#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:33:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178570 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/79/4067985.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_4067985
loop_
_publ_author_name
'Fischer, Peter'
'Götz, Kathrin'
'Eichhorn, Antonius'
'Radius, Udo'
_publ_section_title
;
 Decisive Steps of the Hydrodefluorination of Fluoroaromatics using
 [Ni(NHC)2]
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1374
_journal_paper_doi               10.1021/om2009815
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C25 H35 F7 N4 Ni'
_chemical_formula_weight         583.28
_chemical_name_systematic
; 
Bis-{1,3-di(isopropyl)-imidazolin-2-ylidene}(hydrido)
(heptafluorotolnyl)nickel(II)
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 119.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.229(3)
_cell_length_b                   14.609(2)
_cell_length_c                   11.919(2)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.3
_cell_volume                     3059.0(12)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.677
_diffrn_measurement_device_type  'STOE IPDS 1'
_diffrn_measurement_method       rotation
_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  0.1004
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12346
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0706
_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)+(0.0929P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                2624
_reflns_number_total             3688
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2009815_si_002.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4067985
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.14038(3) 0.5000 0.30361(6) 0.0349(2) Uani 1 2 d S . .
H1 H 0.106(3) 0.5000 0.156(5) 0.033(12) Uiso 1 2 d S . .
F1 F 0.31214(18) 0.5000 0.5288(3) 0.0567(8) Uani 1 2 d S . .
F2 F 0.3716(2) 0.5000 0.7803(3) 0.0678(10) Uani 1 2 d S . .
F3 F 0.06670(18) 0.5000 0.4837(3) 0.0596(9) Uani 1 2 d S . .
F4 F 0.1253(2) 0.5000 0.7340(4) 0.0726(11) Uani 1 2 d S . .
F5A F 0.2367(5) 0.5000 0.9569(8) 0.060(2) Uani 0.50 2 d SP A 1
F6A F 0.3302(5) 0.5714(4) 0.9662(7) 0.068(2) Uani 0.50 1 d P A 1
F5B F 0.2795(14) 0.4327(11) 0.9511(12) 0.278(13) Uani 0.50 1 d P A 2
F6B F 0.3639(11) 0.5000 0.9634(13) 0.230(12) Uani 0.50 2 d SP A 2
N1 N 0.06912(16) 0.32086(18) 0.2426(3) 0.0380(7) Uani 1 1 d . . .
N2 N 0.18261(16) 0.31338(18) 0.2726(3) 0.0397(7) Uani 1 1 d . . .
C1 C 0.13214(18) 0.3729(2) 0.2771(3) 0.0347(7) Uani 1 1 d . . .
C2 C 0.0811(2) 0.2319(2) 0.2161(4) 0.0486(9) Uani 1 1 d . . .
H2A H 0.0460 0.1834 0.1898 0.058 Uiso 1 1 calc R . .
C3 C 0.1521(2) 0.2283(2) 0.2351(4) 0.0477(9) Uani 1 1 d . . .
H3A H 0.1763 0.1767 0.2245 0.057 Uiso 1 1 calc R . .
C4 C -0.00149(19) 0.3558(2) 0.2317(3) 0.0417(8) Uani 1 1 d . . .
H4A H 0.0075 0.4204 0.2606 0.050 Uiso 1 1 calc R . .
C5 C -0.0634(3) 0.3549(5) 0.0937(4) 0.0909(19) Uani 1 1 d . . .
H5A H -0.0450 0.3770 0.0410 0.109 Uiso 1 1 d R . .
H5B H -0.0824 0.2954 0.0659 0.109 Uiso 1 1 d R . .
H5C H -0.1149 0.3756 0.0971 0.109 Uiso 1 1 d R . .
H14B H -0.0908 0.4089 0.0730 0.109 Uiso 1 1 d R . .
C6 C -0.0219(3) 0.3046(3) 0.3190(6) 0.0758(15) Uani 1 1 d . . .
H6A H -0.0656 0.3333 0.3173 0.114 Uiso 1 1 calc R . .
H6B H 0.0209 0.3058 0.4065 0.114 Uiso 1 1 calc R . .
H6C H -0.0341 0.2417 0.2899 0.114 Uiso 1 1 calc R . .
C7 C 0.2600(2) 0.3396(3) 0.3029(4) 0.0454(9) Uani 1 1 d . . .
H7A H 0.2678 0.4050 0.3281 0.054 Uiso 1 1 calc R . .
C8 C 0.3181(3) 0.2841(4) 0.4148(5) 0.0696(13) Uani 1 1 d . . .
H8A H 0.3102 0.2915 0.4881 0.104 Uiso 1 1 calc R . .
H8B H 0.3688 0.3050 0.4378 0.104 Uiso 1 1 calc R . .
H8C H 0.3128 0.2200 0.3905 0.104 Uiso 1 1 calc R . .
C9 C 0.2680(3) 0.3284(4) 0.1846(5) 0.0827(16) Uani 1 1 d . . .
