#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:52:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178921 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/50/4115023.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_4115023
loop_
_publ_author_name
'Juventino J. Garcia'
'Nicole M. Brunkan'
'William D. Jones'
_publ_section_title
;
 Cleavage of Carbon-Carbon Bonds in Aromatic Nitriles Using Nickel(0)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9547
_journal_page_last               9555
_journal_paper_doi               10.1021/ja0204933
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C24 H38 N2 Ni P2'
_chemical_formula_weight         475.21
_chemical_name_common            (dippe)Ni(3-quinolinyl)(CN)
_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                 92.023(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0200(14)
_cell_length_b                   20.925(3)
_cell_length_c                   14.969(3)
_cell_measurement_reflns_used    5215
_cell_measurement_temperature    188(2)
_cell_volume                     2510.5(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      188(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11296
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.8629
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          .10
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .18
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0576P)²+1.7278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                3065
_reflns_number_total             3600
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0204933_5.cif
_cod_data_source_block           sad_jonjg09
_cod_original_cell_volume        2510.6(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4115023
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 0.34514(5) 0.21975(2) 0.12394(3) 0.02636(17) Uani 1 1 d .
P1 P 0.21872(11) 0.12867(4) 0.09527(6) 0.0270(2) Uani 1 1 d .
P2 P 0.12159(11) 0.26923(4) 0.07441(6) 0.0263(2) Uani 1 1 d .
N1 N 0.6547(5) 0.14820(19) 0.1791(3) 0.0538(10) Uani 1 1 d .
N2 N 0.5427(4) 0.37361(16) 0.2708(2) 0.0416(9) Uani 1 1 d .
C1 C 0.5443(5) 0.17526(18) 0.1606(2) 0.0311(9) Uani 1 1 d .
C2 C 0.4732(5) 0.32052(19) 0.2401(3) 0.0381(10) Uani 1 1 d .
H2B H 0.4308 0.2925 0.2838 0.046 Uiso 1 1 calc R
C3 C 0.4537(5) 0.30005(18) 0.1510(3) 0.0329(9) Uani 1 1 d .
C4 C 0.5212(5) 0.34093(18) 0.0889(3) 0.0352(9) Uani 1 1 d .
H4A H 0.5173 0.3294 0.0275 0.042 Uiso 1 1 calc R
C5 C 0.5963(5) 0.39993(18) 0.1156(3) 0.0325(9) Uani 1 1 d .
C6 C 0.6587(5) 0.44469(19) 0.0552(3) 0.0411(10) Uani 1 1 d .
H6A H 0.6526 0.4358 -0.0070 0.049 Uiso 1 1 calc R
C7 C 0.7282(5) 0.5010(2) 0.0850(3) 0.0523(12) Uani 1 1 d .
H7A H 0.7704 0.5305 0.0433 0.063 Uiso 1 1 calc R
C8 C 0.7375(5) 0.5151(2) 0.1756(3) 0.0488(12) Uani 1 1 d .
H8A H 0.7867 0.5541 0.1956 0.059 Uiso 1 1 calc R
C9 C 0.6764(5) 0.4733(2) 0.2357(3) 0.0434(11) Uani 1 1 d .
H9A H 0.6823 0.4836 0.2976 0.052 Uiso 1 1 calc R
C10 C 0.6037(5) 0.41464(19) 0.2075(3) 0.0357(9) Uani 1 1 d .
C11 C 0.1544(5) 0.08385(18) 0.1947(3) 0.0346(9) Uani 1 1 d .
H11A H 0.0644 0.0535 0.1746 0.042 Uiso 1 1 calc R
C12 C 0.2946(5) 0.0444(2) 0.2386(3) 0.0469(11) Uani 1 1 d .
H12A H 0.2521 0.0214 0.2901 0.070 Uiso 1 1 calc R
H12B H 0.3856 0.0728 0.2585 0.070 Uiso 1 1 calc R
H12C H 0.3360 0.0136 0.1953 0.070 Uiso 1 1 calc R
C13 C 0.0801(5) 0.1291(2) 0.2626(3) 0.0423(10) Uani 1 1 d .
H13A H 0.0457 0.1047 0.3146 0.063 Uiso 1 1 calc R
H13B H -0.0170 0.1509 0.2352 0.063 Uiso 1 1 calc R
H13C H 0.1640 0.1608 0.2815 0.063 Uiso 1 1 calc R
C14 C 0.3347(5) 0.07050(17) 0.0288(3) 0.0328(9) Uani 1 1 d .
H14A H 0.4316 0.0555 0.0671 0.039 Uiso 1 1 calc R
C15 C 0.2310(5) 0.01135(19) 0.0034(3) 0.0434(10) Uani 1 1 d .
H15A H 0.2987 -0.0182 -0.0310 0.065 Uiso 1 1 calc R
H15B H 0.1326 0.0243 -0.0328 0.065 Uiso 1 1 calc R
H15C H 0.1954 -0.0100 0.0578 0.065 Uiso 1 1 calc R
C16 C 0.4057(5) 0.1024(2) -0.0529(3) 0.0427(10) Uani 1 1 d .
H16A H 0.4678 0.0709 -0.0869 0.064 Uiso 1 1 calc R
H16B H 0.4808 0.1371 -0.0337 0.064 Uiso 1 1 calc R
H16C H 0.3143 0.1198 -0.0907 0.064 Uiso 1 1 calc R
C17 C 0.1551(5) 0.31172(18) -0.0312(2) 0.0321(9) Uani 1 1 d .
