# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '8949_web_deposit_cif_file_0_AdailtonJ.Bortoluzzi_1326032854.complex_2.cif' _audit_creation_method 'SHELXL97 and manual editing' #======================================================================= # 1. SUBMISSION DETAILS _publ_contact_author_name 'Ademir Neves' _publ_contact_author_address ; Depto. de Qu\'imica - UFSC 88040 - 900 Florian\'opolis, SC Brazil ; _publ_contact_author_email ademir.neves@ufsc.br _publ_contact_author_fax 55(48)37216888 _publ_contact_author_phone 55(48)37216844 _publ_contact_letter ; ? ; #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Doubly Phenoxo/Hydroxo-bridged Dicopper(II) Complexes: Individual Contributions of the Bridges to the Antiferromagnetic Coupling Based on two Related Biomimetic Models for Catechol Oxidases ; loop_ _publ_author_name _publ_author_address A.Neves ; Depto. de Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; N.Rey ; Depto. de Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; A.J.Bortoluzzi ; Depto. de Qu\'imica - UFSC 88040-900 - Florian\'opolis, SC Brazil ; W.Haase ; Institut f\"ur Physikalische Chemie Technische Universit\"at Darmstadt Petersenstrasse, 20 D-64287 - Darmstadt Germany ; Z.Tomkowicz ; Institut f\"ur Physikalische Chemie Technische Universit\"at Darmstadt Petersenstrasse, 20 D-64287 - Darmstadt Germany ; #======================================================================= data_complex(2) _database_code_depnum_ccdc_archive 'CCDC 861493' #TrackingRef '8949_web_deposit_cif_file_0_AdailtonJ.Bortoluzzi_1326032854.complex_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H34 Cu2 N6 O2, 2(Cl O4)' _chemical_formula_sum 'C27 H34 Cl2 Cu2 N6 O10' _chemical_formula_weight 800.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.607(1) _cell_length_b 11.022(2) _cell_length_c 17.330(1) _cell_angle_alpha 90.00 _cell_angle_beta 91.561(5) _cell_angle_gamma 90.00 _cell_volume 3170.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.88 _cell_measurement_theta_max 13.47 _exptl_crystal_description 'irregular plate' _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 1.576 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.5063 _exptl_absorpt_correction_T_max 0.8214 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 5829 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.07 _reflns_number_total 5633 _reflns_number_gt 3680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0452P)^2^+12.3531P] 