# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_e2225a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H26 N4 O4' _chemical_formula_sum 'C32 H26 N4 O4' _chemical_formula_weight 530.57 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.1611(17) _cell_length_b 21.520(7) _cell_length_c 12.209(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.474(6) _cell_angle_gamma 90.00 _cell_volume 1328.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2132 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 28.20 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9938 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11214 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.1166 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.81 _reflns_number_total 6034 _reflns_number_gt 3195 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0810P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration syn _refine_ls_number_reflns 6034 _refine_ls_number_parameters 365 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1445 _refine_ls_R_factor_gt 0.0791 _refine_ls_wR_factor_ref 0.2020 _refine_ls_wR_factor_gt 0.1813 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.0537(8) -0.1017(2) 1.0491(4) 0.0417(12) Uani 1 1 d . . . C2 C -0.0400(12) -0.1615(3) 1.0319(5) 0.0640(16) Uani 1 1 d . . . H2 H -0.0001 -0.1860 0.9726 0.077 Uiso 1 1 calc R . . C3 C -0.1951(12) -0.1854(3) 1.1036(6) 0.0642(17) Uani 1 1 d . . . H3 H -0.2485 -0.2276 1.0935 0.077 Uiso 1 1 calc R . . N1 N -0.2715(9) -0.1553(2) 1.1818(5) 0.0651(14) Uani 1 1 d . . . C4 C -0.1829(11) -0.0967(3) 1.1991(5) 0.0566(14) Uani 1 1 d . . . H4 H -0.2369 -0.0733 1.2567 0.068 Uiso 1 1 calc R . . C5 C -0.0169(9) -0.0683(2) 1.1375(4) 0.0432(12) Uani 1 1 d . . . H5 H 0.0473 -0.0274 1.1548 0.052 Uiso 1 1 calc R . . C6 C 0.2233(8) -0.0713(2) 0.9843(4) 0.0439(13) Uani 1 1 d . . . C7 C 0.3664(8) -0.0408(2) 0.9400(4) 0.0424(13) Uani 1 1 d . . . C8 C 0.5495(8) -0.0021(2) 0.9004(4) 0.0398(12) Uani 1 1 d . . . C9 C 0.6654(8) 0.0493(2) 0.9633(4) 0.0375(11) Uani 1 1 d . . . C10 C 0.6197(8) 0.0733(2) 1.0717(4) 0.0438(13) Uani 1 1 d . . . O1 O 0.4675(6) 0.05319(18) 1.1282(3) 0.0527(9) Uani 1 1 d . . . N2 N 0.7844(8) 0.1237(2) 1.0990(3) 0.0448(10) Uani 1 1 d . . . C11 C 0.9373(9) 0.1345(2) 1.0187(4) 0.0435(12) Uani 1 1 d . . . O2 O 1.0994(7) 0.17511(17) 1.0214(3) 0.0571(10) Uani 1 1 d . . . C12 C 0.8531(8) 0.0872(2) 0.9298(4) 0.0408(12) Uani 1 1 d . . . C13 C 0.8063(11) 0.1558(2) 1.2078(5) 0.0597(16) Uani 1 1 d D . . H13 H 0.6440 0.1451 1.2370 0.072 Uiso 1 1 calc R . . C14 C 0.8183(16) 0.2257(3) 1.2021(7) 0.115(3) Uani 1 1 d D . . H14A H 0.8662 0.2411 1.2800 0.138 Uiso 1 1 calc R . . H14B H 0.9670 0.2364 1.1654 0.138 Uiso 1 1 calc R . . C15 C 0.5969(17) 0.2604(5) 1.1482(14) 0.115(3) Uani 1 1 d D . . H15A H 0.4836 0.2341 1.0929 0.138 Uiso 1 1 calc R . . H15B H 0.6568 0.2963 1.1107 0.138 Uiso 1 1 calc R . . H15C H 0.4967 0.2747 1.2037 0.138 Uiso 1 1 calc R . . C16 C 1.0412(12) 0.1311(4) 1.2918(5) 0.086(2) Uani 1 1 d . . . H16A H 1.0182 0.0865 1.3028 0.128 Uiso 1 1 calc R . . H16B H 1.0530 0.1529 1.3631 0.128 Uiso 1 1 calc R . . H16C H 1.2038 0.1381 1.2636 0.128 Uiso 1 1 calc R . . C17 C 0.9408(8) 0.0781(2) 0.8276(4) 0.0376(11) Uani 1 1 d . . . C18 C 0.8264(8) 0.0268(2) 0.7665(4) 0.0366(11) Uani 1 1 d . . . C19 C 0.8865(10) 0.0013(2) 0.6590(4) 0.0473(13) Uani 1 1 d . . . O3 O 1.0385(7) 0.01933(17) 0.6050(3) 0.0617(11) Uani 1 1 d . . . N3 N 0.7219(8) -0.0512(2) 0.6332(3) 0.0526(12) Uani 1 1 d . . . C20 C 0.5653(9) -0.0611(3) 0.7133(4) 0.0473(13) Uani 1 1 d . . . O4 O 0.3994(7) -0.10067(19) 0.7107(3) 0.0640(11) Uani 1 1 d . . . C21 C 0.6410(8) -0.0115(2) 0.8006(4) 0.0413(12) Uani 1 1 d . . . C22 C 0.7295(10) -0.0921(3) 0.5351(5) 0.0604(16) Uani 1 1 d . . . H22 H 0.8759 -0.0767 0.4995 0.072 Uiso 1 1 calc R . . C23 C 0.4763(11) -0.0848(3) 0.4505(5) 0.0652(16) Uani 1 1 d . . . H23A H 0.3280 -0.0994 0.4843 0.078 Uiso 1 1 calc R . . H23B H 0.4840 -0.1120 0.3858 0.078 Uiso 1 1 calc R . . C24 C 0.4187(13) -0.0191(3) 0.4088(5) 0.0746(18) Uani 1 1 d . . . H24A H 0.3861 0.0072 0.4703 0.112 Uiso 1 1 calc R . . H24B H 0.2620 -0.0189 0.3484 0.112 Uiso 1 1 calc R . . H24C H 0.5706 -0.0028 0.3808 0.112 Uiso 1 1 calc R . . C25 C 0.7955(11) -0.1592(3) 0.5717(6) 0.0741(18) Uani 1 1 d . . . H25A H 0.9696 -0.1606 0.6215 0.111 Uiso 1 1 calc R . . H25B H 0.7978 -0.1850 0.5057 0.111 Uiso 1 1 calc R . . H25C H 0.6616 -0.1750 0.6113 0.111 Uiso 1 1 calc R . . C26 C 1.1306(8) 0.1174(2) 0.7889(4) 0.0376(11) Uani 1 1 d . . . C27 C 1.2774(8) 0.1453(2) 0.7446(4) 0.0365(11) Uani 1 1 d . . . C28 C 1.4506(8) 0.1732(2) 0.6798(4) 0.0311(10) Uani 1 1 d . . . C29 C 1.4768(11) 0.1438(3) 0.5833(4) 0.0570(15) Uani 1 1 d . . . H29 H 1.3781 0.1071 0.5605 0.068 Uiso 1 1 calc R . . C30 C 1.6458(11) 0.1671(3) 0.5191(5) 0.0690(17) Uani 1 1 d . . . H30 H 1.6612 0.1449 0.4535 0.083 Uiso 1 1 calc R . . N4 N 1.7877(8) 0.2181(2) 0.5425(4) 0.0580(12) Uani 1 1 d . . . C31 C 1.7597(10) 0.2483(3) 0.6360(5) 0.0554(15) Uani 1 1 d . . . H31 H 1.8544 0.2860 0.6547 0.067 Uiso 1 1 calc R . . C32 C 1.5948(10) 0.2264(2) 0.7077(5) 0.0492(13) Uani 1 1 d . . . H32 H 1.5843 0.2482 0.7743 0.059 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 C1 0.031(2) 0.048(3) 0.047(3) 0.005(2) 0.008(2) 0.004(2) C2 0.084(4) 0.050(3) 0.071(4) -0.013(3) 0.045(3) -0.011(3) C3 0.075(4) 0.043(3) 0.086(5) 0.003(3) 0.045(4) -0.010(3) N1 0.065(3) 0.054(3) 0.090(4) 0.016(3) 0.048(3) -0.002(2) C4 0.073(4) 0.049(3) 0.056(3) 0.010(3) 0.031(3) -0.001(3) C5 0.050(3) 0.042(3) 0.043(3) 0.006(2) 0.021(2) -0.005(2) C6 0.028(2) 0.063(3) 0.044(3) 0.010(3) 0.014(2) -0.003(2) C7 0.029(2) 0.061(3) 0.037(3) 0.012(2) 0.004(2) -0.001(2) C8 0.026(2) 0.063(3) 0.031(3) 0.018(2) 0.0068(19) -0.001(2) C9 0.025(2) 0.062(3) 0.025(2) 0.016(2) 0.0060(19) 0.007(2) C10 0.027(2) 0.065(4) 0.042(3) 0.019(3) 0.013(2) 0.006(2) O1 0.0466(19) 0.067(2) 0.050(2) 0.0121(18) 0.0243(17) -0.0051(18) N2 0.034(2) 0.063(3) 0.042(3) 0.010(2) 0.0197(19) -0.002(2) C11 0.029(2) 0.051(3) 0.050(3) 0.010(3) 0.007(2) 0.001(2) O2 0.053(2) 0.067(3) 0.059(2) -0.003(2) 0.0285(18) -0.013(2) C12 0.026(2) 0.055(3) 0.040(3) 0.013(2) 0.005(2) 0.003(2) C13 0.062(3) 0.063(4) 0.068(4) 0.001(3) 0.048(3) -0.002(3) C14 0.136(7) 0.079(5) 0.171(9) -0.027(5) 0.128(7) -0.028(5) C15 0.136(7) 0.079(5) 0.171(9) -0.027(5) 0.128(7) -0.028(5) C16 0.053(3) 0.150(7) 0.056(4) -0.030(4) 0.016(3) -0.002(4) C17 0.025(2) 0.052(3) 0.035(3) 0.014(2) 0.004(2) 0.005(2) C18 0.026(2) 0.058(3) 0.030(3) 0.015(2) 0.0147(19) 0.005(2) C19 0.040(3) 0.053(3) 0.048(3) 0.005(3) 0.009(2) -0.005(2) O3 0.064(2) 0.068(3) 0.067(3) 0.002(2) 0.048(2) -0.011(2) N3 0.049(2) 0.073(3) 0.041(3) -0.004(2) 0.020(2) -0.010(2) C20 0.033(3) 0.067(3) 0.041(3) 0.014(3) 0.007(2) -0.010(3) O4 0.056(2) 0.085(3) 0.051(2) 0.006(2) 0.0094(19) -0.022(2) C21 0.024(2) 0.062(3) 0.036(3) 0.010(2) 0.0025(19) -0.005(2) C22 0.040(3) 0.077(4) 0.071(4) -0.001(3) 0.027(3) -0.012(3) C23 0.052(3) 0.088(5) 0.061(4) -0.008(3) 0.024(3) -0.010(3) C24 0.094(5) 0.087(5) 0.044(3) -0.011(3) 0.017(3) 0.020(4) C25 0.048(3) 0.069(4) 0.106(5) -0.007(4) 0.018(3) 0.002(3) C26 0.027(2) 0.051(3) 0.038(3) 0.011(2) 0.014(2) 0.000(2) C27 0.034(2) 0.034(3) 0.043(3) 0.006(2) 0.010(2) 0.007(2) C28 0.026(2) 0.040(3) 0.031(3) 0.001(2) 0.0145(18) 0.003(2) C29 0.059(3) 0.066(4) 0.050(3) -0.004(3) 0.023(3) -0.019(3) C30 0.060(4) 0.104(5) 0.049(4) -0.009(4) 0.027(3) -0.016(4) N4 0.053(3) 0.079(3) 0.048(3) 0.007(3) 0.025(2) -0.004(3) C31 0.045(3) 0.044(3) 0.084(4) 0.012(3) 0.027(3) -0.002(2) C32 0.047(3) 0.042(3) 0.063(4) -0.005(3) 0.022(3) -0.003(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 C1 C2 1.377(7) . ? C1 C5 1.404(6) . ? C1 C6 1.448(6) . ? C2 C3 1.396(8) . ? C2 H2 0.9500 . ? C3 N1 1.279(8) . ? C3 H3 0.9500 . ? N1 C4 1.345(7) . ? C4 C5 1.388(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.195(6) . ? C7 C8 1.415(6) . ? C8 C21 1.407(6) . ? C8 C9 1.411(7) . ? C9 C12 1.388(6) . ? C9 C10 1.483(7) . ? C10 O1 1.223(5) . ? C10 N2 1.377(6) . ? N2 C11 1.396(6) . ? N2 C13 1.482(7) . ? C11 O2 1.205(6) . ? C11 C12 1.488(7) . ? C12 C17 1.423(6) . ? C13 C14 1.507(7) . ? C13 C16 1.519(8) . ? C13 H13 1.0000 . ? C14 C15 1.412(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.395(7) . ? C17 C26 1.443(6) . ? C18 C21 1.388(6) . ? C18 C19 1.512(7) . ? C19 O3 1.186(5) . ? C19 N3 1.411(6) . ? N3 C20 1.404(6) . ? N3 C22 1.492(7) . ? C20 O4 1.204(6) . ? C20 C21 1.504(7) . ? C22 C23 1.504(8) . ? C22 C25 1.530(9) . ? C22 H22 1.0000 . ? C23 C24 1.514(8) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.179(6) . ? C27 C28 1.438(6) . ? C28 C29 1.368(6) . ? C28 C32 1.370(7) . ? C29 C30 1.378(7) . ? C29 H29 0.9500 . ? C30 N4 1.319(8) . ? C30 H30 0.9500 . ? N4 C31 1.347(7) . ? C31 C32 1.418(7) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 C5 117.3(5) . . ? C2 C1 C6 124.9(5) . . ? C5 C1 C6 117.8(5) . . ? C1 C2 C3 118.4(5) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? N1 C3 C2 125.6(5) . . ? N1 C3 H3 117.2 . . ? C2 C3 H3 117.2 . . ? C3 N1 C4 116.5(5) . . ? N1 C4 C5 123.7(5) . . ? N1 C4 H4 118.2 . . ? C5 C4 H4 118.2 . . ? C4 C5 C1 118.3(5) . . ? C4 C5 H5 120.9 . . ? C1 C5 H5 120.9 . . ? C7 C6 C1 172.4(6) . . ? C6 C7 C8 173.2(5) . . ? C21 C8 C9 113.9(4) . . ? C21 C8 C7 125.0(5) . . ? C9 C8 C7 121.0(4) . . ? C12 C9 C8 123.1(4) . . ? C12 C9 C10 107.6(4) . . ? C8 C9 C10 129.3(4) . . ? O1 C10 N2 125.3(5) . . ? O1 C10 C9 127.9(5) . . ? N2 C10 C9 106.8(4) . . ? C10 N2 C11 111.7(4) . . ? C10 N2 C13 121.2(4) . . ? C11 N2 C13 126.8(4) . . ? O2 C11 N2 126.0(5) . . ? O2 C11 C12 128.0(5) . . ? N2 C11 C12 105.9(4) . . ? C9 C12 C17 122.6(5) . . ? C9 C12 C11 107.9(4) . . ? C17 C12 C11 129.5(4) . . ? N2 C13 C14 114.9(5) . . ? N2 C13 C16 110.5(4) . . ? C14 C13 C16 110.2(6) . . ? N2 C13 H13 106.9 . . ? C14 C13 H13 106.9 . . ? C16 C13 H13 106.9 . . ? C15 C14 C13 120.7(8) . . ? C15 C14 H14A 107.1 . . ? C13 C14 H14A 107.1 . . ? C15 C14 H14B 107.1 . . ? C13 C14 H14B 107.1 . . ? H14A C14 H14B 106.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C12 113.8(4) . . ? C18 C17 C26 122.1(4) . . ? C12 C17 C26 124.1(4) . . ? C21 C18 C17 123.6(4) . . ? C21 C18 C19 108.5(4) . . ? C17 C18 C19 127.9(4) . . ? O3 C19 N3 125.0(5) . . ? O3 C19 C18 129.5(5) . . ? N3 C19 C18 105.5(4) . . ? C20 N3 C19 111.7(4) . . ? C20 N3 C22 125.5(4) . . ? C19 N3 C22 122.7(4) . . ? O4 C20 N3 126.4(5) . . ? O4 C20 C21 127.2(5) . . ? N3 C20 C21 106.4(4) . . ? C18 C21 C8 123.0(5) . . ? C18 C21 C20 107.9(4) . . ? C8 C21 C20 129.2(4) . . ? N3 C22 C23 109.4(5) . . ? N3 C22 C25 111.2(5) . . ? C23 C22 C25 114.3(5) . . ? N3 C22 H22 107.2 . . ? C23 C22 H22 107.2 . . ? C25 C22 H22 107.2 . . ? C22 C23 C24 114.4(5) . . ? C22 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? C22 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C17 171.4(5) . . ? C26 C27 C28 172.6(5) . . ? C29 C28 C32 117.4(4) . . ? C29 C28 C27 117.4(4) . . ? C32 C28 C27 125.3(4) . . ? C28 C29 C30 120.2(5) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? N4 C30 C29 124.5(5) . . ? N4 C30 H30 117.7 . . ? C29 C30 H30 117.7 . . ? C30 N4 C31 116.0(4) . . ? N4 C31 C32 122.7(5) . . ? N4 C31 H31 118.6 . . ? C32 C31 H31 118.6 . . ? C28 C32 C31 119.2(5) . . ? C28 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.81 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.230 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 959987' ####################################################################### # # 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_e2220a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H26 Cl2 Hg N4 O4' _chemical_formula_sum 'C32 H26 Cl2 Hg N4 O4' _chemical_formula_weight 802.06 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 21.6201(6) _cell_length_b 29.5433(9) _cell_length_c 5.0964(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3255.22(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7451 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 23.11 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 4.933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7562 _exptl_absorpt_correction_T_max 0.9078 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49104 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.52 _reflns_number_total 7416 _reflns_number_gt 6040 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+14.7050P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.037(13) _chemical_absolute_configuration rm _refine_ls_number_reflns 7416 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg1 Hg 0.242702(18) -0.121593(9) 1.52515(6) 0.03744(13) Uani 1 1 d . . . Cl1 Cl 0.34862(15) -0.11921(10) 1.6239(6) 0.0594(8) Uani 1 1 d . . . Cl2 Cl 0.13643(14) -0.12427(9) 1.6093(5) 0.0528(7) Uani 1 1 d . . . N1 N 0.2431(4) -0.0600(2) 1.2029(14) 0.039(2) Uani 1 1 d . . . C1 C 0.2951(5) -0.0438(4) 1.116(2) 0.041(3) Uani 1 1 d . . . H1 H 0.3331 -0.0543 1.1872 0.050 Uiso 1 1 calc R . . C2 C 0.2958(5) -0.0112(4) 0.919(2) 0.045(3) Uani 1 1 d . . . H2 H 0.3342 0.0005 0.8603 0.054 Uiso 1 1 calc R . . C3 C 0.2423(5) 0.0042(3) 0.8096(16) 0.037(2) Uani 1 1 d . . . C4 C 0.1871(6) -0.0125(3) 0.902(2) 0.044(3) Uani 1 1 d . . . H4 H 0.1488 -0.0025 0.8312 0.053 Uiso 1 1 calc R . . C5 C 0.1890(5) -0.0449(4) 1.104(2) 0.045(3) Uani 1 1 d . . . H5 H 0.1512 -0.0564 1.1720 0.054 Uiso 1 1 calc R . . C6 C 0.2415(6) 0.0374(3) 0.6032(16) 0.043(3) Uani 1 1 d . . . C7 C 0.2413(5) 0.0649(3) 0.4368(17) 0.036(2) Uani 1 1 d . . . C8 C 0.2421(5) 0.0983(3) 0.2278(15) 0.035(2) Uani 1 1 d . . . C9 C 0.2957(5) 0.1194(3) 0.1477(18) 0.039(2) Uani 1 1 d . . . C10 C 0.2960(5) 0.1509(3) -0.064(2) 0.040(2) Uani 1 1 d . . . C11 C 0.2432(5) 0.1627(3) -0.2022(16) 0.039(2) Uani 1 1 d . . . C12 C 0.1893(5) 0.1417(3) -0.1188(16) 0.031(2) Uani 1 1 d . . . C13 C 0.1874(5) 0.1106(3) 0.0921(17) 0.035(2) Uani 1 1 d . . . C14 C 0.3594(5) 0.1174(3) 0.254(2) 0.044(2) Uani 1 1 d . . . O1 O 0.3780(3) 0.0945(2) 0.4358(16) 0.0550(19) Uani 1 1 d . . . N2 N 0.3953(4) 0.1467(3) 0.1054(17) 0.048(2) Uani 1 1 d . . . C15 C 0.3612(5) 0.1674(3) -0.096(2) 0.046(3) Uani 1 1 d . . . O2 O 0.3810(4) 0.1926(2) -0.2554(15) 0.058(2) Uani 1 1 d . . . C16 C 0.4619(6) 0.1544(5) 0.152(3) 0.071(4) Uani 1 1 d . . . H16 H 0.4721 0.1375 0.3168 0.086 Uiso 1 1 calc R . . C17 C 0.4735(5) 0.2044(4) 0.213(3) 0.060(3) Uani 1 1 d . . . H17A H 0.4625 0.2231 0.0590 0.072 Uiso 1 1 calc R . . H17B H 0.4475 0.2140 0.3629 0.072 Uiso 1 1 calc R . . C18 C 0.5389(7) 0.2103(7) 0.277(4) 0.132(9) Uani 1 1 d . . . H18A H 0.5537 0.1839 0.3754 0.198 Uiso 1 1 calc R . . H18B H 0.5441 0.2376 0.3843 0.198 Uiso 1 1 calc R . . H18C H 0.5629 0.2134 0.1149 0.198 Uiso 1 1 calc R . . C19 C 0.5021(9) 0.1354(6) -0.053(4) 0.126(7) Uani 1 1 d . . . H19A H 0.4880 0.1048 -0.0977 0.189 Uiso 1 1 calc R . . H19B H 0.5448 0.1340 0.0116 0.189 Uiso 1 1 calc R . . H19C H 0.5003 0.1546 -0.2094 0.189 Uiso 1 1 calc R . . C20 C 0.1238(5) 0.0953(3) 0.127(2) 0.042(3) Uani 1 1 d . . . O3 O 0.1043(4) 0.0681(2) 0.2840(14) 0.0477(19) Uani 1 1 d . . . N3 N 0.0889(4) 0.1171(3) -0.0740(15) 0.0395(18) Uani 1 1 d . . . C21 C 0.1260(5) 0.1446(3) -0.2241(19) 0.040(3) Uani 1 1 d . . . O4 O 0.1073(4) 0.1671(2) -0.4044(13) 0.052(2) Uani 1 1 d . . . C22 C 0.0238(6) 0.1108(3) -0.1147(19) 0.044(3) Uani 1 1 d . . . H22 H 0.0122 0.1281 -0.2760 0.053 Uiso 1 1 calc R . . C23 C -0.0158(6) 0.1292(3) 0.113(2) 0.051(3) Uani 1 1 d . . . H23A H -0.0599 0.1223 0.0795 0.061 Uiso 1 1 calc R . . H23B H -0.0036 0.1140 0.2782 0.061 Uiso 1 1 calc R . . C24 C -0.0076(6) 0.1788(4) 0.140(3) 0.066(4) Uani 1 1 d . . . H24A H 0.0366 0.1861 0.1384 0.099 Uiso 1 1 calc R . . H24B H -0.0259 0.1889 0.3058 0.099 Uiso 1 1 calc R . . H24C H -0.0281 0.1942 -0.0066 0.099 Uiso 1 1 calc R . . C25 C 0.0072(6) 0.0590(4) -0.167(3) 0.063(3) Uani 1 1 d . . . H25A H 0.0324 0.0475 -0.3121 0.094 Uiso 1 1 calc R . . H25B H -0.0367 0.0564 -0.2113 0.094 Uiso 1 1 calc R . . H25C H 0.0158 0.0413 -0.0081 0.094 Uiso 1 1 calc R . . C26 C 0.2455(5) 0.1953(3) -0.4091(16) 0.037(2) Uani 1 1 d . . . C27 C 0.2482(5) 0.2222(3) -0.5814(17) 0.039(2) Uani 1 1 d . . . C28 C 0.2493(5) 0.2551(2) -0.7892(15) 0.033(2) Uani 1 1 d . . . C29 C 0.3053(5) 0.2715(4) -0.881(2) 0.042(3) Uani 1 1 d . . . H29 H 0.3430 0.2612 -0.8060 0.050 Uiso 1 1 calc R . . C30 C 0.3058(5) 0.3031(3) -1.084(2) 0.037(3) Uani 1 1 d . . . H30 H 0.3447 0.3141 -1.1440 0.044 Uiso 1 1 calc R . . N4 N 0.2566(4) 0.3182(2) -1.1945(13) 0.0337(18) Uani 1 1 d . . . C31 C 0.2025(5) 0.3015(4) -1.101(2) 0.040(3) Uani 1 1 d . . . H31 H 0.1655 0.3120 -1.1805 0.048 Uiso 1 1 calc R . . C32 C 0.1966(5) 0.2712(3) -0.904(2) 0.043(3) Uani 1 1 d . . . H32 H 0.1570 0.2614 -0.8464 0.052 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 Hg1 0.0699(3) 0.02107(14) 0.02140(15) -0.00233(12) -0.00431(16) 0.00625(15) Cl1 0.081(2) 0.0398(14) 0.0570(18) -0.0074(14) -0.0294(14) 0.0082(14) Cl2 0.0766(19) 0.0437(15) 0.0379(14) -0.0002(12) 0.0086(12) 0.0026(13) N1 0.062(6) 0.026(4) 0.031(4) 0.002(3) -0.011(5) 0.018(4) C1 0.049(7) 0.033(6) 0.041(8) 0.007(5) -0.002(5) 0.005(5) C2 0.042(6) 0.050(6) 0.042(7) 0.004(5) 0.006(5) 0.004(5) C3 0.070(7) 0.017(4) 0.023(4) 0.000(3) 0.010(5) -0.001(5) C4 0.072(8) 0.024(5) 0.036(7) 0.011(4) -0.013(6) 0.003(5) C5 0.055(7) 0.036(6) 0.043(8) 0.004(5) -0.007(6) -0.005(5) C6 0.077(8) 0.025(4) 0.025(4) 0.002(3) 0.013(5) 0.010(5) C7 0.063(6) 0.027(4) 0.018(3) 0.003(3) 0.005(5) 0.005(4) C8 0.069(7) 0.017(4) 0.017(3) -0.001(3) 0.007(5) 0.003(4) C9 0.063(7) 0.024(4) 0.030(5) 0.001(4) 0.014(4) 0.014(5) C10 0.076(7) 0.023(4) 0.021(5) -0.002(4) 0.018(5) 0.011(4) C11 0.072(8) 0.023(4) 0.021(4) -0.003(3) 0.011(5) 0.011(5) C12 0.064(7) 0.012(4) 0.018(4) -0.004(3) 0.007(4) 0.003(4) C13 0.065(7) 0.022(5) 0.017(4) -0.003(3) 0.003(4) 0.003(4) C14 0.066(7) 0.027(5) 0.038(5) 0.002(5) 0.013(5) 0.005(5) O1 0.066(5) 0.050(4) 0.049(4) 0.028(4) 0.002(4) 0.010(3) N2 0.067(7) 0.040(5) 0.037(5) 0.018(4) 0.008(4) 0.010(4) C15 0.070(8) 0.033(5) 0.036(6) 0.005(4) 0.015(5) 0.017(5) O2 0.090(6) 0.044(4) 0.039(4) 0.024(4) 0.019(4) 0.007(4) C16 0.068(9) 0.073(9) 0.073(9) 0.039(7) 0.022(7) 0.029(7) C17 0.053(8) 0.063(8) 0.063(8) 0.026(7) 0.002(6) -0.007(6) C18 0.071(12) 0.18(2) 0.142(18) 0.083(16) -0.024(12) -0.020(12) C19 0.139(16) 0.113(14) 0.126(17) -0.001(14) 0.057(14) 0.039(12) C20 0.071(8) 0.026(5) 0.030(5) 0.003(4) 0.000(5) 0.001(5) O3 0.070(5) 0.040(4) 0.033(4) 0.012(3) 0.007(4) -0.003(4) N3 0.063(5) 0.033(4) 0.023(4) -0.001(4) -0.002(4) -0.003(4) C21 0.069(8) 0.023(5) 0.028(5) 0.001(4) -0.002(5) -0.002(4) O4 0.089(6) 0.037(4) 0.028(4) 0.007(3) -0.015(4) 0.002(4) C22 0.075(8) 0.029(5) 0.029(5) -0.002(4) -0.007(5) 0.000(5) C23 0.075(8) 0.041(6) 0.035(6) 0.004(4) -0.006(5) 0.001(5) C24 0.098(10) 0.041(7) 0.060(8) -0.013(6) -0.007(7) 0.013(6) C25 0.081(9) 0.044(7) 0.063(8) -0.007(6) 0.002(7) -0.007(6) C26 0.062(7) 0.026(4) 0.025(4) -0.001(3) 0.004(5) 0.000(5) C27 0.064(7) 0.026(4) 0.027(4) 0.001(3) -0.001(5) -0.003(5) C28 0.058(7) 0.018(4) 0.023(4) 0.004(3) -0.004(5) 0.003(4) C29 0.050(7) 0.042(6) 0.033(6) 0.008(5) -0.007(5) 0.008(5) C30 0.046(6) 0.031(5) 0.033(7) 0.000(4) -0.002(5) 0.001(4) N4 0.052(5) 0.023(3) 0.026(3) 0.008(3) -0.002(4) -0.005(4) C31 0.040(6) 0.039(6) 0.040(7) 0.019(5) -0.012(5) -0.001(4) C32 0.054(7) 0.029(5) 0.047(8) 0.005(5) 0.007(6) -0.013(5) _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 Hg1 Cl2 2.339(3) . ? Hg1 Cl1 2.346(3) . ? Hg1 N4 2.450(6) 3_545 ? Hg1 N1 2.451(7) . ? N1 C1 1.300(13) . ? N1 C5 1.351(13) . ? C1 C2 1.389(14) . ? C1 H1 0.9500 . ? C2 C3 1.363(14) . ? C2 H2 0.9500 . ? C3 C4 1.373(15) . ? C3 C6 1.438(11) . ? C4 C5 1.404(13) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.175(12) . ? C7 C8 1.452(11) . ? C8 C9 1.377(14) . ? C8 C13 1.418(13) . ? C9 C10 1.426(13) . ? C9 C14 1.480(15) . ? C10 C11 1.385(14) . ? C10 C15 1.500(15) . ? C11 C12 1.388(14) . ? C11 C26 1.429(11) . ? C12 C13 1.413(12) . ? C12 C21 1.473(14) . ? C13 C20 1.458(15) . ? C14 O1 1.216(12) . ? C14 N2 1.387(13) . ? N2 C15 1.402(13) . ? N2 C16 1.477(16) . ? C15 O2 1.184(12) . ? C16 C19 1.47(2) . ? C16 C17 1.529(18) . ? C16 H16 1.0000 . ? C17 C18 1.463(18) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O3 1.211(12) . ? C20 N3 1.423(12) . ? N3 C21 1.375(12) . ? N3 C22 1.435(14) . ? C21 O4 1.204(11) . ? C22 C23 1.540(15) . ? C22 C25 1.593(14) . ? C22 H22 1.0000 . ? C23 C24 1.483(14) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.187(12) . ? C27 C28 1.438(11) . ? C28 C32 1.365(14) . ? C28 C29 1.384(14) . ? C29 C30 1.396(13) . ? C29 H29 0.9500 . ? C30 N4 1.284(12) . ? C30 H30 0.9500 . ? N4 C31 1.358(12) . ? N4 Hg1 2.450(6) 3 ? C31 C32 1.350(13) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 Cl2 Hg1 Cl1 157.05(10) . . ? Cl2 Hg1 N4 96.2(2) . 3_545 ? Cl1 Hg1 N4 99.4(2) . 3_545 ? Cl2 Hg1 N1 98.7(2) . . ? Cl1 Hg1 N1 96.8(2) . . ? N4 Hg1 N1 94.5(2) 3_545 . ? C1 N1 C5 120.0(8) . . ? C1 N1 Hg1 120.3(6) . . ? C5 N1 Hg1 119.6(7) . . ? N1 C1 C2 120.7(10) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 121.2(10) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 118.5(8) . . ? C2 C3 C6 122.5(10) . . ? C4 C3 C6 119.0(10) . . ? C3 C4 C5 118.1(10) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? N1 C5 C4 121.6(10) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C3 179.1(12) . . ? C6 C7 C8 178.7(11) . . ? C9 C8 C13 116.2(7) . . ? C9 C8 C7 122.3(9) . . ? C13 C8 C7 121.5(9) . . ? C8 C9 C10 121.6(9) . . ? C8 C9 C14 131.0(9) . . ? C10 C9 C14 107.3(9) . . ? C11 C10 C9 123.0(9) . . ? C11 C10 C15 129.6(9) . . ? C9 C10 C15 107.4(9) . . ? C10 C11 C12 115.1(8) . . ? C10 C11 C26 121.0(10) . . ? C12 C11 C26 123.8(10) . . ? C11 C12 C13 123.2(9) . . ? C11 C12 C21 130.0(8) . . ? C13 C12 C21 106.8(8) . . ? C12 C13 C8 120.8(9) . . ? C12 C13 C20 108.8(8) . . ? C8 C13 C20 130.4(8) . . ? O1 C14 N2 125.2(11) . . ? O1 C14 C9 127.5(10) . . ? N2 C14 C9 107.2(9) . . ? C14 N2 C15 112.2(10) . . ? C14 N2 C16 123.6(9) . . ? C15 N2 C16 124.2(9) . . ? O2 C15 N2 126.0(11) . . ? O2 C15 C10 128.2(11) . . ? N2 C15 C10 105.8(8) . . ? C19 C16 N2 113.7(14) . . ? C19 C16 C17 114.5(12) . . ? N2 C16 C17 110.0(10) . . ? C19 C16 H16 105.9 . . ? N2 C16 H16 105.9 . . ? C17 C16 H16 105.9 . . ? C18 C17 C16 108.7(12) . . ? C18 C17 H17A 110.0 . . ? C16 C17 H17A 110.0 . . ? C18 C17 H17B 110.0 . . ? C16 C17 H17B 110.0 . . ? H17A C17 H17B 108.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 . . ? O3 C20 N3 126.3(11) . . ? O3 C20 C13 127.8(10) . . ? N3 C20 C13 105.8(8) . . ? C21 N3 C20 111.0(9) . . ? C21 N3 C22 124.6(8) . . ? C20 N3 C22 124.4(8) . . ? O4 C21 N3 123.8(11) . . ? O4 C21 C12 128.6(10) . . ? N3 C21 C12 107.6(8) . . ? N3 C22 C23 113.0(8) . . ? N3 C22 C25 111.6(9) . . ? C23 C22 C25 109.7(9) . . ? N3 C22 H22 107.4 . . ? C23 C22 H22 107.4 . . ? C25 C22 H22 107.4 . . ? C24 C23 C22 110.6(10) . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C11 179.2(13) . . ? C26 C27 C28 178.2(12) . . ? C32 C28 C29 117.7(7) . . ? C32 C28 C27 122.4(9) . . ? C29 C28 C27 119.9(9) . . ? C28 C29 C30 119.4(9) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? N4 C30 C29 123.4(10) . . ? N4 C30 H30 118.3 . . ? C29 C30 H30 118.3 . . ? C30 N4 C31 115.7(7) . . ? C30 N4 Hg1 123.2(6) . 3 ? C31 N4 Hg1 120.8(6) . 3 ? C32 C31 N4 125.7(9) . . ? C32 C31 H31 117.1 . . ? N4 C31 H31 117.1 . . ? C31 C32 C28 118.0(9) . . ? C31 C32 H32 121.0 . . ? C28 C32 H32 121.0 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 2.173 _refine_diff_density_min -1.945 _refine_diff_density_rms 0.167 _database_code_depnum_ccdc_archive 'CCDC 959988' ####################################################################### # # 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_e2255a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H28 Cu F12 N4 O8,2(C2 H4 Cl2)' _chemical_formula_sum 'C46 H36 Cl4 Cu F12 N4 O8' _chemical_formula_weight 1206.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.4908(2) _cell_length_b 14.5434(5) _cell_length_c 15.0317(5) _cell_angle_alpha 66.668(2) _cell_angle_beta 82.427(2) _cell_angle_gamma 80.980(2) _cell_volume 1283.01(7) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9882 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 29.35 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 609 _exptl_absorpt_coefficient_mu 0.733 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9303 _exptl_absorpt_correction_T_max 0.9574 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 36928 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.00 _reflns_number_total 12000 _reflns_number_gt 9863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0986P)^2^+0.0586P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.018(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 12000 _refine_ls_number_parameters 650 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1359 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.068 _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 -0.62904(7) 0.68459(4) -0.14143(4) 0.01860(10) Uani 1 1 d . . . N1 N -0.4507(5) 0.5774(3) -0.0363(3) 0.0193(7) Uani 1 1 d . . . C1 C -0.5135(7) 0.4872(3) 0.0178(4) 0.0283(9) Uani 1 1 d . . . H1 H -0.6450 0.4732 0.0081 0.034 Uiso 1 1 calc R . . C2 C -0.3936(7) 0.4134(4) 0.0876(4) 0.0305(11) Uani 1 1 d . . . H2 H -0.4420 0.3495 0.1238 0.037 Uiso 1 1 calc R . . C3 C -0.2025(7) 0.4327(3) 0.1046(3) 0.0237(10) Uani 1 1 d . . . C4 C -0.1397(7) 0.5269(4) 0.0479(4) 0.0263(11) Uani 1 1 d . . . H4 H -0.0092 0.5429 0.0565 0.032 Uiso 1 1 calc R . . C5 C -0.2652(6) 0.5973(4) -0.0205(3) 0.0227(10) Uani 1 1 d . . . H5 H -0.2201 0.6616 -0.0578 0.027 Uiso 1 1 calc R . . C6 C -0.0691(8) 0.3590(3) 0.1741(4) 0.0263(10) Uani 1 1 d . . . C7 C 0.0477(7) 0.3051(4) 0.2329(4) 0.0284(11) Uani 1 1 d . . . C8 C 0.2030(7) 0.2443(3) 0.2992(3) 0.0223(9) Uani 1 1 d . . . C9 C 0.2376(6) 0.1404(4) 0.3342(3) 0.0228(9) Uani 1 1 d . . . C10 C 0.3916(7) 0.0852(3) 0.3973(3) 0.0229(9) Uani 1 1 d . . . C11 C 0.5272(7) 0.1294(4) 0.4291(3) 0.0253(10) Uani 1 1 d . . . C12 C 0.4949(7) 0.2361(3) 0.3919(3) 0.0246(10) Uani 1 1 d . . . C13 C 0.3383(7) 0.2911(4) 0.3304(3) 0.0245(10) Uani 1 1 d . . . C14 C 0.1270(7) 0.0689(4) 0.3126(4) 0.0280(10) Uani 1 1 d . . . O1 O -0.0136(6) 0.0861(3) 0.2617(3) 0.0384(9) Uani 1 1 d . . . N2 N 0.2246(6) -0.0284(3) 0.3667(3) 0.0272(9) Uani 1 1 d . . . C15 C 0.3810(7) -0.0251(4) 0.4207(3) 0.0264(10) Uani 1 1 d . . . O2 O 0.4859(5) -0.0965(2) 0.4747(3) 0.0311(7) Uani 1 1 d . . . C16 C 0.1838(8) -0.1237(4) 0.3625(4) 0.0305(10) Uani 1 1 d . . . H16 H 0.2691 -0.1797 0.4113 0.037 Uiso 1 1 calc R . . C17 C 0.2566(7) -0.1276(4) 0.2639(4) 0.0449(10) Uani 1 1 d . . . H17A H 0.2196 -0.1906 0.2630 0.054 Uiso 1 1 calc R . . H17B H 0.1794 -0.0705 0.2139 0.054 Uiso 1 1 calc R . . C18 C 0.4887(12) -0.1230(7) 0.2366(7) 0.091(3) Uani 1 1 d . . . H18A H 0.5313 -0.0660 0.2463 0.137 Uiso 1 1 calc R . . H18B H 0.5187 -0.1141 0.1683 0.137 Uiso 1 1 calc R . . H18C H 0.5663 -0.1858 0.2776 0.137 Uiso 1 1 calc R . . C19 C -0.0422(7) -0.1402(4) 0.3926(4) 0.0526(12) Uani 1 1 d . . . H19A H -0.0770 -0.1409 0.4583 0.079 Uiso 1 1 calc R . . H19B H -0.0656 -0.2049 0.3919 0.079 Uiso 1 1 calc R . . H19C H -0.1312 -0.0856 0.3472 0.079 Uiso 1 1 calc R . . C20 C 0.3446(7) 0.3997(4) 0.3093(4) 0.0273(10) Uani 1 1 d . . . O3 O 0.2372(6) 0.4711(3) 0.2587(3) 0.0397(9) Uani 1 1 d . . . N3 N 0.5016(6) 0.4026(3) 0.3630(3) 0.0287(9) Uani 1 1 d . . . C21 C 0.6012(7) 0.3087(4) 0.4111(3) 0.0262(10) Uani 1 1 d . . . O4 O 0.7466(6) 0.2880(3) 0.4624(3) 0.0386(9) Uani 1 1 d . . . C22 C 0.5600(9) 0.4956(4) 0.3694(4) 0.0371(12) Uani 1 1 d . . . H22 H 0.6616 0.4727 0.4206 0.045 Uiso 1 1 calc R . . C23 C 0.3705(9) 0.5526(5) 0.4027(5) 0.0694(13) Uani 1 1 d . . . H23A H 0.4170 0.6089 0.4133 0.083 Uiso 1 1 calc R . . H23B H 0.2743 0.5824 0.3499 0.083 Uiso 1 1 calc R . . C24 C 0.2564(11) 0.4927(5) 0.4902(6) 0.0694(13) Uani 1 1 d . . . H24A H 0.1607 0.4567 0.4741 0.104 Uiso 1 1 calc R . . H24B H 0.1760 0.5368 0.5208 0.104 Uiso 1 1 calc R . . H24C H 0.3548 0.4440 0.5351 0.104 Uiso 1 1 calc R . . C25 C 0.6696(9) 0.5596(4) 0.2762(4) 0.0577(14) Uani 1 1 d . . . H25A H 0.7948 0.5200 0.2603 0.087 Uiso 1 1 calc R . . H25B H 0.7105 0.6181 0.2836 0.087 Uiso 1 1 calc R . . H25C H 0.5754 0.5826 0.2239 0.087 Uiso 1 1 calc R . . C26 C 0.6824(7) 0.0710(3) 0.4937(3) 0.0227(9) Uani 1 1 d . . . C27 C 0.8053(7) 0.0139(4) 0.5495(4) 0.0275(11) Uani 1 1 d . . . C28 C 0.9380(7) -0.0608(3) 0.6188(3) 0.0209(9) Uani 1 1 d . . . C29 C 