# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1709 data_global _publ_contact_author ; Dra. Miren Karmele Urtiaga Dpto. de Mineralog\'ia y Petrolog\'ia Universidad del Pa\'is Vasco Apartado 644 48080 Bilbao Spain ; _publ_contact_author_phone '34 4 6012555' _publ_contact_author_fax '34 4 4648500' _publ_contact_author_email nppurgrm@lg.ehu.es _publ_requested_journal 'J.Chem.Soc.Dalton Trans.' loop_ _publ_author_name _publ_author_address 'Serna, Z.E.' ; Dpto. Qu\'imica Inorg\'anica Facultad de CIencias Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Barandika, M.G.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Cortes, R.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Urtiaga, M.K.' ; Dpto. de Mineralog\'ia y Petrolog\'ia Facultad de CIencias Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Barberis, G.' ; Instituto de F\'isica Gleb Wataghin UMICAMP 13087-970 Campinas (SP) Brazil ; 'Rojo, T.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Ciencia Universidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; data_nibpco _audit_creation_method SHELXL _chemical_formula_sum 'C22 H20 N10 Ni2 O5' _chemical_formula_weight 621.90 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.230(3) _cell_length_b 10.358(4) _cell_length_c 13.396(8) _cell_angle_alpha 91.57(4) _cell_angle_beta 105.53(5) _cell_angle_gamma 96.26(3) _cell_volume 1357.1(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.522 _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 1.439 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w-2\q' _diffrn_standards_number 2 _diffrn_standards_interval_count 200 _diffrn_reflns_number 7830 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0886 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 29.96 _reflns_number_total 7830 _reflns_number_observed 3953 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD-4' _computing_cell_refinement 'Enraf-Nonius CAD-4' _computing_data_reduction 'Xtal 3.2 (Hall, Flack & Stewart, 1992)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _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^)+(0.1659P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7830 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1611 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.2620 _refine_ls_wR_factor_gt 0.1951 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 2.676 _refine_ls_shift/su_mean 0.227 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 0.09980(7) 0.18792(7) 0.15729(5) 0.0393(2) Uani 1 1 d . . . Ni2 Ni 0.02569(6) -0.10088(7) 0.08670(5) 0.0354(2) Uani 1 1 d . . . N5 N -0.0315(5) 0.2422(5) 0.0225(4) 0.0446(11) Uani 1 1 d . . . N6 N -0.1142(5) 0.3164(5) 0.0146(4) 