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_7703224
_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         'C9 H16 B10 O2'
_chemical_formula_sum            'C9 H16 B10 O2'
_chemical_formula_weight         264.47
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-10-28 deposited with the CCDC.	2020-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.920(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1038(14)
_cell_length_b                   10.5666(15)
_cell_length_c                   26.989(4)
_cell_measurement_reflns_used    6573
_cell_measurement_temperature    130
_cell_measurement_theta_max      28.79
_cell_measurement_theta_min      2.45
_cell_volume                     2866.1(7)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130.0
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25445
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1032 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.5170.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2251
_exptl_crystal_description       block
_exptl_crystal_F_000             1088.3628
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.4717
_refine_diff_density_min         -0.3325
_refine_diff_density_rms         0.0726
_refine_ls_d_res_high            0.7335
_refine_ls_d_res_low             9.8323
_refine_ls_goodness_of_fit_ref   1.0194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     381
_refine_ls_number_reflns         7574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0194
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.3206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              -11
_reflns_number_gt                5268
_reflns_number_total             7574
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9dt04553h2.cif
_cod_data_source_block           2s
_cod_depositor_comments
'Adding full bibliography for 7703222--7703226.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7703224
_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), C7(H7), C7a(H7aa), C5a(H5aa), C6a(H6aa)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C9a(H9aa,H9ab,H9ac)
2.c Boron cage BH refined with riding coordinates:
 C2(H2), B11(H11), B10(H10), B6(H6a), B5(H5a), B4(H4), B7(H7a), B12(H12),
 B9(H9), B8(H8), C2a(H2a), B11a(H11a), B7a(H7ab), B3a(H3a), B4a(H4a), B5a(H5ab),
  B10a(H10a), B12a(H12a), B8a(H8a), B9a(H9ad)
;
_olex2_submission_special_instructions 'No special instructions were received'