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 5633 _refine_ls_number_parameters 451 _refine_ls_number_restraints 177 _refine_ls_R_factor_all 0.1118 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.154 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.15529(5) 0.38758(7) 1.02043(4) 0.0342(2) Uani 1 1 d . . . Cu2 Cu 0.24678(5) 0.54676(7) 0.91038(4) 0.0376(2) Uani 1 1 d . . . O1 O 0.2117(3) 0.3816(4) 0.9250(3) 0.0473(12) Uani 1 1 d . . . H1 H 0.2414 0.3243 0.8953 0.057 Uiso 1 1 d R . . O10 O 0.1550(3) 0.5621(4) 1.0040(2) 0.0338(10) Uani 1 1 d . . . N1 N 0.1242(3) 0.4079(5) 1.1265(3) 0.0326(12) Uani 1 1 d . . . C2 C 0.1256(4) 0.5041(6) 1.1659(4) 0.0357(15) Uani 1 1 d . . . H2 H 0.1069 0.5003 1.2159 0.043 Uiso 1 1 calc R . . C3 C 0.2030(4) 0.7923(6) 0.9552(3) 0.0365(15) Uani 1 1 d . . . H3A H 0.2125 0.8789 0.9517 0.044 Uiso 1 1 calc R . . H3B H 0.1511 0.7763 0.9302 0.044 Uiso 1 1 calc R . . N4 N 0.2666(3) 0.7286(5) 0.9093(3) 0.0362(13) Uani 1 1 d . . . C5 C 0.2017(5) 0.9253(6) 1.2332(4) 0.053(2) Uani 1 1 d . . . H5A H 0.2209 0.9981 1.2094 0.080 Uiso 1 1 calc R . . H5B H 0.2396 0.9000 1.2729 0.080 Uiso 1 1 calc R . . H5C H 0.1505 0.9408 1.2555 0.080 Uiso 1 1 calc R . . C11 C 0.1545(4) 0.6206(5) 1.1384(3) 0.0324(14) Uani 1 1 d . . . C12 C 0.1696(4) 0.6431(5) 1.0591(3) 0.0286(13) Uani 1 1 d . . . C13 C 0.1969(4) 0.7604(5) 1.0390(3) 0.0314(14) Uani 1 1 d . . . C14 C 0.2093(4) 0.8466(6) 1.0956(4) 0.0376(15) Uani 1 1 d . . . H14 H 0.2297 0.9217 1.0814 0.045 Uiso 1 1 calc R . . C15 C 0.1929(4) 0.8269(6) 1.1734(4) 0.0375(15) Uani 1 1 d . . . C16 C 0.1654(4) 0.7138(6) 1.1927(4) 0.0385(16) Uani 1 1 d . . . H16 H 0.1535 0.6983 1.2439 0.046 Uiso 1 1 calc R . . C21 C 0.0867(4) 0.2933(6) 1.1524(4) 0.0397(16) Uani 1 1 d . . . C22 C 0.1432(4) 0.1931(6) 1.1270(4) 0.0410(16) Uani 1 1 d . . . H22A H 0.1921 0.1952 1.1588 0.049 Uiso 1 1 calc R . . H22B H 0.1177 0.1149 1.1344 0.049 Uiso 1 1 calc R . . N23 N 0.1639(3) 0.2071(5) 1.0443(3) 0.0404(13) Uani 1 1 d . . . H23 H 0.2189 0.1759 1.0381 0.048 Uiso 1 1 d R . . C24 C 0.1115(5) 0.1352(7) 0.9906(5) 0.061(2) Uani 1 1 d . . . H24A H 0.1094 0.0520 1.0086 0.073 Uiso 1 1 calc R . . H24B H 0.1348 0.1349 0.9399 0.073 Uiso 1 1 calc R . . C25 C 0.0264(5) 0.1854(8) 0.9841(5) 0.070(2) Uani 1 1 d . . . H25A H 0.0120 0.1971 0.9300 0.084 Uiso 1 1 calc R . . H25B H -0.0105 0.1264 1.0048 0.084 Uiso 1 1 calc R . . N26 N 0.0167(4) 0.3002(5) 1.0247(4) 0.0499(15) Uani 