# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/157 data_zb33 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H52 Cl2 Cu1 N4 O20' _chemical_formula_weight 995.26 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' .3639 .7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' -1.9646 .5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9740(10) _cell_length_b 11.4210(10) _cell_length_c 11.6980(10) _cell_angle_alpha 114.180(4) _cell_angle_beta 93.573(5) _cell_angle_gamma 116.809(6) _cell_volume 1137.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 72.0 _exptl_crystal_description Cubic _exptl_crystal_colour Green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method ? _exptl_crystal_F_000 519 _exptl_absorpt_coefficient_mu 2.461 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.7130 _exptl_absorpt_correction_T_max 0.9983 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54179 _diffrn_radiation_type CuKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Enraf-Nonius-cad-4 _diffrn_measurement_method omega-2-theta _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 4473 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0091 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 72.06 _reflns_number_total 4473 _reflns_number_observed 4229 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0847P)^2^+0.5721P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4472 _refine_ls_number_parameters 326 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_obs 0.0473 _refine_ls_wR_factor_all 0.1416 _refine_ls_wR_factor_obs 0.1375 _refine_ls_goodness_of_fit_all 1.082 _refine_ls_goodness_of_fit_obs 1.100 _refine_ls_restrained_S_all 1.099 _refine_ls_restrained_S_obs 1.100 _refine_ls_shift/esd_max 0.088 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl26 Cl 0.70999(8) 0.92664(8) 1.18527(7) 0.0672(2) Uani 1 d . . O30 O 0.6902(7) 0.8895(6) 1.0560(4) 0.169(2) Uani 1 d . . O27 O 0.6131(14) 0.7773(8) 1.1598(11) 0.171(4) Uani 0.50 d PD 1 O28 O 0.8382(7) 0.9956(15) 1.2769(7) 0.163(5) Uani 0.50 d PD 1 O29 O 0.6343(12) 1.0002(10) 1.2368(15) 0.148(6) Uani 0.50 d PD 1 O27A O 0.7606(16) 0.8536(17) 1.2181(12) 0.156(4) Uani 0.50 d PD 2 O28A O 0.8344(9) 1.0718(7) 1.2090(11) 0.141(3) Uani 0.50 d PD 2 O29A O 0.6237(17) 0.9550(18) 1.2494(19) 0.177(7) Uani 0.50 d PD 2 C8 C 0.7385(3) 0.8996(3) 0.5275(3) 0.0606(7) Uani 1 d . . H8A H 0.6910(20) 0.8663(17) 0.4389(3) 0.091 Uiso 1 calc R . H8B H 0.8113(5) 1.0045(4) 0.5692(20) 0.091 Uiso 1 calc R . H8C H 0.6700(18) 0.8851(20) 0.5754(19) 0.091 Uiso 1 calc R . Cu1 Cu 1.0000 0.5000 0.5000 0.03434(15) Uani 1 d S . O11 O 0.9906(2) 0.5286(2) 0.67516(14) 0.0391(3) Uani 1 d . . O22 O 0.7908(2) 0.2728(2) 0.7064(2) 0.0453(4) Uani 1 d . . N9 N 0.8329(2) 0.6085(2) 0.6906(2) 0.0375(4) Uani 1 d . . H9 H 0.7650(2) 0.6067(2) 0.7242(2) 0.053(8) Uiso 1 calc R . N2 N 0.9312(2) 0.6420(2) 0.5235(2) 0.0351(4) Uani 1 d . . O18 O 0.9782(2) 0.7929(2) 0.9704(2) 0.0576(5) Uani 1 d . . O20 O 0.7331(2) 0.2199(2) 0.9067(2) 0.0627(5) Uani 1 d . . O24 O 0.7497(2) 0.3007(2) 0.4070(2) 0.0712(6) Uani 1 d . . H24 H 0.7446(45) 0.2350(46) 0.3711(41) 0.080 Uiso 1 d . . O31 O 0.6312(2) 0.6437(3) 0.8170(2) 0.0689(6) Uani 1 d . . H31 H 0.6535(45) 0.7126(48) 0.8860(42) 0.090 Uiso 1 d . . C3 C 0.9512(3) 0.7082(2) 0.4472(2) 0.0429(5) Uani 1 d . . H3 H 1.0081(3) 0.6969(2) 0.3930(2) 0.052 Uiso 1 calc R . C4 C 0.8920(3) 0.7907(3) 0.4460(2) 0.0472(5) Uani 1 d . . H4 H 0.9091(3) 0.8338(3) 0.3919(2) 0.057 