# 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_cpd_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C61 H63 F6 N12 Ni2 O12.50' _chemical_formula_weight 1395.65 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' F F 0.0171 0.0103 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 24.1322(7) _cell_length_b 8.2047(3) _cell_length_c 15.4710(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3063.22(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1547 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 20.70 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1446 _exptl_absorpt_coefficient_mu 0.707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6666 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24467 _diffrn_reflns_av_R_equivalents 0.0983 _diffrn_reflns_av_sigmaI/netI 0.1308 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5391 _reflns_number_gt 3271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0073(8) _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 0.12(2) _refine_ls_number_reflns 5391 _refine_ls_number_parameters 421 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _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 0.81435(3) 0.58155(11) 0.97866(6) 0.0222(3) Uani 1 1 d . . . F1 F 0.95179(17) 0.8196(7) 1.3437(3) 0.0644(16) Uani 1 1 d . . . F2 F 1.01346(18) 0.7135(7) 1.2616(3) 0.0572(14) Uani 1 1 d . . . F3 F 1.03753(17) 0.8554(7) 1.3722(3) 0.0682(18) Uani 1 1 d . . . O1 O 0.89870(16) 0.6246(6) 0.9798(3) 0.0303(11) Uani 1 1 d . . . O2 O 0.9378(3) 0.8467(7) 0.9221(3) 0.0615(19) Uani 1 1 d . . . O3 O 0.79526(16) 0.8252(5) 0.9786(3) 0.0259(11) Uani 1 1 d . . . O4 O 0.77048(16) 1.0606(6) 1.0363(3) 0.0271(12) Uani 1 1 d . . . O5 O 0.83052(17) 0.3340(5) 0.9785(3) 0.0337(12) Uani 1 1 d . . . H101 H 0.8555 0.2957 0.9464 0.051 Uiso 1 1 d R . . H102 H 0.8085 0.2646 0.9972 0.051 Uiso 1 1 d R . . N1 N 0.8156(2) 0.5883(8) 0.5710(3) 0.0382(16) Uani 1 1 d . . . N2 N 0.8075(2) 0.5596(8) 0.3866(3) 0.0348(16) Uani 1 1 d . . . N3 N 0.8172(2) 0.5883(7) 0.8426(3) 0.0240(13) Uani 1 1 d . . . N4 N 0.8102(2) 0.5720(7) 0.1133(3) 0.0245(13) Uani 1 1 d . . . N5 N 0.9667(2) 0.6456(8) 0.6380(4) 0.0402(17) Uani 1 1 d . . . N6 N 0.8817(3) 1.0967(10) 0.6357(5) 0.068(2) Uani 1 1 d U . . C1 C 0.9474(3) 0.9822(9) 1.1925(4) 0.0258(17) Uani 1 1 d . . . C2 C 0.9493(2) 0.8903(9) 1.1170(4) 0.0285(19) Uani 1 1 d . . . H2 H 0.9824 0.8389 1.1024 0.034 Uiso 1 1 calc R . . C3 C 0.9044(3) 0.8719(8) 1.0628(4) 0.0224(17) Uani 1 1 d . . . C4 C 0.8530(2) 0.9474(8) 1.0851(4) 0.0217(16) Uani 1 1 d . . . C5 C 0.8511(3) 1.0391(9) 1.1616(4) 0.0304(19) Uani 1 1 d . . . H5A H 0.8182 1.0908 1.1769 0.037 Uiso 1 1 calc R . . C6 C 0.8963(3) 1.0544(10) 1.2144(5) 0.034(2) Uani 1 1 d . . . H6 H 0.8933 1.1135 1.2654 0.040 Uiso 1 1 calc R . . C7 C 1.0000 1.0000 1.2484(6) 0.033(3) Uani 1 2 d S . . C8 C 1.0008(3) 0.8457(12) 1.3071(5) 0.044(2) Uani 1 1 d . . . C9 C 0.9135(3) 0.7750(10) 0.9798(5) 0.0299(17) Uani 1 1 d . . . C10 C 0.8034(2) 0.9417(9) 1.0293(4) 0.0245(16) Uani 1 1 d . . . C11 C 0.8451(3) 0.4626(9) 0.5248(4) 0.0335(18) Uani 1 1 d . A . H11A H 0.8234 0.3630 0.5265 0.040 Uiso 1 1 calc R . . H11B H 0.8799 0.4415 0.5539 0.040 Uiso 1 1 calc R . . C12 C 0.8564(3) 0.5049(11) 0.4337(4) 0.042(2) Uani 1 1 d . A . H12A H 0.8842 0.5903 0.4320 0.050 Uiso 1 1 calc R . . H12B H 0.8717 0.4102 0.4047 0.050 Uiso 1 1 calc R . . C13A C 0.7878(7) 0.712(2) 0.4317(9) 0.029(4) Uiso 0.52 1 d P A 1 H13A H 0.7590 0.7662 0.3987 0.035 Uiso 0.52 1 calc PR A 1 H13B H 0.8181 0.7871 0.4418 0.035 Uiso 0.52 1 calc PR A 1 C14A C 0.7633(5) 0.6378(18) 0.5233(9) 0.020(3) Uiso 0.52 1 d P A 1 H14A H 0.7429 0.7200 0.5551 0.024 Uiso 0.52 1 calc PR A 1 H14B H 0.7395 0.5447 0.5131 0.024 Uiso 0.52 1 calc PR A 1 C13B C 0.7687(7) 0.663(2) 0.4335(11) 0.034(5) Uiso 0.48 1 d P A 2 H13C H 0.7677 0.7683 0.4054 0.041 Uiso 0.48 1 calc PR A 2 H13D H 0.7321 0.6152 0.4283 0.041 Uiso 0.48 1 calc PR A 2 C14B C 0.7800(7) 0.688(2) 0.5230(12) 0.034(5) Uiso 0.48 1 d P A 2 H14C H 0.7940 0.7979 0.5284 0.041 Uiso 0.48 1 calc PR A 2 H14D H 0.7445 0.6854 0.5523 0.041 Uiso 0.48 1 calc PR A 2 C15 C 0.8446(3) 0.4792(10) 0.7963(5) 0.0322(19) Uani 1 1 d . A . H15 H 0.8653 0.4021 0.8262 0.039 Uiso 1 1 calc R . . C16 C 0.8448(3) 0.4704(10) 0.7077(5) 0.034(2) Uani 1 1 d . . . H16 H 0.8648 0.3893 0.6795 0.041 Uiso 1 1 calc R A . C17 C 0.8146(3) 0.5852(10) 0.6605(4) 0.0281(17) Uani 1 1 d . A . C18 C 0.7865(3) 0.7029(10) 0.7077(4) 0.0324(19) Uani 1 1 d . . . H18 H 0.7663 0.7835 0.6796 0.039 Uiso 1 1 calc R A . C19 C 0.7889(3) 0.6993(10) 0.7970(4) 0.0327(19) Uani 1 1 d . A . H19 H 0.7696 0.7791 0.8273 0.039 Uiso 1 1 calc R . . C20 C 0.8524(3) 0.5140(10) 0.1583(4) 0.035(2) Uani 1 1 d . A . H20 H 0.8828 0.4735 0.1281 0.042 Uiso 1 1 calc R . . C21 C 0.8541(3) 0.5100(10) 0.2473(5) 0.038(2) Uani 1 1 d . . . H21 H 0.8852 0.4682 0.2750 0.045 Uiso 1 1 calc R A . C22 C 0.8100(3) 0.5675(9) 0.2964(4) 0.0266(17) Uani 1 1 d . A . C23 C 0.7645(3) 0.6263(10) 0.2477(5) 0.036(2) Uani 1 1 d . . . H23 H 0.7330 0.6638 0.2760 0.044 Uiso 1 1 calc R A . C24 C 0.7665(3) 0.6284(10) 0.1597(4) 0.030(2) Uani 1 1 d . A . H24 H 0.7363 0.6707 0.1298 0.037 Uiso 1 1 calc R . . C25 C 0.9960(3) 0.5922(9) 0.5613(4) 0.042(2) Uani 1 1 d . . . H25A H 1.0318 0.6454 0.5589 0.050 Uiso 1 1 calc R . . H25B H 0.9752 0.6239 0.5104 0.050 Uiso 1 1 calc R . . C26 C 0.9949(3) 0.5915(11) 0.7164(5) 0.046(2) Uani 1 1 d . . . H26A H 0.9727 0.6202 0.7663 0.056 Uiso 1 1 calc R . . H26B H 1.0301 0.6478 0.7212 0.056 Uiso 1 1 calc R . . C27 C 0.8993(4) 1.0230(13) 0.5665(6) 0.065(3) Uani 1 1 d U . . H27 H 0.8907 1.0721 0.5140 0.079 Uiso 1 1 calc R . . C28 C 0.9290(3) 0.8809(11) 0.5626(5) 0.050(2) Uani 1 1 d U . . H28 H 0.9403 0.8400 0.5093 0.060 Uiso 1 1 calc R . . C29 C 0.9421(3) 0.7987(10) 0.6375(5) 0.0331(19) Uani 1 1 d . . . C30 C 0.9252(3) 0.8752(11) 0.7126(5) 0.053(3) Uani 1 1 d . . . H30 H 0.9327 0.8284 0.7661 0.063 Uiso 1 1 calc R . . C31 C 0.8971(4) 1.0207(13) 0.7082(7) 0.068(3) Uani 1 1 d . . . H31 H 0.8879 1.0705 0.7602 0.082 Uiso 1 1 calc R . . O6 O 0.9278(2) 0.1893(8) 0.9265(4) 0.079(2) Uani 1 1 d . . . H103 H 0.9460 0.2787 0.9248 0.119 Uiso 1 1 d R . . H104 H 0.9484 0.1150 0.9055 0.119 Uiso 1 1 d R . . O7 O 0.0000 0.5000 0.9122(9) 0.048(4) Uiso 0.50 2 d SP . . H105 H 0.0337 0.5100 0.8980 0.071 Uiso 0.50 1 d PR . . 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 0.0239(4) 0.0248(5) 0.0181(4) -0.0004(4) -0.0006(4) -0.0002(4) F1 0.035(3) 0.107(5) 0.051(3) 0.032(3) 0.011(2) -0.011(3) F2 0.048(3) 0.051(4) 0.073(4) 0.028(3) -0.004(3) 0.002(3) F3 0.045(3) 0.129(6) 0.031(3) 0.026(3) -0.015(2) -0.012(3) O1 0.025(2) 0.027(3) 0.039(3) -0.003(3) 0.002(2) -0.001(2) O2 0.108(5) 0.044(4) 0.033(3) -0.006(3) 0.033(4) -0.026(4) O3 0.033(2) 0.024(3) 0.021(2) -0.006(3) -0.005(2) -0.001(2) O4 0.023(2) 0.025(3) 0.034(3) -0.006(3) -0.003(2) 0.002(2) O5 0.038(3) 0.026(3) 0.037(3) 0.003(3) 0.012(2) 0.000(2) N1 0.052(4) 0.045(4) 0.018(3) 0.001(3) -0.001(3) 0.015(4) N2 0.045(4) 0.043(5) 0.016(3) -0.001(3) 0.005(3) 0.023(4) N3 0.031(3) 0.024(3) 0.017(3) 0.002(3) 0.006(3) 0.007(4) N4 0.023(3) 0.021(3) 0.030(3) -0.002(3) 0.000(3) -0.003(3) N5 0.042(4) 0.043(5) 0.035(4) 0.000(3) 0.003(3) 0.006(3) N6 0.100(6) 0.051(6) 0.054(5) -0.005(5) 0.007(5) 0.031(5) C1 0.022(4) 0.036(5) 0.020(4) 0.001(4) 0.000(3) -0.005(3) C2 0.013(3) 0.041(5) 0.031(4) -0.004(4) 0.001(3) 0.006(3) C3 0.029(4) 0.013(4) 0.025(4) 0.005(3) 0.001(3) -0.006(3) C4 0.019(3) 0.020(5) 0.026(4) 0.001(3) -0.001(3) -0.001(3) C5 0.024(4) 0.038(6) 0.030(4) -0.007(4) -0.002(3) 0.006(3) C6 0.033(4) 0.041(6) 0.027(4) -0.014(4) -0.004(3) 0.000(4) C7 0.017(5) 0.053(8) 0.030(6) 0.000 0.000 -0.006(5) C8 0.027(4) 0.061(7) 0.043(5) 0.025(5) 0.000(4) 0.004(4) C9 0.026(4) 0.035(5) 0.029(4) -0.009(5) -0.010(4) 0.006(3) C10 0.023(4) 0.032(5) 0.018(4) 0.003(4) 0.004(3) -0.003(3) C11 0.034(4) 0.044(5) 0.022(4) 0.001(4) 0.002(4) 0.012(3) C12 0.041(4) 