# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Xiao-Jun Zhao' _publ_contact_author_email 'xiaojun zhao15@yahoo.com.cn' _publ_section_title ; Ligand-deprotonation induced structural diversity in a ternary CuII-triazole-tetracarboxylate self-assembly system: synthesis, crystal structures, and magnetic behavior ; loop_ _publ_author_name 'En-Cui Yang' 'Zhong-Yi Liu' 'Li-Na Zhao' 'You-Li Yang' 'Cui-Hua Zhang' ; Xiao-Jun Zhao ; # Attachment '- 90730B-3.cif' data_90730b _database_code_depnum_ccdc_archive 'CCDC 804526' #TrackingRef '- 90730B-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cu N8 O9' _chemical_formula_weight 501.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.9180(13) _cell_length_b 7.3603(4) _cell_length_c 12.9038(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.722(2) _cell_angle_gamma 90.00 _cell_volume 1784.40(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4024 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 1.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7542 _exptl_absorpt_correction_T_max 0.7810 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4325 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1575 _reflns_number_gt 1525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+3.8204P] 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 1575 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0723 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.39714(5) 0.2500 0.02017(14) Uani 1 2 d S . . O1 O 0.57565(7) 0.39038(19) 0.37037(12) 0.0211(3) Uani 1 1 d . . . O2 O 0.58562(8) 0.0936(2) 0.34503(13) 0.0277(4) Uani 1 1 d . . . O3 O 0.57491(8) 0.1409(3) 0.58512(13) 0.0364(4) Uani 1 1 d . . . O4 O 0.66255(9) 0.0360(3) 0.70022(13) 0.0386(4) Uani 1 1 d . . . H4 H 0.6293 -0.0031 0.7292 0.058 Uiso 1 1 calc R . . O5 O 0.5000 0.7156(3) 0.2500 0.0419(6) Uani 1 2 d S . . H5 H 0.5202 0.7826 0.2086 0.063 Uiso 1 1 d R . . N1 N 0.37017(9) 0.3107(3) 0.47876(14) 0.0226(4) Uani 1 1 d . . . N2 N 0.42775(9) 0.3814(3) 0.34915(15) 0.0241(4) Uani 1 1 d . . . N3 N 0.35640(10) 0.4239(3) 0.32096(15) 0.0300(5) Uani 1 1 d . . . N4 N 0.35105(10) 0.2552(3) 0.57632(14) 0.0284(4) Uani 1 1 d . . . H4A H 0.3731 0.1494 0.5941 0.043 Uiso 1 1 d R . . H4B H 0.3643 0.3455 0.6215 0.043 Uiso 1 1 d R . . C1 C 0.43437(11) 0.3155(3) 0.44404(17) 0.0247(5) Uani 1 1 d . . . H1 H 0.4768 0.2779 0.4815 0.030 Uiso 1 1 calc R . . C2 C 0.32392(12) 0.3779(3) 0.40048(18) 0.0281(5) Uani 1 1 d . . . H2 H 0.2752 0.3897 0.4031 0.034 Uiso 1 1 calc R . . C3 C 0.67978(10) 0.2461(3) 0.44987(15) 0.0180(4) Uani 1 1 d . . . C4 C 0.69517(10) 0.1807(3) 0.55200(16) 0.0187(4) Uani 1 1 d . . . C5 C 0.73490(11) 0.3158(3) 0.39994(16) 0.0206(4) Uani 1 1 d . . . H5A H 0.7249 0.3614 0.3326 0.025 Uiso 1 1 calc R . . C6 C 0.60723(10) 0.2398(3) 0.38555(15) 0.0183(4) Uani 1 1 d . . . C7 C 0.63763(11) 0.1173(3) 0.61311(17) 0.0227(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0130(2) 0.0279(2) 0.0190(2) 0.000 -0.00086(13) 0.000 O1 0.0152(7) 0.0242(8) 0.0226(8) -0.0014(6) -0.0029(6) 0.0031(6) O2 0.0220(8) 0.0254(8) 0.0347(9) -0.0053(7) -0.0009(7) -0.0006(6) O3 0.0170(8) 0.0578(11) 0.0351(10) 0.0125(9) 0.0059(7) 0.0010(8) O4 0.0255(8) 0.0599(12) 0.0312(9) 0.0205(9) 0.0062(7) -0.0022(8) O5 0.0513(16) 0.0323(13) 0.0452(15) 0.000 0.0179(12) 0.000 N1 0.0195(9) 0.0261(9) 0.0223(9) -0.0013(7) 0.0033(7) -0.0010(7) N2 0.0154(9) 0.0326(10) 0.0235(10) -0.0014(8) -0.0005(7) 0.0016(7) N3 0.0180(9) 0.0465(12) 0.0249(10) -0.0002(9) -0.0001(8) 0.0066(8) N4 0.0302(10) 0.0304(10) 0.0252(10) 0.0033(8) 0.0060(8) -0.0025(8) C1 0.0173(10) 0.0307(12) 0.0256(11) 0.0001(9) 0.0003(8) 0.0009(9) C2 0.0167(10) 0.0391(13) 0.0283(12) -0.0024(10) 0.0014(9) 0.0040(9) C3 0.0135(9) 0.0215(10) 0.0187(10) -0.0005(8) 0.0006(7) 0.0036(8) C4 0.0161(10) 0.0215(10) 0.0189(10) 0.0008(8) 0.0031(8) 0.0017(8) C5 0.0185(10) 0.0270(11) 0.0159(9) 0.0041(8) 0.0006(8) 0.0025(8) C6 0.0139(10) 0.0264(11) 0.0150(9) 0.0007(8) 0.0035(8) 0.0003(8) C7 0.0217(11) 0.0249(11) 0.0221(11) 0.0007(8) 0.0050(9) -0.0004(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.9819(18) . ? Cu1 N2 1.9820(18) 2_655 ? Cu1 O1 1.9857(14) . ? Cu1 O1 1.9857(14) 2_655 ? Cu1 O5 2.344(3) . ? O1 C6 1.264(2) . ? O2 C6 1.244(3) . ? O3 C7 1.212(3) . ? O4 C7 1.312(3) . ? O4 H4 0.8200 . ? O5 H5 0.8499 . ? N1 C1 1.343(3) . ? N1 C2 1.350(3) . ? N1 N4 1.411(3) . ? N2 C1 1.309(3) . ? N2 N3 1.392(3) . ? N3 C2 1.301(3) . ? N4 H4A 0.9001 . ? N4 H4B 0.9001 . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C5 1.387(3) . ? C3 C4 1.401(3) . ? C3 C6 1.519(3) . ? C4 C5 1.394(3) 7_656 ? C4 C7 1.492(3) . ? C5 C4 1.394(3) 7_656 ? C5 H5A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 173.32(11) . 2_655 ? N2 Cu1 O1 88.97(7) . . ? N2 Cu1 O1 90.86(7) 2_655 . ? N2 Cu1 O1 90.86(7) . 2_655 ? N2 Cu1 O1 88.97(7) 2_655 2_655 ? O1 Cu1 O1 177.13(8) . 2_655 ? N2 Cu1 O5 93.34(5) . . ? N2 Cu1 O5 93.34(5) 2_655 . ? O1 Cu1 O5 91.44(4) . . ? O1 Cu1 O5 91.44(4) 2_655 . ? C6 O1 Cu1 115.32(13) . . ? C7 O4 H4 109.5 . . ? Cu1 O5 H5 125.5 . . ? C1 N1 C2 105.84(18) . . ? C1 N1 N4 129.91(18) . . ? C2 N1 N4 124.22(18) . . ? C1 N2 N3 108.15(18) . . ? C1 N2 Cu1 128.86(15) . . ? N3 N2 Cu1 122.63(14) . . ? C2 N3 N2 105.58(19) . . ? N1 N4 H4A 108.6 . . ? N1 N4 H4B 106.5 . . ? H4A N4 H4B 112.9 . . ? N2 C1 N1 109.28(19) . . ? N2 C1 H1 125.4 . . ? N1 C1 H1 125.4 . . ? N3 C2 N1 111.1(2) . . ? N3 C2 H2 124.4 . . ? N1 C2 H2 124.4 . . ? C5 C3 C4 118.64(18) . . ? C5 C3 C6 115.97(18) . . ? C4 C3 C6 125.33(18) . . ? C5 C4 C3 119.60(19) 7_656 . ? C5 C4 C7 118.94(18) 7_656 . ? C3 C4 C7 121.36(18) . . ? C3 C5 C4 121.75(19) . 