# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Partha Mukherjee' _publ_contact_author_address ; Bangalore Karnataka India 560012 ; _publ_contact_author_email psm@ipc.iisc.ernet.in _publ_author_name 'Partha Mukherjee' # Attachment 'complex_1-3.cif' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 774587' #TrackingRef 'complex_1-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 Cu N9 O5, (N, 3O)' _chemical_formula_sum 'C10 H12 Cu N10 O8' _chemical_formula_weight 463.85 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0434(2) _cell_length_b 8.7481(3) _cell_length_c 13.6485(4) _cell_angle_alpha 98.392(2) _cell_angle_beta 92.024(2) _cell_angle_gamma 97.2620(10) _cell_volume 824.05(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 470 _exptl_absorpt_coefficient_mu 1.398 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6956 _exptl_absorpt_correction_T_max 0.7485 _exptl_absorpt_process_details 'SADABS: Blessing, R. (1995), Acta Cryst., A51, 33' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12999 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 30.61 _reflns_number_total 5008 _reflns_number_gt 4136 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows(Farrugia, 1997)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0498P)^2^+0.4964P] 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 5008 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.17026(4) 0.47240(3) 0.253069(18) 0.03088(9) Uani 1 1 d . . . O1 O 0.1206(3) 0.7877(2) 0.37283(14) 0.0413(4) Uani 1 1 d . . . O2 O 0.1281(3) 0.1446(2) 0.13022(14) 0.0447(4) Uani 1 1 d . . . O3 O -0.1575(2) 0.4153(2) 0.26009(12) 0.0386(4) Uani 1 1 d . . . O4 O -0.1881(3) 0.6522(2) 0.23683(13) 0.0477(4) Uani 1 1 d . . . O5 O -0.4377(3) 0.4810(3) 0.23719(16) 0.0637(6) Uani 1 1 d . . . O6 O 0.7648(5) 0.0294(3) 0.16893(18) 0.0818(8) Uani 1 1 d . . . O7 O 0.8953(4) 0.0283(3) 0.3119(2) 0.0870(9) Uani 1 1 d . . . O8 O 0.5943(4) -0.0047(3) 0.2935(2) 0.0798(8) Uani 1 1 d . . . N1 N 0.2428(2) 0.3540(2) 0.36345(13) 0.0281(3) Uani 1 1 d . . . N2 N 0.1696(3) 0.6358(2) 0.36901(13) 0.0308(4) Uani 1 1 d . . . N3 N 0.2300(2) 0.6068(2) 0.14598(13) 0.0291(3) Uani 1 1 d . . . N4 N 0.1566(3) 0.3075(2) 0.13664(13) 0.0316(4) Uani 1 1 d . . . N5 N 0.2926(3) 0.3932(2) 0.53935(14) 0.0349(4) Uani 1 1 d . . . N6 N 0.1979(3) 0.6903(3) 0.54317(15) 0.0363(4) Uani 1 1 d . . . H6A H 0.181(4) 0.780(4) 0.542(2) 0.037(8) Uiso 1 1 d . . . H6B H 0.219(4) 0.652(4) 0.590(2) 0.047(9) Uiso 1 1 d . . . N7 N 0.2762(3) 0.5769(3) -0.02714(15) 0.0400(4) Uani 1 1 d . . . N8 N 0.1938(4) 0.2607(3) -0.03491(16) 0.0430(5) Uani 1 1 d . . . H8A H 0.172(5) 0.166(4) -0.032(2) 0.052(9) Uiso 1 1 d . . . H8B H 0.208(4) 0.301(4) -0.082(2) 0.047(9) Uiso 1 1 d . . . N9 N -0.2643(3) 0.5167(3) 0.24431(13) 0.0365(4) Uani 1 1 d . . . N10 N 0.7490(3) 0.0174(2) 0.25802(17) 0.0431(5) Uani 1 1 d . . . C1 C 0.2850(3) 0.2078(3) 0.35896(18) 0.0356(5) Uani 1 1 d . . . H1 H 0.274(4) 0.149(3) 0.294(2) 0.042(7) Uiso 1 1 d . . . C2 C 0.3273(4) 0.1485(3) 0.44498(19) 0.0404(5) Uani 1 1 d . . . H2 H 0.348(4) 0.041(4) 0.440(2) 0.043(8) Uiso 1 1 d . . . C3 C 0.3287(4) 0.2453(3) 0.53388(18) 0.0383(5) Uani 1 1 d . . . H3 H 0.359(4) 0.211(3) 0.589(2) 0.040(7) Uiso 1 1 d . . . C4 C 0.2511(3) 0.4387(2) 0.45418(15) 0.0280(4) Uani 1 1 d . . . C5 C 0.2044(3) 0.6007(2) 0.45635(15) 0.0276(4) Uani 1 1 d . . . C6 C 0.2775(4) 0.7612(3) 0.15214(19) 0.0387(5) Uani 1 1 d . . . H6 H 0.278(4) 0.814(4) 0.213(2) 0.050(8) Uiso 1 1 d . . . C7 C 0.3238(4) 0.8284(3) 0.0694(2) 0.0438(6) Uani 1 1 d . . . H7 H 0.363(5) 0.943(4) 0.079(2) 0.059(9) Uiso 1 1 d . . . C8 C 0.3199(4) 0.7327(3) -0.0195(2) 0.0447(6) Uani 1 1 d . . . H4 H 0.350(4) 0.772(3) -0.075(2) 0.045(8) Uiso 1 1 d . . . C9 C 0.2353(3) 0.5234(3) 0.05587(15) 0.0283(4) Uani 1 1 d . . . C10 C 0.1925(3) 0.3515(3) 0.05193(15) 0.0290(4) Uani 1 1 d . . . H8 H 0.033(5) 0.773(4) 0.333(3) 0.058(10) Uiso 1 1 d . . . H9 H 0.035(5) 0.129(4) 0.152(3) 0.056(11) Uiso 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 0.04430(16) 0.02889(15) 