# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_yp4_m _database_code_depnum_ccdc_archive 'CCDC 716784' #TrackingRef '- yp4_m_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H54 CL4 CU2 N10 O8' _chemical_formula_sum 'C40 H54 Cl4 Cu2 N10 O8' _chemical_formula_weight 1071.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.187(6) _cell_length_b 10.264(6) _cell_length_c 12.987(8) _cell_angle_alpha 76.354(9) _cell_angle_beta 74.315(9) _cell_angle_gamma 89.607(9) _cell_volume 1143.6(12) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 876 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.50 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 1.226 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.6054 _exptl_absorpt_correction_T_max 0.6470 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12698 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.25 _reflns_number_total 5190 _reflns_number_gt 3883 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART APEX CCD' _computing_cell_refinement 'BRUKER APEX CCD' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'WINGX V1.80.01' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Perchlorate oxygen atoms were solved using ISOR restraints. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1480P)^2^+0.9356P] 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 5190 _refine_ls_number_parameters 294 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1938 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.921 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 N1 N 0.0200(3) 0.0492(3) 0.2751(2) 0.0332(6) Uani 1 1 d . . . N2 N 0.1556(3) 0.0399(3) 0.2010(2) 0.0325(6) Uani 1 1 d . . . N3 N 0.1272(3) 0.2573(3) 0.4627(2) 0.0349(7) Uani 1 1 d . . . N4 N 0.2823(3) 0.2651(3) 0.4296(2) 0.0329(6) Uani 1 1 d . . . N5 N 0.2564(3) 0.1989(3) 0.2728(2) 0.0294(6) Uani 1 1 d . . . O1 O 0.5209(4) 0.7071(4) 0.0813(3) 0.0765(8) Uani 1 1 d U . . O2 O 0.4577(6) 0.5705(6) 0.2617(4) 0.1075(11) Uani 1 1 d U . . O3 O 0.4462(4) 0.8040(4) 0.2318(3) 0.0748(8) Uani 1 1 d U . . O4 O 0.6742(5) 0.7038(4) 0.1938(4) 0.0839(9) Uani 1 1 d U . . C1 C 0.2486(4) 0.3342(4) 0.1965(3) 0.0383(8) Uani 1 1 d . . . H1A H 0.2566 0.4044 0.2337 0.046 Uiso 1 1 calc R . . H1B H 0.3344 0.3479 0.1315 0.046 Uiso 1 1 calc R . . C2 C 0.1054(4) 0.3469(3) 0.1615(3) 0.0337(8) Uani 1 1 d . . . C3 C 0.1001(4) 0.3186(4) 0.0625(3) 0.0358(8) Uani 1 1 d . . . H3 H 0.1869 0.2948 0.0161 0.043 Uiso 1 1 calc R . . C4 C -0.0345(4) 0.3259(4) 0.0334(3) 0.0375(8) Uani 1 1 d . . . H4 H -0.0371 0.3056 -0.0322 0.045 Uiso 1 1 calc R . . C5 C -0.1654(4) 0.3626(4) 0.0997(3) 0.0374(8) Uani 1 1 d . . . C6 C -0.1589(4) 0.3943(4) 0.1965(3) 0.0408(9) Uani 1 1 d . . . H6 H -0.2454 0.4204 0.2416 0.049 Uiso 1 1 calc R . . C7 C -0.0241(4) 0.3874(4) 0.2269(3) 0.0395(9) Uani 1 1 d . . . H7 H -0.0210 0.4102 0.2915 0.047 Uiso 1 1 calc R . . C8 C -0.3115(5) 0.3700(5) 0.0666(4) 0.0551(11) Uani 1 1 d . . . H8A H -0.3711 0.2869 0.1009 0.083 Uiso 1 1 calc R . . H8B H -0.2889 0.3854 -0.0121 0.083 Uiso 1 1 calc R . . H8C H -0.3671 0.4423 0.0900 0.083 Uiso 1 1 calc R . . C9 C 0.2934(4) 0.0904(4) 0.2161(3) 0.0357(8) Uani 1 1 d . . . H9A H 0.3669 0.1239 0.1451 0.043 Uiso 1 1 calc R . . H9B H 0.3369 0.0188 0.2595 0.043 Uiso 1 1 calc R . . C10 C 0.1374(4) -0.0219(4) 0.1241(3) 0.0360(8) Uani 1 1 d . . . C11 C -0.0142(4) -0.0518(4) 0.1472(3) 0.0394(8) Uani 1 1 d . . . H11 H -0.0613 -0.0950 0.1083 0.047 Uiso 1 1 calc R . . C12 C -0.0856(4) -0.0056(3) 0.2405(3) 0.0353(8) Uani 1 1 d . . . C13 C 0.2680(5) -0.0427(4) 0.0331(3) 0.0468(9) Uani 1 1 d . . . H13A H 0.3313 0.0388 0.0016 0.070 Uiso 1 1 calc R . . H13B H 0.2310 -0.0668 -0.0227 0.070 Uiso 1 1 calc R . . H13C H 0.3258 -0.1133 0.0619 0.070 Uiso 1 1 calc R . . C14 C -0.2516(4) -0.0037(4) 0.2924(4) 0.0466(10) Uani 1 1 d . . . H14A H -0.2745 -0.0456 0.3697 0.070 Uiso 1 1 calc R . . H14B H -0.3066 -0.0518 0.2584 0.070 Uiso 1 1 calc R . . H14C H -0.2804 0.0875 0.2824 0.070 Uiso 1 1 calc R . . C15 C 0.3613(4) 0.2097(4) 0.3387(3) 0.0343(8) Uani 1 1 d . . . H15A H 0.3948 0.1217 0.3664 0.041 Uiso 1 1 calc R . . H15B H 0.4496 0.2677 0.2935 0.041 Uiso 1 1 calc R . . C16 C 0.3419(4) 0.3190(4) 0.4963(3) 0.0366(8) Uani 1 1 d . . . C17 C 0.2202(5) 0.3496(4) 0.5734(3) 0.0430(9) Uani 1 1 d . . . H17 H 0.2243 0.3892 0.6301 0.052 Uiso 1 1 calc R . . C18 C 0.0876(4) 0.3098(4) 0.5506(3) 0.0373(8) Uani 1 1 d . . . C19 C 0.5067(5) 0.3310(5) 0.4819(4) 0.0544(11) Uani 1 1 d . . . H19A H 0.5512 0.2505 0.4662 0.082 Uiso 1 1 calc R . . H19B H 0.5248 0.3440 0.5483 0.082 Uiso 1 1 calc R . . H19C H 0.5512 0.4064 0.4219 0.082 Uiso 1 1 calc R . . C20 C -0.0712(5) 0.3239(5) 0.6112(4) 0.0513(11) Uani 1 1 d . . . H20A H -0.1224 0.3750 0.5610 0.077 Uiso 1 1 calc R . . H20B H -0.0721 0.3693 0.6681 0.077 Uiso 1 1 calc R . . H20C H -0.1221 0.2365 0.6438 0.077 Uiso 1 1 calc R . . Cl1 Cl -0.18121(9) 0.08278(9) 0.50911(7) 0.0386(2) Uani 1 1 d . . . Cl2 Cl 0.51864(11) 0.69544(10) 0.19298(8) 0.0456(2) Uani 1 1 d . . . Cu1 Cu 0.04491(4) 0.14105(4) 0.38659(3) 0.03040(11) 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 N1 0.0346(13) 0.0332(15) 0.0345(14) -0.0110(12) -0.0116(11) -0.0051(12) N2 0.0364(14) 0.0307(14) 0.0336(13) -0.0124(11) -0.0108(11) -0.0035(12) N3 0.0355(14) 0.0321(15) 0.0390(15) -0.0143(12) -0.0083(12) -0.0048(12) N4 0.0331(13) 0.0329(15) 0.0377(14) -0.0157(12) -0.0116(11) -0.0044(11) N5 0.0337(13) 0.0281(14) 0.0291(13) -0.0104(11) -0.0101(10) -0.0025(11) O1 0.0783(11) 0.0803(11) 0.0746(11) -0.0214(8) -0.0249(8) 0.0063(8) O2 0.1098(13) 0.1038(13) 0.1074(13) -0.0262(9) -0.0270(8) 0.0037(9) O3 0.0771(11) 0.0732(11) 0.0755(11) -0.0230(8) -0.0190(8) 0.0082(8) O4 0.0827(11) 0.0869(12) 0.0849(12) -0.0222(8) -0.0268(8) 0.0053(8) C1 0.0394(17) 0.0323(18) 0.0409(19) -0.0044(15) -0.0110(15) -0.0080(14) C2 0.0380(17) 0.0258(16) 0.0353(17) -0.0053(13) -0.0087(14) -0.0029(13) C3 0.0389(17) 0.0289(17) 0.0351(17) -0.0060(14) -0.0042(14) 0.0019(14) C4 0.0484(19) 0.0279(17) 0.0367(18) -0.0073(14) -0.0129(15) -0.0035(15) C5 0.0380(17) 0.0263(17) 0.049(2) -0.0088(15) -0.0145(15) -0.0034(14) C6 0.0341(17) 