# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_rbx9_1a _database_code_depnum_ccdc_archive 'CCDC 896745' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-31 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C9 H21 Cl Ni0.5 P)' _chemical_formula_sum 'C18 H42 Cl2 Ni P2' _chemical_formula_weight 450.07 _chemical_melting_point ? 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' P P 0.1023 0.0942 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.2383(16) _cell_length_b 8.8394(18) _cell_length_c 16.113(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.70(3) _cell_angle_gamma 90.00 _cell_volume 1170.9(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8064 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.192 _exptl_absorpt_correction_T_max 0.7629 _exptl_absorpt_correction_T_min 0.6407 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description hexagonal _exptl_crystal_F_000 484 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_unetI/netI 0.0214 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 10964 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.48 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 1860 _reflns_number_total 2076 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.848 _refine_diff_density_min -1.446 _refine_diff_density_rms 0.122 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 112 _refine_ls_number_reflns 2076 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0571 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+4.4194P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1611 _refine_ls_wR_factor_ref 0.1673 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.0000 0.5000 0.0000 0.0228(3) Uani 1 2 d S . . Cl1 Cl -0.0059(3) 0.6784(2) 0.09433(13) 0.0969(8) Uani 1 1 d . . . P1 P 0.12355(12) 0.34488(11) 0.09579(6) 0.0205(3) Uani 1 1 d . . . C1 C -0.1341(7) 0.3557(7) 0.2010(4) 0.0501(14) Uani 1 1 d . . . H1A H -0.0639 0.4181 0.2386 0.075 Uiso 1 1 calc R . . H1B H -0.2102 0.2986 0.2332 0.075 Uiso 1 1 calc R . . H1C H -0.1952 0.4210 0.1609 0.075 Uiso 1 1 calc R . . C2 C -0.0299(5) 0.2462(5) 0.1546(3) 0.0289(10) Uani 1 1 d . . . H2 H 0.0294 0.1801 0.1968 0.035 Uiso 1 1 calc R . . C3 C -0.1379(7) 0.1442(7) 0.0976(4) 0.0576(16) Uani 1 1 d . . . H3A H -0.1955 0.2059 0.0546 0.086 Uiso 1 1 calc R . . H3B H -0.2171 0.0924 0.1305 0.086 Uiso 1 1 calc R . . H3C H -0.0704 0.0691 0.0713 0.086 Uiso 1 1 calc R . . C4 C 0.2904(9) 0.0556(7) 0.1109(4) 0.0583(17) Uani 1 1 d . . . H4A H 0.3725 0.0899 0.1535 0.087 Uiso 1 1 calc R . . H4B H 0.3354 -0.0265 0.0786 0.087 Uiso 1 1 calc R . . H4C H 0.1944 0.0191 0.1377 0.087 Uiso 1 1 calc R . . C5 C 0.2419(6) 0.1872(5) 0.0530(3) 0.0319(10) Uani 1 1 d . . . H5 H 0.1683 0.1420 0.0079 0.038 Uiso 1 1 calc R . . C6 C 0.3889(8) 0.2466(9) 0.0092(5) 0.073(2) Uani 1 1 d . . . H6A H 0.3543 0.3293 -0.0284 0.110 Uiso 1 1 calc R . . H6B H 0.4350 0.1647 -0.0228 0.110 Uiso 1 1 calc R . . H6C H 0.4714 0.2839 0.0508 0.110 Uiso 1 1 calc R . . C7 C 0.3319(8) 0.3430(7) 0.2466(4) 0.0591(17) Uani 1 1 d . . . H7A H 0.2488 0.2801 0.2705 0.089 Uiso 1 1 calc R . . H7B H 0.3839 0.4075 0.2900 0.089 Uiso 1 1 calc R . . H7C H 0.4140 0.2778 0.2234 0.089 Uiso 1 1 calc R . . C8 C 0.2530(6) 0.4412(6) 0.1781(3) 0.0328(10) Uani 1 1 d . . . H8 H 0.1779 0.5101 0.2065 0.039 Uiso 1 1 calc R . . C9 C 0.3780(8) 0.5459(9) 0.1406(4) 0.068(2) Uani 1 1 d . . . H9A H 0.4671 0.4851 0.1208 0.103 Uiso 1 1 calc R . . H9B H 0.4213 0.6169 0.1832 0.103 Uiso 1 1 calc R . . H9C H 0.3254 0.6024 0.0940 0.103 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 0.0302(5) 0.0193(4) 0.0182(4) -0.0011(3) -0.0029(3) 0.0030(3) Cl1 0.146(2) 0.0722(13) 0.0679(12) -0.0104(10) -0.0288(13) 0.0388(13) P1 0.0210(5) 0.0208(5) 0.0196(5) 0.0010(4) 0.0002(4) 0.0019(4) C1 0.042(3) 0.052(3) 0.059(3) 0.002(3) 0.024(3) 0.005(2) C2 0.028(2) 0.030(2) 0.029(2) 0.0040(19) 0.0057(18) 0.0001(18) C3 0.047(3) 0.062(4) 0.065(4) -0.009(3) 0.008(3) -0.029(3) C4 0.083(4) 0.046(3) 0.046(3) 0.003(3) 0.002(3) 0.041(3) C5 0.032(2) 0.035(2) 0.029(2) -0.0016(19) 0.0028(18) 0.011(2) C6 0.058(4) 0.074(5) 0.093(5) -0.002(4) 0.046(4) 0.015(4) C7 0.067(4) 0.056(4) 0.049(3) 0.002(3) -0.033(3) 0.005(3) C8 0.032(2) 0.038(3) 0.028(2) -0.003(2) -0.0068(18) -0.002(2) C9 0.060(4) 0.082(5) 0.061(4) -0.005(4) -0.006(3) -0.043(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 Cl1 2.193(2) 3_565 ? Ni1 Cl1 2.193(2) . ? Ni1 P1 2.2572(11) 3_565 ? Ni1 P1 2.2573(11) . ? P1 C2 1.847(4) . ? P1 C5 1.859(4) . ? P1 C8 1.854(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.522(7) . ? C2 H2 1.0000 . ? C2 C3 1.530(7) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 C5 1.527(7) . ? C5 H5 1.0000 . ? C5 C6 1.534(8) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.517(7) . ? C8 H8 1.0000 . ? C8 C9 1.537(8) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ni1 Cl1 180.0 3_565 . ? Cl1 Ni1 P1 90.45(6) . 3_565 ? Cl1 Ni1 P1 89.55(6) 3_565 3_565 ? Cl1 Ni1 P1 90.45(6) 3_565 . ? Cl1 Ni1 P1 89.55(6) . . ? P1 Ni1 P1 180.0 3_565 . ? C2 P1 Ni1 110.13(15) . . ? C2 P1 C5 103.2(2) . . ? C2 P1 C8 103.4(2) . . ? C5 P1 Ni1 115.23(15) . . ? C8 P1 Ni1 115.02(16) . . ? C8 P1 C5 108.6(2) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? P1 C2 H2 107.7 . . ? C1 C2 P1 112.2(3) . . ? C1 C2 H2 107.7 . . ? C1 C2 C3 110.2(4) . . ? C3 C2 P1 111.2(3) . . ? C3 C2 H2 107.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? P1 C5 H5 105.2 . . ? C4 C5 P1 117.9(3) . . ? C4 C5 H5 105.2 . . ? C4 C5 C6 111.0(5) . . ? C6 C5 P1 111.3(4) . . ? C6 C5 H5 105.2 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P1 C8 H8 105.3 . . ? C7 C8 P1 117.2(4) . . ? C7 C8 H8 105.3 . . ? C7 C8 C9 111.3(5) . . ? C9 C8 P1 111.4(4) . . ? C9 C8 H8 105.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? data_rbd1_1b _database_code_depnum_ccdc_archive 'CCDC 896746' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-06-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C9 H21 Br Ni0.5 P)' _chemical_formula_sum 'C18 H42 Br2 Ni P2' _chemical_formula_weight 538.99 _chemical_melting_point ? 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.1476(5) _cell_length_b 8.9382(6) _cell_length_c 16.3133(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.7970(10) _cell_angle_gamma 90.00 _cell_volume 1185.41(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4034 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 27.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 4.323 _exptl_absorpt_correction_T_max 0.6250 _exptl_absorpt_correction_T_min 0.4785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS BRUKER 2001' _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 556 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_unetI/netI 0.0180 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11551 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 3.39 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 1976 _reflns_number_total 2240 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.589 _refine_diff_density_min -1.371 _refine_diff_density_rms 0.118 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 112 _refine_ls_number_reflns 2240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0478 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+3.6942P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1285 _refine_ls_wR_factor_ref 0.1341 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.55137(9) -0.20096(6) 0.08794(4) 0.0638(3) Uani 1 1 d . . . Ni1 Ni 0.5000 0.0000 0.0000 0.0280(2) Uani 1 2 d S . . P1 P 0.62800(12) 0.15895(12) 0.09394(6) 0.0243(3) Uani 1 1 d . . . C1 C 0.8082(7) 0.4365(6) 0.1093(3) 0.0498(13) Uani 1 1 d . . . H1A H 0.7290 0.4625 0.1497 0.075 Uiso 1 1 calc R . . H1B H 0.8373 0.5266 0.0792 0.075 Uiso 1 1 calc R . . H1C H 0.9074 0.3943 0.1377 0.075 Uiso 1 1 calc R . . C2 C 0.7322(5) 0.3223(5) 0.0495(3) 0.0341(10) Uani 1 1 d . . . H2 H 0.6427 0.3776 0.0174 0.041 Uiso 1 1 calc R . . C3 C 0.8532(8) 0.2780(7) -0.0136(4) 0.0584(15) Uani 1 1 d . . . H3A H 0.9518 0.2342 0.0145 0.088 Uiso 1 1 calc R . . H3B H 0.8840 0.3669 -0.0443 0.088 Uiso 1 1 calc R . . H3C H 0.8016 0.2045 -0.0517 0.088 Uiso 1 1 calc R . . C4 C 0.3791(7) 0.1232(7) 0.2007(3) 0.0496(13) Uani 1 1 d . . . H4A H 0.3251 0.0569 0.1594 0.074 Uiso 1 1 calc R . . H4B H 0.2960 0.1697 0.2332 0.074 Uiso 1 1 calc R . . H4C H 0.4556 0.0650 0.2370 0.074 Uiso 1 1 calc R . . C5 C 0.4732(5) 0.2440(5) 0.1582(3) 0.0310(9) Uani 1 1 d . . . H5 H 0.5347 0.3035 0.2022 0.037 Uiso 1 1 calc R . . C6 C 0.3568(7) 0.3499(7) 0.1115(4) 0.0532(14) Uani 1 1 d . . . H6A H 0.4188 0.4351 0.0917 0.080 Uiso 1 1 calc R . . H6B H 0.2743 0.3859 0.1478 0.080 Uiso 1 1 calc R . . H6C H 0.3019 0.2975 0.0646 0.080 Uiso 1 1 calc R . . C7 C 0.8321(8) 0.1617(7) 0.2460(4) 0.0616(16) Uani 1 1 d . . . H7A H 0.9010 0.2448 0.2294 0.092 Uiso 1 1 calc R . . H7B H 0.8960 0.0977 0.2851 0.092 Uiso 1 1 calc R . . H7C H 0.7362 0.2013 0.2720 0.092 Uiso 1 1 calc R . . C8 C 0.7750(6) 0.0703(5) 0.1706(3) 0.0373(10) Uani 1 1 d . . . H8 H 0.7152 -0.0174 0.1922 0.045 Uiso 1 1 calc R . . C9 C 0.9218(7) 0.0041(8) 0.1294(4) 0.0701(19) Uani 1 1 d . . . H9A H 0.8825 -0.0508 0.0799 0.105 Uiso 1 1 calc R . . H9B H 0.9818 -0.0642 0.1676 0.105 Uiso 1 1 calc R . . H9C H 0.9952 0.0850 0.1142 0.105 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 0.1043(6) 0.0336(3) 0.0483(4) 0.0068(2) -0.0327(3) -0.0114(3) Ni1 0.0330(4) 0.0259(4) 0.0245(4) -0.0049(3) -0.0024(3) -0.0007(3) P1 0.0268(5) 0.0239(5) 0.0220(5) -0.0002(4) 0.0003(4) 0.0003(4) C1 0.054(3) 0.038(3) 0.058(3) -0.001(2) 0.003(2) -0.017(2) C2 0.033(2) 0.033(2) 0.036(2) 0.0037(19) 0.0038(18) -0.0037(18) C3 0.060(3) 0.061(4) 0.057(3) 0.003(3) 0.029(3) -0.009(3) C4 0.046(3) 0.054(3) 0.052(3) 0.001(3) 0.022(2) -0.004(2) C5 0.033(2) 0.031(2) 0.030(2) -0.0039(18) 0.0061(17) 0.0009(18) C6 0.047(3) 0.056(3) 0.057(3) 0.005(3) 0.009(2) 0.022(3) C7 0.077(4) 0.058(4) 0.045(3) 0.004(3) -0.031(3) -0.011(3) C8 0.040(2) 0.038(3) 0.033(2) 0.0048(19) -0.0072(18) 0.002(2) C9 0.050(3) 0.089(5) 0.070(4) 0.013(4) -0.001(3) 0.035(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Ni1 2.3195(5) . ? Ni1 Br1 2.3195(5) 3_655 ? Ni1 P1 2.2898(10) . ? Ni1 P1 2.2898(10) 3_655 ? P1 C2 1.860(4) . ? P1 C5 1.856(4) . ? P1 C8 1.851(4) . ? C1 C2 1.515(7) . ? C2 C3 1.525(7) . ? C4 C5 1.518(7) . ? C5 C6 1.511(7) . ? C7 C8 1.524(7) . ? C8 C9 1.529(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 Br1 Ni1 Br1 180.00(4) 3_655 . ? P1 Ni1 Br1 90.63(3) 3_655 3_655 ? P1 Ni1 Br1 89.37(3) . 3_655 ? P1 Ni1 Br1 90.63(3) . . ? P1 Ni1 Br1 89.37(3) 3_655 . ? P1 Ni1 P1 180.0 . 3_655 ? C2 P1 Ni1 115.20(15) . . ? C5 P1 Ni1 109.64(14) . . ? C5 P1 C2 104.1(2) . . ? C8 P1 Ni1 115.60(16) . . ? C8 P1 C2 107.9(2) . . ? C8 P1 C5 103.1(2) . . ? C1 C2 P1 117.1(3) . . ? C1 C2 C3 110.8(4) . . ? C3 C2 P1 113.1(4) . . ? C4 C5 P1 110.4(3) . . ? C6 C5 P1 113.5(3) . . ? C6 C5 C4 110.9(4) . . ? C7 C8 P1 117.7(4) . . ? C7 C8 C9 110.9(5) . . ? C9 C8 P1 111.0(4) . . ? data_rbs2_1c _database_code_depnum_ccdc_archive 'CCDC 896747' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-27 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H42 I2 Ni P2' _chemical_formula_sum 'C18 H42 I2 Ni P2' _chemical_formula_weight 632.97 _chemical_melting_point ? 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' P P 0.1023 0.0942 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y-1/2, z' _cell_length_a 15.249(3) _cell_length_b 12.623(3) _cell_length_c 25.316(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4873.3(17) _cell_formula_units_Z 8 _cell_measurement_reflns_used 8064 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 3.461 _exptl_absorpt_correction_T_max 0.6074 _exptl_absorpt_correction_T_min 0.3771 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS BRUKER 2001' _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cubes _exptl_crystal_F_000 2512 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.16 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0749 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 49168 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.09 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3921 _reflns_number_total 4972 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.882 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.120 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 4972 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0347 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+4.5432P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0678 _refine_ls_wR_factor_ref 0.0749 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I1 I 1.131154(19) 0.89167(2) 0.178345(12) 0.02975(9) Uani 1 1 d . . . I2 I 0.90307(2) 0.64275(2) 0.122311(13) 0.03453(10) Uani 1 1 d . . . Ni1 Ni 1.00614(3) 0.79608(4) 0.13489(2) 0.02202(13) Uani 1 1 d . . . P1 P 1.09318(7) 0.74324(9) 0.06503(4) 0.0235(2) Uani 1 1 d . . . P2 P 0.90689(7) 0.88330(9) 0.18699(4) 0.0224(2) Uani 1 1 d . . . C1 C 1.2248(3) 0.8329(4) -0.00464(19) 0.0389(12) Uani 1 1 d . . . H1A H 1.1905 0.8260 -0.0372 0.058 Uiso 1 1 calc R . . H1B H 1.2573 0.7672 0.0017 0.058 Uiso 1 1 calc R . . H1C H 1.2661 0.8919 -0.0082 0.058 Uiso 1 1 calc R . . C2 C 1.1631(3) 0.8542(3) 0.04176(17) 0.0273(10) Uani 1 1 d . . . H2 H 1.2025 0.8710 0.0722 0.033 Uiso 1 1 calc R . . C3 C 1.1108(3) 0.9563(4) 0.03179(19) 0.0355(12) Uani 1 1 d . . . H3A H 1.1507 1.0172 0.0324 0.053 Uiso 1 1 calc R . . H3B H 1.0663 0.9647 0.0594 0.053 Uiso 1 1 calc R . . H3C H 1.0821 0.9521 -0.0028 0.053 Uiso 1 1 calc R . . C4 C 1.1301(4) 0.5312(4) 0.0919(2) 0.0507(15) Uani 1 1 d . . . H4A H 1.1751 0.4771 0.0978 0.076 Uiso 1 1 calc R . . H4B H 1.0909 0.5082 0.0634 0.076 Uiso 1 1 calc R . . H4C H 1.0961 0.5413 0.1244 0.076 Uiso 1 1 calc R . . C5 C 1.1738(3) 0.6354(4) 0.07640(18) 0.0317(11) Uani 1 1 d . . . H5 H 1.2044 0.6228 0.0420 0.038 Uiso 1 1 calc R . . C6 C 1.2446(3) 0.6635(4) 0.1169(2) 0.0427(13) Uani 1 1 d . . . H6A H 1.2178 0.6710 0.1519 0.064 Uiso 1 1 calc R . . H6B H 1.2726 0.7304 0.1068 0.064 Uiso 1 1 calc R . . H6C H 1.2887 0.6071 0.1179 0.064 Uiso 1 1 calc R . . C7 C 0.9650(3) 0.7739(4) -0.01373(19) 0.0419(13) Uani 1 1 d . . . H7A H 0.9973 0.8273 -0.0340 0.063 Uiso 1 1 calc R . . H7B H 0.9344 0.8083 0.0157 0.063 Uiso 1 1 calc R . . H7C H 0.9221 0.7390 -0.0367 0.063 Uiso 1 1 calc R . . C8 C 1.0286(3) 0.6921(4) 0.00771(17) 0.0295(10) Uani 1 1 d . . . H8 H 0.9912 0.6341 0.0223 0.035 Uiso 1 1 calc R . . C9 C 1.0807(4) 0.6415(5) -0.0374(2) 0.0526(16) Uani 1 1 d . . . H9A H 1.0400 0.6093 -0.0627 0.079 Uiso 1 1 calc R . . H9B H 1.1197 0.5869 -0.0232 0.079 Uiso 1 1 calc R . . H9C H 1.1155 0.6960 -0.0553 0.079 Uiso 1 1 calc R . . C10 C 0.7236(3) 0.8260(4) 0.1727(2) 0.0413(13) Uani 1 1 d . . . H10A H 0.6682 0.8491 0.1569 0.062 Uiso 1 1 calc R . . H10B H 0.7182 0.8265 0.2113 0.062 Uiso 1 1 calc R . . H10C H 0.7373 0.7540 0.1608 0.062 Uiso 1 1 calc R . . C11 C 0.7963(3) 0.9003(4) 0.15619(17) 0.0302(10) Uani 1 1 d . . . H11 H 0.7763 0.9720 0.1678 0.036 Uiso 1 1 calc R . . C12 C 0.8028(3) 0.9079(4) 0.09614(18) 0.0365(12) Uani 1 1 d . . . H12A H 0.8040 0.8365 0.0810 0.055 Uiso 1 1 calc R . . H12B H 0.8566 0.9457 0.0865 0.055 Uiso 1 1 calc R . . H12C H 0.7519 0.9465 0.0824 0.055 Uiso 1 1 calc R . . C13 C 0.8733(3) 0.7139(4) 0.25800(19) 0.0387(12) Uani 1 1 d . . . H13A H 0.9247 0.6764 0.2443 0.058 Uiso 1 1 calc R . . H13B H 0.8218 0.6957 0.2367 0.058 Uiso 1 1 calc R . . H13C H 0.8631 0.6929 0.2948 0.058 Uiso 1 1 calc R . . C14 C 0.8891(3) 0.8326(4) 0.25531(17) 0.0293(10) Uani 1 1 d . . . H14 H 0.8355 0.8682 0.2695 0.035 Uiso 1 1 calc R . . C15 C 0.9653(3) 0.8614(4) 0.29193(18) 0.0367(12) Uani 1 1 d . . . H15A H 0.9518 0.8382 0.3280 0.055 Uiso 1 1 calc R . . H15B H 0.9741 0.9383 0.2916 0.055 Uiso 1 1 calc R . . H15C H 1.0188 0.8261 0.2797 0.055 Uiso 1 1 calc R . . C16 C 0.8705(3) 1.0814(4) 0.2380(2) 0.0395(12) Uani 1 1 d . . . H16A H 0.8929 1.1524 0.2459 0.059 Uiso 1 1 calc R . . H16B H 0.8659 1.0405 0.2708 0.059 Uiso 1 1 calc R . . H16C H 0.8124 1.0871 0.2216 0.059 Uiso 1 1 calc R . . C17 C 0.9339(3) 1.0248(3) 0.19964(17) 0.0273(10) Uani 1 1 d . . . H17 H 0.9929 1.0256 0.2169 0.033 Uiso 1 1 calc R . . C18 C 0.9428(3) 1.0886(4) 0.1484(2) 0.0382(12) Uani 1 1 d . . . H18A H 0.8849 1.0968 0.1321 0.057 Uiso 1 1 calc R . . H18B H 0.9819 1.0512 0.1240 0.057 Uiso 1 1 calc R . . H18C H 0.9671 1.1586 0.1564 0.057 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 I1 0.02584(16) 0.03520(18) 0.02821(16) -0.00390(13) -0.00207(13) -0.00273(13) I2 0.03377(18) 0.02901(17) 0.04079(19) -0.00693(14) 0.00782(14) -0.00849(13) Ni1 0.0215(3) 0.0212(3) 0.0233(3) -0.0013(2) 0.0017(2) -0.0005(2) P1 0.0223(6) 0.0244(6) 0.0237(6) 0.0000(5) 0.0019(5) 0.0023(5) P2 0.0220(6) 0.0229(6) 0.0223(6) -0.0005(4) 0.0013(4) 0.0007(5) C1 0.034(3) 0.045(3) 0.038(3) 0.002(2) 0.017(2) -0.002(2) C2 0.026(2) 0.030(2) 0.026(2) 0.002(2) 0.0030(19) -0.001(2) C3 0.036(3) 0.032(3) 0.038(3) 0.007(2) 0.006(2) 0.000(2) C4 0.051(4) 0.029(3) 0.072(4) 0.012(3) 0.011(3) 0.007(3) C5 0.033(3) 0.033(3) 0.029(2) -0.001(2) 0.007(2) 0.012(2) C6 0.043(3) 0.039(3) 0.046(3) 0.002(2) -0.004(2) 0.011(2) C7 0.044(3) 0.049(3) 0.033(3) -0.004(2) -0.011(2) 0.003(3) C8 0.031(2) 0.034(3) 0.024(2) -0.006(2) 0.0053(19) -0.005(2) C9 0.050(4) 0.064(4) 0.043(3) -0.025(3) 0.009(3) -0.002(3) C10 0.024(3) 0.059(4) 0.041(3) 0.000(3) -0.001(2) -0.001(2) C11 0.024(2) 0.037(3) 0.029(2) -0.003(2) 0.001(2) 0.002(2) C12 0.032(3) 0.045(3) 0.033(3) 0.002(2) -0.008(2) 0.000(2) C13 0.048(3) 0.033(3) 0.035(3) 0.009(2) -0.002(2) -0.003(2) C14 0.030(2) 0.033(3) 0.026(2) 0.004(2) 0.0058(19) 0.003(2) C15 0.051(3) 0.037(3) 0.022(2) 0.002(2) -0.002(2) 0.005(2) C16 0.044(3) 0.034(3) 0.041(3) -0.008(2) 0.000(2) 0.013(2) C17 0.032(3) 0.021(2) 0.029(2) -0.0059(19) -0.001(2) 0.0036(19) C18 0.046(3) 0.028(3) 0.041(3) 0.000(2) -0.001(2) -0.001(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 I1 Ni1 2.5102(7) . ? I2 Ni1 2.5135(7) . ? Ni1 P1 2.3098(13) . ? Ni1 P2 2.2896(12) . ? P1 C2 1.856(4) . ? P1 C5 1.856(4) . ? P1 C8 1.868(4) . ? P2 C11 1.870(4) . ? P2 C14 1.864(4) . ? P2 C17 1.861(4) . ? C1 C2 1.529(6) . ? C2 C3 1.537(6) . ? C4 C5 1.526(7) . ? C5 C6 1.530(7) . ? C7 C8 1.518(6) . ? C8 C9 1.531(6) . ? C10 C11 1.512(6) . ? C11 C12 1.527(6) . ? C13 C14 1.520(7) . ? C14 C15 1.530(6) . ? C16 C17 1.546(6) . ? C17 C18 1.533(6) . ? 