# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 182/1314 #High-Yield Synthesis of a Chiroporphyrin by Hydrogen Bond-Directed Cyclisation data_2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H32 N2 O3' _chemical_formula_weight 348.48 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0181 0.0091 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.861(2) _cell_length_b 20.595(3) _cell_length_c 8.948(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2001.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 163 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method ? _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.615 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1574 _diffrn_reflns_av_R_equivalents 0.0922 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 50.72 _reflns_number_total 1425 _reflns_number_observed 1287 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.2659P)^2^+9.7118P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.27(180) _refine_ls_number_reflns 1421 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_obs 0.0608 _refine_ls_wR_factor_all 0.1882 _refine_ls_wR_factor_obs 0.1553 _refine_ls_goodness_of_fit_all 1.187 _refine_ls_goodness_of_fit_obs 1.929 _refine_ls_restrained_S_all 1.305 _refine_ls_restrained_S_obs 1.929 _refine_ls_shift/esd_max -0.027 _refine_ls_shift/esd_mean 0.005 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.0310(11) 0.0243(6) 0.0584(18) 0.036(4) Uani 1 d . . C2 C 0.1008(12) 0.0381(7) 0.1098(21) 0.043(4) Uani 1 d . . C3 C 0.0784(12) -0.0020(7) -0.0269(21) 0.046(5) Uani 1 d . . C4 C 0.0966(15) -0.0741(7) -0.0113(27) 0.068(6) Uani 1 d . . C5 C 0.1096(14) 0.0246(8) -0.1770(21) 0.057(5) Uani 1 d . . C6 C 0.1547(13) 0.1031(8) 0.1059(24) 0.057(5) Uani 1 d . . O7 O 0.2045(12) 0.1271(7) 0.2120(19) 0.089(4) Uani 1 d . . C8 C -0.1088(11) 0.0780(6) 0.0033(18) 0.029(4) Uani 1 d . . O9 O -0.0671(7) 0.1276(4) -0.0532(11) 0.040(3) Uani 1 d . . N10 N -0.2339(9) 0.0702(4) 0.0212(13) 0.025(3) Uani 1 d . . C11 C -0.2855(11) 0.0147(6) 0.0921(22) 0.028(4) Uani 1 d . . O12 O -0.3256(9) 0.0188(4) 0.2209(14) 0.038(3) Uani 1 d . . N13 N -0.2916(9) -0.0376(5) 0.0076(14) 0.030(3) Uani 1 d . . C14 C -0.3472(12) -0.0986(6) 0.0572(17) 0.035(4) Uani 1 d . . C15 C -0.4575(15) -0.1135(8) -0.0410(24) 0.071(6) Uani 1 d . . C16 C -0.5167(22) -0.1771(10) 0.0088(32) 0.107(9) Uani 1 d . . C17 C -0.4269(28) -0.2320(8) 0.0067(29) 0.104(9) Uani 1 d . . C18 C -0.3184(18) -0.2163(7) 0.1075(24) 0.068(6) Uani 1 d . . C19 C -0.2570(14) -0.1535(7) 0.0565(20) 0.051(5) Uani 1 d . . C20 C -0.3170(11) 0.1260(6) -0.0133(17) 0.031(4) Uani 1 d . . C21 C -0.3279(13) 0.1724(6) 0.1184(18) 0.042(4) Uani 1 d . . C22 C -0.4068(15) 0.2292(7) 0.0750(21) 0.054(5) Uani 1 d . . C23 C -0.5342(13) 0.2081(8) 0.0192(25) 0.062(5) Uani 1 d . . C24 C -0.5206(14) 0.1614(7) -0.1079(22) 0.053(5) Uani 1 d . . C25 C -0.4420(12) 0.1025(7) -0.0646(19) 0.043(4) Uani 1 d . . H1 H -0.0755 -0.0086 0.1175 0.042 Uiso 1 d . . H2 H 0.1298 0.0127 0.1940 0.060 Uiso 1 d . . H3 H 0.0250 -0.0978 -0.0496 0.080 Uiso 1 d . . H4 H 0.1092 -0.0873 0.0883 0.080 Uiso 1 d . . H5 H 0.1660 -0.0901 -0.0706 0.080 Uiso 1 d . . H6 H 0.1753 0.0000 -0.2251 0.072 Uiso 1 d . . H7 H 0.1365 0.0690 -0.1735 0.072 Uiso 1 d . . H8 H 0.0400 0.0227 -0.2441 0.072 Uiso 1 d . . H9 H 0.1503 0.1291 0.0089 0.097 Uiso 1 d . . H10 H -0.2555 -0.0359 -0.0898 0.097 Uiso 1 d . . H11 H -0.3763 -0.0943 0.1594 0.053 Uiso 1 d . . H12 H -0.4284 -0.1171 -0.1451 0.092 Uiso 1 d . . H13 H -0.5129 -0.0768 -0.0407 0.092 Uiso 1 d . . H14 H -0.5880 -0.1879 -0.0536 0.148 Uiso 1 d . . H15 H -0.5515 -0.1715 0.1097 0.148 Uiso 1 d . . H16 H -0.3970 -0.2376 -0.0903 0.137 Uiso 1 d . . H17 H -0.4650 -0.2712 0.0412 0.137 Uiso 1 d . . H18 H -0.2609 -0.2522 0.1086 0.093 Uiso 1 d . . H19 H -0.3466 -0.2117 0.2111 0.093 Uiso 1 d . . H20 H -0.1869 -0.1429 0.1201 0.067 Uiso 1 d . . H21 H -0.2248 -0.1590 -0.0430 0.067 Uiso 1 d . . H22 H -0.2775 0.1498 -0.0961 0.041 Uiso 1 d . . H23 H -0.2451 0.1863 0.1551 0.061 Uiso 1 d . . H24 H -0.3632 0.1499 0.2050 0.061 Uiso 1 d . . H25 H -0.3623 0.2517 -0.0033 0.077 Uiso 1 d . . H26 H -0.4107 0.2590 0.1589 0.077 Uiso 1 d . . H27 H -0.5804 0.2467 -0.0077 0.078 Uiso 1 d . . H28 H -0.5781 0.1887 0.1029 0.078 Uiso 1 d . . H29 H -0.4837 0.1824 -0.1932 0.075 Uiso 1 d . . H30 H -0.6020 0.1466 -0.1421 0.075 Uiso 1 d . . H31 H -0.4831 0.0790 0.0136 0.056 Uiso 1 d . . H32 H -0.4359 0.0727 -0.1493 0.056 Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(7) 0.037(7) 0.044(12) 0.008(7) 0.002(7) 0.000(6) C2 0.025(7) 0.052(9) 0.053(13) 0.009(9) -0.011(7) 0.002(7) C3 0.020(7) 0.048(9) 0.069(15) 0.002(9) 0.002(9) 0.007(6) C4 0.052(9) 0.050(9) 0.102(17) 0.007(12) 0.009(12) 0.024(8) C5 0.046(9) 0.069(11) 0.055(15) -0.002(10) 0.013(9) 0.009(9) C6 0.026(8) 0.065(10) 0.080(15) -0.010(11) -0.011(10) -0.004(8) O7 0.070(8) 0.103(10) 0.093(11) -0.016(10) -0.021(9) -0.026(8) C8 0.027(8) 0.031(8) 0.029(10) 0.002(8) 0.001(7) 0.002(6) O9 0.030(5) 0.036(5) 0.054(8) 0.012(5) 0.004(5) -0.001(4) N10 0.024(6) 0.029(5) 0.024(8) 0.000(6) -0.002(5) 0.004(5) C11 0.021(7) 0.038(8) 0.024(12) 0.004(8) -0.004(7) 0.000(6) O12 0.045(6) 0.040(5) 0.027(8) 0.000(5) -0.002(6) -0.004(5) N13 0.042(6) 0.028(6) 0.022(7) 0.001(6) 0.001(6) -0.002(5) C14 0.039(8) 0.027(7) 0.038(10) 0.004(7) -0.001(8) -0.002(7) C15 0.057(10) 0.063(10) 0.093(18) 0.035(11) -0.033(11) -0.024(8) C16 0.106(16) 0.083(13) 0.131(23) 0.058(16) -0.059(17) -0.055(13) C17 0.199(26) 0.049(12) 0.065(15) -0.003(12) -0.002(20) -0.057(15) C18 0.090(12) 0.028(8) 0.086(15) 0.012(9) 0.017(13) 0.009(9) C19 0.057(10) 0.044(8) 0.051(12) 0.004(8) 0.018(10) 0.009(7) C20 0.027(7) 0.029(7) 0.035(10) 0.005(7) -0.003(7) 0.006(6) C21 0.045(8) 0.034(7) 0.046(11) -0.010(7) -0.002(9) -0.002(7) C22 0.060(10) 0.039(8) 0.064(14) -0.011(8) -0.001(10) 0.018(8) C23 0.045(9) 0.055(9) 0.086(16) 0.001(11) 0.003(11) 0.021(8) C24 0.044(9) 0.055(9) 0.061(14) 0.008(10) -0.012(9) 0.013(8) C25 0.034(7) 0.044(8) 0.052(13) -0.004(8) -0.011(8) 0.005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C8 1.48(2) . ? C1 C3 1.51(2) . ? C1 C2 1.53(2) . ? C2 C6 1.46(2) . ? C2 C3 1.50(2) . ? C3 C5 1.49(3) . ? C3 C4 1.51(2) . ? C6 O7 1.20(2) . ? C8 O9 1.226(15) . ? C8 N10 1.38(2) . ? N10 C11 1.42(2) . ? N10 C20 1.49(2) . ? C11 O12 1.24(2) . ? C11 N13 1.32(2) . ? N13 C14 1.46(2) . ? C14 C19 1.50(2) . ? C14 C15 1.52(2) . ? C15 C16 1.53(2) . ? C16 C17 1.49(3) . ? C17 C18 1.52(3) . ? C18 C19 1.53(2) . ? C20 C25 1.51(2) . ? C20 C21 1.52(2) . ? C21 C22 1.50(2) . ? C22 C23 1.53(2) . ? C23 C24 1.50(3) . ? C24 C25 1.53(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C1 C3 123.3(14) . . ? C8 C1 C2 119.7(12) . . ? C3 C1 C2 58.9(10) . . ? C6 C2 C3 123.5(16) . . ? C6 C2 C1 122.5(12) . . ? C3 C2 C1 60.0(10) . . ? C5 C3 C2 119.8(12) . . ? C5 C3 C4 