1.1294(6) -0.0402(3) 0.6356(3) 0.0219(9) Uani 1 1 d . . . H29 H 1.1754 0.0245 0.6016 0.026 Uiso 1 1 calc R . . C30 C 1.2493(7) -0.1157(3) 0.7025(3) 0.0217(6) Uani 1 1 d . . . H30 H 1.3801 -0.1018 0.7130 0.026 Uiso 1 1 calc R . . N4 N 1.1914(6) -0.2089(3) 0.7541(3) 0.0217(6) Uani 1 1 d . . . C31 C 1.0104(7) -0.2279(3) 0.7359(3) 0.0232(10) Uani 1 1 d . . . H31 H 0.9679 -0.2931 0.7716 0.028 Uiso 1 1 calc R . . C32 C 0.8803(7) -0.1580(3) 0.6676(4) 0.0237(10) Uani 1 1 d . . . H32 H 0.7561 -0.1758 0.6546 0.028 Uiso 1 1 calc R . . O5 O -0.7803(5) 0.5765(2) -0.1440(2) 0.0242(7) Uani 1 1 d . . . C33 C -0.7277(7) 0.5215(3) -0.1930(4) 0.0255(10) Uani 1 1 d . . . C34 C -0.5726(8) 0.5253(4) -0.2640(4) 0.0378(12) Uani 1 1 d . . . H34 H -0.5606 0.4781 -0.2941 0.045 Uiso 1 1 calc R . . C35 C -0.4271(7) 0.5981(4) -0.2948(4) 0.0302(11) Uani 1 1 d . . . O6 O -0.4085(5) 0.6616(2) -0.2634(3) 0.0297(8) Uani 1 1 d . . . C36 C -0.8716(9) 0.4359(5) -0.1598(5) 0.0401(14) Uani 1 1 d . . . F3 F -0.8350(6) 0.3818(3) -0.2157(3) 0.0738(13) Uani 1 1 d . . . F2 F -1.0697(5) 0.4737(3) -0.1646(3) 0.0615(10) Uani 1 1 d . . . F1 F -0.8438(6) 0.3743(3) -0.0700(3) 0.0651(11) Uani 1 1 d . . . C40 C -0.2751(10) 0.5986(5) -0.3832(5) 0.0506(16) Uani 1 1 d . . . F4 F -0.3576(8) 0.6618(4) -0.4655(3) 0.0902(14) Uani 1 1 d . . . F5 F -0.2320(7) 0.5102(3) -0.3898(3) 0.0873(15) Uani 1 1 d . . . F6 F -0.0956(6) 0.6314(3) -0.3829(3) 0.0751(13) Uani 1 1 d . . . O7 O -0.8548(5) 0.7084(2) -0.0228(2) 0.0272(7) Uani 1 1 d . . . C44 C -0.8457(7) 0.7758(4) 0.0065(4) 0.0260(10) Uani 1 1 d . . . C45 C -0.7009(8) 0.8477(4) -0.0238(4) 0.0305(10) Uani 1 1 d . . . H45 H -0.7197 0.8972 0.0039 0.037 Uiso 1 1 calc R . . C46 C -0.5338(7) 0.8497(3) -0.0914(4) 0.0260(10) Uani 1 1 d . . . O8 O -0.4795(4) 0.7927(2) -0.1382(2) 0.0230(7) Uani 1 1 d . . . C47 C -1.0123(8) 0.7785(4) 0.0895(4) 0.0328(10) Uani 1 1 d . . . F11 F -1.1934(5) 0.7531(3) 0.0777(2) 0.0462(7) Uani 1 1 d . . . F10 F -1.0553(5) 0.8694(2) 0.0937(3) 0.0529(8) Uani 1 1 d . . . F12 F -0.9465(5) 0.7152(3) 0.1740(2) 0.0557(8) Uani 1 1 d . . . C51 C -0.3980(7) 0.9360(4) -0.1211(4) 0.0303(11) Uani 1 1 d . . . F9 F -0.1925(4) 0.9026(3) -0.1251(2) 0.0446(8) Uani 1 1 d . . . F8 F -0.4276(5) 0.9866(3) -0.0642(3) 0.0565(10) Uani 1 1 d . . . F7 F -0.4350(6) 1.0009(2) -0.2119(3) 0.0578(9) Uani 1 1 d . . . Cl1 Cl 0.5023(4) 0.16593(17) 0.1143(2) 0.1005(8) Uani 1 1 d . . . C55 C 0.7422(18) 0.1071(7) 0.0646(7) 0.132(3) Uani 1 1 d D . . H55A H 0.8119 0.0500 0.1174 0.158 Uiso 1 1 calc R . . H55B H 0.7062 0.0821 0.0168 0.158 Uiso 1 1 calc R . . C56 C 0.8692(18) 0.1822(6) 0.0208(7) 0.132(3) Uani 1 1 d D . . H56A H 0.9138 0.2042 0.0690 0.158 Uiso 1 1 calc R . . H56B H 0.7972 0.2411 -0.0296 0.158 Uiso 1 1 calc R . . Cl2 Cl 1.0972(4) 0.1225(2) -0.0344(3) 0.1314(12) Uani 1 1 d . . . Cl3 Cl 0.6430(5) 0.2495(2) 0.7633(3) 0.1304(10) Uani 1 1 d . . . C57 C 0.8607(15) 0.1924(8) 0.7067(10) 0.141 Uani 1 1 d D . . H57A H 0.9295 0.1317 0.7565 0.169 Uiso 1 1 calc R . . H57B H 0.8099 0.1717 0.6589 0.169 Uiso 1 1 calc R . . C58 C 1.0041(15) 0.2635(7) 0.6598(10) 0.141 Uani 1 1 d D . . H58A H 1.0431 0.2894 0.7063 0.169 Uiso 1 1 calc R . . H58B H 0.9391 0.3211 0.6058 0.169 Uiso 1 1 calc R . . Cl4 Cl 1.2324(4) 0.20523(18) 0.6138(2) 0.0988(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02042(14) 0.01265(15) 0.01849(18) 0.00013(14) -0.00919(11) 0.00011(10) N1 0.0174(15) 0.0186(17) 0.0219(19) -0.0076(16) -0.0086(13) 0.0038(12) C1 0.0236(19) 0.024(2) 0.033(3) -0.002(2) -0.0145(17) -0.0032(16) C2 0.033(3) 0.022(2) 0.031(3) -0.003(2) -0.004(2) -0.0058(19) C3 0.023(2) 0.022(2) 0.026(3) -0.010(2) -0.0090(18) 0.0043(18) C4 0.016(2) 0.031(3) 0.032(3) -0.010(2) -0.0083(19) -0.0024(18) C5 0.019(2) 0.022(2) 0.028(3) -0.009(2) -0.0052(18) -0.0045(17) C6 0.035(3) 0.016(2) 0.022(3) 0.000(2) -0.011(2) -0.0009(19) C7 0.031(2) 0.022(2) 0.029(3) -0.007(2) -0.0102(19) 0.0027(17) C8 0.026(2) 0.014(2) 0.020(2) 0.000(2) -0.0059(16) 0.0021(16) C9 0.0223(19) 0.024(2) 0.022(2) -0.007(2) -0.0087(16) 0.0002(16) C10 0.028(2) 0.0152(19) 0.020(2) -0.0030(19) -0.0022(16) 0.0021(15) C11 0.024(2) 0.029(2) 0.019(2) -0.004(2) -0.0111(16) 0.0044(18) C12 0.031(2) 0.017(2) 0.021(2) -0.003(2) -0.0071(17) 0.0035(16) C13 0.027(2) 0.025(2) 0.018(2) -0.003(2) -0.0115(16) 0.0044(16) C14 0.027(2) 0.023(2) 0.032(3) -0.009(2) -0.0073(18) 0.0028(17) O1 0.0393(19) 0.040(2) 0.038(2) -0.012(2) -0.0205(16) -0.0031(16) N2 0.0276(18) 0.0226(19) 0.030(2) -0.0078(19) -0.0065(15) -0.0019(14) C15 0.028(2) 0.023(2) 0.022(2) -0.003(2) -0.0087(16) 0.0052(16) O2 0.0350(16) 0.0168(15) 0.0321(19) 0.0018(15) -0.0114(13) 0.0017(12) C16 0.033(2) 0.023(2) 0.035(3) -0.009(2) -0.0053(18) -0.0043(17) C17 0.051(2) 0.039(2) 0.054(3) -0.027(2) -0.007(2) -0.0029(18) C18 0.082(5) 0.101(6) 0.114(7) -0.076(6) 0.049(5) -0.034(4) C19 0.050(3) 0.041(3) 0.066(4) -0.017(3) 0.002(2) -0.017(2) C20 0.028(2) 0.020(2) 0.030(3) -0.005(2) -0.0026(17) -0.0035(16) O3 0.049(2) 0.0206(17) 0.041(2) -0.0015(17) -0.0200(16) 0.0048(14) N3 0.038(2) 0.0195(18) 0.026(2) -0.0057(18) -0.0070(16) -0.0008(15) C21 0.033(2) 0.022(2) 0.020(2) -0.002(2) -0.0071(17) -0.0041(17) O4 0.042(2) 0.0271(19) 0.045(2) -0.0074(19) -0.0238(17) -0.0004(16) C22 0.050(3) 0.024(2) 0.041(3) -0.013(2) -0.005(2) -0.009(2) C23 0.073(3) 0.060(3) 0.089(4) -0.050(3) 0.028(2) -0.021(2) C24 0.073(3) 0.060(3) 0.089(4) -0.050(3) 0.028(2) -0.021(2) C25 0.078(3) 0.035(3) 0.060(4) -0.020(3) 0.022(3) -0.025(2) C26 0.025(2) 0.017(2) 0.022(2) -0.003(2) -0.0076(16) 0.0004(16) C27 0.025(2) 0.029(3) 0.028(3) -0.010(2) -0.0087(19) 0.0011(19) C28 0.027(2) 0.016(2) 0.011(2) 0.005(2) -0.0075(17) 0.0004(18) C29 0.024(2) 0.017(2) 0.017(2) 0.006(2) -0.0121(16) -0.0036(16) C30 0.0251(15) 0.0154(14) 0.0180(18) 0.0018(14) -0.0049(12) -0.0032(11) N4 0.0251(15) 0.0154(14) 0.0180(18) 0.0018(14) -0.0049(12) -0.0032(11) C31 0.026(2) 0.014(2) 0.016(2) 0.009(2) -0.0066(18) -0.0016(18) C32 0.025(2) 0.018(2) 0.022(3) 0.001(2) -0.0110(19) 0.0000(18) O5 0.0238(16) 0.0214(18) 0.0215(19) -0.0008(16) -0.0043(13) -0.0039(13) C33 0.025(2) 0.019(2) 0.030(3) -0.006(2) -0.007(2) -0.0008(18) C34 0.043(3) 0.032(3) 0.046(3) -0.022(3) 0.005(2) -0.014(2) C35 0.029(2) 0.030(3) 0.033(3) -0.013(2) -0.0066(19) -0.0003(18) O6 0.0308(18) 0.0221(17) 0.036(2) -0.0086(17) -0.0040(15) -0.0066(14) C36 0.040(3) 0.042(3) 0.045(4) -0.022(3) -0.001(2) -0.011(2) F3 0.075(3) 0.078(3) 0.105(4) -0.070(3) 0.026(2) -0.044(2) F2 0.0282(16) 0.064(2) 0.097(3) -0.032(2) -0.0072(16) -0.0146(15) F1 0.079(3) 0.042(2) 0.066(3) -0.001(2) -0.013(2) -0.0314(18) C40 0.059(3) 0.045(3) 0.056(4) -0.030(4) 0.020(3) -0.021(3) F4 0.115(4) 0.094(3) 0.043(2) -0.012(3) 0.005(2) -0.006(3) F5 0.100(3) 0.061(2) 0.113(4) -0.058(3) 0.065(3) -0.038(2) F6 0.057(2) 0.100(3) 0.092(3) -0.062(3) 0.0386(19) -0.045(2) O7 0.0319(18) 0.0212(16) 0.0280(18) -0.0084(16) -0.0047(13) -0.0022(13) C44 0.029(2) 0.021(2) 0.025(3) -0.004(2) -0.0011(18) -0.0059(17) C45 0.030(2) 0.029(2) 0.036(3) -0.015(2) -0.0011(18) -0.0092(18) C46 0.028(2) 0.022(2) 0.030(3) -0.008(2) -0.010(2) -0.0036(19) O8 0.0259(16) 0.0161(16) 0.0230(19) -0.0022(16) -0.0111(14) 0.0026(13) C47 0.038(2) 0.030(2) 0.030(3) -0.008(2) 0.0019(18) -0.0135(18) F11 0.0341(13) 0.0613(19) 0.0483(18) -0.0264(16) 0.0074(11) -0.0138(12) F10 0.0541(17) 0.0454(19) 0.068(2) -0.0360(19) 0.0228(15) -0.0152(14) F12 0.0665(19) 0.064(2) 0.0246(17) -0.0028(18) 0.0025(13) -0.0172(16) C51 0.030(2) 0.022(2) 0.035(3) -0.005(3) -0.001(2) -0.0102(18) F9 0.0332(16) 0.0485(19) 0.054(2) -0.0188(18) -0.0003(13) -0.0166(13) F8 0.056(2) 0.053(2) 0.080(3) -0.043(2) 0.0197(18) -0.0338(17) F7 0.071(2) 0.0272(17) 0.056(3) 0.0142(18) -0.0172(18) -0.0206(15) Cl1 0.1158(17) 0.0692(14) 0.123(2) -0.0528(15) 0.0539(14) -0.0372(12) C55 0.262(9) 0.067(3) 0.091(4) -0.027(3) -0.054(5) -0.065(4) C56 0.262(9) 0.067(3) 0.091(4) -0.027(3) -0.054(5) -0.065(4) Cl2 0.126(2) 0.0717(15) 0.194(3) -0.066(2) 0.0784(19) -0.0389(14) Cl3 0.134(2) 0.0797(17) 0.164(3) -0.052(2) 0.0551(18) -0.0148(15) C57 0.124 0.075 0.162 0.000 0.040 0.000 C58 0.124 0.075 0.162 0.000 0.040 0.000 Cl4 0.1176(18) 0.0695(14) 0.114(2) -0.0429(15) 0.0313(14) -0.0358(13) _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 O8 1.993(3) . ? Cu1 O5 1.995(3) . ? Cu1 N4 2.053(4) 1_364 ? Cu1 N1 2.057(4) . ? Cu1 O7 2.256(3) . ? Cu1 O6 2.273(3) . ? N1 C1 1.336(6) . ? N1 C5 1.352(5) . ? C1 C2 1.386(7) . ? C1 H1 0.9500 . ? C2 C3 1.390(6) . ? C2 H2 0.9500 . ? C3 C4 1.388(7) . ? C3 C6 1.432(6) . ? C4 C5 1.377(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.188(6) . ? C7 C8 1.442(6) . ? C8 C9 1.381(6) . ? C8 C13 1.414(6) . ? C9 C10 1.392(6) . ? C9 C14 1.505(6) . ? C10 C11 1.396(6) . ? C10 C15 1.510(7) . ? C11 C12 1.416(7) . ? C11 C26 1.420(5) . ? C12 C13 1.392(6) . ? C12 C21 1.482(6) . ? C13 C20 1.490(7) . ? C14 O1 1.201(5) . ? C14 N2 1.417(6) . ? N2 C15 1.399(5) . ? N2 C16 1.478(6) . ? C15 O2 1.207(5) . ? C16 C19 1.504(7) . ? C16 C17 1.514(7) . ? C16 H16 1.0000 . ? C17 C18 1.513(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O3 1.196(6) . ? C20 N3 1.396(6) . ? N3 C21 1.367(6) . ? N3 C22 1.502(6) . ? C21 O4 1.223(5) . ? C22 C25 1.499(8) . ? C22 C23 1.516(7) . ? C22 H22 1.0000 . ? C23 C24 1.441(10) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.203(6) . ? C27 C28 1.433(6) . ? C28 C32 1.396(7) . ? C28 C29 1.399(6) . ? C29 C30 1.373(6) . ? C29 H29 0.9500 . ? C30 N4 1.352(6) . ? C30 H30 0.9500 . ? N4 C31 1.333(6) . ? N4 Cu1 2.053(4) 1_746 ? C31 C32 1.390(6) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? O5 C33 1.270(5) . ? C33 C34 1.357(7) . ? C33 C36 1.556(7) . ? C34 C35 1.428(8) . ? C34 H34 0.9500 . ? C35 O6 1.219(5) . ? C35 C40 1.545(8) . ? C36 F1 1.309(7) . ? C36 F2 1.317(6) . ? C36 F3 1.339(6) . ? C40 F5 1.312(6) . ? C40 F6 1.327(7) . ? C40 F4 1.334(8) . ? O7 C44 1.234(5) . ? C44 C45 1.415(7) . ? C44 C47 1.549(7) . ? C45 C46 1.381(7) . ? C45 H45 0.9500 . ? C46 O8 1.269(5) . ? C46 C51 1.533(7) . ? C47 F12 1.318(6) . ? C47 F10 1.333(6) . ? C47 F11 1.339(6) . ? C51 F8 1.311(6) . ? C51 F7 1.344(6) . ? C51 F9 1.348(5) . ? Cl1 C55 1.870(12) . ? C55 C56 1.370(10) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 Cl2 1.864(12) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? Cl3 C57 1.813(10) . ? C57 C58 1.409(10) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 Cl4 1.787(10) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? 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 O8 Cu1 O5 179.62(16) . . ? O8 Cu1 N4 89.72(13) . 1_364 ? O5 Cu1 N4 90.25(13) . 1_364 ? O8 Cu1 N1 90.54(12) . . ? O5 Cu1 N1 89.49(14) . . ? N4 Cu1 N1 179.7(2) 1_364 . ? O8 Cu1 O7 86.98(12) . . ? O5 Cu1 O7 92.64(12) . . ? N4 Cu1 O7 90.85(14) 1_364 . ? N1 Cu1 O7 88.94(12) . . ? O8 Cu1 O6 93.76(12) . . ? O5 Cu1 O6 86.62(12) . . ? N4 Cu1 O6 87.90(13) 1_364 . ? N1 Cu1 O6 92.31(13) . . ? O7 Cu1 O6 178.54(13) . . ? C1 N1 C5 118.3(4) . . ? C1 N1 Cu1 121.5(3) . . ? C5 N1 Cu1 120.2(3) . . ? N1 C1 C2 122.4(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 119.9(5) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 117.0(4) . . ? C4 C3 C6 120.2(4) . . ? C2 C3 C6 122.7(4) . . ? C5 C4 C3 120.5(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 121.9(4) . . ? N1 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C7 C6 C3 173.9(5) . . ? C6 C7 C8 175.3(6) . . ? C9 C8 C13 115.2(4) . . ? C9 C8 C7 124.8(4) . . ? C13 C8 C7 120.0(4) . . ? C8 C9 C10 122.5(4) . . ? C8 C9 C14 128.4(4) . . ? C10 C9 C14 109.0(4) . . ? C9 C10 C11 123.4(4) . . ? C9 C10 C15 107.5(4) . . ? C11 C10 C15 129.1(4) . . ? C10 C11 C12 114.3(4) . . ? C10 C11 C26 122.0(4) . . ? C12 C11 C26 123.7(4) . . ? C13 C12 C11 122.3(4) . . ? C13 C12 C21 107.6(4) . . ? C11 C12 C21 130.1(4) . . ? C12 C13 C8 122.3(5) . . ? C12 C13 C20 107.6(4) . . ? C8 C13 C20 130.1(4) . . ? O1 C14 N2 125.2(4) . . ? O1 C14 C9 129.8(4) . . ? N2 C14 C9 105.0(3) . . ? C15 N2 C14 112.3(4) . . ? C15 N2 C16 122.0(4) . . ? C14 N2 C16 125.6(4) . . ? O2 C15 N2 126.4(4) . . ? O2 C15 C10 127.5(4) . . ? N2 C15 C10 106.1(4) . . ? N2 C16 C19 110.4(4) . . ? N2 C16 C17 111.1(4) . . ? C19 C16 C17 113.5(4) . . ? N2 C16 H16 107.1 . . ? C19 C16 H16 107.1 . . ? C17 C16 H16 107.1 . . ? C18 C17 C16 114.7(4) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 . . ? O3 C20 N3 125.8(4) . . ? O3 C20 C13 128.4(4) . . ? N3 C20 C13 105.8(4) . . ? C21 N3 C20 111.9(4) . . ? C21 N3 C22 122.2(4) . . ? C20 N3 C22 125.8(4) . . ? O4 C21 N3 126.7(4) . . ? O4 C21 C12 126.3(4) . . ? N3 C21 C12 107.0(4) . . ? C25 C22 N3 111.5(4) . . ? C25 C22 C23 113.1(5) . . ? N3 C22 C23 110.6(4) . . ? C25 C22 H22 107.1 . . ? N3 C22 H22 107.1 . . ? C23 C22 H22 107.1 . . ? C24 C23 C22 114.8(5) . . ? C24 C23 H23A 108.6 . . ? C22 C23 H23A 108.6 . . ? C24 C23 H23B 108.6 . . ? C22 C23 H23B 108.6 . . ? H23A C23 H23B 107.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C11 174.0(5) . . ? C26 C27 C28 174.7(5) . . ? C32 C28 C29 118.8(4) . . ? C32 C28 C27 119.5(4) . . ? C29 C28 C27 121.7(4) . . ? C30 C29 C28 118.4(4) . . ? C30 C29 H29 120.8 . . ? C28 C29 H29 120.8 . . ? N4 C30 C29 123.6(4) . . ? N4 C30 H30 118.2 . . ? C29 C30 H30 118.2 . . ? C31 N4 C30 117.2(4) . . ? C31 N4 Cu1 121.4(3) . 1_746 ? C30 N4 Cu1 121.4(3) . 