# Electronic Supplementary Material (ESI) for CrystEngComm # 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 912093' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H32 N4 Ni O8' _chemical_formula_weight 647.32 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9158(3) _cell_length_b 14.3094(4) _cell_length_c 18.5432(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.6850(10) _cell_angle_gamma 90.00 _cell_volume 3151.20(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5259 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.671 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6419 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 30058 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.1057 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.31 _reflns_number_total 7822 _reflns_number_gt 3595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0337P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7822 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1526 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni -0.61563(3) 0.50449(3) 0.74154(2) 0.04085(13) Uani 1 1 d . . . O1 O -0.26426(19) 0.24442(16) 1.00203(13) 0.0632(7) Uani 1 1 d . . . O2 O 0.2271(2) 0.24856(17) 0.96412(14) 0.0835(9) Uani 1 1 d . . . O3 O -0.64546(18) 0.37389(14) 0.69843(12) 0.0495(6) Uani 1 1 d . . . O4 O -0.74986(17) 0.42016(14) 0.78277(12) 0.0491(6) Uani 1 1 d . . . O5 O -0.73987(17) -0.40894(15) 0.68198(12) 0.0506(6) Uani 1 1 d . . . O6 O -0.64115(18) -0.36149(14) 0.77892(12) 0.0494(6) Uani 1 1 d . . . N1 N -0.5073(2) 0.46743(18) 0.82805(14) 0.0437(7) Uani 1 1 d . . . N2 N -0.2778(2) 0.40254(18) 1.00504(14) 0.0474(7) Uani 1 1 d . . . H2N H -0.2545 0.4508 1.0295 0.057 Uiso 1 1 calc R . . N3 N 0.2518(2) 0.09230(18) 0.97301(14) 0.0512(8) Uani 1 1 d . . . H3N H 0.2304 0.0434 0.9951 0.061 Uiso 1 1 calc R . . N4 N 0.4973(2) 0.03660(18) 0.82886(14) 0.0446(7) Uani 1 1 d . . . C1 C -0.4719(3) 0.3806(2) 0.8410(2) 0.0559(10) Uani 1 1 d . . . H1A H -0.4979 0.3347 0.8083 0.067 Uiso 1 1 calc R . . C2 C -0.4000(3) 0.3530(2) 0.89873(19) 0.0532(9) Uani 1 1 d . . . H2A H -0.3800 0.2905 0.9048 0.064 Uiso 1 1 calc R . . C3 C -0.3580(3) 0.4195(2) 0.94761(17) 0.0409(8) Uani 1 1 d . . . C4 C -0.3960(2) 0.5103(2) 0.93574(17) 0.0461(8) Uani 1 1 d . . . H4A H -0.3712 0.5577 0.9674 0.055 Uiso 1 1 calc R . . C5 C -0.4699(3) 0.5301(2) 0.87763(19) 0.0488(9) Uani 1 1 d . . . H5A H -0.4958 0.5912 0.8722 0.059 Uiso 1 1 calc R . . C6 C -0.2316(3) 0.3195(2) 1.02737(18) 0.0468(9) Uani 1 1 d . . . C7 C -0.1389(3) 0.3271(2) 1.08733(18) 0.0522(9) Uani 1 1 d . . . H7A H -0.1725 0.3328 1.1330 0.063 Uiso 1 1 calc R . . H7B H -0.0964 0.3837 1.0803 0.063 Uiso 1 1 calc R . . C8 C -0.0575(3) 0.2438(2) 1.09196(17) 0.0511(9) Uani 1 1 d . . . H8A H -0.0167 0.2430 1.1394 0.061 Uiso 1 1 calc R . . H8B H -0.1004 0.1863 1.0865 0.061 Uiso 1 1 calc R . . C9 C 0.0266(3) 0.2476(2) 1.03424(18) 0.0526(9) Uani 1 1 d . . . H9A H 0.0708 0.3043 1.0406 0.063 Uiso 1 1 calc R . . H9B H -0.0143 0.2501 0.9869 0.063 Uiso 1 1 calc R . . C10 C 0.1060(3) 0.1633(2) 1.03734(17) 0.0521(9) Uani 1 1 d . . . H10A H 0.1386 0.1553 1.0866 0.063 Uiso 1 1 calc R . . H10B H 0.0631 0.1075 1.0239 0.063 Uiso 1 1 calc R . . C11 C 0.1989(3) 0.1742(2) 0.98796(19) 0.0546(10) Uani 1 1 d . . . C12 C 0.3365(3) 0.0788(2) 0.92608(17) 0.0452(8) Uani 1 1 d . . . C13 C 0.3864(3) -0.0085(2) 0.92472(18) 0.0530(9) Uani 1 1 d . . . H13A H 0.3665 -0.0551 0.9562 0.064 Uiso 1 1 calc R . . C14 C 0.4654(3) -0.0259(2) 0.87669(19) 0.0548(10) Uani 1 1 d . . . H14A H 0.4987 -0.0847 0.8774 0.066 Uiso 1 1 calc R . . C15 C 0.4480(3) 0.1196(2) 0.8313(2) 0.0588(10) Uani 1 1 d . . . H15A H 0.4677 0.1644 0.7982 0.071 Uiso 1 1 calc R . . C16 C 0.3708(3) 0.1447(2) 0.87832(19) 0.0607(11) Uani 1 1 d . . . H16A H 0.3419 0.2051 0.8781 0.073 Uiso 1 1 calc R . . C17 C -0.7239(3) 0.3579(2) 0.73861(18) 0.0415(8) Uani 1 1 d . . . C18 C -0.7822(2) 0.2660(2) 0.73443(17) 0.0399(8) Uani 1 1 d . . . C19 C -0.7544(3) 0.2002(2) 0.68482(19) 0.0504(9) Uani 1 1 d . . . H19A H -0.6988 0.2134 0.6539 0.060 Uiso 1 1 calc R . . C20 C -0.8086(3) 0.1146(2) 0.6805(2) 0.0593(10) Uani 1 1 d . . . H20A H -0.7874 0.0702 0.6476 0.071 Uiso 1 1 calc R . . C21 C -0.8934(3) 0.0944(2) 0.7243(2) 0.0495(9) Uani 1 1 d . . . C22 C -0.9193(3) 0.1600(2) 0.77455(19) 0.0551(10) Uani 1 1 d . . . H22A H -0.9741 0.1467 0.8060 0.066 Uiso 1 1 calc R . . C23 C -0.8652(3) 0.2453(2) 0.77907(18) 0.0496(9) Uani 1 1 d . . . H23A H -0.8851 0.2893 0.8127 0.059 Uiso 1 1 calc R . . C24 C -0.9585(3) 0.0041(2) 0.7161(2) 0.0670(11) Uani 1 1 d . . . H24A H -1.0064 0.0066 0.6712 0.080 Uiso 1 1 calc R . . H24B H -1.0073 -0.0005 0.7553 0.080 Uiso 1 1 calc R . . C25 C -0.8875(3) -0.0835(2) 0.7157(2) 0.0487(9) Uani 1 1 d . . . C26 C -0.9033(2) -0.1473(2) 0.66094(19) 0.0484(9) Uani 1 1 d . . . H26A H -0.9523 -0.1334 0.6208 0.058 Uiso 1 1 calc R . . C27 C -0.8479(3) -0.2320(2) 0.66426(18) 0.0453(8) Uani 1 1 d . . . H27A H -0.8617 -0.2753 0.6272 0.054 Uiso 1 1 calc R . . C28 C -0.7721(2) -0.2531(2) 0.72225(17) 0.0374(8) Uani 1 1 d . . . C29 C -0.7506(3) -0.1864(2) 0.77568(19) 0.0518(9) Uani 1 1 d . . . H29A H -0.6971 -0.1984 0.8140 0.062 Uiso 1 1 calc R . . C30 C -0.8079(3) -0.1024(2) 0.7727(2) 0.0595(10) Uani 1 1 d . . . H30A H -0.7930 -0.0583 0.8090 0.071 Uiso 1 1 calc R . . C31 C -0.7150(3) -0.3459(2) 0.72778(19) 0.0423(8) Uani 1 1 d . . . O7 O -0.1890(3) 0.5657(2) 1.07666(19) 0.0687(8) Uani 1 1 d . . . H7WB H -0.200(3) 0.620(3) 1.061(2) 0.085(15) Uiso 1 1 d . . . H7WA H -0.213(4) 0.569(4) 1.118(3) 0.15(3) Uiso 1 1 d . . . O8 O 0.1774(3) -0.0706(2) 1.03994(19) 0.0695(9) Uani 1 1 d . . . H8WB H 0.191(3) -0.117(3) 1.023(2) 0.078(16) Uiso 1 1 d . . . H8WA H 0.209(4) -0.072(3) 1.093(3) 0.15(2) Uiso 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 Ni 0.0438(2) 0.0286(2) 0.0498(3) 0.0016(2) 0.00251(18) 0.0015(2) O1 0.0726(17) 0.0382(15) 0.0750(18) -0.0028(14) -0.0164(13) 0.0084(13) O2 0.119(2) 0.0342(15) 0.106(2) 0.0127(15) 0.0623(19) 0.0150(15) O3 0.0532(14) 0.0332(13) 0.0638(16) -0.0013(11) 0.0151(13) -0.0072(11) O4 0.0519(14) 0.0343(13) 0.0621(16) -0.0078(12) 0.0102(12) -0.0037(11) O5 0.0617(15) 0.0342(13) 0.0540(16) -0.0050(12) -0.0059(12) 0.0043(11) O6 0.0554(15) 0.0377(14) 0.0532(16) 0.0004(12) -0.0077(12) 0.0087(11) N1 0.0427(16) 0.0330(15) 0.0548(19) 0.0020(14) 0.0000(14) 0.0054(12) N2 0.0567(18) 0.0343(16) 0.0494(18) -0.0051(14) -0.0073(14) 0.0105(13) N3 0.0667(19) 0.0328(16) 0.0560(19) 0.0067(14) 0.0170(16) 0.0120(14) N4 0.0501(17) 0.0305(15) 0.0531(19) 0.0006(13) 0.0037(14) 0.0035(13) C1 0.060(2) 0.036(2) 0.070(3) -0.0100(19) -0.009(2) 0.0078(17) C2 0.062(2) 0.033(2) 0.062(3) -0.0018(18) -0.011(2) 0.0140(17) C3 0.0395(19) 0.0359(19) 0.047(2) -0.0003(17) 0.0036(16) 0.0071(15) C4 0.052(2) 0.034(2) 0.052(2) -0.0049(17) -0.0040(17) 0.0037(16) C5 0.052(2) 0.0281(18) 0.065(3) 0.0028(18) 0.0009(19) 0.0061(15) C6 0.053(2) 0.040(2) 0.047(2) -0.0017(18) 0.0074(18) 0.0104(18) C7 0.064(2) 0.047(2) 0.045(2) -0.0028(18) 0.0002(19) 0.0168(18) C8 0.064(2) 