#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:57:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178731 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/42/4084297.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_4084297
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         'C37 H44 N1 Ni1 P2 Si1'
_chemical_formula_sum            'C37 H51 N Ni P2 Si'
_chemical_formula_weight         658.53
_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                90.00
_cell_angle_beta                 92.4110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3790(2)
_cell_length_b                   13.7140(3)
_cell_length_c                   24.6930(7)
_cell_measurement_reflns_used    56934
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     3511.63(14)
_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-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21017
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_correction_T_min  0.8163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.653
_refine_diff_density_min         -1.140
_refine_diff_density_rms         0.258
_refine_ls_extinction_coef       0.0173(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0764P)²+1.8182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                4995
_reflns_number_total             6186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5006353_si_002.cif
_cod_data_source_block           3370
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4084297
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 0.15740(4) 0.21422(3) 0.411966(16) 0.01587(16) Uani 1 1 d .
P1 P -0.03908(7) 0.26563(6) 0.41211(3) 0.0166(2) Uani 1 1 d .
P2 P 0.30350(8) 0.10499(7) 0.38983(3) 0.0200(2) Uani 1 1 d .
Si2 Si 0.18622(8) 0.21521(7) 0.53734(4) 0.0205(2) Uani 1 1 d .
N1 N 0.1805(2) 0.3232(2) 0.36220(10) 0.0166(6) Uani 1 1 d .
C1 C 0.2761(3) 0.3293(2) 0.32207(12) 0.0175(7) Uani 1 1 d .
C2 C 0.3971(3) 0.3703(2) 0.33542(13) 0.0205(7) Uani 1 1 d .
C3 C 0.4297(3) 0.4096(3) 0.39201(13) 0.0230(8) Uani 1 1 d .
H3 H 0.3486 0.4194 0.4085 0.028 Uiso 1 1 d R
C4 C 0.5092(4) 0.3363(3) 0.42571(15) 0.0333(9) Uani 1 1 d .
H4A H 0.5278 0.3625 0.4612 0.040 Uiso 1 1 d R
H4B H 0.5884 0.3240 0.4082 0.040 Uiso 1 1 d R
H4C H 0.4622 0.2764 0.4287 0.040 Uiso 1 1 d R
C5 C 0.4974(3) 0.5088(3) 0.39221(15) 0.0296(8) Uani 1 1 d .
H5A H 0.5143 0.5300 0.4288 0.036 Uiso 1 1 d R
H5B H 0.4437 0.5557 0.3733 0.036 Uiso 1 1 d R
H5C H 0.5774 0.5024 0.3743 0.036 Uiso 1 1 d R
C6 C 0.4879(3) 0.3751(3) 0.29497(14) 0.0256(8) Uani 1 1 d .
H6 H 0.5710 0.4036 0.3032 0.031 Uiso 1 1 d R
C7 C 0.4585(3) 0.3408(3) 0.24306(15) 0.0297(9) Uani 1 1 d .
H7 H 0.5230 0.3433 0.2164 0.036 Uiso 1 1 d R
C8 C 0.3380(3) 0.3019(3) 0.23001(14) 0.0254(8) Uani 1 1 d .
H8 H 0.3184 0.2786 0.1939 0.030 Uiso 1 1 d R
C9 C 0.2449(3) 0.2956(3) 0.26875(13) 0.0221(8) Uani 1 1 d .
C10 C 0.1128(3) 0.2537(3) 0.25378(14) 0.0259(8) Uani 1 1 d .
H10 H 0.0660 0.2537 0.2866 0.031 Uiso 1 1 d R
C11 C 0.1184(4) 0.1497(3) 0.23286(17) 0.0400(10) Uani 1 1 d .
H11A H 0.0328 0.1261 0.2246 0.048 Uiso 1 1 d R
H11B H 0.1599 0.1084 0.2598 0.048 Uiso 1 1 d R
H11C H 0.1669 0.1494 0.2007 0.048 Uiso 1 1 d R
C12 C 0.0386(4) 0.3179(3) 0.21238(16) 0.0360(9) Uani 1 1 d .
H12A H -0.0447 0.2904 0.2036 0.043 Uiso 1 1 d R
H12B H 0.0869 0.3219 0.1801 0.043 Uiso 1 1 d R
H12C H 0.0284 0.3820 0.2271 0.043 Uiso 1 1 d R
C13 C 0.0883(3) 0.3958(2) 0.35662(12) 0.0154(7) Uani 1 1 d .
C14 C 0.1045(3) 0.4834(3) 0.32703(13) 0.0208(7) Uani 1 1 d .
H14 H 0.1827 0.4932 0.3083 0.025 Uiso 1 1 d R
C15 C 0.0084(3) 0.5534(2) 0.32464(13) 0.0211(7) Uani 1 1 d .
H15 H 0.0213 0.6132 0.3053 0.025 Uiso 1 1 d R
C16 C -0.1083(3) 0.5403(3) 0.34988(14) 0.0236(8) Uani 1 1 d .