7_656 ? C3 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 7_656 . ? O2 C6 O1 124.57(18) . . ? O2 C6 C3 119.16(18) . . ? O1 C6 C3 116.00(18) . . ? O3 C7 O4 124.2(2) . . ? O3 C7 C4 123.2(2) . . ? O4 C7 C4 112.61(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 O1 C6 103.16(15) . . . . ? N2 Cu1 O1 C6 -70.16(15) 2_655 . . . ? O1 Cu1 O1 C6 16.48(14) 2_655 . . . ? O5 Cu1 O1 C6 -163.53(13) . . . . ? N2 Cu1 N2 C1 64.6(2) 2_655 . . . ? O1 Cu1 N2 C1 -24.1(2) . . . . ? O1 Cu1 N2 C1 153.1(2) 2_655 . . . ? O5 Cu1 N2 C1 -115.4(2) . . . . ? N2 Cu1 N2 N3 -107.72(17) 2_655 . . . ? O1 Cu1 N2 N3 163.66(17) . . . . ? O1 Cu1 N2 N3 -19.21(17) 2_655 . . . ? O5 Cu1 N2 N3 72.28(17) . . . . ? C1 N2 N3 C2 -1.0(3) . . . . ? Cu1 N2 N3 C2 172.66(16) . . . . ? N3 N2 C1 N1 0.8(3) . . . . ? Cu1 N2 C1 N1 -172.35(15) . . . . ? C2 N1 C1 N2 -0.3(3) . . . . ? N4 N1 C1 N2 -178.3(2) . . . . ? N2 N3 C2 N1 0.9(3) . . . . ? C1 N1 C2 N3 -0.4(3) . . . . ? N4 N1 C2 N3 177.8(2) . . . . ? C5 C3 C4 C5 -1.1(3) . . . 7_656 ? C6 C3 C4 C5 175.92(19) . . . 7_656 ? C5 C3 C4 C7 175.18(19) . . . . ? C6 C3 C4 C7 -7.8(3) . . . . ? C4 C3 C5 C4 1.2(3) . . . 7_656 ? C6 C3 C5 C4 -176.17(19) . . . 7_656 ? Cu1 O1 C6 O2 -14.4(3) . . . . ? Cu1 O1 C6 C3 159.58(13) . . . . ? C5 C3 C6 O2 100.2(2) . . . . ? C4 C3 C6 O2 -76.9(3) . . . . ? C5 C3 C6 O1 -74.1(2) . . . . ? C4 C3 C6 O1 108.8(2) . . . . ? C5 C4 C7 O3 165.9(2) 7_656 . . . ? C3 C4 C7 O3 -10.4(3) . . . . ? C5 C4 C7 O4 -13.3(3) 7_656 . . . ? C3 C4 C7 O4 170.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.335 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.056 # Attachment '- 90820C1-2.cif' data_90820c _database_code_depnum_ccdc_archive 'CCDC 804527' #TrackingRef '- 90820C1-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 Cl2 Cu3 N16 O21' _chemical_formula_weight 1066.08 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.2308(3) _cell_length_b 18.9146(6) _cell_length_c 11.7353(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.2320(10) _cell_angle_gamma 90.00 _cell_volume 1826.56(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7858 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.86 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.938 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1074 _exptl_absorpt_coefficient_mu 1.984 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6694 _exptl_absorpt_correction_T_max 0.9073 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9391 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3321 _reflns_number_gt 3062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. 64 restraints were used while dealing with disordered perchlorate anion, water molecule and 4-amino-1,2,4-triazole ligand. Perchlorate anion is disordered in two positions with the equal site occupancy factors. C3 and N6 atoms of 4-amino-1,2,4-triazole ligand are varied between two mirror-symmetric positions with the same site occupancy. The Cl-O and N-N distances were restrained to 1.45 \%A and 1.41 \%A, respectively. The distances of O, O in perchlorate anion and N8, C3 as well as N8, C4 in 4-amino-1,2,4-triazole ligand are equal by the restraint. The thermal parameters for O12, O12', O6 and N5 atoms were refined with isotropy. dfix 1.45 0.01 o7 cl1 O8 CL1 O9 CL1 O10 CL1 dfix 1.45 0.01 o7' cl1' O8' CL1' O9' CL1' O10' CL1' SADI 0.001 O7 O8 O7 O9 O7 O10 O8 O9 O8 O10 O9 O10 SADI 0.001 O7' O8' O7' O9' O7' O10' O8' O9' O8' O10' O9' O10' dfix 1.41 0.01 n7 n8 sadi 0.001 n8 c3 n8 c4 ISOR 0.005 O12 O12' o6 ISOR 0.001 N5 ; _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^)+(0.0839P)^2^+5.9854P] 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 3321 _refine_ls_number_parameters 324 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1375 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.75509(9) 0.2500 0.74279(6) 0.0244(2) Uani 1 2 d S . . Cu2 Cu 0.95660(6) 0.16219(2) 0.53559(4) 0.02349(19) Uani 1 1 d . . . O1 O 1.1038(3) 0.08413(14) 0.5011(2) 0.0247(6) Uani 1 1 d . A . O2 O 1.2617(4) 0.14943(16) 0.6143(3) 0.0346(7) Uani 1 1 d . A . O3 O 1.4351(4) 0.18352(15) 0.4018(3) 0.0325(7) Uani 1 1 d . . . H3' H 1.4577 0.2254 0.4107 0.049 Uiso 0.50 1 calc PR . . O4 O 1.7002(3) 0.16523(14) 0.4280(3) 0.0278(7) Uani 1 1 d . . . O5 O 0.5013(5) 0.2500 0.6627(4) 0.0387(11) Uani 1 2 d S A . H5' H 0.4442 0.2853 0.6418 0.058 Uiso 1 1 d R . . N1 N 0.8597(4) 0.11012(19) 0.6612(3) 0.0252(7) Uani 1 1 d . A . N2 N 0.7608(4) 0.14282(19) 0.7384(3) 0.0289(8) Uani 1 1 d . A . N3 N 0.7492(5) 0.0297(2) 0.7640(3) 0.0314(8) Uani 1 1 d . A . N4 N 0.7144(6) -0.0391(2) 0.8038(4) 0.0457(11) Uani 1 1 d . . . H4" H 0.7640 -0.0412 0.8729 0.055 Uiso 1 1 d R . . H4' H 0.6054 -0.0418 0.8074 0.055 Uiso 1 1 d R . . N5 N 0.6983(5) 0.2522(6) 0.9005(3) 0.0316(12) Uani 1 2 d SGU A -1 N6 N 0.5496(5) 0.2800(5) 0.9402(4) 0.061(3) Uani 0.50 1 d PG A -1 C3 C 0.5587(6) 0.2816(6) 1.0612(4) 0.063(4) Uani 0.50 1 d PGD A -1 H3 H 0.4778 0.2975 1.1090 0.075 Uiso 0.50 1 calc PR A -1 N7 N 0.7130(6) 0.2548(6) 1.0962(3) 0.036(2) Uani 0.50 1 d PGD A -1 C4 C 0.7993(5) 0.2366(4) 0.9969(4) 0.028(3) Uani 0.50 1 d PGD A -1 H4 H 0.9036 0.2178 0.9953 0.033 Uiso 0.50 1 calc PR A -1 N8 N 0.7731(8) 0.2533(14) 1.2047(5) 0.049(2) Uani 0.50 1 d PD A -1 H8' H 0.7342 0.2906 1.2430 