1 1 d . . . H26 H -0.0215 0.3381 0.9951 0.09(3) Uiso 1 1 d R . . C27 C 0.0064(4) 0.2885(7) 1.1073(4) 0.0516(19) Uani 1 1 d . . . H27A H -0.0202 0.2122 1.1178 0.062 Uiso 1 1 calc R . . H27B H -0.0280 0.3535 1.1248 0.062 Uiso 1 1 calc R . . C28 C 0.0740(5) 0.2830(7) 1.2389(4) 0.061(2) Uani 1 1 d . . . H28A H 0.0386 0.3464 1.2549 0.092 Uiso 1 1 calc R . . H28B H 0.1249 0.2905 1.2661 0.092 Uiso 1 1 calc R . . H28C H 0.0506 0.2055 1.2501 0.092 Uiso 1 1 calc R . . C30 C 0.3483(4) 0.7538(6) 0.9423(4) 0.0435(17) Uani 1 1 d . . . H30A H 0.3480 0.8309 0.9694 0.052 Uiso 1 1 calc R . . H30B H 0.3863 0.7596 0.9010 0.052 Uiso 1 1 calc R . . C31 C 0.3743(4) 0.6542(6) 0.9976(4) 0.0374(16) Uani 1 1 d . . . N32 N 0.3393(3) 0.5461(5) 0.9861(3) 0.0369(13) Uani 1 1 d . . . C33 C 0.3660(5) 0.4525(7) 1.0289(4) 0.0488(18) Uani 1 1 d . . . H33 H 0.3430 0.3766 1.0204 0.059 Uiso 1 1 calc R . . C34 C 0.4260(5) 0.4634(8) 1.0846(4) 0.057(2) Uani 1 1 d . . . H34 H 0.4434 0.3962 1.1130 0.068 Uiso 1 1 calc R . . C35 C 0.4593(5) 0.5746(8) 1.0974(4) 0.059(2) Uani 1 1 d . . . H35 H 0.4994 0.5846 1.1353 0.071 Uiso 1 1 calc R . . C36 C 0.4334(4) 0.6719(8) 1.0540(4) 0.0526(19) Uani 1 1 d . . . H36 H 0.4553 0.7486 1.0624 0.063 Uiso 1 1 calc R . . C40 C 0.2571(4) 0.7692(6) 0.8278(4) 0.0461(18) Uani 1 1 d . . . H40A H 0.3089 0.7660 0.8033 0.055 Uiso 1 1 calc R . . H40B H 0.2385 0.8526 0.8266 0.055 Uiso 1 1 calc R . . C41 C 0.1975(4) 0.6900(7) 0.7834(4) 0.0489(19) Uani 1 1 d . . . N42 N 0.1850(3) 0.5794(5) 0.8127(3) 0.0445(14) Uani 1 1 d . . . C43 C 0.1375(5) 0.5016(8) 0.7728(5) 0.058(2) Uani 1 1 d . . . H43 H 0.1285 0.4250 0.7933 0.069 Uiso 1 1 calc R . . C44 C 0.1016(6) 0.5313(10) 0.7024(5) 0.077(3) Uani 1 1 d . . . H44 H 0.0688 0.4762 0.6757 0.092 Uiso 1 1 calc R . . C45 C 0.1162(6) 0.6466(11) 0.6727(5) 0.085(3) Uani 1 1 d . . . H45 H 0.0939 0.6686 0.6249 0.102 Uiso 1 1 calc R . . C46 C 0.1636(5) 0.7282(10) 0.7138(5) 0.070(3) Uani 1 1 d . . . H46 H 0.1725 0.8062 0.6954 0.084 Uiso 1 1 calc R . . Cl1 Cl 0.40830(13) 0.5707(2) 0.72700(12) 0.0622(6) Uani 1 1 d D . . O1P O 0.3837(4) 0.5398(6) 0.8029(3) 0.094(2) Uani 1 1 d D . . O2P O 0.3357(8) 0.570(3) 0.6823(9) 0.141(8) Uani 0.52(2) 1 d PDU . . O2P' O 0.3676(17) 0.4920(19) 0.6738(8) 0.131(9) Uani 0.48(2) 1 d PDU . . O3P O 0.4394(15) 0.6858(14) 0.7314(12) 0.143(10) Uani 0.52(2) 1 d PDU . . O3P' O 0.3886(15) 0.6888(12) 0.7047(11) 0.099(8) Uani 0.48(2) 1 d PDU . . O4P O 0.4590(14) 0.4891(15) 0.6972(10) 