# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1566 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 'Barandika, G.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Uiversidad 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 Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Cortes, R.' ; Dpto. Qu\'imica Inorg\'anica Facultad de Farmacia Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 450 01080 Vitoria Spain ; 'Lezama, L.' ; Dpto. Qimica Inorg\'anica Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Arriortua, M.I.' ; Dpto. de Mineralog\'ia y Petrolog\'ia Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; 'Rojo, T.' ; Dpto. Qu\'imica Inorg\'anica Facultad de CIencias Uiversidad del Pa\'is Vasco/E.H.U. P.O. Box 644 48080 Bilbao Spain ; data_niclo4 _audit_creation_method SHELXL _chemical_formula_sum 'C30 H26 Cl N15 Ni2 O6' _chemical_formula_weight 845.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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' _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 10.179(2) _cell_length_b 10.8000(10) _cell_length_c 16.866(2) _cell_angle_alpha 85.54(2) _cell_angle_beta 78.49(2) _cell_angle_gamma 72.030(10) _cell_volume 1728.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.625 _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.235 _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_reflns_number 10579 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 29.97 _reflns_number_total 10050 _reflns_number_observed 6891 _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 on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0893P)^2^+0.0520P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method none _refine_ls_number_reflns 10050 _refine_ls_number_parameters 566 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_obs 0.0492 _refine_ls_wR_factor_all 0.1494 _refine_ls_wR_factor_obs 0.1276 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.079 _refine_ls_restrained_S_all 1.037 _refine_ls_restrained_S_obs 1.079 _refine_ls_shift/esd_max 1.371 _refine_ls_shift/esd_mean 0.067 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni1A Ni -0.00518(4) 0.86894(3) 0.79531(2) 0.03244(10) Uani 1 d . . N1A N 0.1300(3) 0.9239(2) 0.69726(15) 0.0436(5) Uani 1 d . . N2A N 0.1496(3) 0.8804(2) 0.8487(2) 0.0400(5) Uani 1 d . . N3A N -0.0804(3) 0.8312(2) 0.91731(14) 0.0383(5) Uani 1 d . . N4A N -0.1426(3) 0.8185(2) 0.73795(14) 0.0383(5) Uani 1 d . . N5A N -0.2198(3) 0.8835(2) 0.6961(2) 0.0483(6) Uani 1 d . . N6A N -0.2916(5) 0.9438(4) 0.6533(3) 0.0947(14) Uani 1 d . . N7A N -0.1288(3) 1.0638(2) 0.8102(2) 0.0457(6) Uani 1 d . . N8A N -0.0911(3) 1.1518(2) 0.77974(14) 0.0421(5) Uani 1 d . . N9A N -0.0552(4) 1.2379(3) 0.7508(2) 0.0730(10) Uani 1 d . . C1A C 0.1066(5) 0.9543(4) 0.6209(2) 0.0570(9) Uani 1 d . . C2A C 0.1993(6) 0.9913(4) 0.5610(3) 0.0736(12) Uani 1 d . . C3A C 0.3215(6) 0.9985(5) 0.5798(3) 0.085(2) Uani 1 d . . C4A C 0.3485(5) 0.9692(4) 0.6570(3) 0.0724(12) Uani 1 d . . C5A C 0.2492(3) 0.9324(3) 0.7158(2) 0.0503(7) Uani 1 d . . C6A C 0.2617(3) 0.9062(3) 0.8021(2) 0.0495(7) Uani 1 d . . C7A C 0.3737(4) 0.9088(4) 0.8370(3) 0.0720(12) Uani 1 d . . C8A C 0.3650(5) 0.8858(5) 0.9198(3) 0.0794(14) Uani 1 d . . C9A C 0.2493(5) 0.8592(4) 0.9662(3) 0.0670(11) Uani 1 d . . C10A C 0.1409(3) 0.8552(3) 0.9287(2) 0.0446(7) Uani 1 d . . C11A C 0.0084(4) 0.8285(3) 0.9678(2) 0.0438(6) Uani 1 d . . C12A C -0.0240(5) 0.8016(4) 1.0501(2) 0.0617(10) Uani 1 d . . C13A C -0.1502(5) 0.7775(4) 1.0806(2) 0.0702(12) Uani 1 d . . C14A C -0.2406(5) 0.7823(4) 1.0298(2) 0.0658(10) Uani 