Chiral Bifunctional Amine-Squaramide-Catalyzed Highly Diastereo- and Enantioselective Michael/Aldol Cascade Reaction of 2-Mercaptobenzaldehyde and α,β-Unsaturated 7-Azaindoline Amides.
Zhang, Yan-Ping; You, Yong; Zhao, Jian-Qiang; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng; The Journal of organic chemistry 84 (2019) 7984–7994; doi:10.1021/acs.joc.9b00837

data_4034666
_publ_section_title
;
 Chiral Bifunctional Amine-Squaramide-Catalyzed Highly Diastereo- and
 Enantioselective Michael/Aldol Cascade Reaction of 2-Mercaptobenzaldehyde
 and \a,\b-Unsaturated 7-Azaindoline Amides.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7984
_journal_page_last               7994
_journal_paper_doi               10.1021/acs.joc.9b00837
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H22 N2 O3 S'
_chemical_formula_weight         418.49
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.590(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.3559(3)
_cell_length_b                   15.3767(4)
_cell_length_c                   9.9606(4)
_cell_measurement_reflns_used    10158
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      28.6790
_cell_measurement_theta_min      3.9980
_cell_volume                     1061.42(7)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23861
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.491
_diffrn_reflns_theta_min         3.291
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5377
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0429P)^2^+0.1045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                4594
_reflns_number_total             5377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00837_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034666
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-4
_shelx_res_checksum              40369
_shelx_hkl_checksum              1822