# 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_Ni_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N4 Ni O5' _chemical_formula_weight 465.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1130(12) _cell_length_b 13.3230(16) _cell_length_c 15.4730(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.2000(13) _cell_angle_gamma 90.00 _cell_volume 2021.1(4) _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 block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.002 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7531 _exptl_absorpt_correction_T_max 0.8247 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12316 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4624 _reflns_number_gt 4059 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART(Bruker,1998) _computing_cell_refinement 'Bruker SMART' _computing_data_reduction SAINT(Bruker,1998) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker,1998)' _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^)+(0.0381P)^2^+0.6564P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4624 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0736 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.754731(17) 0.166598(13) 0.922851(13) 0.01954(7) Uani 1 1 d . . . O3 O 1.54893(11) 0.15322(8) 0.93845(8) 0.0269(2) Uani 1 1 d . . . O5 O 0.88314(13) 0.10381(9) 1.03927(8) 0.0307(3) Uani 1 1 d . . . H5A H 0.873(2) 0.0463(18) 1.0507(15) 0.046 Uiso 1 1 d . . . H5B H 0.956(2) 0.1049(17) 1.0210(14) 0.046 Uiso 1 1 d . . . O4 O 1.59592(10) 0.22973(8) 0.82366(7) 0.0262(2) Uani 1 1 d . . . O2 O 1.06929(11) 0.10798(9) 0.94363(9) 0.0350(3) Uani 1 1 d . . . N4 N 0.76360(15) 0.46940(10) 0.98987(10) 0.0312(3) Uani 1 1 d . . . O1 O 0.90896(10) 0.21182(8) 0.86799(8) 0.0281(2) Uani 1 1 d . . . N2 N 0.74767(14) -0.13700(10) 0.85850(9) 0.0256(3) Uani 1 1 d . . . N1 N 0.73977(13) 0.02830(9) 0.86174(9) 0.0245(3) Uani 1 1 d . . . C3 C 1.26631(15) 0.19169(11) 0.87027(11) 0.0230(3) Uani 1 1 d . . . H3 H 1.2913(19) 0.1399(15) 0.9093(12) 0.028 Uiso 1 1 d . . . C1 C 1.13223(14) 0.22603(11) 0.84667(10) 0.0232(3) Uani 1 1 d . . . C7 C 1.19715(16) 0.35293(12) 0.75223(12) 0.0291(3) Uani 1 1 d . . . C8 C 1.09879(15) 0.30680(12) 0.78835(11) 0.0273(3) Uani 1 1 d . . . H8 H 1.006(2) 0.3309(13) 0.7732(13) 0.033 Uiso 1 1 d . . . C5 C 1.51162(14) 0.20379(11) 0.86773(10) 0.0221(3) Uani 1 1 d . . . C19 C 0.80107(18) -0.00156(12) 0.79533(11) 0.0303(3) Uani 1 1 d . . . H19 H 0.8299(19) 0.0476(15) 0.7603(13) 0.036 Uiso 1 1 d . . . N3 N 0.77204(14) 0.30404(10) 0.98839(10) 0.0281(3) Uani 1 1 d . . . C4 C 1.36575(14) 0.23735(11) 0.83626(10) 0.0222(3) Uani 1 1 d . . . C21 C 0.80743(18) -0.10289(12) 0.79299(11) 0.0316(4) Uani 1 1 d . . . H21 H 0.8446 -0.1417 0.7549 0.038 Uiso 1 1 calc R . . C6 C 1.02887(15) 0.17749(11) 0.88898(11) 0.0236(3) Uani 1 1 d . . . C9 C 1.1608(2) 0.44010(18) 0.68843(17) 0.0487(5) Uani 1 1 d . . . H9A H 1.142(3) 0.424(2) 0.626(2) 0.072 Uiso 1 1 d . . . H9B H 1.234(3) 0.483(2) 0.6949(17) 0.072 Uiso 1 1 d . . . H9C H 1.083(3) 0.477(2) 0.6945(18) 0.072 Uiso 1 1 d . . . C18 C 0.85797(19) 0.70076(13) 0.88679(13) 0.0350(4) Uani 1 1 d . . . H18 H 0.930(2) 0.7249(16) 0.8634(13) 0.042 Uiso 1 1 d . . . C14 C 0.75952(17) 0.57010(11) 0.95711(12) 0.0304(4) Uani 1 1 d . . . C15 C 0.6495(2) 0.63090(13) 0.95915(14) 0.0367(4) Uani 1 1 d . . . H15 H 0.579(2) 0.6075(16) 0.9814(14) 0.044 Uiso 1 1 d . . . C16 C 0.64404(19) 0.72780(13) 0.92536(13) 0.0351(4) Uani 1 1 d . . . H16 H 0.574(2) 0.7674(16) 0.9267(14) 0.042 Uiso 1 1 d . . . C10 C 1.33067(16) 0.31727(12) 0.77701(11) 0.0273(3) Uani 1 1 d . . . H10 H 1.399(2) 0.3462(14) 0.7551(13) 0.033 Uiso 1 1 d . . . C20 C 0.70856(16) -0.05486(11) 0.89747(11) 0.0254(3) Uani 1 1 d . . . H20 H 0.6650 -0.0572 0.9438 0.030 Uiso 1 1 calc R . . C17 C 0.74833(16) 0.76196(11) 0.88946(11) 0.0269(3) Uani 1 1 d . . . C13 C 0.86298(18) 0.60402(12) 0.92065(13) 0.0349(4) Uani 1 1 d . . . H13 H 0.939(2) 0.5630(16) 0.9217(13) 0.042 Uiso 1 1 d . . . C11 C 0.7411(2) 0.33497(14) 1.06552(13) 0.0411(5) Uani 1 1 d . . . H11 H 0.728(2) 0.2894(18) 1.1090(15) 0.049 Uiso 1 1 d . . . C12 C 0.78600(18) 0.38676(12) 0.94528(12) 0.0306(4) Uani 1 1 d . . . H12 H 0.8016(19) 0.3893(15) 0.8889(14) 0.037 Uiso 1 1 d . . . C1A C 0.7343(2) 0.43633(15) 1.06736(14) 0.0462(5) Uani 1 1 d . . . H1A H 0.722(2) 0.4780(18) 1.1068(16) 0.055 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01515(10) 0.01483(10) 0.02961(12) 0.00272(7) 0.00732(8) 0.00162(6) O3 0.0191(5) 0.0295(6) 0.0337(6) 0.0083(5) 0.0093(4) 0.0032(4) O5 0.0304(6) 0.0266(6) 0.0349(7) 0.0055(5) 0.0078(5) 0.0052(5) O4 0.0177(5) 0.0281(6) 0.0354(6) 0.0076(5) 0.0117(4) 0.0033(4) O2 0.0211(5) 0.0335(6) 0.0526(8) 0.0190(6) 0.0130(5) 0.0047(5) N4 0.0423(8) 0.0176(6) 0.0336(8) -0.0007(5) 0.0093(6) 0.0006(6) O1 0.0160(5) 0.0267(6) 0.0433(7) 0.0088(5) 0.0108(5) 0.0024(4) N2 0.0303(7) 0.0172(6) 0.0287(7) -0.0007(5) 0.0060(6) 0.0025(5) N1 0.0245(6) 0.0189(6) 0.0303(7) 0.0009(5) 0.0070(5) 0.0019(5) C3 0.0195(7) 0.0205(7) 0.0294(8) 0.0031(6) 0.0066(6) 0.0020(6) C1 0.0168(6) 0.0228(7) 0.0314(8) 0.0002(6) 0.0082(6) -0.0001(5) C7 0.0236(8) 0.0283(8) 0.0354(9) 0.0096(7) 0.0073(7) 0.0030(6) C8 0.0163(7) 0.0288(8) 0.0365(9) 0.0055(7) 0.0062(6) 0.0037(6) C5 0.0167(6) 0.0197(7) 0.0312(8) 0.0005(6) 0.0087(6) 0.0007(5) C19 0.0364(9) 0.0253(8) 0.0311(8) 0.0028(7) 0.0117(7) 0.0019(7) N3 0.0295(7) 0.0191(6) 0.0354(8) 0.0018(5) 0.0074(6) -0.0006(5) C4 0.0157(6) 0.0235(7) 0.0281(8) -0.0002(6) 0.0064(6) 0.0018(5) C21 0.0395(9) 0.0267(8) 0.0304(9) -0.0029(7) 0.0119(7) 0.0036(7) C6 0.0178(7) 0.0202(7) 0.0338(8) -0.0002(6) 0.0079(6) -0.0008(5) C9 0.0343(10) 0.0495(12) 0.0632(14) 0.0332(11) 0.0136(10) 0.0097(9) C18 0.0338(9) 0.0232(8) 0.0494(11) 0.0029(7) 0.0133(8) 0.0020(7) C14 0.0386(9) 0.0163(7) 0.0341(9) -0.0012(6) 0.0050(7) 0.0001(6) C15 0.0402(10) 0.0236(8) 0.0503(11) 0.0020(8) 0.0186(8) -0.0006(7) C16 0.0358(9) 0.0219(8) 0.0497(11) 0.0006(7) 0.0145(8) 0.0059(7) C10 0.0216(7) 0.0280(8) 0.0345(9) 0.0064(7) 0.0111(7) -0.0009(6) C20 0.0266(7) 0.0194(7) 0.0307(8) -0.0004(6) 0.0082(6) 0.0022(6) C17 0.0323(8) 0.0155(7) 0.0305(8) -0.0020(6) 0.0032(6) 0.0001(6) C13 0.0325(9) 0.0213(8) 0.0508(11) 0.0026(7) 0.0100(8) 0.0063(7) C11 0.0607(13) 0.0281(9) 0.0388(10) 0.0065(8) 0.0202(10) 0.0012(8) C12 0.0395(9) 0.0195(7) 0.0327(9) -0.0013(7) 0.0087(7) 0.0000(7) C1A 0.0765(15) 0.0286(9) 0.0402(11) -0.0038(8) 0.0270(11) 0.0017(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 Ni1 O1 2.0411(11) . ? Ni1 N1 2.0596(13) . ? Ni1 N3 2.0797(14) . ? Ni1 O4 2.1054(11) 1_455 ? Ni1 O5 2.1173(12) . ? Ni1 O3 2.1606(11) 1_455 ? Ni1 C5 2.4472(14) 1_455 ? O3 C5 1.2614(19) . ? O3 Ni1 2.1606(11) 1_655 ? O5 H5A 0.80(2) . ? O5 H5B 0.85(2) . ? O4 C5 1.2635(17) . ? O4 Ni1 2.1054(11) 1_655 ? O2 C6 1.2530(19) . ? N4 C12 1.348(2) . ? N4 C1A 1.376(2) . ? N4 C14 1.431(2) . ? O1 C6 1.2617(17) . ? N2 C20 1.3545(19) . ? N2 C21 1.378(2) . ? N2 C17 1.4284(19) 1_545 ? N1 C20 1.311(2) . ? N1 C19 1.382(2) . ? C3 C4 1.385(2) . ? C3 C1 1.392(2) . ? C3 H3 0.911(19) . ? C1 C8 1.392(2) . ? C1 C6 1.508(2) . ? C7 C10 1.394(2) . ? C7 C8 1.397(2) . ? C7 C9 1.510(2) . ? C8 H8 0.97(2) . ? C5 C4 1.5036(19) . ? C5 Ni1 2.4472(14) 1_655 ? C19 C21 1.352(2) . ? C19 H19 0.94(2) . ? N3 C12 1.314(2) . ? N3 C11 1.370(2) . ? C4 C10 1.393(2) . ? C21 H21 0.9300 . ? C9 H9A 0.96(3) . ? C9 H9B 0.93(3) . ? C9 H9C 0.95(3) . ? C18 C17 1.385(2) . ? C18 C13 1.387(2) . ? C18 H18 0.95(2) . ? C14 C13 1.381(3) . ? C14 C15 1.383(2) . ? C15 C16 1.389(2) . ? C15 H15 0.92(2) . ? C16 C17 1.384(2) . ? C16 H16 0.89(2) . ? C10 H10 0.92(2) . ? C20 H20 0.9300 . ? C17 N2 1.4284(19) 1_565 ? C13 H13 0.94(2) . ? C11 C1A 1.353(3) . ? C11 H11 0.94(2) . ? C12 H12 0.93(2) . ? C1A H1A 0.86(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 O1 Ni1 N1 92.91(5) . . ? O1 Ni1 N3 87.79(5) . . ? N1 Ni1 N3 178.21(5) . . ? O1 Ni1 O4 95.91(4) . 1_455 ? N1 Ni1 O4 93.77(5) . 1_455 ? N3 Ni1 O4 87.80(5) . 1_455 ? O1 Ni1 O5 95.66(5) . . ? N1 Ni1 O5 89.87(5) . . ? N3 Ni1 O5 88.41(5) . . ? O4 Ni1 O5 167.67(5) 1_455 . ? O1 Ni1 O3 157.84(4) . 1_455 ? N1 Ni1 O3 90.76(5) . 1_455 ? N3 Ni1 O3 89.21(5) . 1_455 ? O4 Ni1 O3 62.03(4) 1_455 1_455 ? O5 Ni1 O3 106.20(5) . 1_455 ? O1 Ni1 C5 126.88(5) . 1_455 ? N1 Ni1 C5 93.83(5) . 1_455 ? N3 Ni1 C5 87.07(5) . 1_455 ? O4 Ni1 C5 31.08(4) 1_455 1_455 ? O5 Ni1 C5 136.93(5) . 