H9A H 0.2347 0.3714 0.1188 0.124 Uiso 1 1 calc R . .
H9B H 0.2541 0.2664 0.1519 0.124 Uiso 1 1 calc R . .
H9C H 0.3203 0.3400 0.2069 0.124 Uiso 1 1 calc R . .
C10 C 0.1858(3) 0.5000 0.4906(5) 0.0410(11) Uani 1 2 d S . .
C11 C 0.2636(3) 0.5000 0.5761(5) 0.0414(11) Uani 1 2 d S . .
C12 C 0.2963(3) 0.5000 0.7078(5) 0.0468(13) Uani 1 2 d S . .
C13 C 0.2514(4) 0.5000 0.7668(5) 0.0551(15) Uani 1 2 d S A .
C14 C 0.1731(4) 0.5000 0.6845(6) 0.0512(14) Uani 1 2 d S . .
C15 C 0.1444(3) 0.5000 0.5549(5) 0.0460(12) Uani 1 2 d S . .
C16 C 0.2872(5) 0.5000 0.9113(6) 0.072(2) Uani 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'
F F 0.0171 0.0103 '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'
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
C1 Ni C1 163.2(2) 6_565 .
C1 Ni C10 98.32(10) 6_565 .
C1 Ni C10 98.32(10) . .
C1 Ni H1 81.69(10) 6_565 .
C1 Ni H1 81.69(11) . .
C10 Ni H1 179.2(16) . .
C1 N1 C2 110.4(3) . .
C1 N1 C4 124.1(3) . .
C2 N1 C4 125.5(3) . .
C3 N2 C1 111.7(3) . .
C3 N2 C7 124.9(3) . .
C1 N2 C7 123.4(3) . .
N1 C1 N2 103.9(3) . .
N1 C1 Ni 126.5(2) . .
N2 C1 Ni 129.2(2) . .
C3 C2 N1 107.0(3) . .
C3 C2 H2A 126.5 . .
N1 C2 H2A 126.5 . .
C2 C3 N2 107.0(3) . .
C2 C3 H3A 126.5 . .
N2 C3 H3A 126.5 . .
N1 C4 C5 110.1(3) . .
N1 C4 C6 111.0(3) . .
C5 C4 C6 113.1(4) . .
N1 C4 H4A 107.5 . .
C5 C4 H4A 107.5 . .
C6 C4 H4A 107.5 . .
C4 C5 H5A 110.0 . .
C4 C5 H5B 111.6 . .
H5A C5 H5B 108.1 . .
C4 C5 H5C 104.4 . .
H5A C5 H5C 129.0 . .
H5B C5 H5C 92.2 . .
C4 C5 H14B 110.6 . .
H5A C5 H14B 84.9 . .
H5B C5 H14B 127.5 . .
H5C C5 H14B 47.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N2 C7 C8 110.2(3) . .
N2 C7 C9 109.7(3) . .
C8 C7 C9 111.8(4) . .
N2 C7 H7A 108.3 . .
C8 C7 H7A 108.3 . .
C9 C7 H7A 108.3 . .
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 . .
C11 C10 C15 111.7(5) . .
C11 C10 Ni 124.2(4) . .
C15 C10 Ni 124.1(4) . .
F1 C11 C12 116.1(5) . .
F1 C11 C10 119.2(5) . .
C12 C11 C10 124.7(5) . .
F2 C12 C11 119.5(5) . .
F2 C12 C13 119.6(5) . .
C11 C12 C13 120.9(5) . .
C14 C13 C12 116.3(5) . .
C14 C13 C16 122.8(6) . .
C12 C13 C16 120.9(6) . .
C15 C14 F4 120.0(6) . .
C15 C14 C13 119.9(5) . .
F4 C14 C13 120.1(5) . .
C14 C15 F3 114.7(5) . .
C14 C15 C10 126.5(5) . .
F3 C15 C10 118.7(5) . .
F5B C16 F5B 120(2) 6_565 .
F5B C16 F6A 45.1(13) 6_565 .
F5B C16 F6A 132.6(9) . .
F5B C16 F6A 132.6(9) 6_565 6_565
F5B C16 F6A 45.1(13) . 6_565
F6A C16 F6A 105.8(10) . 6_565
F5B C16 F6B 99.8(15) 6_565 .
F5B C16 F6B 99.8(15) . .
F6A C16 F6B 56.2(6) . .
F6A C16 F6B 56.2(6) 6_565 .
F5B C16 F5A 63.4(15) 6_565 .
F5B C16 F5A 63.4(15) . .
F6A C16 F5A 104.1(6) . .
F6A C16 F5A 104.1(6) 6_565 .
F6B C16 F5A 136.5(9) . .
F5B C16 C13 113.1(8) 6_565 .
F5B C16 C13 113.1(8) . .
F6A C16 C13 113.4(5) . .
F6A C16 C13 113.4(5) 6_565 .
F6B C16 C13 108.4(9) . .
F5A C16 C13 115.1(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni C1 1.877(3) 6_565
Ni C1 1.877(3) .
