# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_zb229 _database_code_depnum_ccdc_archive 'CCDC 915793' #TrackingRef 'zb229.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H24 Br2 Ni P2' _chemical_formula_sum 'C10 H24 Br2 Ni P2' _chemical_formula_weight 424.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7070(2) _cell_length_b 13.3165(2) _cell_length_c 13.7802(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.665(7) _cell_angle_gamma 90.00 _cell_volume 1570.17(12) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 10405 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 68.30 _exptl_crystal_description multi-faceted _exptl_crystal_colour brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 9.435 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.244 _exptl_absorpt_correction_T_max 0.354 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 85(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'micro-focus rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn744+ CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.629 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15593 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 68.24 _reflns_number_total 2854 _reflns_number_gt 2805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r5' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r5' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+2.1350P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2854 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_restrained_S_all 1.207 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.80441(5) 0.25885(3) 0.19808(3) 0.00685(13) Uani 1 1 d . . . Br1 Br 0.62814(3) 0.14120(2) 0.11396(2) 0.01275(11) Uani 1 1 d . . . Br2 Br 1.01900(3) 0.20946(2) 0.12761(2) 0.01028(11) Uani 1 1 d . . . P1 P 0.61951(8) 0.31167(5) 0.26782(5) 0.00873(16) Uani 1 1 d . . . P2 P 0.95582(8) 0.36315(5) 0.28908(5) 0.00710(16) Uani 1 1 d . . . C1 C 0.5746(3) 0.2193(2) 0.3566(2) 0.0143(6) Uani 1 1 d . . . H1A H 0.5207 0.2535 0.4046 0.017 Uiso 1 1 calc R . . H1B H 0.5019 0.1686 0.3211 0.017 Uiso 1 1 calc R . . C2 C 0.7184(3) 0.1661(2) 0.4123(2) 0.0150(6) Uani 1 1 d . . . H2A H 0.7746 0.1342 0.3652 0.023 Uiso 1 1 calc R . . H2B H 0.6866 0.1149 0.4557 0.023 Uiso 1 1 calc R . . H2C H 0.7870 0.2150 0.4522 0.023 Uiso 1 1 calc R . . C3 C 0.4293(3) 0.3411(2) 0.1930(2) 0.0148(6) Uani 1 1 d . . . H3A H 0.3725 0.2775 0.1743 0.018 Uiso 1 1 calc R . . H3B H 0.3681 0.3803 0.2336 0.018 Uiso 1 1 calc R . . C4 C 0.4374(4) 0.4002(2) 0.0992(2) 0.0208(7) Uani 1 1 d . . . H4A H 0.4946 0.4630 0.1166 0.031 Uiso 1 1 calc R . . H4B H 0.3313 0.4155 0.0644 0.031 Uiso 1 1 calc R . . H4C H 0.4915 0.3602 0.0562 0.031 Uiso 1 1 calc R . . C5 C 0.6764(3) 0.4283(2) 0.3357(2) 0.0122(6) Uani 1 1 d . . . H5A H 0.6493 0.4866 0.2912 0.015 Uiso 1 1 calc R . . H5B H 0.6189 0.4346 0.3910 0.015 Uiso 1 1 calc R . . C6 C 0.8525(3) 0.4277(2) 0.3760(2) 0.0116(6) Uani 1 1 d . . . H6A H 0.8737 0.3930 0.4406 0.014 Uiso 1 1 calc R . . H6B H 0.8910 0.4975 