# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address B.Mondal ;Indian Institute of Technalogy Guwahati Assam-781039, India ; A.Kalita '' _publ_contact_author_name 'Dr. Biplab Mondal' _publ_contact_author_address ;Indian Institute of Technology Guwahati Assam-781039, India ; _publ_contact_author_email biplab@iitg.ernet.in _publ_section_title ; First example of Cu(I)-(e2-O,O)nitrite complex derived from Cu(II)-nitrosyl ; data_23 _database_code_depnum_ccdc_archive 'CCDC 838636' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C26 H36 Cl2 Cu N8 O9' _chemical_formula_sum 'C26 H36 Cl2 Cu N8 O9' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Methanol _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour brown _diffrn_ambient_temperature 293(2) _chemical_formula_weight 739.08 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration syn 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 19.3685(12) _cell_length_b 9.3430(6) _cell_length_c 19.1564(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.081(4) _cell_angle_gamma 90.00 _cell_volume 3389.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6352 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 20.65 _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.032 _exptl_crystal_size_min 0.022 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1532.0 _exptl_absorpt_coefficient_mu 0.862 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 33252 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.1023 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 28.36 _reflns_number_total 8483 _reflns_number_gt 3371 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8483 _refine_ls_number_parameters 420 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2115 _refine_ls_R_factor_gt 0.1405 _refine_ls_wR_factor_ref 0.4091 _refine_ls_wR_factor_gt 0.3990 _refine_ls_goodness_of_fit_ref 2.052 _refine_ls_restrained_S_all 2.052 _refine_ls_shift/su_max 2.205 _refine_ls_shift/su_mean 0.072 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 0.19809(6) 0.26127(12) 0.29993(6) 0.0555(5) Uani 1 1 d . . . Cl1 Cl 0.09526(16) 0.2599(4) 0.41965(18) 0.0749(9) Uani 1 1 d . . . O1 O 0.0937(5) 0.1496(12) 0.3720(7) 0.133(4) Uani 1 1 d . . . O2 O 0.1441(5) 0.3539(11) 0.3990(5) 0.110(3) Uani 1 1 d . . . O3 O 0.1201(7) 0.2124(16) 0.4872(7) 0.176(6) Uani 1 1 d . . . O4 O 0.0311(5) 0.3270(16) 0.4127(7) 0.148(5) Uani 1 1 d . . . N1 N 0.2206(5) 0.1140(10) 0.2305(5) 0.069(3) Uani 1 1 d . . . N2 N 0.2698(5) -0.0044(11) 0.1543(6) 0.079(3) Uani 1 1 d . . . N3 N 0.1118(4) 0.3252(9) 0.2343(4) 0.054(2) Uani 1 1 d . . . N4 N 0.0291(5) 0.4532(9) 0.1692(5) 0.065(2) Uani 1 1 d . . . N5 N 0.2661(4) 0.1887(9) 0.3822(4) 0.058(2) Uani 1 1 d . . . N6 N 0.3367(5) 0.0501(10) 0.4594(5) 0.077(3) Uani 1 1 d . . . N7 N 0.2606(4) 0.4355(10) 0.2883(5) 0.071(3) Uani 1 1 d . . . N8 N 0.3366(5) 0.5711(11) 0.2434(5) 0.083(3) Uani 1 1 d . . . C3 C 0.2800(7) 0.0704(14) 0.2144(7) 0.077(3) Uani 1 1 d . . . C4 C 0.1974(7) -0.0115(13) 0.1291(7) 0.081(4) Uani 1 1 d . . . C5 C 0.1684(7) -0.0950(14) 0.0603(6) 0.092(4) Uani 1 1 d . . . H3A H 0.1200 -0.0688 0.0423 0.139 Uiso 1 1 calc R . . H3B H 0.1712 -0.1958 0.0702 0.139 Uiso 1 1 calc R . . H3C H 0.1957 -0.0727 0.0253 0.139 Uiso 1 1 calc R . . C6 C 0.1673(5) 0.0575(12) 0.1727(6) 0.064(3) Uani 1 1 d . . . C2 C 0.3544(8) 0.111(2) 0.2552(10) 0.145(8) Uani 1 1 d . . . H5A H 0.3530 0.2137 0.2604 0.174 Uiso 1 1 calc R . . H5B H 0.3573 0.0720 0.3028 0.174 Uiso 1 1 calc R . . C1 C 0.4052(12) 0.089(7) 0.243(2) 0.50(5) Uani 1 1 d . . . H6C H 0.4025 0.0092 0.2146 0.602 Uiso 1 1 d R . . H53B H 0.4447 0.1233 0.2796 0.602 Uiso 1 1 d R . . H53C H 0.4100 0.1766 0.2027 0.602 Uiso 1 1 d R . . C7 C 0.0898(6) 0.0853(11) 0.1730(6) 0.065(3) Uani 1 1 d . . . H7A H 0.0608 0.0474 0.1294 0.078 Uiso 1 1 calc R . . H7B H 0.0773 0.0348 0.2129 0.078 Uiso 1 1 calc R . . C8 C 0.0741(5) 0.2392(11) 0.1786(6) 0.059(3) Uani 1 1 d . . . C9 C 0.0235(5) 0.3200(11) 0.1385(5) 0.050(2) Uani 1 1 d . . . C11 C 0.0823(6) 0.4491(11) 0.2266(6) 0.063(3) Uani 1 1 d . . . C12 C 0.1014(6) 0.5750(10) 0.2776(6) 0.073(3) Uani 1 1 d . . . H11A H 0.1498 0.5641 0.3035 0.088 Uiso 1 1 calc R . . H11B H 0.0713 0.5731 0.3122 0.088 Uiso 1 1 calc R . . C13 C 0.0934(9) 0.7208(14) 0.2396(9) 0.122(6) Uani 1 1 d . . . H12A H 0.0489 0.7244 0.2063 0.184 Uiso 1 1 calc R . . H12B H 0.1310 0.7332 0.2145 0.184 Uiso 1 1 calc R . . H12C H 0.0954 0.7958 0.2742 0.184 Uiso 1 1 calc R . . C10 C -0.0308(6) 0.2861(12) 0.0719(6) 0.077(4) Uani 1 1 d . . . H13A H -0.0131 0.3006 0.0328 0.092 Uiso 1 1 d R . . H13B H -0.0287 0.1838 0.0642 0.092 Uiso 1 1 d R . . H13C H -0.0688 0.3420 0.0688 0.092 Uiso 1 1 d R . . C24 C 0.2776(6) 0.4895(18) 0.2281(7) 0.102(5) Uani 1 1 d . . . C22 C 0.3629(6) 0.5596(12) 0.3154(7) 0.075(3) Uani 1 1 d . . . C23 C 0.4296(6) 0.6323(15) 0.3497(7) 0.097(4) Uani 1 1 d . . . H17A H 0.4441 0.5998 0.3981 0.145 Uiso 1 1 calc R . . H17B H 0.4222 0.7339 0.3493 0.145 Uiso 1 1 calc R . . H17C H 0.4657 0.6102 0.3238 0.145 Uiso 1 1 calc R . . C21 C 0.3172(5) 0.4806(11) 0.3426(5) 0.054(3) Uani 1 1 d . . . C20 C 0.3181(6) 0.4300(12) 0.4180(6) 0.070(3) Uani 1 1 d . . . H19A H 0.3598 0.4675 0.4498 0.084 Uiso 1 1 calc R . . H19B H 0.2770 0.4677 0.4333 0.084 Uiso 1 1 calc R . . C19 C 0.3181(5) 0.2735(11) 0.4233(5) 0.054(3) Uani 1 1 d . . . C17 C 0.3626(6) 0.1856(12) 0.4728(6) 0.061(3) Uani 1 1 d . . . C16 C 0.2774(6) 0.0567(12) 0.4030(6) 0.073(3) Uani 1 1 d . . . C15 C 