# 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_contact_author_name 'P. Krishnamoorthy' _publ_contact_author_email krishnachemist@gmail.com loop_ _publ_author_name K.Paramasivam S.Palanisamy R.Butorac A.Cowley D.Nallasamy data_shelxl _database_code_depnum_ccdc_archive 'CCDC 796261' #TrackingRef 'niohnfh cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H25 N2 Ni O3 P' _chemical_formula_sum 'C34 H25 N2 Ni O3 P' _chemical_formula_weight 599.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.379(2) _cell_length_b 14.886(3) _cell_length_c 19.785(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.60(2) _cell_angle_gamma 90.00 _cell_volume 2733.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6016 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9163 _exptl_absorpt_correction_T_max 0.9607 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius Kappa CCD' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10219 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.1063 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6193 _reflns_number_gt 3479 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (2008). SHELXL-97. Acat Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0101P)^2^+2.4692P] 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 6193 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1854 _refine_ls_R_factor_gt 0.0880 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.503 _refine_ls_restrained_S_all 1.503 _refine_ls_shift/su_max 0.003 _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 0.97680(6) 0.80537(4) 0.56252(3) 0.03219(17) Uani 1 1 d . . . P1 P 0.79536(12) 0.89965(8) 0.53895(6) 0.0319(3) Uani 1 1 d . . . O1 O 0.8801(3) 0.75496(19) 0.46975(15) 0.0338(7) Uani 1 1 d . . . O2 O 1.0752(3) 0.85249(19) 0.65827(15) 0.0341(7) Uani 1 1 d . . . O3 O 1.4279(3) 0.8127(2) 0.80811(16) 0.0410(8) Uani 1 1 d . . . N1 N 1.1299(4) 0.7263(2) 0.59385(19) 0.0317(9) Uani 1 1 d . . . N2 N 1.2377(4) 0.7403(2) 0.66851(19) 0.0324(9) Uani 1 1 d . . . C1 C 0.9195(4) 0.6851(3) 0.4426(2) 0.0313(10) Uani 1 1 d . . . C2 C 0.8222(5) 0.6609(3) 0.3667(2) 0.0368(11) Uani 1 1 d . . . H2 H 0.7387 0.6964 0.3394 0.044 Uiso 1 1 calc R . . C3 C 0.8468(5) 0.5886(3) 0.3331(2) 0.0368(11) Uani 1 1 d . . . H3 H 0.7794 0.5737 0.2829 0.044 Uiso 1 1 calc R . . C4 C 0.9711(5) 0.5341(3) 0.3710(2) 0.0325(11) Uani 1 1 d . . . C5 C 0.9920(5) 0.4577(3) 0.3351(3) 0.0397(12) Uani 1 1 d . . . H5 H 0.9218 0.4427 0.2855 0.048 Uiso 1 1 calc R . . C6 C 1.1115(5) 0.4050(3) 0.3702(3) 0.0418(12) Uani 1 1 d . . . H6 H 1.1253 0.3543 0.3450 0.050 Uiso 1 1 calc R . . C7 C 1.2131(5) 0.4266(3) 0.4436(3) 0.0383(12) Uani 1 1 d . . . H7 H 1.2956 0.3896 0.4687 0.046 Uiso 1 1 calc R . . C8 C 1.1954(5) 0.5008(3) 0.4802(2) 0.0355(11) Uani 1 1 d . . . H8 H 1.2672 0.5148 0.5296 0.043 Uiso 1 1 calc R . . C9 C 1.0722(5) 0.5567(3) 0.4457(2) 0.0319(10) Uani 1 1 d . . . C10 C 1.0452(4) 0.6342(3) 0.4823(2) 0.0293(10) Uani 1 1 d . . . C11 C 1.1442(4) 0.6572(3) 0.5579(2) 0.0317(10) Uani 1 1 d . . . H11 H 1.2256 0.6195 0.5835 0.038 Uiso 1 1 calc R . . C12 C 1.1969(4) 0.8091(3) 0.6952(2) 0.0308(10) Uani 1 1 d . . . C13 C 1.2889(5) 0.8451(3) 0.7699(2) 0.0358(11) Uani 1 1 d . . . C14 C 1.2670(5) 0.9104(3) 0.8101(3) 0.0493(13) Uani 1 1 d . . . H14 H 1.1810 0.9439 0.7962 0.059 Uiso 1 1 calc R . . C15 C 1.3984(5) 0.9198(4) 0.8779(3) 0.0534(14) Uani 1 1 d . . . H15 H 1.4160 0.9603 0.9182 0.064 Uiso 1 1 calc R . . C16 C 1.4912(5) 0.8613(3) 0.8741(3) 0.0476(13) Uani 1 1 d . . . H16 H 1.5878 0.8539 0.9116 0.057 Uiso 1 1 calc R . . C17 C 0.6859(4) 0.9365(3) 0.4415(2) 0.0316(10) Uani 1 1 d . . . C18 C 0.6205(4) 0.8722(3) 0.3846(2) 0.0358(11) Uani 1 1 d . . . H18 H 0.6317 0.8101 0.3970 0.043 Uiso 1 1 calc R . . C19 C 0.5391(4) 0.8988(3) 0.3100(2) 0.0389(12) Uani 1 1 d . . . H19 H 0.4936 0.8549 0.2718 0.047 Uiso 1 1 calc R . . C20 C 0.5241(5) 0.9886(3) 0.2912(3) 0.0425(12) Uani 1 1 d . . . H20 H 0.4698 1.0067 0.2401 0.051 Uiso 1 1 calc R . . C21 C 0.5886(5) 1.0521(3) 0.3470(3) 0.0432(12) Uani 1 1 d . . . H21 H 0.5778 1.1140 0.3341 0.052 Uiso 1 1 calc R . . C22 C 0.6692(4) 