# 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_1 _database_code_depnum_ccdc_archive 'CCDC 913357' #TrackingRef '1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H44 N10 Ni O12 S2' _chemical_formula_sum 'C46 H44 N10 Ni O12 S2' _chemical_formula_weight 1051.74 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' Ni Ni 0.3393 1.1124 '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' S S 0.1246 0.1234 '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/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.030(9) _cell_length_b 9.674(3) _cell_length_c 22.455(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.951(12) _cell_angle_gamma 90.00 _cell_volume 4928(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1244 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 21.68 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 0.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9420 _exptl_absorpt_correction_T_max 0.9470 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13374 _diffrn_reflns_av_R_equivalents 0.1255 _diffrn_reflns_av_sigmaI/netI 0.1386 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4343 _reflns_number_gt 2162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4343 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1219 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 0.805 _refine_ls_restrained_S_all 0.806 _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 Ni1 Ni 0.2500 0.2500 0.0000 0.0357(2) Uani 1 2 d S . . C1 C -0.0545(3) -0.1007(6) -0.0864(3) 0.0830(17) Uani 1 1 d . . . H1 H -0.0362 -0.0713 -0.0484 0.100 Uiso 1 1 calc R . . C2 C -0.1120(4) -0.0697(7) -0.1069(4) 0.119(3) Uani 1 1 d . . . H2 H -0.1334 -0.0187 -0.0831 0.143 Uiso 1 1 calc R . . C3 C -0.1372(4) -0.1129(10) -0.1612(5) 0.125(4) Uani 1 1 d . . . H3 H -0.1765 -0.0892 -0.1741 0.150 Uiso 1 1 calc R . . C4 C -0.1107(4) -0.1882(10) -0.1990(4) 0.131(4) Uani 1 1 d . . . H4 H -0.1305 -0.2165 -0.2367 0.157 Uiso 1 1 calc R . . C5 C -0.0503(3) -0.2222(6) -0.1777(3) 0.096(2) Uani 1 1 d . . . H5 H -0.0293 -0.2753 -0.2013 0.115 Uiso 1 1 calc R . . C6 C -0.0238(2) -0.1758(5) -0.1225(2) 0.0600(14) Uani 1 1 d . . . C7 C 0.08238(18) 0.0357(4) -0.12021(19) 0.0438(11) Uani 1 1 d . . . C8 C 0.12115(17) 0.0853(4) -0.07035(17) 0.0405(11) Uani 1 1 d . . . H8 H 0.1467 0.0262 -0.0459 0.049 Uiso 1 1 calc R . . C9 C 0.12037(15) 0.2250(4) -0.05847(16) 0.0348(10) Uani 1 1 d . . . C10 C 0.08326(17) 0.3133(4) -0.09573(17) 0.0430(11) Uani 1 1 d . . . H10 H 0.0833 0.4074 -0.0872 0.052 Uiso 1 1 calc R . . C11 C 0.04611(17) 0.2612(5) -0.14565(17) 0.0489(11) Uani 1 1 d . . . H11 H 0.0219 0.3206 -0.1715 0.059 Uiso 1 1 calc R . . C12 C 0.04496(17) 0.1206(5) -0.15714(19) 0.0485(12) Uani 1 1 d . . . H12 H 0.0189 0.0845 -0.1897 0.058 Uiso 1 1 calc R . . C13 C 0.16252(16) 0.4156(4) 0.07730(17) 0.0345(10) Uani 1 1 d . . . C14 C 0.22027(18) 0.3753(4) 0.10803(17) 0.0371(10) Uani 1 1 d . . . C15 C 0.20687(19) 0.5153(5) 0.1956(2) 0.0450(11) Uani 1 1 d . . . C16 C 0.14950(17) 0.5565(4) 0.16244(18) 0.0427(11) Uani 1 1 d . . . C17 C 0.12825(17) 0.5062(4) 0.10568(18) 0.0380(10) Uani 1 1 d . . . C18 C 0.29666(17) 0.3801(5) 0.19894(18) 0.0551(13) Uani 1 1 d . . . H18A H 0.2993 0.4006 0.2412 0.083 Uiso 1 1 calc R . . H18B H 0.3274 0.4279 0.1834 0.083 Uiso 1 1 calc R . . H18C H 0.3009 0.2824 0.1937 0.083 Uiso 1 1 calc R . . C19 C 0.1169(2) 0.6522(6) 0.1923(2) 0.0638(15) Uani 1 1 d . . . C20 C 0.06763(17) 0.5487(5) 0.07405(18) 0.0541(13) Uani 1 1 d . . . H20A H 0.0478 0.5979 0.1018 0.081 Uiso 1 1 calc R . . H20B H 0.0453 0.4678 0.0598 0.081 Uiso 1 1 calc R . . H20C H 0.0712 0.6074 0.0404 0.081 Uiso 1 1 calc R . . C21 C 0.26830(19) -0.0107(5) 0.0706(2) 0.0505(12) Uani 1 1 d . . . H21 H 0.2970 0.0426 0.0942 0.061 Uiso 1 1 calc R . . C22 C 0.2108(3) -0.2194(5) 0.0598(3) 0.102(2) Uani 1 1 d . . . H22A H 0.1811 -0.2330 0.0844 0.152 Uiso 1 1 calc R . . H22B H 0.2268 -0.3072 0.0511 0.152 Uiso 1 1 calc R . . H22C H 0.1935 -0.1753 0.0226 0.152 Uiso 1 1 calc R . . C23 C 0.2893(3) -0.1840(6) 0.1492(2) 0.094(2) Uani 1 1 d . . . H23A H 0.3148 -0.1127 0.1686 0.141 Uiso 1 1 calc R . . H23B H 0.3124 -0.2630 0.1421 0.141 Uiso 1 1 calc R . . H23C H 0.2617 -0.2100 0.1747 0.141 Uiso 1 1 calc R . . N1 N 0.16040(13) 0.2762(3) -0.00660(14) 0.0368(8) Uani 1 1 d . . . N2 N 0.13476(14) 0.3608(3) 0.02393(14) 0.0365(8) Uani 1 1 d . . . N3 N 0.23871(14) 0.4256(3) 0.16585(14) 0.0412(9) Uani 1 1 d . . . N4 N 0.09187(19) 0.7312(6) 0.2155(2) 0.0962(17) Uani 1 1 d . . . N5 N 0.25739(17) -0.1327(4) 0.09171(17) 0.0579(11) Uani 1 1 d . . . O1 O 0.08422(13) -0.1071(3) -0.13411(14) 0.0642(9) Uani 1 1 d . . . O2 O 0.06586(18) -0.1826(4) -0.03405(17) 0.1164(16) Uani 1 1 d U . . O3 O 0.06479(18) -0.3442(4) -0.1196(3) 0.149(2) Uani 1 1 d . . . O4 O 0.25496(11) 0.2978(3) 0.08654(11) 0.0435(8) Uani 1 1 d . . . O5 O 0.22693(13) 0.5570(3) 0.24680(13) 0.0648(10) Uani 1 1 d . . . O6 O 0.24384(12) 0.0400(3) 0.02193(13) 0.0482(8) Uani 1 1 d . . . S1 S 0.05115(6) -0.21385(13) -0.09698(8) 0.0812(5) Uani 1 1 d U . . 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 0.0324(4) 0.0335(4) 0.0399(4) 0.0010(4) 0.0026(3) 0.0027(4) C1 0.105(5) 0.073(4) 0.073(4) 0.013(3) 0.020(4) -0.004(4) C2 0.087(6) 0.105(6) 0.173(8) 0.055(6) 0.048(5) 0.026(5) C3 0.092(6) 0.146(9) 0.122(7) 0.083(7) -0.027(6) -0.043(6) C4 0.125(8) 0.168(9) 0.085(6) 0.019(5) -0.025(5) -0.068(6) C5 0.099(5) 0.108(5) 0.077(4) -0.009(4) -0.001(3) -0.040(4) C6 0.059(3) 0.054(3) 0.064(3) 0.006(3) 0.004(3) -0.015(3) C7 0.037(3) 0.033(3) 0.061(3) -0.010(2) 0.010(2) -0.005(2) C8 0.034(2) 0.036(3) 0.050(3) -0.002(2) 0.002(2) -0.001(2) C9 0.028(2) 0.039(3) 0.036(2) -0.002(2) 0.0023(18) 0.000(2) C10 0.049(3) 0.035(3) 0.043(3) 0.000(2) 0.003(2) 0.006(2) C11 0.050(3) 0.047(3) 0.044(2) 0.002(3) -0.007(2) 0.003(3) C12 0.038(3) 0.056(3) 0.047(3) -0.007(3) -0.004(2) -0.003(3) C13 0.034(2) 0.033(2) 0.036(2) 0.000(2) 0.005(2) -0.004(2) C14 0.042(3) 0.036(3) 0.034(3) 0.005(2) 0.008(2) 0.001(2) C15 0.048(3) 0.043(3) 0.044(3) -0.001(2) 0.009(2) -0.001(2) C16 0.039(3) 0.044(3) 0.045(3) -0.006(2) 0.007(2) 