0.01828(13) 0.00023(9) 0.00079(9) 0.00451(10) O1 0.0564(11) 0.0323(9) 0.0362(9) 0.0029(7) -0.0023(8) 0.0137(8) O2 0.0673(13) 0.0294(9) 0.0359(9) 0.0010(7) 0.0079(9) 0.0036(8) O3 0.0387(8) 0.0452(10) 0.0322(8) 0.0045(7) 0.0020(6) 0.0089(7) O4 0.0645(11) 0.0469(11) 0.0325(9) 0.0084(8) -0.0030(8) 0.0099(9) O5 0.0288(8) 0.112(2) 0.0517(12) 0.0133(12) 0.0010(8) 0.0123(10) O6 0.155(3) 0.0499(13) 0.0413(12) 0.0068(10) 0.0079(14) 0.0153(15) O7 0.0601(14) 0.0761(18) 0.115(2) -0.0103(16) -0.0324(15) 0.0093(12) O8 0.0617(14) 0.0776(17) 0.102(2) 0.0100(15) 0.0304(14) 0.0132(12) N1 0.0301(8) 0.0311(9) 0.0218(8) 0.0017(7) 0.0009(6) 0.0022(6) N2 0.0393(9) 0.0276(9) 0.0244(8) 0.0003(7) -0.0004(7) 0.0055(7) N3 0.0317(8) 0.0323(9) 0.0231(8) 0.0019(7) 0.0003(6) 0.0061(7) N4 0.0404(9) 0.0282(9) 0.0252(8) -0.0001(7) 0.0017(7) 0.0051(7) N5 0.0404(10) 0.0407(11) 0.0242(9) 0.0058(8) 0.0009(7) 0.0067(8) N6 0.0511(11) 0.0337(11) 0.0225(9) -0.0010(8) 0.0010(8) 0.0056(9) N7 0.0521(11) 0.0427(11) 0.0265(9) 0.0080(8) 0.0036(8) 0.0077(9) N8 0.0671(14) 0.0368(12) 0.0243(10) -0.0002(9) 0.0059(9) 0.0080(10) N9 0.0349(9) 0.0559(13) 0.0193(8) 0.0034(8) 0.0015(6) 0.0105(9) N10 0.0513(12) 0.0306(10) 0.0450(12) -0.0015(9) 0.0019(9) 0.0044(9) C1 0.0415(11) 0.0335(11) 0.0311(11) 0.0000(9) 0.0011(9) 0.0080(9) C2 0.0471(13) 0.0370(13) 0.0397(13) 0.0104(10) 0.0013(10) 0.0107(10) C3 0.0429(12) 0.0442(13) 0.0308(11) 0.0124(10) 0.0027(9) 0.0086(10) C4 0.0264(9) 0.0327(10) 0.0237(9) 0.0026(8) 0.0017(7) 0.0008(7) C5 0.0266(8) 0.0299(10) 0.0237(9) -0.0008(8) 0.0001(7) 0.0000(7) C6 0.0464(12) 0.0335(12) 0.0342(12) 0.0010(10) 0.0026(9) 0.0024(9) C7 0.0519(14) 0.0361(13) 0.0449(14) 0.0112(11) 0.0070(11) 0.0041(10) C8 0.0564(15) 0.0441(14) 0.0368(13) 0.0166(11) 0.0048(11) 0.0057(11) C9 0.0290(9) 0.0333(11) 0.0230(9) 0.0039(8) -0.0002(7) 0.0065(7) C10 0.0315(9) 0.0321(10) 0.0229(9) -0.0002(8) -0.0006(7) 0.0081(8) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.9721(18) . ? Cu1 N4 1.9749(18) . ? Cu1 N3 2.0289(18) . ? Cu1 N1 2.0342(18) . ? Cu1 O3 2.3081(17) . ? O1 N2 1.408(2) . ? O1 H8 0.79(4) . ? O2 N4 1.403(3) . ? O2 H9 0.73(3) . ? O3 N9 1.270(3) . ? O4 N9 1.258(3) . ? O5 N9 1.218(3) . ? O6 N10 1.243(3) . ? O7 N10 1.230(3) . ? O8 N10 1.213(3) . ? N1 C4 1.342(3) . ? N1 C1 1.342(3) . ? N2 C5 1.296(3) . ? N3 C6 1.339(3) . ? N3 C9 1.340(3) . ? N4 C10 1.294(3) . ? N5 C4 1.318(3) . ? N5 C3 1.342(3) . ? N6 C5 1.328(3) . ? N6 H6A 0.81(3) . ? N6 H6B 0.78(3) . ? N7 C9 1.315(3) . ? N7 C8 1.347(3) . ? N8 C10 1.328(3) . ? N8 H8A 0.83(3) . ? N8 H8B 0.78(3) . ? C1 C2 1.389(3) . ? C1 H1 0.95(3) . ? C2 C3 1.374(4) . ? C2 H2 0.97(3) . ? C3 H3 0.88(3) . ? C4 C5 1.491(3) . ? C6 C7 1.378(4) . ? C6 H6 0.88(3) . ? C7 C8 1.366(4) . ? C7 H7 1.00(3) . ? C8 H4 0.90(3) . ? C9 C10 1.488(3) . ? 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 N4 177.11(8) . . ? N2 Cu1 N3 100.06(7) . . ? N4 Cu1 N3 80.51(7) . . ? N2 Cu1 N1 79.88(7) . . ? N4 Cu1 N1 100.87(8) . . ? N3 Cu1 N1 153.75(7) . . ? N2 Cu1 O3 88.89(7) . . ? N4 Cu1 O3 88.26(7) . . ? N3 Cu1 O3 109.62(7) . . ? N1 Cu1 O3 96.63(6) . . ? N2 O1 H8 101(3) . . ? N4 O2 H9 104(3) . . ? N9 O3 Cu1 119.45(14) . . ? C4 N1 C1 116.34(19) . . ? C4 N1 Cu1 113.46(14) . . ? C1 N1 Cu1 130.20(15) . . ? C5 N2 O1 112.53(17) . . ? C5 N2 Cu1 118.25(15) . . ? O1 N2 Cu1 129.00(14) . . ? C6 N3 C9 116.01(19) . . ? C6 N3 Cu1 130.76(16) . . ? C9 N3 Cu1 113.02(14) . . ? C10 N4 O2 112.18(18) . . ? C10 N4 Cu1 117.11(15) . . ? O2 N4 Cu1 130.50(14) . . ? C4 N5 C3 115.8(2) . . ? C5 N6 H6A 117(2) . . ? C5 N6 H6B 116(2) . . ? H6A N6 H6B 127(3) . . ? C9 N7 C8 115.8(2) . . ? C10 N8 H8A 114(2) . . ? C10 N8 H8B 118(2) . . ? H8A N8 H8B 128(3) . . ? O5 N9 O4 121.6(2) . . ? O5 N9 O3 119.4(2) . . ? O4 N9 O3 118.98(19) . . ? O8 N10 O7 118.9(3) . . ? O8 N10 O6 122.2(3) . . ? O7 N10 O6 118.8(3) . . ? N1 C1 C2 120.7(2) . . ? N1 C1 H1 114.7(17) . . ? C2 C1 H1 124.4(17) . . ? C3 C2 C1 117.8(2) . . ? C3 C2 H2 122.9(18) . . ? C1 C2 H2 119.2(18) . . ? N5 C3 C2 122.2(2) . . ? N5 C3 H3 118.4(19) . . ? C2 C3 H3 119.4(19) . . ? N5 C4 N1 