0.066(6) 0.019(4) -0.002(4) 0.003(4) 0.017(5) C15 0.042(4) 0.029(5) 0.026(4) 0.000(4) 0.005(4) 0.006(4) C16 0.040(4) 0.037(5) 0.024(4) -0.001(4) 0.003(4) 0.009(4) C17 0.036(4) 0.033(5) 0.015(4) 0.000(4) 0.000(3) -0.004(5) C18 0.043(4) 0.035(5) 0.019(4) -0.001(4) -0.006(3) 0.021(4) C19 0.042(4) 0.033(5) 0.023(4) -0.005(4) 0.002(4) 0.011(4) C20 0.033(4) 0.052(6) 0.020(4) 0.003(4) 0.007(3) 0.003(4) C21 0.029(4) 0.053(6) 0.030(4) -0.005(4) -0.005(4) 0.007(4) C22 0.031(4) 0.035(5) 0.014(3) 0.000(3) 0.007(3) 0.001(4) C23 0.030(4) 0.048(6) 0.031(4) -0.004(4) 0.002(3) 0.013(4) C24 0.029(4) 0.047(6) 0.016(4) -0.002(4) -0.008(3) 0.000(4) C25 0.041(4) 0.048(5) 0.036(4) -0.010(4) 0.004(4) 0.010(5) C26 0.044(4) 0.054(6) 0.040(4) 0.002(5) -0.005(4) 0.018(5) C27 0.080(7) 0.060(7) 0.057(6) 0.009(5) 0.000(5) 0.008(6) C28 0.055(5) 0.051(7) 0.044(5) -0.004(5) -0.001(4) 0.021(5) C29 0.039(4) 0.023(5) 0.038(5) -0.007(4) 0.002(4) 0.000(4) C30 0.068(6) 0.054(7) 0.036(5) -0.012(5) -0.003(4) 0.001(5) C31 0.096(8) 0.057(8) 0.052(6) -0.016(6) 0.008(6) 0.030(6) O6 0.057(4) 0.052(4) 0.129(6) 0.008(4) 0.027(4) 0.005(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 Ni1 O3 2.052(5) . ? Ni1 O1 2.066(4) . ? Ni1 O4 2.067(4) 3_647 ? Ni1 O5 2.068(5) . ? Ni1 N4 2.087(5) 1_556 ? Ni1 N3 2.106(5) . ? F1 C8 1.330(8) . ? F2 C8 1.328(10) . ? F3 C8 1.344(8) . ? O1 C9 1.285(8) . ? O2 C9 1.219(9) . ? O3 C10 1.252(8) . ? O4 C10 1.263(7) . ? O4 Ni1 2.067(4) 3_657 ? N1 C17 1.385(8) . ? N1 C14B 1.398(18) . ? N1 C11 1.442(8) . ? N1 C14A 1.518(14) . ? N2 C22 1.399(8) . ? N2 C13B 1.455(17) . ? N2 C12 1.457(8) . ? N2 C13A 1.507(16) . ? N3 C15 1.324(9) . ? N3 C19 1.339(9) . ? N4 C20 1.324(8) . ? N4 C24 1.355(8) . ? N4 Ni1 2.087(5) 1_554 ? N5 C29 1.388(9) . ? N5 C25 1.449(9) . ? N5 C26 1.460(9) . ? N6 C27 1.301(11) . ? N6 C31 1.335(12) . ? C1 C2 1.391(9) . ? C1 C6 1.410(9) . ? C1 C7 1.542(8) . ? C2 C3 1.378(9) . ? C3 C4 1.429(9) . ? C3 C9 1.527(10) . ? C4 C5 1.404(9) . ? C4 C10 1.476(8) . ? C5 C6 1.368(9) . ? C7 C1 1.542(8) 2_775 ? C7 C8 1.558(9) . ? C7 C8 1.558(9) 2_775 ? C11 C12 1.477(9) . ? C13A C14A 1.65(2) . ? C13B C14B 1.42(2) . ? C15 C16 1.372(9) . ? C16 C17 1.398(10) . ? C17 C18 1.388(10) . ? C18 C19 1.383(9) . ? C20 C21 1.378(9) . ? C21 C22 1.390(9) . ? C22 C23 1.415(9) . ? C23 C24 1.363(9) . ? C25 C25 1.526(15) 2_765 ? C26 C26 1.521(17) 2_765 ? C27 C28 1.370(12) . ? C28 C29 1.379(11) . ? C29 C30 1.383(10) . ? C30 C31 1.374(13) . ? 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 O1 93.12(18) . . ? O3 Ni1 O4 81.88(17) . 3_647 ? O1 Ni1 O4 172.22(19) . 3_647 ? O3 Ni1 O5 177.90(18) . . ? O1 Ni1 O5 88.97(18) . . ? O4 Ni1 O5 96.03(18) 3_647 . ? O3 Ni1 N4 91.5(2) . 1_556 ? O1 Ni1 N4 92.6(2) . 1_556 ? O4 Ni1 N4 93.48(19) 3_647 1_556 ? O5 Ni1 N4 88.5(2) . 1_556 ? O3 Ni1 N3 88.9(2) . . ? O1 Ni1 N3 88.4(2) . . ? O4 Ni1 N3 85.55(19) 3_647 . ? O5 Ni1 N3 91.0(2) . . ? N4 Ni1 N3 178.9(2) 1_556 . ? C9 O1 Ni1 116.0(4) . . ? C10 O3 Ni1 135.1(4) . . ? C10 O4 Ni1 132.7(4) . 3_657 ? C17 N1 C14B 122.1(9) . . ? C17 N1 C11 119.5(6) . . ? C14B N1 C11 117.1(9) . . ? C17 N1 C14A 118.4(7) . . ? C14B N1 C14A 22.2(8) . . ? C11 N1 C14A 111.1(7) . . ? C22 N2 C13B 119.9(8) . . ? C22 N2 C12 118.6(5) . . ? C13B N2 C12 116.8(8) . . ? C22 N2 C13A 115.9(7) . . ? C13B N2 C13A 23.7(8) . . ? C12 N2 C13A 106.3(8) . . ? C15 N3 C19 115.4(6) . . ? C15 N3 Ni1 122.7(5) . . ? C19 N3 Ni1 121.9(5) . . ? C20 N4 C24 116.3(6) . . ? C20 N4 Ni1 120.1(4) . 1_554 ? C24 N4 Ni1 123.6(4) . 1_554 ? C29 N5 C25 118.5(6) . . ? C29 N5 C26 118.6(7) . . ? C25 N5 C26 111.1(6) . . ? C27 N6 C31 112.5(9) . . ? C2 C1 C6 117.3(6) . . ? C2 C1 C7 119.6(6) . . ? C6 C1 C7 123.1(6) . . ? C3 C2 C1 123.0(6) . . ? C2 C3 C4 119.2(6) . . ? C2 C3 C9 117.1(6) . . ? C4 C3 C9 123.6(6) . . ? C5 C4 C3 117.7(6) . . ? C5 C4 C10 118.9(6) . . ? C3 C4 C10 123.4(6) . . ? C6 C5 C4 121.7(6) . . ? C5 C6 C1 121.1(7) . . ? C1 C7 C1 111.8(8) . 2_775 ? C1 C7 C8 105.1(4) . . ? C1 C7 C8 113.1(4) 2_775 . ? C1 C7 C8 113.1(4) . 2_775 ? C1 C7 C8 105.1(4) 2_775 2_775 ? C8 C7 C8 108.7(9) . 2_775 ? F2 C8 F1 107.4(7) . . ? F2 C8 F3 107.1(7) . . ? F1 C8 F3 106.0(6) . . ? F2 C8 C7 111.0(6) . . ? F1 C8 C7 111.6(6) . . ? F3 C8 C7 113.4(7) . . ? O2 C9 O1 126.7(8) . . ? O2 C9 C3 115.7(7) . . ? O1 C9 C3 117.4(7) . . ? O3 C10 O4 122.9(6) . . ? O3 C10 C4 121.2(6) . . ? O4 C10 C4 115.9(6) . . ? N1 C11 C12 113.3(6) . . ? N2 C12 C11 113.5(6) . . ? N2 C13A C14A 101.9(10) . . ? N1 C14A C13A 102.6(10) . . ? C14B C13B N2 116.4(13) . . ? N1 C14B C13B 123.4(14) . . ? N3 C15 C16 125.4(7) . . ? C15 C16 C17 118.9(7) . . ? N1 C17 C18 121.5(7) . . ? N1 C17 C16 121.7(7) . . ? C18 C17 C16 116.7(6) . . ? C19 C18 C17 119.3(7) . . ? N3 C19 C18 124.3(7) . . ? N4 C20 C21 123.8(7) . . ? C20 C21 C22 121.0(7) . . ? C21 C22 N2 124.1(6) . . ? C21 C22 C23 114.8(6) . . ? N2 C22 C23 120.9(6) . . ? C24 C23 C22 120.6(7) . . ? N4 C24 C23 123.5(6) . . ? N5 C25 C25 111.2(5) . 2_765 ? N5 C26 C26 112.0(6) . 2_765 ? N6 C27 C28 127.1(10) . . ? C27 C28 C29 119.9(8) . . ? C28 C29 C30 114.6(8) . . ? C28 C29 N5 123.0(7) . . ? C30 C29 N5 122.2(8) . . ? C31 C30 C29 119.9(9) . . ? N6 C31 C30 125.8(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.830 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.176 _database_code_depnum_ccdc_archive 'CCDC 941432' ####################################################################### # # 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_cpd_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C74 H80 N12 Ni3 O27' _chemical_formula_weight 1745.63 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.0719(6) _cell_length_b 15.3456(6) _cell_length_c 21.2185(9) _cell_angle_alpha 94.012(2) _cell_angle_beta 106.478(2) _cell_angle_gamma 106.321(2) _cell_volume 3864.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5212 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 22.02 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1816 _exptl_absorpt_coefficient_mu 0.814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6710 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49246 _diffrn_reflns_av_R_equivalents 0.0728 _diffrn_reflns_av_sigmaI/netI 0.1051 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 25.02 _reflns_number_total 13504 _reflns_number_gt 7247 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1953P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13504 _refine_ls_number_parameters 1036 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1691 _refine_ls_R_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.2976 _refine_ls_wR_factor_gt 0.2334 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_special_details ; Because of the relatively poor crystal quality and systematic errors, it is not possible to improve the large residual electron density and the slightly high R factors. ; 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 -0.39326(7) 0.65098(6) -0.36032(4) 0.0228(3) Uani 1 1 d . . . Ni2 Ni 0.39280(8) 0.83443(6) 0.35920(4) 0.0283(3) Uani 1 1 d . . . Ni3 Ni 0.41688(9) 1.17284(6) 0.11005(5) 0.0356(3) Uani 1 1 d . . . O1 O -0.8744(5) 0.1799(4) -0.3460(3) 0.0452(15) Uani 1 1 d . . . O2 O -0.5504(5) 0.3599(3) -0.4355(3) 0.0385(14) Uani 1 1 d . . . O3 O -0.6567(4) 0.4466(3) -0.4751(2) 0.0303(12) Uani 1 1 d . . . O4 O -0.5102(4) 0.5493(3) -0.3388(2) 0.0264(11) Uani 1 1 d . . . O5 O -0.6402(5) 0.6121(3) -0.3274(3) 0.0423(14) Uani 1 1 d . . . O6 O -0.7262(7) 0.1812(6) -0.1030(3) 0.096(3) Uani 1 1 d . A . O7A O -0.8650(11) 0.1053(9) -0.0681(6) 0.062(4) Uiso 0.55 1 d PD A 1 O7B O -0.8429(14) 0.0738(10) -0.0736(7) 0.060(4) Uiso 0.45 1 d PD A 2 O8 O -1.0458(7) -0.0031(5) -0.1091(3) 0.089(3) Uani 1 1 d . . . H101 H -0.9670 0.0342 -0.0849 0.133 Uiso 1 1 d R . . O9 O -1.1868(6) -0.0457(4) -0.2003(4) 0.0642(19) Uani 1 1 d . . . O10 O 0.9073(5) 1.2946(4) 0.3566(3) 0.0548(17) Uani 1 1 d . . . O11 O 0.5431(5) 1.1335(4) 0.4241(3) 0.0441(14) Uani 1 1 d . . . O12 O 0.6443(5) 