Uiso 1 calc R . C5 C 0.8060(3) 0.8102(3) 0.5261(2) 0.0435(5) Uani 1 d . . C6 C 0.7874(2) 0.7457(2) 0.6055(2) 0.0402(4) Uani 1 d . . H6 H 0.7309(2) 0.7559(2) 0.6605(2) 0.048 Uiso 1 calc R . C7 C 0.8527(2) 0.6655(2) 0.6037(2) 0.0341(4) Uani 1 d . . C10 C 0.9056(2) 0.5561(2) 0.7286(2) 0.0340(4) Uani 1 d . . C12 C 0.8792(2) 0.5331(2) 0.8425(2) 0.0364(4) Uani 1 d . . C13 C 0.9149(3) 0.6562(3) 0.9655(2) 0.0437(5) Uani 1 d . . C14 C 0.8868(3) 0.6314(3) 1.0693(2) 0.0545(6) Uani 1 d . . H14 H 0.9098(3) 0.7119(3) 1.1512(2) 0.065 Uiso 1 calc R . C15 C 0.8247(3) 0.4877(3) 1.0524(2) 0.0559(6) Uani 1 d . . H15 H 0.8054(3) 0.4728(3) 1.1232(2) 0.067 Uiso 1 calc R . C16 C 0.7904(2) 0.3650(3) 0.9323(2) 0.0475(5) Uani 1 d . . C17 C 0.8184(2) 0.3892(2) 0.8266(2) 0.0386(4) Uani 1 d . . C19 C 1.0554(3) 0.9252(3) 1.0954(3) 0.0663(7) Uani 1 d . . H19A H 0.9895(4) 0.9388(16) 1.1417(10) 0.099 Uiso 1 calc R . H19B H 1.1093(21) 1.0108(5) 1.0837(3) 0.099 Uiso 1 calc R . H19C H 1.1197(19) 0.9156(12) 1.1453(10) 0.099 Uiso 1 calc R . C21 C 0.6887(4) 0.1865(4) 1.0070(4) 0.0790(10) Uani 1 d . . H21A H 0.6460(29) 0.0805(7) 0.9754(11) 0.119 Uiso 1 calc R . H21B H 0.6200(24) 0.2148(31) 1.0303(21) 0.119 Uiso 1 calc R . H21C H 0.7703(6) 0.2417(26) 1.0830(11) 0.119 Uiso 1 calc R . C23 C 0.6435(3) 0.1748(3) 0.6316(3) 0.0640(7) Uani 1 d . . H23A H 0.6338(4) 0.1025(17) 0.5463(9) 0.096 Uiso 1 calc R . H23B H 0.6054(7) 0.2324(5) 0.6222(20) 0.096 Uiso 1 calc R . H23C H 0.5919(5) 0.1232(20) 0.6759(12) 0.096 Uiso 1 calc R . C25 C 0.6264(4) 0.2914(5) 0.3498(4) 0.0868(10) Uani 1 d . . H25A H 0.5855(20) 0.3260(34) 0.4168(6) 0.130 Uiso 1 calc R . H25B H 0.5577(15) 0.1888(7) 0.2850(23) 0.130 Uiso 1 calc R . H25C H 0.6522(7) 0.3532(29) 0.3088(28) 0.130 Uiso 1 calc R . C32 C 0.5257(4) 0.5132(5) 0.8161(5) 0.1009(13) Uani 1 d . . H32A H 0.4873(28) 0.4286(9) 0.7290(9) 0.151 Uiso 1 calc R . H32B H 0.4502(19) 0.5275(16) 0.8425(35) 0.151 Uiso 1 calc R . H32C H 0.5680(10) 0.4947(24) 0.8761(27) 0.151 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl26 0.0729(4) 0.0679(4) 0.0634(4) 0.0269(3) 0.0281(3) 0.0428(4) O30 0.274(6) 0.174(4) 0.090(2) 0.056(3) 0.059(3) 0.148(4) O27 0.216(11) 0.077(4) 0.198(10) 0.065(6) 0.085(8) 0.061(6) O28 0.078(4) 0.207(10) 0.069(4) 0.022(5) -0.006(3) 0.020(5) O29 0.113(6) 0.070(4) 0.209(13) 0.014(6) 0.067(7) 0.054(4) O27A 0.233(11) 0.258(12) 0.192(10) 0.181(10) 0.141(9) 0.214(11) O28A 0.127(6) 0.076(4) 0.178(8) 0.056(5) 0.052(5) 0.028(4) O29A 0.219(13) 0.259(17) 0.253(15) 0.191(15) 0.195(13) 0.199(14) C8 0.080(2) 0.070(2) 0.070(2) 0.0442(14) 0.0329(14) 0.057(2) Cu1 0.0465(3) 0.0386(2) 0.0320(2) 0.0195(2) 0.0195(2) 0.0297(2) O11 0.0492(8) 0.0494(8) 0.0347(7) 0.0230(6) 0.0200(6) 0.0345(7) O22 0.0463(8) 0.0407(8) 0.0476(8) 0.0195(7) 0.0172(7) 0.0235(7) N9 0.0457(9) 0.0470(9) 0.0362(8) 0.0241(8) 0.0217(7) 0.0319(8) N2 0.0455(9) 0.0369(8) 0.0329(8) 0.0186(7) 0.0176(7) 0.0268(7) O18 0.0823(12) 0.0412(9) 0.0377(8) 0.0134(7) 0.0161(8) 0.0294(9) O20 0.0684(11) 0.0691(12) 0.0759(12) 0.0554(11) 0.0317(10) 0.0358(10) O24 0.0619(12) 0.0511(11) 0.0750(14) 0.0201(10) 0.0141(10) 0.0214(10) O31 0.0692(12) 0.0788(14) 0.0638(12) 0.0319(11) 0.0345(11) 0.0436(12) C3 0.0582(13) 0.0446(11) 0.0423(11) 0.0261(9) 0.0258(10) 0.0334(10) C4 0.0661(14) 0.0497(12) 0.0457(12) 0.0300(10) 0.0250(11) 0.0380(11) C5 0.0529(12) 0.0434(11) 0.0439(11) 0.0221(9) 0.0151(9) 0.0317(10) C6 0.0459(11) 0.0450(11) 0.0400(10) 0.0208(9) 0.0182(9) 0.0306(10) C7 0.0395(10) 0.0338(9) 