1.0268(3) 0.4222(3) 0.0348(11) Uani 1 1 d . . . H22 H 0.7127 1.0713 0.4601 0.042 Uiso 1 1 calc R . . C23 C 0.6772(4) 0.8393(3) 0.5691(2) 0.0309(10) Uani 1 1 d . . . C24 C 0.7385(5) 0.8096(3) 0.6445(2) 0.0346(11) Uani 1 1 d . . . H24 H 0.8334 0.8277 0.6786 0.041 Uiso 1 1 calc R . . C25 C 0.6616(5) 0.7544(3) 0.6695(3) 0.0406(12) Uani 1 1 d . . . H25 H 0.7036 0.7348 0.7206 0.049 Uiso 1 1 calc R . . C26 C 0.5238(5) 0.7278(3) 0.6203(3) 0.0414(12) Uani 1 1 d . . . H26 H 0.4712 0.6895 0.6374 0.050 Uiso 1 1 calc R . . C27 C 0.4621(5) 0.7569(3) 0.5459(3) 0.0442(12) Uani 1 1 d . . . H27 H 0.3670 0.7386 0.5122 0.053 Uiso 1 1 calc R . . C28 C 0.5377(4) 0.8122(3) 0.5206(2) 0.0364(11) Uani 1 1 d . . . H28 H 0.4942 0.8320 0.4696 0.044 Uiso 1 1 calc R . . C29 C 0.8439(4) 1.0039(3) 0.5925(2) 0.0318(11) Uani 1 1 d . . . C30 C 0.9745(5) 1.0438(3) 0.6060(2) 0.0368(11) Uani 1 1 d . . . H30 H 1.0400 1.0136 0.5924 0.044 Uiso 1 1 calc R . . C31 C 1.0087(5) 1.1281(3) 0.6395(3) 0.0415(12) Uani 1 1 d . . . H31 H 1.0973 1.1555 0.6480 0.050 Uiso 1 1 calc R . . C32 C 0.9153(5) 1.1728(3) 0.6608(3) 0.0435(13) Uani 1 1 d . . . H32 H 0.9389 1.2306 0.6835 0.052 Uiso 1 1 calc R . . C33 C 0.7856(5) 1.1313(3) 0.6483(2) 0.0414(12) Uani 1 1 d . . . H33 H 0.7208 1.1608 0.6629 0.050 Uiso 1 1 calc R . . C34 C 0.7510(5) 1.0474(3) 0.6147(2) 0.0352(11) Uani 1 1 d . . . H34 H 0.6630 1.0195 0.6069 0.042 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 0.0309(3) 0.0338(3) 0.0300(3) 0.0013(3) 0.0120(3) 0.0028(3) P1 0.0311(6) 0.0323(7) 0.0288(7) 0.0014(5) 0.0105(5) 0.0007(5) O1 0.0311(16) 0.0392(18) 0.0253(17) -0.0002(14) 0.0075(14) 0.0039(14) O2 0.0300(16) 0.0378(18) 0.0292(17) 0.0011(14) 0.0087(14) 0.0058(15) O3 0.0360(18) 0.046(2) 0.0301(18) -0.0068(16) 0.0053(15) 0.0079(16) N1 0.030(2) 0.033(2) 0.029(2) 0.0011(18) 0.0103(18) -0.0004(17) N2 0.032(2) 0.035(2) 0.025(2) 0.0013(17) 0.0081(17) -0.0003(18) C1 0.030(2) 0.033(3) 0.030(2) 0.002(2) 0.013(2) -0.001(2) C2 0.035(3) 0.039(3) 0.030(3) 0.002(2) 0.009(2) 0.000(2) C3 0.037(3) 0.040(3) 0.029(3) 0.001(2) 0.012(2) -0.006(2) C4 0.037(3) 0.031(3) 0.029(3) 0.002(2) 0.015(2) -0.001(2) C5 0.050(3) 0.036(3) 0.036(3) -0.005(2) 0.021(2) -0.008(2) C6 0.054(3) 0.035(3) 0.043(3) -0.002(2) 0.027(3) -0.001(3) C7 0.045(3) 0.030(3) 0.043(3) 0.011(2) 0.023(3) 0.006(2) C8 0.037(3) 0.032(3) 0.032(3) 0.001(2) 0.011(2) 0.003(2) C9 0.036(3) 0.032(2) 0.029(3) 0.002(2) 0.016(2) -0.003(2) C10 0.033(3) 0.029(2) 0.026(2) 0.004(2) 0.014(2) -0.005(2) C11 0.031(2) 0.033(3) 0.033(3) 0.008(2) 0.016(2) 0.004(2) C12 0.032(2) 0.031(2) 0.030(3) 0.008(2) 0.014(2) 0.002(2) C13 0.030(3) 0.043(3) 0.032(3) 0.002(2) 0.011(2) 0.004(2) C14 0.038(3) 0.058(3) 0.051(3) -0.008(3) 0.018(3) 0.010(3) C15 0.046(3) 0.065(4) 0.044(3) -0.021(3) 0.015(3) -0.002(3) C16 0.044(3) 0.058(3) 0.031(3) -0.009(3) 0.008(2) 0.003(3) C17 0.027(2) 0.037(3) 0.033(3) 0.004(2) 0.016(2) 0.002(2) C18 0.034(3) 0.039(3) 0.034(3) 0.001(2) 0.015(2) 0.003(2) C19 0.032(3) 0.049(3) 0.035(3) -0.002(2) 0.015(2) 0.002(2) C20 0.043(3) 0.052(3) 0.031(3) 0.010(3) 0.016(2) 0.008(3) C21 0.049(3) 0.042(3) 0.043(3) 0.010(3) 0.024(3) 0.006(3) C22 0.033(3) 0.038(3) 0.036(3) 0.002(2) 0.018(2) 0.002(2) C23 0.034(3) 0.031(2) 0.026(3) 0.000(2) 0.012(2) 0.003(2) C24 0.031(2) 0.042(3) 0.029(3) -0.002(2) 0.012(2) 0.005(2) C25 0.045(3) 0.046(3) 0.031(3) 0.004(2) 0.016(2) 0.001(2) C26 0.049(3) 0.042(3) 0.045(3) -0.004(2) 0.032(3) -0.010(2) C27 0.042(3) 0.050(3) 0.039(3) -0.001(2) 0.016(3) -0.010(3) C28 0.036(3) 0.040(3) 0.026(3) 0.007(2) 0.007(2) 0.003(2) C29 0.035(3) 0.028(2) 0.029(3) 0.004(2) 0.012(2) 0.000(2) C30 0.041(3) 0.035(3) 0.034(3) -0.002(2) 0.016(2) -0.003(2) C31 0.039(3) 0.038(3) 0.043(3) 0.002(2) 0.015(2) -0.007(2) C32 0.048(3) 0.036(3) 0.036(3) 0.007(2) 0.010(3) -0.001(2) C33 0.044(3) 0.042(3) 0.029(3) -0.006(2) 0.009(2) 0.012(3) C34 0.033(3) 0.040(3) 0.029(3) 0.000(2) 0.010(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O1 1.814(3) . ? Ni1 O2 1.842(3) . ? Ni1 N1 1.847(3) . ? Ni1 P1 2.2241(13) . ? P1 C29 1.818(4) . ? P1 C23 1.822(4) . ? P1 C17 1.829(4) . ? O1 C1 1.316(5) . ? O2 C12 