114.6(16) . . ? C2 C3 C4 116.6(17) . . ? C5 C3 C1 120.1(13) . . ? C2 C3 C1 61.2(10) . . ? C4 C3 C1 114.2(14) . . ? O7 C6 C2 122.6(18) . . ? O9 C8 N10 120.6(11) . . ? O9 C8 C1 123.4(11) . . ? N10 C8 C1 116.0(12) . . ? C8 N10 C11 122.3(10) . . ? C8 N10 C20 118.8(10) . . ? C11 N10 C20 118.2(9) . . ? O12 C11 N13 125.0(12) . . ? O12 C11 N10 120.0(13) . . ? N13 C11 N10 114.9(15) . . ? C11 N13 C14 123.3(12) . . ? N13 C14 C19 112.1(10) . . ? N13 C14 C15 108.9(12) . . ? C19 C14 C15 111.2(13) . . ? C14 C15 C16 109.7(15) . . ? C17 C16 C15 111.8(19) . . ? C16 C17 C18 109.8(15) . . ? C17 C18 C19 110.0(15) . . ? C14 C19 C18 110.7(12) . . ? N10 C20 C25 111.0(10) . . ? N10 C20 C21 111.7(12) . . ? C25 C20 C21 111.5(11) . . ? C22 C21 C20 109.5(12) . . ? C21 C22 C23 112.2(12) . . ? C24 C23 C22 109.9(13) . . ? C23 C24 C25 111.8(14) . . ? C20 C25 C24 108.8(11) . . ? _refine_diff_density_max 0.268 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.054 #===END data_Ni-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C106 H168 N12 Ni O16 S5' _chemical_formula_weight 2085.53 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 Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 15.091(3) _cell_length_b 15.091(3) _cell_length_c 63.545(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 14472(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.957 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4496 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 46236 _diffrn_reflns_av_R_equivalents 0.3052 _diffrn_reflns_av_sigmaI/netI 0.5436 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 70 _diffrn_reflns_theta_min 5.31 _diffrn_reflns_theta_max 24.30 _reflns_number_total 10825 _reflns_number_gt 2864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(5) _refine_ls_number_reflns 10825 _refine_ls_number_parameters 643 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3255 _refine_ls_R_factor_gt 0.1198 _refine_ls_wR_factor_ref 0.3091 _refine_ls_wR_factor_gt 0.2650 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 1.449 _refine_ls_shift/su_mean 0.065 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 1.03562(3) 0.03562(3) 0.5000 0.05629(16) Uani 1 2 d S . . O1 O 1.24165(14) 0.14654(15) 0.55897(3) 0.0906(10) Uani 1 1 d . . . O2 O 1.30611(18) -0.01471(14) 0.61201(3) 0.1129(10) Uani 1 1 d . . . O11 O 0.71851(14) 0.03925(15) 0.47092(3) 0.0896(9) Uani 1 1 d . . . O12 O 0.62135(17) 0.24640(15) 0.43119(4) 0.1155(10) Uani 1 1 d . . . N1 N 1.09533(14) -0.02129(15) 0.52259(3) 0.0471(8) Uani 1 1 d . . . N2 N 0.96740(15) 0.10273(16) 0.51919(3) 0.0627(9) Uani 1 1 d . . . N11 N 1.30679(14) 0.10843(18) 0.58972(4) 0.0745(10) Uani 1 1 d . . . N12 N 1.27713(16) 0.12202(17) 0.62492(4) 0.0801(10) Uani 1 1 d . . . H12 H 1.2808 0.1775 0.6219 0.096 Uiso 1 1 calc R . . N31 N 0.62353(16) 0.11452(17) 0.45077(4) 0.0719(10) Uani 1 1 d . . . N32 N 0.51598(15) 0.22155(18) 0.45544(4) 0.0858(11) Uani 1 1 d . . . H32 H 0.4934 0.1843 0.4642 0.103 Uiso 1 1 calc R . . C1 C 1.1398(2) -0.10417(17) 0.52195(4) 0.0651(13) Uani 1 1 d . . . C2 C 1.1716(2) -0.1225(2) 0.54255(4) 0.0793(14) Uani 1 1 d . . . H2 H 1.2004 -0.1740 0.5467 0.095 Uiso 1 1 calc R . . C3 C 1.15328(18) -0.0532(2) 0.55493(5) 0.0687(13) Uani 1 1 d . . . H3 H 1.1718 -0.0462 0.5688 0.082 Uiso 1 1 calc R . . C4 C 1.1010(2) 0.00749(19) 0.54341(4) 0.0587(12) Uani 1 1 d . . . C5 C 1.0554(2) 0.0747(2) 0.55214(4) 0.0762(13) Uani 1 1 d . . . C6 C 0.98379(18) 0.1133(2) 0.53970(5) 0.0727(13) Uani 1 1 d . . . C7 C 0.91655(18) 0.1689(2) 0.54954(5) 0.0861(14) Uani 1 1 d . . . H7 H 0.9166 0.1925 0.5631 0.103 Uiso 1 1 calc R . . C8 C 0.8564(2) 0.1779(2) 0.53500(5) 0.0813(14) Uani 1 1 d . . . H8 H 0.8012 0.2042 0.5369 0.098 Uiso 1 1 calc R . . C9 C 0.88808(17) 0.1417(2) 0.51588(4) 0.0571(11) Uani 1 1 d . . . C10 C 0.84775(18) 0.1582(2) 0.49642(4) 0.0595(11) Uani 1 1 d . . . C11 C 1.05689(18) 0.0930(2) 0.57517(4) 0.0731(13) Uani 1 1 d . . . H11 H 1.0152 0.0582 0.5836 0.088 Uiso 1 1 calc R . . C12 C 1.0758(2) 0.1897(3) 0.58343(5) 0.1018(14) Uani 1 1 d . . . C13 C 1.0965(3) 0.2646(2) 0.57077(6) 0.1238(18) Uani 1 1 d . . . H13A H 1.1273 0.2455 0.5584 0.186 Uiso 1 1 calc R . . H13B H 1.1334 0.3045 0.5786 0.186 Uiso 1 1 calc R . . H13C H 1.0428 0.2942 0.5668 0.186 Uiso 1 1 calc R . . C14 C 1.0277(3) 0.2017(4) 0.60629(6) 0.181(2) Uani 1 1 d . . . H14A H 1.0379 0.2606 0.6114 0.272 Uiso 1 1 calc R . . H14B H 1.0519 0.1595 0.6161 0.272 Uiso 1 1 calc R . . H14C H 0.9652 0.1918 0.6048 0.272 Uiso 1 1 calc R . . C15 C 1.1427(2) 0.1177(3) 0.58610(5) 0.1038(16) Uani 1 1 d . . . H15 H 1.1438 0.0959 0.6006 0.125 Uiso 1 1 calc R . . C16 C 1.2366(2) 0.1288(2) 0.57734(5) 0.0816(15) Uani 1 1 d . . . C17 C 1.3952(2) 0.1068(2) 0.58013(5) 0.0775(13) Uani 1 1 d . . . H17 H 1.3932 0.1475 0.5681 0.093 Uiso 1 1 calc R . . C18 C 1.4229(2) 0.0198(2) 0.57181(6) 0.1062(16) Uani 1 1 d . . . H18A H 1.3768 -0.0025 0.5626 0.127 Uiso 1 1 calc R . . H18B H 1.4287 -0.0214 0.5835 0.127 Uiso 1 1 calc R . . C19 C 1.5103(2) 0.0219(3) 0.55969(6) 0.1324(19) Uani 1 1 d . . . H19A H 1.5265 -0.0373 0.5552 0.159 Uiso 1 1 calc R . . H19B H 1.5047 0.0592 0.5473 0.159 Uiso 1 1 calc R . . C20 C 1.5800(2) 0.0588(3) 0.57427(6) 0.1268(19) Uani 1 1 d . . . H20A H 1.5919 0.0159 0.5853 0.152 Uiso 1 1 calc R . . H20B H 1.6345 0.0676 0.5664 0.152 Uiso 1 1 calc R . . C21 C 1.5533(2) 0.1450(3) 0.58420(7) 0.1257(19) Uani 1 1 d . . . H21A H 1.5980 0.1620 0.5944 0.151 Uiso 1 1 calc R . . H21B H 1.5515 0.1904 0.5734 0.151 Uiso 1 1 calc R . . C22 C 1.4660(2) 0.1416(2) 0.59485(6) 0.1120(16) Uani 1 1 d . . . H22A H 1.4499 0.2005 0.5996 0.134 Uiso 1 1 calc R . . H22B H 1.4699 0.1034 0.6071 0.134 Uiso 1 1 calc R . . C23 C 1.2950(2) 0.0620(3) 0.61023(5) 0.0935(15) Uani 1 1 d . . . C24 C 1.2508(2) 0.0940(3) 0.64646(6) 0.1058(14) Uiso 1 1 d . . . H24 H 1.2787 0.0358 0.6481 0.127 Uiso 1 1 calc R . . C25 C 1.1570(2) 0.0752(3) 0.64752(6) 0.142(2) Uani 1 1 d . . . H25A H 1.1424 0.0307 0.6371 0.171 Uiso 1 1 calc R . . H25B H 1.1241 0.1285 0.6442 0.171 Uiso 1 1 calc R . . C26 C 1.1279(4) 0.0410(4) 0.66983(6) 0.207(3) Uani 1 1 d . . . H26A H 1.0639 0.0353 0.6706 0.249 Uiso 1 1 calc R . . H26B H 1.1544 -0.0161 0.6728 0.249 Uiso 1 1 calc R . . C27 C 1.1587(5) 0.1067(4) 0.68448(8) 0.273(4) Uani 1 1 d . . . H27A H 1.1347 0.0930 0.6983 0.328 Uiso 1 1 calc R . . H27B H 1.1354 0.1639 0.6803 0.328 Uiso 1 1 calc R . . C28 C 1.2653(3) 0.1144(4) 0.68644(8) 0.177(2) Uiso 1 1 d . . . H28A H 1.2908 0.0566 0.6892 0.213 Uiso 1 1 calc R . . H28B H 1.2809 0.1537 0.6979 0.213 Uiso 1 1 calc R . . C29 C 1.3080(4) 0.1580(3) 0.66182(7) 0.200(3) Uani 1 1 d . . . H29A H 1.2939 0.2201 0.6599 0.239 Uiso 1 1 calc R . . H29B H 1.3713 0.1488 0.6603 0.239 Uiso 1 1 calc R . . C31 C 0.76461(19) 0.2081(2) 0.49602(5) 0.0866(14) Uani 1 1 d . . . H31 H 0.7720 0.2716 0.4987 0.104 Uiso 1 1 calc R . . C32 C 