# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Philippe Gros' _publ_contact_author_name ' Philippe Gros' _publ_contact_author_email philippe.gros@srsmc.uhp-nancy.fr data_jwrr100913 _database_code_depnum_ccdc_archive 'CCDC 893819' #TrackingRef '- jwrr100913.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H27 N5 Ni O, C H2 Cl2' _chemical_formula_sum 'C46 H29 Cl2 N5 Ni O' _chemical_formula_weight 797.35 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 22.2844(6) _cell_length_b 9.7964(3) _cell_length_c 17.6695(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.5330(10) _cell_angle_gamma 90.00 _cell_volume 3635.38(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6941 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8683 _exptl_absorpt_correction_T_max 0.9309 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker APEX-II CCD' _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 24944 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.52 _reflns_number_total 8363 _reflns_number_gt 6381 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+4.9112P] 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 8363 _refine_ls_number_parameters 504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.31554(12) 0.0470(3) 0.57894(15) 0.0225(5) Uani 1 1 d . . . C2 C 0.36897(13) 0.0482(3) 0.65153(17) 0.0302(6) Uani 1 1 d . . . H2 H 0.3700 0.0137 0.7022 0.036 Uiso 1 1 calc R . . C3 C 0.41791(13) 0.1076(3) 0.63475(16) 0.0296(6) Uani 1 1 d . . . H3 H 0.4591 0.1262 0.6717 0.035 Uiso 1 1 calc R . . C4 C 0.39556(12) 0.1372(3) 0.55030(15) 0.0219(5) Uani 1 1 d . . . C5 C 0.43343(12) 0.1890(3) 0.50837(15) 0.0207(5) Uani 1 1 d . . . C6 C 0.49679(12) 0.2464(3) 0.55592(15) 0.0215(5) Uani 1 1 d . . . C7 C 0.49933(15) 0.3738(3) 0.5911(2) 0.0381(7) Uani 1 1 d . . . H7 H 0.4612 0.4244 0.5823 0.046 Uiso 1 1 calc R . . C8 C 0.55715(16) 0.4279(3) 0.6389(2) 0.0413(8) Uani 1 1 d . . . H8 H 0.5586 0.5162 0.6617 0.050 Uiso 1 1 calc R . . C9 C 0.61268(14) 0.3535(3) 0.65358(17) 0.0297(6) Uani 1 1 d . . . H9 H 0.6521 0.3892 0.6875 0.036 Uiso 1 1 calc R . . C10 C 0.61022(13) 0.2269(3) 0.61847(17) 0.0277(6) Uani 1 1 d . . . H10 H 0.6482 0.1757 0.6280 0.033 Uiso 1 1 calc R . . C11 C 0.55275(13) 0.1740(3) 0.56943(17) 0.0254(6) Uani 1 1 d . . . H11 H 0.5517 0.0874 0.5449 0.030 Uiso 1 1 calc R . . C12 C 0.41470(12) 0.1791(3) 0.42531(15) 0.0208(5) Uani 1 1 d . . . C13 C 0.45616(13) 0.1920(3) 0.37873(17) 0.0257(6) Uani 1 1 d . . . H13 H 0.4982 0.2277 0.3967 0.031 Uiso 1 1 calc R . . C14 C 0.42408(13) 0.1437(3) 0.30419(17) 0.0259(6) Uani 1 1 d . . . H14 H 0.4401 0.1351 0.2609 0.031 Uiso 1 1 calc R . . C15 C 0.36142(12) 0.1080(3) 0.30323(15) 0.0205(5) Uani 1 1 d . . . C16 C 0.31129(12) 0.0673(3) 0.23487(15) 