1_746 ? N4 C31 C32 123.8(4) . . ? N4 C31 H31 118.1 . . ? C32 C31 H31 118.1 . . ? C31 C32 C28 117.9(4) . . ? C31 C32 H32 121.0 . . ? C28 C32 H32 121.0 . . ? C33 O5 Cu1 127.8(3) . . ? O5 C33 C34 131.3(5) . . ? O5 C33 C36 110.1(4) . . ? C34 C33 C36 118.6(4) . . ? C33 C34 C35 122.0(4) . . ? C33 C34 H34 119.0 . . ? C35 C34 H34 119.0 . . ? O6 C35 C34 129.6(5) . . ? O6 C35 C40 115.2(5) . . ? C34 C35 C40 115.1(4) . . ? C35 O6 Cu1 122.2(3) . . ? F1 C36 F2 108.1(5) . . ? F1 C36 F3 108.1(5) . . ? F2 C36 F3 107.1(4) . . ? F1 C36 C33 110.7(4) . . ? F2 C36 C33 110.6(5) . . ? F3 C36 C33 112.2(5) . . ? F5 C40 F6 108.0(5) . . ? F5 C40 F4 106.8(5) . . ? F6 C40 F4 106.0(5) . . ? F5 C40 C35 113.7(5) . . ? F6 C40 C35 112.0(4) . . ? F4 C40 C35 110.1(5) . . ? C44 O7 Cu1 122.5(3) . . ? O7 C44 C45 128.7(4) . . ? O7 C44 C47 114.6(4) . . ? C45 C44 C47 116.7(4) . . ? C46 C45 C44 123.5(4) . . ? C46 C45 H45 118.3 . . ? C44 C45 H45 118.3 . . ? O8 C46 C45 129.4(4) . . ? O8 C46 C51 113.2(4) . . ? C45 C46 C51 117.3(4) . . ? C46 O8 Cu1 128.6(3) . . ? F12 C47 F10 107.5(4) . . ? F12 C47 F11 108.8(4) . . ? F10 C47 F11 106.4(4) . . ? F12 C47 C44 110.1(4) . . ? F10 C47 C44 113.0(4) . . ? F11 C47 C44 110.8(4) . . ? F8 C51 F7 108.3(4) . . ? F8 C51 F9 107.3(4) . . ? F7 C51 F9 105.3(4) . . ? F8 C51 C46 114.8(4) . . ? F7 C51 C46 109.1(4) . . ? F9 C51 C46 111.5(4) . . ? C56 C55 Cl1 105.4(7) . . ? C56 C55 H55A 110.7 . . ? Cl1 C55 H55A 110.7 . . ? C56 C55 H55B 110.7 . . ? Cl1 C55 H55B 110.7 . . ? H55A C55 H55B 108.8 . . ? C55 C56 Cl2 103.8(7) . . ? C55 C56 H56A 111.0 . . ? Cl2 C56 H56A 111.0 . . ? C55 C56 H56B 111.0 . . ? Cl2 C56 H56B 111.0 . . ? H56A C56 H56B 109.0 . . ? C58 C57 Cl3 108.5(8) . . ? C58 C57 H57A 110.0 . . ? Cl3 C57 H57A 110.0 . . ? C58 C57 H57B 110.0 . . ? Cl3 C57 H57B 110.0 . . ? H57A C57 H57B 108.4 . . ? C57 C58 Cl4 109.4(7) . . ? C57 C58 H58A 109.8 . . ? Cl4 C58 H58A 109.8 . . ? C57 C58 H58B 109.8 . . ? Cl4 C58 H58B 109.8 . . ? H58A C58 H58B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.750 _refine_diff_density_min -0.850 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 959989' ####################################################################### # # 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_e2843n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H38 Cu2 N4 O12,4(C H Cl3)' _chemical_formula_sum 'C44 H42 Cl12 Cu2 N4 O12' _chemical_formula_weight 1371.30 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 P1 _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.2342(5) _cell_length_b 19.7423(10) _cell_length_c 19.9269(12) _cell_angle_alpha 65.3440(10) _cell_angle_beta 89.542(2) _cell_angle_gamma 86.931(2) _cell_volume 2939.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4988 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 24.62 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 1.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9246 _exptl_absorpt_correction_T_max 0.9488 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26531 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0906 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 29.13 _reflns_number_total 24176 _reflns_number_gt 15034 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.029(14) _chemical_absolute_configuration ad _refine_ls_number_reflns 24176 _refine_ls_number_parameters 1349 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1160 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1626 _refine_ls_wR_factor_gt 0.1394 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.033 _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 Cu1 Cu -0.26198(9) 0.50966(5) 0.74131(4) 0.0194(2) Uani 1 1 d . . . Cu2 Cu -0.31528(9) 0.38912(5) 0.85939(4) 0.0213(2) Uani 1 1 d . . . N1 N -0.2069(8) 0.6056(4) 0.6396(4) 0.0263(17) Uani 1 1 d . . . C1 C -0.2156(11) 0.5999(5) 0.5762(5) 0.035(2) Uani 1 1 d . . . H1 H -0.2619 0.5570 0.5760 0.042 Uiso 1 1 calc R . . C2 C -0.1618(11) 0.6522(5) 0.5104(4) 0.034(2) Uani 1 1 d . . . H2 H -0.1773 0.6465 0.4659 0.040 Uiso 1 1 calc R . . C3 C -0.0841(9) 0.7138(5) 0.5095(4) 0.025(2) Uani 1 1 d . . . C4 C -0.0687(10) 0.7182(5) 0.5771(4) 0.028(2) Uani 1 1 d . . . H4 H -0.0142 0.7582 0.5800 0.034 Uiso 1 1 calc R . . C5 C -0.1342(10) 0.6632(5) 0.6415(4) 0.0246(19) Uani 1 1 d . . . H5 H -0.1260 0.6677 0.6870 0.029 Uiso 1 1 calc R . . C6 C -0.0146(9) 0.7673(5) 0.4473(5) 0.029(2) Uani 1 1 d . . . C7 C 0.0519(10) 0.8163(5) 0.3984(5) 0.0272(19) Uani 1 1 d . . . C8 C 0.1383(9) 0.8750(4) 0.3458(4) 0.0186(16) Uani 1 1 d . . . C9 C 0.1554(9) 0.8897(4) 0.2715(4) 0.0224(17) Uani 1 1 d . . . C10 C 0.0848(9) 0.8517(5) 0.2282(5) 0.0264(18) Uani 1 1 d . . . O1 O 0.0009(7) 0.8002(4) 0.2497(3) 0.0374(15) Uani 1 1 d . . . N2 N 0.1391(9) 0.8915(4) 0.1552(4) 0.0355(18) Uani 1 1 d . . . C11 C 0.2358(9) 0.9481(5) 0.1478(4) 0.0254(18) Uani 1 1 d . . . O2 O 0.2990(8) 0.9894(4) 0.0915(3) 0.0464(17) Uani 1 1 d . . . C12 C 0.2450(9) 0.9492(4) 0.2221(4) 0.0195(16) Uani 1 1 d . . . C13 C 0.3248(8) 0.9963(4) 0.2461(4) 0.0185(16) Uani 1 1 d . . . C14 C 0.3130(9) 0.9808(5) 0.3195(4) 0.0218(17) Uani 1 1 d . . . C15 C 0.3882(9) 1.0150(5) 0.3641(5) 0.0257(17) Uani 1 1 d . . . O3 O 0.4838(7) 1.0653(3) 0.3411(3) 0.0339(14) Uani 1 1 d . . . N3 N 0.3368(8) 0.9796(4) 0.4353(4) 0.0305(16) Uani 1 1 d . . . C16 C 0.2326(10) 0.9234(5) 0.4431(4) 0.0258(18) Uani 1 1 d . . . O4 O 0.1663(7) 0.8855(4) 0.4993(3) 0.0366(15) Uani 1 1 d . . . C17 C 0.2219(9) 0.9234(5) 0.3678(4) 0.0213(17) Uani 1 1 d . . . C18 C 0.0986(13) 0.8729(6) 0.0933(5) 0.060(3) Uani 1 1 d . . . H18 H 0.1550 0.9080 0.0488 0.072 Uiso 1 1 calc R . . C19 C -0.0796(14) 0.8839(8) 0.0762(5) 0.090(4) Uani 1 1 d . . . H19A H -0.1362 0.8450 0.1171 0.108 Uiso 1 1 calc R . . H19B H -0.0989 0.8762 0.0309 0.108 Uiso 1 1 calc R . . C20 C -0.1574(18) 0.9620(10) 0.0645(8) 0.125(7) Uani 1 1 d . . . H20A H -0.1302 0.9726 0.1069 0.188 Uiso 1 1 calc R . . H20B H -0.2758 0.9621 0.0599 0.188 Uiso 1 1 calc R . . H20C H -0.1149 1.0005 0.0194 0.188 Uiso 1 1 calc R . . C21 C 0.1628(17) 0.7936(7) 0.1080(7) 0.102(5) Uani 1 1 d . . . H21A H 0.1225 0.7583 0.1555 0.152 Uiso 1 1 calc R . . H21B H 0.2820 0.7910 0.1095 0.152 Uiso 1 1 calc R . . H21C H 0.1250 0.7807 0.0686 0.152 Uiso 1 1 calc R . . C22 C 0.3943(10) 0.9904(5) 0.5002(4) 0.0328(18) Uani 1 1 d . . . H22 H 0.3197 0.9633 0.5415 0.039 Uiso 1 1 calc R . . C23 C 0.3801(10) 1.0709(5) 0.4880(5) 0.047(2) Uani 1 1 d . . . H23A H 0.4590 1.0989 0.4501 0.057 Uiso 1 1 calc R . . H23B H 0.4101 1.0743 0.5345 0.057 Uiso 1 1 calc R . . C24 C 0.2111(14) 1.1079(8) 0.4636(8) 0.092(5) Uani 1 1 d . . . H24A H 0.1772 1.1020 0.4194 0.139 Uiso 1 1 calc R . . H24B H 0.2131 1.1611 0.4523 0.139 Uiso 1 1 calc R . . H24C H 0.1341 1.0844 0.5033 0.139 Uiso 1 1 calc R . . C25 C 0.5641(12) 0.9534(6) 0.5249(5) 0.047(2) Uani 1 1 d . . . H25A H 0.5650 0.9013 0.5316 0.071 Uiso 1 1 calc R . . H25B H 0.5935 0.9551 0.5717 0.071 Uiso 1 1 calc R . . H25C H 0.6429 0.9800 0.4872 0.071 Uiso 1 1 calc R . . C26 C 0.4087(9) 1.0591(5) 0.1935(4) 0.0238(18) Uani 1 1 d . . . C27 C 0.4696(10) 1.1096(5) 0.1464(4) 0.0272(19) Uani 1 1 d . . . C28 C 0.5317(10) 1.1712(5) 0.0838(4) 0.028(2) Uani 1 1 d . . . C29 C 0.5469(12) 1.1658(6) 0.0159(5) 0.045(3) Uani 1 1 d . . . H29 H 0.5203 1.1220 0.0108 0.054 Uiso 1 1 calc R . . C30 C 0.6009(12) 1.2257(5) -0.0421(5) 0.037(2) Uani 1 1 d . . . H30 H 0.6173 1.2208 -0.0872 0.044 Uiso 1 1 calc R . . N4 N 0.6334(8) 1.2914(4) -0.0414(4) 0.0287(17) Uani 1 1 d . . . C31 C 0.6236(14) 1.2935(6) 0.0237(5) 0.050(3) Uani 1 1 d . . . H31 H 0.6550 1.3374 0.0273 0.060 Uiso 1 1 calc R . . C32 C 0.5715(14) 1.2371(6) 0.0864(5) 0.054(3) Uani 1 1 d . . . H32 H 0.5629 1.2432 0.1312 0.064 Uiso 1 1 calc R . . O5 O -0.1705(7) 0.4368(4) 0.7057(3) 0.0311(15) Uani 1 1 d . . . C33 C -0.1600(10) 0.3678(5) 0.7407(5) 0.028(2) Uani 1 1 d . . . C34 C -0.0828(13) 0.3194(6) 0.7053(6) 0.047(3) Uani 1 1 d . . . H34A H 0.0308 0.3062 0.7220 0.071 Uiso 1 1 calc R . . H34B H -0.0873 0.3470 0.6515 0.071 Uiso 1 1 calc R . . H34C H -0.1422 0.2738 0.7197 0.071 Uiso 1 1 calc R . . O6 O -0.2085(7) 0.3346(3) 0.8068(3) 0.0353(15) Uani 1 1 d . . . O7 O -0.4757(6) 0.4986(3) 0.7064(3) 0.0269(13) Uani 1 1 d . . . C35 C -0.5641(9) 0.4463(5) 0.7445(5) 0.0218(18) Uani 1 1 d . . . C36 C -0.7253(9) 0.4435(6) 0.7142(5) 0.040(2) Uani 1 1 d . . . H36A H -0.7787 0.3993 0.7484 0.060 Uiso 1 1 calc R . . H36B H -0.7121 0.4410 0.6664 0.060 Uiso 1 1 calc R . . H36C H -0.7921 0.4885 0.7077 0.060 Uiso 1 1 calc R . . O8 O -0.5205(7) 0.3959(3) 0.8061(3) 0.0298(14) Uani 1 1 d . . . O9 O -0.3634(7) 0.5624(3) 0.7964(3) 0.0289(14) Uani 1 1 d . . . C37 C -0.4214(9) 0.5285(5) 0.8606(5) 0.025(2) Uani 1 1 d . . . C38 C -0.4999(10) 0.5763(5) 0.8976(5) 0.030(2) Uani 1 1 d . . . H38A H -0.5286 0.5439 0.9484 0.045 Uiso 1 1 calc R . . H38B H -0.5984 0.6032 0.8699 0.045 Uiso 1 1 calc R . . H38C H -0.4230 0.6122 0.8982 0.045 Uiso 1 1 calc R . . O10 O -0.4126(7) 0.4587(4) 0.8985(3) 0.0314(15) Uani 1 1 d . . . O11 O -0.0572(7) 0.5077(4) 0.7906(3) 0.0292(14) Uani 1 1 d . . . C39 C -0.0124(9) 0.4587(5) 0.8519(5) 0.027(2) Uani 1 1 d . . . C40 C 0.1488(10) 0.4628(6) 0.8845(5) 0.038(2) Uani 1 1 d . . . H40A H 0.2303 0.4786 0.8456 0.057 Uiso 1 1 calc R . . H40B H 0.1828 0.4135 0.9228 0.057 Uiso 1 1 calc R . . H40C H 0.1384 0.4990 0.9064 0.057 Uiso 1 1 calc R . . O12 O -0.0946(7) 0.4046(4) 0.8908(3) 0.0346(15) Uani 1 1 d . . . Cu3 Cu 0.66898(9) 0.90252(5) -0.16993(5) 0.0221(2) Uani 1 1 d . . . Cu4 Cu 0.73506(9) 1.02464(5) -0.28178(4) 0.0197(2) Uani 1 1 d . . . N5 N 0.6092(8) 0.8072(4) -0.0722(4) 0.0265(17) Uani 1 1 d . . . C41 C 0.6320(12) 0.8113(6) -0.0060(5) 0.046(3) Uani 1 1 d . . . H41 H 0.6826 0.8534 -0.0058 0.055 Uiso 1 1 calc R . . C42 C 0.5846(11) 0.7569(6) 0.0606(5) 0.042(3) Uani 1 1 d . . . H42 H 0.6035 0.7609 0.1057 0.051 Uiso 1 1 calc R . . C43 C 0.5087(10) 0.6962(5) 0.0594(4) 0.0229(18) Uani 1 1 d . . . C44 C 0.4896(10) 0.6911(5) -0.0077(5) 0.028(2) Uani 1 1 d . . . H44 H 0.4415 0.6492 -0.0094 0.034 Uiso 1 1 calc R . . C45 C 0.5400(10) 0.7464(5) -0.0701(5) 0.031(2) Uani 1 1 d . . . H45 H 0.5257 0.7420 -0.1154 0.038 Uiso 1 1 calc R . . C46 C 0.4513(11) 0.6393(5) 0.1267(4) 0.0279(19) Uani 1 1 d . . . C47 C 0.3863(10) 0.5924(5) 0.1767(5) 0.028(2) Uani 1 1 d . . . C48 C 0.2994(10) 0.5319(5) 0.2309(4) 0.028(2) Uani 1 1 d . . . C49 C 0.2890(9) 0.5177(5) 0.3060(4) 0.0252(19) Uani 1 1 d . . . C50 C 0.3656(11) 0.5575(6) 0.3455(5) 0.036(2) Uani 1 1 d . . . O13 O 0.4488(8) 0.6125(4) 0.3211(4) 0.0450(17) Uani 1 1 d . . . N6 N 0.3209(8) 0.5218(4) 0.4186(4) 0.0348(17) Uani 1 1 d . . . C51 C 0.2202(10) 0.4608(5) 0.4299(5) 0.033(2) Uani 1 1 d . . . O14 O 0.1561(7) 0.4229(4) 0.4868(3) 0.0400(16) Uani 1 1 d . . . C52 C 0.2040(9) 0.4604(5) 0.3547(4) 0.0240(18) Uani 1 1 d . . . C53 C 0.1204(9) 0.4099(5) 0.3371(4) 0.0217(17) Uani 1 1 d . . . C54 C 0.1326(9) 0.4262(5) 0.2602(4) 0.0272(19) Uani 1 1 d . . . C55 C 0.0593(11) 0.3833(6) 0.2219(5) 0.044(3) Uani 1 1 d . . . O15 O -0.0247(8) 0.3326(4) 0.2449(4) 0.055(2) Uani 1 1 d . . . N7 N 0.1124(11) 0.4201(5) 0.1477(4) 0.053(2) Uani 1 1 d . . . C56 C 0.2099(11) 0.4790(6) 0.1382(5) 0.041(2) Uani 1 1 d . . . O16 O 0.2707(9) 0.5190(4) 0.0806(3) 0.057(2) Uani 1 1 d . . . C57 C 0.2185(9) 0.4835(5) 0.2115(4) 0.029(2) Uani 1 1 d . . . C58 C 0.3812(12) 0.5421(6) 0.4792(5) 0.053(3) Uani 1 1 d . . . H58 H 0.4630 0.5807 0.4568 0.064 Uiso 1 1 calc R . . C59 C 0.4708(11) 0.4730(6) 0.5368(4) 0.055(2) Uani 1 1 d . . . H59A H 0.5004 0.4832 0.5796 0.066 Uiso 1 1 calc R . . H59B H 0.3970 0.4313 0.5544 0.066 Uiso 1 1 calc R . . C60 C 0.6143(14) 0.4512(9) 0.5088(7) 0.084(4) Uani 1 1 d . . . H60A H 0.5991 0.4038 0.5055 0.126 Uiso 1 1 calc R . . H60B H 0.7064 0.4451 0.5421 0.126 Uiso 1 1 calc R . . H60C H 0.6362 0.4897 0.4597 0.126 Uiso 1 1 calc R . . C61 C 0.2419(13) 0.5777(6) 0.5048(6) 0.068(3) Uani 1 1 d . . . H61A H 0.1935 0.6206 0.4624 0.102 Uiso 1 1 calc R . . H61B H 0.2821 0.5946 0.5411 0.102 Uiso 1 1 calc R . . H61C H 0.1595 0.5412 0.5274 0.102 Uiso 1 1 calc R . . C62 C 0.0804(17) 0.3949(8) 0.0893(6) 0.111(6) Uani 1 1 d D . . H62 H 0.1336 0.4307 0.0440 0.134 Uiso 1 1 calc R . . C63 C -0.0998(19) 0.4055(10) 0.0723(7) 0.172(12) Uani 1 1 d D . . H63A H -0.1550 0.3665 0.1136 0.206 Uiso 1 1 calc R . . H63B H -0.1182 0.3966 0.0276 0.206 Uiso 1 1 calc R . . C64 C -0.182(2) 0.4805(10) 0.0595(8) 0.215(15) Uani 1 1 d D . . H64A H -0.1523 0.4939 0.0998 0.323 Uiso 1 1 calc R . . H64B H -0.3003 0.4776 0.0580 0.323 Uiso 1 1 calc R . . H64C H -0.1465 0.5186 0.0124 0.323 Uiso 1 1 calc R . . C65 C 0.157(2) 0.3169(9) 0.1040(8) 0.160(10) Uani 1 1 d D . . H65A H 0.2740 0.3155 0.1133 0.240 Uiso 1 1 calc R . . H65B H 0.1388 0.3063 0.0609 0.240 Uiso 1 1 calc R . . H65C H 0.1065 0.2792 0.1473 0.240 Uiso 1 1 calc R . . C66 C 0.0369(9) 0.3507(5) 0.3885(4) 0.0229(17) Uani 1 1 d . . . C67 C -0.0330(9) 0.3022(5) 0.4351(4) 0.0244(19) Uani 1 1 d . . . C68 C -0.1002(9) 0.2418(4) 0.4972(4) 0.0215(17) Uani 1 1 d . . . C69 C -0.1638(10) 0.1814(5) 0.4906(5) 0.0285(19) Uani 1 1 d . . . H69 H -0.1698 0.1791 0.4440 0.034 Uiso 1 1 calc R . . C70 C -0.2185(11) 0.1244(5) 0.5536(4) 0.029(2) Uani 1 1 d . . . H70 H -0.2625 0.0830 0.5491 0.035 Uiso 1 1 calc R . . N8 N -0.2126(8) 0.1248(4) 0.6195(4) 0.0212(15) Uani 1 1 d . . . C71 C -0.1540(10) 0.1827(5) 0.6274(4) 0.0290(19) Uani 1 1 d . . . H71 H -0.1516 0.1837 0.6747 0.035 Uiso 1 1 calc R . . C72 C -0.0956(12) 0.2426(5) 0.5653(5) 0.038(2) Uani 1 1 d . . . H72 H -0.0529 0.2837 0.5709 0.045 Uiso 1 1 calc R . . O17 O 0.7747(7) 0.8533(3) -0.2294(3) 0.0302(14) Uani 1 1 d . . . C73 C 0.8289(9) 0.8885(5) -0.2923(4) 0.0235(19) Uani 1 1 d . . . C74 C 0.9032(11) 0.8464(5) -0.3319(5) 0.038(2) Uani 1 1 d . . . H74A H 0.9586 0.8003 -0.2964 0.056 Uiso 1 1 calc R . . H74B H 0.9822 0.8768 -0.3672 0.056 Uiso 1 1 calc R . . H74C H 0.8183 0.8340 -0.3585 0.056 Uiso 1 1 calc R . . O18 O 0.8260(7) 0.9591(4) -0.3248(3) 0.0286(14) Uani 1 1 d . . . O19 O 0.4616(6) 0.9097(4) -0.2205(3) 0.0309(15) Uani 1 1 d . . . C75 C 0.4250(9) 0.9630(5) -0.2813(4) 0.0241(18) Uani 1 1 d . . . C76 C 0.2616(11) 0.9631(6) -0.3128(5) 0.048(3) Uani 1 1 d . . . H76A H 0.2444 0.9133 -0.3103 0.071 Uiso 1 1 calc R . . H76B H 0.2553 0.9997 -0.3644 0.071 Uiso 1 1 calc R . . H76C H 0.1776 0.9762 -0.2845 0.071 Uiso 1 1 calc R . . O20 O 0.5164(7) 1.0157(3) -0.3168(3) 0.0270(13) Uani 1 1 d . . . O21 O 0.8844(7) 0.9061(4) -0.1299(3) 0.0367(16) Uani 1 1 d . . . C77 C 0.9736(9) 0.9589(5) -0.1637(5) 0.027(2) Uani 1 1 d . . . C78 C 1.1373(11) 0.9613(6) -0.1299(5) 0.041(2) Uani 1 1 d . . . H78A H 1.1556 0.9165 -0.0838 0.062 Uiso 1 1 calc R . . H78B H 1.1378 1.0057 -0.1198 0.062 Uiso 1 1 calc R . . H78C H 1.2240 0.9631 -0.1646 0.062 Uiso 1 1 calc R . . O22 O 0.9421(7) 1.0141(4) -0.2260(3) 0.0322(15) Uani 1 1 d . . . O23 O 0.5787(8) 0.9724(4) -0.1287(4) 0.0377(16) Uani 1 1 d . . . C79 C 0.5829(10) 1.0417(6) -0.1628(5) 0.034(2) Uani 1 1 d . . . C80 C 0.5188(13) 1.0860(6) -0.1211(6) 0.051(3) Uani 1 1 d . . . H80A H 0.4442 1.0562 -0.0829 0.077 Uiso 1 1 calc R . . H80B H 0.4608 1.1320 -0.1554 0.077 Uiso 1 1 calc R . . H80C H 0.6099 1.0987 -0.0979 0.077 Uiso 1 1 calc R . . O24 O 0.6378(7) 1.0778(3) -0.2259(3) 0.0324(15) Uani 1 1 d . . . C81 C 0.4304(10) 0.6919(5) 0.6766(5) 0.040(2) Uani 