#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/44/1514465.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1514465
loop_
_publ_author_name
'Bryan, Zachary J.'
'McNeil, Anne J.'
_publ_section_title
;
 Evidence for a preferential intramolecular oxidative addition in
 Ni-catalyzed cross-coupling reactions and their impact on chain-growth
 polymerizations
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1620
_journal_paper_doi               10.1039/c3sc00090g
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C10 H24 Br2 Ni P2'
_chemical_formula_sum            'C10 H24 Br2 Ni P2'
_chemical_formula_weight         424.76
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.665(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7070(2)
_cell_length_b                   13.3165(2)
_cell_length_c                   13.7802(10)
_cell_measurement_reflns_used    10405
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.30
_cell_volume                     1570.17(13)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r5'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r5'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn744+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15593
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.66
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.435
_exptl_absorpt_correction_T_max  0.354
_exptl_absorpt_correction_T_min  0.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       multi-faceted
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0297
_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/[σ²(Fo²)+(0.0166P)²+2.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                2805
_reflns_number_total             2854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc00090g.txt
_cod_data_source_block           zb229
_cod_original_cell_volume        1570.17(12)
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               1514465
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'
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
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)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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)
