#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:57:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178731 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/42/4084293.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_4084293
loop_
_publ_author_name
'Chen, Ming-Tsz'
'Lee, Wei-Ying'
'Tsai, Tzung-Ling'
'Liang, Lan-Chang'
_publ_section_title
;
 Nickel(II) Complexes Containing Bidentate Diarylamido Phosphine
 Chelates: Kumada Couplings Kinetically Preferred to β-Hydrogen
 Elimination
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5852
_journal_paper_doi               10.1021/om5006353
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C48 H70 Cl2 N2 Ni2 P2'
_chemical_formula_sum            'C48 H70 Cl2 N2 Ni2 P2'
_chemical_formula_weight         925.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(4)
_cell_angle_beta                 92.935(4)
_cell_angle_gamma                90.000(7)
_cell_formula_units_Z            2
_cell_length_a                   11.6246(10)
_cell_length_b                   13.8692(12)
_cell_length_c                   16.3569(18)
_cell_measurement_reflns_used    116156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.037
_cell_volume                     2633.7(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_av_sigmaI/netI    0.1334
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_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            26626
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  1.0139
_exptl_absorpt_correction_T_min  0.8755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            brown-red
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Paralleliped
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_platon_squeeze_details
;
;
_refine_diff_density_max         0.970
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.252
_refine_ls_extinction_coef       0.075(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.2001
_refine_ls_R_factor_gt           0.1290
_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)+(0.1940P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3135
_refine_ls_wR_factor_ref         0.25
_reflns_number_gt                2585
_reflns_number_total             4741
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5006353_si_002.cif
_cod_data_source_block           4766
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4084293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.03184(9) 0.05949(9) 0.41751(7) 0.0442(6) Uani 1 1 d .
Cl1 Cl 0.1164(2) -0.0485(2) 0.49794(16) 0.0627(8) Uani 1 1 d .
P1 P 0.1729(2) 0.06259(19) 0.33952(14) 0.0461(7) Uani 1 1 d .
N1 N -0.0390(6) 0.1490(6) 0.3449(4) 0.0437(19) Uani 1 1 d .
C1 C 0.3098(8) 0.1136(8) 0.3814(6) 0.057(3) Uani 1 1 d .
H1 H 0.3547 0.1301 0.3358 0.069 Uiso 1 1 d R
C2 C 0.3844(9) 0.0432(9) 0.4333(7) 0.068(3) Uani 1 1 d .
H2A H 0.4538 0.0751 0.4528 0.102 Uiso 1 1 calc R
H2B H 0.4036 -0.0113 0.4006 0.102 Uiso 1 1 calc R
H2C H 0.3426 0.0219 0.4791 0.102 Uiso 1 1 calc R
C3 C 0.2871(10) 0.2036(10) 0.4295(8) 0.080(4) Uani 1 1 d .
H3A H 0.3581 0.2310 0.4512 0.097 Uiso 1 1 d R
H3B H 0.2393 0.1875 0.4737 0.097 Uiso 1 1 d R
H3C H 0.2479 0.2495 0.3940 0.097 Uiso 1 1 d R
C4 C 0.2021(8) -0.0569(7) 0.2974(6) 0.055(3) Uani 1 1 d .
H4 H 0.2290 -0.0965 0.3426 0.066 Uiso 1 1 d R
C5 C 0.2930(11) -0.0545(9) 0.2331(7) 0.077(4) Uani 1 1 d .
H5A H 0.3051 -0.1185 0.2131 0.116 Uiso 1 1 calc R
H5B H 0.3639 -0.0297 0.2574 0.116 Uiso 1 1 calc R
H5C H 0.2670 -0.0136 0.1886 0.116 Uiso 1 1 calc R
C6 C 0.0904(10) -0.1026(9) 0.2646(7) 0.074(3) Uani 1 1 d .
H6A H 0.1064 -0.1653 0.2431 0.088 Uiso 1 1 d R
H6B H 0.0576 -0.0625 0.2216 0.088 Uiso 1 1 d R
H6C H 0.0370 -0.1085 0.3072 0.088 Uiso 1 1 d R
C7 C 0.1210(7) 0.1433(6) 0.2617(5) 0.042(2) Uani 1 1 d .
C8 C 0.1797(8) 0.1762(8) 0.1895(6) 0.055(3) Uani 1 1 d .
H8 H 0.2564 0.1530 0.1828 0.065 Uiso 1 1 d R
C9 C 0.1289(9) 0.2378(8) 0.1358(6) 0.055(3) Uani 1 1 d .
H9 H 0.1671 0.2584 0.0882 0.066 Uiso 1 1 d R
C10 C 0.0169(9) 0.2707(8) 0.1506(6) 0.056(3) Uani 1 1 d .
H10 H -0.0166 0.3146 0.1108 0.067 Uiso 1 1 d R
C11 C -0.0386(8) 0.2457(8) 0.2184(6) 0.056(3) Uani 1 1 d .
H11 H -0.1143 0.2712 0.2252 0.067 Uiso 1 1 d R
C12 C 0.0100(8) 0.1802(7) 0.2758(5) 0.042(2) Uani 1 1 d .
