Palladium-catalyzed intramolecular dehydrogenative coupling of BH and OH: synthesis of carborane-fused benzoxaboroles.
Cui, Chun-Xiao; Zhang, Jie; Qiu, Zaozao; Xie, Zuowei; Dalton transactions (Cambridge, England : 2003) 49 (2020) 1380–1383; doi:10.1039/c9dt04553h

data_7703223
_publ_section_title
;
 Palladium-catalyzed intramolecular dehydrogenative coupling of BH and OH:
 synthesis of carborane-fused benzoxaboroles.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1380
_journal_page_last               1383
_journal_paper_doi               10.1039/c9dt04553h
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C12 H22 B10 O'
_chemical_formula_sum            'C12 H22 B10 O'
_chemical_formula_weight         290.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-10-28 deposited with the CCDC.	2020-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.850(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7025(7)
_cell_length_b                   9.3292(10)
_cell_length_c                   13.3822(14)
_cell_measurement_reflns_used    3614
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.65
_cell_measurement_theta_min      2.18
_cell_volume                     835.74(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.684
_diffrn_reflns_theta_min         2.663
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0536 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.9275.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.091
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.2509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2302
_reflns_number_total             2736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt04553h2.cif
_cod_data_source_block           2g
_cod_depositor_comments
'Adding full bibliography for 7703222--7703226.cif.'
_cod_database_code               7703223
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C2, B2}
3. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(B2)
4. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H4A(0.5) H4B(0.5) C2(0.5) H2(0.5) B2(0.5)
 H2A(0.5) H3A(0.5) H3B(0.5) H5A(0.5) H5B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
5.c Boron cage BH refined with riding coordinates:
 B4(H4A), B4(H4B), C2(H2), B2(H2A), B3(H3A), B3(H3B), B5(H5A), B5(H5B),
 B7(H7A), B6(H6)
;
_shelx_res_checksum              62165
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'