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_1573769
_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         'C13 H18 B10 O'
_chemical_formula_sum            'C13 H18 B10 O'
_chemical_formula_weight         298.37
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2024-11-29 deposited with the CCDC.	2025-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.391(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1385(6)
_cell_length_b                   22.1234(14)
_cell_length_c                   10.2306(7)
_cell_measurement_reflns_used    2326
_cell_measurement_temperature    221.42
_cell_measurement_theta_max      54.067
_cell_measurement_theta_min      5.692
_cell_volume                     1608.6(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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      221.42
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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  0.08
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_number            3052
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.956
_diffrn_reflns_theta_min         5.136
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1643 before and 0.1057 after correction.
 
For component 2:
 wR2(int) was 0.1894 before and 0.0991 after correction.
 The Ratio of minimum to maximum transmission is 0.30.

Final HKLF 4 output contains 18636 reflections, Rint = 0.2085
 (8424 with I > 3sig(I), Rint = 0.1859)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0977
_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^)+(0.1791P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2500
_refine_ls_wR_factor_ref         0.2780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2078
_reflns_number_total             3052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08496a2.cif
_cod_data_source_block           2ha
_cod_depositor_comments
'Adding full bibliography for 1573766--1573777.cif.'
_cod_database_code               1573769
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Boron cage BH refined with riding coordinates:
 C1(H1), B3(H3), B4(H4), B5(H5A), B6(H6A), B8(H8A), B9(H9A), B10(H10A),
 B11(H11), B12(H12)
;
_shelx_res_checksum              44261
_olex2_submission_special_instructions 'No special instructions were received'