Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Ramaswamy Murugavel' _publ_contact_author_address ; Department of Chemistry IIT-Bombay Powai Mumbai 400076 INDIA ; _publ_contact_author_email RMV@CHEM.IITB.AC.IN _publ_section_title ; Synthesis, magnetic behaviour, and X-ray structures of dinuclear copper phosphinates with multiple bridges. Efficient and selective catalysts for polymerization of 2,6-dimethylphenol ; loop_ _publ_author_name 'Ramaswamy Murugavel' 'R. Butcher' 'Rodolphe Clerac' 'Nayanmoni Gogoi' 'Lollita Lecren' 'Munirathinam Nethaji' ; R.Pothiraja ; data_rp440_m _database_code_depnum_ccdc_archive 'CCDC 631558' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Copper-alkoxide-phosphinate _chemical_melting_point 189-190 _chemical_formula_moiety 'C38 H50 Cu2 N8 O6 P2, CH2Cl2, 2(H2O)' _chemical_formula_sum 'C39 H56 Cl2 Cu2 N8 O8 P2' _chemical_formula_weight 1024.84 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' P P 0.1023 0.0942 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/m 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 16.360(5) _cell_length_b 17.733(5) _cell_length_c 9.758(5) _cell_angle_alpha 90.00 _cell_angle_beta 125.619(5) _cell_angle_gamma 90.00 _cell_volume 2301.3(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular plate' _exptl_crystal_colour blue _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.168 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5765 _exptl_absorpt_correction_T_max 0.9227 _exptl_absorpt_process_details 'SADABS (SHELDRICK,1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method OMEGA-PHI _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10025 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.04 _reflns_number_total 2813 _reflns_number_gt 2256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX CCD' _computing_cell_refinement 'BRUKER SMART APEX CCD' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'WINGX V.164.05' _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+3.8337P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2813 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1466 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.5000 0.08463(3) 1.0000 0.0437(2) Uani 1 2 d S . . P1 P 0.39802(9) 0.0000 1.21135(16) 0.0472(3) Uani 1 2 d S . . O1 O 0.4117(2) 0.0000 0.8819(3) 0.0341(6) Uani 1 2 d S . . O2 O 0.4478(2) 0.07322(15) 1.2229(4) 0.0592(7) Uani 1 1 d . . . O3 O 0.5000 -0.1701(3) 0.5000 0.0959(16) Uani 1 2 d S . . N1 N 0.38678(18) -0.15606(14) 0.8616(3) 0.0413(6) Uani 1 1 d . . . N2 N 0.31033(18) -0.13793(14) 0.6991(3) 0.0404(6) Uani 1 1 d . . . C1 C 0.3550(2) -0.21655(18) 0.9011(4) 0.0454(7) Uani 1 1 d . . . C2 C 0.2591(3) -0.23662(19) 0.7638(5) 0.0495(8) Uani 1 1 d . . . H2 H 0.2207 -0.2768 0.7582 0.059 Uiso 1 1 calc R . . C3 C 0.2320(2) -0.18571(19) 0.6383(4) 0.0458(7) Uani 1 1 d . . . C4 C 0.3190(2) -0.07069(17) 0.6237(4) 0.0402(7) Uani 1 1 d . . . H4A H 0.2621 -0.0677 0.5063 0.048 Uiso 1 1 calc R . . H4B H 0.3797 -0.0736 0.6282 0.048 Uiso 1 1 calc R . . C5 C 0.3225(3) 0.0000 0.7162(5) 0.0336(8) Uani 1 2 d S . . H5 H 0.2644 0.0000 0.7213 0.040 Uiso 1 2 calc SR . . C6 C 0.4178(3) -0.2511(2) 1.0730(5) 0.0597(10) Uani 1 1 d . . . H6A H 0.4809 -0.2251 1.1404 0.090 Uiso 1 1 calc R . . H6B H 0.4296 -0.3033 1.0637 0.090 Uiso 1 1 calc R . . H6C H 0.3832 -0.2472 1.1252 0.090 Uiso 1 1 calc R . . C7 C 0.1363(3) -0.1790(2) 0.4656(5) 0.0643(10) Uani 1 1 d . . . H7A H 0.1408 -0.1371 0.4080 0.096 Uiso 1 1 calc R . . H7B H 0.0813 -0.1711 0.4741 0.096 Uiso 1 1 calc R . . H7C H 0.1251 -0.2245 0.4036 0.096 Uiso 1 1 calc R . . C8 C 0.2718(3) 0.0000 1.0191(6) 0.0428(10) Uani 1 2 d S . . C9 C 0.2227(3) -0.0674(2) 