127.2(2) . . ? N5 C4 C5 117.94(19) . . ? N1 C4 C5 114.90(18) . . ? N2 C5 N6 127.3(2) . . ? N2 C5 C4 113.44(18) . . ? N6 C5 C4 119.3(2) . . ? N3 C6 C7 121.1(2) . . ? N3 C6 H6 115(2) . . ? C7 C6 H6 124(2) . . ? C8 C7 C6 118.0(2) . . ? C8 C7 H7 124.0(19) . . ? C6 C7 H7 117.9(19) . . ? N7 C8 C7 121.9(2) . . ? N7 C8 H4 117.4(19) . . ? C7 C8 H4 120.8(19) . . ? N7 C9 N3 127.1(2) . . ? N7 C9 C10 117.83(19) . . ? N3 C9 C10 115.02(18) . . ? N4 C10 N8 127.0(2) . . ? N4 C10 C9 114.30(18) . . ? N8 C10 C9 118.7(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 N8 H8B O4 0.78(3) 2.22(3) 2.965(3) 162(3) 2_565 N8 H8A O6 0.83(3) 2.44(3) 2.956(3) 122(3) 2_655 N6 H6B O3 0.78(3) 2.25(3) 2.976(3) 154(3) 2_566 N6 H6A O7 0.81(3) 2.53(3) 3.079(4) 126(2) 2_666 O2 H9 O6 0.73(3) 2.03(3) 2.728(4) 160(4) 1_455 O1 H8 O4 0.79(4) 2.07(4) 2.828(3) 159(3) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 30.61 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.553 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.071 #===END data_complex2 _database_code_depnum_ccdc_archive 'CCDC 774588' #TrackingRef 'complex_1-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 Cu4 N17 O7, (N 3O), (2H O)' _chemical_formula_sum 'C20 H20 Cu4 N18 O11' _chemical_formula_weight 942.6760 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 27.924(6) _cell_length_b 16.597(3) _cell_length_c 15.514(3) _cell_angle_alpha 90.00 _cell_angle_beta 121.934(8) _cell_angle_gamma 90.00 _cell_volume 6102(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.050 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3752 _exptl_absorpt_coefficient_mu 2.826 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 0.735 _exptl_absorpt_process_details 'SADABS: Blessing, R. (1995), Acta Cryst., A51, 33' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59658 _diffrn_reflns_av_R_equivalents 0.1045 _diffrn_reflns_av_sigmaI/netI 0.1029 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 30.77 _reflns_number_total 9270 _reflns_number_gt 4120 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows(Farrugia, 1997)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.1178P)^2^+8.6046P] 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 9270 _refine_ls_number_parameters 495 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1760 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.2403 _refine_ls_wR_factor_gt 0.1651 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.004 _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 0.02672(3) 0.05045(4) 0.43154(6) 0.0362(2) Uani 1 1 d . . . Cu2 Cu -0.07412(4) -0.04643(4) 0.22502(6) 0.0371(2) Uani 1 1 d . . . Cu3 Cu 0.04797(4) 0.33228(5) 0.46459(6) 0.0395(2) Uani 1 1 d . . . Cu4 Cu -0.05938(3) 0.23535(5) 0.27091(6) 0.0376(2) Uani 1 1 d . . . O1 O 0.01283(19) 0.2336(2) 0.3973(4) 0.0419(11) Uani 1 1 d . . . O2 O -0.03971(19) 0.0517(2) 0.2970(3) 0.0395(11) Uani 1 1 d . . . O3 O 0.02375(19) -0.0667(3) 0.4316(3) 0.0453(12) Uani 1 1 d . . . O4 O -0.0586(2) 0.3526(3) 0.2712(4) 0.0485(13) Uani 1 1 d . . . O5 O -0.1031(2) 0.2186(3) 0.3676(4) 0.0568(14) Uani 1 1 d . . . O6 O 0.1770(3) 0.5029(5) 0.8576(6) 0.127(4) Uani 1 1 d . . . O7 O 0.2531(4) 0.4424(5) 0.9534(7) 0.144(4) Uani 1 1 d . . . O8 O 0.2143(6) 0.5070(6) 1.0120(9) 0.176(6) Uani 1 1 d . . . O9 O -0.1798(4) 0.2364(7) 0.3631(8) 0.170(5) Uani 1 1 d . . . O10 O -0.1844(3) 0.1941(5) 0.2344(5) 0.084(2) Uani 1 1 d . . . N1 N -0.0673(2) 0.1202(3) 0.2381(4) 0.0349(12) Uani 1 1 d . . . N2 N 0.0991(3) 0.2632(3) 0.5712(5) 0.0395(14) Uani 1 1 d . . . N3 N 0.0987(2) 0.0456(3) 0.5703(4) 0.0323(12) Uani 1 1 d . . . N4 N 0.0408(2) 0.1651(3) 0.4572(4) 0.0345(12) Uani 1 1 d . . . N5 N -0.1232(3) 0.0239(3) 0.1198(4) 0.0430(14) Uani 1 1 d . . . H5 H -0.156(3) 0.029(4) 0.058(5) 0.036(18) Uiso 1 1 d . . . N6 N -0.0180(2) -0.1025(3) 0.3453(4) 0.0379(13) Uani 1 1 d . . . N7 N 0.0459(3) 0.5782(4) 0.4536(5) 0.0505(16) Uani 1 1 d . . . N8 N -0.0509(3) 0.5157(3) 0.2834(5) 0.0512(17) Uani 1 1 d . . . H8A H -0.0810 0.4968 0.2312 0.061 Uiso 1 1 calc R . . H8B