0.0478(12) Uani 1 1 d . . . N7 N -0.1914(8) 0.3873(9) 0.0068(7) 0.097(3) Uani 1 1 d . . . N8 N 0.0601(9) 0.3416(8) 0.2399(6) 0.078(2) Uani 1 1 d . . . N9A N 0.120(3) 0.417(3) 0.300(3) 0.114(10) Uani 0.50 1 d P . . N9B N 0.077(4) 0.354(3) 0.323(2) 0.171(13) Uani 0.50 1 d P . . N10A N 0.181(4) 0.486(5) 0.377(2) 0.31(2) Uani 0.50 1 d P . . N10B N 0.148(6) 0.417(5) 0.431(3) 0.28(2) Uani 0.50 1 d P . . N1 N 0.1961(5) 0.1146(5) 0.2989(4) 0.0472(12) Uani 1 1 d . . . C1 C 0.3271(7) 0.1530(7) 0.3579(5) 0.0562(17) Uani 1 1 d . . . H1 H 0.3836 0.2101 0.3309 0.077(6) Uiso 1 1 calc R . . C2 C 0.3783(8) 0.1103(9) 0.4555(5) 0.067(2) Uani 1 1 d . . . H2 H 0.4675 0.1381 0.4941 0.077(6) Uiso 1 1 calc R . . C3 C 0.2926(9) 0.0242(9) 0.4952(6) 0.078(2) Uani 1 1 d . . . H3 H 0.3245 -0.0055 0.5612 0.077(6) Uiso 1 1 calc R . . C4 C 0.1638(8) -0.0162(8) 0.4381(5) 0.0644(19) Uani 1 1 d . . . H4 H 0.1067 -0.0739 0.4642 0.077(6) Uiso 1 1 calc R . . C5 C 0.1172(7) 0.0298(7) 0.3393(4) 0.0487(14) Uani 1 1 d . . . C6 C -0.0314(6) -0.0061(7) 0.2705(4) 0.0459(14) Uani 1 1 d . . . O1 O -0.0412(4) 0.0380(4) 0.1732(3) 0.0382(8) Uani 1 1 d . . . O2 O -0.1224(6) 0.0458(6) 0.3198(4) 0.0701(15) Uani 1 1 d . . . H5 H -0.1053 0.1253 0.3265 0.077(6) Uiso 1 1 calc R . . C7 C -0.0744(6) -0.1515(7) 0.2631(5) 0.0508(15) Uani 1 1 d . . . C8 C -0.1249(8) -0.2184(9) 0.3356(6) 0.067(2) Uani 1 1 d . . . H8 H -0.1322 -0.1742 0.3948 0.077(6) Uiso 1 1 calc R . . C9 C -0.1641(9) -0.3497(10) 0.3202(7) 0.080(3) Uani 1 1 d . . . H9 H -0.1977 -0.3950 0.3688 0.077(6) Uiso 1 1 calc R . . C10 C -0.1532(9) -0.4132(9) 0.2326(7) 0.077(2) Uani 1 1 d . . . H10 H -0.1787 -0.5025 0.2214 0.077(6) Uiso 1 1 calc R . . C11 C -0.1044(7) -0.3444(8) 0.1614(6) 0.0600(17) Uani 1 1 d . . . H11 H -0.0993 -0.3879 0.1011 0.077(6) Uiso 1 1 calc R . . N2 N -0.0637(5) -0.2157(5) 0.1763(4) 0.0467(12) Uani 1 1 d . . . N3 N 0.2795(5) 0.2706(5) 0.1292(4) 0.0445(11) Uani 1 1 d . . . C12 C 0.3347(7) 0.3947(7) 0.1537(6) 0.0610(18) Uani 1 1 d . . . H12 H 0.2911 0.4499 0.1864 0.077(6) Uiso 1 1 calc R . . C13 C 0.4537(9) 0.4423(9) 0.1316(8) 0.078(2) Uani 1 1 d . . . H13 H 0.4917 0.5280 0.1509 0.077(6) Uiso 1 1 calc R . . C14 C 0.5155(9) 0.3619(9) 0.0809(8) 0.080(3) Uani 1 1 d . . . H14 H 0.5947 0.3929 0.0634 0.077(6) Uiso 1 1 calc R . . C15 C 0.4592(7) 0.2353(9) 0.0562(6) 0.067(2) Uani 1 1 d . . . H15 H 0.5013 0.1792 0.0229 0.077(6) Uiso 1 1 calc R . . C16 C 0.3397(5) 0.1907(6) 0.0807(5) 0.0436(13) Uani 1 1 d . . . C17 C 0.2672(5) 0.0520(6) 0.0539(4) 0.0397(12) Uani 1 1 d . . . O3 O 0.1287(3) 0.0559(4) 0.0422(3) 0.0338(8) Uani 1 1 d . . . O4 O 0.2931(4) 0.0070(5) -0.0396(3) 0.0481(10) Uani 1 1 d . . . H16 H 0.2536 -0.0668 -0.0567 