0.049(2) 0.040(2) 0.0006(17) 0.0005(18) 0.0133(18) C9 0.062(2) 0.047(2) 0.049(2) 0.0070(18) 0.0044(18) 0.0114(18) C10 0.068(2) 0.040(2) 0.049(2) 0.0040(17) 0.015(2) 0.0170(18) C11 0.072(3) 0.037(2) 0.056(2) 0.0046(18) 0.012(2) 0.0118(19) C12 0.051(2) 0.037(2) 0.047(2) -0.0022(17) 0.0060(18) 0.0076(16) C13 0.066(2) 0.038(2) 0.057(2) 0.0142(19) 0.0184(19) 0.0090(18) C14 0.066(2) 0.034(2) 0.066(3) 0.0059(18) 0.015(2) 0.0123(17) C15 0.068(2) 0.038(2) 0.073(3) 0.0150(19) 0.022(2) 0.0086(18) C16 0.074(3) 0.036(2) 0.076(3) 0.008(2) 0.028(2) 0.0157(18) C17 0.043(2) 0.0306(19) 0.049(2) 0.0043(17) -0.0058(18) 0.0043(15) C18 0.0377(19) 0.0278(18) 0.054(2) -0.0020(16) 0.0016(17) 0.0017(14) C19 0.048(2) 0.038(2) 0.067(3) -0.0017(18) 0.0149(19) 0.0021(16) C20 0.060(2) 0.037(2) 0.082(3) -0.015(2) 0.014(2) 0.0039(18) C21 0.038(2) 0.0284(18) 0.082(3) -0.0014(19) 0.0031(19) 0.0058(15) C22 0.047(2) 0.042(2) 0.078(3) 0.000(2) 0.014(2) -0.0047(17) C23 0.051(2) 0.0351(19) 0.064(2) -0.0096(18) 0.0103(19) 0.0016(17) C24 0.0421(19) 0.037(2) 0.122(3) -0.004(2) 0.007(2) 0.0017(18) C25 0.040(2) 0.0264(18) 0.080(3) 0.0001(19) 0.0064(19) -0.0023(15) C26 0.042(2) 0.039(2) 0.063(3) 0.0082(19) -0.0046(18) 0.0003(16) C27 0.048(2) 0.036(2) 0.052(2) -0.0043(17) -0.0014(18) 0.0010(16) C28 0.0402(19) 0.0276(17) 0.045(2) 0.0006(16) 0.0052(16) -0.0006(14) C29 0.055(2) 0.037(2) 0.061(3) -0.0007(18) -0.0086(19) 0.0052(17) C30 0.067(3) 0.036(2) 0.074(3) -0.014(2) -0.003(2) 0.0014(18) C31 0.046(2) 0.0325(19) 0.049(2) 0.0044(17) 0.0096(18) -0.0007(16) O7 0.109(2) 0.0357(17) 0.060(2) -0.0052(15) -0.0008(18) 0.0074(15) O8 0.108(2) 0.0376(17) 0.062(2) 0.0073(16) 0.0032(18) 0.0055(16) _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 Ni N1 2.045(3) . ? Ni O3 2.052(2) . ? Ni N4 2.050(3) 2_556 ? Ni O6 2.070(2) 1_565 ? Ni O5 2.163(2) 1_565 ? Ni O4 2.191(2) . ? Ni C31 2.449(3) 1_565 ? Ni C17 2.462(3) . ? O1 C6 1.223(4) . ? O2 C11 1.210(4) . ? O3 C17 1.263(3) . ? O4 C17 1.266(3) . ? O5 C31 1.257(4) . ? O5 Ni 2.163(2) 1_545 ? O6 C31 1.260(4) . ? O6 Ni 2.070(2) 1_545 ? N1 C1 1.327(4) . ? N1 C5 1.334(4) . ? N2 C6 1.361(4) . ? N2 C3 1.393(4) . ? N2 H2N 0.8600 . ? N3 C11 1.370(4) . ? N3 C12 1.399(4) . ? N3 H3N 0.8600 . ? N4 C15 1.327(4) . ? N4 C14 1.337(4) . ? N4 Ni 2.050(2) 2_546 ? C1 C2 1.372(4) . ? C1 H1A 0.9300 . ? C2 C3 1.380(4) . ? C2 H2A 0.9300 . ? C3 C4 1.387(4) . ? C4 C5 1.364(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.505(4) . ? C7 C8 1.535(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.526(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.531(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.502(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C16 1.378(4) . ? C12 C13 1.385(4) . ? C13 C14 1.370(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.367(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.486(4) . ? C18 C23 1.372(4) . ? C18 C19 1.375(4) . ? C19 C20 1.384(4) . ? C19 H19A 0.9300 . ? C20 C21 1.378(4) . ? C20 H20A 0.9300 . ? C21 C22 1.376(4) . ? C21 C24 1.509(4) . ? C22 C23 1.380(4) . ? C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? C24 C25 1.513(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.368(4) . ? C25 C30 1.388(5) . ? C26 C27 1.380(4) . ? C26 H26A 0.9300 . ? C27 C28 1.380(4) . ? C27 H27A 0.9300 . ? C28 C29 1.384(4) . ? C28 C31 1.492(4) . ? C29 C30 1.382(4) . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C31 Ni 2.449(3) 1_545 ? O7 H7WB 0.84(4) . ? O7 H7WA 0.84(5) . ? O8 H8WB 0.76(4) . ? O8 H8WA 1.02(5) . ? 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 Ni O3 98.48(10) . . ? N1 Ni N4 97.74(10) . 2_556 ? O3 Ni N4 93.57(9) . 2_556 ? N1 Ni O6 94.48(10) . 1_565 ? O3 Ni O6 161.54(9) . 1_565 ? N4 Ni O6 97.65(9) 2_556 1_565 ? N1 Ni O5 155.62(10) . 1_565 ? O3 Ni O5 103.48(9) . 1_565 ? N4 Ni O5 91.38(9) 2_556 1_565 ? O6 Ni O5 61.79(8) 1_565 1_565 ? N1 Ni O4 90.89(9) . . ? O3 Ni O4 61.72(8) . . ? N4 Ni O4 154.87(9) 2_556 . ? O6 Ni O4 105.19(8) 1_565 . ? O5 Ni O4 90.28(8) 1_565 . ? N1 Ni C31 125.25(12) . 1_565 ? O3 Ni C31 133.50(11) . 1_565 ? N4 Ni C31 95.14(10) 2_556 1_565 ? O6 Ni C31 30.94(9) 1_565 1_565 ? O5 Ni C31 30.85(9) 1_565 1_565 ? O4 Ni C31 99.05(9) . 1_565 ? N1 Ni C17 95.31(10) . . ? O3 Ni C17 30.84(9) . . ? N4 Ni C17 124.30(11) 2_556 . ? O6 Ni C17 134.90(10) 1_565 . ? O5 Ni C17 98.11(9) 1_565 . ? O4 Ni C17 30.88(8) . . ? C31 Ni C17 119.63(10) 1_565 . ? C17 O3 Ni 92.78(18) . . ? C17 O4 Ni 86.46(18) . . ? C31 O5 Ni 87.2(2) . 1_545 ? C31 O6 Ni 91.39(19) . 1_545 ? C1 N1 C5 114.8(3) . . ? C1 N1 Ni 123.8(2) . . ? C5 N1 Ni 121.3(2) . . ? C6 N2 C3 128.4(3) . . ? C6 N2 H2N 115.8 . . ? C3 N2 H2N 115.8 . . ? C11 N3 C12 127.7(3) . . ? C11 N3 H3N 116.2 . . ? C12 N3 H3N 116.2 . . ? C15 N4 C14 115.2(3) . . ? C15 N4 Ni 123.5(2) . 2_546 ? C14 N4 Ni 121.4(2) . 2_546 ? N1 C1 C2 125.4(3) . . ? N1 C1 H1A 117.3 . . ? C2 C1 H1A 117.3 . . ? C1 C2 C3 118.9(3) . . ? C1 C2 H2A 120.6 . . ? C3 C2 H2A 120.6 . . ? C2 C3 C4 116.4(3) . . ? C2 C3 N2 124.8(3) . . ? C4 C3 N2 118.7(3) . . ? C5 C4 C3 120.1(3) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? N1 C5 C4 124.2(3) . . ? N1 C5 H5A 117.9 . . ? C4 C5 H5A 117.9 . . ? O1 C6 N2 122.8(3) . . ? O1 C6 C7 122.6(3) . . ? N2 C6 C7 114.6(3) . . ? C6 C7 C8 114.0(3) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 112.4(3) . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 112.7(3) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 112.3(3) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? O2 C11 N3 122.2(3) . . ? O2 C11 C10 123.7(3) . . ? N3 C11 C10 114.1(3) . . ? C16 C12 C13 117.1(3) . . ? C16 C12 N3 124.9(3) . . ? C13 C12 N3 118.0(3) . . ? C14 C13 C12 119.6(3) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? N4 C14 C13 123.9(3) . . ? N4 C14 H14A 118.0 . . ? C13 C14 H14A 118.0 . . ? N4 C15 C16 125.4(3) . . ? N4 C15 H15A 117.3 . . ? C16 C15 H15A 117.3 . . ? C15 C16 C12 118.7(3) . . ? C15 C16 H16A 120.6 . . ? C12 C16 H16A 120.6 . . ? O3 C17 O4 119.0(3) . . ? O3 C17 C18 119.7(3) . . ? O4 C17 C18 121.3(3) . . ? O3 C17 Ni 56.38(15) . . ? O4 C17 Ni 62.66(16) . . ? C18 C17 Ni 175.8(2) . . ? C23 C18 C19 118.7(3) . . ? C23 C18 C17 121.0(3) . . ? C19 C18 C17 120.2(3) . . ? C18 C19 C20 120.5(3) . . ? C18 C19 H19A 119.8 . . ? C20 C19 H19A 119.8 . . ? C21 C20 C19 120.9(3) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C22 C21 C20 118.1(3) . . ? C22 C21 C24 120.7(3) . . ? C20 C21 C24 121.1(3) . . ? C21 C22 C23 121.0(3) . . ? C21 C22 H22A 119.5 . . ? C23 C22 H22A 119.5 . . ? C18 C23 C22 120.7(3) . . ? C18 C23 H23A 119.7 . . ? C22 C23 H23A 119.7 . . ? C21 C24 C25 115.2(3) . . ? C21 C24 H24A 108.5 . . ? C25 C24 H24A 108.5 . . ? C21 C24 H24B 108.5 . . ? C25 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? C26 C25 C30 118.6(3) . . ? C26 C25 C24 120.9(3) . . ? C30 C25 C24 120.4(3) . . ? C25 C26 C27 121.2(3) . . ? C25 C26 H26A 119.4 . . ? C27 C26 H26A 119.4 . . ? C26 C27 C28 120.5(3) . . ? C26 C27 H27A 119.8 . . ? C28 C27 H27A 119.8 . . ? C27 C28 C29 118.6(3) . . ? C27 C28 C31 120.9(3) . . ? C29 C28 C31 120.5(3) . . ? C28 C29 C30 120.6(3) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C29 C30 C25 120.3(3) . . ? C29 C30 H30A 119.8 . . ? C25 C30 H30A 119.8 . . ? O5 C31 O6 119.6(3) . . ? O5 C31 C28 120.7(3) . . ? O6 C31 C28 119.7(3) . . ? O5 C31 Ni 61.90(17) . 