C15 C14 110.1(6) . . ? N5 C15 C18 121.2(6) . . ? C14 C15 C18 128.7(6) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N7 C19 C20 110.2(7) . . ? N7 C19 C22 122.6(6) . . ? C20 C19 C22 127.2(7) . . ? C21 C20 C19 105.5(7) . . ? C21 C20 C23 126.9(8) . . ? C19 C20 C23 127.6(9) . . ? N8 C21 C20 107.3(7) . . ? N8 C21 C24 120.0(9) . . ? C20 C21 C24 132.7(9) . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N9 C25 C26 110.0(6) . . ? N9 C25 C28 121.7(6) . . ? C26 C25 C28 128.3(6) . . ? C27 C26 C25 105.8(6) . . ? C27 C26 C29 128.4(7) . . ? C25 C26 C29 125.8(7) . . ? N10 C27 C26 107.1(6) . . ? N10 C27 C30 122.7(7) . . ? C26 C27 C30 130.2(7) . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N11 C31 C32 110.7(6) . . ? N11 C31 C34 121.1(6) . . ? C32 C31 C34 128.1(6) . . ? C31 C32 C33 106.1(6) . . ? C31 C32 C35 127.3(7) . . ? C33 C32 C35 126.5(7) . . ? N12 C33 C32 106.6(6) . . ? N12 C33 C36 121.0(6) . . ? C32 C33 C36 132.3(7) . . ? C31 C34 H34A 109.5 . . ? C31 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C31 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N13 C37 C38 110.7(6) . . ? N13 C37 C40 121.5(6) . . ? C38 C37 C40 127.8(6) . . ? C39 C38 C37 105.5(6) . . ? C39 C38 C41 127.3(7) . . ? C37 C38 C41 127.1(7) . . ? N14 C39 C38 106.0(6) . . ? N14 C39 C42 121.3(7) . . ? C38 C39 C42 132.7(7) . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C38 C41 H41A 109.5 . . ? C38 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C38 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C42 H42A 109.5 . . ? C39 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C39 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? N15 C43 C44 110.0(6) . . ? N15 C43 C46 121.2(6) . . ? C44 C43 C46 128.8(6) . . ? C45 C44 C43 106.3(6) . . ? C45 C44 C47 127.5(7) . . ? C43 C44 C47 126.2(7) . . ? N16 C45 C44 106.1(6) . . ? N16 C45 C48 121.5(6) . . ? C44 C45 C48 132.4(7) . . ? C43 C46 H46A 109.5 . . ? C43 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C43 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C44 C47 H47A 109.5 . . ? C44 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C44 