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 I1 Ni1 I2 154.24(3) . . ? P1 Ni1 I1 92.18(4) . . ? P1 Ni1 I2 92.29(4) . . ? P2 Ni1 I1 91.05(4) . . ? P2 Ni1 I2 91.72(4) . . ? P2 Ni1 P1 163.71(5) . . ? C2 P1 Ni1 110.81(14) . . ? C2 P1 C5 102.8(2) . . ? C2 P1 C8 108.5(2) . . ? C5 P1 Ni1 118.26(15) . . ? C5 P1 C8 102.5(2) . . ? C8 P1 Ni1 113.06(14) . . ? C11 P2 Ni1 114.28(15) . . ? C14 P2 Ni1 117.75(15) . . ? C14 P2 C11 107.2(2) . . ? C17 P2 Ni1 114.48(15) . . ? C17 P2 C11 99.3(2) . . ? C17 P2 C14 101.6(2) . . ? C1 C2 P1 117.7(3) . . ? C1 C2 C3 109.9(4) . . ? C3 C2 P1 112.8(3) . . ? C4 C5 P1 112.5(3) . . ? C4 C5 C6 109.6(4) . . ? C6 C5 P1 113.6(3) . . ? C7 C8 P1 112.3(3) . . ? C7 C8 C9 110.4(4) . . ? C9 C8 P1 116.8(3) . . ? C10 C11 P2 118.3(3) . . ? C10 C11 C12 111.3(4) . . ? C12 C11 P2 111.3(3) . . ? C13 C14 P2 113.8(3) . . ? C13 C14 C15 109.1(4) . . ? C15 C14 P2 111.7(3) . . ? C16 C17 P2 114.4(3) . . ? C18 C17 P2 112.2(3) . . ? C18 C17 C16 110.1(4) . . ? data_rbk1_2 _database_code_depnum_ccdc_archive 'CCDC 896748' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-27 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H46 Ni P2' _chemical_formula_sum 'C20 H46 Ni P2' _chemical_formula_weight 407.22 _chemical_melting_point ? 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 11.7420(3) _cell_length_b 13.3060(4) _cell_length_c 16.8905(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.221(2) _cell_angle_gamma 90.00 _cell_volume 2367.40(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4034 _cell_measurement_temperature 173.0 _cell_measurement_theta_max 27.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 0.954 _exptl_absorpt_correction_T_max 0.8941 _exptl_absorpt_correction_T_min 0.7963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour yellow _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_unetI/netI 0.0141 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 25356 _diffrn_reflns_theta_full 26.73 _diffrn_reflns_theta_max 26.73 _diffrn_reflns_theta_min 2.04 _diffrn_ambient_temperature 173.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 4623 _reflns_number_total 5017 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.503 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 5017 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0274 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.6442P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.0751 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.782300(15) 0.134740(12) 0.772089(10) 0.02441(7) Uani 1 1 d . . . P1 P 0.94544(3) 0.22753(2) 0.85324(2) 0.02230(8) Uani 1 1 d . . . P2 P 0.61105(3) 0.20621(3) 0.67381(2) 0.02353(9) Uani 1 1 d . . . C1 C 0.7296(2) -0.00812(13) 0.75627(14) 0.0470(4) Uani 1 1 d . . . C2 C 0.85310(19) 0.00223(12) 0.82126(13) 0.0477(4) Uani 1 1 d . . . C3 C 1.00741(12) 0.18628(11) 0.97020(8) 0.0273(3) Uani 1 1 d . . . H3 H 1.0377 0.1159 0.9707 0.033 Uiso 1 1 calc R . . C4 C 0.90188(14) 0.17665(13) 0.99965(10) 0.0369(3) Uani 1 1 d . . . H4A H 0.9316 0.1348 1.0528 0.055 Uiso 1 1 calc R . . H4B H 0.8271 0.1455 0.9524 0.055 Uiso 1 1 calc R . . H4C H 0.8794 0.2435 1.0126 0.055 Uiso 1 1 calc R . . C5 C 1.12214(14) 0.24170(14) 1.03938(9) 0.0396(4) Uani 1 1 d . . . H5A H 1.0964 0.3090 1.0486 0.059 Uiso 1 1 calc R . . H5B H 1.1880 0.2473 1.0188 0.059 Uiso 1 1 calc R . . H5C H 1.1557 0.2043 1.0951 0.059 Uiso 1 1 calc R . . C6 C 0.92765(14) 0.36759(10) 0.85030(10) 0.0309(3) Uani 1 1 d . . . H6 H 0.8797 0.3850 0.7864 0.037 Uiso 1 1 calc R . . C7 C 0.84165(16) 0.39992(13) 0.89203(11) 0.0429(4) Uani 1 1 d . . . H7A H 0.8890 0.3965 0.9564 0.064 Uiso 1 1 calc R . . H7B H 0.7680 0.3550 0.8722 0.064 Uiso 1 1 calc R . . H7C H 0.8127 0.4690 0.8743 0.064 Uiso 1 1 calc R . . C8 C 1.04742(16) 0.43367(12) 0.88491(11) 0.0438(4) Uani 1 1 d . . . H8A H 1.0227 0.5047 0.8769 0.066 Uiso 1 1 calc R . . H8B H 1.0964 0.4184 0.8521 0.066 Uiso 1 1 calc R . . H8C H 1.0994 0.4200 0.9478 0.066 Uiso 1 1 calc R . . C9 C 1.14893(18) 0.11125(15) 0.85266(13) 0.0489(4) Uani 1 1 d . . . H9A H 1.0887 0.0616 0.8136 0.073 Uiso 1 1 calc R . . H9B H 1.1718 0.0939 0.9142 0.073 Uiso 1 1 calc R . . H9C H 1.2254 0.1115 0.8432 0.073 Uiso 1 1 calc R . . C10 C 1.08814(13) 0.21490(12) 0.83251(9) 0.0307(3) Uani 1 1 d . . . H10 H 1.1529 0.2645 0.8711 0.037 Uiso 1 1 calc R . . C11 C 1.05263(17) 0.24250(14) 0.73652(11) 0.0433(4) Uani 1 1 d . . . H11A H 1.1284 0.2392 0.7262 0.065 Uiso 1 1 calc R . . H11B H 1.0179 0.3108 0.7247 0.065 Uiso 1 1 calc R . . H11C H 0.9888 0.1952 0.6972 0.065 Uiso 1 1 calc R . . C12 C 0.61336(13) 0.34236(11) 0.64626(9) 0.0300(3) Uani 1 1 d . . . H12 H 0.6583 0.3770 0.7045 0.036 Uiso 1 1 calc R . . C13 C 0.69750(17) 0.35872(12) 0.59978(11) 0.0398(4) Uani 1 1 d . . . H13A H 0.6518 0.3377 0.5380 0.060 Uiso 1 1 calc R . . H13B H 0.7753 0.3189 0.6291 0.060 Uiso 1 1 calc R . . H13C H 0.7195 0.4301 0.6023 0.060 Uiso 1 1 calc R . . C14 C 0.48753(16) 0.39950(13) 0.59779(11) 0.0438(4) Uani 1 1 d . . . H14A H 0.5052 0.4703 0.5916 0.066 Uiso 1 1 calc R . . H14B H 0.4382 0.3946 0.6317 0.066 Uiso 1 1 calc R . . H14C H 0.4389 0.3700 0.5392 0.066 Uiso 1 1 calc R . . C15 C 0.47101(13) 0.20353(12) 0.69825(9) 0.0329(3) Uani 1 1 d . . . H15 H 0.4009 0.2416 0.6503 0.040 Uiso 1 1 calc R . . C16 C 0.42183(19) 0.09843(16) 0.70097(15) 0.0572(5) Uani 1 1 d . . . H16A H 0.4883 0.0595 0.7480 0.086 Uiso 1 1 calc R . . H16B H 0.3983 0.0651 0.6441 0.086 Uiso 1 1 calc R . . H16C H 0.3472 0.1030 0.7125 0.086 Uiso 1 1 calc R . . C17 C 0.50328(16) 0.25833(15) 0.78518(11) 0.0468(4) Uani 1 1 d . . . H17A H 0.4273 0.2623 0.7952 0.070 Uiso 1 1 calc R . . H17B H 0.5332 0.3263 0.7822 0.070 Uiso 1 1 calc R . . H17C H 0.5700 0.2215 0.8338 0.070 Uiso 1 1 calc R . . C18 C 0.55355(13) 0.13403(10) 0.56817(9) 0.0287(3) Uani 1 1 d . . . H18 H 0.5308 0.0661 0.5822 0.034 Uiso 1 1 calc R . . C19 C 0.43402(15) 0.17123(14) 0.48959(10) 0.0414(4) Uani 1 1 d . . . H19A H 0.4524 0.2346 0.4680 0.062 Uiso 1 1 calc R . . H19B H 0.3666 0.1821 0.5080 0.062 Uiso 1 1 calc R . . H19C H 0.4062 0.1209 0.4424 0.062 Uiso 1 1 calc R . . C20 C 0.66024(15) 0.11486(12) 0.54114(11) 0.0382(3) Uani 1 1 d . . . H20A H 0.6349 0.0609 0.4972 0.057 Uiso 1 1 calc R . . H20B H 0.7376 0.0951 0.5931 0.057 Uiso 1 1 calc R . . H20C H 0.6764 0.1763 0.5158 0.057 Uiso 1 1 calc R . . H1A H 0.718(2) -0.0329(18) 0.7035(16) 0.064(7) Uiso 1 1 d . . . H1B H 0.668(2) -0.0156(16) 0.7697(14) 0.055(6) Uiso 1 1 d . . . H2A H 0.922(2) -0.0157(17) 0.8079(14) 0.063(6) Uiso 1 1 d . . . H2B H 0.870(2) -0.0002(18) 0.8830(17) 0.078(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02354(11) 0.02213(11) 0.02232(10) -0.00041(6) 0.00535(8) -0.00095(6) P1 0.02056(16) 0.02460(17) 0.01858(16) -0.00114(12) 0.00575(13) 0.00066(12) P2 0.01989(16) 0.02652(18) 0.02126(16) -0.00110(12) 0.00643(13) -0.00149(12) C1 0.0518(11) 0.0292(8) 0.0523(11) -0.0041(7) 0.0159(8) -0.0115(7) C2 0.0561(11) 0.0240(8) 0.0449(10) 0.0038(7) 0.0059(8) 0.0043(7) C3 0.0237(6) 0.0363(7) 0.0197(6) 0.0012(5) 0.0076(5) 0.0005(5) C4 0.0317(7) 0.0526(9) 0.0287(7) 0.0043(6) 0.0155(6) 0.0014(7) C5 0.0310(8) 0.0593(10) 0.0213(7) 0.0002(6) 0.0050(6) -0.0078(7) C6 0.0319(7) 0.0252(7) 0.0266(7) -0.0032(5) 0.0047(6) -0.0004(5) C7 0.0425(9) 0.0349(8) 0.0453(9) -0.0070(7) 0.0140(7) 0.0100(7) C8 0.0459(9) 0.0332(8) 0.0414(9) -0.0052(7) 0.0094(7) -0.0116(7) C9 0.0455(10) 0.0584(11) 0.0525(10) 0.0109(9) 0.0305(8) 0.0208(8) C10 0.0261(7) 0.0415(8) 0.0258(7) 0.0013(6) 0.0125(5) 0.0015(6) C11 0.0451(9) 0.0584(11) 0.0322(8) 0.0064(7) 0.0223(7) 0.0017(8) C12 0.0312(7) 0.0267(7) 0.0266(7) -0.0009(5) 0.0078(6) 0.0014(5) C13 0.0451(9) 0.0329(8) 0.0427(9) 0.0024(6) 0.0207(7) -0.0069(6) C14 0.0436(9) 0.0384(9) 0.0403(9) 0.0030(7) 0.0103(7) 0.0118(7) C15 0.0239(7) 0.0462(9) 0.0287(7) -0.0016(6) 0.0116(6) -0.0015(6) C16 0.0527(11) 0.0636(12) 0.0722(13) -0.0094(10) 0.0429(10) -0.0204(9) C17 0.0389(9) 0.0685(12) 0.0379(9) -0.0096(8) 0.0214(7) 0.0014(8) C18 0.0271(7) 0.0314(7) 0.0248(7) -0.0052(5) 0.0089(5) -0.0034(5) C19 0.0344(8) 0.0535(10) 0.0268(7) -0.0078(7) 0.0049(6) 0.0007(7) C20 0.0388(8) 0.0406(8) 0.0393(8) -0.0106(7) 0.0209(7) -0.0024(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 Ni1 P1 2.1800(4) . ? Ni1 P2 2.1802(4) . ? Ni1 C1 1.9803(17) . ? Ni1 C2 1.9697(16) . ? P1 C3 1.8610(13) . ? P1 C6 1.8735(14) . ? P1 C10 1.8647(14) . ? P2 C12 1.8736(15) . ? P2 C15 1.8643(14) . ? P2 C18 1.8702(14) . ? C1 C2 1.386(3) . ? C1 H1A 0.90(2) . ? C1 H1B 0.85(2) . ? C2 H2A 0.97(2) . ? C2 H2B 0.97(2) . ? C3 H3 1.0000 . ? C3 C4 1.5309(18) . ? C3 C5 1.527(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6 1.0000 . ? C6 C7 1.527(2) . ? C6 C8 1.538(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C9 C10 1.521(2) . ? C10 H10 1.0000 . ? C10 C11 1.530(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12 1.0000 . ? C12 C13 1.525(2) . ? C12 C14 1.537(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15 1.0000 . ? C15 C16 1.521(2) . ? C15 C17 1.530(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18 1.0000 . ? C18 C19 1.527(2) . ? C18 C20 1.532(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Ni1 P2 119.359(15) . . ? C1 Ni1 P1 139.81(6) . . ? C1 Ni1 P2 100.83(6) . . ? C2 Ni1 P1 98.74(6) . . ? C2 Ni1 P2 141.90(6) . . ? C2 Ni1 C1 41.07(8) . . ? C3 P1 Ni1 108.86(5) . . ? C3 P1 C6 107.95(7) . . ? C3 P1 C10 102.15(6) . . ? C6 P1 Ni1 119.34(5) . . ? C10 P1 Ni1 116.34(5) . . ? C10 P1 C6 100.58(7) . . ? C12 P2 Ni1 120.08(5) . . ? C15 P2 Ni1 115.47(5) . . ? C15 P2 C12 100.63(7) . . ? C15 P2 C18 102.68(6) . . ? C18 P2 Ni1 108.98(5) . . ? C18 P2 C12 107.35(6) . . ? Ni1 C1 H1A 112.8(15) . . ? Ni1 C1 H1B 109.1(15) . . ? C2 C1 Ni1 69.05(10) . . ? C2 C1 H1A 118.2(15) . . ? C2 C1 H1B 120.9(15) . . ? H1A C1 H1B 116(2) . . ? Ni1 C2 H2A 111.4(13) . . ? Ni1 C2 H2B 109.3(14) . . ? C1 C2 Ni1 69.88(10) . . ? C1 C2 H2A 119.1(14) . . ? C1 C2 H2B 119.5(15) . . ? H2A C2 H2B 117(2) . . ? P1 C3 H3 104.8 . . ? C4 C3 P1 112.12(9) . . ? C4 C3 H3 104.8 . . ? C5 C3 P1 117.95(10) . . ? C5 C3 H3 104.8 . . ? C5 C3 C4 111.03(12) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? P1 C6 H6 105.2 . . ? C7 C6 P1 110.91(11) . . ? C7 C6 H6 105.2 . . ? C7 C6 C8 110.10(13) . . ? C8 C6 P1 119.08(11) . . ? C8 C6 H6 105.2 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? P1 C10 H10 107.8 . . ? C9 C10 P1 114.30(11) . . ? C9 C10 H10 107.8 . . ? C9 C10 C11 109.64(13) . . ? C11 C10 P1 109.31(10) . . ? C11 C10 H10 107.8 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P2 C12 H12 105.1 . . ? C13 C12 P2 110.47(10) . . ? C13 C12 H12 105.1 . . ? C13 C12 C14 110.14(13) . . ? C14 C12 P2 119.64(11) . . ? C14 C12 H12 105.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? P2 C15 H15 107.6 . . ? C16 C15 P2 114.08(11) . . ? C16 C15 H15 107.6 . . ? C16 C15 C17 110.21(14) . . ? C17 C15 P2 109.56(10) . . ? C17 C15 H15 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? P2 C18 H18 105.0 . . ? C19 C18 P2 117.95(10) . . ? C19 C18 H18 105.0 . . ? C19 C18 C20 110.71(13) . . ? C20 C18 P2 111.82(10) . . ? C20 C18 H18 105.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 Ni1 P1 C3 C4 -48.80(11) . . . . ? Ni1 P1 C3 C5 -179.67(10) . . . . ? Ni1 P1 C6 C7 68.26(11) . . . . ? Ni1 P1 C6 C8 -162.44(10) . . . . ? Ni1 P1 C10 C9 -63.82(13) . . . . ? Ni1 P1 C10 C11 59.48(12) . . . . ? Ni1 P2 C12 C13 67.49(11) . . . . ? Ni1 P2 C12 C14 -163.08(10) . . . . ? Ni1 P2 C15 C16 -63.74(13) . . . . ? Ni1 P2 C15 C17 60.34(13) . . . . ? Ni1 P2 C18 C19 -179.83(10) . . . . ? Ni1 P2 C18 C20 -49.77(11) . . . . ? P1 Ni1 P2 C12 10.21(6) . . . . ? P1 Ni1 P2 C15 -110.59(6) . . . . ? P1 Ni1 P2 C18 134.51(5) . . . . ? P1 Ni1 C1 C2 -1.36(19) . . . . ? P1 Ni1 C2 C1 179.11(13) . . . . ? P2 Ni1 P1 C3 134.19(5) . . . . ? P2 Ni1 P1 C6 9.74(6) . . . . ? P2 Ni1 P1 C10 -111.14(5) . . . . ? P2 Ni1 C1 C2 179.67(13) . . . . ? P2 Ni1 C2 C1 -0.5(2) . . . . ? C1 Ni1 P1 C3 -44.65(12) . . . . ? C1 Ni1 P1 C6 -169.10(12) . . . . ? C1 Ni1 P1 C10 70.02(12) . . . . ? C1 Ni1 P2 C12 -170.55(9) . . . . ? C1 Ni1 P2 C15 68.65(9) . . . . ? C1 Ni1 P2 C18 -46.25(8) . . . . ? C2 Ni1 P1 C3 -45.55(8) . . . . ? C2 Ni1 P1 C6 -170.00(9) . . . . ? C2 Ni1 P1 C10 69.11(9) . . . . ? C2 Ni1 P2 C12 -170.21(12) . . . . ? C2 Ni1 P2 C15 68.99(12) . . . . ? C2 Ni1 P2 C18 -45.90(12) . . . . ? C3 P1 C6 C7 -56.63(12) . . . . ? C3 P1 C6 C8 72.67(13) . . . . ? C3 P1 C10 C9 54.58(13) . . . . ? C3 P1 C10 C11 177.88(11) . . . . ? C6 P1 C3 C4 82.12(12) . . . . ? C6 P1 C3 C5 -48.75(13) . . . . ? C6 P1 C10 C9 165.74(12) . . . . ? C6 P1 C10 C11 -70.96(12) . . . . ? C10 P1 C3 C4 -172.39(11) . . . . ? C10 P1 C3 C5 56.74(13) . . . . ? C10 P1 C6 C7 -163.22(10) . . . . ? C10 P1 C6 C8 -33.92(13) . . . . ? C12 P2 C15 C16 165.40(13) . . . . ? C12 P2 C15 C17 -70.52(13) . . . . ? C12 P2 C18 C19 -48.33(13) . . . . ? C12 P2 C18 C20 81.74(12) . . . . ? C15 P2 C12 C13 -164.61(11) . . . . ? C15 P2 C12 C14 -35.17(13) . . . . ? C15 P2 C18 C19 57.24(13) . . . . ? C15 P2 C18 C20 -172.70(11) . . . . ? C18 P2 C12 C13 -57.59(12) . . . . ? C18 P2 C12 C14 71.84(13) . . . . ? C18 P2 C15 C16 54.71(14) . . . . ? C18 P2 C15 C17 178.79(12) . . . . ? data_rbg7_3a _database_code_depnum_ccdc_archive 'CCDC 896749' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-31 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C9 H21 Cl0.5 Ni0.5 P)' _chemical_formula_sum 'C18 H42 Cl Ni P2' _chemical_formula_weight 414.62 _chemical_melting_point ? 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.620(2) _cell_length_b 13.030(3) _cell_length_c 15.806(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.85(3) _cell_angle_gamma 90.00 _cell_volume 2290.4(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4032 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.100 _exptl_absorpt_correction_T_max 0.8265 _exptl_absorpt_correction_T_min 0.7859 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS BRUKER 2001' _exptl_crystal_colour white _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cube _exptl_crystal_F_000 900 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_unetI/netI 0.0108 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11590 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 2.41 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 2178 _reflns_number_total 2253 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.274 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 2253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0230 _refine_ls_R_factor_gt 0.0224 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+1.2441P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.0621 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 1.0000 0.128295(16) 0.2500 0.02620(9) Uani 1 2 d S . . Cl1 Cl 1.0000 -0.03871(3) 0.2500 0.04281(14) Uani 1 2 d S . . P1 P 0.91842(3) 0.21427(2) 0.339556(19) 0.02366(10) Uani 1 1 d . . . C1 C 0.85257(15) 0.41219(12) 0.39676(11) 0.0429(4) Uani 1 1 d . . . H1A H 0.7693 0.4000 0.3614 0.064 Uiso 1 1 calc R . . H1B H 0.8697 0.4859 0.3984 0.064 Uiso 1 1 calc R . . H1C H 0.8639 0.3871 0.4571 0.064 Uiso 1 1 calc R . . C2 C 0.93831(13) 0.35519(10) 0.35524(9) 0.0302(3) Uani 1 1 d . . . H2 H 0.9229 0.3845 0.2945 0.036 Uiso 1 1 calc R . . C3 C 1.06884(15) 0.38170(11) 0.40349(11) 0.0409(3) Uani 1 1 d . . . H3A H 1.0857 0.3648 0.4663 0.061 Uiso 1 1 calc R . . H3B H 1.0822 0.4552 0.3971 0.061 Uiso 1 1 calc R . . H3C H 1.1224 0.3422 0.3780 0.061 Uiso 1 1 calc R . . C4 C 0.69732(13) 0.24440(13) 0.21563(10) 0.0416(3) Uani 1 1 d . . . H4A H 0.7191 0.3171 0.2162 0.062 Uiso 1 1 calc R . . H4B H 0.6096 0.2378 0.1994 0.062 Uiso 1 1 calc R . . H4C H 0.7279 0.2077 0.1724 0.062 Uiso 1 1 calc R . . C5 C 0.75271(11) 0.19841(11) 0.30761(8) 0.0309(3) Uani 1 1 d . . . H5 H 0.7209 0.2365 0.3510 0.037 Uiso 1 1 calc R . . C6 C 0.71770(14) 0.08556(13) 0.30858(12) 0.0495(4) Uani 1 1 d . . . H6A H 0.7570 0.0457 0.2722 0.074 Uiso 1 1 calc R . . H6B H 0.6303 0.0787 0.2847 0.074 Uiso 1 1 calc R . . H6C H 0.7434 0.0598 0.3694 0.074 Uiso 1 1 calc R . . C7 C 0.92235(15) 0.18741(16) 0.52201(10) 0.0499(4) Uani 1 1 d . . . H7A H 0.9551 0.2559 0.5402 0.075 Uiso 1 1 calc R . . H7B H 0.9464 0.1405 0.5726 0.075 Uiso 1 1 calc R . . H7C H 0.8344 0.1912 0.5008 0.075 Uiso 1 1 calc R . . C8 C 0.97067(12) 0.14804(11) 0.44807(9) 0.0326(3) Uani 1 1 d . . . H8 H 0.9386 0.0766 0.4363 0.039 Uiso 1 1 calc R . . C9 C 1.10756(14) 0.13530(12) 0.47966(11) 0.0418(4) Uani 1 1 d . . . H9A H 1.1353 0.1062 0.4319 0.063 Uiso 1 1 calc R . . H9B H 1.1296 0.0892 0.5308 0.063 Uiso 1 1 calc R . . H9C H 1.1454 0.2024 0.4965 0.063 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 0.02811(14) 0.02320(14) 0.02734(14) 0.000 0.00814(10) 0.000 Cl1 0.0548(3) 0.0222(2) 0.0503(3) 0.000 0.0136(2) 0.000 P1 0.02398(17) 0.02540(17) 0.02130(16) 0.00186(11) 0.00607(12) -0.00267(11) C1 0.0517(9) 0.0362(8) 0.0453(8) -0.0063(6) 0.0212(7) 0.0022(7) C2 0.0388(7) 0.0268(6) 0.0276(6) -0.0003(5) 0.0136(6) -0.0035(5) C3 0.0428(8) 0.0361(8) 0.0457(9) -0.0068(6) 0.0159(7) -0.0145(6) C4 0.0328(7) 0.0533(9) 0.0333(7) 0.0048(6) 0.0010(6) 0.0054(6) C5 0.0245(6) 0.0387(7) 0.0285(6) 0.0012(5) 0.0059(5) -0.0024(5) C6 0.0319(8) 0.0497(10) 0.0598(10) 0.0077(8) 0.0022(7) -0.0160(7) C7 0.0454(9) 0.0784(12) 0.0267(7) 0.0137(8) 0.0118(6) 0.0003(8) C8 0.0306(7) 0.0382(7) 0.0258(6) 0.0096(5) 0.0031(5) -0.0050(5) C9 0.0318(8) 0.0491(9) 0.0382(8) 0.0123(6) 0.0002(6) -0.0005(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 Ni1 Cl1 2.1761(7) . ? Ni1 P1 2.2215(5) . ? Ni1 P1 2.2215(5) 2_755 ? P1 C2 1.8583(14) . ? P1 C5 1.8552(14) . ? P1 C8 1.8578(14) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.534(2) . ? C2 H2 1.0000 . ? C2 C3 1.527(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 C5 1.5313(19) . ? C5 H5 1.0000 . ? C5 C6 1.527(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.525(2) . ? C8 H8 1.0000 . ? C8 C9 1.532(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ni1 P1 120.282(12) . 