0.0206(5) Uani 1 1 d . . . C17 C 0.32564(13) 0.0197(3) 0.16236(16) 0.0235(5) Uani 1 1 d . . . C18 C 0.35788(15) -0.1030(3) 0.1656(2) 0.0337(7) Uani 1 1 d . . . H18 H 0.3734 -0.1520 0.2147 0.040 Uiso 1 1 calc R . . C19 C 0.36739(17) -0.1538(4) 0.0972(2) 0.0452(9) Uani 1 1 d . . . H19 H 0.3883 -0.2389 0.0991 0.054 Uiso 1 1 calc R . . C20 C 0.34644(19) -0.0806(4) 0.0258(2) 0.0492(10) Uani 1 1 d . . . H20 H 0.3526 -0.1160 -0.0211 0.059 Uiso 1 1 calc R . . C21 C 0.31679(17) 0.0430(4) 0.02325(19) 0.0418(8) Uani 1 1 d . . . H21 H 0.3036 0.0942 -0.0252 0.050 Uiso 1 1 calc R . . C22 C 0.30598(15) 0.0936(3) 0.09057(17) 0.0310(6) Uani 1 1 d . . . H22 H 0.2851 0.1790 0.0880 0.037 Uiso 1 1 calc R . . C23 C 0.24872(12) 0.0764(3) 0.23216(15) 0.0204(5) Uani 1 1 d . . . C24 C 0.19401(13) 0.0647(3) 0.16051(16) 0.0255(6) Uani 1 1 d . . . H24 H 0.1937 0.0321 0.1097 0.031 Uiso 1 1 calc R . . C25 C 0.14338(13) 0.1083(3) 0.17880(16) 0.0263(6) Uani 1 1 d . . . H25 H 0.1010 0.1158 0.1427 0.032 Uiso 1 1 calc R . . C26 C 0.16512(12) 0.1417(3) 0.26333(16) 0.0211(5) Uani 1 1 d . . . C27 C 0.14759(12) 0.1415(3) 0.39018(16) 0.0205(5) Uani 1 1 d . . . C28 C 0.12725(12) 0.1762(3) 0.30952(16) 0.0215(5) Uani 1 1 d . . . C29 C 0.06146(12) 0.2283(3) 0.27451(17) 0.0251(6) Uani 1 1 d . . . C30 C 0.04132(14) 0.2976(3) 0.20033(19) 0.0326(6) Uani 1 1 d . . . H30 H 0.0707 0.3139 0.1729 0.039 Uiso 1 1 calc R . . C31 C -0.02107(15) 0.3422(3) 0.1671(2) 0.0383(7) Uani 1 1 d . . . H31 H -0.0342 0.3857 0.1162 0.046 Uiso 1 1 calc R . . C32 C -0.06453(15) 0.3245(3) 0.2069(2) 0.0407(8) Uani 1 1 d . . . H32 H -0.1073 0.3546 0.1833 0.049 Uiso 1 1 calc R . . C33 C -0.04494(14) 0.2624(3) 0.2812(2) 0.0356(7) Uani 1 1 d . . . H33 H -0.0743 0.2515 0.3093 0.043 Uiso 1 1 calc R . . C34 C 0.01754(13) 0.2152(3) 0.31586(18) 0.0274(6) Uani 1 1 d . . . C35 C 0.03694(13) 0.1540(3) 0.39684(18) 0.0267(6) Uani 1 1 d . . . C36 C 0.10340(12) 0.1268(3) 0.43206(16) 0.0236(5) Uani 1 1 d . . . C37 C 0.13531(12) 0.0629(3) 0.50434(16) 0.0233(5) Uani 1 1 d . . . C38 C 0.20200(12) 0.0518(3) 0.50844(15) 0.0213(5) Uani 1 1 d . . . C39 C 0.25320(12) 0.0185(3) 0.57541(15) 0.0216(5) Uani 1 1 d . . . C40 C 0.24196(12) -0.0321(3) 0.64956(16) 0.0222(5) Uani 1 1 d . . . C41 C 0.22978(14) -0.1697(3) 0.65822(18) 0.0287(6) Uani 1 1 d . . . H41 H 0.2315 -0.2336 0.6185 0.034 Uiso 1 1 calc R . . C42 C 0.21521(15) -0.2139(3) 0.72464(19) 0.0325(6) Uani 1 1 d . . . H42 H 0.2067 -0.3077 0.7300 0.039 Uiso 1 1 calc R . . C43 C 0.21307(14) -0.1220(3) 0.78308(18) 0.0314(6) Uani 1 1 d . . . H43 H 0.2026 -0.1526 0.8281 0.038 Uiso 1 1 calc R . . C44 C 0.22615(14) 0.0145(3) 0.77597(17) 0.0281(6) Uani 1 1 d . . . H44 H 0.2253 0.0775 0.8164 0.034 Uiso 1 1 calc R . . C45 C 0.24062(13) 0.0592(3) 0.70937(16) 