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_4123415
_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 rmad
_chemical_formula_moiety         'C22 H22 Br N O3 S'
_chemical_formula_sum            'C22 H22 Br N O3 S'
_chemical_formula_weight         460.37
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                74.143(3)
_cell_angle_beta                 74.315(3)
_cell_angle_gamma                83.209(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4326(13)
_cell_length_b                   8.4705(15)
_cell_length_c                   8.8458(15)
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.47
_cell_volume                     515.18(16)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5139
_diffrn_reflns_point_group_measured_fraction_full 0.668
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.640
_diffrn_reflns_theta_min         2.472
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.119
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0882 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.6932.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.011(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0311
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0650
_reflns_Friedel_coverage         0.295
_reflns_Friedel_fraction_full    0.337
_reflns_Friedel_fraction_max     0.290
_reflns_number_gt                3406
_reflns_number_total             4052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511143b_si_002.cif
_cod_data_source_block           compound4
_cod_depositor_comments
'Adding full bibliography for 4123414--4123415.cif.'
_cod_database_code               4123415
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.728
_shelx_estimated_absorpt_t_min   0.619
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
;
_shelx_res_checksum              10805
_shelx_hkl_checksum              89275
_olex2_submission_special_instructions 'No special instructions were received'