0.9437(5) 0.0501(8) Uani 1 1 d . . . H9 H 0.2551 -0.1129 0.9922 0.060 Uiso 1 1 calc R . . C10 C 0.1255(3) -0.0674(2) 0.7963(5) 0.0566(9) Uani 1 1 d . . . H10 H 0.0934 -0.1128 0.7460 0.068 Uiso 1 1 calc R . . C11 C 0.0766(4) 0.0000 0.7244(7) 0.0592(13) Uani 1 2 d S . . H11 H 0.0108 0.0000 0.6278 0.071 Uiso 1 2 calc SR . . Cl1 Cl 0.0905(3) -0.0362(4) 1.1490(5) 0.170(3) Uani 0.50 1 d P . . C12 C 0.0000 0.0000 1.0000 0.28(2) Uani 1 4 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0266(3) 0.0309(3) 0.0413(3) 0.000 0.0014(2) 0.000 P1 0.0382(6) 0.0543(7) 0.0433(6) 0.000 0.0204(5) 0.000 O1 0.0253(13) 0.0321(14) 0.0285(13) 0.000 0.0064(11) 0.000 O2 0.0438(13) 0.0549(15) 0.0606(16) -0.0091(12) 0.0200(12) -0.0053(11) O3 0.147(5) 0.052(2) 0.088(3) 0.000 0.068(4) 0.000 N1 0.0309(12) 0.0363(13) 0.0386(13) -0.0010(11) 0.0098(11) -0.0019(10) N2 0.0293(12) 0.0380(13) 0.0376(13) -0.0067(10) 0.0103(10) -0.0017(10) C1 0.0404(17) 0.0370(16) 0.0504(18) -0.0031(13) 0.0216(15) -0.0014(13) C2 0.0411(17) 0.0396(17) 0.060(2) -0.0095(15) 0.0245(16) -0.0101(14) C3 0.0298(14) 0.0429(17) 0.0502(18) -0.0128(14) 0.0150(13) -0.0048(13) C4 0.0334(14) 0.0427(17) 0.0325(14) -0.0047(12) 0.0124(12) -0.0025(12) C5 0.0228(17) 0.035(2) 0.0306(19) 0.000 0.0086(15) 0.000 C6 0.057(2) 0.050(2) 0.059(2) 0.0092(17) 0.0271(19) -0.0033(17) C7 0.0369(18) 0.064(2) 0.056(2) -0.0163(19) 0.0069(16) -0.0105(17) C8 0.036(2) 0.048(2) 0.043(2) 0.000 0.023(2) 0.000 C9 0.0459(18) 0.0459(18) 0.057(2) 0.0030(15) 0.0295(17) -0.0018(15) C10 0.0457(19) 0.057(2) 0.061(2) -0.0077(17) 0.0270(18) -0.0137(16) C11 0.039(3) 0.075(4) 0.051(3) 0.000 0.019(2) 0.000 Cl1 0.100(2) 0.310(10) 0.100(2) 0.041(3) 0.057(2) 0.057(4) C12 0.18(2) 0.61(7) 0.084(12) 0.000 0.091(16) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9311(17) . ? Cu1 O1 1.9311(17) 5_657 ? Cu1 N1 1.986(3) 5_657 ? Cu1 N1 1.986(2) 6 ? Cu1 Cu1 3.0016(13) 5_657 ? P1 O2 1.502(3) . ? P1 O2 1.502(3) 6 ? P1 C8 1.808(5) . ? O1 C5 1.412(4) . ? O1 Cu1 1.9311(17) 5_657 ? N1 C1 1.343(4) . ? N1 N2 1.368(3) . ? N1 Cu1 1.986(2) 5_657 ? N2 C3 1.351(4) . ? N2 C4 1.451(4) . ? C1 C2 1.391(5) . ? C1 C6 1.496(5) . ? C2 C3 1.371(5) . ? C2 H2 0.9300 . ? C3 C7 1.495(5) . ? C4 C5 1.526(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C4 1.526(4) 6 ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.388(4) . ? C8 C9 1.388(4) 6 ? C9 C10 1.391(5) . ? C9 H9 0.9300 . ? C10 C11 1.381(5) . ? C10 H10 0.9300 . ? C11 C10 1.381(5) 6 ? C11 H11 0.9300 . ? Cl1 Cl1 1.283(13) 6 ? Cl1 C12 1.487(4) . ? C12 Cl1 1.487(4) 6 ? C12 Cl1 1.487(4) 5_557 ? C12 Cl1 1.487(4) 2_557 ? 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 O1 77.99(12) . 5_657 ? O1 Cu1 N1 168.17(10) . 5_657 ? O1 Cu1 N1 90.71(10) 5_657 5_657 ? O1 Cu1 N1 90.71(10) . 6 ? O1 Cu1 N1 168.17(10) 5_657 6 ? N1 Cu1 N1 100.76(15) 5_657 6 ? O1 Cu1 Cu1 39.00(6) . 5_657 ? O1 Cu1 Cu1 39.00(6) 5_657 5_657 ? N1 Cu1 Cu1 129.62(7) 5_657 5_657 ? N1 Cu1 Cu1 129.62(7) 6 5_657 ? O2 P1 O2 119.7(2) . 6 ? O2 P1 C8 108.65(13) . . ? O2 P1 C8 108.65(13) 6 . ? C5 O1 Cu1 126.74(9) . . ? C5 O1 Cu1 126.74(9) . 5_657 ? Cu1 O1 Cu1 102.01(12) . 5_657 ? C1 N1 N2 105.9(2) . . ? C1 N1 Cu1 132.7(2) . 5_657 ? N2 N1 Cu1 119.9(2) . 5_657 ? C3 N2 N1 110.8(3) . . ? C3 N2 C4 129.8(3) . . ? N1 N2 C4 119.2(2) . . ? N1 C1 C2 109.7(3) . . ? N1 C1 C6 121.4(3) . . ? C2 C1 C6 128.9(3) . . ? C3 C2 C1 106.7(3) . . ? C3 C2 H2 126.6 . . ? C1 C2 H2 126.6 . . ? N2 C3 C2 106.9(3) . . ? N2 C3 C7 123.3(3) . . ? C2 C3 C7 129.8(3) . . ? N2 C4 C5 110.9(3) . . ? N2 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? O1 C5 C4 109.6(2) . 6 ? O1 C5 C4 109.6(2) . . ? C4 C5 C4 110.5(4) 6 . ? O1 C5 H5 109.1 . . ? C4 C5 H5 109.1 6 . ? C4 C5 H5 109.1 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C9 118.9(5) . 