0.040(2) 0.046(2) -0.0131(16) -0.0038(15) 0.0030(15) C7 0.049(2) 0.0334(19) 0.0363(18) -0.0124(15) -0.0086(15) 0.0014(16) C8 0.042(2) 0.053(3) 0.074(3) -0.017(2) -0.022(2) -0.0009(19) C9 0.0317(15) 0.0401(19) 0.0396(17) -0.0190(15) -0.0089(13) -0.0033(14) C10 0.0529(19) 0.0278(17) 0.0341(16) -0.0118(13) -0.0194(15) 0.0038(15) C11 0.0491(19) 0.0355(19) 0.0460(18) -0.0188(15) -0.0259(15) 0.0003(15) C12 0.0416(17) 0.0276(17) 0.0435(18) -0.0104(14) -0.0213(14) -0.0066(14) C13 0.056(2) 0.051(2) 0.0424(19) -0.0251(17) -0.0159(17) 0.0107(18) C14 0.0390(18) 0.044(2) 0.063(2) -0.0175(18) -0.0201(17) -0.0084(16) C15 0.0303(15) 0.0403(19) 0.0350(16) -0.0147(14) -0.0087(13) -0.0028(14) C16 0.0464(18) 0.0315(18) 0.0389(17) -0.0115(14) -0.0206(14) -0.0036(15) C17 0.056(2) 0.038(2) 0.0435(19) -0.0214(15) -0.0189(16) -0.0008(17) C18 0.0486(19) 0.0278(17) 0.0369(18) -0.0107(14) -0.0115(15) -0.0015(15) C19 0.048(2) 0.065(3) 0.064(2) -0.031(2) -0.0244(19) -0.004(2) C20 0.051(2) 0.048(2) 0.058(2) -0.0291(19) -0.0058(18) 0.0013(18) Cl1 0.0314(4) 0.0415(5) 0.0409(4) -0.0116(4) -0.0055(3) -0.0026(3) Cl2 0.0557(5) 0.0402(5) 0.0459(5) -0.0180(4) -0.0158(4) 0.0031(4) Cu1 0.0301(2) 0.0297(2) 0.0336(2) -0.01285(16) -0.00785(15) -0.00557(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C12 1.350(4) . ? N1 N2 1.372(4) . ? N1 Cu1 1.965(3) . ? N2 C10 1.349(5) . ? N2 C9 1.449(5) . ? N3 C18 1.337(5) . ? N3 N4 1.369(4) . ? N3 Cu1 1.986(3) . ? N4 C16 1.359(5) . ? N4 C15 1.446(4) . ? N5 C9 1.464(4) . ? N5 C15 1.472(4) . ? N5 C1 1.518(5) . ? N5 Cu1 2.088(3) . ? O1 Cl2 1.421(4) . ? O2 Cl2 1.398(5) . ? O3 Cl2 1.418(4) . ? O4 Cl2 1.436(4) . ? C1 C2 1.499(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.387(5) . ? C2 C3 1.397(5) . ? C3 C4 1.384(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C4 H4 0.9300 . ? C5 C6 1.387(6) . ? C5 C8 1.512(6) . ? C6 C7 1.395(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.364(5) . ? C10 C13 1.493(5) . ? C11 C12 1.400(5) . ? C11 H11 0.9300 . ? C12 C14 1.494(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.375(5) . ? C16 C19 1.477(6) . ? C17 C18 1.413(6) . ? C17 H17 0.9300 . ? C18 C20 1.483(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cl1 Cu1 2.2329(14) . ? 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 C12 N1 N2 105.2(3) . . ? C12 N1 Cu1 142.7(3) . . ? N2 N1 Cu1 112.0(2) . . ? C10 N2 N1 111.6(3) . . ? C10 N2 C9 129.6(3) . . ? N1 N2 C9 118.8(3) . . ? C18 N3 N4 106.3(3) . . ? C18 N3 Cu1 141.5(3) . . ? N4 N3 Cu1 110.4(2) . . ? C16 N4 N3 111.7(3) . . ? C16 N4 C15 128.2(3) . . ? N3 N4 C15 119.9(3) . . ? C9 N5 C15 111.5(3) . . ? C9 N5 C1 113.8(3) . . ? C15 N5 C1 110.3(3) . . ? C9 N5 Cu1 105.9(2) . . ? C15 N5 Cu1 105.6(2) . . ? C1 N5 Cu1 109.4(2) . . ? C2 C1 N5 113.1(3) . . ? C2 C1 H1A 109.0 . . ? N5 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? N5 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C7 C2 C3 118.9(3) . . ? C7 C2 C1 120.4(3) . . ? C3 C2 C1 120.7(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.6(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C6 118.4(3) . . ? C4 C5 C8 120.8(4) . . ? C6 C5 C8 120.7(4) . . ? C5 C6 C7 120.7(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C2 C7 C6 120.4(4) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 N5 108.6(3) . . ? N2 C9 H9A 110.0 . . ? N5 C9 H9A 110.0 . . ? N2 C9 H9B 110.0 . . ? N5 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? N2 C10 C11 106.5(3) . . ? N2 C10 C13 121.9(3) . . ? C11 C10 C13 131.5(4) . . ? C10 C11 C12 107.2(3) . . ? C10 C11 H11 126.4 . . ? C12 C11 H11 126.4 . . ? N1 C12 C11 109.3(3) . . ? N1 C12 C14 122.6(3) . . ? C11 C12 C14 127.9(3) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N4 C15 N5 108.1(3) . . ? N4 C15 H15A 110.1 . . ? N5 C15 H15A 110.1 . . ? N4 C15 H15B 110.1 . . ? N5 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? N4 C16 C17 105.7(3) . . ? N4 C16 C19 122.2(3) . . ? C17 C16 C19 132.0(4) . . ? C16 C17 C18 107.3(3) . . ? C16 C17 H17 126.3 . . ? C18 C17 H17 126.3 . . ? N3 C18 C17 108.9(3) . . ? N3 C18 C20 124.2(4) . . ? C17 C18 C20 126.9(4) . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 Cl2 O3 112.5(3) . . ? O2 Cl2 O1 112.8(3) . . ? O3 Cl2 O1 110.8(2) . . ? O2 Cl2 O4 106.1(3) . . ? O3 Cl2 O4 108.1(3) . . ? O1 Cl2 O4 106.0(2) . . ? N1 Cu1 N3 162.34(11) . . ? N1 Cu1 N5 81.90(12) . . ? N3 Cu1 N5 80.63(12) . . ? N1 Cu1 Cl1 98.97(9) . . ? N3 Cu1 Cl1 98.47(9) . . ? N5 Cu1 Cl1 178.95(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N1 N2 C10 -1.7(4) . . . . ? Cu1 N1 N2 C10 -179.3(2) . . . . ? C12 N1 N2 C9 -179.7(3) . . . . ? Cu1 N1 N2 C9 2.7(4) . . . . ? C18 N3 N4 C16 1.3(4) . . . . ? Cu1 N3 N4 C16 -166.8(2) . . . . ? C18 N3 N4 C15 176.9(3) . . . . ? Cu1 N3 N4 C15 8.7(4) . . . . ? C9 N5 C1 C2 76.9(4) . . . . ? C15 N5 C1 C2 -157.0(3) . . . . ? Cu1 N5 C1 C2 -41.3(3) . . . . ? N5 C1 C2 C7 85.7(4) . . . . ? N5 C1 C2 C3 -94.5(4) . . . . ? C7 C2 C3 C4 -2.7(5) . . . . ? C1 C2 C3 C4 177.6(3) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? C3 C4 C5 C8 -180.0(3) . . . . ? C4 C5 C6 C7 -0.8(5) . . . . ? C8 C5 C6 C7 180.0(4) . . . . ? C3 C2 C7 C6 2.7(5) . . . . ? C1 C2 C7 C6 -177.5(3) . . . . ? C5 C6 C7 C2 -0.9(6) . . . . ? C10 N2 C9 N5 154.1(3) . . . . ? N1 N2 C9 N5 -28.3(4) . . . . ? C15 N5 C9 N2 151.6(3) . . . . ? C1 N5 C9 N2 -82.9(3) . . . . ? Cu1 N5 C9 N2 37.2(3) . . . . ? N1 N2 C10 C11 1.0(4) . . . . ? C9 N2 C10 C11 178.8(3) . . . . ? N1 N2 C10 C13 179.1(3) . . . . ? C9 N2 C10 C13 -3.1(6) . . . . ? N2 C10 C11 C12 0.1(4) . . . . ? C13 C10 C11 C12 -177.8(4) . . . . ? N2 N1 C12 C11 1.7(4) . . . . ? Cu1 N1 C12 C11 178.1(3) . . . . ? N2 N1 C12 C14 -174.0(3) . . . . ? Cu1 N1 C12 C14 2.4(6) . . . . ? C10 C11 C12 N1 -1.2(4) . . . . ? C10 C11 C12 C14 174.2(4) . . . . ? C16 N4 C15 N5 -164.4(3) . . . . ? N3 N4 C15 N5 20.9(4) . . . . ? C9 N5 C15 N4 -152.2(3) . . . . ? C1 N5 C15 N4 80.4(3) . . . . ? Cu1 N5 C15 N4 -37.7(3) . . . . ? N3 N4 C16 C17 -1.4(4) . . . . ? C15 N4 C16 C17 -176.5(3) . . . . ? N3 N4 C16 C19 176.4(4) . . . . ? C15 N4 C16 C19 1.4(6) . . . . ? N4 C16 C17 C18 0.9(4) . . . . ? C19 C16 C17 C18 -176.6(4) . . . . ? N4 N3 C18 