Cobalt-Catalyzed Enantioselective Vinylation of Activated Ketones and Imines.
Huang, Yuan; Huang, Rui-Zhi; Zhao, Yu; Journal of the American Chemical Society 138 (2016) 6571–6576; doi:10.1021/jacs.6b02372

data_4125087
_publ_section_title
;
 Cobalt-Catalyzed Enantioselective Vinylation of Activated Ketones and
 Imines.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6571
_journal_page_last               6576
_journal_paper_doi               10.1021/jacs.6b02372
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 Cl O3'
_chemical_formula_sum            'C19 H17 Cl O3'
_chemical_formula_weight         328.77
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.565(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9854(7)
_cell_length_b                   7.5004(8)
_cell_length_c                   18.085(2)
_cell_measurement_reflns_used    2574
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.190
_cell_measurement_theta_min      4.934
_cell_volume                     804.82(16)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2015.5.2'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10346
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.190
_diffrn_reflns_theta_min         4.934
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.117
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0233
_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^)+(0.0219P)^2^+0.1451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0587
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                2798
_reflns_number_total             2871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02372_si_002.cif
_cod_data_source_block           g061_final
_cod_depositor_comments
'Adding full bibliography for 4125086--4125088.cif.'
_cod_original_cell_volume        804.81(16)
_cod_database_code               4125087
_shelx_estimated_absorpt_t_min   0.657
_shelx_estimated_absorpt_t_max   0.782
_shelx_res_checksum              2140
_shelx_hkl_checksum              25606