1.0503(3) 0.4773(2) 0.0399(13) Uani 1 1 d . . . O13 O 0.5115(4) 0.9380(3) 0.3406(2) 0.0307(12) Uani 1 1 d . . . O14 O 0.6333(5) 0.8705(4) 0.3202(3) 0.0447(14) Uani 1 1 d . . . O15 O 0.5879(5) 1.2346(4) 0.1571(3) 0.0422(14) Uani 1 1 d . B . O16A O 0.6218(9) 1.3367(7) 0.0904(5) 0.043(3) Uiso 0.57 1 d PD B 1 O16B O 0.6476(13) 1.3083(10) 0.0816(6) 0.047(4) Uiso 0.43 1 d PD B 2 O17A O 0.7869(12) 1.4554(9) 0.0808(6) 0.082(4) Uiso 0.60 1 d P C 1 H10A H 0.7361 1.4035 0.0717 0.122 Uiso 0.60 1 d PR C 1 O17B O 0.7490(13) 1.4847(11) 0.0956(7) 0.050(4) Uiso 0.40 1 d P D 2 H10B H 0.6988 1.4307 0.0886 0.076 Uiso 0.40 1 d PR D 2 O18A O 0.9605(12) 1.5102(10) 0.1258(7) 0.092(4) Uiso 0.60 1 d P C 1 O18B O 0.910(2) 1.5637(19) 0.1502(12) 0.129(9) Uiso 0.40 1 d P D 2 O19 O -0.4709(4) 0.7488(3) -0.3306(2) 0.0300(12) Uani 1 1 d . . . H104 H -0.5417 0.7225 -0.3428 0.045 Uiso 1 1 d R . . H103 H -0.4333 0.7519 -0.2938 0.045 Uiso 1 1 d R . . O20 O -0.5113(4) 0.6279(3) -0.4525(2) 0.0279(11) Uani 1 1 d . . . H105 H -0.5108 0.6321 -0.4921 0.042 Uiso 1 1 d R . . H106 H -0.5595 0.5736 -0.4621 0.042 Uiso 1 1 d R . . O21 O -0.3444(4) 0.5410(3) -0.3963(2) 0.0312(12) Uani 1 1 d . . . H107 H -0.3257 0.5418 -0.4328 0.047 Uiso 1 1 d R . . H108 H -0.4028 0.4923 -0.4047 0.047 Uiso 1 1 d R . . O22 O 0.4643(4) 0.7358(3) 0.3346(2) 0.0357(13) Uani 1 1 d . . . H109 H 0.5223 0.7695 0.3273 0.054 Uiso 1 1 d R . . H110 H 0.4808 0.7008 0.3624 0.054 Uiso 1 1 d R . . O23 O 0.5092(4) 0.8659(3) 0.4560(2) 0.0347(12) Uani 1 1 d . . . H111 H 0.5450 0.9229 0.4599 0.052 Uiso 1 1 d R . . H112 H 0.4834 0.8562 0.4880 0.052 Uiso 1 1 d R . . O24 O 0.3406(4) 0.9473(3) 0.3885(2) 0.0385(13) Uani 1 1 d . . . H113 H 0.3444 0.9516 0.4294 0.058 Uiso 1 1 d R . . H114 H 0.2746 0.9436 0.3637 0.058 Uiso 1 1 d R . . O25 O 0.3902(5) 1.1535(3) 0.2008(2) 0.0417(14) Uani 1 1 d . . . H115 H 0.3347 1.1058 0.1973 0.063 Uiso 1 1 d R . . H116 H 0.4496 1.1620 0.2276 0.063 Uiso 1 1 d R . . O26 O 0.2420(5) 1.1072(4) 0.0645(3) 0.0560(16) Uani 1 1 d . . . H117 H 0.1879 1.0786 0.0795 0.084 Uiso 1 1 d R . . H118 H 0.2237 1.0801 0.0237 0.084 Uiso 1 1 d R . . O27 O 0.4335(5) 1.1826(4) 0.0164(2) 0.0446(14) Uani 1 1 d . . . H119 H 0.5011 1.2168 0.0229 0.067 Uiso 1 1 d R . . H120 H 0.3901 1.1851 -0.0212 0.067 Uiso 1 1 d R . . N1 N -0.0405(7) 0.7037(5) -0.0784(3) 0.064(2) Uani 1 1 d . . . N2 N 0.0909(7) 0.7454(5) 0.0589(3) 0.053(2) Uani 1 1 d . . . N3 N -0.2752(5) 0.6654(4) -0.2693(3) 0.0341(15) Uani 1 1 d . . . N4 N 0.2863(5) 0.8071(4) 0.2615(3) 0.0365(16) Uani 1 1 d . . . N5 N -0.0716(5) 0.9329(4) -0.4751(3) 0.0256(14) Uani 1 1 d . . . N6 N -0.2826(5) 0.7449(4) -0.3944(3) 0.0266(14) Uani 1 1 d . . . N7 N 0.4511(6) 0.7733(4) 0.1077(3) 0.0462(19) Uani 1 1 d . . . N8 N 0.4252(7) 0.5833(4) 0.1152(3) 0.051(2) Uani 1 1 d . . . N9 N 0.4441(6) 1.0453(4) 0.1046(3) 0.0421(17) Uani 1 1 d . . . N10 N 0.3976(6) 0.3043(4) 0.1156(3) 0.0427(17) Uani 1 1 d . . . N11 N 0.0701(6) 0.5693(6) 0.4785(5) 0.078(3) Uani 1 1 d . . . N12 N 0.2784(6) 0.7454(4) 0.3927(3) 0.0361(16) Uani 1 1 d . . . C1 C -0.8080(6) 0.2709(5) -0.3380(3) 0.0320(18) Uani 1 1 d . . . C2 C -0.7464(6) 0.2870(5) -0.3817(3) 0.0281(17) Uani 1 1 d . . . H2 H -0.7461 0.2381 -0.4101 0.034 Uiso 1 1 calc R . . C3 C -0.6849(6) 0.3766(5) -0.3830(3) 0.0248(16) Uani 1 1 d . . . C4 C -0.6831(6) 0.4495(5) -0.3391(3) 0.0247(16) Uani 1 1 d . . . C5 C -0.7469(7) 0.4311(5) -0.2969(4) 0.039(2) Uani 1 1 d . . . H5 H -0.7473 0.4796 -0.2682 0.047 Uiso 1 1 calc R . . C6 C -0.8113(7) 0.3412(5) -0.2960(4) 0.039(2) Uani 1 1 d . . . H6 H -0.8548 0.3297 -0.2678 0.047 Uiso 1 1 calc R . . C7 C -0.6266(6) 0.3956(5) -0.4352(3) 0.0251(16) Uani 1 1 d . . . C8 C -0.6074(6) 0.5452(5) -0.3352(3) 0.0286(17) Uani 1 1 d . . . C9 C -0.9162(7) 0.1447(5) -0.2968(4) 0.036(2) Uani 1 1 d . . . C10 C -0.8563(7) 0.1545(5) -0.2304(4) 0.041(2) Uani 1 1 d . . . H10 H -0.7822 0.1929 -0.2151 0.049 Uiso 1 1 calc R . . C11 C -0.9014(7) 0.1100(5) -0.1859(4) 0.039(2) Uani 1 1 d . A . C12 C -1.0163(8) 0.0525(5) -0.2087(4) 0.043(2) Uani 1 1 d . . . C13 C -1.0755(8) 0.0428(6) -0.2756(4) 0.050(2) Uani 1 1 d . . . H13 H -1.1503 0.0057 -0.2912 0.059 Uiso 1 1 calc R . . C14 C -1.0273(8) 0.0866(5) -0.3208(4) 0.046(2) Uani 1 1 d . . . H14 H -1.0683 0.0773 -0.3657 0.055 Uiso 1 1 calc R . . C15 C -0.8228(9) 0.1269(7) -0.1147(4) 0.057(3) Uani 1 1 d D . . C16 C -1.0889(9) -0.0025(6) -0.1711(5) 0.048(2) Uani 1 1 d . . . C17 C 0.8330(7) 1.2057(5) 0.3507(4) 0.038(2) Uani 1 1 d . . . C18 C 0.7615(7) 1.1962(5) 0.3875(4) 0.040(2) Uani 1 1 d . . . H18 H 0.7611 1.2471 0.4138 0.047 Uiso 1 1 calc R . . C19 C 0.6884(6) 1.1084(5) 0.3850(3) 0.0298(17) Uani 1 1 d . . . C20 C 0.6886(6) 1.0326(5) 0.3434(3) 0.0292(17) Uani 1 1 d . . . C21 C 0.7646(7) 1.0469(6) 0.3085(4) 0.039(2) Uani 1 1 d . . . H21 H 0.7674 0.9972 0.2820 0.047 Uiso 1 1 calc R . . C22 C 0.8371(7) 1.1343(6) 0.3122(4) 0.045(2) Uani 1 1 d . . . H22 H 0.8879 1.1432 0.2883 0.054 Uiso 1 1 calc R . . C23 C 0.6183(7) 1.0959(5) 0.4316(4) 0.0357(19) Uani 1 1 d . . . C24 C 0.6057(7) 0.9404(5) 0.3350(3) 0.0304(17) Uani 1 1 d . . . C25 C 0.8900(7) 1.3357(6) 0.3006(4) 0.041(2) Uani 1 1 d . . . C26 C 0.7876(7) 1.3033(5) 0.2493(4) 0.0389(19) Uani 1 1 d . . . H26 H 0.7307 1.2534 0.2528 0.047 Uiso 1 1 calc R . . C27 C 0.7703(7) 1.3452(5) 0.1928(4) 0.039(2) Uani 1 1 d . B . C28 C 0.8567(9) 1.4213(6) 0.1894(4) 0.065(3) Uani 1 1 d . . . C29 C 0.9571(9) 1.4513(7) 0.2439(5) 0.072(3) Uani 1 1 d . . . H29 H 1.0144 1.5027 0.2428 0.086 Uiso 1 1 calc R . . C30 C 0.9733(9) 1.4079(6) 0.2982(5) 0.062(3) Uani 1 1 d . . . H30 H 1.0411 1.4283 0.3328 0.075 Uiso 1 1 calc R C . C31 C 0.6549(8) 1.2990(6) 0.1419(4) 0.045(2) Uani 1 1 d D . . C32A C 0.8735(17) 1.4652(12) 0.1307(9) 0.062(5) Uiso 0.60 1 d P C 1 C32B C 0.836(2) 1.4896(17) 0.1410(12) 0.052(6) Uiso 0.40 1 d P D 2 C33A C -0.0194(15) 0.6312(10) -0.0411(7) 0.044(4) Uiso 0.60 1 d P E 1 H33A H 0.0520 0.6230 -0.0402 0.053 Uiso 0.60 1 calc PR E 1 H33B H -0.0789 0.5732 -0.0598 0.053 Uiso 0.60 1 calc PR E 1 C34A C -0.0171(14) 0.6703(11) 0.0338(7) 0.051(4) Uiso 0.60 1 d P E 1 H34A H -0.0798 0.6932 0.0315 0.061 Uiso 0.60 1 calc PR E 1 H34B H -0.0191 0.6228 0.0617 0.061 Uiso 0.60 1 calc PR E 1 C35A C 0.0673(17) 0.8203(12) 0.0220(9) 0.057(5) Uiso 0.60 1 d P E 1 H35A H 0.1260 0.8787 0.0406 0.068 Uiso 0.60 1 calc PR E 1 H35B H -0.0047 0.8271 0.0210 0.068 Uiso 0.60 1 calc PR E 1 C36A C 0.0660(14) 0.7789(10) -0.0547(7) 0.049(4) Uiso 0.60 1 d P E 1 H36A H 0.0672 0.8255 -0.0833 0.059 Uiso 0.60 1 calc PR E 1 H36B H 0.1293 0.7564 -0.0518 0.059 Uiso 0.60 1 calc PR E 1 C33B C -0.062(2) 0.6355(15) -0.0333(11) 0.044(6) Uiso 0.40 1 d P E 2 H33C H -0.1290 0.6361 -0.0226 0.053 Uiso 0.40 1 calc PR E 2 H33D H -0.0758 0.5745 -0.0565 0.053 Uiso 0.40 1 calc PR E 2 C34B C 0.0262(19) 0.6527(13) 0.0251(10) 0.037(5) Uiso 0.40 1 d P E 2 H34C H 0.0789 0.6239 0.0159 0.044 Uiso 0.40 1 calc PR E 2 H34D H -0.0037 0.6201 0.0567 0.044 Uiso 0.40 1 calc PR E 2 C35B C 0.103(2) 0.8152(14) 0.0146(10) 0.032(5) Uiso 0.40 1 d P E 2 H35C H 0.1115 0.8738 0.0393 0.039 Uiso 0.40 1 calc PR E 2 H35D H 0.1727 0.8214 0.0047 0.039 Uiso 0.40 1 calc PR E 2 C36B C 0.021(3) 0.8009(19) -0.0430(14) 0.075(8) Uiso 0.40 1 d P E 2 H36C H 0.0533 0.8352 -0.0732 0.090 Uiso 0.40 1 calc PR E 2 H36D H -0.0337 0.8277 -0.0349 0.090 Uiso 0.40 1 calc PR E 2 C37 C -0.2622(7) 0.5937(6) -0.2368(4) 0.046(2) Uani 1 1 d . E . H37 H -0.3079 0.5346 -0.2578 0.055 Uiso 1 1 calc R . . C38 C -0.1869(7) 0.6031(6) -0.1760(4) 0.048(2) Uani 1 1 d . . . H38 H -0.1836 0.5512 -0.1564 0.058 Uiso 1 1 calc R E . C39 C -0.1142(8) 0.6889(6) -0.1424(4) 0.048(2) Uani 1 1 d . E . C40 C -0.1253(8) 0.7611(6) -0.1768(4) 0.057(3) Uani 1 1 d . . . H40 H -0.0783 0.8205 -0.1577 0.069 Uiso 1 1 calc R E . C41 C -0.2031(7) 0.7472(6) -0.2379(4) 0.044(2) Uani 1 1 d . E . H41 H -0.2060 0.7980 -0.2590 0.053 Uiso 1 1 calc R . . C42 C 0.2179(7) 0.7213(6) 0.2312(4) 0.048(2) Uani 1 1 d . E . H42 H 0.2162 0.6740 0.2564 