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C45 C48 H48A 109.5 . . ? C45 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C45 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? N3 Cu1 O2 166.6(2) . . ? N3 Cu1 O1 93.7(2) . . ? O2 Cu1 O1 77.55(17) . . ? N3 Cu1 N1 92.9(2) . . ? O2 Cu1 N1 95.15(19) . . ? O1 Cu1 N1 172.06(19) . . ? N3 Cu1 O3 106.6(2) . . ? O2 Cu1 O3 82.47(15) . . ? O1 Cu1 O3 81.79(16) . . ? N1 Cu1 O3 100.49(17) . . ? N7 Cu2 O4 93.2(2) . . ? N7 Cu2 O3 163.9(2) . . ? O4 Cu2 O3 77.98(17) . . ? N7 Cu2 N5 93.5(2) . . ? O4 Cu2 N5 171.5(2) . . ? O3 Cu2 N5 94.3(2) . . ? N7 Cu2 O1 111.9(2) . . ? O4 Cu2 O1 81.26(16) . . ? O3 Cu2 O1 80.40(15) . . ? N5 Cu2 O1 100.97(18) . . ? N7 Cu2 Cu4 129.49(17) . . ? O4 Cu2 Cu4 39.06(12) . . ? O3 Cu2 Cu4 39.23(12) . . ? N5 Cu2 Cu4 132.82(16) . . ? O1 Cu2 Cu4 81.94(11) . . ? O1 Cu3 N11 170.4(2) . . ? O1 Cu3 O2 77.47(17) . . ? N11 Cu3 O2 94.7(2) . . ? O1 Cu3 N9 93.1(2) . . ? N11 Cu3 N9 93.6(2) . . ? O2 Cu3 N9 166.73(19) . . ? O1 Cu3 O4 82.47(16) . . ? N11 Cu3 O4 102.14(19) . . ? O2 Cu3 O4 82.18(15) . . ? N9 Cu3 O4 106.13(18) . . ? N15 Cu4 O4 168.43(19) . . ? N15 Cu4 O3 93.1(2) . . ? O4 Cu4 O3 77.99(17) . . ? N15 Cu4 N13 94.2(2) . . ? O4 Cu4 N13 93.9(2) . . ? O3 Cu4 N13 170.0(2) . . ? N15 Cu4 O2 103.88(17) . . ? O4 Cu4 O2 82.30(15) . . ? O3 Cu4 O2 81.66(15) . . ? N13 Cu4 O2 103.28(18) . . ? N15 Cu4 Cu2 131.00(15) . . ? O4 Cu4 Cu2 39.07(12) . . ? O3 Cu4 Cu2 39.23(12) . . ? N13 Cu4 Cu2 131.88(16) . . ? O2 Cu4 Cu2 83.43(10) . . ? C1 N1 N2 105.5(5) . . ? C1 N1 Cu1 130.7(4) . . ? N2 N1 Cu1 123.4(4) . . ? C3 N2 N1 111.6(5) . . ? C3 N2 H2 124.2 . . ? N1 N2 H2 124.2 . . ? C7 N3 N4 105.2(6) . . ? C7 N3 Cu1 130.9(5) . . ? N4 N3 Cu1 123.8(4) . . ? C9 N4 N3 112.1(6) . . ? C9 N4 H4 124.0 . . ? N3 N4 H4 124.0 . . ? C15 N5 N6 106.1(5) . . ? C15 N5 Cu2 129.0(5) . . ? N6 N5 Cu2 124.8(4) . . ? C13 N6 N5 110.8(6) . . ? C13 N6 H6 124.6 . . ? N5 N6 H6 124.6 . . ? C19 N7 N8 105.9(6) . . ? C19 N7 Cu2 127.9(5) . . ? N8 N7 Cu2 126.1(5) . . ? C21 N8 N7 111.0(7) . . ? C21 N8 H8 124.5 . . ? N7 N8 H8 124.5 . . ? C25 N9 N10 105.3(5) . . ? C25 