#------------------------------------------------------------------------------
#$Date: 2019-11-02 07:51:08 +0200 (Sat, 02 Nov 2019) $
#$Revision: 221012 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/78/4127840.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_4127840
loop_
_publ_author_name
'Meucci, Elizabeth A.'
'Ariafard, Alireza'
'Canty, Allan J.'
'Kampf, Jeff W.'
'Sanford, Melanie S.'
_publ_section_title
;
 Aryl-Fluoride Bond-Forming Reductive Elimination from Nickel(IV) Centers.
;
_journal_issue                   33
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13261
_journal_page_last               13267
_journal_paper_doi               10.1021/jacs.9b06896
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C21 H18 B F N6 Ni, 2(C2 D3 N)'
_chemical_formula_sum            'C25 H18 B D6 F N8 Ni'
_chemical_formula_weight         531.08
_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   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.48910(10)
_cell_length_b                   18.8696(2)
_cell_length_c                   8.52640(10)
_cell_measurement_reflns_used    23436
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.9490
_cell_measurement_theta_min      4.6320
_cell_volume                     2331.15(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            34440
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.335
_diffrn_reflns_theta_min         5.694
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.00197(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0401P)²+1.4543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2239
_reflns_number_total             2248
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b06896_si_001.cif
_cod_data_source_block           em456
_cod_database_code               4127840
_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   0.814
_shelx_estimated_absorpt_t_max   0.927
_shelxl_version_number           2014/6
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
B1 B 0.16830(14) 0.7500 0.8415(2) 0.0132(4) Uani 1 2 d S T P
H1A H 0.1375 0.7500 0.9464 0.016 Uiso 1 2 calc R U P
F1 F 0.22550(7) 0.7500 0.32701(13) 0.0143(2) Uani 1 2 d S T P
Ni1 Ni 0.27254(2) 0.7500 0.52512(4) 0.00969(13) Uani 1 2 d S T P
N1 N 0.32818(10) 0.7500 0.72535(18) 0.0114(3) Uani 1 2 d S T P
N2 N 0.27435(10) 0.7500 0.85681(19) 0.0122(3) Uani 1 2 d S T P
N3 N 0.14156(7) 0.68411(6) 0.74406(13) 0.0126(2) Uani 1 1 d . . .
N4 N 0.17825(7) 0.67737(6) 0.59744(13) 0.0121(2) Uani 1 1 d . . .
N5 N 0.33581(10) 0.53830(7) -0.15759(16) 0.0290(3) Uani 1 1 d . . .
C1 C 0.41601(13) 0.7500 0.7725(2) 0.0139(4) Uani 1 2 d S T P
H1 H 0.4681 0.7500 0.7048 0.017 Uiso 1 2 calc R U P
C2 C 0.42010(13) 0.7500 0.9349(2) 0.0168(4) Uani 1 2 d S T P
H2 H 0.4739 0.7500 0.9987 0.020 Uiso 1 2 calc R U P
C3 C 0.32925(14) 0.7500 0.9842(2) 0.0149(4) Uani 1 2 d S T P
H3 H 0.3089 0.7500 1.0902 0.018 Uiso 1 2 calc R U P
C4 C 0.07934(9) 0.63214(7) 0.76789(16) 0.0153(3) Uani 1 1 d . . .
H4 H 0.0441 0.6253 0.8606 0.018 Uiso 1 1 calc R U .
C5 C 0.07549(9) 0.59053(7) 0.63526(17) 0.0172(3) Uani 1 1 d . . .
H5 H 0.0381 0.5499 0.6181 0.021 Uiso 1 1 calc R U .
C6 C 0.13844(9) 0.62107(7) 0.53188(15) 0.0141(3) Uani 1 1 d . . .
H6 H 0.1512 0.6041 0.4292 0.017 Uiso 1 1 calc R U .
C7 C 0.36351(9) 0.81923(7) 0.45419(14) 0.0117(3) Uani 1 1 d . . .
C8 C 0.35829(9) 0.89121(7) 0.48088(15) 0.0133(3) Uani 1 1 d . . .
H8 H 0.3111 0.9106 0.5451 0.016 Uiso 1 1 calc R U .
C9 C 0.42451(9) 0.93480(7) 0.41066(16) 0.0151(3) Uani 1 1 d . . .
H9 H 0.4213 0.9847 0.4252 0.018 Uiso 1 1 calc R U .