0.117(8) Uani 0.52(2) 1 d PDU . . O4P' O 0.4917(8) 0.551(3) 0.7218(12) 0.129(9) Uani 0.48(2) 1 d PDU . . Cl2 Cl 0.11156(12) 0.59281(17) 0.42884(11) 0.0537(5) Uani 1 1 d D . . O5P O 0.1620(4) 0.6691(7) 0.3862(4) 0.111(3) Uani 1 1 d D . . O6P O 0.0954(7) 0.4928(11) 0.3813(7) 0.110(5) Uiso 0.69(3) 1 d PDU . . O6P' O 0.1019(12) 0.4700(12) 0.4104(14) 0.072(8) Uiso 0.31(3) 1 d PDU . . O7P O 0.1651(6) 0.5611(10) 0.4939(5) 0.084(4) Uiso 0.69(3) 1 d PDU . . O7P' O 0.1395(15) 0.598(3) 0.5075(9) 0.22(2) Uiso 0.31(3) 1 d PDU . . O8P O 0.0461(6) 0.6500(10) 0.4586(8) 0.109(5) Uiso 0.69(3) 1 d PDU . . O8P' O 0.0332(9) 0.6494(17) 0.4224(16) 0.088(9) Uiso 0.31(3) 1 d PDU . . 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 0.0417(5) 0.0267(4) 0.0342(4) 0.0008(3) 0.0025(3) -0.0024(4) Cu2 0.0487(5) 0.0308(4) 0.0337(4) 0.0010(4) 0.0052(3) 0.0005(4) O1 0.066(3) 0.033(3) 0.044(3) -0.009(2) 0.016(2) -0.001(2) O10 0.047(3) 0.026(2) 0.029(2) 0.0019(18) 0.0037(19) -0.002(2) N1 0.036(3) 0.029(3) 0.034(3) 0.005(2) 0.003(2) -0.007(2) C2 0.037(4) 0.037(4) 0.033(3) 0.004(3) 0.002(3) -0.002(3) C3 0.043(4) 0.030(3) 0.037(4) 0.006(3) 0.004(3) 0.001(3) N4 0.041(3) 0.032(3) 0.035(3) 0.007(2) 0.006(2) 0.003(2) C5 0.078(6) 0.038(4) 0.043(4) -0.007(3) -0.008(4) 0.003(4) C11 0.041(4) 0.025(3) 0.030(3) 0.001(3) 0.000(3) -0.003(3) C12 0.030(3) 0.025(3) 0.030(3) -0.003(3) 0.001(3) 0.004(3) C13 0.031(3) 0.027(3) 0.036(3) 0.005(3) 0.003(3) 0.002(3) C14 0.041(4) 0.025(3) 0.047(4) 0.003(3) -0.001(3) -0.002(3) C15 0.044(4) 0.033(4) 0.035(4) -0.005(3) -0.005(3) 0.003(3) C16 0.049(4) 0.036(4) 0.030(3) -0.001(3) 0.001(3) 0.000(3) C21 0.043(4) 0.035(4) 0.042(4) 0.010(3) 0.005(3) -0.007(3) C22 0.045(4) 0.031(4) 0.047(4) 0.007(3) -0.001(3) -0.003(3) N23 0.046(3) 0.026(3) 0.050(3) 0.004(2) 0.003(3) 0.002(3) C24 0.083(6) 0.040(4) 0.058(5) -0.010(4) -0.008(4) -0.003(4) C25 0.064(6) 0.066(6) 0.080(6) -0.013(5) -0.018(5) -0.011(5) N26 0.045(4) 0.039(3) 0.065(4) 0.000(3) -0.016(3) 0.000(3) C27 0.043(4) 0.046(4) 0.067(5) 0.001(4) 0.006(4) -0.010(4) C28 0.078(6) 0.051(5) 0.055(5) 0.012(4) 0.019(4) -0.014(4) C30 0.042(4) 0.038(4) 0.051(4) 0.006(3) 0.007(3) -0.006(3) C31 0.033(4) 0.045(4) 0.034(4) 0.003(3) 0.005(3) 0.002(3) N32 0.042(3) 0.032(3) 0.037(3) 0.001(3) 0.011(2) 0.003(3) C33 0.061(5) 0.039(4) 0.048(4) 0.008(3) 0.008(4) 0.009(4) C34 0.067(5) 0.058(5) 0.045(4) 0.011(4) -0.003(4) 0.023(5) C35 0.061(5) 0.072(6) 0.045(5) 0.001(4) -0.008(4) 0.020(5) C36 0.043(4) 0.059(5) 