B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling of B-Bromo-Carboranes.
Dziedzic, Rafal M.; Saleh, Liban M. A.; Axtell, Jonathan C.; Martin, Joshua L.; Stevens, Simone L.; Royappa, A. Timothy; Rheingold, Arnold L.; Spokoyny, Alexander M.; Journal of the American Chemical Society 138 (2016) 9081–9084; doi:10.1021/jacs.6b05505

data_4125154
_publ_section_title
;
 B-N, B-O, and B-CN Bond Formation via Palladium-Catalyzed Cross-Coupling
 of B-Bromo-Carboranes.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9081
_journal_page_last               9084
_journal_paper_doi               10.1021/jacs.6b05505
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C2 H11 B10 Br O'
_chemical_formula_sum            'C2 H11 B10 Br O'
_chemical_formula_weight         239.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.5493(3)
_cell_length_b                   13.4359(3)
_cell_length_c                   24.2837(7)
_cell_measurement_reflns_used    5587
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.867
_cell_measurement_theta_min      2.334
_cell_volume                     4094.50(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30712
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.090
_diffrn_reflns_theta_min         2.374
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.958
_exptl_absorpt_correction_T_max  0.2651
_exptl_absorpt_correction_T_min  0.1843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0832 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.6952.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0377P)^2^+0.7102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3906
_reflns_number_total             5386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b05505_si_002.cif
_cod_data_source_block           spok17_a
_cod_depositor_comments
'Adding full bibliography for 4125150--4125156.cif.'
_cod_database_code               4125154
_shelx_estimated_absorpt_t_max   0.693
_shelx_estimated_absorpt_t_min   0.383
_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 O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2B)
2.b Boron cage BH refined with riding coordinates:
 C1(H1A), C2(H2), B1(H1B), B2(H2A), B3(H3), B4(H4), B5(H5), B6(H6), B9(H9),
 B10(H10), C3(H3A), C4(H4A), B11(H11), B12(H12), B13(H13), B14(H14), B15(H15),
 B16(H16), B19(H19), B20(H20)
;
_shelx_res_checksum              13654
_shelx_hkl_checksum              50396
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id Br,OH-mCB
_olex2_submission_special_instructions 'No special instructions were received'