1 d . . C15A C -0.2039(4) 0.8103(3) 0.9480(2) 0.0495(7) Uani 1 d . . Ni1B Ni -0.04061(3) 0.61827(3) 0.71500(2) 0.03132(10) Uani 1 d . . O5 O 0.0806(3) 0.4244(2) 0.7017(2) 0.0512(5) Uani 1 d . . N1B N 0.0542(3) 0.6527(2) 0.59575(13) 0.0364(5) Uani 1 d . . N2B N -0.1840(2) 0.6096(2) 0.65052(13) 0.0346(5) Uani 1 d . . N3B N -0.1889(3) 0.5583(2) 0.80404(14) 0.0379(5) Uani 1 d . . N4B N 0.0963(2) 0.6618(2) 0.77613(14) 0.0360(5) Uani 1 d . . N5B N 0.1628(3) 0.5968(2) 0.8234(2) 0.0438(6) Uani 1 d . . N6B N 0.2268(5) 0.5374(4) 0.8697(2) 0.0838(12) Uani 1 d . . C1B C 0.1835(3) 0.6635(3) 0.5710(2) 0.0456(7) Uani 1 d . . C2B C 0.2345(4) 0.6899(4) 0.4908(2) 0.0541(8) Uani 1 d . . C3B C 0.1497(4) 0.7048(4) 0.4349(2) 0.0562(8) Uani 1 d . . C4B C 0.0172(4) 0.6914(3) 0.4589(2) 0.0492(7) Uani 1 d . . C5B C -0.0278(3) 0.6646(3) 0.5400(2) 0.0371(6) Uani 1 d . . C6B C -0.1660(3) 0.6444(3) 0.5718(2) 0.0381(6) Uani 1 d . . C7B C -0.2719(4) 0.6586(4) 0.5279(2) 0.0546(8) Uani 1 d . . C8B C -0.3947(4) 0.6364(4) 0.5678(2) 0.0646(10) Uani 1 d . . C9B C -0.4118(4) 0.6008(4) 0.6491(2) 0.0558(8) Uani 1 d . . C10B C -0.3019(3) 0.5876(3) 0.6894(2) 0.0401(6) Uani 1 d . . C11B C -0.3004(3) 0.5485(3) 0.7758(2) 0.0406(6) Uani 1 d . . C12B C -0.4015(4) 0.4999(4) 0.8231(2) 0.0582(9) Uani 1 d . . C13B C -0.3881(5) 0.4618(4) 0.9023(2) 0.0674(11) Uani 1 d . . C14B C -0.2763(5) 0.4721(4) 0.9315(2) 0.0613(9) Uani 1 d . . C15B C -0.1776(4) 0.5200(3) 0.8809(2) 0.0484(7) Uani 1 d . . Cl1 Cl -0.45234(9) 0.71663(8) 0.31900(5) 0.0543(2) Uani 1 d . . O1 O -0.4813(3) 0.7820(3) 0.3946(2) 0.0756(8) Uani 1 d . . O2 O -0.3784(4) 0.7826(4) 0.2579(2) 0.0985(11) Uani 1 d . . O3 O -0.5794(3) 0.7177(3) 0.2970(2) 0.0781(8) Uani 1 d . . O4 O -0.3679(4) 0.5859(3) 0.3270(3) 0.1092(14) Uani 1 d . . O6 O -0.5742(4) 0.8923(6) 0.1255(2) 0.113(2) Uani 1 d . . H1A H 0.0208(47) 0.9524(42) 0.6146(26) 0.076(3) Uiso 1 d . . H2A H 0.1764(45) 1.0105(41) 0.5070(27) 0.076(3) Uiso 1 d . . H3A H 0.3899(49) 1.0154(43) 0.5467(27) 0.076(3) Uiso 1 d . . H4A H 0.4245(49) 0.9555(44) 0.6764(28) 0.076(3) Uiso 1 d . . H7A H 0.4540(47) 0.9316(41) 0.7987(26) 0.076(3) Uiso 1 d . . H8A H 0.4474(47) 0.8779(40) 0.9379(27) 0.076(3) Uiso 1 d . . H9A H 0.2403(48) 0.8452(43) 1.0158(28) 0.076(3) Uiso 1 d . . H12A H 0.0298(46) 0.8042(42) 1.0841(28) 0.076(3) Uiso 1 d . . H13A H -0.1830(46) 0.7598(40) 1.1339(27) 0.076(3) Uiso 1 d . . H14A H -0.3200(48) 0.7718(42) 1.0470(27) 0.076(3) Uiso 1 d . . H15A H -0.2617(47) 0.8158(41) 0.9146(27) 0.076(3) Uiso 1 d . . H1B H 0.2394(47) 0.6471(40) 0.6088(27) 0.076(3) Uiso 1 d . . H2B H 0.3240(48) 0.6950(41) 0.4735(26) 0.076(3) Uiso 1 d . . H3B H 0.1868(46) 0.7209(41) 0.3823(27) 0.076(3) Uiso 1 d . . H4B H -0.0349(46) 0.6980(41) 0.4233(28) 0.076(3) Uiso 1 d . . H7B H -0.2556(44) 0.6754(40) 0.4681(27) 0.076(3) Uiso 1 d . . H8B H -0.4782(43) 0.6502(39) 0.5448(24) 0.076(3) Uiso 1 d . . H9B H -0.4854(47) 0.5831(41) 0.6797(26) 0.076(3) Uiso 1 d . . H12B H -0.4796(47) 0.5016(40) 0.8000(26) 0.076(3) Uiso 1 d . . H13B H -0.4539(46) 0.4237(39) 0.9323(26) 0.076(3) Uiso 1 d . . H14B H -0.2563(44) 0.4470(40) 0.9871(27) 0.076(3) Uiso 1 d . . H15B H -0.0986(45) 0.5318(41) 0.9000(26) 0.076(3) Uiso 1 d . . H51 H 0.0486(47) 0.3691(42) 0.7241(27) 0.076(3) Uiso 1 d . . H52 H 0.1621(50) 0.4022(42) 0.7061(27) 0.076(3) Uiso 1 d . . H61 H -0.6587(51) 0.9086(44) 0.1439(28) 0.076(3) Uiso 1 d . . H62 H -0.5487(54) 0.8780(51) 0.1616(30) 0.076(3) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1A 0.0387(2) 0.0338(2) 0.0312(2) 0.00011(12) -0.01013(13) -0.01799(14) N1A 0.0507(14) 0.0397(12) 