N9 Cu3 129.0(4) . . ? N10 N9 Cu3 125.7(4) . . ? C27 N10 N9 111.7(6) . . ? C27 N10 H10 124.2 . . ? N9 N10 H10 124.2 . . ? N12 N11 C31 104.9(5) . . ? N12 N11 Cu3 124.8(4) . . ? C31 N11 Cu3 130.1(5) . . ? C33 N12 N11 111.6(5) . . ? C33 N12 H12 124.2 . . ? N11 N12 H12 124.2 . . ? C37 N13 N14 105.5(5) . . ? C37 N13 Cu4 129.9(5) . . ? N14 N13 Cu4 124.5(4) . . ? C39 N14 N13 112.3(6) . . ? C39 N14 H14 123.9 . . ? N13 N14 H14 123.9 . . ? N16 N15 C43 105.0(5) . . ? N16 N15 Cu4 125.2(4) . . ? C43 N15 Cu4 129.8(4) . . ? C45 N16 N15 112.7(5) . . ? C45 N16 H16 123.7 . . ? N15 N16 H16 123.7 . . ? Cu3 O1 Cu1 102.8(2) . . ? Cu3 O1 Cu2 96.59(16) . . ? Cu1 O1 Cu2 97.11(16) . . ? Cu3 O1 H1 118.7 . . ? Cu1 O1 H1 118.7 . . ? Cu2 O1 H1 118.7 . . ? Cu1 O2 Cu3 101.86(18) . . ? Cu1 O2 Cu4 96.55(14) . . ? Cu3 O2 Cu4 96.45(16) . . ? Cu1 O2 H2A 119.1 . . ? Cu3 O2 H2A 119.1 . . ? Cu4 O2 H2A 119.1 . . ? Cu4 O3 Cu2 101.54(19) . . ? Cu4 O3 Cu1 97.05(16) . . ? Cu2 O3 Cu1 98.61(17) . . ? Cu4 O3 H3 118.5 . . ? Cu2 O3 H3 118.5 . . ? Cu1 O3 H3 118.5 . . ? Cu4 O4 Cu2 101.87(18) . . ? Cu4 O4 Cu3 97.09(16) . . ? Cu2 O4 Cu3 97.21(17) . . ? Cu4 O4 H4D 118.8 . . ? Cu2 O4 H4D 118.8 . . ? Cu3 O4 H4D 118.8 . . ? O5 Cl1 O8 113.0(4) . . ? O5 Cl1 O7 109.2(4) . . ? O8 Cl1 O7 109.1(4) . . ? O5 Cl1 O6 109.1(3) . . ? O8 Cl1 O6 109.2(3) . . ? O7 Cl1 O6 107.0(4) . . ? O12 Cl2 O9 112.5(8) . . ? O12 Cl2 O10 111.3(9) . . ? O9 Cl2 O10 105.3(7) . . ? O12 Cl2 O11 109.9(5) . . ? O9 Cl2 O11 109.1(4) . . ? O10 Cl2 O11 108.6(5) . . ? O15 Cl3 O13 110.6 . . ? O15 Cl3 O14 112.5 . . ? O13 Cl3 O14 110.0 . . ? O15 Cl3 O16 109.5 . . ? O13 Cl3 O16 108.4 . . ? O14 Cl3 O16 105.6 . . ? O19 Cl4 O17 110.6 . . ? O19 Cl4 O18 112.5 . . ? O17 Cl4 O18 110.0 . . ? O19 Cl4 O20 109.5 . . ? O17 Cl4 O20 108.4 . . ? O18 Cl4 O20 105.6 . . ? 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 1.3(7) . . . . ? C4 C1 C2 C3 -177.3(6) . . . . ? N1 C1 C2 C5 -178.9(6) . . . . ? C4 C1 C2 C5 2.6(11) . . . . ? C1 C2 C3 N2 -1.4(7) . . . . ? C5 C2 C3 N2 178.8(6) . . . . ? C1 C2 C3 C6 -179.7(7) . . . . ? C5 C2 C3 C6 0.5(11) . . . . ? N3 C7 C8 C9 -0.7(10) . . . . ? C10 