1.311(5) . ? O3 C16 1.375(5) . ? O3 C13 1.382(5) . ? N1 C11 1.296(5) . ? N1 N2 1.413(4) . ? N2 C12 1.307(5) . ? C1 C10 1.405(6) . ? C1 C2 1.432(6) . ? C2 C3 1.348(6) . ? C2 H2 0.9500 . ? C3 C4 1.421(6) . ? C3 H3 0.9500 . ? C4 C5 1.408(6) . ? C4 C9 1.417(6) . ? C5 C6 1.366(6) . ? C5 H5 0.9500 . ? C6 C7 1.398(6) . ? C6 H6 0.9500 . ? C7 C8 1.377(6) . ? C7 H7 0.9500 . ? C8 C9 1.419(6) . ? C8 H8 0.9500 . ? C9 C10 1.454(6) . ? C10 C11 1.427(6) . ? C11 H11 0.9500 . ? C12 C13 1.456(6) . ? C13 C14 1.337(6) . ? C14 C15 1.429(6) . ? C14 H14 0.9500 . ? C15 C16 1.325(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.387(6) . ? C17 C18 1.400(6) . ? C18 C19 1.390(6) . ? C18 H18 0.9500 . ? C19 C20 1.378(6) . ? C19 H19 0.9500 . ? C20 C21 1.378(6) . ? C20 H20 0.9500 . ? C21 C22 1.392(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C28 1.391(6) . ? C23 C24 1.406(6) . ? C24 C25 1.381(6) . ? C24 H24 0.9500 . ? C25 C26 1.380(6) . ? C25 H25 0.9500 . ? C26 C27 1.384(6) . ? C26 H26 0.9500 . ? C27 C28 1.377(6) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.386(6) . ? C29 C30 1.393(6) . ? C30 C31 1.388(6) . ? C30 H30 0.9500 . ? C31 C32 1.389(6) . ? C31 H31 0.9500 . ? C32 C33 1.399(6) . ? C32 H32 0.9500 . ? C33 C34 1.384(6) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ni1 O2 177.90(13) . . ? O1 Ni1 N1 94.54(14) . . ? O2 Ni1 N1 84.25(14) . . ? O1 Ni1 P1 90.92(10) . . ? O2 Ni1 P1 90.16(10) . . ? N1 Ni1 P1 173.08(12) . . ? C29 P1 C23 106.3(2) . . ? C29 P1 C17 103.8(2) . . ? C23 P1 C17 107.53(19) . . ? C29 P1 Ni1 115.38(14) . . ? C23 P1 Ni1 104.51(14) . . ? C17 P1 Ni1 118.56(15) . . ? C1 O1 Ni1 127.4(3) . . ? C12 O2 Ni1 109.7(3) . . ? C16 O3 C13 105.9(3) . . ? C11 N1 N2 117.3(3) . . ? C11 N1 Ni1 127.9(3) . . ? N2 N1 Ni1 114.6(3) . . ? C12 N2 N1 106.8(3) . . ? O1 C1 C10 125.3(4) . . ? O1 C1 C2 115.1(4) . . ? C10 C1 C2 119.5(4) . . ? C3 C2 C1 121.2(4) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C2 C3 C4 121.6(4) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C9 120.6(4) . . ? C5 C4 C3 120.2(4) . . ? C9 C4 C3 119.2(4) . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.2(4) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 120.9(4) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 121.4(4) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C4 C9 C8 116.7(4) . . ? C4 C9 C10 119.3(4) . . ? C8 C9 C10 124.0(4) . . ? C1 C10 C11 120.6(4) . . ? C1 C10 C9 119.2(4) . . ? C11 C10 C9 120.3(4) . . ? N1 C11 C10 124.1(4) . . ? N1 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? N2 C12 O2 124.5(4) . . ? N2 C12 C13 121.0(4) . . ? O2 C12 C13 114.5(4) . . ? C14 C13 O3 110.0(4) . . ? C14 C13 C12 131.5(4) . . ? O3 C13 C12 118.4(4) . . ? C13 C14 C15 106.6(4) . . ? C13 C14 H14 126.7 . . ? C15 C14 H14 126.7 . . ? C16 C15 C14 107.1(4) . . ? C16 C15 H15 126.4 . . ? C14 C15 H15 126.4 . . ? C15 C16 O3 110.4(4) . . ? C15 C16 H16 124.8 . . ? O3 C16 H16 124.8 . . ? C22 C17 C18 119.0(4) . . ? C22 C17 P1 121.5(3) . . ? C18 C17 P1 119.4(3) . . ? C19 C18 C17 120.3(4) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.3(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 119.5(4) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 121.0(5) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C17 C22 C21 119.8(4) . . ? C17 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C28 C23 C24 118.5(4) . . ? C28 C23 P1 124.3(3) . . ? C24 C23 P1 116.8(3) . . ? C25 C24 C23 120.5(4) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 120.1(4) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.0(4) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C28 C27 C26 120.3(4) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C23 120.6(4) . . ? C27 C28 H28 119.7 . . ? C23 C28 H28 119.7 . . ? C34 C29 C30 119.7(4) . . ? C34 C29 P1 122.2(3) . . ? C30 C29 P1 117.9(3) . . ? C31 C30 C29 119.8(4) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C32 120.9(4) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? C31 C32 C33 118.8(4) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? C34 C33 C32 120.4(4) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C29 