H16 H -0.1750 0.5888 0.3479 0.028 Uiso 1 1 d R
C17 C -0.1268(3) 0.4548(3) 0.37848(13) 0.0202(7) Uani 1 1 d .
H17 H -0.2061 0.4445 0.3963 0.024 Uiso 1 1 d R
C18 C -0.0305(3) 0.3833(2) 0.38178(12) 0.0173(7) Uani 1 1 d .
C19 C -0.1305(3) 0.1869(3) 0.36401(13) 0.0188(7) Uani 1 1 d .
C20 C -0.2042(3) 0.2264(3) 0.32073(14) 0.0226(8) Uani 1 1 d .
H20 H -0.2109 0.2958 0.3168 0.027 Uiso 1 1 d R
C21 C -0.2669(3) 0.1653(3) 0.28362(14) 0.0277(8) Uani 1 1 d .
H21 H -0.3157 0.1938 0.2538 0.033 Uiso 1 1 d R
C22 C -0.2599(3) 0.0655(3) 0.28907(14) 0.0274(8) Uani 1 1 d .
H22 H -0.3046 0.0244 0.2630 0.033 Uiso 1 1 d R
C23 C -0.1882(3) 0.0259(3) 0.33223(14) 0.0260(8) Uani 1 1 d .
H23 H -0.1844 -0.0435 0.3370 0.031 Uiso 1 1 d R
C24 C -0.1227(3) 0.0858(3) 0.36891(14) 0.0234(8) Uani 1 1 d .
H24 H -0.0707 0.0577 0.3980 0.028 Uiso 1 1 d R
C25 C -0.1421(3) 0.2769(2) 0.46980(13) 0.0183(7) Uani 1 1 d .
C26 C -0.2186(3) 0.1989(3) 0.48597(14) 0.0214(7) Uani 1 1 d .
H26 H -0.2203 0.1397 0.4653 0.026 Uiso 1 1 d R
C27 C -0.2918(3) 0.2073(3) 0.53161(14) 0.0250(8) Uani 1 1 d .
H27 H -0.3435 0.1531 0.5423 0.030 Uiso 1 1 d R
C28 C -0.2902(3) 0.2922(3) 0.56143(14) 0.0269(8) Uani 1 1 d .
H28 H -0.3401 0.2980 0.5931 0.032 Uiso 1 1 d R
C29 C -0.2156(3) 0.3706(3) 0.54607(14) 0.0268(8) Uani 1 1 d .
H29 H -0.2160 0.4304 0.5664 0.032 Uiso 1 1 d R
C30 C -0.1410(3) 0.3627(3) 0.50047(13) 0.0223(7) Uani 1 1 d .
H30 H -0.0878 0.4163 0.4902 0.027 Uiso 1 1 d R
C31 C 0.1294(3) 0.1375(3) 0.47834(13) 0.0212(7) Uani 1 1 d .
H31A H 0.0394 0.1222 0.4801 0.025 Uiso 1 1 d R
H31B H 0.1784 0.0783 0.4770 0.025 Uiso 1 1 d R
C32 C 0.2112(3) 0.3464(3) 0.51908(14) 0.0277(8) Uani 1 1 d .
H32A H 0.2397 0.3820 0.5509 0.033 Uiso 1 1 d R
H32B H 0.1316 0.3735 0.5049 0.033 Uiso 1 1 d R
H32C H 0.2752 0.3508 0.4923 0.033 Uiso 1 1 d R
C33 C 0.0674(3) 0.2064(3) 0.59241(14) 0.0255(8) Uani 1 1 d .
H33A H 0.0959 0.2464 0.6225 0.031 Uiso 1 1 d R
H33B H 0.0611 0.1399 0.6041 0.031 Uiso 1 1 d R
H33C H -0.0156 0.2285 0.5788 0.031 Uiso 1 1 d R
C34 C 0.3453(3) 0.1721(3) 0.56732(15) 0.0350(9) Uani 1 1 d .
H34A H 0.3717 0.2133 0.5972 0.042 Uiso 1 1 d R
H34B H 0.4090 0.1744 0.5403 0.042 Uiso 1 1 d R
H34C H 0.3365 0.1063 0.5799 0.042 Uiso 1 1 d R
C35 C 0.2155(3) -0.0059(3) 0.37076(15) 0.0272(8) Uani 1 1 d .
H35A H 0.2755 -0.0554 0.3609 0.033 Uiso 1 1 d R
H35B H 0.1568 0.0075 0.3407 0.033 Uiso 1 1 d R
H35C H 0.1681 -0.0281 0.4010 0.033 Uiso 1 1 d R
C36 C 0.4203(3) 0.0592(3) 0.44122(14) 0.0266(8) Uani 1 1 d .
H36A H 0.4765 0.0128 0.4251 0.032 Uiso 1 1 d R
H36B H 0.3753 0.0283 0.4697 0.032 Uiso 1 1 d R
H36C H 0.4704 0.1126 0.4559 0.032 Uiso 1 1 d R
C37 C 0.4115(3) 0.1165(3) 0.33386(15) 0.0294(9) Uani 1 1 d .