H -0.0457 0.5669 0.2913 0.061 Uiso 1 1 calc R . . N9 N -0.1006(2) -0.1597(3) 0.1764(4) 0.0396(13) Uani 1 1 d . . . N10 N 0.0757(3) 0.4445(3) 0.5065(5) 0.0435(14) Uani 1 1 d . . . N11 N -0.1268(2) 0.2409(3) 0.1292(4) 0.0372(13) Uani 1 1 d . . . N12 N 0.0179(2) -0.2309(3) 0.4114(4) 0.0394(13) Uani 1 1 d . . . H12A H 0.0454 -0.2126 0.4680 0.047 Uiso 1 1 calc R . . H12B H 0.0139 -0.2820 0.4008 0.047 Uiso 1 1 calc R . . N13 N -0.1860(2) 0.1547(3) -0.0089(4) 0.0418(13) Uani 1 1 d . . . N14 N 0.1643(3) 0.1334(4) 0.7005(4) 0.0469(15) Uani 1 1 d . . . N15 N -0.1559(3) 0.2194(4) 0.3236(5) 0.0528(16) Uani 1 1 d . . . N16 N -0.0133(2) 0.3877(3) 0.3517(4) 0.0436(14) Uani 1 1 d . . . N17 N -0.0747(3) -0.2928(3) 0.2351(4) 0.0446(14) Uani 1 1 d . . . N18 N 0.2142(4) 0.4829(4) 0.9401(7) 0.074(2) Uani 1 1 d . . . C1 C 0.0849(3) 0.1876(4) 0.5454(5) 0.0361(15) Uani 1 1 d . . . C2 C 0.0389(3) 0.4994(4) 0.4411(5) 0.0395(16) Uani 1 1 d . . . C3 C -0.0121(3) 0.4654(4) 0.3523(5) 0.0402(16) Uani 1 1 d . . . C4 C -0.0179(3) -0.1812(3) 0.3416(5) 0.0310(13) Uani 1 1 d . . . C5 C -0.1106(3) 0.0992(4) 0.1494(5) 0.0366(15) Uani 1 1 d . . . C6 C -0.1439(3) 0.1679(4) 0.0840(5) 0.0351(14) Uani 1 1 d . . . C7 C 0.1187(3) 0.1191(4) 0.6115(5) 0.0359(15) Uani 1 1 d . . . C8 C -0.0664(3) -0.2145(4) 0.2470(5) 0.0382(15) Uani 1 1 d . . . C9 C -0.2140(3) 0.2193(5) -0.0630(5) 0.0449(18) Uani 1 1 d . . . H9 H -0.2437 0.2123 -0.1297 0.054 Uiso 1 1 calc R . . C10 C 0.1939(3) 0.0694(5) 0.7550(6) 0.054(2) Uani 1 1 d . . . H10 H 0.2260 0.0770 0.8191 0.065 Uiso 1 1 calc R . . C11 C -0.1555(3) 0.3067(4) 0.0738(5) 0.0416(16) Uani 1 1 d . . . H11 H -0.1448 0.3579 0.1017 0.050 Uiso 1 1 calc R . . C12 C 0.1291(3) -0.0184(4) 0.6247(6) 0.0505(19) Uani 1 1 d . . . H12 H 0.1172 -0.0702 0.5994 0.061 Uiso 1 1 calc R . . C13 C 0.1778(4) -0.0073(5) 0.7179(6) 0.061(2) Uani 1 1 d . . . H13 H 0.1996 -0.0513 0.7552 0.073 Uiso 1 1 calc R . . C14 C 0.1228(3) 0.4706(5) 0.5902(6) 0.054(2) Uani 1 1 d . . . H14 H 0.1487 0.4331 0.6353 0.064 Uiso 1 1 calc R . . C15 C -0.1576(4) -0.2644(5) 0.0747(6) 0.055(2) Uani 1 1 d . . . H15 H -0.1898 -0.2829 0.0160 0.066 Uiso 1 1 calc R . . C16 C -0.1464(3) -0.1848(4) 0.0911(6) 0.0507(19) Uani 1 1 d . . . H16 H -0.1707 -0.1476 0.0428 0.061 Uiso 1 1 calc R . . C17 C -0.2002(3) 0.2969(5) -0.0234(5) 0.0487(18) Uani 1 1 d . . . H17 H -0.2209 0.3411 -0.0621 0.058 Uiso 1 1 calc R . . C18 C 0.1335(4) 0.5504(5) 0.6109(7) 0.063(2) Uani 1 1 d . . . H18 H 0.1657 0.5689 0.6695 0.076 Uiso 1 1 calc R . . C19 C -0.1193(4) -0.3181(4) 0.1488(6) 0.058(2) Uani 1 1 d . . . H19 H -0.1254 -0.3732 0.1372 0.069 Uiso 1 1 calc R . . C20 C 0.0930(4) 0.6031(5) 0.5384(7) 0.064(2) Uani 1 1 d . . . H20 H 0.0992 0.6583 0.5495 0.077 Uiso 1 1 calc R . . O1W O 0.2070(3) 0.3430(5) 0.7617(6) 0.087(2) Uani 1 1 d D . . H1W H 0.235(3) 0.308(5) 0.782(7) 0.08(3) Uiso 1 1 d D . . H2W H 0.219(3) 0.370(4) 0.813(4) 0.04(2) Uiso 1 1 d D . . H2 H 0.121(2) 0.270(3) 0.627(4) 0.012(15) Uiso 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 0.0401(5) 0.0283(4) 0.0357(5) 0.0052(3) 0.0170(4) 0.0009(3) Cu2 0.0460(5) 0.0292(4) 0.0346(5) 0.0036(3) 0.0203(4) 0.0052(3) Cu3 0.0414(5) 0.0278(4) 0.0431(5) 0.0046(3) 0.0181(4) 0.0023(3) Cu4 0.0424(5) 0.0289(4) 0.0353(5) 0.0055(3) 0.0164(4) 0.0019(3) O1 0.040(3) 0.024(2) 0.044(3) 0.0098(19) 0.010(2) 0.0057(19) O2 0.046(3) 0.026(2) 0.039(3) 0.0050(18) 0.017(2) -0.0013(19) O3 0.047(3) 0.031(2) 0.040(3) 0.005(2) 0.011(2) 0.001(2) O4 0.051(3) 0.025(2) 0.042(3) 0.0089(19) 0.006(2) 0.002(2) O5 0.060(4) 0.067(4) 0.041(3) -0.005(3) 0.025(3) -0.004(3) O6 0.093(6) 0.083(5) 0.109(6) 0.018(5) -0.013(5) 0.018(4) O7 0.109(7) 0.110(7) 0.148(9) -0.024(6) 0.025(6) 0.048(6) O8 0.331(18) 0.109(8) 0.164(11) 0.044(7) 0.183(12) 0.061(9) O9 0.117(7) 0.286(13) 0.164(9) -0.146(9) 0.113(7) -0.087(8) O10 0.073(4) 0.109(6) 0.064(5) 0.019(4) 0.032(4) 0.014(4) N1 0.041(3) 0.029(3) 0.030(3) 0.008(2) 0.016(2) 0.004(2) N2 0.037(3) 0.036(3) 0.032(3) -0.006(3) 0.010(3) -0.008(2) N3 0.034(3) 0.025(2) 0.038(3) 0.007(2) 0.020(2) 0.004(2) N4 