1_545 ? O6 C31 Ni 57.67(16) . 1_545 ? C28 C31 Ni 177.4(3) . 1_545 ? H7WB O7 H7WA 102(4) . . ? H8WB O8 H8WA 107(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.567 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.058 data_2 _database_code_depnum_ccdc_archive 'CCDC 912094' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 N4 Ni O8' _chemical_formula_weight 631.27 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 12.4702(2) _cell_length_b 22.7872(4) _cell_length_c 11.0779(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3147.91(9) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 6571 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 23.99 _exptl_crystal_description BLOCK _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6314 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 27766 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3921 _reflns_number_gt 2667 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0607P)^2^+1.1549P] 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 3921 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.62252(3) 0.2500 0.2500 0.03812(14) Uani 1 2 d S . . O1 O 1.0628(2) 0.05746(13) 0.1438(3) 0.1346(13) Uani 1 1 d . A . O2 O 0.50252(14) 0.31498(7) 0.27488(14) 0.0506(4) Uani 1 1 d . . . O3 O 0.58912(13) 0.30645(7) 0.10502(14) 0.0489(4) Uani 1 1 d . . . O4 O 0.2500 0.5000 -0.0487(2) 0.0879(11) Uani 1 2 d S . . N1 N 0.73994(15) 0.20203(8) 0.17118(16) 0.0444(4) Uani 1 1 d . . . N2 N 1.00708(18) 0.12576(9) 0.0079(2) 0.0651(6) Uani 1 1 d . A . H2A H 1.0223 0.1403 -0.0617 0.078 Uiso 1 1 calc R . . C1 C 0.7706(2) 0.21533(11) 0.0591(2) 0.0549(6) Uani 1 1 d . . . H1A H 0.7297 0.2422 0.0158 0.066 Uiso 1 1 calc R . . C2 C 0.8586(2) 0.19173(11) 0.0045(2) 0.0587(7) Uani 1 1 d . . . H2B H 0.8772 0.2028 -0.0736 0.070 Uiso 1 1 calc R . . C3 C 0.9204(2) 0.15077(10) 0.0674(2) 0.0513(6) Uani 1 1 d . . . C4 C 0.8907(2) 0.13790(12) 0.1846(3) 0.0580(7) Uani 1 1 d . . . H4A H 0.9308 0.1118 0.2306 0.070 Uiso 1 1 calc R . . C5 C 0.8014(2) 0.16410(11) 0.2320(2) 0.0531(6) Uani 1 1 d . . . H5A H 0.7824 0.1550 0.3110 0.064 Uiso 1 1 calc R . . C6 C 1.0715(3) 0.08065(13) 0.0463(4) 0.0901(12) Uani 1 1 d . . . C7 C 1.1622(9) 0.0644(5) -0.0188(7) 0.070(3) Uani 0.50 1 d P A 1 H7A H 1.2135 0.0962 -0.0114 0.084 Uiso 0.50 1 calc PR A 1 H7B H 1.1414 0.0626 -0.1031 0.084 Uiso 0.50 1 calc PR A 1 C8 C 1.2214(4) 0.0081(3) 0.0094(7) 0.0657(16) Uani 0.50 1 d P . 1 H8A H 1.1997 0.0020 0.0926 0.079 Uiso 0.50 1 calc PR . 1 H8B H 1.1790 -0.0198 -0.0362 0.079 Uiso 0.50 1 calc PR . 1 C7' C 1.1438(10) 0.0636(6) -0.0775(8) 0.085(3) Uani 0.50 1 d P A 2 H7C H 1.0983 0.0684 -0.1479 0.103 Uiso 0.50 1 calc PR A 2 H7D H 1.2021 0.0915 -0.0846 0.103 Uiso 0.50 1 calc PR A 2 C8' C 1.1899(5) 0.0030(3) -0.0797(8) 0.085(2) Uani 0.50 1 d P . 2 H8C H 1.1626 -0.0168 -0.1510 0.102 Uiso 0.50 1 calc PR . 2 H8D H 1.1624 -0.0180 -0.0101 0.102 Uiso 0.50 1 calc PR . 2 C9 C 0.51661(18) 0.33048(9) 0.1666(2) 0.0431(5) Uani 1 1 d . . . C10 C 0.44695(18) 0.37680(10) 0.1127(2) 0.0453(5) Uani 1 1 d . . . C11 C 0.3525(2) 0.39291(12) 0.1691(3) 0.0617(7) Uani 1 1 d . . . H11A H 0.3337 0.3753 0.2418 0.074 Uiso 1 1 calc R . . C12 C 0.2852(2) 0.43475(13) 0.1191(3) 0.0707(8) Uani 1 1 d . . . H12A H 0.2213 0.4450 0.1570 0.085 Uiso 1 1 calc R . . C13 C 0.3148(2) 0.46089(11) 0.0120(2) 0.0605(7) Uani 1 1 d . . . C14 C 0.4092(2) 0.44628(11) -0.0442(2) 0.0576(7) Uani 1 1 d . . . H14A H 0.4292 0.4650 -0.1153 0.069 Uiso 1 1 calc R . . C15 C 0.4744(2) 0.40362(10) 0.0052(2) 0.0513(6) Uani 1 1 d . . . H15A H 0.5373 0.3929 -0.0341 0.062 Uiso 1 1 calc R . . O5 O 0.6207(8) 0.2500 -0.2500 0.419(10) Uani 1 2 d S . . H5E H 0.6612 0.2208 -0.2639 0.503 Uiso 1 1 d 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 Ni 0.0365(2) 0.0382(2) 0.0397(2) 0.00001(16) 0.000 0.000 O1 0.104(2) 0.123(2) 0.176(3) 0.083(2) 0.043(2) 0.0695(18) O2 0.0506(9) 0.0511(9) 0.0501(10) 0.0053(7) 0.0086(8) 0.0100(8) O3 0.0491(9) 0.0502(9) 0.0476(9) 0.0011(7) 0.0034(8) 0.0129(7) O4 0.120(3) 0.093(2) 0.0507(16) 0.000 0.000 0.069(2) N1 0.0462(10) 0.0456(10) 0.0414(10) 0.0027(8) 0.0024(8) 0.0090(8) N2 0.0589(13) 0.0554(12) 0.0810(16) 0.0135(12) 0.0225(12) 0.0224(11) C1 0.0611(16) 0.0548(14) 0.0489(14) 0.0071(11) 0.0042(12) 0.0249(12) C2 0.0691(17) 0.0606(15) 0.0466(14) 0.0128(12) 0.0148(12) 0.0254(13) C3 0.0456(13) 0.0476(13) 0.0607(15) 0.0060(11) 0.0073(11) 0.0135(11) C4 0.0556(15) 0.0604(15) 0.0580(16) 0.0163(13) -0.0013(13) 0.0180(12) C5 0.0547(14) 0.0584(14) 0.0463(14) 0.0113(11) 0.0023(11) 0.0106(12) C6 0.0604(19) 0.0585(17) 0.151(4) 0.033(2) 0.035(2) 0.0258(15) C7 0.065(5) 0.062(4) 0.084(7) 0.022(5) 0.030(5) 0.022(4) C8 0.051(4) 0.052(4) 0.094(4) 0.011(3) 0.012(3) 0.021(3) C7' 0.082(6) 0.082(5) 0.093(7) 0.020(6) 0.031(6) 0.054(4) C8' 0.074(4) 0.066(4) 0.115(6) 0.004(4) -0.019(4) 0.035(3) C9 0.0413(12) 0.0401(11) 0.0478(13) -0.0036(10) -0.0003(10) 0.0027(9) C10 0.0477(13) 0.0407(11) 0.0474(13) -0.0038(10) 0.0011(11) 0.0082(10) C11 0.0599(16) 0.0681(17) 0.0572(16) 0.0112(13) 0.0109(13) 0.0213(13) C12 0.0657(18) 0.0802(19) 0.0662(18) 0.0065(15) 0.0099(15) 0.0337(15) C13 0.0778(19) 0.0554(15) 0.0484(15) -0.0049(12) -0.0040(13) 0.0304(14) C14 0.0829(18) 0.0470(13) 0.0429(13) -0.0017(11) 0.0050(13) 0.0179(13) C15 0.0582(15) 0.0469(12) 0.0487(14) -0.0057(11) 0.0071(11) 0.0131(12) O5 0.272(13) 0.51(2) 0.47(2) 0.277(16) 0.000 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 Ni N1 2.0252(18) 4 ? Ni N1 2.0252(18) . ? Ni O3 2.0995(15) . ? Ni O3 2.0995(15) 4 ? Ni O2 2.1231(16) 4 ? Ni O2 2.1232(16) . ? Ni C9 2.441(2) . ? Ni C9 2.441(2) 4 ? O1 C6 1.208(4) . ? O2 C9 1.262(3) . ? O3 C9 1.258(3) . ? O4 C13 1.378(3) . ? O4 C13 1.378(3) 2_565 ? N1 C1 1.334(3) . ? N1 C5 1.338(3) . ? N2 C6 1.373(3) . ? N2 C3 1.388(3) . ? N2 H2A 0.8600 . ? C1 C2 1.364(3) . ? C1 H1A 0.9300 . ? C2 C3 1.397(3) . ? C2 H2B 0.9300 . ? C3 C4 1.381(4) . ? C4 C5 1.368(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.391(11) . ? C6 C7' 1.686(11) . ? C7 C8 1.512(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C8 0.803(9) 2_755 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7' C8' 1.496(13) . ? C7' H7C 0.9700 . ? C7' H7D 0.9700 . ? C8' C8' 1.506(13) 2_755 ? C8' H8C 0.9700 . ? C8' H8D 0.9700 . ? C9 C10 1.492(3) . ? C10 C15 1.382(3) . ? C10 C11 1.383(3) . ? C11 C12 1.386(4) . ? C11 H11A 0.9300 . ? C12 C13 1.378(4) . ? C12 H12A 0.9300 . ? C13 C14 1.373(4) . ? C14 C15 1.381(3) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? O5 H5E 0.8499 . ? 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 Ni N1 87.38(11) 4 . ? N1 Ni O3 98.20(7) 4 . ? N1 Ni O3 98.30(7) . . ? N1 Ni O3 98.30(7) 4 4 ? N1 Ni O3 98.20(7) . 4 ? O3 Ni O3 157.12(9) . 4 ? N1 Ni O2 160.39(7) 4 4 ? N1 Ni O2 94.43(7) . 4 ? O3 Ni O2 100.85(6) . 