C13 C -0.1487(8) 0.1857(8) 0.3587(6) 0.052(3) Uani 1 1 d .
C14 C -0.1592(8) 0.2638(8) 0.4169(5) 0.049(2) Uani 1 1 d .
C15 C -0.0538(9) 0.3017(8) 0.4636(6) 0.059(3) Uani 1 1 d .
H15 H 0.0011 0.2501 0.4628 0.071 Uiso 1 1 d R
C16 C -0.0759(12) 0.3249(11) 0.5545(7) 0.090(4) Uani 1 1 d .
H16A H -0.0055 0.3473 0.5813 0.108 Uiso 1 1 d R
H16B H -0.1027 0.2690 0.5824 0.108 Uiso 1 1 d R
H16C H -0.1330 0.3749 0.5555 0.108 Uiso 1 1 d R
C17 C -0.0017(12) 0.3894(11) 0.4212(8) 0.089(4) Uani 1 1 d .
H17A H 0.0654 0.4107 0.4528 0.107 Uiso 1 1 d R
H17B H -0.0577 0.4403 0.4179 0.107 Uiso 1 1 d R
H17C H 0.0193 0.3724 0.3671 0.107 Uiso 1 1 d R
C18 C -0.2718(12) 0.2972(9) 0.4271(7) 0.077(4) Uani 1 1 d .
H18 H -0.2823 0.3498 0.4642 0.092 Uiso 1 1 d R
C19 C -0.3662(9) 0.2610(11) 0.3852(8) 0.073(4) Uani 1 1 d .
H19 H -0.4418 0.2867 0.3919 0.088 Uiso 1 1 d R
C20 C -0.3503(10) 0.1880(11) 0.3327(8) 0.078(3) Uani 1 1 d .
H20 H -0.4177 0.1614 0.3047 0.093 Uiso 1 1 d R
C21 C -0.2462(8) 0.1465(8) 0.3194(7) 0.061(3) Uani 1 1 d .
C22 C -0.2379(11) 0.0641(10) 0.2614(7) 0.074(3) Uani 1 1 d .
H22 H -0.1568 0.0541 0.2563 0.089 Uiso 1 1 d R
C23 C -0.2962(15) 0.0838(15) 0.1763(9) 0.125(6) Uani 1 1 d .
H23A H -0.2884 0.0297 0.1403 0.150 Uiso 1 1 d R
H23B H -0.2596 0.1392 0.1539 0.150 Uiso 1 1 d R
H23C H -0.3765 0.0972 0.1819 0.150 Uiso 1 1 d R
C24 C -0.2814(16) -0.0292(13) 0.2946(10) 0.122(6) Uani 1 1 d .
H24A H -0.2728 -0.0798 0.2553 0.147 Uiso 1 1 d R
H24B H -0.3615 -0.0217 0.3048 0.147 Uiso 1 1 d R
H24C H -0.2393 -0.0455 0.3447 0.147 Uiso 1 1 d R
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
N1 Ni1 P1 86.2(2) .
N1 Ni1 Cl1 177.7(2) .
P1 Ni1 Cl1 92.18(10) .
N1 Ni1 Cl1 96.2(2) 3_556
P1 Ni1 Cl1 177.17(11) 3_556
Cl1 Ni1 Cl1 85.37(10) 3_556
Ni1 Cl1 Ni1 94.63(10) 3_556
C7 P1 C4 111.3(5) .
C7 P1 C1 106.2(4) .
C4 P1 C1 108.3(5) .
C7 P1 Ni1 101.4(3) .
C4 P1 Ni1 111.8(3) .
C1 P1 Ni1 117.6(3) .
C12 N1 C13 116.1(7) .
C12 N1 Ni1 123.1(6) .
C13 N1 Ni1 120.8(5) .
C3 C1 C2 110.3(9) .
C3 C1 P1 110.0(7) .
C2 C1 P1 114.5(8) .
C3 C1 H1 109.0 .
C2 C1 H1 105.5 .
P1 C1 H1 107.3 .
C1 C2 H2A 109.5 .
C1 C2 H2B 109.5 .
H2A C2 H2B 109.5 .
C1 C2 H2C 109.5 .
H2A C2 H2C 109.5 .
H2B C2 H2C 109.5 .
C1 C3 H3A 110.6 .
C1 C3 H3B 108.9 .
H3A C3 H3B 109.5 .
C1 C3 H3C 108.9 .
H3A C3 H3C 109.5 .
H3B C3 H3C 109.5 .
C6 C4 C5 112.1(9) .
C6 C4 P1 109.8(7) .
C5 C4 P1 112.8(8) .
C6 C4 H4 105.8 .
C5 C4 H4 109.4 .
P1 C4 H4 106.7 .
C4 C5 H5A 109.5 .
C4 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C4 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C4 C6 H6A 109.2 .
C4 C6 H6B 108.5 .
H6A C6 H6B 109.5 .
C4 C6 H6C 110.7 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
C12 C7 C8 118.9(8) .
C12 C7 P1 112.9(6) .