0.2360(8) -0.0700(13) 0.3759(7) 0.099(5) Uani 1 1 d . . . H23A H 0.1869 -0.0408 0.3629 0.119 Uiso 1 1 calc R . . H23B H 0.2500 -0.0985 0.3321 0.119 Uiso 1 1 calc R . . C14 C 0.2390(12) -0.188(2) 0.4172(11) 0.182(10) Uani 1 1 d . . . H24A H 0.1942 -0.2013 0.4303 0.272 Uiso 1 1 calc R . . H24B H 0.2751 -0.1755 0.4595 0.272 Uiso 1 1 calc R . . H24C H 0.2497 -0.2696 0.3912 0.272 Uiso 1 1 calc R . . C18 C 0.4255(7) 0.2194(14) 0.5300(7) 0.091(4) Uani 1 1 d . . . H25A H 0.4172 0.2916 0.5587 0.109 Uiso 1 1 d R . . H42B H 0.4555 0.2824 0.5062 0.109 Uiso 1 1 d R . . H42C H 0.4504 0.1359 0.5447 0.109 Uiso 1 1 d R . . C25 C 0.2347(8) 0.468(2) 0.1510(9) 0.133(7) Uani 1 1 d . . . H70A H 0.1994 0.3946 0.1523 0.159 Uiso 1 1 calc R . . H70B H 0.2097 0.5560 0.1358 0.159 Uiso 1 1 calc R . . C26 C 0.2677(13) 0.433(4) 0.1052(12) 0.251(18) Uani 1 1 d . . . H72A H 0.2937 0.3471 0.1197 0.376 Uiso 1 1 calc R . . H72B H 0.2998 0.5087 0.0997 0.376 Uiso 1 1 calc R . . H72C H 0.2353 0.4176 0.0606 0.376 Uiso 1 1 calc R . . Cl2 Cl 0.41655(17) 0.7666(3) 0.09140(17) 0.0703(9) Uani 1 1 d . . . O8 O 0.4717(10) 0.841(2) 0.0984(11) 0.243(10) Uani 1 1 d . . . O7 O 0.4111(7) 0.6827(19) 0.0342(10) 0.220(9) Uani 1 1 d . . . O5 O 0.4099(14) 0.713(3) 0.1496(12) 0.307(14) Uani 1 1 d . . . O6 O 0.3611(15) 0.843(4) 0.0838(11) 0.42(2) Uani 1 1 d . . . O9 O 0.292(3) 0.753(5) 0.2005(15) 1.01(8) 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 0.0531(9) 0.0489(8) 0.0553(9) 0.0018(6) -0.0100(6) -0.0072(6) Cl1 0.067(2) 0.084(2) 0.071(2) 0.0034(18) 0.0095(16) -0.0071(17) O1 0.113(8) 0.112(8) 0.166(10) -0.043(8) 0.010(7) -0.024(6) O2 0.115(7) 0.102(7) 0.110(8) -0.015(6) 0.016(6) -0.042(6) O3 0.140(10) 0.242(15) 0.146(11) 0.125(11) 0.032(8) 0.039(10) O4 0.056(6) 0.233(14) 0.157(10) 0.027(10) 0.027(6) 0.044(8) N1 0.054(6) 0.085(7) 0.059(6) -0.008(5) -0.006(5) 0.000(5) N2 0.080(8) 0.081(7) 0.073(7) -0.005(6) 0.006(6) 0.026(5) N3 0.045(5) 0.048(5) 0.062(6) -0.001(4) -0.008(4) -0.004(4) N4 0.066(6) 0.063(6) 0.059(6) -0.011(5) 0.001(5) 0.003(5) N5 0.057(5) 0.050(5) 0.056(6) -0.006(4) -0.013(4) -0.010(4) N6 0.067(6) 0.074(7) 0.074(7) 0.023(5) -0.022(5) -0.008(5) N7 0.049(5) 0.087(7) 0.067(6) 0.016(5) -0.015(5) -0.020(5) N8 0.066(6) 0.108(8) 0.070(7) 0.020(6) 0.004(5) -0.028(6) C3 0.072(9) 0.098(9) 0.058(8) -0.001(7) 0.006(7) 0.019(7) C4 0.069(9) 0.070(8) 0.086(10) -0.020(7) -0.021(7) 0.016(6) C5 0.114(10) 0.076(9) 0.078(9) -0.036(7) -0.002(8) 0.005(8) C6 0.046(7) 0.072(7) 0.063(7) -0.016(6) -0.014(6) 0.003(5) C2 0.055(9) 0.205(19) 0.148(15) -0.082(14) -0.042(10) 0.037(10) C1 0.061(15) 0.98(13) 0.45(6) -0.40(8) 0.04(2) -0.02(4) C7 0.090(9) 0.049(6) 0.057(7) -0.030(5) 0.021(6) -0.019(6) C8 0.051(6) 0.062(7) 0.061(7) -0.002(6) 0.006(5) -0.010(5) C9 0.038(6) 0.059(6) 0.046(6) 0.001(5) -0.007(5) 0.003(5) C11 0.072(7) 0.044(6) 0.066(8) 0.002(5) 0.002(6) -0.002(5) C12 0.075(8) 0.044(6) 0.092(9) -0.020(6) -0.002(7) 0.004(5) C13 0.147(15) 0.075(10) 0.136(14) -0.006(9) 0.010(11) -0.029(9) C10 0.060(7) 0.079(8) 0.076(8) -0.023(6) -0.022(6) 0.009(6) C24 0.047(7) 0.165(14) 0.078(10) 0.057(10) -0.020(7) -0.019(8) C22 0.076(8) 0.071(8) 0.067(8) 0.010(6) -0.011(7) -0.019(6) C23 0.068(8) 0.101(10) 0.118(11) 0.017(8) 0.013(8) -0.052(7) C21 0.047(6) 0.056(6) 0.048(7) 0.006(5) -0.018(5) -0.008(5) C20 0.073(8) 0.071(8) 0.063(8) -0.014(6) 0.004(6) -0.030(6) C19 0.055(6) 0.058(6) 0.042(6) -0.001(5) -0.003(5) -0.014(5) C17 0.062(7) 0.055(6) 0.056(7) 0.007(5) -0.007(5) -0.011(5) C16 0.089(9) 0.050(7) 0.073(8) 0.004(6) 0.003(7) 0.002(6) C15 0.125(11) 0.056(7) 0.091(10) 0.004(7) -0.038(8) -0.025(7) C14 0.22(2) 0.110(13) 0.172(19) 0.044(14) -0.047(16) -0.089(15) C18 0.083(9) 0.101(10) 0.069(8) 0.005(7) -0.027(7) -0.027(7) C25 0.098(12) 0.20(2) 0.083(12) 0.023(12) -0.014(9) -0.081(12) C26 0.21(3) 0.44(5) 0.110(18) -0.05(2) 0.069(18) -0.12(3) Cl2 0.074(2) 0.0700(19) 0.068(2) -0.0032(16) 0.0171(15) -0.0035(16) O8 0.221(17) 0.27(2) 0.28(2) -0.112(17) 0.134(16) -0.160(17) O7 0.152(12) 0.243(16) 0.273(19) -0.211(16) 0.061(11) -0.075(11) O5 0.35(3) 0.36(3) 0.23(2) 0.17(2) 0.10(2) -0.05(2) O6 0.43(3) 0.61(5) 0.22(2) -0.04(2) 0.08(2) 0.41(4) O9 1.44(13) 1.06(10) 0.31(3) -0.40(5) -0.34(5) 1.11(11) _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 1.952(8) . ? Cu1 N3 1.962(7) . ? Cu1 N1 2.025(10) . ? Cu1 N7 2.069(9) . ? Cl1 O3 1.357(11) . ? Cl1 O4 1.373(10) . ? Cl1 O1 1.373(11) . ? Cl1 O2 1.407(10) . ? N1 C3 1.315(14) . ? N1 C6 1.446(12) . ? N2 C3 1.327(14) . ? N2 C4 1.385(14) . ? N3 C11 1.285(12) . ? N3 C8 1.411(12) . ? N4 C11 1.342(12) . ? N4 C9 1.371(12) . ? N5 C16 1.300(13) . ? N5 C19 1.389(11) . ? N6 C17 1.366(13) . ? N6 C16 1.404(14) . ? N7 C24 1.360(14) . ? N7 C21 1.408(11) . ? N8 C24 1.354(14) . ? N8 C22 1.369(14) . ? C3 C2 1.535(17) . ? C4 C6 1.287(15) . ? C4 C5 1.535(15) . ? C5 H3A 0.9600 . ? C5 H3B 0.9600 . ? C5 H3C 0.9600 . ? C6 C7 1.525(15) . ? C2 C1 1.07(2) . ? C2 H5A 0.9700 . ? C2 H5B 0.9700 . ? C1 H6C 0.9243 . ? C1 H53B 0.9712 . ? C1 H53C 1.1484 . ? C7 C8 1.479(14) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.342(13) . ? C9 C10 1.508(13) . ? C11 C12 1.524(14) . ? C12 C13 1.538(17) . ? C12 H11A 0.9700 . ? C12 H11B 0.9700 . ? C13 H12A 0.9600 . ? C13 H12B 0.9600 . ? C13 H12C 0.9600 . ? C10 H13A 0.8972 . ? C10 H13B 0.9688 . ? C10 H13C 0.8951 . ? C24 C25 1.550(18) . ? C22 C21 1.340(14) . ? C22 C23 1.486(14) . ? C23 H17A 0.9600 . ? C23 H17B 0.9600 . ? C23 H17C 0.9600 . ? C21 C20 1.516(14) . ? C20 C19 1.466(14) . ? C20 H19A 0.9700 . ? C20 H19B 0.9700 . ? C19 C17 1.404(13) . ? C17 C18 1.492(14) . ? C16 C15 1.463(15) . ? C15 C14 1.348(18) . ? C15 H23A 0.9700 . ? C15 H23B 0.9700 . ? C14 H24A 0.9600 . ? C14 H24B 0.9600 . ? C14 H24C 0.9600 . ? C18 H25A 0.9058 . ? C18 H42B 1.0013 . ? C18 H42C 0.9295 . ? C25 C26 1.23(3) . ? C25 H70A 0.9700 . ? C25 H70B 0.9700 . ? C26 H72A 0.9600 . ? C26 H72B 0.9600 . ? C26 H72C 0.9600 . ? Cl2 O5 1.252(16) . ? Cl2 O8 1.260(13) . ? Cl2 O6 1.274(16) . ? Cl2 O7 1.333(12) . ? 