0.056(5) -0.005(4) -0.002(4) -0.001(4) C40 0.055(5) 0.044(4) 0.039(4) 0.013(3) 0.009(3) 0.001(4) C41 0.052(5) 0.064(5) 0.031(4) 0.003(4) 0.009(3) 0.016(4) N42 0.047(3) 0.052(4) 0.034(3) -0.007(3) 0.000(3) 0.009(3) C43 0.058(5) 0.055(5) 0.060(5) -0.023(4) 0.001(4) 0.010(4) C44 0.069(6) 0.098(8) 0.062(6) -0.037(6) -0.017(5) 0.033(6) C45 0.079(7) 0.126(10) 0.048(5) -0.019(6) -0.016(5) 0.051(7) C46 0.070(6) 0.098(7) 0.041(5) 0.012(5) 0.006(4) 0.026(5) Cl1 0.0676(14) 0.0642(13) 0.0546(12) -0.0010(10) -0.0041(10) 0.0081(11) O1P 0.110(5) 0.110(6) 0.062(4) 0.016(4) 0.014(4) 0.038(5) O2P 0.131(14) 0.20(2) 0.094(11) -0.014(14) -0.023(10) 0.029(15) O2P' 0.21(2) 0.088(14) 0.089(11) 0.009(10) -0.051(13) -0.073(14) O3P 0.16(2) 0.068(12) 0.21(2) -0.023(12) 0.107(17) -0.029(12) O3P' 0.161(19) 0.039(8) 0.100(12) 0.020(8) 0.064(13) 0.035(10) O4P 0.153(17) 0.078(11) 0.121(13) -0.028(9) 0.063(13) 0.045(11) O4P' 0.085(12) 0.16(2) 0.150(18) 0.026(16) 0.048(12) 0.025(14) Cl2 0.0569(12) 0.0478(11) 0.0570(11) -0.0035(9) 0.0134(9) 0.0053(9) O5P 0.100(6) 0.143(7) 0.091(5) 0.021(5) 0.025(4) -0.033(5) 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 O1 1.923(4) . y Cu1 N1 1.936(5) . y Cu1 O10 1.944(4) . y Cu1 N23 2.036(5) . y Cu1 N26 2.498(6) . y Cu1 Cu2 3.0302(11) . y Cu2 O1 1.930(5) . y Cu2 N42 1.989(6) . y Cu2 N32 1.994(5) . y Cu2 N4 2.032(5) . y Cu2 O10 2.262(4) . y Cu2 O1P 2.979(6) . y O10 C12 1.325(7) . ? N1 C2 1.260(8) . ? N1 C21 1.483(8) . ? C2 C11 1.456(8) . ? C3 C13 1.501(8) . ? C3 N4 1.512(8) . ? N4 C30 1.484(8) . ? N4 C40 1.485(8) . ? C5 C15 1.505(9) . ? C11 C16 1.401(8) . ? C11 C12 1.425(8) . ? C12 C13 1.417(8) . ? C13 C14 1.377(9) . ? C14 C15 1.400(9) . ? C15 C16 1.372(9) . ? C21 C22 1.522(9) . ? C21 C28 1.524(9) . ? C21 C27 1.529(10) . ? C22 N23 1.491(8) . ? N23 C24 1.486(9) . ? C24 C25 1.519(11) . ? C25 N26 1.458(10) . ? N26 C27 1.452(9) . ? C30 C31 1.513(9) . ? C31 N32 1.338(8) . ? C31 C36 1.379(9) . ? N32 C33 1.339(8) . ? C33 C34 1.374(10) . ? C34 C35 1.360(11) . ? C35 C36 1.373(11) . ? C40 C41 1.514(10) . ? C41 N42 1.338(9) . ? C41 C46 1.383(10) . ? N42 C43 1.344(9) . ? C43 C44 1.383(11) . ? C44 C45 1.395(14) . ? C45 C46 1.381(13) . ? Cl1 O4P 1.345(10) . ? Cl1 O3P 1.371(11) . ? Cl1 O3P' 1.394(10) . ? Cl1 O4P' 1.407(11) . ? Cl1 O2P 1.415(11) . ? Cl1 O2P' 1.423(11) . ? Cl1 O1P 1.430(6) . ? O2P O2P' 1.025(18) . ? O2P O3P' 1.62(2) . ? O2P' O4P 1.56(2) . ? O3P O3P' 0.951(18) . ? O3P O4P' 1.73(2) . ? O4P O4P' 