Chiral Hypervalent Bromine(III) (Bromonium Salt): Hydrogen- and Halogen-Bonding Bifunctional Asymmetric Catalysis by Diaryl-λ3-bromanes
Yoshida, Yasushi; Mino, Takashi; Sakamoto, Masami; ACS Catalysis  (2021) 13028–13033; doi:10.1021/acscatal.1c04070

data_4519091
_publ_section_title
;
 Chiral Hypervalent Bromine(III) (Bromonium Salt): Hydrogen- and
 Halogen-Bonding Bifunctional Asymmetric Catalysis by Diaryl-\l3-bromanes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              13028
_journal_page_last               13033
_journal_paper_doi               10.1021/acscatal.1c04070
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C32 H26 B Br Cl3 F4 N O'
_chemical_formula_weight         713.61
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 104.181(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7600(3)
_cell_length_b                   10.7865(3)
_cell_length_c                   13.7635(4)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.5460
_cell_measurement_theta_min      3.3120
_cell_volume                     1548.75(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25852
_diffrn_reflns_theta_full        66.694
_diffrn_reflns_theta_max         66.694
_diffrn_reflns_theta_min         3.312
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    4.639
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.278
_refine_ls_abs_structure_details
;
Flack x determined using 2239 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.686
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5382
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.686
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0310
_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^)+(0.1000P)^2^+0.5425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                5146
_reflns_number_total             5382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c04070_si_002.cif
_cod_data_source_block           I
_cod_database_code               4519091
_shelx_hkl_checksum              13893