# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 867537' #TrackingRef 'shelxl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H37 N2, C18 H15 Br3 Ni P' _chemical_formula_sum 'C45 H52 Br3 N2 Ni P' _chemical_formula_weight 950.30 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y, z+1/2' _cell_length_a 17.4911(18) _cell_length_b 14.3761(14) _cell_length_c 17.6688(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4442.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 18099 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 3.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.236 _exptl_absorpt_correction_T_max 0.464 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24646 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.1307 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 8189 _reflns_number_gt 6372 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0853P)^2^+0.8695P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.012(14) _refine_ls_number_reflns 8189 _refine_ls_number_parameters 473 _refine_ls_number_restraints 53 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1732 _refine_ls_wR_factor_gt 0.1601 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.098 _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 Br1 Br 0.59532(5) 0.46641(6) 0.35012(8) 0.0771(3) Uani 1 1 d . A . Br2 Br 0.74303(11) 0.58612(14) 0.45682(11) 0.0597(5) Uiso 0.50 1 d P A 1 Br2' Br 0.76939(11) 0.56824(13) 0.47299(12) 0.0598(5) Uiso 0.50 1 d P A 2 Br3 Br 0.74346(6) 0.30662(7) 0.48369(6) 0.0799(3) Uani 1 1 d . A . Ni1 Ni 0.71675(5) 0.43876(6) 0.40815(6) 0.0499(2) Uani 1 1 d . . . P1 P 0.79778(10) 0.40963(12) 0.30764(10) 0.0413(4) Uani 1 1 d . A . N1 N 0.9498(3) 0.7902(4) 0.2882(3) 0.0426(13) Uani 1 1 d . . . N2 N 0.9118(3) 0.8165(4) 0.4021(4) 0.0493(14) Uani 1 1 d . . . C1 C 0.8148(4) 0.5020(5) 0.2386(4) 0.0395(14) Uani 1 1 d . . . C2 C 0.7566(4) 0.5649(5) 0.2212(5) 0.0483(18) Uani 1 1 d . A . H2 H 0.7102 0.5631 0.2480 0.058 Uiso 1 1 calc R . . C3 C 0.7676(6) 0.6298(6) 0.1643(5) 0.064(2) Uani 1 1 d . . . H3 H 0.7282 0.6719 0.1524 0.076 Uiso 1 1 calc R A . C4 C 0.8354(6) 0.6334(6) 0.1249(5) 0.067(2) Uani 1 1 d . A . H4 H 0.8420 0.6778 0.0863 0.080 Uiso 1 1 calc R . . C5 C 0.8925(5) 0.5736(5) 0.1413(5) 0.059(2) Uani 1 1 d . . . H5 H 0.9384 0.5760 0.1137 0.071 Uiso 1 1 calc R A . C6 C 0.8839(5) 0.5081(5) 0.1990(4) 0.0525(17) Uani 1 1 d . A . H6 H 0.9245 0.4681 0.2112 0.063 Uiso 1 1 calc R . . C7 C 0.8942(3) 0.3786(4) 0.3399(4) 0.0437(15) Uani 1 1 d . . . C8 C 0.9308(5) 0.4394(7) 0.3890(5) 0.073(3) Uani 1 1 d . A . H8 H 0.9068 0.4947 0.4046 0.087 Uiso 1 1 calc R . . C9 C 1.0027(5) 0.4172(10) 0.4144(7) 0.096(4) Uani 1 1 d . . . H9 H 1.0281 0.4600 0.4457 0.115 Uiso 1 1 calc R A . C10 C 1.0386(6) 0.3374(10) 0.3967(8) 0.101(4) Uani 1 1 d . A . H10 H 1.0871 0.3233 0.4166 0.121 Uiso 1 1 calc R . . C11 C 1.0023(6) 0.2776(8) 0.3490(9) 0.099(4) Uani 1 1 d . . . H11 H 1.0266 0.2219 0.3351 0.119 Uiso 1 1 calc R A . C12 C 0.9293(5) 0.2974(6) 0.3201(6) 0.069(2) Uani 1 1 d . A . H12 H 0.9048 0.2552 0.2875 0.083 Uiso 1 1 calc R . . C13 C 0.7653(4) 0.3121(5) 0.2499(5) 0.0489(17) Uani 1 1 d . . . C14 C 0.7800(6) 0.3062(7) 0.1742(6) 0.074(3) Uani 1 1 d . A . H14 H 0.8067 0.3541 0.1494 0.089 Uiso 1 1 calc R . . C15 C 0.7554(6) 0.2291(8) 0.1342(7) 0.087(3) Uani 1 1 d . . . H15 H 0.7679 0.2238 0.0827 0.104 Uiso 1 1 calc R A . C16 C 0.7137(5) 0.1611(6) 0.1676(6) 0.068(2) Uani 1 1 d . A . H16 H 0.6976 0.1093 0.1394 0.081 Uiso 1 1 calc R . . C17 C 0.6949(7) 0.1681(7) 0.2427(6) 0.087(3) Uani 1 1 d . . . H17 H 0.6644 0.1226 0.2660 0.104 Uiso 1 1 calc R A . C18 C 0.7218(6) 0.2433(6) 0.2835(5) 0.077(3) Uani 1 1 d . A . H18 H 0.7102 0.2478 0.3353 0.092 Uiso 1 1 calc R . . C19 C 0.9620(4) 0.8412(5) 0.3503(4) 0.0478(15) Uani 1 1 d . . . H19 H 1.0000 0.8869 0.3560 0.057 Uiso 1 1 calc R . . C20 C 0.8909(4) 0.7300(5) 0.3024(5) 0.0539(18) Uani 1 1 d . . . H20 H 0.8710 0.6860 0.2684 0.065 Uiso 1 1 calc R . . C21 C 0.8670(4) 0.7446(5) 0.3724(5) 0.0557(19) Uani 1 1 d . . . H21 H 0.8274 0.7127 0.3974 0.067 Uiso 1 1 calc R . . C22 C 0.9885(5) 0.7960(6) 0.2152(5) 0.0619(15) Uani 1 1 d U . . C23 C 0.9597(5) 0.8598(7) 0.1618(6) 0.0746(17) Uani 1 1 d U C . C24 C 0.9945(6) 0.8521(9) 0.0899(6) 0.0878(18) Uani 1 1 d U . . H24 H 0.9781 0.8911 0.0503 0.105 Uiso 1 1 calc R . . C25 C 1.0507(7) 0.7900(9) 0.0768(7) 0.0906(19) Uani 1 1 d U . . H25 H 1.0728 0.7896 0.0283 0.109 Uiso 1 1 calc R . . C26 C 1.0776(6) 0.7290(8) 0.1274(6) 0.0818(18) Uani 1 1 d U . . H26 H 1.1156 0.6859 0.1137 0.098 Uiso 1 1 calc R . . C27 C 1.0474(5) 0.7306(7) 0.2026(5) 0.0684(16) Uani 1 1 d U . . C28 C 0.8978(7) 0.9325(8) 0.1845(10) 0.108(5) Uani 1 1 d D . . H28 H 0.9001 0.9166 0.2389 0.130 Uiso 1 1 calc R B 1 C29 C 0.9180(14) 1.0307(13) 0.1969(15) 0.099(7) Uiso 0.50 1 d PD C 1 C29' C 0.9059(19) 1.006(2) 0.1227(17) 0.134(10) Uiso 0.50 1 d PD C 2 C30 C 0.8204(8) 0.9013(12) 0.1761(12) 0.142(6) Uani 1 1 d . C . H30A H 0.7864 0.9432 0.2030 0.214 Uiso 1 1 calc R . . H30B H 0.8154 0.8391 0.1968 0.214 Uiso 1 1 calc R . . H30C H 0.8069 0.9005 0.1228 0.214 Uiso 1 1 calc R . . C31 C 1.0774(5) 0.6689(7) 0.2622(7) 0.080(3) Uani 1 1 d . . . H31 H 1.0357 0.6601 0.2994 0.097 Uiso 1 1 calc R . . C32 C 1.1432(7) 0.7152(9) 0.3040(8) 0.106(4) Uani 1 1 d . . . H32A H 1.1822 0.7335 0.2679 0.159 Uiso 1 1 calc R . . H32B H 1.1648 0.6718 0.3402 0.159 Uiso 1 1 calc R . . H32C H 1.1245 0.7698 0.3304 0.159 Uiso 1 1 calc R . . C33 C 1.0997(8) 0.5734(9) 0.2345(11) 0.130(6) Uani 1 1 d . . . H33A H 1.0570 0.5457 0.2077 0.195 Uiso 1 1 calc R . . H33B H 1.1132 0.5346 0.2774 0.195 Uiso 1 1 calc R . . H33C H 1.1431 0.5785 0.2007 0.195 Uiso 1 1 calc R . . C34 C 0.9050(4) 0.8531(5) 0.4785(5) 0.0523(17) Uani 1 1 d . . . C35 C 0.9424(5) 0.8049(6) 0.5370(5) 0.062(2) Uani 1 1 d . E . C36 C 0.9331(6) 0.8404(9) 0.6098(6) 0.083(3) Uani 1 1 d . . . H36 H 0.9574 0.8110 0.6509 0.099 Uiso 1 1 calc R . . C37 C 0.8878(6) 0.9192(8) 0.6225(6) 0.080(3) Uani 1 1 d . . . H37 H 0.8824 0.9431 0.6717 0.096 Uiso 1 1 calc R . . C38 C 0.8514(6) 0.9615(8) 0.5628(6) 0.078(3) Uani 1 1 d . . . H38 H 0.8210 1.0141 0.5724 0.094 Uiso 1 1 calc R . . C39 C 0.8577(5) 0.9296(6) 0.4890(5) 0.063(2) Uani 1 1 d . . . C40 C 0.9945(6) 0.7203(7) 0.5215(6) 0.084(3) Uani 1 1 d D . . H40 H 0.9847 0.7076 0.4672 0.100 Uiso 1 1 calc R D 1 C41 C 1.0762(7) 0.7539(13) 0.5210(12) 0.150(7) Uani 1 1 d . E . H41A H 1.0973 0.7492 0.5716 0.225 Uiso 1 1 calc R . . H41B H 1.0777 0.8182 0.5044 0.225 Uiso 1 1 calc R . . H41C H 1.1060 0.7158 0.4866 0.225 Uiso 1 1 calc R . . C42 C 0.9701(14) 0.6301(13) 0.5587(14) 0.084(6) Uiso 0.50 1 d PD E 1 C42' C 0.9921(14) 0.6501(17) 0.5865(13) 0.090(7) Uiso 0.50 1 d PD E 2 C43 C 0.8177(5) 0.9775(6) 0.4243(6) 0.070(2) Uani 1 1 d . . . H43 H 0.8195 0.9356 0.3798 0.084 Uiso 1 1 calc R . . C44 C 0.8559(7) 1.0677(7) 0.4027(11) 0.115(4) Uani 1 1 d . . . H44A H 0.8508 1.1119 0.4439 0.172 Uiso 1 1 calc R . . H44B H 0.8318 1.0927 0.3576 0.172 Uiso 1 1 calc R . . H44C H 0.9097 1.0566 0.3928 0.172 Uiso 1 1 calc R . . C45 C 0.7341(6) 0.9950(10) 0.4434(7) 0.098(4) Uani 1 1 d . . . H45A H 0.7085 0.9361 0.4520 0.148 Uiso 1 1 calc R . . H45B H 0.7097 1.0272 0.4017 0.148 Uiso 1 1 calc R . . H45C H 0.7308 1.0329 0.4887 0.148 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 Br1 0.0530(4) 0.0621(5) 0.1162(8) -0.0032(6) 0.0033(5) 0.0092(4) Br3 0.1116(8) 0.0658(5) 0.0624(5) 0.0205(5) 0.0077(5) -0.0021(5) Ni1 0.0566(5) 0.0430(5) 0.0501(5) -0.0025(4) 0.0122(5) -0.0020(4) P1 0.0470(9) 0.0340(8) 0.0428(9) 0.0002(7) 0.0018(8) 0.0001(7) N1 0.040(3) 0.038(3) 0.050(3) -0.005(3) 0.005(2) -0.006(2) N2 0.050(3) 0.039(3) 0.059(4) -0.009(3) 0.007(3) -0.008(2) C1 0.050(4) 0.038(3) 0.030(3) -0.007(3) 0.000(3) -0.004(3) C2 0.057(4) 0.029(3) 0.059(5) 0.004(3) -0.012(3) -0.006(3) C3 0.082(6) 0.053(5) 0.056(5) -0.005(4) -0.028(5) -0.001(4) C4 0.116(7) 0.044(4) 0.042(4) 0.008(3) -0.016(5) -0.007(5) C5 0.080(5) 0.046(4) 0.051(5) -0.008(4) 0.012(4) -0.009(4) C6 0.063(4) 0.054(4) 0.040(4) 0.000(3) 0.005(3) 0.002(4) C7 0.042(3) 0.044(3) 0.045(4) 0.012(3) 0.001(3) 0.005(3) C8 0.062(5) 0.090(7) 0.067(6) -0.016(5) -0.014(4) 0.014(5) C9 0.052(5) 0.152(11) 0.084(7) -0.011(8) -0.027(5) 0.005(6) C10 0.046(5) 0.142(11) 0.113(9) 0.037(9) -0.003(6) 0.018(6) C11 0.061(5) 0.080(6) 0.157(12) 0.025(8) 0.003(7) 0.025(5) C12 0.067(5) 0.048(4) 0.091(7) 0.000(4) 0.005(5) -0.002(4) C13 0.048(4) 0.039(4) 0.060(5) -0.003(3) 0.009(3) 0.004(3) C14 0.095(7) 0.066(6) 