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#$Date: 2019-11-02 06:11:25 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/75/4127557.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_4127557
loop_
_publ_author_name
'Bour, James R.'
'Ferguson, Devin M.'
'McClain, Edward J.'
'Kampf, Jeff W.'
'Sanford, Melanie S.'
_publ_section_title
;
 Connecting Organometallic Ni(III) and Ni(IV): Reactions of
 Carbon-Centered Radicals with High-Valent Organonickel Complexes.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8914
_journal_page_last               8920
_journal_paper_doi               10.1021/jacs.9b02411
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C12 H10 B F9 N6 Ni'
_chemical_formula_sum            'C12 H10 B F9 N6 Ni'
_chemical_formula_weight         478.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0863(11)
_cell_length_b                   13.4144(3)
_cell_length_c                   7.63650(10)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.40
_cell_measurement_theta_min      3.30
_cell_volume                     1647.87(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 29.257
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            24534
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.020
_diffrn_reflns_theta_min         5.500
_exptl_absorpt_coefficient_mu    2.769
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+1.8256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1516
_reflns_number_total             1575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b02411_si_004.cif
_cod_data_source_block           jrb2073
_cod_database_code               4127557
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.681
_shelx_estimated_absorpt_t_max   0.947
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Ni1 Ni 0.66802(3) 0.250000 0.51223(6) 0.01487(19) Uani 1 2 d S T P
F1 F 0.74611(9) 0.32906(10) 0.80849(16) 0.0287(3) Uani 1 1 d . . .
F5 F 0.67681(8) 0.42597(10) 0.32489(19) 0.0286(3) Uani 1 1 d . . .
F2 F 0.83089(11) 0.250000 0.6409(3) 0.0377(6) Uani 1 2 d S T P
F4 F 0.78537(9) 0.34028(11) 0.2814(2) 0.0391(4) Uani 1 1 d . . .
F3 F 0.77073(12) 0.42177(13) 0.5189(2) 0.0469(5) Uani 1 1 d . . .
N2 N 0.51340(14) 0.250000 0.3208(3) 0.0134(5) Uani 1 2 d S T P
N1 N 0.59730(15) 0.250000 0.3012(3) 0.0151(5) Uani 1 2 d S T P
N3 N 0.51087(10) 0.34152(12) 0.6024(2) 0.0144(4) Uani 1 1 d . . .
N4 N 0.59471(11) 0.35396(13) 0.6228(2) 0.0165(4) Uani 1 1 d . . .
C3 C 0.47714(19) 0.250000 0.1619(4) 0.0169(6) Uani 1 2 d S T P
H3 H 0.418985 0.250000 0.140257 0.020 Uiso 1 2 calc R U P
C4 C 0.47029(15) 0.41689(15) 0.6803(3) 0.0208(5) Uani 1 1 d . . .
H4 H 0.411662 0.425014 0.684695 0.025 Uiso 1 1 calc R U .
C2 C 0.5384(2) 0.250000 0.0360(4) 0.0197(6) Uani 1 2 d S T P
H2 H 0.531409 0.250000 -0.087532 0.024 Uiso 1 2 calc R U P
C1 C 0.61247(19) 0.250000 0.1283(4) 0.0188(6) Uani 1 2 d S T P
H1 H 0.666229 0.250000 0.076740 0.023 Uiso 1 2 calc R U P
C7 C 0.75209(19) 0.250000 0.7017(4) 0.0249(7) Uani 1 2 d S T P
C6 C 0.60469(15) 0.43896(16) 0.7139(3) 0.0232(5) Uani 1 1 d . . .
H6 H 0.656803 0.466516 0.746835 0.028 Uiso 1 1 calc R U .
C8 C 0.73029(14) 0.36487(17) 0.4036(3) 0.0234(5) Uani 1 1 d . . .
C5 C 0.52810(16) 0.48049(15) 0.7529(3) 0.0258(5) Uani 1 1 d . . .
H5 H 0.517619 0.540156 0.816134 0.031 Uiso 1 1 calc R U .
B1 B 0.4766(2) 0.250000 0.5062(4) 0.0138(6) Uani 1 2 d S T P
H1B H 0.407(2) 0.250000 0.502(4) 0.016(9) Uiso 1 2 d S . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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 C7 172.14(11) . .
N1 Ni1 N4 90.29(7) . 7_565
C7 Ni1 N4 95.37(8) . 7_565
N1 Ni1 N4 90.29(7) . .
C7 Ni1 N4 95.37(8) . .
N4 Ni1 N4 87.75(10) 7_565 .
N1 Ni1 C8 87.16(8) . .
C7 Ni1 C8 87.78(9) . .
N4 Ni1 C8 173.44(8) 7_565 .
N4 Ni1 C8 86.23(8) . .