1 1 d . . . H81 H 0.5170 0.6506 0.6952 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.2472(3) 0.6560(2) 0.71475(17) 0.0679(9) Uani 1 1 d . . . Cl2 Cl 0.4209(5) 0.7271(2) 0.57929(16) 0.0775(10) Uani 1 1 d . . . Cl3 Cl 0.4831(5) 0.7625(2) 0.7029(2) 0.0813(10) Uani 1 1 d . . . C82 C 0.8287(11) 0.0967(6) 0.2765(5) 0.046(2) Uani 1 1 d . . . H82 H 0.7075 0.1032 0.2718 0.055 Uiso 1 1 calc R . . Cl4 Cl 0.9037(4) 0.0725(2) 0.2086(2) 0.0788(10) Uani 1 1 d . . . Cl5 Cl 0.9081(5) 0.1806(2) 0.2702(2) 0.0961(12) Uani 1 1 d . . . Cl6 Cl 0.8846(4) 0.0265(2) 0.3665(2) 0.0961(13) Uani 1 1 d . . . C83 C 0.4058(12) 0.1990(6) 0.6605(6) 0.053(3) Uani 1 1 d . . . H83 H 0.4993 0.1610 0.6741 0.063 Uiso 1 1 calc R . . Cl7 Cl 0.2292(3) 0.1542(2) 0.70538(19) 0.0790(10) Uani 1 1 d . . . Cl8 Cl 0.4506(6) 0.2679(2) 0.6895(3) 0.1095(14) Uani 1 1 d . . . Cl9 Cl 0.3755(5) 0.2374(3) 0.56372(19) 0.0995(13) Uani 1 1 d . . . C84 C 0.7866(11) 0.5991(6) 0.2621(6) 0.045(2) Uani 1 1 d . . . H84 H 0.6816 0.6298 0.2525 0.054 Uiso 1 1 calc R . . Cl10 Cl 0.8908(4) 0.6261(2) 0.18078(19) 0.0956(12) Uani 1 1 d . . . Cl11 Cl 0.9012(4) 0.6155(2) 0.3277(2) 0.0917(12) Uani 1 1 d . . . Cl12 Cl 0.7424(4) 0.50284(17) 0.29844(19) 0.0706(8) Uani 1 1 d . . . C85 C 0.0423(12) 0.2151(7) 0.9247(6) 0.058(3) Uani 1 1 d . . . H85 H -0.0523 0.2525 0.9098 0.070 Uiso 1 1 calc R . . Cl13 Cl 0.2118(4) 0.2628(2) 0.8828(2) 0.0929(12) Uani 1 1 d . . . Cl14 Cl 0.0007(6) 0.1480(2) 0.8918(2) 0.1022(13) Uani 1 1 d . . . Cl15 Cl 0.0560(5) 0.1774(2) 1.0202(2) 0.1008(13) Uani 1 1 d . . . C86 C 0.6569(15) 0.8084(6) 0.3043(6) 0.059(3) Uani 1 1 d . . . H86 H 0.7620 0.7778 0.3145 0.071 Uiso 1 1 calc R . . Cl16 Cl 0.5487(5) 0.7978(2) 0.2359(2) 0.0922(11) Uani 1 1 d . . . Cl17 Cl 0.5391(5) 0.7787(3) 0.3844(2) 0.138(2) Uani 1 1 d . . . Cl18 Cl 0.6939(5) 0.9005(2) 0.2810(3) 0.1253(18) Uani 1 1 d . . . C87 C -0.0097(13) 0.7264(6) 0.8905(6) 0.052(3) Uani 1 1 d . . . H87 H -0.0987 0.7665 0.8768 0.063 Uiso 1 1 calc R . . Cl19 Cl 0.1656(3) 0.76618(19) 0.84518(17) 0.0672(9) Uani 1 1 d . . . Cl20 Cl -0.0690(4) 0.65778(19) 0.86025(18) 0.0736(9) Uani 1 1 d . . . Cl21 Cl 0.0138(5) 0.6866(2) 0.98497(18) 0.0885(11) Uani 1 1 d . . . C88 C 0.5982(18) 0.3116(7) 0.2878(8) 0.095(5) Uani 1 1 d . . . H88 H 0.7178 0.2985 0.2924 0.114 Uiso 1 1 calc R . . Cl22 Cl 0.4986(8) 0.2326(3) 0.3013(3) 0.157(2) Uani 1 1 d . . . Cl23 Cl 0.5384(4) 0.3349(2) 0.36458(19) 0.0772(10) Uani 1 1 d . . . Cl24 Cl 0.5615(5) 0.3815(2) 0.2076(2) 0.1000(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0210(5) 0.0188(6) 0.0158(5) -0.0042(4) 0.0060(4) -0.0057(4) Cu2 0.0239(5) 0.0170(6) 0.0201(5) -0.0044(5) 0.0076(4) -0.0058(4) N1 0.026(3) 0.036(5) 0.013(3) -0.004(3) 0.005(2) -0.019(3) C1 0.057(6) 0.031(6) 0.024(5) -0.015(4) 0.013(4) -0.024(4) C2 0.052(5) 0.029(6) 0.016(4) -0.004(4) 0.002(4) -0.019(4) C3 0.024(4) 0.035(6) 0.016(4) -0.009(4) 0.003(3) -0.010(4) C4 0.037(5) 0.027(6) 0.018(4) -0.005(4) 0.004(3) -0.018(4) C5 0.032(4) 0.030(5) 0.010(4) -0.006(4) 0.005(3) -0.005(4) C6 0.020(4) 0.039(6) 0.023(4) -0.009(4) 0.005(3) -0.007(4) C7 0.029(4) 0.029(5) 0.020(4) -0.006(4) -0.002(3) -0.002(4) C8 0.018(3) 0.014(4) 0.020(4) -0.003(3) 0.005(3) -0.005(3) C9 0.030(4) 0.008(4) 0.029(4) -0.008(3) 0.000(3) -0.002(3) C10 0.029(4) 0.025(5) 0.030(4) -0.016(4) 0.005(3) -0.005(3) O1 0.046(3) 0.037(4) 0.036(3) -0.019(3) 0.017(2) -0.032(3) N2 0.046(4) 0.045(5) 0.026(3) -0.022(3) 0.015(3) -0.032(3) C11 0.027(4) 0.032(5) 0.021(4) -0.014(4) 0.002(3) -0.008(3) O2 0.062(4) 0.053(4) 0.024(3) -0.012(3) 0.012(3) -0.029(3) C12 0.021(3) 0.022(5) 0.013(3) -0.005(3) 0.010(2) -0.010(3) C13 0.015(3) 0.013(4) 0.020(4) 0.000(3) -0.001(3) -0.002(3) C14 0.029(4) 0.018(4) 0.018(4) -0.007(3) 0.005(3) -0.010(3) C15 0.026(4) 0.018(4) 0.030(4) -0.007(3) -0.005(3) -0.004(3) O3 0.038(3) 0.034(3) 0.032(3) -0.014(3) 0.004(2) -0.017(2) N3 0.034(3) 0.039(4) 0.016(3) -0.008(3) 0.003(3) -0.013(3) C16 0.029(4) 0.036(5) 0.015(4) -0.012(4) 0.004(3) -0.012(3) O4 0.043(3) 0.046(4) 0.023(3) -0.015(3) 0.010(3) -0.018(3) C17 0.025(4) 0.020(5) 0.014(3) -0.002(3) -0.002(3) -0.002(3) C18 0.080(7) 0.082(8) 0.038(5) -0.040(5) 0.016(5) -0.053(6) C19 0.079(8) 0.143(12) 0.042(6) -0.025(7) -0.013(5) -0.070(8) C20 0.102(12) 0.108(14) 0.102(12) 0.020(10) -0.060(9) -0.015(10) C21 0.146(12) 0.112(11) 0.101(10) -0.093(9) 0.044(9) -0.060(9) C22 0.048(4) 0.034(5) 0.017(4) -0.010(3) 0.002(3) -0.017(4) C23 0.054(5) 0.058(6) 0.045(5) -0.036(5) -0.005(4) -0.003(4) C24 0.072(8) 0.108(11) 0.119(11) -0.074(9) -0.041(7) 0.042(7) C25 0.067(6) 0.046(6) 0.040(5) -0.029(5) -0.012(4) 0.007(5) C26 0.021(3) 0.031(5) 0.014(3) -0.004(3) -0.001(3) -0.006(3) C27 0.030(4) 0.030(5) 0.020(4) -0.008(4) 0.007(3) -0.019(4) C28 0.024(4) 0.036(6) 0.018(4) -0.004(4) 0.002(3) -0.012(4) C29 0.071(6) 0.033(6) 0.039(5) -0.020(5) 0.027(4) -0.026(5) C30 0.069(6) 0.020(5) 0.027(4) -0.015(4) 0.020(4) -0.016(4) N4 0.027(4) 0.023(5) 0.035(4) -0.011(4) 0.008(3) -0.007(3) C31 0.087(8) 0.037(7) 0.028(5) -0.012(5) 0.006(5) -0.035(5) C32 0.100(8) 0.043(7) 0.021(5) -0.012(5) 0.012(5) -0.040(6) O5 0.040(3) 0.032(4) 0.020(3) -0.009(3) 0.013(3) -0.003(3) C33 0.030(4) 0.031(6) 0.031(5) -0.019(5) 0.008(4) -0.006(4) C34 0.066(6) 0.047(7) 0.043(6) -0.033(5) 0.008(5) -0.005(5) O6 0.044(4) 0.021(4) 0.038(4) -0.010(3) 0.002(3) 0.000(3) O7 0.021(3) 0.032(4) 0.023(3) -0.006(3) 0.001(2) -0.009(2) C35 0.022(4) 0.025(5) 0.024(4) -0.015(4) 0.004(3) -0.007(3) C36 0.018(4) 0.074(8) 0.043(5) -0.038(5) -0.004(3) -0.006(4) O8 0.022(3) 0.028(4) 0.035(4) -0.008(3) 0.006(2) -0.008(2) O9 0.040(3) 0.019(4) 0.022(3) -0.003(3) 0.008(2) -0.001(3) C37 0.014(4) 0.029(6) 0.037(5) -0.019(4) -0.008(3) 0.001(3) C38 0.036(4) 0.028(5) 0.034(5) -0.021(4) 0.006(3) 0.003(3) O10 0.042(4) 0.027(4) 0.029(3) -0.015(3) 0.013(3) -0.002(3) O11 0.026(3) 0.033(4) 0.019(3) -0.001(3) 0.000(2) -0.004(3) C39 0.015(4) 0.048(6) 0.027(5) -0.024(4) 0.005(3) -0.002(3) C40 0.028(4) 0.063(7) 0.027(5) -0.020(5) 0.001(3) -0.013(4) O12 0.026(3) 0.045(4) 0.030(3) -0.012(3) -0.003(3) -0.008(3) Cu3 0.0226(5) 0.0224(6) 0.0198(5) -0.0066(5) 0.0071(4) -0.0080(4) Cu4 0.0198(5) 0.0182(6) 0.0195(5) -0.0060(5) 0.0048(4) -0.0036(4) N5 0.028(4) 0.019(4) 0.030(4) -0.007(3) 0.002(3) -0.005(3) C41 0.054(6) 0.048(7) 0.028(5) -0.004(5) 0.003(4) -0.043(5) C42 0.048(6) 0.061(8) 0.026(5) -0.023(5) 0.007(4) -0.031(5) C43 0.028(4) 0.012(5) 0.021(4) 0.000(3) 0.013(3) -0.004(3) C44 0.038(5) 0.020(5) 0.028(5) -0.011(4) 0.011(4) -0.009(4) C45 0.038(5) 0.029(6) 0.033(5) -0.016(4) 0.005(4) -0.017(4) C46 0.046(5) 0.018(5) 0.020(4) -0.006(4) 0.006(3) -0.012(4) C47 0.026(4) 0.033(6) 0.025(4) -0.010(4) 0.003(3) -0.010(4) C48 0.023(4) 0.031(6) 0.021(4) -0.002(4) 0.002(3) -0.005(3) C49 0.021(4) 0.031(5) 0.014(4) 0.000(3) 0.005(3) -0.003(3) C50 0.045(5) 0.040(6) 0.024(4) -0.012(4) 0.008(3) -0.012(4) O13 0.050(4) 0.047(4) 0.046(4) -0.024(3) 0.019(3) -0.031(3) N6 0.038(4) 0.040(5) 0.032(4) -0.019(3) 0.009(3) -0.027(3) C51 0.024(4) 0.045(6) 0.026(4) -0.009(4) 0.007(3) -0.003(3) O14 0.050(3) 0.056(4) 0.014(3) -0.011(3) 0.011(2) -0.025(3) C52 0.020(3) 0.028(5) 0.021(4) -0.008(4) -0.001(3) -0.001(3) C53 0.022(4) 0.029(5) 0.013(3) -0.008(3) 0.002(3) -0.003(3) C54 0.021(4) 0.035(5) 0.023(4) -0.008(4) 0.006(3) -0.011(3) C55 0.053(6) 0.062(7) 0.026(4) -0.026(5) 0.018(4) -0.024(5) O15 0.073(5) 0.061(5) 0.045(4) -0.031(4) 0.025(3) -0.047(4) N7 0.080(6) 0.068(6) 0.028(4) -0.031(4) 0.021(4) -0.049(5) C56 0.049(5) 0.050(7) 0.020(4) -0.008(4) 0.003(4) -0.024(5) O16 0.074(5) 0.080(6) 0.015(3) -0.013(3) 0.015(3) -0.045(4) C57 0.027(4) 0.043(6) 0.013(4) -0.008(4) 0.008(3) -0.011(4) C58 0.063(6) 0.078(8) 0.037(5) -0.040(5) 0.017(4) -0.037(5) C59 0.064(6) 0.078(7) 0.029(4) -0.025(5) 0.005(4) -0.030(5) C60 0.060(7) 0.118(12) 0.060(7) -0.025(8) -0.007(6) 0.008(7) C61 0.080(7) 0.070(8) 0.076(7) -0.052(6) 0.025(6) -0.016(6) C62 0.170(15) 0.162(16) 0.027(6) -0.054(8) 0.037(7) -0.106(12) C63 0.23(2) 0.26(3) 0.041(8) -0.058(12) 0.029(10) -0.20(2) C64 0.186(19) 0.25(2) 0.081(11) 0.080(13) -0.084(12) -0.162(19) C65 0.25(2) 0.19(2) 0.127(15) -0.135(16) 0.111(15) -0.109(18) C66 0.022(4) 0.025(5) 0.023(4) -0.011(4) 0.004(3) -0.007(3) C67 0.027(4) 0.021(5) 0.020(4) -0.005(4) -0.002(3) 0.003(3) C68 0.023(4) 0.012(4) 0.027(4) -0.005(3) 0.006(3) -0.003(3) C69 0.042(5) 0.022(5) 0.018(4) -0.005(4) -0.001(3) -0.009(4) C70 0.049(5) 0.018(5) 0.018(4) -0.003(4) -0.003(4) -0.016(4) N8 0.025(3) 0.017(4) 0.016(3) -0.001(3) -0.002(3) -0.008(3) C71 0.041(4) 0.027(5) 0.018(4) -0.008(4) 0.008(3) -0.012(4) C72 0.059(5) 0.027(5) 0.033(5) -0.015(4) 0.014(4) -0.021(4) O17 0.037(3) 0.025(4) 0.032(3) -0.014(3) 0.009(3) -0.010(3) C73 0.024(4) 0.032(6) 0.023(4) -0.020(4) 0.002(3) -0.001(3) C74 0.042(5) 0.025(5) 0.043(5) -0.012(4) 0.008(4) 0.006(4) O18 0.038(3) 0.024(4) 0.026(3) -0.012(3) 0.006(3) -0.004(3) O19 0.019(3) 0.036(4) 0.033(3) -0.009(3) 0.006(2) -0.013(2) C75 0.024(4) 0.031(5) 0.018(4) -0.009(4) 0.007(3) -0.008(3) C76 0.031(5) 0.083(8) 0.037(5) -0.031(5) 0.008(4) -0.019(5) O20 0.031(3) 0.024(3) 0.020(3) -0.002(2) 0.003(2) -0.008(2) O21 0.037(3) 0.040(4) 0.027(3) -0.006(3) 0.002(3) -0.016(3) C77 0.018(4) 0.047(6) 0.022(4) -0.021(4) -0.004(3) 0.011(4) C78 0.043(5) 0.047(6) 0.031(5) -0.013(4) -0.005(4) -0.008(4) O22 0.023(3) 0.049(5) 0.030(3) -0.019(3) 0.004(2) -0.012(3) O23 0.050(4) 0.030(4) 0.041(4) -0.023(3) 0.021(3) -0.011(3) C79 0.021(4) 0.052(8) 0.037(6) -0.028(6) -0.002(4) -0.002(4) C80 0.061(6) 0.048(7) 0.055(6) -0.035(6) 0.001(5) 0.022(5) O24 0.036(3) 0.033(4) 0.037(4) -0.024(3) 0.009(3) -0.004(3) C81 0.023(4) 0.028(6) 0.050(6) 0.001(4) 0.000(4) 0.008(4) Cl1 0.0344(13) 0.085(2) 0.0676(18) -0.0145(15) 0.0010(11) -0.0080(13) Cl2 0.110(3) 0.068(2) 0.0354(14) -0.0063(14) 0.0059(14) 0.0250(18) Cl3 0.105(3) 0.067(2) 0.071(2) -0.0239(17) 0.0194(17) -0.0373(19) C82 0.038(5) 0.047(7) 0.050(6) -0.019(5) 0.007(4) 0.005(4) Cl4 0.0643(18) 0.090(3) 0.098(3) -0.056(2) 0.0073(16) 0.0077(16) Cl5 0.097(3) 0.068(3) 0.139(4) -0.057(3) 0.031(2) -0.0272(19) Cl6 0.0570(18) 0.110(3) 0.092(3) -0.016(2) 0.0084(16) 0.0236(18) C83 0.041(5) 0.034(6) 0.054(6) 0.009(5) -0.001(4) 0.011(4) Cl7 0.0408(14) 0.094(3) 0.0742(19) -0.0086(17) 0.0133(13) 0.0061(14) Cl8 0.140(4) 0.053(3) 0.128(3) -0.030(2) 0.018(3) -0.011(2) Cl9 0.109(3) 0.101(3) 0.053(2) 0.0005(19) 0.0092(18) 0.010(2) C84 0.024(4) 0.058(7) 0.059(6) -0.030(5) 0.003(4) 0.001(4) Cl10 0.065(2) 0.121(3) 0.068(2) -0.008(2) 0.0254(15) 0.0006(19) Cl11 0.070(2) 0.102(3) 0.135(3) -0.082(3) -0.0112(19) 0.0029(18) Cl12 0.0568(17) 0.0445(19) 0.103(2) -0.0232(16) 0.0147(15) -0.0039(12) C85 0.042(5) 0.050(7) 0.070(7) -0.012(6) 0.016(5) 0.003(5) Cl13 0.0548(18) 0.073(2) 0.114(3) -0.003(2) 0.0262(17) -0.0009(15) Cl14 0.149(4) 0.054(2) 0.098(3) -0.027(2) 0.035(2) -0.006(2) Cl15 0.116(3) 0.084(3) 0.068(2) 0.001(2) 0.000(2) -0.002(2) C86 0.077(8) 0.030(6) 0.062(7) -0.010(5) 0.008(5) 0.003(5) Cl16 0.092(2) 0.115(3) 0.089(2) -0.061(2) -0.0153(18) -0.003(2) Cl17 0.090(3) 0.214(5) 0.063(2) -0.019(3) 0.0054(19) 0.064(3) Cl18 0.067(2) 0.069(3) 0.255(6) -0.085(3) -0.029(3) 0.0120(17) C87 0.061(7) 0.049(7) 0.035(5) -0.007(5) 0.011(5) -0.004(5) Cl19 0.0412(14) 0.080(2) 0.0657(18) -0.0159(15) 0.0091(12) -0.0082(13) Cl20 0.098(2) 0.057(2) 0.0635(19) -0.0217(16) 0.0178(16) -0.0195(17) Cl21 0.111(3) 0.093(3) 0.0423(17) -0.0090(17) -0.0009(16) -0.010(2) C88 0.124(12) 0.035(8) 0.114(11) -0.020(7) 0.073(9) -0.001(7) Cl22 0.233(6) 0.117(5) 0.156(5) -0.083(4) 0.053(4) -0.090(4) Cl23 0.0663(19) 0.088(3) 0.081(2) -0.041(2) -0.0061(16) 0.0155(17) Cl24 0.119(3) 0.086(3) 0.065(2) -0.0057(19) 0.0067(19) 0.032(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 Cu1 O11 1.949(6) . ? Cu1 O7 1.953(5) . ? Cu1 O9 1.957(6) . ? Cu1 O5 1.967(6) . ? Cu1 N1 2.186(7) . ? Cu1 Cu2 2.6108(12) . ? Cu2 O6 1.963(6) . ? Cu2 O8 1.971(6) . ? Cu2 O10 1.975(6) . ? Cu2 O12 2.006(6) . ? Cu2 N4 2.168(7) 1_446 ? N1 C1 1.315(10) . ? N1 C5 1.328(11) . ? C1 C2 1.376(12) . ? C1 H1 0.9500 . ? C2 C3 1.398(12) . ? C2 H2 0.9500 . ? C3 C4 1.392(11) . ? C3 C6 1.394(12) . ? C4 C5 1.416(11) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.203(12) . ? C7 C8 1.417(12) . ? C8 C9 1.392(11) . ? C8 C17 1.416(10) . ? C9 C12 1.417(10) . ? C9 C10 1.498(11) . ? C10 O1 1.184(10) . ? C10 N2 1.416(10) . ? N2 C11 1.364(10) . ? N2 C18 1.472(10) . ? C11 O2 1.211(10) . ? C11 C12 1.494(10) . ? C12 C13 1.401(10) . ? C13 C14 1.367(10) . ? C13 C26 1.452(11) . ? C14 C17 1.394(11) . ? C14 C15 1.478(11) . ? C15 O3 1.230(9) . ? C15 N3 1.370(10) . ? N3 C16 1.396(11) . ? N3 C22 1.480(10) . ? C16 O4 1.203(10) . ? C16 C17 1.502(10) . ? C18 C19 1.493(14) . ? C18 C21 1.531(16) . ? C18 H18 1.0000 . ? C19 C20 1.56(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.503(12) . ? C22 C25 1.527(12) . ? C22 H22 1.0000 . ? C23 C24 1.520(13) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.180(11) . ? C27 C28 1.444(11) . ? C28 C32 1.379(13) . ? C28 C29 1.406(12) . ? C29 C30 1.357(12) . ? C29 H29 0.9500 . ? C30 N4 1.344(11) . ? C30 H30 0.9500 . ? N4 C31 1.315(11) . ? N4 Cu2 2.168(7) 1_664 ? C31 C32 1.367(14) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? O5 C33 1.242(10) . ? C33 O6 1.273(10) . ? C33 C34 1.518(12) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O7 C35 1.262(10) . ? C35 O8 1.254(10) . ? C35 C36 1.476(10) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? O9 C37 1.274(10) . ? C37 O10 1.263(10) . ? C37 C38 1.537(11) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? O11 C39 1.244(10) . ? C39 O12 1.255(10) . ? C39 C40 1.504(10) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? Cu3 O19 1.958(6) . ? Cu3 O21 1.967(6) . ? Cu3 O17 1.989(6) . ? Cu3 O23 1.990(6) . ? Cu3 N5 2.146(7) . ? Cu3 Cu4 2.5912(13) . ? Cu4 O18 1.945(6) . ? Cu4 O24 1.963(6) . ? Cu4 O20 1.979(6) . ? Cu4 O22 1.996(6) . ? Cu4 N8 2.190(7) 1_664 ? N5 C45 1.341(11) . ? N5 C41 1.370(11) . ? C41 C42 1.383(13) . ? C41 H41 0.9500 . ? C42 C43 1.389(12) . ? C42 H42 0.9500 . ? C43 C44 1.392(11) . ? C43 C46 1.440(11) . ? C44 C45 1.350(12) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 C47 1.188(11) . ? C47 C48 1.452(12) . ? C48 C57 1.374(12) . ? C48 C49 1.406(11) . ? C49 C52 1.367(11) . ? C49 C50 1.486(12) . ? C50 O13 1.233(11) . ? C50 N6 1.384(11) . ? N6 C51 1.437(11) . ? N6 C58 1.517(11) . ? C51 O14 1.205(10) . ? C51 C52 1.507(11) . ? C52 C53 1.400(11) . ? C53 C66 1.401(11) . ? C53 C54 1.433(10) . ? C54 C57 1.372(12) . ? C54 C55 1.505(12) . ? C55 O15 1.173(11) . ? C55 N7 1.425(11) . ? N7 C56 1.395(12) . ? N7 C62 1.473(13) . ? C56 O16 1.212(10) . ? C56 C57 1.502(12) . ? C58 C61 1.508(13) . ? C58 C59 1.524(14) . ? C58 H58 1.0000 . ? C59 C60 1.424(14) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 0.9800 . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? C62 C63 1.509(15) . ? C62 C65 1.543(15) . ? C62 H62 1.0000 . ? C63 C64 1.516(17) . ? C63 H63A 0.9900 . ? C63 H63B 0.9900 . ? C64 H64A 0.9800 . ? C64 H64B 0.9800 . ? C64 H64C 0.9800 . ? C65 H65A 0.9800 . ? C65 H65B 0.9800 . ? C65 H65C 0.9800 . ? C66 C67 1.192(11) . ? C67 C68 1.445(11) . ? C68 C72 1.364(12) . ? C68 C69 1.384(11) . ? C69 C70 1.382(12) . ? C69 H69 0.9500 . ? C70 N8 1.318(10) . ? C70 H70 0.9500 . ? N8 C71 1.332(11) . ? N8 Cu4 2.190(7) 1_446 ? C71 C72 1.412(12) . ? C71 H71 0.9500 . ? C72 H72 0.9500 . ? O17 C73 1.245(10) . ? C73 O18 1.267(10) . ? C73 C74 1.475(12) . ? C74 H74A 0.9800 . ? C74 H74B 0.9800 . ? C74 H74C 0.9800 . ? O19 C75 1.254(10) . ? C75 O20 1.270(9) . ? C75 C76 1.490(11) . ? C76 H76A 0.9800 . ? C76 H76B 0.9800 . ? C76 H76C 0.9800 . ? O21 C77 1.252(11) . ? C77 O22 1.281(10) . ? C77 C78 1.523(11) . ? C78 H78A 0.9800 . ? C78 H78B 0.9800 . ? C78 H78C 0.9800 . ? O23 C79 1.250(12) . ? C79 O24 1.253(11) . ? C79 C80 1.513(13) . ? C80 H80A 0.9800 . ? C80 H80B 0.9800 . ? C80 H80C 0.9800 . ? C81 Cl1 1.732(9) . ? C81 Cl3 1.757(11) . ? C81 Cl2 1.766(10) . ? C81 H81 1.0000 . ? C82 Cl4 1.712(10) . ? C82 Cl5 1.767(11) . ? C82 Cl6 1.795(11) . ? C82 H82 1.0000 . ? C83 Cl8 1.742(13) . ? C83 Cl9 1.767(11) . ? C83 Cl7 1.776(10) . ? C83 H83 1.0000 . ? C84 Cl10 1.718(10) . ? C84 Cl11 1.763(10) . ? C84 Cl12 1.787(11) . ? C84 H84 1.0000 . ? C85 Cl13 1.731(11) . ? C85 Cl15 1.732(12) . ? C85 Cl14 1.754(13) . ? C85 H85 1.0000 . ? C86 Cl18 1.722(11) . ? C86 Cl16 1.725(12) . ? C86 Cl17 1.757(12) . ? C86 H86 1.0000 . ? C87 Cl21 1.720(10) . ? C87 Cl19 1.739(11) . ? C87 Cl20 1.786(12) . ? C87 H87 1.0000 . ? C88 Cl24 1.635(14) . ? C88 Cl22 1.722(14) . ? C88 Cl23 1.828(13) . ? C88 H88 1.0000 . ? 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 O11 Cu1 O7 171.0(2) . . ? O11 Cu1 O9 87.9(3) . . ? O7 Cu1 O9 90.3(3) . . ? O11 Cu1 O5 91.3(3) . . ? O7 Cu1 O5 88.6(3) . . ? O9 Cu1 O5 167.3(3) . . ? O11 Cu1 N1 94.6(2) . . ? O7 Cu1 N1 94.3(2) . . ? O9 Cu1 N1 99.3(3) . . ? O5 Cu1 N1 93.5(3) . . ? O11 Cu1 Cu2 84.77(18) . . ? O7 Cu1 Cu2 86.31(17) . . ? O9 Cu1 Cu2 84.75(18) . . ? O5 Cu1 Cu2 82.51(18) . . ? N1 Cu1 Cu2 175.9(2) . . ? O6 Cu2 O8 89.8(3) . . ? O6 Cu2 O10 170.7(3) . . ? O8 Cu2 O10 89.8(3) . . ? O6 Cu2 O12 88.6(3) . . ? O8 Cu2 O12 165.7(3) . . ? O10 Cu2 O12 89.5(3) . . ? O6 Cu2 N4 96.3(3) . 1_446 ? O8 Cu2 N4 97.1(3) . 1_446 ? O10 Cu2 N4 93.0(3) . 1_446 ? O12 Cu2 N4 97.1(3) . 1_446 ? O6 Cu2 Cu1 85.80(18) . . ? O8 Cu2 Cu1 82.11(18) . . ? O10 Cu2 Cu1 84.92(19) . . ? O12 Cu2 Cu1 83.63(18) . . ? N4 Cu2 Cu1 177.82(19) 1_446 . ? C1 N1 C5 118.5(7) . . ? C1 N1 Cu1 119.1(6) . . ? C5 N1 Cu1 121.0(5) . . ? N1 C1 C2 124.2(8) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 119.4(8) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C6 119.0(8) . . ? C4 C3 C2 116.4(8) . . ? C6 C3 C2 124.5(8) . . ? C3 C4 C5 120.0(8) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 121.4(7) . . ? N1 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C3 173.2(10) . . ? C6 C7 C8 174.8(9) . . ? C9 C8 C17 113.9(7) . . ? C9 C8 C7 125.9(7) . . ? C17 C8 C7 120.1(7) . . ? C8 C9 C12 122.8(7) . . ? C8 C9 C10 129.5(7) . . ? C12 C9 C10 107.6(7) . . ? O1 C10 N2 127.4(8) . . ? O1 C10 C9 127.9(8) . . ? N2 C10 C9 104.7(7) . . ? C11 N2 C10 113.6(6) . . ? C11 N2 C18 122.8(7) . . ? C10 N2 C18 123.5(7) . . ? O2 C11 N2 126.3(7) . . ? O2 C11 C12 127.4(7) . . ? N2 C11 C12 106.2(6) . . ? C13 C12 C9 121.4(7) . . ? C13 C12 C11 130.8(7) . . ? C9 C12 C11 107.7(6) . . ? C14 C13 C12 116.3(7) . . ? C14 C13 C26 123.6(7) . . ? C12 C13 C26 120.1(7) . . ? C13 C14 C17 122.4(7) . . ? C13 C14 C15 131.0(7) . . ? C17 C14 C15 106.6(7) . . ? O3 C15 N3 126.3(7) . . ? O3 C15 C14 125.4(8) . . ? N3 C15 C14 108.2(7) . . ? C15 N3 C16 111.5(7) . . ? C15 N3 C22 126.7(7) . . ? C16 N3 C22 121.3(6) . . ? O4 C16 N3 125.0(7) . . ? O4 C16 C17 129.7(7) . . ? N3 C16 C17 105.3(6) . . ? C14 C17 C8 123.1(7) . . ? C14 C17 C16 108.3(7) . . ? C8 C17 C16 128.6(7) . . ? N2 C18 C19 111.7(9) . . ? N2 C18 C21 111.0(9) . . ? C19 C18 C21 111.6(9) . . ? N2 C18 H18 107.4 . . ? C19 C18 H18 107.4 . . ? C21 C18 H18 107.4 . . ? C18 C19 C20 115.1(10) . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 C23 112.3(7) . . ? N3 C22 C25 110.9(7) . . ? C23 C22 C25 113.7(7) . . ? N3 C22 H22 106.5 . . ? C23 C22 H22 106.5 . . ? C25 C22 H22 106.5 . . ? C22 C23 C24 113.9(9) . . ? C22 C23 H23A 108.8 . . ? C24 C23 H23A 108.8 . . ? C22 C23 H23B 108.8 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C13 174.7(8) . . ? C26 C27 C28 174.2(8) . . ? C32 C28 C29 117.7(8) . . ? C32 C28 C27 123.1(8) . . ? C29 C28 C27 119.2(8) . . ? C30 C29 C28 117.4(8) . . ? C30 C29 H29 121.3 . . ? C28 C29 H29 121.3 . . ? N4 C30 C29 125.6(8) . . ? N4 C30 H30 117.2 . . ? C29 C30 H30 117.2 . . ? C31 N4 C30 115.1(8) . . ? C31 N4 Cu2 122.0(6) . 1_664 ? C30 N4 Cu2 122.8(6) . 1_664 ? N4 C31 C32 124.9(9) . . ? N4 C31 H31 117.5 . . ? C32 C31 H31 117.5 . . ? C31 C32 C28 119.0(9) . . ? C31 C32 H32 120.5 . . ? C28 C32 H32 120.5 . . ? C33 O5 Cu1 126.5(5) . . ? O5 C33 O6 123.1(8) . . ? O5 C33 C34 119.8(8) . . ? O6 C33 C34 117.1(9) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 O6 Cu2 122.0(6) . . ? C35 O7 Cu1 122.0(5) . . ? O8 C35 O7 123.2(7) . . ? O8 C35 C36 118.6(8) . . ? O7 C35 C36 118.1(8) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 O8 Cu2 126.2(5) . . ? C37 O9 Cu1 122.7(6) . . ? O10 C37 O9 125.7(8) . . ? O10 C37 C38 116.5(8) . . ? O9 C37 C38 117.7(8) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 O10 Cu2 121.8(5) . . ? C39 O11 Cu1 124.5(5) . . ? O11 C39 O12 124.4(7) . . ? O11 C39 C40 119.9(8) . . ? O12 C39 C40 115.7(8) . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 O12 Cu2 122.6(5) . . ? O19 Cu3 O21 173.0(3) . . ? O19 Cu3 O17 89.8(3) . . ? O21 Cu3 O17 89.0(3) . . ? O19 Cu3 O23 90.4(3) . . ? O21 Cu3 O23 89.2(3) . . ? O17 Cu3 O23 167.2(3) . . ? O19 Cu3 N5 94.6(3) . . ? O21 Cu3 N5 92.4(3) . . ? O17 Cu3 N5 100.9(3) . . ? O23 Cu3 N5 91.7(3) . . ? O19 Cu3 Cu4 86.34(18) . . ? O21 Cu3 Cu4 86.66(18) . . ? O17 Cu3 Cu4 83.92(18) . . ? O23 Cu3 Cu4 83.4(2) . . ? N5 Cu3 Cu4 175.0(2) . . ? O18 Cu4 O24 171.9(3) . . ? O18 Cu4 O20 89.3(2) . . ? O24 Cu4 O20 90.2(2) . . ? O18 Cu4 O22 90.9(3) . . ? O24 Cu4 O22 87.7(3) . . ? O20 Cu4 O22 167.1(2) . . ? O18 Cu4 N8 92.2(3) . 1_664 ? O24 Cu4 N8 96.0(3) . 1_664 ? O20 Cu4 N8 94.6(2) . 1_664 ? O22 Cu4 N8 98.2(2) . 1_664 ? O18 Cu4 Cu3 85.22(18) . . ? O24 Cu4 Cu3 86.65(18) . . ? O20 Cu4 Cu3 83.35(16) . . ? O22 Cu4 Cu3 83.87(19) . . ? N8 Cu4 Cu3 176.71(18) 1_664 . ? C45 N5 C41 116.9(7) . . ? C45 N5 Cu3 126.0(6) . . ? C41 N5 Cu3 116.9(6) . . ? N5 C41 C42 122.8(8) . . ? N5 C41 H41 118.6 . . ? C42 C41 H41 118.6 . . ? C41 C42 C43 118.0(8) . . ? C41 C42 H42 121.0 . . ? C43 C42 H42 121.0 . . ? C42 C43 C44 119.0(8) . . ? C42 C43 C46 120.4(8) . . ? C44 C43 C46 120.6(8) . . ? C45 C44 C43 119.3(8) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? N5 C45 C44 123.9(8) . . ? N5 C45 H45 118.1 . . ? C44 C45 H45 118.1 . . ? C47 C46 C43 171.2(9) . . ? C46 C47 C48 172.7(9) . . ? C57 C48 C49 114.4(8) . . ? C57 C48 C47 121.3(8) . . ? C49 C48 C47 124.3(8) . . ? C52 C49 C48 122.0(8) . . ? C52 C49 C50 109.8(7) . . ? C48 C49 C50 128.3(8) . . ? O13 C50 N6 124.2(8) . . ? O13 C50 C49 129.6(8) . . ? N6 C50 C49 106.1(7) . . ? C50 N6 C51 111.4(7) . . ? C50 N6 C58 123.5(7) . . ? C51 N6 C58 125.0(7) . . ? O14 C51 N6 125.8(8) . . ? O14 C51 C52 129.3(8) . . ? N6 C51 C52 104.8(7) . . ? C49 C52 C53 125.3(8) . . ? C49 C52 C51 107.8(7) . . ? C53 C52 C51 126.8(7) . . ? C52 C53 C66 124.1(7) . . ? C52 C53 C54 111.4(7) . . ? C66 C53 C54 124.5(7) . . ? C57 C54 C53 123.2(8) . . ? C57 C54 C55 110.7(7) . . ? C53 C54 C55 126.1(8) . . ? O15 C55 N7 126.4(8) . . ? O15 C55 C54 130.1(8) . . ? N7 C55 C54 103.5(8) . . ? C56 N7 C55 112.2(7) . . ? C56 N7 C62 123.6(8) . . ? C55 N7 C62 124.0(8) . . ? O16 C56 N7 125.3(8) . . ? O16 C56 C57 128.0(9) . . ? N7 C56 C57 106.7(7) . . ? C54 C57 C48 123.8(8) . . ? C54 C57 C56 106.8(8) . . ? C48 C57 C56 129.4(8) . . ? C61 C58 N6 109.2(8) . . ? C61 C58 C59 117.7(8) . . ? N6 C58 C59 107.7(8) . . ? C61 C58 H58 107.3 . . ? N6 C58 H58 107.3 . . ? C59 C58 H58 107.3 . . ? C60 C59 C58 112.6(8) . . ? C60 C59 H59A 109.1 . . ? C58 C59 H59A 109.1 . . ? C60 C59 H59B 109.1 . . ? C58 C59 H59B 109.1 . . ? H59A C59 H59B 107.8 . . ? C59 C60 H60A 109.5 . . ? C59 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C59 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? C58 C61 H61A 109.5 . . ? C58 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C58 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? N7 C62 C63 108.4(10) . . ? N7 C62 C65 114.6(11) . . ? C63 C62 C65 115.1(13) . . ? N7 C62 H62 106.0 . . ? C63 C62 H62 106.0 . . ? C65 C62 H62 106.0 . . ? C62 C63 C64 117.2(13) . . ? C62 C63 H63A 108.0 . . ? C64 C63 H63A 108.0 . . ? C62 C63 H63B 108.0 . . ? C64 C63 H63B 108.0 . . ? H63A C63 H63B 107.2 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C62 C65 H65A 109.5 . . ? C62 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C62 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? C67 C66 C53 176.2(9) . . ? C66 C67 C68 172.9(8) . . ? C72 C68 C69 118.6(8) . . ? C72 C68 C67 119.3(7) . . ? C69 C68 C67 122.1(8) . . ? C70 C69 C68 118.2(8) . . ? C70 C69 H69 120.9 . . ? C68 C69 H69 120.9 . . ? N8 C70 C69 123.3(8) . . ? N8 C70 H70 118.3 . . ? C69 C70 H70 118.3 . . ? C70 N8 C71 119.8(7) . . ? C70 N8 Cu4 120.5(6) . 1_446 ? C71 N8 Cu4 119.2(5) . 1_446 ? N8 C71 C72 119.7(8) . . ? N8 C71 H71 120.1 . . ? C72 C71 H71 120.1 . . ? C68 C72 C71 120.4(8) . . ? C68 C72 H72 119.8 . . ? C71 C72 H72 119.8 . . ? C73 O17 Cu3 123.3(6) . . ? O17 C73 O18 124.1(8) . . ? O17 C73 C74 118.8(8) . . ? O18 C73 C74 117.1(7) . . ? C73 C74 H74A 109.5 . . ? C73 C74 H74B 109.5 . . ? H74A C74 H74B 109.5 . . ? C73 C74 H74C 109.5 . . ? H74A C74 H74C 109.5 . . ? H74B C74 H74C 109.5 . . ? C73 O18 Cu4 123.5(5) . . ? C75 O19 Cu3 121.7(5) . . ? O19 C75 O20 124.8(7) . . ? O19 C75 C76 116.4(7) . . ? O20 C75 C76 118.8(8) . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? C75 O20 Cu4 123.7(5) . . ? C77 O21 Cu3 120.9(6) . . ? O21 C77 O22 126.6(7) . . ? O21 C77 C78 119.5(8) . . ? O22 C77 C78 113.9(8) . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? C77 O22 Cu4 121.9(5) . . ? C79 O23 Cu3 122.4(6) . . ? O23 C79 O24 127.7(9) . . ? O23 C79 C80 115.2(9) . . ? O24 C79 C80 117.1(10) . . ? C79 C80 H80A 109.5 . . ? C79 C80 H80B 109.5 . . ? H80A C80 H80B 109.5 . . ? C79 C80 H80C 109.5 . . ? H80A C80 H80C 109.5 . . ? H80B C80 H80C 109.5 . . ? C79 O24 Cu4 119.9(6) . . ? Cl1 C81 Cl3 110.9(6) . . ? Cl1 C81 Cl2 110.8(5) . . ? Cl3 C81 Cl2 109.8(6) . . ? Cl1 C81 H81 108.4 . . ? Cl3 C81 H81 108.4 . . ? Cl2 C81 H81 108.4 . . ? Cl4 C82 Cl5 111.2(6) . . ? Cl4 C82 Cl6 111.1(6) . . ? Cl5 C82 Cl6 106.6(6) . . ? Cl4 C82 H82 109.3 . . ? Cl5 C82 H82 109.3 . . ? Cl6 C82 H82 109.3 . . ? Cl8 C83 Cl9 110.9(6) . . ? Cl8 C83 Cl7 109.9(6) . . ? Cl9 C83 Cl7 109.8(6) . . ? Cl8 C83 H83 108.7 . . ? Cl9 C83 H83 108.7 . . ? Cl7 C83 H83 108.7 . . ? Cl10 C84 Cl11 109.8(5) . . ? Cl10 C84 Cl12 111.8(6) . . ? Cl11 C84 Cl12 109.5(6) . . ? Cl10 C84 H84 108.6 . . ? Cl11 C84 H84 108.6 . . ? Cl12 C84 H84 108.6 . . ? Cl13 C85 Cl15 112.6(7) . . ? Cl13 C85 Cl14 111.2(6) . . ? Cl15 C85 Cl14 112.2(7) . . ? Cl13 C85 H85 106.8 . . ? Cl15 C85 H85 106.8 . . ? Cl14 C85 H85 106.8 . . ? Cl18 C86 Cl16 111.8(7) . . ? Cl18 C86 Cl17 106.8(7) . . ? Cl16 C86 Cl17 108.4(7) . . ? Cl18 C86 H86 109.9 . . ? Cl16 C86 H86 109.9 . . ? Cl17 C86 H86 109.9 . . ? Cl21 C87 Cl19 112.7(6) . . ? Cl21 C87 Cl20 109.7(6) . . ? Cl19 C87 Cl20 109.6(6) . . ? Cl21 C87 H87 108.2 . . ? Cl19 C87 H87 108.2 . . ? Cl20 C87 H87 108.2 . . ? Cl24 C88 Cl22 114.4(10) . . ? Cl24 C88 Cl23 112.2(7) . . ? Cl22 C88 Cl23 105.5(7) . . ? Cl24 C88 H88 108.2 . . ? Cl22 C88 H88 108.2 . . ? Cl23 C88 H88 108.2 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.865 _refine_diff_density_min -0.864 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 959990' ####################################################################### # # 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_e2913a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C64 H52 Cl2 N8 Ni O8,3(C2 H2 Cl4),2(H2 O)' _chemical_formula_sum 'C70 H62 Cl14 N8 Ni O10' _chemical_formula_weight 1730.29 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 24.5378(9) _cell_length_b 24.9529(11) _cell_length_c 19.2940(7) _cell_angle_alpha 90.00 _cell_angle_beta 121.6010(10) _cell_angle_gamma 90.00 _cell_volume 10061.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9906 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.82 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3536 _exptl_absorpt_coefficient_mu 0.612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9701 _exptl_absorpt_process_details sadabs _exptl_special_details ; Because we didn't identify all the solvents we used the squeezze command We constrained some atoms of the chains bacause of theit flopiness. The hydrogen atoms in the water molecule where not introduced. Note however that these Hs are taken into account in the formula of the product. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26843 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 29.88 _reflns_number_total 26843 _reflns_number_gt 14436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1817P)^2^+0.5000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 26843 _refine_ls_number_parameters 932 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1472 _refine_ls_R_factor_gt 0.0957 _refine_ls_wR_factor_ref 0.2605 _refine_ls_wR_factor_gt 0.2411 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.067 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 Ni1 Ni 0.5000 1.00028(3) 0.5000 0.0296(3) Uani 1 2 d S . . Cl1 Cl 0.41196(8) 1.00049(6) 0.52556(8) 0.0422(4) Uani 1 1 d . . . Ni2 Ni 0.5000 -0.17383(3) 0.0000 0.0292(3) Uani 1 2 d S . . Cl2 Cl 0.41408(8) -0.17428(6) 0.02831(8) 0.0444(4) Uani 1 1 d . . . N1 N 0.5496(2) 0.9413(2) 0.5920(3) 0.0349(12) Uani 1 1 d . . . C1 C 0.6114(3) 0.9426(3) 0.6453(4) 0.0436(16) Uani 1 1 d . . . H1 H 0.6355 0.9694 0.6380 0.052 Uiso 1 1 calc R . . C2 C 0.6438(3) 0.9094(3) 0.7093(3) 0.0455(16) Uani 1 1 d . . . H2 H 0.6886 0.9131 0.7458 0.055 Uiso 1 1 calc R . . C3 C 0.6090(3) 0.8688(3) 0.7207(4) 0.0435(16) Uani 1 1 d . . . C4 C 0.5467(4) 0.8622(3) 0.6619(5) 0.061(2) Uani 1 1 d . . . H4 H 0.5236 0.8324 0.6642 0.073 Uiso 1 1 calc R . . C5 C 0.5169(4) 0.8979(3) 0.5996(5) 0.071(3) Uani 1 1 d . . . H5 H 0.4727 0.8933 0.5603 0.086 Uiso 1 1 calc R . . C6 C 0.6411(4) 0.8381(4) 0.7907(4) 0.063(2) Uani 1 1 d . . . C7 C 0.6662(4) 0.8085(3) 0.8515(4) 0.064(2) Uani 1 1 d . . . C8 C 0.6986(3) 0.7786(3) 0.9257(4) 0.061(2) Uani 1 1 d . . . C9 C 0.6761(3) 0.7320(3) 0.9376(4) 0.0461(17) Uani 1 1 d . . . C10 C 0.6112(4) 0.7027(4) 0.8782(5) 0.075(3) Uani 1 1 d . . . O1 O 0.5762(3) 0.7155(3) 0.8143(3) 0.086(2) Uani 1 1 d . . . N2 N 0.6170(4) 0.6545(3) 0.9244(5) 0.086(2) Uani 1 1 d D . . C11 C 0.6704(4) 0.6526(3) 0.9979(4) 0.0520(18) Uani 1 1 d . . . O2 O 0.6817(4) 0.6193(3) 1.0490(4) 0.091(2) Uani 1 1 d D . . C12 C 0.7072(3) 0.6992(3) 1.0071(4) 0.0411(16) Uani 1 1 d . . . C13 C 0.7653(4) 0.7119(3) 1.0681(5) 0.065(3) Uani 1 1 d . . . C14 C 0.7929(4) 0.7648(4) 1.0615(5) 0.065(2) Uani 1 1 d . . . C15 C 0.7599(4) 0.7932(3) 0.9899(4) 0.0529(19) Uani 1 1 d . . . C16 C 0.8579(4) 0.7872(5) 1.1170(7) 0.100(4) Uani 1 1 d . . . O3 O 0.9007(3) 0.7743(3) 1.1802(4) 0.111(3) Uani 1 1 d . . . N3 N 0.8578(3) 0.8314(3) 1.0659(4) 0.087(3) Uani 1 1 d D . . C17 C 0.8054(5) 0.8370(3) 0.9967(4) 0.077(3) Uani 1 1 d . . . O4 O 0.7886(4) 0.8732(3) 0.9481(4) 0.108(3) Uani 1 1 d . . . C18 C 0.5591(5) 0.6172(4) 0.8797(6) 0.111(4) Uani 1 1 d D . . H18 H 0.5326 0.6405 0.8312 0.133 Uiso 1 1 calc R . . C19 C 0.5198(6) 0.6256(9) 0.9211(8) 0.111(4) Uani 0.664(12) 1 d PD C 1 H19A H 0.4858 0.5981 0.9024 0.133 Uiso 0.664(12) 1 calc PR C 1 H19B H 0.4997 0.6615 0.9079 0.133 Uiso 0.664(12) 1 calc PR C 1 C20 C 0.5683(6) 0.6203(7) 1.0142(7) 0.111(4) Uani 0.664(12) 1 d PD C 1 H20A H 0.6089 0.6061 1.0236 0.133 Uiso 0.664(12) 1 calc PR C 1 H20B H 0.5511 0.5957 1.0377 0.133 Uiso 0.664(12) 1 calc PR C 1 H20C H 0.5755 0.6555 1.0398 0.133 Uiso 0.664(12) 1 calc PR C 1 C21 C 0.5710(5) 0.5720(5) 0.8358(8) 0.176(9) Uani 1 1 d D . . H21A H 0.6104 0.5794 0.8361 0.264 Uiso 1 1 calc R C 4 H21B H 0.5349 0.5697 0.7795 0.264 Uiso 1 1 calc R C 4 H21C H 0.5755 0.5380 0.8637 0.264 Uiso 1 1 calc R C 4 C22 C 0.9073(6) 0.8763(7) 1.1036(8) 0.176(9) Uani 1 1 d D . . H22 H 0.8817 0.9060 1.0657 0.264 Uiso 1 1 calc R C 4 C23 C 0.9418(17) 0.8564(11) 1.061(3) 0.176(9) Uani 1 1 d D C . H23A H 0.9098 0.8584 1.0015 0.264 Uiso 1 1 calc R . . H23B H 0.9747 0.8838 1.0717 0.264 Uiso 1 1 calc R . . C24 C 0.9737(8) 0.8040(15) 1.074(2) 0.176(9) Uani 1 1 d D . . H24A H 0.9591 0.7868 1.0215 0.264 Uiso 1 1 calc R C . H24B H 0.9631 0.7812 1.1067 0.264 Uiso 1 1 calc R . . H24C H 1.0202 0.8093 1.1030 0.264 Uiso 1 1 calc R . . C25 C 0.9160(7) 0.8991(6) 1.1830(9) 0.176(9) Uani 1 1 d D C . H25A H 0.9242 0.9377 1.1856 0.264 Uiso 1 1 calc R . . H25B H 0.9523 0.8813 1.2297 0.264 Uiso 1 1 calc R . . H25C H 0.8770 0.8928 1.1840 0.264 Uiso 1 1 calc R . . C26 C 0.8020(3) 0.6822(3) 1.1410(4) 0.0465(17) Uani 1 1 d . . . C27 C 0.8343(3) 0.6582(3) 1.2056(4) 0.0463(17) Uani 1 1 d . . . C28 C 0.3743(3) 1.1234(3) 0.2726(3) 0.0359(14) Uani 1 1 d . . . C29 C 0.3694(3) 1.1267(3) 0.3437(3) 0.0383(15) Uani 1 1 d . . . H29 H 0.3404 1.1510 0.3457 0.046 Uiso 1 1 calc R . . C30 C 0.4077(4) 1.0940(2) 0.4084(3) 0.0476(18) Uani 1 1 d . . . H30 H 0.4045 1.0956 0.4553 0.057 Uiso 1 1 calc R . . N4 N 0.4503(3) 1.0593(2) 0.4076(2) 0.0350(12) Uani 1 1 d . . . C31 C 0.4525(4) 1.0588(3) 0.3425(4) 0.0456(16) Uani 1 1 d . . . H31 H 0.4820 1.0345 0.3417 0.055 Uiso 1 1 calc R . . C32 C 0.4165(4) 1.0898(3) 0.2732(3) 0.0457(2) Uani 1 1 d . . . H32 H 0.4218 1.0871 0.2280 0.065 Uiso 1 1 calc R . . N5 N 0.5490(2) -0.11354(19) 0.0893(3) 0.0394(14) Uani 1 1 d . . . C33 C 0.6137(3) -0.1146(3) 0.1369(3) 0.0450(17) Uani 1 1 d . . . H33 H 0.6370 -0.1398 0.1256 0.054 Uiso 1 1 calc R . . C34 C 0.6473(4) -0.0787(3) 0.2035(4) 0.058(2) Uani 1 1 d . . . H34 H 0.6927 -0.0787 0.2350 0.069 Uiso 1 1 calc R . . C35 C 0.6138(3) -0.0450(3) 0.2208(4) 0.0505(18) Uani 1 1 d . . . C36 C 0.5489(5) -0.0453(5) 0.1730(8) 0.0505(18) Uani 1 1 d . . . H36 H 0.5232 -0.0242 0.1858 0.066 Uiso 1 1 calc R . . C37 C 0.5219(3) -0.0780(3) 0.1040(5) 0.0505(18) Uani 1 1 d . . . H37 H 0.4781 -0.0721 0.0644 0.066 Uiso 1 1 calc R . . C38 C 0.6451(3) -0.0092(3) 0.2930(4) 0.0519(18) Uani 1 1 d . . . C39 C 0.6713(3) 0.0149(3) 0.3553(4) 0.0478(17) Uani 1 1 d . . . C40 C 0.7029(3) 0.0475(2) 0.4244(3) 0.0377(15) Uani 1 1 d . . . C41 C 0.7632(3) 0.0374(3) 0.4915(4) 0.0431(15) Uani 1 1 d . . . C42 C 0.8066(4) -0.0115(4) 0.5070(5) 0.064(2) Uani 1 1 d . . . O5 O 0.7983(3) -0.0464(3) 0.4576(3) 0.0829(19) Uani 1 1 d . . . N6 N 0.8613(3) -0.0031(3) 0.5830(3) 0.0673(18) Uani 1 1 d D . . C43 C 0.8535(4) 0.0417(3) 0.6151(4) 0.0528(18) Uani 1 1 d . . . O6 O 0.8970(3) 0.0592(3) 0.6842(3) 0.086(2) Uani 1 1 d . . . C44 C 0.7930(3) 0.0680(3) 0.5605(3) 0.0407(15) Uani 1 1 d . . . C45 C 0.7658(3) 0.1108(2) 0.5726(3) 0.0364(14) Uani 1 1 d . . . C46 C 0.7054(4) 0.1249(3) 0.5033(4) 0.0484(18) Uani 1 1 d . . . C47 C 0.6595(4) 0.1703(3) 0.4909(4) 0.055(2) Uani 1 1 d . . . O7 O 0.6703(3) 0.2065(2) 0.5386(3) 0.0576(13) Uani 1 1 d . . . N7 N 0.6067(2) 0.1641(2) 0.4137(3) 0.0439(13) Uani 1 1 d D . . C48 C 0.6146(4) 0.1192(3) 0.3775(4) 0.0527(19) Uani 1 1 d . . . O8 O 0.5709(2) 0.1057(2) 0.3043(3) 0.0584(13) Uani 1 1 d . . . C49 C 0.6740(3) 0.0949(3) 0.4321(3) 0.0447(18) Uani 1 1 d . . . C50 C 0.9210(4) -0.0350(4) 0.6172(6) 0.092(3) Uani 1 1 d D . . H50 H 0.9484 -0.0213 0.6741 0.110 Uiso 1 1 calc R . . C51 C 0.9598(6) -0.0255(7) 0.5800(8) 0.121(5) Uani 1 1 d D . . H51A H 1.0050 -0.0307 0.6241 0.146 Uiso 1 1 calc R . . H51B H 0.9494 -0.0551 0.5408 0.146 Uiso 1 1 calc R . . C52 C 0.9581(14) 0.0240(12) 0.538(3) 0.121(5) Uani 1 1 d D . . H52A H 0.9887 0.0212 0.5196 0.146 Uiso 0.50 1 calc PR . . H52B H 0.9696 0.0546 0.5746 0.146 Uiso 0.50 1 calc PR . . H52C H 0.9150 0.0293 0.4901 0.146 Uiso 0.50 1 calc PR . . H52D H 0.9268 0.0488 0.5366 0.146 Uiso 0.50 1 calc PR . . H52E H 0.9459 0.0155 0.4817 0.146 Uiso 0.50 1 calc PR . . H52F H 1.0006 0.0407 0.5661 0.146 Uiso 0.50 1 calc PR . . C53 C 0.9110(6) -0.0931(4) 0.6282(9) 0.123(4) Uani 1 1 d D . . H53A H 0.9324 -0.1155 0.6080 0.184 Uiso 1 1 calc R . . H53B H 0.8650 -0.1010 0.5977 0.184 Uiso 1 1 calc R . . H53C H 0.9288 -0.1004 0.6861 0.184 Uiso 1 1 calc R . . C54 C 0.5524(4) 0.2023(3) 0.3744(5) 0.075(2) Uani 1 1 d D . . H54 H 0.5218 0.1887 0.3183 0.091 Uiso 1 1 calc R . . C55 C 0.5753(5) 0.2545(4) 0.3662(6) 0.092(3) Uani 1 1 d D . . H55A H 0.6083 0.2673 0.4212 0.110 Uiso 1 1 calc R . . H55B H 0.5392 0.2802 0.3441 0.110 Uiso 1 1 calc R . . C56 C 0.6036(6) 0.2558(5) 0.3119(9) 0.134(5) Uani 1 1 d D . . H56A H 0.5791 0.2318 0.2654 0.201 Uiso 1 1 calc R . . H56B H 0.6483 0.2440 0.3433 0.201 Uiso 1 1 calc R . . H56C H 0.6015 0.2924 0.2923 0.201 Uiso 1 1 calc R . . C57 C 0.5165(4) 0.2065(3) 0.4179(6) 0.070(2) Uani 1 1 d D . . H57A H 0.4796 0.2304 0.3874 0.105 Uiso 1 1 calc R . . H57B H 0.5448 0.2210 0.4726 0.105 Uiso 1 1 calc R . . H57C H 0.5016 0.1709 0.4220 0.105 Uiso 1 1 calc R . . C58 C 0.7991(4) 0.1439(3) 0.6454(4) 0.0515(19) Uani 1 1 d . . . C59 C 0.8282(3) 0.1716(3) 0.7005(4) 0.0466(17) Uani 1 1 d . . . C60 C 0.6343(4) -0.2974(3) 0.2271(4) 0.0480(17) Uani 1 1 d . . . C61 C 0.5862(4) -0.2616(3) 0.2282(5) 0.065(2) Uani 1 1 d . . . H61 H 0.5818 -0.2607 0.2744 0.078 Uiso 1 1 calc R . . C62 C 0.5481(4) -0.2298(3) 0.1617(3) 0.063(2) Uani 1 1 d . . . H62 H 0.5191 -0.2055 0.1636 0.058 Uiso 1 1 calc R . . N8 N 0.5509(2) -0.23246(16) 0.0933(3) 0.0308(11) Uani 1 1 d . . . C63 C 0.5916(3) -0.2665(2) 0.0919(3) 0.0374(15) Uani 1 1 d . . . H63 H 0.5927 -0.2689 0.0435 0.045 Uiso 1 1 calc R . . C64 C 0.6335(4) -0.2992(3) 0.1581(4) 0.0509(18) Uani 1 1 d . . . H64 H 0.6616 -0.3228 0.1531 0.061 Uiso 1 1 calc R . . Cl3 Cl 0.2622(3) 0.8072(2) 0.7206(4) 0.273(4) Uani 1 1 d D . . Cl4 Cl 0.1461(4) 0.7812(2) 0.7100(3) 0.239(4) Uani 1 1 d D . . C65 C 0.1813(4) 0.8028(3) 0.6596(5) 0.075(2) Uani 1 1 d D . . H65 H 0.1729 0.7744 0.6186 0.090 Uiso 1 1 calc R . . Cl5 Cl 0.16547(14) 0.90488(10) 0.69061(18) 0.1006(8) Uani 1 1 d D . . Cl6 Cl 0.0769(2) 0.8457(2) 0.5463(2) 0.1704(18) Uani 1 1 d D . . C66 C 0.1689(5) 0.8596(3) 0.6124(4) 0.116(5) Uani 1 1 d D . . H66 H 0.1939 0.8701 0.5870 0.139 Uiso 1 1 calc R . . Cl7 Cl 0.2804(3) 1.0224(3) 0.0511(4) 0.247(4) Uani 1 1 d . . . Cl8 Cl 0.39698(17) 0.97030(13) 0.15515(17) 0.1061(10) Uani 1 1 d . . . C67 C 0.3223(9) 0.9585(6) 0.0690(11) 0.164(8) Uani 1 1 d . . . H67 H 0.2995 0.9295 0.0798 0.197 Uiso 1 1 calc R . . Cl9 Cl 0.36797(16) 0.99499(14) -0.0267(2) 0.1089(9) Uani 1 1 d . . . Cl10 Cl 0.25332(16) 0.9260(3) -0.0914(2) 0.170(2) Uani 1 1 d . . . C68 C 0.3241(8) 0.9461(5) -0.0041(7) 0.124(5) Uani 1 1 d . . . H68 H 0.3516 0.9134 0.0118 0.149 Uiso 1 1 calc R . . Cl11 Cl 0.7482(2) 0.81278(17) 0.4889(3) 0.1583(16) Uani 1 1 d . . . Cl12 Cl 0.61730(18) 0.85269(15) 0.36057(19) 0.1190(11) Uani 1 1 d . . . C69 C 0.6922(5) 0.8673(5) 0.4506(8) 0.110(4) Uani 1 1 d . . . H69 H 0.7122 0.8987 0.4400 0.132 Uiso 1 1 calc R . . Cl13 Cl 0.74628(15) 0.90982(19) 0.5943(2) 0.1356(13) Uani 1 1 d . . . Cl14 Cl 0.64089(19) 0.83251(18) 0.5397(2) 0.1303(11) Uani 1 1 d . . . C70 C 0.6738(4) 0.8840(4) 0.5148(6) 0.083(3) Uani 1 1 d . . . H70 H 0.6420 0.9139 0.4913 0.100 Uiso 1 1 calc R . . O9 O 0.8799(3) 0.9499(3) 0.7870(3) 0.0843(17) Uani 1 1 d . . . O10 O 0.2414(3) 0.0283(2) 0.2713(4) 0.0865(18) Uani 1 1 d . . . C19A C 0.5509(16) 0.5958(10) 0.9485(15) 0.107 Uani 0.336(12) 1 d PD C 2 H19C H 0.5056 0.5865 0.9276 0.128 Uiso 0.336(12) 1 calc PR C 2 H19D H 0.5650 0.6228 0.9923 0.128 Uiso 0.336(12) 1 calc PR C 2 C20A C 0.5937(16) 0.5453(11) 0.9803(14) 0.107 Uani 0.336(12) 1 d PD C 2 H20D H 0.6316 0.5528 1.0338 0.160 Uiso 0.336(12) 1 calc PR C 2 H20E H 0.6070 0.5353 0.9421 0.160 Uiso 0.336(12) 1 calc PR C 2 H20F H 0.5696 0.5157 0.9850 0.160 Uiso 0.336(12) 1 calc PR C 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 Ni1 0.0437(6) 0.0150(5) 0.0105(4) 0.000 0.0007(4) 0.000 Cl1 0.0609(10) 0.0322(8) 0.0251(6) -0.0028(6) 0.0166(7) -0.0060(8) Ni2 0.0486(6) 0.0159(5) 0.0066(3) 0.000 0.0031(4) 0.000 Cl2 0.0723(11) 0.0306(8) 0.0360(7) 0.0067(7) 0.0323(8) 0.0096(8) N1 0.050(3) 0.026(3) 0.020(2) 0.0084(19) 0.012(2) 0.000(2) C1 0.039(4) 0.046(4) 0.040(3) 0.019(3) 0.016(3) 0.002(3) C2 0.032(3) 0.071(5) 0.021(2) 0.016(3) 0.006(3) 0.003(3) C3 0.052(4) 0.030(3) 0.028(3) 0.022(2) 0.007(3) 0.012(3) C4 0.054(5) 0.040(4) 0.063(4) 0.028(3) 0.014(4) 0.002(3) C5 0.059(5) 0.044(4) 0.067(5) 0.016(4) 0.002(4) -0.024(4) C6 0.075(5) 0.075(6) 0.050(4) 0.047(4) 0.041(4) 0.047(4) C7 0.076(5) 0.076(6) 0.052(4) 0.049(4) 0.042(4) 0.046(4) C8 0.073(5) 0.073(6) 0.048(4) 0.048(4) 0.040(4) 0.045(4) C9 0.049(4) 0.038(4) 0.033(3) 0.022(3) 0.009(3) 0.009(3) C10 0.065(5) 0.097(7) 0.035(4) 0.014(4) 0.005(4) -0.012(5) O1 0.093(4) 0.095(5) 0.025(2) 0.018(3) 0.000(3) 0.005(4) N2 0.102(6) 0.054(4) 0.093(6) 0.024(4) 0.045(5) 0.010(4) C11 0.060(4) 0.045(4) 0.039(3) 0.023(3) 0.018(3) 0.015(3) O2 0.143(6) 0.042(3) 0.081(4) 0.030(3) 0.053(4) 0.007(4) C12 0.056(4) 0.045(4) 0.025(3) 0.012(3) 0.023(3) 0.020(3) C13 0.096(7) 0.064(5) 0.059(5) 0.039(4) 0.058(5) 0.050(5) C14 0.075(6) 0.054(5) 0.055(4) 0.021(4) 0.027(4) 0.009(4) C15 0.065(5) 0.049(4) 0.038(3) 0.028(3) 0.023(4) 0.021(4) C16 0.047(5) 0.112(8) 0.101(7) 0.064(7) 0.010(5) -0.001(5) O3 0.085(5) 0.109(6) 0.067(4) 0.060(4) -0.009(4) 0.001(4) N3 0.063(4) 0.084(5) 0.067(4) 0.043(4) 0.003(4) -0.014(4) C17 0.109(7) 0.052(5) 0.033(3) 0.025(3) 0.012(4) 0.012(5) O4 0.150(6) 0.062(4) 0.069(4) 0.036(3) 0.028(4) 0.002(4) C18 0.145(10) 0.105(9) 0.065(5) -0.037(6) 0.043(6) -0.073(8) C19 0.145(10) 0.105(9) 0.065(5) -0.037(6) 0.043(6) -0.073(8) C20 0.145(10) 0.105(9) 0.065(5) -0.037(6) 0.043(6) -0.073(8) C21 0.064(7) 0.097(10) 0.203(15) -0.036(10) -0.043(9) 0.000(6) C22 0.064(7) 0.097(10) 0.203(15) -0.036(10) -0.043(9) 0.000(6) C23 0.064(7) 0.097(10) 0.203(15) -0.036(10) -0.043(9) 0.000(6) C24 0.064(7) 0.097(10) 0.203(15) -0.036(10) -0.043(9) 0.000(6) C25 0.064(7) 0.097(10) 0.203(15) -0.036(10) -0.043(9) 0.000(6) C26 0.057(4) 0.046(4) 0.028(3) 0.012(3) 0.017(3) 0.018(3) C27 0.051(4) 0.045(4) 0.028(3) 0.010(3) 0.010(3) 0.016(3) C28 0.035(3) 0.032(3) 0.013(2) 0.011(2) -0.006(2) 0.008(2) C29 0.035(3) 0.037(3) 0.020(2) -0.001(2) -0.001(2) 0.015(3) C30 0.097(5) 0.024(3) 0.025(3) 0.008(2) 0.033(3) 0.025(3) N4 0.051(3) 0.034(3) 0.0110(19) 0.0019(18) 0.010(2) 0.009(2) C31 0.067(4) 0.025(3) 0.034(3) 0.004(2) 0.018(3) 0.005(3) C32 0.068(6) 0.025(3) 0.036(2) 0.002(2) 0.019(3) 0.006(4) N5 0.046(3) 0.016(2) 0.015(2) -0.0007(17) -0.013(2) 0.005(2) C33 0.051(4) 0.052(4) 0.023(3) -0.030(3) 0.012(3) -0.024(3) C34 0.064(5) 0.052(4) 0.037(3) -0.030(3) 0.012(3) -0.025(4) C35 0.052(4) 0.059(5) 0.031(3) -0.017(3) 0.015(3) -0.005(3) C36 0.053(6) 0.056(10) 0.034(11) -0.013(10) 0.019(7) -0.008(6) C37 0.051(4) 0.058(4) 0.036(4) -0.017(4) 0.020(4) -0.010(3) C38 0.057(4) 0.040(4) 0.030(3) -0.021(3) 0.003(3) -0.010(3) C39 0.037(3) 0.040(4) 0.057(4) -0.016(3) 0.019(3) -0.001(3) C40 0.068(4) 0.033(3) 0.028(3) -0.006(2) 0.037(3) -0.010(3) C41 0.051(4) 0.039(4) 0.035(3) -0.011(3) 0.020(3) -0.008(3) C42 0.076(5) 0.068(5) 0.067(5) -0.009(4) 0.052(5) 0.005(4) O5 0.085(4) 0.083(4) 0.066(3) -0.049(3) 0.030(3) 0.005(3) N6 0.074(4) 0.077(5) 0.031(3) -0.018(3) 0.014(3) -0.004(4) C43 0.055(4) 0.063(5) 0.027(3) -0.007(3) 0.013(3) -0.006(4) O6 0.079(4) 0.113(5) 0.036(2) -0.019(3) 0.009(3) 0.029(4) C44 0.051(4) 0.042(3) 0.027(3) -0.021(2) 0.018(3) -0.025(3) C45 0.050(4) 0.037(3) 0.016(2) -0.012(2) 0.013(3) -0.010(3) C46 0.070(5) 0.035(4) 