C17 -0.7(4) . . . . ? Cu1 N3 C18 C17 161.3(3) . . . . ? N4 N3 C18 C20 178.6(3) . . . . ? Cu1 N3 C18 C20 -19.4(6) . . . . ? C16 C17 C18 N3 -0.2(4) . . . . ? C16 C17 C18 C20 -179.4(4) . . . . ? C12 N1 Cu1 N3 -152.4(4) . . . . ? N2 N1 Cu1 N3 23.8(5) . . . . ? C12 N1 Cu1 N5 -160.7(4) . . . . ? N2 N1 Cu1 N5 15.5(2) . . . . ? C12 N1 Cu1 Cl1 18.7(4) . . . . ? N2 N1 Cu1 Cl1 -165.1(2) . . . . ? C18 N3 Cu1 N1 166.0(4) . . . . ? N4 N3 Cu1 N1 -32.6(5) . . . . ? C18 N3 Cu1 N5 174.3(4) . . . . ? N4 N3 Cu1 N5 -24.2(2) . . . . ? C18 N3 Cu1 Cl1 -5.1(4) . . . . ? N4 N3 Cu1 Cl1 156.4(2) . . . . ? C9 N5 Cu1 N1 -29.6(2) . . . . ? C15 N5 Cu1 N1 -147.9(2) . . . . ? C1 N5 Cu1 N1 93.4(2) . . . . ? C9 N5 Cu1 N3 153.0(2) . . . . ? C15 N5 Cu1 N3 34.6(2) . . . . ? C1 N5 Cu1 N3 -84.0(2) . . . . ? C9 N5 Cu1 Cl1 -176(69) . . . . ? C15 N5 Cu1 Cl1 65(4) . . . . ? C1 N5 Cu1 Cl1 -53(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.038 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.125 data_yp5_m _database_code_depnum_ccdc_archive 'CCDC 716785' #TrackingRef '- yp5_m_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H48 CL6 CU2 N10 O8' _chemical_formula_sum 'C38 H48 Cl6 Cu2 N10 O8' _chemical_formula_weight 1112.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINI _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1275(12) _cell_length_b 10.1836(14) _cell_length_c 13.1067(18) _cell_angle_alpha 75.730(2) _cell_angle_beta 73.331(2) _cell_angle_gamma 89.528(2) _cell_volume 1128.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 968 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.50 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.5771 _exptl_absorpt_correction_T_max 0.6197 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13118 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5217 _reflns_number_gt 4701 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER SMART APEX CCD' _computing_cell_refinement 'BRUKER SMART APEX CCD' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS -97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'WINGX V1.80.01' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Perchlorate oxygen atoms were solved using ISOR restraints ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1105P)^2^+1.0278P] 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 5217 _refine_ls_number_parameters 293 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 0.695 _refine_ls_restrained_S_all 0.811 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_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_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 C1 C 0.7460(3) 0.3463(2) 0.6962(2) 0.0366(5) Uani 1 1 d . . . H1A H 0.7488 0.4163 0.7344 0.044 Uiso 1 1 calc R . . H1B H 0.8349 0.3639 0.6315 0.044 Uiso 1 1 calc R . . C2 C 0.6033(3) 0.3549(2) 0.66034(19) 0.0325(4) Uani 1 1 d . . . C3 C 0.6040(3) 0.3237(2) 0.56243(19) 0.0348(5) Uani 1 1 d . . . H3 H 0.6948 0.3022 0.5172 0.042 Uiso 1 1 calc R . . C4 C 0.4708(3) 0.3243(2) 0.5318(2) 0.0368(5) Uani 1 1 d . . . H4 H 0.4711 0.3019 0.4672 0.044 Uiso 1 1 calc R . . C5 C 0.3374(3) 0.3589(2) 0.5987(2) 0.0375(5) Uani 1 1 d . . . C6 C 0.3341(3) 0.3948(3) 0.6941(2) 0.0403(5) Uani 1 1 d . . . H6 H 0.2438 0.4201 0.7371 0.048 Uiso 1 1 calc R . . C7 C 0.4680(3) 0.3924(3) 0.7248(2) 0.0372(5) Uani 1 1 d . . . H7 H 0.4671 0.4161 0.7891 0.045 Uiso 1 1 calc R . . C8 C 0.7965(3) 0.1009(3) 0.7131(2) 0.0343(5) Uani 1 1 d . . . H8A H 0.8693 0.1376 0.6412 0.041 Uiso 1 1 calc R . . H8B H 0.8432 0.0295 0.7547 0.041 Uiso 1 1 calc R . . C9 C 0.6403(3) -0.0155(2) 0.6250(2) 0.0349(5) Uani 1 1 d . . . C10 C 0.4860(3) -0.0470(3) 0.6498(2) 0.0384(5) Uani 1 1 d . . . H10 H 0.4388 -0.0911 0.6121 0.046 Uiso 1 1 calc R . . C11 C 0.4128(3) -0.0001(2) 0.7428(2) 0.0342(5) Uani 1 1 d . . . C12 C 0.7734(3) -0.0379(3) 0.5346(2) 0.0457(6) Uani 1 1 d . . . H12A H 0.8280 0.0477 0.4929 0.069 Uiso 1 1 calc R . . H12B H 0.7369 -0.0787 0.4870 0.069 Uiso 1 1 calc R . . H12C H 0.8406 -0.0969 0.5657 0.069 Uiso 1 1 calc R . . C13 C 0.2446(3) 0.0003(3) 0.7950(2) 0.0443(6) Uani 1 1 d . . . H13A H 0.2201 -0.0423 0.8724 0.066 Uiso 1 1 calc R . . H13B H 0.1903 -0.0487 0.7617 0.066 Uiso 1 1 calc R . . H13C H 0.2151 0.0923 0.7845 0.066 Uiso 1 1 calc R . . C14 C 0.8632(3) 0.2207(3) 0.83411(19) 0.0336(5) Uani 1 1 d . . . H14A H 0.9009 0.1328 0.8589 0.040 Uiso 1 1 calc R . . H14B H 0.9500 0.2832 0.7881 0.040 Uiso 1 1 calc R . . C15 C 0.8395(3) 0.3189(2) 0.9966(2) 0.0362(5) Uani 1 1 d . . . C16 C 0.7152(3) 0.3463(3) 1.0758(2) 0.0410(5) Uani 1 1 d . . . H16 H 0.7184 0.3819 1.1340 0.049 Uiso 1 1 calc R . . C17 C 0.5838(3) 0.3104(2) 1.0520(2) 0.0363(5) Uani 1 1 d . . . C18 C 1.0065(3) 0.3300(3) 0.9816(3) 0.0501(7) Uani 1 1 d . . . H18A H 1.0504 0.2479 0.9675 0.075 Uiso 1 1 calc R . . H18B H 1.0238 0.3437 1.0472 0.075 Uiso 1 1 calc R . . H18C H 1.0536 0.4055 0.9205 0.075 Uiso 1 1 calc R . . C19 C 0.4209(3) 0.3238(3) 1.1126(3) 0.0499(7) Uani 1 1 d . . . H19A H 0.3662 0.3616 1.0608 0.075 Uiso 1 1 calc R . . H19B H 0.4178 0.3825 1.1602 0.075 Uiso 1 1 calc R . . H19C H 0.3741 0.2360 1.1558 0.075 Uiso 1 1 calc R . . N1 N 0.7555(2) 0.20905(19) 0.77137(15) 0.0291(4) Uani 1 1 d . . . N2 N 0.6573(2) 0.0464(2) 0.70111(16) 0.0313(4) Uani 1 1 d . . . N3 N 0.5194(2) 0.0552(2) 0.77520(16) 0.0313(4) Uani 1 1 d . . . N4 N 0.6236(2) 0.2621(2) 0.96190(17) 0.0332(4) Uani 1 1 d . . . N5 N 0.7808(2) 0.2708(2) 0.92817(16) 0.0319(4) Uani 1 1 d . . . O1 O 0.8127(3) 0.2937(3) 0.3106(2) 0.0686(6) Uani 1 1 d U . . O2 O 0.9783(3) 0.2973(3) 0.4144(2) 0.0653(6) Uani 1 1 d U . . O3 O 1.0385(4) 0.4308(3) 0.2325(3) 0.0854(8) Uani 1 1 d U . . O4 O 1.0458(3) 0.1948(3) 0.2676(2) 0.0682(6) Uani 1 1 d U . . Cl1 Cl 0.31538(6) 0.07907(6) 1.01265(5) 0.03806(13) Uani 1 1 d . . . Cl2 Cl 0.17155(8) 0.36004(8) 0.55866(7) 0.05728(19) Uani 1 1 d . . . Cl3 Cl 0.97150(7) 0.30466(6) 0.30554(5) 0.04039(13) Uani 1 1 d . . . Cu1 Cu 0.54331(3) 0.14439(3) 0.88741(2) 0.02923(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 C1 0.0324(11) 0.0344(11) 0.0386(12) -0.0017(9) -0.0101(9) -0.0043(9) C2 0.0311(11) 0.0300(10) 0.0317(10) -0.0021(8) -0.0068(8) 