0.0254(6) Uani 1 1 d . . . H45 H 0.2497 0.1529 0.7046 0.030 Uiso 1 1 calc R . . C46 C 0.0687(2) -0.0165(5) -0.0658(3) 0.0706(13) Uani 1 1 d . . . H46A H 0.0540 0.0738 -0.0539 0.085 Uiso 1 1 calc R . . H46B H 0.0421 -0.0424 -0.1210 0.085 Uiso 1 1 calc R . . N1 N 0.33270(10) 0.0986(2) 0.51666(13) 0.0199(4) Uani 1 1 d . . . N2 N 0.35572(10) 0.1304(2) 0.37715(13) 0.0186(4) Uani 1 1 d . . . N3 N 0.22943(10) 0.1173(2) 0.29573(13) 0.0193(4) Uani 1 1 d . . . N4 N 0.20720(10) 0.0982(2) 0.43648(13) 0.0196(4) Uani 1 1 d . . . N5 N 0.10835(13) 0.0202(3) 0.55694(16) 0.0321(6) Uani 1 1 d . . . O1 O -0.00152(10) 0.1295(2) 0.43246(14) 0.0352(5) Uani 1 1 d . . . Ni1 Ni 0.281401(14) 0.11183(3) 0.406760(19) 0.01717(10) Uani 1 1 d . . . Cl1 Cl 0.05869(6) -0.13637(11) 0.00168(7) 0.0656(3) Uani 1 1 d . . . Cl2 Cl 0.14877(6) -0.00379(14) -0.06114(7) 0.0732(3) Uani 1 1 d . . . H1N H 0.1286(18) -0.035(4) 0.599(2) 0.048(11) Uiso 1 1 d . . . H2N H 0.069(2) 0.023(4) 0.545(2) 0.056(12) 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 C1 0.0220(13) 0.0272(13) 0.0189(12) 0.0001(10) 0.0074(10) 0.0005(10) C2 0.0232(13) 0.0462(17) 0.0205(13) 0.0048(12) 0.0064(11) 0.0015(12) C3 0.0208(13) 0.0473(17) 0.0182(13) -0.0007(12) 0.0033(10) -0.0008(12) C4 0.0182(12) 0.0277(13) 0.0197(12) -0.0030(10) 0.0061(10) 0.0012(10) C5 0.0166(12) 0.0237(12) 0.0215(13) -0.0024(10) 0.0061(10) 0.0004(10) C6 0.0197(12) 0.0257(13) 0.0180(12) -0.0009(10) 0.0050(10) -0.0031(10) C7 0.0264(15) 0.0367(17) 0.0424(18) -0.0155(14) -0.0003(13) 0.0060(13) C8 0.0348(17) 0.0336(16) 0.0446(19) -0.0160(14) -0.0012(14) 0.0001(13) C9 0.0257(14) 0.0376(16) 0.0220(14) -0.0005(12) 0.0031(11) -0.0091(12) C10 0.0191(12) 0.0317(14) 0.0321(15) 0.0060(12) 0.0083(11) 0.0006(11) C11 0.0242(13) 0.0211(12) 0.0318(15) -0.0010(11) 0.0108(11) -0.0017(10) C12 0.0192(12) 0.0217(12) 0.0215(13) -0.0009(10) 0.0069(10) -0.0011(10) C13 0.0222(13) 0.0308(14) 0.0270(14) 0.0018(11) 0.0118(11) -0.0053(11) C14 0.0240(13) 0.0335(14) 0.0244(14) -0.0004(11) 0.0138(11) -0.0029(11) C15 0.0215(12) 0.0217(12) 0.0197(12) 0.0003(10) 0.0086(10) -0.0002(10) C16 0.0250(13) 0.0195(11) 0.0192(12) 0.0006(10) 0.0099(10) -0.0001(10) C17 0.0259(13) 0.0264(13) 0.0213(13) -0.0048(10) 0.0118(11) -0.0062(11) C18 0.0382(17) 0.0318(15) 0.0404(17) -0.0024(13) 0.0253(14) -0.0004(13) C19 0.049(2) 0.0414(18) 0.059(2) -0.0147(17) 0.0364(19) -0.0034(15) C20 0.059(2) 0.063(2) 0.041(2) -0.0240(17) 0.0359(18) -0.0221(19) C21 0.0468(19) 0.059(2) 0.0239(15) -0.0060(15) 0.0172(14) -0.0152(17) C22 0.0372(16) 0.0349(16) 0.0235(14) -0.0033(12) 0.0138(12) -0.0061(13) C23 0.0250(13) 0.0200(12) 0.0159(12) -0.0009(9) 0.0066(10) -0.0019(10) C24 0.0276(14) 0.0301(14) 0.0189(13) 0.0003(11) 0.0080(11) -0.0031(11) C25 0.0242(13) 