Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Prof Joao Costa Pessoa' _publ_contact_author_address ; Departamento de Engenharia Quimica Instituto Superior Tecnico Centro Quimica Estrutural Av. Rovisco Pais Lisboa 1049-001 Lisboa PORTUGAL ; _publ_contact_author_email PCJPESSOA@MAIL.IST.UTL.PT _publ_section_title ; Enantioselectivity in Ni(II)-Schiff base complexes derived from amino-acids and S-o-(N-(N-benzylprolyl)amino)benzophenone. Molecular structure of several chiral Ni(II) Schiff base complexes, circular dichroism and Molecular Mechanics studies ; loop_ _publ_author_name 'Joao Costa Pessoa' 'Isabel Correia' 'Vitor Felix' 'E. Fiuza' 'Adelino M. Galvao' 'A. Gameiro' data_BBPIM _database_code_depnum_ccdc_archive 'CCDC 266340' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H27 N3 Ni O4' _chemical_formula_weight 528.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ni Ni 0.2850 1.1130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0020 0.0020 '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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.564(2) _cell_length_b 10.1150(10) _cell_length_c 25.500(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2466.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 14.0 _exptl_crystal_description Parallelepiped _exptl_crystal_colour red/orange _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.827 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 85.5 _exptl_absorpt_correction_T_max 95.6 _exptl_absorpt_process_details psi-scans _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type MACH3 _diffrn_measurement_method omega-2-teta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.06 _diffrn_reflns_number 2493 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2493 _reflns_number_gt 1862 _reflns_threshold_expression >2sigma(I) _computing_data_collection MOLEN _computing_cell_refinement MOLEN _computing_data_reduction MOLEN _computing_structure_solution SHELXS86 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _computing_publication_material WINGX _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^)+(0.0721P)^2^+2.8991P] 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 -0.01(4) _refine_ls_number_reflns 2493 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.12928(12) 0.14395(9) 0.10018(4) 0.0500(3) Uani 1 1 d . . . N1 N 0.1691(7) 0.0421(6) 0.0426(2) 0.0442(16) Uani 1 1 d . . . N2 N 0.1083(8) 0.0006(6) 0.1442(2) 0.0453(16) Uani 1 1 d . . . O2 O 0.1477(10) 0.2891(5) 0.0553(2) 0.081(2) Uani 1 1 d . . . N3 N 0.0835(9) 0.2538(7) 0.1600(3) 0.061(2) Uani 1 1 d . . . O1 O -0.0272(7) -0.0545(7) 0.2163(2) 0.0733(19) Uani 1 1 d . . . C1 C 0.0251(9) 0.0265(8) 0.1865(3) 0.049(2) Uani 1 1 d . . . C2 C -0.0133(9) 0.1696(9) 0.1920(3) 0.058(2) Uani 1 1 d . . . H2 H -0.0063 0.1954 0.2290 0.069 Uiso 1 1 calc R . . C3 C -0.1601(11) 0.2016(13) 0.1718(4) 0.091(4) Uani 1 1 d . . . H3A H -0.2211 0.2279 0.2003 0.109 Uiso 1 1 calc R . . H3B H -0.2007 0.1257 0.1542 0.109 Uiso 1 1 calc R . . C4 C -0.1382(15) 0.3172(13) 0.1329(4) 0.106(5) Uani 1 1 d . . . H4A H -0.1397 0.2857 0.0970 0.127 Uiso 1 1 calc R . . H4B H -0.2104 0.3836 0.1372 0.127 Uiso 1 1 calc R . . C5 C 0.0016(15) 0.3724(10) 0.1463(4) 0.091(4) Uani 1 1 d . . . H5A H 0.0424 0.4183 0.1166 0.109 Uiso 1 1 calc R . . H5B H -0.0044 0.4328 0.1758 0.109 Uiso 1 1 calc R . . C6 C 0.2142(13) 0.2965(10) 0.1881(3) 0.073(3) Uani 1 1 d . . . H6A H 0.2677 0.3530 0.1648 0.088 Uiso 1 1 calc R . . H6B H 0.1875 0.3492 0.2182 0.088 Uiso 1 1 calc R . . C7 C 0.3057(12) 0.1886(10) 0.2062(4) 0.072(3) Uani 1 1 d . . . C8 C 0.2990(14) 0.1404(16) 0.2567(5) 0.108(4) Uani 1 1 d . . . H8 H 0.2373 0.1784 0.2805 0.130 Uiso 1 1 calc R . . C9 C 0.384(2) 0.035(3) 0.2727(9) 0.194(13) Uani 1 1 d . . . H9 H 0.3800 -0.0031 0.3058 0.233 Uiso 1 1 calc R . . C10 C 0.474(4) -0.005(4) 0.2344(19) 0.25(3) Uani 1 1 d . . . H10 H 0.5306 -0.0760 0.2439 0.298 Uiso 1 1 calc R . . C11 C 0.493(4) 0.035(4) 0.1886(13) 0.21(2) Uani 1 1 d . . . H11 H 0.5603 -0.0015 0.1667 0.256 Uiso 1 1 calc R . . C12 C 0.4065(14) 0.1412(17) 0.1722(7) 0.130(6) Uani 1 1 d . . . H12 H 0.4174 0.1782 0.1391 0.156 Uiso 1 1 calc R . . O3 O 0.1308(15) 0.3455(8) -0.0272(3) 0.143(4) Uani 1 1 d . . . C13 C 0.1419(18) 0.2584(11) 0.0055(4) 0.089(4) Uani 1 1 d . . . C14 C 0.1351(11) 0.1157(8) -0.0055(3) 0.057(2) Uani 1 1 d . A . H14 H 0.2015 0.0928 -0.0333 0.068 Uiso 1 1 calc R . . C15 C -0.0158(17) 0.0804(15) -0.0230(5) 0.110(5) Uani 1 1 d . . . H15A H -0.0242 -0.0147 -0.0267 0.132 Uiso 0.398(19) 1 calc PR A 1 H15B H -0.0814 0.1089 0.0038 0.132 Uiso 0.398(19) 1 calc PR A 1 H15C H -0.0500 0.1475 -0.0470 0.132 Uiso 0.602(19) 1 calc PR A 2 H15D H -0.0152 -0.0036 -0.0413 0.132 Uiso 0.602(19) 1 calc PR A 2 O15A O -0.049(3) 0.141(3) -0.0705(7) 0.129(11) Uani 0.398(19) 1 d P A 1 H15E H 0.0145 0.1906 -0.0792 0.155 Uiso 0.398(19) 1 calc PR A 1 O15B O -0.094(2) 0.073(5) 0.0151(14) 0.34(3) Uani 0.602(19) 1 d P A 2 H15F H -0.1599 0.1245 0.0112 0.412 Uiso 0.602(19) 1 calc PR A 2 C19 C 0.2168(8) -0.0769(7) 0.0415(3) 0.0433(18) Uani 1 1 d . . . C20 C 0.2536(8) -0.1416(9) -0.0097(3) 0.0456(17) Uani 1 1 d . . . C21 C 0.3719(10) -0.1041(7) -0.0376(3) 0.055(2) Uani 1 1 d . . . H21 H 0.4269 -0.0345 -0.0256 0.066 Uiso 1 1 calc R . . C22 C 0.4083(12) -0.1701(9) -0.0833(3) 0.073(3) Uani 1 1 d . . . H22 H 0.4881 -0.1455 -0.1018 0.087 Uiso 1 1 calc R . . C23 C 0.3267(13) -0.2712(11) -0.1011(3) 0.083(3) Uani 1 1 d . . . H23 H 0.3497 -0.3138 -0.1323 0.100 Uiso 1 1 calc R . . C24 C 0.2098(13) -0.3107(12) -0.0732(4) 0.088(4) Uani 1 1 d . . . H24 H 0.1559 -0.3815 -0.0847 0.106 Uiso 1 1 calc R . . C25 C 0.1746(11) -0.2435(11) -0.0279(4) 0.081(3) Uani 1 1 d . . . H25 H 0.0950 -0.2685 -0.0094 0.098 Uiso 1 1 calc R . . C26 C 0.2344(8) -0.1541(8) 0.0898(3) 0.0458(18) Uani 1 1 d . . . C27 C 0.1765(8) -0.1192(7) 0.1386(3) 0.0423(18) Uani 1 1 d . . . C28 C 0.1998(11) -0.2043(8) 0.1801(3) 0.060(2) Uani 1 1 d . . . H28 H 0.1630 -0.1824 0.2127 0.073 Uiso 1 1 calc R . . C29 C 0.2740(12) -0.3185(9) 0.1756(4) 0.077(3) Uani 1 1 d . . . H29 H 0.2856 -0.3729 0.2047 0.092 Uiso 1 1 calc R . . C30 C 0.3316(12) -0.3538(11) 0.1284(4) 0.085(3) Uani 1 1 d . . . H30 H 0.3832 -0.4313 0.1250 0.102 Uiso 1 1 calc R . . C31 C 0.3110(10) -0.2722(9) 0.0865(3) 0.062(2) Uani 1 1 d . . . H31 H 0.3494 -0.2958 0.0543 0.075 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 Ni 0.0741(7) 0.0361(4) 0.0397(5) -0.0007(4) 0.0048(5) -0.0016(6) N1 0.047(4) 0.045(3) 0.040(3) -0.004(3) 0.001(3) -0.004(3) N2 0.056(4) 0.041(3) 0.040(3) -0.005(3) 0.005(3) -0.009(3) O2 0.137(7) 0.037(3) 0.068(4) 0.004(3) 0.012(5) 0.001(4) N3 0.091(6) 0.037(3) 0.054(4) -0.005(3) 0.002(4) 0.006(4) O1 0.093(5) 0.066(4) 0.061(4) 0.005(3) 0.030(4) -0.013(4) C1 0.052(5) 0.053(5) 0.042(4) -0.008(4) -0.004(4) -0.002(4) C2 0.069(6) 0.063(6) 0.041(4) -0.004(4) 0.001(4) 0.007(5) C3 0.082(8) 0.114(9) 0.077(7) -0.026(7) -0.016(6) 0.021(7) C4 0.125(11) 0.124(11) 0.069(6) 0.008(7) -0.021(7) 0.072(10) C5 0.158(12) 0.060(6) 0.055(5) 0.000(5) -0.006(7) 0.041(8) C6 0.114(8) 0.058(5) 0.049(5) -0.021(4) 0.007(6) -0.028(6) C7 0.073(6) 0.058(6) 0.083(7) -0.012(5) -0.007(6) -0.023(5) C8 0.104(9) 0.132(11) 0.088(8) 0.010(9) -0.041(7) -0.041(11) C9 0.141(17) 0.21(3) 0.23(2) 0.13(2) -0.124(19) -0.088(18) C10 0.10(2) 0.127(19) 0.52(8) -0.08(5) -0.08(5) 0.008(18) C11 0.083(14) 0.23(5) 0.32(4) -0.17(4) -0.02(3) 0.00(2) C12 0.069(8) 0.148(13) 0.172(14) -0.108(13) 0.000(9) -0.012(10) O3 0.268(13) 0.079(5) 0.083(5) 0.022(5) 0.012(8) -0.001(10) C13 0.151(12) 0.059(5) 0.056(5) 0.019(5) 0.001(7) -0.018(8) C14 0.073(6) 0.052(5) 0.046(4) 0.007(3) 0.006(5) 0.010(5) C15 0.123(12) 0.119(10) 0.088(8) 0.025(8) -0.035(8) 0.007(10) O15A 0.20(3) 0.116(19) 0.067(13) -0.018(12) -0.069(16) 0.054(19) O15B 0.112(18) 0.62(7) 0.30(3) 0.31(4) -0.09(2) -0.11(3) C19 0.041(4) 0.044(4) 0.045(4) -0.001(3) -0.003(4) -0.004(4) C20 0.046(4) 0.051(4) 0.040(4) 0.003(4) 0.001(3) 0.004(4) C21 0.057(5) 0.048(4) 0.059(4) 0.006(4) 0.020(5) 0.012(5) C22 0.094(8) 0.064(6) 0.060(5) 0.011(5) 0.030(5) 0.032(6) C23 0.130(10) 0.089(7) 0.030(4) -0.010(5) 0.014(6) 0.031(7) C24 0.101(8) 0.099(9) 0.065(6) -0.033(6) 0.007(6) -0.006(7) C25 0.062(6) 0.095(8) 0.087(7) -0.039(6) 0.016(5) -0.013(6) C26 0.047(4) 0.046(4) 0.045(4) 0.000(4) 0.002(3) -0.001(4) C27 0.052(4) 0.039(4) 0.036(3) -0.004(3) -0.004(3) -0.007(4) C28 0.088(7) 0.051(5) 0.042(4) 0.006(4) -0.003(5) -0.003(5) C29 0.106(8) 0.056(6) 0.069(6) 0.017(5) -0.009(6) 0.020(6) C30 0.115(9) 0.059(5) 0.082(6) 0.005(6) 0.002(6) 0.036(7) C31 0.077(6) 0.055(5) 0.055(5) -0.008(4) 0.001(5) 0.016(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 Ni N1 1.834(6) . ? Ni N2 1.845(6) . ? Ni O2 1.869(6) . ? Ni N3 1.938(7) . ? N1 C19 1.288(10) . ? N1 C14 1.471(10) . ? N2 C1 1.365(10) . ? N2 C27 1.383(9) . ? O2 C13 1.310(12) . ? N3 C5 1.474(12) . ? N3 C2 1.499(11) . ? N3 C6 1.504(13) . ? O1 C1 1.225(10) . ? C1 C2 1.500(12) . ? C2 C3 1.531(13) . ? C3 C4 1.548(16) . ? C4 C5 1.489(18) . ? C6 C7 1.472(15) . ? C7 C8 1.380(15) . ? C7 C12 1.382(16) . ? C8 C9 1.40(2) . ? C9 C10 1.36(4) . ? C10 C11 1.25(6) . ? C11 C12 1.42(4) . ? O3 C13 1.217(12) . ? C13 C14 1.473(14) . ? C14 C15 1.552(17) . ? C15 O15B 1.23(3) . ? C15 O15A 1.40(2) . ? C19 C26 1.468(10) . ? C19 C20 1.503(10) . ? C20 C25 1.359(12) . ? C20 C21 1.389(11) . ? C21 C22 1.387(11) . ? C22 C23 1.365(14) . ? C23 C24 1.384(15) . ? C24 C25 1.383(13) . ? C26 C31 1.404(12) . ? C26 C27 1.407(10) . ? C27 C28 1.381(10) . ? C28 C29 1.361(13) . ? C29 C30 1.372(13) . ? C30 C31 1.364(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 N1 Ni N2 93.9(3) . . ? N1 Ni O2 86.1(3) . . ? N2 Ni O2 179.1(4) . . ? N1 Ni N3 178.5(3) . . ? N2 Ni N3 87.0(3) . . ? O2 Ni N3 93.0(3) . . ? C19 N1 C14 122.2(6) . . ? C19 N1 Ni 128.0(6) . . ? C14 N1 Ni 109.7(5) . . ? C1 N2 C27 121.6(6) . . ? C1 N2 Ni 113.1(5) . . ? C27 N2 Ni 125.1(5) . . ? C13 O2 Ni 113.8(6) . . ? C5 N3 C2 105.3(8) . . ? C5 N3 C6 108.7(8) . . ? C2 N3 C6 114.7(7) . . ? C5 N3 Ni 113.6(6) . . ? C2 N3 Ni 104.0(5) . . ? C6 N3 Ni 110.6(6) . . ? O1 C1 N2 126.8(8) . . ? O1 C1 C2 119.2(7) . . ? N2 C1 C2 113.7(7) . . ? N3 C2 C1 110.2(7) . . ? N3 C2 