0.0012(8) C3 0.0343(11) 0.0343(11) 0.0302(10) -0.0040(9) -0.0043(9) 0.0049(9) C4 0.0427(13) 0.0337(11) 0.0339(11) -0.0076(9) -0.0121(10) 0.0027(9) C5 0.0337(12) 0.0312(11) 0.0463(13) -0.0044(10) -0.0142(10) 0.0006(9) C6 0.0329(12) 0.0397(13) 0.0428(13) -0.0097(10) -0.0035(10) 0.0075(10) C7 0.0402(13) 0.0360(12) 0.0346(11) -0.0111(9) -0.0079(10) 0.0040(9) C8 0.0279(10) 0.0409(12) 0.0367(11) -0.0151(10) -0.0089(9) 0.0014(9) C9 0.0422(13) 0.0327(11) 0.0344(11) -0.0111(9) -0.0165(10) 0.0062(9) C10 0.0436(13) 0.0363(12) 0.0426(13) -0.0136(10) -0.0207(11) 0.0016(10) C11 0.0351(12) 0.0306(11) 0.0399(12) -0.0076(9) -0.0167(10) -0.0016(9) C12 0.0510(15) 0.0507(15) 0.0414(13) -0.0214(12) -0.0149(12) 0.0120(12) C13 0.0338(13) 0.0483(14) 0.0526(15) -0.0130(12) -0.0152(11) -0.0059(10) C14 0.0255(10) 0.0438(12) 0.0342(11) -0.0135(10) -0.0098(8) 0.0000(9) C15 0.0406(13) 0.0347(11) 0.0379(12) -0.0095(9) -0.0181(10) 0.0008(9) C16 0.0486(14) 0.0407(13) 0.0391(12) -0.0168(10) -0.0155(11) 0.0031(11) C17 0.0406(13) 0.0321(11) 0.0361(11) -0.0108(9) -0.0092(10) 0.0020(9) C18 0.0410(14) 0.0656(18) 0.0553(16) -0.0261(14) -0.0228(12) 0.0027(13) C19 0.0442(15) 0.0518(16) 0.0531(16) -0.0250(13) -0.0037(12) 0.0048(12) N1 0.0261(9) 0.0330(9) 0.0291(9) -0.0084(7) -0.0089(7) 0.0001(7) N2 0.0300(9) 0.0333(9) 0.0314(9) -0.0097(7) -0.0088(7) 0.0015(7) N3 0.0278(9) 0.0341(9) 0.0316(9) -0.0081(7) -0.0082(7) -0.0018(7) N4 0.0276(9) 0.0367(10) 0.0361(10) -0.0121(8) -0.0082(7) -0.0005(7) N5 0.0290(9) 0.0352(10) 0.0333(9) -0.0107(8) -0.0102(7) -0.0014(7) O1 0.0595(10) 0.0843(11) 0.0699(10) -0.0231(9) -0.0284(8) 0.0072(9) O2 0.0670(10) 0.0798(11) 0.0587(10) -0.0227(8) -0.0292(8) 0.0091(9) O3 0.0945(13) 0.0660(11) 0.0857(12) -0.0107(9) -0.0180(10) -0.0070(9) O4 0.0704(11) 0.0643(10) 0.0709(11) -0.0262(9) -0.0147(8) 0.0169(9) Cl1 0.0270(3) 0.0441(3) 0.0383(3) -0.0083(2) -0.0039(2) 0.0002(2) Cl2 0.0398(3) 0.0597(4) 0.0769(5) -0.0122(4) -0.0285(3) 0.0009(3) Cl3 0.0425(3) 0.0414(3) 0.0397(3) -0.0130(2) -0.0136(2) 0.0048(2) Cu1 0.02476(14) 0.03252(14) 0.02988(14) -0.00894(11) -0.00628(10) -0.00183(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.501(3) . ? C1 N1 1.517(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.392(3) . ? C2 C3 1.394(3) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? C4 C5 1.381(4) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 Cl2 1.738(2) . ? C6 C7 1.391(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N2 1.454(3) . ? C8 N1 1.477(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.348(3) . ? C9 C10 1.374(4) . ? C9 C12 1.495(4) . ? C10 C11 1.406(4) . ? C10 H10 0.9300 . ? C11 N3 1.344(3) . ? C11 C13 1.492(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N5 1.455(3) . ? C14 N1 1.473(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N5 1.352(3) . ? C15 C16 1.380(4) . ? C15 C18 1.482(4) . ? C16 C17 1.396(4) . ? C16 H16 0.9300 . ? C17 N4 1.343(3) . ? C17 C19 1.494(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 Cu1 2.0822(18) . ? N2 N3 1.369(3) . ? N3 Cu1 1.9704(19) . ? N4 N5 1.371(3) . ? N4 Cu1 1.982(2) . ? O1 Cl3 1.436(3) . ? O2 Cl3 1.430(2) . ? O3 Cl3 1.418(3) . ? O4 Cl3 1.424(2) . ? Cl1 Cu1 2.2340(6) . ? 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 C2 C1 N1 112.71(18) . . ? C2 C1 H1A 109.1 . . ? N1 C1 H1A 109.1 . . ? C2 C1 H1B 109.1 . . ? N1 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? C7 C2 C3 119.0(2) . . ? C7 C2 C1 120.6(2) . . ? C3 C2 C1 120.4(2) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 119.0(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C6 C5 C4 121.7(2) . . ? C6 C5 Cl2 119.8(2) . . ? C4 C5 Cl2 118.4(2) . . ? C5 C6 C7 118.8(2) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C6 C7 C2 120.7(2) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? N2 C8 N1 108.29(18) . . ? N2 C8 H8A 110.0 . . ? N1 C8 H8A 110.0 . . ? N2 C8 H8B 110.0 . . ? N1 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? N2 C9 C10 106.3(2) . . ? N2 C9 C12 122.3(2) . . ? C10 C9 C12 131.3(2) . . ? C9 C10 C11 107.0(2) . . ? C9 C10 H10 126.5 . . ? C11 C10 H10 126.5 . . ? N3 C11 C10 109.0(2) . . ? N3 C11 C13 123.6(2) . . ? C10 C11 C13 127.2(2) . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 N1 107.60(18) . . ? N5 C14 H14A 110.2 . . ? N1 C14 H14A 110.2 . . ? N5 C14 H14B 110.2 . . ? N1 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? N5 C15 C16 105.9(2) . . ? N5 C15 C18 122.2(2) . . ? C16 C15 C18 131.9(2) . . ? C15 C16 C17 107.1(2) . . ? C15 C16 H16 126.5 . . ? C17 C16 H16 126.5 . . ? N4 C17 C16 109.8(2) . . ? N4 C17 C19 122.9(2) . . ? C16 C17 C19 127.4(2) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 N1 C8 110.82(18) . . ? C14 N1 C1 109.94(18) . . ? C8 N1 C1 113.60(18) . . ? C14 N1 Cu1 106.20(14) . . ? C8 N1 Cu1 105.98(13) . . ? C1 N1 Cu1 109.98(14) . . ? C9 N2 N3 111.61(19) . . ? C9 N2 C8 129.3(2) . . ? N3 N2 C8 119.12(19) . . ? C11 N3 N2 105.94(19) . . ? C11 N3 Cu1 142.19(17) . . ? N2 N3 Cu1 111.86(14) . . ? C17 N4 N5 105.42(19) . . ? C17 N4 Cu1 141.66(17) . . ? N5 N4 Cu1 110.25(14) . . ? C15 N5 N4 111.8(2) . . ? C15 N5 C14 127.9(2) . . ? N4 N5 C14 120.04(18) . . ? O3 Cl3 O4 110.64(18) . . ? O3 Cl3 O2 110.84(18) . . ? O4 Cl3 O2 110.10(16) . . ? O3 Cl3 O1 108.68(19) . . ? O4 Cl3 O1 108.94(17) . . ? O2 Cl3 O1 107.56(15) . . ? N3 Cu1 N4 162.08(8) . . ? N3 Cu1 N1 81.88(8) . . ? N4 Cu1 N1 80.53(8) . . ? N3 Cu1 Cl1 99.02(6) . . ? N4 Cu1 Cl1 98.53(6) . . ? N1 Cu1 Cl1 178.86(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 N1 C1 C2 C7 86.8(3) . . . . ? N1 C1 C2 C3 -92.5(3) . . . . ? C7 C2 C3 C4 -2.7(3) . . . . ? C1 C2 C3 C4 176.5(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? C3 C4 C5 Cl2 179.66(18) . . . . ? C4 C5 C6 C7 -1.8(4) . . . . ? Cl2 C5 C6 C7 179.67(19) . . . . ? C5 C6 C7 C2 0.2(4) . . . . ? C3 C2 C7 C6 2.0(4) . . . . ? C1 C2 C7 C6 -177.2(2) . . . . ? N2 C9 C10 C11 0.5(3) . . . . ? C12 C9 C10 C11 -178.8(3) . . . . ? C9 C10 C11 N3 -1.4(3) . . . . ? C9 C10 C11 C13 174.2(2) . . . . ? N5 C15 C16 C17 1.0(3) . . . . ? C18 C15 C16 C17 -176.9(3) . . . . ? C15 C16 C17 N4 0.2(3) . . . . ? C15 C16 C17 C19 -178.6(3) . . . . ? N5 