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_4130334
_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, C6 D6'
_chemical_formula_sum            'C54 H50 D6 F4 N4 Ni'
_chemical_formula_weight         901.77
_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
_atom_sites_solution_primary     iterative
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                92.736(19)
_cell_angle_beta                 101.401(13)
_cell_angle_gamma                91.53(2)
_cell_formula_units_Z            2
_cell_length_a                   10.652(5)
_cell_length_b                   14.778(5)
_cell_length_c                   14.855(4)
_cell_measurement_reflns_used    9736
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.43
_cell_volume                     2288.1(15)
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.11-0 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_molecular_graphics    'shelXle (Huebschle et al., 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47351
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         1.380
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_preparation
'Crystal fragment soaked in perfluoro polyether oil.'
_exptl_crystal_recrystallization_method
'crystallised from C6D6 by evaporation'
_exptl_crystal_size_max          0.636
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.217
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         9016
_refine_ls_number_restraints     534
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0301P)^2^+1.4738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8289
_reflns_number_total             9016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02337_si_002.cif
_cod_data_source_block           compound_5_C6D6
_cod_database_code               4130334
_shelx_estimated_absorpt_t_min   0.749
_shelx_estimated_absorpt_t_max   0.903
_shelx_res_checksum              33956
_shelx_hkl_checksum              42996