C7 C8 C9 179.0(8) . . . . ? N3 C7 C8 C11 177.9(9) . . . . ? C10 C7 C8 C11 -2.4(15) . . . . ? C7 C8 C9 N4 0.4(10) . . . . ? C11 C8 C9 N4 -178.1(10) . . . . ? C7 C8 C9 C12 -179.3(11) . . . . ? C11 C8 C9 C12 2.2(19) . . . . ? N6 C13 C14 C15 -0.3(9) . . . . ? C16 C13 C14 C15 -177.9(9) . . . . ? N6 C13 C14 C17 -178.7(8) . . . . ? C16 C13 C14 C17 3.6(16) . . . . ? C13 C14 C15 N5 -0.6(8) . . . . ? C17 C14 C15 N5 178.0(8) . . . . ? C13 C14 C15 C18 176.9(8) . . . . ? C17 C14 C15 C18 -4.6(13) . . . . ? N7 C19 C20 C21 0.9(9) . . . . ? C22 C19 C20 C21 -178.4(7) . . . . ? N7 C19 C20 C23 -178.9(8) . . . . ? C22 C19 C20 C23 1.7(14) . . . . ? C19 C20 C21 N8 -0.9(9) . . . . ? C23 C20 C21 N8 179.0(8) . . . . ? C19 C20 C21 C24 178.1(9) . . . . ? C23 C20 C21 C24 -2.0(15) . . . . ? N9 C25 C26 C27 2.0(9) . . . . ? C28 C25 C26 C27 -178.2(8) . . . . ? N9 C25 C26 C29 -179.4(8) . . . . ? C28 C25 C26 C29 0.4(13) . . . . ? C25 C26 C27 N10 -1.4(9) . . . . ? C29 C26 C27 N10 -179.9(8) . . . . ? C25 C26 C27 C30 177.7(9) . . . . ? C29 C26 C27 C30 -0.9(15) . . . . ? N11 C31 C32 C33 0.5(9) . . . . ? C34 C31 C32 C33 178.7(8) . . . . ? N11 C31 C32 C35 179.3(9) . . . . ? C34 C31 C32 C35 -2.6(14) . . . . ? C31 C32 C33 N12 -0.6(9) . . . . ? C35 C32 C33 N12 -179.3(9) . . . . ? C31 C32 C33 C36 -178.3(9) . . . . ? C35 C32 C33 C36 2.9(16) . . . . ? N13 C37 C38 C39 0.0(8) . . . . ? C40 C37 C38 C39 177.9(7) . . . . ? N13 C37 C38 C41 176.8(8) . . . . ? C40 C37 C38 C41 -5.2(13) . . . . ? C37 C38 C39 N14 0.2(8) . . . . ? C41 C38 C39 N14 -176.6(8) . . . . ? C37 C38 C39 C42 -179.0(9) . . . . ? C41 C38 C39 C42 4.2(15) . . . . ? N15 C43 C44 C45 0.8(8) . . . . ? C46 C43 C44 C45 -178.9(7) . . . . ? N15 C43 C44 C47 178.5(7) . . . . ? C46 C43 C44 C47 -1.1(12) . . . . ? C43 C44 C45 N16 -1.1(7) . . . . ? C47 C44 C45 N16 -178.8(7) . . . . ? C43 C44 C45 C48 -179.7(8) . . . . ? C47 C44 C45 C48 2.6(13) . . . . ? N7 Cu2 Cu4 N15 145.7(3) . . . . ? O4 Cu2 Cu4 N15 171.4(3) . . . . ? O3 Cu2 Cu4 N15 -17.9(3) . . . . ? N5 Cu2 Cu4 N15 -5.0(3) . . . . ? O1 Cu2 Cu4 N15 -102.5(2) . . . . ? N7 Cu2 Cu4 O4 -25.7(3) . . . . ? O3 Cu2 Cu4 