0.077(6) Uiso 1 1 calc R . . C18 C 0.3217(5) -0.0427(6) 0.1363(4) 0.0405(12) Uani 1 1 d . . . C19 C 0.4607(6) -0.0553(8) 0.1693(5) 0.063(2) Uani 1 1 d . . . H19 H 0.5240 -0.0018 0.1458 0.077(6) Uiso 1 1 calc R . . C20 C 0.5022(7) -0.1507(9) 0.2387(6) 0.071(2) Uani 1 1 d . . . H20 H 0.5942 -0.1620 0.2618 0.077(6) Uiso 1 1 calc R . . C21 C 0.4082(8) -0.2268(9) 0.2722(6) 0.070(2) Uani 1 1 d . . . H21 H 0.4344 -0.2913 0.3178 0.077(6) Uiso 1 1 calc R . . C22 C 0.2712(7) -0.2063(7) 0.2370(5) 0.0564(16) Uani 1 1 d . . . H22 H 0.2066 -0.2570 0.2611 0.077(6) Uiso 1 1 calc R . . N4 N 0.2297(5) -0.1163(5) 0.1698(3) 0.0418(11) Uani 1 1 d . . . OW1 O 0.320(2) 0.5750(19) 0.4976(16) 0.292(11) Uani 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 0.0400(4) 0.0396(5) 0.0375(4) -0.0007(3) 0.0092(3) 0.0058(3) Ni2 0.0342(3) 0.0368(5) 0.0361(3) 0.0040(3) 0.0107(2) 0.0050(3) N5 0.046(2) 0.046(3) 0.043(2) 0.004(2) 0.0107(19) 0.014(2) N6 0.046(3) 0.037(3) 0.060(3) 0.002(2) 0.013(2) 0.009(2) N7 0.094(5) 0.087(6) 0.106(6) -0.012(5) 0.006(4) 0.050(5) N8 0.095(5) 0.070(5) 0.064(4) -0.025(4) 0.007(4) 0.026(4) N9A 0.097(13) 0.12(2) 0.14(3) 0.04(2) 0.044(15) 0.033(14) N9B 0.35(4) 0.13(2) 0.073(15) 0.010(14) 0.086(18) 0.11(2) N10A 0.28(4) 0.49(6) 0.106(17) -0.19(3) -0.06(2) 0.17(4) N10B 0.45(6) 0.26(5) 0.18(3) 0.10(3) 0.16(3) 0.06(4) N1 0.049(3) 0.048(3) 0.041(2) -0.005(2) 0.0055(19) 0.009(2) C1 0.055(3) 0.056(4) 0.047(3) -0.007(3) -0.001(3) 0.001(3) C2 0.066(4) 0.075(6) 0.047(3) -0.006(4) -0.007(3) 0.006(4) C3 0.094(6) 0.084(6) 0.044(3) 0.016(4) -0.002(4) 0.015(5) C4 0.086(5) 0.065(5) 0.038(3) 0.013(3) 0.009(3) 0.009(4) C5 0.061(3) 0.047(4) 0.040(3) -0.001(3) 0.016(2) 0.009(3) C6 0.052(3) 0.057(4) 0.034(2) 0.004(2) 0.018(2) 0.014(3) O1 0.0386(17) 0.043(2) 0.0359(17) 0.0074(16) 0.0142(14) 0.0061(16) O2 0.091(4) 0.078(4) 0.063(3) 0.017(3) 0.046(3) 0.037(3) C7 0.045(3) 0.062(5) 0.048(3) 0.015(3) 0.016(2) 0.009(3) C8 0.070(4) 0.078(6) 0.066(4) 0.026(4) 0.040(4) 0.010(4) C9 0.089(6) 0.074(7) 0.085(6) 0.036(5) 0.043(5) -0.009(5) C10 0.078(5) 0.057(5) 0.095(6) 0.032(5) 0.024(4) -0.010(4) C11 0.059(4) 0.057(5) 0.066(4) 0.008(3) 0.023(3) -0.004(3) N2 0.048(3) 0.044(3) 0.051(3) 0.009(2) 0.021(2) -0.004(2) N3 0.042(2) 0.036(3) 0.055(3) 0.006(2) 0.0134(19) 0.000(2) C12 0.062(4) 0.039(4) 0.076(5) -0.003(3) 0.015(3) -0.009(3) C13 0.076(5) 0.048(5) 0.106(6) 0.005(5) 0.030(5) -0.020(4) C14 0.068(5) 0.063(6) 0.115(7) 0.001(5) 0.045(5) -0.022(4) C15 0.046(3) 0.079(6) 0.075(5) 0.000(4) 0.022(3) -0.014(3) C16 0.038(2) 0.042(4) 0.050(3) 0.001(2) 0.013(2) -0.005(2) C17 0.029(2) 0.048(4) 0.043(3) -0.002(2) 0.0112(18) 0.004(2) O3 0.0273(15) 0.035(2) 0.0380(17) 0.0024(15) 0.0074(12) 