Palladium-catalyzed intramolecular aerobic oxidative cross-coupling of BH/CH between <i>o</i>-carborane and arenes.
Wang, Zhen; Yu, Jiahui; Zhang, Jie; Zhang, Dengsong; Qiu, Zaozao; Xie, Zuowei; Chemical science 16 (2025) 3705–3712; doi:10.1039/d4sc08496a

data_1573767
_publ_section_title
;
 Palladium-catalyzed intramolecular aerobic oxidative cross-coupling of
 BH/CH between <i>o</i>-carborane and arenes.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              3705
_journal_page_last               3712
_journal_paper_doi               10.1039/d4sc08496a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C26 H24 B10'
_chemical_formula_sum            'C26 H24 B10'
_chemical_formula_weight         444.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                75.392(2)
_cell_angle_beta                 80.868(2)
_cell_angle_gamma                87.318(2)
_cell_formula_units_Z            8
_cell_length_a                   10.8412(3)
_cell_length_b                   19.4475(6)
_cell_length_c                   23.3896(7)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      2.98
_cell_volume                     4711.3(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            68999
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.996
_diffrn_reflns_theta_min         2.978
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1299 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.8478.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1297
_refine_ls_number_reflns         17788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0873P)^2^+1.4672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13094
_reflns_number_total             17788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08496a2.cif
_cod_data_source_block           12
_cod_depositor_comments
'Adding full bibliography for 1573766--1573777.cif.'
_cod_database_code               1573767
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.979
_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:
 C4(H4A), C5(H5), C6(H6A), C7(H7), C11(H11A), C12(H12A), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26),
  C4A(H4AB), C5A(H5A), C6A(H6AB), C7A(H7A), C11A(H11C), C12A(H12C), C13A(H13A),
 C14A(H14A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C23A(H23A),
 C24A(H24A), C25A(H25A), C26A(H26A), C4B(H4BA), C5B(H5B), C6B(H6BA), C7B(H7B),
 C11B(H11E), C12B(H12E), C13B(H13B), C14B(H14B), C16B(H16B), C17B(H17B),
 C18B(H18B), C19B(H19B), C23B(H23B), C24B(H24B), C25B(H25B), C26B(H26B),
 C4C(H4CA), C5C(H5C), C6C(H6CA), C7C(H7C), C11C(H11G), C12C(H12G), C13C(H13C),
 C14C(H14C), C16C(H16C), C17C(H17C), C18C(H18C), C19C(H19C), C23C(H23C),
 C24C(H24C), C25C(H25C), C26C(H26C)
2.b Boron cage BH refined with riding coordinates:
 B3(H3), B4(H4), B6(H6), B8(H8), B9(H9), B10(H10), B11(H11), B12(H12),
 B3A(H3A), B4A(H4AA), B6A(H6AA), B8A(H8A), B9A(H9A), B10A(H10A), B11A(H11B),
 B12A(H12B), B3B(H3B), B4B(H4B), B6B(H6B), B8B(H8B), B9B(H9B), B10B(H10B),
 B11B(H11D), B12B(H12D), B3C(H3C), B4C(H4C), B6C(H6C), B8C(H8C), B9C(H9C),
 B10C(H10C), B11C(H11F), B12C(H12F)
;
_shelx_res_checksum              72687
_olex2_submission_special_instructions 'No special instructions were received'