O4 170.7(3) . . . . ? N5 Cu2 Cu4 O4 -176.4(3) . . . . ? O1 Cu2 Cu4 O4 86.0(2) . . . . ? N7 Cu2 Cu4 O3 163.6(3) . . . . ? O4 Cu2 Cu4 O3 -170.7(3) . . . . ? N5 Cu2 Cu4 O3 12.8(3) . . . . ? O1 Cu2 Cu4 O3 -84.7(2) . . . . ? N7 Cu2 Cu4 N13 -9.6(3) . . . . ? O4 Cu2 Cu4 N13 16.1(3) . . . . ? O3 Cu2 Cu4 N13 -173.2(3) . . . . ? N5 Cu2 Cu4 N13 -160.4(3) . . . . ? O1 Cu2 Cu4 N13 102.1(2) . . . . ? N7 Cu2 Cu4 O2 -111.6(2) . . . . ? O4 Cu2 Cu4 O2 -85.9(2) . . . . ? O3 Cu2 Cu4 O2 84.9(2) . . . . ? N5 Cu2 Cu4 O2 97.7(2) . . . . ? O1 Cu2 Cu4 O2 0.17(14) . . . . ? C2 C1 N1 N2 -0.6(7) . . . . ? C4 C1 N1 N2 178.0(5) . . . . ? C2 C1 N1 Cu1 -174.0(4) . . . . ? C4 C1 N1 Cu1 4.6(9) . . . . ? N3 Cu1 N1 C1 99.1(6) . . . . ? O2 Cu1 N1 C1 -70.2(5) . . . . ? O3 Cu1 N1 C1 -153.4(5) . . . . ? N3 Cu1 N1 N2 -73.3(5) . . . . ? O2 Cu1 N1 N2 117.4(4) . . . . ? O3 Cu1 N1 N2 34.2(5) . . . . ? C2 C3 N2 N1 1.1(7) . . . . ? C6 C3 N2 N1 179.6(5) . . . . ? C1 N1 N2 C3 -0.3(7) . . . . ? Cu1 N1 N2 C3 173.7(4) . . . . ? C8 C7 N3 N4 0.7(8) . . . . ? C10 C7 N3 N4 -179.1(7) . . . . ? C8 C7 N3 Cu1 179.1(5) . . . . ? C10 C7 N3 Cu1 -0.7(11) . . . . ? O2 Cu1 N3 C7 19.3(13) . . . . ? O1 Cu1 N3 C7 68.1(6) . . . . ? N1 Cu1 N3 C7 -107.5(6) . . . . ? O3 Cu1 N3 C7 150.6(6) . . . . ? O2 Cu1 N3 N4 -162.5(7) . . . . ? O1 Cu1 N3 N4 -113.7(5) . . . . ? N1 Cu1 N3 N4 70.7(5) . . . . ? O3 Cu1 N3 N4 -31.2(6) . . . . ? C8 C9 N4 N3 0.0(10) . . . . ? C12 C9 N4 N3 179.7(8) . . . . ? C7 N3 N4 C9 -0.4(8) . . . . ? Cu1 N3 N4 C9 -179.0(6) . . . . ? C14 C15 N5 N6 1.1(7) . . . . ? C18 C15 N5 N6 -176.6(6) . . . . ? C14 C15 N5 Cu2 176.8(5) . . . . ? C18 C15 N5 Cu2 -0.9(9) . . . . ? N7 Cu2 N5 C15 -94.6(6) . . . . ? O3 Cu2 N5 C15 71.3(6) . . . . ? O1 Cu2 N5 C15 152.3(5) . . . . ? Cu4 Cu2 N5 C15 63.2(6) . . . . ? N7 Cu2 N5 N6 80.4(5) . . . . ? O3 Cu2 N5 N6 -113.8(5) . . . . ? O1 Cu2 N5 N6 -32.7(5) . . . . ? Cu4 Cu2 N5 N6 -121.9(5) . . . . ? C14 C13 N6 N5 1.0(9) . . . . ? C16 C13 N6 N5 178.9(8) . . . . ? C15 N5 N6 C13 -1.3(8) . . . . ? Cu2 N5 N6 C13 -177.2(5) . . . . ? C20 C19 N7 N8 -0.6(8) . . . . ? C22 C19 N7 N8 178.8(7) . . . . ? C20 C19 N7 Cu2 -177.5(5) . . . . ? C22 C19 N7 Cu2 1.9(10) . . . . ? O4 Cu2 N7 C19 -69.5(6) . . . . ? O3 Cu2 N7 C19 -13.4(12) . . . . ? N5 Cu2 N7 C19 105.4(6) . . . . ? O1 Cu2 N7 C19 -151.3(6) . . . . ? Cu4 Cu2 N7 C19 -53.6(7) . . . . ? O4 Cu2 N7 N8 114.2(5) . . . . ? O3 Cu2 N7 N8 170.2(6) . . . . ? N5 Cu2 N7 N8 -71.0(6) . . . . ? O1 Cu2 N7 N8 32.3(6) . . . . ? Cu4 Cu2 N7 N8 130.1(5) . . . . ? C20 C21 N8 N7 0.6(9) . . . . ? C24 C21 N8 N7 -178.6(7) . . . . ? C19 N7 N8 C21 0.0(8) . . . . ? Cu2 N7 N8 C21 177.0(5) . . . . ? C26 C25 N9 N10 -1.8(8) . . . . ? C28 C25 N9 N10 178.4(6) . . . . ? C26 C25 N9 Cu3 -179.6(5) . . . . ? C28 C25 N9 Cu3 0.6(10) . . . . ? O1 Cu3 N9 C25 -69.7(6) . . . . ? N11 Cu3 N9 C25 103.5(6) . . . . ? O2 Cu3 N9 C25 -25.2(12) . . . . ? O4 Cu3 N9 C25 -152.7(6) . . . . ? O1 Cu3 N9 N10 112.9(5) . . . . ? N11 Cu3 N9 N10 -73.9(5) . . . . ? O2 Cu3 N9 N10 157.4(6) . . . . ? O4 Cu3 N9 N10 29.9(5) . . . . ? C26 C27 N10 N9 0.3(9) . . . . ? C30 C27 N10 N9 -178.8(7) . . . . ? C25 N9 N10 C27 0.9(8) . . . . ? Cu3 N9 N10 C27 178.9(5) . . . . ? C32 C31 N11 N12 -0.3(8) . . . . ? C34 C31 N11 N12 -178.6(6) . . . . ? C32 C31 N11 Cu3 175.7(5) . . . . ? C34 C31 N11 Cu3 -2.6(10) . . . . ? O2 Cu3 N11 N12 -117.7(5) . . . . ? N9 Cu3 N11 N12 72.6(5) . . . . ? O4 Cu3 N11 N12 -34.7(5) . . . . ? O2 Cu3 N11 C31 67.0(6) . . . . ? N9 Cu3 N11 C31 -102.7(6) . . . . ? O4 Cu3 N11 C31 150.0(6) . . . . ? C32 C33 N12 N11 0.4(9) . . . . ? C36 C33 N12 N11 178.5(8) . . . . ? C31 N11 N12 C33 -0.1(8) . . . . ? Cu3 N11 N12 C33 -176.4(5) . . . . ? C38 C37 N13 N14 -0.2(7) . . . . ? C40 C37 N13 N14 -178.3(6) . . . . ? C38 C37 N13 Cu4 -178.2(5) . . . . ? C40 C37 N13 Cu4 3.7(10) . . . . ? N15 Cu4 N13 C37 -108.5(6) . . . . ? O4 Cu4 N13 C37 63.1(6) . . . . ? O3 Cu4 N13 C37 27.6(15) . . . . ? O2 Cu4 N13 C37 146.1(6) . . . . ? Cu2 Cu4 N13 C37 53.0(6) . . . . ? N15 Cu4 N13 N14 73.8(5) . . . . ? O4 Cu4 N13 N14 -114.5(5) . . . . ? O3 Cu4 N13 N14 -150.1(9) . . . . ? O2 Cu4 N13 N14 -31.5(5) . . . . ? Cu2 Cu4 N13 N14 -124.6(5) . . . . ? C38 C39 N14 N13 -0.4(9) . . . . ? C42 C39 N14 N13 179.0(7) . . . . ? C37 N13 N14 C39 