0.0039(14) O4 0.0364(18) 0.061(3) 0.047(2) -0.010(2) 0.0148(15) 0.0043(18) C18 0.037(2) 0.043(3) 0.039(2) -0.004(2) 0.0066(19) 0.007(2) C19 0.041(3) 0.091(6) 0.056(4) -0.006(4) 0.006(3) 0.021(3) C20 0.049(4) 0.091(6) 0.060(4) -0.004(4) -0.012(3) 0.030(4) C21 0.068(5) 0.067(5) 0.064(4) 0.004(4) -0.007(4) 0.024(4) C22 0.062(4) 0.046(4) 0.054(3) 0.008(3) 0.001(3) 0.014(3) N4 0.043(2) 0.042(3) 0.040(2) 0.003(2) 0.0076(18) 0.011(2) OW1 0.32(3) 0.26(2) 0.33(2) 0.194(18) 0.13(2) 0.027(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N8 2.051(7) . ? Ni1 O1 2.058(4) . ? Ni1 N3 2.074(5) . ? Ni1 N5 2.074(5) . ? Ni1 N1 2.095(5) . ? Ni1 O3 2.133(4) . ? Ni2 N2 2.030(5) . ? Ni2 O3 2.030(4) . ? Ni2 N5 2.058(5) 2 ? Ni2 O1 2.105(4) . ? Ni2 O3 2.107(4) 2 ? Ni2 N4 2.111(4) . ? N5 N6 1.190(7) . ? N5 Ni2 2.058(5) 2 ? N6 N7 1.123(8) . ? N8 N9A 1.11(4) . ? N8 N9B 1.09(3) . ? N9A N9B 0.86(4) . ? N9A N10A 1.22(4) . ? N9A N10B 1.70(5) . ? N9B N10B 1.52(5) . ? N9B N10A 1.65(6) . ? N10A N10B 1.12(6) . ? N1 C5 1.350(9) . ? N1 C1 1.371(8) . ? C1 C2 1.377(10) . ? C1 H1 0.9300 . ? C2 C3 1.397(13) . ? C2 H2 0.9300 . ? C3 C4 1.348(11) . ? C3 H3 0.9300 . ? C4 C5 1.396(9) . ? C4 H4 0.9300 . ? C5 C6 1.551(9) . ? C6 O1 1.374(7) . ? C6 O2 1.419(7) . ? C6 C7 1.515(10) . ? O2 H5 0.8200 . ? C7 N2 1.359(8) . ? C7 C8 1.385(9) . ? C8 C9 1.368(13) . ? C8 H8 0.9300 . ? C9 C10 1.366(13) . ? C9 H9 0.9300 . ? C10 C11 1.373(11) . ? C10 H10 0.9300 . ? C11 N2 1.345(9) . ? C11 H11 0.9300 . ? N3 C12 1.340(9) . ? N3 C16 1.335(8) . ? C12 C13 1.372(11) . ? C12 H12 0.9300 . ? C13 C14 1.368(13) . ? C13 H13 0.9300 . ? C14 C15 1.367(12) . ? C14 H14 0.9300 . ? C15 C16 1.386(9) . ? C15 H15 0.9300 . ? C16 C17 1.529(9) . ? C17 O3 1.388(5) . ? C17 O4 1.424(6) . ? C17 C18 1.530(8) . ? O3 Ni2 2.107(4) 2 ? O4 H16 0.8200 . ? C18 N4 1.326(8) . ? C18 C19 1.394(8) . ? C19 C20 1.397(11) . ? C19 H19 0.9300 . ? C20 C21 1.354(12) . ? C20 H20 0.9300 . ? C21 C22 1.396(10) . ? C21 H21 0.9300 . ? C22 N4 1.337(8) . ? C22 H22 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 N8 Ni1 O1 103.4(3) . . ? N8 Ni1 N3 99.1(3) . . ? O1 Ni1 N3 155.71(18) . . ? N8 Ni1 N5 90.5(3) . . ? O1 Ni1 N5 92.16(19) . . ? N3 Ni1 N5 96.6(2) . . ? N8 Ni1 N1 88.1(3) . . ? O1 Ni1 N1 76.95(19) . . ? N3 Ni1 N1 95.0(2) . . ? N5 Ni1 N1 168.4(2) . . ? N8 Ni1 O3 166.8(3) . . ? O1 Ni1 O3 83.05(15) . . ? N3 Ni1 O3 76.79(18) . . ? N5 Ni1 O3 77.68(17) . . ? N1 Ni1 O3 104.62(17) . . ? N2 Ni2 O3 159.89(19) . . ? N2 Ni2 N5 98.1(2) . 2 ? O3 Ni2 N5 101.36(19) . 2 ? N2 Ni2 O1 78.43(19) . . ? O3 Ni2 O1 84.42(15) . . ? N5 Ni2 O1 163.04(17) 2 . ? N2 Ni2 O3 108.08(18) . 2 ? O3 Ni2 O3 81.04(15) . 2 ? N5 Ni2 O3 78.63(17) 2 2 ? O1 Ni2 O3 86.66(14) . 