0.0427(13) -0.0016(10) -0.0015(11) -0.0211(11) N2A 0.0409(12) 0.0400(12) 0.0474(13) -0.0079(10) -0.0126(10) -0.0194(10) N3A 0.0465(13) 0.0384(11) 0.0339(11) -0.0012(9) -0.0091(10) -0.0172(10) N4A 0.0440(12) 0.0370(11) 0.0412(12) -0.0003(9) -0.0209(10) -0.0146(10) N5A 0.0522(15) 0.0392(13) 0.058(2) -0.0051(11) -0.0241(13) -0.0110(11) N6A 0.106(3) 0.067(2) 0.119(3) 0.006(2) -0.081(3) -0.002(2) N7A 0.0470(14) 0.0359(12) 0.0539(15) 0.0005(11) -0.0063(11) -0.0141(11) N8A 0.059(2) 0.0369(12) 0.0369(12) 0.0009(9) -0.0166(11) -0.0194(11) N9A 0.105(3) 0.051(2) 0.075(2) 0.012(2) -0.015(2) -0.044(2) C1A 0.076(2) 0.052(2) 0.045(2) 0.0066(14) -0.005(2) -0.027(2) C2A 0.098(3) 0.060(2) 0.053(2) 0.007(2) 0.011(2) -0.028(2) C3A 0.090(4) 0.073(3) 0.074(3) 0.003(2) 0.032(3) -0.031(2) C4A 0.057(2) 0.065(2) 0.093(3) -0.007(2) 0.012(2) -0.030(2) C5A 0.045(2) 0.0408(15) 0.065(2) -0.0053(14) 0.0033(15) -0.0207(13) C6A 0.042(2) 0.042(2) 0.072(2) -0.0101(14) -0.0120(14) -0.0204(13) C7A 0.047(2) 0.074(3) 0.108(4) -0.009(2) -0.022(2) -0.030(2) C8A 0.062(2) 0.082(3) 0.116(4) -0.007(3) -0.049(3) -0.030(2) C9A 0.082(3) 0.062(2) 0.074(3) -0.005(2) -0.047(2) -0.025(2) C10A 0.054(2) 0.0400(14) 0.047(2) -0.0064(12) -0.0226(13) -0.0148(13) C11A 0.061(2) 0.0365(13) 0.0365(14) -0.0036(11) -0.0180(13) -0.0128(13) C12A 0.089(3) 0.061(2) 0.034(2) -0.0056(14) -0.020(2) -0.014(2) C13A 0.102(3) 0.066(2) 0.034(2) 0.001(2) 0.001(2) -0.022(2) C14A 0.074(3) 0.069(2) 0.049(2) -0.001(2) 0.010(2) -0.027(2) C15A 0.055(2) 0.052(2) 0.044(2) -0.0033(13) -0.0011(14) -0.0235(15) Ni1B 0.0371(2) 0.0333(2) 0.0300(2) 0.00030(12) -0.01388(13) -0.01521(13) O5 0.0472(12) 0.0364(11) 0.073(2) 0.0012(10) -0.0174(12) -0.0139(10) N1B 0.0441(12) 0.0405(11) 0.0303(10) 0.0017(9) -0.0125(9) -0.0179(10) N2B 0.0408(12) 0.0376(11) 0.0330(11) -0.0015(9) -0.0149(9) -0.0174(9) N3B 0.0458(13) 0.0364(11) 0.0378(12) -0.0013(9) -0.0136(10) -0.0175(10) N4B 0.0415(12) 0.0365(11) 0.0375(11) -0.0009(9) -0.0189(9) -0.0154(9) N5B 0.0518(14) 0.0402(12) 0.0443(13) -0.0038(10) -0.0214(11) -0.0123(11) N6B 0.114(3) 0.065(2) 0.081(2) 0.008(2) -0.066(2) -0.011(2) C1B 0.044(2) 0.057(2) 0.0401(15) 0.0016(13) -0.0104(12) -0.0198(14) C2B 0.046(2) 0.070(2) 0.045(2) -0.001(2) -0.0010(14) -0.022(2) C3B 0.067(2) 0.065(2) 0.035(2) 0.0013(14) -0.0062(15) -0.022(2) C4B 0.065(2) 0.055(2) 0.0323(14) 0.0006(12) -0.0168(13) -0.020(2) C5B 0.0487(15) 0.0335(12) 0.0337(13) -0.0001(10) -0.0161(11) -0.0138(11) C6B 0.050(2) 0.0377(13) 0.0341(13) -0.0001(10) -0.0199(12) -0.0171(12) C7B 0.064(2) 0.063(2) 0.052(2) 0.008(2) -0.037(2) -0.026(2) C8B 0.059(2) 0.084(3) 0.069(2) 0.009(2) -0.043(2) -0.029(2) C9B 0.046(2) 0.070(2) 0.064(2) 0.006(2) -0.022(2) -0.028(2) C10B 0.0381(14) 0.0423(14) 0.047(2) -0.0064(12) -0.0150(12) -0.0168(11) C11B 0.0424(15) 0.0418(14) 0.0425(14) -0.0058(11) -0.0086(12) -0.0182(12) C12B 0.054(2) 0.074(2) 0.055(2) -0.008(2) -0.002(2) -0.036(2) C13B 0.075(3) 0.087(3) 0.049(2) -0.004(2) 0.008(2) -0.049(2) C14B 0.078(3) 0.067(2) 0.041(2) 0.003(2) -0.003(2) -0.030(2) C15B 0.059(2) 0.052(2) 0.0387(15) 0.0002(13) -0.0104(14) -0.0231(15) Cl1 0.0449(4) 0.0583(5) 0.0618(5) 0.0040(4) -0.0092(3) -0.0202(3) O1 0.089(2) 0.096(2) 0.0545(15) 0.0021(14) -0.0189(14) -0.044(2) O2 0.113(3) 0.116(3) 0.075(2) -0.003(2) 0.019(2) -0.068(2) O3 0.062(2) 0.097(2) 0.085(2) -0.004(2) -0.031(2) -0.027(2) O4 0.068(2) 0.062(2) 0.192(4) 0.008(2) -0.031(2) -0.010(2) O6 0.061(2) 0.196(5) 0.081(3) 0.031(3) -0.014(2) -0.042(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1A N2A 2.003(2) . ? Ni1A N4A 2.069(2) . ? Ni1A N7A 2.097(2) . ? Ni1A N3A 2.102(2) . ? Ni1A N1A 2.103(2) . ? Ni1A