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_4132126
_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_formula_moiety         'C9 H13 B10 I O'
_chemical_formula_sum            'C9 H13 B10 I O'
_chemical_formula_weight         372.19
_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
_audit_creation_date             2017-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.709(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.104(3)
_cell_length_b                   7.3271(16)
_cell_length_c                   11.901(3)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.33
_cell_volume                     760.3(4)
_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      293.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5233
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_min         2.500
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.7843.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0278P)^2^+0.2436P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.793
_reflns_Friedel_fraction_max     0.787
_reflns_number_gt                2385
_reflns_number_total             2661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01754_si_002.cif
_cod_data_source_block           (R)-4a
_cod_original_cell_volume        760.4(3)
_cod_database_code               4132126
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.818
_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)
2.b Boron cage BH refined with riding coordinates:
 C2(H2), B6(H6A), B11(H11), B7(H7A), B3(H3), B5(H5A), B10(H10), B8(H8A), B9(H9)
;
_shelx_res_checksum              85431
_shelx_hkl_checksum              74568
_olex2_submission_special_instructions 'No special instructions were received'