Stereoselective thiosulfonylation of alkynes using sodium thiosulfate as a sulfur transfer agent to access <i>bis</i>-(<i>Z</i>)-vinyl sulfones.
Tiwari, Shashikant; Kumar, Nitin; Rawat, Diwan S.; Chemical communications (Cambridge, England) 62 (2026) 6751–6754; doi:10.1039/d5cc07298k

data_7135450
_publ_section_title
;
 Stereoselective thiosulfonylation of alkynes using sodium thiosulfate as
 a sulfur transfer agent to access <i>bis</i>-(<i>Z</i>)-vinyl sulfones.
;
_journal_issue                   25
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6751
_journal_page_last               6754
_journal_paper_doi               10.1039/d5cc07298k
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C15 H12 Br O2 S1.5'
_chemical_formula_sum            'C15 H12 Br O2 S1.5'
_chemical_formula_weight         352.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2026-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.989(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6288(7)
_cell_length_b                   9.5465(4)
_cell_length_c                   19.9075(9)
_cell_measurement_reflns_used    4428
_cell_measurement_temperature    153(4)
_cell_measurement_theta_max      31.2250
_cell_measurement_theta_min      2.1480
_cell_volume                     3005.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.799
_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    -22.00  27.00   0.50    3.97    --   -5.22 -99.00  60.00   98
  2  \w     29.00  63.00   0.50    3.97    --   -5.22  38.00 150.00   68
  3  \w    -39.00  77.00   0.50    3.97    --    6.31   0.00   0.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0027119000
_diffrn_orient_matrix_UB_12      -0.0446061000
_diffrn_orient_matrix_UB_13      -0.0291326000
_diffrn_orient_matrix_UB_21      -0.0119239000
_diffrn_orient_matrix_UB_22      -0.0564773000
_diffrn_orient_matrix_UB_23      0.0180268000
_diffrn_orient_matrix_UB_31      -0.0431398000
_diffrn_orient_matrix_UB_32      0.0184199000
_diffrn_orient_matrix_UB_33      -0.0151966000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.799
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10176
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.046
_diffrn_reflns_theta_min         2.151
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0310P)^2^+2.1546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0745
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3035
_reflns_number_total             3837
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc07298k2.cif
_cod_data_source_block           rs-14l_auto
_cod_depositor_comments
'Adding full bibliography for 7135450--7135451.cif.'
_cod_original_formula_sum        'C15 H12 Br O2 S1.50'
_cod_database_code               7135450
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N Cl O'
_chemical_oxdiff_usercomment     23-01-2025
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00F,H00K)
;
_shelx_res_checksum              88452
_shelx_hkl_checksum              94628
_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 7.550
_oxdiff_exptl_absorpt_empirical_full_min 0.649