0.062(5) -0.025(5) 0.016(5) -0.024(5) C15 0.096(7) 0.079(7) 0.085(7) -0.028(6) 0.034(6) -0.020(6) C16 0.069(5) 0.047(4) 0.087(7) -0.023(4) -0.006(5) -0.004(4) C17 0.132(9) 0.051(5) 0.078(7) -0.005(5) 0.002(6) -0.035(6) C18 0.117(8) 0.059(5) 0.054(5) -0.003(4) -0.005(5) -0.036(5) C19 0.046(3) 0.044(3) 0.053(4) -0.010(3) 0.005(3) -0.007(3) C20 0.056(4) 0.052(4) 0.053(4) -0.010(4) 0.003(4) -0.020(3) C21 0.054(4) 0.041(4) 0.072(5) -0.003(3) 0.010(4) -0.019(3) C22 0.060(3) 0.067(4) 0.058(3) 0.000(3) 0.006(3) -0.021(3) C23 0.072(4) 0.081(4) 0.071(3) 0.011(3) -0.005(3) -0.025(3) C24 0.091(4) 0.100(4) 0.073(3) 0.015(3) -0.003(3) -0.030(3) C25 0.094(4) 0.106(5) 0.072(4) 0.003(3) 0.014(3) -0.030(3) C26 0.081(4) 0.094(4) 0.071(4) -0.008(3) 0.021(3) -0.018(3) C27 0.065(3) 0.075(4) 0.066(3) -0.010(3) 0.015(3) -0.018(3) C28 0.094(8) 0.069(7) 0.161(13) 0.040(7) -0.039(9) -0.001(6) C30 0.087(8) 0.121(11) 0.219(19) -0.028(13) 0.022(11) -0.015(8) C31 0.063(5) 0.061(5) 0.118(8) 0.020(6) 0.024(6) 0.012(4) C32 0.120(9) 0.100(8) 0.098(9) 0.009(7) -0.012(8) 0.015(8) C33 0.086(8) 0.080(8) 0.222(18) 0.004(10) -0.020(10) 0.030(6) C34 0.050(4) 0.053(4) 0.054(4) -0.011(4) 0.008(3) -0.004(3) C35 0.047(4) 0.072(5) 0.067(5) -0.020(5) -0.002(4) 0.003(4) C36 0.069(5) 0.107(8) 0.072(7) -0.011(6) -0.004(5) -0.010(6) C37 0.085(6) 0.091(7) 0.064(6) -0.028(6) 0.013(5) 0.004(6) C38 0.080(6) 0.084(7) 0.070(6) -0.027(5) 0.008(5) 0.014(5) C39 0.062(5) 0.061(5) 0.066(5) -0.022(4) 0.007(4) -0.001(4) C40 0.089(7) 0.089(7) 0.073(6) -0.012(6) -0.018(5) 0.024(6) C41 0.063(6) 0.145(13) 0.24(2) -0.031(14) 0.030(10) 0.018(8) C43 0.073(5) 0.053(5) 0.085(7) -0.016(5) -0.002(5) 0.010(4) C44 0.106(8) 0.060(6) 0.177(13) 0.022(8) -0.008(10) -0.002(6) C45 0.075(6) 0.129(10) 0.091(8) -0.031(8) -0.009(6) 0.009(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 Br1 Ni1 2.3917(14) . ? Br2 Ni1 2.332(2) . ? Br2' Ni1 2.372(2) . ? Br3 Ni1 2.3681(14) . ? Ni1 P1 2.310(2) . ? P1 C13 1.825(8) . ? P1 C1 1.827(7) . ? P1 C7 1.835(6) . ? N1 C19 1.336(9) . ? N1 C20 1.369(9) . ? N1 C22 1.459(10) . ? N2 C19 1.318(9) . ? N2 C21 1.400(9) . ? N2 C34 1.454(10) . ? C1 C2 1.396(10) . ? C1 C6 1.399(10) . ? C2 C3 1.386(12) . ? C2 H2 0.9400 . ? C3 C4 1.377(13) . ? C3 H3 0.9400 . ? C4 C5 1.349(13) . ? C4 H4 0.9400 . ? C5 C6 1.395(11) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C12 1.365(11) . ? C7 C8 1.388(11) . ? C8 C9 1.373(13) . ? C8 H8 0.9400 . ? C9 C10 1.346(17) . ? C9 H9 0.9400 . ? C10 C11 1.361(18) . ? C10 H10 0.9400 . ? C11 C12 1.405(14) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 C14 1.365(12) . ? C13 C18 1.381(11) . ? C14 C15 1.383(14) . ? C14 H14 0.9400 . ? C15 C16 1.355(14) . ? C15 H15 0.9400 . ? C16 C17 1.369(14) . ? C16 H16 0.9400 . ? C17 C18 1.382(12) . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? C19 H19 0.9400 . ? C20 C21 1.321(11) . ? C20 H20 0.9400 . ? C21 H21 0.9400 . ? C22 C23 1.409(13) . ? C22 C27 1.411(13) . ? C23 C24 1.414(14) . ? C23 C28 1.557(17) . ? C24 C25 1.349(17) . ? C24 H24 0.9400 . ? C25 C26 1.338(16) . ? C25 H25 0.9400 . ? C26 C27 1.430(13) . ? C26 H26 0.9400 . ? C27 C31 1.474(14) . ? C28 C30 1.435(17) . ? C28 C29 1.471(17) . ? C28 C29' 1.527(18) . ? C28 H28 0.9900 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C30 H30C 0.9700 . ? C31 C33 1.508(16) . ? C31 C32 1.521(16) . ? C31 H31 0.9900 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C34 C39 1.388(11) . ? C34 C35 1.406(12) . ? C35 C36 1.394(13) . ? C35 C40 1.545(13) . ? C36 C37 1.400(15) . ? C36 H36 0.9400 . ? C37 C38 1.374(15) . ? C37 H37 0.9400 . ? C38 C39 1.388(13) . ? C38 H38 0.9400 . ? C39 C43 1.508(14) . ? C40 C41 1.509(16) . ? C40 C42 1.515(16) . ? C40 C42' 1.530(17) . ? C40 H40 0.9900 . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C41 H41C 0.9700 . ? C43 C44 1.509(14) . ? C43 C45 1.521(14) . ? C43 H43 0.9900 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C44 H44C 0.9700 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C45 H45C 0.9700 . ? 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 P1 Ni1 Br2 109.09(7) . . ? P1 Ni1 Br3 99.60(6) . . ? Br2 Ni1 Br3 118.81(8) . . ? P1 Ni1 Br2' 105.98(7) . . ? Br2 Ni1 Br2' 14.63(5) . . ? Br3 Ni1 Br2' 106.31(7) . . ? P1 Ni1 Br1 104.20(7) . . ? Br2 Ni1 Br1 100.49(7) . . ? Br3 Ni1 Br1 123.38(5) . . ? Br2' Ni1 Br1 114.92(7) . . ? C13 P1 C1 103.7(3) . . ? C13 P1 C7 105.9(3) . . ? C1 P1 C7 103.5(3) . . ? C13 P1 Ni1 112.2(2) . . ? C1 P1 Ni1 118.8(2) . . ? C7 P1 Ni1 111.6(3) . . ? C19 N1 C20 108.4(6) . . ? C19 N1 C22 128.3(6) . . ? C20 N1 C22 123.2(6) . . ? C19 N2 C21 108.2(6) . . ? C19 N2 C34 127.0(6) . . ? C21 N2 C34 124.7(6) . . ? C2 C1 C6 118.6(7) . . ? C2 C1 P1 119.9(5) . . ? C6 C1 P1 121.4(5) . . ? C3 C2 C1 119.7(8) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 120.8(8) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.3(8) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.5(8) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.1(7) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C12 C7 C8 119.5(7) . . ? C12 C7 P1 122.7(6) . . ? C8 C7 P1 117.7(6) . . ? C9 C8 C7 118.7(9) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C10 C9 C8 123.4(11) . . ? C10 C9 H9 118.3 . . ? C8 C9 H9 118.3 . . ? C9 C10 C11 117.7(9) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? C10 C11 C12 121.5(10) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C7 C12 C11 119.2(10) . . ? C7 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C14 C13 C18 118.8(8) . . ? C14 C13 P1 122.4(6) . . ? C18 C13 P1 118.7(6) . . ? C13 C14 C15 119.4(9) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 121.6(10) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 119.8(9) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 118.8(9) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C13 C18 C17 121.5(9) . . ? C13 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? N2 C19 N1 108.4(6) . . ? N2 C19 H19 125.8 . . ? N1 C19 H19 125.8 . . ? C21 C20 N1 108.1(7) . . ? C21 C20 H20 126.0 . . ? N1 C20 H20 126.0 . . ? C20 C21 N2 106.9(6) . . ? C20 C21 H21 126.6 . . ? N2 C21 H21 126.6 . . ? C23 C22 C27 126.0(8) . . ? C23 C22 N1 117.6(8) . . ? C27 C22 N1 116.1(8) . . ? C22 C23 C24 113.4(10) . . ? C22 C23 C28 120.9(10) . . ? C24 C23 C28 125.6(11) . . ? C25 C24 C23 121.3(11) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 C24 125.2(11) . . ? C26 C25 H25 117.4 . . ? C24 C25 H25 117.4 . . ? C25 C26 C27 118.7(11) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C22 C27 C26 115.3(9) . . ? C22 C27 C31 123.2(8) . . ? C26 C27 C31 121.5(9) . . ? C30 C28 C29 122.8(15) . . ? C30 C28 C29' 103.3(17) . . ? C29 C28 C29' 54.5(17) . . ? C30 C28 C23 114.8(11) . . ? C29 C28 C23 121.1(13) . . ? C29' C28 C23 102.6(17) . . ? C30 C28 H28 93.8 . . ? C29 C28 H28 93.8 . . ? C29' C28 H28 148.3 . . ? C23 C28 H28 93.8 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 C33 114.1(12) . . ? C27 C31 C32 110.6(8) . . ? C33 C31 C32 111.1(9) . . ? C27 C31 H31 106.9 . . ? C33 C31 H31 106.9 . . ? C32 C31 H31 106.9 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C39 C34 C35 124.7(8) . . ? C39 C34 N2 117.3(7) . . ? C35 C34 N2 117.8(7) . . ? C36 C35 C34 116.4(8) . . ? C36 C35 C40 121.4(9) . . ? C34 C35 C40 122.1(8) . . ? C35 C36 C37 120.6(10) . . ? C35 C36 H36 119.7 . . ? C37 C36 H36 119.7 . . ? C38 C37 C36 119.9(9) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C38 C39 122.5(9) . . ? C37 C38 H38 118.7 . . ? C39 C38 H38 118.7 . . ? C38 C39 C34 115.8(9) . . ? C38 C39 C43 121.6(8) . . ? C34 C39 C43 122.5(8) . . ? C41 C40 C42 122.9(14) . . ? C41 C40 C42' 104.0(14) . . ? C42 C40 C42' 26.0(12) . . ? C41 C40 C35 107.9(10) . . ? C42 C40 C35 115.6(12) . . ? C42' C40 C35 111.7(12) . . ? C41 C40 H40 102.4 . . ? C42 C40 H40 102.4 . . ? C42' C40 H40 127.0 . . ? C35 C40 H40 102.4 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C43 C44 112.2(9) . . ? C39 C43 C45 110.7(9) . . ? C44 C43 C45 109.9(9) . . ? C39 C43 H43 108.0 . . ? C44 C43 H43 108.0 . . ? C45 C43 H43 108.0 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br2 Ni1 P1 C13 -164.2(3) . . . . ? Br3 Ni1 P1 C13 70.6(3) . . . . ? Br2' Ni1 P1 C13 -179.2(3) . . . . ? Br1 Ni1 P1 C13 -57.6(3) . . . . ? Br2 Ni1 P1 C1 -43.2(3) . . . . ? Br3 Ni1 P1 C1 -168.4(2) . . . . ? Br2' Ni1 P1 C1 -58.2(3) . . . . ? Br1 Ni1 P1 C1 63.4(2) . . . . ? Br2 Ni1 P1 C7 77.1(2) . . . . ? Br3 Ni1 P1 C7 -48.0(2) . . . . ? Br2' Ni1 P1 C7 62.1(2) . . . . ? Br1 Ni1 P1 C7 -176.2(2) . . . . ? C13 P1 C1 C2 