#------------------------------------------------------------------------------
#$Date: 2019-11-10 07:21:16 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/57/4515701.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_4515701
loop_
_publ_author_name
'Tamang, Sem Raj'
'Singh, Arpita'
'Unruh, Daniel K.'
'Findlater, Michael'
_publ_section_title
;
 Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6186
_journal_paper_doi               10.1021/acscatal.8b01166
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C22 H22 F6 N2 Ni O4'
_chemical_formula_sum            'C22 H22 F6 N2 Ni O4'
_chemical_formula_weight         551.12
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                86.398(4)
_cell_angle_beta                 79.115(5)
_cell_angle_gamma                86.957(5)
_cell_formula_units_Z            1
_cell_length_a                   6.3927(15)
_cell_length_b                   8.606(2)
_cell_length_c                   10.965(2)
_cell_measurement_reflns_used    3494
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.38
_cell_volume                     590.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8026
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_min         1.894
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       blade
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0305
_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)+(0.0350P)²+0.1792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2370
_reflns_number_total             2593
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b01166_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4515701
_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   0.672
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.5000 0.5000 0.02756(11) Uani 1 2 d S . P . .
F1A F 0.6635(18) 0.178(3) -0.0226(11) 0.094(5) Uani 0.43(3) 1 d . . P A 1
F2A F 0.870(2) 0.1261(16) 0.1068(11) 0.091(3) Uani 0.43(3) 1 d . . P A 1
F3A F 0.8511(17) 0.3485(13) 0.0232(14) 0.074(2) Uani 0.43(3) 1 d . . P A 1
F1B F 0.8957(12) 0.1578(12) 0.1080(8) 0.076(2) Uani 0.57(3) 1 d . . P A 2
F2B F 0.6609(16) 0.1079(13) 0.0105(13) 0.093(3) Uani 0.57(3) 1 d . . P A 2
F3B F 0.793(3) 0.3293(13) -0.0149(11) 0.099(4) Uani 0.57(3) 1 d . . P A 2
O1 O -0.17067(19) 0.57291(13) 0.36973(11) 0.0323(3) Uani 1 1 d . . . . .
O2 O 0.15440(19) 0.70277(13) 0.47667(11) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.2433(2) 0.39960(16) 0.35798(13) 0.0308(3) Uani 1 1 d . . . . .
C1 C -0.1496(3) 0.6991(2) 0.30378(15) 0.0311(4) Uani 1 1 d . . . . .
C2 C -0.0104(3) 0.8153(2) 0.31359(17) 0.0382(4) Uani 1 1 d . . . . .
H2 H -0.0111 0.9048 0.2583 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1307(3) 0.81208(19) 0.39780(16) 0.0323(4) Uani 1 1 d . . . . .
C4 C -0.2876(3) 0.7189(2) 0.20546(19) 0.0449(5) Uani 1 1 d . . . . .
H4A H -0.2741 0.8240 0.1657 0.067 Uiso 1 1 calc R U . . .
H4B H -0.4367 0.7035 0.2443 0.067 Uiso 1 1 calc R U . . .
H4C H -0.2413 0.6418 0.1427 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2666(3) 0.9512(2) 0.3957(2) 0.0475(5) Uani 1 1 d . . . . .
H5A H 0.4143 0.9152 0.3968 0.071 Uiso 1 1 calc R U . . .
H5B H 0.2123 1.0114 0.4688 0.071 Uiso 1 1 calc R U . . .
H5C H 0.2614 1.0171 0.3200 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2082(3) 0.3853(2) 0.24236(17) 0.0391(4) Uani 1 1 d . . . . .
H6 H 0.0721 0.4176 0.2248 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3583(3) 0.3265(2) 0.14825(17) 0.0417(4) Uani 1 1 d . . . . .
H7 H 0.3262 0.3184 0.0678 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5579(3) 0.2792(2) 0.17275(17) 0.0339(4) Uani 1 1 d . . . . .
C9 C 0.5961(3) 0.2908(2) 0.29121(17) 0.0345(4) Uani 1 1 d . . . . .
