# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_12084 _database_code_depnum_ccdc_archive 'CCDC 915452' #TrackingRef '12084.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H31 Cl N2 Ni O2' _chemical_formula_weight 593.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.7071(2) _cell_length_b 15.6490(3) _cell_length_c 15.7529(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.715(7) _cell_angle_gamma 90.00 _cell_volume 2844.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 32048 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 68.2 _exptl_crystal_description needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 2.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7422 _exptl_absorpt_correction_T_max 0.9017 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private Communication' _exptl_special_details ; 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn 944+ CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 22.2 _diffrn_reflns_number 61785 _diffrn_reflns_av_R_equivalents 0.1301 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 66.60 _reflns_number_total 5028 _reflns_number_gt 4001 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0809P)^2^+2.8513P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5028 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1592 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.12892(5) 0.30088(4) 0.15872(4) 0.0304(2) Uani 1 1 d . . . Cl1 Cl -0.00847(7) 0.27184(6) 0.23260(6) 0.0389(3) Uani 1 1 d . . . C1 C 0.0317(4) 0.3758(3) 0.0548(2) 0.0400(9) Uani 1 1 d . . . H1 H -0.0380 0.4056 0.0585 0.048 Uiso 1 1 calc R . . C2 C 0.0394(4) 0.2884(3) 0.0272(2) 0.0432(10) Uani 1 1 d . . . H2 H -0.0243 0.2512 0.0096 0.052 Uiso 1 1 calc R . . C3 C 0.1549(4) 0.2679(3) 0.0306(2) 0.0408(9) Uani 1 1 d . . . H3 H 0.1848 0.2156 0.0129 0.049 Uiso 1 1 calc R . . C4 C 0.2215(3) 0.3407(3) 0.0661(2) 0.0385(9) Uani 1 1 d . . . H4 H 0.3035 0.3430 0.0810 0.046 Uiso 1 1 calc R . . C5 C 0.1428(3) 0.4093(3) 0.0751(2) 0.0394(9) Uani 1 1 d . . . H5 H 0.1629 0.4664 0.0918 0.047 Uiso 1 1 calc R . . C6 C 0.2478(3) 0.2790(2) 0.2513(2) 0.0293(8) Uani 1 1 d . . . N1 N 0.3119(2) 0.33825(18) 0.30356(17) 0.0269(6) Uani 1 1 d . . . C21 C 0.2534(3) 0.1207(2) 0.2424(2) 0.0272(7) Uani 1 1 d . . . C22 C 0.1694(3) 0.0677(2) 0.2689(2) 0.0289(8) Uani 1 1 d . . . C27 C 0.1139(3) 0.0884(2) 0.3457(2) 0.0328(8) Uani 1 1 d . . . H27A H 0.1679 0.0750 0.3985 0.049 Uiso 1 1 calc R . . H27B H 0.0432 0.0544 0.3435 0.049 Uiso 1 1 calc R . . H27C H 0.0943 0.1493 0.3450 0.049 Uiso 1 1 calc R . . C23 C 0.1421(3) -0.0074(2) 0.2226(2) 0.0290(7) Uani 1 1 d . . . H23 H 0.0856 -0.0446 0.2392 0.035 Uiso 1 1 calc R . . C24 C 0.1949(3) -0.0300(2) 0.1527(2) 0.0316(8) Uani 1 1 d . . . C28 C 0.1594(4) -0.1093(2) 0.1012(3) 0.0416(9) Uani 1 1 d . . . H28A H 0.1110 -0.0935 0.0465 0.062 Uiso 1 1 calc R . . H28B H 0.1154 -0.1467 0.1338 0.062 Uiso 1 1 calc R . . H28C H 0.2287 -0.1394 0.0898 0.062 Uiso 1 1 calc R . . C25 C 0.2814(3) 0.0234(2) 0.1315(2) 0.0312(8) Uani 1 1 d . . . H25 H 0.3196 0.0079 0.0850 0.037 Uiso 1 1 calc R . . C26 C 0.3132(3) 0.0984(2) 0.1764(2) 0.0293(8) Uani 1 1 d . . . C29 C 0.4097(3) 0.1523(2) 0.1527(2) 0.0359(8) Uani 1 1 d . . . H29A H 0.4558 0.1180 0.1189 0.054 Uiso 1 1 calc R . . H29B H 0.4593 0.1725 0.2052 0.054 Uiso 1 1 calc R . . H29C H 0.3767 0.2015 0.1185 0.054 Uiso 1 1 calc R . . C7 C 0.3686(3) 0.2122(2) 0.3578(2) 0.0255(7) Uani 1 1 d . . . C8 C 0.4315(3) 0.1480(2) 0.4150(2) 0.0285(7) Uani 1 1 d . . . O1 O 0.4881(2) 0.41279(16) 0.44422(16) 0.0375(6) Uani 1 1 d . . . C9 C 0.5308(3) 0.1832(2) 0.4770(2) 0.0282(7) Uani 1 1 d . . . C10 C 0.6068(3) 0.1254(2) 0.5252(2) 0.0326(8) Uani 1 1 d . . . H10 H 0.5934 0.0656 0.5191 0.039 Uiso 1 1 calc R . . C11 C 0.7017(3) 0.1556(3) 0.5817(2) 0.0365(9) Uani 1 1 d . . . H11 H 0.7530 0.1163 0.6146 0.044 Uiso 1 1 calc R . . C12 C 0.7228(3) 0.2425(3) 0.5909(2) 0.0372(9) Uani 1 1 d . . . H12 H 0.7889 0.2624 0.6292 0.045 Uiso 1 1 calc R . . C13 C 0.6469(3) 0.3004(2) 0.5442(2) 0.0312(8) Uani 1 1 d . . . H13 H 0.6602 0.3600 0.5518 0.037 Uiso 1 1 calc R . . C14 C 0.5517(3) 0.2718(2) 0.4864(2) 0.0285(7) Uani 1 1 d . . . C15 C 0.4754(3) 0.3356(2) 0.4345(2) 0.0290(7) Uani 1 1 d . . . O2 O 0.4048(2) 0.07238(15) 0.41195(15) 0.0323(6) Uani 1 1 d . . . C16 C 0.3868(3) 0.2981(2) 0.3684(2) 0.0261(7) Uani 1 1 d . . . N2 N 0.2840(2) 0.20124(17) 0.28622(17) 0.0259(6) Uani 1 1 d . . . C31 C 0.3059(3) 0.4289(2) 0.2836(2) 0.0269(7) Uani 1 1 d . . . C32 C 0.2200(3) 0.4781(2) 0.3107(2) 0.0280(7) Uani 1 1 d . . . C37 C 0.1484(3) 0.4433(2) 0.3732(2) 0.0330(8) Uani 1 1 d . . . H37A H 0.1103 0.3904 0.3503 0.049 Uiso 1 1 calc R . . H37B H 0.0896 0.4854 0.3821 0.049 Uiso 1 1 calc R . . H37C H 0.1986 0.4314 0.4283 0.049 Uiso 1 1 calc R . . C33 C 0.2061(3) 0.5613(2) 0.2791(2) 0.0309(8) Uani 1 1 d . . . H33 H 0.1469 0.5962 0.2953 0.037 Uiso 1 1 calc R . . C34 C 0.2768(3) 0.5948(2) 0.2244(2) 0.0337(8) Uani 1 1 d . . . C38 C 0.2579(4) 0.6835(2) 0.1871(3) 0.0436(10) Uani 1 1 d . . . H38A H 0.3172 0.7221 0.2172 0.065 Uiso 1 1 calc R . . H38B H 0.1809 0.7039 0.1941 0.065 Uiso 1 1 calc R . . H38C H 0.2633 0.6820 0.1257 0.065 Uiso 1 1 calc R . . C35 C 0.3663(3) 0.5445(2) 0.2049(2) 0.0347(8) Uani 1 1 d . . . H35 H 0.4173 0.5679 0.1700 0.042 Uiso 1 1 calc R . . C36 C 0.3841(3) 0.4609(2) 0.2345(2) 0.0304(8) Uani 1 1 d . . . C39 C 