2_755 ? Cl1 Ni1 P1 120.282(12) . . ? P1 Ni1 P1 119.44(2) . 2_755 ? C2 P1 Ni1 121.59(4) . . ? C5 P1 Ni1 111.80(5) . . ? C5 P1 C2 103.03(7) . . ? C5 P1 C8 103.60(7) . . ? C8 P1 Ni1 105.57(5) . . ? C8 P1 C2 109.94(7) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? P1 C2 H2 105.6 . . ? C1 C2 P1 117.67(10) . . ? C1 C2 H2 105.6 . . ? C3 C2 P1 110.94(10) . . ? C3 C2 C1 110.56(12) . . ? C3 C2 H2 105.6 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? P1 C5 H5 108.6 . . ? C4 C5 P1 109.41(10) . . ? C4 C5 H5 108.6 . . ? C6 C5 P1 111.29(10) . . ? C6 C5 C4 110.27(12) . . ? C6 C5 H5 108.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P1 C8 H8 104.8 . . ? C7 C8 P1 117.20(11) . . ? C7 C8 H8 104.8 . . ? C7 C8 C9 111.40(12) . . ? C9 C8 P1 112.45(10) . . ? C9 C8 H8 104.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? data_rbg2_3b _database_code_depnum_ccdc_archive 'CCDC 896750' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-30 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C9 H21 Br0.5 Ni0.5 P)' _chemical_formula_sum 'C18 H42 Br Ni P2' _chemical_formula_weight 459.08 _chemical_melting_point ? 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.714(2) _cell_length_b 13.115(3) _cell_length_c 15.899(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.94(3) _cell_angle_gamma 90.00 _cell_volume 2336.6(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6028 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 2.675 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.753262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0996 before and 0.0228 after correction. The Ratio of minimum to maximum transmission is 0.753262. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour white _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description cube _exptl_crystal_F_000 972 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11892 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 2.39 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2045 _reflns_number_total 2307 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.06A (Bruker, 2003)' _computing_data_collection ? _computing_data_reduction 'SAINT v7.06A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.590 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.076 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 2307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0270 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+1.1827P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.0772 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.0000 -0.04327(2) 0.2500 0.04451(12) Uani 1 2 d S . . Ni1 Ni 0.0000 0.13235(3) 0.2500 0.02891(12) Uani 1 2 d S . . P1 P 0.08099(4) 0.21688(4) 0.16047(3) 0.02700(13) Uani 1 1 d . . . C1 C -0.10520(19) 0.1376(2) 0.01997(16) 0.0475(6) Uani 1 1 d . . . H1A H -0.1433 0.2038 0.0018 0.071 Uiso 1 1 calc R . . H1B H -0.1332 0.1096 0.0676 0.071 Uiso 1 1 calc R . . H1C H -0.1259 0.0907 -0.0302 0.071 Uiso 1 1 calc R . . C2 C 0.03050(18) 0.15145(18) 0.05229(13) 0.0376(5) Uani 1 1 d . . . H2 H 0.0632 0.0807 0.0639 0.045 Uiso 1 1 calc R . . C3 C 0.0788(2) 0.1919(2) -0.02057(15) 0.0580(7) Uani 1 1 d . . . H3A H 0.0563 0.1454 -0.0710 0.087 Uiso 1 1 calc R . . H3B H 0.1660 0.1967 0.0012 0.087 Uiso 1 1 calc R . . H3C H 0.0452 0.2596 -0.0388 0.087 Uiso 1 1 calc R . . C4 C 0.29842(19) 0.2442(2) 0.28623(14) 0.0461(6) Uani 1 1 d . . . H4A H 0.2649 0.2074 0.3272 0.069 Uiso 1 1 calc R . . H4B H 0.2790 0.3168 0.2867 0.069 Uiso 1 1 calc R . . H4C H 0.3853 0.2356 0.3042 0.069 Uiso 1 1 calc R . . C5 C 0.24563(17) 0.20159(17) 0.19354(13) 0.0343(4) Uani 1 1 d . . . H5 H 0.2778 0.2420 0.1522 0.041 Uiso 1 1 calc R . . C6 C 0.2821(2) 0.0905(2) 0.18975(19) 0.0546(7) Uani 1 1 d . . . H6A H 0.3687 0.0841 0.2152 0.082 Uiso 1 1 calc R . . H6B H 0.2593 0.0676 0.1284 0.082 Uiso 1 1 calc R . . H6C H 0.2418 0.0483 0.2232 0.082 Uiso 1 1 calc R . . C7 C 0.1448(2) 0.41453(19) 0.10430(17) 0.0483(6) Uani 1 1 d . . . H7A H 0.1326 0.3907 0.0439 0.072 Uiso 1 1 calc R . . H7B H 0.2277 0.4021 0.1388 0.072 Uiso 1 1 calc R . . H7C H 0.1278 0.4877 0.1038 0.072 Uiso 1 1 calc R . . C8 C 0.06077(18) 0.35681(15) 0.14551(13) 0.0342(4) Uani 1 1 d . . . H8 H 0.0759 0.3856 0.2060 0.041 Uiso 1 1 calc R . . C9 C -0.0696(2) 0.38285(18) 0.09711(16) 0.0459(6) Uani 1 1 d . . . H9A H -0.0827 0.4561 0.1023 0.069 Uiso 1 1 calc R . . H9B H -0.1225 0.3445 0.1233 0.069 Uiso 1 1 calc R . . H9C H -0.0867 0.3646 0.0349 0.069 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 0.0540(2) 0.02696(19) 0.0508(2) 0.000 0.01246(16) 0.000 Ni1 0.0300(2) 0.0265(2) 0.0298(2) 0.000 0.00814(15) 0.000 P1 0.0273(2) 0.0296(3) 0.0237(2) -0.00197(19) 0.00675(19) 0.00249(19) C1 0.0383(12) 0.0546(14) 0.0420(13) -0.0140(11) -0.0005(10) -0.0007(10) C2 0.0350(11) 0.0447(12) 0.0302(10) -0.0118(9) 0.0050(8) 0.0041(9) C3 0.0502(14) 0.094(2) 0.0308(12) -0.0182(13) 0.0129(10) -0.0036(14) C4 0.0356(12) 0.0605(15) 0.0364(12) -0.0024(11) 0.0015(9) -0.0078(10) C5 0.0287(10) 0.0413(12) 0.0325(10) 0.0005(9) 0.0082(8) 0.0014(8) C6 0.0348(12) 0.0563(16) 0.0671(17) -0.0072(13) 0.0063(11) 0.0146(11) C7 0.0567(15) 0.0420(13) 0.0491(14) 0.0096(11) 0.0199(12) -0.0018(11) C8 0.0435(11) 0.0323(11) 0.0294(10) 0.0021(8) 0.0151(9) 0.0036(9) C9 0.0487(13) 0.0418(13) 0.0493(13) 0.0092(10) 0.0175(11) 0.0164(10) _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 2.3033(7) . ? Ni1 P1 2.2230(7) . ? Ni1 P1 2.2231(7) 2 ? P1 C2 1.858(2) . ? P1 C5 1.856(2) . ? P1 C8 1.857(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.532(3) . ? C2 H2 1.0000 . ? C2 C3 1.525(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 C5 1.528(3) . ? C5 H5 1.0000 . ? C5 C6 1.525(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.532(3) . ? C8 H8 1.0000 . ? C8 C9 1.535(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Ni1 Br1 119.911(17) . . ? P1 Ni1 Br1 119.911(17) 2 . ? P1 Ni1 P1 120.18(3) . 2 ? C2 P1 Ni1 106.40(8) . . ? C5 P1 Ni1 111.52(7) . . ? C5 P1 C2 103.68(10) . . ? C5 P1 C8 103.08(10) . . ? C8 P1 Ni1 120.84(6) . . ? C8 P1 C2 110.09(10) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? P1 C2 H2 104.8 . . ? C1 C2 P1 112.60(14) . . ? C1 C2 H2 104.8 . . ? C3 C2 P1 117.01(16) . . ? C3 C2 C1 111.39(18) . . ? C3 C2 H2 104.8 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? P1 C5 H5 108.4 . . ? C4 C5 P1 109.20(15) . . ? C4 C5 H5 108.4 . . ? C6 C5 P1 111.85(15) . . ? C6 C5 C4 110.38(19) . . ? C6 C5 H5 108.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P1 C8 H8 105.6 . . ? C7 C8 P1 118.00(15) . . ? C7 C8 H8 105.6 . . ? C7 C8 C9 110.17(18) . . ? C9 C8 P1 110.81(15) . . ? C9 C8 H8 105.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? data_rbm2_3c _database_code_depnum_ccdc_archive 'CCDC 896751' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-06-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H42 I Ni P2' _chemical_formula_sum 'C18 H42 I Ni P2' _chemical_formula_weight 506.07 _chemical_melting_point ? 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' I I -0.4742 1.8119 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 11.741(2) _cell_length_b 13.153(3) _cell_length_c 17.089(6) _cell_angle_alpha 90.00 _cell_angle_beta 114.76(2) _cell_angle_gamma 90.00 _cell_volume 2396.4(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6034 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 2.229 _exptl_absorpt_correction_T_max 0.7916 _exptl_absorpt_correction_T_min 0.5093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1044 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.11 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_unetI/netI 0.0177 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 23211 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 2.03 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 4010 _reflns_number_total 4480 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.321 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.086 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 4480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0357 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+3.7319P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.0865 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I1 I 0.22831(2) 0.468798(18) 0.759981(16) 0.04827(10) Uani 1 1 d . . . Ni1 Ni 0.25463(3) 0.65414(3) 0.74613(2) 0.03377(12) Uani 1 1 d . . . P1 P 0.43488(7) 0.72795(6) 0.83278(5) 0.02928(17) Uani 1 1 d . . . P2 P 0.08925(7) 0.73204(6) 0.64429(5) 0.02924(17) Uani 1 1 d . . . C1 C 0.6251(4) 0.6850(4) 1.0028(3) 0.0791(16) Uani 1 1 d . . . H1A H 0.6208 0.7519 1.0266 0.119 Uiso 1 1 calc R . . H1B H 0.6841 0.6876 0.9758 0.119 Uiso 1 1 calc R . . H1C H 0.6537 0.6345 1.0492 0.119 Uiso 1 1 calc R . . C2 C 0.4949(3) 0.6554(3) 0.9352(2) 0.0422(8) Uani 1 1 d . . . H2 H 0.5042 0.5840 0.9187 0.051 Uiso 1 1 calc R . . C3 C 0.4009(4) 0.6489(3) 0.9752(2) 0.0543(10) Uani 1 1 d . . . H3A H 0.4291 0.5979 1.0213 0.082 Uiso 1 1 calc R . . H3B H 0.3186 0.6294 0.9309 0.082 Uiso 1 1 calc R . . H3C H 0.3945 0.7153 0.9992 0.082 Uiso 1 1 calc R . . C4 C 0.5884(4) 0.5992(3) 0.7891(3) 0.0637(11) Uani 1 1 d . . . H4A H 0.5106 0.5613 0.7580 0.096 Uiso 1 1 calc R . . H4B H 0.6309 0.5725 0.8479 0.096 Uiso 1 1 calc R . . H4C H 0.6433 0.5918 0.7593 0.096 Uiso 1 1 calc R . . C5 C 0.5581(3) 0.7112(3) 0.7927(2) 0.0387(7) Uani 1 1 d . . . H5 H 0.6359 0.7470 0.8327 0.046 Uiso 1 1 calc R . . C6 C 0.5138(4) 0.7588(3) 0.7037(2) 0.0525(10) Uani 1 1 d . . . H6A H 0.5783 0.7496 0.6820 0.079 Uiso 1 1 calc R . . H6B H 0.4988 0.8315 0.7074 0.079 Uiso 1 1 calc R . . H6C H 0.4359 0.7259 0.6645 0.079 Uiso 1 1 calc R . . C7 C 0.5663(4) 0.9179(3) 0.8987(3) 0.0572(10) Uani 1 1 d . . . H7A H 0.5547 0.9914 0.9012 0.086 Uiso 1 1 calc R . . H7B H 0.6161 0.9042 0.8659 0.086 Uiso 1 1 calc R . . H7C H 0.6102 0.8910 0.9573 0.086 Uiso 1 1 calc R . . C8 C 0.4381(3) 0.8663(3) 0.8543(2) 0.0385(7) Uani 1 1 d . . . H8 H 0.3975 0.8989 0.7962 0.046 Uiso 1 1 calc R . . C9 C 0.3542(4) 0.8934(3) 0.8996(3) 0.0529(9) Uani 1 1 d . . . H9A H 0.3957 0.8733 0.9603 0.079 Uiso 1 1 calc R . . H9B H 0.2741 0.8575 0.8718 0.079 Uiso 1 1 calc R . . H9C H 0.3391 0.9669 0.8958 0.079 Uiso 1 1 calc R . . C10 C 0.1510(4) 0.6268(3) 0.5231(3) 0.0525(10) Uani 1 1 d . . . H10A H 0.1243 0.5762 0.4768 0.079 Uiso 1 1 calc R . . H10B H 0.2196 0.5989 0.5744 0.079 Uiso 1 1 calc R . . H10C H 0.1800 0.6882 0.5044 0.079 Uiso 1 1 calc R . . C11 C 0.0402(3) 0.6538(3) 0.5447(2) 0.0374(7) Uani 1 1 d . . . H11 H 0.0099 0.5878 0.5581 0.045 Uiso 1 1 calc R . . C12 C -0.0701(4) 0.6975(4) 0.4666(2) 0.0560(10) Uani 1 1 d . . . H12A H -0.0433 0.7593 0.4470 0.084 Uiso 1 1 calc R . . H12B H -0.1389 0.7139 0.4827 0.084 Uiso 1 1 calc R . . H12C H -0.0989 0.6472 0.4199 0.084 Uiso 1 1 calc R . . C13 C -0.1189(3) 0.6248(3) 0.6500(2) 0.0470(8) Uani 1 1 d . . . H13A H -0.0614 0.5680 0.6760 0.070 Uiso 1 1 calc R . . H13B H -0.1572 0.6173 0.5872 0.070 Uiso 1 1 calc R . . H13C H -0.1846 0.6250 0.6711 0.070 Uiso 1 1 calc R . . C14 C -0.0465(3) 0.7244(3) 0.6743(2) 0.0357(7) Uani 1 1 d . . . H14 H -0.1058 0.7808 0.6442 0.043 Uiso 1 1 calc R . . C15 C 0.0006(4) 0.7410(3) 0.7715(2) 0.0476(9) Uani 1 1 d . . . H15A H -0.0711 0.7444 0.7867 0.071 Uiso 1 1 calc R . . H15B H 0.0478 0.8049 0.7877 0.071 Uiso 1 1 calc R . . H15C H 0.0552 0.6844 0.8024 0.071 Uiso 1 1 calc R . . C16 C 0.1718(4) 0.8886(3) 0.5681(3) 0.0565(10) Uani 1 1 d . . . H16A H 0.1627 0.9594 0.5487 0.085 Uiso 1 1 calc R . . H16B H 0.1572 0.8433 0.5193 0.085 Uiso 1 1 calc R . . H16C H 0.2567 0.8778 0.6128 0.085 Uiso 1 1 calc R . . C17 C 0.0764(3) 0.8656(3) 0.6048(2) 0.0439(8) Uani 1 1 d . . . H17 H -0.0089 0.8736 0.5567 0.053 Uiso 1 1 calc R . . C18 C 0.0875(4) 0.9426(3) 0.6733(3) 0.0543(10) Uani 1 1 d . . . H18A H 0.1700 0.9364 0.7218 0.081 Uiso 1 1 calc R . . H18B H 0.0219 0.9300 0.6934 0.081 Uiso 1 1 calc R . . H18C H 0.0776 1.0113 0.6491 0.081 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 I1 0.05068(16) 0.03952(15) 0.04995(16) 0.00040(10) 0.01649(12) -0.00522(10) Ni1 0.0273(2) 0.0394(2) 0.0305(2) -0.00232(16) 0.00807(17) -0.00108(16) P1 0.0285(4) 0.0329(4) 0.0239(4) 0.0004(3) 0.0084(3) -0.0005(3) P2 0.0280(4) 0.0332(4) 0.0255(4) -0.0035(3) 0.0103(3) -0.0012(3) C1 0.054(3) 0.110(4) 0.043(2) 0.034(2) -0.009(2) -0.021(3) C2 0.0379(18) 0.050(2) 0.0307(17) 0.0094(14) 0.0070(14) -0.0037(15) C3 0.063(2) 0.066(3) 0.0381(19) 0.0056(18) 0.0253(18) -0.005(2) C4 0.059(2) 0.055(2) 0.091(3) -0.008(2) 0.044(2) 0.008(2) C5 0.0317(16) 0.0446(19) 0.0404(18) -0.0026(14) 0.0157(14) -0.0024(14) C6 0.051(2) 0.073(3) 0.0402(19) -0.0042(18) 0.0255(17) -0.0130(19) C7 0.057(2) 0.051(2) 0.060(2) -0.0158(19) 0.020(2) -0.0149(19) C8 0.0419(18) 0.0389(18) 0.0316(16) -0.0039(14) 0.0126(14) -0.0009(14) C9 0.054(2) 0.050(2) 0.056(2) -0.0116(18) 0.0249(19) 0.0047(18) C10 0.062(2) 0.056(2) 0.052(2) -0.0195(18) 0.037(2) -0.0098(19) C11 0.0387(17) 0.0444(19) 0.0304(16) -0.0099(14) 0.0156(14) -0.0079(14) C12 0.048(2) 0.084(3) 0.0283(17) -0.0078(18) 0.0087(16) -0.006(2) C13 0.0404(19) 0.056(2) 0.050(2) -0.0001(17) 0.0243(17) -0.0073(16) C14 0.0307(16) 0.0459(19) 0.0309(16) 0.0029(14) 0.0133(13) 0.0053(13) C15 0.050(2) 0.064(2) 0.0353(18) -0.0004(17) 0.0246(16) 0.0088(18) C16 0.071(3) 0.045(2) 0.067(3) 0.0035(19) 0.042(2) -0.0072(19) C17 0.0455(19) 0.0384(18) 0.051(2) 0.0033(15) 0.0235(17) 0.0027(15) C18 0.061(2) 0.045(2) 0.061(2) -0.0026(18) 0.029(2) 0.0032(18) _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 I1 Ni1 2.4810(7) . ? Ni1 P1 2.2336(10) . ? Ni1 P2 2.2402(10) . ? P1 C2 1.854(3) . ? P1 C5 1.855(3) . ? P1 C8 1.853(3) . ? P2 C11 1.863(3) . ? P2 C14 1.870(3) . ? P2 C17 1.866(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.530(5) . ? C2 H2 1.0000 . ? C2 C3 1.525(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 C5 1.523(5) . ? C5 H5 1.0000 . ? C5 C6 1.521(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.532(5) . ? C8 H8 1.0000 . ? C8 C9 1.528(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 C11 1.535(5) . ? C11 H11 1.0000 . ? C11 C12 1.530(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 C14 1.521(5) . ? C14 H14 1.0000 . ? C14 C15 1.532(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 C17 1.525(5) . ? C17 H17 1.0000 . ? C17 C18 1.512(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Ni1 I1 119.02(3) . . ? P1 Ni1 P2 126.05(4) . . ? P2 Ni1 I1 114.93(3) . . ? C2 P1 Ni1 106.39(11) . . ? C2 P1 C5 103.92(16) . . ? C5 P1 Ni1 111.88(11) . . ? C8 P1 Ni1 119.53(11) . . ? C8 P1 C2 110.48(16) . . ? C8 P1 C5 103.63(16) . . ? C11 P2 Ni1 107.03(12) . . ? C11 P2 C14 104.36(15) . . ? C11 P2 C17 104.03(16) . . ? C14 P2 Ni1 108.86(10) . . ? C17 P2 Ni1 128.64(12) . . ? C17 P2 C14 101.59(15) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? P1 C2 H2 105.0 . . ? C1 C2 P1 116.5(3) . . ? C1 C2 H2 105.0 . . ? C3 C2 P1 113.1(3) . . ? C3 C2 C1 111.0(3) . . ? C3 C2 H2 105.0 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? P1 C5 H5 108.8 . . ? C4 C5 P1 111.2(3) . . ? C4 C5 H5 108.8 . . ? C6 C5 P1 109.1(2) . . ? C6 C5 C4 110.2(3) . . ? C6 C5 H5 108.8 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P1 C8 H8 105.2 . . ? C7 C8 P1 117.8(3) . . ? C7 C8 H8 105.2 . . ? C9 C8 P1 111.5(3) . . ? C9 C8 C7 110.7(3) . . ? C9 C8 H8 105.2 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? P2 C11 H11 105.9 . . ? C10 C11 P2 112.2(2) . . ? C10 C11 H11 105.9 . . ? C12 C11 P2 114.5(3) . . ? C12 C11 C10 111.7(3) . . ? C12 C11 H11 105.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? P2 C14 H14 108.0 . . ? C13 C14 P2 114.5(2) . . ? C13 C14 H14 108.0 . . ? C13 C14 C15 109.0(3) . . ? C15 C14 P2 109.1(2) . . ? C15 C14 H14 108.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? P2 C17 H17 107.3 . . ? C16 C17 P2 111.9(3) . . ? C16 C17 H17 107.3 . . ? C18 C17 P2 112.5(3) . . ? C18 C17 C16 110.2(3) . . ? C18 C17 H17 107.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? data_rbl2_4 _database_code_depnum_ccdc_archive 'CCDC 896752' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-30 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H43 Cl Ni P2' _chemical_formula_sum 'C18 H43 Cl Ni P2' _chemical_formula_weight 415.62 _chemical_melting_point ? 