#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:03:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178735 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/46/4084633.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_4084633
loop_
_publ_author_name
'Vabre, Boris'
'Deschamps, Félix'
'Zargarian, Davit'
_publ_section_title
;
 Ortho Derivatization of Phenols through C--H Nickelation: Synthesis,
 Characterization, and Reactivities of Ortho-Nickelated Phosphinite
 Complexes
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6623
_journal_paper_doi               10.1021/om500938u
_journal_volume                  33
_journal_year                    2014
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C24 H38 Br2 Ni O2 P2'
_chemical_formula_sum            'C24 H38 Br2 Ni O2 P2'
_chemical_formula_weight         639.01
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.64(4)
_cell_angle_beta                 93.043(4)
_cell_angle_gamma                114.612(3)
_cell_formula_units_Z            1
_cell_length_a                   8.2865(8)
_cell_length_b                   8.7999(8)
_cell_length_c                   10.9270(10)
_cell_measurement_reflns_used    27392
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.31
_cell_measurement_theta_min      4.41
_cell_volume                     664.7(3)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0163
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35089
_diffrn_reflns_theta_full        69.65
_diffrn_reflns_theta_max         69.65
_diffrn_reflns_theta_min         4.41
_exptl_absorpt_coefficient_mu    5.854
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0282
_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/[σ²(Fo²)+(0.0558P)²+0.3498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                2452
_reflns_number_total             2481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om500938u_si_002.cif
_cod_data_source_block           bors90
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4084629--4084634.cif.
;
_cod_original_cell_volume        664.70(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4084633
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.30862(3) 0.69848(2) 0.371574(18) 0.02775(10) Uani 1 1 d .
C1 C 0.3499(2) 1.2258(2) 0.83869(18) 0.0214(4) Uani 1 1 d .
C2 C 0.2843(3) 1.2684(3) 0.74261(19) 0.0261(4) Uani 1 1 d .
H2 H 0.3000 1.2260 0.6541 0.031 Uiso 1 1 calc R
C3 C 0.1947(3) 1.3748(3) 0.7778(2) 0.0298(4) Uani 1 1 d .
H3 H 0.1479 1.4040 0.7125 0.036 Uiso 1 1 calc R
C4 C 0.1732(3) 1.4384(3) 0.9069(2) 0.0307(4) Uani 1 1 d .
H4 H 0.1124 1.5113 0.9301 0.037 Uiso 1 1 calc R
C5 C 0.2403(3) 1.3957(3) 1.0018(2) 0.0302(4) Uani 1 1 d .
H5 H 0.2260 1.4397 1.0906 0.036 Uiso 1 1 calc R
C6 C 0.3287(3) 1.2885(3) 0.96830(19) 0.0254(4) Uani 1 1 d .
H6 H 0.3743 1.2585 1.0336 0.031 Uiso 1 1 calc R
C7 C 0.5530(3) 0.8783(3) 0.7539(2) 0.0264(4) Uani 1 1 d .
H7 H 0.5060 0.8562 0.8319 0.032 Uiso 1 1 calc R
C8 C 0.5437(3) 0.7005(3) 0.6581(2) 0.0349(5) Uani 1 1 d .
H8A H 0.5937 0.7188 0.5820 0.052 Uiso 1 1 calc R
H8B H 0.4165 0.6058 0.6263 0.052 Uiso 1 1 calc R
H8C H 0.6148 0.6628 0.7047 0.052 Uiso 1 1 calc R
C9 C 0.7500(3) 1.0288(3) 0.8069(2) 0.0379(5) Uani 1 1 d .
H9A H 0.8219 0.9909 0.8525 0.057 Uiso 1 1 calc R
H9B H 0.7529 1.1403 0.8698 0.057 Uiso 1 1 calc R
H9C H 0.8015 1.0518 0.7325 0.057 Uiso 1 1 calc R
C10 C 0.1726(3) 0.7847(3) 0.6616(2) 0.0255(4) Uani 1 1 d .
H10 H 0.1606 0.6621 0.6073 0.031 Uiso 1 1 calc R
C11 C 0.1293(3) 0.7810(3) 0.7956(2) 0.0339(5) Uani 1 1 d .
H11A H 0.1274 0.8946 0.8488 0.051 Uiso 1 1 calc R
H11B H 0.2229 0.7683 0.8438 0.051 Uiso 1 1 calc R
H11C H 0.0099 0.6779 0.7798 0.051 Uiso 1 1 calc R
C12 C 0.0306(3) 0.8082(3) 0.5857(2) 0.0345(5) Uani 1 1 d .
H12A H -0.0877 0.7000 0.5603 0.052 Uiso 1 1 calc R
H12B H 0.0675 0.8242 0.5053 0.052 Uiso 1 1 calc R
H12C H 0.0208 0.9155 0.6428 0.052 Uiso 1 1 calc R
Ni1 Ni 0.5000 1.0000 0.5000 0.01872(13) Uani 1 2 d S
O1 O 0.44569(18) 1.12549(18) 0.81545(13) 0.0229(3) Uani 1 1 d .