N1 Ni1 C8 87.16(8) . 7_565
C7 Ni1 C8 87.78(9) . 7_565
N4 Ni1 C8 86.23(8) 7_565 7_565
N4 Ni1 C8 173.44(8) . 7_565
C8 Ni1 C8 99.67(13) . 7_565
C3 N2 N1 109.3(2) . .
C3 N2 B1 131.6(2) . .
N1 N2 B1 119.0(2) . .
C1 N1 N2 106.8(2) . .
C1 N1 Ni1 134.3(2) . .
N2 N1 Ni1 118.87(17) . .
C4 N3 N4 109.68(17) . .
C4 N3 B1 129.8(2) . .
N4 N3 B1 120.46(18) . .
C6 N4 N3 106.27(17) . .
C6 N4 Ni1 137.26(15) . .
N3 N4 Ni1 116.44(12) . .
N2 C3 C2 108.6(3) . .
N2 C3 H3 125.7 . .
C2 C3 H3 125.7 . .
N3 C4 C5 108.4(2) . .
N3 C4 H4 125.8 . .
C5 C4 H4 125.8 . .
C3 C2 C1 105.1(3) . .
C3 C2 H2 127.4 . .
C1 C2 H2 127.4 . .
N1 C1 C2 110.1(3) . .
N1 C1 H1 124.9 . .
C2 C1 H1 124.9 . .
F1 C7 F1 104.5(2) . 7_565
F1 C7 F2 106.05(18) . .
F1 C7 F2 106.05(18) 7_565 .
F1 C7 Ni1 113.28(15) . .
F1 C7 Ni1 113.28(15) 7_565 .
F2 C7 Ni1 113.0(2) . .
N4 C6 C5 110.2(2) . .
N4 C6 H6 124.9 . .
C5 C6 H6 124.9 . .
F4 C8 F5 105.45(17) . .
F4 C8 F3 106.28(19) . .
F5 C8 F3 105.1(2) . .
F4 C8 Ni1 115.51(16) . .
F5 C8 Ni1 109.58(14) . .
F3 C8 Ni1 114.08(15) . .
C4 C5 C6 105.37(19) . .
C4 C5 H5 127.3 . .
C6 C5 H5 127.3 . .
N3 B1 N3 106.4(2) 7_565 .
N3 B1 N2 107.66(16) 7_565 .
N3 B1 N2 107.66(16) . .
N3 B1 H1B 111.9(9) 7_565 .
N3 B1 H1B 111.9(9) . .
N2 B1 H1B 111.0(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.973(2) .
Ni1 C7 1.981(3) .
Ni1 N4 2.0121(18) 7_565
Ni1 N4 2.0121(18) .
Ni1 C8 2.016(2) .
Ni1 C8 2.016(2) 7_565
F1 C7 1.341(2) .
F5 C8 1.332(3) .
F2 C7 1.350(4) .
F4 C8 1.328(3) .
F3 C8 1.334(3) .
N2 C3 1.346(4) .
N2 N1 1.358(3) .
N2 B1 1.534(4) .
N1 C1 1.343(4) .
N3 C4 1.343(3) .
N3 N4 1.368(2) .
N3 B1 1.533(2) .
N4 C6 1.345(3) .
C3 C2 1.377(4) .
C3 H3 0.9500 .
C4 C5 1.378(3) .
C4 H4 0.9500 .
C2 C1 1.384(4) .
C2 H2 0.9500 .
C1 H1 0.9500 .
C6 C5 1.384(3) .
C6 H6 0.9500 .
C5 H5 0.9500 .
B1 H1B 1.12(4) .
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_4
C3 N2 N1 C1 0.000(0) .
B1 N2 N1 C1 180.000(0) .
C3 N2 N1 Ni1 180.0 .
B1 N2 N1 Ni1 0.000(0) .
C4 N3 N4 C6 -0.4(2) .
B1 N3 N4 C6 -178.88(18) .
C4 N3 N4 Ni1 -179.06(13) .
B1 N3 N4 Ni1 2.5(2) .
N1 N2 C3 C2 0.000(0) .
B1 N2 C3 C2 180.000(0) .
N4 N3 C4 C5 0.3(2) .
B1 N3 C4 C5 178.54(19) .
N2 C3 C2 C1 0.000(0) .
N2 N1 C1 C2 0.000(0) .
Ni1 N1 C1 C2 180.000(0) .
C3 C2 C1 N1 0.000(0) .
N3 N4 C6 C5 0.4(2) .
Ni1 N4 C6 C5 178.62(16) .
N3 C4 C5 C6 0.0(2) .
N4 C6 C5 C4 -0.3(2) .
C4 N3 B1 N3 -121.5(2) 7_565
N4 N3 B1 N3 56.6(3) 7_565
C4 N3 B1 N2 123.3(2) .
N4 N3 B1 N2 -58.5(2) .
C3 N2 B1 N3 122.82(15) 7_565
N1 N2 B1 N3 -57.18(15) 7_565
C3 N2 B1 N3 -122.82(15) .
N1 N2 B1 N3 57.18(15) .