Ni C10 1.945(5) .
Ni H1 1.54(5) .
F1 C11 1.353(6) .
F2 C12 1.328(6) .
F3 C15 1.367(6) .
F4 C14 1.357(6) .
F5A C16 1.375(12) .
F6A C16 1.308(8) .
F5B C16 1.136(11) .
F6B C16 1.356(19) .
N1 C1 1.361(4) .
N1 C2 1.387(4) .
N1 C4 1.460(4) .
N2 C3 1.361(4) .
N2 C1 1.362(4) .
N2 C7 1.473(4) .
C2 C3 1.340(6) .
C2 H2A 0.9400 .
C3 H3A 0.9400 .
C4 C5 1.494(6) .
C4 C6 1.495(5) .
C4 H4A 0.9900 .
C5 H5A 0.9333 .
C5 H5B 0.9417 .
C5 H5C 1.1044 .
C5 H14B 0.9238 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C6 H6C 0.9700 .
C7 C8 1.504(5) .
C7 C9 1.505(6) .
C7 H7A 0.9900 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 H8C 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 H9C 0.9700 .
C10 C11 1.386(7) .
C10 C15 1.388(7) .
C11 C12 1.368(7) .
C12 C13 1.397(8) .
C13 C14 1.391(9) .
C13 C16 1.501(8) .
C14 C15 1.355(8) .
C16 F5B 1.136(11) 6_565
C16 F6A 1.308(8) 6_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 N1 C1 N2 -0.8(4) . .
C4 N1 C1 N2 -179.0(3) . .
C2 N1 C1 Ni 172.5(3) . .
C4 N1 C1 Ni -5.8(5) . .
C3 N2 C1 N1 0.9(4) . .
C7 N2 C1 N1 179.9(3) . .
C3 N2 C1 Ni -172.2(3) . .
C7 N2 C1 Ni 6.9(5) . .
C1 Ni C1 N1 -75.1(8) 6_565 .
C10 Ni C1 N1 97.2(3) . .
C1 Ni C1 N2 96.5(7) 6_565 .
C10 Ni C1 N2 -91.2(3) . .
C1 N1 C2 C3 0.4(4) . .
C4 N1 C2 C3 178.7(3) . .
N1 C2 C3 N2 0.1(4) . .
C1 N2 C3 C2 -0.6(4) . .
C7 N2 C3 C2 -179.7(3) . .
C1 N1 C4 C5 112.1(4) . .
C2 N1 C4 C5 -65.8(5) . .
C1 N1 C4 C6 -121.8(4) . .
C2 N1 C4 C6 60.2(5) . .
C3 N2 C7 C8 -61.2(5) . .
C1 N2 C7 C8 119.9(4) . .
C3 N2 C7 C9 62.4(5) . .
C1 N2 C7 C9 -116.6(4) . .
C1 Ni C10 C11 -91.12(10) 6_565 .
C1 Ni C10 C11 91.12(10) . .
C1 Ni C10 C15 88.88(10) 6_565 .
C1 Ni C10 C15 -88.88(10) . .
C15 C10 C11 F1 180.000(1) . .
Ni C10 C11 F1 0.000(2) . .
C15 C10 C11 C12 0.000(2) . .
Ni C10 C11 C12 180.000(2) . .
F1 C11 C12 F2 0.000(2) . .
C10 C11 C12 F2 180.000(1) . .
F1 C11 C12 C13 180.000(2) . .
C10 C11 C12 C13 0.000(3) . .
F2 C12 C13 C14 180.000(2) . .
C11 C12 C13 C14 0.000(3) . .
F2 C12 C13 C16 0.000(3) . .
C11 C12 C13 C16 180.000(3) . .
C12 C13 C14 C15 0.000(2) . .
C16 C13 C14 C15 180.000(2) . .
C12 C13 C14 F4 180.000(2) . .
C16 C13 C14 F4 0.000(3) . .
F4 C14 C15 F3 0.000(2) . .
C13 C14 C15 F3 180.000(2) . .
F4 C14 C15 C10 180.000(2) . .
C13 C14 C15 C10 0.000(3) . .
C11 C10 C15 C14 0.000(2) . .
Ni C10 C15 C14 180.000(2) . .
C11 C10 C15 F3 180.000(1) . .
Ni C10 C15 F3 0.000(2) . .
C14 C13 C16 F5B -70.3(18) . 6_565
C12 C13 C16 F5B 109.7(18) . 6_565
C14 C13 C16 F5B 70.3(18) . .
C12 C13 C16 F5B -109.7(18) . .
C14 C13 C16 F6A -119.6(7) . .
C12 C13 C16 F6A 60.4(7) . .
C14 C13 C16 F6A 119.6(7) . 6_565
C12 C13 C16 F6A -60.4(7) . 6_565
C14 C13 C16 F6B 180.000(6) . .
C12 C13 C16 F6B 0.000(5) . .
C14 C13 C16 F5A 0.000(4) . .
C12 C13 C16 F5A 180.000(4) . .