0.4851(3) 0.4093(2) 0.2142(3) 0.0393(9) Uani 1 1 d . . . H39A H 0.5197 0.4387 0.1698 0.059 Uiso 1 1 calc R . . H39B H 0.4579 0.3527 0.1933 0.059 Uiso 1 1 calc R . . H39C H 0.5432 0.4032 0.2665 0.059 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 0.0284(4) 0.0339(4) 0.0268(3) 0.0012(2) -0.0012(3) -0.0005(2) Cl1 0.0274(5) 0.0516(6) 0.0361(5) 0.0025(4) 0.0008(4) -0.0039(4) C1 0.042(2) 0.046(2) 0.0296(19) 0.0048(17) -0.0007(16) 0.0072(18) C2 0.043(2) 0.056(3) 0.0261(19) -0.0026(17) -0.0075(17) -0.0068(19) C3 0.055(3) 0.042(2) 0.0264(18) 0.0001(16) 0.0090(17) 0.0081(19) C4 0.039(2) 0.046(2) 0.0294(19) 0.0051(17) 0.0007(16) 0.0024(18) C5 0.047(2) 0.037(2) 0.033(2) 0.0066(16) 0.0029(17) -0.0005(18) C6 0.0310(19) 0.0242(17) 0.0325(19) -0.0004(14) 0.0046(15) -0.0034(14) N1 0.0283(15) 0.0231(14) 0.0272(15) 0.0022(11) -0.0012(12) 0.0012(12) C21 0.0265(17) 0.0256(17) 0.0271(17) -0.0021(13) -0.0026(14) 0.0000(14) C22 0.0285(18) 0.0303(18) 0.0259(17) 0.0015(14) -0.0007(14) 0.0004(14) C27 0.0299(19) 0.039(2) 0.0299(19) -0.0044(15) 0.0056(15) -0.0025(16) C23 0.0287(18) 0.0285(18) 0.0278(17) 0.0014(14) -0.0014(14) -0.0046(14) C24 0.0323(19) 0.0294(18) 0.0317(18) -0.0027(15) 0.0016(15) 0.0029(15) C28 0.053(2) 0.032(2) 0.039(2) -0.0078(16) 0.0039(18) -0.0031(18) C25 0.0331(19) 0.0333(19) 0.0273(18) 0.0015(14) 0.0055(14) 0.0047(15) C26 0.0277(18) 0.0309(19) 0.0281(18) 0.0008(14) 0.0016(14) -0.0025(14) C29 0.0306(19) 0.037(2) 0.040(2) 0.0027(17) 0.0080(16) -0.0010(16) C7 0.0248(17) 0.0277(18) 0.0233(16) 0.0002(13) 0.0022(14) -0.0025(13) C8 0.0287(18) 0.0309(19) 0.0252(17) 0.0007(14) 0.0025(14) 0.0028(15) O1 0.0412(15) 0.0283(14) 0.0389(14) -0.0026(11) -0.0052(12) -0.0015(11) C9 0.0281(18) 0.0321(19) 0.0242(17) 0.0013(14) 0.0042(14) 0.0000(14) C10 0.0317(19) 0.035(2) 0.0312(19) 0.0061(15) 0.0046(15) 0.0052(15) C11 0.0285(19) 0.045(2) 0.034(2) 0.0046(17) -0.0011(15) 0.0056(16) C12 0.0292(19) 0.048(2) 0.033(2) 0.0013(17) -0.0002(16) -0.0011(17) C13 0.0290(19) 0.033(2) 0.0308(19) -0.0020(15) 0.0038(15) -0.0023(15) C14 0.0279(18) 0.0301(18) 0.0270(17) 0.0004(14) 0.0029(14) -0.0016(14) C15 0.0288(18) 0.0285(19) 0.0287(18) -0.0016(14) 0.0025(14) -0.0014(14) O2 0.0334(14) 0.0250(13) 0.0365(14) 0.0025(10) 0.0002(11) -0.0019(10) C16 0.0237(17) 0.0297(18) 0.0239(16) 0.0017(13) 0.0014(13) -0.0003(13) N2 0.0279(15) 0.0239(14) 0.0239(14) -0.0003(11) -0.0015(11) -0.0012(11) C31 0.0273(18) 0.0260(17) 0.0258(17) 0.0018(13) -0.0002(14) -0.0015(14) C32 0.0242(17) 0.0300(18) 0.0273(17) 0.0027(14) -0.0030(13) -0.0020(14) C37 0.0320(19) 0.036(2) 0.0301(18) -0.0006(15) 0.0036(15) 0.0005(16) C33 0.0309(19) 0.0298(19) 0.0307(18) 0.0000(15) 0.0014(15) 0.0037(15) C34 0.039(2) 