92.0(6) . . . . ? C7 P1 C1 C2 -157.7(6) . . . . ? Ni1 P1 C1 C2 -33.3(6) . . . . ? C13 P1 C1 C6 -84.0(6) . . . . ? C7 P1 C1 C6 26.3(6) . . . . ? Ni1 P1 C1 C6 150.7(5) . . . . ? C6 C1 C2 C3 1.6(10) . . . . ? P1 C1 C2 C3 -174.5(6) . . . . ? C1 C2 C3 C4 -0.3(12) . . . . ? C2 C3 C4 C5 -0.1(12) . . . . ? C3 C4 C5 C6 -0.8(12) . . . . ? C4 C5 C6 C1 2.1(11) . . . . ? C2 C1 C6 C5 -2.5(10) . . . . ? P1 C1 C6 C5 173.6(6) . . . . ? C13 P1 C7 C12 0.9(8) . . . . ? C1 P1 C7 C12 -107.9(7) . . . . ? Ni1 P1 C7 C12 123.2(7) . . . . ? C13 P1 C7 C8 -176.4(7) . . . . ? C1 P1 C7 C8 74.9(7) . . . . ? Ni1 P1 C7 C8 -54.0(7) . . . . ? C12 C7 C8 C9 2.1(14) . . . . ? P1 C7 C8 C9 179.5(9) . . . . ? C7 C8 C9 C10 -2.9(18) . . . . ? C8 C9 C10 C11 2(2) . . . . ? C9 C10 C11 C12 -1(2) . . . . ? C8 C7 C12 C11 -0.9(14) . . . . ? P1 C7 C12 C11 -178.2(8) . . . . ? C10 C11 C12 C7 0.4(18) . . . . ? C1 P1 C13 C14 20.8(8) . . . . ? C7 P1 C13 C14 -87.8(8) . . . . ? Ni1 P1 C13 C14 150.1(7) . . . . ? C1 P1 C13 C18 -156.8(7) . . . . ? C7 P1 C13 C18 94.6(8) . . . . ? Ni1 P1 C13 C18 -27.4(8) . . . . ? C18 C13 C14 C15 -4.1(15) . . . . ? P1 C13 C14 C15 178.3(8) . . . . ? C13 C14 C15 C16 3.2(17) . . . . ? C14 C15 C16 C17 0.1(18) . . . . ? C15 C16 C17 C18 -2.4(18) . . . . ? C14 C13 C18 C17 1.8(16) . . . . ? P1 C13 C18 C17 179.5(9) . . . . ? C16 C17 C18 C13 1.5(18) . . . . ? C21 N2 C19 N1 1.8(8) . . . . ? C34 N2 C19 N1 179.1(7) . . . . ? C20 N1 C19 N2 -1.5(8) . . . . ? C22 N1 C19 N2 176.7(7) . . . . ? C19 N1 C20 C21 0.5(9) . . . . ? C22 N1 C20 C21 -177.7(7) . . . . ? N1 C20 C21 N2 0.6(9) . . . . ? C19 N2 C21 C20 -1.5(9) . . . . ? C34 N2 C21 C20 -178.9(7) . . . . ? C19 N1 C22 C23 -87.0(10) . . . . ? C20 N1 C22 C23 90.9(10) . . . . ? C19 N1 C22 C27 98.6(9) . . . . ? C20 N1 C22 C27 -83.5(9) . . . . ? C27 C22 C23 C24 1.4(13) . . . . ? N1 C22 C23 C24 -172.4(7) . . . . ? C27 C22 C23 C28 -176.3(9) . . . . ? N1 C22 C23 C28 10.0(12) . . . . ? C22 C23 C24 C25 -1.3(14) . . . . ? C28 C23 C24 C25 176.2(10) . . . . ? C23 C24 C25 C26 2.1(18) . . . . ? C24 C25 C26 C27 -2.6(17) . . . . ? C23 C22 C27 C26 -2.0(13) . . . . ? N1 C22 C27 C26 171.9(7) . . . . ? C23 C22 C27 C31 177.0(9) . . . . ? N1 C22 C27 C31 -9.2(12) . . . . ? C25 C26 C27 C22 2.4(13) . . . . ? C25 C26 C27 C31 -176.6(10) . . . . ? C22 C23 C28 C30 -89.2(16) . . . . ? C24 C23 C28 C30 93.5(16) . . . . ? C22 C23 C28 C29 103.6(18) . . . . ? C24 C23 C28 C29 -74(2) . . . . ? C22 C23 C28 C29' 159.6(16) . . . . ? C24 C23 C28 C29' -17.8(19) . . . . ? C22 C27 C31 C33 144.5(10) . . . . ? C26 C27 C31 C33 -36.6(13) . . . . ? C22 C27 C31 C32 -89.3(11) . . . . ? C26 C27 C31 C32 89.6(12) . . . . ? C19 N2 C34 C39 90.0(9) . . . . ? C21 N2 C34 C39 -93.2(9) . . . . ? C19 N2 C34 C35 -94.2(9) . . . . ? C21 N2 C34 C35 82.6(9) . . . . ? C39 C34 C35 C36 -2.9(13) . . . . ? N2 C34 C35 C36 -178.3(7) . . . . ? C39 C34 C35 C40 -179.8(8) . . . . ? N2 C34 C35 C40 4.7(12) . . . . ? C34 C35 C36 C37 0.7(14) . . . . ? C40 C35 C36 C37 177.7(9) . . . . ? C35 C36 C37 C38 0.9(16) . . . . ? C36 C37 C38 C39 -0.4(17) . . . . ? C37 C38 C39 C34 -1.5(15) . . . . ? C37 C38 C39 C43 -179.6(10) . . . . ? C35 C34 C39 C38 3.3(13) . . . . ? N2 C34 C39 C38 178.7(8) . . . . ? C35 C34 C39 C43 -178.7(8) . . . . ? N2 C34 C39 C43 -3.2(12) . . . . ? C36 C35 C40 C41 -78.6(14) . . . . ? C34 C35 C40 C41 98.2(12) . . . . ? C36 C35 C40 C42 63.3(16) . . . . ? C34 C35 C40 C42 -119.9(14) . . . . ? C36 C35 C40 C42' 35.1(17) . . . . ? C34 C35 C40 C42' -148.1(14) . . . . ? C38 C39 C43 C44 74.6(13) . . . . ? C34 C39 C43 C44 -103.4(11) . . . . ? C38 C39 C43 C45 -48.6(12) . . . . ? C34 C39 C43 C45 133.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.043 _refine_diff_density_min -1.161 _refine_diff_density_rms 0.088 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 867538' #TrackingRef 'shelxl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 N2, C18 H15 Br3 Ni P' _chemical_formula_sum 'C27 H32 Br3 N2 Ni P' _chemical_formula_weight 713.96 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' Br Br -0.2901 2.4595 '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' P P 0.1023 0.0942 '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' _symmetry_Int_Tables_number 14 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 16.0114(5) _cell_length_b 9.7678(8) _cell_length_c 19.4056(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.043(11) _cell_angle_gamma 90.00 _cell_volume 3034.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7632 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 4.660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.139 _exptl_absorpt_correction_T_max 0.257 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15163 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5628 _reflns_number_gt 3910 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1060P)^2^+3.6845P] 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 5628 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1069 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.2047 _refine_ls_wR_factor_gt 0.1837 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 Br1 Br 0.39604(6) 0.47299(11) 0.42682(6) 0.0736(3) Uani 1 1 d . . . Br2 Br 0.31503(8) 0.12277(10) 0.38090(7) 0.0870(4) Uani 1 1 d . . . Br3 Br 0.27920(6) 0.45507(9) 0.24972(4) 0.0619(3) Uani 1 1 d . . . Ni1 Ni 0.29501(5) 0.35735(10) 0.36046(5) 0.0414(3) Uani 1 1 d . . . P1 P 0.17108(10) 0.41463(18) 0.41205(9) 0.0353(4) Uani 1 1 d . . . N1 N 0.3613(4) 0.6767(7) 0.6156(4) 0.0562(17) Uani 1 1 d . . . N2 N 0.3838(4) 0.4862(7) 0.6667(3) 0.0484(15) Uani 1 1 d . . . C1 C 0.1407(4) 0.5909(7) 0.3964(3) 0.0373(15) Uani 1 1 d . . . C2 C 0.2016(5) 0.6883(8) 0.3828(5) 0.056(2) Uani 1 1 d . . . H2 H 0.2577 0.6610 0.3795 0.068 Uiso 1 1 calc R . . C3 C 0.1811(6) 0.8225(9) 0.3741(5) 0.070(3) Uani 1 1 d . . . H3 H 0.2235 0.8866 0.3655 0.084 Uiso 1 1 calc R . . C4 C 0.1004(6) 0.8660(9) 0.3775(5) 0.064(2) Uani 1 1 d . . . H4 H 0.0871 0.9591 0.3719 0.077 Uiso 1 1 calc R . . C5 C 0.0394(6) 0.7723(9) 0.3893(4) 0.059(2) Uani 1 1 d . . . H5 H -0.0165 0.8015 0.3900 0.070 Uiso 1 1 calc R . . C6 C 0.0574(4) 0.6347(8) 0.4003(4) 0.0465(18) Uani 1 1 d . . . H6 H 0.0147 0.5721 0.4102 0.056 Uiso 1 1 calc R . . C7 C 0.0813(4) 0.3111(7) 0.3847(3) 0.0389(15) Uani 1 1 d . . . C8 C 0.0650(6) 0.2910(9) 0.3164(4) 0.061(2) Uani 1 1 d . . . H8 H 0.1006 0.3301 0.2839 0.073 Uiso 1 1 calc R . . C9 C -0.0028(7) 0.2144(11) 0.2938(5) 0.077(3) Uani 1 1 d . . . H9 H -0.0132 0.2042 0.2462 0.092 Uiso 1 1 calc R . . C10 C -0.0540(5) 0.1544(9) 0.3388(5) 0.062(2) Uani 1 1 d . . . H10 H -0.1002 0.1030 0.3231 0.074 Uiso 1 1 calc R . . C11 C -0.0379(5) 0.1692(8) 0.4076(5) 0.054(2) Uani 1 1 d . . . H11 H -0.0723 0.1253 0.4395 0.065 Uiso 1 1 calc R . . C12 C 0.0292(4) 0.2490(7) 0.4313(4) 0.0470(18) Uani 1 1 d . . . H12 H 0.0388 0.2603 0.4788 0.056 Uiso 1 1 calc R . . C13 C 0.1755(4) 0.3966(7) 0.5051(3) 0.0372(15) Uani 1 1 d . . . C14 C 0.1997(5) 0.2722(8) 0.5332(4) 0.0501(18) Uani 1 1 d . . . H14 H 0.2128 0.1979 0.5046 0.060 Uiso 1 1 calc R . . C15 C 0.2044(6) 0.2590(10) 0.6042(4) 0.063(2) Uani 1 1 d . . . H15 H 0.2227 0.1754 0.6231 0.075 Uiso 1 1 calc R . . C16 C 0.1839(5) 0.3609(11) 0.6471(4) 0.061(2) Uani 1 1 d . . . H16 H 0.1856 0.3474 0.6951 0.073 Uiso 1 1 calc R . . C17 C 0.1604(5) 0.4848(10) 0.6200(4) 0.054(2) Uani 1 1 d . . . H17 H 0.1471 0.5569 0.6499 0.064 Uiso 1 1 calc R . . C18 C 0.1557(4) 0.5063(8) 0.5492(4) 0.0445(17) Uani 1 1 d . . . H18 H 0.1398 0.5919 0.5312 0.053 Uiso 1 1 calc R . . C19 C 0.3884(5) 0.5489(9) 0.6078(5) 0.057(2) Uani 1 1 d . . . H19 H 0.4077 0.5104 0.5666 0.068 Uiso 1 1 calc R . . C20 C 0.3383(6) 0.6931(9) 0.6829(5) 0.062(2) Uani 1 1 d . . . H20 H 0.3170 0.7733 0.7027 0.074 Uiso 1 1 calc R . . C21 C 0.3518(5) 0.5747(10) 0.7148(4) 0.061(2) Uani 1 1 d . . . H21 H 0.3415 0.5550 0.7613 0.073 Uiso 1 1 calc R . . C22 C 0.3610(6) 0.7785(10) 0.5575(5) 0.073(3) Uani 1 1 d . . . H22 H 0.3584 0.7238 0.5145 0.087 Uiso 1 1 calc R . . C23 C 0.2826(6) 0.8592(11) 0.5582(5) 0.078(3) Uani 1 1 d . . . H23A H 0.2832 0.9193 0.5980 0.117 Uiso 1 1 calc R . . H23B H 0.2352 0.7976 0.5606 0.117 Uiso 1 1 calc R . . H23C H 0.2780 0.9135 0.5165 0.117 Uiso 1 1 calc R . . C24 C 0.4382(7) 0.8507(13) 0.5561(7) 0.106(4) Uani 1 1 d . . . H24A H 0.4593 0.8506 0.5096 0.160 Uiso 1 1 calc R . . H24B H 0.4784 0.8064 0.5868 0.160 Uiso 1 1 calc R . . H24C H 0.4297 0.9444 0.5710 0.160 Uiso 1 1 calc R . . C25 C 0.4093(5) 0.3411(9) 0.6819(5) 0.064(2) Uani 1 1 d . . . H25 