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 N3 164.4(4) . . ? N5 Cu1 N1 95.3(4) . . ? N3 Cu1 N1 93.3(3) . . ? N5 Cu1 N7 92.8(3) . . ? N3 Cu1 N7 97.5(3) . . ? N1 Cu1 N7 104.6(4) . . ? O3 Cl1 O4 112.0(8) . . ? O3 Cl1 O1 110.0(9) . . ? O4 Cl1 O1 112.6(8) . . ? O3 Cl1 O2 110.3(7) . . ? O4 Cl1 O2 109.7(8) . . ? O1 Cl1 O2 101.8(7) . . ? C3 N1 C6 103.2(10) . . ? C3 N1 Cu1 133.1(8) . . ? C6 N1 Cu1 122.2(7) . . ? C3 N2 C4 106.5(10) . . ? C11 N3 C8 106.2(8) . . ? C11 N3 Cu1 130.2(7) . . ? C8 N3 Cu1 123.2(7) . . ? C11 N4 C9 107.6(8) . . ? C16 N5 C19 108.2(9) . . ? C16 N5 Cu1 128.2(7) . . ? C19 N5 Cu1 123.1(7) . . ? C17 N6 C16 108.2(8) . . ? C24 N7 C21 103.1(9) . . ? C24 N7 Cu1 129.4(9) . . ? C21 N7 Cu1 122.6(7) . . ? C24 N8 C22 107.0(10) . . ? N1 C3 N2 112.8(11) . . ? N1 C3 C2 125.4(12) . . ? N2 C3 C2 121.6(12) . . ? C6 C4 N2 108.3(10) . . ? C6 C4 C5 132.7(12) . . ? N2 C4 C5 119.1(12) . . ? C4 C5 H3A 109.6 . . ? C4 C5 H3B 109.4 . . ? H3A C5 H3B 109.5 . . ? C4 C5 H3C 109.4 . . ? H3A C5 H3C 109.5 . . ? H3B C5 H3C 109.5 . . ? C4 C6 N1 109.3(10) . . ? C4 C6 C7 131.9(10) . . ? N1 C6 C7 118.8(10) . . ? C1 C2 C3 131(2) . . ? C1 C2 H5A 104.7 . . ? C3 C2 H5A 104.5 . . ? C1 C2 H5B 104.4 . . ? C3 C2 H5B 104.8 . . ? H5A C2 H5B 105.7 . . ? C2 C1 H6C 109.7 . . ? C2 C1 H53B 114.2 . . ? H6C C1 H53B 129.0 . . ? C2 C1 H53C 102.6 . . ? H6C C1 H53C 99.7 . . ? H53B C1 H53C 95.0 . . ? C8 C7 C6 112.6(9) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C9 C8 N3 108.2(9) . . ? C9 C8 C7 129.9(10) . . ? N3 C8 C7 121.8(9) . . ? C8 C9 N4 106.4(9) . . ? C8 C9 C10 131.4(10) . . ? N4 C9 C10 122.1(9) . . ? N3 C11 N4 111.5(9) . . ? N3 C11 C12 125.4(10) . . ? N4 C11 C12 123.0(9) . . ? C11 C12 C13 113.1(10) . . ? C11 C12 H11A 108.9 . . ? C13 C12 H11A 108.9 . . ? C11 C12 H11B 109.0 . . ? C13 C12 H11B 109.0 . . ? H11A C12 H11B 107.8 . . ? C12 C13 H12A 109.4 . . ? C12 C13 H12B 109.5 . . ? H12A C13 H12B 109.5 . . ? C12 C13 H12C 109.5 . . ? H12A C13 H12C 109.5 . . ? H12B C13 H12C 109.5 . . ? C9 C10 H13A 110.8 . . ? C9 C10 H13B 107.1 . . ? H13A C10 H13B 89.2 . . ? C9 C10 H13C 110.7 . . ? H13A C10 H13C 107.9 . . ? H13B C10 H13C 128.6 . . ? N7 C24 N8 111.6(10) . . ? N7 C24 C25 125.6(12) . . ? N8 C24 C25 122.7(12) . . ? C21 C22 N8 107.3(9) . . ? C21 C22 C23 131.6(11) . . ? N8 C22 C23 121.0(11) . . ? C22 C23 H17A 109.5 . . ? C22 C23 H17B 109.5 . . ? H17A C23 H17B 109.5 . . ? C22 C23 H17C 109.5 . . ? H17A C23 H17C 109.5 . . ? H17B C23 H17C 109.5 . . ? C22 C21 N7 110.6(9) . . ? C22 C21 C20 131.7(9) . . ? N7 C21 C20 117.6(9) . . ? C19 C20 C21 112.2(9) . . ? C19 C20 H19A 109.3 . . ? C21 C20 H19A 109.2 . . ? C19 C20 H19B 109.1 . . ? C21 C20 H19B 109.1 . . ? H19A C20 H19B 107.9 . . ? N5 C19 C17 108.6(9) . . ? N5 C19 C20 122.7(9) . . ? C17 C19 C20 128.4(9) . . ? N6 C17 C19 105.4(8) . . ? N6 C17 C18 123.0(10) . . ? C19 C17 C18 131.6(10) . . ? N5 C16 N6 109.6(9) . . ? N5 C16 C15 127.9(11) . . ? N6 C16 C15 122.4(10) . . ? C14 C15 C16 119.9(12) . . ? C14 C15 H23A 107.4 . . ? C16 C15 H23A 107.4 . . ? C14 C15 H23B 107.3 . . ? C16 C15 H23B 107.3 . . ? H23A C15 H23B 106.9 . . ? C15 C14 H24A 109.4 . . ? C15 C14 H24B 109.5 . . ? H24A C14 H24B 109.5 . . ? C15 C14 H24C 109.5 . . ? H24A C14 H24C 109.5 . . ? H24B C14 H24C 109.5 . . ? C17 C18 H25A 112.5 . . ? C17 C18 H42B 104.7 . . ? H25A C18 H42B 91.8 . . ? C17 C18 H42C 109.8 . . ? H25A C18 H42C 125.9 . . ? H42B C18 H42C 108.5 . . ? C26 C25 C24 117.3(18) . . ? C26 C25 H70A 108.1 . . ? C24 C25 H70A 108.0 . . ? C26 C25 H70B 108.0 . . ? C24 C25 H70B 107.9 . . ? H70A C25 H70B 107.2 . . ? C25 C26 H72A 109.4 . . ? C25 C26 H72B 109.6 . . ? H72A C26 H72B 109.5 . . ? C25 C26 H72C 109.4 . . ? H72A C26 H72C 109.5 . . ? H72B C26 H72C 109.5 . . ? O5 Cl2 O8 111.7(16) . . ? O5 Cl2 O6 94.9(18) . . ? O8 Cl2 O6 112(2) . . ? O5 Cl2 O7 119.4(16) . . ? O8 Cl2 O7 109.5(10) . . ? O6 Cl2 O7 108.4(14) . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 1.562 _refine_diff_density_min -0.721 _refine_diff_density_rms 0.153 # Attachment '- complex 3_revised.cif' data_13 _database_code_depnum_ccdc_archive 'CCDC 838637' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C26 H36 Cu N9 O6' _chemical_formula_sum 'C26 H36 Cu N9 O6' _chemical_compound_source Synthesised _exptl_crystal_recrystallization_method Water _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour yellow _diffrn_ambient_temperature 296(2) _chemical_formula_weight 634.19 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_int_tables_number 13 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.4710(2) _cell_length_b 9.4545(2) _cell_length_c 18.3295(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.0540(10) _cell_angle_gamma 90.00 _cell_volume 1641.29(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7546 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.31 _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.716 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 19006 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.38 _reflns_number_total 4113 _reflns_number_gt 3330 _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^)+(0.1404P)^2^+0.0127P] 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 4113 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.2020 _refine_ls_wR_factor_gt 0.1951 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.81549(4) 0.2500 0.03301(19) Uani 1 2 d S . . O1 O -0.1040(3) 1.0385(3) 0.26901(14) 0.0711(7) Uani 1 1 d . . . N1 N -0.0689(2) 0.8311(2) 0.14805(12) 0.0350(5) Uani 1 1 d . . . N2 N -0.2009(3) 0.8483(3) 0.04974(14) 0.0457(6) Uani 1 1 d . . . N3 N 0.1526(3) 0.6623(2) 0.21444(12) 0.0384(5) Uani 1 1 d . . . N4 N 0.2634(3) 0.4627(2) 0.19123(13) 0.0459(6) Uani 1 1 d . . . N9 N 0.0000 1.1136(4) 0.2500 0.0632(11) Uani 1 2 d S . . C1 C -0.4514(4) 0.7886(5) 0.1520(3) 0.0836(13) Uani 1 1 d . . . H17A H -0.4619 0.7771 0.1003 0.125 Uiso 1 1 calc R . . H17B H -0.5360 0.8291 0.1718 0.125 Uiso 1 1 calc R . . H17C H -0.4345 0.6982 0.1741 0.125 Uiso 1 1 calc R . . C2 C -0.3266(3) 0.8868(4) 0.16761(18) 0.0518(7) Uani 1 1 d . . . H1A H -0.3550 0.9835 0.1579 0.062 Uiso 1 1 calc R . . H1B H -0.3025 0.8802 0.2189 0.062 Uiso 1 1 calc R . . C3 C -0.1990(3) 0.8537(3) 0.12349(16) 0.0405(6) Uani 1 1 d . . . C4 C -0.0650(3) 0.8222(3) 0.02622(17) 0.0437(7) Uani 1 1 d . . . C5 C -0.0318(5) 0.8097(4) -0.05391(18) 0.0609(9) Uani 1 1 d . . . H5A H 0.0653 0.8340 -0.0621 0.091 Uiso 1 1 calc R . . H5B H -0.0914 0.8729 -0.0810 0.091 Uiso 1 1 calc R . . H5C H -0.0483 0.7143 -0.0697 0.091 Uiso 1 1 calc R . . C6 C 0.0156(3) 0.8122(2) 0.08609(15) 0.0353(5) Uani 1 1 d . . . C7 C 0.1699(3) 0.7887(3) 0.09438(15) 0.0388(6) Uani 1 1 d . . . H6A H 0.2130 0.8729 0.1148 0.047 Uiso 1 1 calc R . . H6B H 0.2112 0.7724 0.0467 0.047 Uiso 1 1 calc R . . C8 C 0.2015(3) 0.6647(3) 0.14289(14) 0.0347(5) Uani 1 1 d . . . C9 C 0.2700(3) 0.5420(3) 0.12740(15) 0.0400(6) Uani 1 1 d . . . C10 C 0.3420(4) 0.4907(4) 0.06068(19) 0.0607(9) Uani 1 1 d . . . H9A H 0.4039 0.4140 0.0731 0.091 Uiso 1 1 calc R . . H9B H 0.3958 0.5664 0.0396 0.091 Uiso 1 1 calc R . . H9C H 0.2728 0.4586 0.0262 0.091 Uiso 1 1 calc R . . C11 C 0.1916(3) 0.5392(3) 0.24151(15) 0.0443(6) Uani 1 1 d . . . C12 C 0.1596(5) 0.4813(4) 0.31588(18) 0.0660(10) Uani 1 1 d . . . H11A H 0.0743 0.4249 0.3129 0.079 Uiso 1 1 calc R . . H11B H 0.1408 0.5598 0.3485 0.079 Uiso 1 1 calc R . . C13 C 0.2760(5) 0.3915(6) 0.3485(2) 0.0940(16) Uani 1 1 d . . . H23A H 0.2772 0.3008 0.3250 0.141 Uiso 1 1 calc R . . H23B H 0.2592 0.3793 0.3998 0.141 Uiso 1 1 calc R . . H23C H 0.3653 0.4375 0.3414 0.141 Uiso 1 1 calc R . . O3 O 0.4663(4) 0.1305(3) 0.04350(13) 0.0840(10) Uani 1 1 d . . . O2 O 0.3764(3) 0.1748(2) 0.20103(15) 0.0651(7) 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 0.0295(3) 0.0357(3) 0.0339(3) 0.000 0.00153(18) 0.000 O1 0.0558(14) 0.095(2) 0.0624(15) 0.0038(13) -0.0056(12) -0.0034(14) N1 0.0282(10) 0.0383(11) 0.0385(12) 0.0005(8) 0.0003(9) 0.0014(8) N2 0.0434(13) 0.0509(13) 0.0429(13) -0.0020(10) -0.0077(10) 0.0103(11) N3 0.0434(13) 0.0379(11) 0.0340(11) 0.0032(8) 0.0062(10) 0.0033(9) N4 0.0534(15) 0.0417(12) 0.0426(13) 0.0029(9) 0.0015(11) 0.0091(10) N9 0.082(3) 0.0362(18) 0.071(3) 0.000 -0.015(2) 0.000 C1 0.0382(18) 0.101(3) 0.112(4) -0.012(3) 0.008(2) -0.018(2) C2 0.0315(13) 0.066(2) 0.0577(18) -0.0054(15) 0.0001(12) 0.0081(13) C3 0.0335(13) 0.0414(13) 0.0467(15) -0.0019(11) -0.0034(11) 0.0041(11) C4 0.0456(16) 0.0429(15) 0.0427(15) 0.0012(11) 0.0006(13) 0.0077(11) C5 0.073(2) 0.073(2) 0.0361(16) 0.0003(13) -0.0029(16) 0.0126(17) C6 0.0339(12) 0.0335(12) 0.0384(13) 0.0027(9) 0.0024(10) 0.0026(9) C7 0.0317(12) 0.0451(13) 0.0396(14) 0.0078(11) 0.0066(11) 0.0026(10) C8 0.0298(12) 0.0389(12) 0.0355(13) 0.0035(9) 0.0030(10) 0.0023(9) C9 0.0358(13) 0.0452(14) 0.0389(13) 0.0021(11) 0.0021(10) 0.0046(11) C10 0.069(2) 0.0614(19) 0.0514(18) -0.0024(15) 0.0112(16) 0.0170(17) C11 0.0535(17) 0.0420(14) 0.0374(14) 0.0062(11) 0.0053(12) 0.0055(12) C12 0.095(3) 0.0608(19) 0.0421(16) 0.0188(14) 0.0116(17) 0.0136(19) C13 0.099(3) 0.130(4) 0.053(2) 0.033(3) -0.014(2) 0.008(3) O3 0.146(3) 0.0564(13) 0.0493(13) -0.0142(11) -0.0609(16) 0.0364(17) O2 0.0814(19) 0.0541(14) 0.0598(15) 0.0022(10) -0.0053(14) 0.0103(11) _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 1.984(2) 2 ? Cu1 N1 1.984(2) . ? Cu1 N3 2.148(2) . ? Cu1 N3 2.148(2) 2 ? Cu1 O1 2.353(3) . ? Cu1 O1 2.353(3) 2 ? O1 N9 1.263(3) . ? N1 C3 1.329(3) . ? N1 C6 1.401(3) . ? N2 C3 1.353(4) . ? N2 C4 1.380(4) . ? N3 C11 1.318(3) . ? N3 C8 1.391(3) . ? N4 C11 1.355(3) . ? N4 C9 1.391(4) . ? N9 O1 1.263(3) 2 ? C1 C2 1.530(5) . ? C1 H17A 0.9600 . ? C1 H17B 0.9600 . ? C1 H17C 0.9600 . ? C2 C3 1.488(4) . ? C2 H1A 0.9700 . ? C2 H1B 0.9700 . ? C4 C6 1.339(4) . ? C4 C5 1.507(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.486(4) . ? C7 C8 1.501(3) . ? C7 H6A 0.9700 . ? C7 H6B 0.9700 . ? C8 C9 1.360(4) . ? C9 C10 1.482(4) . ? C10 H9A 0.9600 . ? C10 H9B 0.9600 . ? C10 H9C 0.9600 . ? C11 C12 1.500(4) . ? C12 C13 1.514(6) . ? C12 H11A 0.9700 . ? C12 H11B 0.9700 . ? C13 H23A 0.9600 . ? C13 H23B 0.9600 . ? C13 H23C 0.9600 . ? 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 171.47(12) 2 . ? N1 Cu1 N3 96.62(9) 2 . ? N1 Cu1 N3 89.14(9) . . ? N1 Cu1 N3 89.14(9) 2 2 ? N1 Cu1 N3 96.62(9) . 2 ? N3 Cu1 N3 95.21(12) . 2 ? N1 Cu1 O1 86.05(9) 2 . ? N1 Cu1 O1 86.31(9) . . ? N3 Cu1 O1 158.59(10) . . ? N3 Cu1 O1 106.10(8) 2 . ? N1 Cu1 O1 86.31(9) 2 2 ? N1 Cu1 O1 86.05(9) . 2 ? N3 Cu1 O1 106.10(8) . 2 ? N3 Cu1 O1 158.59(10) 2 2 ? O1 Cu1 O1 52.74(13) . 