Photoredox catalysed reductive cleavage of dibenzothiophene dioxides enabled by a temperature-controlled photoreactor
Wang, Siyuan; Le, Quang Truong; Shishido, Yoshiteru; Kokculer, Ismail Y.; Yamazaki, Ken; Perry, Gregory J. P.; Nightingale, Adrian Matthew; Yorimitsu, Hideki; Chemical Science  (2025) –; doi:10.1039/D5SC05889A

data_1576070
_publ_section_title
;
 Photoredox catalysed reductive cleavage of dibenzothiophene dioxides
 enabled by a temperature-controlled photoreactor
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC05889A
_journal_year                    2025
_chemical_formula_moiety         'C16 H11 F O2 S'
_chemical_formula_sum            'C16 H11 F O2 S'
_chemical_formula_weight         286.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-09
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.11.29 svn.rc9064207 for OlexSys, GUI svn.r7097)
;
_audit_update_record
;
2025-08-04 deposited with the CCDC.	2025-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5177(10)
_cell_length_b                   15.8556(8)
_cell_length_c                   8.0579(3)
_cell_measurement_reflns_used    14879
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.0480
_cell_measurement_theta_min      2.5630
_cell_volume                     2621.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -66.00  -7.00   0.50    5.00    --  -25.88 120.00  79.00  118
  2  \w    -48.00 -14.00   0.50    5.00    --   28.84 -20.00-162.00   68
  3  \w     23.00 106.00   0.50    5.00    --   28.84  20.00   4.00  166
  4  \w     21.00  52.00   0.50    5.00    --  -25.88  19.00 -60.00   62
  5  \w     21.00  52.00   0.50    5.00    --  -25.88  19.00 150.00   62
  6  \w     13.00  41.00   0.50    5.00    --   28.84  68.00 -65.62   56
  7  \w     14.00  48.00   0.50    5.00    --   28.84  66.00 -85.14   68
  8  \w     13.00  39.00   0.50    5.00    --   28.84  69.00 117.04   52
  9  \w     13.00  39.00   0.50    5.00    --   28.84  69.00 -38.83   52
 10  \w     13.00  41.00   0.50    5.00    --   28.84  68.00  64.13   56
 11  \w     13.00  39.00   0.50    5.00    --   28.84  69.00 163.35   52
 12  \w     13.00  39.00   0.50    5.00    --   28.84  69.00-129.45   52
 13  \w    -48.00 -17.00   0.50    5.00    --   28.84 -19.00  90.00   62
 14  \w    -48.00 -17.00   0.50    5.00    --   28.84 -19.00  60.00   62
 15  \w     13.00  38.00   0.50    5.00    --   28.84-120.00  -4.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041580000
_diffrn_orient_matrix_UB_12      0.0214404000
_diffrn_orient_matrix_UB_13      -0.0349944000
_diffrn_orient_matrix_UB_21      -0.0223393000
_diffrn_orient_matrix_UB_22      -0.0259538000
_diffrn_orient_matrix_UB_23      -0.0272904000
_diffrn_orient_matrix_UB_31      -0.0850872000
_diffrn_orient_matrix_UB_32      0.0078816000
_diffrn_orient_matrix_UB_33      0.0054016000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28432
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.489
_diffrn_reflns_theta_min         1.985
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.754
_refine_diff_density_min         -0.991
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.1184
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1399P)^2^+32.9093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3662
_refine_ls_wR_factor_ref         0.3682
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3034
_reflns_number_total             3322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05889a4.cif
_cod_data_source_block           2024sot0085_r1_100k
_cod_database_code               1576070
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C16H11F2O2S
_chemical_oxdiff_usercomment     SW-01-016
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id SW-01-016
_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 2.244
_oxdiff_exptl_absorpt_empirical_full_min 0.592