C3 105.3(8) . . ? C1 C2 C3 113.3(8) . . ? C2 C3 C4 104.5(9) . . ? C5 C4 C3 104.9(8) . . ? N3 C5 C4 103.1(9) . . ? C7 C6 N3 115.5(7) . . ? C8 C7 C12 119.7(14) . . ? C8 C7 C6 121.8(12) . . ? C12 C7 C6 118.4(13) . . ? C7 C8 C9 120.9(17) . . ? C10 C9 C8 113(3) . . ? C11 C10 C9 131(5) . . ? C10 C11 C12 116(4) . . ? C7 C12 C11 119(2) . . ? O3 C13 O2 119.8(10) . . ? O3 C13 C14 125.1(10) . . ? O2 C13 C14 114.8(8) . . ? N1 C14 C13 109.1(7) . . ? N1 C14 C15 109.2(8) . . ? C13 C14 C15 108.7(11) . . ? O15B C15 O15A 125(2) . . ? O15B C15 C14 110.7(17) . . ? O15A C15 C14 111.2(16) . . ? N1 C19 C26 121.3(7) . . ? N1 C19 C20 120.6(7) . . ? C26 C19 C20 118.1(7) . . ? C25 C20 C21 119.1(8) . . ? C25 C20 C19 119.7(7) . . ? C21 C20 C19 121.1(8) . . ? C22 C21 C20 120.2(9) . . ? C23 C22 C21 119.7(9) . . ? C22 C23 C24 120.5(9) . . ? C25 C24 C23 119.0(11) . . ? C20 C25 C24 121.5(10) . . ? C31 C26 C27 118.2(7) . . ? C31 C26 C19 117.5(7) . . ? C27 C26 C19 124.4(7) . . ? C28 C27 N2 122.9(7) . . ? C28 C27 C26 117.2(7) . . ? N2 C27 C26 119.7(7) . . ? C29 C28 C27 123.3(9) . . ? C28 C29 C30 120.3(9) . . ? C31 C30 C29 118.1(9) . . ? C30 C31 C26 122.9(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ni N1 C19 -22.7(7) . . . . ? O2 Ni N1 C19 158.2(7) . . . . ? N3 Ni N1 C19 -149(12) . . . . ? N2 Ni N1 C14 156.0(6) . . . . ? O2 Ni N1 C14 -23.1(6) . . . . ? N3 Ni N1 C14 29(12) . . . . ? N1 Ni N2 C1 -155.4(6) . . . . ? O2 Ni N2 C1 -65(19) . . . . ? N3 Ni N2 C1 23.4(6) . . . . ? N1 Ni N2 C27 29.4(7) . . . . ? O2 Ni N2 C27 120(18) . . . . ? N3 Ni N2 C27 -151.8(7) . . . . ? N1 Ni O2 C13 16.7(10) . . . . ? N2 Ni O2 C13 -74(19) . . . . ? N3 Ni O2 C13 -162.1(10) . . . . ? N1 Ni N3 C5 -18(13) . . . . ? N2 Ni N3 C5 -144.7(8) . . . . ? O2 Ni N3 C5 34.4(8) . . . . ? N1 Ni N3 C2 96(12) . . . . ? N2 Ni N3 C2 -30.8(5) . . . . ? O2 Ni N3 C2 148.3(6) . . . . ? N1 Ni N3 C6 -140(12) . . . . ? N2 Ni N3 C6 92.8(6) . . . . ? O2 Ni N3 C6 -88.1(6) . . . . ? C27 N2 C1 O1 -19.0(13) . . . . ? Ni N2 C1 O1 165.6(7) . . . . ? C27 N2 C1 C2 166.9(7) . . . . ? Ni N2 C1 C2 -8.5(9) . . . . ? C5 N3 C2 C1 152.3(7) . . . . ? C6 N3 C2 C1 -88.2(9) . . . . ? Ni N3 C2 C1 32.6(8) . . . . ? C5 N3 C2 C3 29.7(9) . . . . ? C6 N3 C2 C3 149.2(8) . . . . ? Ni N3 C2 C3 -90.0(7) . . . . ? O1 C1 C2 N3 168.0(7) . . . . ? N2 C1 C2 N3 -17.4(10) . . . . ? O1 C1 C2 C3 -74.3(11) . . . . ? N2 C1 C2 C3 100.3(9) . . . . ? N3 C2 C3 C4 -6.6(10) . . . . ? C1 C2 C3 C4 -127.1(9) . . . . ? C2 C3 C4 C5 -18.5(11) . . . . ? C2 N3 C5 C4 -41.7(9) . . . . ? C6 N3 C5 C4 -165.0(8) . . . . ? Ni N3 C5 C4 71.5(9) . . . . ? C3 C4 C5 N3 36.9(10) . . . . ? C5 N3 C6 C7 177.9(9) . . . . ? C2 N3 C6 C7 60.5(10) . . . . ? Ni N3 C6 C7 -56.7(9) . . . . ? N3 C6 C7 C8 -95.8(11) . . . . ? N3 C6 C7 C12 88.4(11) . . . . ? C12 C7 C8 C9 -6.2(18) . . . . ? C6 C7 C8 C9 178.1(12) . . . . ? C7 C8 C9 C10 3(3) . . . . ? C8 C9 C10 C11 1(7) . . . . ? C9 C10 C11 C12 -1(8) . . . . ? C8 C7 C12 C11 6(2) . . . . ? C6 C7 C12 C11 -178.6(18) . . . . ? C10 C11 C12 C7 -2(5) . . . . ? Ni O2 C13 O3 168.6(13) . . . . ? Ni O2 C13 C14 -5.3(17) . . . . ? C19 N1 C14 C13 -156.1(10) . . . . ? Ni N1 C14 C13 25.2(11) . . . . ? C19 N1 C14 C15 85.3(10) . . . . ? Ni N1 C14 C15 -93.5(8) . . . . ? O3 C13 C14 N1 173.5(15) . . . . ? O2 C13 C14 N1 -13.0(18) . . . . ? O3 C13 C14 C15 -67.5(19) . . . . ? O2 C13 C14 C15 106.0(14) . . . . ? N1 C14 C15 O15B 41(3) . . . . ? C13 C14 C15 O15B -78(3) . . . . ? N1 C14 C15 O15A -175.9(14) . . . . ? C13 C14 C15 O15A 65.2(17) . . . . ? C14 N1 C19 C26 -172.7(7) . . . . ? Ni N1 C19 C26 5.9(11) . . . . ? C14 N1 C19 C20 6.1(11) . . . . ? Ni N1 C19 C20 -175.3(5) . . . . ? N1 C19 C20 C25 -110.9(10) . . . . ? C26 C19 C20 C25 68.0(11) . . . . ? N1 C19 C20 C21 72.8(10) . . . . ? C26 C19 C20 C21 -108.4(9) . . . . ? C25 C20 C21 C22 0.0(13) . . . . ? C19 C20 C21 C22 176.4(8) . . . . ? C20 C21 C22 C23 0.7(13) . . . . ? C21 C22 C23 C24 -1.7(15) . . . . ? C22 C23 C24 C25 2.1(17) . . . . ? C21 C20 C25 C24 0.4(15) . . . . ? C19 C20 C25 C24 -176.1(10) . . . . ? C23 C24 C25 C20 -1.4(18) . . . . ? N1 C19 C26 C31 -168.2(8) . . . . ? C20 C19 C26 C31 13.0(11) . . . . ? N1 C19 C26 C27 13.6(12) . . . . ? C20 C19 C26 C27 -165.3(7) . . . . ? C1 N2 C27 C28 -19.2(12) . . . . ? Ni N2 C27 C28 155.6(7) . . . . ? C1 N2 C27 C26 165.4(7) . . . . ? Ni N2 C27 C26 -19.7(10) . . . . ? C31 C26 C27 C28 0.2(12) . . . . ? C19 C26 C27 C28 178.4(8) . . . . ? C31 C26 C27 N2 175.8(7) . . . . ? C19 C26 C27 N2 -6.0(12) . . . . ? N2 C27 C28 C29 -176.0(9) . . . . ? C26 C27 C28 C29 -0.5(14) . . . . ? C27 C28 C29 C30 0.8(17) . . . . ? C28 C29 C30 C31 -0.7(17) . . . . ? C29 C30 C31 C26 0.3(17) . . . . ? C27 C26 C31 C30 0.0(14) . . . . ? C19 C26 C31 C30 -178.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.409 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.079 data_bbpim_b _database_code_depnum_ccdc_archive 'CCDC 266341' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H29 N7 Ni O3' _chemical_formula_weight 642.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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 10.8750(10) _cell_length_b 12.042(2) _cell_length_c 24.834(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3252.