0.3860 0.014 Uiso 1 1 calc R . . C7 C 1.0303(3) 0.4611(2) 0.2180(2) 0.0116(6) Uani 1 1 d . . . H7A H 1.0907 0.5100 0.2640 0.014 Uiso 1 1 calc R . . H7B H 1.1023 0.4306 0.1785 0.014 Uiso 1 1 calc R . . C8 C 0.8996(4) 0.5165(2) 0.1487(2) 0.0168(6) Uani 1 1 d . . . H8A H 0.8339 0.4678 0.1067 0.025 Uiso 1 1 calc R . . H8B H 0.9457 0.5633 0.1072 0.025 Uiso 1 1 calc R . . H8C H 0.8357 0.5540 0.1878 0.025 Uiso 1 1 calc R . . C9 C 1.1247(3) 0.3057(2) 0.3679(2) 0.0102(5) Uani 1 1 d . . . H9A H 1.0870 0.2552 0.4107 0.012 Uiso 1 1 calc R . . H9B H 1.1870 0.2699 0.3255 0.012 Uiso 1 1 calc R . . C10 C 1.2312(3) 0.3800(2) 0.4333(2) 0.0138(6) Uani 1 1 d . . . H10A H 1.2826 0.4237 0.3919 0.021 Uiso 1 1 calc R . . H10B H 1.3105 0.3429 0.4793 0.021 Uiso 1 1 calc R . . H10C H 1.1687 0.4208 0.4706 0.021 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 0.0057(2) 0.0082(2) 0.0066(3) -0.00163(17) 0.00098(19) -0.00024(17) Br1 0.01042(17) 0.01258(17) 0.01376(19) -0.00394(10) -0.00163(13) -0.00252(10) Br2 0.00878(17) 0.01389(17) 0.00855(17) -0.00375(10) 0.00258(12) 0.00122(9) P1 0.0064(3) 0.0116(3) 0.0083(3) 0.0003(3) 0.0019(3) 0.0009(2) P2 0.0067(3) 0.0079(3) 0.0068(4) -0.0013(2) 0.0014(3) 0.0000(2) C1 0.0106(14) 0.0202(14) 0.0136(15) 0.0036(11) 0.0064(12) -0.0013(11) C2 0.0160(15) 0.0188(14) 0.0100(14) 0.0033(11) 0.0013(12) 0.0002(11) C3 0.0077(13) 0.0236(15) 0.0131(15) 0.0005(12) 0.0023(12) 0.0036(11) C4 0.0193(15) 0.0263(17) 0.0156(16) 0.0053(13) 0.0003(13) 0.0092(13) C5 0.0104(13) 0.0136(13) 0.0139(15) -0.0012(11) 0.0054(12) 0.0028(10) C6 0.0158(14) 0.0105(13) 0.0091(14) -0.0015(10) 0.0037(11) 0.0013(10) C7 0.0131(14) 0.0087(12) 0.0134(14) 0.0007(11) 0.0032(12) -0.0022(10) C8 0.0185(15) 0.0142(14) 0.0165(15) 0.0042(12) 0.0003(12) -0.0014(12) C9 0.0082(13) 0.0111(13) 0.0111(14) -0.0006(10) 0.0015(11) 0.0016(10) C10 0.0119(14) 0.0188(14) 0.0101(14) -0.0038(11) 0.0004(12) -0.0007(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 2.1407(8) . ? Ni1 P2 2.1512(8) . ? Ni1 Br1 2.3442(5) . ? Ni1 Br2 2.3533(5) . ? P1 C3 1.824(3) . ? P1 C1 1.827(3) . ? P1 C5 1.833(3) . ? P2 C7 1.820(3) . ? P2 C9 1.826(3) . ? P2 C6 1.838(3) . ? C1 C2 1.518(4) . ? C3 C4 1.527(4) . ? C5 C6 1.531(4) . ? C7 C8 1.533(4) . ? C9 C10 1.530(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Ni1 P2 87.52(3) . . ? P1 Ni1 Br1 87.91(2) . . ? P2 Ni1 Br1 173.86(3) . . ? P1 Ni1 Br2 175.98(3) . . ? P2 Ni1 Br2 88.47(2) . . ? Br1 Ni1 Br2 96.104(18) . . ? C3 P1 C1 103.80(14) . . ? C3 P1 C5 103.78(13) . . ? C1 P1 C5 107.45(14) . . ? C3 P1 Ni1 119.75(10) . . ? C1 P1 Ni1 110.56(10) . . ? C5 P1 Ni1 110.64(9) . . ? C7 P2 C9 106.99(13) . . ? C7 P2 C6 106.35(13) . . ? C9 P2 C6 104.21(13) . . ? C7 P2 Ni1 112.93(10) . . ? C9 P2 Ni1 114.55(9) . . ? C6 P2 Ni1 111.13(10) . . ? C2 C1 P1 113.2(2) . . ? C4 C3 P1 114.2(2) . . ? C6 C5 P1 109.79(19) . . ? C5 C6 P2 110.14(19) . . ? C8 C7 P2 112.5(2) . . ? C10 C9 P2 114.41(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.600 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.123