0.6769(2) 0.1689(3) 0.50505(5) 0.1071(16) Uani 1 1 d . . . C33 C 0.6160(2) 0.2374(3) 0.51629(6) 0.1204(18) Uani 1 1 d . . . H33A H 0.5662 0.2073 0.5224 0.181 Uiso 1 1 calc R . . H33B H 0.5955 0.2803 0.5062 0.181 Uiso 1 1 calc R . . H33C H 0.6489 0.2668 0.5272 0.181 Uiso 1 1 calc R . . C34 C 0.6749(2) 0.0796(3) 0.51541(5) 0.137(2) Uani 1 1 d . . . H34A H 0.6165 0.0682 0.5207 0.206 Uiso 1 1 calc R . . H34B H 0.7166 0.0786 0.5268 0.206 Uiso 1 1 calc R . . H34C H 0.6904 0.0349 0.5053 0.206 Uiso 1 1 calc R . . C35 C 0.68363(19) 0.1857(2) 0.48187(4) 0.0725(13) Uani 1 1 d . . . H35 H 0.6503 0.2373 0.4769 0.087 Uiso 1 1 calc R . . C36 C 0.67798(19) 0.1083(2) 0.46841(5) 0.0624(12) Uani 1 1 d . . . C37 C 0.6245(2) 0.0429(2) 0.43407(5) 0.0842(14) Uani 1 1 d . . . H37 H 0.6352 -0.0132 0.4414 0.101 Uiso 1 1 calc R . . C38 C 0.6947(3) 0.0532(2) 0.41925(6) 0.1165(18) Uani 1 1 d . . . H38A H 0.6869 0.1094 0.4121 0.140 Uiso 1 1 calc R . . H38B H 0.7502 0.0561 0.4269 0.140 Uiso 1 1 calc R . . C39 C 0.7011(3) -0.0134(3) 0.40417(7) 0.1475(18) Uiso 1 1 d . . . H39A H 0.7597 -0.0116 0.3979 0.177 Uiso 1 1 calc R . . H39B H 0.6943 -0.0705 0.4110 0.177 Uiso 1 1 calc R . . C40 C 0.6488(10) -0.0070(3) 0.39105(8) 0.482(10) Uani 1 1 d . . . H40A H 0.6605 -0.0480 0.3796 0.578 Uiso 1 1 calc R . . H40B H 0.6467 0.0528 0.3855 0.578 Uiso 1 1 calc R . . C41 C 0.5474(4) -0.0350(5) 0.40462(10) 0.240(3) Uiso 1 1 d . . . H41A H 0.4979 -0.0324 0.3949 0.287 Uiso 1 1 calc R . . H41B H 0.5512 -0.0949 0.4101 0.287 Uiso 1 1 calc R . . C42 C 0.5310(2) 0.0369(3) 0.42452(6) 0.1187(16) Uani 1 1 d . . . H42A H 0.5109 0.0940 0.4194 0.142 Uiso 1 1 calc R . . H42B H 0.4885 0.0142 0.4346 0.142 Uiso 1 1 calc R . . C43 C 0.58737(19) 0.20158(19) 0.44465(5) 0.0535(12) Uani 1 1 d . . . C44 C 0.4757(2) 0.3086(2) 0.45228(6) 0.1020(16) Uani 1 1 d . . . H44 H 0.5127 0.3477 0.4436 0.122 Uiso 1 1 calc R . . C45 C 0.3932(4) 0.2850(4) 0.44188(13) 0.306(4) Uani 1 1 d . . . H45A H 0.3573 0.2477 0.4509 0.367 Uiso 1 1 calc R . . H45B H 0.4050 0.2534 0.4289 0.367 Uiso 1 1 calc R . . C46 C 0.3426(3) 0.3786(4) 0.43705(9) 0.204(3) Uani 1 1 d . . . H46A H 0.3775 0.4169 0.4280 0.245 Uiso 1 1 calc R . . H46B H 0.2847 0.3692 0.4308 0.245 Uiso 1 1 calc R . . C47 C 0.3357(3) 0.4153(3) 0.45932(6) 0.240(2) Uani 1 1 d . . . H47A H 0.3166 0.3686 0.4688 0.288 Uiso 1 1 calc R . . H47B H 0.2914 0.4619 0.4597 0.288 Uiso 1 1 calc R . . C48 C 0.4391(7) 0.4586(5) 0.46825(10) 0.498(5) Uani 1 1 d . . . H48A H 0.4757 0.4857 0.4575 0.598 Uiso 1 1 calc R . . H48B H 0.4362 0.4942 0.4810 0.598 Uiso 1 1 calc R . . C49 C 0.4565(6) 0.3456(3) 0.47220(7) 0.426(4) Uani 1 1 d . . . H49A H 0.5057 0.3363 0.4818 0.511 Uiso 1 1 calc R . . H49B H 0.4040 0.3183 0.4781 0.511 Uiso 1 1 calc R . . S1A S 1.15372(18) -0.41228(19) 0.25870(4) 0.1470(12) Uani 0.50 1 d P . . S1B S 1.08693(19) -0.4610(2) 0.25078(5) 0.1716(13) Uani 0.50 1 d P . . O51 O 1.0602(2) -0.3821(2) 0.26176(5) 0.2163(15) Uani 1 1 d . . . C51 C 1.1252(6) -0.5212(5) 0.27129(12) 0.318(4) Uani 1 1 d . . . C52 C 1.1615(3) -0.4390(4) 0.23610(6) 0.220(3) Uani 1 1 d . . . S2 S 0.8152(3) -0.1079(3) 0.36652(9) 0.306(3) Uani 0.50 1 d P . . C61 C 0.8546(7) -0.1891(7) 0.38450(13) 0.195(5) Uani 0.50 1 d P . . O61 O 0.7380(10) -0.1024(10) 0.3490(2) 0.375(6) Uiso 0.50 1 d P . . C62 C 0.8971(5) -0.0827(5) 0.34581(10) 0.088(2) Uiso 0.50 1 d P . . S3 S 1.11218(11) -0.21550(11) 0.37419(2) 0.1760(8) Uani 1 1 d . . . O71 