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_1573920
_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 H27 N O5 S, C23 H23 N O5 S'
_chemical_formula_sum            'C47 H46 N3 O10 S2'
_chemical_formula_weight         876.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                78.612(9)
_cell_angle_beta                 77.456(10)
_cell_angle_gamma                84.925(9)
_cell_formula_units_Z            2
_cell_length_a                   9.952(3)
_cell_length_b                   12.022(3)
_cell_length_c                   18.755(5)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      28.703
_cell_measurement_theta_min      2.171
_cell_volume                     2144.8(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'Four-circle Kappa diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            90521
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.099
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1644 before and 0.1244 after correction.
The Ratio of minimum to maximum transmission is 0.8000.
The \l/2 correction factor is Not present.
;
_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    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             922
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.134
_refine_diff_density_max         1.854
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         8133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0933
_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^)+(0.0997P)^2^+5.0012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2287
_refine_ls_wR_factor_ref         0.2319
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7536
_reflns_number_total             8133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08380f2.cif
_cod_data_source_block           skmpd6
_cod_depositor_comments
'Adding full bibliography for 1573911--1573921.cif.'
_cod_original_cell_volume        2144.7(10)
_cod_database_code               1573920
_shelx_shelxl_version_number     2018/3
_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. Others
 Fixed Sof: C30(0.5) C40(0.5)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C15(H15A,H15B),
 C16(H16A,H16B), C28(H28A,H28B), C32(H32A,H32B), C33(H33A,H33B), C38(H38A,H38B),
  C39(H39A,H39B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22), C23(H23), C26(H26),
 C35(H35), C36(H36), C37(H37), C43(H43), C46(H46), C47(H47)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C45(H45A,H45B,H45C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 16 electrons were 
found in a volume of 60\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
0.5[CH4O] per Unit Cell 
which account for 18 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              17463
_shelx_hkl_checksum              57719
_shelx_fab_checksum              46405
_olex2_submission_special_instructions 'No special instructions were received'