2 ? N9 O1 Cu1 97.8(2) . . ? C3 N1 C6 106.0(2) . . ? C3 N1 Cu1 129.4(2) . . ? C6 N1 Cu1 124.52(18) . . ? C3 N2 C4 107.9(2) . . ? C11 N3 C8 106.0(2) . . ? C11 N3 Cu1 132.03(19) . . ? C8 N3 Cu1 119.97(17) . . ? C11 N4 C9 107.9(2) . . ? O1 N9 O1 111.6(4) 2 . ? C2 C1 H17A 109.5 . . ? C2 C1 H17B 109.5 . . ? H17A C1 H17B 109.5 . . ? C2 C1 H17C 109.5 . . ? H17A C1 H17C 109.5 . . ? H17B C1 H17C 109.5 . . ? C3 C2 C1 113.5(3) . . ? C3 C2 H1A 108.9 . . ? C1 C2 H1A 108.9 . . ? C3 C2 H1B 108.9 . . ? C1 C2 H1B 108.9 . . ? H1A C2 H1B 107.7 . . ? N1 C3 N2 110.1(2) . . ? N1 C3 C2 127.1(3) . . ? N2 C3 C2 122.8(3) . . ? C6 C4 N2 106.7(3) . . ? C6 C4 C5 132.4(3) . . ? N2 C4 C5 120.9(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 N1 109.3(3) . . ? C4 C6 C7 130.8(3) . . ? N1 C6 C7 119.9(2) . . ? C6 C7 C8 111.9(2) . . ? C6 C7 H6A 109.2 . . ? C8 C7 H6A 109.2 . . ? C6 C7 H6B 109.2 . . ? C8 C7 H6B 109.2 . . ? H6A C7 H6B 107.9 . . ? C9 C8 N3 110.0(2) . . ? C9 C8 C7 129.6(2) . . ? N3 C8 C7 120.3(2) . . ? C8 C9 N4 105.2(2) . . ? C8 C9 C10 132.2(3) . . ? N4 C9 C10 122.6(3) . . ? C9 C10 H9A 109.5 . . ? C9 C10 H9B 109.5 . . ? H9A C10 H9B 109.5 . . ? C9 C10 H9C 109.5 . . ? H9A C10 H9C 109.5 . . ? H9B C10 H9C 109.5 . . ? N3 C11 N4 110.8(2) . . ? N3 C11 C12 127.4(3) . . ? N4 C11 C12 121.7(3) . . ? C11 C12 C13 114.6(3) . . ? C11 C12 H11A 108.6 . . ? C13 C12 H11A 108.6 . . ? C11 C12 H11B 108.6 . . ? C13 C12 H11B 108.6 . . ? H11A C12 H11B 107.6 . . ? C12 C13 H23A 109.5 . . ? C12 C13 H23B 109.5 . . ? H23A C13 H23B 109.5 . . ? C12 C13 H23C 109.5 . . ? H23A C13 H23C 109.5 . . ? H23B C13 H23C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.346 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.112 # Attachment '- complex 1_revised.cif' data_14 _database_code_depnum_ccdc_archive 'CCDC 852717' #TrackingRef '- complex 1_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C30 H42 Cl2 Cu N10 O8' _chemical_formula_sum 'C30 H42 Cl2 Cu N10 O8' _chemical_compound_source synthesised _exptl_crystal_recrystallization_method Acetonitrile _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour brown _diffrn_ambient_temperature 296(2) _chemical_formula_weight 805.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3488(6) _cell_length_b 11.1223(7) _cell_length_c 18.8929(11) _cell_angle_alpha 77.839(3) _cell_angle_beta 86.532(3) _cell_angle_gamma 82.881(3) _cell_volume 1904.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6824 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 20.68 _exptl_crystal_size_max 0.042 _exptl_crystal_size_mid 0.031 _exptl_crystal_size_min 0.019 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 838 _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 23654 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 28.32 _reflns_number_total 9262 _reflns_number_gt 6429 _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^)+(0.1045P)^2^+0.8891P] 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 9262 _refine_ls_number_parameters 472 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1888 _refine_ls_wR_factor_gt 0.1675 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.009 _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 1.0000 1.0000 0.0000 0.05489(19) Uani 1 2 d S . . N1 N 0.8996(3) 0.9687(2) 0.09968(13) 0.0475(6) Uani 1 1 d . . . N2 N 0.7716(3) 0.9709(3) 0.20009(14) 0.0529(7) Uani 1 1 d . . . N3 N 0.9354(3) 0.8415(2) -0.01231(13) 0.0472(6) Uani 1 1 d . . . N4 N 0.8305(4) 0.6979(3) -0.04455(17) 0.0605(8) Uani 1 1 d . . . N10 N 0.7098(5) 0.0937(4) 0.9549(2) 0.0891(12) Uani 1 1 d . . . C2 C 0.7537(6) 1.1727(3) 0.1116(2) 0.0730(12) Uani 1 1 d . . . H1A H 0.8215 1.2127 0.0762 0.088 Uiso 1 1 calc R . . H1B H 0.6635 1.1776 0.0878 0.088 Uiso 1 1 calc R . . C3 C 0.8105(4) 1.0394(3) 0.13548(18) 0.0527(8) Uani 1 1 d . . . C4 C 0.8365(3) 0.8511(3) 0.20601(17) 0.0463(7) Uani 1 1 d . . . C5 C 0.8116(5) 0.7523(3) 0.27073(19) 0.0625(9) Uani 1 1 d . . . H4A H 0.7977 0.7911 0.3135 0.075 Uiso 1 1 d R . . H4B H 0.7213 0.7203 0.2658 0.075 Uiso 1 1 d R . . H4C H 0.8873 0.6893 0.2778 0.075 Uiso 1 1 d R . . C6 C 0.9155(3) 0.8501(3) 0.14339(15) 0.0419(6) Uani 1 1 d . . . C7 C 0.9980(3) 0.7458(3) 0.11507(17) 0.0458(7) Uani 1 1 d . . . H6A H 0.9902 0.6687 0.1495 0.055 Uiso 1 1 calc R . . H6B H 1.0991 0.7586 0.1084 0.055 Uiso 1 1 calc R . . C8 C 0.9391(3) 0.7393(3) 0.04461(16) 0.0423(6) Uani 1 1 d . . . C9 C 0.8744(4) 0.6498(3) 0.02521(19) 0.0523(8) Uani 1 1 d . . . C10 C 0.8423(5) 0.5250(3) 0.0657(3) 0.0747(11) Uani 1 1 d . . . H10A H 0.8862 0.5067 0.1119 0.112 Uiso 1 1 calc R . . H10B H 0.8801 0.4636 0.0384 0.112 Uiso 1 1 calc R . . H10C H 0.7398 0.5243 0.0727 0.112 Uiso 1 1 calc R . . C11 C 0.8692(4) 0.8133(3) -0.06594(18) 0.0550(8) Uani 1 1 d . . . C12 C 0.8367(6) 0.8916(4) -0.1386(2) 0.0757(12) Uani 1 1 d . . . H11A H 0.8480 0.9768 -0.1377 0.091 Uiso 1 1 calc R . . H11B H 0.9064 0.8652 -0.1740 0.091 Uiso 1 1 calc R . . C1 C 0.7288(7) 1.2416(4) 0.1713(3) 0.1043(18) Uani 1 1 d . . . H12A H 0.6649 1.2008 0.2077 0.156 Uiso 1 1 calc R . . H12B H 0.6862 1.3245 0.1525 0.156 Uiso 1 1 calc R . . H12C H 0.8190 1.2443 0.1923 0.156 Uiso 1 1 calc R . . C13 C 0.6887(9) 0.8863(6) -0.1623(3) 0.134(3) Uani 1 1 d . . . H23A H 0.6777 0.8029 -0.1652 0.201 Uiso 1 1 calc R . . H23B H 0.6744 0.9396 -0.2090 0.201 Uiso 1 1 calc R . . H23C H 0.6187 0.9132 -0.1279 0.201 Uiso 1 1 calc R . . C29 C 0.5940(5) 0.1297(4) 0.9423(3) 0.0771(12) Uani 1 1 d . . . C30 C 0.4471(6) 0.1766(6) 0.9250(5) 