0.059 Uiso 1 1 d R A -1 N9 N 1.0415(4) 0.21384(18) 0.4055(3) 0.0224(7) Uani 1 1 d . . . N10 N 1.1441(6) 0.2500 0.2485(5) 0.0317(12) Uani 1 2 d S . . N11 N 1.2189(9) 0.2500 0.1422(6) 0.0562(19) Uani 1 2 d S . . H11' H 1.1899 0.2858 0.0955 0.067 Uiso 1 1 d R . . C1 C 0.6959(6) 0.0934(2) 0.7990(4) 0.0363(11) Uani 1 1 d . . . H1 H 0.6236 0.1007 0.8577 0.044 Uiso 1 1 calc R A . C2 C 0.8507(5) 0.0421(2) 0.6785(4) 0.0276(9) Uani 1 1 d . . . H2 H 0.9059 0.0078 0.6379 0.033 Uiso 1 1 calc R A . C5 C 1.1045(5) 0.1929(2) 0.3099(4) 0.0292(9) Uani 1 1 d . . . H5 H 1.1194 0.1461 0.2880 0.035 Uiso 1 1 calc R A . C6 C 1.3780(4) 0.0499(2) 0.5197(3) 0.0212(8) Uani 1 1 d . A . C7 C 1.5222(4) 0.0707(2) 0.4678(3) 0.0201(8) Uani 1 1 d . . . C8 C 1.3588(5) -0.0205(2) 0.5499(3) 0.0218(8) Uani 1 1 d . . . H8 H 1.2624 -0.0345 0.5833 0.026 Uiso 1 1 calc R . . C9 C 1.2410(5) 0.0997(2) 0.5476(4) 0.0230(8) Uani 1 1 d . . . C10 C 1.5576(5) 0.1455(2) 0.4307(3) 0.0207(8) Uani 1 1 d . . . Cl1 Cl 0.7465(18) 0.0343(8) 0.1249(13) 0.0612(8) Uani 0.319(10) 1 d PD B 1 O7 O 0.661(3) 0.0871(9) 0.1892(17) 0.122(4) Uani 0.319(10) 1 d PD B 1 O8 O 0.821(3) 0.0669(13) 0.0294(15) 0.134(5) Uani 0.319(10) 1 d PD B 1 O9 O 0.6305(19) -0.0180(10) 0.085(2) 0.153(6) Uani 0.319(10) 1 d PD B 1 O10 O 0.866(2) 0.0010(13) 0.1965(17) 0.116(4) Uani 0.319(10) 1 d PD B 1 Cl1' Cl 0.7557(8) 0.0413(3) 0.1413(5) 0.0612(8) Uani 0.681(10) 1 d PD B 2 O7' O 0.6809(13) -0.0256(4) 0.1724(8) 0.122(4) Uani 0.681(10) 1 d PD B 2 O8' O 0.8064(14) 0.0366(6) 0.0276(6) 0.134(5) Uani 0.681(10) 1 d PD B 2 O9' O 0.6320(10) 0.0948(5) 0.1496(12) 0.153(6) Uani 0.681(10) 1 d PD B 2 O10' O 0.8844(9) 0.0558(6) 0.2167(7) 0.116(4) Uani 0.681(10) 1 d PD B 2 O11 O 0.8482(4) 0.2500 0.5887(3) 0.0192(8) Uani 1 2 d S . . H11 H 0.7632 0.2500 0.5463 0.029 Uiso 1 2 d SR . . O12 O 0.1008(11) 0.1294(5) 0.0106(8) 0.062(2) Uani 0.50 1 d PU C 1 O12' O 0.266(2) 0.1720(9) 0.8517(14) 0.124(5) Uani 0.50 1 d PU D 2 O6 O 1.0535(13) 0.2500 0.7938(9) 0.132(4) Uani 1 2 d SU A . H6 H 1.0949 0.2910 0.8006 0.198 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0320(4) 0.0181(4) 0.0235(4) 0.000 0.0087(3) 0.000 Cu2 0.0242(3) 0.0165(3) 0.0302(3) 0.00345(18) 0.0101(2) 0.00654(18) O1 0.0183(13) 0.0184(13) 0.0376(16) -0.0011(12) 0.0025(11) 0.0033(11) O2 0.0315(16) 0.0237(15) 0.0487(19) -0.0126(14) 0.0014(14) 0.0028(13) O3 0.0254(15) 0.0144(14) 0.057(2) 0.0052(14) -0.0068(14) 0.0016(12) O4 0.0206(14) 0.0190(15) 0.0439(18) 0.0041(12) 0.0005(12) -0.0030(11) O5 0.028(2) 0.029(2) 0.058(3) 0.000 -0.011(2) 0.000 N1 0.0267(17) 0.0205(17) 0.0287(18) 0.0025(14) 0.0053(14) 0.0061(14) N2 0.037(2) 0.0209(18) 0.0293(19) 0.0024(15) 0.0098(15) 0.0049(15) N3 0.043(2) 0.0199(18) 0.0321(19) 0.0045(15) 0.0092(16) -0.0018(15) N4 0.063(3) 0.021(2) 0.053(3) 0.0097(18) 0.015(2) -0.0065(19) N5 0.0319(14) 0.0315(15) 0.0314(14) -0.0006(11) 0.0024(10) 0.0001(11) N6 0.032(4) 0.120(11) 0.031(4) -0.010(5) 0.006(3) 0.001(4) C3 0.033(5) 0.123(12) 0.033(5) 0.003(6) 0.009(4) -0.005(6) N7 0.035(3) 0.046(5) 0.026(3) 0.027(7) 0.008(2) 0.016(7) C4 0.039(4) 0.012(10) 0.033(4) 0.000(3) 0.007(3) -0.004(3) N8 0.050(4) 0.061(7) 0.035(4) 0.016(14) 0.001(3) 0.003(14) N9 0.0181(15) 0.0206(16) 0.0288(18) 0.0002(14) 0.0043(13) 0.0025(13) N10 0.029(3) 0.037(3) 0.029(3) 0.000 0.011(2) 0.000 N11 0.073(5) 0.061(4) 0.036(3) 0.000 0.030(3) 0.000 C1 0.045(3) 0.028(2) 0.037(2) 0.0053(19) 0.016(2) 0.001(2) C2 0.031(2) 0.022(2) 0.030(2) 0.0019(17) 0.0037(17) 0.0034(17) C5 0.029(2) 0.027(2) 0.032(2) -0.0023(18) 0.0073(17) 0.0041(18) C6 0.0172(18) 0.0164(18) 0.030(2) -0.0014(16) -0.0021(15) 0.0009(15) C7 0.0176(18) 0.0144(18) 0.028(2) 0.0003(15) 0.0002(15) -0.0001(14) C8 0.0178(18) 0.0174(18) 0.030(2) -0.0001(16) 0.0021(15) -0.0016(15) C9 0.023(2) 0.0147(18) 0.032(2) 0.0025(16) 0.0047(16) 0.0013(15) C10 0.0211(19) 0.0160(18) 0.0250(19) -0.0032(16) 0.0015(15) 0.0003(15) Cl1 0.0769(13) 0.0621(16) 0.044(2) -0.0054(14) -0.0032(12) 0.0048(11) O7 0.189(12) 0.066(5) 0.113(7) 0.017(5) 0.027(8) -0.014(6) O8 0.184(9) 0.161(14) 0.056(4) -0.016(6) 0.021(4) -0.074(9) O9 0.064(5) 0.112(9) 0.282(19) -0.018(10) 0.003(8) 0.007(5) O10 0.083(5) 0.194(14) 0.069(5) 0.017(8) -0.020(4) -0.025(8) Cl1' 0.0769(13) 0.0621(16) 0.044(2) -0.0054(14) -0.0032(12) 0.0048(11) O7' 0.189(12) 0.066(5) 0.113(7) 0.017(5) 0.027(8) -0.014(6) O8' 0.184(9) 0.161(14) 0.056(4) -0.016(6) 0.021(4) -0.074(9) O9' 0.064(5) 0.112(9) 0.282(19) -0.018(10) 0.003(8) 0.007(5) O10' 0.083(5) 0.194(14) 0.069(5) 0.017(8) -0.020(4) -0.025(8) O11 0.0161(17) 0.0172(18) 0.0242(19) 0.000 0.0015(14) 0.000 O12 0.068(4) 0.052(4) 0.066(4) -0.014(3) 0.001(3) -0.004(3) O12' 0.126(6) 0.119(6) 0.127(7) -0.006(5) -0.008(5) -0.001(5) O6 0.114(5) 0.168(6) 0.113(5) 0.000 -0.002(4) 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 N5 1.919(3) . ? Cu1 O11 1.979(4) . ? Cu1 N2 2.028(4) . ? Cu1 N2 2.028(4) 4_565 ? Cu1 O5 2.272(4) . ? Cu1 O6 2.516(11) . ? Cu2 N9 1.954(3) . ? Cu2 N1 1.957(3) . ? Cu2 O1 1.957(3) . ? Cu2 O11 1.992(2) . ? Cu2 O4 2.436(3) 1_455 ? O1 C9 1.278(5) . ? O2 C9 1.234(5) . ? O3 C10 1.279(5) . ? O3 H3' 0.8200 . ? O4 C10 1.233(5) . ? O4 Cu2 2.436(3) 1_655 ? O5 H5' 0.8500 . ? N1 C2 1.304(6) . ? N1 N2 1.378(5) . ? N2 C1 1.297(6) . ? N3 C2 1.340(6) . ? N3 C1 1.349(6) . ? N3 N4 1.414(5) . ? N4 H4" 0.9010 . ? N4 H4' 0.9005 . ? N5 N6 1.4200 . ? N5 C4 1.4200 . ? N6 C3 1.4200 . ? C3 N7 1.4200 . ? C3 H3 0.9300 . ? N7 N8 1.356(6) . ? N7 C4 1.4200 . ? C4 H4 0.9300 . ? N8 H8' 0.9000 . ? N9 C5 1.308(6) . ? N9 N9 1.368(7) 4_565 ? N10 C5 1.342(5) . ? N10 C5 1.342(5) 4_565 ? N10 N11 1.403(8) . ? N11 H11' 0.9004 . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.389(5) . ? C6 C7 1.402(5) . ? C6 C9 1.510(5) . ? C7 C8 1.383(5) 3_856 ? C7 C10 1.510(5) . ? C8 C7 1.383(5) 3_856 ? C8 H8 0.9300 . ? Cl1 O10 1.427(10) . ? Cl1 O8 1.429(10) . ? Cl1 O7 1.443(10) . ? Cl1 O9 1.448(10) . ? Cl1' O10' 1.393(7) . ? Cl1' O8' 1.409(7) . ? Cl1' O9' 1.439(7) . ? Cl1' O7' 1.456(7) . ? O11 Cu2 1.992(2) 4_565 ? O11 H11 0.8500 . ? O6 H6 0.8502 . ? 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 N5 Cu1 O11 171.23(19) . . ? N5 Cu1 N2 93.0(4) . . ? O11 Cu1 N2 88.10(10) . . ? N5 Cu1 N2 90.6(4) . 4_565 ? O11 Cu1 N2 88.11(10) . 4_565 ? N2 Cu1 N2 176.0(2) . 4_565 ? N5 Cu1 O5 99.10(19) . . ? O11 Cu1 O5 89.59(17) . . ? N2 Cu1 O5 90.63(11) . . ? N2 Cu1 O5 90.63(11) 4_565 . ? N5 Cu1 O6 91.5(3) . . ? O11 Cu1 O6 79.8(3) . . ? N2 Cu1 O6 89.03(11) . . ? N2 Cu1 O6 89.03(11) 4_565 . ? O5 Cu1 O6 169.3(3) . . ? N9 Cu2 N1 176.74(14) . . ? N9 Cu2 O1 89.00(13) . . ? N1 Cu2 O1 92.29(13) . . ? N9 Cu2 O11 89.85(13) . . ? N1 Cu2 O11 89.52(14) . . ? O1 Cu2 O11 167.68(13) . . ? N9 Cu2 O4 84.47(12) . 1_455 ? N1 Cu2 O4 92.28(12) . 1_455 ? O1 Cu2 O4 116.34(11) . 1_455 ? O11 Cu2 O4 75.73(13) . 1_455 ? C9 O1 Cu2 106.5(2) . . ? C10 O3 H3' 109.5 . . ? C10 O4 Cu2 142.6(3) . 1_655 ? Cu1 O5 H5' 128.1 . . ? C2 N1 N2 107.7(3) . . ? C2 N1 Cu2 129.7(3) . . ? N2 N1 Cu2 121.7(3) . . ? C1 N2 N1 107.0(4) . . ? C1 N2 Cu1 134.1(3) . . ? N1 N2 Cu1 118.7(3) . . ? C2 N3 C1 106.5(4) . . ? C2 N3 N4 122.9(4) . . ? C1 N3 N4 130.6(4) . . ? N3 N4 H4" 104.3 . . ? N3 N4 H4' 106.1 . . ? H4" N4 H4' 112.8 . . ? N6 N5 C4 108.0 . . ? N6 N5 Cu1 123.6(3) . . ? C4 N5 Cu1 127.9(3) . . ? C3 N6 N5 108.0 . . ? N6 C3 N7 108.0 . . ? N6 C3 H3 126.0 . . ? N7 C3 H3 126.0 . . ? N8 N7 C4 125.86(8) . . ? N8 N7 C3 125.86(9) . . ? C4 N7 C3 108.0 . . ? N7 C4 N5 108.0 . . ? N7 C4 H4 126.0 . . ? N5 C4 H4 126.0 . . ? N7 N8 H8' 109.0 . . ? C5 N9 N9 107.6(2) . 4_565 ? C5 N9 Cu2 132.4(3) . . ? N9 N9 Cu2 120.00(10) 4_565 . ? C5 N10 C5 107.1(5) . 4_565 ? C5 N10 N11 126.4(3) . . ? C5 N10 N11 126.4(3) 4_565 . ? N10 N11 H11' 115.2 . . ? N2 C1 N3 109.6(4) . . ? N2 C1 H1 125.2 . . ? N3 C1 H1 125.2 . . ? N1 C2 N3 109.2(4) . . ? N1 C2 H2 125.4 . . ? N3 C2 H2 125.4 . . ? N9 C5 N10 108.8(4) . . ? N9 C5 H5 125.6 . . ? N10 C5 H5 125.6 . . ? C8 C6 C7 118.8(4) . . ? C8 C6 C9 116.9(3) . . ? C7 C6 C9 124.3(4) . . ? C8 C7 C6 118.8(4) 3_856 . ? C8 C7 C10 117.3(3) 3_856 . ? C6 C7 C10 123.9(3) . . ? C7 C8 C6 122.3(4) 3_856 . ? C7 C8 H8 118.8 3_856 . ? C6 C8 H8 118.8 . . ? O2 C9 O1 123.7(4) . . ? O2 C9 C6 121.3(4) . . ? O1 C9 C6 115.0(3) . . ? O4 C10 O3 124.7(4) . . ? O4 C10 C7 118.7(3) . . ? O3 C10 C7 116.6(3) . . ? O10 Cl1 O8 110.5(6) . . ? O10 Cl1 O7 109.6(6) . . ? O8 Cl1 O7 109.5(6) . . ? O10 Cl1 O9 109.4(6) . . ? O8 Cl1 O9 109.3(6) . . ? O7 Cl1 O9 108.5(6) . . ? O10' Cl1' O8' 112.2(4) . . ? O10' Cl1' O9' 110.3(4) . . ? O8' Cl1' O9' 109.4(4) . . ? O10' Cl1' O7' 109.4(4) . . ? O8' Cl1' O7' 108.5(4) . . ? O9' Cl1' O7' 106.9(4) . . ? Cu1 O11 Cu2 118.07(11) . . ? Cu1 O11 Cu2 118.07(11) . 4_565 ? Cu2 O11 Cu2 113.02(17) . 4_565 ? Cu1 O11 H11 101.8 . . ? Cu2 O11 H11 100.7 . . ? Cu2 O11 H11 100.7 4_565 . ? Cu1 O6 H6 114.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N9 Cu2 O1 C9 83.8(3) . . . . ? N1 Cu2 O1 C9 -99.2(3) . . . . ? O11 Cu2 O1 C9 -0.9(7) . . . . ? O4 Cu2 O1 C9 167.1(2) 1_455 . . . ? N9 Cu2 N1 C2 89(2) . . . . ? O1 Cu2 N1 C2 -24.5(4) . . . . ? O11 Cu2 N1 C2 167.7(4) . . . . ? O4 Cu2 N1 C2 92.0(4) 1_455 . . . ? N9 Cu2 N1 N2 -79(3) . . . . ? O1 Cu2 N1 N2 167.7(3) . . . . ? O11 Cu2 N1 N2 -0.1(3) . . . . ? O4 Cu2 N1 N2 -75.8(3) 1_455 . . . ? C2 N1 N2 C1 -0.1(5) . . . . ? Cu2 N1 N2 C1 170.1(3) . . . . ? C2 N1 N2 Cu1 176.3(3) . . . . ? Cu2 N1 N2 Cu1 -13.5(4) . . . . ? N5 Cu1 N2 C1 22.6(5) . . . . ? O11 Cu1 N2 C1 -166.2(5) . . . . ? N2 Cu1 N2 C1 175(3) 4_565 . . . ? O5 Cu1 N2 C1 -76.6(5) . . . . ? O6 Cu1 N2 C1 114.1(5) . . . . ? N5 Cu1 N2 N1 -152.6(3) . . . . ? O11 Cu1 N2 N1 18.6(3) . . . . ? N2 Cu1 N2 N1 0(3) 4_565 . . . ? O5 Cu1 N2 N1 108.2(3) . . . . ? O6 Cu1 N2 N1 -61.1(4) . . . . ? O11 Cu1 N5 N6 146.5(19) . . . . ? N2 Cu1 N5 N6 -116.5(6) . . . . ? N2 Cu1 N5 N6 65.4(6) 4_565 . . . ? O5 Cu1 N5 N6 -25.3(6) . . . . ? O6 Cu1 N5 N6 154.4(5) . . . . ? O11 Cu1 N5 C4 -24(3) . . . . ? N2 Cu1 N5 C4 72.9(8) . . . . ? N2 Cu1 N5 C4 -105.3(8) 4_565 . . . ? O5 Cu1 N5 C4 164.0(7) . . . . ? O6 Cu1 N5 C4 -16.2(8) . . . . ? C4 N5 N6 C3 0.0 . . . . ? Cu1 N5 N6 C3 -172.3(9) . . . . ? N5 N6 C3 N7 0.0 . . . . ? N6 C3 N7 N8 174.2(15) . . . . ? N6 C3 N7 C4 0.0 . . . . ? N8 N7 C4 N5 -174.2(15) . . . . ? C3 N7 C4 N5 0.0 . . . . ? N6 N5 C4 N7 0.0 . . . . ? Cu1 N5 C4 N7 171.8(10) . . . . ? N1 Cu2 N9 C5 -85(3) . . . . ? O1 Cu2 N9 C5 27.9(4) . . . . ? O11 Cu2 N9 C5 -164.3(4) . . . . ? O4 Cu2 N9 C5 -88.7(4) 1_455 . . . ? N1 Cu2 N9 N9 95(2) . . . 4_565 ? O1 Cu2 N9 N9 -151.78(10) . . . 4_565 ? O11 Cu2 N9 N9 15.96(12) . . . 4_565 ? O4 Cu2 N9 N9 91.63(9) 1_455 . . 4_565 ? N1 N2 C1 N3 0.0(5) . . . . ? Cu1 N2 C1 N3 -175.6(3) . . . . ? C2 N3 C1 N2 0.0(6) . . . . ? N4 N3 C1 N2 179.5(5) . . . . ? N2 N1 C2 N3 0.1(5) . . . . ? Cu2 N1 C2 N3 -169.0(3) . . . . ? C1 N3 C2 N1 -0.1(5) . . . . ? N4 N3 C2 N1 -179.6(4) . . . . ? N9 N9 C5 N10 -0.3(4) 4_565 . . . ? Cu2 N9 C5 N10 180.0(3) . . . . ? C5 N10 C5 N9 0.4(7) 4_565 . . . ? N11 N10 C5 N9 178.1(6) . . . . ? C8 C6 C7 C8 -0.9(6) . . . 