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_7250709
_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         '2(C18 H14 O2 S2)'
_chemical_formula_sum            'C36 H28 O4 S4'
_chemical_formula_weight         652.82
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-06 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7120(2)
_cell_length_b                   9.99449(19)
_cell_length_c                   21.0468(4)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      69.9230
_cell_measurement_theta_min      7.4570
_cell_volume                     3094.70(9)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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     41.00  97.00   1.00    1.50    --  108.00 -77.00  90.00   56
  2  \w     77.00 130.00   1.00    1.00    --   54.00-161.00  67.00   53
  3  \w    100.00 138.00   1.00    1.50    --  108.00 -77.00 -30.00   38
  4  \w    146.00 178.00   1.00    1.50    --  108.00   0.00-120.00   32
  5  \w    101.00 143.00   1.00    1.50    --  108.00 111.00 -30.00   42
  6  \w    146.00 172.00   1.00    1.50    --  108.00 117.00 -54.00   26
  7  \w    114.00 173.00   1.00    1.50    --  108.00  50.00  90.00   59
  8  \w     73.00 150.00   1.00    1.50    --  108.00 178.00 -90.00   77
  9  \w     59.00 120.00   1.00    1.00    --   54.00  77.00-150.00   61
 10  \w     37.00 133.00   1.00    1.50    --  108.00 -38.00-120.00   96
 11  \w     45.00  70.00   1.00    1.50    --  108.00 -77.00 -30.00   25
 12  \w     36.00 101.00   1.00    1.50    --  108.00-111.00  60.00   65
 13  \w     43.00  68.00   1.00    1.50    --  108.00 -25.00 150.00   25
 14  \w      4.00  31.00   1.00    1.00    --   54.00 -99.00   0.00   27
 15  \w     32.00  77.00   1.00    1.00    --   54.00 -38.00-120.00   45
 16  \w     20.00  58.00   1.00    1.00    --    0.00  57.00-180.00   38
 17  \w    -24.00  36.00   1.00    1.00    --    0.00  38.00 -30.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0292457000
_diffrn_orient_matrix_UB_12      -0.0206803000
_diffrn_orient_matrix_UB_13      -0.0696272000
_diffrn_orient_matrix_UB_21      0.0103868000
_diffrn_orient_matrix_UB_22      -0.1511710000
_diffrn_orient_matrix_UB_23      0.0123026000
_diffrn_orient_matrix_UB_31      -0.0999819000
_diffrn_orient_matrix_UB_32      -0.0218573000
_diffrn_orient_matrix_UB_33      -0.0190139000
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10511
_diffrn_reflns_point_group_measured_fraction_full 0.790
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.876
_diffrn_reflns_theta_min         4.201
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73438
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1460 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(10)
_refine_ls_extinction_coef       0.00041(9)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0511P)^2^+0.1679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_full    0.568
_reflns_Friedel_fraction_max     0.552
_reflns_number_gt                4448
_reflns_number_total             4576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc02103k2.cif
_cod_data_source_block           baichunyan_1118
_cod_depositor_comments
'Adding full bibliography for 7250708--7250709.cif.'
_cod_database_code               7250709
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.723
_shelx_estimated_absorpt_t_min   0.519
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
  C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32),
 C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              62487
_shelx_hkl_checksum              62822
_olex2_date_sample_data_collection 2024-11-18
_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 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.690