H17A H 0.2292 0.3489 -0.0162 0.038 Uiso 1 1 calc R
C18 C -0.0038(5) 0.3390(2) -0.0759(3) 0.0472(11) Uani 1 1 d .
H18A H 0.0241 0.3611 -0.1312 0.071 Uiso 1 1 calc R
H18B H -0.0554 0.3693 -0.0353 0.071 Uiso 1 1 calc R
H18C H -0.0821 0.3042 -0.0899 0.071 Uiso 1 1 calc R
C19 C 0.2490(6) 0.2699(2) -0.0964(3) 0.0435(11) Uani 1 1 d .
H19A H 0.2657 0.2937 -0.1517 0.065 Uiso 1 1 calc R
H19B H 0.1838 0.2312 -0.1099 0.065 Uiso 1 1 calc R
H19C H 0.3576 0.2579 -0.0693 0.065 Uiso 1 1 calc R
C20 C 0.0127(5) 0.32839(18) 0.1431(3) 0.0342(9) Uani 1 1 d .
H20A H -0.1005 0.3348 0.1143 0.041 Uiso 1 1 calc R
C21 C -0.0138(6) 0.3023(2) 0.2368(3) 0.0581(13) Uani 1 1 d .
H21A H -0.0721 0.3342 0.2719 0.087 Uiso 1 1 calc R
H21B H 0.0946 0.2927 0.2660 0.087 Uiso 1 1 calc R
H21C H -0.0808 0.2632 0.2326 0.087 Uiso 1 1 calc R
C22 C 0.0955(6) 0.39379(19) 0.1485(3) 0.0468(11) Uani 1 1 d .
H22A H 0.0294 0.4223 0.1853 0.070 Uiso 1 1 calc R
H22B H 0.1023 0.4117 0.0883 0.070 Uiso 1 1 calc R
H22C H 0.2080 0.3895 0.1755 0.070 Uiso 1 1 calc R
C23 C 0.0241(4) 0.14431(17) 0.0293(3) 0.0325(9) Uani 1 1 d .
H23A H 0.0463 0.1418 -0.0353 0.039 Uiso 1 1 calc R
H23B H -0.0599 0.1114 0.0429 0.039 Uiso 1 1 calc R
C24 C -0.0443(4) 0.21061(17) 0.0511(3) 0.0324(9) Uani 1 1 d .
H24A H -0.1150 0.2073 0.1038 0.039 Uiso 1 1 calc R
H24B H -0.1154 0.2258 0.0000 0.039 Uiso 1 1 calc 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'
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
C1 Ni1 C3 89.85(15)
C1 Ni1 P2 176.78(12)
C3 Ni1 P2 91.01(12)
C1 Ni1 P1 90.50(11)
C3 Ni1 P1 178.95(12)
P2 Ni1 P1 88.69(4)
C14 P1 C23 105.14(17)
C14 P1 C11 105.08(17)
C23 P1 C11 105.45(18)
C14 P1 Ni1 116.12(12)
C23 P1 Ni1 109.06(12)
C11 P1 Ni1 115.05(13)
C24 P2 C17 106.65(18)
C24 P2 C20 101.54(17)
C17 P2 C20 103.90(17)
C24 P2 Ni1 109.25(12)
C17 P2 Ni1 112.23(12)
C20 P2 Ni1 121.92(13)
C2 N2 C10 116.1(3)
N1 C1 Ni1 177.1(4)
N2 C2 C3 128.3(4)
C4 C3 C2 114.5(3)
C4 C3 Ni1 125.5(3)
C2 C3 Ni1 120.0(3)
C3 C4 C5 121.2(4)
C6 C5 C10 118.6(4)
C6 C5 C4 123.7(4)
C10 C5 C4 117.8(4)
C7 C6 C5 120.9(4)
C6 C7 C8 120.6(4)
C9 C8 C7 120.1(4)
C8 C9 C10 120.9(4)
N2 C10 C5 122.1(4)
N2 C10 C9 119.0(4)
C5 C10 C9 118.9(4)
C12 C11 C13 110.4(3)
C12 C11 P1 113.5(3)
C13 C11 P1 110.4(3)
C16 C14 C15 111.8(3)
C16 C14 P1 110.7(3)
C15 C14 P1 112.8(3)
C18 C17 C19 110.9(3)
C18 C17 P2 114.3(3)
C19 C17 P2 111.2(3)
C22 C20 C21 110.3(3)
C22 C20 P2 114.7(3)
C21 C20 P2 110.8(3)
C24 C23 P1 110.4(3)
C23 C24 P2 112.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni1 C1 1.912(4)
Ni1 C3 1.929(4)
Ni1 P2 2.1776(11)
Ni1 P1 2.1941(11)
P1 C14 1.845(4)
P1 C23 1.847(4)
P1 C11 1.848(4)
P2 C24 1.834(4)
P2 C17 1.841(4)
P2 C20 1.848(4)
N1 C1 1.079(5)
N2 C2 1.319(5)
N2 C10 1.382(5)
C2 C3 1.404(5)
C3 C4 1.387(5)
C4 C5 1.425(5)
C5 C6 1.405(5)
C5 C10 1.409(5)
C6 C7 1.370(6)
C7 C8 1.387(6)
C8 C9 1.358(6)
C9 C10 1.417(5)
C11 C12 1.525(5)
C11 C13 1.525(5)
C14 C16 1.521(5)
C14 C15 1.531(5)
C17 C18 1.530(5)
C17 C19 1.529(5)
C20 C22 1.522(6)
C20 C21 1.527(6)
C23 C24 1.531(5)