0.0305(14) 0.0215(13) 0.0030(11) 0.0040(11) -0.0031(11) C26 0.0195(12) 0.0209(12) 0.0215(13) 0.0029(10) 0.0052(10) -0.0023(9) C27 0.0177(12) 0.0209(12) 0.0238(13) -0.0022(10) 0.0079(10) -0.0013(9) C28 0.0179(12) 0.0216(12) 0.0241(13) 0.0017(10) 0.0058(10) 0.0001(10) C29 0.0197(12) 0.0210(12) 0.0328(15) 0.0017(11) 0.0064(11) 0.0008(10) C30 0.0291(15) 0.0298(15) 0.0377(17) 0.0073(13) 0.0094(13) 0.0032(12) C31 0.0310(16) 0.0325(16) 0.0464(19) 0.0119(14) 0.0066(14) 0.0057(13) C32 0.0265(15) 0.0362(17) 0.054(2) 0.0086(15) 0.0066(14) 0.0092(13) C33 0.0229(14) 0.0361(16) 0.0490(19) 0.0027(14) 0.0135(13) 0.0035(12) C34 0.0221(13) 0.0244(13) 0.0350(15) 0.0000(11) 0.0087(12) 0.0016(10) C35 0.0225(13) 0.0263(13) 0.0340(15) -0.0024(11) 0.0131(12) -0.0007(11) C36 0.0188(12) 0.0278(13) 0.0253(13) -0.0014(11) 0.0089(10) -0.0013(10) C37 0.0217(13) 0.0259(13) 0.0256(13) -0.0054(11) 0.0125(11) -0.0033(10) C38 0.0214(12) 0.0236(12) 0.0214(13) -0.0015(10) 0.0103(10) -0.0029(10) C39 0.0233(13) 0.0238(12) 0.0201(12) -0.0013(10) 0.0104(10) -0.0007(10) C40 0.0200(12) 0.0262(13) 0.0216(13) 0.0014(10) 0.0086(10) 0.0007(10) C41 0.0335(15) 0.0244(13) 0.0323(15) -0.0029(11) 0.0166(13) 0.0004(11) C42 0.0374(16) 0.0245(14) 0.0407(17) 0.0058(12) 0.0199(14) 0.0004(12) C43 0.0327(15) 0.0356(16) 0.0309(15) 0.0109(12) 0.0173(13) 0.0051(12) C44 0.0328(15) 0.0307(14) 0.0247(14) 0.0008(11) 0.0150(12) 0.0052(12) C45 0.0296(14) 0.0222(13) 0.0249(14) 0.0023(10) 0.0096(11) 0.0014(11) C46 0.072(3) 0.058(3) 0.080(3) 0.026(2) 0.023(3) -0.004(2) N1 0.0167(10) 0.0238(11) 0.0205(11) -0.0011(9) 0.0078(8) 0.0008(8) N2 0.0175(10) 0.0208(10) 0.0184(10) -0.0020(8) 0.0075(8) -0.0005(8) N3 0.0182(10) 0.0208(10) 0.0198(10) -0.0007(8) 0.0073(8) -0.0011(8) N4 0.0188(10) 0.0215(10) 0.0187(10) -0.0001(8) 0.0063(8) -0.0006(8) N5 0.0225(13) 0.0477(16) 0.0299(14) 0.0028(12) 0.0138(11) -0.0022(11) O1 0.0244(10) 0.0434(12) 0.0435(13) 0.0036(10) 0.0189(9) 0.0025(9) Ni1 0.01530(16) 0.02036(16) 0.01672(16) -0.00126(12) 0.00651(12) -0.00069(12) Cl1 0.0818(8) 0.0586(6) 0.0644(7) 0.0052(5) 0.0351(6) -0.0092(5) Cl2 0.0760(8) 0.0962(9) 0.0586(7) -0.0107(6) 0.0376(6) -0.0172(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.376(3) . ? C1 C39 1.398(4) . ? C1 C2 1.429(4) . ? C2 C3 1.354(4) . ? C2 H2 0.9500 . ? C3 C4 1.436(4) . ? C3 H3 0.9500 . ? C4 N1 1.379(3) . ? C4 C5 1.392(4) . ? C5 C12 1.389(4) . ? C5 C6 1.491(3) . ? C6 C11 1.384(4) . ? C6 C7 1.386(4) . ? C7 C8 1.388(4) . ? C7 H7 0.9500 . ? C8 C9 1.384(4) . ? C8 H8 0.9500 . ? C9 C10 1.379(4) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 N2 1.390(3) . ? C12 C13 1.434(4) . ? C13 C14 1.356(4) . ? C13 H13 0.9500 . ? C14 C15 1.434(4) . ? C14 H14 0.9500 . ? C15 N2 1.372(3) . ? C15 C16 1.401(4) . ? C16 C23 