An organophotocatalytic redox-neutral strategy for late-stage drug functionalization with SO<sub>2</sub> gas.
Datta, Paramita; Maji, Subir; Biswas, Prativa; Jain, Divya; Dey, Partha Protim; Mandal, Swadhin K.; Chemical science 16 (2025) 5064–5075; doi:10.1039/d4sc08380f

data_1573918
_publ_section_title
;
 An organophotocatalytic redox-neutral strategy for late-stage drug
 functionalization with SO<sub>2</sub> gas.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              5064
_journal_page_last               5075
_journal_paper_doi               10.1039/d4sc08380f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C23 H20 Cl N3 O3 S'
_chemical_formula_sum            'C23 H20 Cl N3 O3 S'
_chemical_formula_weight         453.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-08-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-08-28 deposited with the CCDC.	2025-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.52030(10)
_cell_length_b                   11.14400(10)
_cell_length_c                   23.4626(2)
_cell_measurement_reflns_used    36331
_cell_measurement_temperature    290(9)
_cell_measurement_theta_max      68.2250
_cell_measurement_theta_min      2.6350
_cell_volume                     4319.52(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      290.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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   -109.00 -14.00   0.50    1.09    --  -40.83 -75.00-170.00  190
  2  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -75.00-170.00  190
  3  \w    -67.00  29.00   0.50    1.09    --  -40.83  75.00 -43.00  192
  4  \w    -61.00  27.00   0.50    1.09    --  -40.83  55.00 104.00  176
  5  \w    -74.00  29.00   0.50    1.09    --  -40.83  97.00-157.00  206
  6  \w    -74.00  29.00   0.50    1.09    --  -40.83  97.00-157.00  206
  7  \w     -7.00  74.00   0.50    1.09    --   40.83 -97.00  94.00  162
  8  \w    -26.00  62.00   0.50    1.09    --   40.83 -55.00 -37.00  176
  9  \w    -81.00  -9.00   0.50    4.50    --  -82.50  97.00-157.00  144
 10  \w   -155.00 -84.00   0.50    4.50    --  -82.50 -97.00  94.00  142
 11  \w    -98.00 -13.00   0.50    4.50    --  -82.50  75.00 -43.00  170
 12  \w    -63.00 -14.00   0.50    4.50    --  -82.50  55.00 104.00   98
 13  \w     76.00 164.00   0.50    4.50    --   96.35  55.00 104.00  176
 14  \w     70.00 166.00   0.50    4.50    --   96.35  75.00 -43.00  192
 15  \w     24.00 107.00   0.50    4.50    --   96.35 -97.00  94.00  166
 16  \w     27.00  98.00   0.50    4.50    --   96.35 -75.00-170.00  142
 17  \w     29.00  63.00   0.50    4.50    --   96.35 -55.00 -37.00   68
 18  \w   -108.00 -20.00   0.50    1.09    --  -40.83 -55.00 -37.00  176
 19  \w   -108.00 -63.00   0.50    1.09    --  -40.83-139.00-180.00   90
 20  \w   -108.00 -63.00   0.50    1.09    --  -40.83-139.00 150.00   90
 21  \w    -31.00  28.00   0.50    1.09    --   40.83 -21.00  30.00  118
 22  \w     20.00 109.00   0.50    1.09    --   40.83  55.00 104.00  178
 23  \w     20.00 109.00   0.50    1.09    --   40.83  55.00 104.00  178
 24  \w     30.00  57.00   0.50    4.50    --   96.35 -50.00-150.00   54
 25  \w     30.00  57.00   0.50    4.50    --   96.35 -50.00 -30.00   54
 26  \w     30.00  57.00   0.50    4.50    --   96.35 -50.00  60.00   54
 27  \w     30.00  57.00   0.50    4.50    --   96.35 -50.00-180.00   54
 28  \w     99.00 160.00   0.50    4.50    --   96.35 117.00 -90.00  122
 29  \w     28.00  68.00   0.50    4.50    --   96.35 -59.00 -90.00   80
 30  \w     28.00  68.00   0.50    4.50    --   96.35 -59.00-180.00   80
 31  \w     30.00  57.00   0.50    4.50    --   96.35 -50.00 -90.00   54
 32  \w     29.00  83.00   0.50    4.50    --   96.35 -68.00-120.00  108
 33  \w     29.00  83.00   0.50    4.50    --   96.35 -68.00  90.00  108
 34  \w     30.00  57.00   0.50    4.50    --   96.35 -50.00  90.00   54
 35  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -77.00-150.00  190
 36  \w    -37.00  27.00   0.50    1.09    --  -40.83  32.00-150.00  128
 37  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -77.00 120.00  190
 38  \w   -108.00 -17.00   0.50    1.09    --  -40.83 -66.00 -60.00  182
 39  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -77.00-120.00  190
 40  \w   -108.00 -17.00   0.50    1.09    --  -40.83 -66.00 150.00  182
 41  \w   -109.00 -28.00   0.50    1.09    --  -40.83 -32.00   0.00  162
 42  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -77.00  60.00  190
 43  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -77.00 -90.00  190
 44  \w   -109.00 -14.00   0.50    1.09    --  -40.83 -77.00   0.00  190
 45  \w     14.00 110.00   0.50    1.09    --   40.83  77.00   0.00  192
 46  \w    -35.00  24.00   0.50    1.09    --   40.83 -11.00  90.00  118
 47  \w    -35.00  24.00   0.50    1.09    --   40.83 -11.00 -30.00  118
 48  \w     41.00 101.00   0.50    1.09    --   40.83-139.00  60.00  120
 49  \w   -151.00 -63.00   0.50    4.50    --  -82.50 -77.00 -90.00  176
 50  \w     37.00 174.00   0.50    4.50    --   96.35   8.00 -90.00  274
 51  \w     72.00 164.00   0.50    4.50    --   96.35  68.00  60.00  184
 52  \w     77.00 163.00   0.50    4.50    --   96.35  50.00 -60.00  172
 53  \w     71.00 170.00   0.50    4.50    --   96.35  17.00  60.00  198
 54  \w     77.00 163.00   0.50    4.50    --   96.35  50.00 150.00  172
 55  \w     81.00 165.00   0.50    4.50    --   96.35 145.00 150.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            56123
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_min         3.768
_exptl_absorpt_coefficient_mu    2.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.119a (Rigaku Oxford Diffraction, 2024)
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    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0547P)^2^+1.0676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3536
_reflns_number_total             3935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08380f2.cif
_cod_data_source_block           3x_auto
_cod_depositor_comments
'Adding full bibliography for 1573911--1573921.cif.'
_cod_database_code               1573918
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.708
_shelx_estimated_absorpt_t_min   0.688
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C7(H7A,H7B), C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C20(H20), C16(H16), C2(H2), C6(H6), C19(H19), C17(H17),
 C18(H18), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              21413
_shelx_hkl_checksum              91296
_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
;