0.039(3) 0.024(2) 0.039(3) 0.002(2) 0.019(3) 0.002(2) N5 0.055(4) 0.034(3) 0.029(3) 0.003(2) 0.014(3) 0.009(3) N6 0.038(3) 0.029(3) 0.041(3) -0.001(2) 0.017(3) 0.000(2) N7 0.054(4) 0.036(3) 0.050(4) 0.007(3) 0.020(3) 0.005(3) N8 0.065(4) 0.020(3) 0.055(4) 0.008(2) 0.023(3) 0.004(3) N9 0.047(3) 0.036(3) 0.033(3) 0.001(2) 0.019(3) 0.006(2) N10 0.045(3) 0.031(3) 0.048(4) 0.001(2) 0.020(3) -0.002(2) N11 0.041(3) 0.030(3) 0.034(3) 0.007(2) 0.015(3) 0.008(2) N12 0.046(3) 0.022(2) 0.047(4) 0.002(2) 0.022(3) -0.001(2) N13 0.044(3) 0.050(3) 0.031(3) 0.008(3) 0.020(3) 0.009(3) N14 0.053(4) 0.052(4) 0.030(3) -0.002(3) 0.018(3) 0.002(3) N15 0.054(4) 0.051(4) 0.049(4) -0.005(3) 0.025(4) -0.007(3) N16 0.045(3) 0.035(3) 0.040(3) 0.005(2) 0.015(3) 0.001(2) N17 0.056(4) 0.037(3) 0.039(3) 0.001(3) 0.024(3) 0.001(3) N18 0.074(6) 0.045(4) 0.087(7) 0.000(4) 0.033(5) 0.003(4) C1 0.046(4) 0.031(3) 0.033(4) 0.003(3) 0.022(3) 0.005(3) C2 0.044(4) 0.033(3) 0.043(4) 0.004(3) 0.024(3) -0.004(3) C3 0.046(4) 0.032(3) 0.043(4) 0.009(3) 0.024(3) 0.007(3) C4 0.038(3) 0.028(3) 0.031(3) 0.008(2) 0.021(3) 0.005(2) C5 0.048(4) 0.042(4) 0.029(3) 0.002(3) 0.027(3) 0.004(3) C6 0.041(4) 0.042(3) 0.026(3) 0.010(3) 0.021(3) 0.013(3) C7 0.040(4) 0.048(4) 0.027(3) 0.014(3) 0.022(3) 0.014(3) C8 0.052(4) 0.037(4) 0.032(4) -0.001(3) 0.026(3) 0.002(3) C9 0.029(3) 0.069(5) 0.030(4) 0.011(3) 0.011(3) 0.016(3) C10 0.049(4) 0.055(5) 0.044(4) 0.007(4) 0.015(4) 0.004(4) C11 0.044(4) 0.042(4) 0.030(4) 0.004(3) 0.013(3) 0.000(3) C12 0.056(5) 0.036(4) 0.049(5) 0.000(3) 0.020(4) 0.007(3) C13 0.064(5) 0.045(4) 0.055(5) 0.013(4) 0.019(4) 0.015(4) C14 0.047(4) 0.045(4) 0.051(5) 0.003(3) 0.014(4) 0.002(3) C15 0.060(5) 0.048(4) 0.038(4) -0.003(3) 0.013(4) 0.004(4) C16 0.057(5) 0.043(4) 0.038(4) -0.002(3) 0.016(4) 0.004(3) C17 0.049(4) 0.060(5) 0.036(4) 0.015(3) 0.022(4) 0.019(4) C18 0.064(5) 0.049(5) 0.064(6) 0.000(4) 0.024(5) 0.004(4) C19 0.079(6) 0.031(4) 0.063(5) -0.004(3) 0.037(5) -0.009(4) C20 0.086(7) 0.034(4) 0.068(6) -0.008(4) 0.038(5) -0.003(4) O1W 0.074(5) 0.098(6) 0.072(5) -0.011(4) 0.026(4) 0.019(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.924(5) . ? Cu1 N4 1.941(5) . ? Cu1 O3 1.945(5) . ? Cu1 N3 2.026(5) . ? Cu2 N5 1.881(6) . ? Cu2 O2 1.920(4) . ? Cu2 N6 1.926(5) . ? Cu2 N9 2.014(5) . ? Cu3 N2 1.895(6) . ? Cu3 O1 1.911(4) . ? Cu3 N16 1.916(5) . ? Cu3 N10 1.989(5) . ? Cu4 O1 1.931(5) . ? Cu4 O4 1.947(4) . ? Cu4 N1 1.960(5) . ? Cu4 N11 2.002(5) . ? Cu4 O5 2.400(6) . ? O1 N4 1.415(6) . ? O2 N1 1.407(6) . ? O3 N6 1.361(7) . ? O4 N16 1.351(7) . ? O5 N15 1.255(8) . ? O6 N18 1.192(10) . ? O7 N18 1.197(10) . ? O8 N18 1.185(11) . ? O9 N15 1.155(10) . ? O10 N15 1.249(9) . ? N1 C5 1.310(8) . ? N2 C1 1.314(8) . ? N2 H2 0.76(6) . ? N3 C12 1.342(8) . ? N3 C7 1.353(8) . ? N4 C1 1.320(8) . ? N5 C5 1.314(8) . ? N5 H5 0.91(7) . ? N6 C4 1.308(8) . ? N7 C2 1.323(9) . ? N7 C20 1.343(10) . ? N8 C3 1.337(8) . ? N8 H8A 0.8600 . ? N8 H8B 0.8600 . ? N9 C16 1.331(9) . ? N9 C8 1.353(8) . ? N10 C14 1.341(9) . ? N10 C2 1.346(9) . ? N11 C6 1.354(8) . ? N11 C11 1.358(8) . ? N12 C4 1.307(8) . ? N12 H12A 0.8600 . ? N12 H12B 0.8600 . ? N13 C6 1.309(9) . ? N13 C9 1.330(8) . ? N14 C7 1.314(8) . ? N14 C10 1.338(9) . ? N16 C3 1.290(8) . ? N17 C8 1.317(8) . ? N17 C19 1.326(10) . ? C1 C7 1.487(8) . ? C2 C3 1.472(10) . ? C4 C8 1.480(9) . ? C5 C6 1.481(9) . ? C9 C17 1.392(11) . ? C9 H9 0.9300 . ? C10 C13 1.370(11) . ? C10 H10 0.9300 . ? C11 C17 1.366(10) . ? C11 H11 0.9300 . ? C12 C13 1.378(11) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C18 1.360(10) . ? C14 H14 0.9300 . ? C15 C16 1.350(10) . ? C15 C19 1.400(11) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C20 1.401(11) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O1W H1W 0.89(5) . ? O1W H2W 0.81(4) . ? 