0.003(2) C17 0.034(2) 0.037(2) 0.043(3) 0.003(2) 0.007(2) 0.000(2) C18 0.048(3) 0.066(3) 0.046(3) 0.003(2) -0.006(2) 0.009(3) C19 0.045(3) 0.094(4) 0.045(3) -0.021(3) -0.012(2) 0.009(3) C20 0.042(3) 0.065(3) 0.054(3) -0.010(3) 0.002(2) 0.013(3) C21 0.048(3) 0.038(3) 0.065(3) 0.001(3) 0.008(2) 0.003(2) C22 0.138(6) 0.050(4) 0.114(5) 0.013(3) 0.014(4) -0.025(4) C23 0.127(5) 0.081(4) 0.075(4) 0.036(3) 0.021(4) 0.026(4) N1 0.0340(18) 0.033(2) 0.0418(19) -0.0002(17) 0.0026(15) 0.0000(17) N2 0.040(2) 0.029(2) 0.038(2) -0.0027(17) 0.0020(17) 0.0025(17) N3 0.039(2) 0.045(2) 0.037(2) 0.0003(18) -0.0027(17) 0.0005(18) N4 0.070(3) 0.133(5) 0.079(3) -0.060(3) -0.007(2) 0.030(3) N5 0.070(3) 0.038(2) 0.066(3) 0.013(2) 0.015(2) 0.003(2) O1 0.059(2) 0.0376(19) 0.094(2) -0.0176(19) 0.0087(18) -0.0072(17) O2 0.124(3) 0.117(4) 0.089(3) 0.047(2) -0.038(3) -0.045(3) O3 0.103(3) 0.030(2) 0.313(6) -0.017(3) 0.032(4) 0.008(2) O4 0.0393(17) 0.0413(18) 0.0471(17) -0.0055(14) -0.0003(14) 0.0065(14) O5 0.060(2) 0.083(3) 0.0447(19) -0.0191(18) -0.0081(16) 0.0082(18) O6 0.0443(18) 0.0446(19) 0.0524(18) 0.0059(15) -0.0005(15) 0.0044(15) S1 0.0670(9) 0.0387(8) 0.1272(13) 0.0078(8) -0.0129(9) -0.0068(7) _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 O4 1.982(3) . ? Ni1 O4 1.982(3) 7 ? Ni1 N1 2.059(3) 7 ? Ni1 N1 2.059(3) . ? Ni1 O6 2.100(3) . ? Ni1 O6 2.100(3) 7 ? C1 C2 1.356(8) . ? C1 C6 1.372(7) . ? C1 H1 0.9300 . ? C2 C3 1.323(9) . ? C2 H2 0.9300 . ? C3 C4 1.343(11) . ? C3 H3 0.9300 . ? C4 C5 1.430(9) . ? C4 H4 0.9300 . ? C5 C6 1.360(6) . ? C5 H5 0.9300 . ? C6 S1 1.760(5) . ? C7 C12 1.363(5) . ? C7 C8 1.391(5) . ? C7 O1 1.418(5) . ? C8 C9 1.378(5) . ? C8 H8 0.9300 . ? C9 C10 1.383(5) . ? C9 N1 1.443(4) . ? C10 C11 1.383(5) . ? C10 H10 0.9300 . ? C11 C12 1.384(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N2 1.364(4) . ? C13 C17 1.404(5) . ? C13 C14 1.442(5) . ? C14 O4 1.251(4) . ? C14 N3 1.383(5) . ? C15 O5 1.231(4) . ? C15 N3 1.380(5) . ? C15 C16 1.455(5) . ? C16 C17 1.373(5) . ? C16 C19 1.430(6) . ? C17 C20 1.510(5) . ? C18 N3 1.478(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N4 1.136(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O6 1.240(4) . ? C21 N5 1.313(5) . ? C21 H21 0.9300 . ? C22 N5 1.451(6) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 N5 1.458(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? N1 N2 1.276(4) . ? O1 S1 1.600(3) . ? O2 S1 1.427(4) . ? O3 S1 1.415(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Ni1 O4 180.00(4) . 7 ? O4 Ni1 N1 94.07(11) . 7 ? O4 Ni1 N1 85.93(11) 7 7 ? O4 Ni1 N1 85.93(11) . . ? O4 Ni1 N1 94.07(11) 7 . ? N1 Ni1 N1 180.00(17) 7 . ? O4 Ni1 O6 89.45(11) . . ? O4 Ni1 O6 90.55(11) 7 . ? N1 Ni1 O6 88.37(12) 7 . ? N1 Ni1 O6 91.63(12) . . ? O4 Ni1 O6 90.55(11) . 7 ? O4 Ni1 O6 89.45(11) 7 7 ? N1 Ni1 O6 91.63(12) 7 7 ? N1 Ni1 O6 88.37(12) . 7 ? O6 Ni1 O6 180.00(16) . 7 ? C2 C1 C6 119.3(6) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? C3 C2 C1 119.4(8) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 125.3(9) . . ? C2 C3 H3 117.4 . . ? C4 C3 H3 117.4 . . ? C3 C4 C5 115.8(8) . . ? C3 C4 H4 122.1 . . ? C5 C4 H4 122.1 . . ? C6 C5 C4 119.1(7) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 121.1(5) . . ? C5 C6 S1 119.2(5) . . ? C1 C6 S1 119.7(5) . . ? C12 C7 C8 122.1(4) . . ? C12 C7 O1 119.5(4) . . ? C8 C7 O1 118.3(4) . . ? C9 C8 C7 117.8(4) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C8 C9 C10 121.1(3) . . ? C8 C9 N1 117.7(3) . . ? C10 C9 N1 121.2(4) . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 119.3(4) . . ? C7 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? N2 C13 C17 115.3(3) . . ? N2 C13 C14 124.6(4) . . ? C17 C13 C14 119.7(4) . . ? O4 C14 N3 117.4(4) . . ? O4 C14 C13 125.1(4) . . ? N3 C14 C13 117.5(4) . . ? O5 C15 N3 120.8(4) . . ? O5 C15 C16 123.3(4) . . ? N3 C15 C16 115.9(4) . . ? C17 C16 C19 122.2(4) . . ? C17 C16 C15 121.6(4) . . ? C19 C16 C15 116.2(4) . . ? C16 C17 C13 120.3(4) . . ? C16 C17 C20 119.5(4) . . ? C13 C17 C20 120.2(4) . . ? N3 C18 H18A 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N4 C19 C16 178.0(6) . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O6 C21 N5 126.0(4) . . ? O6 C21 H21 117.0 . . ? N5 C21 H21 117.0 . . ? N5 C22 H22A 109.5 . . ? N5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 H23A 109.5 . . ? N5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N2 N1 C9 111.3(3) . . ? N2 N1 Ni1 126.3(2) . . ? C9 N1 Ni1 120.6(2) . . ? N1 N2 C13 122.1(3) . . ? C15 N3 C14 124.9(3) . . ? C15 N3 C18 116.9(3) . . ? C14 N3 C18 118.1(4) . . ? C21 N5 C22 120.8(4) . . ? C21 N5 C23 121.8(4) . . ? C22 N5 C23 117.3(4) . . ? C7 O1 S1 118.6(3) . . ? C14 O4 Ni1 125.8(2) . . ? C21 O6 Ni1 123.4(3) . . ? O3 S1 O2 121.0(3) . . ? O3 S1 O1 103.5(3) . . ? O2 S1 O1 109.0(2) . . ? O3 S1 C6 109.6(3) . . ? O2 S1 C6 109.2(3) . . ? O1 S1 C6 102.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(10) . . . . ? C1 C2 C3 C4 0.7(13) . . . . ? C2 C3 C4 C5 -0.3(13) . . . . ? C3 C4 C5 C6 -1.0(10) . . . . ? C4 C5 C6 C1 1.9(8) . . . . ? C4 C5 C6 S1 -178.4(5) . . . . ? C2 C1 C6 C5 -1.5(8) . . . . ? C2 C1 C6 S1 178.8(4) . . . . ? C12 C7 C8 C9 0.7(6) . . . . ? O1 C7 C8 C9 177.8(4) . . . . ? C7 C8 C9 C10 -1.5(6) . . . . ? C7 C8 C9 N1 179.7(3) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? N1 C9 C10 C11 178.9(3) . . . . ? C9 C10 C11 C12 1.9(6) . . . . ? C8 C7 C12 C11 1.3(7) . . . . ? O1 C7 C12 C11 -175.8(4) . . . . ? C10 C11 C12 C7 -2.6(7) . . . . ? N2 C13 C14 O4 9.0(6) . . . . ? C17 C13 C14 O4 -178.4(4) . . . . ? N2 C13 C14 N3 -170.7(3) . . . . ? C17 C13 C14 N3 1.9(5) . . . . ? O5 C15 C16 C17 -179.0(4) . . . . ? N3 C15 C16 C17 1.4(6) . . . . ? O5 C15 C16 C19 1.1(6) . . . . ? N3 C15 C16 C19 -178.5(4) . . . . ? C19 C16 C17 C13 178.1(4) . . . . ? C15 C16 C17 C13 -1.8(6) . . . . ? C19 C16 C17 C20 -2.1(6) . . . . ? C15 C16 C17 C20 178.0(4) . . . . ? N2 C13 C17 C16 173.4(4) . . . . ? C14 C13 C17 C16 0.0(6) . . . . ? N2 C13 C17 C20 -6.4(5) . . . . ? C14 C13 C17 C20 -179.7(4) . . . . ? C8 C9 N1 N2 -135.3(4) . . . . ? C10 C9 N1 N2 45.9(5) . . . . ? C8 C9 N1 Ni1 59.2(4) . . . . ? C10 