H37A H 0.4654 0.0598 0.3326 0.035 Uiso 1 1 d R
H37B H 0.4644 0.1734 0.3396 0.035 Uiso 1 1 d R
H37C H 0.3624 0.1229 0.3003 0.035 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'
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'
Si Si 0.0817 0.0704 '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
N1 Ni1 C31 162.28(13)
N1 Ni1 P1 83.81(8)
C31 Ni1 P1 90.04(10)
N1 Ni1 P2 104.97(8)
C31 Ni1 P2 88.31(10)
P1 Ni1 P2 151.36(4)
C18 P1 C25 107.01(15)
C18 P1 C19 107.08(15)
C25 P1 C19 104.53(14)
C18 P1 Ni1 103.37(10)
C25 P1 Ni1 127.90(10)
C19 P1 Ni1 105.61(10)
C37 P2 C35 101.16(17)
C37 P2 C36 98.32(16)
C35 P2 C36 101.69(17)
C37 P2 Ni1 125.29(12)
C35 P2 Ni1 106.66(11)
C36 P2 Ni1 120.10(12)
C32 Si2 C33 109.71(16)
C32 Si2 C34 105.62(18)
C33 Si2 C34 106.73(16)
C32 Si2 C31 113.56(16)
C33 Si2 C31 109.30(16)
C34 Si2 C31 111.65(17)
C13 N1 C1 112.7(3)
C13 N1 Ni1 120.6(2)
C1 N1 Ni1 125.8(2)
C2 C1 C9 121.0(3)
C2 C1 N1 120.0(3)
C9 C1 N1 119.0(3)
C1 C2 C6 118.2(3)
C1 C2 C3 121.3(3)
C6 C2 C3 120.4(3)
C2 C3 C4 111.2(3)
C2 C3 C5 113.7(3)
C4 C3 C5 110.3(3)
C7 C6 C2 120.9(3)
C8 C7 C6 120.5(3)
C7 C8 C9 120.7(3)
C8 C9 C1 118.7(3)
C8 C9 C10 120.2(3)
C1 C9 C10 121.2(3)
C9 C10 C11 113.0(3)
C9 C10 C12 111.6(3)
C11 C10 C12 109.8(3)
N1 C13 C18 118.8(3)
N1 C13 C14 124.3(3)
C18 C13 C14 116.9(3)
C15 C14 C13 120.5(3)
C14 C15 C16 121.9(3)
C17 C16 C15 118.5(3)
C16 C17 C18 120.6(3)
C17 C18 C13 121.6(3)
C17 C18 P1 127.6(2)
C13 C18 P1 110.7(2)
C24 C19 C20 118.7(3)
C24 C19 P1 120.1(3)
C20 C19 P1 121.1(3)
C21 C20 C19 119.9(3)
C22 C21 C20 121.0(3)
C21 C22 C23 119.3(3)
C24 C23 C22 120.3(3)
C23 C24 C19 120.7(3)
C30 C25 C26 118.7(3)
C30 C25 P1 120.2(2)
C26 C25 P1 121.1(3)
C27 C26 C25 120.3(3)
C28 C27 C26 120.5(3)
C27 C28 C29 120.2(3)
C28 C29 C30 119.6(3)
C25 C30 C29 120.6(3)
Si2 C31 Ni1 106.73(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 N1 1.956(3)
Ni1 C31 1.980(3)
Ni1 P1 2.1578(9)
Ni1 P2 2.2162(9)
P1 C18 1.783(3)
P1 C25 1.823(3)
P1 C19 1.840(3)
P2 C37 1.823(3)
P2 C35 1.826(4)
P2 C36 1.829(3)
Si2 C32 1.875(4)
Si2 C33 1.878(3)
Si2 C34 1.876(4)
Si2 C31 1.880(3)
N1 C13 1.383(4)
N1 C1 1.434(4)
C1 C2 1.402(5)
C1 C9 1.420(5)
C2 C6 1.404(5)
C2 C3 1.523(5)
C3 C4 1.526(5)
C3 C5 1.530(5)
C6 C7 1.387(5)
C7 C8 1.384(5)
C8 C9 1.391(5)
C9 C10 1.518(5)
C10 C11 1.518(5)
C10 C12 1.532(5)
C13 C18 1.415(4)
C13 C14 1.420(5)
C14 C15 1.384(5)
C15 C16 1.397(5)
C16 C17 1.386(5)
C17 C18 1.399(4)
C19 C24 1.393(5)
C19 C20 1.397(5)
C20 C21 1.384(5)
C21 C22 1.377(5)
C22 C23 1.385(5)
C23 C24 1.381(5)
C25 C30 1.399(5)
C25 C26 1.400(5)
C26 C27 1.391(5)
C27 C28 1.377(5)
C28 C29 1.388(5)
C29 C30 1.397(5)