120.4(4) . . ? C33 C34 H34 119.8 . . ? C29 C34 H34 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Ni1 P1 C29 -155.12(18) . . . . ? O2 Ni1 P1 C29 26.68(18) . . . . ? O1 Ni1 P1 C23 88.49(17) . . . . ? O2 Ni1 P1 C23 -89.71(17) . . . . ? O1 Ni1 P1 C17 -31.18(19) . . . . ? O2 Ni1 P1 C17 150.61(19) . . . . ? N1 Ni1 O1 C1 0.6(3) . . . . ? P1 Ni1 O1 C1 -175.2(3) . . . . ? N1 Ni1 O2 C12 1.7(3) . . . . ? P1 Ni1 O2 C12 177.6(3) . . . . ? O1 Ni1 N1 C11 -4.3(4) . . . . ? O2 Ni1 N1 C11 174.0(4) . . . . ? O1 Ni1 N1 N2 -178.9(3) . . . . ? O2 Ni1 N1 N2 -0.6(3) . . . . ? C11 N1 N2 C12 -175.8(4) . . . . ? Ni1 N1 N2 C12 -0.5(4) . . . . ? Ni1 O1 C1 C10 1.7(6) . . . . ? Ni1 O1 C1 C2 -179.1(3) . . . . ? O1 C1 C2 C3 -177.4(4) . . . . ? C10 C1 C2 C3 1.9(6) . . . . ? C1 C2 C3 C4 -1.0(7) . . . . ? C2 C3 C4 C5 178.5(4) . . . . ? C2 C3 C4 C9 -0.6(6) . . . . ? C9 C4 C5 C6 -1.7(7) . . . . ? C3 C4 C5 C6 179.3(4) . . . . ? C4 C5 C6 C7 1.1(7) . . . . ? C5 C6 C7 C8 -1.1(7) . . . . ? C6 C7 C8 C9 1.5(7) . . . . ? C5 C4 C9 C8 2.0(6) . . . . ? C3 C4 C9 C8 -179.0(4) . . . . ? C5 C4 C9 C10 -177.9(4) . . . . ? C3 C4 C9 C10 1.2(6) . . . . ? C7 C8 C9 C4 -2.0(6) . . . . ? C7 C8 C9 C10 177.9(4) . . . . ? O1 C1 C10 C11 -1.1(6) . . . . ? C2 C1 C10 C11 179.7(4) . . . . ? O1 C1 C10 C9 178.0(4) . . . . ? C2 C1 C10 C9 -1.2(6) . . . . ? C4 C9 C10 C1 -0.3(6) . . . . ? C8 C9 C10 C1 179.8(4) . . . . ? C4 C9 C10 C11 178.8(4) . . . . ? C8 C9 C10 C11 -1.0(6) . . . . ? N2 N1 C11 C10 -179.7(4) . . . . ? Ni1 N1 C11 C10 5.8(6) . . . . ? C1 C10 C11 N1 -2.7(6) . . . . ? C9 C10 C11 N1 178.2(4) . . . . ? N1 N2 C12 O2 2.2(5) . . . . ? N1 N2 C12 C13 -176.1(4) . . . . ? Ni1 O2 C12 N2 -2.8(5) . . . . ? Ni1 O2 C12 C13 175.6(3) . . . . ? C16 O3 C13 C14 0.0(5) . . . . ? C16 O3 C13 C12 176.9(4) . . . . ? N2 C12 C13 C14 -175.7(5) . . . . ? O2 C12 C13 C14 5.9(7) . . . . ? N2 C12 C13 O3 8.3(6) . . . . ? O2 C12 C13 O3 -170.2(4) . . . . ? O3 C13 C14 C15 -0.5(6) . . . . ? C12 C13 C14 C15 -176.9(5) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C14 C15 C16 O3 -1.0(6) . . . . ? C13 O3 C16 C15 0.6(5) . . . . ? C29 P1 C17 C22 6.4(4) . . . . ? C23 P1 C17 C22 118.8(4) . . . . ? Ni1 P1 C17 C22 -123.1(3) . . . . ? C29 P1 C17 C18 -175.4(3) . . . . ? C23 P1 C17 C18 -63.0(4) . . . . ? Ni1 P1 C17 C18 55.1(4) . . . . ? C22 C17 C18 C19 -0.5(6) . . . . ? P1 C17 C18 C19 -178.8(3) . . . . ? C17 C18 C19 C20 1.1(6) . . . . ? C18 C19 C20 C21 -1.0(7) . . . . ? C19 C20 C21 C22 0.3(7) . . . . ? C18 C17 C22 C21 -0.2(6) . . . . ? P1 C17 C22 C21 178.1(3) . . . . ? C20 C21 C22 C17 0.3(7) . . . . ? C29 P1 C23 C28 122.1(4) . . . . ? C17 P1 C23 C28 11.5(4) . . . . ? Ni1 P1 C23 C28 -115.4(4) . . . . ? C29 P1 C23 C24 -65.6(4) . . . . ? C17 P1 C23 C24 -176.2(3) . . . . ? Ni1 P1 C23 C24 56.9(3) . . . . ? C28 C23 C24 C25 0.4(6) . . . . ? P1 C23 C24 C25 -172.4(3) . . . . ? C23 C24 C25 C26 0.1(7) . . . . ? C24 C25 C26 C27 -0.4(7) . . . . ? C25 C26 C27 C28 0.2(7) . . . . ? C26 C27 C28 C23 0.3(7) . . . . ? C24 C23 C28 C27 -0.6(6) . . . . ? P1 C23 C28 C27 171.6(4) . . . . ? C23 P1 C29 C34 -32.0(4) . . . . ? C17 P1 C29 C34 81.2(4) . . . . ? Ni1 P1 C29 C34 -147.4(3) . . . . ? C23 P1 C29 C30 153.1(3) . . . . ? C17 P1 C29 C30 -93.6(4) . . . . ? Ni1 P1 C29 C30 37.7(4) . . . . ? C34 C29 C30 C31 -1.9(6) . . . . ? P1 C29 C30 C31 173.1(3) . . . . ? C29 C30 C31 C32 0.9(7) . . . . ? C30 C31 C32 C33 0.3(7) . . . . ? C31 C32 C33 C34 -0.5(6) . . . . ? C32 C33 C34 C29 -0.6(6) . . . . ? C30 C29 C34 C33 1.8(6) . . . . ? P1 C29 C34 C33 -173.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.678 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.112 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 851587' #TrackingRef 'NiOHNTH.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H25 N2 Ni1 O2 P S' _chemical_formula_sum 'C34 H25 N2 Ni O2 P S' _chemical_formula_weight 615.30 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.499(3) _cell_length_b 10.844(5) _cell_length_c 21.084(4) _cell_angle_alpha 90.00 _cell_angle_beta 125.601(15) _cell_angle_gamma 90.00 _cell_volume 2881.