C9 N1 Ni1 -119.5(3) . . . . ? O4 Ni1 N1 N2 32.2(3) . . . . ? O4 Ni1 N1 N2 -147.8(3) 7 . . . ? O6 Ni1 N1 N2 121.5(3) . . . . ? O6 Ni1 N1 N2 -58.5(3) 7 . . . ? O4 Ni1 N1 C9 -164.7(3) . . . . ? O4 Ni1 N1 C9 15.3(3) 7 . . . ? O6 Ni1 N1 C9 -75.4(3) . . . . ? O6 Ni1 N1 C9 104.6(3) 7 . . . ? C9 N1 N2 C13 175.4(3) . . . . ? Ni1 N1 N2 C13 -20.2(5) . . . . ? C17 C13 N2 N1 -179.5(3) . . . . ? C14 C13 N2 N1 -6.6(6) . . . . ? O5 C15 N3 C14 -178.9(4) . . . . ? C16 C15 N3 C14 0.7(6) . . . . ? O5 C15 N3 C18 1.5(6) . . . . ? C16 C15 N3 C18 -178.9(4) . . . . ? O4 C14 N3 C15 177.9(4) . . . . ? C13 C14 N3 C15 -2.4(6) . . . . ? O4 C14 N3 C18 -2.4(5) . . . . ? C13 C14 N3 C18 177.3(3) . . . . ? O6 C21 N5 C22 -3.9(7) . . . . ? O6 C21 N5 C23 179.1(4) . . . . ? C12 C7 O1 S1 -102.3(4) . . . . ? C8 C7 O1 S1 80.6(4) . . . . ? N3 C14 O4 Ni1 -163.4(2) . . . . ? C13 C14 O4 Ni1 16.9(5) . . . . ? N1 Ni1 O4 C14 150.4(3) 7 . . . ? N1 Ni1 O4 C14 -29.6(3) . . . . ? O6 Ni1 O4 C14 -121.3(3) . . . . ? O6 Ni1 O4 C14 58.7(3) 7 . . . ? N5 C21 O6 Ni1 166.1(3) . . . . ? O4 Ni1 O6 C21 -32.2(3) . . . . ? O4 Ni1 O6 C21 147.8(3) 7 . . . ? N1 Ni1 O6 C21 61.9(3) 7 . . . ? N1 Ni1 O6 C21 -118.1(3) . . . . ? C7 O1 S1 O3 -176.7(3) . . . . ? C7 O1 S1 O2 -46.7(4) . . . . ? C7 O1 S1 C6 69.2(4) . . . . ? C5 C6 S1 O3 -32.6(5) . . . . ? C1 C6 S1 O3 147.1(4) . . . . ? C5 C6 S1 O2 -167.3(4) . . . . ? C1 C6 S1 O2 12.4(5) . . . . ? C5 C6 S1 O1 77.0(4) . . . . ? C1 C6 S1 O1 -103.4(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.372 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.063 data_2 _database_code_depnum_ccdc_archive 'CCDC 913358' #TrackingRef '1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H44 Cu N10 O12 S2' _chemical_formula_sum 'C46 H44 Cu N10 O12 S2' _chemical_formula_weight 1056.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.524(4) _cell_length_b 9.9036(16) _cell_length_c 22.397(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.079(3) _cell_angle_gamma 90.00 _cell_volume 4933.6(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2706 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.69 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2188 _exptl_absorpt_coefficient_mu 0.599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9316 _exptl_absorpt_correction_T_max 0.9425 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (BRUKER, 2000) and successive difference Fourier syntheses. ; _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 Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12644 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4347 _reflns_number_gt 2721 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0464P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4347 _refine_ls_number_parameters 326 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.912 _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 0.2500 0.2500 0.0000 0.03787(18) Uani 1 2 d S . . C1 C 0.27987(12) 0.1362(3) -0.10671(14) 0.0373(7) Uani 1 1 d . . . C2 C 0.29376(13) 0.0014(3) -0.19515(16) 0.0492(8) Uani 1 1 d . . . C3 C 0.35089(12) -0.0406(3) -0.16246(15) 0.0462(8) Uani 1 1 d . . . C4 C 0.37321(11) 0.0047(3) -0.10540(14) 0.0419(8) Uani 1 1 d . . . C5 C 0.33816(11) 0.0938(3) -0.07688(13) 0.0350(7) Uani 1 1 d . . . C6 C 0.20371(12) 0.1411(3) -0.19708(15) 0.0553(9) Uani 1 1 d . . . H6A H 0.1744 0.1459 -0.1692 0.083 Uiso 1 1 calc R . . H6B H 0.1889 0.0796 -0.2304 0.083 Uiso 1 1 calc R . . H6C H 0.2094 0.2312 -0.2133 0.083 Uiso 1 1 calc R . . C7 C 0.38301(14) -0.1357(4) -0.19263(18) 0.0692(12) Uani 1 1 d . . . C8 C 0.43346(12) -0.0403(3) -0.07366(15) 0.0555(9) Uani 1 1 d . . . H8A H 0.4288 -0.0850 -0.0357 0.083 Uiso 1 1 calc R . . H8B H 0.4599 0.0383 -0.0651 0.083 Uiso 1 1 calc R . . H8C H 0.4512 -0.1036 -0.0995 0.083 Uiso 1 1 calc R . . C9 C 0.37852(11) 0.2812(3) 0.05828(13) 0.0373(7) Uani 1 1 d . . . C10 C 0.41635(12) 0.1975(3) 0.09619(14) 0.0441(8) Uani 1 1 d . . . H10 H 0.4169 0.1031 0.0888 0.053 Uiso 1 1 calc R . . C11 C 0.45310(14) 0.2531(4) 0.14473(15) 0.0533(9) Uani 1 1 d . . . H11 H 0.4785 0.1962 0.1717 0.064 Uiso 1 1 calc R . . C12 C 0.45354(13) 0.3899(4) 0.15477(15) 0.0526(9) Uani 1 1 d . . . H12 H 0.4797 0.4282 0.1879 0.063 Uiso 1 1 calc R . . C13 C 0.41592(12) 0.4694(3) 0.11645(15) 0.0454(8) Uani 1 1 d . . . C14 C 0.37720(12) 0.4176(3) 0.06851(14) 0.0413(8) Uani 1 1 d . . . H14 H 0.3502 0.4746 0.0431 0.050 Uiso 1 1 calc R . . C15 C 0.52505(15) 0.6744(4) 0.12061(18) 0.0599(10) Uani 1 1 d . . . C16 C 0.5480(2) 0.7213(5) 0.1760(2) 0.1036(16) Uani 1 1 d U . . H16 H 0.5244 0.7759 0.1982 0.124 Uiso 1 1 calc R . . C17 C 0.6075(3) 0.6875(7) 0.2002(3) 0.140(2) Uani 1 1 d U . . H17 H 0.6250 0.7171 0.2394 0.168 Uiso 1 1 calc R . . C18 C 0.6394(3) 0.6118(7) 0.1663(4) 0.137(3) Uani 1 1 d . . . H18 H 0.6797 0.5886 0.1822 0.165 Uiso 1 1 calc R . . C19 C 0.6162(2) 0.5690(6) 0.1116(3) 0.125(2) Uani 1 1 d . . . H19 H 0.6401 0.5164 0.0890 0.150 Uiso 1 1 calc R . . C20 C 0.55838(18) 0.5992(4) 0.0872(2) 0.0812(12) Uani 1 1 d . . . H20 H 0.5418 0.5687 0.0479 0.097 Uiso 1 1 calc R . . C21 C 0.27007(15) -0.0362(4) 0.06840(19) 0.0592(10) Uani 1 1 d . . . H21 H 0.3016 0.0150 0.0910 0.071 Uiso 1 1 calc R . . C22 C 0.2061(2) -0.2313(4) 0.0608(2) 0.1134(18) Uani 1 1 d . . . H22A H 0.1732 -0.2316 0.0847 0.170 Uiso 1 1 calc R . . H22B H 0.2194 -0.3241 0.0557 0.170 Uiso 1 1 calc R . . H22C H 0.1919 -0.1915 0.0210 0.170 Uiso 1 1 calc R . . C23 C 0.2869(2) -0.1999(5) 0.1493(2) 0.1084(17) Uani 1 1 d . . . H23A H 0.3188 -0.1361 0.1651 0.163 Uiso 1 1 calc R . . H23B H 0.3045 -0.2886 0.1439 0.163 Uiso 1 1 calc R . . H23C H 0.2583 -0.2075 0.1779 0.163 Uiso 1 1 calc R . . N1 N 0.26134(9) 0.0908(2) -0.16471(11) 0.0404(6) Uani 1 1 d . . . N2 N 0.40846(15) -0.2134(4) -0.21586(17) 0.1081(14) Uani 1 1 d . . . N3 N 0.36559(9) 0.1477(2) -0.02400(11) 0.0368(6) Uani 1 1 d . . . N4 N 0.33851(9) 0.2285(2) 0.00747(11) 0.0366(6) Uani 1 1 d . . . N5 N 0.25595(14) -0.1520(3) 0.09181(14) 0.0655(9) Uani 1 1 d . . . O1 O 0.24541(8) 0.21430(19) -0.08467(9) 0.0416(5) Uani 1 1 d . . . O2 O 0.27321(10) -0.0371(2) -0.24578(11) 