0.0247(18) 0.037(2) 0.0020(15) 0.0035(16) 0.0023(15) C38 0.055(3) 0.033(2) 0.046(2) 0.0078(17) 0.017(2) 0.0053(18) C35 0.040(2) 0.0291(19) 0.036(2) 0.0019(15) 0.0095(16) 0.0029(16) C36 0.0318(19) 0.0261(18) 0.0336(19) -0.0023(14) 0.0062(15) -0.0007(14) C39 0.039(2) 0.034(2) 0.047(2) -0.0001(17) 0.0123(18) 0.0039(17) _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 C6 1.869(4) . ? Ni1 C4 2.055(4) . ? Ni1 C3 2.153(4) . ? Ni1 C2 2.167(4) . ? Ni1 C5 2.170(4) . ? Ni1 C1 2.173(4) . ? Ni1 Cl1 2.1864(11) . ? C1 C5 1.389(6) . ? C1 C2 1.442(6) . ? C1 H1 0.9500 . ? C2 C3 1.383(6) . ? C2 H2 0.9500 . ? C3 C4 1.438(6) . ? C3 H3 0.9500 . ? C4 C5 1.437(6) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 N2 1.373(4) . ? C6 N1 1.376(4) . ? N1 C16 1.380(4) . ? N1 C31 1.452(4) . ? C21 C26 1.393(5) . ? C21 C22 1.403(5) . ? C21 N2 1.452(4) . ? C22 C23 1.392(5) . ? C22 C27 1.502(5) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C23 C24 1.397(5) . ? C23 H23 0.9500 . ? C24 C25 1.396(5) . ? C24 C28 1.501(5) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C25 C26 1.389(5) . ? C25 H25 0.9500 . ? C26 C29 1.507(5) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C7 C16 1.366(5) . ? C7 N2 1.380(4) . ? C7 C8 1.463(5) . ? C8 O2 1.222(4) . ? C8 C9 1.492(5) . ? O1 C15 1.224(4) . ? C9 C10 1.399(5) . ? C9 C14 1.412(5) . ? C10 C11 1.385(5) . ? C10 H10 0.9500 . ? C11 C12 1.384(6) . ? C11 H11 0.9500 . ? C12 C13 1.391(5) . ? C12 H12 0.9500 . ? C13 C14 1.388(5) . ? C13 H13 0.9500 . ? C14 C15 1.488(5) . ? C15 C16 1.464(5) . ? C31 C36 1.388(5) . ? C31 C32 1.390(5) . ? C32 C33 1.394(5) . ? C32 C37 1.499(5) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C33 C34 1.393(5) . ? C33 H33 0.9500 . ? C34 C35 1.386(5) . ? C34 C38 1.510(5) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C35 C36 1.393(5) . ? C35 H35 0.9500 . ? C36 C39 1.509(5) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? 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 C6 Ni1 C4 101.36(15) . . ? C6 Ni1 C3 118.84(16) . . ? C4 Ni1 C3 39.88(16) . . ? C6 Ni1 C2 154.89(16) . . ? C4 Ni1 C2 64.95(16) . . ? C3 Ni1 C2 37.33(16) . . ? C6 Ni1 C5 119.63(15) . . ? C4 Ni1 C5 39.65(15) . . ? C3 Ni1 C5 65.29(15) . . ? C2 Ni1 C5 64.14(16) . . ? C6 Ni1 C1 155.91(16) . . ? C4 Ni1 C1 64.76(15) . . ? C3 Ni1 C1 64.05(15) . . ? C2 Ni1 C1 38.81(15) . . ? C5 Ni1 C1 37.30(15) . . ? C6 Ni1 Cl1 93.70(11) . . ? C4 Ni1 Cl1 164.62(11) . . ? C3 Ni1 Cl1 133.00(12) . . ? C2 Ni1 Cl1 102.10(12) . . ? C5 Ni1 Cl1 128.50(11) . . ? C1 Ni1 Cl1 100.03(11) . . ? C5 C1 C2 108.9(4) . . ? C5 C1 Ni1 71.2(2) . . ? C2 C1 Ni1 70.4(2) . . ? C5 C1 H1 125.6 . . ? C2 C1 H1 125.6 . . ? Ni1 C1 H1 124.4 . . ? C3 C2 C1 108.6(4) . . ? C3 