C8 C7 P1 128.2(7) .
C9 C8 C7 121.2(9) .
C9 C8 H8 121.3 .
C7 C8 H8 117.4 .
C8 C9 C10 118.2(8) .
C8 C9 H9 121.0 .
C10 C9 H9 120.8 .
C11 C10 C9 122.6(9) .
C11 C10 H10 121.5 .
C9 C10 H10 115.8 .
C10 C11 C12 121.3(9) .
C10 C11 H11 118.6 .
C12 C11 H11 120.0 .
N1 C12 C11 126.1(8) .
N1 C12 C7 116.3(8) .
C11 C12 C7 117.6(8) .
C21 C13 N1 120.8(10) .
C21 C13 C14 120.2(9) .
N1 C13 C14 119.0(9) .
C18 C14 C13 115.7(9) .
C18 C14 C15 124.3(10) .
C13 C14 C15 120.0(8) .
C14 C15 C17 112.1(9) .
C14 C15 C16 112.8(9) .
C17 C15 C16 110.8(10) .
C14 C15 H15 104.8 .
C17 C15 H15 107.8 .
C16 C15 H15 108.1 .
C15 C16 H16A 109.0 .
C15 C16 H16B 111.2 .
H16A C16 H16B 109.5 .
C15 C16 H16C 108.3 .
H16A C16 H16C 109.4 .
H16B C16 H16C 109.5 .
C15 C17 H17A 109.2 .
C15 C17 H17B 109.0 .
H17A C17 H17B 109.5 .
C15 C17 H17C 110.2 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.4 .
C19 C18 C14 123.5(11) .
C19 C18 H18 118.2 .
C14 C18 H18 118.3 .
C20 C19 C18 117.7(11) .
C20 C19 H19 120.6 .
C18 C19 H19 121.7 .
C19 C20 C21 124.7(12) .
C19 C20 H20 117.2 .
C21 C20 H20 118.0 .
C20 C21 C13 118.2(12) .
C20 C21 C22 120.7(11) .
C13 C21 C22 121.1(10) .
C21 C22 C24 113.3(11) .
C21 C22 C23 113.5(12) .
C24 C22 C23 109.8(12) .
C21 C22 H22 105.1 .
C24 C22 H22 105.0 .
C23 C22 H22 109.6 .
C22 C23 H23A 111.3 .
C22 C23 H23B 107.7 .
H23A C23 H23B 109.5 .
C22 C23 H23C 109.5 .
H23A C23 H23C 109.4 .
H23B C23 H23C 109.5 .
C22 C24 H24A 109.8 .
C22 C24 H24B 108.5 .
H24A C24 H24B 109.3 .
C22 C24 H24C 110.2 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.878(7) .
Ni1 P1 2.129(2) .
Ni1 Cl1 2.192(3) .
Ni1 Cl1 2.269(2) 3_556
Cl1 Ni1 2.269(2) 3_556
P1 C7 1.777(9) .
P1 C4 1.833(10) .
P1 C1 1.841(10) .
N1 C12 1.362(10) .
N1 C13 1.402(11) .
C1 C3 1.506(17) .
C1 C2 1.533(15) .
C1 H1 0.9597 .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 H3A 0.9601 .
C3 H3B 0.9604 .
C3 H3C 0.9607 .
C4 C6 1.517(15) .
C4 C5 1.527(14) .
C4 H4 0.9604 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 H6A 0.9599 .
C6 H6B 0.9601 .
C6 H6C 0.9601 .
C7 C12 1.419(12) .
C7 C8 1.466(12) .
C8 C9 1.341(14) .
C8 H8 0.9594 .
C9 C10 1.411(14) .
C9 H9 0.9596 .
C10 C11 1.356(13) .
C10 H10 0.9596 .
C11 C12 1.404(13) .
C11 H11 0.9601 .
C13 C21 1.385(14) .
C13 C14 1.451(14) .
C14 C18 1.406(15) .
C14 C15 1.505(14) .
C15 C17 1.540(17) .
C15 C16 1.555(14) .
C15 H15 0.9594 .
C16 H16A 0.9601 .
C16 H16B 0.9597 .
C16 H16C 0.9607 .
C17 H17A 0.9600 .
C17 H17B 0.9599 .
C17 H17C 0.9594 .
C18 C19 1.360(17) .
C18 H18 0.9609 .
C19 C20 1.347(17) .
C19 H19 0.9598 .
C20 C21 1.367(15) .
C20 H20 0.9606 .
C21 C22 1.493(16) .
C22 C24 1.50(2) .
C22 C23 1.541(18) .
C22 H22 0.9606 .
C23 H23A 0.9609 .
C23 H23B 0.9602 .
C23 H23C 0.9606 .
C24 H24A 0.9604 .
C24 H24B 0.9600 .
C24 H24C 0.9597 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 123 34 ' '
2 0.121 0.195 0.621 20 9 ' '
3 0.500 0.500 0.500 123 34 ' '
4 0.379 0.695 0.879 20 9 ' '
5 0.621 0.305 0.121 20 9 ' '
6 0.879 0.805 0.379 20 9 ' '