6 ? C9 C8 P1 120.6(2) . . ? C9 C8 P1 120.6(2) 6 . ? C8 C9 C10 120.6(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C10 119.9(5) 6 . ? C10 C11 H11 120.0 6 . ? C10 C11 H11 120.0 . . ? Cl1 Cl1 C12 64.4(2) 6 . ? Cl1 C12 Cl1 128.9(5) 6 5_557 ? Cl1 C12 Cl1 180.0(3) 6 2_557 ? Cl1 C12 Cl1 51.1(5) 5_557 2_557 ? Cl1 C12 Cl1 51.1(5) 6 . ? Cl1 C12 Cl1 180.0(3) 5_557 . ? Cl1 C12 Cl1 128.9(5) 2_557 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 C5 -157.2(4) 5_657 . . . ? N1 Cu1 O1 C5 -139.6(5) 5_657 . . . ? N1 Cu1 O1 C5 26.3(3) 6 . . . ? Cu1 Cu1 O1 C5 -157.2(4) 5_657 . . . ? O1 Cu1 O1 Cu1 0.0 5_657 . . 5_657 ? N1 Cu1 O1 Cu1 17.6(6) 5_657 . . 5_657 ? N1 Cu1 O1 Cu1 -176.46(13) 6 . . 5_657 ? C1 N1 N2 C3 0.4(4) . . . . ? Cu1 N1 N2 C3 -167.8(2) 5_657 . . . ? C1 N1 N2 C4 175.4(3) . . . . ? Cu1 N1 N2 C4 7.2(4) 5_657 . . . ? N2 N1 C1 C2 0.2(4) . . . . ? Cu1 N1 C1 C2 166.2(2) 5_657 . . . ? N2 N1 C1 C6 -177.7(3) . . . . ? Cu1 N1 C1 C6 -11.8(5) 5_657 . . . ? N1 C1 C2 C3 -0.7(4) . . . . ? C6 C1 C2 C3 177.0(4) . . . . ? N1 N2 C3 C2 -0.8(4) . . . . ? C4 N2 C3 C2 -175.1(3) . . . . ? N1 N2 C3 C7 178.3(3) . . . . ? C4 N2 C3 C7 4.0(5) . . . . ? C1 C2 C3 N2 0.9(4) . . . . ? C1 C2 C3 C7 -178.1(4) . . . . ? C3 N2 C4 C5 110.1(4) . . . . ? N1 N2 C4 C5 -63.8(4) . . . . ? Cu1 O1 C5 C4 15.2(4) . . . 6 ? Cu1 O1 C5 C4 -136.5(2) 5_657 . . 6 ? Cu1 O1 C5 C4 136.5(2) . . . . ? Cu1 O1 C5 C4 -15.2(4) 5_657 . . . ? N2 C4 C5 O1 66.0(4) . . . . ? N2 C4 C5 C4 -173.26(18) . . . 6 ? O2 P1 C8 C9 155.6(3) . . . . ? O2 P1 C8 C9 23.9(4) 6 . . . ? O2 P1 C8 C9 -23.9(4) . . . 6 ? O2 P1 C8 C9 -155.6(3) 6 . . 6 ? C9 C8 C9 C10 -0.8(7) 6 . . . ? P1 C8 C9 C10 179.7(3) . . . . ? C8 C9 C10 C11 -0.6(6) . . . . ? C9 C10 C11 C10 2.0(8) . . . 6 ? Cl1 Cl1 C12 Cl1 -163(100) 6 . . 5_557 ? Cl1 Cl1 C12 Cl1 180.0 6 . . 2_557 ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.610 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.076 data_rp243ms(Compound2) _database_code_depnum_ccdc_archive 'CCDC 631559' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Copper-alkoxide-phosphinate _chemical_melting_point 196-198 _chemical_formula_moiety 'C50 H60 Cu2 N8 O6 P2, 2(C12 H10 O2 P)' _chemical_formula_sum 'C74 H80 Cu2 N8 O10 P4' _chemical_formula_weight 1492.42 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.206(2) _cell_length_b 13.439(2) _cell_length_c 13.497(2) _cell_angle_alpha 71.321(3) _cell_angle_beta 61.987(2) _cell_angle_gamma 69.552(3) _cell_volume 1945.8(5) _cell_formula_units_Z 1 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description plate _exptl_crystal_colour 'deep blue' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 778 _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15003 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 28.41 _reflns_number_total 9035 _reflns_number_gt 7246 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0870P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9035 _refine_ls_number_parameters 448 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.60653(2) 0.55084(2) 0.42940(2) 0.01334(9) Uani 1 1 d . . . P1 P 0.76869(5) 0.28530(5) 0.42202(5) 0.01493(13) Uani 1 1 d . . . P2 P 0.68397(5) 0.17166(5) 0.17285(5) 0.01833(14) Uani 1 1 d . . . O1 O 0.47828(13) 0.52003(13) 0.41715(12) 0.0152(3) Uani 1 1 d . . . O2 O 0.75122(14) 0.40233(13) 0.36639(13) 0.0179(3) Uani 1 1 d . . . O3 O 0.68176(15) 0.22388(14) 0.43338(15) 0.0217(4) Uani 1 1 d . . . H3 H 0.6827 0.2309 0.3688 0.104(19) Uiso 1 1 calc R . . O4 O 0.68622(18) 0.23093(16) 0.05631(15) 0.0322(4) Uani 1 1 d . . . O5 O 0.69765(15) 0.23368(14) 0.24114(15) 0.0245(4) Uani 1 1 d . . . N1 N 