1.382(4) . ? C16 C17 1.495(3) . ? C17 C18 1.392(4) . ? C17 C22 1.398(4) . ? C18 C19 1.388(4) . ? C18 H18 0.9500 . ? C19 C20 1.388(6) . ? C19 H19 0.9500 . ? C20 C21 1.373(5) . ? C20 H20 0.9500 . ? C21 C22 1.382(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 N3 1.389(3) . ? C23 C24 1.439(4) . ? C24 C25 1.343(4) . ? C24 H24 0.9500 . ? C25 C26 1.445(4) . ? C25 H25 0.9500 . ? C26 N3 1.375(3) . ? C26 C28 1.398(4) . ? C27 N4 1.374(3) . ? C27 C28 1.386(4) . ? C27 C36 1.423(4) . ? C28 C29 1.478(3) . ? C29 C34 1.409(4) . ? C29 C30 1.410(4) . ? C30 C31 1.386(4) . ? C30 H30 0.9500 . ? C31 C32 1.384(5) . ? C31 H31 0.9500 . ? C32 C33 1.380(5) . ? C32 H32 0.9500 . ? C33 C34 1.399(4) . ? C33 H33 0.9500 . ? C34 C35 1.476(4) . ? C35 O1 1.244(3) . ? C35 C36 1.427(4) . ? C36 C37 1.386(4) . ? C37 N5 1.332(4) . ? C37 C38 1.467(3) . ? C38 C39 1.380(4) . ? C38 N4 1.391(3) . ? C39 C40 1.498(4) . ? C40 C45 1.393(4) . ? C40 C41 1.393(4) . ? C41 C42 1.387(4) . ? C41 H41 0.9500 . ? C42 C43 1.383(4) . ? C42 H42 0.9500 . ? C43 C44 1.383(4) . ? C43 H43 0.9500 . ? C44 C45 1.391(4) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C46 Cl1 1.741(4) . ? C46 Cl2 1.762(5) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? N1 Ni1 1.900(2) . ? N2 Ni1 1.905(2) . ? N3 Ni1 1.917(2) . ? N4 Ni1 1.900(2) . ? N5 H1N 0.91(4) . ? N5 H2N 0.84(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C39 125.1(2) . . ? N1 C1 C2 110.1(2) . . ? C39 C1 C2 124.0(2) . . ? C3 C2 C1 107.3(2) . . ? C3 C2 H2 126.3 . . ? C1 C2 H2 126.3 . . ? C2 C3 C4 106.8(2) . . ? C2 C3 H3 126.6 . . ? C4 C3 H3 126.6 . . ? N1 C4 C5 125.4(2) . . ? N1 C4 C3 110.0(2) . . ? C5 C4 C3 124.4(2) . . ? C12 C5 C4 121.0(2) . . ? C12 C5 C6 121.0(2) . . ? C4 C5 C6 117.8(2) . . ? C11 C6 C7 119.0(2) . . ? C11 C6 C5 122.2(2) . . ? C7 C6 C5 118.8(2) . . ? C6 C7 C8 120.5(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C6 C11 C10 120.5(3) . . ? C6 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C5 C12 N2 124.0(2) . . ? C5 C12 C13 125.2(2) . . ? N2 C12 C13 109.8(2) . . ? C14 C13 C12 107.2(2) . . ? C14 C13 H13 126.4 . . ? C12 C13 H13 126.4 . . ? C13 C14 C15 107.0(2) . . ? C13 C14 H14 126.5 . . ? C15 C14 H14 126.5 . . ? N2 C15 C16 124.4(2) . . ? N2 C15 C14 110.5(2) . . ? C16 C15 C14 124.9(2) . . ? C23 C16 C15 121.1(2) . . ? C23 C16 C17 119.5(2) . . ? C15 C16 C17 119.3(2) . . ? C18 C17 C22 119.1(3) . . ? C18 C17 C16 119.3(2) . . ? C22 C17 C16 121.6(2) . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 119.9(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 120.5(3) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C17 120.2(3) . . ? C21 C22 H22 119.9 . . ? C17 C22 H22 119.9 . . ? C16 C23 N3 124.9(2) . . ? C16 C23 C24 125.0(2) . . ? N3 C23 C24 109.5(2) . . ? C25 C24 C23 107.2(2) . . ? C25 C24 H24 126.4 . . ? C23 C24 H24 126.4 . . ? C24 C25 C26 107.6(2) . . ? C24 C25 H25 126.2 . . ? C26 C25 H25 126.2 . . ? N3 C26 C28 123.2(2) . . ? N3 C26 C25 109.5(2) . . ? C28 C26 C25 126.8(2) . . ? N4 C27 C28 127.4(2) . . ? N4 C27 C36 111.0(2) . . ? C28 C27 C36 121.0(2) . . ? C27 C28 C26 119.2(2) . . ? C27 C28 C29 116.9(2) . . ? C26 C28 C29 123.2(2) . . ? C34 C29 C30 117.7(2) . . ? C34 C29 C28 121.0(2) . . ? C30 C29 C28 121.2(3) . . ? C31 C30 C29 120.5(3) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C32 C31 C30 121.3(3) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C33 C32 C31 119.1(3) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C32 C33 C34 120.9(3) . . ? C32 C33 H33 119.5 . . ? C34 C33 H33 119.5 . . ? C33 C34 C29 120.4(3) . . ? C33 C34 C35 118.9(3) . . ? C29 C34 C35 120.7(2) . . ? O1 C35 C36 122.2(3) . . ? O1 C35 C34 122.7(3) . . ? C36 C35 C34 115.1(2) . . ? C37 C36 C27 107.1(2) . . ? C37 C36 C35 128.6(2) . . ? C27 C36 C35 123.5(2) . . ? N5 C37 C36 124.9(3) . . ? N5 C37 C38 128.9(3) . . ? C36 C37 C38 106.1(2) . . ? C39 C38 N4 124.3(2) . . ? C39 C38 C37 126.4(2) . . ? N4 C38 C37 108.9(2) . . ? C38 C39 C1 121.0(2) . . ? C38 C39 C40 119.7(2) . . ? C1 C39 C40 118.8(2) . . ? C45 C40 C41 118.9(2) . . ? C45 C40 C39 120.2(2) . . ? C41 C40 C39 120.8(2) . . ? C42 C41 C40 120.2(3) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C43 C42 C41 120.3(3) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C42 C43 C44 120.0(3) . . ? C42 C43 H43 120.0 . . ? C44 C43 H43 120.0 . . ? C43 C44 C45 119.8(3) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C44 C45 C40 120.6(3) . . ? C44 C45 H45 119.7 . . ? C40 C45 H45 119.7 . . ? Cl1 C46 Cl2 112.0(3) . . ? Cl1 C46 H46A 109.2 . . ? Cl2 C46 H46A 109.2 . . ? Cl1 C46 H46B 109.2 . . ? Cl2 C46 H46B 109.2 . . ? H46A C46 H46B 107.9 . . ? C1 N1 C4 105.7(2) . . ? C1 N1 Ni1 127.53(17) . . ? C4 N1 Ni1 126.81(18) . . ? C15 N2 C12 105.6(2) . . ? C15 N2 Ni1 127.74(17) . . ? C12 N2 Ni1 126.57(17) . . ? C26 N3 C23 105.9(2) . . ? C26 N3 Ni1 128.32(17) . . ? C23 N3 Ni1 125.12(17) . . ? C27 N4 C38 106.6(2) . . ? C27 N4 Ni1 124.84(17) . . ? C38 N4 Ni1 128.46(17) . . ? C37 N5 H1N 123(2) . . ? C37 N5 H2N 120(3) . . ? H1N N5 H2N 114(4) . . ? N4 Ni1 N1 89.68(9) . . ? N4 Ni1 N2 178.55(9) . . ? N1 Ni1 N2 90.35(9) . . ? N4 Ni1 N3 90.06(9) . . ? N1 Ni1 N3 177.69(9) . . ? N2 Ni1 N3 89.97(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 3.4(3) . . . . ? C39 C1 C2 C3 -167.0(3) . . . . ? C1 C2 C3 C4 -2.9(3) . . . . ? C2 C3 C4 N1 1.5(3) . . . . ? C2 C3 C4 C5 -174.7(3) . . . . ? N1 C4 C5 C12 -14.2(4) . . . . ? C3 C4 C5 C12 161.5(3) . . . . ? N1 C4 C5 C6 170.1(2) . . . . ? C3 C4 C5 C6 -14.2(4) . . . . ? C12 C5 C6 C11 -74.6(3) . . . . ? C4 C5 C6 C11 