O 1.1950(2) -0.2602(2) 0.37377(6) 0.1830(17) Uani 1 1 d . . . C71 C 1.0784(6) -0.1999(5) 0.39920(7) 0.329(5) Uani 1 1 d . . . C72 C 1.0257(5) -0.3000(6) 0.37248(8) 0.294(4) Uani 1 1 d . . . O21 O 0.9870(4) -0.0534(5) 0.61485(11) 0.194(3) Uani 0.50 1 d P . . O23 O 0.8647(3) -0.1459(3) 0.43465(10) 0.159(3) Uani 0.553(3) 1 d P . . O22 O 0.8131(3) -0.1723(4) 0.46023(7) 0.096(2) Uani 0.447(3) 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 0.05352(19) 0.05352(19) 0.0618(3) -0.0123(3) 0.0123(3) 0.0090(4) O1 0.0902(17) 0.0985(18) 0.0831(16) -0.0045(15) -0.0155(15) -0.0077(15) O2 0.192(2) 0.0717(16) 0.0745(16) -0.0061(13) 0.0043(17) 0.0741(16) O11 0.1069(17) 0.0720(15) 0.0898(16) 0.0118(15) -0.0384(14) 0.0015(16) O12 0.146(2) 0.0755(17) 0.1252(18) 0.0023(15) 0.0857(16) 0.0187(16) N1 0.0376(14) 0.0640(16) 0.0396(14) -0.0064(14) 0.0091(12) -0.0004(14) N2 0.0360(14) 0.1087(18) 0.0435(13) -0.0491(14) 0.0182(13) -0.0075(16) N11 0.0295(14) 0.123(2) 0.0713(18) -0.0122(17) -0.0300(14) 0.0455(15) N12 0.0791(18) 0.0736(18) 0.0874(19) -0.0402(16) 0.0107(17) 0.0408(15) N31 0.0612(18) 0.0758(19) 0.0785(19) -0.0170(17) -0.0046(16) -0.0153(16) N32 0.0544(17) 0.121(2) 0.0818(19) 0.0095(18) -0.0093(16) -0.0585(17) C1 0.111(3) 0.0147(17) 0.070(2) 0.0165(17) 0.004(2) 0.0050(19) C2 0.106(3) 0.085(3) 0.047(2) 0.028(2) 0.023(2) 0.032(2) C3 0.043(2) 0.102(3) 0.061(2) -0.011(2) -0.0016(18) 0.005(2) C4 0.065(2) 0.069(2) 0.0416(18) 0.0021(17) -0.0204(17) 0.0174(19) C5 0.082(2) 0.091(2) 0.0561(19) -0.0444(18) -0.0214(19) 0.046(2) C6 0.033(2) 0.083(2) 0.102(2) -0.049(2) 0.0267(19) 0.0030(19) C7 0.0357(19) 0.156(3) 0.066(2) -0.059(2) -0.0285(18) 0.046(2) C8 0.057(2) 0.125(3) 0.062(2) -0.014(2) -0.0146(19) 0.030(2) C9 0.0169(17) 0.098(2) 0.0566(19) -0.0444(18) 0.0109(16) -0.0049(18) C10 0.0490(19) 0.098(2) 0.0320(17) -0.0464(18) 0.0017(17) 0.0034(17) C11 0.040(2) 0.121(3) 0.058(2) -0.025(2) -0.0221(17) 0.031(2) C12 0.082(2) 0.163(3) 0.061(2) -0.064(2) -0.0249(19) 0.088(2) C13 0.123(3) 0.056(3) 0.192(4) 0.021(3) -0.083(3) 0.003(2) C14 0.103(3) 0.314(6) 0.126(3) -0.108(4) 0.005(3) 0.049(4) C15 0.064(2) 0.186(4) 0.061(2) -0.064(2) -0.001(2) -0.013(3) C16 0.093(3) 0.087(3) 0.065(2) 0.010(2) 0.025(2) 0.000(2) C17 0.080(2) 0.059(2) 0.093(3) -0.023(2) -0.025(2) 0.020(2) C18 0.045(2) 0.131(3) 0.142(3) -0.024(3) -0.006(2) -0.023(2) C19 0.064(3) 0.209(4) 0.124(3) -0.066(3) -0.013(2) -0.008(3) C20 0.057(2) 0.214(4) 0.110(3) -0.058(3) -0.030(2) 0.024(3) C21 0.024(2) 0.163(4) 0.190(4) -0.036(3) -0.032(2) -0.028(2) C22 0.071(2) 0.091(3) 0.175(3) 0.014(3) -0.071(3) 0.021(2) C23 0.094(3) 0.126(3) 0.061(2) -0.008(2) -0.013(2) 0.052(2) C25 0.072(3) 0.229(5) 0.125(3) 0.009(4) 0.031(3) 0.056(3) C26 0.195(4) 0.326(6) 0.102(3) -0.052(4) 0.012(3) 0.128(4) C27 0.426(9) 0.224(6) 0.170(4) 0.079(4) 0.144(5) 0.067(6) C29 0.309(6) 0.143(4) 0.147(4) -0.059(3) -0.039(4) -0.090(4) C31 0.056(2) 0.131(3) 0.073(2) -0.058(2) -0.027(2) 0.020(2) C32 0.037(2) 0.197(4) 0.087(3) -0.079(3) -0.028(2) 0.027(2) C33 0.081(3) 0.175(4) 0.106(3) -0.054(3) -0.023(2) 0.055(3) C34 0.072(3) 0.268(5) 0.072(3) -0.010(3) -0.012(2) -0.016(3) C35 0.056(2) 0.103(3) 0.058(2) -0.0639(19) -0.0239(18) 0.017(2) C36 0.049(2) 0.054(2) 0.084(2) 0.024(2) -0.006(2) -0.0044(19) C37 0.078(2) 0.064(2) 0.110(3) -0.042(2) -0.005(2) -0.014(2) C38 0.127(3) 0.105(3) 0.118(3) -0.060(3) -0.020(3) 0.002(3) C40 1.29(3) 0.053(3) 0.106(4) -0.058(3) 0.062(9) 