2 ? N2 Ni2 N4 96.5(2) . . ? O3 Ni2 N4 77.99(17) . . ? N5 Ni2 N4 91.30(18) 2 . ? O1 Ni2 N4 105.54(17) . . ? O3 Ni2 N4 154.45(17) 2 . ? N6 N5 Ni2 126.7(4) . 2 ? N6 N5 Ni1 127.9(4) . . ? Ni2 N5 Ni1 103.2(2) 2 . ? N7 N6 N5 179.3(9) . . ? N9A N8 N9B 46(2) . . ? N9A N8 Ni1 137.0(15) . . ? N9B N8 Ni1 127.5(16) . . ? N9B N9A N8 66(3) . . ? N9B N9A N10A 104(5) . . ? N8 N9A N10A 170(4) . . ? N9B N9A N10B 63(4) . . ? N8 N9A N10B 129(3) . . ? N10A N9A N10B 41(4) . . ? N9A N9B N8 68(4) . . ? N9A N9B N10B 87(5) . . ? N8 N9B N10B 154(4) . . ? N9A N9B N10A 45(4) . . ? N8 N9B N10A 114(4) . . ? N10B N9B N10A 41(2) . . ? N10B N10A N9A 93(5) . . ? N10B N10A N9B 63(4) . . ? N9A N10A N9B 30.1(19) . . ? N10A N10B N9B 76(3) . . ? N10A N10B N9A 46(2) . . ? N9B N10B N9A 30.2(17) . . ? C5 N1 C1 117.4(6) . . ? C5 N1 Ni1 116.3(4) . . ? C1 N1 Ni1 126.1(5) . . ? N1 C1 C2 122.6(7) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 118.2(7) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 120.3(7) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.2(8) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 122.4(6) . . ? N1 C5 C6 114.8(5) . . ? C4 C5 C6 122.7(6) . . ? O1 C6 O2 113.1(5) . . ? O1 C6 C7 110.2(5) . . ? O2 C6 C7 103.8(5) . . ? O1 C6 C5 109.2(5) . . ? O2 C6 C5 109.0(5) . . ? C7 C6 C5 111.6(5) . . ? C6 O1 Ni1 118.4(4) . . ? C6 O1 Ni2 108.2(3) . . ? Ni1 O1 Ni2 94.77(15) . . ? C6 O2 H5 109.5 . . ? N2 C7 C8 120.2(7) . . ? N2 C7 C6 115.0(5) . . ? C8 C7 C6 124.8(7) . . ? C9 C8 C7 120.1(8) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 120.0 . . ? C10 C9 C8 119.3(7) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.5(8) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.2 . . ? N2 C11 C10 121.8(8) . . ? N2 C11 H11 119.0 . . ? C10 C11 H11 119.2 . . ? C11 N2 C7 119.1(6) . . ? C11 N2 Ni2 127.4(5) . . ? C7 N2 Ni2 113.3(4) . . ? C12 N3 C16 119.9(6) . . ? C12 N3 Ni1 125.3(5) . . ? C16 N3 Ni1 114.8(4) . . ? N3 C12 C13 121.7(8) . . ? N3 C12 H12 119.1 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 119.0(8) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 119.2(7) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.4 . . ? C14 C15 C16 120.0(8) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? N3 C16 C15 120.2(6) . . ? N3 C16 C17 116.0(5) . . ? C15 C16 C17 123.8(6) . . ? O3 C17 O4 111.9(4) . . ? O3 C17 C16 108.0(4) . . ? O4 C17 C16 107.4(5) . . ? O3 C17 C18 109.8(4) . . ? O4 C17 C18 106.8(4) . . ? C16 C17 C18 113.0(4) . . ? C17 O3 Ni2 116.6(3) . . ? C17 O3 Ni2 130.2(3) . 2 ? Ni2 O3 Ni2 98.96(15) . 