101.1(3) . . . . ? C12 C5 C6 C7 108.7(3) . . . . ? C4 C5 C6 C7 -75.6(3) . . . . ? C11 C6 C7 C8 0.1(5) . . . . ? C5 C6 C7 C8 176.9(3) . . . . ? C6 C7 C8 C9 -1.6(6) . . . . ? C7 C8 C9 C10 1.7(5) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C7 C6 C11 C10 1.2(4) . . . . ? C5 C6 C11 C10 -175.5(3) . . . . ? C9 C10 C11 C6 -1.0(4) . . . . ? C4 C5 C12 N2 6.4(4) . . . . ? C6 C5 C12 N2 -178.0(2) . . . . ? C4 C5 C12 C13 -161.1(3) . . . . ? C6 C5 C12 C13 14.4(4) . . . . ? C5 C12 C13 C14 165.4(3) . . . . ? N2 C12 C13 C14 -3.7(3) . . . . ? C12 C13 C14 C15 3.2(3) . . . . ? C13 C14 C15 N2 -1.7(3) . . . . ? C13 C14 C15 C16 173.1(3) . . . . ? N2 C15 C16 C23 14.9(4) . . . . ? C14 C15 C16 C23 -159.2(3) . . . . ? N2 C15 C16 C17 -168.0(2) . . . . ? C14 C15 C16 C17 17.9(4) . . . . ? C23 C16 C17 C18 -114.7(3) . . . . ? C15 C16 C17 C18 68.2(3) . . . . ? C23 C16 C17 C22 63.6(4) . . . . ? C15 C16 C17 C22 -113.5(3) . . . . ? C22 C17 C18 C19 -3.2(4) . . . . ? C16 C17 C18 C19 175.2(3) . . . . ? C17 C18 C19 C20 1.9(5) . . . . ? C18 C19 C20 C21 0.6(5) . . . . ? C19 C20 C21 C22 -1.8(5) . . . . ? C20 C21 C22 C17 0.5(5) . . . . ? C18 C17 C22 C21 2.0(4) . . . . ? C16 C17 C22 C21 -176.3(3) . . . . ? C15 C16 C23 N3 -3.9(4) . . . . ? C17 C16 C23 N3 179.0(2) . . . . ? C15 C16 C23 C24 166.4(3) . . . . ? C17 C16 C23 C24 -10.6(4) . . . . ? C16 C23 C24 C25 -166.7(3) . . . . ? N3 C23 C24 C25 4.9(3) . . . . ? C23 C24 C25 C26 -2.8(3) . . . . ? C24 C25 C26 N3 -0.2(3) . . . . ? C24 C25 C26 C28 -172.3(3) . . . . ? N4 C27 C28 C26 13.3(4) . . . . ? C36 C27 C28 C26 -156.4(2) . . . . ? N4 C27 C28 C29 -176.3(2) . . . . ? C36 C27 C28 C29 14.0(4) . . . . ? N3 C26 C28 C27 -22.5(4) . . . . ? C25 C26 C28 C27 148.6(3) . . . . ? N3 C26 C28 C29 167.7(2) . . . . ? C25 C26 C28 C29 -21.2(4) . . . . ? C27 C28 C29 C34 -13.4(4) . . . . ? C26 C28 C29 C34 156.6(3) . . . . ? C27 C28 C29 C30 163.9(3) . . . . ? C26 C28 C29 C30 -26.1(4) . . . . ? C34 C29 C30 C31 -4.6(4) . . . . ? C28 C29 C30 C31 178.1(3) . . . . ? C29 C30 C31 C32 2.3(5) . . . . ? C30 C31 C32 C33 0.6(5) . . . . ? C31 C32 C33 C34 -1.2(5) . . . . ? C32 C33 C34 C29 -1.1(5) . . . . ? C32 C33 C34 C35 177.8(3) . . . . ? C30 C29 C34 C33 4.0(4) . . . . ? C28 C29 C34 C33 -178.7(3) . . . . ? C30 C29 C34 C35 -174.9(3) . . . . ? C28 C29 C34 C35 2.5(4) . . . . ? C33 C34 C35 O1 7.7(4) . . . . ? C29 C34 C35 O1 -173.5(3) . . . . ? C33 C34 C35 C36 -171.4(3) . . . . ? C29 C34 C35 C36 7.5(4) . . . . ? N4 C27 C36 C37 -4.5(3) . . . . ? C28 C27 C36 C37 166.8(2) . . . . ? N4 C27 C36 C35 -175.2(2) . . . . ? C28 C27 C36 C35 -4.0(4) . . . . ? O1 C35 C36 C37 5.2(5) . . . . ? C34 C35 C36 C37 -175.7(3) . . . . ? O1 C35 C36 C27 173.9(3) . . . . ? C34 C35 C36 C27 -7.1(4) . . . . ? C27 C36 C37 N5 -173.6(3) . . . . ? C35 C36 