C14 N1 C8 -151.30(19) . . . . ? N5 C14 N1 C1 82.3(2) . . . . ? N5 C14 N1 Cu1 -36.6(2) . . . . ? N2 C8 N1 C14 151.52(19) . . . . ? N2 C8 N1 C1 -84.1(2) . . . . ? N2 C8 N1 Cu1 36.7(2) . . . . ? C2 C1 N1 C14 -159.9(2) . . . . ? C2 C1 N1 C8 75.2(2) . . . . ? C2 C1 N1 Cu1 -43.3(2) . . . . ? C10 C9 N2 N3 0.6(3) . . . . ? C12 C9 N2 N3 180.0(2) . . . . ? C10 C9 N2 C8 -179.8(2) . . . . ? C12 C9 N2 C8 -0.4(4) . . . . ? N1 C8 N2 C9 154.4(2) . . . . ? N1 C8 N2 N3 -26.0(3) . . . . ? C10 C11 N3 N2 1.7(3) . . . . ? C13 C11 N3 N2 -174.1(2) . . . . ? C10 C11 N3 Cu1 -179.8(2) . . . . ? C13 C11 N3 Cu1 4.3(4) . . . . ? C9 N2 N3 C11 -1.5(3) . . . . ? C8 N2 N3 C11 178.8(2) . . . . ? C9 N2 N3 Cu1 179.59(15) . . . . ? C8 N2 N3 Cu1 -0.1(2) . . . . ? C16 C17 N4 N5 -1.3(3) . . . . ? C19 C17 N4 N5 177.6(2) . . . . ? C16 C17 N4 Cu1 156.8(2) . . . . ? C19 C17 N4 Cu1 -24.4(4) . . . . ? C16 C15 N5 N4 -1.9(3) . . . . ? C18 C15 N5 N4 176.3(2) . . . . ? C16 C15 N5 C14 -176.7(2) . . . . ? C18 C15 N5 C14 1.5(4) . . . . ? C17 N4 N5 C15 2.0(3) . . . . ? Cu1 N4 N5 C15 -163.70(16) . . . . ? C17 N4 N5 C14 177.3(2) . . . . ? Cu1 N4 N5 C14 11.6(3) . . . . ? N1 C14 N5 C15 -167.4(2) . . . . ? N1 C14 N5 N4 18.1(3) . . . . ? C11 N3 Cu1 N4 -149.9(3) . . . . ? N2 N3 Cu1 N4 28.5(3) . . . . ? C11 N3 Cu1 N1 -160.9(3) . . . . ? N2 N3 Cu1 N1 17.46(14) . . . . ? C11 N3 Cu1 Cl1 18.4(3) . . . . ? N2 N3 Cu1 Cl1 -163.26(13) . . . . ? C17 N4 Cu1 N3 165.7(3) . . . . ? N5 N4 Cu1 N3 -36.8(3) . . . . ? C17 N4 Cu1 N1 176.8(3) . . . . ? N5 N4 Cu1 N1 -25.76(15) . . . . ? C17 N4 Cu1 Cl1 -2.5(3) . . . . ? N5 N4 Cu1 Cl1 154.89(14) . . . . ? C14 N1 Cu1 N3 -148.28(15) . . . . ? C8 N1 Cu1 N3 -30.37(14) . . . . ? C1 N1 Cu1 N3 92.81(15) . . . . ? C14 N1 Cu1 N4 35.14(15) . . . . ? C8 N1 Cu1 N4 153.05(15) . . . . ? C1 N1 Cu1 N4 -83.77(15) . . . . ? C14 N1 Cu1 Cl1 70(3) . . . . ? C8 N1 Cu1 Cl1 -172(2) . . . . ? C1 N1 Cu1 Cl1 -49(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.616 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.062 data_i _database_code_depnum_ccdc_archive 'CCDC 716786' #TrackingRef '- complex_1.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H50 Cl2 Cu2 N10, 2(ClO4)' _chemical_formula_sum 'C38 H50 Cl4 Cu2 N10 O8' _chemical_formula_weight 1043.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/C _symmetry_space_group_name_hall '-P 2ybc' 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 8.427 _cell_length_b 21.205 _cell_length_c 12.694 _cell_angle_alpha 90.00 _cell_angle_beta 96.68 _cell_angle_gamma 90.00 _cell_volume 2252.949 _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 578 _cell_measurement_theta_min 1.88 _cell_measurement_theta_max 25.05 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 1.242 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.563 _exptl_absorpt_correction_T_max 0.608 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD' _diffrn_measurement_method OMEGA _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16028 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3987 _reflns_number_gt 3288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX CCD' _computing_cell_refinement 'BRUKER SMART APEX CCD' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0522P)^2^+0.4947P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3987 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0489 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.47266(4) 0.070680(14) 0.92577(2) 0.03550(12) Uani 1 1 d . . . Cl1 Cl 0.70443(8) 0.03770(3) 1.01250(6) 0.04504(19) Uani 1 1 d . . . Cl2 Cl 0.07030(14) 0.16471(4) 0.43905(8) 0.0770(3) Uani 1 1 d . . . O1 O 0.0551(4) 0.15127(16) 0.5441(2) 0.1077(10) Uani 1 1 d . A . O11 O 0.2549(16) 0.1531(14) 0.4283(10) 0.201(12) Uani 0.355(12) 1 d P A 1 O13 O 0.069(3) 0.2250(9) 0.404(2) 0.110(8) Uani 0.355(12) 1 d P A 1 O16 O 0.004(2) 0.1289(6) 0.3567(8) 0.101(6) Uani 0.355(12) 1 d P A 1 O12 O -0.1052(10) 0.1714(5) 0.4040(9) 0.188(6) Uani 0.645(12) 1 d P A 2 O14 O 0.1217(17) 0.1152(3) 0.3935(9) 0.174(7) Uani 0.645(12) 1 d P A 2 O15 O 0.135(2) 0.2200(6) 0.4258(14) 0.162(6) Uani 0.645(12) 1 d P A 2 N1 N 0.3939(2) 0.12141(10) 1.03922(18) 0.0395(5) Uani 1 1 d . . . N2 N 0.2328(3) 0.13266(10) 1.01952(18) 0.0408(5) Uani 1 1 d . . . C3 C 0.1760(4) 0.16101(13) 1.1021(2) 0.0450(7) Uani 1 1 d . . . C4 C 0.3055(4) 0.17003(13) 1.1768(3) 0.0494(7) Uani 1 1 d . . . H4 H 0.3046 0.1892 1.2426 0.059 Uiso 1 1 calc R . . C5 C 0.4381(3) 0.14533(12) 1.1359(2) 0.0419(7) Uani 1 1 d . . . C6 C 0.1451(3) 0.10817(14) 0.9232(2) 0.0446(7) Uani 1 1 d . . . H6A H 0.0609(18) 0.1357(6) 0.8987(5) 0.054 Uiso 1 1 calc R . . H6B H 0.1017(10) 0.0683(8) 0.9359(3) 0.054 Uiso 1 1 calc R . . C7 C 0.0037(4) 0.17616(17) 1.1038(3) 0.0626(9) Uani 1 1 d . . . H7A H -0.0258 0.2102 1.0556 0.094 Uiso 1 1 calc R . . H7B H -0.0146 0.1883 1.1742 0.094 Uiso 1 1 calc R . . H7C H -0.0597 0.1397 1.0826 0.094 Uiso 1 1 calc R . . C8 C 0.6072(4) 0.14663(16) 1.1859(3) 0.0573(8) Uani 1 1 d . . . H8A H 0.6477 0.1043 1.1929 0.086 Uiso 1 1 calc R . . H8B H 0.6121 0.1657 1.2548 0.086 Uiso 1 1 calc R . . H8C H 0.6707 0.1707 1.1423 0.086 Uiso 1 1 calc R . . N9 N 0.2597(2) 0.10299(10) 0.84380(17) 0.0388(5) Uani 1 1 d . . . N11 N 0.4913(2) 0.02982(10) 0.78795(17) 0.0374(5) Uani 1 1 d . . . N12 N 0.3480(2) 0.02742(10) 0.72584(17) 0.0384(5) Uani 1 1 d . . . C13 C 0.3573(3) -0.00423(13) 0.6351(2) 0.0437(7) Uani 1 1 d . . . C14 C 0.5137(3) -0.02219(13) 0.6379(2) 0.0463(7) Uani 1 1 d . . . H14 H 0.5579 -0.0452 0.5862 0.056 Uiso 1 1 calc R . . C15 C 0.5947(3) 0.00034(12) 0.7324(2) 0.0385(6) Uani 1 1 d . . . C16 C 0.2077(3) 0.05454(14) 0.7650(2) 0.0455(7) Uani 1 1 d . . . H16A H 0.1497(13) 0.0227(7) 0.7964(7) 0.055 Uiso 1 1 calc R . . H16B H 0.1400(15) 0.0727(4) 0.7081(12) 0.055 Uiso 1 1 calc R . . C17 C 0.2152(4) -0.01508(17) 0.5558(3) 0.0605(9) Uani 1 1 d . . . H17A H 0.1325 -0.0352 0.5897 0.091 Uiso 1 1 calc R . . H17B H 0.2445 -0.0417 0.5000 0.091 Uiso 1 1 calc R . . H17C H 0.1768 0.0246 0.5266 0.091 Uiso 1 1 calc R . . C18 C 0.7695(3) -0.00271(16) 0.7672(2) 0.0522(8) Uani 1 1 d . . . H18A H 0.8122 0.0393 0.7738 0.078 Uiso 1 1 calc R . . H18B H 0.8214 -0.0256 0.7157 0.078 Uiso 1 1 calc R . . H18C H 0.7876 -0.0237 0.8345 0.078 Uiso 1 1 calc R . . C21 C 0.2881(4) 0.16681(14) 0.7959(3) 0.0511(8) Uani 1 1 d . . . H21A H 0.2083(18) 0.1736(2) 0.7360(13) 0.061 Uiso 1 1 calc R . . H21B H 0.2745(5) 0.1990(7) 0.8478(11) 0.061 Uiso 1 1 calc R . . C22 C 0.4493(4) 0.17393(13) 0.7601(3) 0.0498(8) Uani 1 1 d . . . C23 C 0.4743(5) 0.16178(16) 0.6563(3) 0.0735(11) Uani 1 1 d . . . H23 H 0.3888 0.1506 0.6068 0.088 Uiso 1 1 calc R . . C24 C 0.6271(8) 0.1662(2) 0.6258(5) 0.1059(18) Uani 1 1 d . . . H24 H 0.6443 0.1576 0.5562 0.127 Uiso 1 1 calc R . . C25 C 0.7501(7) 0.1830(2) 0.6978(7) 0.121(3) Uani 1 1 d . . . H25 H 0.8521 0.1854 0.6769 0.145 Uiso 1 1 calc R . . C26 C 0.7298(6) 0.1965(2) 0.7991(6) 0.1034(18) Uani 1 1 d . . . H26 H 0.8164 0.2086 0.8470 0.124 Uiso 1 1 calc R . . C27 C 0.5774(5) 0.19201(15) 0.8315(3) 0.0720(10) Uani 1 1 d . . . H27 H 0.5622 0.2012 0.9012 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.03270(19) 0.0381(2) 0.0357(2) -0.00231(14) 0.00388(13) 0.00719(13) Cl1 0.0371(4) 0.0505(4) 0.0458(4) -0.0033(3) -0.0025(3) 0.0086(3) Cl2 0.1194(9) 0.0534(5) 0.0585(6) 0.0054(4) 0.0122(5) 0.0015(5) O1 0.127(3) 0.132(3) 0.0672(19) 0.0172(18) 0.0267(18) 0.003(2) O11 0.094(9) 0.42(3) 0.101(9) 0.069(14) 0.048(8) 0.120(13) O13 0.155(16) 0.041(7) 0.139(12) 0.036(8) 0.035(10) 0.035(10) O16 0.177(15) 0.066(8) 0.062(6) -0.012(5) 0.029(7) -0.035(8) O12 0.146(7) 0.198(9) 0.197(9) 0.075(8) -0.072(6) 0.005(6) O14 0.293(17) 0.065(4) 0.198(12) 0.014(5) 0.176(12) 0.057(7) O15 0.244(16) 0.091(9) 0.174(12) -0.026(7) 0.121(12) -0.088(8) N1 0.0344(12) 0.0403(12) 0.0448(14) -0.0042(10) 0.0091(10) 0.0047(10) N2 0.0371(12) 0.0435(13) 0.0433(14) -0.0019(11) 0.0111(10) 0.0071(10) C3 0.0489(17) 0.0354(14) 0.0546(19) -0.0026(13) 0.0229(15) 0.0026(12) C4 0.0562(19) 0.0419(16) 0.0539(19) -0.0140(14) 0.0225(15) -0.0051(14) C5 0.0477(16) 0.0334(14) 0.0464(17) -0.0065(12) 0.0134(13) -0.0057(12) C6 0.0332(14) 0.0535(17) 0.0474(17) 0.0005(14) 0.0062(12) 0.0090(13) C7 0.0521(19) 0.068(2) 0.072(2) -0.0117(18) 0.0258(17) 0.0078(16) C8 0.0530(19) 0.061(2) 0.058(2) -0.0200(16) 0.0082(15) -0.0098(15) N9 0.0351(12) 0.0418(12) 0.0397(13) 0.0022(10) 0.0057(10) 0.0116(10) N11 0.0344(12) 0.0396(12) 0.0378(13) -0.0003(10) 0.0028(10) 0.0054(9) N12 0.0360(12) 0.0423(12) 0.0363(13) -0.0012(10) 0.0019(10) 0.0039(10) C13 0.0520(17) 0.0400(15) 0.0386(16) -0.0017(13) 0.0033(13) -0.0038(13) C14 0.0532(18) 0.0447(16) 0.0430(17) -0.0076(13) 0.0141(14) 0.0004(13) C15 0.0415(15) 0.0368(14) 0.0387(16) 0.0008(12) 0.0110(12) 0.0051(12) C16 0.0348(15) 0.0580(18) 0.0422(17) -0.0022(14) -0.0016(12) 0.0085(13) C17 0.062(2) 0.066(2) 0.0507(19) -0.0099(16) -0.0039(15) -0.0081(16) C18 0.0425(17) 0.063(2) 0.0526(19) -0.0060(15) 0.0125(14) 0.0102(14) C21 0.0538(18) 0.0445(17) 0.0554(19) 0.0114(14) 0.0083(15) 0.0156(14) C22 0.0490(18) 0.0373(15) 0.064(2) 0.0128(14) 0.0111(15) 0.0067(13) C23 0.093(3) 0.055(2) 0.079(3) 0.0042(19) 0.037(2) -0.0007(19) C24 0.137(5) 0.066(3) 0.132(5) 0.010(3) 0.088(4) 0.008(3) C25 0.083(4) 0.068(3) 0.223(8) 0.056(4) 0.064(5) 0.011(3) C26 0.062(3) 0.068(3) 0.175(6) 0.049(3) -0.009(3) -0.008(2) C27 0.076(3) 0.0470(19) 0.089(3) 0.0226(18) -0.009(2) -0.0052(17) _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 1.974(2) . ? Cu1 N11 1.975(2) . ? Cu1 N9 2.083(2) . ? Cu1 Cl1 2.2396(7) . ? Cl2 O14 1.298(6) . ? Cl2 O15 1.312(12) . ? Cl2 O13 1.354(17) . ? Cl2 O16 1.360(10) . ? Cl2 O1 1.384(3) . ? Cl2 O12 1.501(8) . ? Cl2 O11 1.596(10) . ? N1 C5 1.340(3) . ? N1 N2 1.372(3) . ? N2 C3 1.344(3) . ? N2 C6 1.449(3) . ? C3 C4 1.373(4) . ? C3 C7 1.490(4) . ? C4 C5 1.388(4) . ? C5 C8 1.492(4) . ? C6 N9 1.479(3) . ? N9 C16 1.465(4) . ? N9 C21 1.514(4) . ? N11 C15 1.338(3) . ? N11 N12 1.364(3) . ? N12 C13 1.343(3) . ? N12 C16 1.454(3) . ? C13 C14 1.369(4) . ? C13 C17 1.490(4) . ? C14 C15 1.394(4) . ? C15 C18 1.489(4) . ? C21 C22 1.489(4) . ? C22 C27 1.380(5) . ? C22 C23 1.382(5) . ? C23 C24 1.390(6) . ? C24 C25 1.347(8) . ? C25 C26 1.348(8) . ? C26 C27 1.397(6) . ? 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 N11 162.52(9) . . ? N1 Cu1 N9 80.90(9) . . ? N11 Cu1 N9 81.63(8) . . ? N1 Cu1 Cl1 99.19(7) . . ? N11 Cu1 Cl1 98.27(6) . . ? N9 Cu1 Cl1 178.75(7) . . ? O14 Cl2 O15 120.1(8) . . ? O14 Cl2 O13 127.3(13) . . ? O15 Cl2 O13 25.9(15) . . ? O14 Cl2 O16 48.3(6) . . ? O15 Cl2 O16 122.8(9) . . ? O13 Cl2 O16 106.6(14) . . ? O14 Cl2 O1 109.6(5) . . ? O15 Cl2 O1 113.2(8) . . ? O13 Cl2 O1 121.1(13) . . ? O16 Cl2 O1 123.3(5) . . ? O14 Cl2 O12 108.3(8) . . ? O15 Cl2 O12 106.6(7) . . ? O13 Cl2 O12 81.1(11) . . ? O16 Cl2 O12 61.4(7) . . ? O1 Cl2 O12 96.1(5) . . ? O14 Cl2 O11 57.2(9) . . ? O15 Cl2 O11 72.8(11) . . ? O13 Cl2 O11 94.9(13) . . ? O16 Cl2 O11 99.7(10) . . ? O1 Cl2 O11 104.5(5) . . ? O12 Cl2 O11 157.8(7) . . ? C5 N1 N2 105.4(2) . . ? C5 N1 Cu1 142.49(19) . . ? N2 N1 Cu1 111.80(16) . . ? C3 N2 N1 111.7(2) . . ? C3 N2 C6 128.7(2) . . ? N1 N2 C6 119.2(2) . . ? N2 C3 C4 105.9(2) . . ? N2 C3 C7 122.9(3) . . ? C4 C3 C7 131.1(3) . . ? C3 C4 C5 107.4(3) . . ? N1 C5 C4 109.6(3) . . ? N1 C5 C8 123.2(2) . . ? C4 C5 C8 127.2(3) . . ? N2 C6 N9 107.0(2) . . ? C16 N9 C6 110.5(2) . . ? C16 N9 C21 113.7(2) . . ? C6 N9 C21 110.7(2) . . ? C16 N9 Cu1 106.40(15) . . ? C6 N9 Cu1 106.07(16) . . ? C21 N9 Cu1 109.11(17) . . ? C15 N11 N12 105.4(2) . . ? C15 N11 Cu1 142.71(19) . . ? N12 N11 Cu1 111.86(15) . . ? C13 N12 N11 112.3(2) . . ? C13 N12 C16 128.4(2) . . ? N11 N12 C16 119.2(2) . . ? N12 C13 C14 105.6(2) . . ? N12 C13 C17 122.3(3) . . ? C14 C13 C17 132.1(3) . . ? C13 C14 C15 107.5(2) . . ? N11 C15 C14 109.3(2) . . ? N11 C15 C18 123.1(2) . . ? C14 C15 C18 127.5(2) . . ? N12 C16 N9 108.7(2) . . ? C22 C21 N9 113.9(2) . . ? C27 C22 C23 118.9(4) . . ? C27 C22 C21 120.0(3) . . ? C23 C22 C21 121.1(3) . . ? C22 C23 C24 120.1(5) . . ? C25 C24 C23 119.6(5) . . ? C24 C25 C26 122.0(5) . . ? C25 C26 C27 119.3(5) . . ? C22 C27 C26 120.1(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.335 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.059 data_ma _database_code_depnum_ccdc_archive 'CCDC 893810' #TrackingRef '- complex_2.