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' P P 0.1023 0.0942 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 16.264(3) _cell_length_b 8.9520(18) _cell_length_c 15.834(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.85(3) _cell_angle_gamma 90.00 _cell_volume 2300.2(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6028 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_T_max 0.8025 _exptl_absorpt_correction_T_min 0.6501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description bloc _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 23069 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 1.25 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 4045 _reflns_number_total 4517 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.778 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.063 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 215 _refine_ls_number_reflns 4517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0337 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+1.5479P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.0858 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.247616(15) 0.02665(3) 0.486835(16) 0.02410(9) Uani 1 1 d . . . H1 H 0.2495(15) -0.079(3) 0.5389(17) 0.054(8) Uiso 1 1 d . . . Cl1 Cl 0.24618(5) 0.20988(7) 0.39356(4) 0.0593(2) Uani 1 1 d . . . P1 P 0.19319(3) -0.14848(6) 0.40486(3) 0.02458(13) Uani 1 1 d . . . P2 P 0.30529(3) 0.14735(6) 0.59524(3) 0.02349(13) Uani 1 1 d . . . C1 C 0.42861(16) -0.0672(3) 0.63001(17) 0.0479(6) Uani 1 1 d . . . H1A H 0.4033 -0.1094 0.5774 0.072 Uiso 1 1 calc R . . H1B H 0.4476 -0.1483 0.6680 0.072 Uiso 1 1 calc R . . H1C H 0.4756 -0.0045 0.6172 0.072 Uiso 1 1 calc R . . C2 C 0.36519(13) 0.0275(3) 0.67275(14) 0.0322(5) Uani 1 1 d . . . H2 H 0.3247 -0.0449 0.6942 0.039 Uiso 1 1 calc R . . C3 C 0.40474(17) 0.1049(3) 0.75101(16) 0.0505(7) Uani 1 1 d . . . H3A H 0.4500 0.1687 0.7347 0.076 Uiso 1 1 calc R . . H3B H 0.4262 0.0295 0.7916 0.076 Uiso 1 1 calc R . . H3C H 0.3634 0.1662 0.7771 0.076 Uiso 1 1 calc R . . C4 C 0.17145(14) 0.1164(3) 0.69580(16) 0.0424(6) Uani 1 1 d . . . H4A H 0.1438 0.0573 0.6502 0.064 Uiso 1 1 calc R . . H4B H 0.1301 0.1663 0.7281 0.064 Uiso 1 1 calc R . . H4C H 0.2052 0.0504 0.7334 0.064 Uiso 1 1 calc R . . C5 C 0.22638(13) 0.2333(2) 0.65799(13) 0.0294(4) Uani 1 1 d . . . H5 H 0.2550 0.2908 0.7055 0.035 Uiso 1 1 calc R . . C6 C 0.17380(16) 0.3420(3) 0.60302(16) 0.0490(7) Uani 1 1 d . . . H6A H 0.2082 0.4251 0.5858 0.074 Uiso 1 1 calc R . . H6B H 0.1292 0.3808 0.6354 0.074 Uiso 1 1 calc R . . H6C H 0.1503 0.2899 0.5526 0.074 Uiso 1 1 calc R . . C7 C 0.44182(17) 0.2580(4) 0.5157(2) 0.0637(9) Uani 1 1 d . . . H7A H 0.4831 0.2105 0.5548 0.096 Uiso 1 1 calc R . . H7B H 0.4662 0.3450 0.4894 0.096 Uiso 1 1 calc R . . H7C H 0.4231 0.1864 0.4717 0.096 Uiso 1 1 calc R . . C8 C 0.36846(13) 0.3079(3) 0.56435(14) 0.0339(5) Uani 1 1 d . . . H8 H 0.3321 0.3643 0.5220 0.041 Uiso 1 1 calc R . . C9 C 0.3941(2) 0.4222(4) 0.63193(19) 0.0687(10) Uani 1 1 d . . . H9A H 0.3457 0.4539 0.6609 0.103 Uiso 1 1 calc R . . H9B H 0.4187 0.5090 0.6055 0.103 Uiso 1 1 calc R . . H9C H 0.4347 0.3774 0.6730 0.103 Uiso 1 1 calc R . . C10 C 0.05842(15) -0.1969(3) 0.50357(16) 0.0442(6) Uani 1 1 d . . . H10A H 0.0822 -0.1102 0.5341 0.066 Uiso 1 1 calc R . . H10B H 0.0340 -0.2646 0.5436 0.066 Uiso 1 1 calc R . . H10C H 0.0157 -0.1633 0.4612 0.066 Uiso 1 1 calc R . . C11 C 0.12592(13) -0.2788(2) 0.45955(14) 0.0321(5) Uani 1 1 d . . . H11 H 0.1622 -0.3235 0.5064 0.039 Uiso 1 1 calc R . . C12 C 0.09083(17) -0.4121(3) 0.40837(17) 0.0495(7) Uani 1 1 d . . . H12A H 0.0487 -0.3771 0.3658 0.074 Uiso 1 1 calc R . . H12B H 0.0662 -0.4831 0.4464 0.074 Uiso 1 1 calc R . . H12C H 0.1352 -0.4615 0.3801 0.074 Uiso 1 1 calc R . . C13 C 0.06335(16) 0.0103(4) 0.3227(2) 0.0672(10) Uani 1 1 d . . . H13A H 0.0190 -0.0582 0.3360 0.101 Uiso 1 1 calc R . . H13B H 0.0458 0.0694 0.2726 0.101 Uiso 1 1 calc R . . H13C H 0.0759 0.0773 0.3709 0.101 Uiso 1 1 calc R . . C14 C 0.13977(14) -0.0789(3) 0.30518(13) 0.0355(5) Uani 1 1 d . . . H14 H 0.1785 -0.0046 0.2824 0.043 Uiso 1 1 calc R . . C15 C 0.1227(3) -0.1924(3) 0.23349(18) 0.0776(11) Uani 1 1 d . . . H15A H 0.1735 -0.2466 0.2236 0.116 Uiso 1 1 calc R . . H15B H 0.1032 -0.1399 0.1817 0.116 Uiso 1 1 calc R . . H15C H 0.0805 -0.2633 0.2494 0.116 Uiso 1 1 calc R . . C16 C 0.33688(18) -0.1754(3) 0.3224(2) 0.0601(8) Uani 1 1 d . . . H16A H 0.3088 -0.1274 0.2728 0.090 Uiso 1 1 calc R . . H16B H 0.3811 -0.2397 0.3041 0.090 Uiso 1 1 calc R . . H16C H 0.3603 -0.0987 0.3611 0.090 Uiso 1 1 calc R . . C17 C 0.27523(14) -0.2696(2) 0.36768(14) 0.0341(5) Uani 1 1 d . . . H17 H 0.2493 -0.3425 0.3261 0.041 Uiso 1 1 calc R . . C18 C 0.31889(17) -0.3572(3) 0.43938(18) 0.0502(7) Uani 1 1 d . . . H18A H 0.3410 -0.2879 0.4831 0.075 Uiso 1 1 calc R . . H18B H 0.3641 -0.4149 0.4176 0.075 Uiso 1 1 calc R . . H18C H 0.2797 -0.4254 0.4638 0.075 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 0.02802(15) 0.02289(15) 0.02113(14) -0.00088(10) -0.00032(10) -0.00151(10) Cl1 0.1115(6) 0.0351(3) 0.0282(3) 0.0082(2) -0.0176(3) -0.0251(4) P1 0.0265(3) 0.0240(3) 0.0229(3) 0.0001(2) -0.0010(2) -0.0029(2) P2 0.0225(3) 0.0255(3) 0.0222(3) 0.0000(2) -0.00088(19) -0.0009(2) C1 0.0444(14) 0.0505(16) 0.0477(15) -0.0023(12) -0.0054(11) 0.0183(12) C2 0.0288(11) 0.0348(12) 0.0321(11) 0.0037(9) -0.0045(9) 0.0056(9) C3 0.0532(15) 0.0608(17) 0.0348(13) -0.0019(12) -0.0166(11) 0.0104(13) C4 0.0370(12) 0.0495(15) 0.0420(13) -0.0042(11) 0.0128(10) -0.0052(11) C5 0.0309(10) 0.0320(11) 0.0254(10) -0.0029(9) 0.0014(8) 0.0009(9) C6 0.0493(15) 0.0551(17) 0.0433(14) 0.0049(12) 0.0080(12) 0.0243(12) C7 0.0408(15) 0.064(2) 0.089(2) 0.0178(17) 0.0255(15) -0.0062(14) C8 0.0332(11) 0.0334(12) 0.0349(12) 0.0043(10) -0.0007(9) -0.0104(9) C9 0.095(2) 0.0585(19) 0.0507(17) -0.0008(15) -0.0090(16) -0.0461(18) C10 0.0393(13) 0.0531(16) 0.0413(13) 0.0008(12) 0.0109(11) -0.0063(11) C11 0.0325(11) 0.0325(12) 0.0311(11) 0.0049(9) 0.0004(9) -0.0068(9) C12 0.0556(16) 0.0407(14) 0.0529(16) -0.0040(12) 0.0077(12) -0.0211(12) C13 0.0374(15) 0.105(3) 0.0583(19) 0.0369(18) -0.0038(13) 0.0167(15) C14 0.0399(12) 0.0389(13) 0.0260(11) 0.0053(10) -0.0097(9) -0.0087(10) C15 0.133(3) 0.0492(18) 0.0442(16) 0.0062(14) -0.0403(19) -0.0314(19) C16 0.0538(17) 0.0514(17) 0.079(2) 0.0071(15) 0.0367(15) 0.0054(13) C17 0.0372(12) 0.0271(11) 0.0387(12) -0.0068(9) 0.0075(9) -0.0002(9) C18 0.0475(15) 0.0413(15) 0.0618(17) 0.0015(13) 0.0025(13) 0.0144(12) _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 H1 1.25(3) . ? Ni1 Cl1 2.2062(7) . ? Ni1 P1 2.1845(7) . ? Ni1 P2 2.1858(7) . ? P1 C11 1.853(2) . ? P1 C14 1.858(2) . ? P1 C17 1.846(2) . ? P2 C2 1.856(2) . ? P2 C5 1.843(2) . ? P2 C8 1.852(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C1 C2 1.528(3) . ? C2 H2 1.0000 . ? C2 C3 1.524(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 C5 1.524(3) . ? C5 H5 1.0000 . ? C5 C6 1.529(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.530(4) . ? C8 H8 1.0000 . ? C8 C9 1.518(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 C11 1.527(3) . ? C11 H11 1.0000 . ? C11 C12 1.531(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 C14 1.518(4) . ? C14 H14 1.0000 . ? C14 C15 1.535(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 C17 1.526(3) . ? C17 H17 1.0000 . ? C17 C18 1.516(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Ni1 H1 178.8(12) . . ? P1 Ni1 H1 80.8(12) . . ? P1 Ni1 Cl1 98.64(3) . . ? P1 Ni1 P2 163.10(2) . . ? P2 Ni1 H1 82.3(12) . . ? P2 Ni1 Cl1 98.21(3) . . ? C11 P1 Ni1 113.73(7) . . ? C11 P1 C14 110.55(10) . . ? C14 P1 Ni1 114.32(8) . . ? C17 P1 Ni1 109.78(8) . . ? C17 P1 C11 103.96(10) . . ? C17 P1 C14 103.47(11) . . ? C2 P2 Ni1 114.34(8) . . ? C5 P2 Ni1 110.61(7) . . ? C5 P2 C2 103.78(10) . . ? C5 P2 C8 103.72(10) . . ? C8 P2 Ni1 113.13(7) . . ? C8 P2 C2 110.33(10) . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? P2 C2 H2 105.7 . . ? C1 C2 P2 111.57(16) . . ? C1 C2 H2 105.7 . . ? C3 C2 P2 116.71(17) . . ? C3 C2 C1 110.59(19) . . ? C3 C2 H2 105.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? P2 C5 H5 108.3 . . ? C4 C5 P2 111.90(16) . . ? C4 C5 H5 108.3 . . ? C4 C5 C6 109.91(19) . . ? C6 C5 P2 110.00(15) . . ? C6 C5 H5 108.3 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P2 C8 H8 104.8 . . ? C7 C8 P2 111.79(18) . . ? C7 C8 H8 104.8 . . ? C9 C8 P2 117.90(17) . . ? C9 C8 C7 111.4(2) . . ? C9 C8 H8 104.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? P1 C11 H11 105.1 . . ? C10 C11 P1 112.10(16) . . ? C10 C11 H11 105.1 . . ? C10 C11 C12 111.23(19) . . ? C12 C11 P1 117.00(16) . . ? C12 C11 H11 105.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? P1 C14 H14 105.1 . . ? C13 C14 P1 111.27(17) . . ? C13 C14 H14 105.1 . . ? C13 C14 C15 112.0(2) . . ? C15 C14 P1 117.19(19) . . ? C15 C14 H14 105.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? P1 C17 H17 108.2 . . ? C16 C17 P1 109.70(16) . . ? C16 C17 H17 108.2 . . ? C18 C17 P1 112.15(16) . . ? C18 C17 C16 110.4(2) . . ? C18 C17 H17 108.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? data_twin5b _database_code_depnum_ccdc_archive 'CCDC 896753' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2012-08-16T11:42:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H84 Ni2 N2 P2' _chemical_formula_sum 'C36 H84 N2 Ni2 P4' _chemical_formula_weight 786.35 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.950(4) _cell_length_b 21.071(5) _cell_length_c 15.531(4) _cell_angle_alpha 90 _cell_angle_beta 114.158(5) _cell_angle_gamma 90 _cell_volume 4464(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7800 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.17 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.011 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_unetI/netI 0.0898 _diffrn_reflns_number 34028 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _reflns_number_total 34032 _reflns_number_gt 23468 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0000P)^2^+39.4245P] 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_number_reflns 34032 _refine_ls_number_parameters 426 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1381 _refine_ls_R_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.1921 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.244 _refine_ls_restrained_S_all 1.243 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.276 _refine_diff_density_min -1.775 _refine_diff_density_rms 0.161 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' P P 0.1023 0.0942 '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' 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 0.30268(5) 0.62187(4) 0.17935(6) 0.0306(2) Uiso 1 1 d . B . Ni2 Ni 0.64563(5) 0.62253(4) 0.31556(6) 0.0361(2) Uani 1 1 d . . . P2 P 0.22650(12) 0.68349(7) 0.23794(12) 0.0287(4) Uani 1 1 d . B . P3 P 0.71645(12) 0.54562(7) 0.41031(12) 0.0335(4) Uani 1 1 d . D . P1 P 0.23551(14) 0.55628(8) 0.06396(12) 0.0445(5) Uani 1 1 d . . . N1 N 0.4311(4) 0.6232(2) 0.2305(4) 0.0310(12) Uani 1 1 d U . . N2 N 0.5160(4) 0.6226(2) 0.2659(3) 0.0355(13) Uani 1 1 d . . . C28 C 0.6467(5) 0.7765(3) 0.2535(4) 0.0396(17) Uani 1 1 d . . . H28 H 0.6895 0.809 0.2424 0.048 Uiso 1 1 calc R A 1 C24 C 0.8764(4) 0.4558(3) 0.4766(5) 0.055(2) Uani 1 1 d . D . H241 H 0.9415 0.4466 0.4786 0.083 Uiso 1 1 calc R . . H242 H 0.8319 0.4206 0.4458 0.083 Uiso 1 1 calc R . . H243 H 0.8812 0.4609 0.5411 0.083 Uiso 1 1 calc R . . C22 C 0.8366(4) 0.5174(3) 0.4207(4) 0.0348(16) Uani 1 1 d . . . H221 H 0.8836 0.5511 0.4581 0.042 Uiso 1 1 calc R D . C19 C 0.6438(5) 0.4695(3) 0.3838(6) 0.052(2) Uani 1 1 d . . . H19 H 0.6852 0.4366 0.4288 0.063 Uiso 1 1 calc R D . C29 C 0.5475(5) 0.7748(3) 0.1730(5) 0.071(2) Uani 1 1 d . D . H291 H 0.5092 0.7398 0.1824 0.107 Uiso 1 1 calc R . . H292 H 0.5549 0.7684 0.1138 0.107 Uiso 1 1 calc R . . H293 H 0.5136 0.815 0.1703 0.107 Uiso 1 1 calc R . . C23 C 0.8467(5) 0.5156(3) 0.3260(5) 0.051(2) Uani 1 1 d . D . H231 H 0.9154 0.5084 0.3376 0.077 Uiso 1 1 calc R . . H232 H 0.8248 0.5562 0.2931 0.077 Uiso 1 1 calc R . . H233 H 0.8063 0.4812 0.2869 0.077 Uiso 1 1 calc R . . C30 C 0.6327(6) 0.7908(3) 0.3413(5) 0.085(3) Uani 1 1 d . D . H301 H 0.5934 0.8295 0.332 0.128 Uiso 1 1 calc R . . H302 H 0.6968 0.7971 0.3938 0.128 Uiso 1 1 calc R . . H303 H 0.5988 0.7553 0.3558 0.128 Uiso 1 1 calc R . . C21 C 0.6226(5) 0.4467(3) 0.2849(5) 0.070(2) Uani 1 1 d . D . H211 H 0.5842 0.4074 0.2723 0.105 Uiso 1 1 calc R . . H212 H 0.6845 0.4386 0.2792 0.105 Uiso 1 1 calc R . . H213 H 0.5854 0.4792 0.2392 0.105 Uiso 1 1 calc R . . C16 C 0.1180(5) 0.6522(4) 0.2546(5) 0.063(2) Uani 1 1 d . . . C81 C 0.2539(9) 0.4661(7) 0.2062(9) 0.039(4) Uiso 0.5 1 d P B 1 H81A H 0.235 0.4255 0.2247 0.058 Uiso 0.5 1 calc PR B 1 H81B H 0.251 0.4996 0.2487 0.058 Uiso 0.5 1 calc PR B 1 H81C H 0.3208 0.463 0.2099 0.058 Uiso 0.5 1 calc PR B 1 C25 C 0.7388(6) 0.5623(3) 0.5365(5) 0.063(2) Uani 1 1 d U . . H25 H 0.731 0.5212 0.565 0.075 Uiso 1 1 calc R D . C71 C 0.1851(10) 0.4816(5) 0.1073(8) 0.025(3) Uiso 0.5 1 d P B 1 H71 H 0.1215 0.4945 0.1092 0.03 Uiso 0.5 1 calc PR B 1 C20 C 0.5504(5) 0.4768(3) 0.4001(6) 0.100(3) Uani 1 1 d . D . H201 H 0.5046 0.5048 0.3518 0.15 Uiso 1 1 calc R . . H202 H 0.5666 0.4951 0.4627 0.15 Uiso 1 1 calc R . . H203 H 0.52 0.4351 0.3963 0.15 Uiso 1 1 calc R . . C17 C 0.0262(5) 0.6550(5) 0.1636(5) 0.127(4) Uani 1 1 d . C . H171 H 0.0419 0.6416 0.1109 0.191 Uiso 1 1 calc R . . H172 H 0.001 0.6985 0.1528 0.191 Uiso 1 1 calc R . . H173 H -0.0236 0.6266 0.1681 0.191 Uiso 1 1 calc R . . C26 C 0.6598(7) 0.6059(4) 0.5364(6) 0.114(4) Uani 1 1 d U D . H261 H 0.6738 0.6492 0.5226 0.171 Uiso 1 1 calc R . . H262 H 0.6574 0.6048 0.5985 0.171 Uiso 1 1 calc R . . H263 H 0.5966 0.5921 0.4882 0.171 Uiso 1 1 calc R . . C27 C 0.8389(7) 0.5870(4) 0.5960(5) 0.105(4) Uani 1 1 d U D . H271 H 0.8523 0.6244 0.5657 0.158 Uiso 1 1 calc R . . H272 H 0.8877 0.5541 0.6031 0.158 Uiso 1 1 calc R . . H273 H 0.8423 0.5988 0.6583 0.158 Uiso 1 1 calc R . . C181 C 0.1219(9) 0.5903(6) 0.2815(10) 0.049(3) Uani 0.5 1 d P C 1 H181 H 0.1823 0.5829 0.338 0.073 Uiso 0.5 1 calc PR C 1 H182 H 0.1211 0.5627 0.2304 0.073 Uiso 0.5 1 calc PR C 1 H183 H 0.0651 0.5806 0.2955 0.073 Uiso 0.5 1 calc PR C 1 C182 C 0.0986(9) 0.6701(6) 0.3312(9) 0.049(3) Uani 0.5 1 d P C 2 H184 H 0.0421 0.6463 0.3306 0.073 Uiso 0.5 1 calc PR C 2 H185 H 0.0841 0.7157 0.3274 0.073 Uiso 0.5 1 calc PR C 2 H186 H 0.156 0.6611 0.3898 0.073 Uiso 0.5 1 calc PR C 2 C10 C 0.1780(4) 0.7544(3) 0.1626(4) 0.0380(17) Uani 1 1 d . . . H10 H 0.1178 0.7397 0.108 0.046 Uiso 1 1 calc R C . C15 C 0.3386(5) 0.6606(3) 0.4267(4) 0.069(2) Uani 1 1 d . C . H151 H 0.3786 0.6322 0.4069 0.103 Uiso 1 1 calc R . . H152 H 0.2826 0.637 0.428 0.103 Uiso 1 1 calc R . . H153 H 0.3783 0.6771 0.4899 0.103 Uiso 1 1 calc R . . C13 C 0.3017(4) 0.7154(3) 0.3575(4) 0.0372(16) Uani 1 1 d . . . H13 H 0.2599 0.7438 0.3774 0.045 Uiso 1 1 calc R C . C11 C 0.1451(5) 0.8101(3) 0.2062(5) 0.056(2) Uani 1 1 d . C . H111 H 0.2025 0.8299 0.2556 0.084 Uiso 1 1 calc R . . H112 H 0.1008 0.7946 0.2337 0.084 Uiso 1 1 calc R . . H113 H 0.1108 0.8415 0.1571 0.084 Uiso 1 1 calc R . . C14 C 0.3899(4) 0.7535(3) 0.3583(5) 0.063(2) Uani 1 1 d . C . H141 H 0.4336 0.764 0.4236 0.094 Uiso 1 1 calc R . . H142 H 0.3666 0.7927 0.3221 0.094 Uiso 1 1 calc R . . H143 H 0.4255 0.7281 0.3299 0.094 Uiso 1 1 calc R . . C1 C 0.3112(6) 0.5316(4) 0.0017(5) 0.082(3) Uani 1 1 d . B . H1 H 0.2729 0.5015 -0.0502 0.098 Uiso 1 1 calc R . . C3 C 0.3404(6) 0.5905(4) -0.0409(5) 0.103(4) Uani 1 1 d . . . H31 H 0.3765 0.6205 0.0097 0.154 Uiso 1 1 calc R B . H32 H 0.2812 0.611 -0.0866 0.154 Uiso 1 1 calc R . . H33 H 0.3821 0.5772 -0.0726 0.154 Uiso 1 1 calc R . . C12 C 0.2477(5) 0.7769(3) 0.1204(5) 0.065(2) Uani 1 1 d . C . H121 H 0.2148 0.8086 0.0715 0.097 Uiso 1 1 calc R . . H122 H 0.2675 0.7407 0.0925 0.097 Uiso 1 1 calc R . . H123 H 0.3059 0.7958 0.17 0.097 Uiso 1 1 calc R . . C5 C 0.1114(5) 0.6468(3) -0.0579(5) 0.066(2) Uani 1 1 d . . . H51 H 0.1612 0.6577 -0.0812 0.099 Uiso 1 1 calc R B . H52 H 0.1229 0.6714 -0.0008 0.099 Uiso 1 1 calc R . . H53 H 0.0462 0.6568 -0.1064 0.099 Uiso 1 1 calc R . . C6 C 0.0880(6) 0.5382(3) -0.1262(5) 0.090(3) Uani 1 1 d . . . H61 H 0.0212 0.5497 -0.1697 0.135 Uiso 1 1 calc R B . H62 H 0.0906 0.4928 -0.1117 0.135 Uiso 1 1 calc R . . H63 H 0.1334 0.5476 -0.1555 0.135 Uiso 1 1 calc R . . C2 C 0.4052(5) 0.4984(3) 0.0709(5) 0.081(3) Uani 1 1 d . . . H21 H 0.4474 0.4883 0.0383 0.121 Uiso 1 1 calc R B . H22 H 0.3876 0.4591 0.0941 0.121 Uiso 1 1 calc R . . H23 H 0.4404 0.5266 0.1243 0.121 Uiso 1 1 calc R . . C4 C 0.1173(5) 0.5765(3) -0.0351(4) 0.0486(19) Uani 1 1 d . B . H4 H 0.0653 0.5682 -0.0115 0.058 Uiso 1 1 calc R . . P41 P 0.6979(5) 0.6916(4) 0.2555(6) 0.0256(15) Uani 0.5 1 d P D 1 C311 C 0.6763(10) 0.6832(7) 0.1284(10) 0.041(4) Uiso 0.5 1 d P D 1 H311 H 0.6726 0.7261 0.0998 0.049 Uiso 0.5 1 calc PR D 1 C321 C 0.5788(8) 0.6469(5) 0.0745(8) 0.037(3) Uiso 0.5 1 d P D 1 H321 H 0.5679 0.642 0.0082 0.055 Uiso 0.5 1 calc PR D 1 H322 H 0.5244 0.6708 0.0784 0.055 Uiso 0.5 1 calc PR D 1 H323 H 0.5826 0.6049 0.1029 0.055 Uiso 0.5 1 calc PR D 1 C331 C 0.7503(9) 0.6427(5) 0.1099(9) 0.044(4) Uiso 0.5 1 d P D 1 H331 H 0.7558 0.6013 0.1403 0.065 Uiso 0.5 1 calc PR D 1 H332 H 0.8143 0.6639 0.1357 0.065 Uiso 0.5 1 calc PR D 1 H333 H 0.7288 0.6369 0.0417 0.065 Uiso 0.5 1 calc PR D 1 C341 C 0.8354(9) 0.7088(6) 0.3057(9) 0.035(3) Uiso 0.5 1 d P D 1 H341 H 0.8668 0.6709 0.291 0.042 Uiso 0.5 1 calc PR D 1 C351 C 0.8784(10) 0.7143(6) 0.4116(10) 0.051(4) Uiso 0.5 1 d P D 1 H351 H 0.948 0.703 0.4374 0.077 Uiso 0.5 1 calc PR D 1 H352 H 0.8437 0.6856 0.4371 0.077 Uiso 0.5 1 calc PR D 1 H353 H 0.8714 0.7581 0.4294 0.077 Uiso 0.5 1 calc PR D 1 C361 C 0.8643(8) 0.7670(5) 0.2602(8) 0.040(4) Uiso 0.5 1 d P D 1 H361 H 0.8548 0.8062 0.2894 0.06 Uiso 0.5 1 calc PR D 1 H362 H 0.8228 0.768 0.1923 0.06 Uiso 0.5 1 calc PR D 1 H363 H 0.9332 0.7634 0.2702 0.06 Uiso 0.5 1 calc PR D 1 P42 P 0.7268(6) 