3_856 ? C9 C6 C7 C8 177.9(4) . . . 3_856 ? C8 C6 C7 C10 179.8(4) . . . . ? C9 C6 C7 C10 -1.4(6) . . . . ? C7 C6 C8 C7 1.0(7) . . . 3_856 ? C9 C6 C8 C7 -177.9(4) . . . 3_856 ? Cu2 O1 C9 O2 9.7(5) . . . . ? Cu2 O1 C9 C6 -173.3(3) . . . . ? C8 C6 C9 O2 117.3(4) . . . . ? C7 C6 C9 O2 -61.5(6) . . . . ? C8 C6 C9 O1 -59.8(5) . . . . ? C7 C6 C9 O1 121.4(4) . . . . ? Cu2 O4 C10 O3 137.5(4) 1_655 . . . ? Cu2 O4 C10 C7 -44.0(6) 1_655 . . . ? C8 C7 C10 O4 -27.1(5) 3_856 . . . ? C6 C7 C10 O4 152.2(4) . . . . ? C8 C7 C10 O3 151.5(4) 3_856 . . . ? C6 C7 C10 O3 -29.3(6) . . . . ? N5 Cu1 O11 Cu2 79(2) . . . . ? N2 Cu1 O11 Cu2 -18.4(2) . . . . ? N2 Cu1 O11 Cu2 160.3(2) 4_565 . . . ? O5 Cu1 O11 Cu2 -109.05(16) . . . . ? O6 Cu1 O11 Cu2 70.95(16) . . . . ? N5 Cu1 O11 Cu2 -63(2) . . . 4_565 ? N2 Cu1 O11 Cu2 -160.3(2) . . . 4_565 ? N2 Cu1 O11 Cu2 18.4(2) 4_565 . . 4_565 ? O5 Cu1 O11 Cu2 109.05(16) . . . 4_565 ? O6 Cu1 O11 Cu2 -70.95(16) . . . 4_565 ? N9 Cu2 O11 Cu1 -169.28(19) . . . . ? N1 Cu2 O11 Cu1 13.92(19) . . . . ? O1 Cu2 O11 Cu1 -84.7(6) . . . . ? O4 Cu2 O11 Cu1 106.39(18) 1_455 . . . ? N9 Cu2 O11 Cu2 -25.56(19) . . . 4_565 ? N1 Cu2 O11 Cu2 157.64(19) . . . 4_565 ? O1 Cu2 O11 Cu2 59.1(7) . . . 4_565 ? O4 Cu2 O11 Cu2 -109.89(19) 1_455 . . 4_565 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.617 _refine_diff_density_min -1.115 _refine_diff_density_rms 0.121 # Attachment '- 90928A-4.cif' data_90928a _database_code_depnum_ccdc_archive 'CCDC 804528' #TrackingRef '- 90928A-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cu N8 O10' _chemical_formula_weight 519.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.067(4) _cell_length_b 7.563(4) _cell_length_c 9.867(5) _cell_angle_alpha 69.266(7) _cell_angle_beta 88.868(8) _cell_angle_gamma 75.042(7) _cell_volume 475.0(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2247 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.92 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.817 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 265 _exptl_absorpt_coefficient_mu 1.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7407 _exptl_absorpt_correction_T_max 0.8372 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2329 _diffrn_reflns_av_R_equivalents 0.0079 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1646 _reflns_number_gt 1589 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.4546P] 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 1646 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0692 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.5000 0.0000 0.01831(13) Uani 1 2 d S . . O1 O 0.2213(2) 0.3505(2) 0.15703(15) 0.0216(3) Uani 1 1 d . . . O2 O 0.2491(2) 0.0449(2) 0.16780(17) 0.0311(4) Uani 1 1 d . . . O3 O 0.6671(2) 0.0905(2) 0.13233(16) 0.0331(4) Uani 1 1 d . . . O4 O 0.8681(2) -0.1839(2) 0.28561(17) 0.0359(4) Uani 1 1 d . . . H4 H 0.9227 -0.1835 0.2114 0.054 Uiso 1 1 calc R . . O5 O 0.0284(2) 0.7874(2) 0.04500(16) 0.0239(3) Uani 1 1 d . . . H5A H -0.0630 0.8719 -0.0166 0.036 Uiso 1 1 d R . . H5B H 0.1341 0.7984 0.0044 0.036 Uiso 1 1 d R . . N1 N -0.1923(3) 0.4771(3) 0.14858(18) 0.0222(4) Uani 1 1 d . . . N2 N -0.1437(3) 0.3651(3) 0.2944(2) 0.0331(5) Uani 1 1 d . . . N3 N -0.4506(3) 0.5352(3) 0.26346(19) 0.0228(4) Uani 1 1 d . . . N4 N -0.6425(3) 0.6053(3) 0.2997(2) 0.0281(4) Uani 1 1 d . . . H4" H -0.6827 0.7372 0.2625 0.042 Uiso 1 1 d R . . H4' H -0.7236 0.5488 0.2708 0.042 Uiso 1 1 d R . . C1 C 0.4023(3) 0.0863(3) 0.3607(2) 0.0186(4) Uani 1 1 d . . . C2 C 0.6004(3) -0.0224(3) 0.3810(2) 0.0190(4) Uani 1 1 d . . . C3 C 0.3051(3) 0.1084(3) 0.4794(2) 0.0212(4) Uani 1 1 d . . . H3 H 0.1746 0.1819 0.4658 0.025 Uiso 1 1 calc R . . C4 C 0.2831(3) 0.1660(3) 0.2156(2) 0.0193(4) Uani 1 1 d . . . C5 C 0.7127(3) -0.0321(3) 0.2535(2) 0.0221(4) Uani 1 1 d . . . C6 C -0.3016(3) 0.4046(4) 0.3597(2) 0.0319(5) Uani 1 1 d . . . H6 H -0.3109 0.3502 0.4593 0.038 Uiso 1 1 calc R . . C7 C -0.3773(3) 0.5763(3) 0.1332(2) 0.0244(5) Uani 1 1 d . . . H7 H -0.4468 0.6620 0.0455 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 Cu1 0.01704(19) 0.0179(2) 0.01384(19) -0.00217(14) -0.00140(13) 0.00083(13) O1 0.0211(7) 0.0196(7) 0.0175(7) -0.0023(6) -0.0039(6) 0.0001(6) O2 0.0360(9) 0.0234(8) 0.0291(9) -0.0081(7) -0.0127(7) -0.0008(7) O3 0.0270(8) 0.0398(9) 0.0173(8) -0.0006(7) 0.0020(6) 0.0026(7) O4 0.0316(9) 0.0367(9) 0.0236(8) -0.0066(7) 0.0050(7) 0.0111(7) O5 0.0210(7) 0.0226(7) 0.0228(8) -0.0052(6) 0.0008(6) -0.0012(6) N1 0.0220(9) 0.0219(9) 0.0167(9) -0.0031(7) -0.0011(7) -0.0014(7) N2 0.0271(10) 0.0379(11) 0.0179(9) 0.0005(8) -0.0006(8) 0.0041(9) N3 0.0196(9) 0.0253(9) 0.0198(9) -0.0065(7) 0.0020(7) -0.0024(7) N4 0.0192(9) 0.0325(10) 0.0285(10) -0.0102(8) 0.0035(8) -0.0011(8) C1 0.0178(10) 0.0168(9) 0.0162(10) -0.0020(8) -0.0019(8) -0.0015(8) C2 0.0177(10) 0.0175(10) 0.0176(10) -0.0039(8) 0.0003(8) -0.0010(8) C3 0.0164(9) 0.0206(10) 0.0204(10) -0.0045(8) -0.0009(8) 0.0011(8) C4 0.0146(9) 0.0219(10) 0.0167(10) -0.0043(8) 0.0011(8) -0.0008(8) C5 0.0182(10) 0.0243(11) 0.0214(11) -0.0071(9) -0.0007(8) -0.0028(8) C6 0.0288(12) 0.0367(13) 0.0176(11) -0.0015(10) 0.0015(9) 0.0007(10) C7 0.0223(10) 0.0267(11) 0.0181(10) -0.0030(9) -0.0009(8) -0.0034(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9719(19) . ? Cu1 N1 1.9719(19) 2_565 ? Cu1 O1 2.0168(15) . ? Cu1 O1 2.0168(15) 2_565 ? Cu1 O5 2.4233(18) 2_565 ? Cu1 O5 2.4233(18) . ? O1 C4 1.264(3) . ? O2 C4 1.242(3) . ? O3 C5 1.212(3) . ? O4 C5 1.315(3) . ? O4 H4 0.8200 . ? O5 H5A 0.8500 . ? O5 H5B 0.8499 . ? N1 C7 1.310(3) . ? N1 N2 1.382(3) . ? N2 C6 1.298(3) . ? N3 C7 1.338(3) . ? N3 C6 1.350(3) . ? N3 N4 1.412(3) . ? N4 H4" 0.9000 . ? N4 H4' 0.9000 . ? C1 C3 1.386(3) . ? C1 C2 1.405(3) . ? C1 C4 1.515(3) . ? C2 C3 1.394(3) 2_656 ? C2 C5 1.488(3) . ? C3 C2 1.394(3) 2_656 ? C3 H3 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 . 