0.63122(16) 0.65263(16) 0.28016(15) 0.0166(4) Uani 1 1 d . . . N2 N 0.62388(17) 0.62408(16) 0.19442(15) 0.0163(4) Uani 1 1 d . . . N3 N 0.28817(17) 0.41637(16) 0.52255(16) 0.0172(4) Uani 1 1 d . . . N4 N 0.32427(17) 0.40586(16) 0.41162(16) 0.0173(4) Uani 1 1 d . . . C1 C 0.6445(2) 0.8182(2) 0.3152(2) 0.0227(5) Uani 1 1 d . . . H1A H 0.6054 0.8945 0.2985 0.034 Uiso 1 1 calc R . . H1B H 0.7268 0.8121 0.2987 0.034 Uiso 1 1 calc R . . H1C H 0.6036 0.7883 0.3960 0.034 Uiso 1 1 calc R . . C2 C 0.6409(2) 0.75634(19) 0.24202(19) 0.0178(4) Uani 1 1 d . . . C3 C 0.6418(2) 0.7929(2) 0.1316(2) 0.0232(5) Uani 1 1 d . . . H3A H 0.6491 0.8621 0.0850 0.028 Uiso 1 1 calc R . . C4 C 0.6297(2) 0.7072(2) 0.10415(19) 0.0218(5) Uani 1 1 d . . . C5 C 0.6221(3) 0.6994(3) -0.0010(2) 0.0321(6) Uani 1 1 d . . . H5A H 0.6798 0.6350 -0.0301 0.048 Uiso 1 1 calc R . . H5B H 0.6392 0.7640 -0.0597 0.048 Uiso 1 1 calc R . . H5C H 0.5425 0.6941 0.0185 0.048 Uiso 1 1 calc R . . C6 C 0.5963(2) 0.52010(19) 0.21512(18) 0.0164(4) Uani 1 1 d . . . H6A H 0.6580 0.4599 0.2334 0.020 Uiso 1 1 calc R . . H6B H 0.5958 0.5117 0.1451 0.020 Uiso 1 1 calc R . . C7 C 0.47512(19) 0.51498(18) 0.31470(18) 0.0155(4) Uani 1 1 d . . . H7A H 0.4135 0.5777 0.2974 0.019 Uiso 1 1 calc R . . C8 C 0.4452(2) 0.40882(19) 0.32885(19) 0.0178(4) Uani 1 1 d . . . H8A H 0.4552 0.4012 0.2540 0.021 Uiso 1 1 calc R . . H8B H 0.5009 0.3469 0.3544 0.021 Uiso 1 1 calc R . . C9 C 0.2501(2) 0.3743(2) 0.2853(2) 0.0302(6) Uani 1 1 d . . . H9A H 0.3156 0.3118 0.2618 0.045 Uiso 1 1 calc R . . H9B H 0.2670 0.4390 0.2267 0.045 Uiso 1 1 calc R . . H9C H 0.1772 0.3616 0.2947 0.045 Uiso 1 1 calc R . . C10 C 0.2357(2) 0.39060(19) 0.3971(2) 0.0205(5) Uani 1 1 d . . . C11 C 0.1384(2) 0.3930(2) 0.5014(2) 0.0232(5) Uani 1 1 d . . . H11A H 0.0629 0.3851 0.5183 0.028 Uiso 1 1 calc R . . C12 C 0.1741(2) 0.4095(2) 0.5769(2) 0.0204(5) Uani 1 1 d . . . C13 C 0.1023(2) 0.4194(2) 0.7003(2) 0.0264(5) Uani 1 1 d . . . H13A H 0.1163 0.4795 0.7146 0.040 Uiso 1 1 calc R . . H13B H 0.1255 0.3521 0.7491 0.040 Uiso 1 1 calc R . . H13C H 0.0183 0.4331 0.7177 0.040 Uiso 1 1 calc R . . C1A C 0.91668(19) 0.2132(2) 0.33955(19) 0.0181(5) Uani 1 1 d . . . C2A C 0.9843(2) 0.2654(2) 0.2332(2) 0.0288(6) Uani 1 1 d . . . H2AA H 0.9565 0.3402 0.2076 0.035 Uiso 1 1 calc R . . C3A C 1.0940(2) 0.2076(3) 0.1632(2) 0.0392(7) Uani 1 1 d . . . H3AA H 1.1399 0.2431 0.0904 0.047 Uiso 1 1 calc R . . C4A C 1.1343(2) 0.0991(3) 0.2012(2) 0.0354(7) Uani 1 1 d . . . H4AA H 1.2074 0.0600 0.1532 0.042 Uiso 1 1 calc R . . C5A C 1.0699(2) 0.0463(2) 0.3082(3) 0.0310(6) Uani 1 1 d . . . H5AA H 1.0993 -0.0279 0.3341 0.037 Uiso 1 1 calc R . . C6A C 0.9602(2) 0.1039(2) 0.3783(2) 0.0248(5) Uani 1 1 d . . . H6AA H 0.9158 0.0685 0.4519 0.030 Uiso 1 1 calc R . . C1B C 0.75711(19) 0.26329(18) 0.56673(19) 0.0173(4) Uani 1 1 d . . . C2B C 0.8257(2) 0.3105(2) 0.5845(2) 0.0214(5) Uani 1 1 d . . . H2BA H 0.8773 0.3511 0.5216 0.026 Uiso 1 1 calc R . . C3B C 0.8179(2) 0.2976(2) 0.6952(2) 0.0256(5) Uani 1 1 d . . . H3BA H 0.8627 0.3309 0.7075 0.031 Uiso 1 1 calc R . . C4B C 0.7440(2) 0.2356(2) 0.7872(2) 0.0261(5) Uani 1 1 d . . . H4BA H 0.7404 0.2251 0.8618 0.031 Uiso 1 1 calc R . . C5B C 0.6754(2) 0.1891(2) 0.7697(2) 0.0241(5) Uani 1 1 d . . . H5BA H 0.6243 0.1481 0.8326 0.029 Uiso 1 1 calc R . . C6B C 0.6820(2) 0.20281(19) 0.65937(19) 0.0197(5) Uani 1 1 d . . . H6BA H 0.6354 0.1710 0.6477 0.024 Uiso 1 1 calc R . . C1C C 0.5454(2) 0.12884(19) 0.2570(2) 0.0195(5) Uani 1 1 d . . . C2C C 0.4883(2) 0.1221(2) 0.3758(2) 0.0246(5) Uani 1 1 d . . . H2CA H 0.5217 0.1409 0.4143 0.030 Uiso 1 1 calc R . . C3C C 0.3823(2) 0.0877(2) 0.4388(3) 0.0343(6) Uani 1 1 d . . . H3CA H 0.3438 