H 0.3608 0.2948 0.7025 0.076 Uiso 1 1 calc R . . C26 C 0.4284(7) 0.2671(10) 0.6158(6) 0.083(3) Uani 1 1 d . . . H26A H 0.3797 0.2693 0.5854 0.124 Uiso 1 1 calc R . . H26B H 0.4431 0.1728 0.6260 0.124 Uiso 1 1 calc R . . H26C H 0.4749 0.3117 0.5935 0.124 Uiso 1 1 calc R . . C27 C 0.4795(6) 0.3424(12) 0.7363(6) 0.088(3) Uani 1 1 d . . . H27A H 0.5300 0.3781 0.7161 0.132 Uiso 1 1 calc R . . H27B H 0.4894 0.2499 0.7527 0.132 Uiso 1 1 calc R . . H27C H 0.4635 0.4000 0.7746 0.132 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 Br1 0.0552(5) 0.0865(7) 0.0789(7) -0.0128(5) -0.0026(5) -0.0100(5) Br2 0.1071(8) 0.0507(6) 0.1042(9) -0.0064(5) 0.0336(7) -0.0068(5) Br3 0.0857(6) 0.0561(5) 0.0441(5) -0.0015(4) 0.0054(4) -0.0042(4) Ni1 0.0408(5) 0.0432(5) 0.0405(5) -0.0029(4) 0.0081(4) -0.0022(4) P1 0.0356(8) 0.0366(9) 0.0336(9) -0.0014(7) 0.0015(7) -0.0022(7) N1 0.051(4) 0.051(4) 0.067(5) 0.015(3) 0.004(3) 0.002(3) N2 0.038(3) 0.054(4) 0.053(4) 0.007(3) -0.001(3) -0.007(3) C1 0.050(4) 0.034(3) 0.028(3) -0.003(3) 0.003(3) 0.000(3) C2 0.051(4) 0.041(4) 0.077(6) -0.008(4) 0.011(4) 0.005(4) C3 0.073(6) 0.044(5) 0.093(7) -0.005(5) 0.017(5) -0.006(4) C4 0.082(6) 0.043(5) 0.068(6) 0.000(4) 0.007(5) 0.010(5) C5 0.063(5) 0.060(5) 0.052(5) 0.007(4) 0.006(4) 0.018(4) C6 0.043(4) 0.054(5) 0.043(4) 0.006(4) 0.007(3) 0.008(4) C7 0.037(3) 0.042(4) 0.037(4) -0.001(3) 0.000(3) 0.003(3) C8 0.076(6) 0.066(5) 0.040(4) 0.010(4) -0.007(4) -0.024(5) C9 0.088(7) 0.088(7) 0.052(5) -0.003(5) -0.029(5) -0.020(6) C10 0.046(4) 0.053(5) 0.086(7) -0.009(5) -0.015(4) -0.008(4) C11 0.038(4) 0.051(5) 0.074(6) -0.008(4) 0.005(4) 0.000(3) C12 0.043(4) 0.046(4) 0.053(4) -0.011(4) 0.005(3) -0.008(3) C13 0.030(3) 0.051(4) 0.030(3) -0.003(3) -0.001(3) -0.002(3) C14 0.058(5) 0.046(4) 0.047(4) 0.010(4) 0.003(4) 0.007(4) C15 0.070(5) 0.071(6) 0.047(5) 0.015(4) -0.005(4) 0.006(5) C16 0.053(5) 0.094(7) 0.035(4) 0.013(5) -0.004(4) -0.010(5) C17 0.043(4) 0.081(6) 0.037(4) -0.008(4) 0.002(3) 0.001(4) C18 0.037(3) 0.051(4) 0.046(4) -0.001(3) -0.001(3) 0.000(3) C19 0.046(4) 0.061(5) 0.064(5) 0.013(4) 0.011(4) 0.008(4) C20 0.065(5) 0.051(5) 0.069(6) -0.011(5) -0.006(4) 0.001(4) C21 0.066(5) 0.072(6) 0.045(5) 0.005(4) -0.008(4) -0.016(5) C22 0.084(6) 0.062(6) 0.073(6) 0.022(5) 0.016(5) 0.002(5) C23 0.072(6) 0.084(7) 0.078(7) 0.017(6) -0.011(5) 0.013(5) C24 0.079(7) 0.100(9) 0.140(12) 0.064(9) -0.002(7) -0.010(7) C25 0.047(4) 0.049(5) 0.095(7) 0.027(5) 0.008(4) 0.003(4) C26 0.076(6) 0.055(6) 0.118(9) 0.002(6) 0.019(6) 0.002(5) C27 0.068(6) 0.094(8) 0.102(8) 0.040(7) -0.007(6) 0.010(6) _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 Br1 Ni1 2.3399(13) . ? Br2 Ni1 2.3464(14) . ? Br3 Ni1 2.3607(13) . ? Ni1 P1 2.3076(19) . ? P1 C1 1.813(7) . ? P1 C13 1.814(7) . ? P1 C7 1.829(7) . ? N1 C19 1.332(11) . ? N1 C20 1.373(11) . ? N1 C22 1.504(11) . ? N2 C19 1.301(10) . ? N2 C21 1.378(11) . ? N2 C25 1.503(10) . ? C1 C2 1.392(11) . ? C1 C6 1.403(10) . ? C2 C3 1.361(13) . ? C2 H2 0.9400 . ? C3 C4 1.364(13) . ? C3 H3 0.9400 . ? C4 C5 1.361(13) . ? C4 H4 0.9400 . ? C5 C6 1.391(11) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C8 1.359(10) . ? C7 C12 1.382(10) . ? C8 C9 1.383(12) . ? C8 H8 0.9400 . ? C9 C10 1.344(14) . ? C9 H9 0.9400 . ? C10 C11 1.363(12) . ? C10 H10 0.9400 . ? C11 C12 1.398(10) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 C14 1.385(10) . ? C13 C18 1.411(10) . ? C14 C15 1.384(11) . ? C14 H14 0.9400 . ? C15 C16 1.343(13) . ? C15 H15 0.9400 . ? C16 C17 1.370(13) . ? C16 H16 0.9400 . ? C17 C18 1.390(11) . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? C19 H19 0.9400 . ? C20 C21 1.328(13) . ? C20 H20 0.9400 . ? C21 H21 0.9400 . ? C22 C24 1.425(14) . ? C22 C23 1.482(13) . ? C22 H22 0.9900 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 C26 1.508(15) . ? C25 C27 1.528(14) . ? C25 H25 0.9900 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 H26C 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? 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 P1 Ni1 Br1 103.62(6) . . ? P1 Ni1 Br2 106.22(6) . . ? Br1 Ni1 Br2 106.70(6) . . ? P1 Ni1 Br3 102.60(6) . . ? Br1 Ni1 Br3 111.56(5) . . ? Br2 Ni1 Br3 124.11(5) . . ? C1 P1 C13 105.3(3) . . ? C1 P1 C7 105.6(3) . . ? C13 P1 C7 104.6(3) . . ? C1 P1 Ni1 112.8(2) . . ? C13 P1 Ni1 113.0(2) . . ? C7 P1 Ni1 114.7(2) . . ? C19 N1 C20 108.2(7) . . ? C19 N1 C22 122.1(8) . . ? C20 N1 C22 129.8(8) . . ? C19 N2 C21 109.2(7) . . ? C19 N2 C25 126.6(7) . . ? C21 N2 C25 124.2(7) . . ? C2 C1 C6 118.2(7) . . ? C2 C1 P1 119.6(6) . . ? C6 C1 P1 122.2(6) . . ? C3 C2 C1 120.9(8) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.4(9) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.9(8) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 121.9(8) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.7(7) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C8 C7 C12 117.8(7) . . ? C8 C7 P1 119.9(6) . . ? C12 C7 P1 122.3(5) . . ? C7 C8 C9 121.6(8) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 120.9(9) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.0(8) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C10 C11 C12 120.7(8) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C7 C12 C11 120.0(7) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C18 119.4(7) . . ? C14 C13 P1 118.9(6) . . ? C18 C13 P1 121.7(6) . . ? C15 C14 C13 118.9(8) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 122.6(8) . . ? C16 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? C15 C16 C17 119.0(8) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C18 121.5(8) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C13 118.4(8) . . ? C17 C18 H18 120.8 . . ? C13 C18 H18 120.8 . . ? N2 C19 N1 108.5(8) . . ? N2 C19 H19 125.8 . . ? N1 C19 H19 125.8 . . ? C21 C20 N1 107.3(8) . . ? C21 C20 H20 126.3 . . ? N1 C20 H20 126.3 . . ? C20 C21 N2 106.8(8) . . ? C20 C21 H21 126.6 . . ? N2 C21 H21 126.6 . . ? C24 C22 C23 118.2(10) . . ? C24 C22 N1 110.5(9) . . ? C23 C22 N1 109.6(8) . . ? C24 C22 H22 105.9 . . ? C23 C22 H22 105.9 . . ? N1 C22 H22 105.9 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 C26 110.1(8) . . ? N2 C25 C27 108.7(8) . . ? C26 C25 C27 115.7(8) . . ? N2 C25 H25 107.3 . . ? C26 C25 H25 107.3 . . ? C27 C25 H25 107.3 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br1 Ni1 P1 C1 72.0(2) . . . . ? Br2 Ni1 P1 C1 -175.8(2) . . . . ? Br3 Ni1 P1 C1 -44.2(2) . . . . ? Br1 Ni1 P1 C13 -47.3(3) . . . . ? Br2 Ni1 P1 C13 64.9(3) . . . . ? Br3 Ni1 P1 C13 -163.5(3) . . . . ? Br1 Ni1 P1 C7 -167.0(3) . . . . ? Br2 Ni1 P1 C7 -54.8(3) . . . . ? Br3 Ni1 P1 C7 76.8(3) . . . . ? C13 P1 C1 C2 97.6(6) . . . . ? C7 P1 C1 C2 -152.1(6) . . . . ? Ni1 P1 C1 C2 -26.0(7) . . . . ? C13 P1 C1 C6 -79.8(6) . . . . ? C7 P1 C1 C6 30.5(6) . . . . ? Ni1 P1 C1 C6 156.6(5) . . . . ? C6 C1 C2 C3 0.6(12) . . . . ? P1 C1 C2 C3 -176.9(7) . . . . ? C1 C2 C3 C4 -0.8(14) . . . . ? C2 C3 C4 C5 -0.6(15) . . . . ? C3 C4 C5 C6 2.4(14) . . . . ? C4 C5 C6 C1 -2.6(12) . . . . ? C2 C1 C6 C5 1.0(11) . . . . ? P1 C1 C6 C5 178.5(6) . . . . ? C1 P1 C7 C8 75.7(7) . . . . ? C13 P1 C7 C8 -173.5(7) . . . . ? Ni1 P1 C7 C8 -49.2(7) . . . . ? C1 P1 C7 C12 -105.6(6) . . . . ? C13 P1 C7 C12 5.2(7) . . . . ? Ni1 P1 C7 C12 129.5(6) . . . . ? C12 C7 C8 C9 1.9(14) . . . . ? P1 C7 C8 C9 -179.4(8) . . . . ? C7 C8 C9 C10 -1.5(16) . . . . ? C8 C9 C10 C11 -0.5(16) . . . . ? C9 C10 C11 C12 2.0(13) . . . . ? C8 C7 C12 C11 -0.3(11) . . . . ? P1 C7 C12 C11 -179.1(6) . . . . ? C10 C11 C12 C7 -1.6(12) . . . . ? C1 P1 C13 C14 -178.2(6) . . . . ? C7 P1 C13 C14 70.8(6) . . . . ? Ni1 P1 C13 C14 -54.6(6) . . . . ? C1 P1 C13 C18 1.2(6) . . . . ? C7 P1 C13 C18 -109.9(6) . . . . ? Ni1 P1 C13 C18 124.7(5) . . . . ? C18 C13 C14 C15 -0.4(11) . . . . ? P1 C13 C14 C15 178.9(6) . . . . ? C13 C14 C15 C16 2.2(13) . . . . ? C14 C15 C16 C17 -2.6(13) . . . . ? C15 C16 C17 C18 1.3(12) . . . . ? C16 C17 C18 C13 0.3(11) . . . . ? C14 C13 C18 C17 -0.8(10) . . . . ? P1 C13 C18 C17 179.9(5) . . . . ? C21 N2 C19 N1 0.7(9) . . . . ? C25 N2 C19 N1 -178.9(7) . . . . ? C20 N1 C19 N2 -0.4(9) . . . . ? C22 N1 C19 N2 178.1(7) . . . . ? C19 N1 C20 C21 0.0(10) . . . . ? C22 N1 C20 C21 -178.4(8) . . . . ? N1 C20 C21 N2 0.4(9) . . . . ? C19 N2 C21 C20 -0.7(9) . . . . ? C25 N2 C21 C20 178.9(7) . . . . ? C19 N1 C22 C24 -89.4(12) . . . . ? C20 N1 C22 C24 88.8(12) . . . . ? C19 N1 C22 C23 138.7(9) . . . . ? C20 N1 C22 C23 -43.2(13) . . . . ? C19 N2 C25 C26 -9.5(11) . . . . ? C21 N2 C25 C26 171.0(8) . . . . ? C19 N2 C25 C27 118.2(9) . . . . ? C21 N2 C25 C27 -61.3(10) . . . . ? 