1_455 ? O3 Ni1 C5 30.98(5) 1_455 1_455 ? C5 O3 Ni1 87.16(8) . 1_655 ? Ni1 O5 H5A 118.9(16) . . ? Ni1 O5 H5B 96.4(15) . . ? H5A O5 H5B 105(2) . . ? C5 O4 Ni1 89.56(9) . 1_655 ? C12 N4 C1A 106.48(15) . . ? C12 N4 C14 125.34(15) . . ? C1A N4 C14 127.95(15) . . ? C6 O1 Ni1 124.76(10) . . ? C20 N2 C21 106.84(13) . . ? C20 N2 C17 126.15(14) . 1_545 ? C21 N2 C17 126.20(14) . 1_545 ? C20 N1 C19 105.58(13) . . ? C20 N1 Ni1 124.10(11) . . ? C19 N1 Ni1 127.08(11) . . ? C4 C3 C1 120.48(14) . . ? C4 C3 H3 118.3(12) . . ? C1 C3 H3 121.2(12) . . ? C8 C1 C3 119.36(14) . . ? C8 C1 C6 121.93(13) . . ? C3 C1 C6 118.64(14) . . ? C10 C7 C8 118.48(14) . . ? C10 C7 C9 120.41(15) . . ? C8 C7 C9 121.11(15) . . ? C1 C8 C7 121.05(14) . . ? C1 C8 H8 118.7(11) . . ? C7 C8 H8 120.2(11) . . ? O3 C5 O4 121.09(13) . . ? O3 C5 C4 120.05(13) . . ? O4 C5 C4 118.82(13) . . ? O3 C5 Ni1 61.86(7) . 1_655 ? O4 C5 Ni1 59.35(7) . 1_655 ? C4 C5 Ni1 174.30(11) . 1_655 ? C21 C19 N1 109.88(15) . . ? C21 C19 H19 131.0(12) . . ? N1 C19 H19 119.1(12) . . ? C12 N3 C11 105.44(14) . . ? C12 N3 Ni1 119.85(12) . . ? C11 N3 Ni1 132.84(12) . . ? C3 C4 C10 119.63(13) . . ? C3 C4 C5 119.50(13) . . ? C10 C4 C5 120.78(13) . . ? C19 C21 N2 106.09(15) . . ? C19 C21 H21 127.0 . . ? N2 C21 H21 127.0 . . ? O2 C6 O1 125.14(14) . . ? O2 C6 C1 117.62(13) . . ? O1 C6 C1 117.22(13) . . ? C7 C9 H9A 116.1(17) . . ? C7 C9 H9B 110.3(17) . . ? H9A C9 H9B 102(2) . . ? C7 C9 H9C 113.8(16) . . ? H9A C9 H9C 104(2) . . ? H9B C9 H9C 110(2) . . ? C17 C18 C13 119.40(17) . . ? C17 C18 H18 120.6(13) . . ? C13 C18 H18 120.0(13) . . ? C13 C14 C15 120.81(16) . . ? C13 C14 N4 119.51(15) . . ? C15 C14 N4 119.63(16) . . ? C14 C15 C16 119.58(17) . . ? C14 C15 H15 120.9(14) . . ? C16 C15 H15 119.6(13) . . ? C17 C16 C15 119.54(16) . . ? C17 C16 H16 120.4(14) . . ? C15 C16 H16 120.0(14) . . ? C4 C10 C7 120.98(14) . . ? C4 C10 H10 117.9(12) . . ? C7 C10 H10 121.1(12) . . ? N1 C20 N2 111.61(14) . . ? N1 C20 H20 124.2 . . ? N2 C20 H20 124.2 . . ? C16 C17 C18 120.85(16) . . ? C16 C17 N2 120.21(14) . 1_565 ? C18 C17 N2 118.87(15) . 1_565 ? C14 C13 C18 119.81(16) . . ? C14 C13 H13 119.9(13) . . ? C18 C13 H13 120.2(13) . . ? C1A C11 N3 110.00(17) . . ? C1A C11 H11 127.8(14) . . ? N3 C11 H11 122.2(14) . . ? N3 C12 N4 111.89(16) . . ? N3 C12 H12 125.1(13) . . ? N4 C12 H12 122.8(13) . . ? C11 C1A N4 106.18(17) . . ? C11 C1A H1A 132.8(16) . . ? N4 C1A H1A 120.9(16) . . ? 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 N1 Ni1 O1 C6 -70.25(13) . . . . ? N3 Ni1 O1 C6 108.10(13) . . . . ? O4 Ni1 O1 C6 -164.34(13) 1_455 . . . ? O5 Ni1 O1 C6 19.92(13) . . . . ? O3 Ni1 O1 C6 -169.44(12) 1_455 . . . ? C5 Ni1 O1 C6 -167.24(12) 1_455 . . . ? O1 Ni1 N1 C20 145.81(12) . . . . ? N3 Ni1 N1 C20 33.0(17) . . . . ? O4 Ni1 N1 C20 -118.06(12) 1_455 . . . ? O5 Ni1 N1 C20 50.15(12) . . . . ? O3 Ni1 N1 C20 -56.05(12) 1_455 . . . ? C5 Ni1 N1 C20 -86.91(13) 1_455 . . . ? O1 Ni1 N1 C19 -10.85(14) . . . . ? N3 Ni1 N1 C19 -123.6(16) . . . . ? O4 Ni1 N1 C19 85.28(13) 1_455 . . . ? O5 Ni1 N1 C19 -106.51(14) . . . . ? O3 Ni1 N1 C19 147.29(13) 1_455 . . . ? C5 Ni1 N1 C19 116.43(13) 1_455 . . . ? C4 C3 C1 C8 0.1(2) . . . . ? C4 C3 C1 C6 -176.90(14) . . . . ? C3 C1 C8 C7 0.9(3) . . . . ? C6 C1 C8 C7 177.78(15) . . . . ? C10 C7 C8 C1 -1.0(3) . . . . ? C9 C7 C8 C1 179.55(19) . . . . ? Ni1 O3 C5 O4 3.98(14) 1_655 . . . ? Ni1 O3 C5 C4 -173.85(13) 1_655 . . . ? Ni1 O4 C5 O3 -4.08(15) 1_655 . . . ? Ni1 O4 C5 C4 173.78(12) 1_655 . . . ? C20 N1 C19 C21 -0.83(19) . . . . ? Ni1 N1 C19 C21 159.26(12) . . . . ? O1 Ni1 N3 C12 43.57(13) . . . . ? N1 Ni1 N3 C12 156.4(16) . . . . ? O4 Ni1 N3 C12 -52.44(13) 1_455 . . . ? O5 Ni1 N3 C12 139.30(13) . . . . ? O3 Ni1 N3 C12 -114.47(13) 1_455 . . . ? C5 Ni1 N3 C12 -83.54(13) 1_455 . . . ? O1 Ni1 N3 C11 -154.50(17) . . . . ? N1 Ni1 N3 C11 -41.7(17) . . . . ? O4 Ni1 N3 C11 109.49(17) 1_455 . . . ? O5 Ni1 N3 C11 -58.77(17) . . . . ? O3 Ni1 N3 C11 47.45(17) 1_455 . . . ? C5 Ni1 N3 C11 78.38(17) 1_455 . . . ? C1 C3 C4 C10 -0.9(2) . . . . ? C1 C3 C4 C5 175.66(14) . . . . ? O3 C5 C4 C3 -17.0(2) . . . . ? O4 C5 C4 C3 165.08(14) . . . . ? Ni1 C5 C4 C3 -125.1(11) 1_655 . . . ? O3 C5 C4 C10 159.51(15) . . . . ? O4 C5 C4 C10 -18.4(2) . . . . ? Ni1 C5 C4 C10 51.5(12) 1_655 . . . ? N1 C19 C21 N2 0.6(2) . . . . ? C20 N2 C21 C19 -0.22(18) . . . . ? C17 N2 C21 C19 -170.38(15) 1_545 . . . ? Ni1 O1 C6 O2 3.1(2) . . . . ? Ni1 O1 C6 C1 -175.12(10) . . . . ? C8 C1 C6 O2 -176.99(15) . . . . ? C3 C1 C6 O2 -0.1(2) . . . . ? C8 C1 C6 O1 1.4(2) . . . . ? C3 C1 C6 O1 178.29(14) . . . . ? C12 N4 C14 C13 -49.0(2) . . . . ? C1A N4 C14 C13 137.3(2) . . . . ? C12 N4 C14 C15 128.5(2) . . . . ? C1A N4 C14 C15 -45.2(3) . . . . ? C13 C14 C15 C16 -1.0(3) . . . . ? N4 C14 C15 C16 -178.44(17) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C3 C4 C10 C7 0.8(2) . . . . ? C5 C4 C10 C7 -175.71(15) . . . . ? C8 C7 C10 C4 0.1(3) . . . . ? C9 C7 C10 C4 179.57(19) . . . . ? C19 N1 C20 N2 0.69(17) . . . . ? Ni1 N1 C20 N2 -160.16(10) . . . . ? C21 N2 C20 N1 -0.31(18) . . . . ? C17 N2 C20 N1 169.86(14) 1_545 . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C15 C16 C17 N2 -176.88(16) . . . 1_565 ? C13 C18 C17 C16 0.0(3) . . . . ? C13 C18 C17 N2 176.90(16) . . . 1_565 ? C15 C14 C13 C18 1.0(3) . . . . ? N4 C14 C13 C18 178.43(17) . . . . ? C17 C18 C13 C14 -0.5(3) . . . . ? C12 N3 C11 C1A 1.1(2) . . . . ? Ni1 N3 C11 C1A -162.73(15) . . . . ? C11 N3 C12 N4 -1.0(2) . . . . ? Ni1 N3 C12 N4 165.40(11) . . . . ? C1A N4 C12 N3 0.5(2) . . . . ? C14 N4 C12 N3 -174.34(15) . . . . ? N3 C11 C1A N4 -0.8(3) . . . . ? C12 N4 C1A C11 0.2(2) . . . . ? C14 N4 C1A C11 174.85(18) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.420 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 890910' ####################################################################### # # 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_Ni_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 N8 Ni O7' _chemical_formula_weight 603.20 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.405(3) _cell_length_b 17.494(5) _cell_length_c 17.621(4) _cell_angle_alpha 90.000 _cell_angle_beta 100.421(8) _cell_angle_gamma 90.000 _cell_volume 2548.2(18) _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 block _exptl_crystal_colour green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.825 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7783 _exptl_absorpt_correction_T_max 0.8266 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15574 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5808 _reflns_number_gt 4628 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART(Bruker,1998) _computing_cell_refinement 'Bruker SMART' _computing_data_reduction SAINT(Bruker,1998) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker,1998)' _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^)+(0.0506P)^2^+1.2318P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5808 _refine_ls_number_parameters 378 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.1020 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.034 _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 Ni1 Ni 0.79964(3) 0.248466(13) 0.762091(13) 0.02854(9) Uani 1 1 d . . . O2 O 1.16659(19) 0.30186(10) 0.85119(9) 0.0537(4) Uani 1 1 d . . . O1 O 0.95390(17) 0.23104(9) 0.86569(8) 0.0397(3) Uani 1 1 d . . . N8 N 0.6023(2) 0.43097(10) 0.87281(9) 0.0373(4) Uani 1 1 d . . . N2 N 0.5179(2) 0.10571(10) 0.88101(10) 0.0354(4) Uani 1 1 d . . . C6 C 1.4348(2) 0.21204(11) 1.05569(11) 0.0320(4) Uani 1 1 d . . . C2 C 1.1895(2) 0.22043(12) 0.95977(11) 0.0330(4) Uani 1 1 d . . . O7 O 0.9719(2) 0.31915(11) 0.72037(10) 0.0513(4) Uani 1 1 d D . . O3 O 1.6992(2) 0.25029(9) 1.04173(10) 0.0476(4) Uani 1 1 d . . . O4 O 1.6402(2) 0.23555(10) 1.16020(9) 0.0493(4) Uani 1 1 d . . . C18 C 0.5082(2) 0.05285(12) 0.94153(12) 0.0358(4) Uani 1 1 d U . . N4 N 0.9645(2) 0.06622(10) 0.64062(11) 0.0426(4) Uani 1 1 d . . . C7 C 1.3493(2) 0.24159(11) 0.98694(11) 0.0328(4) Uani 1 1 d . . . H7 H 1.3997 0.2760 0.9587 0.039 Uiso 1 1 calc R . . C5 C 1.3614(2) 0.15877(11) 1.09622(11) 0.0359(4) Uani 1 1 d . . . H5 H 1.4154 0.1393 1.1430 0.043 Uiso 1 1 calc R . . C4 C 1.2064(3) 0.13516(12) 1.06583(12) 0.0379(4) Uani 1 1 d . . . C24 C 0.5493(3) 0.46566(11) 0.93696(12) 0.0363(4) Uani 1 1 d . . . O6 O 0.9998(3) 0.05334(15) 1.08252(14) 