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 14.0 _exptl_crystal_description Parallelepiped _exptl_crystal_colour red/orange _exptl_crystal_size_max .5 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.641 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 87.3 _exptl_absorpt_correction_T_max 96.2 _exptl_absorpt_process_details psi-scans _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type MACH3 _diffrn_measurement_method omega-2-teta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.06 _diffrn_reflns_number 4381 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1247 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.97 _reflns_number_total 4381 _reflns_number_gt 2097 _reflns_threshold_expression >2sigma(I) _computing_data_collection MOLEN _computing_cell_refinement MOLEN _computing_data_reduction MOLEN _computing_structure_solution SHELXS86 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _computing_publication_material WINGX _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^)+(0.1169P)^2^+7.6123P] 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 0.03(6) _refine_ls_number_reflns 4381 _refine_ls_number_parameters 391 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.2154 _refine_ls_R_factor_gt 0.1061 _refine_ls_wR_factor_ref 0.2900 _refine_ls_wR_factor_gt 0.2247 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.003 _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 0.28019(14) 0.12269(13) 0.28407(7) 0.0405(4) Uani 1 1 d . . . O1 O 0.2939(10) 0.4389(8) 0.2545(5) 0.064(3) Uani 1 1 d . . . O2 O 0.3131(8) -0.0275(7) 0.2711(4) 0.052(3) Uani 1 1 d . . . O3 O 0.2178(11) -0.1906(7) 0.2662(5) 0.071(3) Uani 1 1 d . . . N1 N 0.1364(9) 0.0748(8) 0.3185(4) 0.039(2) Uani 1 1 d . . . N2 N 0.2533(9) 0.2724(8) 0.2982(4) 0.039(3) Uani 1 1 d . . . N3 N 0.4324(10) 0.1670(9) 0.2501(5) 0.045(3) Uani 1 1 d . . . N4 N 0.0378(10) 0.0266(9) 0.2100(5) 0.049(3) Uani 1 1 d . . . N5 N 0.1317(17) 0.0805(17) 0.1346(7) 0.101(6) Uani 1 1 d . . . C1 C 0.3180(11) 0.3394(11) 0.2623(5) 0.041(3) Uani 1 1 d . . . C2 C 0.4162(12) 0.2849(9) 0.2325(5) 0.042(3) Uani 1 1 d . . . H2 H 0.4928 0.3244 0.2407 0.051 Uiso 1 1 calc R . . C3 C 0.403(2) 0.2813(15) 0.1716(6) 0.083(6) Uani 1 1 d . . . H31 H 0.3178 0.2783 0.1607 0.099 Uiso 1 1 calc R . . H32 H 0.4429 0.3445 0.1547 0.099 Uiso 1 1 calc R . . C4 C 0.469(4) 0.1751(18) 0.1593(9) 0.173(17) Uani 1 1 d . . . H41 H 0.4330 0.1410 0.1277 0.207 Uiso 1 1 calc R . . H42 H 0.5548 0.1908 0.1516 0.207 Uiso 1 1 calc R . . C5 C 0.4619(14) 0.1032(12) 0.2017(5) 0.054(4) Uani 1 1 d . . . H51 H 0.5396 0.0649 0.2063 0.065 Uiso 1 1 calc R . . H52 H 0.3985 0.0482 0.1950 0.065 Uiso 1 1 calc R . . C6 C 0.5335(13) 0.1515(11) 0.2903(7) 0.058(4) Uani 1 1 d . . . H61 H 0.6103 0.1739 0.2736 0.070 Uiso 1 1 calc R . . H62 H 0.5398 0.0730 0.2986 0.070 Uiso 1 1 calc R . . C7 C 0.5191(14) 0.2149(12) 0.3427(6) 0.055(4) Uani 1 1 d . . . C8 C 0.587(2) 0.3105(14) 0.3504(8) 0.086(6) Uani 1 1 d . . . H8 H 0.6393 0.3343 0.3231 0.104 Uiso 1 1 calc R . . C9 C 0.580(3) 0.3717(19) 0.3971(10) 0.130(10) Uani 1 1 d . . . H9 H 0.6249 0.4366 0.4023 0.156 Uiso 1 1 calc R . . C10 C 0.502(3) 0.330(2) 0.4352(10) 0.120(9) Uani 1 1 d . . . H10 H 0.4964 0.3701 0.4669 0.144 Uiso 1 1 calc R . . C11 C 0.429(2) 0.233(2) 0.4326(7) 0.093(7) Uani 1 1 d . . . H11 H 0.3770 0.2080 0.4600 0.111 Uiso 1 1 calc R . . C12 C 0.4449(16) 0.1767(15) 0.3815(6) 0.068(5) Uani 1 1 d . . . H12 H 0.4019 0.1112 0.3753 0.082 Uiso 1 1 calc R . . C13 C 0.2218(13) -0.0922(9) 0.2775(6) 0.049(3) Uani 1 1 d . . . C14 C 0.1019(12) -0.0373(10) 0.2983(5) 0.043(3) Uani 1 1 d . . . H14 H 0.0725 -0.0809 0.3290 0.052 Uiso 1 1 calc R . . C15 C 0.0017(14) -0.0372(12) 0.2560(6) 0.050(3) Uani 1 1 d . . . H151 H -0.0156 -0.1129 0.2451 0.060 Uiso 1 1 calc R . . H152 H -0.0729 -0.0060 0.2712 0.060 Uiso 1 1 calc R . . C16 C 0.0085(16) 0.1372(13) 0.1991(8) 0.075(5) Uani 1 1 d . . . H16 H -0.0431 0.1819 0.2196 0.091 Uiso 1 1 calc R . . C17 C 0.0683(17) 0.169(2) 0.1533(8) 0.084(6) Uani 1 1 d . . . H17 H 0.0659 0.2388 0.1377 0.100 Uiso 1 1 calc R . . C18 C 0.1132(17) -0.0041(16) 0.1671(7) 0.077(5) Uani 1 1 d . . . H18 H 0.1460 -0.0747 0.1621 0.092 Uiso 1 1 calc R . . C19 C 0.0739(10) 0.1247(11) 0.3534(5) 0.040(3) Uani 1 1 d . . . C20 C -0.0288(11) 0.0703(10) 0.3811(6) 0.039(3) Uani 1 1 d . . . C21 C -0.0058(14) -0.0047(12) 0.4236(5) 0.052(4) Uani 1 1 d . . . H21 H 0.0752 -0.0219 0.4321 0.063 Uiso 1 1 calc R . . C22 C -0.0976(18) -0.0526(13) 0.4524(7) 0.077(5) Uani 1 1 d . . . H22 H -0.0801 -0.1002 0.4809 0.092 Uiso 1 1 calc R . . C23 C -0.2202(16) -0.0285(14) 0.4382(8) 0.080(5) Uani 1 1 d . . . H23 H -0.2847 -0.0640 0.4557 0.096 Uiso 1 1 calc R . . C24 C -0.2437(15) 0.0470(15) 0.3986(8) 0.083(6) Uani 1 1 d . . . H24 H -0.3247 0.0668 0.3916 0.100 Uiso 1 1 calc R . . C25 C -0.1521(14) 0.0943(15) 0.3690(7) 0.078(6) Uani 1 1 d . . . H25 H -0.1711 0.1424 0.3409 0.093 Uiso 1 1 calc R . . C26 C 0.1057(12) 0.2406(11) 0.3693(5) 