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 C25 H25 Br3 0.99 2.92 3.814(8) 150.1 4_566 C20 H20 Br3 0.94 2.87 3.799(9) 168.4 4_576 C21 H21 Br2 0.94 2.94 3.811(9) 155.5 4_566 C3 H3 Br2 0.94 2.75 3.634(9) 157.7 1_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.545 _refine_diff_density_min -1.406 _refine_diff_density_rms 0.117 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 867539' #TrackingRef 'shelxl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 N2, C18 H15 Cl3 Ni P' _chemical_formula_sum 'C27 H32 Cl3 N2 Ni P' _chemical_formula_weight 580.58 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 15.958(4) _cell_length_b 9.663(2) _cell_length_c 19.083(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.547(4) _cell_angle_gamma 90.00 _cell_volume 2942.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8586 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.004 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.608 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22080 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.0997 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5339 _reflns_number_gt 2895 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0679P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5339 _refine_ls_number_parameters 312 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1651 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.942 _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 0.30101(4) 0.35936(6) 0.36156(3) 0.0548(2) Uani 1 1 d . . . Cl1 Cl 0.39552(8) 0.46853(14) 0.42795(8) 0.0792(4) Uani 1 1 d . . . Cl2 Cl 0.31232(12) 0.13335(13) 0.37611(10) 0.1053(6) Uani 1 1 d . . . Cl3 Cl 0.28635(9) 0.45024(13) 0.25415(7) 0.0756(4) Uani 1 1 d . . . P1 P 0.17537(7) 0.41681(11) 0.41362(6) 0.0465(3) Uani 1 1 d . . . N1 N 0.3612(3) 0.6816(5) 0.6183(3) 0.0749(12) Uani 1 1 d . . . N2 N 0.3844(2) 0.4880(4) 0.6688(2) 0.0614(11) Uani 1 1 d . . . C1 C 0.1463(3) 0.5947(4) 0.3984(2) 0.0496(11) Uani 1 1 d . . . C2 C 0.2090(3) 0.6893(5) 0.3855(3) 0.0683(14) Uani 1 1 d . . . H2 H 0.2641 0.6588 0.3827 0.082 Uiso 1 1 calc R . . C3 C 0.1919(4) 0.8271(5) 0.3768(3) 0.0865(19) Uani 1 1 d . . . H3 H 0.2350 0.8896 0.3688 0.104 Uiso 1 1 calc R . . C4 C 0.1102(5) 0.8723(5) 0.3801(3) 0.0841(18) Uani 1 1 d . . . H4 H 0.0981 0.9657 0.3742 0.101 Uiso 1 1 calc R . . C5 C 0.0471(4) 0.7807(6) 0.3920(3) 0.0722(15) Uani 1 1 d . . . H5 H -0.0080 0.8116 0.3941 0.087 Uiso 1 1 calc R . . C6 C 0.0650(3) 0.6422(5) 0.4011(2) 0.0558(12) Uani 1 1 d . . . H6 H 0.0216 0.5800 0.4090 0.067 Uiso 1 1 calc R . . C7 C 0.0848(3) 0.3158(4) 0.3852(2) 0.0476(11) Uani 1 1 d . . . C8 C 0.0706(4) 0.3000(6) 0.3144(3) 0.0809(16) Uani 1 1 d . . . H8 H 0.1061 0.3419 0.2824 0.097 Uiso 1 1 calc R . . C9 C 0.0033(4) 0.2212(7) 0.2911(3) 0.100(2) Uani 1 1 d . . . H9 H -0.0063 0.2117 0.2432 0.120 Uiso 1 1 calc R . . C10 C -0.0488(4) 0.1577(6) 0.3365(4) 0.0809(17) Uani 1 1 d . . . H10 H -0.0935 0.1048 0.3199 0.097 Uiso 1 1 calc R . . C11 C -0.0352(3) 0.1720(5) 0.4068(3) 0.0728(15) Uani 1 1 d . . . H11 H -0.0706 0.1294 0.4386 0.087 Uiso 1 1 calc R . . C12 C 0.0319(3) 0.2506(4) 0.4302(3) 0.0587(13) Uani 1 1 d . . . H12 H 0.0412 0.2593 0.4782 0.070 Uiso 1 1 calc R . . C13 C 0.1774(2) 0.3966(4) 0.5079(2) 0.0450(10) Uani 1 1 d . . . C14 C 0.2026(3) 0.2714(5) 0.5360(3) 0.0645(13) Uani 1 1 d . . . H14 H 0.2177 0.1993 0.5064 0.077 Uiso 1 1 calc R . . C15 C 0.2056(4) 0.2526(6) 0.6079(3) 0.0765(16) Uani 1 1 d . . . H15 H 0.2230 0.1680 0.6261 0.092 Uiso 1 1 calc R . . C16 C 0.1833(3) 0.3574(6) 0.6525(3) 0.0691(15) Uani 1 1 d . . . H16 H 0.1853 0.3437 0.7007 0.083 Uiso 1 1 calc R . . C17 C 0.1582(3) 0.4819(6) 0.6257(3) 0.0658(13) Uani 1 1 d . . . H17 H 0.1429 0.5531 0.6557 0.079 Uiso 1 1 calc R . . C18 C 0.1556(3) 0.5025(5) 0.5533(2) 0.0553(12) Uani 1 1 d . . . H18 H 0.1390 0.5879 0.5354 0.066 Uiso 1 1 calc R . . C19 C 0.3909(3) 0.5557(5) 0.6088(3) 0.0685(14) Uani 1 1 d . . . H19 H 0.4126 0.5207 0.5674 0.082 Uiso 1 1 calc R . . C20 C 0.3375(3) 0.6965(6) 0.6862(3) 0.0750(15) Uani 1 1 d . . . H20 H 0.3166 0.7762 0.7069 0.090 Uiso 1 1 calc R . . C21 C 0.3500(3) 0.5743(6) 0.7171(3) 0.0744(15) Uani 1 1 d . . . H21 H 0.3376 0.5521 0.7633 0.089 Uiso 1 1 calc R . . C22 C 0.3611(4) 0.7907(7) 0.5615(4) 0.119(3) Uani 1 1 d D . . H22 H 0.3578 0.7358 0.5184 0.143 Uiso 1 1 calc R . . C23 C 0.2801(4) 0.8651(6) 0.5617(4) 0.108(2) Uani 1 1 d D . . H23A H 0.2776 0.9241 0.6021 0.162 Uiso 1 1 calc R . . H23B H 0.2350 0.7993 0.5632 0.162 Uiso 1 1 calc R . . H23C H 0.2750 0.9201 0.5200 0.162 Uiso 1 1 calc R . . C24 C 0.4382(5) 0.8563(8) 0.5559(5) 0.147(3) Uani 1 1 d D . . H24A H 0.4386 0.9120 0.5143 0.221 Uiso 1 1 calc R . . H24B H 0.4818 0.7881 0.5535 0.221 Uiso 1 1 calc R . . H24C H 0.4473 0.9141 0.5962 0.221 Uiso 1 1 calc R . . C25 C 0.4114(4) 0.3432(5) 0.6813(3) 0.0810(17) Uani 1 1 d . . . H25 H 0.3641 0.2935 0.7019 0.097 Uiso 1 1 calc R . . C26 C 0.4337(4) 0.2711(6) 0.6144(4) 0.107(2) Uani 1 1 d . . . H26A H 0.3890 0.2825 0.5808 0.160 Uiso 1 1 calc R . . H26B H 0.4421 0.1743 0.6234 0.160 Uiso 1 1 calc R . . H26C H 0.4842 0.3103 0.5961 0.160 Uiso 1 1 calc R . . C27 C 0.4827(4) 0.3430(7) 0.7345(4) 0.118(2) Uani 1 1 d . . . H27A H 0.5292 0.3940 0.7162 0.177 Uiso 1 1 calc R . . H27B H 0.4996 0.2495 0.7439 0.177 Uiso 1 1 calc R . . H27C H 0.4642 0.3855 0.7772 0.177 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 0.0562(4) 0.0547(4) 0.0536(4) -0.0064(3) 0.0082(3) -0.0043(3) Cl1 0.0634(9) 0.0903(10) 0.0836(10) -0.0129(8) -0.0069(7) -0.0118(7) Cl2 0.1307(15) 0.0534(8) 0.1326(15) -0.0119(8) 0.0499(12) -0.0098(8) Cl3 0.1080(11) 0.0679(8) 0.0509(8) -0.0034(6) 0.0062(7) -0.0074(7) P1 0.0507(8) 0.0455(7) 0.0432(7) -0.0005(5) 0.0006(5) -0.0018(5) N1 0.063(3) 0.072(3) 0.090(4) 0.017(3) 0.003(2) 0.002(2) N2 0.051(2) 0.064(3) 0.069(3) 0.014(2) 0.001(2) -0.0036(19) C1 0.061(3) 0.049(2) 0.039(3) -0.001(2) -0.001(2) -0.003(2) C2 0.063(3) 0.053(3) 0.089(4) -0.002(3) 0.013(3) 0.000(3) C3 0.089(5) 0.052(3) 0.119(5) 0.008(3) 0.025(4) -0.005(3) C4 0.119(6) 0.051(3) 0.082(4) 0.006(3) -0.001(4) 0.018(4) C5 0.075(4) 0.075(4) 0.066(4) 0.006(3) 0.008(3) 0.015(3) C6 0.054(3) 0.057(3) 0.056(3) 0.010(2) 0.003(2) 0.004(2) C7 0.048(3) 0.050(3) 0.044(3) -0.003(2) 0.001(2) 0.002(2) C8 0.086(4) 0.094(4) 0.063(4) 0.001(3) -0.008(3) -0.029(3) C9 0.115(6) 0.121(5) 0.063(4) -0.016(4) -0.026(4) -0.021(4) C10 0.063(4) 0.074(4) 0.106(5) -0.015(4) -0.017(3) -0.007(3) C11 0.059(4) 0.072(3) 0.087(5) -0.012(3) 0.004(3) -0.005(3) C12 0.058(3) 0.059(3) 0.060(3) -0.010(2) -0.001(2) -0.008(2) C13 0.039(3) 0.050(2) 0.046(3) 0.001(2) 0.0028(19) -0.006(2) C14 0.072(4) 0.062(3) 0.059(3) 0.006(3) -0.002(3) 0.012(3) C15 0.090(4) 0.077(4) 0.062(4) 0.024(3) -0.006(3) 0.011(3) C16 0.065(3) 0.099(4) 0.043(3) 0.013(3) -0.001(2) -0.004(3) C17 0.063(3) 0.085(4) 0.050(3) -0.009(3) -0.006(2) 0.002(3) C18 0.052(3) 0.063(3) 0.050(3) -0.002(2) -0.008(2) -0.002(2) C19 0.054(3) 0.074(4) 0.079(4) 0.014(3) 0.010(3) 0.011(3) C20 0.083(4) 0.059(3) 0.083(4) -0.010(3) -0.003(3) -0.003(3) C21 0.082(4) 0.087(4) 0.055(3) -0.005(3) 0.003(3) -0.015(3) C22 0.100(6) 0.105(5) 0.153(7) 0.071(5) 0.008(5) 0.010(5) C23 0.105(5) 0.105(5) 0.115(6) 0.024(4) -0.019(4) 0.029(4) C24 0.117(7) 0.132(6) 0.193(9) 0.089(6) 0.004(6) -0.027(5) C25 0.069(4) 0.060(3) 0.114(5) 0.028(3) 0.007(3) 0.005(3) C26 0.108(5) 0.065(4) 0.148(7) -0.004(4) 0.031(5) 0.004(3) C27 0.084(5) 0.118(5) 0.151(7) 0.052(5) -0.027(5) 0.004(4) _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 Cl2 2.2087(16) . ? Ni1 Cl1 2.2261(14) . ? Ni1 Cl3 2.2402(15) . ? Ni1 P1 2.3136(13) . ? P1 C1 1.803(4) . ? P1 C13 1.811(4) . ? P1 C7 1.822(4) . ? N1 C19 1.319(6) . ? N1 C20 1.360(7) . ? N1 C22 1.512(7) . ? N2 C19 1.323(6) . ? N2 C21 1.362(6) . ? N2 C25 1.482(6) . ? C1 C6 1.376(6) . ? C1 C2 1.379(6) . ? C2 C3 1.369(7) . ? C2 H2 0.9300 . ? C3 C4 1.377(8) . ? C3 H3 0.9300 . ? C4 C5 1.360(7) . ? C4 H4 0.9300 . ? C5 C6 1.380(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.364(6) . ? C7 C8 1.377(6) . ? C8 C9 1.387(7) . ? C8 H8 0.9300 . ? C9 C10 1.353(8) . ? C9 H9 0.9300 . ? C10 C11 1.364(7) . ? C10 H10 0.9300 . ? C11 C12 1.383(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.382(6) . ? C13 C18 1.387(6) . ? C14 C15 1.384(7) . ? C14 H14 0.9300 . ? C15 C16 1.372(7) . ? C15 H15 0.9300 . ? C16 C17 1.366(7) . ? C16 H16 0.9300 . ? C17 C18 1.395(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.334(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C24 1.388(8) . ? C22 C23 1.480(8) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.500(8) . ? C25 C27 1.518(8) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? 