0.0950(9) Uani 1 1 d . . . N1 N 0.6271(2) 0.18389(10) 0.80595(10) 0.0356(4) Uani 1 1 d . . . N7 N 0.7083(2) 0.34747(9) 0.80235(9) 0.0361(4) Uani 1 1 d . . . C8 C 1.6083(2) 0.23510(11) 1.08788(11) 0.0333(4) Uani 1 1 d . . . O5 O 1.2231(3) 0.04219(14) 1.15936(14) 0.0912(8) Uani 1 1 d . . . N6 N 0.3721(3) 0.00682(12) 0.93874(13) 0.0561(5) Uani 1 1 d U . . H6 H 0.2922 0.0110 0.9009 0.067 Uiso 1 1 calc R . . N3 N 0.8996(2) 0.15205(10) 0.72113(10) 0.0369(4) Uani 1 1 d . . . C3 C 1.1177(2) 0.16590(12) 0.99937(12) 0.0386(5) Uani 1 1 d . . . H3 H 1.0118 0.1503 0.9815 0.046 Uiso 1 1 calc R . . C26 C 0.5270(3) 0.46399(13) 1.07075(13) 0.0488(6) Uani 1 1 d . . . H26 H 0.5455 0.4395 1.1184 0.059 Uiso 1 1 calc R . . N5 N 1.1379(2) 0.07270(12) 1.10561(12) 0.0521(5) Uani 1 1 d . . . C20 C 0.3652(3) -0.04568(13) 0.99674(13) 0.0438(5) Uani 1 1 d U . . H20 H 0.2743 -0.0765 0.9942 0.053 Uiso 1 1 calc R . . C14 C 0.9583(3) -0.07546(13) 0.48530(15) 0.0537(6) Uani 1 1 d . . . H14 H 0.9304 -0.1264 0.4752 0.064 Uiso 1 1 calc R . . C25 C 0.5760(3) 0.42989(13) 1.00799(13) 0.0468(5) Uani 1 1 d . . . H25 H 0.6272 0.3826 1.0137 0.056 Uiso 1 1 calc R . . C17 C 0.3971(3) 0.12852(15) 0.82234(14) 0.0500(6) Uani 1 1 d . . . H17 H 0.2890 0.1140 0.8151 0.060 Uiso 1 1 calc R . . C12 C 0.9852(3) 0.03234(13) 0.56945(14) 0.0445(5) Uani 1 1 d . . . C9 C 0.9420(3) 0.08483(13) 0.76022(13) 0.0458(5) Uani 1 1 d . . . H9 H 0.9442 0.0775 0.8127 0.055 Uiso 1 1 calc R . . C11 C 0.9153(3) 0.13868(12) 0.64941(12) 0.0385(5) Uani 1 1 d . . . H11 H 0.8952 0.1745 0.6098 0.046 Uiso 1 1 calc R . . C21 C 0.6645(3) 0.41167(13) 0.75942(13) 0.0460(5) Uani 1 1 d . . . H21 H 0.6775 0.4186 0.7086 0.055 Uiso 1 1 calc R . . C15 C 0.6529(3) 0.14161(13) 0.86838(13) 0.0417(5) Uani 1 1 d . . . H15 H 0.7532 0.1369 0.9005 0.050 Uiso 1 1 calc R . . C1 C 1.0960(2) 0.25432(11) 0.88578(11) 0.0329(4) Uani 1 1 d . . . C16 C 0.4652(3) 0.17596(13) 0.77718(14) 0.0455(5) Uani 1 1 d . . . H16 H 0.4104 0.1998 0.7329 0.055 Uiso 1 1 calc R . . C22 C 0.6696(3) 0.36084(12) 0.87006(12) 0.0387(5) Uani 1 1 d . . . H22 H 0.6863 0.3265 0.9110 0.046 Uiso 1 1 calc R . . C13 C 0.9428(3) -0.04365(13) 0.55505(15) 0.0528(6) Uani 1 1 d . . . H13 H 0.9043 -0.0727 0.5921 0.063 Uiso 1 1 calc R . . C23 C 0.5999(3) 0.46345(13) 0.80150(13) 0.0516(6) Uani 1 1 d . . . H23 H 0.5613 0.5117 0.7855 0.062 Uiso 1 1 calc R . . C10 C 0.9796(3) 0.03165(13) 0.71186(14) 0.0505(6) Uani 1 1 d . . . H10 H 1.0100 -0.0186 0.7239 0.061 Uiso 1 1 calc R . . H7A H 1.051(3) 0.3183(18) 0.7570(12) 0.081(10) Uiso 1 1 d D . . H7B H 1.000(4) 0.307(3) 0.6788(12) 0.142(18) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02816(14) 0.03417(15) 0.02138(13) 0.00032(9) -0.00065(9) -0.00026(9) O2 0.0449(9) 0.0610(10) 0.0482(9) 0.0223(8) -0.0101(7) -0.0142(8) O1 0.0324(8) 0.0549(9) 0.0276(7) 0.0072(6) -0.0053(6) -0.0055(6) N8 0.0458(10) 0.0331(9) 0.0322(9) -0.0012(7) 0.0054(7) 0.0037(7) N2 0.0314(9) 0.0369(9) 0.0386(9) -0.0046(7) 0.0085(7) -0.0063(7) C6 0.0330(10) 0.0340(10) 0.0264(9) -0.0024(8) -0.0015(7) 0.0003(8) C2 0.0337(10) 0.0357(10) 0.0264(9) -0.0004(8) -0.0031(7) 0.0014(8) O7 0.0510(10) 0.0648(11) 0.0366(9) 0.0105(8) 0.0037(8) -0.0140(8) O3 0.0409(9) 0.0586(10) 0.0425(9) -0.0043(7) 0.0055(7) -0.0103(7) O4 0.0472(9) 0.0644(10) 0.0291(8) 0.0062(7) -0.0124(7) -0.0135(8) C18 0.0362(10) 0.0372(10) 0.0363(10) -0.0072(8) 0.0129(8) -0.0047(8) N4 0.0506(11) 0.0352(9) 0.0441(10) 0.0022(8) 0.0147(8) 0.0094(8) C7 0.0335(10) 0.0357(10) 0.0269(9) 0.0011(7) -0.0007(8) -0.0023(8) C5 0.0371(11) 0.0399(11) 0.0276(9) 0.0052(8) -0.0020(8) 0.0019(8) C4 0.0392(11) 0.0400(11) 0.0333(10) 0.0056(8) 0.0032(8) -0.0035(9) C24 0.0402(11) 0.0334(10) 0.0344(10) -0.0027(8) 0.0047(8) 0.0013(8) O6 0.0609(13) 0.1183(19) 0.0937(16) 0.0531(15) -0.0183(11) -0.0448(13) N1 0.0320(9) 0.0381(9) 0.0358(9) -0.0024(7) 0.0038(7) -0.0041(7) N7 0.0418(10) 0.0358(9) 0.0290(8) -0.0021(7) 0.0021(7) 0.0003(7) C8 0.0343(10) 0.0303(9) 0.0310(10) 0.0009(7) -0.0056(8) 0.0000(8) O5 0.0671(13) 0.1038(17) 0.0941(16) 0.0661(14) -0.0082(11) -0.0197(12) N6 0.0491(11) 0.0626(13) 0.0557(12) 0.0017(9) 0.0073(10) -0.0175(9) N3 0.0379(9) 0.0384(9) 0.0340(9) 0.0022(7) 0.0053(7) 0.0059(7) C3 0.0328(10) 0.0431(11) 0.0367(11) 0.0025(9) -0.0027(8) -0.0062(9) C26 0.0701(16) 0.0419(12) 0.0342(11) 0.0047(9) 0.0095(10) 0.0172(11) N5 0.0479(12) 0.0574(12) 0.0491(12) 0.0165(10) 0.0039(9) -0.0096(10) C20 0.0340(11) 0.0514(13) 0.0461(12) -0.0045(9) 0.0081(9) -0.0167(9) C14 0.0741(17) 0.0315(11) 0.0618(16) -0.0030(10) 0.0287(13) 0.0007(11) C25 0.0632(15) 0.0357(11) 0.0414(12) 0.0025(9) 0.0089(11) 0.0150(10) C17 0.0312(11) 0.0606(15) 0.0559(14) 0.0051(12) 0.0022(10) -0.0093(10) C12 0.0516(13) 0.0368(11) 0.0489(13) 0.0004(9) 0.0192(10) 0.0098(10) C9 0.0520(13) 0.0463(12) 0.0405(12) 0.0102(10) 0.0121(10) 0.0085(10) C11 0.0433(12) 0.0346(10) 0.0380(11) 0.0025(9) 0.0082(9) 0.0069(9) C21 0.0655(15) 0.0403(12) 0.0323(11) 0.0035(9) 0.0087(10) 0.0005(10) C15 0.0311(10) 0.0523(13) 0.0405(11) 0.0054(10) 0.0031(9) -0.0088(9) C1 0.0335(10) 0.0346(10) 0.0275(9) 0.0000(8) -0.0022(8) 0.0013(8) C16 0.0362(11) 0.0518(13) 0.0457(13) 0.0039(10) -0.0004(9) -0.0037(10) C22 0.0477(12) 0.0356(11) 0.0322(10) 0.0004(8) 0.0055(9) 0.0055(9) C13 0.0712(17) 0.0368(12) 0.0575(15) 0.0025(10) 0.0306(13) 0.0041(11) C23 0.0803(18) 0.0380(12) 0.0365(12) 0.0063(9) 0.0105(11) 0.0122(11) C10 0.0621(15) 0.0386(12) 0.0533(14) 0.0114(10) 0.0172(12) 0.0130(11) _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 2.0561(16) 4_465 ? Ni1 O1 2.0616(15) . ? Ni1 N7 2.0711(17) . ? Ni1 N3 2.0715(18) . ? Ni1 N1 2.0936(18) . ? Ni1 O7 2.1331(18) . ? O2 C1 1.243(2) . ? O1 C1 1.251(3) . ? N8 C22 1.356(3) . ? N8 C23 1.376(3) . ? N8 C24 1.424(3) . ? N2 C15 1.350(3) . ? N2 C17 1.371(3) . ? N2 C18 1.425(3) . ? C6 C5 1.385(3) . ? C6 C7 1.392(3) . ? C6 C8 1.520(3) . ? C2 C3 1.383(3) . ? C2 C7 1.392(3) . ? C2 C1 1.516(3) . ? O7 H7A 0.838(10) . ? O7 H7B 0.837(10) . ? O3 C8 1.241(3) . ? O4 C8 1.254(2) . ? O4 Ni1 2.0561(16) 4_666 ? C18 C20 1.383(3) 3_657 ? C18 N6 1.392(3) . ? N4 C11 1.351(3) . ? N4 C10 1.378(3) . ? N4 C12 1.426(3) . ? C7 H7 0.9300 . ? C5 C4 1.379(3) . ? C5 H5 0.9300 . ? C4 C3 1.379(3) . ? C4 N5 1.471(3) . ? C24 C25 1.381(3) . ? C24 C26 1.383(3) 3_667 ? O6 N5 1.206(3) . ? N1 C15 1.311(3) . ? N1 C16 1.370(3) . ? N7 C22 1.313(3) . ? N7 C21 1.367(3) . ? O5 N5 1.204(3) . ? N6 C20 1.383(3) . ? N6 H6 0.8600 . ? N3 C11 1.315(3) . ? N3 C9 1.377(3) . ? C3 H3 0.9300 . ? C26 C24 1.383(3) 3_667 ? C26 C25 1.383(3) . ? C26 H26 0.9300 . ? C20 C18 1.383(3) 3_657 ? C20 H20 0.9300 . ? C14 C12 1.375(3) 3_756 ? C14 C13 1.377(3) . ? C14 H14 0.9300 . ? C25 H25 0.9300 . ? C17 C16 1.347(3) . ? C17 H17 0.9300 . ? C12 C14 1.375(3) 3_756 ? C12 C13 1.388(3) . ? C9 C10 1.337(3) . ? C9 H9 0.9300 . ? C11 H11 0.9300 . ? C21 C23 1.346(3) . ? C21 H21 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C22 H22 0.9300 . ? C13 H13 0.9300 . ? C23 H23 0.9300 . ? C10 H10 0.9300 . ? 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 O1 178.26(6) 4_465 . ? O4 Ni1 N7 87.81(7) 4_465 . ? O1 Ni1 N7 91.90(7) . . ? O4 Ni1 N3 92.75(7) 4_465 . ? O1 Ni1 N3 87.61(7) . . ? N7 Ni1 N3 177.56(7) . . ? O4 Ni1 N1 90.57(8) 4_465 . ? O1 Ni1 N1 87.71(7) . . ? N7 Ni1 N1 90.01(7) . . ? N3 Ni1 N1 92.36(7) . . ? O4 Ni1 O7 89.78(8) 4_465 . ? O1 Ni1 O7 91.92(7) . . ? N7 Ni1 O7 87.14(8) . . ? N3 Ni1 O7 90.49(8) . . ? N1 Ni1 O7 177.12(7) . . ? C1 O1 Ni1 128.16(13) . . ? C22 N8 C23 106.16(17) . . ? C22 N8 C24 127.35(17) . . ? C23 N8 C24 126.46(18) . . ? C15 N2 C17 105.66(18) . . ? C15 N2 C18 126.09(18) . . ? C17 N2 C18 128.20(18) . . ? C5 C6 C7 119.37(18) . . ? C5 C6 C8 118.23(17) . . ? C7 C6 C8 122.39(18) . . ? C3 C2 C7 119.47(18) . . ? C3 C2 C1 119.86(18) . . ? C7 C2 C1 120.64(18) . . ? Ni1 O7 H7A 102(2) . . ? Ni1 O7 H7B 118(3) . . ? H7A O7 H7B 111(2) . . ? C8 O4 Ni1 150.92(16) . 4_666 ? C20 C18 N6 119.1(2) 3_657 . ? C20 C18 N2 120.48(18) 3_657 . ? N6 C18 N2 120.45(19) . . ? C11 N4 C10 106.68(18) . . ? C11 N4 C12 125.40(18) . . ? C10 N4 C12 127.79(19) . . ? C6 C7 C2 120.99(19) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? C4 C5 C6 118.62(18) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C3 C4 C5 122.73(19) . . ? C3 C4 N5 119.75(19) . . ? C5 C4 N5 117.48(18) . . ? C25 C24 C26 119.27(19) . 