0.0840 0.5191 0.041 Uiso 1 1 calc R . . C4C C 0.3343(2) 0.0591(2) 0.3827(3) 0.0380(7) Uani 1 1 d . . . H4CA H 0.2627 0.0359 0.4248 0.046 Uiso 1 1 calc R . . C5C C 0.3909(3) 0.0644(2) 0.2646(3) 0.0357(7) Uani 1 1 d . . . H5CA H 0.3580 0.0441 0.2268 0.043 Uiso 1 1 calc R . . C6C C 0.4952(2) 0.0993(2) 0.2020(2) 0.0279(6) Uani 1 1 d . . . H6CA H 0.5328 0.1032 0.1216 0.034 Uiso 1 1 calc R . . C1D C 0.7978(2) 0.0461(2) 0.1594(2) 0.0199(5) Uani 1 1 d . . . C2D C 0.8480(2) 0.0004(2) 0.2400(2) 0.0249(5) Uani 1 1 d . . . H2DA H 0.8229 0.0357 0.3013 0.030 Uiso 1 1 calc R . . C3D C 0.9347(2) -0.0969(2) 0.2312(3) 0.0310(6) Uani 1 1 d . . . H3DA H 0.9683 -0.1271 0.2862 0.037 Uiso 1 1 calc R . . C4D C 0.9717(2) -0.1493(2) 0.1416(3) 0.0323(6) Uani 1 1 d . . . H4DA H 1.0305 -0.2154 0.1355 0.039 Uiso 1 1 calc R . . C5D C 0.9222(2) -0.1046(2) 0.0607(2) 0.0302(6) Uani 1 1 d . . . H5DA H 0.9474 -0.1403 -0.0003 0.036 Uiso 1 1 calc R . . C6D C 0.8357(2) -0.0076(2) 0.0695(2) 0.0245(5) Uani 1 1 d . . . H6DA H 0.8022 0.0224 0.0144 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.01681(15) 0.01306(15) 0.01161(14) -0.00188(10) -0.00581(10) -0.00551(10) P1 0.0148(3) 0.0136(3) 0.0162(3) -0.0045(2) -0.0056(2) -0.0026(2) P2 0.0233(3) 0.0174(3) 0.0158(3) -0.0034(2) -0.0078(2) -0.0065(2) O1 0.0191(8) 0.0180(8) 0.0101(7) -0.0032(6) -0.0056(6) -0.0061(6) O2 0.0199(8) 0.0143(8) 0.0188(8) -0.0042(6) -0.0079(6) -0.0022(6) O3 0.0206(8) 0.0223(9) 0.0249(9) -0.0053(7) -0.0090(7) -0.0076(7) O4 0.0433(11) 0.0304(11) 0.0199(9) 0.0010(8) -0.0131(8) -0.0100(9) O5 0.0284(9) 0.0220(9) 0.0284(9) -0.0092(7) -0.0119(8) -0.0073(7) N1 0.0181(9) 0.0198(10) 0.0117(8) -0.0045(7) -0.0058(7) -0.0033(8) N2 0.0205(9) 0.0161(10) 0.0134(9) -0.0035(7) -0.0065(7) -0.0053(7) N3 0.0211(9) 0.0155(10) 0.0170(9) -0.0036(7) -0.0084(8) -0.0052(8) N4 0.0219(9) 0.0156(10) 0.0171(9) -0.0047(7) -0.0087(8) -0.0048(8) C1 0.0277(12) 0.0152(12) 0.0239(12) -0.0041(9) -0.0079(10) -0.0068(10) C2 0.0177(10) 0.0146(11) 0.0176(11) -0.0019(8) -0.0051(9) -0.0037(9) C3 0.0252(12) 0.0198(12) 0.0211(12) 0.0032(9) -0.0093(10) -0.0078(10) C4 0.0220(11) 0.0261(13) 0.0139(10) -0.0001(9) -0.0058(9) -0.0074(10) C5 0.0451(16) 0.0422(17) 0.0159(12) 0.0038(11) -0.0168(11) -0.0202(13) C6 0.0206(11) 0.0174(11) 0.0128(10) -0.0035(8) -0.0070(9) -0.0056(9) C7 0.0200(11) 0.0141(11) 0.0139(10) -0.0057(8) -0.0073(9) -0.0023(8) C8 0.0203(11) 0.0167(11) 0.0176(11) -0.0074(9) -0.0063(9) -0.0041(9) C9 0.0357(14) 0.0362(16) 0.0306(14) -0.0098(12) -0.0196(12) -0.0099(12) C10 0.0261(12) 0.0153(11) 0.0279(12) -0.0046(9) -0.0164(10) -0.0053(9) C11 0.0203(11) 0.0224(13) 0.0319(13) -0.0067(10) -0.0116(10) -0.0077(10) C12 0.0209(11) 0.0169(12) 0.0241(12) -0.0040(9) -0.0087(10) -0.0058(9) C13 0.0240(12) 0.0293(14) 0.0250(12) -0.0077(10) -0.0034(10) -0.0121(10) C1A 0.0166(10) 0.0218(12) 0.0191(11) -0.0120(9) -0.0070(9) -0.0010(9) C2A 0.0213(12) 0.0322(15) 0.0239(13) -0.0070(11) -0.0051(10) -0.0004(11) C3A 0.0235(13) 0.059(2) 0.0226(13) -0.0130(13) -0.0008(11) -0.0033(13) C4A 0.0210(12) 0.053(2) 0.0323(15) -0.0269(14) -0.0103(11) 0.0073(12) C5A 0.0262(13) 0.0280(15) 0.0425(16) -0.0195(12) -0.0196(12) 0.0091(11) C6A 0.0244(12) 0.0221(13) 0.0277(13) -0.0087(10) -0.0123(10) 0.0007(10) C1B 0.0173(10) 0.0147(11) 0.0160(10) -0.0050(8) -0.0054(9) 0.0007(8) C2B 0.0205(11) 0.0227(13) 0.0202(11) -0.0046(9) -0.0081(9) -0.0039(10) C3B 0.0265(12) 0.0272(14) 0.0256(13) -0.0082(10) -0.0142(11) -0.0010(10) C4B 0.0289(13) 0.0255(13) 0.0199(12) -0.0076(10) -0.0125(10) 0.0050(10) C5B 0.0239(12) 0.0190(12) 0.0175(11) -0.0019(9) -0.0033(9) 0.0000(10) C6B 0.0203(11) 0.0149(11) 0.0193(11) -0.0037(9) -0.0063(9) -0.0011(9) C1C 0.0243(11) 0.0136(11) 