4 ? O3 Ni O2 62.11(6) 4 4 ? N1 Ni O2 94.43(7) 4 . ? N1 Ni O2 160.39(7) . . ? O3 Ni O2 62.11(6) . . ? O3 Ni O2 100.85(6) 4 . ? O2 Ni O2 90.37(10) 4 . ? N1 Ni C9 98.56(7) 4 . ? N1 Ni C9 129.31(8) . . ? O3 Ni C9 31.02(7) . . ? O3 Ni C9 129.97(7) 4 . ? O2 Ni C9 95.37(7) 4 . ? O2 Ni C9 31.12(7) . . ? N1 Ni C9 129.31(8) 4 4 ? N1 Ni C9 98.56(7) . 4 ? O3 Ni C9 129.96(7) . 4 ? O3 Ni C9 31.03(7) 4 4 ? O2 Ni C9 31.12(7) 4 4 ? O2 Ni C9 95.37(7) . 4 ? C9 Ni C9 114.50(11) . 4 ? C9 O2 Ni 88.49(13) . . ? C9 O3 Ni 89.67(13) . . ? C13 O4 C13 121.7(3) . 2_565 ? C1 N1 C5 116.8(2) . . ? C1 N1 Ni 119.08(15) . . ? C5 N1 Ni 123.10(16) . . ? C6 N2 C3 128.0(3) . . ? C6 N2 H2A 116.0 . . ? C3 N2 H2A 116.0 . . ? N1 C1 C2 123.6(2) . . ? N1 C1 H1A 118.2 . . ? C2 C1 H1A 118.2 . . ? C1 C2 C3 119.1(2) . . ? C1 C2 H2B 120.5 . . ? C3 C2 H2B 120.5 . . ? C4 C3 N2 124.6(2) . . ? C4 C3 C2 117.5(2) . . ? N2 C3 C2 117.8(2) . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? N1 C5 C4 123.7(2) . . ? N1 C5 H5A 118.2 . . ? C4 C5 H5A 118.2 . . ? O1 C6 N2 123.5(3) . . ? O1 C6 C7 114.8(4) . . ? N2 C6 C7 121.0(4) . . ? O1 C6 C7' 132.4(4) . . ? N2 C6 C7' 103.5(4) . . ? C7 C6 C7' 23.5(6) . . ? C6 C7 C8 121.1(7) . . ? C6 C7 H7A 107.1 . . ? C8 C7 H7A 107.1 . . ? C6 C7 H7B 107.1 . . ? C8 C7 H7B 107.1 . . ? H7A C7 H7B 106.8 . . ? C8 C8 C7 145.6(12) 2_755 . ? C8 C8 H8A 100.5 2_755 . ? C7 C8 H8A 100.5 . . ? C8 C8 H8B 100.5 2_755 . ? C7 C8 H8B 100.5 . . ? H8A C8 H8B 104.3 . . ? C8' C7' C6 115.5(7) . . ? C8' C7' H7C 108.4 . . ? C6 C7' H7C 108.4 . . ? C8' C7' H7D 108.4 . . ? C6 C7' H7D 108.4 . . ? H7C C7' H7D 107.5 . . ? C7' C8' C8' 117.8(9) . 2_755 ? C7' C8' H8C 107.9 . . ? C8' C8' H8C 107.9 2_755 . ? C7' C8' H8D 107.9 . . ? C8' C8' H8D 107.9 2_755 . ? H8C C8' H8D 107.2 . . ? O3 C9 O2 119.6(2) . . ? O3 C9 C10 120.6(2) . . ? O2 C9 C10 119.8(2) . . ? O3 C9 Ni 59.31(11) . . ? O2 C9 Ni 60.38(11) . . ? C10 C9 Ni 176.33(16) . . ? C15 C10 C11 118.9(2) . . ? C15 C10 C9 120.9(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 121.2(3) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C13 C12 C11 118.6(3) . . ? C13 C12 H12A 120.7 . . ? C11 C12 H12A 120.7 . . ? C14 C13 C12 121.0(2) . . ? C14 C13 O4 116.0(2) . . ? C12 C13 O4 122.8(2) . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? C14 C15 C10 120.5(2) . . ? C14 C15 H15A 119.8 . . ? C10 C15 H15A 119.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.443 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.052 data_3 _database_code_depnum_ccdc_archive 'CCDC 912095' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 N4 Ni O10 S' _chemical_formula_weight 697.35 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ima2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1/2, z+1/2' '-x+1, y+1/2, z+1/2' _cell_length_a 24.5212(18) _cell_length_b 11.1701(8) _cell_length_c 12.2369(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3351.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4899 _cell_measurement_theta_min 2.469 _cell_measurement_theta_max 32.726 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.700 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6673 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 13590 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 33.00 _reflns_number_total 5574 _reflns_number_gt 5002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1053P)^2^+4.0574P] 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 SHELXL _refine_ls_extinction_coef 0.0017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(2) _refine_ls_number_reflns 5574 _refine_ls_number_parameters 342 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1760 _refine_ls_wR_factor_gt 0.1706 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.090 _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 Ni Ni 0.5000 0.5000 0.45728(7) 0.01973(12) Uani 1 2 d S . . S S 0.2500 0.82487(11) 0.08708(11) 0.0297(2) Uani 1 2 d S . . O1 O 0.43875(9) 0.4834(2) 0.3321(3) 0.0290(5) Uani 1 1 d . . . O2 O 0.45298(9) 0.64940(19) 0.4215(2) 0.0251(4) Uani 1 1 d . . . O3 O 0.2500 0.7803(4) -0.0237(3) 0.0397(10) Uani 1 2 d S . . O4 O 0.2500 0.9514(4) 0.1072(5) 0.0505(12) Uani 1 2 d S . . C1 C 0.42853(10) 0.5934(3) 0.3475(2) 0.0206(5) Uani 1 1 d . A . C2 C 0.38719(11) 0.6556(3) 0.2781(3) 0.0236(5) Uani 1 1 d . . . C3 C 0.3630(3) 0.5845(6) 0.1917(6) 0.0229(11) Uani 0.50 1 d P A 1 H3A H 0.3740 0.5044 0.1777 0.027 Uiso 0.50 1 calc PR A 1 C4 C 0.3225(3) 0.6411(7) 0.1302(6) 0.0249(12) Uani 0.50 1 d P A 1 H4A H 0.3059 0.6007 0.0705 0.030 Uiso 0.50 1 calc PR A 1 C3' C 0.3774(2) 0.6287(6) 0.1716(6) 0.0222(11) Uani 0.50 1 d P A 2 H3'A H 0.4002 0.5710 0.1372 0.027 Uiso 0.50 1 calc PR A 2 C4' C 0.3358(3) 0.6811(7) 0.1096(6) 0.0242(12) Uani 0.50 1 d P A 2 H4'A H 0.3295 0.6589 0.0358 0.029 Uiso 0.50 1 calc PR A 2 C5 C 0.30586(11) 0.7622(3) 0.1583(3) 0.0244(6) Uani 1 1 d . . . C6 C 0.3322(3) 0.8198(8) 0.2402(8) 0.0269(16) Uani 0.50 1 d P A 1 H6A H 0.3228 0.9006 0.2559 0.032 Uiso 0.50 1 calc PR A 1 C7 C 0.3731(3) 0.7637(7) 0.3031(7) 0.0199(14) Uani 0.50 1 d P A 1 H7A H 0.3899 0.8043 0.3624 0.024 Uiso 0.50 1 calc PR A 1 C6' C 0.3151(3) 0.8095(7) 0.2637(7) 0.0245(14) Uani 0.50 1 d P A 2 H6'A H 0.2940 0.8737 0.2923 0.029 Uiso 0.50 1 calc PR A 2 C7' C 0.3567(3) 0.7564(8) 0.3230(8) 0.0205(14) Uani 0.50 1 d P A 2 H7'A H 0.3655 0.7860 0.3937 0.025 Uiso 0.50 1 calc PR A 2 N1 N 0.5400(4) 0.5720(9) 0.5788(10) 0.0215(16) Uani 0.50 1 d P . . O5 O 0.6583(2) 0.5855(4) 0.9376(4) 0.0366(13) Uani 0.50 1 d P . . N2 N 0.60880(18) 0.7334(4) 0.8572(4) 0.0215(9) Uani 0.50 1 d P . . H2A H 0.5999 0.8110 0.8654 0.026 Uiso 0.50 1 d PR . . C8 C 0.5340(5) 0.6954(11) 0.6023(12) 0.022(2) Uani 0.50 1 d PU . . H8A H 0.5174 0.7502 0.5517 0.026 Uiso 0.50 1 d PR . . C9 C 0.54768(16) 0.7344(3) 0.7093(4) 0.041(3) Uani 0.50 1 d PU . . H9A H 0.5295 0.8024 0.7407 0.049 Uiso 0.50 1 d PR . . C10 C 0.58585(16) 0.6744(3) 0.7675(4) 0.0189(9) Uani 0.50 1 d PR . . C11 C 0.60061(16) 0.5649(3) 0.7302(4) 0.0289(13) Uani 0.50 1 d PR . . H11A H 0.6294 0.5221 0.7661 0.035 Uiso 0.50 1 d PR . . C12 C 0.5759(2) 0.5139(5) 0.6419(6) 0.0229(11) Uani 0.50 1 d P . . H12A H 0.5789 0.4292 0.6301 0.028 Uiso 0.50 1 d PR . . C13 C 0.6449(3) 0.6855(6) 0.9319(6) 0.0286(13) Uani 0.50 1 d P . . C14 C 0.6707(2) 0.7751(6) 1.0074(5) 0.0243(11) Uani 0.50 1 d P . . H14A H 0.6755 0.7390 1.0780 0.029 Uiso 0.50 1 d PR . . H14B H 0.6469 0.8427 1.0160 0.029 Uiso 0.50 1 d PR . . C15 C 0.7256(2) 0.8186(5) 0.9627(6) 0.0226(10) Uani 0.50 1 d P . . H15A H 0.7453 0.7510 0.9344 0.027 Uiso 0.50 1 d PR . . H15B H 0.7500 0.8517 1.0217 0.027 Uiso 1 2 d SR . . N4 N 0.9468(4) 0.5923(10) 0.5622(11) 0.027(2) Uani 0.50 1 d P . . O6 O 0.76692(17) 0.7669(6) 0.7094(5) 0.0372(13) Uani 0.50 1 d P . . N3 N 0.8531(2) 0.8269(5) 0.7484(5) 0.0237(10) Uani 0.50 1 d P . . H3B H 0.8725 0.8805 0.7870 0.028 Uiso 0.50 1 d PR . . C22 C 0.9749(7) 0.6766(15) 0.6210(14) 0.034(3) Uani 0.50 1 d PU . . H22A H 1.0133 0.6926 0.6159 0.040 Uiso 0.50 1 d PR . . C23 C 0.9405(3) 0.7578(7) 0.6830(7) 0.0284(18) Uani 0.50 1 d PU . . H23A H 0.9565 0.8258 0.7189 0.034 Uiso 0.50 1 d PR . . C19 C 0.8824(2) 0.7439(6) 0.6877(5) 0.0230(11) Uani 0.50 1 d P . . C20 C 0.8599(2) 0.6419(5) 0.6386(5) 0.0209(10) Uani 0.50 1 d P . . H20A H 0.8220 0.6233 0.6470 0.025 Uiso 0.50 1 d PR . . C21 C 0.8935(2) 0.5686(6) 0.5775(5) 0.0238(10) Uani 0.50 1 d P . . H21A H 0.8768 0.5060 0.5356 0.029 Uiso 0.50 1 d PR . . C18 C 0.7976(2) 0.8370(6) 0.7544(6) 0.0283(12) Uani 0.50 1 d P . . C17 C 0.7761(2) 0.9401(6) 0.8224(8) 0.0254(12) Uani 0.50 1 d P . . H17A H 0.7739 1.0110 0.7783 0.031 Uiso 0.50 1 d PR . . H17B H 0.8014 0.9555 0.8805 0.031 Uiso 0.50 1 d PR . . C16 C 0.7201(3) 0.9122(6) 0.8737(7) 0.0232(11) Uani 0.50 1 d P . . H16A H 0.7049 0.9842 0.9035 0.028 Uiso 0.50 1 d PR . . H16B H 0.6960 0.8828 0.8181 0.028 Uiso 0.50 1 d PR . . O8' O 0.5075(4) 0.8894(12) 0.4133(11) 0.082(3) Uiso 0.50 1 d P B 1 O8 O 0.4816(9) 0.9717(19) 0.485(2) 0.147(7) Uiso 0.50 1 d P . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0288(2) 0.01281(17) 0.0176(2) 0.000 0.000 0.00122(15) S 0.0200(4) 0.0368(5) 0.0323(6) 0.0184(5) 0.000 0.000 O1 0.0204(9) 0.0280(10) 0.0385(15) -0.0145(10) -0.0058(9) 0.0031(7) O2 0.0314(10) 0.0197(9) 0.0241(10) -0.0009(8) -0.0059(8) 0.0020(7) O3 0.0239(14) 0.068(3) 0.027(2) 0.0199(18) 0.000 0.000 O4 0.058(3) 0.033(2) 0.061(3) 0.029(2) 0.000 0.000 C1 0.0157(9) 0.0269(12) 0.0193(12) -0.0008(10) 0.0008(9) 0.0022(8) C2 0.0152(10) 0.0320(14) 0.0235(14) -0.0018(11) 0.0016(9) 0.0025(9) C3 0.022(3) 0.025(3) 0.022(3) 0.000(2) -0.003(2) -0.003(2) C4 0.022(3) 0.027(3) 0.026(3) 0.002(3) -0.008(2) -0.004(2) C3' 0.018(2) 0.023(3) 0.026(3) 0.001(2) 0.006(2) 0.001(2) C4' 0.020(3) 0.025(3) 0.028(3) 0.006(2) 0.001(2) 0.001(2) C5 0.0149(10) 0.0306(14) 0.0275(15) 0.0093(11) 0.0005(9) -0.0017(9) C6 0.017(3) 0.023(3) 0.041(5) 0.003(3) 0.002(3) 0.002(3) C7 0.011(3) 0.019(3) 0.029(4) -0.002(2) -0.004(3) 0.002(3) C6' 0.021(3) 0.021(3) 0.031(4) 0.002(2) 0.002(3) 0.004(3) C7' 0.013(3) 0.021(3) 0.027(4) -0.001(2) 0.003(3) -0.001(3) N1 0.029(4) 0.011(3) 0.025(3) 0.000(2) -0.009(3) -0.002(2) O5 0.065(3) 0.0198(18) 0.025(3) 0.0053(16) -0.024(2) -0.0032(18) N2 0.0182(17) 0.025(2) 0.021(2) -0.0052(18) -0.0069(16) 0.0008(15) C8 0.018(3) 0.016(3) 0.031(5) -0.005(3) -0.005(3) 0.006(3) C9 0.041(5) 0.038(5) 0.043(5) 0.008(4) -0.015(4) 0.006(3) C10 0.021(2) 0.019(2) 0.017(2) -0.0035(17) -0.0036(17) -0.0024(17) C11 0.024(2) 0.028(3) 0.034(3) -0.011(2) -0.015(2) 0.009(2) C12 0.025(2) 0.014(2) 0.029(3) -0.0014(19) -0.006(2) 0.0047(17) C13 0.030(3) 0.028(3) 0.028(3) -0.004(2) -0.014(2) 0.002(2) C14 0.020(2) 0.033(3) 0.020(3) -0.003(2) -0.0036(19) 0.002(2) C15 0.019(2) 0.027(2) 0.022(3) -0.005(2) -0.001(2) 0.0022(16) N4 0.022(4) 0.021(5) 0.039(6) -0.012(4) 0.011(3) -0.004(3) O6 0.0212(16) 0.055(3) 0.035(3) -0.026(3) -0.0009(18) -0.0054(18) N3 0.025(2) 0.024(2) 0.022(2) -0.0104(18) 0.0020(18) -0.0076(17) C22 0.038(6) 0.032(6) 0.032(6) -0.014(4) 0.006(4) -0.001(4) C23 0.023(2) 0.027(3) 0.035(4) -0.025(3) 0.019(3) -0.018(3) C19 0.0172(19) 0.030(3) 0.021(3) -0.004(2) 0.0036(18) -0.0071(19) C20 0.020(2) 0.023(2) 0.020(3) -0.0023(19) 0.0009(18) -0.0088(18) C21 0.026(2) 0.030(3) 0.015(2) -0.003(2) 0.0001(19) -0.0140(19) C18 0.022(2) 0.038(3) 0.024(3) -0.012(2) -0.001(2) -0.002(2) C17 0.019(3) 0.024(3) 0.033(4) -0.010(3) -0.004(3) -0.0019(19) C16 0.023(3) 0.024(3) 0.023(3) -0.005(2) -0.004(2) 0.0029(19) _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 Ni N1 1.955(12) . ? Ni N1 1.955(12) 2_665 ? Ni O2 2.075(2) 2_665 ? Ni O2 2.075(2) . ? Ni N4 2.101(11) 4_655 ? Ni N4 2.101(11) 3_465 ? Ni O1 2.153(3) . ? Ni O1 2.153(3) 2_665 ? Ni C1 2.442(3) . ? Ni C1 2.442(3) 2_665 ? S O4 1.434(5) . ? S O3 1.444(4) . ? S C5 1.768(3) . ? S C5 1.768(3) 4 ? O1 C1 1.268(4) . ? O2 C1 1.253(4) . ? C1 C2 1.493(4) . ? C2 C7 1.292(9) . ? C2 C3' 1.359(7) . ? C2 C3 1.450(7) . ? C2 C7' 1.460(9) . ? C3 C4 1.397(9) . ? C3 H3A 0.9500 . ? C4 C5 1.454(8) . ? C4 H4A 0.9500 . ? C3' C4' 1.401(9) . ? C3' H3'A 0.9500 . ? C4' C5 1.308(8) . ? C4' H4'A 0.9500 . ? C5 C6 1.355(10) . ? C5 C6' 1.413(10) . ? C6 C7 1.412(11) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C6' C7' 1.385(11) . ? C6' H6'A 0.9500 . ? C7' H7'A 0.9500 . ? N1 N4 0.443(11) 4_655 ? N1 C22 1.33(2) 4_655 ? N1 C12 1.338(13) . ? N1 C8 1.417(17) . ? N1 C21 1.629(11) 4_655 ? O5 C13 1.166(8) . ? N2 C13 1.380(8) . ? N2 C10 1.398(6) . ? N2 H2A 0.8999 . ? C8 C22 0.38(2) 4_655 ? C8 N4 1.338(18) 4_655 ? C8 C23 1.362(16) 4_655 ? C8 C9 1.421(16) . ? C8 H8A 0.9599 . ? C9 C23 0.507(13) 4_655 ? C9 C10 1.3535 . ? C9 C22 1.375(18) 4_655 ? C9 C19 1.737(7) 4_655 ? C9 H9A 0.9601 . ? C10 C11 1.3552 . ? C10 C19 1.470(8) 4_655 ? C10 C23 1.534(10) 4_655 ? C11 C12 1.364(8) . ? C11 C20 1.712(8) 4_655 ? C11 C21 1.875(8) 4_655 ? C11 H11A 0.9600 . ? C12 C21 1.248(9) 4_655 ? C12 N4 1.424(14) 4_655 ? C12 H12A 0.9600 . ? C13 C14 1.503(9) . ? C14 C15 1.532(8) . ? C14 C20 2.001(9) 6_665 ? C14 H14A 0.9601 . ? C14 H14B 0.9598 . ? C15 C15 1.196(10) 4_655 ? C15 C16 1.516(11) . ? C15 C16 2.012(9) 4_655 ? C15 H15A 0.9601 . ? C15 H15B 1.0071 . ? N4 N1 0.443(11) 4_655 ? N4 C8 1.338(18) 4_655 ? N4 C21 1.346(11) . ? N4 C22 1.37(2) . ? N4 C12 1.424(14) 4_655 ? N4 Ni 2.101(11) 3_565 ? O6 O6 0.830(9) 4_655 ? O6 C18 1.218(8) . ? O6 C18 1.850(8) 4_655 ? N3 C18 1.366(8) . ? N3 C19 1.389(8) . ? N3 H3B 0.8998 . ? C22 C8 0.38(2) 4_655 ? C22 N1 1.33(2) 4_655 ? C22 C9 1.375(18) 4_655 ? C22 C23 1.453(18) . ? C22 H22A 0.9599 . ? C23 C9 0.507(13) 4_655 ? C23 C8 1.362(16) 4_655 ? C23 C19 1.432(9) . ? C23 C10 1.534(10) 4_655 ? C23 H23A 0.9602 . ? C19 C20 1.401(8) . ? C19 C10 1.470(8) 4_655 ? C19 C9 1.737(7) 4_655 ? C20 C21 1.381(9) . ? C20 C11 1.712(8) 4_655 ? C20 C14 2.001(9) 6_664 ? C20 H20A 0.9599 . ? C21 C12 1.248(9) 4_655 ? C21 N1 1.629(11) 4_655 ? C21 C11 1.875(8) 4_655 ? C21 H21A 0.9600 . ? C18 C17 1.516(9) . ? C18 C16 1.740(9) 4_655 ? C18 O6 1.850(8) 4_655 ? C17 C16 0.707(9) 4_655 ? C17 C17 1.280(11) 4_655 ? C17 C16 1.541(8) . ? C17 H17A 0.9602 . ? C17 H17B 0.9598 . ? C16 C17 0.707(9) 4_655 ? C16 C16 1.464(12) 4_655 ? C16 C18 1.740(9) 4_655 ? C16 C15 2.012(9) 4_655 ? C16 H16A 0.9600 . ? C16 H16B 0.9601 . ? O8 O8 1.10(4) 2_675 ? 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 Ni N1 81.0(5) . 2_665 ? N1 Ni O2 102.3(4) . 2_665 ? N1 Ni O2 96.2(3) 2_665 2_665 ? N1 Ni O2 96.2(3) . . ? N1 Ni O2 102.3(4) 2_665 . ? O2 Ni O2 155.64(14) 2_665 . ? N1 Ni N4 11.9(4) . 4_655 ? N1 Ni N4 92.8(4) 2_665 4_655 ? O2 Ni N4 100.3(3) 2_665 4_655 ? O2 Ni N4 94.5(3) . 4_655 ? N1 Ni N4 92.8(4) . 3_465 ? N1 Ni N4 11.9(4) 2_665 3_465 ? O2 Ni N4 94.5(3) 2_665 3_465 ? O2 Ni N4 100.3(3) . 3_465 ? N4 Ni N4 104.6(6) 4_655 3_465 ? N1 Ni O1 158.0(4) . . ? N1 Ni O1 98.9(3) 2_665 . ? O2 Ni O1 99.68(9) 2_665 . ? O2 Ni O1 62.07(9) . . ? N4 Ni O1 155.5(3) 4_655 . ? N4 Ni O1 87.7(3) 3_465 . ? N1 Ni O1 98.9(3) . 2_665 ? N1 Ni O1 158.0(4) 2_665 2_665 ? O2 Ni O1 62.07(9) 2_665 2_665 ? O2 Ni O1 99.68(9) . 2_665 ? N4 Ni O1 87.7(3) 4_655 2_665 ? N4 Ni O1 155.5(3) 3_465 2_665 ? O1 Ni O1 89.31(15) . 