0.057 Uiso 1 1 calc R . . C43 C 0.1526(8) 0.7004(6) 0.1673(4) 0.060(3) Uani 1 1 d . . . H43 H 0.1063 0.6402 0.1504 0.072 Uiso 1 1 calc R E . C44 C 0.1526(7) 0.7664(6) 0.1260(4) 0.040(2) Uani 1 1 d . E . C45 C 0.2228(7) 0.8553(6) 0.1567(4) 0.045(2) Uani 1 1 d . . . H45 H 0.2268 0.9035 0.1324 0.054 Uiso 1 1 calc R E . C46 C 0.2856(7) 0.8714(6) 0.2228(4) 0.040(2) Uani 1 1 d . E . H46 H 0.3307 0.9313 0.2418 0.047 Uiso 1 1 calc R . . C47 C 0.0297(6) 0.9194(5) -0.4830(4) 0.0283(17) Uani 1 1 d . . . H47A H 0.0118 0.8829 -0.5262 0.034 Uiso 1 1 calc R . . H47B H 0.0596 0.8860 -0.4490 0.034 Uiso 1 1 calc R . . C48 C 0.1184(6) 1.0118(5) -0.4774(4) 0.0316(18) Uani 1 1 d . . . H48A H 0.1435 1.0451 -0.4324 0.038 Uiso 1 1 calc R . . H48B H 0.1828 1.0012 -0.4867 0.038 Uiso 1 1 calc R . . C49 C -0.1842(6) 0.7367(5) -0.3974(4) 0.0366(19) Uani 1 1 d . . . H49 H -0.1623 0.6884 -0.3800 0.044 Uiso 1 1 calc R . . C50 C -0.1145(6) 0.7947(5) -0.4243(4) 0.037(2) Uani 1 1 d . . . H50 H -0.0489 0.7835 -0.4260 0.045 Uiso 1 1 calc R . . C51 C -0.1398(6) 0.8705(5) -0.4494(3) 0.0274(17) Uani 1 1 d . . . C52 C -0.2427(7) 0.8776(5) -0.4477(4) 0.038(2) Uani 1 1 d . . . H52 H -0.2674 0.9244 -0.4658 0.046 Uiso 1 1 calc R . . C53 C -0.3083(7) 0.8168(5) -0.4199(4) 0.0349(19) Uani 1 1 d . . . H53 H -0.3751 0.8256 -0.4185 0.042 Uiso 1 1 calc R . . C54 C 0.3563(8) 0.7007(6) 0.0618(4) 0.055(3) Uani 1 1 d . . . H54A H 0.3334 0.7211 0.0193 0.066 Uiso 1 1 calc R . . H54B H 0.2934 0.6881 0.0792 0.066 Uiso 1 1 calc R . . C55 C 0.3856(10) 0.6149(6) 0.0518(4) 0.070(3) Uani 1 1 d . . . H55A H 0.3201 0.5671 0.0224 0.084 Uiso 1 1 calc R . . H55B H 0.4439 0.6261 0.0307 0.084 Uiso 1 1 calc R . . C56 C 0.5181(9) 0.6545(6) 0.1627(5) 0.068(3) Uani 1 1 d . . . H56A H 0.5841 0.6638 0.1485 0.082 Uiso 1 1 calc R . . H56B H 0.5344 0.6341 0.2057 0.082 Uiso 1 1 calc R . . C57 C 0.4948(9) 0.7444(6) 0.1704(4) 0.055(3) Uani 1 1 d . . . H57A H 0.4413 0.7388 0.1947 0.066 Uiso 1 1 calc R . . H57B H 0.5639 0.7915 0.1967 0.066 Uiso 1 1 calc R . . C58 C 0.3969(8) 0.9812(5) 0.0504(4) 0.046(2) Uani 1 1 d . . . H58 H 0.3605 0.9980 0.0110 0.056 Uiso 1 1 calc R . . C59 C 0.3981(8) 0.8924(5) 0.0484(4) 0.046(2) Uani 1 1 d . . . H59 H 0.3628 0.8511 0.0087 0.055 Uiso 1 1 calc R . . C60 C 0.4522(7) 0.8635(5) 0.1058(4) 0.037(2) Uani 1 1 d . . . C61 C 0.5121(8) 0.9328(6) 0.1605(4) 0.047(2) Uani 1 1 d . . . H61 H 0.5571 0.9203 0.1990 0.056 Uiso 1 1 calc R . . C62 C 0.5043(8) 1.0190(5) 0.1571(4) 0.048(2) Uani 1 1 d . . . H62 H 0.5447 1.0634 0.1948 0.058 Uiso 1 1 calc R . . C63 C 0.4587(8) 0.3675(5) 0.1687(4) 0.044(2) Uani 1 1 d . . . H63 H 0.4954 0.3484 0.2070 0.052 Uiso 1 1 calc R . . C64 C 0.4710(8) 0.4593(5) 0.1705(4) 0.048(2) Uani 1 1 d . . . H64 H 0.5155 0.5003 0.2094 0.058 Uiso 1 1 calc R . . C65 C 0.4183(7) 0.4921(5) 0.1153(4) 0.041(2) Uani 1 1 d . . . C66 C 0.3522(7) 0.4243(5) 0.0588(4) 0.045(2) Uani 1 1 d . . . H66 H 0.3140 0.4408 0.0197 0.054 Uiso 1 1 calc R . . C67 C 0.3451(8) 0.3342(5) 0.0621(4) 0.045(2) Uani 1 1 d . . . H67 H 0.3005 0.2908 0.0244 0.053 Uiso 1 1 calc R . . C68 C -0.0423(8) 0.5706(6) 0.4761(5) 0.060(3) Uani 1 1 d . . . H68A H -0.0382 0.6063 0.5168 0.071 Uiso 1 1 calc R . . H68B H -0.0720 0.5998 0.4391 0.071 Uiso 1 1 calc R . . C69 C -0.1156(8) 0.4791(7) 0.4683(6) 0.073(3) Uani 1 1 d . . . H69A H -0.1257 0.4455 0.4254 0.088 Uiso 1 1 calc R . . H69B H -0.1886 0.4813 0.4693 0.088 Uiso 1 1 calc R . . C70 C 0.3113(7) 0.6899(6) 0.4328(5) 0.050(2) Uani 1 1 d . . . H70 H 0.3851 0.6897 0.4417 0.060 Uiso 1 1 calc R . . C71 C 0.2460(8) 0.6329(6) 0.4622(5) 0.058(3) Uani 1 1 d . . . H71 H 0.2765 0.5963 0.4902 0.070 Uiso 1 1 calc R . . C72 C 0.1352(7) 0.6281(6) 0.4515(4) 0.045(2) Uani 1 1 d . . . C73 C 0.0987(8) 0.6869(7) 0.4093(5) 0.067(3) Uani 1 1 d . . . H73 H 0.0251 0.6881 0.3994 0.081 Uiso 1 1 calc R . . C74 C 0.1709(7) 0.7424(6) 0.3825(5) 0.054(2) Uani 1 1 d . . . H74 H 0.1439 0.7811 0.3552 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0206(5) 0.0278(5) 0.0190(5) 0.0096(4) 0.0056(4) 0.0053(4) Ni2 0.0279(6) 0.0329(6) 0.0223(5) 0.0087(4) 0.0031(4) 0.0108(5) Ni3 0.0439(7) 0.0288(6) 0.0327(6) 0.0073(4) 0.0098(5) 0.0115(5) O1 0.053(4) 0.035(3) 0.034(3) 0.000(2) 0.023(3) -0.015(3) O2 0.048(4) 0.041(3) 0.048(3) 0.024(3) 0.031(3) 0.028(3) O3 0.046(3) 0.029(3) 0.020(2) 0.011(2) 0.014(2) 0.013(2) O4 0.028(3) 0.031(3) 0.020(2) 0.009(2) 0.007(2) 0.008(2) O5 0.036(3) 0.032(3) 0.063(4) 0.006(3) 0.022(3) 0.012(3) O6 0.062(5) 0.132(7) 0.054(5) 0.036(5) 0.000(4) -0.017(5) O8 0.107(7) 0.080(5) 0.056(5) 0.021(4) 0.037(5) -0.021(5) O9 0.052(5) 0.048(4) 0.090(5) 0.010(4) 0.039(4) -0.004(4) O10 0.042(4) 0.054(4) 0.046(4) 0.022(3) -0.003(3) -0.005(3) O11 0.049(4) 0.045(3) 0.057(4) 0.020(3) 0.027(3) 0.030(3) O12 0.057(4) 0.034(3) 0.034(3) 0.010(2) 0.018(3) 0.017(3) O13 0.029(3) 0.036(3) 0.027(3) 0.008(2) 0.007(2) 0.011(2) O14 0.052(4) 0.038(3) 0.054(4) 0.012(3) 0.028(3) 0.017(3) O15 0.041(4) 0.037(3) 0.044(3) 0.014(3) 0.009(3) 0.006(3) O19 0.028(3) 0.035(3) 0.023(3) 0.003(2) 0.006(2) 0.007(2) O20 0.032(3) 0.035(3) 0.015(2) 0.007(2) 0.007(2) 0.008(2) O21 0.037(3) 0.031(3) 0.029(3) 0.012(2) 0.015(2) 0.010(2) O22 0.042(3) 0.033(3) 0.035(3) 0.010(2) 0.011(3) 0.016(3) O23 0.034(3) 0.044(3) 0.026(3) 0.010(2) 0.006(2) 0.014(3) O24 0.040(3) 0.051(3) 0.030(3) 0.011(2) 0.009(3) 0.025(3) O25 0.039(3) 0.043(3) 0.036(3) 0.005(2) 0.012(3) 0.001(3) O26 0.058(4) 0.057(4) 0.044(4) 0.010(3) 0.018(3) 0.002(3) O27 0.045(4) 0.055(4) 0.030(3) 0.009(3) 0.006(3) 0.016(3) N1 0.073(6) 0.045(5) 0.041(4) 0.015(4) -0.015(4) 0.000(4) N2 0.063(5) 0.051(5) 0.025(4) 0.007(3) -0.004(4) 0.004(4) N3 0.028(4) 0.034(4) 0.030(3) 0.010(3) 0.003(3) -0.002(3) N4 0.026(4) 0.046(4) 0.028(4) 0.009(3) 0.002(3) 0.005(3) N5 0.013(3) 0.031(3) 0.041(4) 0.025(3) 0.013(3) 0.010(3) N6 0.026(4) 0.031(3) 0.025(3) 0.016(3) 0.010(3) 0.009(3) N7 0.073(6) 0.023(4) 0.033(4) 0.005(3) 0.003(4) 0.013(4) N8 0.082(6) 0.021(4) 0.029(4) 0.006(3) -0.003(4) 0.008(4) N9 0.051(5) 0.036(4) 0.030(4) 0.009(3) 0.005(3) 0.007(4) N10 0.057(5) 0.031(4) 0.035(4) 0.001(3) 0.006(4) 0.014(4) N11 0.022(4) 0.089(6) 0.139(8) 0.089(6) 0.027(5) 0.024(4) N12 0.037(4) 0.042(4) 0.033(4) 0.015(3) 0.008(3) 0.021(3) C1 0.024(4) 0.033(4) 0.027(4) 0.006(3) 0.001(3) -0.002(4) C2 0.029(4) 0.030(4) 0.025(4) 0.010(3) 0.009(3) 0.007(4) C3 0.024(4) 0.029(4) 0.019(4) 0.007(3) 0.006(3) 0.006(3) C4 0.016(4) 0.027(4) 0.022(4) 0.001(3) 0.002(3) -0.004(3) C5 0.041(5) 0.039(5) 0.029(4) -0.002(4) 0.017(4) -0.005(4) C6 0.026(5) 0.047(5) 0.041(5) 0.004(4) 0.019(4) -0.002(4) C7 0.030(4) 0.022(4) 0.023(4) 0.006(3) 0.010(3) 0.005(3) C8 0.028(5) 0.035(4) 0.020(4) 0.000(3) 0.008(3) 0.004(4) C9 0.048(6) 0.041(5) 0.025(4) 0.006(3) 0.014(4) 0.018(4) C10 0.041(5) 0.035(5) 0.038(5) 0.005(4) 0.013(4) -0.002(4) C11 0.036(5) 0.035(5) 0.038(5) 0.012(4) 0.008(4) -0.001(4) C12 0.055(6) 0.036(5) 0.039(5) 0.010(4) 0.023(5) 0.009(4) C13 0.035(5) 0.048(5) 0.049(6) 0.007(4) 0.009(4) -0.007(4) C14 0.054(6) 0.038(5) 0.035(5) 0.004(4) 0.012(4) 0.000(5) C15 0.054(7) 0.061(6) 0.036(5) 0.024(5) 0.008(5) -0.006(5) C16 0.061(7) 0.040(5) 0.046(6) 0.011(4) 0.031(5) 0.006(5) C17 0.036(5) 0.032(5) 0.036(5) 0.014(4) 0.003(4) 0.000(4) C18 0.036(5) 0.036(5) 0.034(4) 0.005(4) -0.007(4) 0.010(4) C19 0.026(4) 0.031(4) 0.026(4) 0.010(3) -0.002(3) 0.009(4) C20 0.020(4) 0.040(5) 0.024(4) 0.011(3) 0.000(3) 0.009(4) C21 0.036(5) 0.045(5) 0.028(4) 0.000(4) 0.002(4) 0.008(4) C22 0.028(5) 0.058(6) 0.043(5) 0.007(4) 0.013(4) 0.002(4) C23 0.040(5) 0.028(4) 0.037(4) 0.003(3) 0.009(4) 0.010(4) C24 0.036(5) 0.035(4) 0.024(4) 0.012(3) 0.011(4) 0.013(4) C25 0.033(5) 0.039(5) 0.045(5) 0.010(4) 0.008(4) 0.006(4) C26 0.027(5) 0.032(4) 0.048(5) 0.005(4) 0.007(4) 0.000(4) C27 0.040(5) 0.043(5) 0.037(5) 0.009(4) 0.018(4) 0.011(4) C28 0.082(8) 0.053(6) 0.035(5) 0.013(4) 0.011(5) -0.013(6) C29 0.053(7) 0.062(7) 0.062(7) 0.022(5) 0.001(5) -0.027(5) C30 0.055(7) 0.047(6) 0.067(7) 0.019(5) 