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_4129374
_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         'C7 H12 Br Cl O2'
_chemical_formula_sum            'C7 H12 Br Cl O2'
_chemical_formula_weight         243.53
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_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   6.1762(7)
_cell_length_b                   6.3096(8)
_cell_length_c                   23.492(3)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      3.34
_cell_volume                     915.47(19)
_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 1.000
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16292
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.471
_diffrn_reflns_theta_min         1.734
_exptl_absorpt_coefficient_mu    4.732
_exptl_absorpt_correction_T_max  0.7554
_exptl_absorpt_correction_T_min  0.5818
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/2 (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_description       rod
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 891 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         2321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0159
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0166P)^2^+0.0365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0386
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2239
_reflns_number_total             2321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b01384_si_004.cif
_cod_data_source_block           su1426a
_cod_original_cell_volume        915.46(19)
_cod_database_code               4129374
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.537
_shelx_estimated_absorpt_t_max   0.675
_shelx_res_checksum              31682
_shelx_hkl_checksum              94285