2_565 ? N1 Cu1 O1 90.13(8) . . ? N1 Cu1 O1 89.87(8) 2_565 . ? N1 Cu1 O1 89.87(8) . 2_565 ? N1 Cu1 O1 90.13(8) 2_565 2_565 ? O1 Cu1 O1 180.0 . 2_565 ? N1 Cu1 O5 93.90(6) . 2_565 ? N1 Cu1 O5 86.10(6) 2_565 2_565 ? O1 Cu1 O5 94.67(6) . 2_565 ? O1 Cu1 O5 85.33(6) 2_565 2_565 ? N1 Cu1 O5 86.10(6) . . ? N1 Cu1 O5 93.90(6) 2_565 . ? O1 Cu1 O5 85.33(6) . . ? O1 Cu1 O5 94.67(6) 2_565 . ? O5 Cu1 O5 180.0 2_565 . ? C4 O1 Cu1 126.04(13) . . ? C5 O4 H4 109.5 . . ? Cu1 O5 H5A 98.0 . . ? Cu1 O5 H5B 98.0 . . ? H5A O5 H5B 105.2 . . ? C7 N1 N2 108.04(17) . . ? C7 N1 Cu1 127.81(15) . . ? N2 N1 Cu1 123.76(14) . . ? C6 N2 N1 105.96(18) . . ? C7 N3 C6 105.86(18) . . ? C7 N3 N4 129.37(18) . . ? C6 N3 N4 124.77(18) . . ? N3 N4 H4" 111.2 . . ? N3 N4 H4' 109.2 . . ? H4" N4 H4' 112.9 . . ? C3 C1 C2 119.41(19) . . ? C3 C1 C4 117.70(18) . . ? C2 C1 C4 122.66(18) . . ? C3 C2 C1 119.46(19) 2_656 . ? C3 C2 C5 120.14(18) 2_656 . ? C1 C2 C5 120.22(18) . . ? C1 C3 C2 121.13(19) . 2_656 ? C1 C3 H3 119.4 . . ? C2 C3 H3 119.4 2_656 . ? O2 C4 O1 126.00(19) . . ? O2 C4 C1 117.40(18) . . ? O1 C4 C1 116.55(18) . . ? O3 C5 O4 123.4(2) . . ? O3 C5 C2 123.05(19) . . ? O4 C5 C2 113.58(18) . . ? N2 C6 N3 110.8(2) . . ? N2 C6 H6 124.6 . . ? N3 C6 H6 124.6 . . ? N1 C7 N3 109.28(18) . . ? N1 C7 H7 125.4 . . ? N3 C7 H7 125.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 O1 C4 84.12(16) . . . . ? N1 Cu1 O1 C4 -95.87(16) 2_565 . . . ? O1 Cu1 O1 C4 89(16) 2_565 . . . ? O5 Cu1 O1 C4 -9.80(16) 2_565 . . . ? O5 Cu1 O1 C4 170.20(16) . . . . ? N1 Cu1 N1 C7 -67(8) 2_565 . . . ? O1 Cu1 N1 C7 164.62(19) . . . . ? O1 Cu1 N1 C7 -15.38(19) 2_565 . . . ? O5 Cu1 N1 C7 -100.69(19) 2_565 . . . ? O5 Cu1 N1 C7 79.31(19) . . . . ? N1 Cu1 N1 N2 121(8) 2_565 . . . ? O1 Cu1 N1 N2 -7.32(17) . . . . ? O1 Cu1 N1 N2 172.68(17) 2_565 . . . ? O5 Cu1 N1 N2 87.37(17) 2_565 . . . ? O5 Cu1 N1 N2 -92.63(17) . . . . ? C7 N1 N2 C6 -0.7(3) . . . . ? Cu1 N1 N2 C6 172.56(16) . . . . ? C3 C1 C2 C3 0.9(3) . . . 2_656 ? C4 C1 C2 C3 -173.31(18) . . . 2_656 ? C3 C1 C2 C5 -174.22(19) . . . . ? C4 C1 C2 C5 11.5(3) . . . . ? C2 C1 C3 C2 -1.0(3) . . . 2_656 ? C4 C1 C3 C2 173.58(18) . . . 2_656 ? Cu1 O1 C4 O2 16.2(3) . . . . ? Cu1 O1 C4 C1 -161.01(13) . . . . ? C3 C1 C4 O2 -108.4(2) . . . . ? C2 C1 C4 O2 65.9(3) . . . . ? C3 C1 C4 O1 69.0(2) . . . . ? C2 C1 C4 O1 -116.6(2) . . . . ? C3 C2 C5 O3 -152.4(2) 2_656 . . . ? C1 C2 C5 O3 22.7(3) . . . . ? C3 C2 C5 O4 26.2(3) 2_656 . . . ? C1 C2 C5 O4 -158.7(2) . . . . ? N1 N2 C6 N3 0.5(3) . . . . ? C7 N3 C6 N2 -0.1(3) . . . . ? N4 N3 C6 N2 178.8(2) . . . . ? N2 N1 C7 N3 0.7(2) . . . . ? Cu1 N1 C7 N3 -172.25(14) . . . . ? C6 N3 C7 N1 -0.4(2) . . . . ? N4 N3 C7 N1 -179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.316 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.056 # Attachment '- 1.cif' data_n100603d _database_code_depnum_ccdc_archive 'CCDC 804529' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14.50 Cu2 N8 O10.25' _chemical_formula_weight 585.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1419(14) _cell_length_b 8.3005(11) _cell_length_c 24.505(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.030(5) _cell_angle_gamma 90.00 _cell_volume 1961.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5370 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.23 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1178 _exptl_absorpt_coefficient_mu 2.247 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7292 _exptl_absorpt_correction_T_max 0.7901 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8869 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3445 _reflns_number_gt 2906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+6.4952P] 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 3445 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 Cu2 Cu 0.44278(5) 1.03161(6) 0.562867(19) 0.02430(15) Uani 1 1 d . . . Cu1 Cu 0.24111(5) 0.88353(6) 0.652610(19) 0.02242(14) Uani 1 1 d . . . O1 O 0.2590(6) 0.7614(4) 0.77009(14) 0.0795(16) Uani 1 1 d . . . O2 O 0.2418(3) 0.9914(4) 0.72293(11) 0.0278(7) Uani 1 1 d . . . O3 O 0.5516(4) 0.8305(5) 0.85349(14) 0.0489(10) Uani 1 1 d . . . O4 O 0.4511(3) 0.7307(3) 0.91601(11) 0.0280(7) Uani 1 1 d . . . O5 O 0.3918(3) 1.3945(3) 0.98313(11) 0.0246(6) Uani 1 1 d . . . O6 O 0.2145(4) 1.2622(4) 0.99872(13) 0.0413(8) Uani 1 1 d . . . O7 O 0.0780(3) 1.4621(4) 0.88442(15) 0.0442(9) Uani 1 1 d . . . O8 O -0.0735(3) 1.2619(4) 0.85206(12) 0.0282(7) Uani 1 1 d . . . O9 O 0.2212(3) 1.1317(4) 0.61004(12) 0.0338(7) Uani 1 1 d . . . H9A H 0.1948 1.1287 0.5736 0.051 Uiso 1 1 d R . . H9B H 0.2845 1.1989 0.6262 0.051 Uiso 1 1 d R . . O10 O 0.0345(5) 0.7489(6) 0.8304(3) 0.122(3) Uani 1 1 d . . . H10A H 0.0228 0.6664 0.8489 0.182 Uiso 1 1 d R . . H10B H 0.1031 0.7476 0.8174 0.182 Uiso 1 1 d R . . O11 O 0.0000 0.5000 0.0000 0.084(5) Uani 0.50 2 d SP . . N1 N 0.2326(4) 0.7910(4) 0.57514(15) 0.0295(8) Uani 1 1 d . . . N2 N 0.3049(3) 0.8541(4) 0.54058(13) 