0.137(3) Uani 1 1 d . . . H30A H 0.3902 0.1775 0.9690 0.206 Uiso 1 1 calc R . . H30B H 0.4091 0.1243 0.8981 0.206 Uiso 1 1 calc R . . H30C H 0.4439 0.2591 0.8965 0.206 Uiso 1 1 calc R . . Cu2 Cu 0.0000 0.5000 0.5000 0.03937(15) Uani 1 2 d S . . N9 N 0.2221(5) 0.5548(4) 0.5858(3) 0.0928(12) Uani 1 1 d . . . N5 N -0.1061(2) 0.4594(2) 0.59553(13) 0.0395(5) Uani 1 1 d . . . N6 N -0.2026(3) 0.4511(3) 0.70428(15) 0.0560(7) Uani 1 1 d . . . N7 N 0.0972(2) 0.3239(2) 0.52352(13) 0.0381(5) Uani 1 1 d . . . N8 N 0.2410(3) 0.1508(2) 0.53762(16) 0.0492(6) Uani 1 1 d . . . C14 C -0.0348(7) 0.6588(6) 0.7199(3) 0.1045(19) Uani 1 1 d . . . H29A H 0.0437 0.5948 0.7325 0.157 Uiso 1 1 calc R . . H29B H -0.1079 0.6511 0.7580 0.157 Uiso 1 1 calc R . . H29C H -0.0003 0.7383 0.7135 0.157 Uiso 1 1 calc R . . C15 C -0.0974(4) 0.6466(3) 0.6506(2) 0.0574(8) Uani 1 1 d . . . H15 H -0.1841 0.7045 0.6420 0.069 Uiso 1 1 calc R . . H16 H -0.0289 0.6702 0.6110 0.069 Uiso 1 1 calc R . . C16 C -0.1338(3) 0.5211(3) 0.64945(17) 0.0461(7) Uani 1 1 d . . . C17 C -0.2209(4) 0.3407(3) 0.68571(18) 0.0536(8) Uani 1 1 d . . . C18 C -0.2913(5) 0.2399(5) 0.7364(2) 0.0831(13) Uani 1 1 d . . . H18A H -0.2915 0.1705 0.7136 0.125 Uiso 1 1 calc R . . H18B H -0.3888 0.2703 0.7477 0.125 Uiso 1 1 calc R . . H18C H -0.2386 0.2145 0.7801 0.125 Uiso 1 1 calc R . . C19 C -0.1605(3) 0.3462(3) 0.61836(16) 0.0418(6) Uani 1 1 d . . . C20 C -0.1391(3) 0.2509(3) 0.57249(17) 0.0445(7) Uani 1 1 d . . . H35A H -0.1932 0.2801 0.5288 0.053 Uiso 1 1 calc R . . H35B H -0.1745 0.1750 0.5987 0.053 Uiso 1 1 calc R . . C21 C 0.0183(3) 0.2260(3) 0.55286(16) 0.0398(6) Uani 1 1 d . . . C22 C 0.1063(4) 0.1182(3) 0.56148(19) 0.0497(7) Uani 1 1 d . . . C23 C 0.0810(5) -0.0134(3) 0.5919(3) 0.0780(13) Uani 1 1 d . . . H38A H -0.0171 -0.0162 0.6098 0.117 Uiso 1 1 calc R . . H38B H 0.1450 -0.0476 0.6308 0.117 Uiso 1 1 calc R . . H38C H 0.0990 -0.0607 0.5546 0.117 Uiso 1 1 calc R . . C24 C 0.2328(3) 0.2750(3) 0.51546(16) 0.0416(6) Uani 1 1 d . . . C25 C 0.3601(3) 0.3407(3) 0.4891(2) 0.0541(8) Uani 1 1 d . . . H40A H 0.3315 0.4292 0.4805 0.065 Uiso 1 1 calc R . . H40B H 0.3952 0.3200 0.4432 0.065 Uiso 1 1 calc R . . C27 C 0.3008(6) 0.5576(5) 0.6293(3) 0.0791(12) Uani 1 1 d . . . C26 C 0.4813(4) 0.3077(5) 0.5422(3) 0.0916(16) Uani 1 1 d . . . H44A H 0.4457 0.3238 0.5885 0.137 Uiso 1 1 calc R . . H44B H 0.5583 0.3569 0.5245 0.137 Uiso 1 1 calc R . . H44C H 0.5164 0.2216 0.5473 0.137 Uiso 1 1 calc R . . C28 C 0.3995(7) 0.5596(7) 0.6849(4) 0.126(2) Uani 1 1 d . . . H60A H 0.4942 0.5249 0.6718 0.189 Uiso 1 1 calc R . . H60B H 0.3674 0.5116 0.7302 0.189 Uiso 1 1 calc R . . H60C H 0.4026 0.6434 0.6897 0.189 Uiso 1 1 calc R . . Cl2 Cl 0.46380(10) 0.06591(9) 0.35559(5) 0.0615(2) Uani 1 1 d . . . O7 O 0.5204(5) 0.0576(5) 0.4238(2) 0.1355(19) Uani 1 1 d . . . O5 O 0.5539(4) -0.0082(4) 0.3163(2) 0.1066(12) Uani 1 1 d . . . O8 O 0.4399(5) 0.1893(3) 0.3194(2) 0.1140(13) Uani 1 1 d . . . O6 O 0.3271(5) 0.0251(5) 0.3656(3) 0.1510(19) Uani 1 1 d . . . Cl1 Cl 0.37285(11) 0.51244(9) 0.11346(5) 0.0652(3) Uani 1 1 d . . . O1 O 0.2391(5) 0.4799(5) 0.1458(3) 0.1358(17) Uani 1 1 d . . . O2 O 0.4323(5) 0.4089(4) 0.0842(3) 0.1205(14) Uani 1 1 d . . . O3 O 0.3448(7) 0.6138(4) 0.0559(3) 0.1456(18) Uani 1 1 d . . . O4 O 0.4591(7) 0.5397(5) 0.1625(3) 0.155(2) 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 0.0906(5) 0.0416(3) 0.0374(3) -0.0129(2) 0.0214(3) -0.0298(3) N1 0.0677(17) 0.0383(13) 0.0374(13) -0.0091(10) 0.0133(12) -0.0143(12) N2 0.0685(18) 0.0484(15) 0.0394(14) -0.0090(11) 0.0140(12) -0.0051(13) N3 0.0655(17) 0.0415(13) 0.0373(13) -0.0105(10) 0.0079(12) -0.0169(12) N4 0.078(2) 0.0486(16) 0.0594(18) -0.0130(13) -0.0103(15) -0.0184(14) N10 0.092(3) 0.080(3) 0.091(3) -0.016(2) -0.013(2) 0.012(2) C2 0.110(3) 0.045(2) 0.059(2) -0.0066(16) 0.011(2) -0.001(2) C3 0.074(2) 0.0422(17) 0.0413(17) -0.0092(13) 0.0073(15) -0.0064(15) C4 0.0514(17) 0.0445(16) 0.0410(16) -0.0048(13) 0.0039(13) -0.0074(13) C5 0.078(2) 0.059(2) 0.0424(18) 0.0037(15) 0.0126(17) -0.0070(18) C6 0.0496(16) 0.0404(15) 0.0360(14) -0.0070(12) 0.0050(12) -0.0113(12) C7 0.0472(16) 0.0442(16) 0.0448(16) -0.0077(13) 0.0064(13) -0.0068(13) C8 0.0498(16) 0.0337(14) 0.0425(16) -0.0077(12) 0.0086(13) -0.0066(12) C9 0.064(2) 0.0377(16) 0.056(2) -0.0090(14) 0.0008(16) -0.0122(14) C10 0.099(3) 0.0405(19) 0.084(3) -0.0055(18) -0.001(2) -0.0211(19) C11 0.075(2) 0.0438(17) 0.0479(18) -0.0119(14) 0.0007(16) -0.0116(16) C12 0.118(4) 0.062(2) 0.048(2) -0.0065(17) -0.011(2) -0.017(2) C1 0.156(5) 0.055(3) 0.097(4) -0.020(2) 0.011(4) 0.006(3) C13 0.210(8) 0.090(4) 0.108(4) 0.015(3) -0.095(5) -0.057(4) C29 0.078(3) 0.062(3) 0.084(3) -0.001(2) -0.001(2) -0.005(2) C30 0.061(3) 0.102(4) 0.214(8) 0.049(5) -0.009(4) -0.013(3) Cu2 0.0389(3) 0.0350(3) 0.0385(3) -0.00070(19) 0.01014(19) 0.00062(19) N9 0.093(3) 0.096(3) 0.088(3) -0.019(2) 0.010(2) -0.011(2) N5 0.0361(12) 0.0429(13) 0.0362(12) -0.0037(10) 0.0044(9) -0.0022(10) N6 0.0532(16) 0.0691(19) 0.0421(15) -0.0079(13) 0.0094(12) -0.0049(14) N7 0.0353(12) 0.0380(12) 0.0386(12) -0.0044(9) 0.0032(9) -0.0030(9) N8 0.0434(14) 0.0389(13) 0.0631(17) -0.0093(12) -0.0069(12) 0.0039(11) C14 0.147(5) 0.123(4) 0.061(3) -0.036(3) 0.009(3) -0.059(4) C15 0.060(2) 0.056(2) 0.058(2) -0.0200(16) 0.0025(16) 0.0000(16) C16 0.0402(15) 0.0553(18) 0.0398(16) -0.0082(13) 0.0043(12) 0.0007(13) C17 0.0449(17) 0.066(2) 0.0435(17) 0.0023(15) 0.0066(13) -0.0098(15) C18 0.088(3) 0.091(3) 0.063(3) 0.007(2) 