N4B 2.175(2) . ? N1A C5A 1.343(4) . ? N1A C1A 1.354(4) . ? N2A C6A 1.342(4) . ? N2A C10A 1.345(4) . ? N3A C15A 1.341(4) . ? N3A C11A 1.352(4) . ? N4A N5A 1.188(3) . ? N4A Ni1B 2.119(2) . ? N5A N6A 1.150(4) . ? N7A N8A 1.177(3) . ? N8A N9A 1.142(4) . ? C1A C2A 1.364(5) . ? C1A H1A 0.91(4) . ? C2A C3A 1.369(8) . ? C2A H2A 0.98(4) . ? C3A C4A 1.378(8) . ? C3A H3A 0.86(5) . ? C4A C5A 1.396(5) . ? C4A H4A 0.87(5) . ? C5A C6A 1.484(5) . ? C6A C7A 1.392(5) . ? C7A C8A 1.390(7) . ? C7A H7A 1.02(4) . ? C8A C9A 1.374(7) . ? C8A H8A 0.93(5) . ? C9A C10A 1.390(5) . ? C9A H9A 0.83(4) . ? C10A C11A 1.481(5) . ? C11A C12A 1.390(4) . ? C12A C13A 1.380(6) . ? C12A H12A 0.88(5) . ? C13A C14A 1.364(7) . ? C13A H13A 0.92(4) . ? C14A C15A 1.391(5) . ? C14A H14A 0.84(5) . ? C15A H15A 0.88(4) . ? Ni1B N2B 2.013(2) . ? Ni1B N4B 2.068(2) . ? Ni1B O5 2.080(2) . ? Ni1B N1B 2.108(2) . ? Ni1B N3B 2.122(2) . ? O5 H51 0.80(5) . ? O5 H52 0.81(5) . ? N1B C1B 1.337(4) . ? N1B C5B 1.352(3) . ? N2B C10B 1.329(4) . ? N2B C6B 1.344(3) . ? N3B C15B 1.346(4) . ? N3B C11B 1.350(4) . ? N4B N5B 1.192(3) . ? N5B N6B 1.146(4) . ? C1B C2B 1.390(5) . ? C1B H1B 0.91(4) . ? C2B C3B 1.370(5) . ? C2B H2B 0.92(5) . ? C3B C4B 1.376(5) . ? C3B H3B 0.92(4) . ? C4B C5B 1.390(4) . ? C4B H4B 0.86(5) . ? C5B C6B 1.478(4) . ? C6B C7B 1.391(4) . ? C7B C8B 1.377(6) . ? C7B H7B 1.00(4) . ? C8B C9B 1.386(5) . ? C8B H8B 0.97(4) . ? C9B C10B 1.387(4) . ? C9B H9B 0.88(4) . ? C10B C11B 1.487(4) . ? C11B C12B 1.383(5) . ? C12B C13B 1.388(6) . ? C12B H12B 0.95(4) . ? C13B C14B 1.363(6) . ? C13B H13B 0.94(4) . ? C14B C15B 1.385(5) . ? C14B H14B 1.00(4) . ? C15B H15B 0.97(4) . ? Cl1 O3 1.411(3) . ? Cl1 O4 1.421(3) . ? Cl1 O2 1.430(3) . ? Cl1 O1 1.440(3) . ? O6 H61 0.82(5) . ? O6 H62 0.70(5) . ? 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 N2A Ni1A N4A 168.65(9) . . ? N2A Ni1A N7A 97.09(10) . . ? N4A Ni1A N7A 94.25(10) . . ? N2A Ni1A N3A 78.06(10) . . ? N4A Ni1A N3A 101.63(10) . . ? N7A Ni1A N3A 89.28(10) . . ? N2A Ni1A N1A 78.43(10) . . ? N4A Ni1A N1A 102.12(10) . . ? N7A Ni1A N1A 90.11(10) . . ? N3A Ni1A N1A 156.23(10) . . ? N2A Ni1A N4B 90.85(9) . . ? N4A Ni1A N4B 77.80(9) . . ? N7A Ni1A N4B 171.76(9) . . ? N3A Ni1A N4B 90.25(9) . . ? N1A Ni1A N4B 93.62(9) . . ? C5A N1A C1A 118.7(3) . . ? C5A N1A Ni1A 114.1(2) . . ? C1A N1A Ni1A 127.1(2) . . ? C6A N2A C10A 122.6(3) . . ? C6A N2A Ni1A 118.2(2) . . ? C10A N2A Ni1A 119.1(2) . . ? C15A N3A C11A 118.9(3) . . ? C15A N3A Ni1A 126.6(2) . . ? C11A N3A Ni1A 114.4(2) . . ? N5A N4A Ni1A 129.2(2) . . ? N5A N4A Ni1B 121.1(2) . . ? Ni1A N4A Ni1B 102.46(10) . . ? N6A N5A N4A 177.6(4) . . ? N8A N7A Ni1A 123.2(2) . . ? N9A N8A N7A 179.4(3) . . ? N1A C1A C2A 123.3(4) . . ? N1A C1A H1A 113.0(28) . . ? C2A C1A H1A 123.6(29) . . ? C1A C2A C3A 117.9(4) . . ? C1A C2A H2A 119.0(28) . . ? C3A C2A H2A 123.1(27) . . ? C2A C3A C4A 120.5(4) . . ? C2A C3A H3A 126.4(32) . . ? C4A C3A H3A 113.0(32) . . ? C3A C4A C5A 119.0(5) . . ? C3A C4A H4A 131.7(32) . . ? C5A C4A H4A 108.4(32) . . ? N1A C5A C4A 120.6(4) . . ? N1A C5A C6A 115.1(3) . . ? C4A C5A C6A 124.2(4) . . ? N2A C6A C7A 119.5(4) . . ? N2A C6A C5A 113.9(3) . . ? C7A C6A C5A 126.6(3) . . ? C8A C7A C6A 118.6(4) . . ? C8A C7A H7A 125.8(25) . . ? C6A C7A H7A 115.5(26) . . ? C9A C8A C7A 120.8(4) . . ? C9A C8A H8A 124.6(28) . . ? C7A C8A H8A 114.0(28) . . ? C8A C9A C10A 118.7(4) . . ? C8A C9A H9A 123.5(33) . . ? C10A C9A H9A 117.8(34) . . ? N2A C10A C9A 119.7(3) . . ? N2A C10A C11A 113.3(3) . . ? C9A C10A C11A 126.9(3) . . ? N3A C11A C12A 121.6(3) . . ? N3A C11A C10A 115.0(3) . . ? C12A C11A C10A 123.4(3) . . ? C13A