0.0229(7) Uani 1 1 d . . . N3 N 0.1530(4) 0.6863(5) 0.48983(18) 0.0468(12) Uani 1 1 d . . . N4 N 0.0675(5) 0.5939(7) 0.4437(2) 0.085(2) Uani 1 1 d . . . H4" H 0.0985 0.6044 0.4132 0.102 Uiso 1 1 d R . . H4' H -0.0086 0.6539 0.4408 0.102 Uiso 1 1 d R . . N5 N 0.4521(3) 0.8975(4) 0.67768(13) 0.0232(7) Uani 1 1 d . . . N6 N 0.5261(3) 0.9509(4) 0.64202(13) 0.0219(7) Uani 1 1 d . . . N7 N 0.6701(3) 0.9211(4) 0.72744(14) 0.0277(8) Uani 1 1 d . . . N8 N 0.7908(5) 0.9281(6) 0.7753(2) 0.0713(17) Uani 1 1 d . . . H8" H 0.8518 1.0096 0.7864 0.086 Uiso 1 1 d R . . H8' H 0.8320 0.8311 0.7783 0.086 Uiso 1 1 d R . . C1 C 0.2543(5) 0.7892(5) 0.48954(18) 0.0326(10) Uani 1 1 d . . . H1 H 0.2842 0.8113 0.4581 0.039 Uiso 1 1 calc R . . C2 C 0.1427(5) 0.6893(6) 0.5435(2) 0.0455(13) Uani 1 1 d . . . H2 H 0.0809 0.6281 0.5561 0.055 Uiso 1 1 calc R . . C3 C 0.6562(4) 0.9641(5) 0.67294(16) 0.0236(8) Uani 1 1 d . . . H3 H 0.7279 0.9979 0.6594 0.028 Uiso 1 1 calc R . . C4 C 0.5421(4) 0.8819(5) 0.72876(17) 0.0298(10) Uani 1 1 d . . . H4 H 0.5209 0.8487 0.7613 0.036 Uiso 1 1 calc R . . C5 C 0.2586(4) 1.0035(5) 0.82068(15) 0.0211(8) Uani 1 1 d . . . C6 C 0.3654(4) 0.9751(5) 0.87197(16) 0.0218(8) Uani 1 1 d . . . C7 C 0.3769(4) 1.0746(5) 0.91873(16) 0.0222(8) Uani 1 1 d . . . H7 H 0.4521 1.0625 0.9518 0.027 Uiso 1 1 calc R . . C8 C 0.2777(4) 1.1923(5) 0.91693(15) 0.0200(8) Uani 1 1 d . . . C9 C 0.1624(4) 1.2072(5) 0.86815(16) 0.0199(8) Uani 1 1 d . . . C10 C 0.1565(4) 1.1164(5) 0.81950(15) 0.0199(8) Uani 1 1 d . . . H10 H 0.0834 1.1317 0.7859 0.024 Uiso 1 1 calc R . . C11 C 0.2510(5) 0.9084(5) 0.76726(17) 0.0306(10) Uani 1 1 d . . . C12 C 0.4655(4) 0.8344(5) 0.87949(16) 0.0275(10) Uani 1 1 d . . . C13 C 0.2928(4) 1.2911(5) 0.97034(16) 0.0244(9) Uani 1 1 d . . . C14 C 0.0470(4) 1.3218(5) 0.86815(15) 0.0242(9) 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 Cu2 0.0313(3) 0.0264(3) 0.0141(2) 0.00169(19) 0.00529(19) -0.0104(2) Cu1 0.0208(3) 0.0320(3) 0.0176(2) -0.0017(2) 0.01042(19) -0.0056(2) O1 0.174(5) 0.029(2) 0.0198(17) -0.0026(15) 0.008(2) 0.031(3) O2 0.0261(15) 0.0459(19) 0.0138(13) -0.0008(12) 0.0099(11) -0.0035(13) O3 0.061(2) 0.062(2) 0.0380(18) 0.0203(17) 0.0356(17) 0.0384(19) O4 0.0365(17) 0.0299(16) 0.0200(14) 0.0029(12) 0.0121(12) 0.0122(13) O5 0.0256(15) 0.0288(16) 0.0191(13) -0.0035(12) 0.0064(11) 0.0055(13) O6 0.063(2) 0.044(2) 0.0282(16) -0.0079(14) 0.0310(16) -0.0141(17) O7 0.0312(18) 0.0344(19) 0.061(2) -0.0113(17) 0.0058(16) 0.0137(15) O8 0.0209(15) 0.0388(17) 0.0290(15) 0.0025(13) 0.0134(12) 0.0078(13) O9 0.0423(18) 0.0374(18) 0.0186(14) -0.0006(13) 0.0047(13) -0.0113(15) O10 0.047(3) 0.046(3) 0.249(8) 0.048(4) 0.013(4) -0.001(2) O11 0.049(7) 0.134(13) 0.075(8) -0.068(8) 0.031(6) -0.044(8) N1 0.034(2) 0.030(2) 0.0332(19) -0.0054(16) 0.0226(16) -0.0112(16) N2 0.0257(18) 0.0271(19) 0.0202(16) -0.0013(14) 0.0132(14) -0.0070(15) N3 0.046(2) 0.058(3) 0.048(2) -0.039(2) 0.031(2) -0.033(2) N4 0.073(4) 0.122(5) 0.087(4) -0.087(4) 0.062(3) -0.071(4) N5 0.0227(17) 0.0320(19) 0.0175(16) 0.0041(14) 0.0101(14) 0.0003(15) N6 0.0230(18) 0.0271(19) 0.0195(16) -0.0008(14) 0.0125(14) -0.0038(14) N7 0.0237(18) 0.033(2) 0.0220(17) 0.0013(15) 0.0006(14) 0.0025(15) N8 0.052(3) 0.062(3) 0.062(3) 0.015(3) -0.037(2) -0.007(3) C1 0.036(2) 0.037(3) 0.030(2) -0.012(2) 0.019(2) -0.011(2) C2 0.053(3) 0.048(3) 0.051(3) -0.024(2) 0.039(3) -0.028(3) C3 0.024(2) 0.025(2) 0.025(2) -0.0033(17) 0.0112(17) -0.0007(17) C4 0.032(2) 0.037(3) 0.020(2) 0.0051(18) 0.0086(18) 0.004(2) C5 0.026(2) 0.024(2) 0.0168(18) 0.0006(15) 0.0111(16) 0.0013(16) C6 0.025(2) 0.024(2) 0.0192(19) 0.0041(16) 0.0115(16) 0.0046(17) C7 0.022(2) 0.028(2) 0.0159(18) 0.0011(16) 0.0055(16) 0.0054(17) C8 0.021(2) 0.024(2) 0.0152(18) -0.0009(16) 0.0073(15) 0.0017(16) C9 0.0187(19) 0.023(2) 0.0215(19) 0.0043(16) 0.0109(16) 0.0026(16) C10 0.0201(19) 0.027(2) 0.0129(17) 0.0027(16) 0.0051(15) 0.0007(17) C11 0.036(2) 0.034(3) 0.020(2) -0.0023(19) 0.0076(18) 0.013(2) C12 0.033(2) 0.035(2) 0.0152(19) -0.0015(17) 0.0089(17) 0.0119(19) C13 0.031(2) 0.024(2) 0.0194(19) 0.0046(17) 0.0085(17) 0.0100(18) C14 0.030(2) 0.032(2) 0.0138(18) 0.0027(17) 0.0109(16) 0.0079(19) _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 Cu2 O4 1.953(3) 2_656 ? Cu2 O5 1.958(3) 4_585 ? Cu2 N6 1.978(3) . ? Cu2 N2 1.988(3) . ? Cu1 O2 1.940(3) . ? Cu1 O8 1.950(3) 2_546 ? Cu1 N1 2.025(3) . ? Cu1 N5 2.039(3) . ? Cu1 O9 2.289(3) . ? O1 C11 1.223(6) . ? O2 C11 1.265(5) . ? O3 C12 1.230(5) . ? O4 C12 1.282(5) . ? O4 Cu2 1.953(3) 2_646 ? O5 C13 1.284(5) . ? O5 Cu2 1.958(3) 4_586 ? O6 C13 1.230(5) . ? O7 C14 1.239(5) . ? O8 C14 1.264(5) . ? O8 Cu1 1.950(3) 2_556 ? O9 H9A 0.8500 . ? O9 H9B 0.8500 . ? O10 H10A 0.8501 . ? O10 H10B 0.8502 . ? N1 C2 1.306(6) . ? N1 N2 1.384(4) . ? N2 C1 1.312(5) . ? N3 C1 1.338(6) . ? N3 C2 1.352(6) . ? N3 N4 1.417(5) . ? N4 H4" 0.9000 . ? N4 H4' 0.9019 . ? N5 C4 1.307(5) . ? N5 N6 1.389(4) . ? N6 C3 1.307(5) . ? N7 C3 1.347(5) . ? N7 C4 1.349(6) . ? N7 N8 1.410(5) . ? N8 H8" 0.8999 . ? N8 H8' 0.8999 . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C10 1.391(5) . ? C5 C6 1.402(5) . ? C5 C11 1.510(5) . ? C6 C7 1.388(5) . ? C6 C12 1.521(6) . ? C7 C8 1.393(5) . ? C7 H7 0.9300 . ? C8 C9 1.395(5) . ? C8 C13 1.511(5) . ? C9 C10 1.395(5) . ? C9 C14 1.509(5) . ? C10 H10 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu2 O5 87.31(11) 2_656 4_585 ? O4 Cu2 N6 89.64(13) 2_656 . ? O5 Cu2 N6 170.17(13) 4_585 . ? O4 Cu2 N2 169.51(14) 2_656 . ? O5 Cu2 N2 90.68(12) 4_585 . ? N6 Cu2 N2 93.96(13) . . ? O2 Cu1 O8 93.10(12) . 