0.7051(4) 0.2835(6) 0.0308(17) Uani 0.5 1 d P D 2 C312 C 0.7513(9) 0.6843(5) 0.1835(8) 0.035(3) Uiso 0.5 1 d P D 2 H312 H 0.8083 0.6544 0.2063 0.042 Uiso 0.5 1 calc PR D 2 C322 C 0.6672(9) 0.6502(6) 0.1089(9) 0.032(4) Uiso 0.5 1 d P D 2 H324 H 0.625 0.6809 0.0629 0.048 Uiso 0.5 1 calc PR D 2 H325 H 0.6293 0.6278 0.1382 0.048 Uiso 0.5 1 calc PR D 2 H326 H 0.6924 0.6195 0.0769 0.048 Uiso 0.5 1 calc PR D 2 C332 C 0.7769(9) 0.7382(6) 0.1320(9) 0.054(4) Uiso 0.5 1 d P D 2 H334 H 0.7874 0.721 0.0783 0.081 Uiso 0.5 1 calc PR D 2 H335 H 0.8367 0.7594 0.1754 0.081 Uiso 0.5 1 calc PR D 2 H336 H 0.7229 0.7689 0.1093 0.081 Uiso 0.5 1 calc PR D 2 C342 C 0.8479(9) 0.7387(6) 0.3630(10) 0.038(4) Uiso 0.5 1 d P D 2 H342 H 0.8609 0.7768 0.3314 0.045 Uiso 0.5 1 calc PR D 2 C352 C 0.8471(14) 0.7591(8) 0.4521(13) 0.120(8) Uiso 0.5 1 d P D 2 H354 H 0.8248 0.724 0.4799 0.18 Uiso 0.5 1 calc PR D 2 H355 H 0.8025 0.7952 0.4411 0.18 Uiso 0.5 1 calc PR D 2 H356 H 0.9134 0.7717 0.4955 0.18 Uiso 0.5 1 calc PR D 2 C362 C 0.9283(9) 0.6926(6) 0.3805(9) 0.043(4) Uiso 0.5 1 d P D 2 H364 H 0.9891 0.7093 0.4294 0.065 Uiso 0.5 1 calc PR D 2 H365 H 0.9374 0.6859 0.3222 0.065 Uiso 0.5 1 calc PR D 2 H366 H 0.9116 0.6522 0.4016 0.065 Uiso 0.5 1 calc PR D 2 C91 C 0.1650(9) 0.4195(5) 0.0470(9) 0.044(4) Uiso 0.5 1 d P B 1 H91A H 0.2228 0.4091 0.035 0.066 Uiso 0.5 1 calc PR B 1 H91B H 0.1085 0.426 -0.0132 0.066 Uiso 0.5 1 calc PR B 1 H91C H 0.1513 0.3845 0.0813 0.066 Uiso 0.5 1 calc PR B 1 C92 C 0.1307(9) 0.4614(6) 0.0949(11) 0.062(4) Uiso 0.5 1 d P B 2 H92A H 0.1318 0.4294 0.1411 0.093 Uiso 0.5 1 calc PR B 2 H92B H 0.0928 0.4454 0.031 0.093 Uiso 0.5 1 calc PR B 2 H92C H 0.1003 0.5004 0.1047 0.093 Uiso 0.5 1 calc PR B 2 C72 C 0.2369(11) 0.4759(6) 0.1075(10) 0.048(4) Uiso 0.5 1 d P B 2 H72 H 0.2558 0.4456 0.0682 0.058 Uiso 0.5 1 calc PR B 2 C82 C 0.3071(10) 0.4678(7) 0.2117(10) 0.053(4) Uiso 0.5 1 d P B 2 H82A H 0.2865 0.4957 0.2507 0.08 Uiso 0.5 1 calc PR B 2 H82B H 0.3738 0.4789 0.2201 0.08 Uiso 0.5 1 calc PR B 2 H82C H 0.3056 0.4236 0.2307 0.08 Uiso 0.5 1 calc PR B 2 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 Ni2 0.0443(5) 0.0303(4) 0.0447(6) 0.0169(4) 0.0293(5) 0.0143(4) P2 0.0267(9) 0.0329(10) 0.0288(10) -0.0036(8) 0.0136(8) 0.0020(8) P3 0.0386(11) 0.0331(10) 0.0379(11) 0.0122(8) 0.0249(9) 0.0125(8) P1 0.0754(14) 0.0303(11) 0.0297(11) -0.0002(9) 0.0233(10) 0.0125(10) N1 0.053(3) 0.016(2) 0.031(3) -0.004(3) 0.023(3) 0.009(3) N2 0.045(3) 0.025(3) 0.042(4) 0.009(3) 0.024(4) 0.009(4) C28 0.036(4) 0.030(4) 0.049(5) -0.001(3) 0.014(4) 0.001(3) C24 0.048(4) 0.030(4) 0.067(5) 0.004(4) 0.003(4) -0.009(3) C22 0.027(4) 0.033(4) 0.037(4) 0.002(3) 0.005(3) -0.001(3) C19 0.038(4) 0.027(4) 0.098(7) 0.034(4) 0.034(5) 0.013(3) C29 0.075(6) 0.045(5) 0.084(6) 0.030(4) 0.021(5) -0.001(4) C23 0.058(5) 0.043(5) 0.069(6) 0.004(4) 0.044(4) 0.004(4) C30 0.110(7) 0.088(6) 0.084(7) -0.052(5) 0.066(6) -0.027(5) C21 0.061(5) 0.038(4) 0.092(7) 0.000(5) 0.011(5) -0.004(3) C16 0.039(5) 0.133(8) 0.026(4) -0.036(5) 0.021(4) -0.032(5) C25 0.115(7) 0.059(5) 0.033(5) 0.039(4) 0.050(5) 0.059(5) C20 0.048(5) 0.083(6) 0.195(10) 0.083(6) 0.075(6) 0.034(4) C17 0.054(6) 0.279(13) 0.054(6) -0.031(7) 0.027(5) -0.079(7) C26 0.177(11) 0.096(7) 0.104(8) 0.055(6) 0.092(8) 0.115(7) C27 0.183(11) 0.088(7) 0.019(5) -0.025(5) 0.017(6) 0.003(7) C181 0.037(6) 0.049(7) 0.078(9) -0.005(6) 0.041(6) -0.006(5) C182 0.037(6) 0.049(7) 0.078(9) -0.005(6) 0.041(6) -0.006(5) C10 0.051(4) 0.022(4) 0.054(5) 0.002(3) 0.035(4) 0.010(3) C15 0.092(7) 0.065(6) 0.024(4) -0.008(4) -0.002(4) -0.031(5) C13 0.032(4) 0.044(4) 0.042(4) -0.008(3) 0.021(4) 0.003(3) C11 0.080(6) 0.022(4) 0.058(5) 0.002(4) 0.021(4) 0.018(4) C14 0.039(4) 0.084(5) 0.055(5) -0.038(4) 0.009(4) -0.027(4) C1 0.118(8) 0.095(7) 0.029(5) 0.004(5) 0.026(5) 0.062(6) C3 0.080(7) 0.184(10) 0.076(7) 0.056(7) 0.064(6) 0.093(7) C12 0.121(7) 0.032(4) 0.061(5) 0.007(4) 0.057(5) 0.001(4) C5 0.078(6) 0.070(6) 0.038(5) 0.008(4) 0.010(4) 0.007(4) C6 0.130(8) 0.077(6) 0.046(5) -0.019(5) 0.019(5) -0.029(6) C2 0.091(7) 0.095(7) 0.049(5) -0.016(5) 0.022(5) 0.045(5) C4 0.058(5) 0.047(5) 0.036(4) -0.010(4) 0.014(4) -0.014(4) P41 0.010(4) 0.020(4) 0.051(5) 0.004(3) 0.018(3) -0.002(2) P42 0.021(4) 0.020(4) 0.049(5) 0.010(3) 0.011(3) -0.009(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 1.752(5) . ? Ni1 P1 2.1580(19) . ? Ni1 P2 2.1585(17) . ? Ni2 N2 1.769(5) . ? Ni2 P41 2.049(9) . ? Ni2 P3 2.1535(17) . ? Ni2 P42 2.290(9) . ? P2 C10 1.852(6) . ? P2 C13 1.859(6) . ? P2 C16 1.865(7) . ? P3 C22 1.835(6) . ? P3 C25 1.881(7) . ? P3 C19 1.885(6) . ? P1 C72 1.821(13) . ? P1 C1 1.839(7) . ? P1 C4 1.856(6) . ? P1 C71 1.978(12) . ? N1 N2 1.158(5) . ? C28 C30 1.492(8) . ? C28 C29 1.498(8) . ? C28 P42 1.859(12) . ? C28 P41 1.941(11) . ? C28 H28 1 . ? C24 C22 1.541(7) . ? C24 H241 0.98 . ? C24 H242 0.98 . ? C24 H243 0.98 . ? C22 C23 1.539(8) . ? C22 H221 1 . ? C19 C21 1.515(9) . ? C19 C20 1.525(8) . ? C19 H19 1 . ? C29 H291 0.98 . ? C29 H292 0.98 . ? C29 H293 0.98 . ? C23 H231 0.98 . ? C23 H232 0.98 . ? C23 H233 0.98 . ? C30 H301 0.98 . ? C30 H302 0.98 . ? C30 H303 0.98 . ? C21 H211 0.98 . ? C21 H212 0.98 . ? C21 H213 0.98 . ? C16 C181 1.364(12) . ? C16 C182 1.387(12) . ? C16 C17 1.516(9) . ? C81 C71 1.493(17) . ? C81 H81A 0.98 . ? C81 H81B 0.98 . ? C81 H81C 0.98 . ? C25 C27 1.494(10) . ? C25 C26 1.496(8) . ? C25 H25 1 . ? C71 C91 1.566(15) . ? C71 H71 1 . ? C20 H201 0.98 . ? C20 H202 0.98 . ? C20 H203 0.98 . ? C17 H171 0.98 . ? C17 H172 0.98 . ? C17 H173 0.98 . ? C26 H261 0.98 . ? C26 H262 0.98 . ? C26 H263 0.98 . ? C27 H271 0.98 . ? C27 H272 0.98 . ? C27 H273 0.98 . ? C181 H181 0.98 . ? C181 H182 0.98 . ? C181 H183 0.98 . ? C182 H184 0.98 . ? C182 H185 0.98 . ? C182 H186 0.98 . ? C10 C12 1.516(7) . ? C10 C11 1.534(7) . ? C10 H10 1 . ? C15 C13 1.520(8) . ? C15 H151 0.98 . ? C15 H152 0.98 . ? C15 H153 0.98 . ? C13 C14 1.539(8) . ? C13 H13 1 . ? C11 H111 0.98 . ? C11 H112 0.98 . ? C11 H113 0.98 . ? C14 H141 0.98 . ? C14 H142 0.98 . ? C14 H143 0.98 . ? C1 C2 1.545(9) . ? C1 C3 1.550(10) . ? C1 H1 1 . ? C3 H31 0.98 . ? C3 H32 0.98 . ? C3 H33 0.98 . ? C12 H121 0.98 . ? C12 H122 0.98 . ? C12 H123 0.98 . ? C5 C4 1.518(8) . ? C5 H51 0.98 . ? C5 H52 0.98 . ? C5 H53 0.98 . ? C6 C4 1.529(8) . ? C6 H61 0.98 . ? C6 H62 0.98 . ? C6 H63 0.98 . ? C2 H21 0.98 . ? C2 H22 0.98 . ? C2 H23 0.98 . ? C4 H4 1 . ? P41 C311 1.873(17) . ? P41 C341 1.911(13) . ? C311 C331 1.515(17) . ? C311 C321 1.553(17) . ? C311 H311 1 . ? C321 H321 0.98 . ? C321 H322 0.98 . ? C321 H323 0.98 . ? C331 H331 0.98 . ? C331 H332 0.98 . ? C331 H333 0.98 . ? C341 C351 1.506(17) . ? C341 C361 1.563(15) . ? C341 H341 1 . ? C351 H351 0.98 . ? C351 H352 0.98 . ? C351 H353 0.98 . ? C361 H361 0.98 . ? C361 H362 0.98 . ? C361 H363 0.98 . ? P42 C312 1.791(15) . ? P42 C342 1.864(14) . ? C312 C322 1.499(16) . ? C312 C332 1.526(14) . ? C312 H312 1 . ? C322 H324 0.98 . ? C322 H325 0.98 . ? C322 H326 0.98 . ? C332 H334 0.98 . ? C332 H335 0.98 . ? C332 H336 0.98 . ? C342 C352 1.45(2) . ? C342 C362 1.481(16) . ? C342 H342 1 . ? C352 H354 0.98 . ? C352 H355 0.98 . ? C352 H356 0.98 . ? C362 H364 0.98 . ? C362 H365 0.98 . ? C362 H366 0.98 . ? C91 H91A 0.98 . ? C91 H91B 0.98 . ? C91 H91C 0.98 . ? C92 C72 1.548(17) . ? C92 H92A 0.98 . ? C92 H92B 0.98 . ? C92 H92C 0.98 . ? C72 C82 1.535(18) . ? C72 H72 1 . ? C82 H82A 0.98 . ? C82 H82B 0.98 . ? C82 H82C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 P1 116.00(17) . . ? N1 Ni1 P2 117.91(17) . . ? P1 Ni1 P2 126.08(7) . . ? N2 Ni2 P41 110.8(3) . . ? N2 Ni2 P3 116.29(17) . . ? P41 Ni2 P3 132.3(3) . . ? N2 Ni2 P42 119.3(3) . . ? P41 Ni2 P42 13.1(3) . . ? P3 Ni2 P42 124.4(2) . . ? C10 P2 C13 105.0(3) . . ? C10 P2 C16 103.6(3) . . ? C13 P2 C16 101.2(3) . . ? C10 P2 Ni1 110.88(19) . . ? C13 P2 Ni1 115.6(2) . . ? C16 P2 Ni1 119.0(3) . . ? C22 P3 C25 102.6(3) . . ? C22 P3 C19 101.5(3) . . ? C25 P3 C19 103.1(3) . . ? C22 P3 Ni2 119.5(2) . . ? C25 P3 Ni2 113.6(2) . . ? C19 P3 Ni2 114.4(2) . . ? C72 P1 C1 90.9(5) . . ? C72 P1 C4 112.5(5) . . ? C1 P1 C4 102.2(3) . . ? C72 P1 C71 23.3(5) . . ? C1 P1 C71 110.9(5) . . ? C4 P1 C71 95.6(4) . . ? C72 P1 Ni1 110.9(4) . . ? C1 P1 Ni1 116.1(3) . . ? C4 P1 Ni1 120.2(2) . . ? C71 P1 Ni1 109.8(4) . . ? N2 N1 Ni1 178.0(6) . . ? N1 N2 Ni2 177.7(5) . . ? C30 C28 C29 107.9(6) . . ? C30 C28 P42 104.6(6) . . ? C29 C28 P42 120.4(5) . . ? C30 C28 P41 112.0(6) . . ? C29 C28 P41 103.9(4) . . ? P42 C28 P41 16.5(3) . . ? C30 C28 H28 110.9 . . ? C29 C28 H28 110.9 . . ? P42 C28 H28 101.8 . . ? P41 C28 H28 110.9 . . ? C22 C24 H241 109.5 . . ? C22 C24 H242 109.5 . . ? H241 C24 H242 109.5 . . ? C22 C24 H243 109.5 . . ? H241 C24 H243 109.5 . . ? H242 C24 H243 109.5 . . ? C23 C22 C24 110.6(5) . . ? C23 C22 P3 113.6(4) . . ? C24 C22 P3 117.4(4) . . ? C23 C22 H221 104.6 . . ? C24 C22 H221 104.6 . . ? P3 C22 H221 104.6 . . ? C21 C19 C20 112.0(7) . . ? C21 C19 P3 110.8(4) . . ? C20 C19 P3 111.3(5) . . ? C21 C19 H19 107.5 . . ? C20 C19 H19 107.5 . . ? P3 C19 H19 107.5 . . ? C28 C29 H291 109.5 . . ? C28 C29 H292 109.5 . . ? H291 C29 H292 109.5 . . ? C28 C29 H293 109.5 . . ? H291 C29 H293 109.5 . . ? H292 C29 H293 109.5 . . ? C22 C23 H231 109.5 . . ? C22 C23 H232 109.5 . . ? H231 C23 H232 109.5 . . ? C22 C23 H233 109.5 . . ? H231 C23 H233 109.5 . . ? H232 C23 H233 109.5 . . ? C28 C30 H301 109.5 . . ? C28 C30 H302 109.5 . . ? H301 C30 H302 109.5 . . ? C28 C30 H303 109.5 . . ? H301 C30 H303 109.5 . . ? H302 C30 H303 109.5 . . ? C19 C21 H211 109.5 . . ? C19 C21 H212 109.5 . . ? H211 C21 H212 109.5 . . ? C19 C21 H213 109.5 . . ? H211 C21 H213 109.5 . . ? H212 C21 H213 109.5 . . ? C181 C16 C182 89.8(9) . . ? C181 C16 C17 103.4(8) . . ? C182 C16 C17 111.3(8) . . ? C181 C16 P2 116.7(7) . . ? C182 C16 P2 121.4(7) . . ? C17 C16 P2 111.3(5) . . ? C27 C25 C26 112.1(7) . . ? C27 C25 P3 114.6(5) . . ? C26 C25 P3 108.1(5) . . ? C27 C25 H25 107.3 . . ? C26 C25 H25 107.3 . . ? P3 C25 H25 107.3 . . ? C81 C71 C91 108.3(9) . . ? C81 C71 P1 109.0(9) . . ? C91 C71 P1 117.8(9) . . ? C81 C71 H71 107 . . ? C91 C71 H71 107 . . ? P1 C71 H71 107 . . ? C19 C20 H201 109.5 . . ? C19 C20 H202 109.5 . . ? H201 C20 H202 109.5 . . ? C19 C20 H203 109.5 . . ? H201 C20 H203 109.5 . . ? H202 C20 H203 109.5 . . ? C16 C17 H171 109.5 . . ? C16 C17 H172 109.5 . . ? H171 C17 H172 109.5 . . ? C16 C17 H173 109.5 . . ? H171 C17 H173 109.5 . . ? H172 C17 H173 109.5 . . ? C25 C26 H261 109.5 . . ? C25 C26 H262 109.5 . . ? H261 C26 H262 109.5 . . ? C25 C26 H263 109.5 . . ? H261 C26 H263 109.5 . . ? H262 C26 H263 109.5 . . ? C25 C27 H271 109.5 . . ? C25 C27 H272 109.5 . . ? H271 C27 H272 109.5 . . ? C25 C27 H273 109.5 . . ? H271 C27 H273 109.5 . . ? H272 C27 H273 109.5 . . ? C16 C181 H181 109.5 . . ? C16 C181 H182 109.5 . . ? C16 C181 H183 109.5 . . ? C16 C182 H184 109.5 . . ? C16 C182 H185 109.5 . . ? H184 C182 H185 109.5 . . ? C16 C182 H186 109.5 . . ? H184 C182 H186 109.5 . . ? H185 C182 H186 109.5 . . ? C12 C10 C11 110.7(5) . . ? C12 C10 P2 111.4(4) . . ? C11 C10 P2 116.9(4) . . ? C12 C10 H10 105.7 . . ? C11 C10 H10 105.7 . . ? P2 C10 H10 105.7 . . ? C13 C15 H151 109.5 . . ? C13 C15 H152 109.5 . . ? H151 C15 H152 109.5 . . ? C13 C15 H153 109.5 . . ? H151 C15 H153 109.5 . . ? H152 C15 H153 109.5 . . ? C15 C13 C14 109.2(5) . . ? C15 C13 P2 109.1(4) . . ? C14 C13 P2 111.3(4) . . ? C15 C13 H13 109.1 . . ? C14 C13 H13 109.1 . . ? P2 C13 H13 109.1 . . ? C10 C11 H111 109.5 . . ? C10 C11 H112 109.5 . . ? H111 C11 H112 109.5 . . ? C10 C11 H113 109.5 . . ? H111 C11 H113 109.5 . . ? H112 C11 H113 109.5 . . ? C13 C14 H141 109.5 . . ? C13 C14 H142 109.5 . . ? H141 C14 H142 109.5 . . ? C13 C14 H143 109.5 . . ? H141 C14 H143 109.5 . . ? H142 C14 H143 109.5 . . ? C2 C1 C3 108.9(7) . . ? C2 C1 P1 110.0(5) . . ? C3 C1 P1 109.9(5) . . ? C2 C1 H1 109.3 . . ? C3 C1 H1 109.3 . . ? P1 C1 H1 109.3 . . ? C1 C3 H31 109.5 . . ? C1 C3 H32 109.5 . . ? H31 C3 H32 109.5 . . ? C1 C3 H33 109.5 . . ? H31 C3 H33 109.5 . . ? H32 C3 H33 109.5 . . ? C10 C12 H121 109.5 . . ? C10 C12 H122 109.5 . . ? H121 C12 H122 109.5 . . ? C10 C12 H123 109.5 . . ? H121 C12 H123 109.5 . . ? H122 C12 H123 109.5 . . ? C4 C5 H51 109.5 . . ? C4 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C4 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? C4 C6 H61 109.5 . . ? C4 C6 H62 109.5 . . ? H61 C6 H62 109.5 . . ? C4 C6 H63 109.5 . . ? H61 C6 H63 109.5 . . ? H62 C6 H63 109.5 . . ? C1 C2 H21 109.5 . . ? C1 C2 H22 109.5 . . ? H21 C2 H22 109.5 . . ? C1 C2 H23 109.5 . . ? H21 C2 H23 109.5 . . ? H22 C2 H23 109.5 . . ? C5 C4 C6 109.4(6) . . ? C5 C4 P1 111.2(4) . . ? C6 C4 P1 117.4(5) . . ? C5 C4 H4 106 . . ? C6 C4 H4 106 . . ? P1 C4 H4 106 . . ? C311 P41 C341 98.1(7) . . ? C311 P41 C28 100.1(7) . . ? C341 P41 C28 100.6(5) . . ? C311 P41 Ni2 118.6(5) . . ? C341 P41 Ni2 119.7(6) . . ? C28 P41 Ni2 116.1(5) . . ? C331 C311 C321 102.6(12) . . ? C331 C311 P41 115.4(10) . . ? C321 C311 P41 109.6(9) . . ? C331 C311 H311 109.7 . . ? C321 C311 H311 109.7 . . ? P41 C311 H311 109.7 . . ? C351 C341 C361 111.1(10) . . ? C351 C341 P41 111.6(9) . . ? C361 C341 P41 114.4(9) . . ? C351 C341 H341 106.4 . . ? C361 C341 H341 106.4 . . ? P41 C341 H341 106.4 . . ? C312 P42 C28 108.7(7) . . ? C312 P42 C342 100.3(7) . . ? C28 P42 C342 102.2(6) . . ? C312 P42 Ni2 108.5(5) . . ? C28 P42 Ni2 108.9(5) . . ? C342 P42 Ni2 127.1(7) . . ? C322 C312 C332 105.2(10) . . ? C322 C312 P42 112.5(9) . . ? C332 C312 P42 117.1(9) . . ? C322 C312 H312 107.1 . . ? C332 C312 H312 107.1 . . ? P42 C312 H312 107.1 . . ? C312 C322 H324 109.5 . . ? C312 C322 H325 109.5 . . ? H324 C322 H325 109.5 . . ? C312 C322 H326 109.5 . . ? H324 C322 H326 109.5 . . ? H325 C322 H326 109.5 . . ? C312 C332 H334 109.5 . . ? C312 C332 H335 109.5 . . ? H334 C332 H335 109.5 . . ? C312 C332 H336 109.5 . . ? H334 C332 H336 109.5 . . ? H335 C332 H336 109.5 . . ? C352 C342 C362 109.9(14) . . ? C352 C342 P42 110.9(11) . . ? C362 C342 P42 111.6(9) . . ? C352 C342 H342 108.1 . . ? C362 C342 H342 108.1 . . ? P42 C342 H342 108.1 . . ? C342 C352 H354 109.5 . . ? C342 C352 H355 109.5 . . ? H354 C352 H355 109.5 . . ? C342 C352 H356 109.5 . . ? H354 C352 H356 109.5 . . ? H355 C352 H356 109.5 . . ? C342 C362 H364 109.5 . . ? C342 C362 H365 109.5 . . ? H364 C362 H365 109.5 . . ? C342 C362 H366 109.5 . . ? H364 C362 H366 109.5 . . ? H365 C362 H366 109.5 . . ? C72 C92 H92A 109.5 . . ? C72 C92 H92B 109.5 . . ? H92A C92 H92B 109.5 . . ? C72 C92 H92C 109.5 . . ? H92A C92 H92C 109.5 . . ? H92B C92 H92C 109.5 . . ? C82 C72 C92 109.5(11) . . ? C82 C72 P1 113.2(9) . . ? C92 C72 P1 106.3(10) . . ? C82 C72 H72 109.2 . . ? C92 C72 H72 109.2 . . ? P1 C72 H72 109.2 . . ? C72 C82 H82A 109.5 . . ? C72 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C72 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? data_rbm1_7 _database_code_depnum_ccdc_archive 'CCDC 896754' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-30 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H42 Ni O2 P2' _chemical_formula_sum 'C19 H42 Ni O2 P2' _chemical_formula_weight 423.18 _chemical_melting_point ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.1143(3) _cell_length_b 8.4650(4) _cell_length_c 18.9139(3) _cell_angle_alpha 89.3380(10) _cell_angle_beta 77.635(2) _cell_angle_gamma 64.2520(10) _cell_volume 1138.11(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6032 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.002 _exptl_absorpt_correction_T_max 0.7878 _exptl_absorpt_correction_T_min 0.6614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_crystal_colour orange _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needles _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_unetI/netI 0.0493 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 11781 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.11 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3953 _reflns_number_total 4610 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.452 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 4610 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0488 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0179P)^2^+1.1647P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.0996 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.64792(6) 0.89453(5) 0.77027(2) 0.02335(12) Uani 1 1 d . . . P1 P 0.53587(11) 0.73704(11) 0.84800(4) 0.02396(19) Uani 1 1 d . . . P2 P 0.64090(11) 0.87318(11) 0.65836(4) 0.02297(18) Uani 1 1 d . . . O1 O 0.7239(4) 1.0141(3) 0.83367(13) 0.0396(6) Uani 1 1 d . . . O2 O 0.8152(4) 1.1408(4) 0.73405(15) 0.0495(7) Uani 1 1 d . . . C1 C 0.7518(5) 1.0500(5) 0.76839(19) 0.0344(8) Uani 1 1 d . . . C2 C 0.2228(5) 1.0608(5) 0.8996(2) 0.0397(9) Uani 1 1 d . . . H2A H 0.2865 1.1060 0.8606 0.060 Uiso 1 1 calc R . . H2B H 0.1521 1.1519 0.9405 0.060 Uiso 1 1 calc R . . H2C H 0.1361 1.0284 0.8815 0.060 Uiso 1 1 calc R . . C3 C 0.3688(5) 0.8986(4) 0.92508(17) 0.0312(8) Uani 1 1 d . . . H3 H 0.4462 0.9430 0.9456 0.037 Uiso 1 1 calc R . . C4 C 0.2777(6) 0.8288(6) 0.9893(2) 0.0475(10) Uani 1 1 d . . . H4A H 0.1816 0.8027 0.9756 0.071 Uiso 1 1 calc R . . H4B H 0.2191 0.9179 1.0310 0.071 Uiso 1 1 calc R . . H4C H 0.3740 0.7211 1.0022 0.071 Uiso 1 1 calc R . . C5 C 0.7958(5) 0.6704(5) 0.9354(2) 0.0410(9) Uani 1 1 d . . . H5A H 0.8322 0.7520 0.9065 0.062 Uiso 1 1 calc R . . H5B H 0.9053 0.5821 0.9507 0.062 Uiso 1 1 calc R . . H5C H 0.6965 0.7360 0.9784 0.062 Uiso 1 1 calc R . . C6 C 0.7234(5) 0.5788(4) 0.88941(19) 0.0326(8) Uani 1 1 d . . . H6 H 0.6700 0.5098 0.9217 0.039 Uiso 1 1 calc R . . C7 C 0.8846(5) 0.4503(5) 0.8290(2) 0.0473(10) Uani 1 1 d . . . H7A H 0.8376 0.3858 0.8027 0.071 Uiso 