3_667 ? C25 C24 N8 120.23(18) . . ? C26 C24 N8 120.49(19) 3_667 . ? C15 N1 C16 104.82(17) . . ? C15 N1 Ni1 126.43(14) . . ? C16 N1 Ni1 128.75(15) . . ? C22 N7 C21 105.68(18) . . ? C22 N7 Ni1 128.92(14) . . ? C21 N7 Ni1 125.24(14) . . ? O3 C8 O4 128.4(2) . . ? O3 C8 C6 118.34(18) . . ? O4 C8 C6 113.26(19) . . ? C20 N6 C18 120.1(2) . . ? C20 N6 H6 119.9 . . ? C18 N6 H6 119.9 . . ? C11 N3 C9 105.47(18) . . ? C11 N3 Ni1 126.67(14) . . ? C9 N3 Ni1 127.29(14) . . ? C4 C3 C2 118.63(19) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C24 C26 C25 120.3(2) 3_667 . ? C24 C26 H26 119.8 3_667 . ? C25 C26 H26 119.8 . . ? O5 N5 O6 122.7(2) . . ? O5 N5 C4 118.4(2) . . ? O6 N5 C4 118.9(2) . . ? C18 C20 N6 120.80(19) 3_657 . ? C18 C20 H20 119.6 3_657 . ? N6 C20 H20 119.6 . . ? C12 C14 C13 120.3(2) 3_756 . ? C12 C14 H14 119.8 3_756 . ? C13 C14 H14 119.8 . . ? C24 C25 C26 120.4(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C16 C17 N2 106.81(19) . . ? C16 C17 H17 126.6 . . ? N2 C17 H17 126.6 . . ? C14 C12 C13 120.5(2) 3_756 . ? C14 C12 N4 120.1(2) 3_756 . ? C13 C12 N4 119.4(2) . . ? C10 C9 N3 110.2(2) . . ? C10 C9 H9 124.9 . . ? N3 C9 H9 124.9 . . ? N3 C11 N4 111.29(18) . . ? N3 C11 H11 124.4 . . ? N4 C11 H11 124.4 . . ? C23 C21 N7 110.08(19) . . ? C23 C21 H21 125.0 . . ? N7 C21 H21 125.0 . . ? N1 C15 N2 112.62(19) . . ? N1 C15 H15 123.7 . . ? N2 C15 H15 123.7 . . ? O2 C1 O1 126.49(19) . . ? O2 C1 C2 117.66(18) . . ? O1 C1 C2 115.85(18) . . ? C17 C16 N1 110.1(2) . . ? C17 C16 H16 125.0 . . ? N1 C16 H16 125.0 . . ? N7 C22 N8 111.54(18) . . ? N7 C22 H22 124.2 . . ? N8 C22 H22 124.2 . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C21 C23 N8 106.54(19) . . ? C21 C23 H23 126.7 . . ? N8 C23 H23 126.7 . . ? C9 C10 N4 106.36(19) . . ? C9 C10 H10 126.8 . . ? N4 C10 H10 126.8 . . ? 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 O4 Ni1 O1 C1 -171(2) 4_465 . . . ? N7 Ni1 O1 C1 -90.34(18) . . . . ? N3 Ni1 O1 C1 87.26(18) . . . . ? N1 Ni1 O1 C1 179.72(18) . . . . ? O7 Ni1 O1 C1 -3.15(18) . . . . ? C15 N2 C18 C20 13.6(3) . . . 3_657 ? C17 N2 C18 C20 -169.3(2) . . . 3_657 ? C15 N2 C18 N6 -165.4(2) . . . . ? C17 N2 C18 N6 11.7(3) . . . . ? C5 C6 C7 C2 2.2(3) . . . . ? C8 C6 C7 C2 -178.74(18) . . . . ? C3 C2 C7 C6 -3.8(3) . . . . ? C1 C2 C7 C6 178.56(18) . . . . ? C7 C6 C5 C4 1.7(3) . . . . ? C8 C6 C5 C4 -177.35(19) . . . . ? C6 C5 C4 C3 -4.3(3) . . . . ? C6 C5 C4 N5 173.59(19) . . . . ? C22 N8 C24 C25 5.3(3) . . . . ? C23 N8 C24 C25 -172.4(2) . . . . ? C22 N8 C24 C26 -175.8(2) . . . 3_667 ? C23 N8 C24 C26 6.5(3) . . . 3_667 ? O4 Ni1 N1 C15 167.82(18) 4_465 . . . ? O1 Ni1 N1 C15 -12.47(18) . . . . ? N7 Ni1 N1 C15 -104.37(18) . . . . ? N3 Ni1 N1 C15 75.05(18) . . . . ? O7 Ni1 N1 C15 -95.2(13) . . . . ? O4 Ni1 N1 C16 -12.17(19) 4_465 . . . ? O1 Ni1 N1 C16 167.54(19) . . . . ? N7 Ni1 N1 C16 75.64(19) . . . . ? N3 Ni1 N1 C16 -104.95(19) . . . . ? O7 Ni1 N1 C16 84.8(13) . . . . ? O4 Ni1 N7 C22 136.47(19) 4_465 . . . ? O1 Ni1 N7 C22 -41.81(19) . . . . ? N3 Ni1 N7 C22 -120.2(15) . . . . ? N1 Ni1 N7 C22 45.90(19) . . . . ? O7 Ni1 N7 C22 -133.64(19) . . . . ? O4 Ni1 N7 C21 -38.28(18) 4_465 . . . ? O1 Ni1 N7 C21 143.44(18) . . . . ? N3 Ni1 N7 C21 65.1(15) . . . . ? N1 Ni1 N7 C21 -128.85(19) . . . . ? O7 Ni1 N7 C21 51.61(18) . . . . ? Ni1 O4 C8 O3 -0.6(5) 4_666 . . . ? Ni1 O4 C8 C6 179.0(2) 4_666 . . . ? C5 C6 C8 O3 145.87(19) . . . . ? C7 C6 C8 O3 -33.2(3) . . . . ? C5 C6 C8 O4 -33.7(3) . . . . ? C7 C6 C8 O4 147.27(19) . . . . ? C20 C18 N6 C20 -0.6(4) 3_657 . . . ? N2 C18 N6 C20 178.41(19) . . . . ? O4 Ni1 N3 C11 31.84(19) 4_465 . . . ? O1 Ni1 N3 C11 -149.86(18) . . . . ? N7 Ni1 N3 C11 -71.4(15) . . . . ? N1 Ni1 N3 C11 122.53(18) . . . . ? O7 Ni1 N3 C11 -57.96(18) . . . . ? O4 Ni1 N3 C9 -138.24(19) 4_465 . . . ? O1 Ni1 N3 C9 40.05(19) . . . . ? N7 Ni1 N3 C9 118.5(15) . . . . ? N1 Ni1 N3 C9 -47.56(19) . . . . ? O7 Ni1 N3 C9 131.95(19) . . . . ? C5 C4 C3 C2 2.8(3) . . . . ? N5 C4 C3 C2 -175.1(2) . . . . ? C7 C2 C3 C4 1.3(3) . . . . ? C1 C2 C3 C4 178.98(19) . . . . ? C3 C4 N5 O5 173.3(3) . . . . ? C5 C4 N5 O5 -4.6(3) . . . . ? C3 C4 N5 O6 -5.6(4) . . . . ? C5 C4 N5 O6 176.5(3) . . . . ? C18 N6 C20 C18 0.6(4) . . . 3_657 ? C26 C24 C25 C26 0.0(4) 3_667 . . . ? N8 C24 C25 C26 178.9(2) . . . . ? C24 C26 C25 C24 0.0(4) 3_667 . . . ? C15 N2 C17 C16 0.7(3) . . . . ? C18 N2 C17 C16 -176.9(2) . . . . ? C11 N4 C12 C14 35.6(4) . . . 3_756 ? C10 N4 C12 C14 -148.9(3) . . . 3_756 ? C11 N4 C12 C13 -142.3(2) . . . . ? C10 N4 C12 C13 33.2(4) . . . . ? C11 N3 C9 C10 -1.1(3) . . . . ? Ni1 N3 C9 C10 170.62(17) . . . . ? C9 N3 C11 N4 0.4(2) . . . . ? Ni1 N3 C11 N4 -171.40(14) . . . . ? C10 N4 C11 N3 0.4(3) . . . . ? C12 N4 C11 N3 176.7(2) . . . . ? C22 N7 C21 C23 0.1(3) . . . . ? Ni1 N7 C21 C23 175.87(17) . . . . ? C16 N1 C15 N2 1.1(3) . . . . ? Ni1 N1 C15 N2 -178.92(13) . . . . ? C17 N2 C15 N1 -1.1(3) . . . . ? C18 N2 C15 N1 176.54(18) . . . . ? Ni1 O1 C1 O2 10.7(3) . . . . ? Ni1 O1 C1 C2 -169.21(13) . . . . ? C3 C2 C1 O2 -178.4(2) . . . . ? C7 C2 C1 O2 -0.7(3) . . . . ? C3 C2 C1 O1 1.5(3) . . . . ? C7 C2 C1 O1 179.20(19) . . . . ? N2 C17 C16 N1 -0.1(3) . . . . ? C15 N1 C16 C17 -0.6(3) . . . . ? Ni1 N1 C16 C17 179.38(16) . . . . ? C21 N7 C22 N8 0.1(2) . . . . ? Ni1 N7 C22 N8 -175.44(14) . . . . ? C23 N8 C22 N7 -0.3(3) . . . . ? C24 N8 C22 N7 -178.37(19) . . . . ? C12 C14 C13 C12 -0.1(4) 3_756 . . . ? C14 C12 C13 C14 0.1(4) 3_756 . . . ? N4 C12 C13 C14 178.0(2) . . . . ? N7 C21 C23 N8 -0.3(3) . . . . ? C22 N8 C23 C21 0.3(3) . . . . ? C24 N8 C23 C21 178.4(2) . . . . ? N3 C9 C10 N4 1.4(3) . . . . ? C11 N4 C10 C9 -1.1(3) . . . . ? C12 N4 C10 C9 -177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.294 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 890911' ####################################################################### # # 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_Ni_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 N6 Ni O4' _chemical_formula_weight 594.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 17.3102(7) _cell_length_b 10.8871(4) _cell_length_c 30.2298(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.4120(5) _cell_angle_gamma 90.00 _cell_volume 5603.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2472 _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8086 _exptl_absorpt_correction_T_max 0.8542 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16977 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.55 _reflns_number_total 6402 _reflns_number_gt 5197 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART(Bruker,1998) _computing_cell_refinement 'Bruker SMART' _computing_data_reduction SAINT(Bruker,1998) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker,1998)' _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^)+(0.0502P)^2^+2.6633P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6402 _refine_ls_number_parameters 374 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0444 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.001 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 0.020811(12) 0.996289(18) 0.137626(7) 0.01990(8) Uani 1 1 d . . . O3 O 0.42482(7) 1.36950(11) 0.14138(4) 0.0250(3) Uani 1 1 d . . . O2 O 0.16649(8) 1.20457(13) 0.17538(5) 0.0371(3) Uani 1 1 d . . . O4 O 0.41219(8) 1.50599(11) 0.08703(5) 0.0309(3) Uani 1 1 d . . . O1 O 0.08656(7) 1.12830(12) 0.11493(4) 0.0316(3) Uani 1 1 d . . . N4 N 0.12720(9) 0.75700(13) 0.23736(5) 0.0287(3) Uani 1 1 d . . . N5 N 0.08266(9) 0.27651(13) 0.29616(5) 0.0254(3) Uani 1 1 d . . . N2 N 0.12914(10) 0.78650(15) 0.04860(6) 0.0348(4) Uani 1 1 d . . . C22 C 0.09603(11) 0.49967(16) 0.31378(7) 0.0287(4) Uani 1 1 d . . . N6 N 0.03211(8) 0.11317(13) 0.32329(5) 0.0244(3) Uani 1 1 d . . . N1 N 0.06022(9) 0.87240(14) 0.09458(5) 0.0301(4) Uani 1 1 d . . . C5 C 0.38410(10) 1.42039(16) 0.10723(6) 0.0235(4) Uani 1 1 d . . . C23 C 0.09672(10) 0.40108(15) 0.28415(6) 0.0239(4) Uani 1 1 d . . . C2 C 0.18555(10) 1.26718(16) 0.10297(6) 0.0249(4) Uani 1 1 d . . . C3 C 0.26146(10) 1.31055(16) 0.11873(6) 0.0245(4) Uani 1 1 d . . . H3 H 0.2855 1.2947 0.1482 0.029 Uiso 1 1 calc R . . C21 C 0.10691(10) 0.61640(16) 0.29712(6) 0.0283(4) Uani 1 1 d . . . H21 H 0.1045 0.6843 0.3155 0.034 Uiso 1 1 calc R . . C4 C 0.30137(10) 1.37710(16) 0.09079(6) 0.0246(4) Uani 1 1 d . . . C25 C 0.12760(11) 0.53573(17) 0.22547(7) 0.0289(4) Uani 1 1 d . . . C24 C 0.11318(10) 0.41932(16) 0.24123(6) 