2_665 ? N1 Ni C1 127.1(4) . . ? N1 Ni C1 103.5(3) 2_665 . ? O2 Ni C1 128.77(11) 2_665 . ? O2 Ni C1 30.87(9) . . ? N4 Ni C1 124.9(3) 4_655 . ? N4 Ni C1 95.8(3) 3_465 . ? O1 Ni C1 31.24(9) . . ? O1 Ni C1 94.15(9) 2_665 . ? N1 Ni C1 103.5(3) . 2_665 ? N1 Ni C1 127.1(4) 2_665 2_665 ? O2 Ni C1 30.87(9) 2_665 2_665 ? O2 Ni C1 128.77(11) . 2_665 ? N4 Ni C1 95.8(3) 4_655 2_665 ? N4 Ni C1 124.9(3) 3_465 2_665 ? O1 Ni C1 94.15(9) . 2_665 ? O1 Ni C1 31.24(9) 2_665 2_665 ? C1 Ni C1 113.25(14) . 2_665 ? O4 S O3 120.0(3) . . ? O4 S C5 107.80(17) . . ? O3 S C5 109.03(16) . . ? O4 S C5 107.80(17) . 4 ? O3 S C5 109.03(16) . 4 ? C5 S C5 101.57(19) . 4 ? C1 O1 Ni 87.06(18) . . ? C1 O2 Ni 90.98(17) . . ? O2 C1 O1 119.7(3) . . ? O2 C1 C2 120.2(3) . . ? O1 C1 C2 120.0(3) . . ? O2 C1 Ni 58.15(14) . . ? O1 C1 Ni 61.70(16) . . ? C2 C1 Ni 176.7(2) . . ? C7 C2 C3' 112.7(5) . . ? C7 C2 C3 125.1(5) . . ? C3' C2 C3 26.7(3) . . ? C7 C2 C7' 18.7(4) . . ? C3' C2 C7' 116.2(5) . . ? C3 C2 C7' 119.2(5) . . ? C7 C2 C1 118.8(4) . . ? C3' C2 C1 124.2(3) . . ? C3 C2 C1 116.0(4) . . ? C7' C2 C1 119.5(4) . . ? C4 C3 C2 115.8(6) . . ? C4 C3 H3A 122.1 . . ? C2 C3 H3A 122.1 . . ? C3 C4 C5 119.5(6) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C2 C3' C4' 123.7(5) . . ? C2 C3' H3'A 118.2 . . ? C4' C3' H3'A 118.2 . . ? C5 C4' C3' 116.9(6) . . ? C5 C4' H4'A 121.6 . . ? C3' C4' H4'A 121.6 . . ? C4' C5 C6 113.5(5) . . ? C4' C5 C6' 125.8(5) . . ? C6 C5 C6' 21.6(3) . . ? C4' C5 C4 24.7(3) . . ? C6 C5 C4 118.9(5) . . ? C6' C5 C4 121.3(5) . . ? C4' C5 S 118.9(4) . . ? C6 C5 S 123.1(4) . . ? C6' C5 S 115.2(4) . . ? C4 C5 S 118.0(3) . . ? C5 C6 C7 122.0(7) . . ? C5 C6 H6A 119.0 . . ? C7 C6 H6A 119.0 . . ? C2 C7 C6 118.5(7) . . ? C2 C7 H7A 120.8 . . ? C6 C7 H7A 120.8 . . ? C7' C6' C5 115.9(7) . . ? C7' C6' H6'A 122.1 . . ? C5 C6' H6'A 122.1 . . ? C6' C7' C2 120.7(8) . . ? C6' C7' H7'A 119.7 . . ? C2 C7' H7'A 119.7 . . ? N4 N1 C22 86(3) 4_655 4_655 ? N4 N1 C12 92(3) 4_655 . ? C22 N1 C12 112.5(12) 4_655 . ? N4 N1 C8 71(3) 4_655 . ? C22 N1 C8 15.5(9) 4_655 . ? C12 N1 C8 115.1(10) . . ? N4 N1 C21 44(3) 4_655 4_655 ? C22 N1 C21 107.4(9) 4_655 4_655 ? C12 N1 C21 48.5(5) . 4_655 ? C8 N1 C21 97.4(7) . 4_655 ? N4 N1 Ni 103(3) 4_655 . ? C22 N1 Ni 121.3(10) 4_655 . ? C12 N1 Ni 124.7(8) . . ? C8 N1 Ni 120.1(9) . . ? C21 N1 Ni 119.0(7) 4_655 . ? C13 N2 C10 126.5(5) . . ? C13 N2 H2A 117.1 . . ? C10 N2 H2A 116.3 . . ? C22 C8 N4 87(5) 4_655 4_655 ? C22 C8 C23 96(5) 4_655 4_655 ? N4 C8 C23 123.0(11) 4_655 4_655 ? C22 C8 N1 69(4) 4_655 . ? N4 C8 N1 18.2(5) 4_655 . ? C23 C8 N1 126.7(11) 4_655 . ? C22 C8 C9 75(5) 4_655 . ? N4 C8 C9 121.2(11) 4_655 . ? C23 C8 C9 20.9(6) 4_655 . ? N1 C8 C9 117.4(10) . . ? C22 C8 H8A 120.0 4_655 . ? N4 C8 H8A 117.5 4_655 . ? C23 C8 H8A 109.6 4_655 . ? N1 C8 H8A 122.3 . . ? C9 C8 H8A 119.9 . . ? C23 C9 C10 101.1(9) 4_655 . ? C23 C9 C22 88.5(11) 4_655 4_655 ? C10 C9 C22 117.4(7) . 4_655 ? C23 C9 C8 73.0(10) 4_655 . ? C10 C9 C8 119.8(5) . . ? C22 C9 C8 15.5(8) 4_655 . ? C23 C9 C19 46.0(9) 4_655 4_655 ? C10 C9 C19 55.1(3) . 4_655 ? C22 C9 C19 107.8(8) 4_655 4_655 ? C8 C9 C19 96.4(6) . 4_655 ? C23 C9 H9A 96.4 4_655 . ? C10 C9 H9A 120.1 . . ? C22 C9 H9A 119.9 4_655 . ? C8 C9 H9A 120.1 . . ? C19 C9 H9A 118.0 4_655 . ? C9 C10 C11 117.0 . . ? C9 C10 N2 117.3(2) . . ? C11 C10 N2 125.6(2) . . ? C9 C10 C19 75.8(2) . 4_655 ? C11 C10 C19 96.4(3) . 4_655 ? N2 C10 C19 93.4(4) . 4_655 ? C9 C10 C23 18.9(4) . 4_655 ? C11 C10 C23 115.7(3) . 4_655 ? N2 C10 C23 114.3(4) . 4_655 ? C19 C10 C23 56.9(5) 4_655 4_655 ? C10 C11 C12 121.7(3) . . ? C10 C11 C20 85.3(2) . 4_655 ? C12 C11 C20 86.7(4) . 4_655 ? C10 C11 C21 109.6(2) . 4_655 ? C12 C11 C21 41.7(4) . 4_655 ? C20 C11 C21 45.0(3) 4_655 4_655 ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 118.9 . . ? C20 C11 H11A 97.7 4_655 . ? C21 C11 H11A 114.3 4_655 . ? C21 C12 N1 78.0(6) 4_655 . ? C21 C12 C11 91.6(5) 4_655 . ? N1 C12 C11 123.2(7) . . ? C21 C12 N4 60.1(5) 4_655 4_655 ? N1 C12 N4 18.1(4) . 4_655 ? C11 C12 N4 117.4(6) . 4_655 ? C21 C12 H12A 110.0 4_655 . ? N1 C12 H12A 116.2 . . ? C11 C12 H12A 119.7 . . ? N4 C12 H12A 122.2 4_655 . ? O5 C13 N2 126.3(6) . . ? O5 C13 C14 118.8(6) . . ? N2 C13 C14 114.8(5) . . ? C13 C14 C15 111.2(5) . . ? C13 C14 C20 130.1(5) . 6_665 ? C15 C14 C20 118.0(4) . 6_665 ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 110.3 . . ? C20 C14 H14A 61.2 6_665 . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 108.9 . . ? C20 C14 H14B 47.1 6_665 . ? H14A C14 H14B 107.9 . . ? C15 C15 C16 95.1(3) 4_655 . ? C15 C15 C14 151.5(3) 4_655 . ? C16 C15 C14 113.4(5) . . ? C15 C15 C16 48.6(3) 4_655 4_655 ? C16 C15 C16 46.5(5) . 4_655 ? C14 C15 C16 159.9(5) . 4_655 ? C15 C15 H15A 59.9 4_655 . ? C16 C15 H15A 109.1 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15A 83.2 4_655 . ? C15 C15 H15B 53.6 4_655 . ? C16 C15 H15B 108.3 . . ? C14 C15 H15B 112.5 . . ? C16 C15 H15B 78.7 4_655 . ? H15A C15 H15B 104.4 . . ? N1 N4 C8 91(3) 4_655 4_655 ? N1 N4 C21 123(3) 4_655 . ? C8 N4 C21 117.4(10) 4_655 . ? N1 N4 C22 75(3) 4_655 . ? C8 N4 C22 16.0(9) 4_655 . ? C21 N4 C22 123.3(12) . . ? N1 N4 C12 70(3) 4_655 4_655 ? C8 N4 C12 114.6(12) 4_655 4_655 ? C21 N4 C12 53.5(6) . 4_655 ? C22 N4 C12 105.0(12) . 4_655 ? N1 N4 Ni 65(3) 4_655 3_565 ? C8 N4 Ni 115.3(9) 4_655 3_565 ? C21 N4 Ni 126.2(8) . 3_565 ? C22 N4 Ni 110.3(9) . 3_565 ? C12 N4 Ni 111.1(6) 4_655 3_565 ? O6 O6 C18 128.2(4) 4_655 . ? O6 O6 C18 31.2(2) 4_655 4_655 ? C18 O6 C18 97.0(6) . 4_655 ? C18 N3 C19 126.8(5) . . ? C18 N3 H3B 116.5 . . ? C19 N3 H3B 116.7 . . ? C8 C22 N1 95(5) 4_655 4_655 ? C8 C22 N4 77(4) 4_655 . ? N1 C22 N4 18.8(5) 4_655 . ? C8 C22 C9 89(5) 4_655 4_655 ? N1 C22 C9 127.4(14) 4_655 4_655 ? N4 C22 C9 122.2(14) . 4_655 ? C8 C22 C23 69(5) 4_655 . ? N1 C22 C23 126.3(14) 4_655 . ? N4 C22 C23 114.3(13) . . ? C9 C22 C23 20.4(5) 4_655 . ? C8 C22 H22A 114.8 4_655 . ? N1 C22 H22A 114.1 4_655 . ? N4 C22 H22A 125.9 . . ? C9 C22 H22A 111.0 4_655 . ? C23 C22 H22A 119.2 . . ? C9 C23 C8 86.1(11) 4_655 4_655 ? C9 C23 C19 119.2(12) 4_655 . ? C8 C23 C19 115.5(7) 4_655 . ? C9 C23 C22 71.1(11) 4_655 . ? C8 C23 C22 15.0(9) 4_655 . ? C19 C23 C22 122.0(8) . . ? C9 C23 C10 59.9(9) 4_655 4_655 ? C8 C23 C10 111.8(7) 4_655 4_655 ? C19 C23 C10 59.3(4) . 4_655 ? C22 C23 C10 102.5(9) . 4_655 ? C9 C23 H23A 83.3 4_655 . ? C8 C23 H23A 123.2 4_655 . ? C19 C23 H23A 118.3 . . ? C22 C23 H23A 119.6 . . ? C10 C23 H23A 110.1 4_655 . ? N3 C19 C20 124.6(5) . . ? N3 C19 C23 117.6(5) . . ? C20 C19 C23 117.5(5) . . ? N3 C19 C10 105.7(5) . 4_655 ? C20 C19 C10 93.7(5) . 4_655 ? C23 C19 C10 63.8(5) . 4_655 ? N3 C19 C9 118.1(4) . 4_655 ? C20 C19 C9 113.8(5) . 4_655 ? C23 C19 C9 14.8(5) . 4_655 ? C10 C19 C9 49.1(2) 4_655 4_655 ? C21 C20 C19 118.6(5) . . ? C21 C20 C11 73.7(4) . 4_655 ? C19 C20 C11 84.6(4) . 4_655 ? C21 C20 C14 93.7(5) . 6_664 ? C19 C20 C14 96.6(4) . 6_664 ? C11 C20 C14 166.0(4) 4_655 6_664 ? C21 C20 H20A 120.6 . . ? C19 C20 H20A 120.8 . . ? C11 C20 H20A 111.7 4_655 . ? C14 C20 H20A 79.7 6_664 . ? C12 C21 N4 66.5(6) 4_655 . ? C12 C21 C20 107.8(6) 4_655 . ? N4 C21 C20 122.5(7) . . ? C12 C21 N1 53.4(5) 4_655 4_655 ? N4 C21 N1 13.2(7) . 