Electrochemical regioselective synthesis of sulfonyl 2,5-dihydrofuran-fused spiropyrimidines via multi-component radical cascade reactions
Yang, Qi-Liang; Xu, Rong-Yi; Ni, Cheng-Yang; Liu, Xin; Qiao, Zu-Lin; Zhang, Qi-Ying; Wang, Dong-Chao; Guo, Hai-Ming; Green Chemistry 27 (2025) 1499–1509; doi:10.1039/D4GC05637J

data_7249724
_publ_section_title
;
 Electrochemical regioselective synthesis of sulfonyl
 2,5-dihydrofuran-fused spiropyrimidines via multi-component radical
 cascade reactions
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              1499
_journal_page_last               1509
_journal_paper_doi               10.1039/D4GC05637J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C21 H20 N2 O6 S'
_chemical_formula_sum            'C21 H20 N2 O6 S'
_chemical_formula_weight         428.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-18 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.197(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4420(3)
_cell_length_b                   11.3110(2)
_cell_length_c                   21.1840(4)
_cell_measurement_reflns_used    4919
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0370
_cell_measurement_theta_min      4.4450
_cell_volume                     4099.76(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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    -72.00   4.00   1.00    2.16    --  -35.62 101.00 134.00   76
  2  \w     11.00  37.00   1.00    2.16    --   35.62-101.00  30.00   26
  3  \w     65.00  92.00   1.00    8.64    --  106.81-101.00  30.00   27
  4  \w    119.00 172.00   1.00    8.64    --  106.81 101.00 134.00   53
  5  \w   -108.00 -41.00   1.00    2.16    --  -35.62-178.00-120.00   67
  6  \w    -99.00 -22.00   1.00    2.16    --  -35.62 -57.00-180.00   77
  7  \w    -98.00 -43.00   1.00    2.16    --  -35.62-178.00-180.00   55
  8  \w     47.00  74.00   1.00    2.16    --   35.62-101.00  30.00   27
  9  \w     22.00  74.00   1.00    2.16    --   35.62 -99.00-120.00   52
 10  \w    115.00 168.00   1.00    8.64    --  106.81 111.00-180.00   53
 11  \w     89.00 174.00   1.00    8.64    --  106.81  61.00 -30.00   85
 12  \w     92.00 119.00   1.00    8.64    --  106.81  61.00 -60.00   27
 13  \w     38.00  99.00   1.00    8.64    --  106.81 -95.00  90.00   61
 14  \w     57.00 102.00   1.00    8.64    --  106.81-111.00-150.00   45
 15  \w     89.00 174.00   1.00    8.64    --  106.81  61.00  30.00   85
 16  \w    143.00 169.00   1.00    8.64    --  106.81  61.00 -60.00   26
 17  \w     41.00  79.00   1.00    8.64    --  106.81-111.00-180.00   38
 18  \w    109.00 137.00   1.00    8.64    --  106.81 111.00  90.00   28
 19  \w     41.00 115.00   1.00    8.64    --  106.81 -61.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011440000
_diffrn_orient_matrix_UB_12      0.0165930000
_diffrn_orient_matrix_UB_13      -0.0723819000
_diffrn_orient_matrix_UB_21      0.0275074000
_diffrn_orient_matrix_UB_22      0.1287634000
_diffrn_orient_matrix_UB_23      0.0125233000
_diffrn_orient_matrix_UB_31      0.0857040000
_diffrn_orient_matrix_UB_32      -0.0411492000
_diffrn_orient_matrix_UB_33      0.0101228000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9116
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.384
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_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     274
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0737P)^2^+1.7890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3409
_reflns_number_total             3910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05637j2.cif
_cod_data_source_block           gnn-20230525_auto
_cod_depositor_comments          'Adding full bibliography for 7249724.cif.'
_cod_database_code               7249724
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Na1 S1 N1 O1 C1'
_shelx_estimated_absorpt_t_max   0.719
_shelx_estimated_absorpt_t_min   0.620
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C30(H30), C26(H26), C15(H15), C14(H14), C13(H13),
 C29(H29), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O22(H22)
;
_shelx_res_checksum              81276
_shelx_hkl_checksum              48176
_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 1.578
_oxdiff_exptl_absorpt_empirical_full_min 0.646