Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents.
Goh, Shermin S.; Guduguntla, Sureshbabu; Kikuchi, Takashi; Lutz, Martin; Otten, Edwin; Fujita, Makoto; Feringa, Ben L.; Journal of the American Chemical Society 140 (2018) 7052–7055; doi:10.1021/jacs.8b02992

data_4132335
_publ_section_title
;
 Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed
 Asymmetric Allylic Substitution with Organolithium Reagents.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7052
_journal_page_last               7055
_journal_paper_doi               10.1021/jacs.8b02992
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H17 Br O2'
_chemical_formula_weight         285.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.058(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6584(11)
_cell_length_b                   5.6840(5)
_cell_length_c                   16.1484(14)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      3.00
_cell_volume                     1184.95(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18426
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.926
_diffrn_reflns_theta_min         2.998
_exptl_absorpt_coefficient_mu    3.452
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1197 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0184
_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^)+(0.0208P)^2^+0.5343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0480
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2755
_reflns_number_total             2821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02992_si_004.cif
_cod_data_source_block           mo_molan418_0m
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4132335
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.231
_shelx_estimated_absorpt_t_max   0.874
_shelx_res_checksum              10590
_shelx_hkl_checksum              89387