2 ? C17 O3 Ni1 110.2(3) . . ? Ni2 O3 Ni1 94.73(15) . . ? Ni2 O3 Ni1 99.57(15) 2 . ? C17 O4 H16 109.4 . . ? N4 C18 C19 122.2(6) . . ? N4 C18 C17 116.7(4) . . ? C19 C18 C17 121.0(6) . . ? C20 C19 C18 118.0(7) . . ? C20 C19 H19 120.9 . . ? C18 C19 H19 121.1 . . ? C21 C20 C19 119.9(6) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 118.6(7) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.8 . . ? N4 C22 C21 122.3(7) . . ? N4 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C18 N4 C22 119.1(5) . . ? C18 N4 Ni2 113.8(4) . . ? C22 N4 Ni2 126.0(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 N8 Ni1 N5 N6 -14.6(7) . . . . ? O1 Ni1 N5 N6 88.9(6) . . . . ? N3 Ni1 N5 N6 -113.8(6) . . . . ? N1 Ni1 N5 N6 68.5(12) . . . . ? O3 Ni1 N5 N6 171.3(6) . . . . ? N8 Ni1 N5 Ni2 -178.4(3) . . . 2 ? O1 Ni1 N5 Ni2 -75.0(2) . . . 2 ? N3 Ni1 N5 Ni2 82.3(2) . . . 2 ? N1 Ni1 N5 Ni2 -95.3(9) . . . 2 ? O3 Ni1 N5 Ni2 7.45(18) . . . 2 ? Ni2 N5 N6 N7 -98(70) 2 . . . ? Ni1 N5 N6 N7 102(70) . . . . ? O1 Ni1 N8 N9A 131(3) . . . . ? N3 Ni1 N8 N9A -40(3) . . . . ? N5 Ni1 N8 N9A -136(3) . . . . ? N1 Ni1 N8 N9A 55(3) . . . . ? O3 Ni1 N8 N9A -110(2) . . . . ? O1 Ni1 N8 N9B 69(3) . . . . ? N3 Ni1 N8 N9B -102(3) . . . . ? N5 Ni1 N8 N9B 161(3) . . . . ? N1 Ni1 N8 N9B -7(3) . . . . ? O3 Ni1 N8 N9B -173(3) . . . . ? Ni1 N8 N9A N9B -102(3) . . . . ? N9B N8 N9A N10A 11(17) . . . . ? Ni1 N8 N9A N10A -90(18) . . . . ? N9B N8 N9A N10B 6(3) . . . . ? Ni1 N8 N9A N10B -96(4) . . . . ? N10A N9A N9B N8 -178(3) . . . . ? N10B N9A N9B N8 -175(3) . . . . ? N8 N9A N9B N10B 175(3) . . . . ? N10A N9A N9B N10B -3(4) . . . . ? N8 N9A N9B N10A 178(3) . . . . ? N10B N9A N9B N10A 3(4) . . . . ? Ni1 N8 N9B N9A 123(3) . . . . ? N9A N8 N9B N10B -11(7) . . . . ? Ni1 N8 N9B N10B 112(7) . . . . ? N9A N8 N9B N10A -2(2) . . . . ? Ni1 N8 N9B N10A 121(2) . . . . ? N9B N9A N10A N10B 4(6) . . . . ? N8 N9A N10A N10B -7(21) . . . . ? N8 N9A N10A N9B -11(16) . . . . ? N10B N9A N10A N9B -4(6) . . . . ? N9A N9B N10A N10B -176(7) . . . . ? N8 N9B N10A N10B -174(5) . . . . ? N8 N9B N10A N9A 2(3) . . . . ? N10B N9B N10A N9A 176(7) . . . . ? N9A N10A N10B N9B -2(3) . . . . ? N9B N10A N10B N9A 2(3) . . . . ? N9A N9B N10B N10A 3(5) . . . . ? N8 N9B N10B N10A 13(10) . . . . ? N8 N9B N10B N9A 10(6) . . . . ? N10A N9B N10B N9A -3(5) . . . . ? N9B N9A N10B N10A -176(6) . . . . ? N8 N9A N10B N10A 178(5) . . . . ? N8 N9A N10B N9B -6(3) . . . . ? N10A N9A N10B N9B 176(6) . . . . ? N8 Ni1 N1 C5 92.5(5) . . . . ? O1 Ni1 N1 C5 -11.7(4) . . . . ? N3 Ni1 N1 C5 -168.5(4) . . . . ? N5 Ni1 N1 C5 9.2(12) . . . . ? O3 Ni1 N1 C5 -90.8(4) . . . . ? N8 Ni1 N1 C1 -81.5(6) . . . . ? O1 Ni1 N1 C1 174.3(5) . . . . ? N3 Ni1 N1 C1 17.5(5) . . . . ? N5 Ni1 N1 C1 -164.8(8) . . . . ? O3 Ni1 N1 C1 95.2(5) . . . . ? C5 N1 C1 C2 -1.2(10) . . . . ? Ni1 N1 C1 C2 172.8(5) . . . . ? N1 C1 C2 C3 0.2(12) . . . . ? C1 