Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters.
Yang, Lei; Zhao, Jian-Qiang; You, Yong; Wang, Zhen-Hua; Yuan, Wei-Cheng; Chemical communications (Cambridge, England) 56 (2020) 12363–12366; doi:10.1039/d0cc04840b

data_7127187
_publ_section_title
;
 Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to
 access dihydrothiopyran-fused benzosulfolane skeletons bearing three
 contiguous stereocenters.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12363
_journal_page_last               12366
_journal_paper_doi               10.1039/d0cc04840b
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H21 N O5 S2'
_chemical_formula_sum            'C22 H21 N O5 S2'
_chemical_formula_weight         443.52
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-03 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.71695(13)
_cell_length_b                   13.36161(18)
_cell_length_c                   17.6913(2)
_cell_measurement_reflns_used    11357
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9570
_cell_measurement_theta_min      4.1410
_cell_volume                     2060.55(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega -101.00  -37.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 128

  2 omega -108.00  -83.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 50

  3 omega  -76.00  -43.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 66

  4 omega  -33.00   -6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 54

  5 omega -100.00  -41.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  150.0000 118

  6 omega   74.00  100.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 52

  7 omega  -32.00   58.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 180

  8 omega   -9.00   16.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  108.0000  -20.8188 50

  9 omega    9.00   59.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 100

 10 omega   14.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  -30.0000 184

 11 omega   37.00   70.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   90.0000 66

 12 omega   57.00  106.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 98

 13 omega   -4.00   49.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 106

 14 omega   -9.00   16.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  108.0000   52.3759 50

 15 omega   26.00   52.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 52

 16 omega   31.00   57.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -60.0000 52

 17 omega   69.00   96.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 54

 18 omega    3.00   29.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  120.0000 52

 19 omega   29.00   90.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 122

 20 omega   79.00  109.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 60

 21 omega  107.00  177.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 140

 22 omega   37.00   88.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 102

 23 omega   60.00   88.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 56

 24 omega   82.00  161.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 158

 25 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 52

 26 omega   82.00  108.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 52

 27 omega   90.00  119.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 58

 28 omega  141.00  173.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 64

 29 omega   82.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 64

 30 omega   83.00  115.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 64

 31 omega  122.00  160.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 76

 32 omega   87.00  113.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -75.2507 52

 33 omega  122.00  175.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 106

 34 omega   79.00  104.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 50

 35 omega  148.00  175.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 54

 36 omega   79.00  170.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 182

 37 omega  102.00  178.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 152

 38 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 52

 39 omega   79.00  104.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 50

 40 omega   87.00  113.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 52

 41 omega   79.00  105.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 52

 42 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 52

 43 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 52

 44 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 52

 45 omega   88.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 52

 46 omega   91.00  116.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 50

 47 omega   79.00  171.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 184

 48 omega   89.00  114.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 50

 49 omega  120.00  153.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 66

 50 omega  116.00  157.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 82

 51 omega  100.00  173.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 146

 52 omega   79.00  105.00   0.5000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   26.0000  -71.9268 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0558471000
_diffrn_orient_matrix_UB_12      -0.0964207000
_diffrn_orient_matrix_UB_13      0.0389073000
_diffrn_orient_matrix_UB_21      0.0399668000
_diffrn_orient_matrix_UB_22      0.0452475000
_diffrn_orient_matrix_UB_23      0.0777097000
_diffrn_orient_matrix_UB_31      -0.1628260000
_diffrn_orient_matrix_UB_32      0.0441364000
_diffrn_orient_matrix_UB_33      0.0056937000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.065
_diffrn_reflns_theta_min         4.146
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.1988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3862
_reflns_number_total             3953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04840b2.cif
_cod_data_source_block           20190357
_cod_depositor_comments
'Adding full bibliography for 7127187--7127188.cif.'
_cod_database_code               7127187
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4S2
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.692
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O3(H3A)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'