C10 C 0.49496(9) 0.90631(7) 0.31999(16) 0.0154(3) Uani 1 1 d . . .
H10 H 0.5386 0.9367 0.2712 0.018 Uiso 1 1 calc R U .
C11 C 0.50179(9) 0.83307(7) 0.30046(15) 0.0140(3) Uani 1 1 d . . .
H11 H 0.5512 0.8134 0.2415 0.017 Uiso 1 1 calc R U .
C12 C 0.43536(9) 0.78876(7) 0.36842(15) 0.0121(3) Uani 1 1 d . . .
C13 C 0.30102(10) 0.56100(8) -0.04815(18) 0.0200(3) Uani 1 1 d . . .
C14 C 0.25717(11) 0.58780(9) 0.09339(18) 0.0250(3) Uani 1 1 d . . .
D14A D 0.2348 0.5479 0.1565 0.037 Uiso 1 1 calc R U .
D14B D 0.2051 0.6183 0.0647 0.037 Uiso 1 1 calc R U .
D14C D 0.3020 0.6152 0.1543 0.037 Uiso 1 1 calc R U .
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'
D D 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
N2 B1 N3 107.19(10) . 7_575
N2 B1 N3 107.19(10) . .
N3 B1 N3 107.21(15) 7_575 .
N2 B1 H1A 111.7 . .
N3 B1 H1A 111.7 7_575 .
N3 B1 H1A 111.7 . .
F1 Ni1 N1 176.70(6) . .
F1 Ni1 C7 88.01(4) . 7_575
N1 Ni1 C7 89.53(5) . 7_575
F1 Ni1 C7 88.02(4) . .
N1 Ni1 C7 89.53(5) . .
C7 Ni1 C7 84.02(8) 7_575 .
F1 Ni1 N4 91.71(4) . 7_575
N1 Ni1 N4 90.73(5) . 7_575
C7 Ni1 N4 179.50(5) 7_575 7_575
C7 Ni1 N4 95.55(5) . 7_575
F1 Ni1 N4 91.71(4) . .
N1 Ni1 N4 90.73(5) . .
C7 Ni1 N4 95.55(5) 7_575 .
C7 Ni1 N4 179.50(5) . .
N4 Ni1 N4 84.88(6) 7_575 .
C1 N1 N2 107.29(15) . .
C1 N1 Ni1 132.82(13) . .
N2 N1 Ni1 119.90(12) . .
C3 N2 N1 108.96(15) . .
C3 N2 B1 131.07(16) . .
N1 N2 B1 119.96(15) . .
C4 N3 N4 109.33(11) . .
C4 N3 B1 132.27(13) . .
N4 N3 B1 118.04(11) . .
C6 N4 N3 106.87(10) . .
C6 N4 Ni1 134.60(9) . .
N3 N4 Ni1 118.51(8) . .
N1 C1 C2 109.99(17) . .
N1 C1 H1 125.0 . .
C2 C1 H1 125.0 . .
C3 C2 C1 105.26(17) . .
C3 C2 H2 127.4 . .
C1 C2 H2 127.4 . .
N2 C3 C2 108.50(17) . .
N2 C3 H3 125.8 . .
C2 C3 H3 125.8 . .
N3 C4 C5 108.55(12) . .
N3 C4 H4 125.7 . .
C5 C4 H4 125.7 . .
C4 C5 C6 104.89(12) . .
C4 C5 H5 127.6 . .
C6 C5 H5 127.6 . .
N4 C6 C5 110.36(12) . .
N4 C6 H6 124.8 . .
C5 C6 H6 124.8 . .
C8 C7 C12 122.20(12) . .
C8 C7 Ni1 124.81(10) . .
C12 C7 Ni1 112.97(10) . .
C7 C8 C9 118.09(12) . .
C7 C8 H8 121.0 . .
C9 C8 H8 121.0 . .
C10 C9 C8 120.99(13) . .
C10 C9 H9 119.5 . .
C8 C9 H9 119.5 . .
C9 C10 C11 120.13(12) . .
C9 C10 H10 119.9 . .
C11 C10 H10 119.9 . .
C10 C11 C12 119.55(12) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C7 C12 C11 118.90(12) . .
C7 C12 C12 114.32(8) . 7_575
C11 C12 C12 126.66(8) . 7_575
N5 C13 C14 178.24(16) . .