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 Cl2 Ni1 Cl1 110.05(7) . . ? Cl2 Ni1 Cl3 120.68(6) . . ? Cl1 Ni1 Cl3 113.53(6) . . ? Cl2 Ni1 P1 104.68(5) . . ? Cl1 Ni1 P1 103.13(5) . . ? Cl3 Ni1 P1 102.44(5) . . ? C1 P1 C13 105.33(19) . . ? C1 P1 C7 105.1(2) . . ? C13 P1 C7 104.14(19) . . ? C1 P1 Ni1 112.51(16) . . ? C13 P1 Ni1 113.18(14) . . ? C7 P1 Ni1 115.60(14) . . ? C19 N1 C20 109.4(5) . . ? C19 N1 C22 122.8(6) . . ? C20 N1 C22 127.7(6) . . ? C19 N2 C21 108.5(4) . . ? C19 N2 C25 125.5(5) . . ? C21 N2 C25 126.0(5) . . ? C6 C1 C2 118.1(4) . . ? C6 C1 P1 123.6(3) . . ? C2 C1 P1 118.3(4) . . ? C3 C2 C1 121.4(5) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 119.4(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.0(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.8(5) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C12 C7 C8 118.0(4) . . ? C12 C7 P1 123.7(4) . . ? C8 C7 P1 118.3(4) . . ? C7 C8 C9 119.7(5) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 121.5(6) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.4(5) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C11 C12 119.3(5) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C7 C12 C11 122.1(5) . . ? C7 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C14 C13 C18 118.6(4) . . ? C14 C13 P1 118.8(3) . . ? C18 C13 P1 122.6(3) . . ? C13 C14 C15 120.4(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.7(5) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 119.6(5) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.2(5) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 120.4(4) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? N1 C19 N2 107.8(5) . . ? N1 C19 H19 126.1 . . ? N2 C19 H19 126.1 . . ? C21 C20 N1 106.6(5) . . ? C21 C20 H20 126.7 . . ? N1 C20 H20 126.7 . . ? C20 C21 N2 107.6(5) . . ? C20 C21 H21 126.2 . . ? N2 C21 H21 126.2 . . ? C24 C22 C23 123.6(6) . . ? C24 C22 N1 112.3(6) . . ? C23 C22 N1 109.3(6) . . ? C24 C22 H22 103.0 . . ? C23 C22 H22 103.0 . . ? N1 C22 H22 103.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C25 C26 111.9(5) . . ? N2 C25 C27 108.8(5) . . ? C26 C25 C27 112.8(6) . . ? N2 C25 H25 107.7 . . ? C26 C25 H25 107.7 . . ? C27 C25 H25 107.7 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Ni1 P1 C1 -172.66(17) . . . . ? Cl1 Ni1 P1 C1 72.19(17) . . . . ? Cl3 Ni1 P1 C1 -45.93(16) . . . . ? Cl2 Ni1 P1 C13 68.08(16) . . . . ? Cl1 Ni1 P1 C13 -47.07(15) . . . . ? Cl3 Ni1 P1 C13 -165.19(15) . . . . ? Cl2 Ni1 P1 C7 -51.91(18) . . . . ? Cl1 Ni1 P1 C7 -167.07(16) . . . . ? Cl3 Ni1 P1 C7 74.81(17) . . . . ? C13 P1 C1 C6 -80.1(4) . . . . ? C7 P1 C1 C6 29.6(4) . . . . ? Ni1 P1 C1 C6 156.2(3) . . . . ? C13 P1 C1 C2 98.0(4) . . . . ? C7 P1 C1 C2 -152.4(4) . . . . ? Ni1 P1 C1 C2 -25.8(4) . . . . ? C6 C1 C2 C3 1.3(7) . . . . ? P1 C1 C2 C3 -176.9(4) . . . . ? C1 C2 C3 C4 -0.9(9) . . . . ? C2 C3 C4 C5 0.1(9) . . . . ? C3 C4 C5 C6 0.2(9) . . . . ? C2 C1 C6 C5 -1.0(7) . . . . ? P1 C1 C6 C5 177.1(4) . . . . ? C4 C5 C6 C1 0.3(8) . . . . ? C1 P1 C7 C12 -107.1(4) . . . . ? C13 P1 C7 C12 3.4(4) . . . . ? Ni1 P1 C7 C12 128.2(3) . . . . ? C1 P1 C7 C8 75.4(4) . . . . ? C13 P1 C7 C8 -174.1(4) . . . . ? Ni1 P1 C7 C8 -49.3(4) . . . . ? C12 C7 C8 C9 1.0(8) . . . . ? P1 C7 C8 C9 178.6(5) . . . . ? C7 C8 C9 C10 -0.7(10) . . . . ? C8 C9 C10 C11 0.4(10) . . . . ? C9 C10 C11 C12 -0.3(8) . . . . ? C8 C7 C12 C11 -0.9(7) . . . . ? P1 C7 C12 C11 -178.4(4) . . . . ? C10 C11 C12 C7 0.6(7) . . . . ? C1 P1 C13 C14 -176.4(4) . . . . ? C7 P1 C13 C14 73.3(4) . . . . ? Ni1 P1 C13 C14 -53.0(4) . . . . ? C1 P1 C13 C18 2.8(4) . . . . ? C7 P1 C13 C18 -107.5(4) . . . . ? Ni1 P1 C13 C18 126.1(3) . . . . ? C18 C13 C14 C15 0.2(7) . . . . ? P1 C13 C14 C15 179.5(4) . . . . ? C13 C14 C15 C16 0.3(8) . . . . ? C14 C15 C16 C17 -0.3(8) . . . . ? C15 C16 C17 C18 -0.2(8) . . . . ? C14 C13 C18 C17 -0.7(6) . . . . ? P1 C13 C18 C17 -179.9(3) . . . . ? C16 C17 C18 C13 0.7(7) . . . . ? C20 N1 C19 N2 1.9(6) . . . . ? C22 N1 C19 N2 177.9(5) . . . . ? C21 N2 C19 N1 -0.3(6) . . . . ? C25 N2 C19 N1 -179.4(4) . . . . ? C19 N1 C20 C21 -2.7(6) . . . . ? C22 N1 C20 C21 -178.5(5) . . . . ? N1 C20 C21 N2 2.5(6) . . . . ? C19 N2 C21 C20 -1.4(6) . . . . ? C25 N2 C21 C20 177.7(5) . . . . ? C19 N1 C22 C24 -81.5(9) . . . . ? C20 N1 C22 C24 93.7(8) . . . . ? C19 N1 C22 C23 137.5(6) . . . . ? C20 N1 C22 C23 -47.2(9) . . . . ? C19 N2 C25 C26 -10.1(7) . . . . ? C21 N2 C25 C26 170.9(5) . . . . ? C19 N2 C25 C27 115.2(6) . . . . ? C21 N2 C25 C27 -63.8(7) . . . . ? 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 C25 H25 Cl3 0.98 2.85 3.743(5) 152.4 4_566 C20 H20 Cl3 0.93 2.84 3.745(6) 166.2 4_576 C21 H21 Cl2 0.93 2.83 3.692(6) 154.0 4_566 C3 H3 Cl2 0.93 2.66 3.529(6) 155.5 1_565 C19 H19 Cl1 0.93 2.72 3.555(6) 149.9 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.631 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.081 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 874238' #TrackingRef 'shelxl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H37 N2, C18 H15 Cl3 Ni P' _chemical_formula_sum 'C45 H52 Cl3 N2 Ni P' _chemical_formula_weight 816.92 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y, z+1/2' _cell_length_a 17.270(7) _cell_length_b 14.224(5) _cell_length_c 17.322(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4255(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 12452 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.562 _exptl_absorpt_correction_T_max 0.707 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19076 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7031 _reflns_number_gt 6354 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0820P)^2^+0.1454P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(19) _refine_ls_number_reflns 7031 _refine_ls_number_parameters 467 _refine_ls_number_restraints 57 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.147 _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 Ni1 Ni 0.28334(3) 0.55607(3) 0.59135(4) 0.03525(16) Uani 1 1 d . . . Cl1 Cl 0.39851(7) 0.52771(9) 0.64793(10) 0.0552(3) Uani 1 1 d . . . Cl2 Cl 0.24064(11) 0.42215(10) 0.54031(10) 0.0714(5) Uani 1 1 d . . . Cl3 Cl 0.26401(11) 0.68530(10) 0.52007(10) 0.0656(4) Uani 1 1 d . . . P1 P 0.20065(6) 0.58954(7) 0.69313(7) 0.0291(2) Uani 1 1 d . . . N1 N 0.0466(2) 0.2073(2) 0.7122(3) 0.0367(9) Uani 1 1 d . . . N2 N 0.0836(2) 0.1812(2) 0.5952(3) 0.0462(10) Uani 1 1 d . . . C1 C 0.1821(2) 0.4958(3) 0.7630(3) 0.0327(9) Uani 1 1 d . . . C2 C 0.2410(3) 0.4317(3) 0.7798(3) 0.0398(11) Uani 1 1 d . . . H2 H 0.2879 0.4329 0.7523 0.048 Uiso 1 1 calc R . . C3 C 0.2287(3) 0.3656(3) 0.8385(4) 0.0505(14) Uani 1 1 d . . . H3 H 0.2685 0.3231 0.8508 0.061 Uiso 1 1 calc R . . C4 C 0.1606(3) 0.3610(3) 0.8785(3) 0.0485(13) Uani 1 1 d . . . H4 H 0.1538 0.3161 0.9178 0.058 Uiso 1 1 calc R . . C5 C 0.1018(3) 0.4233(3) 0.8603(3) 0.0479(12) Uani 1 1 d . . . H5 H 0.0543 0.4197 0.8867 0.057 Uiso 1 1 calc R . . C6 C 0.1122(3) 0.4914(3) 0.8035(3) 0.0397(10) Uani 1 1 d . . . H6 H 0.0723 0.5343 0.7923 0.048 Uiso 1 1 calc R . . C7 C 0.1055(3) 0.6232(3) 0.6602(3) 0.0361(10) Uani 1 1 d . . . C8 C 0.0671(3) 0.5633(4) 0.6088(3) 0.0521(14) Uani 1 1 d . . . H8 H 0.0906 0.5069 0.5928 0.062 Uiso 1 1 calc R . . C9 C -0.0059(3) 0.5873(5) 0.5817(4) 0.0691(17) Uani 1 1 d . . . H9 H -0.0323 0.5456 0.5488 0.083 Uiso 1 1 calc R . . C10 C -0.0400(3) 0.6702(5) 0.6016(4) 0.0660(17) Uani 1 1 d . . . H10 H -0.0883 0.6867 0.5805 0.079 Uiso 1 1 calc R . . C11 C -0.0034(4) 0.7297(4) 0.6528(4) 0.0641(16) Uani 1 1 d . . . H11 H -0.0273 0.7862 0.6679 0.077 Uiso 1 1 calc R . . C12 C 0.0696(3) 0.7057(3) 0.6822(4) 0.0519(13) Uani 1 1 d . . . H12 H 0.0943 0.7461 0.7174 0.062 Uiso 1 1 calc R . . C13 C 0.2346(3) 0.6871(3) 0.7523(3) 0.0346(10) Uani 1 1 d . . . C14 C 0.2221(3) 0.6924(4) 0.8301(3) 0.0493(13) Uani 1 1 d . . . H14 H 0.1961 0.6434 0.8556 0.059 Uiso 1 1 calc R . . C15 C 0.2481(4) 0.7710(4) 0.8724(4) 0.0614(16) Uani 1 1 d . . . H15 H 0.2384 0.7748 0.9257 0.074 Uiso 1 1 calc R . . C16 C 0.2867(3) 0.8406(4) 0.8367(4) 0.0568(16) Uani 1 1 d . . . H16 H 0.3025 0.8939 0.8647 0.068 Uiso 1 1 calc R . . C17 C 0.3031(5) 0.8337(4) 0.7592(5) 0.076(2) Uani 1 1 d . . . H17 H 0.3325 