0.0231(12) -0.0028(9) -0.0126(10) -0.0034(9) C2C 0.0269(12) 0.0196(12) 0.0260(12) -0.0040(10) -0.0084(10) -0.0074(10) C3C 0.0315(14) 0.0290(15) 0.0339(15) -0.0047(12) -0.0045(12) -0.0110(12) C4C 0.0247(13) 0.0287(15) 0.058(2) -0.0036(14) -0.0131(13) -0.0124(12) C5C 0.0386(16) 0.0254(15) 0.059(2) -0.0029(13) -0.0330(15) -0.0114(12) C6C 0.0351(14) 0.0210(13) 0.0354(14) -0.0059(11) -0.0209(12) -0.0053(11) C1D 0.0199(11) 0.0206(12) 0.0193(11) -0.0064(9) -0.0042(9) -0.0080(9) C2D 0.0272(12) 0.0243(13) 0.0264(13) -0.0061(10) -0.0126(10) -0.0059(10) C3D 0.0280(13) 0.0267(14) 0.0412(16) -0.0064(12) -0.0193(12) -0.0020(11) C4D 0.0220(12) 0.0217(14) 0.0494(17) -0.0124(12) -0.0085(12) -0.0042(10) C5D 0.0277(13) 0.0272(15) 0.0329(14) -0.0159(11) -0.0026(11) -0.0081(11) C6D 0.0247(12) 0.0276(14) 0.0226(12) -0.0097(10) -0.0051(10) -0.0096(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O1 1.9375(15) 2_666 ? Cu O1 1.9658(16) . ? Cu N1 1.9911(19) . ? Cu N3 2.0016(19) 2_666 ? Cu O2 2.2921(16) . ? P1 O2 1.4979(17) . ? P1 O3 1.5615(17) . ? P1 C1B 1.818(2) . ? P1 C1A 1.823(2) . ? P2 O4 1.5098(19) . ? P2 O5 1.5267(17) . ? P2 C1D 1.818(3) . ? P2 C1C 1.826(3) . ? O1 C7 1.426(2) . ? O1 Cu 1.9375(15) 2_666 ? O3 H3 0.8400 . ? N1 C2 1.352(3) . ? N1 N2 1.383(2) . ? N2 C4 1.356(3) . ? N2 C6 1.474(3) . ? N3 C12 1.353(3) . ? N3 N4 1.381(3) . ? N3 Cu 2.0016(19) 2_666 ? N4 C10 1.363(3) . ? N4 C8 1.463(3) . ? C1 C2 1.505(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.408(3) . ? C3 C4 1.394(4) . ? C3 H3A 0.9500 . ? C4 C5 1.507(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.539(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.542(3) . ? C7 H7A 1.0000 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.508(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.391(3) . ? C11 C12 1.407(3) . ? C11 H11A 0.9500 . ? C12 C13 1.504(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C1A C2A 1.393(4) . ? C1A C6A 1.401(3) . ? C2A C3A 1.412(4) . ? C2A H2AA 0.9500 . ? C3A C4A 1.381(5) . ? C3A H3AA 0.9500 . ? C4A C5A 1.388(4) . ? C4A H4AA 0.9500 . ? C5A C6A 1.411(3) . ? C5A H5AA 0.9500 . ? C6A H6AA 0.9500 . ? C1B C6B 1.398(3) . ? C1B C2B 1.409(3) . ? C2B C3B 1.406(3) . ? C2B H2BA 0.9500 . ? C3B C4B 1.398(4) . ? C3B H3BA 0.9500 . ? C4B C5B 1.401(4) . ? C4B H4BA 0.9500 . ? C5B C6B 1.404(3) . ? C5B H5BA 0.9500 . ? C6B H6BA 0.9500 . ? C1C C2C 1.403(3) . ? C1C C6C 1.409(3) . ? C2C C3C 1.407(4) . ? C2C H2CA 0.9500 . ? C3C C4C 1.389(4) . ? C3C H3CA 0.9500 . ? C4C C5C 1.396(5) . ? C4C H4CA 0.9500 . ? C5C C6C 1.391(4) . ? C5C H5CA 0.9500 . ? C6C H6CA 0.9500 . ? C1D C2D 1.402(3) . ? C1D C6D 1.408(3) . ? C2D C3D 1.399(4) . ? C2D H2DA 0.9500 . ? C3D C4D 1.397(4) . ? C3D H3DA 0.9500 . ? C4D C5D 1.399(4) . ? C4D H4DA 0.9500 . ? C5D C6D 1.396(4) . ? C5D H5DA 0.9500 . ? C6D H6DA 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu O1 76.49(7) 2_666 . ? O1 Cu N1 158.33(7) 2_666 . ? O1 Cu N1 88.10(7) . . ? O1 Cu N3 92.41(7) 2_666 2_666 ? O1 Cu N3 167.39(7) . 2_666 ? N1 Cu N3 100.87(8) . 2_666 ? O1 Cu O2 97.94(6) 2_666 . ? O1 Cu O2 97.88(6) . . ? N1 Cu O2 99.22(7) . . ? N3 Cu O2 89.47(7) 2_666 . ? O2 P1 O3 116.65(10) . . ? O2 P1 C1B 112.88(10) . . ? O3 P1 C1B 104.54(10) . . ? O2 P1 C1A 108.89(10) . . ? O3 P1 C1A 106.36(10) . . ? C1B P1 C1A 106.91(10) . . ? O4 P2 O5 116.46(11) . . ? O4 P2 C1D 109.65(11) . . ? O5 P2 C1D 108.50(10) . . ? O4 P2 C1C 108.34(11) . . ? O5 P2 C1C 108.72(10) . . ? C1D P2 C1C 104.51(11) . . ? C7 O1 Cu 126.62(14) . 2_666 ? C7 O1 Cu 126.40(13) . . ? Cu O1 Cu 103.51(7) 2_666 . ? P1 O2 Cu 131.19(9) . . ? P1 O3 H3 109.5 . . ? C2 N1 N2 106.00(18) . . ? C2 N1 Cu 134.32(15) . . ? N2 N1 Cu 119.12(15) . . ? C4 N2 N1 111.12(19) . . ? C4 N2 C6 128.52(19) . . ? N1 N2 C6 119.80(18) . . ? C12 N3 N4 105.87(18) . . ? C12 N3 Cu 132.51(16) . 