1 1 calc R . . H7B H 0.9847 0.3668 0.8505 0.071 Uiso 1 1 calc R . . H7C H 0.9346 0.5162 0.7953 0.071 Uiso 1 1 calc R . . C8 C 0.2399(5) 0.7163(5) 0.8002(2) 0.0394(9) Uani 1 1 d . . . H8A H 0.1420 0.7673 0.8451 0.059 Uiso 1 1 calc R . . H8B H 0.2069 0.6440 0.7712 0.059 Uiso 1 1 calc R . . H8C H 0.2502 0.8111 0.7723 0.059 Uiso 1 1 calc R . . C9 C 0.4290(5) 0.6011(4) 0.81912(18) 0.0300(7) Uani 1 1 d . . . H9 H 0.5155 0.5332 0.7724 0.036 Uiso 1 1 calc R . . C10 C 0.4096(6) 0.4628(5) 0.8689(2) 0.0411(9) Uani 1 1 d . . . H10A H 0.5339 0.3802 0.8754 0.062 Uiso 1 1 calc R . . H10B H 0.3552 0.3984 0.8468 0.062 Uiso 1 1 calc R . . H10C H 0.3273 0.5215 0.9162 0.062 Uiso 1 1 calc R . . C11 C 0.2559(5) 1.0836(5) 0.6708(2) 0.0437(10) Uani 1 1 d . . . H11A H 0.2442 0.9771 0.6589 0.066 Uiso 1 1 calc R . . H11B H 0.1579 1.1859 0.6555 0.066 Uiso 1 1 calc R . . H11C H 0.2415 1.0996 0.7234 0.066 Uiso 1 1 calc R . . C12 C 0.4502(4) 1.0650(4) 0.63100(18) 0.0295(7) Uani 1 1 d . . . H12 H 0.4633 1.0443 0.5777 0.035 Uiso 1 1 calc R . . C13 C 0.4639(6) 1.2362(5) 0.6442(2) 0.0498(11) Uani 1 1 d . . . H13A H 0.4577 1.2563 0.6958 0.075 Uiso 1 1 calc R . . H13B H 0.3594 1.3346 0.6302 0.075 Uiso 1 1 calc R . . H13C H 0.5835 1.2275 0.6150 0.075 Uiso 1 1 calc R . . C14 C 0.8739(6) 0.8529(6) 0.51648(19) 0.0473(10) Uani 1 1 d . . . H14A H 0.8861 0.7373 0.5013 0.071 Uiso 1 1 calc R . . H14B H 0.9852 0.8660 0.4909 0.071 Uiso 1 1 calc R . . H14C H 0.7612 0.9455 0.5047 0.071 Uiso 1 1 calc R . . C15 C 0.8572(4) 0.8684(5) 0.59857(18) 0.0306(7) Uani 1 1 d . . . H15 H 0.8520 0.9859 0.6097 0.037 Uiso 1 1 calc R . . C16 C 1.0359(5) 0.7348(6) 0.6185(2) 0.0507(11) Uani 1 1 d . . . H16A H 1.0210 0.7464 0.6712 0.076 Uiso 1 1 calc R . . H16B H 1.1425 0.7565 0.5941 0.076 Uiso 1 1 calc R . . H16C H 1.0591 0.6155 0.6028 0.076 Uiso 1 1 calc R . . C17 C 0.5600(6) 0.6788(5) 0.55470(19) 0.0420(9) Uani 1 1 d . . . H17A H 0.4532 0.7905 0.5513 0.063 Uiso 1 1 calc R . . H17B H 0.5270 0.5816 0.5499 0.063 Uiso 1 1 calc R . . H17C H 0.6690 0.6620 0.5157 0.063 Uiso 1 1 calc R . . C18 C 0.6081(5) 0.6824(4) 0.62851(18) 0.0291(7) Uani 1 1 d . . . H18 H 0.4978 0.6852 0.6652 0.035 Uiso 1 1 calc R . . C19 C 0.7741(5) 0.5088(5) 0.6353(2) 0.0422(9) Uani 1 1 d . . . H19A H 0.8818 0.4869 0.5948 0.063 Uiso 1 1 calc R . . H19B H 0.7385 0.4122 0.6340 0.063 Uiso 1 1 calc R . . H19C H 0.8084 0.5159 0.6814 0.063 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 0.0276(2) 0.0222(2) 0.0229(2) 0.00351(16) -0.00756(17) -0.01269(18) P1 0.0255(4) 0.0232(4) 0.0239(4) 0.0060(3) -0.0074(3) -0.0107(4) P2 0.0239(4) 0.0233(4) 0.0227(4) 0.0028(3) -0.0052(3) -0.0114(3) O1 0.0588(17) 0.0408(15) 0.0319(14) 0.0028(11) -0.0170(12) -0.0305(14) O2 0.069(2) 0.0542(18) 0.0484(17) 0.0088(14) -0.0130(14) -0.0487(17) C1 0.038(2) 0.033(2) 0.036(2) 0.0018(16) -0.0106(16) -0.0186(17) C2 0.034(2) 0.035(2) 0.038(2) -0.0006(16) -0.0022(16) -0.0075(17) C3 0.0337(18) 0.0314(19) 0.0256(17) 0.0025(14) -0.0062(14) -0.0121(16) C4 0.051(2) 0.054(3) 0.031(2) 0.0058(18) 0.0007(18) -0.022(2) C5 0.042(2) 0.044(2) 0.042(2) 0.0133(18) -0.0225(18) -0.0176(19) C6 0.0342(19) 0.0289(19) 0.0366(19) 0.0131(15) -0.0158(16) -0.0125(16) C7 0.038(2) 0.033(2) 0.060(3) 0.0022(19) -0.023(2) -0.0006(17) C8 0.039(2) 0.047(2) 0.045(2) 0.0136(18) -0.0197(17) -0.0264(19) C9 0.0343(18) 0.0314(19) 0.0314(18) 0.0057(15) -0.0108(15) -0.0195(16) C10 0.052(2) 0.038(2) 0.045(2) 0.0143(18) -0.0157(19) -0.029(2) C11 0.0276(19) 0.046(2) 0.045(2) 0.0115(18) -0.0088(17) -0.0048(17) C12 0.0299(17) 0.0285(18) 0.0299(18) 0.0085(14) -0.0135(14) -0.0101(15) C13 0.057(3) 0.028(2) 0.066(3) 0.013(2) -0.028(2) -0.0142(19) C14 0.050(2) 0.064(3) 0.031(2) -0.0010(19) 0.0062(17) -0.035(2) C15 0.0278(17) 0.0310(19) 0.0340(18) 0.0008(15) -0.0028(14) -0.0160(15) C16 0.027(2) 0.060(3) 0.061(3) 0.002(2) -0.0046(19) -0.018(2) C17 0.051(2) 0.053(3) 0.034(2) 0.0023(18) -0.0126(18) -0.032(2) C18 0.0341(18) 0.0310(19) 0.0278(17) 0.0021(14) -0.0049(14) -0.0205(16) C19 0.047(2) 0.0260(19) 0.050(2) -0.0026(17) -0.0077(19) -0.0146(18) _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 P1 2.2806(9) . ? Ni1 P2 2.1412(9) . ? Ni1 O1 1.932(2) . ? Ni1 C1 1.842(3) . ? P1 C3 1.850(3) . ? P1 C6 1.854(3) . ? P1 C9 1.860(3) . ? P2 C12 1.854(3) . ? P2 C15 1.857(3) . ? P2 C18 1.859(3) . ? O1 C1 1.265(4) . ? O2 C1 1.211(4) . ? C2 C3 1.528(5) . ? C3 C4 1.532(5) . ? C5 C6 1.527(5) . ? C6 C7 1.533(5) . ? C8 C9 1.536(5) . ? C9 C10 1.533(4) . ? C11 C12 1.535(5) . ? C12 C13 1.528(5) . ? C14 C15 1.531(5) . ? C15 C16 1.524(5) . ? C17 C18 1.532(5) . ? C18 C19 1.530(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P2 Ni1 P1 117.98(3) . . ? O1 Ni1 P1 102.39(8) . . ? O1 Ni1 P2 139.63(8) . . ? C1 Ni1 P1 141.45(12) . . ? C1 Ni1 P2 100.56(11) . . ? C1 Ni1 O1 39.07(13) . . ? C3 P1 Ni1 104.95(11) . . ? C3 P1 C6 103.88(16) . . ? C3 P1 C9 109.92(16) . . ? C6 P1 Ni1 110.68(11) . . ? C6 P1 C9 103.19(15) . . ? C9 P1 Ni1 122.81(11) . . ? C12 P2 Ni1 114.40(11) . . ? C12 P2 C15 102.94(15) . . ? C12 P2 C18 103.50(15) . . ? C15 P2 Ni1 110.40(11) . . ? C15 P2 C18 108.85(15) . . ? C18 P2 Ni1 115.78(11) . . ? C1 O1 Ni1 66.66(19) . . ? O1 C1 Ni1 74.3(2) . . ? O2 C1 Ni1 149.0(3) . . ? O2 C1 O1 136.7(4) . . ? C2 C3 P1 111.9(2) . . ? C2 C3 C4 111.7(3) . . ? C4 C3 P1 117.3(3) . . ? C5 C6 P1 112.5(2) . . ? C5 C6 C7 110.6(3) . . ? C7 C6 P1 109.1(2) . . ? C8 C9 P1 111.5(2) . . ? C10 C9 P1 117.8(2) . . ? C10 C9 C8 110.0(3) . . ? C11 C12 P2 111.1(2) . . ? C13 C12 P2 111.9(2) . . ? C13 C12 C11 109.9(3) . . ? C14 C15 P2 116.8(2) . . ? C16 C15 P2 112.5(2) . . ? C16 C15 C14 111.1(3) . . ? C17 C18 P2 118.8(2) . . ? C19 C18 P2 110.7(2) . . ? C19 C18 C17 110.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Ni1 P1 C3 C2 52.5(3) . . . . ? Ni1 P1 C3 C4 -176.5(3) . . . . ? Ni1 P1 C6 C5 62.5(3) . . . . ? Ni1 P1 C6 C7 -60.6(3) . . . . ? Ni1 P1 C9 C8 -68.3(3) . . . . ? Ni1 P1 C9 C10 163.3(2) . . . . ? Ni1 P2 C12 C11 -64.5(3) . . . . ? Ni1 P2 C12 C13 58.7(3) . . . . ? Ni1 P2 C15 C14 179.8(2) . . . . ? Ni1 P2 C15 C16 49.7(3) . . . . ? Ni1 P2 C18 C17 167.2(2) . . . . ? Ni1 P2 C18 C19 -63.5(3) . . . . ? Ni1 O1 C1 O2 -179.7(6) . . . . ? P1 Ni1 P2 C12 103.52(12) . . . . ? P1 Ni1 P2 C15 -140.95(12) . . . . ? P1 Ni1 P2 C18 -16.73(13) . . . . ? P1 Ni1 O1 C1 -179.7(2) . . . . ? P1 Ni1 C1 O1 0.5(3) . . . . ? P1 Ni1 C1 O2 -179.9(5) . . . . ? P2 Ni1 P1 C3 -129.35(12) . . . . ? P2 Ni1 P1 C6 119.17(13) . . . . ? P2 Ni1 P1 C9 -3.08(14) . . . . ? P2 Ni1 O1 C1 0.1(3) . . . . ? P2 Ni1 C1 O1 -179.92(18) . . . . ? P2 Ni1 C1 O2 -0.3(6) . . . . ? O1 Ni1 P1 C3 50.51(14) . . . . ? O1 Ni1 P1 C6 -60.98(15) . . . . ? O1 Ni1 P1 C9 176.78(15) . . . . ? O1 Ni1 P2 C12 -76.27(17) . . . . ? O1 Ni1 P2 C15 39.26(18) . . . . ? O1 Ni1 P2 C18 163.48(17) . . . . ? O1 Ni1 C1 O2 179.6(7) . . . . ? C1 Ni1 P1 C3 50.2(2) . . . . ? C1 Ni1 P1 C6 -61.3(2) . . . . ? C1 Ni1 P1 C9 176.5(2) . . . . ? C1 Ni1 P2 C12 -76.19(16) . . . . ? C1 Ni1 P2 C15 39.34(17) . . . . ? C1 Ni1 P2 C18 163.56(17) . . . . ? C3 P1 C6 C5 -49.7(3) . . . . ? C3 P1 C6 C7 -172.8(3) . . . . ? C3 P1 C9 C8 55.8(3) . . . . ? C3 P1 C9 C10 -72.7(3) . . . . ? C6 P1 C3 C2 168.8(3) . . . . ? C6 P1 C3 C4 -60.3(3) . . . . ? C6 P1 C9 C8 166.1(2) . . . . ? C6 P1 C9 C10 37.6(3) . . . . ? C9 P1 C3 C2 -81.4(3) . . . . ? C9 P1 C3 C4 49.6(3) . . . . ? C9 P1 C6 C5 -164.4(3) . . . . ? C9 P1 C6 C7 72.5(3) . . . . ? C12 P2 C15 C14 -57.6(3) . . . . ? C12 P2 C15 C16 172.2(3) . . . . ? C12 P2 C18 C17 41.2(3) . . . . ? C12 P2 C18 C19 170.5(2) . . . . ? C15 P2 C12 C11 175.7(3) . . . . ? C15 P2 C12 C13 -61.1(3) . . . . ? C15 P2 C18 C17 -67.8(3) . . . . ? C15 P2 C18 C19 61.5(3) . . . . ? C18 P2 C12 C11 62.4(3) . . . . ? C18 P2 C12 C13 -174.4(3) . . . . ? C18 P2 C15 C14 51.7(3) . . . . ? C18 P2 C15 C16 -78.5(3) . . . . ? data_rby9_8 _database_code_depnum_ccdc_archive 'CCDC 896755' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-05-30 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C10 H21 Ni0.5 O P)' _chemical_formula_sum 'C20 H42 Ni O2 P2' _chemical_formula_weight 435.19 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.660(2) _cell_length_b 14.224(3) _cell_length_c 15.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.17(3) _cell_angle_gamma 90.00 _cell_volume 2346.4(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6032 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 0.974 _exptl_absorpt_correction_T_max 0.9529 _exptl_absorpt_correction_T_min 0.7929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour white _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0296 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 12374 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 2.36 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 2137 _reflns_number_total 2404 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.405 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.060 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 2404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0324 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+1.3146P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.0776 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 1.0000 0.16778(2) 0.2500 0.02132(12) Uani 1 2 d S . . P1 P 0.88313(4) 0.24689(3) 0.31360(3) 0.02112(13) Uani 1 1 d . . . C3 C 0.79237(19) 0.16633(14) 0.36013(15) 0.0307(5) Uani 1 1 d . . . H3 H 0.7486 0.2056 0.3928 0.037 Uiso 1 1 calc R . . C6 C 0.97232(18) 0.31651(14) 0.42110(13) 0.0276(4) Uani 1 1 d . . . H6 H 1.0475 0.2784 0.4546 0.033 Uiso 1 1 calc R . . C9 C 0.76708(18) 0.33195(13) 0.23808(14) 0.0282(4) Uani 1 1 d . . . H9 H 0.8139 0.3910 0.2388 0.034 Uiso 1 1 calc R . . C4 C 0.8764(2) 0.09847(17) 0.43268(17) 0.0447(6) Uani 1 1 d . . . H4A H 0.8282 0.0630 0.4626 0.067 Uiso 1 1 calc R . . H4B H 0.9410 0.1340 0.4809 0.067 Uiso 1 1 calc R . . H4C H 0.9141 0.0548 0.4011 0.067 Uiso 1 1 calc R . . C7 C 1.0195(2) 0.40829(14) 0.39426(15) 0.0361(5) Uani 1 1 d . . . H7A H 0.9528 0.4546 0.3746 0.054 Uiso 1 1 calc R . . H7B H 1.0484 0.3967 0.3421 0.054 Uiso 1 1 calc R . . H7C H 1.0876 0.4324 0.4489 0.054 Uiso 1 1 calc R . . C5 C 0.9139(2) 0.33607(18) 0.49498(16) 0.0457(6) Uani 1 1 d . . . H5A H 0.9734 0.3686 0.5492 0.069 Uiso 1 1 calc R . . H5B H 0.8901 0.2765 0.5159 0.069 Uiso 1 1 calc R . . H5C H 0.8409 0.3756 0.4670 0.069 Uiso 1 1 calc R . . C10 C 0.7141(2) 0.30144(17) 0.13442(15) 0.0396(5) Uani 1 1 d . . . H10A H 0.6588 0.2479 0.1277 0.059 Uiso 1 1 calc R . . H10B H 0.7814 0.2831 0.1136 0.059 Uiso 1 1 calc R . . H10C H 0.6683 0.3538 0.0955 0.059 Uiso 1 1 calc R . . C2 C 0.6954(2) 0.11066(17) 0.28202(17) 0.0451(6) Uani 1 1 d . . . H2A H 0.7358 0.0728 0.2477 0.068 Uiso 1 1 calc R . . H2B H 0.6374 0.1543 0.2382 0.068 Uiso 1 1 calc R . . H2C H 0.6509 0.0692 0.3102 0.068 Uiso 1 1 calc R . . C1 C 1.10546(19) 0.10497(14) 0.34566(14) 0.0300(5) Uani 1 1 d . . . O1 O 1.17590(15) 0.06605(12) 0.40826(11) 0.0496(4) Uani 1 1 d . . . C8 C 0.6644(2) 0.36048(18) 0.27273(18) 0.0461(6) Uani 1 1 d . . . H8A H 0.6126 0.4084 0.2304 0.069 Uiso 1 1 calc R . . H8B H 0.7003 0.3861 0.3368 0.069 Uiso 1 1 calc R . . H8C H 0.6143 0.3053 0.2732 0.069 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 0.0273(2) 0.01802(19) 0.02162(19) 0.000 0.01238(14) 0.000 P1 0.0235(3) 0.0194(3) 0.0224(3) -0.00051(18) 0.0106(2) -0.00056(18) C3 0.0363(11) 0.0284(11) 0.0367(11) 0.0022(9) 0.0243(10) -0.0007(9) C6 0.0286(10) 0.0308(11) 0.0230(10) -0.0053(8) 0.0089(8) 0.0013(8) C9 0.0252(10) 0.0231(10) 0.0347(11) 0.0020(8) 0.0087(8) 0.0023(8) C4 0.0547(15) 0.0392(13) 0.0514(14) 0.0169(11) 0.0326(13) 0.0029(11) C7 0.0382(12) 0.0280(11) 0.0378(12) -0.0084(9) 0.0086(10) -0.0071(9) C5 0.0502(14) 0.0569(16) 0.0365(13) -0.0159(11) 0.0235(11) 0.0001(12) C10 0.0348(12) 0.0421(13) 0.0327(12) 0.0033(10) 0.0009(10) 0.0016(10) C2 0.0489(14) 0.0373(13) 0.0572(15) -0.0058(11) 0.0290(12) -0.0194(11) C1 0.0389(12) 0.0263(11) 0.0305(11) 0.0020(9) 0.0193(10) 0.0035(9) O1 0.0564(10) 0.0509(11) 0.0401(9) 0.0204(8) 0.0157(8) 0.0181(8) C8 0.0371(13) 0.0465(14) 0.0575(16) 0.0061(12) 0.0206(12) 0.0143(11) _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 P1 2.2370(6) . ? Ni1 P1 2.2370(6) 2_755 ? Ni1 C1 1.768(2) . ? Ni1 C1 1.768(2) 2_755 ? P1 C3 1.863(2) . ? P1 C6 1.870(2) . ? P1 C9 1.868(2) . ? C3 C4 1.525(3) . ? C3 C2 1.530(3) . ? C6 C7 1.528(3) . ? C6 C5 1.532(3) . ? C9 C10 1.530(3) . ? C9 C8 1.527(3) . ? C1 O1 1.149(2) . ? 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 P1 119.60(3) 2_755 . ? C1 Ni1 P1 104.56(6) . . ? C1 Ni1 P1 104.88(7) 2_755 . ? C1 Ni1 P1 104.55(6) 2_755 2_755 ? C1 Ni1 P1 104.88(7) . 2_755 ? C1 Ni1 C1 119.31(13) . 2_755 ? C3 P1 Ni1 111.84(7) . . ? C3 P1 C6 102.02(9) . . ? C3 P1 C9 104.25(9) . . ? C6 P1 Ni1 114.15(7) . . ? C9 P1 Ni1 118.71(7) . . ? C9 P1 C6 104.09(9) . . ? C4 C3 P1 110.97(14) . . ? C4 C3 C2 109.51(18) . . ? C2 C3 P1 112.75(14) . . ? C7 C6 P1 111.12(13) . . ? C7 C6 C5 109.73(17) . . ? C5 C6 P1 118.69(15) . . ? C10 C9 P1 112.39(14) . . ? C8 C9 P1 116.46(15) . . ? C8 C9 C10 110.72(18) . . ? O1 C1 Ni1 178.30(19) . . ? data_rbx6_9 _database_code_depnum_ccdc_archive 'CCDC 896756' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-06-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C10 H21 Ni P S2)' _chemical_formula_sum 'C20 H42 Ni2 P2 S4' _chemical_formula_weight 590.14 _chemical_melting_point ? 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' 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.6433(15) _cell_length_b 11.110(2) _cell_length_c 17.163(3) _cell_angle_alpha 87.22(3) _cell_angle_beta 79.83(3) _cell_angle_gamma 71.63(2) _cell_volume 1361.5(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6032 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.813 _exptl_absorpt_correction_T_max 0.9310 _exptl_absorpt_correction_T_min 0.6599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0863 _diffrn_reflns_av_unetI/netI 0.1128 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 13248 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.93 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3155 _reflns_number_total 4779 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.590 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.117 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 4779 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0579 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.1091 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.70375(10) 0.35596(7) 0.03987(4) 0.0192(2) Uani 1 1 d . . . Ni2 Ni 0.38358(10) 0.91990(7) 0.42814(4) 0.0206(2) Uani 1 1 d . . . S1 S 0.7202(2) 0.21987(15) -0.04940(10) 0.0331(4) Uani 1 1 d . . . S2 S 0.5752(2) 0.53932(14) 0.09443(9) 0.0250(4) Uani 1 1 d . . . S3 S 0.5006(2) 0.82850(14) 0.52848(9) 0.0258(4) Uani 1 1 d . . . S4 S 0.3157(2) 1.08065(15) 0.35052(10) 0.0307(4) Uani 1 1 d . . . P1 P 0.9160(2) 0.26959(15) 0.11849(9) 0.0207(4) Uani 1 1 d . . . P2 P 0.3099(2) 0.76330(15) 0.37884(9) 0.0207(4) Uani 1 1 d . . . C1 C 0.5806(8) 0.3691(5) -0.0429(3) 0.0217(14) Uani 1 1 d . . . C2 C 1.2011(9) 0.1978(6) -0.0146(4) 0.0420(19) Uani 1 1 d . . . H2A H 1.2510 0.2664 -0.0062 0.063 Uiso 1 1 calc R . . H2B H 1.0997 0.2296 -0.0455 0.063 Uiso 1 1 calc R . . H2C H 1.3008 0.1279 -0.0435 0.063 Uiso 1 1 calc R . . C3 C 1.1263(8) 0.1507(6) 0.0647(4) 0.0289(16) Uani 1 1 d . . . H3 H 1.0822 0.0795 0.0519 0.035 Uiso 1 1 calc R . . C4 C 1.2814(8) 0.0910(6) 0.1128(4) 0.049(2) Uani 1 1 d . . . H4A H 1.3748 0.0186 0.0836 0.074 Uiso 1 1 calc R . . H4B H 1.2280 0.0621 0.1637 0.074 Uiso 1 1 calc R . . H4C H 1.3409 0.1540 0.1223 0.074 Uiso 1 1 calc R . . C5 C 0.7752(10) 0.0698(6) 0.1676(4) 0.045(2) Uani 1 1 d . . . H5A H 0.7005 0.0360 0.2101 0.067 Uiso 1 1 calc R . . H5B H 0.8909 0.0026 0.1473 0.067 Uiso 1 1 calc R . . H5C H 0.7034 0.1006 0.1247 0.067 Uiso 1 1 calc R . . C6 C 0.8234(9) 0.1796(6) 0.2000(3) 0.0276(15) Uani 1 1 d . . . H6 H 0.9219 0.1435 0.2335 0.033 Uiso 1 1 calc R . . C7 C 0.6519(9) 0.2692(6) 0.2512(4) 0.045(2) Uani 1 1 d . . . H7A H 0.5560 0.3083 0.2185 0.068 Uiso 1 1 calc R . . H7B H 0.6877 0.3354 0.2738 0.068 Uiso 1 1 calc R . . H7C H 0.6020 0.2212 0.2940 0.068 Uiso 1 1 calc R . . C8 C 1.0871(9) 0.3434(6) 0.2379(4) 0.0339(17) Uani 1 1 d . . . H8A H 1.2177 0.2956 0.2177 0.051 Uiso 1 1 calc R . . H8B H 1.0286 0.2889 0.2726 0.051 Uiso 1 1 calc R . . H8C H 1.0825 0.4174 0.2680 0.051 Uiso 1 1 calc R . . C9 C 0.9824(8) 0.3870(5) 0.1691(3) 0.0200(14) Uani 1 1 d . . . H9 H 0.8612 0.4503 0.1926 0.024 Uiso 1 1 calc R . . C10 C 1.0823(9) 0.4622(6) 0.1110(4) 0.0396(18) Uani 1 1 d . . . H10A H 1.0845 0.5376 0.1377 0.059 Uiso 1 1 calc R . . H10B H 1.0158 0.4882 0.0661 0.059 Uiso 1 1 calc R . . H10C H 1.2108 0.4090 0.0919 0.059 Uiso 1 1 calc R . . C11 C 0.5804(8) 0.9259(5) 0.5715(3) 0.0214(14) Uani 1 1 d . . . C12 C 0.0957(9) 0.7088(6) 0.5182(4) 0.0399(18) Uani 1 1 d . . . H12A H -0.0226 0.7373 0.4979 0.060 Uiso 1 1 calc R . . H12B H 0.1188 0.7817 0.5394 0.060 Uiso 1 1 calc R . . H12C H 0.0886 0.6470 0.5604 0.060 Uiso 1 1 calc R . . C13 C 0.2560(8) 0.6468(5) 0.4509(3) 0.0259(15) Uani 1 1 d . . . H13 H 0.3693 0.6123 0.4766 0.031 Uiso 1 1 calc R . . C14 C 0.2242(9) 0.5308(6) 0.4183(4) 0.0397(18) Uani 1 1 d . . . H14A H 0.2254 0.4672 0.4600 0.060 Uiso 1 1 calc R . . H14B H 0.3239 0.4945 0.3736 0.060 Uiso 1 1 calc R . . H14C H 0.1029 0.5564 0.4004 0.060 Uiso 1 1 calc R . . C15 C -0.0592(9) 0.9055(6) 0.3670(4) 0.0416(19) Uani 1 1 d . . . H15A H -0.1418 0.9558 0.3316 0.062 Uiso 1 1 calc R . . H15B H -0.0318 0.9625 0.4017 0.062 Uiso 1 1 calc R . . H15C H -0.1208 0.8504 0.3993 0.062 Uiso 1 1 calc R . . C16 C 0.1236(8) 0.8241(6) 0.3178(3) 0.0286(16) Uani 