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_4129373
_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 rmad
_chemical_formula_moiety         'C8 H14 Br Cl O2'
_chemical_formula_sum            'C8 H14 Br Cl O2'
_chemical_formula_weight         257.55
_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     vecmap
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90
_cell_angle_beta                 100.7510(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9216(3)
_cell_length_b                   7.4237(3)
_cell_length_c                   8.8915(4)
_cell_measurement_reflns_used    8713
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.74
_cell_measurement_theta_min      5.06
_cell_volume                     513.71(4)
_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 0.992
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9058
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.745
_diffrn_reflns_theta_min         5.063
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    7.544
_exptl_absorpt_correction_T_max  0.8635
_exptl_absorpt_correction_T_min  0.5301
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       tablet
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 842 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.070(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1927
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0158
_refine_ls_R_factor_gt           0.0158
_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^)+(0.0226P)^2^+0.0638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0403
_refine_ls_wR_factor_ref         0.0404
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                1924
_reflns_number_total             1927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b01384_si_003.cif
_cod_data_source_block           su1417
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129373
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.350
_shelx_estimated_absorpt_t_max   0.800
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              92515
_shelx_hkl_checksum              68528