0.021(8) C42 0.112(3) 0.110(3) 0.134(3) -0.026(3) -0.023(3) -0.052(3) C43 0.045(2) 0.041(2) 0.075(2) -0.0095(19) -0.0019(19) 0.0117(17) C44 0.058(2) 0.108(3) 0.140(3) 0.033(3) 0.022(3) 0.049(2) C45 0.184(5) 0.200(6) 0.535(10) 0.021(6) -0.181(5) 0.076(4) C46 0.110(3) 0.240(5) 0.262(5) 0.102(4) -0.061(4) 0.049(4) C47 0.382(4) 0.189(4) 0.149(3) 0.059(3) 0.213(3) 0.198(3) C48 0.899(13) 0.419(7) 0.176(5) -0.149(5) -0.226(7) 0.437(7) C49 0.974(12) 0.243(4) 0.061(3) -0.041(3) -0.013(5) 0.408(5) S1A 0.139(2) 0.174(2) 0.128(2) -0.0608(18) 0.0083(17) -0.0272(19) S1B 0.139(2) 0.209(3) 0.167(2) 0.047(3) -0.009(2) -0.010(2) O51 0.198(3) 0.273(3) 0.178(3) -0.094(2) 0.032(2) 0.162(2) C51 0.382(8) 0.267(7) 0.304(7) 0.104(6) -0.128(7) -0.156(6) C52 0.167(4) 0.416(7) 0.076(3) 0.081(4) 0.002(3) -0.162(4) S2 0.194(3) 0.299(4) 0.426(6) -0.080(4) 0.082(4) -0.112(3) C61 0.269(10) 0.233(9) 0.084(6) 0.013(6) -0.019(7) 0.182(7) S3 0.1872(14) 0.1891(14) 0.1519(12) -0.0036(12) 0.0125(12) 0.0323(12) O71 0.118(2) 0.158(3) 0.272(4) -0.003(3) 0.057(3) 0.020(2) C71 0.662(12) 0.230(6) 0.095(3) 0.008(4) 0.182(5) 0.036(8) C72 0.289(7) 0.458(9) 0.134(4) 0.125(5) -0.098(4) -0.117(7) O21 0.160(6) 0.214(6) 0.209(6) -0.037(5) 0.005(5) 0.041(5) O23 0.096(3) 0.047(3) 0.333(7) 0.024(4) -0.060(4) 0.047(2) O22 0.048(3) 0.152(5) 0.088(4) 0.001(4) 0.038(3) -0.033(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 Ni N2 1.890(2) 7_646 ? Ni N2 1.890(2) . ? Ni N1 1.900(2) . ? Ni N1 1.900(2) 7_646 ? O1 C16 1.200(4) . ? O2 C23 1.175(4) . ? O11 C36 1.218(4) . ? O12 C43 1.205(4) . ? N1 C4 1.395(3) . ? N1 C1 1.420(3) . ? N2 C6 1.336(4) . ? N2 C9 1.350(3) . ? N11 C16 1.355(4) . ? N11 C17 1.467(4) . ? N11 C23 1.490(4) . ? N12 C23 1.328(4) . ? N12 C24 1.487(4) . ? N31 C36 1.393(4) . ? N31 C43 1.475(4) . ? N31 C37 1.515(4) . ? N32 C43 1.312(4) . ? N32 C44 1.462(4) . ? C1 C10 1.402(4) 7_646 ? C1 C2 1.422(4) . ? C2 C3 1.337(4) . ? C3 C4 1.414(4) . ? C4 C5 1.344(4) . ? C5 C6 1.461(4) . ? C5 C11 1.490(4) . ? C6 C7 1.458(4) . ? C7 C8 1.302(4) . ? C8 C9 1.415(4) . ? C9 C10 1.401(4) . ? C10 C1 1.402(4) 7_646 ? C10 C31 1.463(4) . ? C11 C15 1.516(4) . ? C11 C12 1.578(5) . ? C12 C13 1.421(5) . ? C12 C15 1.493(5) . ? C12 C14 1.633(5) . ? C15 C16 1.532(5) . ? C17 C18 1.477(5) . ? C17 C22 1.514(5) . ? C18 C19 1.527(5) . ? C19 C20 1.509(5) . ? C20 C21 1.500(6) . ? C21 C22 1.482(5) . ? C24 C25 1.445(5) . ? C24 C29 1.621(6) . ? C25 C26 1.571(6) . ? C26 C27 1.437(8) . ? C27 C28 1.618(9) . ? C28 C29 1.815(7) . ? C31 C35 1.554(4) . ? C31 C32 1.559(4) . ? C32 C35 1.498(4) . ? C32 C34 1.501(6) . ? C32 C33 1.556(5) . ? C35 C36 1.450(4) . ? C37 C38 1.425(5) . ? C37 C42 1.539(5) . ? C38 C39 1.393(6) . ? C39 C40 1.152(12) . ? C40 C41 1.807(15) . ? C41 C42 1.684(7) . ? C44 C49 1.413(6) . ? C44 C45 1.453(7) . ? C45 C46 1.635(8) . ? C46 C47 1.523(7) . ? C47 C48 1.784(11) . ? C48 C49 1.743(9) . ? S1A S1B 1.346(4) . ? S1A O51 1.496(4) . ? S1A C52 1.497(5) . ? S1A C51 1.878(8) . ? S1B O51 1.438(4) . ? S1B C52 1.499(5) . ? S1B C51 1.690(8) . ? S2 O61 1.613(15) . ? S2 C61 1.778(10) . ? S2 C62 1.845(8) . ? S3 O71 1.421(3) . ? S3 C71 1.686(6) . ? S3 C72 1.828(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 N2 Ni N2 179.28(15) 7_646 . ? N2 Ni N1 89.26(9) 7_646 . ? N2 Ni N1 90.75(9) . . ? N2 Ni N1 90.75(9) 7_646 7_646 ? N2 Ni N1 89.26(9) . 7_646 ? N1 Ni N1 178.20(14) . 