Metal-Free sp(2)-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes.
Chernichenko, Konstantin; Lindqvist, Markus; Kótai, Bianka; Nieger, Martin; Sorochkina, Kristina; Pápai, Imre; Repo, Timo; Journal of the American Chemical Society 138 (2016) 4860–4868; doi:10.1021/jacs.6b00819

data_4130151
_publ_section_title
;
 Metal-Free sp(2)-C-H Borylation as a Common Reactivity Pattern of
 Frustrated 2-Aminophenylboranes.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4860
_journal_page_last               4868
_journal_paper_doi               10.1021/jacs.6b00819
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C39 H40 B N'
_chemical_formula_sum            'C39 H40 B N'
_chemical_formula_weight         533.53
_chemical_name_systematic
;
 5-([1,1'-biphenyl]-2-yl)-5-(2-(2,2,6,6-tetramethylpiperidin-
1-ium-1-yl)phenyl)-5H-dibenzo[b,d]borol-5-uide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 115.643(1)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.1800(4)
_cell_length_b                   18.5354(4)
_cell_length_c                   18.4087(4)
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.7
_cell_measurement_theta_min      3.4
_cell_volume                     5899.9(2)
_computing_cell_refinement       SAINT
_computing_data_collection       APEX2
_computing_data_reduction        SAINT
_computing_molecular_graphics    Shelxtl
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture with Photon100 detector'
_diffrn_measurement_method       'rotation in \f and \w, 0.5\%, shutterless'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            56050
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.143
_diffrn_reflns_theta_min         2.555
_diffrn_source                   'I\mS microfocus'
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       plates
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.256
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     754
_refine_ls_number_reflns         11434
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0617P)^2^+4.9700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8813
_reflns_number_total             11434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b00819_si_002.cif
_cod_data_source_block           les131_compound_41
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4130151
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014-3
_shelx_res_checksum              5301