H9 H 0.7301 0.2575 0.3113 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4356(3) 0.3520(2) 0.38042(16) 0.0324(4) Uani 1 1 d . . . . .
H10 H 0.4635 0.3607 0.4617 0.039 Uiso 1 1 calc R U . . .
C11 C 0.7288(3) 0.2232(2) 0.07038(19) 0.0454(5) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 '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
O1 Ni1 O1 180.0 2_566 .
O1 Ni1 O2 89.08(5) 2_566 .
O1 Ni1 O2 90.92(5) . .
O1 Ni1 O2 90.92(5) 2_566 2_566
O1 Ni1 O2 89.08(5) . 2_566
O2 Ni1 O2 180.0 . 2_566
O1 Ni1 N1 89.94(5) 2_566 2_566
O1 Ni1 N1 90.06(5) . 2_566
O2 Ni1 N1 90.03(5) . 2_566
O2 Ni1 N1 89.97(5) 2_566 2_566
O1 Ni1 N1 90.07(5) 2_566 .
O1 Ni1 N1 89.93(5) . .
O2 Ni1 N1 89.97(5) . .
O2 Ni1 N1 90.03(5) 2_566 .
N1 Ni1 N1 180.0 2_566 .
C1 O1 Ni1 126.08(11) . .
C3 O2 Ni1 125.49(11) . .
C10 N1 C6 116.98(16) . .
C10 N1 Ni1 121.84(12) . .
C6 N1 Ni1 121.16(12) . .
O1 C1 C2 125.68(16) . .
O1 C1 C4 114.93(16) . .
C2 C1 C4 119.38(16) . .
C1 C2 C3 125.97(16) . .
C1 C2 H2 117.0 . .
C3 C2 H2 117.0 . .
O2 C3 C2 125.72(16) . .
O2 C3 C5 116.15(16) . .
C2 C3 C5 118.13(16) . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N1 C6 C7 123.55(17) . .
N1 C6 H6 118.2 . .
C7 C6 H6 118.2 . .
C6 C7 C8 118.75(17) . .
C6 C7 H7 120.6 . .
C8 C7 H7 120.6 . .
C9 C8 C7 118.60(17) . .
C9 C8 C11 121.34(17) . .
C7 C8 C11 120.01(17) . .
C8 C9 C10 118.77(17) . .
C8 C9 H9 120.6 . .
C10 C9 H9 120.6 . .
N1 C10 C9 123.35(16) . .
N1 C10 H10 118.3 . .
C9 C10 H10 118.3 . .
F1A C11 F2A 112.2(8) . .
F3B C11 F1B 108.1(7) . .
F3B C11 F2B 105.4(5) . .
F1B C11 F2B 102.6(6) . .
F1A C11 F3A 104.2(7) . .
F2A C11 F3A 101.6(7) . .
F1A C11 C8 115.1(5) . .
F3B C11 C8 114.0(4) . .
F2A C11 C8 114.5(6) . .
F1B C11 C8 114.2(4) . .
F2B C11 C8 111.4(5) . .
F3A C11 C8 107.6(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0069(12) 2_566
Ni1 O1 2.0069(12) .
Ni1 O2 2.0288(12) .
Ni1 O2 2.0288(12) 2_566
Ni1 N1 2.1685(15) 2_566
Ni1 N1 2.1685(15) .
F1A C11 1.263(10) .
F2A C11 1.298(9) .
F3A C11 1.381(10) .
F1B C11 1.303(7) .
F2B C11 1.356(8) .
F3B C11 1.290(8) .
O1 C1 1.265(2) .
O2 C3 1.260(2) .
N1 C10 1.337(2) .
N1 C6 1.343(2) .
C1 C2 1.395(3) .
C1 C4 1.513(2) .
C2 C3 1.406(3) .
C2 H2 0.9500 .
C3 C5 1.513(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.371(3) .
C6 H6 0.9500 .
C7 C8 1.389(3) .
C7 H7 0.9500 .
C8 C9 1.377(2) .
C8 C11 1.495(3) .
C9 C10 1.384(3) .
C9 H9 0.9500 .
C10 H10 0.9500 .