7_646 ? C4 N1 C1 105.8(2) . . ? C4 N1 Ni 127.20(19) . . ? C1 N1 Ni 126.90(17) . . ? C6 N2 C9 105.3(2) . . ? C6 N2 Ni 126.3(2) . . ? C9 N2 Ni 128.01(18) . . ? C16 N11 C17 118.3(3) . . ? C16 N11 C23 121.4(3) . . ? C17 N11 C23 117.7(2) . . ? C23 N12 C24 120.5(3) . . ? C36 N31 C43 119.4(2) . . ? C36 N31 C37 120.6(2) . . ? C43 N31 C37 117.0(2) . . ? C43 N32 C44 118.5(3) . . ? C10 C1 N1 125.0(2) 7_646 . ? C10 C1 C2 126.8(3) 7_646 . ? N1 C1 C2 107.7(2) . . ? C3 C2 C1 108.7(3) . . ? C2 C3 C4 108.5(3) . . ? C5 C4 N1 126.5(3) . . ? C5 C4 C3 124.1(3) . . ? N1 C4 C3 108.9(2) . . ? C4 C5 C6 117.1(3) . . ? C4 C5 C11 122.5(3) . . ? C6 C5 C11 117.9(3) . . ? N2 C6 C7 111.0(3) . . ? N2 C6 C5 128.1(3) . . ? C7 C6 C5 120.9(3) . . ? C8 C7 C6 103.9(3) . . ? C7 C8 C9 109.5(3) . . ? N2 C9 C10 126.9(2) . . ? N2 C9 C8 109.5(2) . . ? C10 C9 C8 122.8(3) . . ? C9 C10 C1 118.3(3) . 7_646 ? C9 C10 C31 118.7(2) . . ? C1 C10 C31 122.1(2) 7_646 . ? C5 C11 C15 120.6(3) . . ? C5 C11 C12 120.1(3) . . ? C15 C11 C12 57.7(2) . . ? C13 C12 C15 119.6(3) . . ? C13 C12 C11 125.9(3) . . ? C15 C12 C11 59.1(2) . . ? C13 C12 C14 120.9(3) . . ? C15 C12 C14 106.2(3) . . ? C11 C12 C14 108.5(3) . . ? C12 C15 C11 63.3(2) . . ? C12 C15 C16 120.3(3) . . ? C11 C15 C16 130.6(3) . . ? O1 C16 N11 124.4(3) . . ? O1 C16 C15 115.9(3) . . ? N11 C16 C15 119.2(3) . . ? N11 C17 C18 114.9(3) . . ? N11 C17 C22 112.3(3) . . ? C18 C17 C22 109.2(3) . . ? C17 C18 C19 113.9(3) . . ? C20 C19 C18 107.5(3) . . ? C21 C20 C19 113.0(3) . . ? C22 C21 C20 113.7(3) . . ? C21 C22 C17 110.9(3) . . ? O2 C23 N12 129.3(3) . . ? O2 C23 N11 122.1(3) . . ? N12 C23 N11 108.5(3) . . ? C25 C24 N12 111.1(3) . . ? C25 C24 C29 127.7(4) . . ? N12 C24 C29 104.0(3) . . ? C24 C25 C26 112.4(3) . . ? C27 C26 C25 105.5(5) . . ? C26 C27 C28 115.0(5) . . ? C27 C28 C29 108.2(4) . . ? C24 C29 C28 96.6(3) . . ? C10 C31 C35 124.9(3) . . ? C10 C31 C32 121.8(3) . . ? C35 C31 C32 57.52(19) . . ? C35 C32 C34 125.8(3) . . ? C35 C32 C33 112.3(3) . . ? C34 C32 C33 112.5(3) . . ? C35 C32 C31 61.1(2) . . ? C34 C32 C31 121.3(3) . . ? C33 C32 C31 114.7(3) . . ? C36 C35 C32 116.1(3) . . ? C36 C35 C31 124.2(3) . . ? C32 C35 C31 61.4(2) . . ? O11 C36 N31 117.3(3) . . ? O11 C36 C35 125.6(3) . . ? N31 C36 C35 117.0(3) . . ? C38 C37 N31 113.1(3) . . ? C38 C37 C42 115.3(3) . . ? N31 C37 C42 108.0(3) . . ? C39 C38 C37 115.3(4) . . ? C40 C39 C38 112.9(5) . . ? C39 C40 C41 102.5(5) . . ? C42 C41 C40 109.4(4) . . ? C37 C42 C41 101.5(3) . . ? O12 C43 N32 126.3(3) . . ? O12 C43 N31 122.0(3) . . ? N32 C43 N31 111.7(3) . . ? C49 C44 C45 109.2(5) . . ? C49 C44 N32 108.5(3) . . ? C45 C44 N32 101.4(3) . . ? C44 C45 C46 105.9(4) . . ? C47 C46 C45 99.9(4) . . ? C46 C47 C48 111.7(4) . . ? C49 C48 C47 79.6(5) . . ? C44 C49 C48 106.8(4) . . ? S1B S1A O51 60.6(2) . . ? S1B S1A C52 63.4(3) . . ? O51 S1A C52 106.3(3) . . ? S1B S1A C51 60.6(3) . . ? O51 S1A C51 89.7(3) . . ? C52 S1A C51 101.0(4) . . ? S1A S1B O51 64.9(2) . . ? S1A S1B C52 63.2(2) . . ? O51 S1B C52 109.2(3) . . ? S1A S1B C51 75.5(3) . . ? O51 S1B C51 99.6(3) . . ? C52 S1B C51 110.0(4) . . ? S1B O51 S1A 54.55(19) . . ? S1B C51 S1A 43.9(2) . . ? S1A C52 S1B 53.4(2) . . ? O61 S2 C61 136.1(7) . . ? O61 S2 C62 88.9(6) . . ? C61 S2 C62 112.0(4) . . ? O71 S3 C71 110.5(4) . . ? O71 S3 C72 107.2(3) . . ? C71 S3 C72 86.4(4) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 24.30 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.558 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.075