4_655 ? C20 C21 N1 125.3(6) . 4_655 ? C12 C21 C11 46.6(4) 4_655 4_655 ? N4 C21 C11 93.9(7) . 4_655 ? C20 C21 C11 61.2(4) . 4_655 ? N1 C21 C11 85.1(5) 4_655 4_655 ? C12 C21 H21A 103.8 4_655 . ? N4 C21 H21A 119.0 . . ? C20 C21 H21A 117.7 . . ? N1 C21 H21A 116.8 4_655 . ? C11 C21 H21A 123.3 4_655 . ? O6 C18 N3 122.5(6) . . ? O6 C18 C17 121.5(6) . . ? N3 C18 C17 116.0(5) . . ? O6 C18 C16 122.4(6) . 4_655 ? N3 C18 C16 109.5(5) . 4_655 ? C17 C18 C16 23.8(3) . 4_655 ? O6 C18 O6 20.7(3) . 4_655 ? N3 C18 O6 143.2(5) . 4_655 ? C17 C18 O6 100.8(4) . 4_655 ? C16 C18 O6 103.9(4) 4_655 4_655 ? C16 C17 C17 97.5(7) 4_655 4_655 ? C16 C17 C18 96.1(9) 4_655 . ? C17 C17 C18 110.4(3) 4_655 . ? C16 C17 C16 70.5(9) 4_655 . ? C17 C17 C16 27.1(3) 4_655 . ? C18 C17 C16 112.3(6) . . ? C16 C17 H17A 150.5 4_655 . ? C17 C17 H17A 86.7 4_655 . ? C18 C17 H17A 109.8 . . ? C16 C17 H17A 110.2 . . ? C16 C17 H17B 48.4 4_655 . ? C17 C17 H17B 130.3 4_655 . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.1 . . ? H17A C17 H17B 107.8 . . ? C17 C16 C16 82.5(7) 4_655 4_655 ? C17 C16 C15 158.6(10) 4_655 . ? C16 C16 C15 84.9(3) 4_655 . ? C17 C16 C17 55.4(7) 4_655 . ? C16 C16 C17 27.1(3) 4_655 . ? C15 C16 C17 110.7(5) . . ? C17 C16 C18 60.0(8) 4_655 4_655 ? C16 C16 C18 104.5(3) 4_655 4_655 ? C15 C16 C18 107.0(5) . 4_655 ? C17 C16 C18 88.8(5) . 4_655 ? C17 C16 C15 128.6(9) 4_655 4_655 ? C16 C16 C15 48.6(3) 4_655 4_655 ? C15 C16 C15 36.3(3) . 4_655 ? C17 C16 C15 74.8(4) . 4_655 ? C18 C16 C15 111.7(4) 4_655 4_655 ? C17 C16 H16A 91.1 4_655 . ? C16 C16 H16A 113.0 4_655 . ? C15 C16 H16A 109.8 . . ? C17 C16 H16A 109.4 . . ? C18 C16 H16A 128.8 4_655 . ? C15 C16 H16A 119.2 4_655 . ? C17 C16 H16B 66.6 4_655 . ? C16 C16 H16B 128.1 4_655 . ? C15 C16 H16B 109.2 . . ? C17 C16 H16B 109.3 . . ? C18 C16 H16B 23.9 4_655 . ? C15 C16 H16B 127.9 4_655 . ? H16A C16 H16B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.395 _refine_diff_density_min -0.662 _refine_diff_density_rms 0.124 data_4 _database_code_depnum_ccdc_archive 'CCDC 912096' #TrackingRef 'all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H50 N4 Ni2 O20 S2' _chemical_formula_weight 1160.44 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' 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/c 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 21.5324(3) _cell_length_b 12.8686(2) _cell_length_c 20.5775(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.4970(10) _cell_angle_gamma 90.00 _cell_volume 5691.24(14) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 9943 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 28.28 _exptl_crystal_description BLOCK _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2408 _exptl_absorpt_coefficient_mu 0.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7936 _exptl_absorpt_correction_T_max 0.8551 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 27173 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.29 _reflns_number_total 7030 _reflns_number_gt 4606 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2010)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0858P)^2^+8.8677P] 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 7030 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0990 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1736 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.495460(17) 0.49869(3) 0.434060(17) 0.02969(10) Uani 1 1 d . . . S S 0.88361(4) 0.36209(6) 0.51110(7) 0.0693(4) Uani 1 1 d . . . O1 O 0.6762(2) 0.2355(3) 0.20992(17) 0.1146(14) Uani 1 1 d . . . O2 O 0.57652(10) 0.45567(16) 0.48976(10) 0.0369(5) Uani 1 1 d . . . O3 O 0.59292(10) 0.45390(17) 0.59654(10) 0.0385(5) Uani 1 1 d . . . O4 O 0.89307(13) 0.3139(2) 0.4498(2) 0.1012(13) Uani 1 1 d . . . O5 O 0.90926(13) 0.3158(2) 0.5702(2) 0.0983(13) Uani 1 1 d . . . O6 O 0.97658(10) 0.85284(15) 0.55789(10) 0.0366(5) Uani 1 1 d . . . O7 O 0.96472(10) 0.85238(14) 0.44860(9) 0.0346(5) Uani 1 1 d . . . N1 N 0.53928(12) 0.46688(19) 0.35323(12) 0.0347(6) Uani 1 1 d . . . N2 N 0.63946(15) 0.3972(2) 0.19134(13) 0.0552(8) Uani 1 1 d . . . H2B H 0.6392 0.4472 0.1636 0.066 Uiso 1 1 calc R . . C1 C 0.55626(19) 0.5387(3) 0.31183(17) 0.0561(10) Uani 1 1 d . . . H1A H 0.5450 0.6073 0.3191 0.067 Uiso 1 1 calc R . . C2 C 0.5897(2) 0.5172(3) 0.25847(18) 0.0602(11) Uani 1 1 d . . . H2A H 0.6001 0.5701 0.2304 0.072 Uiso 1 1 calc R . . C3 C 0.60750(16) 0.4167(2) 0.24723(14) 0.0407(8) Uani 1 1 d . . . C4 C 0.59118(18) 0.3416(3) 0.29095(16) 0.0517(9) Uani 1 1 d . . . H4A H 0.6034 0.2729 0.2860 0.062 Uiso 1 1 calc R . . C5 C 0.55679(17) 0.3702(2) 0.34159(15) 0.0465(9) Uani 1 1 d . . . H5A H 0.5449 0.3184 0.3698 0.056 Uiso 1 1 calc R . . C6 C 0.6707(2) 0.3108(3) 0.17483(18) 0.0607(11) Uani 1 1 d . . . C7 C 0.6984(2) 0.3180(3) 0.10985(19) 0.0674(12) Uani 1 1 d . . . H7A H 0.6648 0.3238 0.0764 0.081 Uiso 1 1 calc R . . H7B H 0.7227 0.3813 0.1088 0.081 Uiso 1 1 calc R . . C8 C 0.7386(2) 0.2292(4) 0.0934(2) 0.0760(14) Uani 1 1 d . . . H8A H 0.7134 0.1667 0.0893 0.091 Uiso 1 1 calc R . . H8B H 0.7699 0.2185 0.1286 0.091 Uiso 1 1 calc R . . C9 C 0.7712(2) 0.2464(5) 0.0293(2) 0.0839(15) Uani 1 1 d . . . H9A H 0.7954 0.3099 0.0332 0.101 Uiso 1 1 calc R . . H9B H 0.7999 0.1895 0.0237 0.101 Uiso 1 1 calc R . . C10 C 0.61179(13) 0.4417(2) 0.53974(14) 0.0313(6) Uani 1 1 d . . . C11 C 0.67840(14) 0.4139(2) 0.53210(15) 0.0338(7) Uani 1 1 d . . . C12 C 0.71647(16) 0.3874(3) 0.58560(18) 0.0479(8) Uani 1 1 d . . . H12A H 0.7003 0.3823 0.6264 0.057 Uiso 1 1 calc R . . C13 C 0.77930(17) 0.3682(3) 0.5785(2) 0.0559(10) Uani 1 1 d . . . H13A H 0.8053 0.3495 0.6144 0.067 Uiso 1 1 calc R . . C14 C 0.80250(16) 0.3771(2) 0.5184(2) 0.0486(9) Uani 1 1 d . . . C15 C 0.76488(17) 0.4012(3) 0.4648(2) 0.0548(10) Uani 1 1 d . . . H15A H 0.7812 0.4053 0.4241 0.066 Uiso 1 1 calc R . . C16 C 0.70205(16) 0.4198(3) 0.47137(17) 0.0479(9) Uani 1 1 d . . . H16A H 0.6761 0.4361 0.4350 0.057 Uiso 1 1 calc R . . C17 C 0.90998(16) 0.4926(2) 0.5084(2) 0.0503(10) Uani 1 1 d . . . C18 C 0.92100(18) 0.5452(3) 0.5658(2) 0.0569(10) Uani 1 1 d . . . H18A H 0.9165 0.5119 0.6054 0.068 Uiso 1 1 calc R . . C19 C 0.93883(17) 0.6482(3) 0.56434(17) 0.0472(9) Uani 1 1 d . . . H19A H 0.9462 0.6847 0.6031 0.057 Uiso 1 1 calc R . . C20 C 0.94576(14) 0.6974(2) 0.50516(15) 0.0346(7) Uani 1 1 d . . . C21 C 0.93541(17) 0.6428(2) 0.44794(18) 0.0458(8) Uani 1 1 d . . . H21A H 0.9406 0.6753 0.4083 0.055 Uiso 1 1 calc R . . C22 C 0.91710(17) 0.5389(3) 0.4494(2) 0.0525(10) Uani 1 1 d . . . H22A H 0.9098 0.5017 0.4109 0.063 Uiso 1 1 calc R . . C23 C 0.96422(13) 0.8102(2) 0.50371(14) 0.0319(6) Uani 1 1 d . . . O8 O 0.9239(5) 0.7429(9) 0.8152(5) 0.312(5) Uiso 1 1 d . . . H8C H 0.9296 0.7840 0.8473 0.374 Uiso 1 1 d R . . H8E H 0.9094 0.6856 0.8282 0.374 Uiso 1 1 d R . . O9 O 1.0000 0.655(3) 0.7500 0.60(2) Uiso 1 2 d S . . H9C H 0.9958 0.6943 0.7828 0.726 Uiso 1 1 d R . . O10 O 0.5000 0.0546(17) 0.2500 0.442(12) Uiso 1 2 d S . . H10A H 0.5315 0.0156 0.2465 0.531 Uiso 1 1 d R . . O11' O 0.8171(18) 0.483(3) 0.2823(18) 0.406(19) Uiso 0.50 1 d P . . O11 O 0.7795(16) 0.509(2) 0.2608(16) 0.347(16) Uiso 0.50 1 d P . . 