C2 Ni1 70.8(2) . . ? C1 C2 Ni1 70.8(2) . . ? C3 C2 H2 125.7 . . ? C1 C2 H2 125.7 . . ? Ni1 C2 H2 124.3 . . ? C2 C3 C4 107.1(4) . . ? C2 C3 Ni1 71.9(2) . . ? C4 C3 Ni1 66.4(2) . . ? C2 C3 H3 126.5 . . ? C4 C3 H3 126.5 . . ? Ni1 C3 H3 126.8 . . ? C5 C4 C3 108.4(3) . . ? C5 C4 Ni1 74.5(2) . . ? C3 C4 Ni1 73.7(2) . . ? C5 C4 H4 125.8 . . ? C3 C4 H4 125.8 . . ? Ni1 C4 H4 117.9 . . ? C1 C5 C4 106.7(4) . . ? C1 C5 Ni1 71.5(2) . . ? C4 C5 Ni1 65.9(2) . . ? C1 C5 H5 126.7 . . ? C4 C5 H5 126.7 . . ? Ni1 C5 H5 127.5 . . ? N2 C6 N1 104.9(3) . . ? N2 C6 Ni1 127.9(2) . . ? N1 C6 Ni1 127.1(3) . . ? C6 N1 C16 110.5(3) . . ? C6 N1 C31 121.8(3) . . ? C16 N1 C31 127.4(3) . . ? C26 C21 C22 122.6(3) . . ? C26 C21 N2 117.3(3) . . ? C22 C21 N2 120.1(3) . . ? C23 C22 C21 117.0(3) . . ? C23 C22 C27 120.7(3) . . ? C21 C22 C27 122.2(3) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 C23 C24 122.3(3) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? C25 C24 C23 118.2(3) . . ? C25 C24 C28 120.7(3) . . ? C23 C24 C28 121.0(3) . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C25 C24 121.8(3) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 C26 C21 117.9(3) . . ? C25 C26 C29 119.6(3) . . ? C21 C26 C29 122.5(3) . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C16 C7 N2 107.3(3) . . ? C16 C7 C8 123.3(3) . . ? N2 C7 C8 129.5(3) . . ? O2 C8 C7 122.8(3) . . ? O2 C8 C9 123.3(3) . . ? C7 C8 C9 113.9(3) . . ? C10 C9 C14 119.7(3) . . ? C10 C9 C8 118.1(3) . . ? C14 C9 C8 122.2(3) . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C9 119.4(3) . . ? C13 C14 C15 118.9(3) . . ? C9 C14 C15 121.6(3) . . ? O1 C15 C16 122.8(3) . . ? O1 C15 C14 123.0(3) . . ? C16 C15 C14 114.2(3) . . ? C7 C16 N1 106.9(3) . . ? C7 C16 C15 124.0(3) . . ? N1 C16 C15 129.0(3) . . ? C6 N2 C7 110.4(3) . . ? C6 N2 C21 122.9(3) . . ? C7 N2 C21 125.5(3) . . ? C36 C31 C32 123.4(3) . . ? C36 C31 N1 117.4(3) . . ? C32 C31 N1 119.1(3) . . ? C31 C32 C33 117.0(3) . . ? C31 C32 C37 121.0(3) . . ? C33 C32 C37 122.0(3) . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C33 C32 121.8(3) . . ? C34 C33 H33 119.1 . . ? C32 C33 H33 119.1 . . ? C35 C34 C33 118.3(3) . . ? C35 C34 C38 120.1(3) . . ? C33 C34 C38 121.6(3) . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C34 C35 C36 122.3(4) . . ? C34 C35 H35 118.8 . . ? C36 C35 H35 118.8 . . ? C31 C36 C35 116.7(3) . . ? C31 C36 C39 122.6(3) . . ? C35 C36 C39 120.7(3) . . ? C36 C39 H39A 109.5 . . ? C36 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C36 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 66.60 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.474 _refine_diff_density_min -0.807 _refine_diff_density_rms 0.086