Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes.
Meucci, Elizabeth A.; Nguyen, Shay N.; Camasso, Nicole M.; Chong, Eugene; Ariafard, Alireza; Canty, Allan J.; Sanford, Melanie S.; Journal of the American Chemical Society 141 (2019) 12872–12879; doi:10.1021/jacs.9b06383

data_4127767
_publ_section_title
;
 Nickel(IV)-Catalyzed C-H Trifluoromethylation of (Hetero)arenes.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12872
_journal_page_last               12879
_journal_paper_doi               10.1021/jacs.9b06383
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.04116(11)
_cell_length_b                   13.40403(8)
_cell_length_c                   7.62996(5)
_cell_measurement_reflns_used    18004
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      69.0490
_cell_measurement_theta_min      5.4880
_cell_volume                     1640.565(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_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            23763
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.235
_diffrn_reflns_theta_min         5.516
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    2.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71377
_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            yellow
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0296
_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/[\s^2^(Fo^2^)+(0.0490P)^2^+0.9682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1589
_reflns_number_total             1600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06383_si_002.cif
_cod_data_source_block           sn087
_cod_original_cell_volume        1640.564(19)
_cod_database_code               4127767
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.665
_shelx_estimated_absorpt_t_max   0.873
_shelx_res_checksum              37241
_shelx_hkl_checksum              47107