0.045(3) Uani 1 1 d . . . C27 C 0.1879(11) 0.3114(10) 0.3409(5) 0.041(3) Uani 1 1 d . . . C28 C 0.2074(13) 0.4164(10) 0.3632(6) 0.047(3) Uani 1 1 d . . . H28 H 0.2586 0.4644 0.3443 0.057 Uiso 1 1 calc R . . C29 C 0.1608(19) 0.4532(15) 0.4078(9) 0.092(7) Uani 1 1 d . . . H29 H 0.1781 0.5248 0.4196 0.110 Uiso 1 1 calc R . . C30 C 0.0818(19) 0.3818(15) 0.4388(7) 0.085(6) Uani 1 1 d . . . H30 H 0.0544 0.4022 0.4729 0.102 Uiso 1 1 calc R . . C31 C 0.0476(9) 0.2794(7) 0.4153(4) 0.073(5) Uani 1 1 d . . . H311 H -0.0148 0.2375 0.4310 0.087 Uiso 1 1 calc R . . N41 N 0.3190(9) -0.1401(7) 0.4262(4) 0.206(12) Uani 1 1 d RU . . C42 C 0.2232(9) -0.2196(7) 0.4220(4) 0.115(8) Uani 1 1 d RU . . C45 C 0.1714(9) -0.2347(7) 0.4739(4) 0.135(10) Uani 1 1 d RU . . N44 N 0.2353(9) -0.1644(7) 0.5104(4) 0.181(11) Uani 1 1 d RU . . C43 C 0.3266(9) -0.1060(7) 0.4809(4) 0.158(12) Uani 1 1 d RU . . 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 0.0349(7) 0.0332(7) 0.0533(9) -0.0002(8) 0.0021(8) -0.0013(7) O1 0.057(6) 0.044(5) 0.090(7) 0.016(5) 0.006(6) 0.002(5) O2 0.049(5) 0.030(4) 0.078(7) -0.013(5) 0.014(5) 0.008(4) O3 0.072(6) 0.026(4) 0.115(9) 0.002(5) 0.018(7) -0.004(5) N1 0.037(5) 0.030(5) 0.049(6) 0.015(5) 0.006(5) -0.009(4) N2 0.048(6) 0.031(5) 0.039(6) 0.003(4) -0.003(4) -0.003(4) N3 0.044(6) 0.037(6) 0.056(7) -0.006(5) 0.001(5) 0.006(5) N4 0.043(6) 0.050(6) 0.054(7) -0.002(6) -0.001(6) 0.011(5) N5 0.095(13) 0.124(15) 0.084(12) 0.038(11) 0.023(10) -0.006(12) C1 0.027(6) 0.049(7) 0.047(7) 0.012(6) 0.001(5) 0.000(5) C2 0.040(6) 0.024(6) 0.063(9) 0.009(6) -0.009(6) -0.006(5) C3 0.115(15) 0.082(13) 0.052(10) 0.025(9) 0.014(11) 0.027(12) C4 0.37(5) 0.068(15) 0.083(17) 0.007(13) 0.05(2) 0.07(2) C5 0.059(8) 0.050(9) 0.054(9) 0.002(7) 0.007(7) 0.015(7) C6 0.050(8) 0.043(8) 0.081(11) 0.009(8) -0.006(9) -0.012(6) C7 0.060(9) 0.045(8) 0.061(10) -0.005(7) -0.012(8) 0.004(7) C8 0.122(16) 0.057(10) 0.081(13) -0.010(10) -0.039(13) -0.012(11) C9 0.22(3) 0.069(13) 0.098(16) 0.015(14) -0.042(19) -0.04(2) C10 0.17(3) 0.099(18) 0.089(17) -0.028(15) -0.044(18) 0.022(19) C11 0.110(16) 0.130(19) 0.039(9) 0.021(11) -0.010(10) 0.008(15) C12 0.069(10) 0.084(12) 0.053(9) 0.014(9) -0.002(8) -0.006(10) C13 0.045(6) 0.030(6) 0.072(9) 0.004(6) -0.013(8) 0.001(6) C14 0.044(7) 0.035(6) 0.051(8) 0.002(6) -0.003(6) -0.001(6) C15 0.046(7) 0.046(8) 0.057(8) 0.011(7) 0.000(7) -0.017(6) C16 0.076(11) 0.045(9) 0.106(14) 0.004(10) 0.011(10) 0.029(8) C17 0.076(13) 0.112(17) 0.063(12) 0.021(12) -0.016(10) 0.023(12) C18 0.083(13) 0.071(12) 0.076(12) -0.011(10) -0.008(11) 0.008(10) C19 0.036(6) 0.034(6) 0.049(7) -0.009(7) 0.003(5) 0.013(6) C20 0.030(6) 0.029(6) 0.059(8) 0.008(6) 0.003(6) 0.000(5) C21 0.058(9) 0.053(8) 0.046(8) 0.021(7) -0.009(7) 0.002(7) C22 0.093(13) 0.049(9) 0.088(12) 0.030(9) 0.027(11) 0.003(9) C23 0.049(9) 0.070(11) 0.122(15) 0.034(11) 0.011(11) -0.003(10) C24 0.050(10) 0.094(13) 0.105(14) 0.036(11) 0.007(9) 0.016(9) C25 0.044(8) 0.106(15) 0.083(12) 0.050(11) 0.020(8) 0.010(9) C26 0.049(7) 0.038(7) 0.049(8) 0.004(6) 0.011(6) 0.008(6) C27 0.035(6) 0.039(7) 0.049(8) 0.004(6) 0.006(6) -0.005(5) C28 0.046(7) 0.036(6) 0.060(8) -0.002(6) -0.005(7) -0.007(6) C29 0.106(15) 0.048(10) 0.121(17) -0.035(11) 0.026(14) 0.006(11) C30 0.120(15) 0.058(10) 0.075(11) -0.023(10) 0.031(11) 0.023(12) C31 0.094(13) 0.046(9) 0.079(12) 0.004(9) 0.039(10) 0.011(9) N41 0.17(2) 0.20(2) 0.24(2) 0.090(19) 0.080(19) 0.093(18) C42 0.115(15) 0.062(11) 0.168(19) -0.026(12) -0.024(16) 0.028(12) C45 0.123(17) 0.081(13) 0.20(2) 0.075(15) 0.011(17) 0.034(13) N44 0.27(2) 0.22(2) 0.053(9) 0.000(12) -0.024(14) 0.13(2) C43 0.123(18) 0.114(17) 0.24(3) -0.073(19) -0.051(19) 0.009(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 1.859(9) . ? Ni1 O2 1.872(8) . ? Ni1 N1 1.874(9) . ? Ni1 N3 1.933(11) . ? O1 C1 1.241(15) . ? O2 C13 1.271(15) . ? O3 C13 1.218(14) . ? N1 C19 1.255(15) . ? N1 C14 1.488(15) . ? N2 C27 1.360(15) . ? N2 C1 1.394(15) . ? N3 C5 1.464(16) . ? N3 C6 1.495(18) . ? N3 C2 1.497(15) . ? N4 C18 1.39(2) . ? N4 C16 1.396(18) . ? N4 C15 1.433(17) . ? N5 C18 1.31(2) . ? N5 C17 1.35(3) . ? C1 C2 1.456(17) . ? C2 C3 1.52(2) . ? C3 C4 1.50(3) . ? C4 C5 1.36(2) . ? C6 C7 1.52(2) . ? C7 C12 1.34(2) . ? C7 C8 1.38(2) . ? C8 C9 1.38(3) . ? C9 C10 1.37(3) . ? C10 C11 1.42(3) . ? C11 C12 1.45(2) . ? C13 C14 1.550(18) . ? C14 C15 1.513(19) . ? C16 C17 1.36(2) . ? C19 C20 1.466(17) . ? C19 C26 1.491(18) . ? C20 C25 1.404(19) . ? C20 C21 1.410(17) . ? C21 C22 1.36(2) . ? C22 C23 1.41(2) . ? C23 C24 1.36(2) . ? C24 C25 1.36(2) . ? C26 C31 1.388(15) . ? C26 C27 1.423(17) . ? C27 C28 1.397(17) . ? C28 C29 1.30(2) . ? C29 C30 1.44(3) . ? C30 C31 1.414(19) . ? N41 C42 1.4200 . ? N41 C43 1.4200 . ? C42 C45 1.4200 . ? C45 N44 1.4200 . ? N44 C43 1.4200 . ? 