Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization.
Su, Yuanting; Huan Do, Dinh Cao; Li, Yongxin; Kinjo, Rei; Journal of the American Chemical Society 141 (2019) 13729–13733; doi:10.1021/jacs.9b06022

data_4128825
_publ_section_title
;
 Metal-Free Selective Borylation of Arenes by a Diazadiborinine via
 C-H/C-F Bond Activation and Dearomatization.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13729
_journal_page_last               13733
_journal_paper_doi               10.1021/jacs.9b06022
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C74 H77 B2 Cl2 N5'
_chemical_formula_weight         1128.92
_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
_cell_angle_alpha                96.7682(12)
_cell_angle_beta                 99.3960(13)
_cell_angle_gamma                107.4614(12)
_cell_formula_units_Z            2
_cell_length_a                   14.2653(5)
_cell_length_b                   15.3826(5)
_cell_length_c                   15.3931(5)
_cell_measurement_reflns_used    9508
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.9828
_cell_measurement_theta_min      2.3957
_cell_volume                     3128.59(18)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            101889
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         2.40
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.339
_exptl_crystal_size_min          0.252
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.736
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     800
_refine_ls_number_reflns         19565
_refine_ls_number_restraints     258
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+3.0101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                13069
_reflns_number_total             19565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06022_si_003.cif
_cod_data_source_block           rei752m
_cod_database_code               4128825
_shelx_res_checksum              84960
_shelx_hkl_checksum              61218