2_666 ? N4 N3 Cu 121.37(14) . 2_666 ? C10 N4 N3 111.01(19) . . ? C10 N4 C8 128.82(19) . . ? N3 N4 C8 120.14(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.7(2) . . ? N1 C2 C1 121.7(2) . . ? C3 C2 C1 128.6(2) . . ? C4 C3 C2 106.4(2) . . ? C4 C3 H3A 126.8 . . ? C2 C3 H3A 126.8 . . ? N2 C4 C3 106.8(2) . . ? N2 C4 C5 122.6(2) . . ? C3 C4 C5 130.6(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 110.56(17) . . ? N2 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? O1 C7 C6 109.54(17) . . ? O1 C7 C8 110.22(18) . . ? C6 C7 C8 109.26(17) . . ? O1 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N4 C8 C7 111.84(17) . . ? N4 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? N4 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C10 C11 106.8(2) . . ? N4 C10 C9 123.0(2) . . ? C11 C10 C9 130.2(2) . . ? C10 C11 C12 106.3(2) . . ? C10 C11 H11A 126.8 . . ? C12 C11 H11A 126.8 . . ? N3 C12 C11 110.0(2) . . ? N3 C12 C13 121.9(2) . . ? C11 C12 C13 128.1(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2A C1A C6A 119.5(2) . . ? C2A C1A P1 119.51(19) . . ? C6A C1A P1 120.82(18) . . ? C1A C2A C3A 120.2(3) . . ? C1A C2A H2AA 119.9 . . ? C3A C2A H2AA 119.9 . . ? C4A C3A C2A 119.6(3) . . ? C4A C3A H3AA 120.2 . . ? C2A C3A H3AA 120.2 . . ? C3A C4A C5A 121.0(2) . . ? C3A C4A H4AA 119.5 . . ? C5A C4A H4AA 119.5 . . ? C4A C5A C6A 119.4(3) . . ? C4A C5A H5AA 120.3 . . ? C6A C5A H5AA 120.3 . . ? C1A C6A C5A 120.1(2) . . ? C1A C6A H6AA 119.9 . . ? C5A C6A H6AA 119.9 . . ? C6B C1B C2B 119.8(2) . . ? C6B C1B P1 122.15(18) . . ? C2B C1B P1 118.01(18) . . ? C3B C2B C1B 120.1(2) . . ? C3B C2B H2BA 120.0 . . ? C1B C2B H2BA 120.0 . . ? C4B C3B C2B 119.8(2) . . ? C4B C3B H3BA 120.1 . . ? C2B C3B H3BA 120.1 . . ? C3B C4B C5B 120.1(2) . . ? C3B C4B H4BA 119.9 . . ? C5B C4B H4BA 119.9 . . ? C4B C5B C6B 120.2(2) . . ? C4B C5B H5BA 119.9 . . ? C6B C5B H5BA 119.9 . . ? C1B C6B C5B 119.9(2) . . ? C1B C6B H6BA 120.0 . . ? C5B C6B H6BA 120.0 . . ? C2C C1C C6C 118.7(2) . . ? C2C C1C P2 121.92(18) . . ? C6C C1C P2 119.39(19) . . ? C1C C2C C3C 120.7(2) . . ? C1C C2C H2CA 119.6 . . ? C3C C2C H2CA 119.6 . . ? C4C C3C C2C 119.6(3) . . ? C4C C3C H3CA 120.2 . . ? C2C C3C H3CA 120.2 . . ? C3C C4C C5C 120.2(3) . . ? C3C C4C H4CA 119.9 . . ? C5C C4C H4CA 119.9 . . ? C6C C5C C4C 120.3(3) . . ? C6C C5C H5CA 119.8 . . ? C4C C5C H5CA 119.8 . . ? C5C C6C C1C 120.4(3) . . ? C5C C6C H6CA 119.8 . . ? C1C C6C H6CA 119.8 . . ? C2D C1D C6D 118.9(2) . . ? C2D C1D P2 120.25(18) . . ? C6D C1D P2 120.87(19) . . ? C3D C2D C1D 120.7(2) . . ? C3D C2D H2DA 119.7 . . ? C1D C2D H2DA 119.7 . . ? C4D C3D C2D 119.9(3) . . ? C4D C3D H3DA 120.0 . . ? C2D C3D H3DA 120.0 . . ? C3D C4D C5D 120.0(2) . . ? C3D C4D H4DA 120.0 . . ? C5D C4D H4DA 120.0 . . ? C6D C5D C4D 120.1(2) . . ? C6D C5D H5DA 120.0 . . ? C4D C5D H5DA 120.0 . . ? C5D C6D C1D 120.5(2) . . ? C5D C6D H6DA 119.8 . . ? C1D C6D H6DA 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu O1 C7 -159.9(2) 2_666 . . . ? N1 Cu O1 C7 35.46(17) . . . . ? N3 Cu O1 C7 171.2(3) 2_666 . . . ? O2 Cu O1 C7 -63.59(17) . . . . ? O1 Cu O1 Cu 0.0 2_666 . . 2_666 ? N1 Cu O1 Cu -164.62(8) . . . 2_666 ? N3 Cu O1 Cu -28.9(4) 2_666 . . 2_666 ? O2 Cu O1 Cu 96.33(7) . . . 