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 Ni1 O2 177.8(5) . . ? N2 Ni1 N1 94.6(4) . . ? O2 Ni1 N1 86.6(4) . . ? N2 Ni1 N3 87.1(4) . . ? O2 Ni1 N3 91.6(4) . . ? N1 Ni1 N3 177.5(5) . . ? C13 O2 Ni1 114.9(8) . . ? C19 N1 C14 122.1(11) . . ? C19 N1 Ni1 128.3(9) . . ? C14 N1 Ni1 109.6(8) . . ? C27 N2 C1 124.2(10) . . ? C27 N2 Ni1 124.4(8) . . ? C1 N2 Ni1 111.2(8) . . ? C5 N3 C6 108.8(11) . . ? C5 N3 C2 106.5(11) . . ? C6 N3 C2 113.5(10) . . ? C5 N3 Ni1 113.7(9) . . ? C6 N3 Ni1 107.7(9) . . ? C2 N3 Ni1 106.8(8) . . ? C18 N4 C16 103.8(14) . . ? C18 N4 C15 129.0(13) . . ? C16 N4 C15 127.1(14) . . ? C18 N5 C17 108.7(16) . . ? O1 C1 N2 123.5(12) . . ? O1 C1 C2 120.7(12) . . ? N2 C1 C2 115.8(11) . . ? C1 C2 N3 111.4(11) . . ? C1 C2 C3 116.8(13) . . ? N3 C2 C3 106.0(12) . . ? C4 C3 C2 100.5(15) . . ? C5 C4 C3 111.0(19) . . ? C4 C5 N3 108.2(14) . . ? N3 C6 C7 115.7(12) . . ? C12 C7 C8 120.6(17) . . ? C12 C7 C6 120.5(14) . . ? C8 C7 C6 118.9(16) . . ? C9 C8 C7 122(2) . . ? C10 C9 C8 115(2) . . ? C9 C10 C11 129(2) . . ? C10 C11 C12 110.7(19) . . ? C7 C12 C11 123.1(18) . . ? O3 C13 O2 126.6(14) . . ? O3 C13 C14 117.4(13) . . ? O2 C13 C14 115.9(9) . . ? N1 C14 C15 114.5(10) . . ? N1 C14 C13 106.7(10) . . ? C15 C14 C13 112.1(11) . . ? N4 C15 C14 110.9(11) . . ? C17 C16 N4 108.5(16) . . ? N5 C17 C16 108.2(18) . . ? N5 C18 N4 110.7(17) . . ? N1 C19 C20 121.5(12) . . ? N1 C19 C26 120.3(11) . . ? C20 C19 C26 118.1(11) . . ? C25 C20 C21 117.4(12) . . ? C25 C20 C19 122.3(12) . . ? C21 C20 C19 120.2(11) . . ? C22 C21 C20 122.4(14) . . ? C21 C22 C23 118.4(15) . . ? C24 C23 C22 119.7(16) . . ? C25 C24 C23 122.0(16) . . ? C24 C25 C20 119.8(14) . . ? C31 C26 C27 119.5(12) . . ? C31 C26 C19 115.3(11) . . ? C27 C26 C19 125.1(12) . . ? N2 C27 C28 122.9(12) . . ? N2 C27 C26 120.5(11) . . ? C28 C27 C26 116.1(12) . . ? C29 C28 C27 126.1(15) . . ? C28 C29 C30 119.2(16) . . ? C31 C30 C29 117.2(14) . . ? C26 C31 C30 120.9(12) . . ? C42 N41 C43 108.0 . . ? N41 C42 C45 108.0 . . ? N44 C45 C42 108.0 . . ? C45 N44 C43 108.0 . . ? N44 C43 N41 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Ni1 N3 C6 C7 -57.9(13) . . . . ? Ni1 N1 C14 C15 -99.8(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.777 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.118 data_jpnov _database_code_depnum_ccdc_archive 'CCDC 266342' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H25 N3 Ni O3' _chemical_formula_weight 498.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Ni Ni 0.2850 1.1130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0020 0.0020 '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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.0440(10) _cell_length_b 9.7220(10) _cell_length_c 26.445(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2325.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 14.0 _exptl_crystal_description Parallelepiped _exptl_crystal_colour red/orange _exptl_crystal_size_max .6 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.869 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 80.2 _exptl_absorpt_correction_T_max 94.3 _exptl_absorpt_process_details psi-scans _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type MACH3 _diffrn_measurement_method omega-2-teta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.03 _diffrn_reflns_number 2893 _diffrn_reflns_av_R_equivalents 0.4176 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 26.96 _reflns_number_total 2888 _reflns_number_gt 1963 _reflns_threshold_expression >2sigma(I) _computing_data_collection MOLEN _computing_cell_refinement MOLEN _computing_data_reduction MOLEN _computing_structure_solution SHELXS86 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _computing_publication_material WINGX _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^+5.3876P] 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 -0.10(4) _refine_ls_number_reflns 2888 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 0.97511(10) 0.02824(11) 0.11075(4) 0.0326(2) Uani 1 1 d . . . N1 N 0.8918(6) 0.0165(7) 0.1750(2) 0.0330(16) Uani 1 1 d . . . N2 N 1.1511(7) -0.0566(7) 0.1286(2) 0.0337(16) Uani 1 1 d . . . N3 N 1.0334(7) 0.0151(7) 0.0401(2) 0.0338(15) Uani 1 1 d . . . O1 O 1.3325(7) -0.1886(7) 0.0886(2) 0.0549(19) Uani 1 1 d . . . O2 O 0.8060(7) 0.1216(7) 0.0912(2) 0.0466(17) Uani 1 1 d . . . O3 O 0.5789(6) 0.1755(8) 0.1157(3) 0.070(2) Uani 1 1 d . . . C1 C 1.2315(9) -0.1042(9) 0.0880(3) 0.037(2) Uani 1 1 d . . . C2 C 1.1908(8) -0.0347(9) 0.0399(3) 0.0337(18) Uani 1 1 d . . . H2 H 1.2060 -0.0978 0.0115 0.05(3) Uiso 1 1 calc R . . C3 C 1.2849(10) 0.0976(9) 0.0321(4) 0.050(3) Uani 1 1 d . . . H3A H 1.3564 0.1079 0.0591 0.05(3) Uiso 1 1 calc R . . H3B H 1.3372 0.0938 0.0001 0.07(3) Uiso 1 1 calc R . . C4 C 1.1759(10) 0.2151(10) 0.0324(4) 0.054(3) Uani 1 1 d . . . H4A H 1.1626 0.2513 0.0663 0.11(5) Uiso 1 1 calc R . . H4B H 1.2079 0.2888 0.0102 0.03(2) Uiso 1 1 calc R . . C5 C 1.0368(11) 0.1495(9) 0.0133(4) 0.050(2) Uani 1 1 d . . . H5A H 0.9509 0.2047 0.0218 0.04(3) Uiso 1 1 calc R . . H5B H 1.0404 0.1367 -0.0230 0.11(4) Uiso 1 1 calc R . . C6 C 0.9280(10) -0.0804(10) 0.0151(3) 0.046(3) Uani 1 1 d . . . H6A H 0.9710 -0.1104 -0.0167 0.06(3) Uiso 1 1 calc R . . H6B H 0.8384 -0.0299 0.0071 0.024(19) Uiso 1 1 calc R . . C7 C 0.8861(10) -0.2065(10) 0.0454(3) 0.045(2) Uani 1 1 d . . . C8 C 0.9802(14) -0.3161(10) 