1 1 d . . . H16 H 0.1668 0.8855 0.2810 0.034 Uiso 1 1 calc R . . C17 C 0.0949(9) 0.7320(6) 0.2644(4) 0.0420(19) Uani 1 1 d . . . H17A H 0.0412 0.6726 0.2963 0.063 Uiso 1 1 calc R . . H17B H 0.2154 0.6849 0.2330 0.063 Uiso 1 1 calc R . . H17C H 0.0094 0.7782 0.2289 0.063 Uiso 1 1 calc R . . C18 C 0.6723(9) 0.5971(6) 0.3528(4) 0.0402(18) Uani 1 1 d . . . H18A H 0.7820 0.5516 0.3145 0.060 Uiso 1 1 calc R . . H18B H 0.6326 0.5363 0.3892 0.060 Uiso 1 1 calc R . . H18C H 0.7045 0.6576 0.3828 0.060 Uiso 1 1 calc R . . C19 C 0.5132(8) 0.6685(6) 0.3089(3) 0.0263(15) Uani 1 1 d . . . H19 H 0.4751 0.6056 0.2817 0.032 Uiso 1 1 calc R . . C20 C 0.5799(9) 0.7546(6) 0.2470(4) 0.0357(17) Uani 1 1 d . . . H20A H 0.6028 0.8230 0.2735 0.054 Uiso 1 1 calc R . . H20B H 0.4838 0.7910 0.2141 0.054 Uiso 1 1 calc R . . H20C H 0.6959 0.7052 0.2137 0.054 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 0.0179(4) 0.0180(4) 0.0214(5) 0.0013(3) -0.0065(3) -0.0039(3) Ni2 0.0223(5) 0.0193(4) 0.0213(5) 0.0003(3) -0.0053(4) -0.0073(4) S1 0.0369(10) 0.0228(9) 0.0373(11) -0.0059(8) -0.0146(9) -0.0009(8) S2 0.0270(9) 0.0233(9) 0.0250(9) -0.0023(7) -0.0127(7) -0.0035(7) S3 0.0344(10) 0.0204(9) 0.0268(9) 0.0033(7) -0.0111(8) -0.0115(7) S4 0.0425(11) 0.0261(9) 0.0295(10) 0.0068(7) -0.0172(8) -0.0141(8) P1 0.0168(8) 0.0205(9) 0.0241(9) 0.0032(7) -0.0053(7) -0.0044(7) P2 0.0195(9) 0.0213(9) 0.0224(9) -0.0016(7) -0.0051(7) -0.0068(7) C1 0.021(3) 0.018(3) 0.028(4) -0.002(3) 0.003(3) -0.013(3) C2 0.027(4) 0.037(4) 0.055(5) -0.015(4) 0.009(4) -0.006(3) C3 0.024(4) 0.024(4) 0.039(4) -0.002(3) -0.012(3) -0.003(3) C4 0.021(4) 0.039(4) 0.081(6) -0.019(4) -0.011(4) 0.005(3) C5 0.051(5) 0.039(5) 0.054(5) 0.018(4) -0.020(4) -0.025(4) C6 0.035(4) 0.030(4) 0.024(4) 0.013(3) -0.014(3) -0.016(3) C7 0.052(5) 0.054(5) 0.029(4) 0.009(4) 0.007(4) -0.023(4) C8 0.032(4) 0.042(4) 0.027(4) -0.001(3) -0.015(3) -0.005(3) C9 0.018(3) 0.018(3) 0.025(4) 0.002(3) -0.008(3) -0.005(3) C10 0.054(5) 0.046(5) 0.032(4) 0.006(3) -0.015(4) -0.029(4) C11 0.018(3) 0.022(3) 0.021(3) 0.001(3) -0.004(3) -0.001(3) C12 0.034(4) 0.038(4) 0.047(5) 0.012(3) 0.001(4) -0.016(3) C13 0.021(4) 0.025(4) 0.032(4) 0.005(3) -0.009(3) -0.007(3) C14 0.049(5) 0.024(4) 0.050(5) 0.002(3) -0.002(4) -0.021(3) C15 0.034(4) 0.048(5) 0.044(5) 0.001(4) -0.014(4) -0.009(4) C16 0.033(4) 0.032(4) 0.023(4) -0.002(3) -0.006(3) -0.011(3) C17 0.036(4) 0.053(5) 0.042(5) 0.001(4) -0.019(4) -0.015(4) C18 0.030(4) 0.041(4) 0.042(5) -0.013(4) -0.004(3) 0.001(3) C19 0.028(4) 0.029(4) 0.024(4) -0.013(3) -0.002(3) -0.013(3) C20 0.033(4) 0.040(4) 0.035(4) -0.008(3) 0.006(3) -0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S1 2.1648(19) . ? Ni1 S2 2.1427(18) . ? Ni1 P1 2.2450(18) . ? Ni1 C1 1.814(6) . ? Ni2 S3 2.1445(18) . ? Ni2 S4 2.1594(19) . ? Ni2 P2 2.2334(18) . ? Ni2 C11 1.820(6) 2_676 ? S1 C1 1.662(6) . ? S2 C1 1.660(6) 2_665 ? S3 C11 1.656(6) . ? S4 C11 1.660(6) 2_676 ? P1 C3 1.854(6) . ? P1 C6 1.848(6) . ? P1 C9 1.843(6) . ? P2 C13 1.838(6) . ? P2 C16 1.853(6) . ? P2 C19 1.843(6) . ? C1 S2 1.660(6) 2_665 ? C2 C3 1.516(8) . ? C3 C4 1.525(8) . ? C5 C6 1.535(8) . ? C6 C7 1.529(8) . ? C8 C9 1.518(7) . ? C9 C10 1.526(8) . ? C11 Ni2 1.820(6) 2_676 ? C11 S4 1.660(6) 2_676 ? C12 C13 1.534(8) . ? C13 C14 1.534(8) . ? C15 C16 1.531(8) . ? C16 C17 1.496(8) . ? C18 C19 1.527(8) . ? C19 C20 1.524(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 S1 Ni1 P1 109.98(7) . . ? S2 Ni1 S1 150.15(7) . . ? S2 Ni1 P1 99.85(7) . . ? C1 Ni1 S1 48.38(18) . . ? C1 Ni1 S2 101.89(18) . . ? C1 Ni1 P1 158.16(18) . . ? S3 Ni2 S4 151.14(7) . . ? S3 Ni2 P2 100.99(7) . . ? S4 Ni2 P2 107.77(7) . . ? C11 Ni2 S3 102.75(18) 2_676 . ? C11 Ni2 S4 48.39(18) 2_676 . ? C11 Ni2 P2 155.86(18) 2_676 . ? C1 S1 Ni1 54.7(2) . . ? C1 S2 Ni1 110.6(2) 2_665 . ? C11 S3 Ni2 109.5(2) . . ? C11 S4 Ni2 55.0(2) 2_676 . ? C3 P1 Ni1 111.8(2) . . ? C6 P1 Ni1 111.2(2) . . ? C6 P1 C3 104.4(3) . . ? C9 P1 Ni1 113.85(18) . . ? C9 P1 C3 110.7(3) . . ? C9 P1 C6 104.2(3) . . ? C13 P2 Ni2 115.7(2) . . ? C13 P2 C16 111.0(3) . . ? C13 P2 C19 104.0(3) . . ? C16 P2 Ni2 112.0(2) . . ? C19 P2 Ni2 109.0(2) . . ? C19 P2 C16 104.2(3) . . ? S1 C1 Ni1 76.9(2) . . ? S2 C1 Ni1 147.4(3) 2_665 . ? S2 C1 S1 135.6(4) 2_665 . ? C2 C3 P1 113.0(4) . . ? C2 C3 C4 111.7(5) . . ? C4 C3 P1 115.3(4) . . ? C5 C6 P1 111.0(4) . . ? C7 C6 P1 109.5(4) . . ? C7 C6 C5 110.9(5) . . ? C8 C9 P1 118.5(4) . . ? C8 C9 C10 109.9(5) . . ? C10 C9 P1 112.1(4) . . ? S3 C11 Ni2 147.7(4) . 2_676 ? S3 C11 S4 135.7(4) . 2_676 ? S4 C11 Ni2 76.6(2) 2_676 2_676 ? C12 C13 P2 112.3(4) . . ? C14 C13 P2 117.2(4) . . ? C14 C13 C12 110.2(5) . . ? C15 C16 P2 111.5(4) . . ? C17 C16 P2 117.6(4) . . ? C17 C16 C15 113.0(5) . . ? C18 C19 P2 110.5(4) . . ? C20 C19 P2 109.9(4) . . ? C20 C19 C18 109.7(5) . . ? data_rbl9_10 _database_code_depnum_ccdc_archive 'CCDC 896757' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-06-10 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C21 H31 Ni P2)' _chemical_formula_sum 'C42 H62 Ni2 P4' _chemical_formula_weight 808.22 _chemical_melting_point ? 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 10.8561(5) _cell_length_b 17.7577(3) _cell_length_c 11.3609(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.813(3) _cell_angle_gamma 90.00 _cell_volume 2085.15(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8064 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.084 _exptl_absorpt_correction_T_max 0.9478 _exptl_absorpt_correction_T_min 0.6412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour red _exptl_crystal_colour_primary brown _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description hexagonal _exptl_crystal_F_000 860 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_unetI/netI 0.0157 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 20752 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 1.97 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3637 _reflns_number_total 3959 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.701 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.102 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 223 _refine_ls_number_reflns 3959 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0293 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.6527P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.0903 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.060282(19) 0.972304(12) 0.05983(2) 0.02211(10) Uani 1 1 d . . . P1 P 0.13912(4) 0.96630(3) 0.11924(4) 0.02407(13) Uani 1 1 d . . . P2 P -0.18284(4) 0.91764(3) 0.15004(4) 0.02525(13) Uani 1 1 d . . . C1 C 0.24240(18) 1.01681(10) 0.25689(18) 0.0267(4) Uani 1 1 d . . . C2 C 0.1932(2) 1.06162(12) 0.33381(19) 0.0338(4) Uani 1 1 d . . . H2 H 0.1022 1.0618 0.3192 0.041 Uiso 1 1 calc R . . C3 C 0.2694(2) 1.10630(13) 0.4311(2) 0.0420(5) Uani 1 1 d . . . H3 H 0.2303 1.1361 0.4794 0.050 Uiso 1 1 calc R . . C4 C 0.3955(2) 1.10618(13) 0.4541(2) 0.0430(5) Uani 1 1 d . . . H4 H 0.4502 1.1353 0.5195 0.052 Uiso 1 1 calc R . . C5 C 0.4458(2) 1.06170(13) 0.3790(2) 0.0404(5) Uani 1 1 d . . . H5 H 0.5370 1.0611 0.3953 0.048 Uiso 1 1 calc R . . C6 C 0.37086(19) 1.01774(11) 0.2808(2) 0.0319(4) Uani 1 1 d . . . H6 H 0.4107 0.9890 0.2320 0.038 Uiso 1 1 calc R . . C7 C 0.21677(17) 0.87579(10) 0.12205(18) 0.0277(4) Uani 1 1 d . . . C8 C 0.2983(2) 0.84417(12) 0.2323(2) 0.0369(5) Uani 1 1 d . . . H8 H 0.3172 0.8709 0.3082 0.044 Uiso 1 1 calc R . . C9 C 0.3500(2) 0.77375(13) 0.2280(3) 0.0495(6) Uani 1 1 d . . . H9 H 0.4055 0.7517 0.3013 0.059 Uiso 1 1 calc R . . C10 C 0.3205(2) 0.73381(13) 0.1140(3) 0.0543(7) Uani 1 1 d . . . H10 H 0.3578 0.6856 0.1124 0.065 Uiso 1 1 calc R . . C11 C 0.2380(2) 0.76394(13) 0.0042(3) 0.0489(6) Uani 1 1 d . . . H11 H 0.2179 0.7365 -0.0711 0.059 Uiso 1 1 calc R . . C12 C 0.1869(2) 0.83426(12) 0.0083(2) 0.0387(5) Uani 1 1 d . . . H12 H 0.1309 0.8558 -0.0652 0.046 Uiso 1 1 calc R . . C13 C -0.2822(2) 0.82513(13) -0.0705(2) 0.0433(5) Uani 1 1 d . . . H13A H -0.2130 0.8502 -0.0943 0.065 Uiso 1 1 calc R . . H13B H -0.3586 0.8198 -0.1433 0.065 Uiso 1 1 calc R . . H13C H -0.2528 0.7752 -0.0367 0.065 Uiso 1 1 calc R . . C14 C -0.31769(18) 0.87314(12) 0.02920(19) 0.0335(4) Uani 1 1 d . . . H14 H -0.3708 0.9159 -0.0171 0.040 Uiso 1 1 calc R . . C15 C -0.4059(2) 0.83103(15) 0.0874(2) 0.0514(6) Uani 1 1 d . . . H15A H -0.3623 0.7853 0.1277 0.077 Uiso 1 1 calc R . . H15B H -0.4861 0.8173 0.0232 0.077 Uiso 1 1 calc R . . H15C H -0.4263 0.8633 0.1489 0.077 Uiso 1 1 calc R . . C16 C -0.3633(2) 1.02731(13) 0.1445(2) 0.0450(6) Uani 1 1 d . . . H16A H -0.3305 1.0481 0.0800 0.067 Uiso 1 1 calc R . . H16B H -0.3932 1.0684 0.1865 0.067 Uiso 1 1 calc R . . H16C H -0.4354 0.9931 0.1070 0.067 Uiso 1 1 calc R . . C17 C -0.2563(2) 0.98460(12) 0.2372(2) 0.0351(5) Uani 1 1 d . . . H17 H -0.2942 0.9552 0.2928 0.042 Uiso 1 1 calc R . . C18 C -0.1618(2) 1.04233(15) 0.3140(2) 0.0495(6) Uani 1 1 d . . . H18A H -0.0869 1.0163 0.3697 0.074 Uiso 1 1 calc R . . H18B H -0.2047 1.0721 0.3627 0.074 Uiso 1 1 calc R . . H18C H -0.1330 1.0758 0.2590 0.074 Uiso 1 1 calc R . . C19 C -0.0257(2) 0.87242(16) 0.3939(2) 0.0491(6) Uani 1 1 d . . . H19A H 0.0470 0.8978 0.3765 0.074 Uiso 1 1 calc R . . H19B H 0.0069 0.8303 0.4505 0.074 Uiso 1 1 calc R . . H19C H -0.0708 0.9081 0.4320 0.074 Uiso 1 1 calc R . . C20 C -0.12032(19) 0.84248(12) 0.2719(2) 0.0372(5) Uani 1 1 d . . . H20 H -0.1967 0.8210 0.2918 0.045 Uiso 1 1 calc R . . C21 C -0.0618(3) 0.77954(13) 0.2148(3) 0.0539(6) Uani 1 1 d . . . H21A H -0.1298 0.7561 0.1472 0.081 Uiso 1 1 calc R . . H21B H -0.0231 0.7416 0.2779 0.081 Uiso 1 1 calc R . . H21C H 0.0050 0.8005 0.1825 0.081 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 0.01458(14) 0.02523(15) 0.02667(16) 0.00145(8) 0.00654(10) -0.00104(8) P1 0.0159(2) 0.0278(3) 0.0278(3) 0.00226(18) 0.00550(19) 0.00001(16) P2 0.0187(2) 0.0295(3) 0.0280(3) 0.00215(18) 0.00766(19) -0.00235(18) C1 0.0211(9) 0.0278(9) 0.0292(10) 0.0047(7) 0.0046(7) -0.0004(7) C2 0.0285(10) 0.0351(11) 0.0386(11) -0.0004(9) 0.0113(8) -0.0002(8) C3 0.0506(13) 0.0365(11) 0.0399(12) -0.0049(9) 0.0155(10) -0.0011(10) C4 0.0432(13) 0.0379(12) 0.0390(12) -0.0021(9) -0.0005(10) -0.0090(10) C5 0.0271(10) 0.0396(12) 0.0476(12) 0.0045(10) 0.0014(9) -0.0067(9) C6 0.0222(9) 0.0336(10) 0.0386(11) 0.0039(8) 0.0072(8) -0.0003(8) C7 0.0185(8) 0.0266(9) 0.0396(10) 0.0026(8) 0.0114(8) -0.0019(7) C8 0.0305(10) 0.0338(11) 0.0451(12) 0.0061(9) 0.0095(9) 0.0014(8) C9 0.0354(12) 0.0387(12) 0.0733(17) 0.0176(12) 0.0149(11) 0.0092(10) C10 0.0419(13) 0.0283(11) 0.104(2) 0.0033(13) 0.0387(14) 0.0039(10) C11 0.0471(13) 0.0352(12) 0.0734(17) -0.0140(12) 0.0318(13) -0.0082(10) C12 0.0320(11) 0.0368(11) 0.0474(12) -0.0052(9) 0.0122(9) -0.0037(9) C13 0.0528(14) 0.0350(11) 0.0382(12) -0.0025(9) 0.0082(10) -0.0083(10) C14 0.0245(9) 0.0369(11) 0.0359(11) 0.0033(8) 0.0044(8) -0.0082(8) C15 0.0344(12) 0.0609(15) 0.0570(15) 0.0029(12) 0.0110(11) -0.0222(11) C16 0.0306(11) 0.0536(14) 0.0537(14) -0.0001(11) 0.0173(11) 0.0081(9) C17 0.0275(10) 0.0458(12) 0.0361(11) -0.0009(9) 0.0159(9) 0.0001(9) C18 0.0391(13) 0.0565(14) 0.0516(14) -0.0187(12) 0.0119(11) 0.0001(11) C19 0.0415(13) 0.0637(16) 0.0370(12) 0.0077(11) 0.0043(10) 0.0065(11) C20 0.0270(10) 0.0410(11) 0.0417(12) 0.0146(9) 0.0079(9) -0.0029(9) C21 0.0494(14) 0.0354(12) 0.0630(16) 0.0042(11) -0.0034(12) 0.0053(10) _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 Ni1 2.3702(4) 3_575 ? Ni1 P1 2.0638(5) . ? Ni1 P1 2.2349(5) 3_575 ? Ni1 P2 2.1440(5) . ? P1 Ni1 2.2349(5) 3_575 ? P1 C1 1.853(2) . ? P1 C7 1.8107(19) . ? P2 C14 1.850(2) . ? P2 C17 1.875(2) . ? P2 C20 1.893(2) . ? C1 C2 1.403(3) . ? C1 C6 1.337(3) . ? C2 H2 0.9500 . ? C2 C3 1.406(3) . ? C3 H3 0.9500 . ? C3 C4 1.313(3) . ? C4 H4 0.9500 . ? C4 C5 1.392(4) . ? C5 H5 0.9500 . ? C5 C6 1.400(3) . ? C6 H6 0.9500 . ? C7 C8 1.411(3) . ? C7 C12 1.436(3) . ? C8 H8 0.9500 . ? C8 C9 1.378(3) . ? C9 H9 0.9500 . ? C9 C10 1.425(4) . ? C10 H10 0.9500 . ? C10 C11 1.401(4) . ? C11 H11 0.9500 . ? C11 C12 1.373(3) . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 C14 1.557(3) . ? C14 H14 1.0000 . ? C14 C15 1.517(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 C17 1.511(3) . ? C17 H17 1.0000 . ? C17 C18 1.522(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 C20 1.545(3) . ? C20 H20 1.0000 . ? C20 C21 1.525(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Ni1 Ni1 53.152(15) 3_575 3_575 ? P1 Ni1 Ni1 60.064(16) . 3_575 ? P1 Ni1 P1 113.217(16) . 3_575 ? P1 Ni1 P2 124.23(2) . . ? P2 Ni1 Ni1 173.92(2) . 3_575 ? P2 Ni1 P1 122.353(19) . 3_575 ? Ni1 P1 Ni1 66.783(16) . 3_575 ? C1 P1 Ni1 119.76(6) . 3_575 ? C1 P1 Ni1 123.66(7) . . ? C7 P1 Ni1 119.72(7) . 3_575 ? C7 P1 Ni1 119.19(6) . . ? C7 P1 C1 104.87(9) . . ? C14 P2 Ni1 107.74(7) . . ? C14 P2 C17 107.16(10) . . ? C14 P2 C20 105.48(9) . . ? C17 P2 Ni1 113.07(7) . . ? C17 P2 C20 100.14(10) . . ? C20 P2 Ni1 122.19(7) . . ? C2 C1 P1 123.55(14) . . ? C6 C1 P1 120.13(16) . . ? C6 C1 C2 116.02(18) . . ? C1 C2 H2 117.8 . . ? C1 C2 C3 124.42(19) . . ? C3 C2 H2 117.8 . . ? C2 C3 H3 120.6 . . ? C4 C3 C2 118.8(2) . . ? C4 C3 H3 120.6 . . ? C3 C4 H4 121.3 . . ? C3 C4 C5 117.4(2) . . ? C5 C4 H4 121.3 . . ? C4 C5 H5 117.9 . . ? C4 C5 C6 124.3(2) . . ? C6 C5 H5 117.9 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C8 C7 P1 122.08(16) . . ? C8 C7 C12 120.17(18) . . ? C12 C7 P1 117.65(15) . . ? C7 C8 H8 120.6 . . ? C9 C8 C7 118.8(2) . . ? C9 C8 H8 120.6 . . ? C8 C9 H9 119.9 . . ? C8 C9 C10 120.3(2) . . ? C10 C9 H9 119.9 . . ? C9 C10 H10 119.2 . . ? C11 C10 C9 121.6(2) . . ? C11 C10 H10 119.2 . . ? C10 C11 H11 120.9 . . ? C12 C11 C10 118.2(2) . . ? C12 C11 H11 120.9 . . ? C7 C12 H12 119.5 . . ? C11 C12 C7 121.0(2) . . ? C11 C12 H12 119.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? P2 C14 H14 105.3 . . ? C13 C14 P2 117.25(15) . . ? C13 C14 H14 105.3 . . ? C15 C14 P2 110.43(15) . . ? C15 C14 C13 112.13(19) . . ? C15 C14 H14 105.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? P2 C17 H17 109.0 . . ? C16 C17 P2 108.08(15) . . ? C16 C17 H17 109.0 . . ? C16 C17 C18 107.50(19) . . ? C18 C17 P2 114.12(15) . . ? C18 C17 H17 109.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? P2 C20 H20 107.4 . . ? C19 C20 P2 113.86(16) . . ? C19 C20 H20 107.4 . . ? C21 C20 P2 107.95(16) . . ? C21 C20 C19 112.61(18) . . ? C21 C20 H20 107.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 Ni1 Ni1 P1 C1 111.30(7) 3_575 . . . ? Ni1 Ni1 P1 C7 -112.22(8) 3_575 . . . ? Ni1 P1 C1 C2 1.8(2) . . . . ? Ni1 P1 C1 C2 82.31(17) 3_575 . . . ? Ni1 P1 C1 C6 -171.68(13) . . . . ? Ni1 P1 C1 C6 -91.16(16) 3_575 . . . ? Ni1 P1 C7 C8 162.26(13) 3_575 . . . ? Ni1 P1 C7 C8 -119.34(15) . . . . ? Ni1 P1 C7 C12 -21.28(17) 3_575 . . . ? Ni1 P1 C7 C12 57.12(16) . . . . ? Ni1 P2 C14 C13 47.97(16) . . . . ? Ni1 P2 C14 C15 178.06(15) . . . . ? Ni1 P2 C17 C16 75.08(15) . . . . ? Ni1 P2 C17 C18 -44.44(19) . . . . ? Ni1 P2 C20 C19 68.60(18) . . . . ? Ni1 P2 C20 C21 -57.22(17) . . . . ? P1 Ni1 P1 Ni1 0.0 3_575 . . 3_575 ? P1 Ni1 P1 C1 111.31(7) 3_575 . . . ? P1 Ni1 P1 C7 -112.22(8) 3_575 . . . ? P1 Ni1 P2 C14 -135.54(7) . . . . ? P1 Ni1 P2 C14 38.93(8) 3_575 . . . ? P1 Ni1 P2 C17 -79.29(8) 3_575 . . . ? P1 Ni1 P2 C17 106.24(8) . . . . ? P1 Ni1 P2 C20 -13.37(9) . . . . ? P1 Ni1 P2 C20 161.10(9) 3_575 . . . ? P1 C1 C2 C3 -173.35(17) . . . . ? P1 C1 C6 C5 174.41(15) . . . . ? P1 C7 C8 C9 177.54(16) . . . . ? P1 C7 C12 C11 -177.42(16) . . . . ? P2 Ni1 P1 Ni1 174.92(3) . . . 3_575 ? P2 Ni1 P1 C1 -73.78(8) . . . . ? P2 Ni1 P1 C7 62.70(8) . . . . ? C1 P1 C7 C8 24.29(18) . . . . ? C1 P1 C7 C12 -159.25(15) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C6 C1 C2 C3 0.4(3) . . . . ? C7 P1 C1 C2 -139.74(16) . . . . ? C7 P1 C1 C6 46.79(18) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C7 C12 C11 -0.9(3) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C12 C7 C8 C9 1.2(3) . . . . ? C14 P2 C17 C16 -43.48(17) . . . . ? C14 P2 C17 C18 -163.00(17) . . . . ? C14 P2 C20 C19 -168.19(16) . . . . ? C14 P2 C20 C21 65.99(16) . . . . ? C17 P2 C14 C13 169.93(15) . . . . ? C17 P2 C14 C15 -59.98(19) . . . . ? C17 P2 C20 C19 -57.06(18) . . . . ? C17 P2 C20 C21 177.12(15) . . . . ? C20 P2 C14 C13 -84.02(17) . . . . ? C20 P2 C14 C15 46.08(19) . . . . ? C20 P2 C17 C16 -153.29(15) . . . . ? C20 P2 C17 C18 87.19(18) . . . . ? data_rbr4_11 _database_code_depnum_ccdc_archive 'CCDC 896758' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-06-10 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H48 Ni P2 S' _chemical_formula_sum 'C24 H48 Ni P2 S' _chemical_formula_weight 489.33 _chemical_melting_point ? 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' 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.1831(18) _cell_length_b 11.038(2) _cell_length_c 13.734(3) _cell_angle_alpha 81.49(2) _cell_angle_beta 88.23(3) _cell_angle_gamma 84.88(3) _cell_volume 1371.1(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8064 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 28.