0.3(8) . . . . ? Cu4 N13 N14 C39 178.5(5) . . . . ? C44 C43 N15 N16 -0.1(7) . . . . ? C46 C43 N15 N16 179.5(6) . . . . ? C44 C43 N15 Cu4 -178.5(4) . . . . ? C46 C43 N15 Cu4 1.2(9) . . . . ? O4 Cu4 N15 N16 156.7(8) . . . . ? O3 Cu4 N15 N16 117.5(5) . . . . ? N13 Cu4 N15 N16 -69.4(5) . . . . ? O2 Cu4 N15 N16 35.4(5) . . . . ? Cu2 Cu4 N15 N16 128.7(4) . . . . ? O4 Cu4 N15 C43 -25.3(13) . . . . ? O3 Cu4 N15 C43 -64.4(5) . . . . ? N13 Cu4 N15 C43 108.6(5) . . . . ? O2 Cu4 N15 C43 -146.6(5) . . . . ? Cu2 Cu4 N15 C43 -53.2(6) . . . . ? C44 C45 N16 N15 1.1(8) . . . . ? C48 C45 N16 N15 179.9(6) . . . . ? C43 N15 N16 C45 -0.6(7) . . . . ? Cu4 N15 N16 C45 177.8(4) . . . . ? O2 Cu3 O1 Cu1 -4.32(16) . . . . ? N9 Cu3 O1 Cu1 166.2(2) . . . . ? O4 Cu3 O1 Cu1 -87.93(18) . . . . ? O2 Cu3 O1 Cu2 94.54(16) . . . . ? N9 Cu3 O1 Cu2 -94.94(18) . . . . ? O4 Cu3 O1 Cu2 10.93(14) . . . . ? N3 Cu1 O1 Cu3 -165.3(2) . . . . ? O2 Cu1 O1 Cu3 4.36(17) . . . . ? O3 Cu1 O1 Cu3 88.41(18) . . . . ? N3 Cu1 O1 Cu2 96.2(2) . . . . ? O2 Cu1 O1 Cu2 -94.09(17) . . . . ? O3 Cu1 O1 Cu2 -10.04(15) . . . . ? N7 Cu2 O1 Cu3 77.0(2) . . . . ? O4 Cu2 O1 Cu3 -12.91(17) . . . . ? O3 Cu2 O1 Cu3 -92.10(18) . . . . ? N5 Cu2 O1 Cu3 175.4(2) . . . . ? Cu4 Cu2 O1 Cu3 -52.40(13) . . . . ? N7 Cu2 O1 Cu1 -179.1(2) . . . . ? O4 Cu2 O1 Cu1 90.94(18) . . . . ? O3 Cu2 O1 Cu1 11.75(17) . . . . ? N5 Cu2 O1 Cu1 -80.8(2) . . . . ? Cu4 Cu2 O1 Cu1 51.44(13) . . . . ? N3 Cu1 O2 Cu3 46.0(9) . . . . ? O1 Cu1 O2 Cu3 -4.28(16) . . . . ? N1 Cu1 O2 Cu3 172.58(18) . . . . ? O3 Cu1 O2 Cu3 -87.49(17) . . . . ? N3 Cu1 O2 Cu4 144.0(8) . . . . ? O1 Cu1 O2 Cu4 93.75(17) . . . . ? N1 Cu1 O2 Cu4 -89.40(18) . . . . ? O3 Cu1 O2 Cu4 10.54(15) . . . . ? O1 Cu3 O2 Cu1 4.32(16) . . . . ? N11 Cu3 O2 Cu1 -170.07(19) . . . . ? N9 Cu3 O2 Cu1 -41.5(9) . . . . ? O4 Cu3 O2 Cu1 88.29(17) . . . . ? O1 Cu3 O2 Cu4 -93.79(16) . . . . ? N11 Cu3 O2 Cu4 91.82(19) . . . . ? N9 Cu3 O2 Cu4 -139.6(8) . . . . ? O4 Cu3 O2 Cu4 -9.81(14) . . . . ? N15 Cu4 O2 Cu1 78.8(2) . . . . ? O4 Cu4 O2 Cu1 -91.22(18) . . . . ? O3 Cu4 O2 Cu1 -12.31(17) . . . . ? N13 Cu4 O2 Cu1 176.60(19) . . . . ? Cu2 Cu4 