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_1573916
_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         'C16 H20 N6 O2 S2'
_chemical_formula_sum            'C16 H20 N6 O2 S2'
_chemical_formula_weight         392.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 104.1190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.04170(10)
_cell_length_b                   21.49460(10)
_cell_length_c                   12.97610(10)
_cell_measurement_reflns_used    17378
_cell_measurement_temperature    283.2(7)
_cell_measurement_theta_max      68.1150
_cell_measurement_theta_min      3.4680
_cell_volume                     1904.71(3)
_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      283.15
_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     14.00 110.00   0.50    0.20    --   40.83  77.00-180.00  192
  2  \w     17.00 110.00   0.50    0.20    --   40.83  66.00 -90.00  186
  3  \w     21.00 108.00   0.50    0.20    --   40.83  54.00 -30.00  174
  4  \w     24.00 108.00   0.50    0.20    --   40.83  43.00 -90.00  168
  5  \w     14.00 110.00   0.50    0.20    --   40.83  77.00   0.00  192
  6  \w     14.00 110.00   0.50    0.20    --   40.83  77.00  30.00  192
  7  \w     21.00 108.00   0.50    0.20    --   40.83  54.00 150.00  174
  8  \w    105.00 170.00   0.50    0.67    --   96.35  96.00 120.00  130
  9  \w    106.00 167.00   0.50    0.67    --   96.35 102.00 137.00  122
 10  \w     77.00 163.00   0.50    0.67    --   96.35  50.00  60.00  172
 11  \w     83.00 164.00   0.50    0.67    --   96.35  33.00  30.00  162
 12  \w     81.00 167.00   0.50    0.67    --   96.35  25.00 120.00  172
 13  \w     81.00 167.00   0.50    0.67    --   96.35  25.00 -30.00  172
 14  \w     77.00 163.00   0.50    0.67    --   96.35  50.00 -90.00  172
 15  \w     80.00 164.00   0.50    0.67    --   96.35  42.00-180.00  168
 16  \w     99.00 160.00   0.50    0.67    --   96.35 117.00-180.00  122
 17  \w     81.00 167.00   0.50    0.67    --   96.35  25.00-120.00  172
 18  \w     33.00 110.00   0.50    0.67    --   96.35-117.00-150.00  154
 19  \w     23.00 106.00   0.50    0.67    --   96.35 -96.00-120.00  166
 20  \w     18.00  78.00   0.50    0.20    --   40.83-104.00-180.00  120
 21  \w      7.00  77.00   0.50    0.20    --   40.83-102.00  35.00  140
 22  \w     26.00 107.00   0.50    0.67    --   96.35-102.00  35.00  162
 23  \w     26.00 127.00   0.50    0.67    --   96.35 -87.00  60.00  202
 24  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00 -60.00   54
 25  \w     29.00  83.00   0.50    0.67    --   96.35 -68.00 -90.00  108
 26  \w     28.00  68.00   0.50    0.67    --   96.35 -59.00-120.00   80
 27  \w     28.00  68.00   0.50    0.67    --   96.35 -59.00-180.00   80
 28  \w     28.00  68.00   0.50    0.67    --   96.35 -59.00  30.00   80
 29  \w     28.00  68.00   0.50    0.67    --   96.35 -59.00  60.00   80
 30  \w     28.00  68.00   0.50    0.67    --   96.35 -59.00  90.00   80
 31  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00  60.00   54
 32  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00 120.00   54
 33  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00 150.00   54
 34  \w     28.00  68.00   0.50    0.67    --   96.35 -59.00   0.00   80
 35  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00  30.00   54
 36  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00  90.00   54
 37  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00   0.00   54
 38  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00 -90.00   54
 39  \w     30.00  57.00   0.50    0.67    --   96.35 -50.00-120.00   54
 40  \w    -26.00  61.00   0.50    0.20    --   40.83 -54.00-180.00  174
 41  \w    -37.00  27.00   0.50    0.20    --  -40.83  32.00   0.00  128
 42  \w    -31.00  28.00   0.50    0.20    --   40.83 -21.00  90.00  118
 43  \w    -27.00  37.00   0.50    0.20    --   40.83 -32.00  30.00  128
 44  \w    -24.00  35.00   0.50    0.20    --  -40.83  11.00  60.00  118
 45  \w    -28.00  31.00   0.50    0.20    --  -40.83  21.00  30.00  118
 46  \w    -47.00 -15.00   0.50    0.67    --  -82.50  42.00 -30.00   64
 47  \w    -47.00 -15.00   0.50    0.67    --  -82.50  42.00 -60.00   64
 48  \w    -57.00 -16.00   0.50    0.67    --  -82.50  50.00 -90.00   82
 49  \w    -47.00 -15.00   0.50    0.67    --  -82.50  42.00   0.00   64
 50  \w    -47.00 -15.00   0.50    0.67    --  -82.50  42.00  90.00   64
 51  \w   -153.00 -84.00   0.50    0.67    --  -82.50-102.00  35.00  138
 52  \w   -108.00 -63.00   0.50    0.20    --  -40.83-139.00-150.00   90
 53  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00-180.00  190
 54  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00 -90.00  190
 55  \w   -109.00 -14.00   0.50    0.20    --  -40.83 -77.00  60.00  190
 56  \w   -108.00 -17.00   0.50    0.20    --  -40.83 -66.00  90.00  182
 57  \w   -151.00 -55.00   0.50    0.67    --  -82.50 -77.00   0.00  192
 58  \w    -81.00 -11.00   0.50    0.67    --  -82.50 102.00 137.00  140
 59  \w    -77.00  15.00   0.50    0.20    --  -40.83 102.00 137.00  184
;
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25618
_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         68.153
_diffrn_reflns_theta_min         4.071
_exptl_absorpt_coefficient_mu    2.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67314
_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    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0593P)^2^+0.3721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3168
_reflns_number_total             3475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08380f2.cif
_cod_data_source_block           skm-3aa_auto
_cod_depositor_comments
'Adding full bibliography for 1573911--1573921.cif.'
_cod_database_code               1573916
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B)
1.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3), C7(H7), C2(H2), C6(H6), C3(H3A), C4(H4A), C5(H5)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              80129
_shelx_hkl_checksum              23675
_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
;