0.0318(9) 0.0155(8) 0.0126(8) 0.0216(8) C10 0.0406(10) 0.0326(9) 0.0296(9) 0.0129(7) 0.0118(8) 0.0216(8) C12 0.0421(10) 0.0444(11) 0.0329(9) 0.0208(9) 0.0167(8) 0.0278(9) C13 0.0531(12) 0.0498(12) 0.0335(10) 0.0191(9) 0.0167(9) 0.0315(10) C14 0.068(2) 0.068(2) 0.0326(11) 0.0228(11) 0.0219(10) 0.0401(13) C15 0.0616(15) 0.082(2) 0.0451(13) 0.0421(13) 0.0272(11) 0.0416(14) C16 0.0455(12) 0.0610(14) 0.0537(13) 0.0391(12) 0.0214(10) 0.0305(11) C17 0.0395(10) 0.0461(11) 0.0402(10) 0.0248(9) 0.0171(8) 0.0260(9) C19 0.075(2) 0.0516(14) 0.0479(14) 0.0067(12) 0.0127(13) 0.0316(14) C21 0.071(2) 0.098(2) 0.095(2) 0.078(2) 0.036(2) 0.035(2) C23 0.0539(14) 0.0533(14) 0.064(2) 0.0152(13) 0.0065(12) 0.0259(12) C25 0.066(2) 0.086(2) 0.080(2) 0.026(2) 0.007(2) 0.034(2) C32 0.076(2) 0.085(3) 0.122(3) 0.041(2) 0.045(2) 0.035(2) _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 Cl26 O29A 1.315(11) . ? Cl26 O27A 1.344(6) . ? Cl26 O30 1.365(4) . ? Cl26 O28 1.367(7) . ? Cl26 O27 1.427(8) . ? Cl26 O29 1.427(10) . ? Cl26 O28A 1.491(7) . ? C8 C5 1.504(3) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? Cu1 O11 1.9553(14) . ? Cu1 O11 1.9553(14) 2_766 ? Cu1 N2 2.011(2) 2_766 ? Cu1 N2 2.011(2) . ? Cu1 O24 2.423(2) . ? Cu1 O24 2.423(2) 2_766 ? O11 C10 1.239(2) . ? O22 C17 1.374(3) . ? O22 C23 1.421(3) . ? N9 C10 1.340(3) . ? N9 C7 1.395(3) . ? N9 H9 0.86 . ? N2 C7 1.340(3) . ? N2 C3 1.357(3) . ? O18 C13 1.366(3) . ? O18 C19 1.421(3) . ? O20 C16 1.364(3) . ? O20 C21 1.425(3) . ? O24 C25 1.410(4) . ? O24 H24 0.67(4) . ? O31 C32 1.411(5) . ? O31 H31 0.78(4) . ? C3 C4 1.368(3) . ? C3 H3 0.93 . ? C4 C5 1.395(3) . ? C4 H4 0.93 . ? C5 C6 1.376(3) . ? C6 C7 1.391(3) . ? C6 H6 0.93 . ? C10 C12 1.482(3) . ? C12 C17 1.388(3) . ? C12 C13 1.405(3) . ? C13 C14 1.379(3) . ? C14 C15 1.380(4) . ? C14 H14 0.93 . ? C15 C16 1.387(4) . ? C15 H15 0.93 . ? C16 C17 1.397(3) . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C23 H23A 0.96 . ? C23 H23B 0.96 . ? C23 H23C 0.96 . ? C25 H25A 0.96 . ? C25 H25B 0.96 . ? C25 H25C 0.96 . ? C32 H32A 0.96 . ? C32 H32B 0.96 . ? C32 H32C 0.96 . ? 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 O29A Cl26 O27A 114.9(8) . . ? O29A Cl26 O30 122.4(9) . . ? O27A Cl26 O30 112.9(5) . . ? O30 Cl26 O28 125.8(5) . . ? O30 Cl26 O27 95.3(5) . . ? O28 Cl26 O27 112.8(7) . . ? O30 Cl26 O29 108.2(7) . . ? O28 Cl26 O29 109.7(7) . . ? O27 Cl26 O29 101.8(7) . . ? O29A Cl26 O28A 108.8(8) . . ? O27A Cl26 O28A 108.3(7) . . ? O30 Cl26 O28A 84.0(5) . . ? C5 C8 H8A 109.47(14) . . ? C5 C8 H8B 109.47(15) . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.47(14) . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O11 Cu1 O11 180.0 . 2_766 ? O11 Cu1 N2 90.82(6) . 2_766 ? O11 Cu1 N2 89.18(6) 2_766 2_766 ? O11 Cu1 N2 89.17(6) . . ? O11 Cu1 N2 90.83(6) 2_766 . ? N2 Cu1 N2 179.999(2) 2_766 . ? O11 Cu1 O24 89.91(8) . . ? O11 Cu1 O24 90.09(8) 2_766 . ? N2 Cu1 O24 93.45(8) 2_766 . ? N2 Cu1 O24 86.55(8) . . ? O11 Cu1 O24 90.09(8) . 2_766 ? O11 Cu1 O24 89.91(8) 2_766 2_766 ? N2 Cu1 O24 86.55(8) 2_766 2_766 ? N2 Cu1 O24 93.45(8) . 2_766 ? O24 Cu1 O24 180.0 . 2_766 ? C10 O11 Cu1 125.49(13) . . ? C17 O22 C23 114.4(2) . . ? C10 N9 C7 128.6(2) . . ? C10 N9 H9 115.72(11) . . ? C7 N9 H9 115.71(10) . . ? C7 N2 C3 116.4(2) . . ? C7 N2 Cu1 123.02(13) . . ? C3 N2 Cu1 120.25(14) . . ? C13 O18 C19 118.5(2) . . ? C16 O20 C21 117.6(3) . . ? C25 O24 Cu1 132.1(2) . . ? C25 O24 H24 107.7(37) . . ? Cu1 O24 H24 109.2(37) . . ? C32 O31 H31 107.6(32) . . ? N2 C3 C4 123.5(2) . . ? N2 C3 H3 118.27(12) . . ? C4 C3 H3 118.27(13) . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.04(13) . . ? C5 C4 H4 120.04(13) . . ? C6 C5 C4 117.0(2) . . ? C6 C5 C8 121.3(2) . . ? C4 C5 C8 121.7(2) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.90(13) . . ? C7 C6 H6 119.90(12) . . ? N2 C7 C6 122.9(2) . . ? N2 C7 N9 120.4(2) . . ? C6 C7 N9 116.6(2) . . ? O11 C10 N9 124.0(2) . . ? O11 C10 C12 120.6(2) . . ? N9 C10 C12 115.3(2) . . ? C17 C12 C13 120.4(2) . . ? C17 C12 C10 119.5(2) . . ? C13 C12 C10 120.1(2) . . ? O18 C13 C14 125.8(2) . . ? O18 C13 C12 115.2(2) . . ? C14 C13 C12 119.0(2) . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 119.84(15) . . ? C15 C14 H14 119.84(14) . . ? C14 C15 C16 121.6(2) . . ? C14 C15 H15 119.20(13) . . ? C16 C15 H15 119.20(14) . . ? O20 C16 C15 126.1(2) . . ? O20 C16 C17 115.5(2) . . ? C15 C16 C17 118.4(2) . . ? O22 C17 C12 118.6(2) . . ? O22 C17 C16 121.1(2) . . ? C12 C17 C16 120.3(2) . . ? O18 C19 H19A 109.5(2) . . ? O18 C19 H19B 109.5(2) . . ? H19A C19 H19B 109.5 . . ? O18 C19 H19C 109.5(2) . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O20 C21 H21A 109.5(2) . . ? O20 C21 H21B 109.5(2) . . ? H21A C21 H21B 109.47(6) . . ? O20 C21 H21C 109.5(2) . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O22 C23 H23A 109.47(14) . . ? O22 C23 H23B 109.47(14) . . ? H23A C23 H23B 109.5 . . ? O22 C23 H23C 109.5(2) . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O24 C25 H25A 109.5(2) . . ? O24 C25 H25B 109.5(2) . . ? H25A C25 H25B 109.5 . . ? O24 C25 H25C 109.5(2) . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O31 C32 H32A 109.5(2) . . ? O31 C32 H32B 109.5(2) . . ? H32A C32 H32B 109.47(5) . . ? O31 C32 H32C 109.5(2) . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 O11 Cu1 O11 C10 90.3(288) 2_766 . . . ? N2 Cu1 O11 C10 -149.5(2) 2_766 . . . ? N2 Cu1 O11 C10 30.5(2) . . . . ? O24 Cu1 O11 C10 -56.1(2) . . . . ? O24 Cu1 O11 C10 123.9(2) 2_766 . . . ? O11 Cu1 N2 C7 -25.5(2) . . . . ? O11 Cu1 N2 C7 154.5(2) 2_766 . . . ? N2 Cu1 N2 C7 -6.9(191) 2_766 . . . ? O24 Cu1 N2 C7 64.4(2) . . . . ? O24 Cu1 N2 C7 -115.6(2) 2_766 . . . ? O11 Cu1 N2 C3 161.0(2) . . . . ? O11 Cu1 N2 C3 -19.0(2) 2_766 . . . ? N2 Cu1 N2 C3 179.6(191) 2_766 . . . ? O24 Cu1 N2 C3 -109.0(2) . . . . ? O24 Cu1 N2 C3 71.0(2) 2_766 . . . ? O11 Cu1 O24 C25 110.8(3) . . . . ? O11 Cu1 O24 C25 -69.2(3) 2_766 . . . ? N2 Cu1 O24 C25 -158.4(3) 2_766 . . . ? N2 Cu1 O24 C25 21.6(3) . . . . ? O24 Cu1 O24 C25 -174.8(52) 2_766 . . . ? C7 N2 C3 C4 -2.3(3) . . . . ? Cu1 N2 C3 C4 171.6(2) . . . . ? N2 C3 C4 C5 0.0(4) . . . . ? C3 C4 C5 C6 1.2(4) . . . . ? C3 C4 C5 C8 -179.8(2) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C8 C5 C6 C7 -179.0(2) . . . . ? C3 N2 C7 C6 3.5(3) . . . . ? Cu1 N2 C7 C6 -170.2(2) . . . . ? C3 N2 C7 N9 -176.6(2) . . . . ? Cu1 N2 C7 N9 9.7(3) . . . . ? C5 C6 C7 N2 -2.4(3) . . . . ? C5 C6 C7 N9 177.7(2) . . . . ? C10 N9 C7 N2 15.4(3) . . . . ? C10 N9 C7 C6 -164.7(2) . . . . ? Cu1 O11 C10 N9 -18.1(3) . . . . ? Cu1 O11 C10 C12 162.46(14) . . . . ? C7 N9 C10 O11 -11.7(3) . . . . ? C7 N9 C10 C12 167.8(2) . . . . ? O11 C10 C12 C17 -63.3(3) . . . . ? N9 C10 C12 C17 117.2(2) . . . . ? O11 C10 C12 C13 117.0(2) . . . . ? N9 C10 C12 C13 -62.5(3) . . . . ? C19 O18 C13 C14 17.4(4) . . . . ? C19 O18 C13 C12 -161.4(2) . . . . ? C17 C12 C13 O18 178.0(2) . . . . ? C10 C12 C13 O18 -2.3(3) . . . . ? C17 C12 C13 C14 -0.9(3) . . . . ? C10 C12 C13 C14 178.8(2) . . . . ? O18 