0.967(18) . ? Cl2 O8P 1.369(9) . ? Cl2 O6P' 1.399(12) . ? Cl2 O6P 1.399(9) . ? Cl2 O5P 1.410(6) . ? Cl2 O7P' 1.430(13) . ? Cl2 O8P' 1.445(13) . ? Cl2 O7P 1.460(8) . ? O6P O6P' 0.57(2) . ? O7P O7P' 0.64(3) . ? O8P O8P' 0.66(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 165.7(2) . . y O1 Cu1 O10 84.65(18) . . y N1 Cu1 O10 91.46(19) . . y O1 Cu1 N23 96.2(2) . . y N1 Cu1 N23 86.5(2) . . y O10 Cu1 N23 175.0(2) . . y O1 Cu1 N26 118.9(2) . . y N1 Cu1 N26 75.3(2) . . y O10 Cu1 N26 112.79(19) . . y N23 Cu1 N26 71.2(2) . . y O1 Cu2 N42 97.6(2) . . y O1 Cu2 N32 98.1(2) . . y N42 Cu2 N32 158.7(2) . . y O1 Cu2 N4 168.9(2) . . y N42 Cu2 N4 83.9(2) . . y N32 Cu2 N4 83.5(2) . . y O1 Cu2 O10 76.37(17) . . y N42 Cu2 O10 104.8(2) . . y N32 Cu2 O10 92.87(18) . . y N4 Cu2 O10 92.62(18) . . y O1 Cu2 O1P 107.23(19) . . y N42 Cu2 O1P 81.8(2) . . y N32 Cu2 O1P 79.88(19) . . y N4 Cu2 O1P 83.9(2) . . y O10 Cu2 O1P 172.23(17) . . y Cu1 O1 Cu2 103.7(2) . . y C12 O10 Cu1 124.1(4) . . y C12 O10 Cu2 117.0(4) . . y Cu1 O10 Cu2 91.87(16) . . y C2 N1 C21 123.7(5) . . ? C2 N1 Cu1 127.6(4) . . ? C21 N1 Cu1 108.3(4) . . ? N1 C2 C11 124.5(6) . . ? C13 C3 N4 117.9(5) . . ? C30 N4 C40 112.5(5) . . ? C30 N4 C3 110.8(5) . . ? C40 N4 C3 107.6(5) . . ? C30 N4 Cu2 109.1(4) . . ? C40 N4 Cu2 107.0(4) . . ? C3 N4 Cu2 109.7(4) . . ? C16 C11 C12 119.8(6) . . ? C16 C11 C2 117.7(5) . . ? C12 C11 C2 122.5(5) . . ? O10 C12 C13 119.4(5) . . ? O10 C12 C11 123.0(5) . . ? C13 C12 C11 117.5(5) . . ? C14 C13 C12 119.8(6) . . ? C14 C13 C3 121.0(6) . . ? C12 C13 C3 118.8(5) . . ? C13 C14 C15 123.3(6) . . ? C16 C15 C14 116.8(6) . . ? C16 C15 C5 121.0(6) . . ? C14 C15 C5 122.2(6) . . ? C15 C16 C11 122.7(6) . . ? N1 C21 C22 105.3(5) . . ? N1 C21 C28 115.6(6) . . ? C22 C21 C28 109.5(6) . . ? N1 C21 C27 104.0(5) . . ? C22 C21 C27 111.3(6) . . ? C28 C21 C27 110.9(6) . . ? N23 C22 C21 111.3(5) . . ? C24 N23 C22 113.6(6) . . ? C24 N23 Cu1 110.9(4) . . ? C22 N23 Cu1 106.2(4) . . ? N23 C24 C25 112.3(6) . . ? N26 C25 C24 113.3(6) . . ? C27 N26 C25 114.6(6) . . ? C27 N26 Cu1 101.3(4) . . ? C25 N26 Cu1 101.9(5) . . ? N26 C27 C21 112.1(6) . . ? N4 C30 C31 110.6(5) . . ? N32 C31 C36 121.9(6) . . ? N32 C31 C30 115.9(6) . . ? C36 C31 C30 122.1(7) . . ? C31 N32 C33 117.9(6) . . ? C31 N32 Cu2 114.7(4) . . ? C33 N32 Cu2 127.2(5) . . ? N32 C33 C34 123.0(7) . . ? C35 C34 C33 118.5(7) . . ? C34 C35 C36 119.7(8) . . ? C35 C36 C31 118.9(8) . . ? N4 C40 C41 111.2(5) . . ? N42 C41 C46 123.0(8) . . ? N42 