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_4129371
_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         'C18 H17 Br2 Cl O2'
_chemical_formula_sum            'C18 H17 Br2 Cl O2'
_chemical_formula_weight         460.59
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                63.959(3)
_cell_angle_beta                 86.221(3)
_cell_angle_gamma                74.140(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6359(8)
_cell_length_b                   10.3823(9)
_cell_length_c                   11.5035(10)
_cell_measurement_reflns_used    6084
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      2.26
_cell_volume                     889.68(14)
_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)'
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_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 Kappa X8-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  0.0341
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20736
_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         27.262
_diffrn_reflns_theta_min         1.974
_exptl_absorpt_coefficient_mu    4.712
_exptl_absorpt_correction_T_max  0.9156
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.037
_refine_diff_density_max         1.944
_refine_diff_density_min         -1.742
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 2666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7919
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0353P)^2^+0.0898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                6587
_reflns_number_total             7919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b01384_si_002.cif
_cod_data_source_block           su1415
_cod_database_code               4129371
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.569
_shelx_estimated_absorpt_t_max   0.845
_shelx_res_checksum              81437
_shelx_hkl_checksum              69084