Metal-Free Borylation of Heteroarenes using Ambiphilic Aminoboranes: On the Importance of Sterics in Frustrated Lewis Pair C-H Bond Activation.
Légaré Lavergne, Julien; Jayaraman, Arumugam; Misal-Castro, Luis C; Rochette, Etienne; Fontaine, Frédéric-Georges; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b08143

data_4126565
_publ_section_title
;
 Metal-Free Borylation of Heteroarenes using Ambiphilic Aminoboranes: On
 the Importance of Sterics in Frustrated Lewis Pair C-H Bond Activation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b08143
_journal_year                    2017
_chemical_formula_moiety         'C20 H32 B2 N2'
_chemical_formula_sum            'C20 H32 B2 N2'
_chemical_formula_weight         322.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2017-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.721(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9852(12)
_cell_length_b                   12.8546(14)
_cell_length_c                   16.2845(18)
_cell_measurement_reflns_used    5515
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.5643
_cell_measurement_theta_min      2.5098
_cell_volume                     2190.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SMART APEX II (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'bruker SMART CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19795
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.818
_diffrn_reflns_theta_min         1.989
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0533 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.9263.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.977
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0276P)^2^+0.6379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3493
_reflns_number_total             4230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08143_si_002.cif
_cod_data_source_block           jll20160810_02_0m_a_sq
_cod_database_code               4126565
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.7453
_shelx_estimated_absorpt_t_min   0.6904
_olex2_refinement_description
;
;
_shelx_res_checksum              48210
_shelx_hkl_checksum              84116
_shelx_fab_checksum              2509
_olex2_submission_special_instructions 'No special instructions were received'