#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:57:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178731 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/42/4084294.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_4084294
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         'C36 H32 N2 Ni1 P2'
_chemical_formula_sum            'C65 H55 N2 Ni P2'
_chemical_formula_weight         984.76
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           70
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-F 2uv 2vw'
_symmetry_space_group_name_H-M   'F d d d :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   18.7260(3)
_cell_length_b                   21.5820(3)
_cell_length_c                   49.7350(8)
_cell_measurement_reflns_used    52453
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     20100.1(5)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            25822
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.8646
_exptl_absorpt_correction_T_min  0.8258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             8272
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.264
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       0.00090(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0936P)²+74.2306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1645
_reflns_number_gt                3706
_reflns_number_total             4439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5006353_si_002.cif
_cod_data_source_block           3309
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               4084294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'
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 0.3750 0.3750 0.185604(9) 0.0205(2) Uani 1 2 d S
P1 P 0.33144(4) 0.30814(4) 0.213412(14) 0.0227(2) Uani 1 1 d .
N1 N 0.38242(13) 0.30277(11) 0.16170(5) 0.0221(5) Uani 1 1 d .
C1 C 0.40228(17) 0.30570(13) 0.13383(6) 0.0228(6) Uani 1 1 d .
C2 C 0.35181(17) 0.29322(13) 0.11361(6) 0.0252(7) Uani 1 1 d .
C3 C 0.27618(18) 0.27662(15) 0.12023(6) 0.0329(8) Uani 1 1 d .
H3A H 0.2501 0.2703 0.1039 0.039 Uiso 1 1 d R
H3B H 0.2544 0.3095 0.1303 0.039 Uiso 1 1 d R
H3C H 0.2756 0.2392 0.1307 0.039 Uiso 1 1 d R
C4 C 0.37446(18) 0.29463(14) 0.08687(6) 0.0289(7) Uani 1 1 d .
H4 H 0.3410 0.2868 0.0727 0.035 Uiso 1 1 d R
C5 C 0.44487(19) 0.30707(14) 0.08027(6) 0.0319(7) Uani 1 1 d .
H5 H 0.4595 0.3079 0.0618 0.038 Uiso 1 1 d R
C6 C 0.49409(18) 0.31816(14) 0.10038(6) 0.0312(7) Uani 1 1 d .
H6 H 0.5430 0.3262 0.0958 0.037 Uiso 1 1 d R
C7 C 0.47355(17) 0.31799(14) 0.12740(6) 0.0263(7) Uani 1 1 d .
C8 C 0.52738(17) 0.32869(16) 0.14914(6) 0.0331(7) Uani 1 1 d .
H8A H 0.5735 0.3366 0.1414 0.040 Uiso 1 1 d R
H8B H 0.5298 0.2925 0.1603 0.040 Uiso 1 1 d R
H8C H 0.5130 0.3637 0.1598 0.040 Uiso 1 1 d R
C9 C 0.37739(15) 0.24370(14) 0.17176(6) 0.0244(7) Uani 1 1 d .
C10 C 0.39108(18) 0.18850(14) 0.15741(6) 0.0299(7) Uani 1 1 d .
H10 H 0.4015 0.1911 0.1385 0.036 Uiso 1 1 d R
C11 C 0.38860(19) 0.13153(15) 0.16982(7) 0.0340(8) Uani 1 1 d .
H11 H 0.4001 0.0955 0.1593 0.041 Uiso 1 1 d R
C12 C 0.37172(18) 0.12552(15) 0.19699(7) 0.0316(8) Uani 1 1 d .
H12 H 0.3706 0.0851 0.2051 0.038 Uiso 1 1 d R
C13 C 0.35569(17) 0.17840(15) 0.21143(6) 0.0285(7) Uani 1 1 d .
H13 H 0.3436 0.1753 0.2301 0.034 Uiso 1 1 d R
C14 C 0.35768(15) 0.23604(14) 0.19916(6) 0.0230(6) Uani 1 1 d .
C15 C 0.34575(17) 0.30066(14) 0.24936(6) 0.0249(7) Uani 1 1 d .
C16 C 0.41472(17) 0.28820(15) 0.25805(6) 0.0303(7) Uani 1 1 d .
H16 H 0.4521 0.2829 0.2450 0.036 Uiso 1 1 d R
C17 C 0.43084(19) 0.28330(16) 0.28505(6) 0.0333(7) Uani 1 1 d .
H17 H 0.4789 0.2746 0.2904 0.040 Uiso 1 1 d R
C18 C 0.3771(2) 0.29074(16) 0.30384(6) 0.0353(8) Uani 1 1 d .