0.031(3) -0.029(3) 0.020(3) -0.016(3) C47 0.076(5) 0.051(4) 0.036(3) -0.013(3) 0.027(3) -0.027(4) O7 0.090(4) 0.044(3) 0.040(2) -0.017(2) 0.034(3) -0.001(3) N7 0.041(3) 0.048(3) 0.023(2) -0.014(2) 0.003(2) -0.003(2) C48 0.079(5) 0.046(4) 0.051(4) -0.014(3) 0.047(4) -0.029(4) O8 0.049(3) 0.072(4) 0.029(2) -0.017(2) 0.004(2) -0.011(2) C49 0.054(4) 0.060(5) 0.024(3) -0.018(3) 0.024(3) -0.030(4) C50 0.092(7) 0.080(6) 0.073(6) -0.021(5) 0.022(6) 0.005(5) C51 0.074(7) 0.151(13) 0.120(9) -0.024(9) 0.037(7) 0.006(8) C52 0.074(7) 0.151(13) 0.120(9) -0.024(9) 0.037(7) 0.006(8) C53 0.126(9) 0.086(8) 0.129(10) 0.023(7) 0.047(8) 0.040(7) C54 0.095(6) 0.053(5) 0.064(5) -0.005(4) 0.032(5) -0.017(5) C55 0.123(8) 0.063(5) 0.091(6) 0.032(5) 0.057(6) -0.001(5) C56 0.107(8) 0.105(9) 0.222(15) 0.083(10) 0.108(10) 0.046(7) C57 0.061(5) 0.051(4) 0.100(6) -0.009(4) 0.044(5) -0.013(3) C58 0.070(5) 0.051(5) 0.037(3) -0.028(3) 0.031(4) -0.026(4) C59 0.057(4) 0.028(3) 0.032(3) -0.015(3) 0.007(3) -0.004(3) C60 0.090(5) 0.024(3) 0.024(3) 0.010(2) 0.026(3) 0.012(3) C61 0.076(5) 0.050(5) 0.050(4) 0.017(3) 0.021(4) 0.044(4) C62 0.079(5) 0.049(4) 0.049(2) 0.018(2) 0.025(3) 0.042(4) N8 0.051(3) 0.006(2) 0.020(2) 0.0037(16) 0.008(2) 0.002(2) C63 0.045(3) 0.033(3) 0.015(2) 0.009(2) 0.003(3) -0.005(3) C64 0.081(5) 0.029(3) 0.045(3) 0.023(3) 0.035(4) 0.010(3) Cl3 0.179(4) 0.170(5) 0.254(6) -0.080(4) -0.036(4) 0.107(4) Cl4 0.433(10) 0.152(4) 0.110(3) -0.015(3) 0.126(4) -0.140(5) C65 0.128(7) 0.040(4) 0.088(6) -0.004(4) 0.079(6) -0.016(4) Cl5 0.1169(19) 0.0670(14) 0.1074(18) -0.0239(13) 0.0514(16) -0.0103(13) Cl6 0.157(3) 0.205(5) 0.086(2) -0.027(2) 0.019(2) -0.005(3) C66 0.215(12) 0.024(3) 0.036(3) 0.007(3) 0.015(5) -0.043(5) Cl7 0.244(6) 0.288(8) 0.278(7) 0.010(6) 0.185(6) 0.153(6) Cl8 0.157(3) 0.097(2) 0.0919(17) -0.0368(15) 0.0849(18) -0.0467(18) C67 0.29(2) 0.090(9) 0.217(16) -0.093(10) 0.201(17) -0.069(11) Cl9 0.136(2) 0.0858(19) 0.132(2) 0.0360(18) 0.089(2) 0.0363(18) Cl10 0.085(2) 0.297(7) 0.090(2) 0.000(3) 0.0194(18) 0.004(3) C68 0.191(13) 0.084(8) 0.079(7) 0.004(6) 0.057(8) 0.032(9) Cl11 0.148(3) 0.130(3) 0.214(4) 0.023(3) 0.107(3) 0.074(3) Cl12 0.148(3) 0.108(2) 0.0961(19) -0.0395(17) 0.0606(19) -0.029(2) C69 0.094(7) 0.136(11) 0.119(8) 0.074(8) 0.068(7) 0.046(7) Cl13 0.090(2) 0.147(3) 0.136(3) -0.011(2) 0.036(2) 0.006(2) Cl14 0.161(3) 0.108(3) 0.148(3) 0.011(2) 0.099(3) -0.002(2) C70 0.053(5) 0.103(8) 0.082(6) 0.010(5) 0.028(5) 0.019(5) O9 0.089(4) 0.089(4) 0.071(3) -0.023(3) 0.039(3) 0.004(3) O10 0.073(3) 0.060(3) 0.127(5) -0.039(3) 0.052(4) -0.006(3) C19A 0.120 0.094 0.092 0.000 0.045 0.000 C20A 0.120 0.094 0.092 0.000 0.045 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.130(5) . ? Ni1 N1 2.130(5) 2_656 ? Ni1 N4 2.135(5) . ? Ni1 N4 2.135(5) 2_656 ? Ni1 Cl1 2.4549(17) . ? Ni1 Cl1 2.4549(17) 2_656 ? Ni2 N5 2.123(4) 2_655 ? Ni2 N5 2.123(4) . ? Ni2 N8 2.141(4) . ? Ni2 N8 2.141(4) 2_655 ? Ni2 Cl2 2.4394(16) 2_655 ? Ni2 Cl2 2.4394(16) . ? N1 C1 1.312(8) . ? N1 C5 1.400(9) . ? C1 C2 1.348(9) . ? C1 H1 0.9500 . ? C2 C3 1.413(10) . ? C2 H2 0.9500 . ? C3 C4 1.353(10) . ? C3 C6 1.385(8) . ? C4 C5 1.362(10) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.242(8) . ? C7 C8 1.430(7) . ? C8 C9 1.357(10) . ? C8 C15 1.406(11) . ? C9 C12 1.407(8) . ? C9 C10 1.572(11) . ? C10 O1 1.119(9) . ? C10 N2 1.459(12) . ? N2 C11 1.335(10) . ? N2 C18 1.532(8) . ? C11 O2 1.204(8) . ? C11 C12 1.426(11) . ? C12 C13 1.327(12) . ? C13 C26 1.419(9) . ? C13 C14 1.519(13) . ? C14 C15 1.376(10) . ? C14 C16 1.487(14) . ? C15 C17 1.519(13) . ? C16 O3 1.162(10) . ? C16 N3 1.479(12) . ? N3 C17 1.288(10) . ? N3 C22 1.527(13) . ? C17 O4 1.207(9) . ? C18 C21 1.527(9) . ? C18 C19A 1.539(9) . ? C18 C19 1.555(9) . ? C18 H18 1.0000 . ? C19 C20 1.555(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C21 H21A 0.9803 . ? C21 H21B 0.9803 . ? C21 H21C 0.9803 . ? C22 C25 1.540(17) . ? C22 C23 1.544(18) . ? C22 H22 1.0000 . ? C23 C24 1.477(18) . ? C27 C28 1.435(8) 3_546 ? C28 C32 1.328(10) . ? C28 C27 1.434(8) 3_454 ? C28 C29 1.440(8) . ? C29 C30 1.371(8) . ? C29 H29 0.9500 . ? C30 N4 1.363(8) . ? C30 H30 0.9500 . ? N4 C31 1.286(8) . ? C31 C32 1.389(8) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? N5 C37 1.227(8) . ? N5 C33 1.356(9) . ? C33 C34 1.421(8) . ? C33 H33 0.9500 . ? C34 C35 1.335(10) . ? C34 H34 0.9500 . ? C35 C36 1.358(12) . ? C35 C38 1.485(9) . ? C36 C37 1.397(10) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 C39 1.188(9) . ? C39 C40 1.399(9) . ? C40 C41 1.385(9) . ? C40 C49 1.428(10) . ? C41 C44 1.367(8) . ? C41 C42 1.544(11) . ? C42 O5 1.226(9) . ? C42 N6 1.391(10) . ? N6 C43 1.339(10) . ? N6 C50 1.485(8) . ? C43 O6 1.272(8) . ? C43 C44 1.451(10) . ? C44 C45 1.344(9) . ? C45 C46 1.425(10) . ? C45 C58 1.456(8) . ? C46 C49 1.388(8) . ? C46 C47 1.525(12) . ? C47 O7 1.215(8) . ? C47 N7 1.377(8) . ? N7 C48 1.388(9) . ? N7 C54 1.483(9) . ? C48 O8 1.292(8) . ? C48 C49 1.410(11) . ? C50 C51 1.480(9) . ? C50 C53 1.502(9) . ? C50 H50 1.0000 . ? C51 C52 1.472(10) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C52 H52D 0.9800 . ? C52 H52E 0.9800 . ? C52 H52F 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 C55 1.459(10) . ? C54 C57 1.506(10) . ? C54 H54 1.0000 . ? C55 C56 1.531(13) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 H56A 0.9801 . ? C56 H56B 0.9801 . ? C56 H56C 0.9801 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C58 C59 1.150(8) . ? C59 C60 1.430(8) 4_656 ? C60 C64 1.323(9) . ? C60 C59 1.430(8) 4_646 ? C60 C61 1.490(10) . ? C61 C62 1.376(8) . ? C61 H61 0.9500 . ? C62 N8 1.357(7) . ? C62 H62 0.9500 . ? N8 C63 1.323(8) . ? C63 C64 1.405(8) . ? C63 H63 0.9500 . ? C64 H64 0.9500 . ? Cl3 C65 1.701(10) . ? Cl4 C65 1.690(8) . ? C65 C66 1.624(9) . ? C65 H65 1.0000 . ? Cl5 C66 1.922(8) . ? Cl6 C66 1.955(9) . ? C66 H66 1.0000 . ? Cl7 C67 1.830(17) . ? Cl8 C67 1.736(19) . ? C67 C68 1.467(18) . ? C67 H67 1.0000 . ? Cl9 C68 1.824(16) . ? Cl10 C68 1.743(15) . ? C68 H68 1.0000 . ? Cl11 C69 1.795(11) . ? Cl12 C69 1.784(14) . ? C69 C70 1.580(15) . ? C69 H69 1.0000 . ? Cl13 C70 1.752(10) . ? Cl14 C70 1.715(11) . ? C70 H70 1.0000 . ? C19A C20A 1.548(10) . ? C19A H19C 0.9900 . ? C19A H19D 0.9900 . ? 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 Ni1 N1 92.6(3) . 2_656 ? N1 Ni1 N4 179.9(2) . . ? N1 Ni1 N4 87.37(17) 2_656 . ? N1 Ni1 N4 87.37(17) . 2_656 ? N1 Ni1 N4 179.9(2) 2_656 2_656 ? N4 Ni1 N4 92.7(3) . 2_656 ? N1 Ni1 Cl1 90.75(14) . . ? N1 Ni1 Cl1 89.42(15) 2_656 . ? N4 Ni1 Cl1 89.35(15) . . ? N4 Ni1 Cl1 90.48(15) 2_656 . ? N1 Ni1 Cl1 89.42(15) . 2_656 ? N1 Ni1 Cl1 90.75(14) 2_656 2_656 ? N4 Ni1 Cl1 90.48(15) . 2_656 ? N4 Ni1 Cl1 89.35(15) 2_656 2_656 ? Cl1 Ni1 Cl1 179.75(8) . 2_656 ? N5 Ni2 N5 89.7(2) 2_655 . ? N5 Ni2 N8 177.95(18) 2_655 . ? N5 Ni2 N8 88.24(15) . . ? N5 Ni2 N8 88.23(15) 2_655 2_655 ? N5 Ni2 N8 177.95(18) . 2_655 ? N8 Ni2 N8 93.8(2) . 2_655 ? N5 Ni2 Cl2 90.56(17) 2_655 2_655 ? N5 Ni2 Cl2 89.82(17) . 2_655 ? N8 Ni2 Cl2 89.65(15) . 2_655 ? N8 Ni2 Cl2 89.99(15) 2_655 2_655 ? N5 Ni2 Cl2 89.81(17) 2_655 . ? N5 Ni2 Cl2 90.55(17) . . ? N8 Ni2 Cl2 89.99(15) . . ? N8 Ni2 Cl2 89.65(15) 2_655 . ? Cl2 Ni2 Cl2 179.48(8) 2_655 . ? C1 N1 C5 115.3(5) . . ? C1 N1 Ni1 123.8(4) . . ? C5 N1 Ni1 120.8(4) . . ? N1 C1 C2 125.9(6) . . ? N1 C1 H1 117.0 . . ? C2 C1 H1 117.1 . . ? C1 C2 C3 118.0(6) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C6 124.4(7) . . ? C4 C3 C2 117.8(5) . . ? C6 C3 C2 117.8(7) . . ? C3 C4 C5 120.5(7) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 N1 121.8(7) . . ? C4 C5 H5 119.1 . . ? N1 C5 H5 119.1 . . ? C7 C6 C3 175.8(10) . . ? C6 C7 C8 174.8(10) . . ? C9 C8 C15 114.5(5) . . ? C9 C8 C7 123.7(8) . . ? C15 C8 C7 121.5(7) . . ? C8 C9 C12 126.5(6) . . ? C8 C9 C10 128.4(6) . . ? C12 C9 C10 105.1(6) . . ? O1 C10 N2 133.0(9) . . ? O1 C10 C9 124.8(9) . . ? N2 C10 C9 101.6(6) . . ? C11 N2 C10 114.0(7) . . ? C11 N2 C18 132.8(8) . . ? C10 N2 C18 113.1(7) . . ? O2 C11 N2 124.9(8) . . ? O2 C11 C12 126.9(7) . . ? N2 C11 C12 107.9(6) . . ? C13 C12 C9 120.0(7) . . ? C13 C12 C11 128.5(6) . . ? C9 C12 C11 111.4(6) . . ? C12 C13 C26 125.6(8) . . ? C12 C13 C14 117.0(6) . . ? C26 C13 C14 117.3(8) . . ? C15 C14 C16 112.1(8) . . ? C15 C14 C13 118.5(8) . . ? C16 C14 C13 128.5(7) . . ? C14 C15 C8 123.1(8) . . ? C14 C15 C17 105.3(7) . . ? C8 C15 C17 131.4(6) . . ? O3 C16 N3 126.2(9) . . ? O3 C16 C14 133.6(9) . . ? N3 C16 C14 99.9(7) . . ? C17 N3 C16 115.2(8) . . ? C17 N3 C22 121.8(8) . . ? C16 N3 C22 120.4(7) . . ? O4 C17 N3 129.4(10) . . ? O4 C17 C15 122.4(8) . . ? N3 C17 C15 107.5(6) . . ? C21 C18 N2 111.6(9) . . ? C21 C18 C19A 111.9(10) . . ? N2 C18 C19A 103.2(14) . . ? C21 C18 C19 137.3(11) . . ? N2 C18 C19 105.8(9) . . ? C19A C18 C19 37.5(10) . . ? C21 C18 H18 97.5 . . ? N2 C18 H18 97.4 . . ? C19A C18 H18 134.0 . . ? C19 C18 H18 97.4 . . ? C18 C19 C20 106.0(9) . . ? C18 C19 H19A 110.5 . . ? C20 C19 H19A 110.6 . . ? C18 C19 H19B 110.5 . . ? C20 C19 H19B 110.5 . . ? H19A C19 H19B 108.7 . . ? N3 C22 C25 113.9(11) . . ? N3 C22 C23 91.9(13) . . ? C25 C22 C23 145.4(18) . . ? C27 C26 C13 177.6(8) . . ? C26 C27 C28 169.5(7) . 3_546 ? C32 C28 C27 123.5(6) . 3_454 ? C32 C28 C29 118.8(5) . . ? C27 C28 C29 117.7(6) 3_454 . ? C30 C29 C28 118.3(5) . . ? C30 C29 H29 120.8 . . ? C28 C29 H29 120.9 . . ? N4 C30 C29 122.1(5) . . ? N4 C30 H30 118.9 . . ? C29 C30 H30 118.9 . . ? C31 N4 C30 116.3(5) . . ? C31 N4 Ni1 120.7(4) . . ? C30 N4 Ni1 122.3(4) . . ? N4 C31 C32 127.1(7) . . ? N4 C31 H31 116.5 . . ? C32 C31 H31 116.5 . . ? C28 C32 C31 117.4(6) . . ? C28 C32 H32 121.3 . . ? C31 C32 H32 121.3 . . ? C37 N5 C33 116.1(5) . . ? C37 N5 Ni2 123.8(4) . . ? C33 N5 Ni2 120.0(4) . . ? N5 C33 C34 121.3(7) . . ? N5 C33 H33 119.3 . . ? C34 C33 H33 119.4 . . ? C35 C34 C33 118.8(7) . . ? C35 C34 H34 120.6 . . ? C33 C34 H34 120.6 . . ? C34 C35 C36 118.8(7) . . ? C34 C35 C38 122.0(7) . . ? C36 C35 C38 119.1(7) . . ? C35 C36 C37 116.9(9) . . ? C35 C36 H36 121.6 . . ? C37 C36 H36 121.5 . . ? N5 C37 C36 126.8(7) . . ? N5 C37 H37 116.6 . . ? C36 C37 H37 116.6 . . ? C39 C38 C35 173.4(8) . . ? C38 C39 C40 174.3(8) . . ? C41 C40 C39 124.9(6) . . ? C41 C40 C49 113.5(5) . . ? C39 C40 C49 121.6(6) . . ? C44 C41 C40 125.0(6) . . ? C44 C41 C42 106.9(6) . . ? C40 C41 C42 127.9(6) . . ? O5 C42 N6 127.1(8) . . ? O5 C42 C41 126.5(7) . . ? N6 C42 C41 105.7(6) . . ? C43 N6 C42 108.7(6) . . ? C43 N6 C50 126.2(6) . . ? C42 N6 C50 124.7(7) . . ? O6 C43 N6 121.7(7) . . ? O6 C43 C44 125.7(7) . . ? N6 C43 C44 112.5(5) . . ? C45 C44 C41 123.5(6) . . ? C45 C44 C43 130.2(5) . . ? C41 C44 C43 106.0(6) . . ? C44 C45 C46 113.5(5) . . ? C44 C45 C58 122.7(6) . . ? C46 C45 C58 123.3(6) . . ? C49 C46 C45 124.1(7) . . ? C49 C46 C47 105.3(6) . . ? C45 C46 C47 130.5(5) . . ? O7 C47 N7 127.7(8) . . ? O7 C47 C46 125.6(7) . . ? N7 C47 C46 106.6(6) . . ? C47 N7 C48 109.5(6) . . ? C47 N7 C54 124.3(6) . . ? C48 N7 C54 126.0(6) . . ? O8 C48 N7 120.4(7) . . ? O8 C48 C49 130.2(7) . . ? N7 C48 C49 109.4(6) . . ? C46 C49 C48 109.2(7) . . ? C46 C49 C40 120.1(7) . . ? C48 C49 C40 130.7(6) . . ? C51 C50 N6 115.7(9) . . ? C51 C50 C53 114.7(11) . . ? N6 C50 C53 112.6(8) . . ? C51 C50 H50 104.0 . . ? N6 C50 H50 104.0 . . ? C53 C50 H50 104.1 . . ? C52 C51 C50 124.6(18) . . ? C52 C51 H51A 106.3 . . ? C50 C51 H51A 106.2 . . ? C52 C51 H51B 106.1 . . ? C50 C51 H51B 106.1 . . ? H51A C51 H51B 106.4 . . ? C50 C53 H53A 109.5 . . ? C50 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C50 C53 H53C 109.4 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C55 C54 N7 109.7(7) . . ? C55 C54 C57 111.6(8) . . ? N7 C54 C57 113.0(7) . . ? C55 C54 H54 107.4 . . ? N7 C54 H54 107.4 . . ? C57 C54 H54 107.4 . . ? C54 C55 C56 115.5(10) . . ? C54 C55 H55A 108.4 . . ? C56 C55 H55A 108.4 . . ? C54 C55 H55B 108.4 . . ? C56 C55 H55B 108.5 . . ? H55A C55 H55B 107.5 . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C54 C57 H57A 109.5 . . ? C54 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C54 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C59 C58 C45 174.6(8) . . ? C58 C59 C60 175.6(8) . 4_656 ? C64 C60 C59 128.8(7) . 4_646 ? C64 C60 C61 116.1(6) . . ? C59 C60 C61 114.9(6) 4_646 . ? C62 C61 C60 119.2(7) . . ? C62 C61 H61 120.4 . . ? C60 C61 H61 120.4 . . ? N8 C62 C61 121.6(6) . . ? N8 C62 H62 119.2 . . ? C61 C62 H62 119.2 . . ? C63 N8 C62 118.3(5) . . ? C63 N8 Ni2 122.3(4) . . ? C62 N8 Ni2 118.7(4) . . ? N8 C63 C64 123.7(6) . . ? N8 C63 H63 118.2 . . ? C64 C63 H63 118.2 . . ? C60 C64 C63 120.9(7) . . ? C60 C64 H64 119.5 . . ? C63 C64 H64 119.5 . . ? C66 C65 Cl4 126.8(7) . . ? C66 C65 Cl3 98.0(6) . . ? Cl4 C65 Cl3 112.7(6) . . ? C66 C65 H65 105.9 . . ? Cl4 C65 H65 105.9 . . ? Cl3 C65 H65 105.9 . . ? C65 C66 Cl5 98.4(5) . . ? C65 C66 Cl6 91.4(5) . . ? Cl5 C66 Cl6 96.1(5) . . ? C65 C66 H66 121.4 . . ? Cl5 C66 H66 121.4 . . ? Cl6 C66 H66 121.4 . . ? C68 C67 Cl8 114.1(12) . . ? C68 C67 Cl7 107.4(13) . . ? Cl8 C67 Cl7 103.9(6) . . ? C68 C67 H67 110.4 . . ? Cl8 C67 H67 110.4 . . ? Cl7 C67 H67 110.5 . . ? C67 C68 Cl10 118.2(13) . . ? C67 C68 Cl9 114.1(10) . . ? Cl10 C68 Cl9 112.0(7) . . ? C67 C68 H68 103.5 . . ? Cl10 C68 H68 103.4 . . ? Cl9 C68 H68 103.3 . . ? C70 C69 Cl12 104.3(7) . . ? C70 C69 Cl11 110.4(7) . . ? Cl12 C69 Cl11 115.0(9) . . ? C70 C69 H69 109.0 . . ? Cl12 C69 H69 109.0 . . ? Cl11 C69 H69 109.0 . . ? C69 C70 Cl14 113.0(8) . . ? C69 C70 Cl13 102.0(7) . . ? Cl14 C70 Cl13 116.2(6) . . ? C69 C70 H70 108.4 . . ? Cl14 C70 H70 108.4 . . ? Cl13 C70 H70 108.4 . . ? C18 C19A C20A 104.8(10) . . ? C18 C19A H19C 110.8 . . ? C20A C19A H19C 111.2 . . ? C18 C19A H19D 110.7 . . ? C20A C19A H19D 110.5 . . ? H19C C19A H19D 108.9 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 29.88 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.519 _refine_diff_density_min -1.011 _refine_diff_density_rms 0.129 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.017 -0.280 -0.017 1447 363 ' ' 2 0.368 0.220 -0.132 1447 363 ' ' 3 0.483 0.854 0.208 8 1 ' ' 4 0.983 0.354 0.208 8 1 ' ' 5 0.483 0.337 0.354 8 1 ' ' 6 0.983 0.837 0.354 8 1 ' ' 7 0.017 0.837 0.646 8 1 ' ' 8 0.517 0.337 0.646 8 1 ' ' 9 0.017 0.354 0.791 8 1 ' ' 10 0.517 0.854 0.791 8 1 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 959991'