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H62 Cl4 Cu2 N10 O12' _chemical_formula_weight 1167.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4248(14) _cell_length_b 11.5255(17) _cell_length_c 12.6536(19) _cell_angle_alpha 85.280(8) _cell_angle_beta 86.063(9) _cell_angle_gamma 78.893(8) _cell_volume 1342.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1943 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 1.056 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_T_max 0.881 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX-II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18104 _diffrn_reflns_av_R_equivalents 0.1390 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.01 _reflns_number_total 5858 _reflns_number_gt 3739 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART APEX II CCD' _computing_cell_refinement 'BRUKER SMART APEX II CCD' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 2.4' _computing_publication_material 'WINGX V1.80.01' _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. Two positions of carbon atoms of methanol solvent were found with equal occupacy. O-H bond length of solvent methanol was fixed. Thermal parameters for oxygen atoms of perchlorte ion were fixed. Bond distances and bond angles in perchlorate ions are fixed in space. ; _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^)+(0.1718P)^2^+0.8051P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5858 _refine_ls_number_parameters 326 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1158 _refine_ls_R_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.2807 _refine_ls_wR_factor_gt 0.2422 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.50597(8) 0.99616(6) 0.86395(5) 0.0489(3) Uani 1 1 d . . . Cl1 Cl 0.68366(18) 0.91034(14) 0.96793(12) 0.0602(4) Uani 1 1 d . . . N5 N 0.4045(6) 0.8606(4) 0.8630(4) 0.0541(12) Uani 1 1 d . . . O1 O 0.6666(7) 0.5847(5) 0.5630(6) 0.0934(18) Uani 1 1 d . . . O6 O 0.9852(5) 0.5583(4) 0.1555(6) 0.0881(19) Uani 1 1 d D . . N3 N 0.3477(5) 1.0715(4) 0.7585(4) 0.0461(10) Uani 1 1 d . . . C20 C 0.6218(8) 0.8897(7) 0.6392(5) 0.0633(17) Uani 1 1 d . . . H20 H 0.6757 0.9421 0.6611 0.076 Uiso 1 1 calc R . . N1 N 0.5668(6) 1.1525(4) 0.8302(4) 0.0568(13) Uani 1 1 d . . . C3 C 0.6429(10) 1.3226(7) 0.7888(7) 0.077(2) Uani 1 1 d . . . H3 H 0.7001 1.3804 0.7831 0.092 Uiso 1 1 calc R . . C10 C 0.2945(10) 0.7062(7) 0.8659(7) 0.079(2) Uani 1 1 d . . . H10 H 0.2773 0.6293 0.8766 0.094 Uiso 1 1 calc R . . N4 N 0.2708(6) 0.8955(5) 0.8248(4) 0.0551(12) Uani 1 1 d . . . C7 C 0.2215(7) 1.0199(6) 0.7923(5) 0.0584(15) Uani 1 1 d . . . H7A H 0.1574 1.0275 0.7343 0.070 Uiso 1 1 calc R . . H7B H 0.1687 1.0608 0.8511 0.070 Uiso 1 1 calc R . . C13 C 0.4041(9) 1.0526(6) 0.6446(5) 0.0630(16) Uani 1 1 d . . . H13A H 0.3238 1.0764 0.5986 0.076 Uiso 1 1 calc R . . H13B H 0.4730 1.1043 0.6250 0.076 Uiso 1 1 calc R . . C14 C 0.4756(7) 0.9285(6) 0.6246(4) 0.0525(14) Uani 1 1 d . . . C19 C 0.6884(8) 0.7767(7) 0.6223(5) 0.0695(19) Uani 1 1 d . . . H19 H 0.7857 0.7514 0.6356 0.083 Uiso 1 1 calc R . . C17 C 0.6110(8) 0.6996(6) 0.5853(5) 0.0633(16) Uani 1 1 d . . . C18 C 0.8243(13) 0.5451(11) 0.5713(14) 0.142(6) Uani 1 1 d . . . H18A H 0.8513 0.4639 0.5542 0.212 Uiso 1 1 calc R . . H18B H 0.8494 0.5520 0.6425 0.212 Uiso 1 1 calc R . . H18C H 0.8747 0.5935 0.5227 0.212 Uiso 1 1 calc R . . C16 C 0.4662(8) 0.7363(6) 0.5688(5) 0.0639(16) Uani 1 1 d . . . H16 H 0.4139 0.6842 0.5444 0.077 Uiso 1 1 calc R . . C15 C 0.3986(7) 0.8492(6) 0.5882(4) 0.0537(14) Uani 1 1 d . . . H15 H 0.3005 0.8733 0.5769 0.064 Uiso 1 1 calc R . . C6 C 0.3190(7) 1.1989(5) 0.7748(5) 0.0581(15) Uani 1 1 d . . . H6A H 0.2601 1.2146 0.8398 0.070 Uiso 1 1 calc R . . H6B H 0.2684 1.2438 0.7159 0.070 Uiso 1 1 calc R . . N2 N 0.4628(6) 1.2319(4) 0.7816(4) 0.0577(13) Uani 1 1 d . . . C1 C 0.6810(9) 1.2064(6) 0.8337(6) 0.0691(19) Uani 1 1 d . . . C4 C 0.5055(10) 1.3350(6) 0.7550(6) 0.071(2) Uani 1 1 d . . . C5 C 0.4100(13) 1.4388(7) 0.7011(8) 0.094(3) Uani 1 1 d . . . H5A H 0.3194 1.4175 0.6885 0.141 Uiso 1 1 calc R . . H5B H 0.4564 1.4612 0.6347 0.141 Uiso 1 1 calc R . . H5C H 0.3931 1.5041 0.7456 0.141 Uiso 1 1 calc R . . C2 C 0.8212(8) 1.1489(8) 0.8775(8) 0.079(2) Uani 1 1 d . . . H2A H 0.8167 1.0689 0.9033 0.119 Uiso 1 1 calc R . . H2B H 0.8409 1.1922 0.9347 0.119 Uiso 1 1 calc R . . H2C H 0.8971 1.1483 0.8227 0.119 Uiso 1 1 calc R . . C8 C 0.1971(9) 0.8054(6) 0.8245(6) 0.0699(19) Uani 1 1 d . . . C11 C 0.4197(9) 0.7426(5) 0.8879(5) 0.0635(17) Uani 1 1 d . . . C12 C 0.5536(10) 0.6688(6) 0.9269(7) 0.081(2) Uani 1 1 d . . . H12A H 0.6230 0.7181 0.9348 0.121 Uiso 1 1 calc R . . H12B H 0.5925 0.6110 0.8769 0.121 Uiso 1 1 calc R . . H12C H 0.5327 0.6293 0.9943 0.121 Uiso 1 1 calc R . . C9 C 0.0504(10) 0.8201(9) 0.7881(9) 0.094(3) Uani 1 1 d . . . H9A H 0.0168 0.9016 0.7650 0.141 Uiso 1 1 calc R . . H9B H -0.0129 0.7969 0.8453 0.141 Uiso 1 1 calc R . . H9C H 0.0508 0.7713 0.7301 0.141 Uiso 1 1 calc R . . Cl2 Cl -0.0469(4) 1.1697(3) 0.5664(2) 0.1124(9) Uani 1 1 d D . . O4 O 0.0176(13) 1.2270(9) 0.6326(9) 0.159(4) Uani 1 1 d D . . O5 O 0.0549(18) 1.0685(12) 0.5485(17) 0.336(16) Uani 1 1 d D . . O3 O -0.1670(15) 1.1301(13) 0.6119(11) 0.218(6) Uani 1 1 d D . . O2 O -0.0841(17) 1.2368(15) 0.4750(10) 0.226(7) Uani 1 1 d D . . C21B C 0.986(2) 0.6409(18) 0.2332(18) 0.079(5) Uani 0.40 1 d P A 2 H21D H 1.0782 0.6257 0.2640 0.118 Uiso 0.40 1 calc PR A 2 H21E H 0.9115 0.6326 0.2877 0.118 Uiso 0.40 1 calc PR A 2 H21F H 0.9674 0.7200 0.2003 0.118 Uiso 0.40 1 calc PR A 2 C21A C 0.8554(14) 0.5686(13) 0.1064(11) 0.080(4) Uani 0.60 1 d P A 1 H21A H 0.7798 0.5572 0.1589 0.121 Uiso 0.60 1 calc P B 1 H21B H 0.8652 0.5096 0.0557 0.121 Uiso 0.60 1 calc P C 1 H21C H 0.8314 0.6460 0.0707 0.121 Uiso 0.60 1 calc P D 1 H6 H 1.056(9) 0.502(7) 0.136(9) 0.121 Uiso 1 1 d 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 0.0653(5) 0.0351(4) 0.0449(4) -0.0019(3) 0.0079(3) -0.0106(3) Cl1 0.0665(9) 0.0537(9) 0.0570(8) -0.0021(7) 0.0025(7) -0.0059(7) N5 0.080(4) 0.034(2) 0.047(2) -0.0038(19) 0.008(2) -0.012(2) O1 