0.0681(7) Uani 1 1 d . . . O3 O 0.41389(9) 0.6102(2) 0.12794(11) 0.0635(7) Uani 1 1 d . . . O4 O 0.43870(13) 0.6734(3) 0.02917(14) 0.1013(10) Uani 1 1 d . . . O5 O 0.43436(12) 0.8379(3) 0.10933(19) 0.1263(14) Uani 1 1 d . . . O6 O 0.24619(9) 0.0104(2) 0.02046(12) 0.0611(7) Uani 1 1 d . . . S1 S 0.45034(4) 0.70964(10) 0.09077(6) 0.0747(4) 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 0.0329(2) 0.0419(4) 0.0392(3) -0.0031(3) 0.0070(2) 0.0019(2) C1 0.0392(15) 0.0388(19) 0.035(2) 0.0026(15) 0.0101(15) -0.0087(13) C2 0.0459(17) 0.058(2) 0.044(2) -0.0073(18) 0.0095(16) -0.0041(16) C3 0.0397(15) 0.057(2) 0.044(2) -0.0115(17) 0.0131(16) -0.0033(14) C4 0.0363(14) 0.048(2) 0.043(2) -0.0026(16) 0.0112(15) -0.0013(14) C5 0.0337(13) 0.0382(18) 0.0347(19) -0.0001(15) 0.0107(14) -0.0009(12) C6 0.0462(17) 0.076(3) 0.041(2) 0.0016(18) 0.0011(16) 0.0127(16) C7 0.0459(18) 0.103(3) 0.057(3) -0.033(2) 0.0008(18) 0.0113(19) C8 0.0415(15) 0.073(2) 0.052(2) -0.0126(19) 0.0072(16) 0.0129(15) C9 0.0329(14) 0.043(2) 0.0376(19) -0.0020(15) 0.0094(14) -0.0001(12) C10 0.0405(16) 0.048(2) 0.044(2) 0.0013(16) 0.0066(16) 0.0066(14) C11 0.0476(17) 0.062(3) 0.047(2) 0.003(2) -0.0023(16) 0.0059(16) C12 0.0420(16) 0.071(3) 0.045(2) -0.0135(19) 0.0054(16) -0.0079(16) C13 0.0411(16) 0.045(2) 0.053(2) -0.0104(17) 0.0152(16) -0.0067(14) C14 0.0391(14) 0.038(2) 0.047(2) 0.0008(16) 0.0063(15) -0.0013(13) C15 0.0545(19) 0.059(2) 0.065(3) 0.002(2) 0.004(2) -0.0170(17) C16 0.085(3) 0.138(4) 0.083(3) -0.009(3) 0.001(3) -0.044(3) C17 0.123(5) 0.194(6) 0.092(5) 0.025(4) -0.016(4) -0.067(4) C18 0.076(4) 0.164(7) 0.158(7) 0.105(6) -0.024(4) -0.038(4) C19 0.074(3) 0.123(5) 0.185(7) 0.060(5) 0.044(4) 0.023(3) C20 0.079(3) 0.080(3) 0.090(3) 0.014(3) 0.029(3) 0.002(2) C21 0.057(2) 0.049(3) 0.073(3) 0.003(2) 0.014(2) 0.0005(17) C22 0.141(4) 0.077(3) 0.122(4) 0.010(3) 0.019(4) -0.047(3) C23 0.134(4) 0.114(4) 0.082(4) 0.040(3) 0.030(3) 0.039(3) N1 0.0385(12) 0.0470(16) 0.0357(16) -0.0035(13) 0.0062(12) 0.0021(11) N2 0.068(2) 0.167(4) 0.084(3) -0.071(3) -0.005(2) 0.035(2) N3 0.0375(12) 0.0368(15) 0.0373(16) -0.0015(13) 0.0097(12) -0.0011(11) N4 0.0345(11) 0.0391(16) 0.0365(15) -0.0032(12) 0.0063(11) -0.0001(10) N5 0.083(2) 0.050(2) 0.067(2) 0.0171(17) 0.0230(19) 0.0126(16) O1 0.0383(10) 0.0498(14) 0.0376(13) -0.0043(10) 0.0089(10) 0.0070(9) O2 0.0627(13) 0.092(2) 0.0469(16) -0.0239(14) -0.0014(12) 0.0117(13) O3 0.0560(13) 0.0482(16) 0.087(2) -0.0235(13) 0.0136(13) -0.0072(11) O4 0.104(2) 0.104(2) 0.081(2) 0.0274(18) -0.0306(18) -0.0330(17) O5 0.0893(19) 0.0458(19) 0.242(4) -0.019(2) 0.020(2) -0.0022(15) O6 0.0624(14) 0.0469(15) 0.0705(19) 0.0133(13) -0.0007(14) -0.0020(11) S1 0.0603(6) 0.0491(7) 0.1093(10) -0.0001(6) -0.0035(6) -0.0089(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.916(2) . ? Cu1 O1 1.916(2) 7 ? Cu1 N4 1.986(2) 7 ? Cu1 N4 1.986(2) . ? Cu1 O6 2.421(2) 7 ? Cu1 O6 2.421(2) . ? C1 O1 1.251(3) . ? C1 N1 1.376(4) . ? C1 C5 1.439(4) . ? C2 O2 1.217(3) . ? C2 N1 1.393(4) . ? C2 C3 1.438(4) . ? C3 C4 1.373(4) . ? C3 C7 1.421(5) . ? C4 C5 1.404(4) . ? C4 C8 1.497(4) . ? C5 N3 1.356(3) . ? C6 N1 1.470(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 N2 1.134(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.371(4) . ? C9 C10 1.381(4) . ? C9 N4 1.434(3) . ? C10 C11 1.373(4) . ? C10 H10 0.9500 . ? C11 C12 1.373(4) . ? C11 H11 0.9500 . ? C12 C13 1.358(4) . ? C12 H12 0.9500 . ? C13 C14 1.371(4) . ? C13 O3 1.420(4) . ? C14 H14 0.9500 . ? C15 C16 1.349(5) . ? C15 C20 1.362(5) . ? C15 S1 1.745(3) . ? C16 C17 1.405(7) . ? C16 H16 0.9500 . ? C17 C18 1.351(9) . ? C17 H17 0.9500 . ? C18 C19 1.323(8) . ? C18 H18 0.9500 . ? C19 C20 1.363(6) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 O6 1.214(4) . ? C21 N5 1.321(4) . ? C21 H21 0.9500 . ? C22 N5 1.454(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N5 1.444(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N3 N4 1.282(3) . ? O3 S1 1.598(3) . ? O4 S1 1.410(3) . ? O5 S1 1.401(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.00(11) . 7 ? O1 Cu1 N4 92.28(9) . 7 ? O1 Cu1 N4 87.72(9) 7 7 ? O1 Cu1 N4 87.72(9) . . ? O1 Cu1 N4 92.28(9) 7 . ? N4 Cu1 N4 180.000(17) 7 . ? O1 Cu1 O6 89.51(9) . 7 ? O1 Cu1 O6 90.49(9) 7 7 ? N4 Cu1 O6 86.79(8) 7 7 ? N4 Cu1 O6 93.21(8) . 7 ? O1 Cu1 O6 90.49(9) . . ? O1 Cu1 O6 89.51(9) 7 . ? N4 Cu1 O6 93.21(8) 7 . ? N4 Cu1 O6 86.79(8) . . ? O6 Cu1 O6 180.00(12) 7 . ? O1 C1 N1 117.4(3) . . ? O1 C1 C5 125.1(3) . . ? N1 C1 C5 117.5(3) . . ? O2 C2 N1 120.3(3) . . ? O2 C2 C3 124.2(3) . . ? N1 C2 C3 115.5(3) . . ? C4 C3 C7 121.3(3) . . ? C4 C3 C2 123.1(3) . . ? C7 C3 C2 115.6(3) . . ? C3 C4 C5 118.7(3) . . ? C3 C4 C8 121.1(3) . . ? C5 C4 C8 120.3(3) . . ? N3 C5 C4 115.7(2) . . ? N3 C5 C1 123.2(3) . . ? C4 C5 C1 120.7(3) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C3 178.7(5) . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 121.1(3) . . ? C14 C9 N4 117.7(3) . . ? C10 C9 N4 121.2(3) . . ? C11 C10 C9 118.8(3) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 118.7(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 122.3(3) . . ? C12 C13 O3 119.3(3) . . ? C14 C13 O3 118.3(3) . . ? C9 C14 C13 118.1(3) . . ? C9 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C16 C15 C20 121.9(4) . . ? C16 C15 S1 119.3(4) . . ? C20 C15 S1 118.8(3) . . ? C15 C16 C17 118.4(6) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 118.4(6) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C19 C18 C17 122.1(6) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C18 C19 C20 120.9(6) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C15 C20 C19 118.3(5) . . ? C15 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? O6 C21 N5 125.5(4) . . ? O6 C21 H21 117.3 . . ? N5 C21 H21 117.3 . . ? N5 C22 H22A 109.5 . . ? N5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 H23A 109.5 . . ? N5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 N1 C2 124.5(3) . . ? C1 N1 C6 117.9(3) . . ? C2 N1 C6 117.6(3) . . ? N4 N3 C5 122.3(2) . . ? N3 N4 C9 111.7(2) . . ? N3 N4 Cu1 125.39(17) . . ? C9 N4 Cu1 121.64(18) . . ? C21 N5 C23 