0.0509(4) 0.063(3) Uani 1 1 d . . . H8 H 1.0731 -0.3140 0.0358 0.08(4) Uiso 1 1 calc R . . C9 C 0.9371(17) -0.4303(13) 0.0788(5) 0.089(4) Uani 1 1 d . . . H9 H 0.9997 -0.5059 0.0815 0.08(4) Uiso 1 1 calc R . . C10 C 0.8017(19) -0.4314(18) 0.1027(6) 0.108(6) Uani 1 1 d . . . H10 H 0.7752 -0.5062 0.1227 0.17(7) Uiso 1 1 calc R . . C11 C 0.7058(18) -0.3237(16) 0.0973(5) 0.096(5) Uani 1 1 d . . . H11 H 0.6123 -0.3274 0.1119 0.13(6) Uiso 1 1 calc R . . C12 C 0.7490(13) -0.2089(13) 0.0699(4) 0.061(3) Uani 1 1 d . . . H12 H 0.6865 -0.1332 0.0678 0.08(4) Uiso 1 1 calc R . . C13 C 0.6985(10) 0.1241(10) 0.1234(4) 0.049(3) Uani 1 1 d . . . C14 C 0.7315(8) 0.0494(11) 0.1719(3) 0.046(2) Uani 1 1 d . . . H14A H 0.7034 0.1064 0.2005 0.06(3) Uiso 1 1 calc R . . H14B H 0.6743 -0.0349 0.1734 0.08(4) Uiso 1 1 calc R . . C19 C 0.9476(8) -0.0336(10) 0.2159(3) 0.0332(18) Uani 1 1 d . . . C20 C 0.8519(8) -0.0548(9) 0.2613(3) 0.035(2) Uani 1 1 d . . . C21 C 0.8138(10) 0.0516(9) 0.2916(3) 0.046(2) Uani 1 1 d . . . H21 H 0.8463 0.1399 0.2839 0.05(3) Uiso 1 1 calc R . . C22 C 0.7255(10) 0.0296(13) 0.3344(4) 0.057(3) Uani 1 1 d . . . H22 H 0.6998 0.1031 0.3551 0.12(5) Uiso 1 1 calc R . . C23 C 0.6767(11) -0.1018(13) 0.3458(4) 0.061(3) Uani 1 1 d . . . H23 H 0.6182 -0.1168 0.3742 0.18(7) Uiso 1 1 calc R . . C24 C 0.7149(11) -0.2095(11) 0.3151(3) 0.052(3) Uani 1 1 d . . . H24 H 0.6808 -0.2975 0.3225 0.15(6) Uiso 1 1 calc R . . C25 C 0.8047(10) -0.1881(10) 0.2729(4) 0.045(2) Uani 1 1 d . . . H25 H 0.8327 -0.2618 0.2526 0.06(3) Uiso 1 1 calc R . . C26 C 1.1043(8) -0.0644(8) 0.2196(3) 0.031(2) Uani 1 1 d . . . C27 C 1.2024(9) -0.0741(9) 0.1777(3) 0.037(2) Uani 1 1 d . . . C28 C 1.3525(9) -0.0981(10) 0.1877(4) 0.049(3) Uani 1 1 d . . . H28 H 1.4189 -0.1039 0.1609 0.04(3) Uiso 1 1 calc R . . C29 C 1.4031(10) -0.1130(11) 0.2361(4) 0.062(3) Uani 1 1 d . . . H29 H 1.5037 -0.1266 0.2414 0.06(3) Uiso 1 1 calc R . . C30 C 1.3094(10) -0.1085(12) 0.2776(4) 0.060(3) Uani 1 1 d . . . H30 H 1.3449 -0.1212 0.3103 0.15(6) Uiso 1 1 calc R . . C31 C 1.1619(10) -0.0845(10) 0.2684(4) 0.046(3) Uani 1 1 d . . . H31 H 1.0973 -0.0814 0.2957 0.06(3) 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 0.0254(4) 0.0373(5) 0.0353(5) 0.0013(6) -0.0013(5) 0.0043(5) N1 0.022(3) 0.039(4) 0.038(4) -0.006(4) -0.008(3) 0.001(3) N2 0.024(3) 0.031(4) 0.046(4) 0.006(3) 0.001(3) -0.001(3) N3 0.033(3) 0.043(4) 0.025(3) 0.005(3) 0.004(3) 0.002(4) O1 0.048(4) 0.062(5) 0.055(4) 0.010(4) 0.009(3) 0.032(4) O2 0.039(4) 0.063(4) 0.037(3) 0.000(3) -0.008(3) 0.025(3) O3 0.038(3) 0.110(6) 0.062(4) -0.011(5) -0.005(4) 0.037(4) C1 0.029(4) 0.034(5) 0.048(5) 0.006(4) 0.002(4) 0.001(4) C2 0.029(4) 0.036(4) 0.037(4) -0.001(5) 0.007(4) 0.007(5) C3 0.034(5) 0.053(6) 0.062(7) 0.017(5) 0.009(5) -0.007(5) C4 0.042(6) 0.046(6) 0.075(8) 0.022(6) 0.008(5) -0.008(5) C5 0.044(5) 0.042(5) 0.065(7) 0.020(5) 0.004(6) 0.004(5) C6 0.043(6) 0.057(6) 0.038(5) -0.001(5) -0.007(4) -0.001(5) C7 0.047(6) 0.057(6) 0.032(5) -0.003(5) -0.009(5) -0.008(5) C8 0.058(7) 0.064(7) 0.066(6) 0.004(6) -0.016(7) -0.012(7) C9 0.115(12) 0.059(8) 0.094(10) 0.012(7) -0.052(9) -0.006(8) C10 0.128(14) 0.119(14) 0.078(10) 0.032(10) -0.017(10) -0.055(12) C11 0.093(12) 0.118(13) 0.076(10) -0.006(9) 0.002(9) -0.051(10) C12 0.065(7) 0.068(8) 0.050(7) -0.018(6) 0.009(6) -0.017(7) C13 0.034(5) 0.056(6) 0.057(7) -0.012(5) -0.011(5) 0.018(5) C14 0.024(4) 0.063(7) 0.051(6) 0.000(6) -0.003(4) 0.013(5) C19 0.025(4) 0.032(4) 0.043(4) -0.005(5) -0.003(3) 0.004(4) C20 0.025(4) 0.034(5) 0.046(5) 0.002(4) 0.000(4) 0.001(4) C21 0.049(5) 0.036(6) 0.054(6) -0.001(5) 0.020(5) -0.001(5) C22 0.057(6) 0.063(6) 0.050(6) -0.005(7) 0.001(5) 0.000(7) C23 0.040(6) 0.076(8) 0.066(7) 0.016(7) 0.003(6) 0.005(6) C24 0.050(6) 0.059(7) 0.047(6) 0.024(5) 0.010(5) -0.007(6) C25 0.044(6) 0.039(5) 0.053(6) 0.004(5) 0.007(5) 0.006(5) C26 0.025(4) 0.034(5) 0.036(5) -0.001(4) -0.003(4) 0.004(4) C27 0.025(4) 0.038(5) 0.048(5) 0.002(4) 0.004(4) 0.004(4) C28 0.024(4) 0.064(7) 0.058(6) 0.018(5) 0.000(5) 0.010(5) C29 0.030(5) 0.095(9) 0.062(7) 0.025(7) -0.016(5) 0.015(6) C30 0.046(6) 0.094(9) 0.039(6) 0.001(6) -0.016(5) -0.002(6) C31 0.032(5) 0.065(7) 0.041(5) 0.008(5) -0.004(4) 0.000(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 O2 1.853(6) . ? Ni1 N2 1.854(6) . ? Ni1 N1 1.862(6) . ? Ni1 N3 1.945(5) . ? N1 C19 1.288(9) . ? N1 C14 1.487(9) . ? N2 C1 1.376(10) . ? N2 C27 1.389(10) . ? N3 C5 1.486(9) . ? N3 C6 1.487(10) . ? N3 C2 1.503(9) . ? O1 C1 1.227(9) . ? O2 C13 1.292(10) . ? O3 C13 1.209(9) . ? C1 C2 1.488(11) . ? C2 C3 1.556(11) . ? C3 C4 1.509(12) . ? C4 C5 1.498(12) . ? C6 C7 1.513(12) . ? C7 C8 1.371(13) . ? C7 C12 1.400(13) . ? C8 C9 1.390(14) . ? C9 C10 1.378(17) . ? C10 C11 1.367(19) . ? C11 C12 1.387(16) . ? C13 C14 1.505(12) . ? C19 C26 1.452(9) . ? C19 C20 1.496(11) . ? C20 C21 1.352(11) . ? C20 C25 1.398(12) . ? C21 C22 1.402(11) . ? C22 C23 1.385(14) . ? C23 C24 1.369(14) . ? C24 C25 1.397(12) . ? C26 C31 1.404(11) . ? C26 C27 1.424(11) . ? C27 C28 1.402(10) . ? C28 C29 1.367(12) . ? C29 C30 1.387(12) . ? C30 