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 O2 Cu1 N4 100.8(2) . . ? O2 Cu1 O3 89.67(18) . . ? N4 Cu1 O3 169.5(2) . . ? O2 Cu1 N3 177.0(2) . . ? N4 Cu1 N3 80.9(2) . . ? O3 Cu1 N3 88.76(19) . . ? N5 Cu2 O2 83.6(2) . . ? N5 Cu2 N6 170.5(2) . . ? O2 Cu2 N6 86.9(2) . . ? N5 Cu2 N9 107.4(2) . . ? O2 Cu2 N9 168.7(2) . . ? N6 Cu2 N9 82.1(2) . . ? N2 Cu3 O1 83.7(2) . . ? N2 Cu3 N16 170.0(2) . . ? O1 Cu3 N16 87.7(2) . . ? N2 Cu3 N10 107.3(2) . . ? O1 Cu3 N10 168.4(2) . . ? N16 Cu3 N10 81.6(2) . . ? O1 Cu4 O4 90.44(18) . . ? O1 Cu4 N1 99.41(19) . . ? O4 Cu4 N1 167.2(2) . . ? O1 Cu4 N11 170.4(2) . . ? O4 Cu4 N11 87.7(2) . . ? N1 Cu4 N11 81.2(2) . . ? O1 Cu4 O5 88.1(2) . . ? O4 Cu4 O5 97.1(2) . . ? N1 Cu4 O5 91.4(2) . . ? N11 Cu4 O5 101.5(2) . . ? N4 O1 Cu3 112.6(4) . . ? N4 O1 Cu4 126.6(4) . . ? Cu3 O1 Cu4 120.1(2) . . ? N1 O2 Cu2 112.0(4) . . ? N1 O2 Cu1 126.6(4) . . ? Cu2 O2 Cu1 121.4(2) . . ? N6 O3 Cu1 116.8(3) . . ? N16 O4 Cu4 115.9(4) . . ? N15 O5 Cu4 119.9(5) . . ? C5 N1 O2 110.6(5) . . ? C5 N1 Cu4 116.6(4) . . ? O2 N1 Cu4 132.2(4) . . ? C1 N2 Cu3 110.1(5) . . ? C1 N2 H2 115(4) . . ? Cu3 N2 H2 133(4) . . ? C12 N3 C7 116.8(6) . . ? C12 N3 Cu1 129.9(5) . . ? C7 N3 Cu1 113.3(4) . . ? C1 N4 O1 109.9(5) . . ? C1 N4 Cu1 117.8(4) . . ? O1 N4 Cu1 132.2(4) . . ? C5 N5 Cu2 110.5(5) . . ? C5 N5 H5 102(4) . . ? Cu2 N5 H5 147(4) . . ? C4 N6 O3 117.3(5) . . ? C4 N6 Cu2 117.3(4) . . ? O3 N6 Cu2 125.2(4) . . ? C2 N7 C20 116.2(6) . . ? C3 N8 H8A 120.0 . . ? C3 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C16 N9 C8 119.3(6) . . ? C16 N9 Cu2 129.4(5) . . ? C8 N9 Cu2 111.2(4) . . ? C14 N10 C2 118.6(6) . . ? C14 N10 Cu3 129.2(5) . . ? C2 N10 Cu3 112.2(5) . . ? C6 N11 C11 117.6(6) . . ? C6 N11 Cu4 113.4(4) . . ? C11 N11 Cu4 129.0(5) . . ? C4 N12 H12A 120.0 . . ? C4 N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? C6 N13 C9 116.5(6) . . ? C7 N14 C10 116.9(6) . . ? O9 N15 O10 117.6(8) . . ? O9 N15 O5 123.8(8) . . ? O10 N15 O5 118.4(7) . . ? C3 N16 O4 116.5(5) . . ? C3 N16 Cu3 117.7(5) . . ? O4 N16 Cu3 125.8(4) . . ? C8 N17 C19 117.1(6) . . ? O8 N18 O6 118.8(11) . . ? O8 N18 O7 118.5(11) . . ? O6 N18 O7 122.6(11) . . ? N2 C1 N4 123.6(6) . . ? N2 C1 C7 122.7(6) . . ? N4 C1 C7 113.7(5) . . ? N7 C2 N10 124.4(6) . . ? N7 C2 C3 120.8(6) . . ? N10 C2 C3 114.9(6) . . ? N16 C3 N8 127.7(7) . . ? N16 C3 C2 113.5(6) . . ? N8 C3 C2 118.8(6) . . ? N6 C4 N12 127.8(6) . . ? N6 C4 C8 113.3(5) . . ? N12 C4 C8 118.9(6) . . ? N5 C5 N1 123.2(6) . . ? N5 C5 C6 122.6(6) . . ? N1 C5 C6 114.3(6) . . ? N13 C6 N11 125.8(6) . . ? N13 C6 C5 119.9(6) . . ? N11 C6 C5 114.3(6) . . ? N14 C7 N3 126.0(6) . . ? N14 C7 C1 119.7(6) . . ? N3 C7 C1 114.3(6) . . ? N17 C8 N9 123.6(6) . . ? N17 C8 C4 120.6(6) . . ? N9 C8 C4 115.8(6) . . ? N13 C9 C17 122.3(7) . . ? N13 C9 H9 118.9 . . ? C17 C9 H9 118.9 . . ? N14 C10 C13 121.1(7) . . ? N14 C10 H10 119.5 . . ? C13 C10 H10 119.5 . . ? N11 C11 C17 119.5(7) . . ? N11 C11 H11 120.2 . . ? C17 C11 H11 120.2 . . ? N3 C12 C13 119.9(7) . . ? N3 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C10 C13 C12 119.2(7) . . ? C10 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? N10 C14 C18 121.7(7) . . ? N10 C14 H14 119.2 . . ? C18 C14 H14 119.2 . . ? C16 C15 C19 117.9(7) . . ? C16 C15 H15 121.1 . . ? C19 C15 H15 121.1 . . ? N9 C16 C15 120.0(7) . . ? N9 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C11 C17 C9 118.3(6) . . ? C11 C17 H17 120.8 . . ? C9 C17 H17 120.8 . . ? C14 C18 C20 115.8(8) . . ? C14 C18 H18 122.1 . . ? C20 C18 H18 122.1 . . ? N17 C19 C15 122.0(7) . . ? N17 C19 H19 119.0 . . ? C15 C19 H19 119.0 . . ? N7 C20 C18 123.5(7) . . ? N7 C20 H20 118.3 . . ? C18 C20 H20 118.3 . . ? H1W O1W H2W 100(8) . . ? 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 N5 H5 N13 0.91(7) 2.28(7) 2.841(8) 119(5) . N5 H5 O7 0.91(7) 2.61(7) 3.317(11) 134(5) 3_444 N8 H8A O6 0.86 2.28 3.022(10) 145.2 5_566 N8 H8B N17 0.86 2.47 3.252(8) 152.1 1_565 N12 H12A O5 0.86 2.18 2.971(8) 152.2 5_556 N12 H12B N17 0.86 2.46 2.782(8) 103.2 . O1W H1W O9 0.89(5) 2.15(6) 2.990(11) 158(9) 8_556 O1W H2W O7 0.81(4) 2.22(5) 3.029(12) 179(8) . N2 H2 O1W 0.76(6) 2.51(6) 3.186(10) 149(6) . _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.77 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.724 _refine_diff_density_min -1.184 _refine_diff_density_rms 0.217 #===END data_complex3 _database_code_depnum_ccdc_archive 'CCDC 774589' #TrackingRef 'complex_1-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 Cl2 Cu2 N16 Ni2 O4, 2(O)' _chemical_formula_sum 'C20 H18 Cl2 Cu2 N16 Ni2 O5' _chemical_formula_weight 893.85 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' Ni Ni 0.3393 1.1124 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6134(11) _cell_length_b 9.7382(12) _cell_length_c 10.3083(13) _cell_angle_alpha 66.030(2) _cell_angle_beta 83.795(2) _cell_angle_gamma 65.826(2) _cell_volume 719.03(16) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.074 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 3.005 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4975 _exptl_absorpt_correction_T_max 0.5448 _exptl_absorpt_process_details 'SADABS: Blessing, R. (1995), Acta Cryst., A51, 33' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7421 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2921 _reflns_number_gt 2527 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows(Farrugia, 1997)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0376P)^2^+0.9348P] 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 2921 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.003 _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 Cl1 Cl 1.16341(10) -0.28291(10) 0.34233(9) 0.0311(2) Uani 1 1 d . . . Cu1 Cu 1.21676(5) -0.19123(4) 0.51808(4) 0.02468(13) Uani 1 1 d . . . Ni1 Ni 0.99514(5) 0.38129(4) 0.24691(4) 0.02128(12) Uani 1 1 d . . . N1 N 0.9703(4) 0.5993(3) 0.1156(3) 0.0276(6) Uani 1 1 d . . . N2 N 0.7542(4) 0.8693(3) 0.0063(3) 0.0324(7) Uani 1 1 d . . . N3 N 0.7566(3) 0.4885(3) 0.2522(3) 0.0250(6) Uani 1 1 d . . . N4 N 0.5169(4) 0.7390(4) 0.1561(4) 0.0344(7) Uani 1 1 d . . . H4A H 0.457(6) 0.691(6) 0.200(5) 0.059(15) Uiso 1 1 d . . . H4B H 0.491(5) 0.830(6) 0.100(4) 0.039(12) Uiso 1 1 d . . . N5 N 1.4453(3) -0.1837(3) 0.4543(3) 0.0235(6) Uani 1 1 d . . . N6 N 1.5678(3) 0.0036(3) 0.3125(3) 0.0296(6) Uani 1 1 d . . . N7 N 1.1451(3) 0.0491(3) 0.4061(3) 0.0244(6) Uani 1 1 d . . . N8 N 1.2267(4) 0.2551(3) 0.2532(3) 0.0261(6) Uani 1 1 d . . . H8A H 1.316(5) 0.273(4) 0.212(4) 0.029(10) Uiso 1 1 d . . . C1 C 0.8066(4) 0.7112(4) 0.0909(3) 0.0246(7) Uani 1 1 d . . . C2 C 0.8760(6) 0.9179(5) -0.0611(4) 0.0386(9) Uani 1 1 d . . . H2 H 0.845(6) 1.016(6) -0.125(5) 0.058(14) Uiso 1 1 d . . . C3 C 1.0451(6) 0.8126(5) -0.0453(4) 0.0420(9) Uani 1 1 d . . . H3 H 1.132(6) 0.846(6) -0.097(5) 0.054(13) Uiso 1 1 d . . . C4 C 1.0900(5) 0.6519(5) 0.0475(4) 0.0365(8) Uani 1 1 d . . . H4 H 1.200(5) 0.577(5) 0.068(4) 0.031(10) Uiso 1 1 d . . . C5 C 0.6833(4) 0.6437(4) 0.1696(3) 0.0247(7) Uani 1 1 d . . . C6 C 1.4367(4) -0.0331(4) 0.3687(3) 0.0216(6) Uani 1 1 d . . . C7 C 1.6001(4) -0.3090(4) 0.4868(4) 0.0291(7) Uani 1 1 d . . . H7 H 1.598(5) -0.413(5) 0.546(4) 0.038(11) Uiso 1 1 d . . . C8 C 1.7442(4) -0.2809(4) 0.4345(4) 0.0317(8) Uani 1 1 d . . . H8 H 1.865(6) -0.368(5) 0.458(5) 0.054(13) Uiso 1 1 d . . . C9 C 1.7227(4) -0.1232(4) 0.3477(4) 0.0327(8) Uani 1 1 d . . . H9 H 1.829(5) -0.099(4) 0.316(4) 0.030(10) Uiso 1 1 d . . . C10 C 1.2636(4) 0.0989(4) 0.3385(3) 0.0224(6) Uani 1 1 d . . . O1 O 0.6565(3) 0.4129(3) 0.3321(2) 0.0293(5) Uani 1 1 d . . . O2 O 0.9847(3) 0.1816(3) 0.3706(2) 0.0273(5) Uani 1 1 d . . . O1W O 0.4789(5) 0.6358(6) 0.8721(4) 0.0847(13) 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 Cl1 0.0257(4) 0.0229(4) 0.0368(5) -0.0075(3) 0.0000(3) -0.0063(3) Cu1 0.0178(2) 0.0153(2) 0.0293(2) -0.00238(16) 0.00331(16) -0.00277(15) Ni1 0.0186(2) 0.0116(2) 0.0239(2) -0.00271(16) 0.00179(15) -0.00146(15) N1 0.0259(14) 0.0256(14) 0.0283(15) -0.0093(12) 0.0023(12) -0.0092(12) N2 0.0415(17) 0.0191(14) 0.0292(16) -0.0047(12) -0.0001(13) -0.0096(13) N3 0.0230(14) 0.0169(13) 0.0271(14) -0.0048(11) 0.0029(11) -0.0049(11) N4 0.0246(16) 0.0181(15) 0.0402(18) -0.0002(14) 0.0015(13) -0.0008(13) N5 0.0184(13) 0.0188(13) 0.0284(14) -0.0078(11) 0.0025(11) -0.0047(10) N6 0.0194(14) 0.0252(15) 0.0383(17) -0.0104(13) 