Iridium-catalyzed selective arylation of B(6)-H of 3-aryl-<i>o</i>-carboranes with arylboronic acid <i>via</i> direct B-H activation.
Yang, Han-Bo; Guo, Yan; Cao, Ke; Jiang, Qi-Jia; Teng, Chao-Chao; Zhu, Dao-Yong; Wang, Shao-Hua; Chemical communications (Cambridge, England) 60 (2024) 1124–1127; doi:10.1039/d3cc05630a

data_7132557
_publ_section_title
;
 Iridium-catalyzed selective arylation of B(6)-H of
 3-aryl-<i>o</i>-carboranes with arylboronic acid <i>via</i> direct B-H
 activation.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1124
_journal_page_last               1127
_journal_paper_doi               10.1039/d3cc05630a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C14 H20 B10'
_chemical_formula_sum            'C14 H20 B10'
_chemical_formula_weight         296.41
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-10-05 deposited with the CCDC.	2024-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.451(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8355(12)
_cell_length_b                   10.9790(9)
_cell_length_c                   9.9081(7)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.766
_cell_measurement_theta_min      2.269
_cell_volume                     1694.0(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12698
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.425
_diffrn_reflns_theta_min         2.270
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.7287.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0669P)^2^+0.6867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2059
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05630a2.cif
_cod_data_source_block           yhb-16
_cod_depositor_comments
;
       Adding full bibliography for 7132557.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.15 H3.08 B1.54'
_cod_original_formula_weight         45.60
_cod_original_formula_moiety         '0.154(C14 H20 B10)'
_cod_original_formula_units_Z            26
_cod_database_code               7132557
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C10(H10), C2(H2), C4(H4), C3(H3), C14(H14), C11(H11),
 C12(H12), C13(H13)
2.b Boron cage BH refined with riding coordinates:
 C8(H8), C7(H7), B2A(H2A), B3A(H3A), B9A(H9A), B8A(H8A), B6A(H6A), B5A(H5A),
 B7A(H7A), B10A(H10A)
;
_olex2_submission_special_instructions 'No special instructions were received'