Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives
Yu, Ji-cong; Yu, Le-mao; Zhao, Xiao-yun; Gan, Lu; Zhu, Wei-wei; Wang, Ze-chen; Wang, Rui; Jiang, Xianxing; Organic Chemistry Frontiers 5 (2018) 2040–; doi:10.1039/C8QO00305J

data_1554302
_publ_section_title
;
 Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol
 with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2040
_journal_paper_doi               10.1039/C8QO00305J
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C15 H19 N O3 S'
_chemical_formula_sum            'C15 H19 N O3 S'
_chemical_formula_weight         293.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-17 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.176(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0093(2)
_cell_length_b                   14.3918(3)
_cell_length_c                   10.7208(2)
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.8690
_cell_measurement_theta_min      3.0530
_cell_volume                     1497.32(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      1.00  53.00   1.00    3.00    --   44.40 -57.00  60.00   52
  2  \w     89.00 114.00   1.00    3.00    --   44.40  57.00  30.00   25
  3  \w     74.00 111.00   1.00    3.00    --   44.40 125.00  30.00   37
  4  \w    107.00 170.00   1.00    8.00    --  100.00  61.00   0.00   63
  5  \w     36.00 117.00   1.00    8.00    --  100.00-125.00-120.00   81
  6  \w     94.00 120.00   1.00    8.00    --  100.00-125.00-180.00   26
  7  \w     28.00 129.00   1.00    8.00    --  100.00 -77.00-120.00  101
  8  \w     27.00  90.00   1.00    8.00    --  100.00-125.00-180.00   63
  9  \w     19.00  46.00   1.00    3.00    --   44.40  57.00  30.00   27
 10  \w    -55.00 -18.00   1.00    8.00    --  -90.00 125.00 -60.00   37
 11  \w   -115.00 -90.00   1.00    8.00    --  -90.00 125.00 -60.00   25
 12  \w   -160.00-107.00   1.00    8.00    --  -90.00 -61.00  30.00   53
 13  \w   -117.00 -77.00   1.00    3.00    --  -44.40-125.00 -90.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0230452000
_diffrn_orient_matrix_UB_12      0.0459827000
_diffrn_orient_matrix_UB_13      -0.1228276000
_diffrn_orient_matrix_UB_21      0.0394183000
_diffrn_orient_matrix_UB_22      0.0915593000
_diffrn_orient_matrix_UB_23      0.0742349000
_diffrn_orient_matrix_UB_31      0.1520452000
_diffrn_orient_matrix_UB_32      -0.0308070000
_diffrn_orient_matrix_UB_33      0.0372873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.556
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.301
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0371P)^2^+0.5750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0756
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2520
_reflns_number_total             2663
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00305j2.cif
_cod_data_source_block           yjc_h1_161025_2
_cod_original_cell_volume        1497.33(6)
_cod_database_code               1554302
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.826
_shelx_estimated_absorpt_t_min   0.505
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C12(H12), C16(H16), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              91342
_shelx_hkl_checksum              57464
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.951
_oxdiff_exptl_absorpt_empirical_full_min 0.593