0.0262(4) Uani 1 1 d . . . H24 H 0.1146 0.3518 0.2225 0.031 Uiso 1 1 calc R . . C1 C 0.14354(10) 1.19432(16) 0.13429(6) 0.0244(4) Uani 1 1 d . . . N3 N 0.09453(8) 0.91432(13) 0.19175(5) 0.0255(3) Uani 1 1 d . . . C13 C 0.19172(11) 0.76754(17) 0.02366(7) 0.0306(4) Uani 1 1 d . . . C7 C 0.18837(12) 1.36257(19) 0.03070(6) 0.0352(5) Uani 1 1 d . . . C28 C 0.11457(12) 0.17437(17) 0.27892(7) 0.0349(5) Uani 1 1 d . . . H28 H 0.1505 0.1739 0.2594 0.042 Uiso 1 1 calc R . . C20 C 0.12120(10) 0.63412(16) 0.25399(6) 0.0259(4) Uani 1 1 d . . . C15 C 0.32391(12) 0.7184(2) 0.02255(7) 0.0391(5) Uani 1 1 d . . . H15 H 0.3742 0.6970 0.0370 0.047 Uiso 1 1 calc R . . C27 C 0.03245(10) 0.23336(16) 0.32225(6) 0.0253(4) Uani 1 1 d . . . H27 H 0.0021 0.2830 0.3375 0.030 Uiso 1 1 calc R . . C19 C 0.19162(11) 0.83282(17) 0.24271(7) 0.0306(4) Uani 1 1 d . . . H19 H 0.2396 0.8208 0.2618 0.037 Uiso 1 1 calc R . . C17 C 0.07106(11) 0.80993(17) 0.20664(7) 0.0320(4) Uani 1 1 d . . . H17 H 0.0214 0.7765 0.1971 0.038 Uiso 1 1 calc R . . C8 C 0.15057(11) 1.29271(18) 0.05889(7) 0.0332(4) Uani 1 1 d . . . H8 H 0.1006 1.2623 0.0479 0.040 Uiso 1 1 calc R . . C10 C 0.11675(12) 0.88788(18) 0.07177(7) 0.0351(5) Uani 1 1 d . . . H10 H 0.1451 0.9604 0.0716 0.042 Uiso 1 1 calc R . . C9 C 0.14952(15) 1.3940(3) -0.01691(8) 0.0556(7) Uani 1 1 d . . . H9A H 0.0964 1.3645 -0.0223 0.083 Uiso 1 1 calc R . . H9B H 0.1780 1.3560 -0.0377 0.083 Uiso 1 1 calc R . . H9C H 0.1496 1.4815 -0.0209 0.083 Uiso 1 1 calc R . . C6 C 0.26435(11) 1.40427(18) 0.04716(6) 0.0325(4) Uani 1 1 d . . . H6 H 0.2905 1.4508 0.0287 0.039 Uiso 1 1 calc R . . C18 C 0.17079(10) 0.92916(17) 0.21434(7) 0.0290(4) Uani 1 1 d . . . H18 H 0.2031 0.9952 0.2107 0.035 Uiso 1 1 calc R . . C29 C 0.08321(12) 0.07612(18) 0.29600(7) 0.0343(5) Uani 1 1 d . . . H29 H 0.0945 -0.0052 0.2902 0.041 Uiso 1 1 calc R . . C14 C 0.26484(12) 0.73601(19) 0.04752(7) 0.0356(5) Uani 1 1 d . . . C12 C 0.07734(14) 0.6998(2) 0.05788(9) 0.0525(7) Uani 1 1 d . . . H12 H 0.0720 0.6199 0.0469 0.063 Uiso 1 1 calc R . . C26 C 0.15086(15) 0.5506(2) 0.18013(7) 0.0460(6) Uani 1 1 d . . . H26A H 0.2012 0.5901 0.1837 0.069 Uiso 1 1 calc R . . H26B H 0.1124 0.5999 0.1612 0.069 Uiso 1 1 calc R . . H26C H 0.1538 0.4714 0.1666 0.069 Uiso 1 1 calc R . . C11 C 0.03556(13) 0.7536(2) 0.08610(8) 0.0459(6) Uani 1 1 d . . . H11 H -0.0042 0.7156 0.0981 0.055 Uiso 1 1 calc R . . C40 C 0.08485(18) 0.4888(2) 0.36200(8) 0.0494(6) Uani 1 1 d . . . H40A H 0.1064 0.5599 0.3785 0.074 Uiso 1 1 calc R . . H40B H 0.1112 0.4165 0.3752 0.074 Uiso 1 1 calc R . . H40C H 0.0298 0.4830 0.3629 0.074 Uiso 1 1 calc R . . C16 C 0.27706(15) 0.7131(3) 0.09734(8) 0.0555(6) Uani 1 1 d . . . H16A H 0.3312 0.6931 0.1082 0.083 Uiso 1 1 calc R . . H16B H 0.2445 0.6459 0.1033 0.083 Uiso 1 1 calc R . . H16C H 0.2633 0.7855 0.1123 0.083 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 0.01785(12) 0.01833(12) 0.02475(13) -0.00105(8) 0.00717(9) -0.00243(8) O3 0.0210(6) 0.0255(6) 0.0289(7) 0.0016(5) 0.0055(5) -0.0030(5) O2 0.0414(8) 0.0404(8) 0.0306(8) -0.0015(6) 0.0098(6) -0.0153(6) O4 0.0263(7) 0.0328(7) 0.0339(7) 0.0075(6) 0.0061(6) -0.0092(5) O1 0.0297(7) 0.0306(7) 0.0360(8) -0.0003(6) 0.0103(6) -0.0143(5) N4 0.0257(8) 0.0192(7) 0.0400(9) 0.0058(6) 0.0025(7) 0.0005(6) N5 0.0265(7) 0.0201(7) 0.0313(8) 0.0022(6) 0.0097(6) 0.0005(6) N2 0.0352(9) 0.0334(9) 0.0414(10) -0.0081(7) 0.0221(8) -0.0026(7) C22 0.0301(9) 0.0270(10) 0.0292(10) -0.0003(7) 0.0058(8) 0.0013(7) N6 0.0253(7) 0.0228(8) 0.0260(8) 0.0019(6) 0.0068(6) -0.0001(6) N1 0.0275(8) 0.0304(8) 0.0361(9) -0.0070(7) 0.0155(7) -0.0046(6) C5 0.0212(8) 0.0233(8) 0.0270(9) -0.0022(7) 0.0073(7) -0.0044(7) C23 0.0218(8) 0.0196(8) 0.0305(10) 0.0025(7) 0.0050(7) 0.0005(6) C2 0.0236(8) 0.0219(9) 0.0299(10) -0.0005(7) 0.0065(7) -0.0046(7) C3 0.0228(8) 0.0250(9) 0.0256(9) 0.0009(7) 0.0045(7) -0.0051(7) C21 0.0282(9) 0.0218(9) 0.0345(10) -0.0039(7) 0.0043(8) 0.0021(7) C4 0.0229(8) 0.0246(9) 0.0268(9) -0.0003(7) 0.0055(7) -0.0054(7) C25 0.0298(9) 0.0252(9) 0.0319(10) 0.0042(8) 0.0064(8) 0.0016(7) C24 0.0267(9) 0.0208(9) 0.0312(10) -0.0008(7) 0.0055(7) 0.0004(7) C1 0.0231(8) 0.0200(8) 0.0321(10) -0.0016(7) 0.0101(7) -0.0031(7) N3 0.0249(7) 0.0194(7) 0.0324(8) 0.0013(6) 0.0059(6) 0.0001(6) C13 0.0317(10) 0.0274(10) 0.0375(11) -0.0046(8) 0.0190(8) 0.0022(7) C7 0.0345(10) 0.0413(11) 0.0267(10) 0.0039(8) -0.0027(8) -0.0104(9) C28 0.0433(11) 0.0240(9) 0.0438(12) 0.0016(8) 0.0255(10) 0.0031(8) C20 0.0219(8) 0.0182(8) 0.0364(10) 0.0064(7) 0.0019(7) 0.0002(6) C15 0.0325(10) 0.0487(13) 0.0372(12) -0.0024(9) 0.0090(9) 0.0114(9) C27 0.0243(9) 0.0235(9) 0.0296(9) 0.0031(7) 0.0085(7) 0.0022(7) C19 0.0229(9) 0.0267(9) 0.0402(11) 0.0014(8) 0.0003(8) -0.0010(7) C17 0.0246(9) 0.0258(10) 0.0427(11) 0.0060(8) -0.0015(8) -0.0020(7) C8 0.0263(9) 0.0364(11) 0.0350(11) 0.0010(8) 0.0006(8) -0.0119(8) C10 0.0348(10) 0.0290(10) 0.0470(12) -0.0085(9) 0.0218(9) -0.0055(8) C9 0.0533(15) 0.0733(18) 0.0345(13) 0.0134(12) -0.0075(11) -0.0182(13) C6 0.0326(10) 0.0359(11) 0.0290(10) 0.0065(8) 0.0058(8) -0.0122(8) C18 0.0249(9) 0.0231(9) 0.0383(11) 0.0019(8) 0.0037(8) -0.0032(7) C29 0.0464(12) 0.0218(9) 0.0406(11) -0.0022(8) 0.0232(9) 0.0015(8) C14 0.0405(11) 0.0369(11) 0.0321(11) -0.0013(8) 0.0133(9) 0.0063(9) C12 0.0571(14) 0.0387(13) 0.0719(17) -0.0254(12) 0.0390(13) -0.0183(11) C26 0.0667(15) 0.0362(12) 0.0397(12) 0.0066(10) 0.0217(11) -0.0026(11) C11 0.0465(12) 0.0370(12) 0.0628(15) -0.0167(11) 0.0333(12) -0.0155(10) C40 0.0831(19) 0.0340(12) 0.0356(12) -0.0026(9) 0.0231(12) -0.0015(11) C16 0.0563(15) 0.0720(18) 0.0410(14) 0.0023(12) 0.0161(11) 0.0115(13) _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 O1 2.0283(12) . ? Ni1 N6 2.0605(14) 2_565 ? Ni1 N1 2.0733(15) . ? Ni1 N3 2.0850(15) . ? Ni1 O3 2.1788(12) 3_445 ? Ni1 O4 2.2014(14) 3_445 ? Ni1 C5 2.5183(17) 3_445 ? O3 C5 1.268(2) . ? O3 Ni1 2.1788(12) 3 ? O2 C1 1.239(2) . ? O4 C5 1.259(2) . ? O4 Ni1 2.2014(14) 3 ? O1 C1 1.274(2) . ? N4 C17 1.346(2) . ? N4 C19 1.373(2) . ? N4 C20 1.440(2) . ? N5 C27 1.359(2) . ? N5 C28 1.385(2) . ? N5 C23 1.436(2) . ? N2 C10 1.345(2) . ? N2 C12 1.365(3) . ? N2 C13 1.442(2) . ? C22 C21 1.392(3) . ? C22 C23 1.399(3) . ? C22 C40 1.509(3) . ? N6 C27 1.309(2) . ? N6 C29 1.375(2) . ? N6 Ni1 2.0605(14) 2_545 ? N1 C10 1.306(2) . ? N1 C11 1.372(2) . ? C5 C4 1.504(2) . ? C5 Ni1 2.5183(17) 3 ? C23 C24 1.392(2) . ? C2 C8 1.389(3) . ? C2 C3 1.396(2) . ? C2 C1 1.518(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9300 . ? C21 C20 1.384(3) . ? C21 H21 0.9300 . ? C4 C6 1.390(3) . ? C25 C20 1.392(3) . ? C25 C24 1.392(3) . ? C25 C26 1.505(3) . ? C24 H24 0.9300 . ? N3 C17 1.314(2) . ? N3 C18 1.382(2) . ? C13 C14 1.382(3) . ? C13 C15 1.383(3) 7_565 ? C7 C8 1.391(3) . ? C7 C6 1.395(3) . ? C7 C9 1.513(3) . ? C28 C29 1.344(3) . ? C28 H28 0.9300 . ? C15 C13 1.383(3) 7_565 ? C15 C14 1.390(3) . ? C15 H15 0.9300 . ? C27 H27 0.9300 . ? C19 C18 1.362(3) . ? C19 H19 0.9300 . ? C17 H17 0.9300 . ? C8 H8 0.9300 . ? C10 H10 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C6 H6 0.9300 . ? C18 H18 0.9300 . ? C29 H29 0.9300 . ? C14 C16 1.503(3) . ? C12 C11 1.348(3) . ? C12 H12 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C11 H11 0.9300 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 N6 95.23(6) . 2_565 ? O1 Ni1 N1 88.87(6) . . ? N6 Ni1 N1 172.95(6) 2_565 . ? O1 Ni1 N3 105.52(6) . . ? N6 Ni1 N3 94.98(6) 2_565 . ? N1 Ni1 N3 89.43(6) . . ? O1 Ni1 O3 161.15(5) . 3_445 ? N6 Ni1 O3 86.51(5) 2_565 3_445 ? N1 Ni1 O3 87.77(5) . 3_445 ? N3 Ni1 O3 93.00(5) . 3_445 ? O1 Ni1 O4 101.07(5) . 3_445 ? N6 Ni1 O4 87.50(6) 2_565 3_445 ? N1 Ni1 O4 86.08(6) . 3_445 ? N3 Ni1 O4 152.94(5) . 3_445 ? O3 Ni1 O4 60.19(4) 3_445 3_445 ? O1 Ni1 C5 131.06(6) . 3_445 ? N6 Ni1 C5 85.76(6) 2_565 3_445 ? N1 Ni1 C5 87.22(6) . 3_445 ? N3 Ni1 C5 123.19(6) . 3_445 ? O3 Ni1 C5 30.22(5) 3_445 3_445 ? O4 Ni1 C5 29.99(5) 3_445 3_445 ? C5 O3 Ni1 89.87(9) . 3 ? C5 O4 Ni1 89.08(11) . 3 ? C1 O1 Ni1 132.80(12) . . ? C17 N4 C19 107.07(15) . . ? C17 N4 C20 123.36(15) . . ? C19 N4 C20 128.74(15) . . ? C27 N5 C28 106.34(14) . . ? C27 N5 C23 128.95(15) . . ? C28 N5 C23 124.47(15) . . ? C10 N2 C12 106.71(16) . . ? C10 N2 C13 126.53(16) . . ? C12 N2 C13 126.29(17) . . ? C21 C22 C23 116.83(17) . . ? C21 C22 C40 118.06(17) . . ? C23 C22 C40 125.11(17) . . ? C27 N6 C29 105.83(15) . . ? C27 N6 Ni1 129.46(12) . 