0.0053(12) -0.0067(11) N7 0.0156(12) 0.0143(12) 0.0327(15) -0.0063(11) 0.0031(11) 0.0004(10) N8 0.0232(14) 0.0184(13) 0.0318(15) -0.0058(12) 0.0049(12) -0.0086(11) C1 0.0284(17) 0.0189(15) 0.0233(16) -0.0085(13) 0.0012(13) -0.0063(13) C2 0.055(2) 0.0231(19) 0.032(2) -0.0027(16) 0.0033(18) -0.0181(18) C3 0.050(2) 0.041(2) 0.042(2) -0.0135(18) 0.0129(19) -0.030(2) C4 0.030(2) 0.037(2) 0.043(2) -0.0150(17) 0.0055(16) -0.0146(17) C5 0.0239(16) 0.0176(15) 0.0249(16) -0.0062(13) 0.0008(13) -0.0033(13) C6 0.0203(15) 0.0186(15) 0.0235(16) -0.0072(12) 0.0023(12) -0.0070(12) C7 0.0252(17) 0.0204(17) 0.0322(19) -0.0078(14) -0.0002(14) -0.0025(13) C8 0.0186(16) 0.0321(18) 0.038(2) -0.0157(16) 0.0011(14) -0.0026(14) C9 0.0213(17) 0.0336(19) 0.040(2) -0.0138(16) 0.0047(14) -0.0097(15) C10 0.0220(15) 0.0183(15) 0.0243(16) -0.0074(13) 0.0027(12) -0.0068(12) O1 0.0205(11) 0.0190(11) 0.0320(13) 0.0005(9) 0.0033(9) -0.0037(9) O2 0.0150(10) 0.0158(10) 0.0353(13) -0.0037(9) 0.0067(9) 0.0009(8) O1W 0.092(3) 0.128(4) 0.085(3) -0.057(3) 0.033(2) -0.083(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl1 Cu1 2.4740(10) . ? Cu1 O2 1.965(2) 2_756 ? Cu1 O1 1.990(2) 2_756 ? Cu1 N7 1.992(3) . ? Cu1 N5 2.028(3) . ? Ni1 N8 1.857(3) . ? Ni1 O2 1.875(2) . ? Ni1 N3 1.892(3) . ? Ni1 N1 1.934(3) . ? N1 C4 1.343(5) . ? N1 C1 1.354(4) . ? N2 C1 1.327(4) . ? N2 C2 1.337(5) . ? N3 C5 1.303(4) . ? N3 O1 1.355(3) . ? N4 C5 1.336(4) . ? N4 H4A 0.82(5) . ? N4 H4B 0.79(4) . ? N5 C6 1.345(4) . ? N5 C7 1.346(4) . ? N6 C6 1.327(4) . ? N6 C9 1.352(4) . ? N7 C10 1.319(4) . ? N7 O2 1.404(3) . ? N8 C10 1.329(4) . ? N8 H8A 0.89(4) . ? C1 C5 1.473(5) . ? C2 C3 1.375(6) . ? C2 H2 0.86(5) . ? C3 C4 1.372(5) . ? C3 H3 0.96(5) . ? C4 H4 0.91(4) . ? C6 C10 1.475(4) . ? C7 C8 1.385(5) . ? C7 H7 0.96(4) . ? C8 C9 1.371(5) . ? C8 H8 1.01(5) . ? C9 H9 1.02(4) . ? O1 Cu1 1.990(2) 2_756 ? O2 Cu1 1.965(2) 2_756 ? 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 O2 Cu1 O1 87.79(9) 2_756 2_756 ? O2 Cu1 N7 97.85(9) 2_756 . ? O1 Cu1 N7 157.98(11) 2_756 . ? O2 Cu1 N5 160.84(11) 2_756 . ? O1 Cu1 N5 88.01(10) 2_756 . ? N7 Cu1 N5 79.69(10) . . ? O2 Cu1 Cl1 101.28(8) 2_756 . ? O1 Cu1 Cl1 97.32(8) 2_756 . ? N7 Cu1 Cl1 102.37(9) . . ? N5 Cu1 Cl1 97.80(8) . . ? N8 Ni1 O2 84.45(10) . . ? N8 Ni1 N3 173.84(11) . . ? O2 Ni1 N3 89.42(10) . . ? N8 Ni1 N1 103.59(12) . . ? O2 Ni1 N1 171.68(11) . . ? N3 Ni1 N1 82.52(11) . . ? C4 N1 C1 117.4(3) . . ? C4 N1 Ni1 129.4(3) . . ? C1 N1 Ni1 113.2(2) . . ? C1 N2 C2 115.6(3) . . ? C5 N3 O1 118.0(3) . . ? C5 N3 Ni1 117.6(2) . . ? O1 N3 Ni1 124.27(19) . . ? C5 N4 H4A 115(4) . . ? C5 N4 H4B 115(3) . . ? H4A N4 H4B 130(5) . . ? C6 N5 C7 117.6(3) . . ? C6 N5 Cu1 114.3(2) . . ? C7 N5 Cu1 128.1(2) . . ? C6 N6 C9 115.9(3) . . ? C10 N7 O2 110.2(2) . . ? C10 N7 Cu1 117.0(2) . . ? O2 N7 Cu1 132.47(19) . . ? C10 N8 Ni1 110.7(2) . . ? C10 N8 H8A 114(2) . . ? Ni1 N8 H8A 136(2) . . ? N2 C1 N1 125.6(3) . . ? N2 C1 C5 120.3(3) . . ? N1 C1 C5 114.0(3) . . ? N2 C2 C3 123.0(3) . . ? N2 C2 H2 118(3) . . ? C3 C2 H2 119(3) . . ? C4 C3 C2 117.9(4) . . ? C4 C3 H3 119(3) . . ? C2 C3 H3 123(3) . . ? N1 C4 C3 120.4(4) . . ? N1 C4 H4 117(2) . . ? C3 C4 H4 123(2) . . ? N3 C5 N4 126.4(3) . . ? N3 C5 C1 112.5(3) . . ? N4 C5 C1 121.1(3) . . ? N6 C6 N5 125.7(3) . . ? N6 C6 C10 119.4(3) . . ? N5 C6 C10 114.9(3) . . ? N5 C7 C8 120.3(3) . . ? N5 C7 H7 114(2) . . ? C8 C7 H7 126(2) . . ? C9 C8 C7 117.8(3) . . ? C9 C8 H8 117(3) . . ? C7 C8 H8 125(3) . . ? N6 C9 C8 122.6(3) . . ? N6 C9 H9 119(2) . . ? C8 C9 H9 118(2) . . ? N7 C10 N8 121.7(3) . . ? N7 C10 C6 113.9(3) . . ? N8 C10 C6 124.4(3) . . ? N3 O1 Cu1 114.58(17) . 2_756 ? N7 O2 Ni1 112.98(17) . . ? N7 O2 Cu1 125.75(18) . 2_756 ? Ni1 O2 Cu1 117.59(10) . 2_756 ? 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 N4 H4A Cl1 0.82(5) 2.75(5) 3.455(4) 145(4) 1_465 N4 H4B N2 0.79(4) 2.65(4) 3.341(4) 146(4) 2_675 N8 H8A O1W 0.89(4) 2.23(4) 3.100(4) 166(3) 2_766 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.678 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.092