2_666 ? O3 P1 O2 Cu 71.57(14) . . . . ? C1B P1 O2 Cu -49.54(15) . . . . ? C1A P1 O2 Cu -168.11(11) . . . . ? O1 Cu O2 P1 5.09(13) 2_666 . . . ? O1 Cu O2 P1 -72.28(13) . . . . ? N1 Cu O2 P1 -161.63(12) . . . . ? N3 Cu O2 P1 97.45(13) 2_666 . . . ? O1 Cu N1 C2 85.7(3) 2_666 . . . ? O1 Cu N1 C2 129.9(2) . . . . ? N3 Cu N1 C2 -41.2(2) 2_666 . . . ? O2 Cu N1 C2 -132.4(2) . . . . ? O1 Cu N1 N2 -84.4(2) 2_666 . . . ? O1 Cu N1 N2 -40.16(16) . . . . ? N3 Cu N1 N2 148.76(15) 2_666 . . . ? O2 Cu N1 N2 57.52(16) . . . . ? C2 N1 N2 C4 0.5(2) . . . . ? Cu N1 N2 C4 173.09(15) . . . . ? C2 N1 N2 C6 -171.73(18) . . . . ? Cu N1 N2 C6 0.9(3) . . . . ? C12 N3 N4 C10 -1.2(3) . . . . ? Cu N3 N4 C10 -176.05(15) 2_666 . . . ? C12 N3 N4 C8 -179.5(2) . . . . ? Cu N3 N4 C8 5.6(3) 2_666 . . . ? N2 N1 C2 C3 -1.0(2) . . . . ? Cu N1 C2 C3 -172.00(17) . . . . ? N2 N1 C2 C1 176.7(2) . . . . ? Cu N1 C2 C1 5.7(3) . . . . ? N1 C2 C3 C4 1.2(3) . . . . ? C1 C2 C3 C4 -176.3(2) . . . . ? N1 N2 C4 C3 0.3(3) . . . . ? C6 N2 C4 C3 171.6(2) . . . . ? N1 N2 C4 C5 -179.1(2) . . . . ? C6 N2 C4 C5 -7.8(4) . . . . ? C2 C3 C4 N2 -0.9(3) . . . . ? C2 C3 C4 C5 178.5(3) . . . . ? C4 N2 C6 C7 -110.5(2) . . . . ? N1 N2 C6 C7 60.2(2) . . . . ? Cu O1 C7 C6 -146.76(15) 2_666 . . . ? Cu O1 C7 C6 8.7(2) . . . . ? Cu O1 C7 C8 -26.5(2) 2_666 . . . ? Cu O1 C7 C8 128.90(16) . . . . ? N2 C6 C7 O1 -63.0(2) . . . . ? N2 C6 C7 C8 176.21(17) . . . . ? C10 N4 C8 C7 123.9(2) . . . . ? N3 N4 C8 C7 -58.1(3) . . . . ? O1 C7 C8 N4 67.5(2) . . . . ? C6 C7 C8 N4 -172.13(18) . . . . ? N3 N4 C10 C11 1.0(3) . . . . ? C8 N4 C10 C11 179.1(2) . . . . ? N3 N4 C10 C9 -178.7(2) . . . . ? C8 N4 C10 C9 -0.6(4) . . . . ? N4 C10 C11 C12 -0.4(3) . . . . ? C9 C10 C11 C12 179.3(3) . . . . ? N4 N3 C12 C11 0.9(3) . . . . ? Cu N3 C12 C11 174.99(17) 2_666 . . . ? N4 N3 C12 C13 -178.9(2) . . . . ? Cu N3 C12 C13 -4.8(4) 2_666 . . . ? C10 C11 C12 N3 -0.4(3) . . . . ? C10 C11 C12 C13 179.4(2) . . . . ? O2 P1 C1A C2A -10.0(2) . . . . ? O3 P1 C1A C2A 116.5(2) . . . . ? C1B P1 C1A C2A -132.2(2) . . . . ? O2 P1 C1A C6A 174.26(18) . . . . ? O3 P1 C1A C6A -59.3(2) . . . . ? C1B P1 C1A C6A 52.0(2) . . . . ? C6A C1A C2A C3A 2.3(4) . . . . ? P1 C1A C2A C3A -173.5(2) . . . . ? C1A C2A C3A C4A -0.5(4) . . . . ? C2A C3A C4A C5A -1.4(4) . . . . ? C3A C4A C5A C6A 1.4(4) . . . . ? C2A C1A C6A C5A -2.2(4) . . . . ? P1 C1A C6A C5A 173.51(19) . . . . ? C4A C5A C6A C1A 0.4(4) . . . . ? O2 P1 C1B C6B 127.51(18) . . . . ? O3 P1 C1B C6B -0.2(2) . . . . ? C1A P1 C1B C6B -112.78(19) . . . . ? O2 P1 C1B C2B -51.7(2) . . . . ? O3 P1 C1B C2B -179.47(17) . . . . ? C1A P1 C1B C2B 68.0(2) . . . . ? C6B C1B C2B C3B -0.6(3) . . . . ? P1 C1B C2B C3B 178.69(18) . . . . ? C1B C2B C3B C4B 1.6(4) . . . . ? C2B C3B C4B C5B -1.8(4) . . . . ? C3B C4B C5B C6B 1.1(4) . . . . ? C2B C1B C6B C5B -0.2(3) . . . . ? P1 C1B C6B C5B -179.37(17) . . . . ? C4B C5B C6B C1B -0.1(3) . . . . ? O4 P2 C1C C2C -147.7(2) . . . . ? O5 P2 C1C C2C -20.2(2) . . . . ? C1D P2 C1C C2C 95.5(2) . . . . ? O4 P2 C1C C6C 33.8(2) . . . . ? O5 P2 C1C C6C 161.23(19) . . . . ? C1D P2 C1C C6C -83.1(2) . . . . ? C6C C1C C2C C3C -0.7(4) . . . . ? P2 C1C C2C C3C -179.3(2) . . . . ? C1C C2C C3C C4C 0.6(4) . . . . ? C2C C3C C4C C5C 0.0(4) . . . . ? C3C C4C C5C C6C -0.6(4) . . . . ? C4C C5C C6C C1C 0.5(4) . . . . ? C2C C1C C6C C5C 0.2(4) . . . . ? P2 C1C C6C C5C 178.8(2) . . . . ? O4 P2 C1D C2D 152.8(2) . . . . ? O5 P2 C1D C2D 24.6(2) . . . . ? C1C P2 C1D C2D -91.2(2) . . . . ? O4 P2 C1D C6D -28.2(2) . . . . ? O5 P2 C1D C6D -156.4(2) . . . . ? C1C P2 C1D C6D 87.8(2) . . . . ? C6D C1D C2D C3D 0.2(4) . . . . ? P2 C1D C2D C3D 179.3(2) . . . . ? C1D C2D C3D C4D -0.2(4) . . . . ? C2D C3D C4D C5D 0.1(4) . . . . ? C3D C4D C5D C6D -0.1(4) . . . . ? C4D C5D C6D C1D 0.1(4) . . . . ? C2D C1D C6D C5D -0.2(4) . . . . ? P2 C1D C6D C5D -179.2(2) . . . . ? 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 O3 H3 O5 0.84 1.63 2.466(2) 173.7 . _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.886 _refine_diff_density_min -0.821 _refine_diff_density_rms 0.094