H18 H 0.3881 0.2875 0.3226 0.042 Uiso 1 1 d R
C19 C 0.3082(2) 0.30283(15) 0.29563(6) 0.0376(8) Uani 1 1 d .
H19 H 0.2715 0.3083 0.3089 0.045 Uiso 1 1 d R
C20 C 0.29209(18) 0.30797(14) 0.26858(6) 0.0306(7) Uani 1 1 d .
H20 H 0.2442 0.3161 0.2626 0.037 Uiso 1 1 d R
C21 C 0.23498(16) 0.31437(14) 0.20830(6) 0.0257(7) Uani 1 1 d .
C22 C 0.19747(17) 0.36656(15) 0.21690(6) 0.0295(7) Uani 1 1 d .
H22 H 0.2222 0.3987 0.2266 0.035 Uiso 1 1 d R
C23 C 0.12516(17) 0.37298(16) 0.21149(7) 0.0320(8) Uani 1 1 d .
H23 H 0.0995 0.4084 0.2181 0.038 Uiso 1 1 d R
C24 C 0.08970(17) 0.32817(17) 0.19704(7) 0.0362(8) Uani 1 1 d .
H24 H 0.0398 0.3332 0.1932 0.043 Uiso 1 1 d R
C25 C 0.12652(19) 0.27639(18) 0.18801(8) 0.0405(9) Uani 1 1 d .
H25 H 0.1020 0.2457 0.1775 0.049 Uiso 1 1 d R
C26 C 0.19848(18) 0.26902(16) 0.19368(6) 0.0337(7) Uani 1 1 d .
H26 H 0.2230 0.2323 0.1879 0.040 Uiso 1 1 d R
C27 C 0.3077(2) 0.3497(2) 0.00211(9) 0.0594(11) Uani 1 1 d .
H27 H 0.2605 0.3323 0.0024 0.071 Uiso 1 1 d R
C28 C 0.3159(2) 0.4123(2) 0.00237(9) 0.0612(12) Uani 1 1 d .
H28 H 0.2749 0.4390 0.0019 0.073 Uiso 1 1 d R
C29 C 0.3673(2) 0.3119(2) 0.00238(9) 0.0592(12) Uani 1 1 d .
H29 H 0.3617 0.2677 0.0026 0.071 Uiso 1 1 d R
C30 C 0.5628(2) 0.0931(2) 0.12513(10) 0.0643(13) Uani 1 1 d .
H30 H 0.5183 0.0710 0.1255 0.077 Uiso 1 1 d R
C31 C 0.6250 0.0613(3) 0.1250 0.0410(12) Uani 1 2 d S
H31 H 0.6250 0.0168 0.1250 0.049 Uiso 1 2 d SR
C32 C 0.1250 0.1250 0.1084(5) 0.259(11) Uiso 1 2 d S
C33 C 0.1250 0.1250 0.0819(5) 0.211(8) Uiso 1 2 d S
C34 C 0.1936(6) 0.1244(4) 0.1030(2) 0.065(2) Uiso 0.50 1 d P
C35 C 0.1855(6) 0.1250 0.1250 0.097(3) Uiso 1 2 d S
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'
P P 0.1023 0.0942 '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'
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
N1 Ni1 N1 105.57(14) . 14
N1 Ni1 P1 153.00(7) . 14
N1 Ni1 P1 83.34(7) 14 14
N1 Ni1 P1 83.34(7) . .
N1 Ni1 P1 153.00(7) 14 .
P1 Ni1 P1 100.32(4) 14 .
C14 P1 C15 105.90(14) . .
C14 P1 C21 106.36(14) . .
C15 P1 C21 106.81(14) . .
C14 P1 Ni1 103.00(10) . .
C15 P1 Ni1 129.40(10) . .
C21 P1 Ni1 103.59(9) . .
C9 N1 C1 114.2(2) . .
C9 N1 Ni1 120.75(19) . .
C1 N1 Ni1 124.54(18) . .
C7 C1 C2 121.0(3) . .
C7 C1 N1 118.4(3) . .
C2 C1 N1 120.5(3) . .
C4 C2 C1 118.2(3) . .
C4 C2 C3 120.1(3) . .
C1 C2 C3 121.6(3) . .
C5 C4 C2 121.3(3) . .
C4 C5 C6 119.8(3) . .
C5 C6 C7 120.8(3) . .
C1 C7 C6 118.9(3) . .
C1 C7 C8 120.5(3) . .
C6 C7 C8 120.6(3) . .
N1 C9 C10 125.9(3) . .