C13 C14 C15 -178.7(2) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? C21 O20 C16 C15 7.6(4) . . . . ? C21 O20 C16 C17 -173.6(2) . . . . ? C14 C15 C16 O20 177.9(2) . . . . ? C14 C15 C16 C17 -0.9(4) . . . . ? C23 O22 C17 C12 -105.7(2) . . . . ? C23 O22 C17 C16 76.3(3) . . . . ? C13 C12 C17 O22 -177.2(2) . . . . ? C10 C12 C17 O22 3.1(3) . . . . ? C13 C12 C17 C16 0.9(3) . . . . ? C10 C12 C17 C16 -178.9(2) . . . . ? O20 C16 C17 O22 -0.9(3) . . . . ? C15 C16 C17 O22 178.0(2) . . . . ? O20 C16 C17 C12 -178.9(2) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? _refine_diff_density_max .453 _refine_diff_density_min -.773 _refine_diff_density_rms .072 data_zb35 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H32 Cl2 Cu1 N4 O12' _chemical_formula_weight 847.1 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' .3639 .7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' -1.9646 .5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5440(10) _cell_length_b 8.8580(10) _cell_length_c 13.7070(10) _cell_angle_alpha 88.050(5) _cell_angle_beta 72.984(5) _cell_angle_gamma 64.944(4) _cell_volume 893.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 72.0 _exptl_crystal_description Prismatic _exptl_crystal_colour Green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method none _exptl_crystal_F_000 435 _exptl_absorpt_coefficient_mu 2.858 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8056 _exptl_absorpt_correction_T_max 0.9963 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Enraf-Nonius-cad-4 _diffrn_measurement_method omega-2-theta _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 4 _diffrn_reflns_number 3518 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 71.91 _reflns_number_total 3518 _reflns_number_observed 3232 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 w=1/[s^2^(Fo^2^)+( 0.0522P)^2^+0.7501P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3518 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_obs 0.0432 _refine_ls_wR_factor_all 0.1135 _refine_ls_wR_factor_obs 0.1116 _refine_ls_goodness_of_fit_all 1.040 _refine_ls_goodness_of_fit_obs 1.070 _refine_ls_restrained_S_all 1.040 _refine_ls_restrained_S_obs 1.070 _refine_ls_shift/esd_max 0.071 _refine_ls_shift/esd_mean 0.007 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 1.0000 0.0000 1.0000 0.03704(15) Uani 1 d S . N2 N 0.7593(2) 0.0630(2) 0.96375(13) 0.0338(4) Uani 1 d . . C3 C 0.7269(3) -0.0010(3) 0.8860(2) 0.0356(4) Uani 1 d . . C4 C 0.8536(3) -0.1569(3) 0.8301(2) 0.0502(6) Uani 1 d . . H4 H 0.9590(3) -0.2190(3) 0.8473(2) 0.060 Uiso 1 calc R . C5 C 0.8226(4) -0.2173(4) 0.7511(2) 0.0557(7) Uani 1 d . . H5 H 0.9082(4) -0.3197(4) 0.7145(2) 0.067 Uiso 1 calc R . C6 C 0.6633(4) -0.1273(4) 0.7240(2) 0.0548(6) Uani 1 d . . H6 H 0.6466(4) -0.1682(4) 0.6682(2) 0.066 Uiso 1 calc R . C7 C 0.5346(3) 0.0188(4) 0.7792(2) 0.0504(6) Uani 1 d . . H7 H 0.4279(3) 0.0758(4) 0.7624(2) 0.060 Uiso 1 calc R . C8 C 0.5604(3) 0.0860(3) 0.8624(2) 0.0394(5) Uani 1 d . . C9 C 0.4279(3) 0.2326(3) 0.9242(2) 0.0455(5) Uani 1 d . . H9 H 0.3180(3) 0.2908(3) 0.9108(2) 0.055 Uiso 1 calc R . C10 C 0.4595(3) 0.2902(3) 1.0037(2) 0.0423(5) Uani 1 d . . H10 H 0.3708(3) 0.3859(3) 1.0463(2) 0.051 Uiso 1 calc R . C11 C 0.6282(3) 0.2029(3) 1.0202(2) 0.0341(4) Uani 1 d . . C12 C 0.6781(3) 0.2590(3) 1.1030(2) 0.0357(4) Uani 1 d . . O13 O 0.8351(2) 0.1745(2) 1.10940(13) 0.0459(4) Uani 1 d . . N14 N 0.5613(3) 0.3920(2) 1.16731(14) 0.0416(4) Uani 1 