0.010(5) -0.003(5) C31 0.052(6) 0.043(5) 0.034(5) 0.014(4) 0.010(4) 0.010(5) C37 0.049(6) 0.042(5) 0.031(5) 0.016(4) -0.001(4) 0.004(4) C38 0.048(6) 0.045(5) 0.044(5) 0.020(4) 0.002(4) 0.012(5) C39 0.057(6) 0.048(6) 0.028(5) 0.013(4) -0.001(4) 0.013(5) C40 0.063(7) 0.044(5) 0.039(5) 0.006(4) -0.004(5) -0.003(5) C41 0.056(6) 0.039(5) 0.025(4) 0.009(4) 0.000(4) 0.008(5) C42 0.044(6) 0.048(5) 0.029(5) 0.015(4) -0.003(4) -0.007(4) C43 0.061(7) 0.050(6) 0.038(5) 0.006(4) -0.003(5) -0.010(5) C44 0.038(5) 0.055(6) 0.022(4) 0.012(4) 0.002(4) 0.012(4) C45 0.051(6) 0.046(5) 0.032(5) 0.011(4) 0.002(4) 0.018(5) C46 0.040(5) 0.042(5) 0.035(5) 0.008(4) 0.007(4) 0.014(4) C47 0.020(4) 0.029(4) 0.039(4) 0.023(3) 0.010(3) 0.009(3) C48 0.027(4) 0.036(4) 0.037(4) 0.022(3) 0.012(4) 0.013(4) C49 0.027(5) 0.034(4) 0.055(5) 0.028(4) 0.015(4) 0.013(4) C50 0.024(4) 0.040(5) 0.057(5) 0.026(4) 0.016(4) 0.017(4) C51 0.022(4) 0.030(4) 0.031(4) 0.009(3) 0.007(3) 0.009(3) C52 0.032(5) 0.038(5) 0.059(5) 0.033(4) 0.021(4) 0.020(4) C53 0.031(5) 0.039(5) 0.045(5) 0.021(4) 0.018(4) 0.017(4) C54 0.062(7) 0.037(5) 0.054(6) 0.010(4) 0.002(5) 0.014(5) C55 0.108(9) 0.048(6) 0.039(5) 0.007(4) -0.010(5) 0.035(6) C56 0.093(8) 0.031(5) 0.055(6) 0.005(4) -0.013(6) 0.020(5) C57 0.072(7) 0.036(5) 0.038(5) -0.001(4) -0.003(5) 0.011(5) C58 0.077(7) 0.042(5) 0.025(4) 0.008(4) 0.014(4) 0.027(5) C59 0.068(7) 0.035(5) 0.031(4) 0.004(4) 0.010(4) 0.019(5) C60 0.050(6) 0.027(4) 0.037(5) 0.004(3) 0.012(4) 0.016(4) C61 0.058(6) 0.040(5) 0.035(5) 0.014(4) 0.004(4) 0.013(5) C62 0.063(6) 0.033(5) 0.037(5) -0.006(4) -0.001(4) 0.017(5) C63 0.066(6) 0.032(5) 0.034(5) 0.009(4) 0.015(4) 0.016(4) C64 0.075(7) 0.033(5) 0.026(4) 0.006(3) 0.004(4) 0.014(5) C65 0.055(6) 0.028(4) 0.033(4) 0.007(3) 0.006(4) 0.014(4) C66 0.053(6) 0.036(5) 0.029(4) 0.004(4) -0.008(4) 0.011(4) C67 0.061(6) 0.029(4) 0.031(4) 0.003(3) -0.003(4) 0.014(4) C68 0.051(6) 0.059(6) 0.080(7) 0.040(5) 0.019(5) 0.030(5) C69 0.030(6) 0.079(7) 0.114(9) 0.069(7) 0.018(6) 0.015(5) C70 0.030(5) 0.058(6) 0.075(6) 0.039(5) 0.020(5) 0.023(5) C71 0.041(6) 0.061(6) 0.087(7) 0.051(6) 0.021(5) 0.027(5) C72 0.019(5) 0.041(5) 0.071(6) 0.030(4) 0.008(4) 0.006(4) C73 0.035(6) 0.086(7) 0.098(8) 0.072(7) 0.023(6) 0.031(5) C74 0.038(6) 0.057(6) 0.071(6) 0.041(5) 0.010(5) 0.022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O4 2.034(5) . ? Ni1 O20 2.053(4) . ? Ni1 N3 2.054(6) . ? Ni1 N6 2.064(6) . ? Ni1 O21 2.131(5) . ? Ni1 O19 2.184(5) . ? Ni2 O13 2.035(5) . ? Ni2 N12 2.049(7) . ? Ni2 N4 2.079(6) . ? Ni2 O22 2.097(5) . ? Ni2 O23 2.107(5) . ? Ni2 O24 2.147(5) . ? Ni3 O27 2.071(5) . ? Ni3 O15 2.075(6) . ? Ni3 O25 2.078(5) . ? Ni3 N9 2.086(6) . ? Ni3 N10 2.101(6) 1_565 ? Ni3 O26 2.119(6) . ? O1 C9 1.383(9) . ? O1 C1 1.391(9) . ? O2 C7 1.267(8) . ? O3 C7 1.249(8) . ? O4 C8 1.279(8) . ? O5 C8 1.236(8) . ? O6 C15 1.247(11) . ? O7A C15 1.282(12) . ? O7B C15 1.265(13) . ? O8 C16 1.279(11) . ? O9 C16 1.215(11) . ? O10 C25 1.375(9) . ? O10 C17 1.407(9) . ? O11 C23 1.253(9) . ? O12 C23 1.259(9) . ? O13 C24 1.261(9) . ? O14 C24 1.270(9) . ? O15 C31 1.251(9) . ? O16A C31 1.296(10) . ? O16B C31 1.278(12) . ? O17A C32A 1.27(2) . ? O17B C32B 1.24(3) . ? O18A C32A 1.19(2) . ? O18B C32B 1.24(3) . ? N1 C39 1.383(10) . ? N1 C33A 1.454(15) . ? N1 C36A 1.464(17) . ? N1 C33B 1.49(2) . ? N1 C36B 1.51(3) . ? N2 C44 1.385(9) . ? N2 C34B 1.45(2) . ? N2 C34A 1.476(17) . ? N2 C35B 1.48(2) . ? N2 C35A 1.490(18) . ? N3 C41 1.330(10) . ? N3 C37 1.364(9) . ? N4 C46 1.326(9) . ? N4 C42 1.357(10) . ? N5 C51 1.370(9) . ? N5 C47 1.449(8) . ? N5 C48 1.473(8) 2_574 ? N6 C53 1.345(8) . ? N6 C49 1.347(9) . ? N7 C60 1.383(9) . ? N7 C57 1.444(10) . ? N7 C54 1.454(11) . ? N8 C65 1.378(9) . ? N8 C56 1.446(11) . ? N8 C55 1.465(10) . ? N9 C62 1.329(10) . ? N9 C58 1.332(10) . ? N10 C63 1.323(10) . ? N10 C67 1.333(9) . ? N10 Ni3 2.101(6) 1_545 ? N11 C72 1.336(10) . ? N11 C68 1.462(11) . ? N11 C69 1.472(10) 2_566 ? N12 C70 1.318(9) . ? N12 C74 1.346(10) . ? C1 C6 1.369(10) . ? C1 C2 1.382(10) . ? C2 C3 1.391(10) . ? C3 C4 1.395(9) . ? C3 C7 1.513(9) . ? C4 C5 1.381(10) . ? C4 C8 1.505(10) . ? C5 C6 1.405(11) . ? C9 C10 1.379(11) . ? C9 C14 1.397(12) . ? C10 C11 1.374(11) . ? C11 C12 1.433(12) . ? C11 C15 1.523(11) . ? C12 C13 1.385(11) . ? C12 C16 1.525(11) . ? C13 C14 1.401(11) . ? C17 C22 1.344(11) . ? C17 C18 1.363(11) . ? C18 C19 1.403(11) . ? C19 C20 1.410(10) . ? C19 C23 1.516(11) . ? C20 C21 1.380(11) . ? C20 C24 1.484(11) . ? C21 C22 1.389(11) . ? C25 C30 1.334(12) . ? C25 C26 1.396(11) . ? C26 C27 1.391(11) . ? C27 C28 1.400(12) . ? C27 C31 1.520(11) . ? C28 C29 1.414(13) . ? C28 C32A 1.50(2) . ? C28 C32B 1.54(3) . ? C29 C30 1.365(12) . ? C33A C34A 1.65(2) . ? C35A C36A 1.70(2) . ? C33B C34B 1.38(3) . ? C35B C36B 1.33(3) . ? C37 C38 1.352(11) . ? C38 C39 1.389(12) . ? C39 C40 1.388(11) . ? C40 C41 1.360(11) . ? C42 C43 1.342(11) . ? C43 C44 1.386(11) . ? C44 C45 1.400(11) . ? C45 C46 1.374(11) . ? C47 C48 1.530(10) . ? C48 N5 1.473(8) 2_574 ? C49 C50 1.363(10) . ? C50 C51 1.397(9) . ? C51 C52 1.390(10) . ? C52 C53 1.367(10) . ? C54 C55 1.490(12) . ? C56 C57 1.501(11) . ? C58 C59 1.364(10) . ? C59 C60 1.394(10) . ? C60 C61 1.390(11) . ? C61 C62 1.360(11) . ? C63 C64 1.370(10) . ? C64 C65 1.385(10) . ? C65 C66 1.414(10) . ? C66 C67 1.368(10) . ? C68 C69 1.429(13) . ? C69 N11 1.472(10) 2_566 ? C70 C71 1.356(11) . ? C71 C72 1.380(11) . ? C72 C73 1.398(10) . ? C73 C74 1.363(12) . ? 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 O20 85.35(18) . . ? O4 Ni1 N3 92.9(2) . . ? O20 Ni1 N3 176.3(2) . . ? O4 Ni1 N6 172.7(2) . . ? O20 Ni1 N6 88.6(2) . . ? N3 Ni1 N6 93.0(2) . . ? O4 Ni1 O21 84.40(19) . . ? O20 Ni1 O21 87.30(18) . . ? N3 Ni1 O21 89.3(2) . . ? N6 Ni1 O21 91.3(2) . . ? O4 Ni1 O19 88.43(18) . . ? O20 Ni1 O19 86.36(18) . . ? N3 Ni1 O19 96.9(2) . . ? N6 Ni1 O19 95.3(2) . . ? O21 Ni1 O19 170.79(19) . . ? O13 Ni2 N12 170.0(2) . . ? O13 Ni2 N4 93.1(2) . . ? N12 Ni2 N4 94.1(3) . . ? O13 Ni2 O22 92.1(2) . . ? N12 Ni2 O22 94.9(2) . . ? N4 Ni2 O22 89.5(2) . . ? O13 Ni2 O23 83.58(19) . . ? N12 Ni2 O23 89.4(2) . . ? N4 Ni2 O23 176.4(2) . . ? O22 Ni2 O23 89.29(19) . . ? O13 Ni2 O24 81.7(2) . . ? N12 Ni2 O24 90.8(2) . . ? N4 Ni2 O24 94.6(2) . . ? O22 Ni2 O24 172.8(2) . . ? O23 Ni2 O24 86.35(19) . . ? O27 Ni3 O15 92.5(2) . . ? O27 Ni3 O25 175.6(2) . . ? O15 Ni3 O25 91.2(2) . . ? O27 Ni3 N9 89.3(2) . . ? O15 Ni3 N9 89.0(2) . . ? O25 Ni3 N9 88.3(2) . . ? O27 Ni3 N10 89.6(2) . 1_565 ? O15 Ni3 N10 88.5(2) . 1_565 ? O25 Ni3 N10 93.0(2) . 1_565 ? N9 Ni3 N10 177.2(3) . 1_565 ? O27 Ni3 O26 89.1(2) . . ? O15 Ni3 O26 178.1(2) . . ? O25 Ni3 O26 87.2(2) . . ? N9 Ni3 O26 90.0(3) . . ? N10 Ni3 O26 92.5(3) 1_565 . ? C9 O1 C1 122.5(6) . . ? C8 O4 Ni1 130.7(4) . . ? C25 O10 C17 116.1(6) . . ? C24 O13 Ni2 130.2(5) . . ? C31 O15 Ni3 128.8(5) . . ? C39 N1 C33A 124.6(9) . . ? C39 N1 C36A 122.8(9) . . ? C33A N1 C36A 104.4(10) . . ? C39 N1 C33B 119.8(11) . . ? C33A N1 C33B 25.2(10) . . ? C36A N1 C33B 117.1(12) . . ? C39 N1 C36B 119.1(13) . . ? C33A N1 C36B 116.3(13) . . ? C36A N1 C36B 32.7(12) . . ? C33B N1 C36B 114.1(15) . . ? C44 N2 C34B 123.3(10) . . ? C44 N2 C34A 121.3(8) . . ? C34B N2 C34A 29.8(8) . . ? C44 N2 C35B 121.0(10) . . ? C34B N2 C35B 114.9(12) . . ? C34A N2 C35B 113.6(11) . . ? C44 N2 C35A 119.6(9) . . ? C34B N2 C35A 115.7(11) . . ? C34A N2 C35A 103.1(11) . . ? C35B N2 C35A 21.7(11) . . ? C41 N3 C37 114.6(6) . . ? C41 N3 Ni1 121.5(5) . . ? C37 N3 Ni1 123.8(5) . . ? C46 N4 C42 114.9(7) . . ? C46 N4 Ni2 122.3(5) . . ? C42 N4 Ni2 122.6(5) . . ? C51 N5 C47 120.9(5) . . ? C51 N5 C48 120.6(5) . 2_574 ? C47 N5 C48 112.7(5) . 2_574 ? C53 N6 C49 114.6(6) . . ? C53 N6 Ni1 121.4(5) . . ? C49 N6 Ni1 123.8(4) . . ? C60 N7 C57 120.3(6) . . ? C60 N7 C54 118.3(6) . . ? C57 N7 C54 112.0(6) . . ? C65 N8 C56 120.4(7) . . ? C65 N8 C55 119.4(7) . . ? C56 N8 C55 111.7(7) . . ? C62 N9 C58 114.2(7) . . ? C62 N9 Ni3 122.2(5) . . ? C58 N9 Ni3 123.4(5) . . ? C63 N10 C67 116.3(6) . . ? C63 N10 Ni3 120.0(5) . 