2_545 ? C29 N6 Ni1 124.32(12) . 2_545 ? C10 N1 C11 105.10(16) . . ? C10 N1 Ni1 127.61(13) . . ? C11 N1 Ni1 127.17(13) . . ? O4 C5 O3 120.78(15) . . ? O4 C5 C4 119.99(16) . . ? O3 C5 C4 119.23(15) . . ? O4 C5 Ni1 60.93(9) . 3 ? O3 C5 Ni1 59.91(8) . 3 ? C4 C5 Ni1 177.63(13) . 3 ? C24 C23 C22 120.93(16) . . ? C24 C23 N5 116.28(15) . . ? C22 C23 N5 122.77(16) . . ? C8 C2 C3 118.69(16) . . ? C8 C2 C1 121.88(15) . . ? C3 C2 C1 119.43(16) . . ? C4 C3 C2 120.66(17) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C20 C21 C22 121.80(17) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C3 C4 C6 119.58(16) . . ? C3 C4 C5 120.75(16) . . ? C6 C4 C5 119.67(15) . . ? C20 C25 C24 116.70(17) . . ? C20 C25 C26 123.04(18) . . ? C24 C25 C26 120.25(18) . . ? C25 C24 C23 121.89(17) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? O2 C1 O1 126.35(16) . . ? O2 C1 C2 118.38(15) . . ? O1 C1 C2 115.27(16) . . ? C17 N3 C18 105.01(15) . . ? C17 N3 Ni1 117.12(12) . . ? C18 N3 Ni1 137.08(12) . . ? C14 C13 C15 123.26(17) . 7_565 ? C14 C13 N2 117.80(18) . . ? C15 C13 N2 118.94(17) 7_565 . ? C8 C7 C6 118.48(18) . . ? C8 C7 C9 121.93(18) . . ? C6 C7 C9 119.59(18) . . ? C29 C28 N5 106.15(16) . . ? C29 C28 H28 126.9 . . ? N5 C28 H28 126.9 . . ? C21 C20 C25 121.61(16) . . ? C21 C20 N4 119.68(16) . . ? C25 C20 N4 118.69(17) . . ? C13 C15 C14 120.31(19) 7_565 . ? C13 C15 H15 119.8 7_565 . ? C14 C15 H15 119.8 . . ? N6 C27 N5 111.45(16) . . ? N6 C27 H27 124.3 . . ? N5 C27 H27 124.3 . . ? C18 C19 N4 105.78(16) . . ? C18 C19 H19 127.1 . . ? N4 C19 H19 127.1 . . ? N3 C17 N4 112.16(16) . . ? N3 C17 H17 123.9 . . ? N4 C17 H17 123.9 . . ? C2 C8 C7 121.71(17) . . ? C2 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? N1 C10 N2 111.98(17) . . ? N1 C10 H10 124.0 . . ? N2 C10 H10 124.0 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C6 C7 120.82(17) . . ? C4 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C19 C18 N3 109.98(16) . . ? C19 C18 H18 125.0 . . ? N3 C18 H18 125.0 . . ? C28 C29 N6 110.20(16) . . ? C28 C29 H29 124.9 . . ? N6 C29 H29 124.9 . . ? C13 C14 C15 116.44(18) . . ? C13 C14 C16 120.92(19) . . ? C15 C14 C16 122.48(19) . . ? C11 C12 N2 106.11(18) . . ? C11 C12 H12 126.9 . . ? N2 C12 H12 126.9 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C12 C11 N1 110.08(18) . . ? C12 C11 H11 125.0 . . ? N1 C11 H11 125.0 . . ? C22 C40 H40A 109.5 . . ? C22 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C22 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 N6 Ni1 O1 C1 66.94(16) 2_565 . . . ? N1 Ni1 O1 C1 -118.81(17) . . . . ? N3 Ni1 O1 C1 -29.72(17) . . . . ? O3 Ni1 O1 C1 161.46(15) 3_445 . . . ? O4 Ni1 O1 C1 155.40(16) 3_445 . . . ? C5 Ni1 O1 C1 155.86(15) 3_445 . . . ? O1 Ni1 N1 C10 10.83(18) . . . . ? N6 Ni1 N1 C10 136.5(4) 2_565 . . . ? N3 Ni1 N1 C10 -94.70(18) . . . . ? O3 Ni1 N1 C10 172.28(18) 3_445 . . . ? O4 Ni1 N1 C10 112.01(18) 3_445 . . . ? C5 Ni1 N1 C10 142.03(18) 3_445 . . . ? O1 Ni1 N1 C11 -173.51(19) . . . . ? N6 Ni1 N1 C11 -47.8(6) 2_565 . . . ? N3 Ni1 N1 C11 80.96(19) . . . . ? O3 Ni1 N1 C11 -12.07(19) 3_445 . . . ? O4 Ni1 N1 C11 -72.34(19) 3_445 . . . ? C5 Ni1 N1 C11 -42.31(19) 3_445 . . . ? Ni1 O4 C5 O3 -2.72(17) 3 . . . ? Ni1 O4 C5 C4 177.49(14) 3 . . . ? Ni1 O3 C5 O4 2.74(17) 3 . . . ? Ni1 O3 C5 C4 -177.46(14) 3 . . . ? C21 C22 C23 C24 4.5(3) . . . . ? C40 C22 C23 C24 -175.2(2) . . . . ? C21 C22 C23 N5 -177.07(16) . . . . ? C40 C22 C23 N5 3.2(3) . . . . ? C27 N5 C23 C24 -145.16(18) . . . . ? C28 N5 C23 C24 28.5(3) . . . . ? C27 N5 C23 C22 36.3(3) . . . . ? C28 N5 C23 C22 -150.05(19) . . . . ? C8 C2 C3 C4 -0.5(3) . . . . ? C1 C2 C3 C4 179.79(16) . . . . ? C23 C22 C21 C20 -2.8(3) . . . . ? C40 C22 C21 C20 176.96(19) . . . . ? C2 C3 C4 C6 2.2(3) . . . . ? C2 C3 C4 C5 -178.01(16) . . . . ? O4 C5 C4 C3 -161.11(17) . . . . ? O3 C5 C4 C3 19.1(3) . . . . ? Ni1 C5 C4 C3 -49(3) 3 . . . ? O4 C5 C4 C6 18.7(3) . . . . ? O3 C5 C4 C6 -161.08(17) . . . . ? Ni1 C5 C4 C6 131(3) 3 . . . ? C20 C25 C24 C23 -2.9(3) . . . . ? C26 C25 C24 C23 175.62(19) . . . . ? C22 C23 C24 C25 -1.7(3) . . . . ? N5 C23 C24 C25 179.76(16) . . . . ? Ni1 O1 C1 O2 -10.9(3) . . . . ? Ni1 O1 C1 C2 169.71(12) . . . . ? C8 C2 C1 O2 -159.20(18) . . . . ? C3 C2 C1 O2 20.5(2) . . . . ? C8 C2 C1 O1 20.2(3) . . . . ? C3 C2 C1 O1 -160.03(16) . . . . ? O1 Ni1 N3 C17 -166.60(14) . . . . ? N6 Ni1 N3 C17 96.56(14) 2_565 . . . ? N1 Ni1 N3 C17 -77.93(14) . . . . ? O3 Ni1 N3 C17 9.80(14) 3_445 . . . ? O4 Ni1 N3 C17 2.3(2) 3_445 . . . ? C5 Ni1 N3 C17 8.37(16) 3_445 . . . ? O1 Ni1 N3 C18 1.35(19) . . . . ? N6 Ni1 N3 C18 -95.50(18) 2_565 . . . ? N1 Ni1 N3 C18 90.02(18) . . . . ? O3 Ni1 N3 C18 177.75(18) 3_445 . . . ? O4 Ni1 N3 C18 170.25(15) 3_445 . . . ? C5 Ni1 N3 C18 176.32(17) 3_445 . . . ? C10 N2 C13 C14 79.6(3) . . . . ? C12 N2 C13 C14 -91.5(3) . . . . ? C10 N2 C13 C15 -100.4(3) . . . 7_565 ? C12 N2 C13 C15 88.5(3) . . . 7_565 ? C27 N5 C28 C29 -1.0(2) . . . . ? C23 N5 C28 C29 -175.87(18) . . . . ? C22 C21 C20 C25 -1.8(3) . . . . ? C22 C21 C20 N4 176.16(17) . . . . ? C24 C25 C20 C21 4.6(3) . . . . ? C26 C25 C20 C21 -173.85(19) . . . . ? C24 C25 C20 N4 -173.39(15) . . . . ? C26 C25 C20 N4 8.1(3) . . . . ? C17 N4 C20 C21 -106.6(2) . . . . ? C19 N4 C20 C21 85.1(2) . . . . ? C17 N4 C20 C25 71.4(2) . . . . ? C19 N4 C20 C25 -96.8(2) . . . . ? C29 N6 C27 N5 -1.2(2) . . . . ? Ni1 N6 C27 N5 171.85(12) 2_545 . . . ? C28 N5 C27 N6 1.4(2) . . . . ? C23 N5 C27 N6 175.94(17) . . . . ? C17 N4 C19 C18 -0.2(2) . . . . ? C20 N4 C19 C18 169.55(18) . . . . ? C18 N3 C17 N4 0.1(2) . . . . ? Ni1 N3 C17 N4 171.67(13) . . . . ? C19 N4 C17 N3 0.0(2) . . . . ? C20 N4 C17 N3 -170.39(17) . . . . ? C3 C2 C8 C7 -1.7(3) . . . . ? C1 C2 C8 C7 178.08(18) . . . . ? C6 C7 C8 C2 2.0(3) . . . . ? C9 C7 C8 C2 -178.1(2) . . . . ? C11 N1 C10 N2 0.9(2) . . . . ? Ni1 N1 C10 N2 177.31(14) . . . . ? C12 N2 C10 N1 -0.9(3) . . . . ? C13 N2 C10 N1 -173.36(19) . . . . ? C3 C4 C6 C7 -1.8(3) . . . . ? C5 C4 C6 C7 178.37(18) . . . . ? C8 C7 C6 C4 -0.3(3) . . . . ? C9 C7 C6 C4 179.8(2) . . . . ? N4 C19 C18 N3 0.3(2) . . . . ? C17 N3 C18 C19 -0.3(2) . . . . ? Ni1 N3 C18 C19 -169.17(14) . . . . ? N5 C28 C29 N6 0.4(2) . . . . ? C27 N6 C29 C28 0.5(2) . . . . ? Ni1 N6 C29 C28 -172.99(14) 2_545 . . . ? C15 C13 C14 C15 0.0(3) 7_565 . . . ? N2 C13 C14 C15 180.00(18) . . . . ? C15 C13 C14 C16 -175.6(2) 7_565 . . . ? N2 C13 C14 C16 4.5(3) . . . . ? C13 C15 C14 C13 0.0(3) 7_565 . . . ? C13 C15 C14 C16 175.5(2) 7_565 . . . ? C10 N2 C12 C11 0.4(3) . . . . ? C13 N2 C12 C11 173.0(2) . . . . ? N2 C12 C11 N1 0.1(3) . . . . ? C10 N1 C11 C12 -0.6(3) . . . . ? Ni1 N1 C11 C12 -177.04(17) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.631 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 890912' ####################################################################### # # 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_Ni_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 N10 Ni2 O15' _chemical_formula_weight 1066.28 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' 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' H H 0.0000 0.0000 '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 23.1936(10) _cell_length_b 15.0255(7) _cell_length_c 16.4652(13) _cell_angle_alpha 90.00 _cell_angle_beta 124.6951(4) _cell_angle_gamma 90.00 _cell_volume 4717.8(5) _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 block _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 0.878 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7786 _exptl_absorpt_correction_T_max 0.8440 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14448 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5384 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART(Bruker,1998) _computing_cell_refinement 'Bruker SMART' _computing_data_reduction SAINT(Bruker,1998) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker,1998)' _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^)+(0.0440P)^2^+3.