0.8808 0.7349 0.091 Uiso 1 1 calc R . . C18 C 0.2765(4) 0.7571(4) 0.7164(4) 0.0592(16) Uani 1 1 d . . . H18 H 0.2870 0.7533 0.6633 0.071 Uiso 1 1 calc R . . C19 C 0.0344(3) 0.1541(3) 0.6496(3) 0.0429(11) Uani 1 1 d . . . H19 H -0.0025 0.1059 0.6450 0.051 Uiso 1 1 calc R . . C20 C 0.1055(3) 0.2707(3) 0.6956(3) 0.0477(12) Uani 1 1 d . . . H20 H 0.1253 0.3171 0.7289 0.057 Uiso 1 1 calc R . . C21 C 0.1288(3) 0.2533(3) 0.6234(4) 0.0521(14) Uani 1 1 d . . . H21 H 0.1687 0.2845 0.5968 0.063 Uiso 1 1 calc R . . C22 C 0.0068(3) 0.2064(4) 0.7846(3) 0.0480(10) Uani 1 1 d U A . C23 C 0.0343(4) 0.1469(4) 0.8430(4) 0.0646(12) Uani 1 1 d DU . . C24 C -0.0059(5) 0.1642(5) 0.9187(4) 0.0796(14) Uani 1 1 d U A . H24 H 0.0082 0.1285 0.9622 0.096 Uiso 1 1 calc R . . C25 C -0.0617(5) 0.2299(6) 0.9254(5) 0.0842(15) Uani 1 1 d U . . H25 H -0.0843 0.2401 0.9741 0.101 Uiso 1 1 calc R A . C26 C -0.0847(4) 0.2784(5) 0.8689(4) 0.0708(13) Uani 1 1 d U A . H26 H -0.1253 0.3214 0.8768 0.085 Uiso 1 1 calc R . . C27 C -0.0531(3) 0.2711(4) 0.7957(4) 0.0505(11) Uani 1 1 d U . . C28 C 0.0973(8) 0.0725(9) 0.8155(9) 0.064(2) Uiso 0.50 1 d PD A 1 C28' C 0.0909(8) 0.0726(9) 0.8438(8) 0.064(2) Uiso 0.50 1 d PD A 2 C29 C 0.0817(9) -0.0245(10) 0.7887(10) 0.081(3) Uiso 0.50 1 d PD A 1 C29' C 0.0911(9) 0.0076(10) 0.9082(9) 0.081(3) Uiso 0.50 1 d PD A 2 C30 C 0.1796(10) 0.0936(14) 0.8352(12) 0.084(3) Uiso 0.50 1 d PD A 1 C30' C 0.1698(9) 0.1074(14) 0.8121(12) 0.084(3) Uiso 0.50 1 d PD A 2 C31 C -0.0835(3) 0.3296(4) 0.7301(4) 0.0647(17) Uani 1 1 d . A . H31 H -0.0418 0.3335 0.6910 0.078 Uiso 1 1 calc R . . C32 C -0.1526(5) 0.2818(5) 0.6917(5) 0.084(2) Uani 1 1 d . . . H32A H -0.1948 0.2769 0.7284 0.126 Uiso 1 1 calc R A . H32B H -0.1378 0.2194 0.6746 0.126 Uiso 1 1 calc R . . H32C H -0.1692 0.3186 0.6476 0.126 Uiso 1 1 calc R . . C33 C -0.1034(5) 0.4300(5) 0.7536(8) 0.118(4) Uani 1 1 d . . . H33A H -0.0573 0.4610 0.7730 0.178 Uiso 1 1 calc R A . H33B H -0.1426 0.4288 0.7937 0.178 Uiso 1 1 calc R . . H33C H -0.1229 0.4639 0.7092 0.178 Uiso 1 1 calc R . . C34 C 0.0909(3) 0.1441(4) 0.5184(4) 0.0488(13) Uani 1 1 d . . . C35 C 0.0533(4) 0.1901(4) 0.4599(4) 0.0615(16) Uani 1 1 d . B . C36 C 0.0615(4) 0.1561(5) 0.3848(4) 0.0683(17) Uani 1 1 d . . . H36 H 0.0365 0.1863 0.3434 0.082 Uiso 1 1 calc R . . C37 C 0.1075(4) 0.0765(5) 0.3716(5) 0.071(2) Uani 1 1 d . . . H37 H 0.1131 0.0531 0.3212 0.085 Uiso 1 1 calc R . . C38 C 0.1438(4) 0.0331(5) 0.4309(4) 0.0629(16) Uani 1 1 d . . . H38 H 0.1744 -0.0201 0.4208 0.075 Uiso 1 1 calc R . . C39 C 0.1371(3) 0.0652(3) 0.5066(4) 0.0544(15) Uani 1 1 d . . . C40 C 0.0020(4) 0.2761(5) 0.4764(5) 0.080(2) Uani 1 1 d D . . C41 C -0.0802(5) 0.2456(9) 0.4814(8) 0.140(5) Uani 1 1 d . B . H41A H -0.0999 0.2332 0.4300 0.209 Uiso 1 1 calc R . . H41B H -0.1107 0.2949 0.5053 0.209 Uiso 1 1 calc R . . H41C H -0.0836 0.1888 0.5122 0.209 Uiso 1 1 calc R . . C42 C 0.0314(11) 0.3672(11) 0.4378(11) 0.089(3) Uiso 0.50 1 d PD B 1 C42' C 0.0083(11) 0.3525(12) 0.4161(11) 0.089(3) Uiso 0.50 1 d PD B 2 C43 C 0.1801(4) 0.0183(4) 0.5728(4) 0.0650(18) Uani 1 1 d . . . H43 H 0.1804 0.0622 0.6172 0.078 Uiso 1 1 calc R . . C44 C 0.1376(5) -0.0712(5) 0.5974(8) 0.111(3) Uani 1 1 d . . . H44A H 0.1325 -0.1129 0.5534 0.166 Uiso 1 1 calc R . . H44B H 0.0866 -0.0550 0.6167 0.166 Uiso 1 1 calc R . . H44C H 0.1668 -0.1026 0.6377 0.166 Uiso 1 1 calc R . . C45 C 0.2637(4) -0.0070(8) 0.5539(6) 0.098(3) Uani 1 1 d . . . H45A H 0.2890 0.0465 0.5300 0.146 Uiso 1 1 calc R . . H45B H 0.2646 -0.0599 0.5186 0.146 Uiso 1 1 calc R . . H45C H 0.2908 -0.0236 0.6010 0.146 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 0.0380(3) 0.0320(3) 0.0358(3) -0.0034(3) 0.0067(3) -0.0021(2) Cl1 0.0397(6) 0.0512(6) 0.0747(10) -0.0069(7) 0.0002(6) 0.0069(5) Cl2 0.0926(12) 0.0545(7) 0.0670(11) -0.0288(8) 0.0322(9) -0.0336(8) Cl3 0.0972(12) 0.0489(7) 0.0507(9) 0.0151(7) 0.0102(8) 0.0000(7) P1 0.0313(5) 0.0256(5) 0.0304(6) -0.0026(4) 0.0015(4) -0.0008(4) N1 0.0279(18) 0.0281(17) 0.054(3) -0.0031(17) 0.0063(16) -0.0044(14) N2 0.044(2) 0.0369(19) 0.058(3) -0.015(2) 0.016(2) -0.0087(15) C1 0.036(2) 0.030(2) 0.033(2) -0.0045(18) -0.0030(18) -0.0033(17) C2 0.046(3) 0.030(2) 0.043(3) -0.0030(19) -0.008(2) -0.0006(18) C3 0.066(3) 0.030(2) 0.056(4) 0.002(2) -0.024(3) 0.002(2) C4 0.075(4) 0.037(2) 0.033(3) 0.006(2) -0.005(2) -0.017(2) C5 0.067(3) 0.040(2) 0.037(3) 0.000(2) 0.012(2) -0.011(2) C6 0.042(2) 0.039(2) 0.038(3) 0.000(2) 0.002(2) -0.0030(18) C7 0.038(2) 0.040(2) 0.030(3) 0.005(2) -0.0014(18) 0.0033(17) C8 0.042(3) 0.065(3) 0.050(4) -0.012(2) -0.014(2) 0.008(2) C9 0.041(3) 0.104(5) 0.062(4) -0.003(4) -0.019(3) -0.010(3) C10 0.038(3) 0.093(4) 0.067(4) 0.022(4) -0.005(3) 0.015(3) C11 0.056(3) 0.057(3) 0.080(5) 0.010(3) -0.001(3) 0.015(3) C12 0.044(3) 0.041(2) 0.070(4) -0.001(3) 0.000(3) 0.005(2) C13 0.034(2) 0.030(2) 0.039(3) -0.0060(19) -0.0016(18) 0.0006(17) C14 0.063(3) 0.044(3) 0.041(3) -0.012(2) 0.004(2) -0.012(2) C15 0.076(4) 0.056(3) 0.053(4) -0.026(3) 0.008(3) -0.005(3) C16 0.067(4) 0.042(3) 0.062(4) -0.019(3) -0.016(3) -0.007(2) C17 0.114(6) 0.045(3) 0.069(5) -0.006(3) -0.011(4) -0.034(3) C18 0.086(4) 0.037(3) 0.054(4) -0.004(3) -0.002(3) -0.025(3) C19 0.040(2) 0.032(2) 0.057(3) -0.007(2) 0.009(2) -0.0044(18) C20 0.049(3) 0.040(2) 0.054(3) -0.007(2) 0.007(2) -0.018(2) C21 0.055(3) 0.036(2) 0.065(4) -0.011(2) 0.015(3) -0.020(2) C22 0.050(2) 0.044(2) 0.050(2) 0.0027(19) -0.0046(19) -0.0138(18) C23 0.068(3) 0.064(3) 0.062(3) 0.013(2) -0.020(2) -0.024(2) C24 0.092(3) 0.091(3) 0.056(3) 0.018(3) -0.015(3) -0.037(3) C25 0.086(3) 0.106(4) 0.061(3) 0.004(3) 0.010(3) -0.035(3) C26 0.069(3) 0.087(3) 0.056(3) -0.004(2) 0.021(2) -0.024(2) C27 0.046(2) 0.054(2) 0.051(3) -0.008(2) 0.013(2) -0.0140(17) C31 0.049(3) 0.054(3) 0.092(5) 0.001(3) 0.020(3) 0.014(2) C32 0.096(5) 0.069(4) 0.087(6) 0.003(4) -0.024(5) 0.007(4) C33 0.078(5) 0.059(4) 0.218(13) -0.038(6) -0.040(7) 0.027(4) C34 0.045(3) 0.045(3) 0.056(4) -0.016(3) 0.015(2) -0.002(2) C35 0.056(3) 0.062(4) 0.066(4) -0.016(3) 0.013(3) 0.000(3) C36 0.059(4) 0.081(4) 0.065(5) -0.006(3) 0.005(3) -0.001(3) C37 0.060(4) 0.083(4) 0.069(5) -0.033(4) 0.022(3) -0.006(3) C38 0.060(4) 0.062(3) 0.067(4) -0.017(3) 0.012(3) 0.008(3) C39 0.048(3) 0.044(3) 0.071(4) -0.019(3) 0.022(3) -0.007(2) C40 0.066(4) 0.083(5) 0.091(6) -0.011(4) 0.014(4) 0.023(4) C41 0.065(5) 0.185(11) 0.168(12) -0.015(9) -0.006(6) 0.053(6) C43 0.062(3) 0.048(3) 0.084(5) -0.021(3) 0.012(3) 0.000(2) C44 0.094(6) 0.056(4) 0.183(11) 0.021(6) -0.029(7) -0.015(3) C45 0.060(4) 0.146(8) 0.087(6) -0.030(6) -0.001(4) 0.010(5) _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 Cl2 2.2257(15) . ? Ni1 Cl3 2.2394(16) . ? Ni1 Cl1 2.2536(16) . ? Ni1 P1 2.3183(14) . ? P1 C7 1.804(4) . ? P1 C13 1.823(5) . ? P1 C1 1.830(5) . ? N1 C19 1.340(7) . ? N1 C20 1.389(6) . ? N1 C22 1.430(7) . ? N2 C19 1.324(7) . ? N2 C21 1.379(6) . ? N2 C34 1.436(7) . ? C1 C2 1.396(7) . ? C1 C6 1.397(7) . ? C2 C3 1.402(8) . ? C2 H2 0.9400 . ? C3 C4 1.366(9) . ? C3 H3 0.9400 . ? C4 C5 1.386(8) . ? C4 H4 0.9400 . ? C5 C6 1.393(7) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C12 1.381(7) . ? C7 C8 1.401(7) . ? C8 C9 1.388(8) . ? C8 H8 0.9400 . ? C9 C10 1.362(9) . ? C9 H9 0.9400 . ? C10 C11 1.381(10) . ? C10 H10 0.9400 . ? C11 C12 1.401(8) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 C14 1.367(8) . ? C13 C18 1.378(7) . ? C14 C15 1.409(8) . ? C14 H14 0.9400 . ? C15 C16 1.344(9) . ? C15 H15 0.9400 . ? C16 C17 1.377(10) . ? C16 H16 0.9400 . ? C17 C18 1.394(8) . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? C19 H19 0.9400 . ? C20 C21 1.336(8) . ? C20 H20 0.9400 . ? C21 H21 0.9400 . ? C22 C27 1.397(8) . ? C22 C23 1.402(8) . ? C23 C28' 1.440(13) . ? C23 C24 1.504(11) . ? C23 C28 1.591(13) . ? C24 C25 1.347(12) . ? C24 H24 0.9400 . ? C25 C26 1.262(11) . ? C25 H25 0.9400 . ? C26 C27 1.384(9) . ? C26 H26 0.9400 . ? C27 C31 1.503(9) . ? C28 C29 1.481(15) . ? C28 C30 1.492(16) . ? C28' C29' 1.448(15) . ? C28' C30' 1.551(16) . ? C31 C33 1.524(9) . ? C31 C32 1.527(10) . ? C31 H31 0.9900 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 H33C 0.9700 . ? C34 C35 1.371(9) . ? C34 C39 1.392(7) . ? C35 C36 1.395(10) . ? C35 C40 1.537(9) . ? C36 C37 1.401(9) . ? C36 H36 0.9400 . ? C37 C38 1.353(10) . ? C37 H37 0.9400 . ? C38 C39 1.392(9) . ? C38 H38 0.9400 . ? C39 C43 1.521(10) . ? C40 C41 1.486(13) . ? C40 C42' 1.511(15) . ? C40 C42 1.544(15) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C41 H41C 0.9700 . ? C43 C45 1.524(9) . ? C43 C44 1.530(10) . ? C43 H43 0.9900 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C44 H44C 0.9700 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C45 H45C 0.9700 . ? 