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_1573776
_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         'C22 H20 B10'
_chemical_formula_sum            'C22 H20 B10'
_chemical_formula_weight         392.48
_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             2024-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                80.467(3)
_cell_angle_beta                 79.395(3)
_cell_angle_gamma                71.939(3)
_cell_formula_units_Z            4
_cell_length_a                   11.4881(9)
_cell_length_b                   13.9932(11)
_cell_length_c                   14.0464(12)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.903
_cell_measurement_theta_min      2.804
_cell_volume                     2095.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      170.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_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  0.0922
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32354
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.417
_diffrn_reflns_theta_min         2.803
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1515 before and 0.0866 after correction.
The Ratio of minimum to maximum transmission is 0.7247.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0665
_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^)+(0.1225P)^2^+0.4559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.2006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5789
_reflns_number_total             7929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08496a2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 1573766--1573777.cif.'
_cod_database_code               1573776
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.952
_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(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C4A(H4A), C5A(H5AA), C6A(H6AA),
 C8A(H8AA), C9A(H9AA), C10A(H10B), C14A(H14A), C15A(H15A), C16A(H16A),
 C18A(H18A), C19A(H19A), C20A(H20A)
2.b Boron cage BH refined with riding coordinates:
 B3(H3), B5(H5A), B6(H6A), B8(H8A), B9(H9A), B10(H10A), B11(H11), B12(H12),
 B3A(H3A), B5A(H5AB), B6A(H6AB), B8A(H8AB), B9A(H9AB), B10A(H10C), B11A(H11A),
 B12A(H12A)
;
_shelx_res_checksum              72027
_olex2_submission_special_instructions 'No special instructions were received'