0.026(2) -0.032(2) C19 0.0328(14) 0.0478(16) 0.0409(15) -0.0003(12) 0.0006(11) -0.0057(12) C20 0.0388(15) 0.0482(17) 0.0460(17) -0.0054(13) -0.0012(12) -0.0101(12) C21 0.0399(15) 0.0384(14) 0.0408(15) -0.0063(11) -0.0020(11) -0.0065(11) C22 0.0527(18) 0.0389(16) 0.0568(19) -0.0059(13) -0.0126(15) -0.0036(13) C23 0.082(3) 0.0360(18) 0.113(4) -0.003(2) -0.018(3) -0.0099(18) C24 0.0372(14) 0.0421(15) 0.0436(16) -0.0079(12) -0.0013(12) 0.0015(12) C25 0.0382(16) 0.058(2) 0.063(2) -0.0096(16) 0.0111(14) -0.0042(14) C27 0.075(3) 0.087(3) 0.077(3) -0.020(2) 0.009(2) -0.015(2) C26 0.045(2) 0.086(3) 0.132(4) 0.012(3) -0.016(2) -0.015(2) C28 0.108(5) 0.161(7) 0.121(5) -0.038(5) -0.007(4) -0.044(4) Cl2 0.0645(5) 0.0611(5) 0.0524(5) -0.0072(4) 0.0024(4) 0.0086(4) O7 0.156(4) 0.164(4) 0.079(2) -0.053(3) -0.048(2) 0.080(3) O5 0.117(3) 0.111(3) 0.081(2) -0.027(2) 0.027(2) 0.022(2) O8 0.136(3) 0.067(2) 0.124(3) 0.004(2) -0.008(3) 0.009(2) O6 0.093(3) 0.153(4) 0.211(6) -0.043(4) 0.045(3) -0.046(3) Cl1 0.0716(6) 0.0672(6) 0.0628(6) -0.0248(5) 0.0161(4) -0.0205(4) O1 0.118(3) 0.167(4) 0.138(4) -0.059(3) 0.054(3) -0.057(3) O2 0.124(3) 0.106(3) 0.142(4) -0.061(3) 0.019(3) -0.004(2) O3 0.213(6) 0.102(3) 0.112(3) 0.004(3) -0.006(3) -0.024(3) O4 0.199(5) 0.174(5) 0.119(4) -0.047(3) -0.041(4) -0.075(4) _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 N3 1.995(2) . ? Cu1 N3 1.995(2) 2_775 ? Cu1 N1 2.035(2) . ? Cu1 N1 2.035(2) 2_775 ? N1 C3 1.328(4) . ? N1 C6 1.397(4) . ? N2 C3 1.351(4) . ? N2 C4 1.379(4) . ? N3 C11 1.329(4) . ? N3 C8 1.389(4) . ? N4 C11 1.349(4) . ? N4 C9 1.380(5) . ? N10 C29 1.128(6) . ? C2 C1 1.484(6) . ? C2 C3 1.495(5) . ? C2 H1A 0.9700 . ? C2 H1B 0.9700 . ? C4 C6 1.357(4) . ? C4 C5 1.490(4) . ? C5 H4A 0.9879 . ? C5 H4B 0.9726 . ? C5 H4C 0.9267 . ? C6 C7 1.489(4) . ? C7 C8 1.490(4) . ? C7 H6A 0.9700 . ? C7 H6B 0.9700 . ? C8 C9 1.350(4) . ? C9 C10 1.493(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.489(5) . ? C12 C13 1.491(8) . ? C12 H11A 0.9700 . ? C12 H11B 0.9700 . ? C1 H12A 0.9600 . ? C1 H12B 0.9600 . ? C1 H12C 0.9600 . ? C13 H23A 0.9600 . ? C13 H23B 0.9600 . ? C13 H23C 0.9600 . ? C29 C30 1.439(7) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? Cu2 N5 1.999(2) 2_566 ? Cu2 N5 1.999(2) . ? Cu2 N7 2.025(2) 2_566 ? Cu2 N7 2.025(2) . ? N9 C27 1.143(6) . ? N5 C16 1.340(4) . ? N5 C19 1.390(4) . ? N6 C16 1.340(4) . ? N6 C17 1.379(5) . ? N7 C24 1.329(4) . ? N7 C21 1.390(4) . ? N8 C24 1.351(4) . ? N8 C22 1.378(4) . ? C14 C15 1.504(6) . ? C14 H29A 0.9600 . ? C14 H29B 0.9600 . ? C14 H29C 0.9600 . ? C15 C16 1.482(5) . ? C15 H15 0.9700 . ? C15 H16 0.9700 . ? C17 C19 1.353(4) . ? C17 C18 1.504(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.492(4) . ? C20 C21 1.502(4) . ? C20 H35A 0.9700 . ? C20 H35B 0.9700 . ? C21 C22 1.353(4) . ? C22 C23 1.497(5) . ? C23 H38A 0.9600 . ? C23 H38B 0.9600 . ? C23 H38C 0.9600 . ? C24 C25 1.479(4) . ? C25 C26 1.518(6) . ? C25 H40A 0.9700 . ? C25 H40B 0.9700 . ? C27 C28 1.446(8) . ? C26 H44A 0.9600 . ? C26 H44B 0.9600 . ? C26 H44C 0.9600 . ? C28 H60A 0.9600 . ? C28 H60B 0.9600 . ? C28 H60C 0.9600 . ? Cl2 O6 1.398(4) . ? Cl2 O8 1.396(3) . ? Cl2 O5 1.396(3) . ? Cl2 O7 1.404(4) . ? Cl1 O4 1.368(4) . ? Cl1 O3 1.403(5) . ? Cl1 O1 1.412(4) . ? Cl1 O2 1.419(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 N3 Cu1 N3 180.0 . 2_775 ? N3 Cu1 N1 86.66(10) . . ? N3 Cu1 N1 93.34(10) 2_775 . ? N3 Cu1 N1 93.34(10) . 2_775 ? N3 Cu1 N1 86.66(10) 2_775 2_775 ? N1 Cu1 N1 180.000(2) . 2_775 ? C3 N1 C6 106.8(2) . . ? C3 N1 Cu1 133.4(2) . . ? C6 N1 Cu1 119.73(19) . . ? C3 N2 C4 109.3(3) . . ? C11 N3 C8 107.0(3) . . ? C11 N3 Cu1 131.6(2) . . ? C8 N3 Cu1 121.0(2) . . ? C11 N4 C9 109.1(3) . . ? C1 C2 C3 114.2(4) . . ? C1 C2 H1A 108.7 . . ? C3 C2 H1A 108.7 . . ? C1 C2 H1B 108.7 . . ? C3 C2 H1B 108.7 . . ? H1A C2 H1B 107.6 . . ? N1 C3 N2 109.2(3) . . ? N1 C3 C2 128.5(3) . . ? N2 C3 C2 122.3(3) . . ? C6 C4 N2 105.5(3) . . ? C6 C4 C5 132.4(3) . . ? N2 C4 C5 122.0(3) . . ? C4 C5 H4A 107.9 . . ? C4 C5 H4B 108.8 . . ? H4A C5 H4B 106.2 . . ? C4 C5 H4C 112.6 . . ? H4A C5 H4C 109.9 . . ? H4B C5 H4C 111.2 . . ? C4 C6 N1 109.1(3) . . ? C4 C6 C7 130.8(3) . . ? N1 C6 C7 119.8(2) . . ? C6 C7 C8 109.3(3) . . ? C6 C7 H6A 109.8 . . ? C8 C7 H6A 109.8 . . ? C6 C7 H6B 109.8 . . ? C8 C7 H6B 109.8 . . ? H6A C7 H6B 108.3 . . ? C9 C8 N3 109.3(3) . . ? C9 C8 C7 130.7(3) . . ? N3 C8 C7 119.8(3) . . ? C8 C9 N4 105.6(3) . . ? C8 C9 C10 132.1(3) . . ? N4 C9 C10 122.2(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 N4 109.0(3) . . ? N3 C11 C12 128.3(3) . . ? N4 C11 C12 122.7(3) . . ? C13 C12 C11 113.8(4) . . ? C13 C12 H11A 108.8 . . ? C11 C12 H11A 108.8 . . ? C13 C12 H11B 108.8 . . ? C11 C12 H11B 108.8 . . ? H11A C12 H11B 107.7 . . ? C2 C1 H12A 109.5 . . ? C2 C1 H12B 109.5 . . ? H12A C1 H12B 109.5 . . ? C2 C1 H12C 109.5 . . ? H12A C1 H12C 109.5 . . ? H12B C1 H12C 109.5 . . ? C12 C13 H23A 109.5 . . ? C12 C13 H23B 109.5 . . ? H23A C13 H23B 109.5 . . ? C12 C13 H23C 109.5 . . ? H23A C13 H23C 109.5 . . ? H23B C13 H23C 109.5 . . ? N10 C29 C30 179.1(6) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N5 Cu2 N5 180.0 2_566 . ? N5 Cu2 N7 86.31(9) 2_566 2_566 ? N5 Cu2 N7 93.69(9) . 