Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis: Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage.
Zhou, Jing; Kuntze-Fechner, Maximilian W; Bertermann, Rüdiger; Paul, Ursula S. D.; Berthel, Johannes H. J.; Friedrich, Alexandra; Du, Zhenting; Marder, Todd B.; Radius, Udo; Journal of the American Chemical Society 138 (2016) 5250–5253; doi:10.1021/jacs.6b02337

data_4130333
_publ_section_title
;
 Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis:
 Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5250
_journal_page_last               5253
_journal_paper_doi               10.1021/jacs.6b02337
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C48 H50 F4 N4 Ni'
_chemical_formula_sum            'C48 H50 F4 N4 Ni'
_chemical_formula_weight         817.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c 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            8
_cell_length_a                   19.9415(5)
_cell_length_b                   18.3839(5)
_cell_length_c                   22.7755(6)
_cell_measurement_reflns_used    6894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.01
_cell_measurement_theta_min      2.21
_cell_volume                     8349.6(4)
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'Saint-NT v. 7.23'
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_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  helios
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30619
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.072
_diffrn_reflns_theta_min         1.752
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             3440
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.118
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         8192
_refine_ls_number_restraints     336
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+8.3387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5867
_reflns_number_total             8192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02337_si_002.cif
_cod_data_source_block           compound_5
_cod_database_code               4130333
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.941
_shelxl_version_number           2014/6
_shelx_res_checksum              45046
_shelx_hkl_checksum              28908