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5384 _refine_ls_number_parameters 395 _refine_ls_number_restraints 493 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 0.979 _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 Ni1 Ni 0.249627(11) 0.226946(15) 0.098632(14) 0.02179(8) Uani 1 1 d . . . O1 O 0.34012(6) 0.29510(9) 0.18390(9) 0.0285(3) Uani 1 1 d . A . O2 O 0.30020(7) 0.43486(9) 0.13932(10) 0.0354(3) Uani 1 1 d . A . O3 O 0.58696(6) 0.23027(9) 0.42238(9) 0.0303(3) Uani 1 1 d . A . O4 O 0.65968(6) 0.34242(9) 0.51239(9) 0.0293(3) Uani 1 1 d . . . O7 O 0.21348(7) 0.32615(10) -0.01268(9) 0.0257(3) Uani 1 1 d . . . H7A H 0.1690(15) 0.3191(18) -0.0378(19) 0.061(8) Uiso 1 1 d . . . H7B H 0.2338(13) 0.3712(18) 0.0226(19) 0.055(8) Uiso 1 1 d . . . N1 N 0.29154(7) 0.12512(10) 0.19992(10) 0.0265(3) Uani 1 1 d . . . N2 N 0.36754(8) 0.05438(11) 0.33787(11) 0.0333(4) Uani 1 1 d . . . N3 N 0.21109(8) 0.28470(10) 0.17548(11) 0.0290(3) Uani 1 1 d . . . N4 N 0.20833(9) 0.28555(11) 0.30687(11) 0.0310(4) Uani 1 1 d . . . C1 C 0.34654(9) 0.37861(13) 0.19212(12) 0.0275(4) Uani 1 1 d D . . O5 O 0.5727(4) 0.6498(5) 0.4241(11) 0.156(5) Uani 0.428(7) 1 d PU A 1 O6 O 0.4751(4) 0.6720(4) 0.2873(9) 0.139(4) Uani 0.428(7) 1 d PU A 1 N5 N 0.5167(4) 0.6246(4) 0.3529(11) 0.109(4) Uani 0.428(7) 1 d PDU A 1 C2 C 0.4202(2) 0.4071(4) 0.2724(5) 0.033(2) Uani 0.428(7) 1 d PGDU A 1 C3 C 0.4748(4) 0.3486(3) 0.3328(6) 0.0222(18) Uani 0.428(7) 1 d PGU A 1 H3A H 0.4662 0.2877 0.3290 0.027 Uiso 0.428(7) 1 calc PR A 1 C4 C 0.5423(3) 0.3810(3) 0.3989(5) 0.0245(18) Uani 0.428(7) 1 d PGDU A 1 C5 C 0.55518(18) 0.4719(4) 0.4046(4) 0.0444(19) Uani 0.428(7) 1 d PGU A 1 H5A H 0.6003 0.4936 0.4488 0.053 Uiso 0.428(7) 1 calc PR A 1 C6 C 0.5006(2) 0.5304(3) 0.3441(5) 0.0516(18) Uani 0.428(7) 1 d PGDU A 1 C7 C 0.4331(2) 0.4980(4) 0.2780(4) 0.0433(18) Uani 0.428(7) 1 d PGU A 1 H7C H 0.3966 0.5371 0.2376 0.052 Uiso 0.428(7) 1 calc PR A 1 O5B O 0.5722(3) 0.6331(4) 0.4948(5) 0.097(2) Uani 0.572(7) 1 d PU A 2 O6B O 0.4694(3) 0.6680(3) 0.3823(7) 0.159(4) Uani 0.572(7) 1 d PU A 2 N5B N 0.5159(3) 0.6150(3) 0.4235(5) 0.0775(19) Uani 0.572(7) 1 d PDU A 2 C2B C 0.41822(18) 0.4131(3) 0.2775(3) 0.0306(16) Uani 0.572(7) 1 d PGDU A 2 C3B C 0.4711(3) 0.3495(2) 0.3211(5) 0.0285(16) Uani 0.572(7) 1 d PGU A 2 H3B H 0.4615 0.2913 0.2979 0.034 Uiso 0.572(7) 1 calc PR A 2 C4B C 0.5384(2) 0.3729(2) 0.3994(4) 0.0339(18) Uani 0.572(7) 1 d PGDU A 2 C5B C 0.55286(13) 0.4600(3) 0.4341(3) 0.0352(12) Uani 0.572(7) 1 d PGU A 2 H5B H 0.5979 0.4757 0.4865 0.042 Uiso 0.572(7) 1 calc PR A 2 C6B C 0.49995(18) 0.5236(2) 0.3905(3) 0.0416(12) Uani 0.572(7) 1 d PGDU A 2 C7B C 0.43263(15) 0.5002(3) 0.3123(3) 0.0417(13) Uani 0.572(7) 1 d PGU A 2 H7D H 0.3972 0.5427 0.2831 0.050 Uiso 0.572(7) 1 calc PR A 2 C8 C 0.59999(9) 0.31030(13) 0.44797(12) 0.0258(4) Uani 1 1 d D . . C9 C 0.35844(9) 0.11208(13) 0.26837(13) 0.0301(4) Uani 1 1 d . . . H9 H 0.3948 0.1390 0.2690 0.036 Uiso 1 1 calc R . . C10 C 0.25576(10) 0.07300(13) 0.22615(13) 0.0296(4) Uani 1 1 d . . . H10 H 0.2072 0.0691 0.1909 0.035 Uiso 1 1 calc R . . C11 C 0.30147(10) 0.02839(14) 0.31048(14) 0.0345(5) Uani 1 1 d . . . H11 H 0.2908 -0.0115 0.3433 0.041 Uiso 1 1 calc R . . C12 C 0.43486(10) 0.02623(14) 0.42237(14) 0.0349(5) Uani 1 1 d . . . C13 C 0.48231(11) -0.00674(17) 0.40603(15) 0.0445(6) Uani 1 1 d . . . H13 H 0.4696 -0.0108 0.3414 0.053 Uiso 1 1 calc R . . C14 C 0.54902(11) -0.03446(17) 0.48266(16) 0.0464(6) Uani 1 1 d . . . C15 C 0.59779(16) -0.0741(3) 0.4595(2) 0.1037(15) Uani 1 1 d . . . H15A H 0.6321 -0.0306 0.4714 0.155 Uiso 1 1 calc R . . H15B H 0.5714 -0.0920 0.3915 0.155 Uiso 1 1 calc R . . H15C H 0.6210 -0.1250 0.5009 0.155 Uiso 1 1 calc R . . C16 C 0.24817(10) 0.27629(13) 0.27263(13) 0.0314(4) Uani 1 1 d . . . H16 H 0.2961 0.2653 0.3123 0.038 Uiso 1 1 calc R . . C17 C 0.14405(11) 0.30187(15) 0.14712(14) 0.0382(5) Uani 1 1 d . . . H17 H 0.1060 0.3117 0.0825 0.046 Uiso 1 1 calc R . . C18 C 0.14154(11) 0.30233(17) 0.22695(15) 0.0452(6) Uani 1 1 d . . . H18 H 0.1022 0.3121 0.2276 0.054 Uiso 1 1 calc R . . C19 C 0.23005(11) 0.26886(13) 0.40676(13) 0.0308(4) Uani 1 1 d . . . C20 C 0.22801(11) 0.18213(14) 0.43249(14) 0.0370(5) Uani 1 1 d . . . H20 H 0.2130 0.1373 0.3857 0.044 Uiso 1 1 calc R . . C21 C 0.24807(11) 0.16075(13) 0.52747(14) 0.0347(4) Uani 1 1 d . . . C22 C 0.24610(15) 0.06678(15) 0.55684(18) 0.0549(7) Uani 1 1 d . . . H22A H 0.2927 0.0481 0.6081 0.082 Uiso 1 1 calc R . . H22B H 0.2276 0.0284 0.5006 0.082 Uiso 1 1 calc R . . H22C H 0.2167 0.0638 0.5806 0.082 Uiso 1 1 calc R . . O1W O 0.5000 0.12489(16) 0.2500 0.0505(7) Uani 1 2 d S . . H1A H 0.5321 0.1620 0.3004 0.076 Uiso 0.50 1 d PG . . H1B H 0.4803 0.1515 0.1981 0.076 Uiso 0.50 1 d PG . . 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 0.01626(12) 0.03143(14) 0.01304(11) 0.00437(9) 0.00558(9) 0.00377(9) O1 0.0186(6) 0.0344(7) 0.0227(6) 0.0026(5) 0.0060(5) 0.0012(5) O2 0.0249(7) 0.0393(8) 0.0311(7) 0.0050(6) 0.0094(6) 0.0083(6) O3 0.0195(6) 0.0351(7) 0.0257(6) -0.0027(6) 0.0066(5) -0.0027(5) O4 0.0174(6) 0.0384(7) 0.0220(6) -0.0042(5) 0.0051(5) -0.0027(5) O7 0.0186(6) 0.0361(8) 0.0186(6) 0.0024(5) 0.0083(5) 0.0016(6) N1 0.0216(7) 0.0332(8) 0.0183(7) 0.0046(6) 0.0075(6) 0.0032(6) N2 0.0209(8) 0.0431(10) 0.0262(8) 0.0158(7) 0.0076(7) 0.0055(7) N3 0.0294(8) 0.0382(9) 0.0195(7) 0.0022(6) 0.0141(6) 0.0026(7) N4 0.0359(9) 0.0396(9) 0.0215(7) 0.0001(7) 0.0187(7) 0.0007(7) C1 0.0200(9) 0.0388(11) 0.0215(8) 0.0022(8) 0.0104(7) 0.0033(8) O5 0.068(4) 0.054(4) 0.229(10) -0.018(6) 0.016(6) -0.024(3) O6 0.076(4) 0.034(3) 0.227(10) 0.017(5) 0.039(5) 0.004(3) N5 0.044(4) 0.038(3) 0.174(9) -0.011(5) 0.021(5) -0.008(3) C2 0.030(4) 0.032(4) 0.034(3) -0.008(3) 0.017(3) -0.005(3) C3 0.021(3) 0.027(3) 0.014(2) -0.003(2) 0.007(2) 0.004(3) C4 0.006(3) 0.039(3) 0.027(3) -0.007(3) 0.009(2) -0.002(3) C5 0.024(2) 0.035(3) 0.062(4) -0.004(3) 0.018(3) -0.012(2) C6 0.037(3) 0.033(3) 0.063(4) -0.010(3) 0.015(3) 0.000(2) C7 0.023(2) 0.037(3) 0.049(3) -0.010(3) 0.008(2) 0.004(2) O5B 0.062(3) 0.050(3) 0.125(4) -0.039(3) 0.020(3) -0.013(2) O6B 0.076(3) 0.050(3) 0.197(7) -0.042(3) -0.014(4) 0.026(2) N5B 0.048(3) 0.039(2) 0.102(4) -0.021(3) 0.017(3) 0.006(2) C2B 0.016(2) 0.034(3) 0.035(3) 0.003(2) 0.010(2) 0.009(2) C3B 0.020(3) 0.038(3) 0.020(2) 0.003(2) 0.0075(19) -0.002(2) C4B 0.030(3) 0.029(3) 0.033(3) -0.007(2) 0.012(3) -0.004(2) C5B 0.0219(18) 0.037(2) 0.037(2) -0.0032(18) 0.0109(16) -0.0016(16) C6B 0.0293(19) 0.033(2) 0.045(2) -0.0075(18) 0.0106(18) 0.0018(15) C7B 0.031(2) 0.037(2) 0.045(3) -0.006(2) 0.0145(19) 0.0113(16) C8 0.0187(8) 0.0392(10) 0.0170(8) -0.0004(7) 0.0086(7) -0.0005(8) C9 0.0213(9) 0.0387(11) 0.0251(9) 0.0111(8) 0.0101(8) 0.0031(8) C10 0.0207(9) 0.0364(10) 0.0265(9) 0.0043(8) 0.0103(8) -0.0001(8) C11 0.0269(10) 0.0429(11) 0.0314(10) 0.0119(9) 0.0152(8) 0.0000(8) C12 0.0245(9) 0.0407(11) 0.0276(9) 0.0168(8) 0.0078(8) 0.0060(8) C13 0.0327(11) 0.0704(16) 0.0230(9) 0.0142(10) 0.0114(9) 0.0122(11) C14 0.0317(11) 0.0685(16) 0.0315(11) 0.0128(11) 0.0134(9) 0.0160(11) C15 0.0571(19) 0.203(4) 0.0435(16) 0.013(2) 0.0243(15) 0.060(2) C16 0.0288(10) 0.0437(11) 0.0222(9) 0.0019(8) 0.0147(8) 0.0040(8) C17 0.0308(11) 0.0564(13) 0.0237(9) 0.0002(9) 0.0132(8) 0.0098(10) C18 0.0316(11) 0.0731(16) 0.0323(11) -0.0029(11) 0.0190(9) 0.0078(11) C19 0.0381(11) 0.0387(11) 0.0229(9) -0.0015(8) 0.0217(8) -0.0009(9) C20 0.0513(13) 0.0368(11) 0.0281(10) -0.0073(8) 0.0258(10) -0.0042(10) C21 0.0469(12) 0.0340(10) 0.0308(10) 0.0001(8) 0.0266(9) -0.0013(9) C22 0.089(2) 0.0385(13) 0.0442(13) -0.0017(10) 0.0417(14) -0.0074(12) O1W 0.0483(16) 0.0542(16) 0.0320(11) 0.000 0.0128(12) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O1 2.0175(12) . ? Ni1 O4 2.0206(12) 8_455 ? Ni1 N1 2.0547(15) . ? Ni1 N3 2.1073(16) . ? Ni1 O7 2.1295(13) . ? Ni1 O7 2.1795(13) 7 ? O1 C1 1.262(2) . ? O2 C1 1.250(2) . ? O3 C8 1.253(2) . ? O4 C8 1.266(2) . ? O4 Ni1 2.0205(12) 8_556 ? O7 Ni1 2.1795(13) 7 ? O7 H7A 0.87(3) . ? O7 H7B 0.84(3) . ? N1 C9 1.314(2) . ? N1 C10 1.377(2) . ? N2 C9 1.353(2) . ? N2 C11 1.385(2) . ? N2 C12 1.442(2) . ? N3 C16 1.322(2) . ? N3 C17 1.370(2) . ? N4 C16 1.336(2) . ? N4 C18 1.369(3) . ? N4 C19 1.442(2) . ? C1 C2 1.509(4) . ? C1 C2B 1.533(3) . ? O5 N5 1.213(11) . ? O6 N5 1.191(11) . ? N5 C6 1.450(6) . ? C2 C3 1.3900 . ? C2 C7 1.3900 . ? C3 C4 1.3900 . ? C3 H3A 0.9300 . ? C4 C5 1.3900 . ? C4 C8 1.530(4) . ? C5 C6 1.3900 . ? C5 H5A 0.9300 . ? C6 C7 1.3900 . ? C7 H7C 0.9300 . ? O5B N5B 1.187(6) . ? O6B N5B 1.194(6) . ? N5B C6B 1.445(4) . ? C2B C3B 1.3900 . ? C2B C7B 1.3900 . ? C3B C4B 1.3900 . ? C3B H3B 0.9300 . ? C4B C5B 1.3900 . ? C4B C8 1.504(3) . ? C5B C6B 1.3900 . ? C5B H5B 0.9300 . ? C6B C7B 1.3900 . ? C7B H7D 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.351(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.366(3) . ? C12 C14 1.391(3) 5_656 ? C13 C14 1.392(3) . ? C13 H13 0.9300 . ? C14 C12 1.391(3) 5_656 ? C14 C15 1.507(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16 0.9300 . ? C17 C18 1.348(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.379(3) . ? C19 C21 1.387(3) 7_556 ? C20 C21 1.392(3) . ? C20 H20 0.9300 . ? C21 C19 1.387(3) 7_556 ? C21 C22 1.501(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O1W H1A 0.92(11) . ? O1W H1B 0.8085 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 O4 179.11(5) . 