Catalytic chemo-, regio-, and enantioselective bromochlorination of allylic alcohols.
Hu, Dennis X.; Seidl, Frederick J.; Bucher, Cyril; Burns, Noah Z.; Journal of the American Chemical Society 137 (2015) 3795–3798; doi:10.1021/jacs.5b01384

data_4129370
_publ_section_title
;
 Catalytic chemo-, regio-, and enantioselective bromochlorination of
 allylic alcohols.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3795
_journal_page_last               3798
_journal_paper_doi               10.1021/jacs.5b01384
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H16 Br Cl O'
_chemical_formula_sum            'C12 H16 Br Cl O'
_chemical_formula_weight         291.61
_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   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.199(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4404(18)
_cell_length_b                   6.0532(8)
_cell_length_c                   31.206(4)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.32
_cell_volume                     2512.9(6)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-5.0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            54621
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         1.319
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.457
_exptl_absorpt_correction_T_max  0.9396
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       blade
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.037
_refine_diff_density_max         1.053
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Flack x determined using 3700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         10319
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0585P)^2^+2.7246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                9170
_reflns_number_total             10319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b01384_si_001.cif
_cod_data_source_block           su1414
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129370
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.515
_shelx_estimated_absorpt_t_max   0.883
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_shelx_res_checksum              70277
_shelx_hkl_checksum              3269