N1 C9 C14 118.4(3) . .
C10 C9 C14 115.7(3) . .
C11 C10 C9 121.4(3) . .
C10 C11 C12 121.7(3) . .
C13 C12 C11 118.4(3) . .
C12 C13 C14 120.4(3) . .
C13 C14 C9 122.2(3) . .
C13 C14 P1 127.0(2) . .
C9 C14 P1 110.6(2) . .
C16 C15 C20 118.6(3) . .
C16 C15 P1 117.5(2) . .
C20 C15 P1 123.9(2) . .
C17 C16 C15 121.4(3) . .
C16 C17 C18 119.3(3) . .
C19 C18 C17 120.2(3) . .
C18 C19 C20 120.5(3) . .
C19 C20 C15 120.0(3) . .
C22 C21 C26 118.6(3) . .
C22 C21 P1 120.9(2) . .
C26 C21 P1 120.2(2) . .
C23 C22 C21 120.8(3) . .
C24 C23 C22 120.2(3) . .
C23 C24 C25 119.7(3) . .
C26 C25 C24 120.6(3) . .
C25 C26 C21 120.1(3) . .
C28 C27 C29 119.6(4) . .
C27 C28 C29 120.6(4) . 14
C28 C29 C27 119.7(4) 14 .
C31 C30 C30 120.5(3) . 3
C30 C31 C30 119.0(6) 4_655 .
C33 C32 C34 78.2(13) . .
C33 C32 C34 78.2(13) . 2
C34 C32 C34 156(3) . 2
C33 C32 C35 126.2(10) . .
C34 C32 C35 48.0(5) . .
C34 C32 C35 156(2) 2 .
C33 C32 C35 126.2(10) . 2
C34 C32 C35 156(2) . 2
C34 C32 C35 48.0(5) 2 2
C35 C32 C35 108(2) . 2
C33 C32 C32 179.997(1) . 3
C34 C32 C32 101.8(13) . 3
C34 C32 C32 101.8(13) 2 3
C35 C32 C32 53.8(10) . 3
C35 C32 C32 53.8(10) 2 3
C32 C33 C34 50.8(7) . .
C32 C33 C34 50.8(7) . 2
C34 C33 C34 101.6(14) . 2
C35 C34 C32 70.3(12) . .
C35 C34 C33 121.3(12) . .
C32 C34 C33 51.0(12) . .
C34 C35 C34 164.1(17) 3 .
C34 C35 C32 61.8(9) 3 3
C34 C35 C32 134.1(16) . 3
C34 C35 C32 134.1(16) 3 .
C34 C35 C32 61.8(9) . .
C32 C35 C32 72(2) 3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.965(2) .
Ni1 N1 1.965(2) 14
Ni1 P1 2.1588(8) 14
Ni1 P1 2.1588(8) .
P1 C14 1.779(3) .
P1 C15 1.815(3) .
P1 C21 1.829(3) .
N1 C9 1.373(4) .
N1 C1 1.437(4) .
C1 C7 1.398(4) .
C1 C2 1.406(4) .
C2 C4 1.396(4) .
C2 C3 1.498(4) .
C4 C5 1.385(5) .
C5 C6 1.381(5) .
C6 C7 1.398(4) .
C7 C8 1.496(4) .
C9 C10 1.412(4) .
C9 C14 1.421(4) .
C10 C11 1.376(5) .
C11 C12 1.393(5) .
C12 C13 1.381(5) .
C13 C14 1.386(4) .
C15 C16 1.388(4) .
C15 C20 1.396(4) .
C16 C17 1.381(4) .
C17 C18 1.383(5) .
C18 C19 1.379(5) .
C19 C20 1.383(4) .
C21 C22 1.395(4) .
C21 C26 1.398(5) .
C22 C23 1.387(5) .
C23 C24 1.376(5) .
C24 C25 1.388(5) .
C25 C26 1.386(5) .
C27 C28 1.358(7) .
C27 C29 1.384(6) .
C28 C29 1.369(6) 14
C29 C28 1.369(6) 14
C30 C31 1.351(5) .
C30 C30 1.376(10) 3
C31 C30 1.351(5) 4_655
C32 C33 1.32(3) .
C32 C34 1.313(12) .
C32 C34 1.313(12) 2
C32 C35 1.402(15) .
C32 C35 1.402(15) 2
C32 C32 1.65(5) 3
C33 C34 1.659(18) .
C33 C34 1.659(18) 2
C34 C35 1.107(10) .
C35 C34 1.107(10) 3
C35 C32 1.402(15) 3
