A photo-Fenton-like (trideutero)methylation reaction of N/O heterocycles with DMSO(-d6) induced by EDA complex photocatalysis
Qin, Changsheng; Li, Chenxu; Gao, Fang; Wang, Jingfang; Zhang, Zhihua; Zhang, Shuai; Li, Xinyue; Sun, Yi; Hu, Meiqian; Wang, Shoucai; Ji, Fanghua; Jiang, Guangbin; Green Chemistry 27 (2025) 6206–6212; doi:10.1039/D4GC05939E

data_7250349
_publ_section_title
;
 A photo-Fenton-like (trideutero)methylation reaction of N/O heterocycles
 with DMSO(-d6) induced by EDA complex photocatalysis
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              6206
_journal_page_last               6212
_journal_paper_doi               10.1039/D4GC05939E
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C10 H9 N3 O2'
_chemical_formula_sum            'C10 H9 N3 O2'
_chemical_formula_weight         203.20
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2mj9cv
_audit_creation_date             2025-03-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   5.54010(10)
_cell_length_b                   21.2296(6)
_cell_length_c                   31.9506(7)
_cell_measurement_reflns_used    16926
_cell_measurement_temperature    100.02(11)
_cell_measurement_theta_max      29.3180
_cell_measurement_theta_min      1.9000
_cell_volume                     3757.84(15)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.106a 64-bit (release 01-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.889
_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    -11.00  55.00   0.50    2.50    --   10.52 -99.00-120.00  132
  2  \w      7.00  35.00   0.50    2.50    --   10.52 -99.00-180.00   56
  3  \w    -10.00  52.00   0.50    2.50    --   10.52 -99.00 -23.00  124
  4  \w    -34.00  23.00   0.50    2.50    --   10.52 -19.00   0.00  114
  5  \w    -84.00  16.00   0.50    2.50    --  -11.15 -57.00 -60.00  200
  6  \w    -77.00 -42.00   0.50    2.50    --  -11.15 -57.00-120.00   70
  7  \w    -35.00 -10.00   0.50    2.50    --  -11.15 -57.00-120.00   50
  8  \w     20.00  55.00   0.50    2.50    --  -11.15  57.00  90.00   70
  9  \w    -54.00   4.00   0.50    2.50    --  -11.15  99.00  82.00  116
 10  \w    -37.00  -8.00   0.50    2.50    --  -11.15  57.00  90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1053086000
_diffrn_orient_matrix_UB_12      0.0180417000
_diffrn_orient_matrix_UB_13      0.0039377000
_diffrn_orient_matrix_UB_21      -0.0603760000
_diffrn_orient_matrix_UB_22      -0.0274906000
_diffrn_orient_matrix_UB_23      0.0070553000
_diffrn_orient_matrix_UB_31      0.0406023000
_diffrn_orient_matrix_UB_32      0.0059409000
_diffrn_orient_matrix_UB_33      0.0206801000
_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  0.0453
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            42696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.461
_diffrn_reflns_theta_min         1.919
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (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    1.437
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0477P)^2^+1.3521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3629
_reflns_number_total             4638
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05939e2.cif
_cod_data_source_block           1288-n-bn-100k_autored
_cod_depositor_comments          'Adding full bibliography for 7250349.cif.'
_cod_database_code               7250349
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C20(H20), C10(H10), C3(H3), C17(H17), C7(H7), C13(H13),
 C18(H18), C9(H9), C19(H19), C8(H8)
;
_shelx_res_checksum              94695
_shelx_hkl_checksum              74287
_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 1.609
_oxdiff_exptl_absorpt_empirical_full_min 0.399