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11077 _cell_measurement_theta_min 1.6180 _cell_measurement_theta_max 31.0697 _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.836 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7996 _exptl_absorpt_correction_T_max 0.8919 _exptl_absorpt_process_details ; Abscor. T. Higashi. (2001). Rigaku Corp. Tokyo, Japan ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC-12 with Saturn 724+ CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 52023 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6598 _reflns_number_gt 5963 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Farrugia, L. J. (1999) J. Appl. Cryst., 32, 837-838. An Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-ray Diffraction Data. Sheldrick, G. M. (2008). SHELXL-97. Acat Cryst., A64, 112-122. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_acknowledgements ; The data were collected using instrumentation purchased with funds provided by the National Science Foundation Grant No. 0741973. ; _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0352P)^2^+1.7781P] 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 6598 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.05217(11) -0.49010(14) -0.34435(9) 0.0157(3) Uani 1 1 d . . . C2 C 0.02645(12) -0.55678(15) -0.29883(9) 0.0184(3) Uani 1 1 d . . . H2 H 0.0640 -0.6303 -0.2730 0.022 Uiso 1 1 calc R . . C3 C -0.05090(12) -0.51664(15) -0.29198(9) 0.0200(3) Uani 1 1 d . . . H3 H -0.0666 -0.5631 -0.2617 0.024 Uiso 1 1 calc R . . C4 C -0.10894(12) -0.40625(15) -0.32926(9) 0.0193(3) Uani 1 1 d . . . C5 C -0.18774(13) -0.36388(17) -0.32024(10) 0.0238(3) Uani 1 1 d . . . H5 H -0.2022 -0.4100 -0.2891 0.029 Uiso 1 1 calc R . . C6 C -0.24359(13) -0.25750(17) -0.35568(10) 0.0265(4) Uani 1 1 d . . . H6 H -0.2968 -0.2307 -0.3497 0.032 Uiso 1 1 calc R . . C7 C -0.22114(13) -0.18888(17) -0.40089(10) 0.0252(4) Uani 1 1 d . . . H7 H -0.2592 -0.1149 -0.4252 0.030 Uiso 1 1 calc R . . C8 C -0.14444(12) -0.22745(15) -0.41043(9) 0.0210(3) Uani 1 1 d . . . H8 H -0.1300 -0.1789 -0.4408 0.025 Uiso 1 1 calc R . . C9 C -0.08672(11) -0.33820(15) -0.37583(8) 0.0176(3) Uani 1 1 d . . . C10 C -0.00664(11) -0.38382(14) -0.38542(8) 0.0157(3) Uani 1 1 d . . . C11 C 0.00987(11) -0.32246(14) -0.43748(8) 0.0164(3) Uani 1 1 d . . . H11 H -0.0330 -0.2528 -0.4653 0.020 Uiso 1 1 calc R . . C12 C 0.16400(11) -0.33281(13) -0.50305(8) 0.0149(3) Uani 1 1 d . . . C13 C 0.18761(12) -0.27694(14) -0.55451(8) 0.0158(3) Uani 1 1 d . . . C14 C 0.26039(12) -0.31860(15) -0.56779(8) 0.0172(3) Uani 1 1 d . . . H14 H 0.3046 -0.3887 -0.5433 0.021 Uiso 1 1 calc R . . C15 C 0.26022(13) -0.24247(16) -0.62310(9) 0.0231(3) Uani 1 1 d . . . H15 H 0.3052 -0.2561 -0.6394 0.028 Uiso 1 1 calc R . . C16 C 0.18909(14) -0.14840(16) -0.65011(10) 0.0256(4) Uani 1 1 d . . . H16 H 0.1791 -0.0892 -0.6871 0.031 Uiso 1 1 calc R . . C17 C 0.38434(11) -0.61571(15) -0.23408(8) 0.0163(3) Uani 1 1 d . . . C18 C 0.38791(13) -0.50920(17) -0.19613(10) 0.0249(4) Uani 1 1 d . . . H18 H 0.3443 -0.4408 -0.2254 0.030 Uiso 1 1 calc R . . C19 C 0.45573(15) -0.5028(2) -0.11491(11) 0.0345(4) Uani 1 1 d . . . H19 H 0.4588 -0.4297 -0.0889 0.041 Uiso 1 1 calc R . . C20 C 0.51870(14) -0.6030(2) -0.07213(10) 0.0344(5) Uani 1 1 d . . . H20 H 0.5651 -0.5981 -0.0169 0.041 Uiso 1 1 calc R . . C21 C 0.51416(14) -0.70984(19) -0.10957(10) 0.0297(4) Uani 1 1 d . . . H21 H 0.5567 -0.7788 -0.0801 0.036 Uiso 1 1 calc R . . C22 C 0.44729(12) -0.71636(16) -0.19049(9) 0.0220(3) Uani 1 1 d . . . H22 H 0.4445 -0.7898 -0.2162 0.026 Uiso 1 1 calc R . . C23 C 0.41211(11) -0.59800(13) -0.35587(8) 0.0147(3) Uani 1 1 d . . . C24 C 0.51511(12) -0.56314(15) -0.29527(9) 0.0185(3) Uani 1 1 d . . . H24 H 0.5338 -0.5550 -0.2438 0.022 Uiso 1 1 calc R . . C25 C 0.59054(13) -0.54028(16) -0.30973(10) 0.0226(3) Uani 1 1 d . . . H25 H 0.6602 -0.5156 -0.2683 0.027 Uiso 1 1 calc R . . C26 C 0.56399(13) -0.55357(15) -0.38452(10) 0.0223(3) Uani 1 1 d . . . H26 H 0.6152 -0.5369 -0.3945 0.027 Uiso 1 1 calc R . . C27 C 0.46239(13) -0.59124(15) -0.44488(9) 0.0219(3) Uani 1 1 d . . . H27 H 0.4451 -0.6030 -0.4957 0.026 Uiso 