P1 P 0.40958(6) 0.95216(6) 0.67946(4) 0.01906(13) Uani 1 1 d .
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'
O O 0.0492 0.0322 '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'
Ni Ni -3.0029 0.5091 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.92(17) y
C2 C1 O1 . . 123.59(17) y
C6 C1 O1 . . 115.45(16) y
C1 C2 C3 . . 118.84(18) y
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 120.72(19) y
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C5 C4 C3 . . 119.77(19) y
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.34(19) y
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 119.40(18) y
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C9 C7 C8 . . 110.95(18) y
C9 C7 P1 . . 110.67(14) y
C8 C7 P1 . . 112.91(14) y
C9 C7 H7 . . 107.3 ?
C8 C7 H7 . . 107.3 ?
P1 C7 H7 . . 107.3 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C12 C10 C11 . . 110.48(17) y
C12 C10 P1 . . 113.39(15) y
C11 C10 P1 . . 112.61(14) y
C12 C10 H10 . . 106.6 ?
C11 C10 H10 . . 106.6 ?
P1 C10 H10 . . 106.6 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
P1 NI1 P1 . 2_676 180.0 y
P1 NI1 BR1 . . 88.811(14) y
P1 NI1 BR1 2_676 . 91.189(14) y
P1 NI1 BR1 . 2_676 91.189(14) y
P1 NI1 BR1 2_676 2_676 88.811(14) y
BR1 NI1 BR1 . 2_676 180.0 y
C1 O1 P1 . . 127.06(12) y
O1 P1 C7 . . 95.73(8) y
O1 P1 C10 . . 103.39(8) y
C7 P1 C10 . . 105.00(9) y
O1 P1 NI1 . . 119.55(5) y
C7 P1 NI1 . . 110.32(6) y
C10 P1 NI1 . . 119.51(7) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 Ni1 . 2.2979(3) y
C1 C2 . 1.383(3) y
C1 C6 . 1.387(3) y
C1 O1 . 1.389(2) y
C2 C3 . 1.394(3) y
C2 H2 . 0.9500 ?
C3 C4 . 1.383(3) y
C3 H3 . 0.9500 ?
C4 C5 . 1.379(3) y
C4 H4 . 0.9500 ?
C5 C6 . 1.390(3) y
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C9 . 1.529(3) y
C7 C8 . 1.529(3) y
C7 P1 . 1.8420(19) y
C7 H7 . 1.0000 ?
C8 H8a . 0.9800 ?
C8 H8b . 0.9800 ?
C8 H8c . 0.9800 ?
C9 H9a . 0.9800 ?
C9 H9b . 0.9800 ?
C9 H9c . 0.9800 ?
C10 C12 . 1.526(3) y
C10 C11 . 1.534(3) y
C10 P1 . 1.850(2) y
C10 H10 . 1.0000 ?
C11 H11a . 0.9800 ?
C11 H11b . 0.9800 ?
C11 H11c . 0.9800 ?
C12 H12a . 0.9800 ?
C12 H12b . 0.9800 ?
C12 H12c . 0.9800 ?
Ni1 P1 . 2.2433(5) y
Ni1 P1 2_676 2.2433(5) y
Ni1 Br1 2_676 2.2979(3) y
O1 P1 . 1.6349(13) y
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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . -0.5(3) y
O1 C1 C2 C3 . -178.03(18) y
C1 C2 C3 C4 . 0.7(3) y
C2 C3 C4 C5 . -0.3(3) y
C3 C4 C5 C6 . -0.2(3) y
C2 C1 C6 C5 . 0.0(3) y
O1 C1 C6 C5 . 177.71(17) y
C4 C5 C6 C1 . 0.4(3) y
C2 C1 O1 P1 . -37.3(3) y
C6 C1 O1 P1 . 145.03(14) y
C1 O1 P1 C7 . -166.69(15) y
C1 O1 P1 C10 . -59.76(16) y
C1 O1 P1 NI1 . 76.04(15) y
C9 C7 P1 O1 . -60.09(15) y
C8 C7 P1 O1 . 174.86(15) y
C9 C7 P1 C10 . -165.63(15) y
C8 C7 P1 C10 . 69.32(16) y
C9 C7 P1 NI1 . 64.36(15) y
C8 C7 P1 NI1 . -60.69(16) y
C12 C10 P1 O1 . 87.16(15) y
C11 C10 P1 O1 . -39.22(16) y
C12 C10 P1 C7 . -173.04(14) y
C11 C10 P1 C7 . 60.58(16) y
C12 C10 P1 NI1 . -48.66(16) y
C11 C10 P1 NI1 . -175.04(12) y
P1 NI1 P1 O1 2_676 -39(27) y
BR1 NI1 P1 O1 . -162.44(6) y
BR1 NI1 P1 O1 2_676 17.56(6) y
P1 NI1 P1 C7 2_676 -148(27) y
BR1 NI1 P1 C7 . 88.15(7) y
BR1 NI1 P1 C7 2_676 -91.85(7) y
P1 NI1 P1 C10 2_676 90(27) y
BR1 NI1 P1 C10 . -33.63(7) y
BR1 NI1 P1 C10 2_676 146.37(7) y
