Photoredox-catalyzed synthesis of sulfonated dihydrofurans from olefinic carbonyls through the insertion of sulfur dioxide
Sun, Lidan; Xu, Mengze; Feng, Yurou; Lin, Quanjie; Xie, Xiaolan; Shen, Jinhai; Chen, Zhichao; New Journal of Chemistry 49 (2025) 7268–7272; doi:10.1039/D5NJ00238A

data_7063721
_publ_section_title
;
 Photoredox-catalyzed synthesis of sulfonated dihydrofurans from olefinic
 carbonyls through the insertion of sulfur dioxide
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7268
_journal_page_last               7272
_journal_paper_doi               10.1039/D5NJ00238A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C31 H26 O4 S'
_chemical_formula_sum            'C31 H26 O4 S'
_chemical_formula_weight         494.58
_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             2024-08-20
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-21 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.072(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6923(2)
_cell_length_b                   25.6469(5)
_cell_length_c                   10.1345(2)
_cell_measurement_reflns_used    10026
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.8160
_cell_measurement_theta_min      3.4520
_cell_volume                     2432.55(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_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     35.00 101.00   0.50    0.96    --  107.28-125.00   0.00  132
  2  \w     35.00  69.00   0.50    0.96    --  107.28-125.00  60.00   68
  3  \w     77.00 114.00   0.50    0.96    --  107.28-125.00  60.00   74
  4  \w     50.00 103.00   0.50    0.96    --  107.28 -95.00  60.00  106
  5  \w     35.00  62.00   0.50    0.96    --  107.28 -61.00 120.00   54
  6  \w     43.00  68.00   0.50    0.50    --   41.71  55.00 134.00   50
  7  \w     -9.00  16.00   0.50    0.50    --   41.71 -55.00  -8.00   50
  8  \w     34.00  63.00   0.50    0.96    --  107.28 -55.00  -8.00   58
  9  \w     88.00 178.00   0.50    0.96    --  107.28  55.00 134.00  180
 10  \w     91.00 176.00   0.50    0.96    --  107.28  45.00  60.00  170
 11  \w     94.00 119.00   0.50    0.96    --  107.28 125.00 -30.00   50
 12  \w    137.00 162.00   0.50    0.96    --  107.28 125.00 -30.00   50
 13  \w     80.00 113.00   0.50    0.50    --   41.71 178.00   0.00   66
 14  \w     60.00 122.00   0.50    0.50    --   41.71 178.00 -90.00  124
 15  \w    -85.00 -27.00   0.50    0.96    --  -98.00 125.00-150.00  116
 16  \w    -71.00 -28.00   0.50    0.96    --  -98.00  61.00-180.00   86
 17  \w    -70.00 -28.00   0.50    0.96    --  -98.00  61.00-120.00   84
 18  \w    -54.00 -23.00   0.50    0.96    --  -98.00  61.00 -30.00   62
 19  \w   -116.00 -18.00   0.50    0.50    --  -41.71 -55.00  -8.00  196
 20  \w   -148.00-123.00   0.50    0.96    --  -98.00 -55.00  -8.00   50
 21  \w    -51.00 -26.00   0.50    0.96    --  -98.00  45.00 -30.00   50
 22  \w    -51.00 -23.00   0.50    0.96    --  -98.00  45.00 -60.00   56
 23  \w    -50.00 -25.00   0.50    0.96    --  -98.00  45.00 -90.00   50
 24  \w    -51.00 -26.00   0.50    0.96    --  -98.00  45.00-120.00   50
 25  \w    -51.00 -21.00   0.50    0.96    --  -98.00  45.00 120.00   60
 26  \w    -56.00 -26.00   0.50    0.96    --  -98.00  55.00 134.00   60
 27  \w    -56.00 -13.00   0.50    0.50    --  -41.71  55.00 134.00   86
 28  \w     -9.00  29.00   0.50    0.50    --  -41.71  55.00 134.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1416602000
_diffrn_orient_matrix_UB_12      -0.0178898000
_diffrn_orient_matrix_UB_13      0.0979241000
_diffrn_orient_matrix_UB_21      0.0282402000
_diffrn_orient_matrix_UB_22      -0.0356285000
_diffrn_orient_matrix_UB_23      -0.1125072000
_diffrn_orient_matrix_UB_31      0.0789930000
_diffrn_orient_matrix_UB_32      0.0449537000
_diffrn_orient_matrix_UB_33      -0.0501303000
_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  0.0440
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15763
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.552
_diffrn_reflns_theta_min         3.447
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.8970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4139
_reflns_number_total             4705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00238a2.cif
_cod_data_source_block           dw-20231016-lqj_auto
_cod_depositor_comments          'Adding full bibliography for 7063721.cif.'
_cod_database_code               7063721
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.831
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C60(H60A,H60B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C22(H22), C55(H55), C31(H31), C5(H5), C9(H9), C43(H43), C52(H52),
 C13(H13), C54(H54), C29(H29), C4(H4), C56(H56), C58(H58), C14(H14), C26(H26),
 C28(H28), C48(H48), C62(H62)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              4881
_shelx_hkl_checksum              10811
_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 1.902
_oxdiff_exptl_absorpt_empirical_full_min 0.535