1 1 calc R . . C28 C 0.38589(12) -0.61186(14) -0.43118(9) 0.0180(3) Uani 1 1 d . . . H28 H 0.3160 -0.6353 -0.4729 0.022 Uiso 1 1 calc R . . C29 C 0.26303(11) -0.77683(13) -0.36745(8) 0.0146(3) Uani 1 1 d . . . C30 C 0.31417(12) -0.86492(14) -0.38347(9) 0.0180(3) Uani 1 1 d . . . H30 H 0.3773 -0.8440 -0.3787 0.022 Uiso 1 1 calc R . . C31 C 0.27203(13) -0.98328(15) -0.40645(9) 0.0221(3) Uani 1 1 d . . . H31 H 0.3065 -1.0429 -0.4175 0.027 Uiso 1 1 calc R . . C32 C 0.18035(14) -1.01478(15) -0.41334(10) 0.0245(3) Uani 1 1 d . . . H32 H 0.1517 -1.0955 -0.4295 0.029 Uiso 1 1 calc R . . C33 C 0.13025(13) -0.92814(15) -0.39652(10) 0.0238(3) Uani 1 1 d . . . H33 H 0.0679 -0.9502 -0.4006 0.029 Uiso 1 1 calc R . . C34 C 0.17101(12) -0.80925(14) -0.37373(9) 0.0187(3) Uani 1 1 d . . . H34 H 0.1364 -0.7503 -0.3625 0.022 Uiso 1 1 calc R . . N1 N 0.08041(10) -0.35662(11) -0.44889(7) 0.0151(2) Uani 1 1 d . . . N2 N 0.08521(10) -0.28885(12) -0.50332(7) 0.0162(2) Uani 1 1 d . . . Ni1 Ni 0.180318(14) -0.479801(17) -0.399210(10) 0.01325(6) Uani 1 1 d . . . O1 O 0.13193(8) -0.53489(10) -0.34348(6) 0.0173(2) Uani 1 1 d . . . O2 O 0.22484(8) -0.42379(10) -0.45855(6) 0.0161(2) Uani 1 1 d . . . P1 P 0.30948(3) -0.61832(3) -0.33986(2) 0.01241(8) Uani 1 1 d . . . S1 S 0.11974(3) -0.14876(4) -0.61006(2) 0.02464(10) 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 C1 0.0115(6) 0.0178(7) 0.0148(7) -0.0036(5) 0.0060(6) -0.0016(5) C2 0.0152(7) 0.0194(7) 0.0179(7) -0.0017(6) 0.0081(6) -0.0027(6) C3 0.0165(7) 0.0236(8) 0.0204(7) -0.0039(6) 0.0110(6) -0.0060(6) C4 0.0126(7) 0.0251(8) 0.0178(7) -0.0078(6) 0.0074(6) -0.0047(6) C5 0.0176(7) 0.0316(9) 0.0247(8) -0.0098(7) 0.0136(7) -0.0064(7) C6 0.0177(7) 0.0345(10) 0.0285(9) -0.0116(7) 0.0141(7) -0.0005(7) C7 0.0191(8) 0.0272(9) 0.0255(8) -0.0067(7) 0.0109(7) 0.0042(7) C8 0.0173(7) 0.0246(8) 0.0183(7) -0.0041(6) 0.0088(6) 0.0024(6) C9 0.0125(7) 0.0220(8) 0.0144(7) -0.0062(6) 0.0056(6) -0.0013(6) C10 0.0120(6) 0.0179(7) 0.0142(7) -0.0039(5) 0.0058(6) -0.0011(5) C11 0.0130(6) 0.0164(7) 0.0159(7) -0.0020(6) 0.0062(6) 0.0031(6) C12 0.0138(6) 0.0142(7) 0.0121(6) -0.0027(5) 0.0049(6) -0.0009(5) C13 0.0148(7) 0.0152(7) 0.0121(6) -0.0002(5) 0.0049(6) 0.0012(5) C14 0.0154(7) 0.0203(7) 0.0129(6) 0.0008(6) 0.0065(6) -0.0024(6) C15 0.0236(8) 0.0270(9) 0.0209(8) 0.0033(6) 0.0142(7) 0.0032(7) C16 0.0313(9) 0.0266(9) 0.0213(8) 0.0085(7) 0.0168(7) 0.0070(7) C17 0.0117(6) 0.0246(8) 0.0141(7) 0.0002(6) 0.0084(6) -0.0029(6) C18 0.0212(8) 0.0336(9) 0.0221(8) -0.0048(7) 0.0140(7) 0.0020(7) C19 0.0285(9) 0.0544(13) 0.0238(9) -0.0145(8) 0.0170(8) -0.0036(9) C20 0.0214(8) 0.0667(14) 0.0137(7) -0.0019(8) 0.0094(7) -0.0078(9) C21 0.0204(8) 0.0428(11) 0.0188(8) 0.0097(7) 0.0074(7) -0.0047(7) C22 0.0167(7) 0.0266(8) 0.0181(7) 0.0035(6) 0.0074(6) -0.0032(6) C23 0.0145(7) 0.0139(7) 0.0172(7) 0.0023(5) 0.0102(6) 0.0024(5) C24 0.0169(7) 0.0222(8) 0.0172(7) -0.0010(6) 0.0103(6) -0.0017(6) C25 0.0165(7) 0.0267(9) 0.0253(8) 0.0007(7) 0.0125(7) -0.0020(6) C26 0.0230(8) 0.0232(8) 0.0302(9) 0.0052(7) 0.0209(7) 0.0044(6) C27 0.0271(8) 0.0240(8) 0.0204(7) 0.0035(6) 0.0172(7) 0.0044(7) C28 0.0176(7) 0.0202(8) 0.0159(7) 0.0010(6) 0.0095(6) 0.0012(6) C29 0.0132(6) 0.0141(7) 0.0126(6) 0.0015(5) 0.0053(6) 0.0016(5) C30 0.0168(7) 0.0198(8) 0.0168(7) 0.0027(6) 0.0094(6) 0.0041(6) C31 0.0252(8) 0.0178(8) 0.0220(8) -0.0010(6) 0.0129(7) 0.0053(6) C32 0.0253(8) 0.0161(8) 0.0263(8) -0.0031(6) 0.0117(7) -0.0020(6) C33 0.0177(7) 0.0205(8) 0.0311(9) -0.0020(7) 0.0131(7) -0.0031(6) C34 0.0165(7) 0.0173(7) 0.0214(7) 0.0002(6) 0.0105(6) 0.0020(6) N1 0.0140(6) 0.0148(6) 0.0132(6) -0.0005(5) 0.0061(5) 0.0009(5) N2 0.0168(6) 0.0162(6) 0.0146(6) 0.0008(5) 0.0085(5) 0.0016(5) Ni1 0.01132(9) 0.01315(10) 0.01417(10) 0.00127(7) 0.00679(8) 0.00225(7) O1 0.0145(5) 0.0167(5) 0.0210(5) 0.0029(4) 0.0106(4) 0.0035(4) O2 0.0145(5) 0.0166(5) 0.0159(5) 0.0033(4) 0.0081(4) 0.0040(4) P1 0.01050(16) 0.01375(18) 0.01250(17) 0.00099(13) 0.00641(14) 0.00135(13) S1 0.0283(2) 0.0247(2) 0.0230(2) 0.00876(16) 0.01615(18) 0.01097(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 C1 