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_4130149
_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_absolute_configuration ad
_chemical_formula_moiety         'C27 H20 B F5 N2 O'
_chemical_formula_sum            'C27 H20 B F5 N2 O'
_chemical_formula_weight         494.26
_chemical_name_systematic
;
 4,4-dimethyl-3-oxo-1-(perfluorophenyl)-1,2-diphenyl-1,2,3,4-
tetrahydrobenzo[c][1,5,2]diazaborinin-4-ium-1-uide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3517(1)
_cell_length_b                   14.6007(2)
_cell_length_c                   18.7457(2)
_cell_measurement_reflns_used    7208
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      75.9
_cell_measurement_theta_min      3.8
_cell_volume                     2285.86(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'rotation in \w, 1\%'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11251
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.877
_diffrn_reflns_theta_min         3.837
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       rods
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Probably racemic twin. Hooft's parameter = 0.45(4).
;
_refine_ls_abs_structure_Flack   0.46(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0686P)^2^+0.2715P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4569
_reflns_number_total             4775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b00819_si_002.cif
_cod_data_source_block           l_110_cu_compound_7
_cod_database_code               4130149
_shelx_estimated_absorpt_t_min   0.744
_shelx_estimated_absorpt_t_max   0.952
_shelxl_version_number           2013-2
_shelx_res_checksum              35925