Diastereoselective thia-[3 + 2] cyclization of acetylpyranuloses and β-oxodithioesters.
Cheng, Shihao; Ni, Xiao; Cui, Guanyou; Dong, Chenhu; Ma, Yujie; Li, Jinlong; Bao, Xiaofeng; Zhao, Yu; Organic & biomolecular chemistry 23 (2025) 2362–2364; doi:10.1039/d5ob00022j

data_1573821
_publ_section_title
;
 Diastereoselective thia-[3 + 2] cyclization of acetylpyranuloses and
 &#x3b2;-oxodithioesters.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2362
_journal_page_last               2364
_journal_paper_doi               10.1039/d5ob00022j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C15 H14 O3 S2'
_chemical_formula_sum            'C15 H14 O3 S2'
_chemical_formula_weight         306.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-21
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-11-15 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                82.619(4)
_cell_angle_beta                 74.785(5)
_cell_angle_gamma                73.760(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1960(3)
_cell_length_b                   10.6217(6)
_cell_length_c                   11.3470(6)
_cell_measurement_reflns_used    3667
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.4280
_cell_measurement_theta_min      4.0030
_cell_volume                     690.62(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_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      2.00  82.00   1.00    1.00    --   40.73 -99.00 120.00   80
  2  \w     43.00 117.00   1.00    1.00    --  107.58-125.00   0.00   74
  3  \w     45.00 135.00   1.00    1.00    --  107.58 -61.00  30.00   90
  4  \w    112.00 153.00   1.00    1.00    --  107.58  45.00 120.00   41
  5  \w     32.00 135.00   1.00    1.00    --  107.58 -30.00 150.00  103
  6  \w    -18.00  30.00   1.00    1.00    --  -40.73  57.00-180.00   48
  7  \w    141.00 178.00   1.00    1.00    --  107.58  45.00-180.00   37
  8  \w    100.00 128.00   1.00    1.00    --  107.58 125.00-180.00   28
  9  \w     92.00 131.00   1.00    1.00    --  107.58  45.00-180.00   39
 10  \w    -84.00 -16.00   1.00    1.00    --  -40.73 -38.00-120.00   68
 11  \w   -114.00 -86.00   1.00    1.00    --  -40.73 -38.00-120.00   28
 12  \w   -106.00 -15.00   1.00    1.00    --  -40.98 -57.00   0.00   91
 13  \w    -28.00  -2.00   1.00    1.00    --  -40.98 125.00  60.00   26
 14  \w    -28.00  -2.00   1.00    1.00    --   40.98 -57.00-150.00   26
 15  \w     13.00  67.00   1.00    1.00    --   40.98 -57.00-150.00   54
 16  \w     87.00 131.00   1.00    1.00    --  107.58  61.00-120.00   44
 17  \w     82.00 115.00   1.00    1.00    --  107.58-125.00-180.00   33
 18  \w    152.00 178.00   1.00    1.00    --  107.58  30.00 120.00   26
 19  \w     43.00  69.00   1.00    1.00    --  107.58 -77.00 -90.00   26
 20  \w     80.00 133.00   1.00    1.00    --  107.58  30.00 120.00   53
 21  \w     87.00 140.00   1.00    1.00    --  107.58 -77.00 -90.00   53
 22  \w     72.00 102.00   1.00    1.00    --  107.58 -94.00  30.00   30
 23  \w     32.00 102.00   1.00    1.00    --  107.58 -94.00-150.00   70
 24  \w     79.00 122.00   1.00    1.00    --  107.58  61.00   0.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1349399000
_diffrn_orient_matrix_UB_12      0.0210215000
_diffrn_orient_matrix_UB_13      -0.1326997000
_diffrn_orient_matrix_UB_21      0.0348816000
_diffrn_orient_matrix_UB_22      0.1281155000
_diffrn_orient_matrix_UB_23      0.0327639000
_diffrn_orient_matrix_UB_31      0.2272973000
_diffrn_orient_matrix_UB_32      -0.0777568000
_diffrn_orient_matrix_UB_33      0.0344108000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4814
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.163
_diffrn_reflns_theta_min         4.045
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0574
_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^)+(0.1187P)^2^+0.2066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2593
_reflns_number_total             2708
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00022j2.cif
_cod_data_source_block           exp_5389
_cod_depositor_comments          'Adding full bibliography for 1573821.cif.'
_cod_database_code               1573821
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              3988
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.147
_oxdiff_exptl_absorpt_empirical_full_min 0.476