121.8(4) . . ? C21 N5 C22 119.7(3) . . ? C23 N5 C22 118.5(4) . . ? C1 O1 Cu1 124.39(19) . . ? C13 O3 S1 118.5(2) . . ? C21 O6 Cu1 121.1(2) . . ? O5 S1 O4 120.3(2) . . ? O5 S1 O3 103.14(18) . . ? O4 S1 O3 108.74(15) . . ? O5 S1 C15 110.19(19) . . ? O4 S1 C15 110.1(2) . . ? O3 S1 C15 102.76(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.367 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.055 data_3 _database_code_depnum_ccdc_archive 'CCDC 913359' #TrackingRef '1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H36 N10 Ni O10' _chemical_formula_sum 'C38 H36 N10 Ni O10' _chemical_formula_weight 851.48 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0372(5) _cell_length_b 10.4058(5) _cell_length_c 11.1366(6) _cell_angle_alpha 73.1240(10) _cell_angle_beta 74.2220(10) _cell_angle_gamma 77.9910(10) _cell_volume 954.89(9) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2645 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.58 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 442 _exptl_absorpt_coefficient_mu 0.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9335 _exptl_absorpt_correction_T_max 0.9442 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (BRUKER, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5349 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3341 _reflns_number_gt 2927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0429P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3341 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 Ni1 Ni 0.5000 0.0000 0.5000 0.03729(12) Uani 1 2 d S . . C14 C 0.5552(3) 0.41967(19) 0.66369(19) 0.0533(5) Uani 1 1 d . . . C13 C 0.4860(3) 0.5104(2) 0.7412(2) 0.0713(7) Uani 1 1 d . . . H13 H 0.5480 0.5590 0.7608 0.086 Uiso 1 1 calc R . . C12 C 0.3299(3) 0.5286(2) 0.7881(2) 0.0800(8) Uani 1 1 d . . . H12 H 0.2868 0.5884 0.8404 0.096 Uiso 1 1 calc R . . C11 C 0.2340(3) 0.4596(2) 0.7592(2) 0.0738(7) Uani 1 1 d . . . H11 H 0.1272 0.4731 0.7914 0.089 Uiso 1 1 calc R . . C10 C 0.2991(3) 0.3708(2) 0.6823(2) 0.0602(5) Uani 1 1 d . . . H10 H 0.2351 0.3250 0.6617 0.072 Uiso 1 1 calc R . . C9 C 0.4590(2) 0.34824(18) 0.63481(17) 0.0474(5) Uani 1 1 d . . . C8 C 0.5265(2) 0.24788(17) 0.55844(17) 0.0424(4) Uani 1 1 d . . . C7 C 0.6895(2) 0.23244(17) 0.51136(17) 0.0427(4) Uani 1 1 d . . . C15 C 0.7881(2) 0.31498(19) 0.53435(18) 0.0501(5) Uani 1 1 d . . . C16 C 0.8144(3) 0.4789(3) 0.6422(3) 0.0838(8) Uani 1 1 d . . . H16A H 0.7953 0.5724 0.5972 0.126 Uiso 1 1 calc R . . H16B H 0.9215 0.4440 0.6139 0.126 Uiso 1 1 calc R . . H16C H 0.7916 0.4717 0.7331 0.126 Uiso 1 1 calc R . . C4 C 0.82515(19) 0.00340(17) 0.31294(16) 0.0400(4) Uani 1 1 d . . . C5 C 0.9816(2) -0.0223(2) 0.31599(19) 0.0528(5) Uani 1 1 d . . . H5 H 1.0150 0.0064 0.3746 0.063 Uiso 1 1 calc R . . C6 C 1.0870(2) -0.0903(2) 0.23244(19) 0.0570(5) Uani 1 1 d . . . H6 H 1.1919 -0.1067 0.2332 0.068 Uiso 1 1 calc R . . C1 C 1.0349(2) -0.13331(19) 0.14814(17) 0.0497(5) Uani 1 1 d . . . C2 C 0.8814(2) -0.1074(2) 0.14187(18) 0.0551(5) Uani 1 1 d . . . H2 H 0.8491 -0.1360 0.0825 0.066 Uiso 1 1 calc R . . C3 C 0.7762(2) -0.0387(2) 0.22469(17) 0.0487(5) Uani 1 1 d . . . H3 H 0.6719 -0.0204 0.2215 0.058 Uiso 1 1 calc R . . C17 C 0.7049(2) -0.15042(18) 0.68399(17) 0.0442(4) Uani 1 1 d . . . H17 H 0.7766 -0.1691 0.6114 0.053 Uiso 1 1 calc R . . C18 C 0.6275(3) -0.1854(4) 0.9132(2) 0.1063(11) Uani 1 1 d . . . H18A H 0.6427 -0.1033 0.9282 0.159 Uiso 1 1 calc R . . H18B H 0.6441 -0.2600 0.9850 0.159 Uiso 1 1 calc R . . H18C H 0.5234 -0.1769 0.9033 0.159 Uiso 1 1 calc R . . C19 C 0.8829(3) -0.2969(2) 0.8110(2) 0.0717(6) Uani 1 1 d . . . H19A H 0.9439 -0.3056 0.7277 0.108 Uiso 1 1 calc R . . H19B H 0.8620 -0.3848 0.8644 0.108 Uiso 1 1 calc R . . H19C H 0.9391 -0.2578 0.8501 0.108 Uiso 1 1 calc R . . N4 N 0.7147(2) 0.40030(16) 0.61540(16) 0.0570(4) Uani 1 1 d . . . N3 N 0.77346(17) 0.15402(14) 0.43108(14) 0.0428(4) Uani 1 1 d . . . N2 N 0.71135(16) 0.06966(14) 0.40154(13) 0.0400(3) Uani 1 1 d . . . N1 N 1.1461(2) -0.2138(2) 0.06434(17) 0.0692(5) Uani 1 1 d . . . N5 N 0.73678(18) -0.20953(18) 0.79685(15) 0.0548(4) Uani 1 1 d . . . O3 O 0.43608(14) 0.18252(12) 0.53794(12) 0.0460(3) Uani 1 1 d . . . O4 O 0.92778(16) 0.30900(15) 0.48903(14) 0.0642(4) Uani 1 1 d . . . O1 O 1.0965(2) -0.2668(2) 0.0037(2) 0.1106(7) Uani 1 1 d . . . O2 O 1.2827(2) -0.2231(2) 0.06119(18) 0.1033(7) Uani 1 1 d . . . O5 O 0.58492(14) -0.07105(13) 0.66817(12) 0.0496(3) 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 Ni1 0.03125(19) 0.0407(2) 0.0417(2) -0.01520(14) -0.00567(14) -0.00520(13) C14 0.0718(14) 0.0373(10) 0.0469(11) -0.0121(9) -0.0043(10) -0.0091(9) C13 0.0958(19) 0.0515(13) 0.0685(15) -0.0287(12) -0.0088(14) -0.0074(12) C12 0.104(2) 0.0538(14) 0.0694(16) -0.0293(13) 0.0011(15) 0.0085(14) C11 0.0721(16) 0.0553(13) 0.0778(17) -0.0238(13) 0.0027(13) 0.0108(12) C10 0.0605(14) 0.0443(11) 0.0645(13) -0.0154(10) -0.0039(11) 0.0061(10) C9 0.0552(12) 0.0357(10) 0.0455(11) -0.0117(8) -0.0033(9) -0.0017(9) C8 0.0460(11) 0.0360(9) 0.0419(10) -0.0097(8) -0.0060(8) -0.0040(8) C7 0.0428(11) 0.0418(10) 0.0446(10) -0.0161(8) -0.0047(8) -0.0079(8) C15 0.0574(13) 0.0451(11) 0.0504(11) -0.0150(9) -0.0057(10) -0.0167(9) C16 0.098(2) 0.0827(17) 0.0921(18) -0.0460(15) -0.0089(15) -0.0415(15) C4 0.0366(10) 0.0412(9) 0.0400(10) -0.0116(8) -0.0014(8) -0.0079(8) C5 0.0406(11) 0.0674(13) 0.0554(12) -0.0267(11) -0.0067(9) -0.0074(9) C6 0.0382(11) 0.0716(14) 0.0565(12) -0.0200(11) -0.0038(9) -0.0004(10) C1 0.0504(12) 0.0516(11) 0.0403(10) -0.0163(9) 0.0024(9) -0.0021(9) C2 0.0564(13) 0.0688(13) 0.0447(11) -0.0254(10) -0.0038(9) -0.0125(10) C3 0.0395(10) 0.0630(12) 0.0452(11) -0.0212(10) -0.0050(8) -0.0059(9) C17 0.0421(11) 0.0485(11) 0.0463(11) -0.0171(9) -0.0085(9) -0.0103(9) C18 0.0677(18) 0.172(3) 0.0511(15) -0.0182(17) -0.0075(13) 0.0229(18) C19 0.0550(14) 0.0805(16) 0.0770(16) -0.0198(13) -0.0257(12) 0.0106(12) N4 0.0682(12) 0.0513(10) 0.0592(10) -0.0256(9) -0.0047(9) -0.0210(8) N3 0.0422(9) 0.0436(8) 0.0451(9) -0.0158(7) -0.0046(7) -0.0114(7) N2 0.0357(8) 0.0432(8) 0.0428(8) -0.0174(7) -0.0041(7) -0.0058(6) N1 