C2 C3 C4 0.6(13) . . . . ? C2 C3 C4 C5 -0.4(13) . . . . ? C1 N1 C5 C4 1.4(9) . . . . ? Ni1 N1 C5 C4 -173.1(5) . . . . ? C1 N1 C5 C6 178.0(5) . . . . ? Ni1 N1 C5 C6 3.4(6) . . . . ? C3 C4 C5 N1 -0.7(11) . . . . ? C3 C4 C5 C6 -177.0(7) . . . . ? N1 C5 C6 O1 11.8(7) . . . . ? C4 C5 C6 O1 -171.6(6) . . . . ? N1 C5 C6 O2 -112.1(6) . . . . ? C4 C5 C6 O2 64.4(8) . . . . ? N1 C5 C6 C7 133.9(5) . . . . ? C4 C5 C6 C7 -49.6(8) . . . . ? O2 C6 O1 Ni1 98.9(5) . . . . ? C7 C6 O1 Ni1 -145.5(4) . . . . ? C5 C6 O1 Ni1 -22.6(6) . . . . ? O2 C6 O1 Ni2 -155.0(5) . . . . ? C7 C6 O1 Ni2 -39.4(5) . . . . ? C5 C6 O1 Ni2 83.5(5) . . . . ? N8 Ni1 O1 C6 -65.1(4) . . . . ? N3 Ni1 O1 C6 92.6(5) . . . . ? N5 Ni1 O1 C6 -156.2(4) . . . . ? N1 Ni1 O1 C6 19.7(4) . . . . ? O3 Ni1 O1 C6 126.5(4) . . . . ? N8 Ni1 O1 Ni2 -178.8(2) . . . . ? N3 Ni1 O1 Ni2 -21.1(5) . . . . ? N5 Ni1 O1 Ni2 90.17(17) . . . . ? N1 Ni1 O1 Ni2 -93.95(18) . . . . ? O3 Ni1 O1 Ni2 12.86(13) . . . . ? N2 Ni2 O1 C6 34.0(4) . . . . ? O3 Ni2 O1 C6 -135.5(4) . . . . ? N5 Ni2 O1 C6 113.6(7) 2 . . . ? O3 Ni2 O1 C6 143.2(4) 2 . . . ? N4 Ni2 O1 C6 -59.6(4) . . . . ? N2 Ni2 O1 Ni1 156.0(2) . . . . ? O3 Ni2 O1 Ni1 -13.49(13) . . . . ? N5 Ni2 O1 Ni1 -124.5(6) 2 . . . ? O3 Ni2 O1 Ni1 -94.81(15) 2 . . . ? N4 Ni2 O1 Ni1 62.4(2) . . . . ? O1 C6 C7 N2 23.5(7) . . . . ? O2 C6 C7 N2 144.9(5) . . . . ? C5 C6 C7 N2 -98.0(6) . . . . ? O1 C6 C7 C8 -154.8(6) . . . . ? O2 C6 C7 C8 -33.4(8) . . . . ? C5 C6 C7 C8 83.8(8) . . . . ? N2 C7 C8 C9 0.1(11) . . . . ? C6 C7 C8 C9 178.4(7) . . . . ? C7 C8 C9 C10 -0.3(13) . . . . ? C8 C9 C10 C11 -0.5(14) . . . . ? C9 C10 C11 N2 1.5(13) . . . . ? C10 C11 N2 C7 -1.7(10) . . . . ? C10 C11 N2 Ni2 174.4(6) . . . . ? C8 C7 N2 C11 0.8(9) . . . . ? C6 C7 N2 C11 -177.6(6) . . . . ? C8 C7 N2 Ni2 -175.8(5) . . . . ? C6 C7 N2 Ni2 5.9(6) . . . . ? O3 Ni2 N2 C11 -165.5(5) . . . . ? N5 Ni2 N2 C11 -0.6(6) 2 . . . ? O1 Ni2 N2 C11 162.5(6) . . . . ? O3 Ni2 N2 C11 80.0(6) 2 . . . ? N4 Ni2 N2 C11 -92.9(6) . . . . ? O3 Ni2 N2 C7 10.7(8) . . . . ? N5 Ni2 N2 C7 175.6(4) 2 . . . ? O1 Ni2 N2 C7 -21.2(4) . . . . ? O3 Ni2 N2 C7 -103.8(4) 2 . . . ? N4 Ni2 N2 C7 83.4(4) . . . . ? N8 Ni1 N3 C12 -5.6(6) . . . . ? O1 Ni1 N3 C12 -163.7(5) . . . . ? N5 Ni1 N3 C12 85.9(6) . . . . ? N1 Ni1 N3 C12 -94.5(6) . . . . ? O3 Ni1 N3 C12 161.6(6) . . . . ? N8 Ni1 N3 C16 175.8(5) . . . . ? O1 Ni1 N3 C16 17.8(7) . . . . ? N5 Ni1 N3 C16 -92.6(4) . . . . ? N1 Ni1 N3 C16 86.9(4) . . . . ? O3 Ni1 N3 C16 -16.9(4) . . . . ? C16 N3 C12 C13 -1.0(11) . . . . ? Ni1 N3 C12 C13 -179.5(6) . . . . ? N3 C12 C13 C14 1.8(14) . . . . ? C12 C13 C14 C15 -1.9(15) . . . . ? C13 C14 C15 C16 1.3(14) . . . . ? C12 N3 C16 C15 0.3(9) . . . . ? Ni1 N3 C16 C15 