O1 1.3185(18) . ? C1 C10 1.411(2) . ? C1 C2 1.431(2) . ? C2 C3 1.360(2) . ? C2 H2 0.9500 . ? C3 C4 1.427(2) . ? C3 H3 0.9500 . ? C4 C5 1.418(2) . ? C4 C9 1.422(2) . ? C5 C6 1.373(3) . ? C5 H5 0.9500 . ? C6 C7 1.403(3) . ? C6 H6 0.9500 . ? C7 C8 1.381(2) . ? C7 H7 0.9500 . ? C8 C9 1.419(2) . ? C8 H8 0.9500 . ? C9 C10 1.456(2) . ? C10 C11 1.428(2) . ? C11 N1 1.3026(19) . ? C11 H11 0.9500 . ? C12 N2 1.3078(19) . ? C12 O2 1.3087(18) . ? C12 C13 1.463(2) . ? C13 C14 1.387(2) . ? C13 S1 1.7251(16) . ? C14 C15 1.428(2) . ? C14 H14 0.9500 . ? C15 C16 1.360(2) . ? C15 H15 0.9500 . ? C16 S1 1.7103(17) . ? C16 H16 0.9500 . ? C17 C18 1.388(2) . ? C17 C22 1.394(2) . ? C17 P1 1.8190(16) . ? C18 C19 1.395(2) . ? C18 H18 0.9500 . ? C19 C20 1.386(3) . ? C19 H19 0.9500 . ? C20 C21 1.380(3) . ? C20 H20 0.9500 . ? C21 C22 1.390(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.396(2) . ? C23 C28 1.399(2) . ? C23 P1 1.8215(15) . ? C24 C25 1.391(2) . ? C24 H24 0.9500 . ? C25 C26 1.386(2) . ? C25 H25 0.9500 . ? C26 C27 1.390(2) . ? C26 H26 0.9500 . ? C27 C28 1.392(2) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C34 1.398(2) . ? C29 C30 1.402(2) . ? C29 P1 1.8231(17) . ? C30 C31 1.393(2) . ? C30 H30 0.9500 . ? C31 C32 1.384(2) . ? C31 H31 0.9500 . ? C32 C33 1.390(2) . ? C32 H32 0.9500 . ? C33 C34 1.392(2) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? N1 N2 1.4007(17) . ? N1 Ni1 1.8414(13) . ? Ni1 O1 1.8236(11) . ? Ni1 O2 1.8481(11) . ? Ni1 P1 2.2166(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C10 125.09(14) . . ? O1 C1 C2 115.44(14) . . ? C10 C1 C2 119.46(14) . . ? C3 C2 C1 121.10(15) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 121.46(15) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C9 119.90(15) . . ? C5 C4 C3 120.93(15) . . ? C9 C4 C3 119.17(14) . . ? C6 C5 C4 121.25(16) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.21(15) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 120.88(16) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 121.32(16) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 117.42(14) . . ? C8 C9 C10 123.33(14) . . ? C4 C9 C10 119.24(14) . . ? C1 C10 C11 120.78(13) . . ? C1 C10 C9 119.40(14) . . ? C11 C10 C9 119.81(14) . . ? N1 C11 C10 123.68(14) . . ? N1 C11 H11 118.2 . . ? C10 C11 H11 118.2 . . ? N2 C12 O2 124.00(14) . . ? N2 C12 C13 118.80(13) . . ? O2 C12 C13 117.19(13) . . ? C14 C13 C12 126.79(14) . . ? C14 C13 S1 111.82(11) . . ? C12 C13 S1 121.35(11) . . ? C13 C14 C15 111.20(14) . . ? C13 C14 H14 124.4 . . ? C15 C14 H14 124.4 . . ? C16 C15 C14 113.05(15) . . ? C16 C15 H15 123.5 . . ? C14 C15 H15 123.5 . . ? C15 C16 S1 112.38(13) . . ? C15 C16 H16 123.8 . . ? S1 C16 H16 123.8 . . ? C18 C17 C22 119.60(15) . . ? C18 C17 P1 120.18(12) . . ? C22 C17 P1 119.87(12) . . ? C17 C18 C19 119.84(17) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 120.11(18) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.23(16) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 119.87(18) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C17 120.33(17) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? C24 C23 C28 119.32(14) . . ? C24 C23 P1 121.33(11) . . ? C28 C23 P1 119.29(11) . . ? C25 C24 C23 120.45(14) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 119.99(15) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 119.99(15) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C26 C27 C28 120.33(15) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 119.89(14) . . ? C27 C28 H28 120.1 . . ? C23 C28 H28 120.1 . . ? C34 C29 C30 119.62(14) . . ? C34 C29 P1 117.31(11) . . ? C30 C29 P1 123.06(12) . . ? C31 C30 C29 119.68(14) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C32 C31 C30 120.57(15) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C33 119.88(15) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? C32 C33 C34 120.35(15) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C33 C34 C29 119.88(14) . . ? C33 C34 H34 120.1 . . ? C29 C34 H34 120.1 . . ? C11 N1 N2 116.92(12) . . ? C11 N1 Ni1 128.27(11) . . ? N2 N1 Ni1 114.74(9) . . ? C12 N2 N1 