C37 N5 -3.5(5) . . . . ? C27 C36 C37 C38 5.6(3) . . . . ? C35 C36 C37 C38 175.6(3) . . . . ? N5 C37 C38 C39 -13.8(5) . . . . ? C36 C37 C38 C39 167.1(3) . . . . ? N5 C37 C38 N4 174.1(3) . . . . ? C36 C37 C38 N4 -4.9(3) . . . . ? N4 C38 C39 C1 8.8(4) . . . . ? C37 C38 C39 C1 -162.1(3) . . . . ? N4 C38 C39 C40 -179.3(2) . . . . ? C37 C38 C39 C40 9.8(4) . . . . ? N1 C1 C39 C38 -5.5(4) . . . . ? C2 C1 C39 C38 163.5(3) . . . . ? N1 C1 C39 C40 -177.5(2) . . . . ? C2 C1 C39 C40 -8.6(4) . . . . ? C38 C39 C40 C45 -92.1(3) . . . . ? C1 C39 C40 C45 80.0(3) . . . . ? C38 C39 C40 C41 84.9(3) . . . . ? C1 C39 C40 C41 -103.0(3) . . . . ? C45 C40 C41 C42 1.4(4) . . . . ? C39 C40 C41 C42 -175.6(3) . . . . ? C40 C41 C42 C43 -0.4(5) . . . . ? C41 C42 C43 C44 -0.7(5) . . . . ? C42 C43 C44 C45 0.8(5) . . . . ? C43 C44 C45 C40 0.1(4) . . . . ? C41 C40 C45 C44 -1.2(4) . . . . ? C39 C40 C45 C44 175.8(3) . . . . ? C39 C1 N1 C4 167.9(3) . . . . ? C2 C1 N1 C4 -2.4(3) . . . . ? C39 C1 N1 Ni1 -13.1(4) . . . . ? C2 C1 N1 Ni1 176.68(19) . . . . ? C5 C4 N1 C1 176.8(3) . . . . ? C3 C4 N1 C1 0.6(3) . . . . ? C5 C4 N1 Ni1 -2.3(4) . . . . ? C3 C4 N1 Ni1 -178.49(18) . . . . ? C16 C15 N2 C12 -175.4(2) . . . . ? C14 C15 N2 C12 -0.5(3) . . . . ? C16 C15 N2 Ni1 0.6(4) . . . . ? C14 C15 N2 Ni1 175.45(18) . . . . ? C5 C12 N2 C15 -166.7(2) . . . . ? C13 C12 N2 C15 2.5(3) . . . . ? C5 C12 N2 Ni1 17.3(4) . . . . ? C13 C12 N2 Ni1 -173.51(18) . . . . ? C28 C26 N3 C23 175.6(2) . . . . ? C25 C26 N3 C23 3.1(3) . . . . ? C28 C26 N3 Ni1 4.3(4) . . . . ? C25 C26 N3 Ni1 -168.09(18) . . . . ? C16 C23 N3 C26 166.8(2) . . . . ? C24 C23 N3 C26 -4.9(3) . . . . ? C16 C23 N3 Ni1 -21.7(4) . . . . ? C24 C23 N3 Ni1 166.72(17) . . . . ? C28 C27 N4 C38 -169.2(3) . . . . ? C36 C27 N4 C38 1.3(3) . . . . ? C28 C27 N4 Ni1 14.1(4) . . . . ? C36 C27 N4 Ni1 -175.37(17) . . . . ? C39 C38 N4 C27 -170.1(2) . . . . ? C37 C38 N4 C27 2.2(3) . . . . ? C39 C38 N4 Ni1 6.5(4) . . . . ? C37 C38 N4 Ni1 178.75(17) . . . . ? C27 N4 Ni1 N1 158.6(2) . . . . ? C38 N4 Ni1 N1 -17.3(2) . . . . ? C27 N4 Ni1 N3 -23.6(2) . . . . ? C38 N4 Ni1 N3 160.4(2) . . . . ? C1 N1 Ni1 N4 20.3(2) . . . . ? C4 N1 Ni1 N4 -160.8(2) . . . . ? C1 N1 Ni1 N2 -161.2(2) . . . . ? C4 N1 Ni1 N2 17.7(2) . . . . ? C15 N2 Ni1 N1 160.0(2) . . . . ? C12 N2 Ni1 N1 -24.8(2) . . . . ? C15 N2 Ni1 N3 -17.7(2) . . . . ? C12 N2 Ni1 N3 157.4(2) . . . . ? C26 N3 Ni1 N4 15.5(2) . . . . ? C23 N3 Ni1 N4 -154.1(2) . . . . ? C26 N3 Ni1 N2 -163.0(2) . . . . ? C23 N3 Ni1 N2 27.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H2N O1 0.84(4) 2.24(4) 2.855(3) 130(4) 3_556 N5 H2N O1 0.84(4) 2.33(4) 2.894(4) 125(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.394 _refine_diff_density_min -1.192 _refine_diff_density_rms 0.077