C12A C11A 118.9(4) . . ? C13A C12A H12A 118.2(29) . . ? C11A C12A H12A 122.8(30) . . ? C14A C13A C12A 119.5(3) . . ? C14A C13A H13A 114.2(29) . . ? C12A C13A H13A 126.3(29) . . ? C13A C14A C15A 119.6(4) . . ? C13A C14A H14A 121.7(31) . . ? C15A C14A H14A 118.6(32) . . ? N3A C15A C14A 121.4(4) . . ? N3A C15A H15A 117.6(29) . . ? C14A C15A H15A 121.0(30) . . ? N2B Ni1B N4B 169.89(9) . . ? N2B Ni1B O5 96.53(10) . . ? N4B Ni1B O5 92.71(10) . . ? N2B Ni1B N1B 77.66(9) . . ? N4B Ni1B N1B 98.67(9) . . ? O5 Ni1B N1B 87.86(10) . . ? N2B Ni1B N4A 91.69(9) . . ? N4B Ni1B N4A 79.07(9) . . ? O5 Ni1B N4A 171.78(9) . . ? N1B Ni1B N4A 93.69(9) . . ? N2B Ni1B N3B 77.84(9) . . ? N4B Ni1B N3B 106.52(9) . . ? O5 Ni1B N3B 88.81(10) . . ? N1B Ni1B N3B 154.72(9) . . ? N4A Ni1B N3B 93.16(9) . . ? Ni1B O5 H51 118.8(31) . . ? Ni1B O5 H52 120.6(31) . . ? H51 O5 H52 106.3(42) . . ? C1B N1B C5B 118.4(2) . . ? C1B N1B Ni1B 127.1(2) . . ? C5B N1B Ni1B 114.5(2) . . ? C10B N2B C6B 122.0(2) . . ? C10B N2B Ni1B 118.8(2) . . ? C6B N2B Ni1B 118.5(2) . . ? C15B N3B C11B 118.4(3) . . ? C15B N3B Ni1B 127.5(2) . . ? C11B N3B Ni1B 113.8(2) . . ? N5B N4B Ni1B 129.4(2) . . ? N5B N4B Ni1A 120.6(2) . . ? Ni1B N4B Ni1A 100.60(9) . . ? N6B N5B N4B 178.1(3) . . ? N1B C1B C2B 122.4(3) . . ? N1B C1B H1B 116.5(28) . . ? C2B C1B H1B 121.0(28) . . ? C3B C2B C1B 118.9(3) . . ? C3B C2B H2B 118.6(28) . . ? C1B C2B H2B 122.5(28) . . ? C4B C3B C2B 119.6(3) . . ? C4B C3B H3B 123.5(28) . . ? C2B C3B H3B 116.9(28) . . ? C3B C4B C5B 118.9(3) . . ? C3B C4B H4B 119.4(30) . . ? C5B C4B H4B 121.7(30) . . ? N1B C5B C4B 121.8(3) . . ? N1B C5B C6B 114.8(2) . . ? C4B C5B C6B 123.4(3) . . ? N2B C6B C7B 120.5(3) . . ? N2B C6B C5B 113.6(2) . . ? C7B C6B C5B 125.9(3) . . ? C8B C7B C6B 117.8(3) . . ? C8B C7B H7B 121.1(25) . . ? C6B C7B H7B 120.8(25) . . ? C7B C8B C9B 121.0(3) . . ? C7B C8B H8B 125.1(24) . . ? C9B C8B H8B 113.7(24) . . ? C10B C9B C8B 118.4(3) . . ? C10B C9B H9B 113.7(29) . . ? C8B C9B H9B 127.9(28) . . ? N2B C10B C9B 120.3(3) . . ? N2B C10B C11B 113.8(2) . . ? C9B C10B C11B 125.9(3) . . ? N3B C11B C12B 122.0(3) . . ? N3B C11B C10B 115.0(3) . . ? C12B C11B C10B 122.9(3) . . ? C11B C12B C13B 118.5(3) . . ? C11B C12B H12B 116.8(27) . . ? C13B C12B H12B 124.4(27) . . ? C14B C13B C12B 119.8(3) . . ? C14B C13B H13B 122.6(27) . . ? C12B C13B H13B 117.4(27) . . ? C13B C14B C15B 119.0(3) . . ? C13B C14B H14B 126.4(26) . . ? C15B C14B H14B 114.7(26) . . ? N3B C15B C14B 122.2(3) . . ? N3B C15B H15B 116.3(26) . . ? C14B C15B H15B 121.4(26) . . ? O3 Cl1 O4 109.5(2) . . ? O3 Cl1 O2 109.6(2) . . ? O4 Cl1 O2 109.4(2) . . ? O3 Cl1 O1 109.9(2) . . ? O4 Cl1 O1 109.5(2) . . ? O2 Cl1 O1 109.0(2) . . ? H61 O6 H62 99.0(53) . . ? _refine_diff_density_max 0.901 _refine_diff_density_min -1.366 _refine_diff_density_rms 0.081 data_nitn3 _audit_creation_method SHELXL _chemical_formula_sum 'C15 H12 N9 Ni O0.50' _chemical_formula_weight 385.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 20.979(3) _cell_length_b 7.7330(10) _cell_length_c 20.117(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.29(2) _cell_angle_gamma 90.00 _cell_volume 3263.