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_4126569
_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         'C11 H15 B F3 N'
_chemical_formula_sum            'C11 H15 B F3 N'
_chemical_formula_weight         229.05
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-02-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.0093(5)
_cell_length_b                   8.6076(3)
_cell_length_c                   20.1758(8)
_cell_measurement_reflns_used    7660
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      31.9371
_cell_measurement_theta_min      2.2962
_cell_volume                     2186.98(14)
_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)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30343
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.853
_diffrn_reflns_theta_min         1.617
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0459 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.9299.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.048
_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     289
_refine_ls_number_reflns         7914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0530P)^2^+0.4590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6014
_reflns_number_total             7914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08143_si_002.cif
_cod_data_source_block           er20161205_0m_a
_cod_database_code               4126569
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.7465
_shelx_estimated_absorpt_t_min   0.6942
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              37564
_shelx_hkl_checksum              75518
_olex2_submission_special_instructions 'No special instructions were received'