O2 Cu1 -51.85(13) . . . . ? N15 Cu4 O2 Cu3 -178.40(18) . . . . ? O4 Cu4 O2 Cu3 11.55(16) . . . . ? O3 Cu4 O2 Cu3 90.46(18) . . . . ? N13 Cu4 O2 Cu3 -80.6(2) . . . . ? Cu2 Cu4 O2 Cu3 50.92(12) . . . . ? N15 Cu4 O3 Cu2 166.60(19) . . . . ? O4 Cu4 O3 Cu2 -5.97(17) . . . . ? N13 Cu4 O3 Cu2 30.4(12) . . . . ? O2 Cu4 O3 Cu2 -89.81(17) . . . . ? N15 Cu4 O3 Cu1 -93.07(19) . . . . ? O4 Cu4 O3 Cu1 94.36(17) . . . . ? N13 Cu4 O3 Cu1 130.7(11) . . . . ? O2 Cu4 O3 Cu1 10.52(15) . . . . ? Cu2 Cu4 O3 Cu1 100.3(2) . . . . ? N7 Cu2 O3 Cu4 -51.9(8) . . . . ? O4 Cu2 O3 Cu4 5.96(17) . . . . ? N5 Cu2 O3 Cu4 -170.6(2) . . . . ? O1 Cu2 O3 Cu4 88.98(17) . . . . ? N7 Cu2 O3 Cu1 -151.0(7) . . . . ? O4 Cu2 O3 Cu1 -93.10(17) . . . . ? N5 Cu2 O3 Cu1 90.3(2) . . . . ? O1 Cu2 O3 Cu1 -10.09(15) . . . . ? Cu4 Cu2 O3 Cu1 -99.1(2) . . . . ? N3 Cu1 O3 Cu4 177.7(2) . . . . ? O2 Cu1 O3 Cu4 -12.43(17) . . . . ? O1 Cu1 O3 Cu4 -90.85(19) . . . . ? N1 Cu1 O3 Cu4 81.4(2) . . . . ? N3 Cu1 O3 Cu2 -79.4(2) . . . . ? O2 Cu1 O3 Cu2 90.43(19) . . . . ? O1 Cu1 O3 Cu2 12.01(18) . . . . ? N1 Cu1 O3 Cu2 -175.69(19) . . . . ? N15 Cu4 O4 Cu2 -34.1(10) . . . . ? O3 Cu4 O4 Cu2 5.99(17) . . . . ? N13 Cu4 O4 Cu2 -168.1(2) . . . . ? O2 Cu4 O4 Cu2 89.04(17) . . . . ? N15 Cu4 O4 Cu3 -133.1(9) . . . . ? O3 Cu4 O4 Cu3 -92.95(17) . . . . ? N13 Cu4 O4 Cu3 93.00(19) . . . . ? O2 Cu4 O4 Cu3 -9.90(14) . . . . ? Cu2 Cu4 O4 Cu3 -98.9(2) . . . . ? N7 Cu2 O4 Cu4 160.4(2) . . . . ? O3 Cu2 O4 Cu4 -5.99(17) . . . . ? O1 Cu2 O4 Cu4 -87.96(18) . . . . ? N7 Cu2 O4 Cu3 -100.8(2) . . . . ? O3 Cu2 O4 Cu3 92.85(16) . . . . ? O1 Cu2 O4 Cu3 10.88(14) . . . . ? Cu4 Cu2 O4 Cu3 98.8(2) . . . . ? O1 Cu3 O4 Cu4 89.91(18) . . . . ? N11 Cu3 O4 Cu4 -81.6(2) . . . . ? O2 Cu3 O4 Cu4 11.61(17) . . . . ? N9 Cu3 O4 Cu4 -178.98(19) . . . . ? O1 Cu3 O4 Cu2 -13.08(17) . . . . ? N11 Cu3 O4 Cu2 175.4(2) . . . . ? O2 Cu3 O4 Cu2 -91.38(17) . . . . ? N9 Cu3 O4 Cu2 78.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.35 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.737 _refine_diff_density_min -1.021 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 945309'