C41 C40 116.0(6) . . ? C46 C41 C40 120.8(8) . . ? C41 N42 C43 118.8(7) . . ? C41 N42 Cu2 113.9(5) . . ? C43 N42 Cu2 127.2(6) . . ? N42 C43 C44 122.4(9) . . ? C43 C44 C45 117.8(9) . . ? C46 C45 C44 120.4(9) . . ? C45 C46 C41 117.7(10) . . ? O4P Cl1 O3P 113.7(9) . . ? O4P Cl1 O3P' 131.5(10) . . ? O3P Cl1 O3P' 40.2(8) . . ? O4P Cl1 O4P' 41.1(7) . . ? O3P Cl1 O4P' 76.9(10) . . ? O3P' Cl1 O4P' 110.3(8) . . ? O4P Cl1 O2P 108.7(8) . . ? O3P Cl1 O2P 110.4(8) . . ? O3P' Cl1 O2P 70.2(9) . . ? O4P' Cl1 O2P 142.3(10) . . ? O4P Cl1 O2P' 68.6(9) . . ? O3P Cl1 O2P' 140.5(10) . . ? O3P' Cl1 O2P' 106.6(8) . . ? O4P' Cl1 O2P' 108.5(8) . . ? O2P Cl1 O2P' 42.3(8) . . ? O4P Cl1 O1P 113.1(7) . . ? O3P Cl1 O1P 106.6(8) . . ? O3P' Cl1 O1P 114.0(7) . . ? O4P' Cl1 O1P 109.2(8) . . ? O2P Cl1 O1P 104.0(7) . . ? O2P' Cl1 O1P 108.0(7) . . ? Cl1 O1P Cu2 144.3(4) . . ? O2P' O2P Cl1 69.3(9) . . ? O2P' O2P O3P' 115.7(13) . . ? Cl1 O2P O3P' 54.3(6) . . ? O2P O2P' Cl1 68.4(9) . . ? O2P O2P' O4P 118.9(12) . . ? Cl1 O2P' O4P 53.3(6) . . ? O3P' O3P Cl1 71.2(10) . . ? O3P' O3P O4P' 115.1(15) . . ? Cl1 O3P O4P' 52.5(7) . . ? O3P O3P' Cl1 68.5(10) . . ? O3P O3P' O2P 123.9(13) . . ? Cl1 O3P' O2P 55.5(7) . . ? O4P' O4P Cl1 73.0(10) . . ? O4P' O4P O2P' 129.1(14) . . ? Cl1 O4P O2P' 58.1(7) . . ? O4P O4P' Cl1 66.0(9) . . ? O4P O4P' O3P 111.8(13) . . ? Cl1 O4P' O3P 50.6(6) . . ? O8P Cl2 O6P' 116.3(10) . . ? O8P Cl2 O6P 116.3(7) . . ? O6P' Cl2 O6P 23.6(9) . . ? O8P Cl2 O5P 114.3(6) . . ? O6P' Cl2 O5P 121.6(9) . . ? O6P Cl2 O5P 105.6(6) . . ? O8P Cl2 O7P' 82.1(11) . . ? O6P' Cl2 O7P' 106.8(9) . . ? O6P Cl2 O7P' 130.3(11) . . ? O5P Cl2 O7P' 107.1(9) . . ? O8P Cl2 O8P' 26.8(9) . . ? O6P' Cl2 O8P' 107.6(9) . . ? O6P Cl2 O8P' 97.9(11) . . ? O5P Cl2 O8P' 104.4(8) . . ? O7P' Cl2 O8P' 108.9(8) . . ? O8P Cl2 O7P 107.0(6) . . ? O6P' Cl2 O7P 90.5(10) . . ? O6P Cl2 O7P 111.7(6) . . ? O5P Cl2 O7P 100.9(5) . . ? O7P' Cl2 O7P 25.6(11) . . ? O8P' Cl2 O7P 133.8(10) . . ? O6P' O6P Cl2 78.2(17) . . ? O6P O6P' Cl2 78.2(16) . . ? O7P' O7P Cl2 74.5(14) . . ? O7P O7P' Cl2 79.9(15) . . ? O8P' O8P Cl2 83.1(15) . . ? O8P O8P' Cl2 70.1(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N23 H23 O5P 0.98 2.34 3.129(9) 136.1 2_546 y N23 H23 O7P 0.98 2.38 3.345(11) 165.8 2_546 y N23 H23 O7P' 0.98 2.65 3.62(2) 168.9 2_546 y N26 H26 O10 0.91 2.48 3.256(7) 144.4 3_567 y _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.805 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.096