107.46(12) . . ? O1 Ni1 N1 94.54(6) . . ? O1 Ni1 O2 178.13(5) . . ? N1 Ni1 O2 84.16(5) . . ? O1 Ni1 P1 89.38(4) . . ? N1 Ni1 P1 175.38(4) . . ? O2 Ni1 P1 91.97(4) . . ? C1 O1 Ni1 127.19(10) . . ? C12 O2 Ni1 109.63(9) . . ? C17 P1 C23 102.87(7) . . ? C17 P1 C29 104.92(7) . . ? C23 P1 C29 106.28(7) . . ? C17 P1 Ni1 113.79(5) . . ? C23 P1 Ni1 114.36(5) . . ? C29 P1 Ni1 113.56(5) . . ? C16 S1 C13 91.54(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 176.86(14) . . . . ? C10 C1 C2 C3 -2.7(2) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C2 C3 C4 C5 -178.56(15) . . . . ? C2 C3 C4 C9 1.3(2) . . . . ? C9 C4 C5 C6 -0.1(2) . . . . ? C3 C4 C5 C6 179.73(15) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C5 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 C9 0.8(2) . . . . ? C7 C8 C9 C4 -1.6(2) . . . . ? C7 C8 C9 C10 178.80(15) . . . . ? C5 C4 C9 C8 1.3(2) . . . . ? C3 C4 C9 C8 -178.57(14) . . . . ? C5 C4 C9 C10 -179.14(13) . . . . ? C3 C4 C9 C10 1.0(2) . . . . ? O1 C1 C10 C11 6.9(2) . . . . ? C2 C1 C10 C11 -173.66(13) . . . . ? O1 C1 C10 C9 -174.58(13) . . . . ? C2 C1 C10 C9 4.9(2) . . . . ? C8 C9 C10 C1 175.47(14) . . . . ? C4 C9 C10 C1 -4.1(2) . . . . ? C8 C9 C10 C11 -6.0(2) . . . . ? C4 C9 C10 C11 174.47(13) . . . . ? C1 C10 C11 N1 -2.1(2) . . . . ? C9 C10 C11 N1 179.38(14) . . . . ? N2 C12 C13 C14 -173.08(14) . . . . ? O2 C12 C13 C14 7.7(2) . . . . ? N2 C12 C13 S1 4.40(19) . . . . ? O2 C12 C13 S1 -174.80(10) . . . . ? C12 C13 C14 C15 178.58(14) . . . . ? S1 C13 C14 C15 0.90(17) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? C14 C15 C16 S1 -0.2(2) . . . . ? C22 C17 C18 C19 1.2(2) . . . . ? P1 C17 C18 C19 -172.07(13) . . . . ? C17 C18 C19 C20 -0.6(3) . . . . ? C18 C19 C20 C21 -0.4(3) . . . . ? C19 C20 C21 C22 0.9(3) . . . . ? C20 C21 C22 C17 -0.3(2) . . . . ? C18 C17 C22 C21 -0.7(2) . . . . ? P1 C17 C22 C21 172.55(12) . . . . ? C28 C23 C24 C25 1.1(2) . . . . ? P1 C23 C24 C25 -175.79(12) . . . . ? C23 C24 C25 C26 -0.8(2) . . . . ? C24 C25 C26 C27 -0.8(3) . . . . ? C25 C26 C27 C28 2.1(2) . . . . ? C26 C27 C28 C23 -1.8(2) . . . . ? C24 C23 C28 C27 0.2(2) . . . . ? P1 C23 C28 C27 177.16(12) . . . . ? C34 C29 C30 C31 0.8(2) . . . . ? P1 C29 C30 C31 -178.10(12) . . . . ? C29 C30 C31 C32 -0.2(2) . . . . ? C30 C31 C32 C33 -0.6(3) . . . . ? C31 C32 C33 C34 0.8(3) . . . . ? C32 C33 C34 C29 -0.2(2) . . . . ? C30 C29 C34 C33 -0.6(2) . . . . ? P1 C29 C34 C33 178.38(12) . . . . ? C10 C11 N1 N2 178.43(13) . . . . ? C10 C11 N1 Ni1 -4.5(2) . . . . ? O2 C12 N2 N1 -0.10(19) . . . . ? C13 C12 N2 N1 -179.25(12) . . . . ? C11 N1 N2 C12 176.55(13) . . . . ? Ni1 N1 N2 C12 -0.87(14) . . . . ? C11 N1 Ni1 O1 5.41(14) . . . . ? N2 N1 Ni1 O1 -177.52(10) . . . . ? C11 N1 Ni1 O2 -175.93(14) . . . . ? N2 N1 Ni1 O2 1.14(10) . . . . ? C10 C1 O1 Ni1 -4.7(2) . . . . ? C2 C1 O1 Ni1 175.76(10) . . . . ? N1 Ni1 O1 C1 -0.84(13) . . . . ? P1 Ni1 O1 C1 176.73(12) . . . . ? N2 C12 O2 Ni1 0.99(18) . . . . ? C13 C12 O2 Ni1 -179.85(10) . . . . ? N1 Ni1 O2 C12 -1.11(10) . . . . ? P1 Ni1 O2 C12 -178.58(9) . . . . ? C18 C17 P1 C23 100.12(13) . . . . ? C22 C17 P1 C23 -73.10(13) . . . . ? C18 C17 P1 C29 -148.88(13) . . . . ? C22 C17 P1 C29 37.90(14) . . . . ? C18 C17 P1 Ni1 -24.17(14) . . . . ? C22 C17 P1 Ni1 162.62(10) . . . . ? C24 C23 P1 C17 -11.67(14) . . . . ? C28 C23 P1 C17 171.42(12) . . . . ? C24 C23 P1 C29 -121.66(13) . . . . ? C28 C23 P1 C29 61.44(13) . . . . ? C24 C23 P1 Ni1 112.24(12) . . . . ? C28 C23 P1 Ni1 -64.67(13) . . . . ? C34 C29 P1 C17 82.59(12) . . . . ? C30 C29 P1 C17 -98.45(13) . . . . ? C34 C29 P1 C23 -168.87(11) . . . . ? C30 C29 P1 C23 10.09(14) . . . . ? C34 C29 P1 Ni1 -42.28(13) . . . . ? C30 C29 P1 Ni1 136.69(11) . . . . ? O1 Ni1 P1 C17 -51.26(7) . . . . ? O2 Ni1 P1 C17 130.02(6) . . . . ? O1 Ni1 P1 C23 -169.10(6) . . . . ? O2 Ni1 P1 C23 12.18(6) . . . . ? O1 Ni1 P1 C29 68.69(7) . . . . ? O2 Ni1 P1 C29 -110.03(6) . . . . ? C15 C16 S1 C13 0.61(15) . . . . ? C14 C13 S1 C16 -0.87(13) . . . . ? C12 C13 S1 C16 -178.69(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.407 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.055