Enantioselective Conversion of Achiral Cyclohexadienones to Chiral Cyclohexenones by Desymmetrization.
Han, Yixin; Breitler, Simon; Zheng, Shao-Liang; Corey, E. J.; Organic letters 18 (2016) 6172–6175; doi:10.1021/acs.orglett.6b03186

data_1555955
_publ_section_title
;
 Enantioselective Conversion of Achiral Cyclohexadienones to Chiral
 Cyclohexenones by Desymmetrization.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6172
_journal_page_last               6175
_journal_paper_doi               10.1021/acs.orglett.6b03186
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H15 Cl O'
_chemical_formula_weight         222.70
_space_group_crystal_system      orthorhombic
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7518(2)
_cell_length_b                   8.9722(2)
_cell_length_c                   13.5378(3)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.6
_cell_measurement_theta_min      2.49
_cell_volume                     1063.03(4)
_computing_cell_refinement       'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0091
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.721
_diffrn_reflns_theta_min         5.916
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0201
_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^)+(0.0236P)^2^+0.3953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0524
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1876
_reflns_number_total             1877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03186_si_001.cif
_cod_data_source_block           SB-IV-630
_cod_database_code               1555955
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.623
_shelx_estimated_absorpt_t_max   0.722
_shelx_res_checksum              45431
_shelx_hkl_checksum              51188