1_545 ? C67 N10 Ni3 122.0(5) . 1_545 ? C72 N11 C68 122.8(7) . . ? C72 N11 C69 122.7(7) . 2_566 ? C68 N11 C69 111.3(7) . 2_566 ? C70 N12 C74 114.0(7) . . ? C70 N12 Ni2 119.6(6) . . ? C74 N12 Ni2 126.1(5) . . ? C6 C1 C2 121.8(7) . . ? C6 C1 O1 123.6(7) . . ? C2 C1 O1 114.2(6) . . ? C1 C2 C3 119.7(7) . . ? C2 C3 C4 120.0(6) . . ? C2 C3 C7 120.0(6) . . ? C4 C3 C7 119.9(6) . . ? C5 C4 C3 118.8(6) . . ? C5 C4 C8 120.8(6) . . ? C3 C4 C8 120.3(6) . . ? C4 C5 C6 121.8(7) . . ? C1 C6 C5 117.9(7) . . ? O3 C7 O2 124.1(6) . . ? O3 C7 C3 117.4(6) . . ? O2 C7 C3 118.4(6) . . ? O5 C8 O4 125.5(7) . . ? O5 C8 C4 120.0(7) . . ? O4 C8 C4 114.5(6) . . ? C10 C9 O1 126.4(8) . . ? C10 C9 C14 119.3(7) . . ? O1 C9 C14 114.0(7) . . ? C11 C10 C9 122.9(8) . . ? C10 C11 C12 118.9(7) . . ? C10 C11 C15 116.0(7) . . ? C12 C11 C15 125.1(7) . . ? C13 C12 C11 117.8(7) . . ? C13 C12 C16 111.6(8) . . ? C11 C12 C16 130.6(8) . . ? C12 C13 C14 122.5(8) . . ? C9 C14 C13 118.6(8) . . ? O6 C15 O7B 119.4(11) . . ? O6 C15 O7A 122.1(10) . . ? O7B C15 O7A 29.5(8) . . ? O6 C15 C11 116.6(7) . . ? O7B C15 C11 121.9(11) . . ? O7A C15 C11 118.8(10) . . ? O9 C16 O8 120.6(8) . . ? O9 C16 C12 119.9(8) . . ? O8 C16 C12 119.5(9) . . ? C22 C17 C18 122.7(8) . . ? C22 C17 O10 120.4(8) . . ? C18 C17 O10 116.9(7) . . ? C17 C18 C19 119.0(7) . . ? C18 C19 C20 119.4(7) . . ? C18 C19 C23 119.0(7) . . ? C20 C19 C23 121.3(6) . . ? C21 C20 C19 118.5(7) . . ? C21 C20 C24 120.5(7) . . ? C19 C20 C24 120.9(7) . . ? C20 C21 C22 121.1(8) . . ? C17 C22 C21 119.2(8) . . ? O11 C23 O12 124.9(7) . . ? O11 C23 C19 119.0(6) . . ? O12 C23 C19 116.0(6) . . ? O13 C24 O14 125.1(7) . . ? O13 C24 C20 117.0(6) . . ? O14 C24 C20 117.8(7) . . ? C30 C25 O10 117.6(8) . . ? C30 C25 C26 121.9(8) . . ? O10 C25 C26 120.5(7) . . ? C27 C26 C25 120.4(8) . . ? C26 C27 C28 118.6(8) . . ? C26 C27 C31 112.7(7) . . ? C28 C27 C31 128.8(7) . . ? C27 C28 C29 117.8(8) . . ? C27 C28 C32A 130.0(11) . . ? C29 C28 C32A 110.5(11) . . ? C27 C28 C32B 122.4(13) . . ? C29 C28 C32B 117.2(12) . . ? C32A C28 C32B 29.2(9) . . ? C30 C29 C28 122.6(9) . . ? C25 C30 C29 118.7(9) . . ? O15 C31 O16B 122.6(10) . . ? O15 C31 O16A 121.3(9) . . ? O16B C31 O16A 30.0(7) . . ? O15 C31 C27 117.9(6) . . ? O16B C31 C27 115.5(10) . . ? O16A C31 C27 119.6(8) . . ? O18A C32A O17A 115.6(17) . . ? O18A C32A C28 126.5(17) . . ? O17A C32A C28 117.9(16) . . ? O18B C32B O17B 113(2) . . ? O18B C32B C28 118(2) . . ? O17B C32B C28 129(2) . . ? N1 C33A C34A 102.6(11) . . ? N2 C34A C33A 102.8(12) . . ? N2 C35A C36A 100.2(11) . . ? N1 C36A C35A 102.1(12) . . ? C34B C33B N1 113.1(18) . . ? C33B C34B N2 121.6(17) . . ? C36B C35B N2 118(2) . . ? C35B C36B N1 119(2) . . ? C38 C37 N3 124.1(8) . . ? C37 C38 C39 121.1(8) . . ? N1 C39 C40 121.7(8) . . ? N1 C39 C38 123.8(8) . . ? C40 C39 C38 114.4(7) . . ? C41 C40 C39 121.7(8) . . ? N3 C41 C40 124.0(8) . . ? C43 C42 N4 124.2(8) . . ? C42 C43 C44 121.5(8) . . ? N2 C44 C43 122.5(8) . . ? N2 C44 C45 122.7(7) . . ? C43 C44 C45 114.8(7) . . ? C46 C45 C44 120.1(8) . . ? N4 C46 C45 124.4(8) . . ? N5 C47 C48 110.9(6) . . ? N5 C48 C47 110.4(6) 2_574 . ? N6 C49 C50 124.2(6) . . ? C49 C50 C51 121.2(7) . . ? N5 C51 C52 121.5(6) . . ? N5 C51 C50 124.0(6) . . ? C52 C51 C50 114.5(7) . . ? C53 C52 C51 120.9(6) . . ? N6 C53 C52 124.5(7) . . ? N7 C54 C55 111.2(8) . . ? N8 C55 C54 111.4(8) . . ? N8 C56 C57 112.9(8) . . ? N7 C57 C56 113.5(7) . . ? N9 C58 C59 124.6(7) . . ? C58 C59 C60 120.2(7) . . ? N7 C60 C61 122.1(7) . . ? N7 C60 C59 122.7(7) . . ? C61 C60 C59 115.1(7) . . ? C62 C61 C60 119.5(7) . . ? N9 C62 C61 125.7(8) . . ? N10 C63 C64 123.6(7) . . ? C63 C64 C65 121.1(8) . . ? N8 C65 C64 123.3(7) . . ? N8 C65 C66 121.5(7) . . ? C64 C65 C66 115.2(7) . . ? C67 C66 C65 119.3(7) . . ? N10 C67 C66 124.5(7) . . ? C69 C68 N11 110.4(8) . . ? C68 C69 N11 111.2(9) . 2_566 ? N12 C70 C71 125.2(8) . . ? C70 C71 C72 121.3(7) . . ? N11 C72 C71 121.1(7) . . ? N11 C72 C73 124.5(8) . . ? C71 C72 C73 114.4(8) . . ? C74 C73 C72 120.0(8) . . ? N12 C74 C73 125.0(7) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 5.387 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.187 _database_code_depnum_ccdc_archive 'CCDC 941433' ####################################################################### # # 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_cpd_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 N8 Ni2 O11' _chemical_formula_weight 976.28 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 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 18.9270(8) _cell_length_b 15.5587(7) _cell_length_c 15.9579(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.8480(10) _cell_angle_gamma 90.00 _cell_volume 4298.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6703 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 23.85 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6730 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33995 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3798 _reflns_number_gt 2713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1528P)^2^+12.6053P] 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 3798 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2468 _refine_ls_wR_factor_gt 0.2187 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.071 _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 0.26004(4) 0.70833(5) 0.16830(5) 0.0485(3) Uani 1 1 d . . . O1 O 0.0000 0.4010(4) -0.2500 0.0708(19) Uani 1 2 d S . . O2 O 0.2585(3) 0.5902(4) -0.1382(4) 0.0977(18) Uani 1 1 d . . . O3A O 0.1736(3) 0.6946(3) -0.1631(4) 0.0463(13) Uiso 0.80 1 d P . 1 O3B O 0.1493(17) 0.6816(17) -0.145(2) 0.094(10) Uiso 0.20 1 d PD . 2 O4 O 0.2468(2) 0.6429(3) 0.0455(3) 0.0572(11) Uani 1 1 d . . . O5 O 0.1781(3) 0.6054(3) 0.1200(3) 0.0667(12) Uani 1 1 d . . . O6 O 0.1629(4) 0.7855(4) 0.0694(5) 0.113(2) Uani 1 1 d . . . H101 H 0.1776 0.8360 0.0787 0.170 Uiso 1 1 d R . . H102 H 0.1520 0.7711 0.0135 0.170 Uiso 1 1 d R . . N1 N 0.1540(3) 0.8437(3) 0.4666(3) 0.0561(13) Uani 1 1 d . . . N2 N 0.0297(3) 0.9638(3) 0.4129(3) 0.0490(12) Uani 1 1 d . . . N3 N 0.2321(3) 0.7516(3) 0.2714(3) 0.0483(11) Uani 1 1 d . . . N4 N -0.1501(3) 1.1305(3) 0.2521(3) 0.0475(11) Uani 1 1 d . . . C1 C 0.0466(4) 0.4512(4) -0.1758(4) 0.0575(16) Uani 1 1 d . . . C2 C 0.0950(5) 0.5102(5) -0.1883(4) 0.078(2) Uani 1 1 d . . . H2 H 0.0956 0.5168 -0.2459 0.094 Uiso 1 1 calc R . . C3 C 0.1425(4) 0.5596(5) -0.1166(4) 0.0691(19) Uani 1 1 d . . . C4 C 0.1406(4) 0.5481(4) -0.0303(4) 0.0547(15) Uani 1 1 d . . . C5 C 0.0920(4) 0.4865(4) -0.0192(4) 0.0536(15) Uani 1 1 d . . . H5 H 0.0914 0.4787 0.0383 0.064 Uiso 1 1 calc R . . C6 C 0.0452(4) 0.4371(4) -0.0906(4) 0.0602(16) Uani 1 1 d . . . H6 H 0.0134 0.3954 -0.0824 0.072 Uiso 1 1 calc R . . C7 C 0.1971(4) 0.6203(5) -0.1387(4) 0.0651(18) Uani 1 1 d D . . C8 C 0.1913(4) 0.6009(4) 0.0501(4) 0.0523(14) Uani 1 1 d . . . C9 C 0.0803(4) 0.8176(4) 0.4655(5) 0.0657(19) Uani 1 1 d . . . H9A H 0.0818 0.8227 0.5268 0.079 Uiso 1 1 calc R . . H9B H 0.0711 0.7577 0.4474 0.079 Uiso 1 1 calc R . . C10 C 0.0150(4) 0.8711(4) 0.4007(5) 0.0607(16) Uani 1 1 d . . . H10A H 0.0059 0.8557 0.3383 0.073 Uiso 1 1 calc R . . H10B H -0.0316 0.8578 0.4097 0.073 Uiso 1 1 calc R . . C11 C 0.1097(4) 0.9923(4) 0.4363(4) 0.0597(16) Uani 1 1 d . . . H11A H 0.1170 1.0484 0.4650 0.072 Uiso 1 1 calc R . . H11B H 0.1180 0.9980 0.3804 0.072 Uiso 1 1 calc R . . C12 C 0.1692(4) 0.9306(4) 0.5004(4) 0.0623(17) Uani 1 1 d . . . H12A H 0.2203 0.9476 0.5062 0.075 Uiso 1 1 calc R . . H12B H 0.1683 0.9335 0.5606 0.075 Uiso 1 1 calc R . . C13 C 0.1696(4) 0.7188(4) 0.2804(5) 0.0658(19) Uani 1 1 d . . . H13 H 0.1433 0.6741 0.2417 0.079 Uiso 1 1 calc R . . C14 C 0.1428(4) 0.7470(4) 0.3424(5) 0.0680(19) Uani 1 1 d . . . H14 H 0.0995 0.7212 0.3452 0.082 Uiso 1 1 calc R . . C15 C 0.1790(3) 0.8140(4) 0.4021(4) 0.0466(14) Uani 1 1 d . . . C16 C 0.2448(4) 