C(sp(2))-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities.
Obligacion, Jennifer V.; Bezdek, Máté J; Chirik, Paul J.; Journal of the American Chemical Society 139 (2017) 2825–2832; doi:10.1021/jacs.6b13346

data_4125824
_publ_section_title
;
 C(sp(2))-H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt
 Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic
 Opportunities.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2825
_journal_page_last               2832
_journal_paper_doi               10.1021/jacs.6b13346
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C30 H55 Co N O4 P2'
_chemical_formula_weight         614.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-08-26 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 106.9960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2149(5)
_cell_length_b                   19.0932(6)
_cell_length_c                   11.5026(3)
_cell_measurement_reflns_used    9741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.81
_cell_measurement_theta_min      3.67
_cell_volume                     3405.61(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP3 (Farraguia, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23626
_diffrn_reflns_point_group_measured_fraction_full 0.704
_diffrn_reflns_point_group_measured_fraction_max 0.717
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.801
_diffrn_reflns_theta_min         2.314
_exptl_absorpt_coefficient_mu    5.084
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS BRUKER AXS'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.184
_refine_diff_density_max         1.155
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.000(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         8679
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0476P)^2^+1.7485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.469
_reflns_Friedel_fraction_full    0.450
_reflns_Friedel_fraction_max     0.459
_reflns_number_gt                8454
_reflns_number_total             8679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13346_si_001.cif
_cod_data_source_block           jvo18
_cod_database_code               4125824
_shelxl_version_number           2014-3
_shelx_res_checksum              21576
_shelx_hkl_checksum              33377