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 Cl2 Ni1 Cl3 115.72(8) . . ? Cl2 Ni1 Cl1 108.18(7) . . ? Cl3 Ni1 Cl1 121.22(6) . . ? Cl2 Ni1 P1 105.88(5) . . ? Cl3 Ni1 P1 99.14(6) . . ? Cl1 Ni1 P1 104.46(6) . . ? C7 P1 C13 105.6(2) . . ? C7 P1 C1 104.1(2) . . ? C13 P1 C1 103.8(2) . . ? C7 P1 Ni1 112.02(17) . . ? C13 P1 Ni1 112.70(16) . . ? C1 P1 Ni1 117.49(15) . . ? C19 N1 C20 108.3(4) . . ? C19 N1 C22 129.0(4) . . ? C20 N1 C22 122.6(4) . . ? C19 N2 C21 109.1(5) . . ? C19 N2 C34 127.5(4) . . ? C21 N2 C34 123.4(4) . . ? C2 C1 C6 119.8(4) . . ? C2 C1 P1 119.1(4) . . ? C6 C1 P1 121.0(3) . . ? C1 C2 C3 118.6(5) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 122.0(5) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 119.1(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 120.7(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 119.8(5) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 118.7(4) . . ? C12 C7 P1 123.2(4) . . ? C8 C7 P1 118.1(3) . . ? C9 C8 C7 119.7(5) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 121.3(6) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.7(5) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 119.7(5) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C7 C12 C11 120.7(5) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C18 119.2(5) . . ? C14 C13 P1 123.1(4) . . ? C18 C13 P1 117.7(4) . . ? C13 C14 C15 120.4(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.2(6) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.9(5) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.4(6) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 119.8(6) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? N2 C19 N1 108.1(4) . . ? N2 C19 H19 125.9 . . ? N1 C19 H19 125.9 . . ? C21 C20 N1 107.1(4) . . ? C21 C20 H20 126.5 . . ? N1 C20 H20 126.5 . . ? C20 C21 N2 107.4(5) . . ? C20 C21 H21 126.3 . . ? N2 C21 H21 126.3 . . ? C27 C22 C23 123.3(6) . . ? C27 C22 N1 118.1(5) . . ? C23 C22 N1 118.4(5) . . ? C22 C23 C28' 132.9(8) . . ? C22 C23 C24 112.0(6) . . ? C28' C23 C24 115.2(7) . . ? C22 C23 C28 114.7(8) . . ? C28' C23 C28 18.2(8) . . ? C24 C23 C28 133.3(8) . . ? C25 C24 C23 121.3(7) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C26 C25 C24 122.5(8) . . ? C26 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? C25 C26 C27 123.0(8) . . ? C25 C26 H26 118.5 . . ? C27 C26 H26 118.5 . . ? C26 C27 C22 117.9(6) . . ? C26 C27 C31 120.8(6) . . ? C22 C27 C31 121.3(5) . . ? C29 C28 C30 115.6(13) . . ? C29 C28 C23 126.1(11) . . ? C30 C28 C23 116.7(12) . . ? C23 C28' C29' 118.5(11) . . ? C23 C28' C30' 111.0(11) . . ? C29' C28' C30' 118.4(13) . . ? C27 C31 C33 113.3(7) . . ? C27 C31 C32 110.9(5) . . ? C33 C31 C32 110.9(6) . . ? C27 C31 H31 107.1 . . ? C33 C31 H31 107.1 . . ? C32 C31 H31 107.1 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C39 123.2(6) . . ? C35 C34 N2 117.9(5) . . ? C39 C34 N2 118.9(6) . . ? C34 C35 C36 118.4(6) . . ? C34 C35 C40 121.0(6) . . ? C36 C35 C40 120.5(7) . . ? C35 C36 C37 119.3(7) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C38 C37 C36 120.5(7) . . ? C38 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C37 C38 C39 121.8(6) . . ? C37 C38 H38 119.1 . . ? C39 C38 H38 119.1 . . ? C34 C39 C38 116.8(6) . . ? C34 C39 C43 121.5(5) . . ? C38 C39 C43 121.7(5) . . ? C41 C40 C42' 108.7(10) . . ? C41 C40 C35 109.2(7) . . ? C42' C40 C35 113.7(10) . . ? C41 C40 C42 125.7(10) . . ? C42' C40 C42 22.1(10) . . ? C35 C40 C42 113.5(9) . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C39 C43 C45 113.8(6) . . ? C39 C43 C44 109.9(6) . . ? C45 C43 C44 108.6(6) . . ? C39 C43 H43 108.1 . . ? C45 C43 H43 108.1 . . ? C44 C43 H43 108.1 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Ni1 P1 C7 -70.16(17) . . . . ? Cl3 Ni1 P1 C7 50.03(16) . . . . ? Cl1 Ni1 P1 C7 175.74(15) . . . . ? Cl2 Ni1 P1 C13 170.94(18) . . . . ? Cl3 Ni1 P1 C13 -68.87(17) . . . . ? Cl1 Ni1 P1 C13 56.84(17) . . . . ? Cl2 Ni1 P1 C1 50.28(17) . . . . ? Cl3 Ni1 P1 C1 170.46(16) . . . . ? Cl1 Ni1 P1 C1 -63.83(16) . . . . ? C7 P1 C1 C2 157.7(4) . . . . ? C13 P1 C1 C2 -92.0(4) . . . . ? Ni1 P1 C1 C2 33.2(4) . . . . ? C7 P1 C1 C6 -26.8(4) . . . . ? C13 P1 C1 C6 83.5(4) . . . . ? Ni1 P1 C1 C6 -151.3(3) . . . . ? C6 C1 C2 C3 -1.4(7) . . . . ? P1 C1 C2 C3 174.2(4) . . . . ? C1 C2 C3 C4 1.3(8) . . . . ? C2 C3 C4 C5 0.2(8) . . . . ? C3 C4 C5 C6 -1.6(8) . . . . ? C4 C5 C6 C1 1.4(8) . . . . ? C2 C1 C6 C5 0.1(7) . . . . ? P1 C1 C6 C5 -175.4(4) . . . . ? C13 P1 C7 C12 -3.1(5) . . . . ? C1 P1 C7 C12 106.0(5) . . . . ? Ni1 P1 C7 C12 -126.1(4) . . . . ? C13 P1 C7 C8 176.0(4) . . . . ? C1 P1 C7 C8 -75.0(5) . . . . ? Ni1 P1 C7 C8 52.9(4) . . . . ? C12 C7 C8 C9 -0.3(9) . . . . ? P1 C7 C8 C9 -179.4(5) . . . . ? C7 C8 C9 C10 2.6(10) . . . . ? C8 C9 C10 C11 -3.3(11) . . . . ? C9 C10 C11 C12 1.8(10) . . . . ? C8 C7 C12 C11 -1.1(8) . . . . ? P1 C7 C12 C11 177.9(5) . . . . ? C10 C11 C12 C7 0.4(9) . . . . ? C7 P1 C13 C14 90.5(5) . . . . ? C1 P1 C13 C14 -18.7(5) . . . . ? Ni1 P1 C13 C14 -146.9(4) . . . . ? C7 P1 C13 C18 -91.2(4) . . . . ? C1 P1 C13 C18 159.6(4) . . . . ? Ni1 P1 C13 C18 31.4(5) . . . . ? C18 C13 C14 C15 3.4(8) . . . . ? P1 C13 C14 C15 -178.3(4) . . . . ? C13 C14 C15 C16 -1.3(10) . . . . ? C14 C15 C16 C17 -2.1(11) . . . . ? C15 C16 C17 C18 3.4(11) . . . . ? C14 C13 C18 C17 -2.2(9) . . . . ? P1 C13 C18 C17 179.5(5) . . . . ? C16 C17 C18 C13 -1.2(11) . . . . ? C21 N2 C19 N1 0.3(6) . . . . ? C34 N2 C19 N1 -179.6(5) . . . . ? C20 N1 C19 N2 0.5(6) . . . . ? C22 N1 C19 N2 178.2(5) . . . . ? C19 N1 C20 C21 -1.1(6) . . . . ? C22 N1 C20 C21 -178.9(5) . . . . ? N1 C20 C21 N2 1.2(6) . . . . ? C19 N2 C21 C20 -1.0(6) . . . . ? C34 N2 C21 C20 178.9(5) . . . . ? C19 N1 C22 C27 -95.9(6) . . . . ? C20 N1 C22 C27 81.4(6) . . . . ? C19 N1 C22 C23 89.7(6) . . . . ? C20 N1 C22 C23 -92.9(6) . . . . ? C27 C22 C23 C28' 175.8(9) . . . . ? N1 C22 C23 C28' -10.2(12) . . . . ? C27 C22 C23 C24 -2.5(8) . . . . ? N1 C22 C23 C24 171.5(4) . . . . ? C27 C22 C23 C28 174.6(7) . . . . ? N1 C22 C23 C28 -11.4(8) . . . . ? C22 C23 C24 C25 0.5(9) . . . . ? C28' C23 C24 C25 -178.1(9) . . . . ? C28 C23 C24 C25 -175.9(9) . . . . ? C23 C24 C25 C26 2.0(11) . . . . ? C24 C25 C26 C27 -2.5(12) . . . . ? C25 C26 C27 C22 0.4(9) . . . . ? C25 C26 C27 C31 179.1(7) . . . . ? C23 C22 C27 C26 2.2(8) . . . . ? N1 C22 C27 C26 -171.8(5) . . . . ? C23 C22 C27 C31 -176.5(5) . . . . ? N1 C22 C27 C31 9.4(7) . . . . ? C22 C23 C28 C29 -92.3(15) . . . . ? C28' C23 C28 C29 90(3) . . . . ? C24 C23 C28 C29 84.0(17) . . . . ? C22 C23 C28 C30 102.6(14) . . . . ? C28' C23 C28 C30 -75(3) . . . . ? C24 C23 C28 C30 -81.1(16) . . . . ? C22 C23 C28' C29' -163.3(10) . . . . ? C24 C23 C28' C29' 14.9(16) . . . . ? C28 C23 C28' C29' -160(4) . . . . ? C22 C23 C28' C30' 54.6(16) . . . . ? C24 C23 C28' C30' -127.1(11) . . . . ? C28 C23 C28' C30' 58(3) . . . . ? C26 C27 C31 C33 39.7(8) . . . . ? C22 C27 C31 C33 -141.6(6) . . . . ? C26 C27 C31 C32 -85.8(7) . . . . ? C22 C27 C31 C32 92.9(6) . . . . ? C19 N2 C34 C35 96.3(7) . . . . ? C21 N2 C34 C35 -83.6(7) . . . . ? C19 N2 C34 C39 -85.3(7) . . . . ? C21 N2 C34 C39 94.8(6) . . . . ? C39 C34 C35 C36 0.2(9) . . . . ? N2 C34 C35 C36 178.5(5) . . . . ? C39 C34 C35 C40 179.0(6) . . . . ? N2 C34 C35 C40 -2.7(8) . . . . ? C34 C35 C36 C37 0.1(9) . . . . ? C40 C35 C36 C37 -178.7(6) . . . . ? C35 C36 C37 C38 -0.2(10) . . . . ? C36 C37 C38 C39 0.1(10) . . . . ? C35 C34 C39 C38 -0.3(8) . . . . ? N2 C34 C39 C38 -178.6(5) . . . . ? C35 C34 C39 C43 177.8(5) . . . . ? N2 C34 C39 C43 -0.5(8) . . . . ? C37 C38 C39 C34 0.2(9) . . . . ? C37 C38 C39 C43 -177.9(6) . . . . ? C34 C35 C40 C41 -97.1(9) . . . . ? C36 C35 C40 C41 81.8(9) . . . . ? C34 C35 C40 C42' 141.4(10) . . . . ? C36 C35 C40 C42' -39.8(12) . . . . ? C34 C35 C40 C42 117.3(10) . . . . ? C36 C35 C40 C42 -63.9(12) . . . . ? C34 C39 C43 C45 -135.2(6) . . . . ? C38 C39 C43 C45 42.9(8) . . . . ? C34 C39 C43 C44 102.8(7) . . . . ? C38 C39 C43 C44 -79.2(8) . . . . ? 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 C21 H21 Cl2 0.94 2.52 3.402(5) 156.9 . C19 H19 Cl1 0.94 2.56 3.493(5) 173.9 3_455 C18 H18 Cl3 0.94 2.69 3.558(7) 153.5 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.390 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.111