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_1573777
_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, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C28 H28 B10 O'
_chemical_formula_weight         488.60
_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             2023-06-28
_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                90
_cell_angle_beta                 90.849(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0683(8)
_cell_length_b                   18.8770(9)
_cell_length_c                   18.5211(10)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    225.00
_cell_measurement_theta_max      54.621
_cell_measurement_theta_min      3.851
_cell_volume                     5267.6(5)
_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      225.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36906
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.992
_diffrn_reflns_theta_min         2.551
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1673 before and 0.1054 after correction.
The Ratio of minimum to maximum transmission is 0.5808.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         9912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1665
_refine_ls_R_factor_gt           0.1093
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1886P)^2^+3.6012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2944
_refine_ls_wR_factor_ref         0.3440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5804
_reflns_number_total             9912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08496a2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 1573766--1573777.cif.'
_cod_database_code               1573777
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.848(3)
 0.152(3)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6A), C7(H7A), C11(H11), 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(H7AB), C11A(H11A), C12A(H12C), C13A(H13A),
  C14A(H14A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C23A(H23A),
 C24A(H24A), C25A(H25A), C26A(H26A)
3.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C4S(H4SA,H4SB,H4SC)
3.d Boron cage BH refined with riding coordinates:
 B3(H3), B4(H4), B6(H6), B7(H7), B8(H8), B9(H9), B10(H10), B12(H12), B3A(H3A),
 B4A(H4AA), B6A(H6AA), B7A(H7AA), B8A(H8A), B9A(H9A), B10A(H10A), B12A(H12B)
;
_shelx_res_checksum              20115
_olex2_submission_special_instructions 'No special instructions were received'