8_455 ? O1 Ni1 N1 89.37(5) . . ? O4 Ni1 N1 90.49(5) 8_455 . ? O1 Ni1 N3 90.11(6) . . ? O4 Ni1 N3 90.76(6) 8_455 . ? N1 Ni1 N3 89.18(6) . . ? O1 Ni1 O7 89.29(5) . . ? O4 Ni1 O7 90.75(5) 8_455 . ? N1 Ni1 O7 172.95(6) . . ? N3 Ni1 O7 97.75(6) . . ? O1 Ni1 O7 90.01(5) . 7 ? O4 Ni1 O7 89.13(5) 8_455 7 ? N1 Ni1 O7 94.32(6) . 7 ? N3 Ni1 O7 176.50(5) . 7 ? O7 Ni1 O7 78.76(6) . 7 ? C1 O1 Ni1 126.30(11) . . ? C8 O4 Ni1 126.25(12) . 8_556 ? Ni1 O7 Ni1 101.24(6) . 7 ? Ni1 O7 H7A 95.9(17) . . ? Ni1 O7 H7A 116.3(17) 7 . ? Ni1 O7 H7B 100.2(17) . . ? Ni1 O7 H7B 118.0(18) 7 . ? H7A O7 H7B 118(2) . . ? C9 N1 C10 105.93(15) . . ? C9 N1 Ni1 126.12(13) . . ? C10 N1 Ni1 125.94(12) . . ? C9 N2 C11 107.11(15) . . ? C9 N2 C12 124.47(16) . . ? C11 N2 C12 128.41(16) . . ? C16 N3 C17 105.12(16) . . ? C16 N3 Ni1 118.75(13) . . ? C17 N3 Ni1 131.31(12) . . ? C16 N4 C18 106.84(16) . . ? C16 N4 C19 125.94(17) . . ? C18 N4 C19 126.73(17) . . ? O2 C1 O1 126.56(16) . . ? O2 C1 C2 121.0(3) . . ? O1 C1 C2 112.4(3) . . ? O2 C1 C2B 117.6(2) . . ? O1 C1 C2B 115.8(2) . . ? C2 C1 C2B 5.5(5) . . ? O6 N5 O5 124.0(7) . . ? O6 N5 C6 117.6(7) . . ? O5 N5 C6 118.3(7) . . ? C3 C2 C7 120.0 . . ? C3 C2 C1 124.3(4) . . ? C7 C2 C1 115.5(4) . . ? C2 C3 C4 120.0 . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 C8 115.3(4) . . ? C5 C4 C8 123.8(4) . . ? C6 C5 C4 120.0 . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? C7 C6 C5 120.0 . . ? C7 C6 N5 122.1(5) . . ? C5 C6 N5 117.9(5) . . ? C6 C7 C2 120.0 . . ? C6 C7 H7C 120.0 . . ? C2 C7 H7C 120.0 . . ? O5B N5B O6B 122.5(5) . . ? O5B N5B C6B 119.4(5) . . ? O6B N5B C6B 117.7(4) . . ? C3B C2B C7B 120.0 . . ? C3B C2B C1 114.8(3) . . ? C7B C2B C1 125.2(3) . . ? C4B C3B C2B 120.0 . . ? C4B C3B H3B 120.0 . . ? C2B C3B H3B 120.0 . . ? C3B C4B C5B 120.0 . . ? C3B C4B C8 124.0(3) . . ? C5B C4B C8 115.9(3) . . ? C6B C5B C4B 120.0 . . ? C6B C5B H5B 120.0 . . ? C4B C5B H5B 120.0 . . ? C5B C6B C7B 120.0 . . ? C5B C6B N5B 119.8(3) . . ? C7B C6B N5B 120.1(3) . . ? C6B C7B C2B 120.0 . . ? C6B C7B H7D 120.0 . . ? C2B C7B H7D 120.0 . . ? O3 C8 O4 125.95(16) . . ? O3 C8 C4B 116.6(2) . . ? O4 C8 C4B 117.5(2) . . ? O3 C8 C4 121.2(3) . . ? O4 C8 C4 112.8(3) . . ? C4B C8 C4 5.7(4) . . ? N1 C9 N2 111.14(16) . . ? N1 C9 H9 124.4 . . ? N2 C9 H9 124.4 . . ? C11 C10 N1 110.13(16) . . ? C11 C10 H10 124.9 . . ? N1 C10 H10 124.9 . . ? C10 C11 N2 105.68(17) . . ? C10 C11 H11 127.2 . . ? N2 C11 H11 127.2 . . ? C13 C12 C14 121.49(18) . 5_656 ? C13 C12 N2 117.88(18) . . ? C14 C12 N2 120.61(19) 5_656 . ? C12 C13 C14 122.3(2) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C12 C14 C13 116.2(2) 5_656 . ? C12 C14 C15 124.0(2) 5_656 . ? C13 C14 C15 119.8(2) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 N4 111.77(17) . . ? N3 C16 H16 124.1 . . ? N4 C16 H16 124.1 . . ? C18 C17 N3 109.82(17) . . ? C18 C17 H17 125.1 . . ? N3 C17 H17 125.1 . . ? C17 C18 N4 106.43(18) . . ? C17 C18 H18 126.8 . . ? N4 C18 H18 126.8 . . ? C20 C19 C21 122.82(17) . 7_556 ? C20 C19 N4 117.64(17) . . ? C21 C19 N4 119.55(17) 7_556 . ? C19 C20 C21 121.02(18) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C19 C21 C20 116.17(18) 7_556 . ? C19 C21 C22 122.03(18) 7_556 . ? C20 C21 C22 121.80(19) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? H1A O1W H1B 109.4 . . ? 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 O4 Ni1 O1 C1 131(3) 8_455 . . . ? N1 Ni1 O1 C1 -148.55(15) . . . . ? N3 Ni1 O1 C1 -59.38(15) . . . . ? O7 Ni1 O1 C1 38.37(15) . . . . ? O7 Ni1 O1 C1 117.13(15) 7 . . . ? O1 Ni1 O7 Ni1 90.15(6) . . . 7 ? O4 Ni1 O7 Ni1 -88.97(6) 8_455 . . 7 ? N1 Ni1 O7 Ni1 11.1(5) . . . 7 ? N3 Ni1 O7 Ni1 -179.83(6) . . . 7 ? O7 Ni1 O7 Ni1 0.0 7 . . 7 ? O1 Ni1 N1 C9 -18.08(16) . . . . ? O4 Ni1 N1 C9 161.04(16) 8_455 . . . ? N3 Ni1 N1 C9 -108.21(16) . . . . ? O7 Ni1 N1 C9 61.0(5) . . . . ? O7 Ni1 N1 C9 71.88(16) 7 . . . ? O1 Ni1 N1 C10 143.51(15) . . . . ? O4 Ni1 N1 C10 -37.37(15) 8_455 . . . ? N3 Ni1 N1 C10 53.38(15) . . . . ? O7 Ni1 N1 C10 -137.4(4) . . . . ? O7 Ni1 N1 C10 -126.53(15) 7 . . . ? O1 Ni1 N3 C16 -55.47(15) . . . . ? O4 Ni1 N3 C16 124.37(15) 8_455 . . . ? N1 Ni1 N3 C16 33.90(15) . . . . ? O7 Ni1 N3 C16 -144.77(15) . . . . ? O7 Ni1 N3 C16 -147.5(9) 7 . . . ? O1 Ni1 N3 C17 153.09(18) . . . . ? O4 Ni1 N3 C17 -27.06(18) 8_455 . . . ? N1 Ni1 N3 C17 -117.54(18) . . . . ? O7 Ni1 N3 C17 63.79(19) . . . . ? O7 Ni1 N3 C17 61.1(10) 7 . . . ? Ni1 O1 C1 O2 -10.9(3) . . . . ? Ni1 O1 C1 C2 172.2(4) . . . . ? Ni1 O1 C1 C2B 167.4(3) . . . . ? O2 C1 C2 C3 -178.8(3) . . . . ? O1 C1 C2 C3 -1.7(5) . . . . ? C2B C1 C2 C3 127(5) . . . . ? O2 C1 C2 C7 -4.1(6) . . . . ? O1 C1 C2 C7 172.9(4) . . . . ? C2B C1 C2 C7 -59(5) . . . . ? C7 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C4 174.4(6) . . . . ? C2 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C8 -169.6(5) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C8 C4 C5 C6 168.6(6) . . . . ? C4 C5 C6 C7 0.0 . . . . ? C4 C5 C6 N5 179.9(8) . . . . ? O6 N5 C6 C7 -17.3(15) . . . . ? O5 N5 C6 C7 165.9(10) . . . . ? O6 N5 C6 C5 162.8(10) . . . . ? O5 N5 C6 C5 -14.0(15) . . . . ? C5 C6 C7 C2 0.0 . . . . ? N5 C6 C7 C2 -179.9(8) . . . . ? C3 C2 C7 C6 0.0 . . . . ? C1 C2 C7 C6 -174.9(6) . . . . ? O2 C1 C2B C3B -168.0(2) . . . . ? O1 C1 C2B C3B 13.5(3) . . . . ? C2 C1 C2B C3B -40(5) . . . . ? O2 C1 C2B C7B 12.0(5) . . . . ? O1 C1 C2B C7B -166.5(3) . . . . ? C2 C1 C2B C7B 140(6) . . . . ? C7B C2B C3B C4B 0.0 . . . . ? C1 C2B C3B C4B -180.0(4) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C2B C3B C4B C8 -176.7(5) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C8 C4B C5B C6B 177.0(4) . . . . ? C4B C5B C6B C7B 0.0 . . . . ? C4B C5B C6B N5B -176.8(5) . . . . ? O5B N5B C6B C5B -8.5(9) . . . . ? O6B N5B C6B C5B 178.0(7) . . . . ? O5B N5B C6B C7B 174.6(6) . . . . ? O6B N5B C6B C7B 1.2(10) . . . . ? C5B C6B C7B C2B 0.0 . . . . ? N5B C6B C7B C2B 176.8(5) . . . . ? C3B C2B C7B C6B 0.0 . . . . ? C1 C2B C7B C6B 180.0(5) . . . . ? Ni1 O4 C8 O3 -4.4(3) 8_556 . . . ? Ni1 O4 C8 C4B 173.8(3) 8_556 . . . ? Ni1 O4 C8 C4 177.5(3) 8_556 . . . ? C3B C4B C8 O3 -8.1(4) . . . . ? C5B C4B C8 O3 175.1(3) . . . . ? C3B C4B C8 O4 173.6(2) . . . . ? C5B C4B C8 O4 -3.2(5) . . . . ? C3B C4B C8 C4 137(5) . . . . ? C5B C4B C8 C4 -40(5) . . . . ? C3 C4 C8 O3 6.3(4) . . . . ? C5 C4 C8 O3 -162.8(4) . . . . ? C3 C4 C8 O4 -175.4(3) . . . . ? C5 C4 C8 O4 15.4(6) . . . . ? C3 C4 C8 C4B -31(5) . . . . ? C5 C4 C8 C4B 160(5) . . . . ? C10 N1 C9 N2 -0.4(2) . . . . ? Ni1 N1 C9 N2 164.22(13) . . . . ? C11 N2 C9 N1 0.7(2) . . . . ? C12 N2 C9 N1 179.72(18) . . . . ? C9 N1 C10 C11 -0.2(2) . . . . ? Ni1 N1 C10 C11 -164.80(14) . . . . ? N1 C10 C11 N2 0.6(2) . . . . ? C9 N2 C11 C10 -0.8(2) . . . . ? C12 N2 C11 C10 -179.7(2) . . . . ? C9 N2 C12 C13 -52.5(3) . . . . ? C11 N2 C12 C13 126.2(2) . . . . ? C9 N2 C12 C14 126.1(2) . . . 5_656 ? C11 N2 C12 C14 -55.1(3) . . . 5_656 ? C14 C12 C13 C14 0.4(4) 5_656 . . . ? N2 C12 C13 C14 179.1(2) . . . . ? C12 C13 C14 C12 -0.4(4) . . . 5_656 ? C12 C13 C14 C15 177.2(3) . . . . ? C17 N3 C16 N4 1.1(2) . . . . ? Ni1 N3 C16 N4 -157.05(13) . . . . ? C18 N4 C16 N3 -1.0(2) . . . . ? C19 N4 C16 N3 171.38(18) . . . . ? C16 N3 C17 C18 -0.8(3) . . . . ? Ni1 N3 C17 C18 153.42(17) . . . . ? N3 C17 C18 N4 0.3(3) . . . . ? C16 N4 C18 C17 0.4(3) . . . . ? C19 N4 C18 C17 -171.9(2) . . . . ? C16 N4 C19 C20 -82.9(3) . . . . ? C18 N4 C19 C20 87.9(3) . . . . ? C16 N4 C19 C21 97.0(3) . . . 7_556 ? C18 N4 C19 C21 -92.1(3) . . . 7_556 ? C21 C19 C20 C21 0.1(4) 7_556 . . . ? N4 C19 C20 C21 -179.91(19) . . . . ? C19 C20 C21 C19 -0.1(3) . . . 7_556 ? C19 C20 C21 C22 179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.310 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 890913'