0.8463(4) 0.3939(4) 0.0538(15) Uani 1 1 d . . . H16 H 0.2731 0.8901 0.4326 0.065 Uiso 1 1 calc R . . C17 C 0.2679(4) 0.8139(4) 0.3290(4) 0.0516(14) Uani 1 1 d . . . H17 H 0.3118 0.8374 0.3254 0.062 Uiso 1 1 calc R . . C18 C -0.1622(4) 1.0479(4) 0.2661(4) 0.0499(14) Uani 1 1 d . . . H18 H -0.2125 1.0273 0.2390 0.060 Uiso 1 1 calc R . . C19 C -0.1056(4) 0.9920(4) 0.3175(4) 0.0521(15) Uani 1 1 d . . . H19 H -0.1183 0.9352 0.3234 0.063 Uiso 1 1 calc R . . C20 C -0.0288(3) 1.0190(4) 0.3614(3) 0.0449(13) Uani 1 1 d . . . C21 C -0.0168(3) 1.1060(4) 0.3480(4) 0.0519(14) Uani 1 1 d . . . H21 H 0.0326 1.1292 0.3755 0.062 Uiso 1 1 calc R . . C22 C -0.0768(4) 1.1568(4) 0.2951(4) 0.0503(14) Uani 1 1 d . . . H22 H -0.0662 1.2141 0.2884 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0616(6) 0.0528(5) 0.0394(5) -0.0004(3) 0.0292(4) 0.0064(3) O1 0.085(4) 0.039(3) 0.059(4) 0.000 -0.002(3) 0.000 O2 0.097(4) 0.112(5) 0.105(4) 0.003(4) 0.062(3) 0.020(4) O4 0.066(3) 0.064(3) 0.042(2) -0.0072(19) 0.023(2) -0.003(2) O5 0.073(3) 0.081(3) 0.048(2) -0.011(2) 0.028(2) -0.002(2) O6 0.113(5) 0.106(5) 0.111(5) 0.016(4) 0.036(4) 0.049(4) N1 0.069(3) 0.060(3) 0.052(3) 0.000(2) 0.038(3) 0.014(3) N2 0.058(3) 0.052(3) 0.045(3) -0.002(2) 0.029(2) 0.007(2) N3 0.057(3) 0.048(3) 0.051(3) -0.009(2) 0.034(2) -0.005(2) N4 0.058(3) 0.055(3) 0.034(2) -0.001(2) 0.022(2) 0.004(2) C1 0.063(4) 0.035(3) 0.055(4) 0.004(3) 0.005(3) 0.002(3) C2 0.101(6) 0.073(5) 0.039(3) 0.005(3) 0.006(3) -0.021(4) C3 0.084(5) 0.063(4) 0.043(3) 0.005(3) 0.009(3) -0.020(4) C4 0.064(4) 0.048(3) 0.045(3) 0.000(3) 0.015(3) -0.004(3) C5 0.062(4) 0.049(3) 0.050(3) 0.001(3) 0.023(3) 0.006(3) C6 0.071(4) 0.039(3) 0.065(4) 0.008(3) 0.021(3) 0.002(3) C7 0.069(4) 0.080(5) 0.054(4) -0.004(3) 0.033(3) 0.016(4) C8 0.060(4) 0.053(4) 0.045(3) 0.011(3) 0.022(3) 0.007(3) C9 0.089(5) 0.066(4) 0.071(4) 0.013(3) 0.062(4) 0.018(4) C10 0.068(4) 0.054(4) 0.075(4) 0.007(3) 0.045(4) 0.004(3) C11 0.061(4) 0.064(4) 0.055(4) -0.013(3) 0.025(3) 0.002(3) C12 0.065(4) 0.076(5) 0.047(3) -0.014(3) 0.024(3) 0.015(3) C13 0.088(5) 0.051(4) 0.081(5) -0.026(3) 0.059(4) -0.024(3) C14 0.087(5) 0.059(4) 0.087(5) -0.021(4) 0.065(4) -0.024(4) C15 0.056(3) 0.050(3) 0.041(3) 0.006(2) 0.028(3) 0.012(3) C16 0.061(4) 0.057(4) 0.048(3) -0.017(3) 0.027(3) -0.006(3) C17 0.048(3) 0.062(4) 0.049(3) -0.009(3) 0.025(3) -0.006(3) C18 0.056(3) 0.056(4) 0.042(3) 0.002(3) 0.023(3) -0.001(3) C19 0.066(4) 0.049(3) 0.050(3) 0.002(3) 0.032(3) -0.002(3) C20 0.062(4) 0.048(3) 0.038(3) -0.001(2) 0.034(3) 0.001(3) C21 0.052(3) 0.060(4) 0.049(3) -0.003(3) 0.026(3) -0.003(3) C22 0.065(4) 0.050(3) 0.040(3) 0.002(3) 0.026(3) 0.002(3) _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 O3A 1.987(6) 7_565 ? Ni1 N3 2.036(4) . ? Ni1 N4 2.076(5) 3_545 ? Ni1 O4 2.132(4) . ? Ni1 O5 2.144(5) . ? Ni1 O6 2.228(6) . ? Ni1 C8 2.462(6) . ? O1 C1 1.394(7) . ? O1 C1 1.394(7) 2_554 ? O2 C7 1.250(8) . ? O3A C7 1.243(8) . ? O3A Ni1 1.987(6) 7_565 ? O3B C7 1.290(18) . ? O4 C8 1.266(7) . ? O5 C8 1.241(7) . ? N1 C15 1.376(7) . ? N1 C12 1.441(8) . ? N1 C9 1.447(9) . ? N2 C20 1.379(7) . ? N2 C10 1.468(8) . ? N2 C11 1.474(8) . ? N3 C17 1.318(7) . ? N3 C13 1.349(8) . ? N4 C22 1.338(8) . ? N4 C18 1.340(8) . ? N4 Ni1 2.076(5) 3_455 ? C1 C2 1.367(10) . ? C1 C6 1.389(9) . ? C2 C3 1.370(9) . ? C3 C4 1.404(9) . ? C3 C7 1.542(10) . ? C4 C5 1.389(9) . ? C4 C8 1.498(9) . ? C5 C6 1.362(9) . ? C9 C10 1.502(9) . ? C11 C12 1.517(9) . ? C13 C14 1.355(9) . ? C14 C15 1.390(9) . ? C15 C16 1.397(8) . ? C16 C17 1.373(8) . ? C18 C19 1.367(8) . ? C19 C20 1.399(8) . ? C20 C21 1.403(8) . ? C21 C22 1.361(8) . ? 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 O3A Ni1 N3 99.0(2) 7_565 . ? O3A Ni1 N4 95.9(2) 7_565 3_545 ? N3 Ni1 N4 94.88(19) . 3_545 ? O3A Ni1 O4 99.5(2) 7_565 . ? N3 Ni1 O4 158.29(19) . . ? N4 Ni1 O4 94.30(17) 3_545 . ? O3A Ni1 O5 158.5(2) 7_565 . ? N3 Ni1 O5 98.68(18) . . ? N4 Ni1 O5 94.67(19) 3_545 . ? O4 Ni1 O5 60.96(17) . . ? O3A Ni1 O6 85.1(2) 7_565 . ? N3 Ni1 O6 89.1(2) . . ? N4 Ni1 O6 175.6(2) 3_545 . ? O4 Ni1 O6 81.3(2) . . ? O5 Ni1 O6 83.0(2) . . ? O3A Ni1 C8 129.1(2) 7_565 . ? N3 Ni1 C8 127.9(2) . . ? N4 Ni1 C8 98.00(19) 3_545 . ? O4 Ni1 C8 30.93(17) . . ? O5 Ni1 C8 30.26(18) . . ? O6 Ni1 C8 78.1(2) . . ? C1 O1 C1 111.8(6) . 2_554 ? C7 O3A Ni1 124.6(5) . 7_565 ? C8 O4 Ni1 89.1(4) . . ? C8 O5 Ni1 89.2(4) . . ? C15 N1 C12 121.2(5) . . ? C15 N1 C9 121.2(6) . . ? C12 N1 C9 108.3(5) . . ? C20 N2 C10 118.0(5) . . ? C20 N2 C11 117.3(5) . . ? C10 N2 C11 116.7(5) . . ? C17 N3 C13 115.5(5) . . ? C17 N3 Ni1 125.3(4) . . ? C13 N3 Ni1 119.1(4) . . ? C22 N4 C18 114.8(5) . . ? C22 N4 Ni1 124.1(4) . 3_455 ? C18 N4 Ni1 121.0(4) . 3_455 ? C2 C1 C6 121.8(6) . . ? C2 C1 O1 118.9(6) . . ? C6 C1 O1 119.2(6) . . ? C1 C2 C3 120.5(7) . . ? C2 C3 C4 118.6(6) . . ? C2 C3 C7 115.3(6) . . ? C4 C3 C7 126.0(6) . . ? C5 C4 C3 119.6(6) . . ? C5 C4 C8 119.8(5) . . ? C3 C4 C8 120.6(6) . . ? C6 C5 C4 121.6(6) . . ? C5 C6 C1 117.8(6) . . ? O3A C7 O2 124.3(7) . . ? O3A C7 O3B 30.2(16) . . ? O2 C7 O3B 153.7(18) . . ? O3A C7 C3 116.9(6) . . ? O2 C7 C3 118.5(7) . . ? O3B C7 C3 87.7(17) . . ? O5 C8 O4 119.8(6) . . ? O5 C8 C4 120.6(6) . . ? O4 C8 C4 119.5(5) . . ? O5 C8 Ni1 60.6(3) . . ? O4 C8 Ni1 60.0(3) . . ? C4 C8 Ni1 170.1(4) . . ? N1 C9 C10 112.0(5) . . ? N2 C10 C9 113.2(6) . . ? N2 C11 C12 112.8(6) . . ? N1 C12 C11 111.1(5) . . ? N3 C13 C14 124.0(6) . . ? C13 C14 C15 121.1(6) . . ? N1 C15 C14 122.7(5) . . ? N1 C15 C16 122.6(6) . . ? C14 C15 C16 114.7(5) . . ? C17 C16 C15 120.4(6) . . ? N3 C17 C16 124.4(6) . . ? N4 C18 C19 124.4(6) . . ? C18 C19 C20 120.8(6) . . ? N2 C20 C19 122.1(5) . . ? N2 C20 C21 123.4(5) . . ? C19 C20 C21 114.4(5) . . ? C22 C21 C20 120.6(6) . . ? N4 C22 C21 124.9(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.577 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 941434' ####################################################################### # # 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_cpd_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H44 Cd2 N8 O12' _chemical_formula_weight 1113.68 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 13.5733(5) _cell_length_b 15.9205(7) _cell_length_c 20.8014(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4495.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9869 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.97 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2248 _exptl_absorpt_coefficient_mu 1.019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8753 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details 'Bruker SADABS, 1996' _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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 70038 _diffrn_reflns_av_R_equivalents 0.1033 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.10 _reflns_number_total 4972 _reflns_number_gt 3934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+70.4068P] 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 4972 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0814 _refine_ls_wR_factor_ref 0.1761 _refine_ls_wR_factor_gt 0.1690 _refine_ls_goodness_of_fit_ref 1.401 _refine_ls_restrained_S_all 1.401 _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 Cd1 Cd 0.86212(4) 0.05640(4) 0.08118(3) 0.01708(16) Uani 1 1 d . . . O1 O 1.0000 -0.4239(5) 0.2500 0.039(3) Uani 1 2 d S . . O2 O 0.9176(6) -0.0567(4) 0.1463(3) 0.0380(17) Uani 1 1 d . . . O3 O 0.9089(4) -0.1023(4) 0.0457(3) 0.0272(15) Uani 1 1 d . . . O4 O 1.1221(4) -0.0761(3) 0.0328(3) 0.0193(13) Uani 1 1 d . . . O5 O 1.1325(5) -0.1930(4) -0.0238(3) 0.0277(14) Uani 1 1 d . . . O6 O 1.0341(4) 0.0702(4) 0.0750(3) 0.0198(12) Uani 1 1 d . . . H101 H 1.0628 0.0231 0.0783 0.030 Uiso 1 1 d R . . H102 H 1.0502 0.0947 0.0400 0.030 Uiso 1 1 d R . . N1 N 0.8571(6) 0.2988(4) 0.3332(3) 0.0202(15) Uani 1 1 d . . . N2 N 0.9186(5) 0.4099(4) 0.4329(3) 0.0130(13) Uani 1 1 d . . . N3 N 0.8412(6) 