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_4126566
_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         'C22 H32 B2 N2'
_chemical_formula_sum            'C22 H32 B2 N2'
_chemical_formula_weight         346.11
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.3030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3173(17)
_cell_length_b                   10.2417(9)
_cell_length_c                   21.1401(18)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      30.3951
_cell_measurement_theta_min      2.2447
_cell_volume                     4069.8(6)
_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 0.999
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            51110
_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         30.500
_diffrn_reflns_theta_min         1.184
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0516 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.9413.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         12405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0600P)^2^+1.0250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1285
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9418
_reflns_number_total             12405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08143_si_002.cif
_cod_data_source_block           jll20170301_0m
_cod_database_code               4126566
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.7461
_shelx_estimated_absorpt_t_min   0.7023
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C44(H44A,H44B), C7(H7A,H7B), C33(H33A,H33B), C29(H29A,H29B),
 C32(H32A,H32B), C18(H18A,H18B), C43(H43A,H43B), C10(H10A,H10B), C8(H8A,H8B),
 C40(H40A,H40B), C30(H30A,H30B), C22(H22A,H22B), C31(H31A,H31B), C41(H41A,H41B),
  C42(H42A,H42B), C9(H9A,H9B), C19(H19A,H19B), C21(H21A,H21B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C36(H36), C37(H37), C35(H35), C38(H38), C5(H5), C14(H14), C24(H24),
 C2(H2), C15(H15), C16(H16), C27(H27), C4(H4), C3(H3), C25(H25), C26(H26)
;
_shelx_res_checksum              29646
_shelx_hkl_checksum              82088
_olex2_submission_special_instructions 'No special instructions were received'