Organocatalytic enantioselective direct additions of aldehydes to 4-vinylpyridines and electron-deficient vinylarenes and their synthetic applications.
Wang, Sinan; Li, Xiangmin; Liu, Hongwei; Xu, Li; Zhuang, Jinchen; Li, Jian; Li, Hao; Wang, Wei; Journal of the American Chemical Society 137 (2015) 2303–2310; doi:10.1021/ja511143b

data_4123414
_publ_section_title
;
 Organocatalytic enantioselective direct additions of aldehydes to
 4-vinylpyridines and electron-deficient vinylarenes and their synthetic
 applications.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2303
_journal_page_last               2310
_journal_paper_doi               10.1021/ja511143b
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 Br Cl N2 O7 S'
_chemical_formula_sum            'C23 H20 Br Cl N2 O7 S'
_chemical_formula_weight         583.83
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2161(16)
_cell_length_b                   8.7777(18)
_cell_length_c                   17.239(3)
_cell_measurement_reflns_used    6245
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.81
_cell_measurement_theta_min      2.56
_cell_volume                     1242.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8467
_diffrn_reflns_theta_full        66.92
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.437
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.4951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.098(13)
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4017
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.1131P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                3946
_reflns_number_total             4017
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja511143b_si_003.cif
_cod_data_source_block           Compound7
_cod_depositor_comments
'Adding full bibliography for 4123414--4123415.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4123414