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 Ni 0.0321(2) 0.02606(18) 0.03211(18) -0.00188(15) 0.01207(14) 0.00099(16) S 0.0297(4) 0.0228(4) 0.1577(11) 0.0035(5) 0.0229(6) -0.0001(4) O1 0.171(3) 0.088(2) 0.095(2) 0.0346(18) 0.088(2) 0.077(2) O2 0.0315(11) 0.0356(11) 0.0439(12) -0.0005(9) 0.0046(9) 0.0035(9) O3 0.0358(12) 0.0405(11) 0.0403(11) -0.0043(9) 0.0111(9) 0.0032(10) O4 0.0508(17) 0.0404(14) 0.219(4) -0.047(2) 0.061(2) -0.0105(13) O5 0.0349(15) 0.0444(15) 0.215(4) 0.059(2) 0.0020(19) 0.0042(12) O6 0.0452(13) 0.0260(9) 0.0401(11) -0.0007(8) 0.0143(9) -0.0032(9) O7 0.0413(12) 0.0255(9) 0.0381(11) -0.0035(8) 0.0118(9) -0.0027(9) N1 0.0395(15) 0.0345(12) 0.0316(12) 0.0015(10) 0.0136(11) 0.0069(11) N2 0.079(2) 0.0514(16) 0.0387(14) 0.0065(12) 0.0311(14) 0.0198(16) C1 0.086(3) 0.0347(16) 0.0520(19) 0.0048(15) 0.0356(19) 0.0178(18) C2 0.089(3) 0.0415(18) 0.055(2) 0.0125(15) 0.043(2) 0.0139(19) C3 0.0484(19) 0.0438(17) 0.0315(15) 0.0014(13) 0.0152(13) 0.0128(15) C4 0.077(3) 0.0377(17) 0.0435(18) 0.0042(14) 0.0263(17) 0.0188(17) C5 0.067(2) 0.0342(16) 0.0411(16) 0.0047(13) 0.0253(16) 0.0090(16) C6 0.076(3) 0.061(2) 0.0484(19) 0.0045(17) 0.0327(19) 0.022(2) C7 0.083(3) 0.069(3) 0.055(2) -0.0003(19) 0.039(2) 0.017(2) C8 0.084(3) 0.093(3) 0.054(2) 0.000(2) 0.032(2) 0.029(3) C9 0.070(3) 0.122(4) 0.063(2) -0.026(3) 0.030(2) 0.009(3) C10 0.0285(15) 0.0251(13) 0.0411(16) -0.0040(11) 0.0095(12) -0.0019(12) C11 0.0300(16) 0.0253(13) 0.0466(17) -0.0042(12) 0.0061(13) -0.0017(12) C12 0.0357(18) 0.0509(19) 0.057(2) 0.0067(17) 0.0054(16) 0.0036(16) C13 0.039(2) 0.047(2) 0.081(3) 0.0133(19) -0.0047(19) 0.0052(16) C14 0.0286(17) 0.0263(15) 0.092(3) -0.0055(16) 0.0137(18) -0.0017(13) C15 0.043(2) 0.057(2) 0.068(2) -0.0059(18) 0.0275(18) -0.0018(18) C16 0.0373(18) 0.058(2) 0.0490(19) -0.0040(16) 0.0112(15) 0.0047(16) C17 0.0274(17) 0.0270(15) 0.097(3) 0.0026(17) 0.0118(17) 0.0004(13) C18 0.054(2) 0.0411(18) 0.076(3) 0.0208(19) 0.003(2) -0.0080(17) C19 0.053(2) 0.0362(16) 0.0526(19) 0.0079(15) 0.0062(17) -0.0054(16) C20 0.0272(15) 0.0259(13) 0.0516(17) 0.0004(13) 0.0102(13) -0.0016(12) C21 0.050(2) 0.0311(15) 0.058(2) -0.0029(14) 0.0176(16) -0.0058(15) C22 0.045(2) 0.0333(16) 0.080(3) -0.0170(18) 0.0156(19) -0.0076(16) C23 0.0278(15) 0.0257(13) 0.0436(16) -0.0026(12) 0.0141(12) 0.0001(12) _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 Ni N1 2.004(2) . ? Ni O6 2.007(2) 7_666 ? Ni O7 2.0240(19) 3_445 ? Ni O3 2.060(2) 5_666 ? Ni O2 2.103(2) . ? Ni O2 2.345(2) 5_666 ? Ni Ni 2.7091(7) 5_666 ? S O4 1.431(4) . ? S O5 1.435(4) . ? S C14 1.773(3) . ? S C17 1.775(3) . ? O1 C6 1.210(5) . ? O2 C10 1.254(4) . ? O2 Ni 2.345(2) 5_666 ? O3 C10 1.270(3) . ? O3 Ni 2.060(2) 5_666 ? O6 C23 1.257(3) . ? O6 Ni 2.0070(19) 7_666 ? O7 C23 1.258(3) . ? O7 Ni 2.0240(19) 3 ? N1 C1 1.324(4) . ? N1 C5 1.326(4) . ? N2 C6 1.354(5) . ? N2 C3 1.398(4) . ? N2 H2B 0.8600 . ? C1 C2 1.377(5) . ? C1 H1A 0.9300 . ? C2 C3 1.373(4) . ? C2 H2A 0.9300 . ? C3 C4 1.380(4) . ? C4 C5 1.365(4) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.499(5) . ? C7 C8 1.486(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.547(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C9 1.470(9) 7_655 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.496(4) . ? C11 C12 1.375(5) . ? C11 C16 1.380(4) . ? C12 C13 1.392(5) . ? C12 H12A 0.9300 . ? C13 C14 1.368(5) . ? C13 H13A 0.9300 . ? C14 C15 1.364(5) . ? C15 C16 1.388(5) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.369(6) . ? C17 C22 1.370(6) . ? C18 C19 1.381(5) . ? C18 H18A 0.9300 . ? C19 C20 1.388(4) . ? C19 H19A 0.9300 . ? C20 C21 1.377(5) . ? C20 C23 1.506(4) . ? C21 C22 1.394(5) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? O8 H8C 0.8493 . ? O8 H8E 0.8501 . ? O9 H9C 0.8499 . ? O10 H10A 0.8500 . ? O11' O11 0.96(5) . ? 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 Ni O6 96.25(9) . 7_666 ? N1 Ni O7 96.17(9) . 3_445 ? O6 Ni O7 166.53(8) 7_666 3_445 ? N1 Ni O3 106.24(9) . 5_666 ? O6 Ni O3 90.58(9) 7_666 5_666 ? O7 Ni O3 90.94(9) 3_445 5_666 ? N1 Ni O2 88.94(9) . . ? O6 Ni O2 88.33(9) 7_666 . ? O7 Ni O2 86.71(8) 3_445 . ? O3 Ni O2 164.81(8) 5_666 . ? N1 Ni O2 165.86(9) . 5_666 ? O6 Ni O2 85.04(8) 7_666 5_666 ? O7 Ni O2 84.19(8) 3_445 5_666 ? O3 Ni O2 59.63(8) 5_666 5_666 ? O2 Ni O2 105.19(7) . 5_666 ? N1 Ni Ni 145.60(8) . 5_666 ? O6 Ni Ni 84.41(6) 7_666 5_666 ? O7 Ni Ni 82.40(6) 3_445 5_666 ? O3 Ni Ni 108.14(6) 5_666 5_666 ? O2 Ni Ni 56.67(6) . 5_666 ? O2 Ni Ni 48.52(5) 5_666 5_666 ? O4 S O5 119.9(2) . . ? O4 S C14 108.40(19) . . ? O5 S C14 107.7(2) . . ? O4 S C17 108.7(2) . . ? O5 S C17 108.2(2) . . ? C14 S C17 102.60(15) . . ? C10 O2 Ni 157.8(2) . . ? C10 O2 Ni 83.09(16) . 5_666 ? Ni O2 Ni 74.81(7) . 5_666 ? C10 O3 Ni 95.56(18) . 5_666 ? C23 O6 Ni 122.37(18) . 7_666 ? C23 O7 Ni 123.76(18) . 3 ? C1 N1 C5 116.5(3) . . ? C1 N1 Ni 123.6(2) . . ? C5 N1 Ni 119.7(2) . . ? C6 N2 C3 129.1(3) . . ? C6 N2 H2B 115.5 . . ? C3 N2 H2B 115.5 . . ? N1 C1 C2 123.4(3) . . ? N1 C1 H1A 118.3 . . ? C2 C1 H1A 118.3 . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 117.7(3) . . ? C2 C3 N2 117.6(3) . . ? C4 C3 N2 124.7(3) . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? N1 C5 C4 124.3(3) . . ? N1 C5 H5A 117.8 . . ? C4 C5 H5A 117.8 . . ? O1 C6 N2 122.7(3) . . ? O1 C6 C7 123.5(3) . . ? N2 C6 C7 113.8(3) . . ? C8 C7 C6 115.1(4) . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C7 C8 C9 112.7(4) . . ? C7 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C7 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C9 C9 C8 114.6(5) 7_655 . ? C9 C9 H9A 108.6 7_655 . ? C8 C9 H9A 108.6 . . ? C9 C9 H9B 108.6 7_655 . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O2 C10 O3 121.7(3) . . ? O2 C10 C11 119.0(3) . . ? O3 C10 C11 119.3(3) . . ? C12 C11 C16 120.2(3) . . ? C12 C11 C10 120.3(3) . . ? C16 C11 C10 119.4(3) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C14 C13 C12 119.4(4) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C15 C14 C13 121.3(3) . . ? C15 C14 S 119.8(3) . . ? C13 C14 S 118.9(3) . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15A 120.2 . . ? C16 C15 H15A 120.2 . . ? C11 C16 C15 119.6(3) . . ? C11 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? C18 C17 C22 121.8(3) . . ? C18 C17 S 118.7(3) . . ? C22 C17 S 119.5(3) . . ? C17 C18 C19 119.3(4) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? C18 C19 C20 120.1(3) . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C21 C20 C19 119.8(3) . . ? C21 C20 C23 120.2(3) . . ? C19 C20 C23 119.9(3) . . ? C20 C21 C22 120.1(3) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? C17 C22 C21 118.9(4) . . ? C17 C22 H22A 120.6 . . ? C21 C22 H22A 120.6 . . ? O6 C23 O7 126.7(3) . . ? O6 C23 C20 116.5(3) . . ? O7 C23 C20 116.8(3) . . ? H8C O8 H8E 109.5 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.979 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.112 #===END