C13 C14 D14A 109.5 . .
C13 C14 D14B 109.5 . .
D14A C14 D14B 109.5 . .
C13 C14 D14C 109.5 . .
D14A C14 D14C 109.5 . .
D14B C14 D14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 N2 1.542(3) .
B1 N3 1.5445(16) 7_575
B1 N3 1.5446(16) .
B1 H1A 1.0000 .
F1 Ni1 1.8215(11) .
Ni1 N1 1.8879(16) .
Ni1 C7 1.9518(13) 7_575
Ni1 C7 1.9518(13) .
Ni1 N4 2.0310(11) 7_575
Ni1 N4 2.0311(11) .
N1 C1 1.335(2) .
N1 N2 1.366(2) .
N2 C3 1.346(3) .
N3 C4 1.3474(17) .
N3 N4 1.3644(16) .
N4 C6 1.3317(18) .
N5 C13 1.144(2) .
C1 C2 1.386(3) .
C1 H1 0.9500 .
C2 C3 1.382(3) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C5 1.378(2) .
C4 H4 0.9500 .
C5 C6 1.3933(19) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.3793(19) .
C7 C12 1.3961(18) .
C8 C9 1.3985(19) .
C8 H8 0.9500 .
C9 C10 1.389(2) .
C9 H9 0.9500 .
C10 C11 1.3955(19) .
C10 H10 0.9500 .
C11 C12 1.4005(18) .
C11 H11 0.9500 .
C12 C12 1.463(3) 7_575
C13 C14 1.455(2) .
C14 D14A 0.9800 .
C14 D14B 0.9800 .
C14 D14C 0.9800 .
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
C7 Ni1 N1 C1 42.01(4) 7_575 .
C7 Ni1 N1 C1 -42.01(4) . .
N4 Ni1 N1 C1 -137.56(3) 7_575 .
N4 Ni1 N1 C1 137.56(3) . .
C7 Ni1 N1 N2 -137.99(4) 7_575 .
C7 Ni1 N1 N2 137.99(4) . .
N4 Ni1 N1 N2 42.44(3) 7_575 .
N4 Ni1 N1 N2 -42.44(3) . .
C1 N1 N2 C3 0.000(0) . .
Ni1 N1 N2 C3 180.000(0) . .
C1 N1 N2 B1 180.000(0) . .
Ni1 N1 N2 B1 0.000(0) . .
N3 B1 N2 C3 122.59(10) 7_575 .
N3 B1 N2 C3 -122.59(10) . .
N3 B1 N2 N1 -57.41(10) 7_575 .
N3 B1 N2 N1 57.41(10) . .
N2 B1 N3 C4 130.07(15) . .
N3 B1 N3 C4 -115.12(15) 7_575 .
N2 B1 N3 N4 -57.79(15) . .
N3 B1 N3 N4 57.02(18) 7_575 .
C4 N3 N4 C6 -0.12(13) . .
B1 N3 N4 C6 -173.97(12) . .
C4 N3 N4 Ni1 178.55(8) . .
B1 N3 N4 Ni1 4.70(15) . .
N2 N1 C1 C2 0.000(0) . .
Ni1 N1 C1 C2 180.000(0) . .
N1 C1 C2 C3 0.000(0) . .
N1 N2 C3 C2 0.000(0) . .
B1 N2 C3 C2 180.000(0) . .
C1 C2 C3 N2 0.000(0) . .
N4 N3 C4 C5 0.27(14) . .
B1 N3 C4 C5 172.92(14) . .
N3 C4 C5 C6 -0.30(15) . .
N3 N4 C6 C5 -0.07(14) . .
Ni1 N4 C6 C5 -178.43(9) . .
C4 C5 C6 N4 0.23(15) . .
C12 C7 C8 C9 4.06(19) . .
Ni1 C7 C8 C9 -174.39(9) . .
C7 C8 C9 C10 -1.65(19) . .
C8 C9 C10 C11 -1.4(2) . .
C9 C10 C11 C12 2.2(2) . .
C8 C7 C12 C11 -3.32(19) . .
Ni1 C7 C12 C11 175.29(9) . .
C8 C7 C12 C12 172.98(10) . 7_575
Ni1 C7 C12 C12 -8.41(9) . 7_575
C10 C11 C12 C7 0.12(19) . .
C10 C11 C12 C12 -175.67(8) . 7_575