d . . H14 H 0.4560(3) 0.4478(2) 1.15965(14) 0.050 Uiso 1 calc R . C15 C 0.6024(4) 0.4501(3) 1.2522(2) 0.0478(6) Uani 1 d . . H15A H 0.5464(4) 0.5716(3) 1.2609(2) 0.057 Uiso 1 calc R . H15B H 0.7327(4) 0.4115(3) 1.2353(2) 0.057 Uiso 1 calc R . C16 C 0.5344(3) 0.3864(3) 1.3506(2) 0.0468(6) Uani 1 d . . C17 C 0.6408(4) 0.2314(4) 1.3756(2) 0.0617(7) Uani 1 d . . H17 H 0.7562(4) 0.1672(4) 1.3311(2) 0.074 Uiso 1 calc R . C18 C 0.5782(6) 0.1712(5) 1.4653(3) 0.0827(10) Uani 1 d . . H18 H 0.6507(6) 0.0668(5) 1.4811(3) 0.099 Uiso 1 calc R . C19 C 0.4106(7) 0.2649(6) 1.5304(3) 0.0845(11) Uani 1 d . . H19 H 0.3696(7) 0.2238(6) 1.5911(3) 0.101 Uiso 1 calc R . C20 C 0.2996(5) 0.4188(6) 1.5093(2) 0.0796(11) Uani 1 d . . H20 H 0.1848(5) 0.4810(6) 1.5551(2) 0.096 Uiso 1 calc R . C21 C 0.3617(4) 0.4816(4) 1.4172(2) 0.0578(7) Uani 1 d . . O22 O 0.2689(3) 0.6302(3) 1.3855(2) 0.0830(7) Uani 1 d . . C23 C 0.0907(5) 0.7374(6) 1.4501(4) 0.120(2) Uani 1 d . . H23A H 0.0968(10) 0.7631(45) 1.5160(12) 0.180 Uiso 1 calc R . H23B H 0.0133(16) 0.6818(22) 1.4583(27) 0.180 Uiso 1 calc R . H23C H 0.0425(24) 0.8392(23) 1.4194(17) 0.180 Uiso 1 calc R . Cl24 Cl 1.00566(9) -0.30461(10) 1.17371(7) 0.0722(3) Uani 1 d . . O26 O 1.1887(3) -0.3714(3) 1.1662(2) 0.0804(7) Uani 1 d . . O27 O 0.9091(25) -0.3612(29) 1.2488(16) 0.132(9) Uani 0.35 d P 1 O27A O 0.9135(15) -0.3951(14) 1.2147(8) 0.102(3) Uani 0.65 d P 2 O28 O 0.9232(7) -0.1492(6) 1.2535(4) 0.105(2) Uani 0.59 d P 1 O28A O 1.0392(12) -0.4317(11) 1.0696(8) 0.145(4) Uani 0.41 d P 2 O25 O 0.9251(8) -0.1612(9) 1.1415(7) 0.078(2) Uani 0.38 d P 1 O25A O 0.9706(8) -0.2359(7) 1.0876(4) 0.085(2) Uani 0.62 d P 2 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 0.0255(2) 0.0409(3) 0.0375(3) -0.0036(2) -0.0130(2) -0.0050(2) N2 0.0267(8) 0.0375(9) 0.0338(9) 0.0027(7) -0.0106(7) -0.0098(7) C3 0.0303(10) 0.0431(11) 0.0343(10) 0.0040(8) -0.0114(8) -0.0158(9) C4 0.0351(12) 0.0543(14) 0.0550(14) -0.0098(11) -0.0160(11) -0.0109(11) C5 0.0462(14) 0.060(2) 0.0553(15) -0.0149(12) -0.0128(12) -0.0182(12) C6 0.0547(15) 0.072(2) 0.0470(14) -0.0024(12) -0.0216(12) -0.0310(14) C7 0.0429(13) 0.066(2) 0.0487(13) 0.0060(12) -0.0241(11) -0.0225(12) C8 0.0333(11) 0.0483(12) 0.0394(11) 0.0091(9) -0.0153(9) -0.0179(10) C9 0.0301(11) 0.0515(13) 0.0529(14) 0.0083(11) -0.0201(10) -0.0112(10) C10 0.0280(10) 0.0430(12) 0.0467(12) 0.0009(10) -0.0116(9) -0.0067(9) C11 0.0273(10) 0.0379(10) 0.0339(10) 0.0050(8) -0.0087(8) -0.0118(8) C12 0.0290(10) 0.0377(11) 0.0347(10) 0.0016(8) -0.0077(8) -0.0104(8) O13 0.0305(8) 0.0511(9) 0.0467(9) -0.0093(7) -0.0162(7) -0.0051(7) N14 0.0326(9) 0.0413(10) 0.0418(10) -0.0025(8) -0.0094(8) -0.0084(8) C15 0.0457(13) 0.0479(13) 0.0464(13) -0.0088(10) -0.0078(11) -0.0204(11) C16 0.0464(13) 0.0537(14) 0.0443(12) -0.0076(10) -0.0139(10) -0.0244(11) C17 0.066(2) 0.059(2) 0.067(2) 0.0033(13) -0.0273(15) -0.0290(14) C18 0.111(3) 0.083(2) 0.080(2) 0.025(2) -0.049(2) -0.055(2) C19 0.119(3) 0.109(3) 0.057(2) 0.015(2) -0.031(2) -0.077(3) C20 0.073(2) 0.124(3) 0.048(2) -0.023(2) 0.0025(15) -0.060(2) C21 0.0495(15) 0.074(2) 0.0498(14) -0.0160(13) -0.0122(12) -0.0270(14) O22 0.0503(12) 0.088(2) 0.079(2) -0.0176(13) -0.0154(11) -0.0017(11) C23 0.049(2) 0.127(4) 0.136(4) -0.054(3) -0.017(2) 0.003(2) Cl24 0.0342(3) 0.0838(5) 0.0893(5) 0.0435(4) -0.0198(3) -0.0190(3) O26 0.0352(10) 0.0752(14) 0.110(2) -0.0073(13) -0.0262(11) -0.0010(10) O27 0.058(7) 0.152(15) 0.113(12) 0.070(10) 0.024(8) -0.018(7) O27A 0.102(6) 