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.567 _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 1.212 _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_reflns_number 4716 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 23.53 _reflns_number_total 2433 _reflns_number_observed 2185 _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 on F^2^ for ALL reflections except for 18 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1473P)^2^+4.2537P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_extinction_method none _refine_ls_number_reflns 2415 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_obs 0.0675 _refine_ls_wR_factor_all 0.2251 _refine_ls_wR_factor_obs 0.1891 _refine_ls_goodness_of_fit_all 1.062 _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_restrained_S_all 1.212 _refine_ls_restrained_S_obs 1.068 _refine_ls_shift/esd_max 2.968 _refine_ls_shift/esd_mean 0.148 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni Ni 0.67510(3) 0.76152(7) 0.47718(3) 0.0455(3) Uani 1 d . . N1 N 0.63598(15) 0.6686(4) 0.56607(15) 0.0336(8) Uani 1 d . . N2 N 0.61335(14) 0.9471(4) 0.4997(2) 0.0314(7) Uani 1 d . . N3 N 0.6830(2) 0.9274(4) 0.3942(2) 0.0346(8) Uani 1 d . . N4 N 0.6120(2) 0.6085(4) 0.4215(2) 0.0454(9) Uani 1 d . . N5 N 0.5947(2) 0.6405(5) 0.3683(2) 0.0452(9) Uani 1 d . . N6 N 0.5754(3) 0.6722(10) 0.3163(3) 0.103(2) Uani 1 d . . N7 N 0.7512(2) 0.5999(4) 0.4672(2) 0.0383(8) Uani 1 d . . N8 N 0.7615(2) 0.4907(5) 0.4286(2) 0.0487(10) Uani 1 d . . N9 N 0.7693(18) 0.3633(42) 0.3942(20) 0.110(9) Uani 0.50 d P . N9 N 0.7796(18) 0.4136(44) 0.3866(17) 0.081(7) Uani 0.50 d P . C1 C 0.6479(2) 0.5143(5) 0.5953(2) 0.0414(10) Uani 1 d . . H1 H 0.6775(2) 0.4404(5) 0.5761(2) 0.061(4) Uiso 1 calc R . C2 C 0.6175(2) 0.4632(6) 0.6525(2) 0.0498(12) Uani 1 d . . H2 H 0.6269(2) 0.3571(6) 0.6720(2) 0.061(4) Uiso 1 calc R . C3 C 0.5732(2) 0.5710(7) 0.6804(2) 0.0559(13) Uani 1 d . . H3 H 0.5518(2) 0.5381(7) 0.7187(2) 0.061(4) Uiso 1 calc R . C4 C 0.5605(3) 0.7295(6) 0.6509(3) 0.0504(12) Uani 1 d . . H4 H 0.5307(3) 0.8042(6) 0.6693(3) 0.061(4) Uiso 1 calc R . C5 C 0.5927(2) 0.7751(5) 0.5940(2) 0.0350(10) Uani 1 d . . C6 C 0.5825(2) 0.9392(5) 0.5575(2) 0.0342(9) Uani 1 d . . C7 C 0.5438(2) 1.0742(6) 0.5781(2) 0.0475(11) Uani 1 d . . H7 H 0.5217(2) 1.0680(6) 0.6180(2) 0.061(4) Uiso 1 calc R . C8 C 0.5391(2) 1.2177(6) 0.5377(3) 0.0496(12) Uani 1 d . . H8 H 0.5135(2) 1.3099(6) 0.5506(3) 0.061(4) Uiso 1 calc R . C9 C 0.5717(2) 1.2268(5) 0.4783(3) 0.0457(12) Uani 1 d . . H9 H 0.5688(2) 1.3242(5) 0.4513(3) 0.061(4) Uiso 1 calc R . C10 C 0.6091(2) 1.0862(5) 0.4599(2) 0.0350(9) Uani 1 d . . C11 C 0.6451(2) 1.0681(5) 0.3977(2) 0.0367(9) Uani 1 d . . C12 C 0.6391(2) 1.1818(7) 0.3441(2) 0.0530(12) Uani 1 d . . H12 H 0.6134(2) 1.2793(7) 0.3470(2) 0.061(4) Uiso 1 calc R . C13 C 0.6722(3) 1.1457(8) 0.2873(2) 0.0639(14) Uani 1 d . . H13 H 0.6696(3) 1.2209(8) 0.2513(2) 0.061(4) Uiso 1 calc R . C14 C 0.7091(2) 1.0007(8) 0.2829(2) 0.0590(13) Uani 1 d . . H14 H 0.7302(2) 0.9732(8) 0.2438(2) 0.061(4) Uiso 1 calc R . C15 C 0.7138(2) 0.8962(6) 0.3384(2) 0.0451(10) Uani 1 d . . H15 H 0.7399(2) 0.7992(6) 0.3364(2) 0.061(4) Uiso 1 calc R . O O 0.5000 0.9421(10) 0.2500 0.092(2) Uani 1 d S . H16 H 0.5369(26) 0.9107(79) 0.2540(34) 0.061(4) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni 0.0538(5) 0.0400(5) 0.0428(5) 0.0002(2) -0.0007(3) 0.0034(2) N1 0.041(2) 0.030(2) 0.030(2) 0.0015(14) -0.0020(13) -0.0027(14) N2 0.035(2) 0.025(2) 0.034(2) -0.0021(13) -0.0054(13) 0.0000(13) N3 0.042(2) 0.030(2) 0.032(2) 0.0015(13) -0.0054(14) -0.0013(14) N4 0.058(2) 0.032(2) 0.047(2) 0.001(2) -0.012(2) -0.008(2) N5 0.058(2) 0.037(2) 0.040(2) -0.010(2) -0.008(2) -0.010(2) N6 0.138(5) 0.108(5) 0.061(3) 0.000(3) -0.042(3) -0.037(4) N7 0.040(2) 0.037(2) 0.038(2) -0.009(2) -0.0067(14) 0.0073(14) N8 0.045(2) 0.044(2) 0.056(2) -0.017(2) -0.015(2) 0.007(2) N9 0.077(14) 0.060(16) 0.192(24) -0.077(14) -0.038(13) 0.020(11) N9 0.099(14) 0.077(18) 0.068(10) -0.059(11) -0.011(8) 0.001(10) C1 0.051(2) 0.033(2) 0.040(2) 