Enantioselective Synthesis of Chiral-at-Cage o-Carboranes via Pd-Catalyzed Asymmetric B-H Substitution.
Cheng, Ruofei; Li, Bowen; Wu, Jie; Zhang, Jie; Qiu, Zaozao; Tang, Wenjun; You, Shu-Li; Tang, Yong; Xie, Zuowei; Journal of the American Chemical Society 140 (2018) 4508–4511; doi:10.1021/jacs.8b01754

data_4132125
_publ_section_title
;
 Enantioselective Synthesis of Chiral-at-Cage o-Carboranes via
 Pd-Catalyzed Asymmetric B-H Substitution.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4508
_journal_page_last               4511
_journal_paper_doi               10.1021/jacs.8b01754
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C9 H14 B10 O'
_chemical_formula_sum            'C9 H14 B10 O'
_chemical_formula_weight         246.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7015(3)
_cell_length_b                   22.7815(5)
_cell_length_c                   11.3703(3)
_cell_measurement_reflns_used    9235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.003
_cell_measurement_theta_min      3.986
_cell_volume                     2704.30(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1201
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22084
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         82.783
_diffrn_reflns_theta_min         3.985
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1630 before and 0.1017 after correction. The Ratio of minimum to maximum transmission is 0.6906. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_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     721
_refine_ls_number_reflns         9916
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0846
_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^)+(0.0936P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2223
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                6818
_reflns_number_total             9916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01754_si_002.cif
_cod_data_source_block           S-2a
_cod_database_code               4132125
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C5A(H5A), C6A(H6AA), C7A(H7AA), C8A(H8AA),
 C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C5C(H5C), C6C(H6C), C7C(H7C), C8C(H8C)
2.b Boron cage BH refined with riding coordinates:
 C2(H2), B3(H3), B4(H4), B6(H6A), B7(H7A), B8(H8A), B9(H9), B10(H10), B11(H11),
  B12(H12), C2A(H2A), B3A(H3A), B4A(H4A), B6A(H6AB), B7A(H7AB), B8A(H8AB),
 B9A(H9A), B10A(H10A), B11A(H11A), B12A(H12A), C2B(H2B), B3B(H3B), B4B(H4B),
 B6B(H6BA), B7B(H7BA), B8B(H8BA), B9B(H9B), B10B(H10B), B11B(H11B), B12B(H12B),
 C2C(H2C), B3C(H3C), B4C(H4C), B6C(H6CA), B7C(H7CA), B8C(H8CA), B9C(H9C),
 B10C(H10C), B11C(H11C), B12C(H12C)
;
_shelx_res_checksum              29582
_shelx_hkl_checksum              74436
_olex2_submission_special_instructions 'No special instructions were received'