179.0(5) . . . . ? C12 N3 C16 C17 -178.6(6) . . . . ? Ni1 N3 C16 C17 0.0(6) . . . . ? C14 C15 C16 N3 -0.5(11) . . . . ? C14 C15 C16 C17 178.4(7) . . . . ? N3 C16 C17 O3 27.2(7) . . . . ? C15 C16 C17 O3 -151.6(6) . . . . ? N3 C16 C17 O4 148.1(5) . . . . ? C15 C16 C17 O4 -30.8(8) . . . . ? N3 C16 C17 C18 -94.4(6) . . . . ? C15 C16 C17 C18 86.7(7) . . . . ? O4 C17 O3 Ni2 95.6(5) . . . . ? C16 C17 O3 Ni2 -146.4(4) . . . . ? C18 C17 O3 Ni2 -22.8(5) . . . . ? O4 C17 O3 Ni2 -35.0(7) . . . 2 ? C16 C17 O3 Ni2 83.0(5) . . . 2 ? C18 C17 O3 Ni2 -153.5(3) . . . 2 ? O4 C17 O3 Ni1 -158.0(4) . . . . ? C16 C17 O3 Ni1 -40.0(5) . . . . ? C18 C17 O3 Ni1 83.6(4) . . . . ? N2 Ni2 O3 C17 97.0(6) . . . . ? N5 Ni2 O3 C17 -67.7(4) 2 . . . ? O1 Ni2 O3 C17 128.4(3) . . . . ? O3 Ni2 O3 C17 -144.1(4) 2 . . . ? N4 Ni2 O3 C17 21.2(3) . . . . ? N2 Ni2 O3 Ni2 -118.9(5) . . . 2 ? N5 Ni2 O3 Ni2 76.39(18) 2 . . 2 ? O1 Ni2 O3 Ni2 -87.48(15) . . . 2 ? O3 Ni2 O3 Ni2 0.0 2 . . 2 ? N4 Ni2 O3 Ni2 165.30(18) . . . 2 ? N2 Ni2 O3 Ni1 -18.4(5) . . . . ? N5 Ni2 O3 Ni1 176.88(14) 2 . . . ? O1 Ni2 O3 Ni1 13.01(13) . . . . ? O3 Ni2 O3 Ni1 100.49(16) 2 . . . ? N4 Ni2 O3 Ni1 -94.21(17) . . . . ? N8 Ni1 O3 C17 105.7(13) . . . . ? O1 Ni1 O3 C17 -134.0(4) . . . . ? N3 Ni1 O3 C17 32.4(4) . . . . ? N5 Ni1 O3 C17 132.3(4) . . . . ? N1 Ni1 O3 C17 -59.4(4) . . . . ? N8 Ni1 O3 Ni2 -133.6(12) . . . . ? O1 Ni1 O3 Ni2 -13.35(13) . . . . ? N3 Ni1 O3 Ni2 153.01(19) . . . . ? N5 Ni1 O3 Ni2 -107.10(19) . . . . ? N1 Ni1 O3 Ni2 61.2(2) . . . . ? N8 Ni1 O3 Ni2 -33.7(13) . . . 2 ? O1 Ni1 O3 Ni2 86.58(16) . . . 2 ? N3 Ni1 O3 Ni2 -107.1(2) . . . 2 ? N5 Ni1 O3 Ni2 -7.18(18) . . . 2 ? N1 Ni1 O3 Ni2 161.10(19) . . . 2 ? O3 C17 C18 N4 9.6(7) . . . . ? O4 C17 C18 N4 -111.9(5) . . . . ? C16 C17 C18 N4 130.2(5) . . . . ? O3 C17 C18 C19 -174.1(5) . . . . ? O4 C17 C18 C19 64.4(7) . . . . ? C16 C17 C18 C19 -53.5(7) . . . . ? N4 C18 C19 C20 1.0(9) . . . . ? C17 C18 C19 C20 -175.1(6) . . . . ? C18 C19 C20 C21 -0.4(11) . . . . ? C19 C20 C21 C22 -0.7(12) . . . . ? C20 C21 C22 N4 1.5(11) . . . . ? C19 C18 N4 C22 -0.4(9) . . . . ? C17 C18 N4 C22 175.9(5) . . . . ? C19 C18 N4 Ni2 -169.1(5) . . . . ? C17 C18 N4 Ni2 7.1(6) . . . . ? C21 C22 N4 C18 -0.9(10) . . . . ? C21 C22 N4 Ni2 166.4(5) . . . . ? N2 Ni2 N4 C18 -175.3(4) . . . . ? O3 Ni2 N4 C18 -14.9(4) . . . . ? N5 Ni2 N4 C18 86.5(4) 2 . . . ? O1 Ni2 N4 C18 -95.5(4) . . . . ? O3 Ni2 N4 C18 20.7(7) 2 . . . ? N2 Ni2 N4 C22 16.9(5) . . . . ? O3 Ni2 N4 C22 177.3(5) . . . . ? N5 Ni2 N4 C22 -81.4(5) 2 . . . ? O1 Ni2 N4 C22 96.6(5) . . . . ? O3 Ni2 N4 C22 -147.2(5) 2 . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.099 _refine_diff_density_min -0.932 _refine_diff_density_rms 0.160