0.001(2) -0.003(2) -0.002(2) C2 0.065(3) 0.044(3) 0.040(2) 0.013(2) -0.009(2) -0.013(2) C3 0.063(3) 0.069(3) 0.036(2) 0.010(2) 0.007(2) -0.013(3) C4 0.058(3) 0.057(3) 0.037(2) -0.002(2) 0.001(2) -0.001(2) C5 0.036(2) 0.040(2) 0.029(2) -0.004(2) 0.000(2) -0.003(2) C6 0.036(2) 0.033(2) 0.034(2) -0.007(2) -0.003(2) 0.000(2) C7 0.049(2) 0.044(3) 0.049(2) -0.018(2) 0.004(2) 0.000(2) C8 0.044(2) 0.033(2) 0.072(3) -0.015(2) 0.002(2) 0.005(2) C9 0.048(3) 0.023(2) 0.065(3) -0.002(2) -0.009(2) 0.004(2) C10 0.035(2) 0.025(2) 0.045(2) 0.001(2) -0.007(2) -0.001(2) C11 0.039(2) 0.029(2) 0.042(2) 0.006(2) -0.008(2) -0.005(2) C12 0.058(3) 0.043(3) 0.058(3) 0.021(2) -0.006(2) 0.000(2) C13 0.073(3) 0.069(4) 0.049(3) 0.032(3) -0.006(2) -0.001(3) C14 0.066(3) 0.074(4) 0.037(2) 0.009(2) 0.005(2) -0.001(3) C15 0.058(3) 0.048(3) 0.029(2) 0.005(2) 0.003(2) -0.003(2) O 0.105(5) 0.084(5) 0.087(4) 0.000 0.027(5) 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 Ni N2 1.988(3) . ? Ni N7 2.039(3) . ? Ni N4 2.095(4) . ? Ni N1 2.098(3) . ? Ni N3 2.113(3) . ? Ni N7 2.184(3) 7_666 ? N1 C5 1.350(5) . ? N1 C1 1.353(5) . ? N2 C6 1.333(5) . ? N2 C10 1.344(5) . ? N3 C15 1.319(5) . ? N3 C11 1.350(5) . ? N4 N5 1.156(5) . ? N5 N6 1.146(6) . ? N7 N8 1.168(5) . ? N7 Ni 2.184(3) 7_666 ? N8 N9 1.22(4) . ? N8 N9 1.10(4) . ? N9 N9 0.47(5) . ? C1 C2 1.376(6) . ? C1 H1 0.93 . ? C2 C3 1.371(7) . ? C2 H2 0.93 . ? C3 C4 1.387(7) . ? C3 H3 0.93 . ? C4 C5 1.378(7) . ? C4 H4 0.93 . ? C5 C6 1.482(6) . ? C6 C7 1.388(6) . ? C7 C8 1.380(7) . ? C7 H7 0.93 . ? C8 C9 1.383(8) . ? C8 H8 0.93 . ? C9 C10 1.392(6) . ? C9 H9 0.93 . ? C10 C11 1.470(6) . ? C11 C12 1.396(6) . ? C12 C13 1.369(8) . ? C12 H12 0.93 . ? C13 C14 1.365(8) . ? C13 H13 0.93 . ? C14 C15 1.382(6) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? O H16 0.81(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni N7 167.69(13) . . ? N2 Ni N4 96.87(14) . . ? N7 Ni N4 95.39(14) . . ? N2 Ni N1 78.13(13) . . ? N7 Ni N1 100.60(13) . . ? N4 Ni N1 90.77(14) . . ? N2 Ni N3 78.21(13) . . ? N7 Ni N3 103.31(14) . . ? N4 Ni N3 88.41(13) . . ? N1 Ni N3 156.05(13) . . ? N2 Ni N7 89.36(12) . 7_666 ? N7 Ni N7 78.38(14) . 7_666 ? N4 Ni N7 173.77(13) . 7_666 ? N1 Ni N7 90.59(13) . 7_666 ? N3 Ni N7 92.80(13) . 7_666 ? C5 N1 C1 118.7(3) . . ? C5 N1 Ni 114.4(3) . . ? C1 N1 Ni 126.9(3) . . ? C6 N2 C10 121.7(3) . . ? C6 N2 Ni 119.0(3) . . ? C10 N2 Ni 118.9(3) . . ? C15 N3 C11 119.0(3) . . ? C15 N3 Ni 126.9(3) . . ? C11 N3 Ni 113.5(3) . . ? N5 N4 Ni 124.7(3) . . ? N6 N5 N4 177.6(6) . . ? N8 N7 Ni 131.0(3) . . ? N8 N7 Ni 124.2(3) . 7_666 ? Ni N7 Ni 101.62(14) . 7_666 ? N7 N8 N9 172.0(15) . . ? N7 N8 N9 164.9(15) . . ? N9 N8 N9 22.8(23) . . ? N9 N9 N8 65.1(83) . . ? N9 N9 N8 92.1(89) . . ? N1 C1 C2 122.1(4) . . ? N1 C1 H1 118.9(2) . . ? C2 C1 H1 119.0(3) . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120.5(3) . . ? C3 C2 H2 120.5(3) . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3 120.3(3) . . ? C4 C3 H3 120.3(3) . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4(3) . . ? C3 C4 H4 120.4(3) . . ? N1 C5 C4 121.5(4) . . ? N1 C5 C6 114.3(4) . . ? C4 C5 C6 124.2(4) . . ? N2 C6 C7 120.9(4) . . ? N2 C6 C5 113.7(3) . . ? C7 C6 C5 125.3(4) . . ? C8 C7 C6 117.9(4) . . ? C8 C7 H7 121.0(3) . . ? C6 C7 H7 121.0(3) . . ? C7 C8 C9 121.1(4) . . ? C7 C8 H8 119.5(3) . . ? C9 C8 H8 119.4(3) . . ? C8 C9 C10 118.2(4) . . ? C8 C9 H9 120.9(3) . . ? C10 C9 H9 120.9(3) . . ? N2 C10 C9 120.1(4) . . ? N2 C10 C11 113.5(3) . . ? C9 C10 C11 126.3(4) . . ? N3 C11 C12 121.1(4) . . ? N3 C11 C10 115.3(3) . . ? C12 C11 C10 123.5(4) . . ? C13 C12 C11 118.2(5) . . ? C13 C12 H12 120.9(3) . . ? C11 C12 H12 120.9(3) . . ? C14 C13 C12 120.8(4) . . ? C14 C13 H13 119.6(3) . . ? C12 C13 H13 119.6(3) . . ? C13 C14 C15 117.8(5) . . ? C13 C14 H14 121.1(3) . . ? C15 C14 H14 121.1(3) . . ? N3 C15 C14 123.1(5) . . ? N3 C15 H15 118.5(2) . . ? C14 C15 H15 118.