Electrochemical ring-opening oxidation of aryl thianthrenium salts
Yuan, Yong; Bai, Chunyan; Tao, Yuyan; Zhang, Ya-Nan; Bao, Xiazhen; Ji, Dongsheng; Wang, Liwei; Qi, Xiaotian; Huo, Congde; Green Chemistry 27 (2025) 9777–9786; doi:10.1039/D5GC02103K

data_7250708
_publ_section_title
;
 Electrochemical ring-opening oxidation of aryl thianthrenium salts
;
_journal_issue                   32
_journal_name_full               'Green Chemistry'
_journal_page_first              9777
_journal_page_last               9786
_journal_paper_doi               10.1039/D5GC02103K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C21 H18 O S2'
_chemical_formula_sum            'C21 H18 O S2'
_chemical_formula_weight         350.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-15
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-12-06 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.455(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7103(2)
_cell_length_b                   9.7878(2)
_cell_length_c                   15.3735(4)
_cell_measurement_reflns_used    7786
_cell_measurement_temperature    301.20(10)
_cell_measurement_theta_max      76.0200
_cell_measurement_theta_min      4.5240
_cell_volume                     1754.10(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.20(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.950
_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    -67.00 -29.00   1.00    0.15    -- -102.00  61.00 120.00   38
  2  \w    -69.00 -29.00   1.00    0.15    -- -102.00  61.00  90.00   40
  3  \w    -69.00 -44.00   1.00    0.15    -- -102.00  61.00 -60.00   25
  4  \w    -69.00 -44.00   1.00    0.15    -- -102.00  61.00-150.00   25
  5  \w    -25.00  20.00   1.00    0.10    --  -46.68  19.00-150.00   45
  6  \w    -25.00  15.00   1.00    0.10    --  -46.68  19.00-180.00   40
  7  \w    -21.00   4.00   1.00    0.10    --  -46.68  19.00   0.00   25
  8  \w    -22.00  29.00   1.00    0.10    --  -46.68  19.00 120.00   51
  9  \w    -81.00 -21.00   1.00    0.10    --  -46.68 112.00 -97.00   60
 10  \w   -102.00 -67.00   1.00    0.15    -- -102.00 112.00 -97.00   35
 11  \w   -161.00 -91.00   1.00    0.15    -- -102.00-112.00 169.00   70
 12  \w     43.00  70.00   1.00    0.15    --  104.76 -77.00-180.00   27
 13  \w     77.00 103.00   1.00    0.15    --  104.76 -77.00-180.00   26
 14  \w     46.00  72.00   1.00    0.15    --  104.76 -61.00-180.00   26
 15  \w     41.00  67.00   1.00    0.15    --  104.76 -61.00-150.00   26
 16  \w    -27.00  28.00   1.00    0.10    --   46.68 -19.00-180.00   55
 17  \w     43.00  69.00   1.00    0.15    --  104.76 -61.00 -30.00   26
 18  \w    103.00 166.00   1.00    0.15    --  104.76  30.00-120.00   63
 19  \w     92.00 177.00   1.00    0.15    --  104.76  77.00-120.00   85
 20  \w    142.00 167.00   1.00    0.15    --  104.76 112.00 -97.00   25
 21  \w    126.00 171.00   1.00    0.15    --  104.76  30.00   0.00   45
 22  \w     39.00 105.00   1.00    0.15    --  104.76 -94.00 150.00   66
 23  \w     72.00  98.00   1.00    0.15    --  104.76-112.00 169.00   26
 24  \w     22.00  47.00   1.00    0.10    --   46.68-112.00 169.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0056106000
_diffrn_orient_matrix_UB_12      0.1254988000
_diffrn_orient_matrix_UB_13      0.0607433000
_diffrn_orient_matrix_UB_21      0.0359226000
_diffrn_orient_matrix_UB_22      0.0899214000
_diffrn_orient_matrix_UB_23      -0.0749588000
_diffrn_orient_matrix_UB_31      -0.1271032000
_diffrn_orient_matrix_UB_32      0.0308713000
_diffrn_orient_matrix_UB_33      -0.0284680000
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11336
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.564
_diffrn_reflns_theta_min         4.544
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0033(5)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.4478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3174
_reflns_number_total             3509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc02103k2.cif
_cod_data_source_block           p5_auto
_cod_depositor_comments
'Adding full bibliography for 7250708--7250709.cif.'
_cod_original_cell_volume        1754.09(7)
_cod_database_code               7250708
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C14(H14), C6(H6), C5(H5), C13(H13), C11(H11), C18(H18),
 C17(H17), C12(H12), C21(H21), C19(H19), C20(H20)
;
_shelx_res_checksum              76221
_shelx_hkl_checksum              41040
_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 1.603
_oxdiff_exptl_absorpt_empirical_full_min 0.808