0.0640(13) 0.0774(13) 0.0546(11) -0.0246(10) 0.0055(10) 0.0020(10) N5 0.0410(9) 0.0725(11) 0.0470(10) -0.0138(9) -0.0116(8) 0.0008(8) O3 0.0365(7) 0.0459(7) 0.0572(8) -0.0205(6) -0.0059(6) -0.0047(6) O4 0.0509(9) 0.0728(10) 0.0778(10) -0.0331(8) -0.0006(8) -0.0261(7) O1 0.0983(15) 0.1457(19) 0.1109(15) -0.0975(15) -0.0068(12) 0.0042(13) O2 0.0575(12) 0.1459(18) 0.0983(14) -0.0607(14) 0.0054(10) 0.0161(11) O5 0.0400(7) 0.0604(8) 0.0482(8) -0.0172(6) -0.0112(6) -0.0001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O3 1.9990(11) . ? Ni1 O3 1.9990(11) 2_656 ? Ni1 N2 2.0861(14) 2_656 ? Ni1 N2 2.0861(14) . ? Ni1 O5 2.0940(11) . ? Ni1 O5 2.0940(11) 2_656 ? C14 N4 1.389(3) . ? C14 C13 1.401(3) . ? C14 C9 1.404(3) . ? C13 C12 1.358(3) . ? C13 H13 0.9300 . ? C12 C11 1.383(4) . ? C12 H12 0.9300 . ? C11 C10 1.376(3) . ? C11 H11 0.9300 . ? C10 C9 1.392(3) . ? C10 H10 0.9300 . ? C9 C8 1.468(2) . ? C8 O3 1.267(2) . ? C8 C7 1.414(3) . ? C7 N3 1.356(2) . ? C7 C15 1.473(2) . ? C15 O4 1.221(2) . ? C15 N4 1.392(2) . ? C16 N4 1.471(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C4 C3 1.386(2) . ? C4 C5 1.391(2) . ? C4 N2 1.433(2) . ? C5 C6 1.375(3) . ? C5 H5 0.9300 . ? C6 C1 1.369(3) . ? C6 H6 0.9300 . ? C1 C2 1.374(3) . ? C1 N1 1.475(2) . ? C2 C3 1.375(2) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C17 O5 1.239(2) . ? C17 N5 1.310(2) . ? C17 H17 0.9300 . ? C18 N5 1.452(3) . ? C18 H18A 0.9601 . ? C18 H18B 0.9601 . ? C18 H18C 0.9601 . ? C19 N5 1.458(2) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N3 N2 1.2911(19) . ? N1 O1 1.202(2) . ? N1 O2 1.210(2) . ? 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 O3 Ni1 O3 180.0 . 2_656 ? O3 Ni1 N2 94.87(5) . 2_656 ? O3 Ni1 N2 85.13(5) 2_656 2_656 ? O3 Ni1 N2 85.13(5) . . ? O3 Ni1 N2 94.87(5) 2_656 . ? N2 Ni1 N2 180.00(4) 2_656 . ? O3 Ni1 O5 89.02(5) . . ? O3 Ni1 O5 90.98(5) 2_656 . ? N2 Ni1 O5 90.94(5) 2_656 . ? N2 Ni1 O5 89.06(5) . . ? O3 Ni1 O5 90.98(5) . 2_656 ? O3 Ni1 O5 89.02(5) 2_656 2_656 ? N2 Ni1 O5 89.06(5) 2_656 2_656 ? N2 Ni1 O5 90.94(5) . 2_656 ? O5 Ni1 O5 180.00(3) . 2_656 ? N4 C14 C13 121.4(2) . . ? N4 C14 C9 120.22(16) . . ? C13 C14 C9 118.4(2) . . ? C12 C13 C14 121.0(2) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C12 C11 121.0(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C10 C11 C12 119.0(2) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C10 C9 121.2(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C9 C14 119.35(17) . . ? C10 C9 C8 120.24(18) . . ? C14 C9 C8 120.39(18) . . ? O3 C8 C7 124.56(15) . . ? O3 C8 C9 118.43(16) . . ? C7 C8 C9 117.01(16) . . ? N3 C7 C8 126.54(16) . . ? N3 C7 C15 111.03(16) . . ? C8 C7 C15 122.11(15) . . ? O4 C15 N4 120.08(17) . . ? O4 C15 C7 123.48(16) . . ? N4 C15 C7 116.42(17) . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C3 C4 C5 119.73(16) . . ? C3 C4 N2 118.64(15) . . ? C5 C4 N2 121.61(15) . . ? C6 C5 C4 120.08(17) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 118.98(18) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C1 C2 122.07(17) . . ? C6 C1 N1 119.00(18) . . ? C2 C1 N1 118.89(18) . . ? C1 C2 C3 118.97(17) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.14(17) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? O5 C17 N5 123.89(17) . . ? O5 C17 H17 118.1 . . ? N5 C17 H17 118.1 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N5 C19 H19A 109.5 . . ? N5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C14 N4 C15 123.50(16) . . ? C14 N4 C16 119.99(17) . . ? C15 N4 C16 116.39(18) . . ? N2 N3 C7 121.54(15) . . ? N3 N2 C4 109.61(14) . . ? N3 N2 Ni1 125.77(10) . . ? C4 N2 Ni1 122.81(11) . . ? O1 N1 O2 123.7(2) . . ? O1 N1 C1 118.5(2) . . ? O2 N1 C1 117.8(2) . . ? C17 N5 C18 120.16(16) . . ? C17 N5 C19 122.20(17) . . ? C18 N5 C19 117.61(17) . . ? C8 O3 Ni1 124.23(11) . . ? C17 O5 Ni1 127.40(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C14 C13 C12 -179.9(2) . . . . ? C9 C14 C13 C12 0.4(3) . . . . ? C14 C13 C12 C11 -1.0(4) . . . . ? C13 C12 C11 C10 0.4(4) . . . . ? C12 C11 C10 C9 0.8(3) . . . . ? C11 C10 C9 C14 -1.4(3) . . . . ? C11 C10 C9 C8 176.85(18) . . . . ? N4 C14 C9 C10 -178.91(18) . . . . ? C13 C14 C9 C10 0.8(3) . . . . ? N4 C14 C9 C8 2.9(3) . . . . ? C13 C14 C9 C8 -177.48(17) . . . . ? C10 C9 C8 O3 -0.4(3) . . . . ? C14 C9 C8 O3 177.80(17) . . . . ? C10 C9 C8 C7 178.81(17) . . . . ? C14 C9 C8 C7 -3.0(3) . . . . ? O3 C8 C7 N3 4.8(3) . . . . ? C9 C8 C7 N3 -174.43(16) . . . . ? O3 C8 C7 C15 177.68(17) . . . . ? C9 C8 C7 C15 -1.5(3) . . . . ? N3 C7 C15 O4 -2.0(3) . . . . ? C8 C7 C15 O4 -175.87(19) . . . . ? N3 C7 C15 N4 179.87(16) . . . . ? C8 C7 C15 N4 5.9(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? N2 C4 C5 C6 177.77(18) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C5 C6 C1 C2 1.9(3) . . . . ? C5 C6 C1 N1 -176.10(19) . . . . ? C6 C1 C2 C3 -1.4(3) . . . . ? N1 C1 C2 C3 176.58(18) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C5 C4 C3 C2 1.0(3) . . . . ? N2 C4 C3 C2 -177.34(18) . . . . ? C13 C14 N4 C15 -177.62(18) . . . . ? C9 C14 N4 C15 2.0(3) . . . . ? C13 C14 N4 C16 -1.8(3) . . . . ? C9 C14 N4 C16 177.87(19) . . . . ? O4 C15 N4 C14 175.49(19) . . . . ? C7 C15 N4 C14 -6.3(3) . . . . ? O4 C15 N4 C16 -0.5(3) . . . . ? C7 C15 N4 C16 177.77(18) . . . . ? C8 C7 N3 N2 -9.0(3) . . . . ? C15 C7 N3 N2 177.38(15) . . . . ? C7 N3 N2 C4 178.44(15) . . . . ? C7 N3 N2 Ni1 -16.6(2) . . . . ? C3 C4 N2 N3 -150.08(17) . . . . ? C5 C4 N2 N3 31.6(2) . . . . ? C3 C4 N2 Ni1 44.4(2) . . . . ? C5 C4 N2 Ni1 -133.90(16) . . . . ? O3 Ni1 N2 N3 31.86(13) . . . . ? O3 Ni1 N2 N3 -148.14(13) 2_656 . . . ? N2 Ni1 N2 N3 83(100) 2_656 . . . ? O5 Ni1 N2 N3 -57.24(13) . . . . ? O5 Ni1 N2 N3 122.76(13) 2_656 . . . ? O3 Ni1 N2 C4 -165.05(13) . . . . ? O3 Ni1 N2 C4 14.95(13) 2_656 . . . ? N2 Ni1 N2 C4 -114(100) 2_656 . . . ? O5 Ni1 N2 C4 105.86(12) . . . . ? O5 Ni1 N2 C4 -74.14(12) 2_656 . . . ? C6 C1 N1 O1 169.9(2) . . . . ? C2 C1 N1 O1 -8.1(3) . . . . ? C6 C1 N1 O2 -9.7(3) . . . . ? C2 C1 N1 O2 172.3(2) . . . . ? O5 C17 N5 C18 1.0(3) . . . . ? O5 C17 N5 C19 -176.78(19) . . . . ? C7 C8 O3 Ni1 25.7(2) . . . . ? C9 C8 O3 Ni1 -155.17(12) . . . . ? O3 Ni1 O3 C8 -119(100) 2_656 . . . ? N2 Ni1 O3 C8 144.71(14) 2_656 . . . ? N2 Ni1 O3 C8 -35.29(14) . . . . ? O5 Ni1 O3 C8 53.85(14) . . . . ? O5 Ni1 O3 C8 -126.15(14) 2_656 . . . ? N5 C17 O5 Ni1 -167.14(14) . . . . ? O3 Ni1 O5 C17 -140.85(15) . . . . ? O3 Ni1 O5 C17 39.15(15) 2_656 . . . ? N2 Ni1 O5 C17 124.30(15) 2_656 . . . ? N2 Ni1 O5 C17 -55.70(15) . . . . ? O5 Ni1 O5 C17 157(100) 2_656 . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.230 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.041 data_4 _database_code_depnum_ccdc_archive 'CCDC 913360' #TrackingRef '1-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H36 Cu N10 O10' _chemical_formula_sum 'C38 H36 Cu N10 O10' _chemical_formula_weight 856.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.443(5) _cell_length_b 9.828(7) _cell_length_c 11.689(7) _cell_angle_alpha 72.521(10) _cell_angle_beta 69.916(9) _cell_angle_gamma 78.602(9) _cell_volume 966.4(10) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1503 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.49 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 443 _exptl_absorpt_coefficient_mu 0.637 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9274 _exptl_absorpt_correction_T_max 0.9390 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (BRUKER, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER Smart Apex CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6380 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0773 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3367 _reflns_number_gt 2499 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0412P)^2^+0.5723P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3367 _refine_ls_number_parameters 270 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.056 _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 1.0000 0.5000 0.0000 0.0379(2) Uani 1 2 d S . . C1 C 0.4834(4) 0.6454(4) 0.3536(4) 0.0450(9) Uani 1 1 d . . . C2 C 0.4373(5) 0.6176(5) 0.2642(4) 0.0615(12) Uani 1 1 d . . . H2 H 0.3387 0.6468 0.2606 0.074 Uiso 1 1 calc R . . C3 C 0.5390(4) 0.5461(4) 0.1805(4) 0.0538(11) Uani 1 1 d . . . H3 H 0.5091 0.5260 0.1198 0.065 Uiso 1 1 calc R . . C4 C 0.6856(4) 0.5036(3) 0.1855(3) 0.0377(8) Uani 1 1 d . . . C5 C 0.7289(4) 0.5296(4) 0.2774(3) 0.0407(9) Uani 1 1 d . . . H5 H 0.8265 0.4981 0.2828 0.049 Uiso 1 1 calc R . . C6 C 0.6273(4) 0.6023(4) 0.3613(4) 0.0470(10) Uani 1 1 d . . . H6 H 0.6563 0.6219 0.4227 0.056 Uiso 1 1 calc R . . C7 C 0.8148(4) 0.2663(3) -0.0109(3) 0.0402(9) Uani 1 1 d . . . C8 C 0.7183(5) 0.1814(4) -0.0314(4) 0.0465(10) Uani 1 1 d . . . C9 C 0.9481(5) 0.0699(4) -0.1597(4) 0.0526(11) Uani 1 1 d . . . C10 C 1.0153(6) -0.0260(4) -0.2352(4) 0.0671(13) Uani 1 1 d . . . H10 H 0.9550 -0.0766 -0.2524 0.081 Uiso 1 1 calc R . . C11 C 1.1688(7) -0.0456(4) -0.2837(5) 0.0796(16) Uani 1 1 d . . . H11 H 1.2122 -0.1079 -0.3356 0.096 Uiso 1 1 calc R . . C12 C 1.2605(6) 0.0251(4) -0.2572(4) 0.0730(15) Uani 1 1 d . . . H12 H 1.3653 0.0092 -0.2899 0.088 Uiso 1 1 calc R . . C13 C 1.1977(5) 0.1190(4) -0.1826(4) 0.0562(11) Uani 1 1 d . . . H13 H 1.2603 0.1665 -0.1645 0.067 Uiso 1 1 calc R . . C14 C 1.0408(4) 0.1439(3) -0.1336(4) 0.0455(10) Uani 1 1 d . . . C15 C 0.9735(4) 0.2490(3) -0.0597(3) 0.0401(9) Uani 1 1 d . . . C16 C 0.6958(6) 0.0076(5) -0.1326(5) 0.0908(18) Uani 1 1 d . . . H16A H 0.7240 0.0154 -0.2213 0.136 Uiso 1 1 calc R . . H16B H 0.5915 0.0448 -0.1035 0.136 Uiso 1 1 calc R . . H16C H 0.7091 -0.0913 -0.0886 0.136 Uiso 1 1 calc R . . C17 C 1.2074(5) 0.3497(4) 0.2029(4) 0.0497(10) Uani 1 1 d . . . H17 H 1.2870 0.3418 0.1306 0.060 Uiso 1 1 calc R . . C18 C 1.1156(6) 0.2950(8) 0.4262(5) 0.130(3) Uani 1 1 d U . . H18A H 1.0618 0.3894 0.4163 0.195 Uiso 1 1 d R . . H18B H 1.1605 0.2765 0.4924 0.195 Uiso 1 1 d R . . H18C H 1.0464 0.2254 0.4471 0.195 Uiso 1 1 d R . . C19 C 1.3768(5) 0.2065(6) 0.3189(5) 0.0812(15) Uani 1 1 d . . . H19A H 1.4419 0.2033 0.2359 0.122 Uiso 1 1 calc R . . H19B H 1.3613 0.1106 0.3697 0.122 Uiso 1 1 calc R . . H19C H 1.4230 0.2533 0.3561 0.122 Uiso 1 1 calc R . . N1 N 0.3781(5) 0.7299(4) 0.4379(3) 0.0615(10) Uani 1 1 d . . . N2 N 0.7946(3) 0.4340(3) 0.0956(3) 0.0369(7) Uani 1 1 d . . . N3 N 0.7329(3) 0.3476(3) 0.0682(3) 0.0389(7) Uani 1 1 d . . . N4 N 0.7918(4) 0.0900(3) -0.1091(3) 0.0569(9) Uani 1 1 d . . . N5 N 1.2319(4) 0.2857(4) 0.3112(4) 0.0612(10) Uani 1 1 d U . . O1 O 0.4258(4) 0.7706(4) 0.5038(3) 0.0905(12) Uani 1 1 d . . . O2 O 0.2474(4) 0.7541(5) 0.4394(4) 0.1064(14) Uani 1 1 d . . . O3 O 0.5810(3) 0.1890(3) 0.0159(3) 0.0607(8) Uani 1 1 d . . . O4 O 1.0612(3) 0.3170(2) -0.0411(2) 0.0424(6) Uani 1 1 d . . . O5 O 1.0894(3) 0.4190(3) 0.1884(3) 0.0641(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 0.0298(4) 0.0368(3) 0.0457(4) -0.0168(3) -0.0021(3) -0.0077(2) C1 0.044(2) 0.050(2) 0.037(2) -0.0212(18) -0.0012(19) -0.0004(17) C2 0.037(2) 0.090(3) 0.064(3) -0.041(3) -0.011(2) 0.009(2) C3 0.039(2) 0.077(3) 0.057(3) -0.042(2) -0.013(2) 0.004(2) C4 0.032(2) 0.0422(18) 0.037(2) -0.0175(17) 0.0010(17) -0.0082(15) C5 0.035(2) 0.052(2) 0.036(2) -0.0168(18) -0.0060(17) -0.0068(16) C6 0.052(3) 0.057(2) 0.036(2) -0.0214(19) -0.0070(19) -0.0122(19) C7 0.041(2) 0.0389(17) 0.042(2) -0.0229(17) 0.0009(18) -0.0103(15) C8 0.054(3) 0.0450(19) 0.042(2) -0.0178(18) -0.003(2) -0.0190(18) C9 0.070(3) 0.0342(18) 0.045(2) -0.0156(18) 0.003(2) -0.0153(18) C10 0.094(4) 0.046(2) 0.057(3) -0.030(2) 0.001(3) -0.014(2) C11 0.105(4) 0.044(2) 0.065(3) -0.024(2) 0.010(3) -0.001(3) C12 0.070(3) 0.048(2) 0.068(3) -0.017(2) 0.014(3) 0.009(2) C13 0.050(3) 0.0387(19) 0.060(3) -0.010(2) 0.003(2) 0.0009(17) C14 0.052(2) 0.0312(17) 0.041(2) -0.0146(17) 0.0055(19) -0.0043(16) C15 0.039(2) 0.0355(17) 0.040(2) -0.0109(16) -0.0019(18) -0.0074(15) C16 0.088(4) 0.101(4) 0.105(4) -0.070(3) 0.003(3) -0.047(3) C17 0.044(3) 0.057(2) 0.053(3) -0.026(2) -0.009(2) -0.0090(19) C18 0.071(4) 0.221(7) 0.059(4) -0.024(4) -0.006(3) 0.030(4) C19 0.056(3) 0.102(4) 0.091(4) -0.031(3) -0.038(3) 0.019(3) N1 0.057(3) 0.071(2) 