C31 1.376(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 O2 Ni1 N2 176.5(3) . . ? O2 Ni1 N1 87.2(3) . . ? N2 Ni1 N1 95.1(3) . . ? O2 Ni1 N3 89.3(3) . . ? N2 Ni1 N3 89.0(3) . . ? N1 Ni1 N3 169.1(3) . . ? C19 N1 C14 120.6(7) . . ? C19 N1 Ni1 129.0(5) . . ? C14 N1 Ni1 109.4(5) . . ? C1 N2 C27 120.7(7) . . ? C1 N2 Ni1 113.9(5) . . ? C27 N2 Ni1 125.4(5) . . ? C5 N3 C6 110.5(6) . . ? C5 N3 C2 105.2(7) . . ? C6 N3 C2 113.8(6) . . ? C5 N3 Ni1 113.9(5) . . ? C6 N3 Ni1 107.2(5) . . ? C2 N3 Ni1 106.4(4) . . ? C13 O2 Ni1 116.5(5) . . ? O1 C1 N2 127.5(8) . . ? O1 C1 C2 119.9(8) . . ? N2 C1 C2 112.5(7) . . ? C1 C2 N3 112.2(6) . . ? C1 C2 C3 110.7(7) . . ? N3 C2 C3 104.6(7) . . ? C4 C3 C2 105.6(7) . . ? C5 C4 C3 102.9(8) . . ? N3 C5 C4 103.4(8) . . ? N3 C6 C7 115.5(7) . . ? C8 C7 C12 119.2(11) . . ? C8 C7 C6 122.0(9) . . ? C12 C7 C6 118.8(10) . . ? C7 C8 C9 120.2(12) . . ? C10 C9 C8 119.9(15) . . ? C11 C10 C9 120.7(16) . . ? C10 C11 C12 119.5(15) . . ? C11 C12 C7 120.4(13) . . ? O3 C13 O2 124.8(9) . . ? O3 C13 C14 121.3(9) . . ? O2 C13 C14 113.8(7) . . ? N1 C14 C13 110.1(7) . . ? N1 C19 C26 121.2(8) . . ? N1 C19 C20 120.0(7) . . ? C26 C19 C20 118.7(8) . . ? C21 C20 C25 120.2(9) . . ? C21 C20 C19 121.2(8) . . ? C25 C20 C19 118.6(8) . . ? C20 C21 C22 120.4(10) . . ? C23 C22 C21 119.9(10) . . ? C24 C23 C22 119.7(10) . . ? C23 C24 C25 120.5(10) . . ? C24 C25 C20 119.3(9) . . ? C31 C26 C27 118.4(7) . . ? C31 C26 C19 117.0(8) . . ? C27 C26 C19 124.6(8) . . ? N2 C27 C28 121.3(8) . . ? N2 C27 C26 120.8(7) . . ? C28 C27 C26 117.9(8) . . ? C29 C28 C27 121.2(9) . . ? C28 C29 C30 122.2(9) . . ? C31 C30 C29 117.2(9) . . ? C30 C31 C26 123.0(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Ni1 N1 C19 -176.3(8) . . . . ? N2 Ni1 N1 C19 1.0(8) . . . . ? N3 Ni1 N1 C19 112.3(15) . . . . ? O2 Ni1 N1 C14 15.1(6) . . . . ? N2 Ni1 N1 C14 -167.6(6) . . . . ? N3 Ni1 N1 C14 -56.3(19) . . . . ? O2 Ni1 N2 C1 -68(5) . . . . ? N1 Ni1 N2 C1 162.5(6) . . . . ? N3 Ni1 N2 C1 -7.3(6) . . . . ? O2 Ni1 N2 C27 112(5) . . . . ? N1 Ni1 N2 C27 -17.1(7) . . . . ? N3 Ni1 N2 C27 173.1(7) . . . . ? O2 Ni1 N3 C5 53.6(6) . . . . ? N2 Ni1 N3 C5 -123.3(6) . . . . ? N1 Ni1 N3 C5 124.8(15) . . . . ? O2 Ni1 N3 C6 -68.9(5) . . . . ? N2 Ni1 N3 C6 114.2(5) . . . . ? N1 Ni1 N3 C6 2.4(18) . . . . ? O2 Ni1 N3 C2 169.0(5) . . . . ? N2 Ni1 N3 C2 -7.9(5) . . . . ? N1 Ni1 N3 C2 -119.7(15) . . . . ? N2 Ni1 O2 C13 -139(5) . . . . ? N1 Ni1 O2 C13 -9.2(7) . . . . ? N3 Ni1 O2 C13 160.4(7) . . . . ? C27 N2 C1 O1 16.9(13) . . . . ? Ni1 N2 C1 O1 -162.7(7) . . . . ? C27 N2 C1 C2 -159.2(7) . . . . ? Ni1 N2 C1 C2 21.1(8) . . . . ? O1 C1 C2 N3 155.7(8) . . . . ? N2 C1 C2 N3 -27.9(10) . . . . ? O1 C1 C2 C3 -87.9(10) . . . . ? N2 C1 C2 C3 88.6(8) . . . . ? C5 N3 C2 C1 141.9(8) . . . . ? C6 N3 C2 C1 -97.1(8) . . . . ? Ni1 N3 C2 C1 20.7(8) . . . . ? C5 N3 C2 C3 21.8(8) . . . . ? C6 N3 C2 C3 142.9(7) . . . . ? Ni1 N3 C2 C3 -99.4(6) . . . . ? C1 C2 C3 C4 -116.8(9) . . . . ? N3 C2 C3 C4 4.3(9) . . . . ? C2 C3 C4 C5 -28.3(10) . . . . ? C6 N3 C5 C4 -163.5(7) . . . . ? C2 N3 C5 C4 -40.2(9) . . . . ? Ni1 N3 C5 C4 75.9(8) . . . . ? C3 C4 C5 N3 42.3(10) . . . . ? C5 N3 C6 C7 -165.6(8) . . . . ? C2 N3 C6 C7 76.3(9) . . . . ? Ni1 N3 C6 C7 -41.0(9) . . . . ? N3 C6 C7 C8 -75.8(11) . . . . ? N3 C6 C7 C12 102.1(10) . . . . ? C12 C7 C8 C9 2.5(14) . . . . ? C6 C7 C8 C9 -179.7(9) . . . . ? C7 C8 C9 C10 -2.4(17) . . . . ? C8 C9 C10 C11 3(2) . . . . ? C9 C10 C11 C12 -4(2) . . . . ? C10 C11 C12 C7 3.8(18) . . . . ? C8 C7 C12 C11 -3.2(14) . . . . ? C6 C7 C12 C11 178.9(9) . . . . ? Ni1 O2 C13 O3 -176.8(8) . . . . ? Ni1 O2 C13 C14 0.2(11) . . . . ? C19 N1 C14 C13 172.2(8) . . . . ? Ni1 N1 C14 C13 -18.2(10) . . . . ? O3 C13 C14 N1 -170.9(9) . . . . ? O2 C13 C14 N1 12.0(12) . . . . ? C14 N1 C19 C26 -179.1(9) . . . . ? Ni1 N1 C19 C26 13.5(13) . . . . ? C14 N1 C19 C20 -2.0(13) . . . . ? Ni1 N1 C19 C20 -169.5(6) . . . . ? N1 C19 C20 C21 -78.2(11) . . . . ? C26 C19 C20 C21 99.0(11) . . . . ? N1 C19 C20 C25 103.2(10) . . . . ? C26 C19 C20 C25 -79.6(11) . . . . ? C25 C20 C21 C22 -0.6(13) . . . . ? C19 C20 C21 C22 -179.2(7) . . . . ? C20 C21 C22 C23 -0.1(14) . . . . ? C21 C22 C23 C24 0.0(16) . . . . ? C22 C23 C24 C25 1.0(16) . . . . ? C23 C24 C25 C20 -1.8(14) . . . . ? C21 C20 C25 C24 1.6(13) . . . . ? C19 C20 C25 C24 -179.8(7) . . . . ? N1 C19 C26 C31 164.1(8) . . . . ? C20 C19 C26 C31 -13.1(14) . . . . ? N1 C19 C26 C27 -15.3(15) . . . . ? C20 C19 C26 C27 167.6(8) . . . . ? C1 N2 C27 C28 21.0(12) . . . . ? Ni1 N2 C27 C28 -159.4(7) . . . . ? C1 N2 C27 C26 -160.8(8) . . . . ? Ni1 N2 C27 C26 18.8(11) . . . . ? C31 C26 C27 N2 179.4(8) . . . . ? C19 C26 C27 N2 -1.3(14) . . . . ? C31 C26 C27 C28 -2.4(13) . . . . ? C19 C26 C27 C28 176.9(9) . . . . ? N2 C27 C28 C29 178.9(9) . . . . ? C26 C27 C28 C29 0.6(14) . . . . ? C27 C28 C29 C30 1.5(17) . . . . ? C28 C29 C30 C31 -1.7(17) . . . . ? C29 C30 C31 C26 -0.2(17) . . . . ? C27 C26 C31 C30 2.2(15) . . . . ? C19 C26 C31 C30 -177.1(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.611 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.108