2_546 ? O2 Cu1 N1 174.42(14) . . ? O8 Cu1 N1 88.00(13) 2_546 . ? O2 Cu1 N5 89.51(12) . . ? O8 Cu1 N5 149.54(13) 2_546 . ? N1 Cu1 N5 92.32(14) . . ? O2 Cu1 O9 88.01(12) . . ? O8 Cu1 O9 119.11(12) 2_546 . ? N1 Cu1 O9 86.68(13) . . ? N5 Cu1 O9 91.29(12) . . ? C11 O2 Cu1 119.4(3) . . ? C12 O4 Cu2 125.5(3) . 2_646 ? C13 O5 Cu2 113.5(2) . 4_586 ? C14 O8 Cu1 123.8(3) . 2_556 ? Cu1 O9 H9A 114.1 . . ? Cu1 O9 H9B 115.5 . . ? H9A O9 H9B 117.1 . . ? H10A O10 H10B 117.1 . . ? C2 N1 N2 106.6(3) . . ? C2 N1 Cu1 128.4(3) . . ? N2 N1 Cu1 123.6(3) . . ? C1 N2 N1 107.7(3) . . ? C1 N2 Cu2 126.9(3) . . ? N1 N2 Cu2 125.0(2) . . ? C1 N3 C2 106.5(4) . . ? C1 N3 N4 128.5(4) . . ? C2 N3 N4 125.0(4) . . ? N3 N4 H4" 108.9 . . ? N3 N4 H4' 93.6 . . ? H4" N4 H4' 112.9 . . ? C4 N5 N6 106.3(3) . . ? C4 N5 Cu1 129.7(3) . . ? N6 N5 Cu1 123.3(2) . . ? C3 N6 N5 107.9(3) . . ? C3 N6 Cu2 126.0(3) . . ? N5 N6 Cu2 125.1(2) . . ? C3 N7 C4 106.3(3) . . ? C3 N7 N8 127.7(4) . . ? C4 N7 N8 125.8(4) . . ? N7 N8 H8" 128.4 . . ? N7 N8 H8' 107.0 . . ? H8" N8 H8' 112.9 . . ? N2 C1 N3 109.4(4) . . ? N2 C1 H1 125.3 . . ? N3 C1 H1 125.3 . . ? N1 C2 N3 109.8(4) . . ? N1 C2 H2 125.1 . . ? N3 C2 H2 125.1 . . ? N6 C3 N7 109.2(4) . . ? N6 C3 H3 125.4 . . ? N7 C3 H3 125.4 . . ? N5 C4 N7 110.2(4) . . ? N5 C4 H4 124.9 . . ? N7 C4 H4 124.9 . . ? C10 C5 C6 119.7(3) . . ? C10 C5 C11 119.8(3) . . ? C6 C5 C11 120.5(4) . . ? C7 C6 C5 119.0(4) . . ? C7 C6 C12 118.3(3) . . ? C5 C6 C12 122.6(3) . . ? C6 C7 C8 121.0(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 C13 118.3(3) . . ? C9 C8 C13 121.8(3) . . ? C8 C9 C10 119.2(3) . . ? C8 C9 C14 120.0(3) . . ? C10 C9 C14 120.8(3) . . ? C5 C10 C9 120.7(3) . . ? C5 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? O1 C11 O2 125.3(4) . . ? O1 C11 C5 119.2(4) . . ? O2 C11 C5 115.5(4) . . ? O3 C12 O4 126.6(4) . . ? O3 C12 C6 120.8(4) . . ? O4 C12 C6 112.6(3) . . ? O6 C13 O5 125.8(4) . . ? O6 C13 C8 118.3(4) . . ? O5 C13 C8 115.8(3) . . ? O7 C14 O8 126.5(4) . . ? O7 C14 C9 118.2(4) . . ? O8 C14 C9 115.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O8 Cu1 O2 C11 60.7(3) 2_546 . . . ? N1 Cu1 O2 C11 161.9(12) . . . . ? N5 Cu1 O2 C11 -89.0(3) . . . . ? O9 Cu1 O2 C11 179.7(3) . . . . ? O2 Cu1 N1 C2 -102.9(13) . . . . ? O8 Cu1 N1 C2 -1.4(5) 2_546 . . . ? N5 Cu1 N1 C2 148.1(5) . . . . ? O9 Cu1 N1 C2 -120.7(5) . . . . ? O2 Cu1 N1 N2 61.8(14) . . . . ? O8 Cu1 N1 N2 163.2(3) 2_546 . . . ? N5 Cu1 N1 N2 -47.2(3) . . . . ? O9 Cu1 N1 N2 43.9(3) . . . . ? C2 N1 N2 C1 0.8(5) . . . . ? Cu1 N1 N2 C1 -166.7(3) . . . . ? C2 N1 N2 Cu2 173.6(3) . . . . ? Cu1 N1 N2 Cu2 6.1(5) . . . . ? O4 Cu2 N2 C1 102.1(7) 2_656 . . . ? O5 Cu2 N2 C1 23.3(4) 4_585 . . . ? N6 Cu2 N2 C1 -148.1(4) . . . . ? O4 Cu2 N2 N1 -69.4(8) 2_656 . . . ? O5 Cu2 N2 N1 -148.2(3) 4_585 . . . ? N6 Cu2 N2 N1 40.5(3) . . . . ? O2 Cu1 N5 C4 37.6(4) . . . . ? O8 Cu1 N5 C4 -57.6(5) 2_546 . . . ? N1 Cu1 N5 C4 -147.6(4) . . . . ? O9 Cu1 N5 C4 125.6(4) . . . . ? O2 Cu1 N5 N6 -132.3(3) . . . . ? O8 Cu1 N5 N6 132.4(3) 2_546 . . . ? N1 Cu1 N5 N6 42.4(3) . . . . ? O9 Cu1 N5 N6 -44.3(3) . . . . ? C4 N5 N6 C3 0.3(5) . . . . ? Cu1 N5 N6 C3 172.3(3) . . . . ? C4 N5 N6 Cu2 -169.0(3) . . . . ? Cu1 N5 N6 Cu2 3.0(4) . . . . ? O4 Cu2 N6 C3 -42.5(3) 2_656 . . . ? O5 Cu2 N6 C3 29.4(10) 4_585 . . . ? N2 Cu2 N6 C3 147.3(3) . . . . ? O4 Cu2 N6 N5 124.9(3) 2_656 . . . ? O5 Cu2 N6 N5 -163.3(6) 4_585 . . . ? N2 Cu2 N6 N5 -45.3(3) . . . . ? N1 N2 C1 N3 -0.3(5) . . . . ? Cu2 N2 C1 N3 -173.0(3) . . . . ? C2 N3 C1 N2 -0.2(6) . . . . ? N4 N3 C1 N2 177.9(5) . . . . ? N2 N1 C2 N3 -0.9(6) . . . . ? Cu1 N1 C2 N3 165.8(3) . . . . ? C1 N3 C2 N1 0.7(6) . . . . ? N4 N3 C2 N1 -177.5(5) . . . . ? N5 N6 C3 N7 0.1(5) . . . . ? Cu2 N6 C3 N7 169.3(3) . . . . ? C4 N7 C3 N6 -0.5(5) . . . . ? N8 N7 C3 N6 -175.4(4) . . . . ? N6 N5 C4 N7 -0.6(5) . . . . ? Cu1 N5 C4 N7 -171.9(3) . . . . ? C3 N7 C4 N5 0.7(5) . . . . ? N8 N7 C4 N5 175.7(4) . . . . ? C10 C5 C6 C7 -8.1(6) . . . . ? C11 C5 C6 C7 174.0(4) . . . . ? C10 C5 C6 C12 169.0(4) . . . . ? C11 C5 C6 C12 -8.9(6) . . . . ? C5 C6 C7 C8 5.6(6) . . . . ? C12 C6 C7 C8 -171.6(4) . . . . ? C6 C7 C8 C9 2.2(6) . . . . ? C6 C7 C8 C13 177.0(4) . . . . ? C7 C8 C9 C10 -7.4(6) . . . . ? C13 C8 C9 C10 178.0(4) . . . . ? C7 C8 C9 C14 173.4(4) . . . . ? C13 C8 C9 C14 -1.2(6) . . . . ? C6 C5 C10 C9 2.9(6) . . . . ? C11 C5 C10 C9 -179.1(4) . . . . ? C8 C9 C10 C5 4.9(6) . . . . ? C14 C9 C10 C5 -176.0(4) . . . . ? Cu1 O2 C11 O1 -0.5(7) . . . . ? Cu1 O2 C11 C5 176.8(3) . . . . ? C10 C5 C11 O1 -128.1(5) . . . . ? C6 C5 C11 O1 49.9(7) . . . . ? C10 C5 C11 O2 54.4(6) . . . . ? C6 C5 C11 O2 -127.6(4) . . . . ? Cu2 O4 C12 O3 -3.4(7) 2_646 . . . ? Cu2 O4 C12 C6 179.0(2) 2_646 . . . ? C7 C6 C12 O3 -114.1(5) . . . . ? C5 C6 C12 O3 68.8(6) . . . . ? C7 C6 C12 O4 63.7(5) . . . . ? C5 C6 C12 O4 -113.4(4) . . . . ? Cu2 O5 C13 O6 15.1(5) 4_586 . . . ? Cu2 O5 C13 C8 -161.9(2) 4_586 . . . ? C7 C8 C13 O6 -105.5(5) . . . . ? C9 C8 C13 O6 69.3(5) . . . . ? C7 C8 C13 O5 71.8(5) . . . . ? C9 C8 C13 O5 -113.5(4) . . . . ? Cu1 O8 C14 O7 1.8(6) 2_556 . . . ? Cu1 O8 C14 C9 -179.5(2) 2_556 . . . ? C8 C9 C14 O7 49.9(5) . . . . ? C10 C9 C14 O7 -129.3(4) . . . . ? C8 C9 C14 O8 -128.9(4) . . . . ? C10 C9 C14 O8 51.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.614 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.084