Photo-induced intramolecular alkyl/aryl group transfer and SO2 insertion: a new strategy for the synthesis of 3-(alkyl/arylsulfonyl)benzothiophenes
Xu, Tiantian; Wang, Fen-Dou; Yang, Wen-Chao; Lu, Tong; Wang, Min; Li, Pinhua; Green Chemistry 27 (2025) 2386–2391; doi:10.1039/D4GC06127F

data_7249897
_publ_section_title
;
 Photo-induced intramolecular alkyl/aryl group transfer and SO2 insertion:
 a new strategy for the synthesis of 3-(alkyl/arylsulfonyl)benzothiophenes
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2386
_journal_page_last               2391
_journal_paper_doi               10.1039/D4GC06127F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C23 H18 O2 S'
_chemical_formula_sum            'C23 H18 O2 S'
_chemical_formula_weight         358.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-10-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-11-05 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.56(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.64(2)
_cell_length_b                   6.895(5)
_cell_length_c                   18.824(15)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      19.56
_cell_measurement_theta_min      2.48
_cell_volume                     3700(5)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1254
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52356
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.483
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1486 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.8534.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0460P)^2^+2.2194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2653
_reflns_number_total             4250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc06127f2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 7249897--7249899.cif.'
_cod_database_code               7249897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.965
_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. Uiso/Uaniso restraints and constraints
C22 \\sim O2A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Same fragment restrains
{C22, O2A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C22, O2}
4. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C15(H15)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              53696
_shelx_hkl_checksum              15392
_olex2_submission_special_instructions 'No special instructions were received'