2_566 ? N5 Cu2 N7 93.69(9) 2_566 . ? N5 Cu2 N7 86.31(9) . . ? N7 Cu2 N7 180.0 2_566 . ? C16 N5 C19 106.9(2) . . ? C16 N5 Cu2 131.9(2) . . ? C19 N5 Cu2 121.07(19) . . ? C16 N6 C17 109.3(3) . . ? C24 N7 C21 106.6(2) . . ? C24 N7 Cu2 132.5(2) . . ? C21 N7 Cu2 120.88(18) . . ? C24 N8 C22 109.2(2) . . ? C15 C14 H29A 109.5 . . ? C15 C14 H29B 109.5 . . ? H29A C14 H29B 109.5 . . ? C15 C14 H29C 109.5 . . ? H29A C14 H29C 109.5 . . ? H29B C14 H29C 109.5 . . ? C16 C15 C14 114.9(4) . . ? C16 C15 H15 108.5 . . ? C14 C15 H15 108.5 . . ? C16 C15 H16 108.5 . . ? C14 C15 H16 108.5 . . ? H15 C15 H16 107.5 . . ? N5 C16 N6 109.0(3) . . ? N5 C16 C15 127.2(3) . . ? N6 C16 C15 123.8(3) . . ? C19 C17 N6 106.0(3) . . ? C19 C17 C18 131.4(4) . . ? N6 C17 C18 122.6(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 N5 108.9(3) . . ? C17 C19 C20 130.3(3) . . ? N5 C19 C20 120.7(2) . . ? C19 C20 C21 109.9(2) . . ? C19 C20 H35A 109.7 . . ? C21 C20 H35A 109.7 . . ? C19 C20 H35B 109.7 . . ? C21 C20 H35B 109.7 . . ? H35A C20 H35B 108.2 . . ? C22 C21 N7 109.6(3) . . ? C22 C21 C20 130.3(3) . . ? N7 C21 C20 120.0(2) . . ? C21 C22 N8 105.3(3) . . ? C21 C22 C23 132.6(3) . . ? N8 C22 C23 122.0(3) . . ? C22 C23 H38A 109.5 . . ? C22 C23 H38B 109.5 . . ? H38A C23 H38B 109.5 . . ? C22 C23 H38C 109.5 . . ? H38A C23 H38C 109.5 . . ? H38B C23 H38C 109.5 . . ? N7 C24 N8 109.2(3) . . ? N7 C24 C25 127.9(3) . . ? N8 C24 C25 122.9(3) . . ? C24 C25 C26 112.5(3) . . ? C24 C25 H40A 109.1 . . ? C26 C25 H40A 109.1 . . ? C24 C25 H40B 109.1 . . ? C26 C25 H40B 109.1 . . ? H40A C25 H40B 107.8 . . ? N9 C27 C28 179.1(6) . . ? C25 C26 H44A 109.5 . . ? C25 C26 H44B 109.5 . . ? H44A C26 H44B 109.5 . . ? C25 C26 H44C 109.5 . . ? H44A C26 H44C 109.5 . . ? H44B C26 H44C 109.5 . . ? C27 C28 H60A 109.5 . . ? C27 C28 H60B 109.5 . . ? H60A C28 H60B 109.5 . . ? C27 C28 H60C 109.5 . . ? H60A C28 H60C 109.5 . . ? H60B C28 H60C 109.5 . . ? O6 Cl2 O8 104.9(3) . . ? O6 Cl2 O5 109.6(3) . . ? O8 Cl2 O5 113.1(3) . . ? O6 Cl2 O7 108.6(4) . . ? O8 Cl2 O7 110.6(3) . . ? O5 Cl2 O7 109.9(2) . . ? O4 Cl1 O3 111.1(3) . . ? O4 Cl1 O1 111.5(3) . . ? O3 Cl1 O1 107.9(4) . . ? O4 Cl1 O2 113.2(4) . . ? O3 Cl1 O2 108.3(3) . . ? O1 Cl1 O2 104.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C3 -133.6(3) . . . . ? N3 Cu1 N1 C3 46.4(3) 2_775 . . . ? N1 Cu1 N1 C3 70(65) 2_775 . . . ? N3 Cu1 N1 C6 43.4(2) . . . . ? N3 Cu1 N1 C6 -136.6(2) 2_775 . . . ? N1 Cu1 N1 C6 -113(65) 2_775 . . . ? N3 Cu1 N3 C11 -142(31) 2_775 . . . ? N1 Cu1 N3 C11 130.9(3) . . . . ? N1 Cu1 N3 C11 -49.1(3) 2_775 . . . ? N3 Cu1 N3 C8 47(31) 2_775 . . . ? N1 Cu1 N3 C8 -40.2(2) . . . . ? N1 Cu1 N3 C8 139.8(2) 2_775 . . . ? C6 N1 C3 N2 0.9(4) . . . . ? Cu1 N1 C3 N2 178.2(2) . . . . ? C6 N1 C3 C2 -177.5(4) . . . . ? Cu1 N1 C3 C2 -0.2(6) . . . . ? C4 N2 C3 N1 -0.7(4) . . . . ? C4 N2 C3 C2 177.8(4) . . . . ? C1 C2 C3 N1 -147.4(5) . . . . ? C1 C2 C3 N2 34.4(6) . . . . ? C3 N2 C4 C6 0.2(4) . . . . ? C3 N2 C4 C5 -178.5(3) . . . . ? N2 C4 C6 N1 0.4(4) . . . . ? C5 C4 C6 N1 178.9(4) . . . . ? N2 C4 C6 C7 -173.6(3) . . . . ? C5 C4 C6 C7 4.9(6) . . . . ? C3 N1 C6 C4 -0.8(4) . . . . ? Cu1 N1 C6 C4 -178.5(2) . . . . ? C3 N1 C6 C7 173.9(3) . . . . ? Cu1 N1 C6 C7 -3.8(4) . . . . ? C4 C6 C7 C8 120.3(4) . . . . ? N1 C6 C7 C8 -53.2(4) . . . . ? C11 N3 C8 C9 -0.3(4) . . . . ? Cu1 N3 C8 C9 172.8(2) . . . . ? C11 N3 C8 C7 -175.7(3) . . . . ? Cu1 N3 C8 C7 -2.6(4) . . . . ? C6 C7 C8 C9 -116.7(4) . . . . ? C6 C7 C8 N3 57.5(4) . . . . ? N3 C8 C9 N4 0.0(4) . . . . ? C7 C8 C9 N4 174.7(3) . . . . ? N3 C8 C9 C10 -176.7(4) . . . . ? C7 C8 C9 C10 -2.0(6) . . . . ? C11 N4 C9 C8 0.3(4) . . . . ? C11 N4 C9 C10 177.4(4) . . . . ? C8 N3 C11 N4 0.5(4) . . . . ? Cu1 N3 C11 N4 -171.6(2) . . . . ? C8 N3 C11 C12 179.4(4) . . . . ? Cu1 N3 C11 C12 7.4(6) . . . . ? C9 N4 C11 N3 -0.5(4) . . . . ? C9 N4 C11 C12 -179.5(4) . . . . ? N3 C11 C12 C13 -136.6(5) . . . . ? N4 C11 C12 C13 42.2(6) . . . . ? N5 Cu2 N5 C16 96(15) 2_566 . . . ? N7 Cu2 N5 C16 -45.5(3) 2_566 . . . ? N7 Cu2 N5 C16 134.5(3) . . . . ? N5 Cu2 N5 C19 -80(15) 2_566 . . . ? N7 Cu2 N5 C19 138.3(2) 2_566 . . . ? N7 Cu2 N5 C19 -41.7(2) . . . . ? N5 Cu2 N7 C24 42.1(3) 2_566 . . . ? N5 Cu2 N7 C24 -137.9(3) . . . . ? N7 Cu2 N7 C24 101(3) 2_566 . . . ? N5 Cu2 N7 C21 -136.5(2) 2_566 . . . ? N5 Cu2 N7 C21 43.5(2) . . . . ? N7 Cu2 N7 C21 -78(3) 2_566 . . . ? C19 N5 C16 N6 0.0(3) . . . . ? Cu2 N5 C16 N6 -176.5(2) . . . . ? C19 N5 C16 C15 -179.6(3) . . . . ? Cu2 N5 C16 C15 3.8(5) . . . . ? C17 N6 C16 N5 -0.2(4) . . . . ? C17 N6 C16 C15 179.5(3) . . . . ? C14 C15 C16 N5 -135.7(4) . . . . ? C14 C15 C16 N6 44.7(5) . . . . ? C16 N6 C17 C19 0.3(4) . . . . ? C16 N6 C17 C18 178.4(4) . . . . ? N6 C17 C19 N5 -0.3(4) . . . . ? C18 C17 C19 N5 -178.2(4) . . . . ? N6 C17 C19 C20 175.5(3) . . . . ? C18 C17 C19 C20 -2.4(6) . . . . ? C16 N5 C19 C17 0.2(3) . . . . ? Cu2 N5 C19 C17 177.2(2) . . . . ? C16 N5 C19 C20 -176.1(3) . . . . ? Cu2 N5 C19 C20 0.9(4) . . . . ? C17 C19 C20 C21 -122.1(4) . . . . ? N5 C19 C20 C21 53.3(4) . . . . ? C24 N7 C21 C22 -0.9(3) . . . . ? Cu2 N7 C21 C22 178.1(2) . . . . ? C24 N7 C21 C20 176.7(3) . . . . ? Cu2 N7 C21 C20 -4.4(4) . . . . ? C19 C20 C21 C22 126.2(3) . . . . ? C19 C20 C21 N7 -50.8(4) . . . . ? N7 C21 C22 N8 0.5(4) . . . . ? C20 C21 C22 N8 -176.7(3) . . . . ? N7 C21 C22 C23 178.1(4) . . . . ? C20 C21 C22 C23 0.9(6) . . . . ? C24 N8 C22 C21 0.0(4) . . . . ? C24 N8 C22 C23 -177.9(3) . . . . ? C21 N7 C24 N8 0.8(3) . . . . ? Cu2 N7 C24 N8 -177.9(2) . . . . ? C21 N7 C24 C25 -177.4(3) . . . . ? Cu2 N7 C24 C25 3.9(5) . . . . ? C22 N8 C24 N7 -0.5(4) . . . . ? C22 N8 C24 C25 177.8(3) . . . . ? N7 C24 C25 C26 124.7(4) . . . . ? N8 C24 C25 C26 -53.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.740 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.075