0.045(2) -0.0263(19) 0.002(2) 0.0018(19) N2 0.0325(16) 0.0400(15) 0.0401(18) -0.0201(14) -0.0042(14) -0.0051(12) N3 0.0393(17) 0.0388(15) 0.0382(18) -0.0132(14) -0.0045(14) -0.0109(13) N4 0.062(2) 0.0548(19) 0.060(2) -0.0334(18) -0.0012(19) -0.0235(17) N5 0.043(2) 0.090(3) 0.051(2) -0.026(2) -0.0152(19) 0.0049(19) O1 0.085(3) 0.119(3) 0.085(3) -0.076(2) -0.012(2) 0.004(2) O2 0.063(3) 0.159(4) 0.100(3) -0.082(3) -0.011(2) 0.033(2) O3 0.0454(17) 0.0763(19) 0.072(2) -0.0401(17) -0.0042(16) -0.0244(14) O4 0.0326(14) 0.0381(12) 0.0519(17) -0.0148(12) -0.0026(12) -0.0061(10) O5 0.0461(18) 0.082(2) 0.060(2) -0.0183(17) -0.0181(16) 0.0073(15) _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 O4 1.927(2) . ? Cu1 O4 1.927(2) 2_765 ? Cu1 N2 2.001(3) . ? Cu1 N2 2.001(3) 2_765 ? Cu1 O5 2.480(3) . ? C1 C6 1.367(5) . ? C1 C2 1.373(5) . ? C1 N1 1.464(5) . ? C2 C3 1.369(5) . ? C2 H2 0.9300 . ? C3 C4 1.381(5) . ? C3 H3 0.9300 . ? C4 C5 1.376(5) . ? C4 N2 1.430(4) . ? C5 C6 1.377(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N3 1.342(4) . ? C7 C15 1.404(5) . ? C7 C8 1.467(5) . ? C8 O3 1.219(4) . ? C8 N4 1.387(5) . ? C9 N4 1.386(5) . ? C9 C10 1.396(5) . ? C9 C14 1.398(5) . ? C10 C11 1.360(6) . ? C10 H10 0.9300 . ? C11 C12 1.370(7) . ? C11 H11 0.9300 . ? C12 C13 1.370(6) . ? C12 H12 0.9300 . ? C13 C14 1.394(5) . ? C13 H13 0.9300 . ? C14 C15 1.455(5) . ? C15 O4 1.269(4) . ? C16 N4 1.466(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O5 1.223(5) . ? C17 N5 1.310(5) . ? C17 H17 0.9300 . ? C18 N5 1.428(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N5 1.452(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 O1 1.204(4) . ? N1 O2 1.205(5) . ? N2 N3 1.284(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O4 180.000(1) . 2_765 ? O4 Cu1 N2 87.69(10) . . ? O4 Cu1 N2 92.31(10) 2_765 . ? O4 Cu1 N2 92.31(10) . 2_765 ? O4 Cu1 N2 87.69(10) 2_765 2_765 ? N2 Cu1 N2 180.00(15) . 2_765 ? O4 Cu1 O5 93.67(11) . . ? O4 Cu1 O5 86.33(10) 2_765 . ? N2 Cu1 O5 93.48(11) . . ? N2 Cu1 O5 86.52(11) 2_765 . ? C6 C1 C2 121.6(3) . . ? C6 C1 N1 119.4(3) . . ? C2 C1 N1 118.9(4) . . ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.9(3) . . ? C5 C4 N2 119.0(3) . . ? C3 C4 N2 121.0(3) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.4(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? N3 C7 C15 126.3(3) . . ? N3 C7 C8 111.3(3) . . ? C15 C7 C8 122.1(3) . . ? O3 C8 N4 120.7(3) . . ? O3 C8 C7 123.1(3) . . ? N4 C8 C7 116.3(3) . . ? N4 C9 C10 120.8(4) . . ? N4 C9 C14 120.2(3) . . ? C10 C9 C14 119.0(4) . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 121.0(4) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 120.0(5) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.4(4) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 119.3(3) . . ? C13 C14 C15 120.6(3) . . ? C9 C14 C15 120.2(3) . . ? O4 C15 C7 124.1(3) . . ? O4 C15 C14 118.4(3) . . ? C7 C15 C14 117.5(3) . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 N5 125.8(4) . . ? O5 C17 H17 117.1 . . ? N5 C17 H17 117.1 . . ? N5 C18 H18A 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N5 C19 H19A 109.5 . . ? N5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 N1 O2 123.0(4) . . ? O1 N1 C1 118.4(4) . . ? O2 N1 C1 118.6(4) . . ? N3 N2 C4 110.9(3) . . ? N3 N2 Cu1 125.4(2) . . ? C4 N2 Cu1 122.3(2) . . ? N2 N3 C7 121.5(3) . . ? C9 N4 C8 123.5(3) . . ? C9 N4 C16 119.8(3) . . ? C8 N4 C16 116.6(4) . . ? C17 N5 C18 120.2(4) . . ? C17 N5 C19 121.8(4) . . ? C18 N5 C19 118.0(4) . . ? C15 O4 Cu1 123.6(2) . . ? C17 O5 Cu1 130.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.6(7) . . . . ? N1 C1 C2 C3 176.0(4) . . . . ? C1 C2 C3 C4 -0.4(7) . . . . ? C2 C3 C4 C5 1.8(6) . . . . ? C2 C3 C4 N2 -177.5(4) . . . . ? C3 C4 C5 C6 -2.3(5) . . . . ? N2 C4 C5 C6 177.1(3) . . . . ? C2 C1 C6 C5 0.2(6) . . . . ? N1 C1 C6 C5 -176.4(3) . . . . ? C4 C5 C6 C1 1.3(6) . . . . ? N3 C7 C8 O3 1.8(6) . . . . ? C15 C7 C8 O3 175.8(4) . . . . ? N3 C7 C8 N4 -178.3(3) . . . . ? C15 C7 C8 N4 -4.3(6) . . . . ? N4 C9 C10 C11 -179.6(4) . . . . ? C14 C9 C10 C11 -0.8(7) . . . . ? C9 C10 C11 C12 1.6(7) . . . . ? C10 C11 C12 C13 -1.1(7) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C9 1.1(6) . . . . ? C12 C13 C14 C15 -176.8(4) . . . . ? N4 C9 C14 C13 178.2(4) . . . . ? C10 C9 C14 C13 -0.6(6) . . . . ? N4 C9 C14 C15 -3.8(6) . . . . ? C10 C9 C14 C15 177.4(4) . . . . ? N3 C7 C15 O4 -4.9(6) . . . . ? C8 C7 C15 O4 -177.8(3) . . . . ? N3 C7 C15 C14 173.6(3) . . . . ? C8 C7 C15 C14 0.7(5) . . . . ? C13 C14 C15 O4 0.0(5) . . . . ? C9 C14 C15 O4 -177.9(3) . . . . ? C13 C14 C15 C7 -178.6(3) . . . . ? C9 C14 C15 C7 3.5(5) . . . . ? C6 C1 N1 O1 6.8(6) . . . . ? C2 C1 N1 O1 -169.9(4) . . . . ? C6 C1 N1 O2 -172.2(4) . . . . ? C2 C1 N1 O2 11.1(6) . . . . ? C5 C4 N2 N3 142.8(3) . . . . ? C3 C4 N2 N3 -37.9(5) . . . . ? C5 C4 N2 Cu1 -50.2(4) . . . . ? C3 C4 N2 Cu1 129.2(3) . . . . ? O4 Cu1 N2 N3 -31.2(3) . . . . ? O4 Cu1 N2 N3 148.8(3) 2_765 . . . ? N2 Cu1 N2 N3 -123(100) 2_765 . . . ? O5 Cu1 N2 N3 -124.8(3) . . . . ? O4 Cu1 N2 C4 163.6(3) . . . . ? O4 Cu1 N2 C4 -16.4(3) 2_765 . . . ? N2 Cu1 N2 C4 72(100) 2_765 . . . ? O5 Cu1 N2 C4 70.1(3) . . . . ? C4 N2 N3 C7 -177.5(3) . . . . ? Cu1 N2 N3 C7 15.9(5) . . . . ? C15 C7 N3 N2 8.8(6) . . . . ? C8 C7 N3 N2 -177.6(3) . . . . ? C10 C9 N4 C8 178.6(4) . . . . ? C14 C9 N4 C8 -0.2(6) . . . . ? C10 C9 N4 C16 1.3(6) . . . . ? C14 C9 N4 C16 -177.5(4) . . . . ? O3 C8 N4 C9 -176.0(4) . . . . ? C7 C8 N4 C9 4.1(6) . . . . ? O3 C8 N4 C16 1.4(6) . . . . ? C7 C8 N4 C16 -178.5(4) . . . . ? O5 C17 N5 C18 -0.9(7) . . . . ? O5 C17 N5 C19 -179.5(4) . . . . ? C7 C15 O4 Cu1 -24.1(5) . . . . ? C14 C15 O4 Cu1 157.4(2) . . . . ? O4 Cu1 O4 C15 156(100) 2_765 . . . ? N2 Cu1 O4 C15 34.2(3) . . . . ? N2 Cu1 O4 C15 -145.8(3) 2_765 . . . ? O5 Cu1 O4 C15 127.5(3) . . . . ? N5 C17 O5 Cu1 -164.3(3) . . . . ? O4 Cu1 O5 C17 44.9(4) . . . . ? O4 Cu1 O5 C17 -135.1(4) 2_765 . . . ? N2 Cu1 O5 C17 132.8(3) . . . . ? N2 Cu1 O5 C17 -47.2(3) 2_765 . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.415 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.062 #===END