Synthesis of Enantioenriched Bromohydrins via Divergent Reactions of Racemic Intermediates from Anchimeric Oxygen Borrowing.
Cao, Yi-Ming; Lentz, Dieter; Christmann, Mathias; Journal of the American Chemical Society 140 (2018) 10677–10681; doi:10.1021/jacs.8b06432

data_4132785
_publ_section_title
;
 Synthesis of Enantioenriched Bromohydrins via Divergent Reactions of
 Racemic Intermediates from Anchimeric Oxygen Borrowing.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10677
_journal_page_last               10681
_journal_paper_doi               10.1021/jacs.8b06432
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H15 Br O3'
_chemical_formula_weight         383.23
_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_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 95.953(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0480(6)
_cell_length_b                   5.9460(4)
_cell_length_c                   34.639(3)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.55
_cell_measurement_theta_min      2.56
_cell_volume                     1648.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            33229
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.547
_diffrn_reflns_theta_min         3.849
_diffrn_source                   'Incoatec Microfocus Source'
_exptl_absorpt_coefficient_mu    3.523
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       platelett
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.061(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+1.3695P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                6161
_reflns_number_total             6314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b06432_si_001.cif
_cod_data_source_block           0601X_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132785
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.333
_shelx_estimated_absorpt_t_max   0.902
_shelx_res_checksum              27257
_shelx_hkl_checksum              42580