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ni N1 C5 -1.8(3) . . . . ? N7 Ni N1 C5 165.7(3) . . . . ? N4 Ni N1 C5 -98.7(3) . . . . ? N3 Ni N1 C5 -10.8(5) . . . . ? N7 Ni N1 C5 87.4(3) 7_666 . . . ? N2 Ni N1 C1 175.4(3) . . . . ? N7 Ni N1 C1 -17.1(3) . . . . ? N4 Ni N1 C1 78.5(3) . . . . ? N3 Ni N1 C1 166.3(3) . . . . ? N7 Ni N1 C1 -95.4(3) 7_666 . . . ? N7 Ni N2 C6 -79.8(7) . . . . ? N4 Ni N2 C6 94.9(3) . . . . ? N1 Ni N2 C6 5.5(3) . . . . ? N3 Ni N2 C6 -178.2(3) . . . . ? N7 Ni N2 C6 -85.2(3) 7_666 . . . ? N7 Ni N2 C10 93.0(7) . . . . ? N4 Ni N2 C10 -92.3(3) . . . . ? N1 Ni N2 C10 178.3(3) . . . . ? N3 Ni N2 C10 -5.4(3) . . . . ? N7 Ni N2 C10 87.6(3) 7_666 . . . ? N2 Ni N3 C15 -170.6(4) . . . . ? N7 Ni N3 C15 21.9(4) . . . . ? N4 Ni N3 C15 -73.3(4) . . . . ? N1 Ni N3 C15 -161.6(3) . . . . ? N7 Ni N3 C15 100.6(3) 7_666 . . . ? N2 Ni N3 C11 0.4(3) . . . . ? N7 Ni N3 C11 -167.0(3) . . . . ? N4 Ni N3 C11 97.8(3) . . . . ? N1 Ni N3 C11 9.5(5) . . . . ? N7 Ni N3 C11 -88.3(3) 7_666 . . . ? N2 Ni N4 N5 74.8(4) . . . . ? N7 Ni N4 N5 -106.3(4) . . . . ? N1 Ni N4 N5 153.0(4) . . . . ? N3 Ni N4 N5 -3.1(4) . . . . ? N7 Ni N4 N5 -104.4(12) 7_666 . . . ? Ni N4 N5 N6 -121.9(130) . . . . ? N2 Ni N7 N8 -165.6(5) . . . . ? N4 Ni N7 N8 19.8(4) . . . . ? N1 Ni N7 N8 111.6(4) . . . . ? N3 Ni N7 N8 -69.9(4) . . . . ? N7 Ni N7 N8 -160.0(5) 7_666 . . . ? N2 Ni N7 Ni -5.5(7) . . . 7_666 ? N4 Ni N7 Ni 179.79(14) . . . 7_666 ? N1 Ni N7 Ni -88.41(15) . . . 7_666 ? N3 Ni N7 Ni 90.15(15) . . . 7_666 ? N7 Ni N7 Ni 0.0 7_666 . . 7_666 ? Ni N7 N8 N9 -95.7(143) . . . . ? Ni N7 N8 N9 108.2(143) 7_666 . . . ? Ni N7 N8 N9 103.4(85) . . . . ? Ni N7 N8 N9 -52.7(86) 7_666 . . . ? N7 N8 N9 N9 -167.3(52) . . . . ? N9 N8 N9 N9 0.000(10) . . . . ? N8 N9 N9 N8 0.000(4) . . . . ? N7 N8 N9 N9 173.3(31) . . . . ? N9 N8 N9 N9 0.000(8) . . . . ? C5 N1 C1 C2 -0.2(6) . . . . ? Ni N1 C1 C2 -177.3(3) . . . . ? N1 C1 C2 C3 0.8(6) . . . . ? C1 C2 C3 C4 -0.8(7) . . . . ? C2 C3 C4 C5 0.2(7) . . . . ? C1 N1 C5 C4 -0.4(6) . . . . ? Ni N1 C5 C4 177.0(3) . . . . ? C1 N1 C5 C6 -179.0(3) . . . . ? Ni N1 C5 C6 -1.6(4) . . . . ? C3 C4 C5 N1 0.4(7) . . . . ? C3 C4 C5 C6 178.9(4) . . . . ? C10 N2 C6 C7 1.1(5) . . . . ? Ni N2 C6 C7 173.6(3) . . . . ? C10 N2 C6 C5 179.5(3) . . . . ? Ni N2 C6 C5 -7.9(4) . . . . ? N1 C5 C6 N2 6.0(5) . . . . ? C4 C5 C6 N2 -172.6(4) . . . . ? N1 C5 C6 C7 -175.7(4) . . . . ? C4 C5 C6 C7 5.7(7) . . . . ? N2 C6 C7 C8 -1.1(6) . . . . ? C5 C6 C7 C8 -179.3(4) . . . . ? C6 C7 C8 C9 0.2(7) . . . . ? C7 C8 C9 C10 0.7(7) . . . . ? C6 N2 C10 C9 -0.1(6) . . . . ? Ni N2 C10 C9 -172.7(3) . . . . ? C6 N2 C10 C11 -178.4(3) . . . . ? Ni N2 C10 C11 9.0(4) . . . . ? C8 C9 C10 N2 -0.7(6) . . . . ? C8 C9 C10 C11 177.3(4) . . . . ? C15 N3 C11 C12 -1.3(6) . . . . ? Ni N3 C11 C12 -173.1(3) . . . . ? C15 N3 C11 C10 175.8(3) . . . . ? Ni N3 C11 C10 4.0(4) . . . . ? N2 C10 C11 N3 -8.3(5) . . . . ? C9 C10 C11 N3 173.5(4) . . . . ? N2 C10 C11 C12 168.7(4) . . . . ? C9 C10 C11 C12 -9.4(6) . . . . ? N3 C11 C12 C13 0.8(7) . . . . ? C10 C11 C12 C13 -176.1(4) . . . . ? C11 C12 C13 C14 1.2(8) . . . . ? C12 C13 C14 C15 -2.6(8) . . . . ? C11 N3 C15 C14 -0.2(6) . . . . ? Ni N3 C15 C14 170.4(4) . . . . ? C13 C14 C15 N3 2.2(8) . . . . ? _refine_diff_density_max 0.826 _refine_diff_density_min -0.878 _refine_diff_density_rms 0.119