Regioselective Nucleophilic Alkylation/Arylation of B-H Bonds in o-Carboranes: An Alternative Method for Selective Cage Boron Functionalization.
Tang, Cen; Zhang, Jiji; Zhang, Jie; Xie, Zuowei; Journal of the American Chemical Society 140 (2018) 16423–16427; doi:10.1021/jacs.8b10270

data_4133479
_publ_section_title
;
 Regioselective Nucleophilic Alkylation/Arylation of B-H Bonds in
 o-Carboranes: An Alternative Method for Selective Cage Boron
 Functionalization.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16423
_journal_page_last               16427
_journal_paper_doi               10.1021/jacs.8b10270
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C9 H18 B10'
_chemical_formula_weight         234.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9901(9)
_cell_length_b                   13.1211(11)
_cell_length_c                   9.2461(6)
_cell_measurement_reflns_used    107
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1454.63(19)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1069
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6886
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.336
_diffrn_reflns_theta_min         4.996
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3019
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1964
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.1688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1823
_reflns_Friedel_coverage         0.385
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.438
_reflns_number_gt                1055
_reflns_number_total             1964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10270_si_003.cif
_cod_data_source_block           4g
_cod_database_code               4133479
_shelx_estimated_absorpt_t_min   0.848
_shelx_estimated_absorpt_t_max   0.905
_shelxl_version_number           2014/6
_shelx_res_checksum              36848
_shelx_hkl_checksum              47064