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 0.908 _exptl_absorpt_correction_T_max 0.8834 _exptl_absorpt_correction_T_min 0.8252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, BRUKER 2003' _exptl_crystal_colour yellow _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.14 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_unetI/netI 0.0434 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 14382 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 1.50 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 4500 _reflns_number_total 5385 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.547 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.124 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 269 _refine_ls_number_reflns 5385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0387 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0951 _refine_ls_wR_factor_ref 0.1191 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.24440(3) 0.88240(3) 0.25867(2) 0.02117(12) Uani 1 1 d . . . H1 H 0.114(4) 0.941(3) 0.235(3) 0.066(11) Uiso 1 1 d . . . S1 S 0.46978(8) 0.80900(7) 0.29711(7) 0.0365(2) Uani 1 1 d . . . P1 P 0.28585(7) 1.06774(6) 0.27866(5) 0.02135(17) Uani 1 1 d . . . P2 P 0.12657(7) 0.72609(6) 0.23829(5) 0.02099(17) Uani 1 1 d . . . C1 C 0.5334(3) 0.6667(3) 0.2584(2) 0.0302(7) Uani 1 1 d . . . C2 C 0.5577(3) 0.6563(3) 0.1598(3) 0.0396(8) Uani 1 1 d . . . H2 H 0.5327 0.7250 0.1112 0.048 Uiso 1 1 calc R . . C3 C 0.6179(4) 0.5468(4) 0.1310(3) 0.0533(10) Uani 1 1 d . . . H3 H 0.6319 0.5408 0.0630 0.064 Uiso 1 1 calc R . . C4 C 0.6571(4) 0.4478(3) 0.2000(3) 0.0572(11) Uani 1 1 d . . . H4 H 0.6988 0.3733 0.1800 0.069 Uiso 1 1 calc R . . C5 C 0.6362(4) 0.4562(3) 0.2983(3) 0.0517(10) Uani 1 1 d . . . H5 H 0.6637 0.3875 0.3464 0.062 Uiso 1 1 calc R . . C6 C 0.5746(3) 0.5651(3) 0.3276(3) 0.0385(7) Uani 1 1 d . . . H6 H 0.5606 0.5701 0.3957 0.046 Uiso 1 1 calc R . . C7 C 0.4327(4) 1.0877(3) 0.0970(2) 0.0440(8) Uani 1 1 d . . . H7A H 0.4628 0.9994 0.1079 0.066 Uiso 1 1 calc R . . H7B H 0.5019 1.1301 0.0511 0.066 Uiso 1 1 calc R . . H7C H 0.3347 1.1013 0.0691 0.066 Uiso 1 1 calc R . . C8 C 0.4309(3) 1.1383(3) 0.1956(2) 0.0292(6) Uani 1 1 d . . . H8 H 0.4055 1.2292 0.1825 0.035 Uiso 1 1 calc R . . C9 C 0.5851(3) 1.1147(3) 0.2387(2) 0.0354(7) Uani 1 1 d . . . H9A H 0.5899 1.1589 0.2952 0.053 Uiso 1 1 calc R . . H9B H 0.6569 1.1437 0.1883 0.053 Uiso 1 1 calc R . . H9C H 0.6069 1.0264 0.2600 0.053 Uiso 1 1 calc R . . C10 C 0.2610(3) 0.9908(3) 0.4823(2) 0.0346(7) Uani 1 1 d . . . H10A H 0.1588 1.0247 0.4834 0.052 Uiso 1 1 calc R . . H10B H 0.3031 0.9884 0.5474 0.052 Uiso 1 1 calc R . . H10C H 0.2659 0.9073 0.4655 0.052 Uiso 1 1 calc R . . C11 C 0.3478(3) 1.0722(3) 0.4051(2) 0.0267(6) Uani 1 1 d . . . H11 H 0.4507 1.0338 0.4078 0.032 Uiso 1 1 calc R . . C12 C 0.3545(3) 1.2009(3) 0.4322(2) 0.0358(7) Uani 1 1 d . . . H12A H 0.4067 1.2512 0.3800 0.054 Uiso 1 1 calc R . . H12B H 0.4061 1.1951 0.4943 0.054 Uiso 1 1 calc R . . H12C H 0.2550 1.2389 0.4396 0.054 Uiso 1 1 calc R . . C13 C 0.0859(4) 1.2131(3) 0.1511(2) 0.0468(9) Uani 1 1 d . . . H13A H 0.1672 1.2423 0.1086 0.070 Uiso 1 1 calc R . . H13B H 0.0023 1.2751 0.1434 0.070 Uiso 1 1 calc R . . H13C H 0.0579 1.1362 0.1324 0.070 Uiso 1 1 calc R . . C14 C 0.1332(3) 1.1908(3) 0.2580(2) 0.0297(6) Uani 1 1 d . . . H14 H 0.1708 1.2685 0.2723 0.036 Uiso 1 1 calc R . . C15 C 0.0019(3) 1.1662(3) 0.3264(3) 0.0419(8) Uani 1 1 d . . . H15A H -0.0338 1.0875 0.3175 0.063 Uiso 1 1 calc R . . H15B H -0.0759 1.2323 0.3107 0.063 Uiso 1 1 calc R . . H15C H 0.0311 1.1628 0.3948 0.063 Uiso 1 1 calc R . . C16 C -0.1284(3) 0.7929(3) 0.3366(2) 0.0358(7) Uani 1 1 d . . . H16A H -0.0996 0.7275 0.3906 0.054 Uiso 1 1 calc R . . H16B H -0.2351 0.8085 0.3366 0.054 Uiso 1 1 calc R . . H16C H -0.0844 0.8681 0.3455 0.054 Uiso 1 1 calc R . . C17 C -0.0754(3) 0.7532(3) 0.2386(2) 0.0270(6) Uani 1 1 d . . . H17 H -0.1164 0.6735 0.2332 0.032 Uiso 1 1 calc R . . C18 C -0.1334(3) 0.8480(3) 0.1532(2) 0.0366(7) Uani 1 1 d . . . H18A H -0.0878 0.9248 0.1534 0.055 Uiso 1 1 calc R . . H18B H -0.2397 0.8632 0.1606 0.055 Uiso 1 1 calc R . . H18C H -0.1101 0.8167 0.0909 0.055 Uiso 1 1 calc R . . C19 C 0.2027(4) 0.6176(3) 0.4318(2) 0.0419(8) Uani 1 1 d . . . H19A H 0.2833 0.6710 0.4235 0.063 Uiso 1 1 calc R . . H19B H 0.2325 0.5418 0.4759 0.063 Uiso 1 1 calc R . . H19C H 0.1172 0.6603 0.4603 0.063 Uiso 1 1 calc R . . C20 C 0.1638(3) 0.5859(3) 0.3317(2) 0.0310(7) Uani 1 1 d . . . H20 H 0.2534 0.5403 0.3074 0.037 Uiso 1 1 calc R . . C21 C 0.0463(4) 0.4955(3) 0.3447(3) 0.0405(8) Uani 1 1 d . . . H21A H -0.0439 0.5349 0.3702 0.061 Uiso 1 1 calc R . . H21B H 0.0796 0.4230 0.3914 0.061 Uiso 1 1 calc R . . H21C H 0.0275 0.4703 0.2811 0.061 Uiso 1 1 calc R . . C22 C 0.0826(4) 0.5834(3) 0.0829(3) 0.0461(9) Uani 1 1 d . . . H22A H 0.0811 0.5080 0.1304 0.069 Uiso 1 1 calc R . . H22B H 0.1204 0.5631 0.0192 0.069 Uiso 1 1 calc R . . H22C H -0.0169 0.6234 0.0751 0.069 Uiso 1 1 calc R . . C23 C 0.1810(3) 0.6705(3) 0.1202(2) 0.0308(7) Uani 1 1 d . . . H23 H 0.2778 0.6223 0.1322 0.037 Uiso 1 1 calc R . . C24 C 0.2093(4) 0.7775(3) 0.0399(2) 0.0421(8) Uani 1 1 d . . . H24A H 0.1161 0.8232 0.0196 0.063 Uiso 1 1 calc R . . H24B H 0.2578 0.7457 -0.0168 0.063 Uiso 1 1 calc R . . H24C H 0.2721 0.8323 0.0655 0.063 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 0.01896(19) 0.0216(2) 0.0237(2) -0.00510(14) -0.00202(14) -0.00197(13) S1 0.0217(4) 0.0286(4) 0.0613(6) -0.0142(4) -0.0101(3) 0.0015(3) P1 0.0225(4) 0.0218(4) 0.0204(4) -0.0046(3) -0.0017(3) -0.0025(3) P2 0.0186(3) 0.0222(4) 0.0229(4) -0.0054(3) 0.0004(3) -0.0027(3) C1 0.0163(13) 0.0277(15) 0.0474(19) -0.0081(13) -0.0034(12) -0.0013(11) C2 0.0309(17) 0.0413(18) 0.046(2) -0.0063(15) -0.0038(14) -0.0008(14) C3 0.041(2) 0.065(3) 0.059(2) -0.029(2) 0.0038(18) 0.0008(18) C4 0.044(2) 0.039(2) 0.093(3) -0.029(2) -0.004(2) 0.0080(16) C5 0.040(2) 0.0310(18) 0.082(3) -0.0033(18) -0.0061(19) 0.0020(15) C6 0.0324(17) 0.0352(17) 0.047(2) -0.0044(15) -0.0017(14) -0.0013(13) C7 0.054(2) 0.055(2) 0.0246(16) -0.0063(15) 0.0092(15) -0.0150(17) C8 0.0320(16) 0.0280(15) 0.0272(16) 0.0005(12) 0.0021(12) -0.0096(12) C9 0.0315(16) 0.0364(17) 0.0391(18) -0.0057(14) 0.0071(13) -0.0092(13) C10 0.0361(17) 0.0409(18) 0.0258(16) -0.0020(13) 0.0000(13) -0.0023(14) C11 0.0234(14) 0.0344(16) 0.0233(14) -0.0070(12) -0.0030(11) -0.0023(12) C12 0.0374(17) 0.0410(18) 0.0329(17) -0.0162(14) -0.0051(13) -0.0056(14) C13 0.057(2) 0.0347(18) 0.048(2) -0.0016(15) -0.0257(17) 0.0056(16) C14 0.0294(15) 0.0228(14) 0.0370(17) -0.0062(12) -0.0069(13) 0.0020(12) C15 0.0276(16) 0.0331(17) 0.065(2) -0.0103(16) -0.0043(15) 0.0060(13) C16 0.0235(15) 0.0435(18) 0.0424(19) -0.0149(15) 0.0049(13) -0.0017(13) C17 0.0199(13) 0.0297(15) 0.0331(16) -0.0084(12) 0.0005(11) -0.0060(11) C18 0.0260(15) 0.0391(18) 0.0455(19) -0.0082(14) -0.0087(14) -0.0021(13) C19 0.0421(19) 0.050(2) 0.0285(17) 0.0122(15) -0.0032(14) -0.0069(15) C20 0.0273(15) 0.0269(15) 0.0363(17) 0.0018(13) 0.0044(12) -0.0002(12) C21 0.0438(19) 0.0272(16) 0.049(2) 0.0013(14) 0.0062(15) -0.0059(14) C22 0.051(2) 0.052(2) 0.043(2) -0.0243(17) 0.0071(16) -0.0196(17) C23 0.0290(15) 0.0377(17) 0.0287(16) -0.0143(13) 0.0056(12) -0.0062(13) C24 0.047(2) 0.058(2) 0.0254(17) -0.0104(15) 0.0071(14) -0.0213(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 H1 1.33(4) . ? Ni1 S1 2.2046(10) . ? Ni1 P1 2.1721(9) . ? Ni1 P2 2.1727(9) . ? S1 C1 1.776(3) . ? P1 C8 1.873(3) . ? P1 C11 1.853(3) . ? P1 C14 1.861(3) . ? P2 C17 1.852(3) . ? P2 C20 1.871(3) . ? P2 C23 1.857(3) . ? C1 C2 1.385(4) . ? C1 C6 1.391(4) . ? C2 H2 0.9500 . ? C2 C3 1.390(5) . ? C3 H3 0.9500 . ? C3 C4 1.366(5) . ? C4 H4 0.9500 . ? C4 C5 1.373(5) . ? C5 H5 0.9500 . ? C5 C6 1.390(5) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.539(4) . ? C8 H8 1.0000 . ? C8 C9 1.538(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 C11 1.537(4) . ? C11 H11 1.0000 . ? C11 C12 1.527(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 C14 1.523(4) . ? C14 H14 1.0000 . ? C14 C15 1.524(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 C17 1.530(4) . ? C17 H17 1.0000 . ? C17 C18 1.526(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 C20 1.529(4) . ? C20 H20 1.0000 . ? C20 C21 1.524(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22 C23 1.527(4) . ? C23 H23 1.0000 . ? C23 C24 1.526(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Ni1 H1 172.7(15) . . ? P1 Ni1 H1 80.2(15) . . ? P1 Ni1 S1 92.68(4) . . ? P1 Ni1 P2 160.27(3) . . ? P2 Ni1 H1 80.7(15) . . ? P2 Ni1 S1 106.57(4) . . ? C1 S1 Ni1 117.13(10) . . ? C8 P1 Ni1 115.34(10) . . ? C11 P1 Ni1 111.16(9) . . ? C11 P1 C8 104.95(13) . . ? C11 P1 C14 105.02(13) . . ? C14 P1 Ni1 118.25(10) . . ? C14 P1 C8 100.67(14) . . ? C17 P2 Ni1 115.77(9) . . ? C17 P2 C20 104.10(13) . . ? C17 P2 C23 106.57(13) . . ? C20 P2 Ni1 115.15(10) . . ? C23 P2 Ni1 110.98(9) . . ? C23 P2 C20 103.14(14) . . ? C2 C1 S1 121.6(2) . . ? C2 C1 C6 117.8(3) . . ? C6 C1 S1 120.3(2) . . ? C1 C2 H2 119.5 . . ? C1 C2 C3 121.0(3) . . ? C3 C2 H2 119.5 . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 120.1 . . ? C3 C4 C5 119.9(3) . . ? C5 C4 H4 120.1 . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 120.1(3) . . ? C6 C5 H5 120.0 . . ? C1 C6 H6 119.6 . . ? C5 C6 C1 120.9(3) . . ? C5 C6 H6 119.6 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P1 C8 H8 108.3 . . ? C7 C8 P1 109.2(2) . . ? C7 C8 H8 108.3 . . ? C9 C8 P1 113.80(19) . . ? C9 C8 C7 108.7(3) . . ? C9 C8 H8 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? P1 C11 H11 105.9 . . ? C10 C11 P1 111.6(2) . . ? C10 C11 H11 105.9 . . ? C12 C11 P1 115.1(2) . . ? C12 C11 C10 111.8(2) . . ? C12 C11 H11 105.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? P1 C14 H14 107.2 . . ? C13 C14 P1 111.5(2) . . ? C13 C14 H14 107.2 . . ? C13 C14 C15 110.2(3) . . ? C15 C14 P1 113.1(2) . . ? C15 C14 H14 107.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? P2 C17 H17 108.0 . . ? C16 C17 P2 109.28(19) . . ? C16 C17 H17 108.0 . . ? C18 C17 P2 113.5(2) . . ? C18 C17 C16 110.0(2) . . ? C18 C17 H17 108.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? P2 C20 H20 105.9 . . ? C19 C20 P2 112.3(2) . . ? C19 C20 H20 105.9 . . ? C21 C20 P2 116.1(2) . . ? C21 C20 C19 109.8(2) . . ? C21 C20 H20 105.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? P2 C23 H23 105.7 . . ? C22 C23 P2 117.1(2) . . ? C22 C23 H23 105.7 . . ? C24 C23 P2 111.0(2) . . ? C24 C23 C22 110.8(3) . . ? C24 C23 H23 105.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? data_rbt8_12 _database_code_depnum_ccdc_archive 'CCDC 896759' #TrackingRef '13319_web_deposit_cif_file_0_SamuelA.Johnson_1345144865.cifs.cif' _audit_creation_date 2011-06-11 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C15 H26 Ni P S)' _chemical_formula_sum 'C30 H52 Ni2 P2 S2' _chemical_formula_weight 656.20 _chemical_melting_point ? 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.394(3) _cell_length_b 7.8790(16) _cell_length_c 18.951(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.72(2) _cell_angle_gamma 90.00 _cell_volume 1653.0(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4048 _cell_measurement_temperature 173.0 _cell_measurement_theta_max 27.08 _cell_measurement_theta_min 2.18 _exptl_absorpt_coefficient_mu 1.379 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_crystal_colour brown _exptl_crystal_colour_primary brown _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description hexagonal _exptl_crystal_F_000 700 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_unetI/netI 0.0502 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 16026 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 1.84 _diffrn_ambient_temperature 173.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 2384 _reflns_number_total 3029 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 0.785 _refine_diff_density_min -0.796 _refine_diff_density_rms 0.307 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 169 _refine_ls_number_reflns 3029 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0398 _refine_ls_restrained_S_all 1.118 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0916 _refine_ls_wR_factor_ref 0.1232 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.55710(4) 0.08741(6) 0.97853(3) 0.01859(17) Uani 1 1 d . . . S1 S 0.44025(9) -0.11392(12) 0.90609(6) 0.0219(2) Uani 1 1 d . . . P1 P 0.67924(8) 0.24461(12) 0.95289(6) 0.0185(2) Uani 1 1 d . . . C1 C 0.2970(3) -0.0575(5) 0.8272(2) 0.0251(9) Uani 1 1 d . . . C2 C 0.2137(4) -0.1860(6) 0.7892(2) 0.0328(10) Uani 1 1 d . . . H2 H 0.2343 -0.3006 0.8051 0.039 Uiso 1 1 calc R . . C3 C 0.1019(4) -0.1486(8) 0.7289(3) 0.0492(14) Uani 1 1 d . . . H3 H 0.0457 -0.2373 0.7037 0.059 Uiso 1 1 calc R . . C4 C 0.0712(5) 0.0148(9) 0.7051(3) 0.0626(17) Uani 1 1 d . . . H4 H -0.0061 0.0399 0.6633 0.075 Uiso 1 1 calc R . . C5 C 0.1532(5) 0.1450(8) 0.7419(3) 0.0578(16) Uani 1 1 d . . . H5 H 0.1318 0.2591 0.7253 0.069 Uiso 1 1 calc R . . C6 C 0.2665(4) 0.1081(6) 0.8032(3) 0.0383(11) Uani 1 1 d . . . H6 H 0.3227 0.1969 0.8283 0.046 Uiso 1 1 calc R . . C7 C 0.8607(4) 0.0246(5) 1.0546(3) 0.0340(10) Uani 1 1 d . . . H7A H 0.7968 -0.0140 1.0678 0.051 Uiso 1 1 calc R . . H7B H 0.9392 0.0150 1.1013 0.051 Uiso 1 1 calc R . . H7C H 0.8607 -0.0458 1.0120 0.051 Uiso 1 1 calc R . . C8 C 0.8380(3) 0.2102(5) 1.0277(2) 0.0229(9) Uani 1 1 d . . . H8 H 0.8487 0.2774 1.0751 0.027 Uiso 1 1 calc R . . C9 C 0.9359(4) 0.2720(6) 1.0058(3) 0.0393(12) Uani 1 1 d . . . H9A H 0.9299 0.2095 0.9595 0.059 Uiso 1 1 calc R . . H9B H 1.0156 0.2525 1.0503 0.059 Uiso 1 1 calc R . . H9C H 0.9251 0.3935 0.9937 0.059 Uiso 1 1 calc R . . C10 C 0.6664(4) 0.5302(5) 1.0378(3) 0.0374(11) Uani 1 1 d . . . H10A H 0.6235 0.4508 1.0561 0.056 Uiso 1 1 calc R . . H10B H 0.6337 0.6448 1.0348 0.056 Uiso 1 1 calc R . . H10C H 0.7526 0.5298 1.0750 0.056 Uiso 1 1 calc R . . C11 C 0.6500(4) 0.4760(5) 0.9561(2) 0.0259(9) Uani 1 1 d . . . H11 H 0.5622 0.4922 0.9198 0.031 Uiso 1 1 calc R . . C12 C 0.7168(5) 0.5977(5) 0.9267(3) 0.0500(14) Uani 1 1 d . . . H12A H 0.8024 0.6013 0.9650 0.075 Uiso 1 1 calc R . . H12B H 0.6819 0.7115 0.9208 0.075 Uiso 1 1 calc R . . H12C H 0.7090 0.5583 0.8756 0.075 Uiso 1 1 calc R . . C13 C 0.7094(4) 0.0371(5) 0.8433(3) 0.0354(11) Uani 1 1 d . . . H13A H 0.7918 0.0110 0.8830 0.053 Uiso 1 1 calc R . . H13B H 0.7043 0.0265 0.7904 0.053 Uiso 1 1 calc R . . H13C H 0.6528 -0.0424 0.8487 0.053 Uiso 1 1 calc R . . C14 C 0.6773(4) 0.2174(5) 0.8554(2) 0.0260(9) Uani 1 1 d . . . H14 H 0.7380 0.2964 0.8521 0.031 Uiso 1 1 calc R . . C15 C 0.5522(4) 0.2637(6) 0.7901(2) 0.0401(12) Uani 1 1 d . . . H15A H 0.4917 0.1876 0.7927 0.060 Uiso 1 1 calc R . . H15B H 0.5518 0.2521 0.7385 0.060 Uiso 1 1 calc R . . H15C H 0.5332 0.3812 0.7972 0.060 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 0.0172(3) 0.0217(3) 0.0178(3) 0.0013(2) 0.0086(2) -0.0048(2) S1 0.0204(5) 0.0259(5) 0.0189(5) -0.0012(4) 0.0084(4) -0.0041(4) P1 0.0172(5) 0.0173(5) 0.0228(5) 0.0024(4) 0.0107(4) -0.0023(4) C1 0.020(2) 0.039(2) 0.018(2) -0.0023(18) 0.0104(17) -0.0002(18) C2 0.026(2) 0.050(3) 0.022(2) -0.007(2) 0.0105(19) -0.004(2) C3 0.030(3) 0.085(4) 0.026(3) -0.001(3) 0.007(2) -0.012(3) C4 0.026(3) 0.108(5) 0.042(3) 0.025(3) 0.005(2) 0.006(3) C5 0.048(3) 0.069(4) 0.059(4) 0.034(3) 0.027(3) 0.018(3) C6 0.037(3) 0.047(3) 0.036(3) 0.011(2) 0.022(2) 0.005(2) C7 0.033(3) 0.033(2) 0.036(3) 0.008(2) 0.016(2) 0.012(2) C8 0.017(2) 0.024(2) 0.027(2) -0.0047(17) 0.0094(17) -0.0006(16) C9 0.021(2) 0.043(3) 0.054(3) 0.001(2) 0.017(2) -0.004(2) C10 0.041(3) 0.022(2) 0.051(3) -0.003(2) 0.022(2) 0.003(2) C11 0.025(2) 0.017(2) 0.041(3) 0.0055(18) 0.019(2) 0.0039(17) C12 0.060(4) 0.020(2) 0.090(4) 0.012(2) 0.051(3) 0.003(2) C13 0.048(3) 0.035(2) 0.029(2) -0.006(2) 0.023(2) -0.007(2) C14 0.028(2) 0.028(2) 0.024(2) 0.0053(17) 0.0139(19) -0.0052(18) C15 0.032(3) 0.062(3) 0.024(2) 0.012(2) 0.011(2) 0.001(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 Ni1 2.3660(10) 3_657 ? Ni1 S1 2.1818(13) 3_657 ? Ni1 S1 2.1703(11) . ? Ni1 P1 2.1734(11) . ? S1 Ni1 2.1819(12) 3_657 ? S1 C1 1.788(4) . ? P1 C8 1.857(4) . ? P1 C11 1.865(4) . ? P1 C14 1.850(4) . ? C1 C2 1.394(6) . ? C1 C6 1.378(6) . ? C2 H2 0.9500 . ? C2 C3 1.374(6) . ? C3 H3 0.9500 . ? C3 C4 1.360(8) . ? C4 H4 0.9500 . ? C4 C5 1.391(8) . ? C5 H5 0.9500 . ? C5 C6 1.392(7) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 C8 1.533(6) . ? C8 H8 1.0000 . ? C8 C9 1.527(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 C11 1.530(6) . ? C11 H11 1.0000 . ? C11 C12 1.526(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13 C14 1.520(6) . ? C14 H14 1.0000 . ? C14 C15 1.530(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Ni1 Ni1 56.84(3) 3_657 3_657 ? S1 Ni1 Ni1 57.30(4) . 3_657 ? S1 Ni1 S1 114.14(4) . 3_657 ? S1 Ni1 P1 127.50(4) . . ? P1 Ni1 Ni1 173.30(4) . 3_657 ? P1 Ni1 S1 118.13(4) . 3_657 ? Ni1 S1 Ni1 65.86(4) . 3_657 ? C1 S1 Ni1 112.11(13) . 3_657 ? C1 S1 Ni1 118.45(14) . . ? C8 P1 Ni1 110.60(13) . . ? C8 P1 C11 105.84(18) . . ? C11 P1 Ni1 112.61(13) . . ? C14 P1 Ni1 117.37(13) . . ? C14 P1 C8 106.18(18) . . ? C14 P1 C11 103.34(18) . . ? C2 C1 S1 118.6(3) . . ? C6 C1 S1 122.2(3) . . ? C6 C1 C2 119.2(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 C1 120.7(5) . . ? C3 C2 H2 119.7 . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.4(5) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 120.0 . . ? C3 C4 C5 120.0(5) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 120.0(5) . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.8(5) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? P1 C8 H8 106.0 . . ? C7 C8 P1 111.5(3) . . ? C7 C8 H8 106.0 . . ? C9 C8 P1 116.4(3) . . ? C9 C8 C7 110.2(3) . . ? C9 C8 H8 106.0 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? P1 C11 H11 105.6 . . ? C10 C11 P1 111.5(3) . . ? C10 C11 H11 105.6 . . ? C12 C11 P1 117.2(3) . . ? C12 C11 C10 110.3(4) . . ? C12 C11 H11 105.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? P1 C14 H14 108.5 . . ? C13 C14 P1 111.8(3) . . ? C13 C14 H14 108.5 . . ? C13 C14 C15 109.9(4) . . ? C15 C14 P1 109.5(3) . . ? C15 C14 H14 108.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? #===END