0.103(5) 0.141(8) 0.069(5) -0.054(6) -0.074(5) O28 0.092(3) 0.071(3) 0.090(3) -0.033(2) -0.015(3) 0.016(2) O28A 0.105(6) 0.126(6) 0.171(8) -0.070(6) -0.083(6) 0.015(5) O25 0.036(3) 0.059(4) 0.112(6) 0.040(4) -0.012(4) -0.005(3) O25A 0.105(4) 0.117(4) 0.080(3) 0.045(3) -0.054(3) -0.076(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 O13 1.924(2) . ? Cu1 O13 1.924(2) 2_757 ? Cu1 N2 2.097(2) 2_757 ? Cu1 N2 2.097(2) . ? N2 C11 1.331(3) . ? N2 C3 1.371(3) . ? C3 C4 1.410(3) . ? C3 C8 1.430(3) . ? C4 C5 1.362(4) . ? C4 H4 0.93 . ? C5 C6 1.408(4) . ? C5 H5 0.93 . ? C6 C7 1.353(4) . ? C6 H6 0.93 . ? C7 C8 1.417(3) . ? C7 H7 0.93 . ? C8 C9 1.397(3) . ? C9 C10 1.360(3) . ? C9 H9 0.93 . ? C10 C11 1.400(3) . ? C10 H10 0.93 . ? C11 C12 1.489(3) . ? C12 O13 1.257(3) . ? C12 N14 1.312(3) . ? N14 C15 1.475(3) . ? N14 H14 0.86 . ? C15 C16 1.497(4) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.387(4) . ? C16 C21 1.390(4) . ? C17 C18 1.376(5) . ? C17 H17 0.93 . ? C18 C19 1.354(6) . ? C18 H18 0.93 . ? C19 C20 1.371(6) . ? C19 H19 0.93 . ? C20 C21 1.412(5) . ? C20 H20 0.93 . ? C21 O22 1.353(4) . ? O22 C23 1.430(4) . ? C23 H23A 0.96 . ? C23 H23B 0.96 . ? C23 H23C 0.96 . ? Cl24 O25 1.297(6) . ? Cl24 O27 1.34(2) . ? Cl24 O27A 1.350(8) . ? Cl24 O25A 1.363(5) . ? Cl24 O26 1.391(2) . ? Cl24 O28 1.555(4) . ? Cl24 O28A 1.728(7) . ? O28 O25 1.538(10) . ? O28A O25A 1.581(10) . ? 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 O13 Cu1 O13 180.0 . 2_757 ? O13 Cu1 N2 99.15(7) . 2_757 ? O13 Cu1 N2 80.85(7) 2_757 2_757 ? O13 Cu1 N2 80.85(7) . . ? O13 Cu1 N2 99.15(7) 2_757 . ? N2 Cu1 N2 179.999(1) 2_757 . ? C11 N2 C3 118.4(2) . . ? C11 N2 Cu1 110.08(14) . . ? C3 N2 Cu1 130.88(14) . . ? N2 C3 C4 120.9(2) . . ? N2 C3 C8 120.7(2) . . ? C4 C3 C8 118.4(2) . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8(2) . . ? C3 C4 H4 119.77(13) . . ? C4 C5 C6 121.2(2) . . ? C4 C5 H5 119.4(2) . . ? C6 C5 H5 119.42(15) . . ? C7 C6 C5 120.0(2) . . ? C7 C6 H6 120.01(15) . . ? C5 C6 H6 120.01(15) . . ? C6 C7 C8 120.8(2) . . ? C6 C7 H7 119.61(15) . . ? C8 C7 H7 119.60(14) . . ? C9 C8 C7 122.6(2) . . ? C9 C8 C3 118.3(2) . . ? C7 C8 C3 119.0(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.97(13) . . ? C8 C9 H9 119.97(13) . . ? C9 C10 C11 118.8(2) . . ? C9 C10 H10 120.61(13) . . ? C11 C10 H10 120.61(13) . . ? N2 C11 C10 123.7(2) . . ? N2 C11 C12 113.5(2) . . ? C10 C11 C12 122.8(2) . . ? O13 C12 N14 121.3(2) . . ? O13 C12 C11 117.9(2) . . ? N14 C12 C11 120.8(2) . . ? C12 O13 Cu1 116.30(14) . . ? C12 N14 C15 122.9(2) . . ? C12 N14 H14 118.53(13) . . ? C15 N14 H14 118.53(13) . . ? N14 C15 C16 111.4(2) . . ? N14 C15 H15A 109.36(13) . . ? C16 C15 H15A 109.36(13) . . ? N14 C15 H15B 109.36(12) . . ? C16 C15 H15B 109.36(14) . . ? H15A C15 H15B 108.0 . . ? C17 C16 C21 119.2(3) . . ? C17 C16 C15 120.7(2) . . ? C21 C16 C15 120.1(3) . . ? C18 C17 C16 121.0(3) . . ? C18 C17 H17 119.5(2) . . ? C16 C17 H17 119.5(2) . . ? C19 C18 C17 119.6(4) . . ? C19 C18 H18 120.2(2) . . ? C17 C18 H18 120.2(2) . . ? C18 C19 C20 121.8(3) . . ? C18 C19 H19 119.1(2) . . ? C20 C19 H19 119.1(2) . . ? C19 C20 C21 119.2(3) . . ? C19 C20 H20 120.4(2) . . ? C21 C20 H20 120.4(2) . . ? O22 C21 C16 114.6(3) . . ? O22 C21 C20 126.3(3) . . ? C16 C21 C20 119.2(3) . . ? C21 O22 C23 118.3(3) . . ? O22 C23 H23A 109.5(2) . . ? O22 C23 H23B 109.5(2) . . ? H23A C23 H23B 109.5 . . ? O22 C23 H23C 109.5(3) . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O25 Cl24 O27 119.9(10) . . ? O27A Cl24 O25A 114.0(6) . . ? O25 Cl24 O26 121.6(3) . . ? O27 Cl24 O26 113.6(10) . . ? O27A Cl24 O26 117.8(5) . . ? O25A Cl24 O26 112.9(3) . . ? O25 Cl24 O28 64.5(4) . . ? O27 Cl24 O28 83.4(10) . . ? O26 Cl24 O28 101.9(2) . . ? O27A Cl24 O28A 76.4(7) . . ? O25A Cl24 O28A 60.2(4) . . ? O26 Cl24 O28A 94.5(3) . . ? O25 O28 Cl24 49.6(3) . . ? O25A O28A Cl24 48.4(3) . . ? Cl24 O25 O28 65.9(4) . . ? Cl24 O25A O28A 71.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O13 Cu1 N2 C11 10.34(14) . . . . ? O13 Cu1 N2 C11 -169.66(14) 2_757 . . . ? N2 Cu1 N2 C11 -91.4(188) 2_757 . . . ? O13 Cu1 N2 C3 -179.5(2) . . . . ? O13 Cu1 N2 C3 0.5(2) 2_757 . . . ? N2 Cu1 N2 C3 78.7(188) 2_757 . . . ? C11 N2 C3 C4 -173.8(2) . . . . ? Cu1 N2 C3 C4 16.7(3) . . . . ? C11 N2 C3 C8 3.7(3) . . . . ? Cu1 N2 C3 C8 -165.8(2) . . . . ? N2 C3 C4 C5 -178.2(2) . . . . ? C8 C3 C4 C5 4.3(4) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C4 C5 C6 C7 -2.6(5) . . . . ? C5 C6 C7 C8 2.1(4) . . . . ? C6 C7 C8 C9 -177.2(3) . . . . ? C6 C7 C8 C3 1.4(4) . . . . ? N2 C3 C8 C9 -3.5(3) . . . . ? C4 C3 C8 C9 174.1(2) . . . . ? N2 C3 C8 C7 177.8(2) . . . . ? C4 C3 C8 C7 -4.6(3) . . . . ? C7 C8 C9 C10 179.3(2) . . . . ? C3 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C11 1.8(4) . . . . ? C3 N2 C11 C10 -1.1(3) . . . . ? Cu1 N2 C11 C10 170.4(2) . . . . ? C3 N2 C11 C12 179.3(2) . . . . ? Cu1 N2 C11 C12 -9.2(2) . . . . ? C9 C10 C11 N2 -1.7(4) . . . . ? C9 C10 C11 C12 177.9(2) . . . . ? N2 C11 C12 O13 1.8(3) . . . . ? C10 C11 C12 O13 -177.8(2) . . . . ? N2 C11 C12 N14 -177.8(2) . . . . ? C10 C11 C12 N14 2.5(3) . . . . ? N14 C12 O13 Cu1 -172.7(2) . . . . ? C11 C12 O13 Cu1 7.7(3) . . . . ? O13 Cu1 O13 C12 73.4(719) 2_757 . . . ? N2 Cu1 O13 C12 170.2(2) 2_757 . . . ? N2 Cu1 O13 C12 -9.8(2) . . . . ? O13 C12 N14 C15 -1.3(3) . . . . ? C11 C12 N14 C15 178.3(2) . . . . ? C12 N14 C15 C16 -95.9(3) . . . . ? N14 C15 C16 C17 87.3(3) . . . . ? N14 C15 C16 C21 -91.7(3) . . . . ? C21 C16 C17 C18 -0.2(4) . . . . ? C15 C16 C17 C18 -179.2(3) . . . . ? C16 C17 C18 C19 -0.3(5) . . . . ? C17 C18 C19 C20 0.5(6) . . . . ? C18 C19 C20 C21 -0.1(5) . . . . ? C17 C16 C21 O22 -179.8(2) . . . . ? C15 C16 C21 O22 -0.7(4) . . . . ? C17 C16 C21 C20 0.6(4) . . . . ? C15 C16 C21 C20 179.6(2) . . . . ? C19 C20 C21 O22 180.0(3) . . . . ? C19 C20 C21 C16 -0.5(4) . . . . ? C16 C21 O22 C23 -179.2(3) . . . . ? C20 C21 O22 C23 0.4(5) . . . . ? O25 Cl24 O28 O25 0.000(4) . . . . ? O27 Cl24 O28 O25 -127.6(11) . . . . ? O27A Cl24 O28 O25 -117.2(7) . . . . ? O25A Cl24 O28 O25 2.3(5) . . . . ? O26 Cl24 O28 O25 119.6(4) . . . . ? O28A Cl24 O28 O25 -26.9(15) . . . . ? O25 Cl24 O28A O25A 8.9(5) . . . . ? O27 Cl24 O28A O25A 131.2(10) . . . . ? O27A Cl24 O28A O25A 128.5(6) . . . . ? O25A Cl24 O28A O25A 0.000(2) . . . . ? O26 Cl24 O28A O25A -114.0(3) . . . . ? O28 Cl24 O28A O25A 33.3(15) . . . . ? O27 Cl24 O25 O28 65.2(13) . . . . ? O27A Cl24 O25 O28 92.4(7) . . . . ? O25A Cl24 O25 O28 -176.4(8) . . . . ? O26 Cl24 O25 O28 -88.5(4) . . . . ? O28 Cl24 O25 O28 0.000(3) . . . . ? O28A Cl24 O25 O28 171.2(4) . . . . ? Cl24 O28 O25 Cl24 0.000(3) . . . . ? O25 Cl24 O25A O28A -165.9(9) . . . . ? O27 Cl24 O25A O28A -76.6(14) . . . . ? O27A Cl24 O25A O28A -56.5(7) . . . . ? O26 Cl24 O25A O28A 81.6(4) . . . . ? O28 Cl24 O25A O28A -169.2(5) . . . . ? O28A Cl24 O25A O28A 0.000(2) . . . . ? Cl24 O28A O25A Cl24 0.000(3) . . . . ? _refine_diff_density_max .547 _refine_diff_density_min -1.008 _refine_diff_density_rms .064