0.1413(5) 0.1701(4) 0.0265(18) Uani 1 1 d . . . N4 N 1.2059(5) 0.5101(4) 0.4307(3) 0.0147(14) Uani 1 1 d . . . C1 C 1.0000 -0.3488(8) 0.2500 0.024(3) Uani 1 2 d S . . C2 C 1.0330(7) -0.2988(5) 0.1938(4) 0.0183(18) Uani 1 1 d . . . C3 C 0.9763(7) -0.2283(5) 0.1749(4) 0.0194(18) Uani 1 1 d . . . H3 H 0.9220 -0.2124 0.1993 0.023 Uiso 1 1 calc R . . C4 C 1.0010(7) -0.1828(5) 0.1206(4) 0.0175(17) Uani 1 1 d . . . C5 C 1.0830(5) -0.2054(5) 0.0859(4) 0.0119(15) Uani 1 1 d . . . C6 C 1.1411(7) -0.2737(5) 0.1034(4) 0.0202(17) Uani 1 1 d . . . H6 H 1.1962 -0.2882 0.0792 0.024 Uiso 1 1 calc R . . C7 C 1.1158(7) -0.3201(5) 0.1575(4) 0.026(2) Uani 1 1 d . . . H7 H 1.1543 -0.3657 0.1696 0.031 Uiso 1 1 calc R . . C8 C 0.9383(6) -0.1084(5) 0.1016(4) 0.0187(18) Uani 1 1 d . . . C9 C 1.1150(6) -0.1547(5) 0.0276(4) 0.0170(17) Uani 1 1 d . . . C10 C 0.9152(7) 0.2672(5) 0.3883(4) 0.0206(18) Uani 1 1 d . . . H10A H 0.9845 0.2666 0.3767 0.025 Uiso 1 1 calc R . . H10B H 0.8956 0.2099 0.3977 0.025 Uiso 1 1 calc R . . C11 C 0.9012(7) 0.3211(5) 0.4483(4) 0.0204(18) Uani 1 1 d . . . H11A H 0.8347 0.3141 0.4646 0.025 Uiso 1 1 calc R . . H11B H 0.9467 0.3031 0.4815 0.025 Uiso 1 1 calc R . . C12 C 0.8451(6) 0.4376(6) 0.3863(4) 0.0189(17) Uani 1 1 d . . . H12A H 0.8525 0.4974 0.3787 0.023 Uiso 1 1 calc R . . H12B H 0.7796 0.4279 0.4035 0.023 Uiso 1 1 calc R . . C13 C 0.8568(7) 0.3902(5) 0.3232(4) 0.0212(18) Uani 1 1 d . . . H13A H 0.8031 0.4051 0.2945 0.025 Uiso 1 1 calc R . . H13B H 0.9180 0.4069 0.3028 0.025 Uiso 1 1 calc R . . C14 C 0.8193(6) 0.2227(6) 0.1669(4) 0.0234(19) Uani 1 1 d . . . H14 H 0.8001 0.2443 0.1273 0.028 Uiso 1 1 calc R . . C15 C 0.8233(7) 0.2772(6) 0.2186(4) 0.0230(19) Uani 1 1 d . . . H15 H 0.8076 0.3336 0.2129 0.028 Uiso 1 1 calc R . . C16 C 0.8512(6) 0.2478(5) 0.2801(4) 0.0202(18) Uani 1 1 d . . . C17 C 0.8733(9) 0.1604(6) 0.2829(5) 0.037(3) Uani 1 1 d . . . H17 H 0.8913 0.1358 0.3218 0.044 Uiso 1 1 calc R . . C18 C 0.8680(8) 0.1128(6) 0.2282(4) 0.034(2) Uani 1 1 d . . . H18 H 0.8843 0.0563 0.2316 0.040 Uiso 1 1 calc R . . C19 C 1.1852(6) 0.4370(5) 0.4593(4) 0.0191(17) Uani 1 1 d . . . H19 H 1.2363 0.4087 0.4797 0.023 Uiso 1 1 calc R . . C20 C 1.0939(6) 0.4010(5) 0.4604(4) 0.0198(18) Uani 1 1 d . . . H20 H 1.0850 0.3496 0.4808 0.024 Uiso 1 1 calc R . . C21 C 1.0131(6) 0.4410(5) 0.4311(3) 0.0141(15) Uani 1 1 d . . . C22 C 1.0355(7) 0.5176(5) 0.4011(4) 0.0219(19) Uani 1 1 d . . . H22 H 0.9859 0.5481 0.3809 0.026 Uiso 1 1 calc R . . C23 C 1.1299(7) 0.5477(6) 0.4016(4) 0.028(2) Uani 1 1 d . . . H23 H 1.1420 0.5979 0.3801 0.033 Uiso 1 1 calc R . . O7 O 0.8835(12) 0.9272(11) 0.2772(8) 0.053(5) Uani 0.50 1 d P . . H103 H 0.9431 0.9321 0.2837 0.079 Uiso 0.50 1 d PR . . H104 H 0.8520 0.9123 0.3090 0.079 Uiso 0.50 1 d PR . . 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 Cd1 0.0194(3) 0.0147(3) 0.0172(3) -0.0027(3) 0.0044(3) -0.0042(3) O1 0.099(9) 0.008(4) 0.011(4) 0.000 -0.005(5) 0.000 O2 0.067(5) 0.020(3) 0.027(3) 0.005(3) 0.013(3) 0.011(4) O3 0.014(3) 0.050(4) 0.017(3) 0.015(3) 0.003(2) 0.008(3) O4 0.022(3) 0.014(3) 0.021(3) 0.001(2) 0.001(2) -0.002(2) O5 0.046(4) 0.019(3) 0.018(3) -0.001(2) 0.002(3) -0.005(3) O6 0.025(3) 0.018(3) 0.016(3) -0.001(2) -0.001(2) 0.000(2) N1 0.022(4) 0.015(3) 0.023(4) -0.008(3) 0.001(3) 0.000(3) N2 0.018(3) 0.012(3) 0.009(3) -0.001(2) 0.000(3) -0.002(3) N3 0.033(4) 0.027(4) 0.019(4) -0.016(3) 0.014(3) -0.009(3) N4 0.018(3) 0.019(4) 0.007(3) 0.004(3) -0.001(3) -0.002(3) C1 0.045(8) 0.020(6) 0.005(5) 0.000 -0.007(5) 0.000 C2 0.031(5) 0.015(4) 0.008(4) 0.003(3) -0.005(3) 0.000(4) C3 0.033(5) 0.017(4) 0.008(4) 0.003(3) 0.002(3) 0.002(4) C4 0.026(4) 0.014(4) 0.012(4) 0.001(3) 0.000(3) -0.004(4) C5 0.010(3) 0.011(3) 0.015(4) 0.000(3) -0.009(3) -0.001(3) C6 0.025(4) 0.013(4) 0.022(4) -0.005(3) -0.001(4) 0.004(4) C7 0.039(6) 0.011(4) 0.026(5) -0.002(4) -0.015(4) 0.001(4) C8 0.019(4) 0.019(4) 0.017(4) 0.008(3) 0.009(3) 0.001(3) C9 0.016(4) 0.016(4) 0.018(4) -0.002(3) -0.003(3) -0.001(3) C10 0.026(5) 0.014(4) 0.021(4) -0.003(3) -0.003(4) -0.004(4) C11 0.026(4) 0.013(4) 0.022(4) 0.007(3) -0.001(4) -0.007(3) C12 0.015(4) 0.020(4) 0.022(4) -0.003(4) -0.001(3) 0.003(3) C13 0.023(4) 0.019(4) 0.021(4) -0.003(3) -0.007(4) -0.002(4) C14 0.021(4) 0.034(5) 0.015(4) -0.008(4) 0.000(4) 0.002(4) C15 0.024(4) 0.023(5) 0.022(4) -0.011(4) -0.002(4) 0.006(4) C16 0.016(4) 0.022(4) 0.022(4) -0.006(3) 0.005(4) -0.007(4) C17 0.071(8) 0.016(4) 0.024(5) -0.005(4) 0.014(5) -0.011(5) C18 0.055(7) 0.022(5) 0.023(5) 0.001(4) 0.011(5) -0.012(5) C19 0.020(4) 0.015(4) 0.022(4) 0.004(4) -0.002(3) -0.002(4) C20 0.021(4) 0.014(4) 0.025(4) 0.007(3) -0.003(4) 0.000(3) C21 0.020(4) 0.015(4) 0.008(3) -0.005(3) 0.001(3) 0.004(3) C22 0.026(5) 0.020(4) 0.019(4) 0.007(3) -0.008(4) -0.002(4) C23 0.021(4) 0.024(5) 0.037(5) 0.016(4) -0.008(4) -0.010(4) O7 0.044(10) 0.066(12) 0.048(10) 0.016(9) 0.011(8) -0.016(9) _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 Cd1 N4 2.258(7) 6_556 ? Cd1 N3 2.309(7) . ? Cd1 O6 2.348(6) . ? Cd1 O2 2.376(7) . ? Cd1 O4 2.400(6) 5_755 ? Cd1 O5 2.481(6) 5_755 ? O1 C1 1.196(15) . ? O2 C8 1.273(11) . ? O3 C8 1.234(10) . ? O4 C9 1.259(10) . ? O4 Cd1 2.400(6) 5_755 ? O5 C9 1.253(10) . ? O5 Cd1 2.481(6) 5_755 ? N1 C16 1.374(10) . ? N1 C13 1.471(10) . ? N1 C10 1.479(11) . ? N2 C21 1.374(10) . ? N2 C12 1.460(10) . ? N2 C11 1.469(10) . ? N3 C14 1.331(12) . ? N3 C18 1.339(12) . ? N4 C19 1.337(10) . ? N4 C23 1.339(11) . ? N4 Cd1 2.258(7) 6_666 ? C1 C2 1.485(10) 4_755 ? C1 C2 1.485(10) . ? C2 C7 1.396(13) . ? C2 C3 1.416(11) . ? C3 C4 1.383(11) . ? C4 C5 1.375(11) . ? C4 C8 1.511(12) . ? C5 C6 1.392(11) . ? C5 C9 1.521(11) . ? C6 C7 1.389(12) . ? C10 C11 1.529(12) . ? C12 C13 1.523(11) . ? C14 C15 1.383(12) . ? C15 C16 1.414(12) . ? C16 C17 1.424(13) . ? C17 C18 1.370(12) . ? C19 C20 1.365(11) . ? C20 C21 1.407(11) . ? C21 C22 1.403(12) . ? C22 C23 1.368(12) . ? 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 N4 Cd1 N3 99.4(2) 6_556 . ? N4 Cd1 O6 163.3(2) 6_556 . ? N3 Cd1 O6 96.4(2) . . ? N4 Cd1 O2 96.5(3) 6_556 . ? N3 Cd1 O2 91.5(3) . . ? O6 Cd1 O2 77.7(2) . . ? N4 Cd1 O4 91.0(2) 6_556 5_755 ? N3 Cd1 O4 136.5(2) . 5_755 ? O6 Cd1 O4 81.1(2) . 5_755 ? O2 Cd1 O4 129.3(2) . 5_755 ? N4 Cd1 O5 105.1(2) 6_556 5_755 ? N3 Cd1 O5 82.9(2) . 5_755 ? O6 Cd1 O5 82.1(2) . 5_755 ? O2 Cd1 O5 158.3(3) . 5_755 ? O4 Cd1 O5 53.71(19) 5_755 5_755 ? C8 O2 Cd1 98.3(5) . . ? C9 O4 Cd1 93.0(5) . 5_755 ? C9 O5 Cd1 89.4(5) . 5_755 ? C16 N1 C13 118.0(7) . . ? C16 N1 C10 116.9(7) . . ? C13 N1 C10 116.6(7) . . ? C21 N2 C12 120.7(6) . . ? C21 N2 C11 120.2(7) . . ? C12 N2 C11 108.9(6) . . ? C14 N3 C18 115.8(8) . . ? C14 N3 Cd1 123.8(6) . . ? C18 N3 Cd1 119.4(6) . . ? C19 N4 C23 115.4(7) . . ? C19 N4 Cd1 122.0(5) . 6_666 ? C23 N4 Cd1 121.9(5) . 6_666 ? O1 C1 C2 122.5(5) . 4_755 ? O1 C1 C2 122.5(5) . . ? C2 C1 C2 115.1(10) 4_755 . ? C7 C2 C3 118.7(8) . . ? C7 C2 C1 122.6(7) . . ? C3 C2 C1 118.7(8) . . ? C4 C3 C2 120.6(8) . . ? C5 C4 C3 119.2(8) . . ? C5 C4 C8 121.6(7) . . ? C3 C4 C8 119.2(8) . . ? C4 C5 C6 121.7(8) . . ? C4 C5 C9 120.7(7) . . ? C6 C5 C9 117.5(7) . . ? C7 C6 C5 119.1(8) . . ? C6 C7 C2 120.6(8) . . ? O3 C8 O2 124.5(8) . . ? O3 C8 C4 119.4(8) . . ? O2 C8 C4 116.1(7) . . ? O5 C9 O4 122.8(8) . . ? O5 C9 C5 118.4(7) . . ? O4 C9 C5 118.8(7) . . ? N1 C10 C11 112.0(7) . . ? N2 C11 C10 110.0(7) . . ? N2 C12 C13 110.7(7) . . ? N1 C13 C12 111.6(7) . . ? N3 C14 C15 124.3(9) . . ? C14 C15 C16 120.4(8) . . ? N1 C16 C15 123.2(8) . . ? N1 C16 C17 122.1(8) . . ? C15 C16 C17 114.7(8) . . ? C18 C17 C16 119.6(9) . . ? N3 C18 C17 125.2(9) . . ? N4 C19 C20 124.3(8) . . ? C19 C20 C21 120.7(8) . . ? N2 C21 C22 121.9(7) . . ? N2 C21 C20 123.5(7) . . ? C22 C21 C20 114.6(7) . . ? C23 C22 C21 120.4(8) . . ? N4 C23 C22 124.6(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.218 _refine_diff_density_min -2.126 _refine_diff_density_rms 0.173 _database_code_depnum_ccdc_archive 'CCDC 941435'