0.100(4) 0.055(3) 0.112(4) -0.003(3) 0.016(3) 0.010(3) O6 0.044(2) 0.053(3) 0.175(6) -0.059(3) -0.014(3) -0.006(2) N3 0.066(3) 0.028(2) 0.044(2) -0.0026(17) 0.0062(19) -0.0136(19) C20 0.067(4) 0.078(5) 0.047(3) -0.006(3) 0.004(3) -0.023(3) N1 0.070(3) 0.043(3) 0.058(3) 0.000(2) 0.013(2) -0.017(2) C3 0.102(6) 0.052(4) 0.082(5) -0.007(3) 0.021(4) -0.035(4) C10 0.109(6) 0.045(4) 0.086(5) -0.012(3) 0.028(4) -0.032(4) N4 0.067(3) 0.046(3) 0.052(3) 0.000(2) 0.009(2) -0.016(2) C7 0.068(4) 0.049(3) 0.058(3) 0.001(3) -0.002(3) -0.012(3) C13 0.093(5) 0.050(3) 0.043(3) 0.000(3) 0.008(3) -0.010(3) C14 0.067(4) 0.053(3) 0.036(2) -0.001(2) 0.007(2) -0.013(3) C19 0.055(4) 0.087(5) 0.060(4) -0.002(3) 0.000(3) 0.002(3) C17 0.068(4) 0.054(4) 0.061(4) 0.003(3) 0.008(3) -0.002(3) C18 0.098(8) 0.086(7) 0.210(15) 0.016(8) 0.032(8) 0.033(6) C16 0.074(4) 0.058(4) 0.063(4) -0.009(3) 0.003(3) -0.020(3) C15 0.061(3) 0.051(3) 0.048(3) -0.003(3) 0.000(2) -0.007(3) C6 0.076(4) 0.040(3) 0.057(3) -0.005(3) 0.003(3) -0.010(3) N2 0.077(3) 0.040(3) 0.057(3) -0.005(2) 0.009(2) -0.017(2) C1 0.091(5) 0.057(4) 0.064(4) -0.011(3) 0.023(3) -0.032(4) C4 0.108(6) 0.037(3) 0.065(4) -0.008(3) 0.023(4) -0.014(3) C5 0.149(9) 0.040(4) 0.090(5) 0.015(4) 0.000(5) -0.021(4) C2 0.066(5) 0.068(5) 0.102(6) 0.004(4) 0.008(4) -0.018(4) C8 0.092(5) 0.052(4) 0.070(4) -0.013(3) 0.021(4) -0.030(4) C11 0.094(5) 0.035(3) 0.059(3) -0.007(3) 0.020(3) -0.012(3) C12 0.109(6) 0.041(4) 0.088(5) 0.000(3) -0.006(4) -0.008(4) C9 0.084(6) 0.084(6) 0.122(7) -0.006(5) 0.006(5) -0.039(5) Cl2 0.121(2) 0.116(2) 0.1032(18) -0.0143(16) -0.0193(15) -0.0210(18) O4 0.182(9) 0.139(8) 0.170(9) -0.033(7) -0.064(7) -0.035(7) O5 0.29(2) 0.153(12) 0.56(4) -0.014(18) -0.27(3) 0.039(13) O3 0.268(17) 0.217 0.209(13) -0.071(10) 0.075(12) -0.150(11) O2 0.244 0.271(19) 0.175(13) 0.066(12) -0.070(10) -0.089(13) C21B 0.074(11) 0.070(12) 0.098(14) -0.015(10) -0.022(10) -0.018(9) C21A 0.066(7) 0.082(9) 0.089(9) -0.032(7) -0.010(6) 0.007(6) _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 1.984(5) . ? Cu1 N1 1.999(5) . ? Cu1 N3 2.084(5) . ? Cu1 Cl1 2.2281(18) . ? N5 C11 1.353(8) . ? N5 N4 1.356(8) . ? O1 C17 1.372(9) . ? O1 C18 1.477(14) . ? O6 C21A 1.390(14) . ? O6 C21B 1.43(2) . ? O6 H6 0.87(2) . ? N3 C7 1.453(8) . ? N3 C6 1.470(7) . ? N3 C13 1.520(7) . ? C20 C19 1.360(11) . ? C20 C14 1.385(9) . ? C20 H20 0.9300 . ? N1 C1 1.347(9) . ? N1 N2 1.349(8) . ? C3 C4 1.369(13) . ? C3 C1 1.402(11) . ? C3 H3 0.9300 . ? C10 C11 1.379(12) . ? C10 C8 1.409(12) . ? C10 H10 0.9300 . ? N4 C8 1.355(9) . ? N4 C7 1.454(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C13 C14 1.494(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.394(9) . ? C19 C17 1.381(11) . ? C19 H19 0.9300 . ? C17 C16 1.374(10) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C16 C15 1.367(10) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? C6 N2 1.486(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N2 C4 1.337(9) . ? C1 C2 1.481(12) . ? C4 C5 1.496(12) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C8 C9 1.462(13) . ? C11 C12 1.470(12) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Cl2 O4 1.350(8) . ? Cl2 O2 1.364(10) . ? Cl2 O3 1.374(10) . ? Cl2 O5 1.384(12) . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 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 N5 Cu1 N1 162.5(2) . . ? N5 Cu1 N3 81.2(2) . . ? N1 Cu1 N3 81.4(2) . . ? N5 Cu1 Cl1 98.46(17) . . ? N1 Cu1 Cl1 98.79(18) . . ? N3 Cu1 Cl1 176.33(12) . . ? C11 N5 N4 106.0(6) . . ? C11 N5 Cu1 142.5(5) . . ? N4 N5 Cu1 111.4(4) . . ? C17 O1 C18 116.4(8) . . ? C21A O6 C21B 115.4(10) . . ? C21A O6 H6 117(8) . . ? C21B O6 H6 128(8) . . ? C7 N3 C6 110.6(5) . . ? C7 N3 C13 115.0(5) . . ? C6 N3 C13 109.4(4) . . ? C7 N3 Cu1 105.7(3) . . ? C6 N3 Cu1 105.0(4) . . ? C13 N3 Cu1 110.6(4) . . ? C19 C20 C14 121.5(7) . . ? C19 C20 H20 119.2 . . ? C14 C20 H20 119.2 . . ? C1 N1 N2 106.6(5) . . ? C1 N1 Cu1 141.7(5) . . ? N2 N1 Cu1 111.6(4) . . ? C4 C3 C1 107.1(7) . . ? C4 C3 H3 126.5 . . ? C1 C3 H3 126.5 . . ? C11 C10 C8 108.5(6) . . ? C11 C10 H10 125.8 . . ? C8 C10 H10 125.8 . . ? C8 N4 N5 113.1(6) . . ? C8 N4 C7 127.9(6) . . ? N5 N4 C7 119.0(5) . . ? N3 C7 N4 108.2(5) . . ? N3 C7 H7A 110.1 . . ? N4 C7 H7A 110.1 . . ? N3 C7 H7B 110.1 . . ? N4 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C14 C13 N3 114.9(5) . . ? C14 C13 H13A 108.5 . . ? N3 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? N3 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C20 C14 C15 118.0(6) . . ? C20 C14 C13 120.7(6) . . ? C15 C14 C13 121.3(6) . . ? C20 C19 C17 119.8(6) . . ? C20 C19 H19 120.1 . . ? C17 C19 H19 120.1 . . ? O1 C17 C16 114.9(7) . . ? O1 C17 C19 125.2(7) . . ? C16 C17 C19 119.8(6) . . ? O1 C18 H18A 109.5 . . ? O1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C16 C17 120.3(7) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C15 C14 120.6(6) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? N3 C6 N2 106.2(5) . . ? N3 C6 H6A 110.5 . . ? N2 C6 H6A 110.5 . . ? N3 C6 H6B 110.5 . . ? N2 C6 H6B 110.5 . . ? H6A C6 H6B 108.7 . . ? C4 N2 N1 111.7(6) . . ? C4 N2 C6 130.0(6) . . ? N1 N2 C6 118.0(5) . . ? N1 C1 C3 108.1(7) . . ? N1 C1 C2 124.4(7) . . ? C3 C1 C2 127.5(7) . . ? N2 C4 C3 106.5(7) . . ? N2 C4 C5 122.6(9) . . ? C3 C4 C5 130.9(8) . . ? 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 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N4 C8 C10 103.5(7) . . ? N4 C8 C9 123.8(8) . . ? C10 C8 C9 132.7(7) . . ? N5 C11 C10 108.8(7) . . ? N5 C11 C12 123.4(7) . . ? C10 C11 C12 127.7(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 Cl2 O2 112.5(8) . . ? O4 Cl2 O3 113.6(8) . . ? O2 Cl2 O3 108.8(10) . . ? O4 Cl2 O5 103.6(8) . . ? O2 Cl2 O5 112.8(12) . . ? O3 Cl2 O5 105.4(10) . . ? O6 C21B H21D 109.5 . . ? O6 C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? O6 C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? O6 C21A H21A 109.5 . . ? O6 C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? O6 C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.988 _refine_diff_density_min -1.019 _refine_diff_density_rms 0.122