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_1554303
_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                 102.1649(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.54242(11)
_cell_length_b                   22.4359(3)
_cell_length_c                   10.03319(17)
_cell_measurement_reflns_used    4455
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.0450
_cell_measurement_theta_min      6.0210
_cell_volume                     1439.65(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     20.00  45.00   1.00    3.00    --   44.52  57.00 -30.00   25
  2  \w     83.00 109.00   1.00    3.00    --   44.52  57.00 -30.00   26
  3  \w    122.00 171.00   1.00    8.00    --  100.00  30.00-150.00   49
  4  \w     68.00 126.00   1.00    8.00    --  100.00  77.00 150.00   58
  5  \w     19.00 107.00   1.00    8.00    --  100.00 -94.00 120.00   88
  6  \w     26.00 119.00   1.00    8.00    --  100.00-125.00  60.00   93
  7  \w    -70.00  23.00   1.00    3.00    --  -44.52  57.00 -90.00   93
  8  \w   -126.00 -85.00   1.00    3.00    --  -44.52 -99.00-180.00   41
  9  \w   -149.00 -74.00   1.00    8.00    --  -90.00-125.00-180.00   75
 10  \w   -163.00 -89.00   1.00    8.00    --  -90.00-125.00 -60.00   74
;
_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      -0.0649995000
_diffrn_orient_matrix_UB_12      0.0087418000
_diffrn_orient_matrix_UB_13      -0.1555063000
_diffrn_orient_matrix_UB_21      0.0028521000
_diffrn_orient_matrix_UB_22      0.0681419000
_diffrn_orient_matrix_UB_23      0.0201246000
_diffrn_orient_matrix_UB_31      0.2317183000
_diffrn_orient_matrix_UB_32      0.0015617000
_diffrn_orient_matrix_UB_33      -0.0094666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6007
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         5.993
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75691
_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    1.354
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0560P)^2^+0.4649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             2540
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00305j2.cif
_cod_data_source_block           yjc_h2_161018
_cod_database_code               1554303
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.577
_reflns_odcompleteness_completeness 99.43
_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:
 C9(H9), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C6(H6), C8(H8), C12(H12), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              90410
_shelx_hkl_checksum              67649
_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 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.580