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_7250077
_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         'C22 H22 N2 O6 S'
_chemical_formula_sum            'C22 H22 N2 O6 S'
_chemical_formula_weight         442.47
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-15
_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.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1273(3)
_cell_length_b                   13.8387(2)
_cell_length_c                   19.0079(3)
_cell_measurement_reflns_used    4471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9750
_cell_measurement_theta_min      4.6620
_cell_volume                     4242.20(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.139a 64-bit (release 02-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.139a (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    '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 0.982
_diffrn_measured_fraction_theta_max 0.966
_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     31.00  57.00   1.00    2.59    --   35.62 -99.00  18.00   26
  2  \w     13.00  38.00   1.00    2.59    --   35.62 -95.00 -81.00   25
  3  \w    -25.00  11.00   1.00    2.59    --   35.62 -38.00 122.00   36
  4  \w    112.00 149.00   1.00   10.36    --  106.81  99.00 124.00   37
  5  \w     54.00  84.00   1.00   10.36    --  106.81 -95.00 -81.00   30
  6  \w     98.00 176.00   1.00   10.36    --  106.81  38.00 -82.00   78
  7  \w   -103.00 -22.00   1.00    2.59    --  -35.62 -38.00 -90.00   81
  8  \w    -31.00   0.00   1.00    2.59    --   35.62 -57.00 -90.00   31
  9  \w     82.00 108.00   1.00    2.59    --   35.62 178.00-180.00   26
 10  \w      9.00  51.00   1.00    2.59    --   35.62 -57.00 -90.00   42
 11  \w    100.00 144.00   1.00   10.36    --  106.81 -15.00  90.00   44
 12  \w     52.00  98.00   1.00   10.36    --  106.81 -94.00 -30.00   46
 13  \w     73.00 100.00   1.00   10.36    --  106.81 -94.00  60.00   27
 14  \w     35.00  61.00   1.00   10.36    --  106.81 -15.00  90.00   26
 15  \w     47.00 102.00   1.00   10.36    --  106.81 -94.00-180.00   55
;
_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      0.0287164000
_diffrn_orient_matrix_UB_12      -0.0491293000
_diffrn_orient_matrix_UB_13      -0.0686485000
_diffrn_orient_matrix_UB_21      0.0855724000
_diffrn_orient_matrix_UB_22      -0.0191770000
_diffrn_orient_matrix_UB_23      0.0331189000
_diffrn_orient_matrix_UB_31      -0.0310639000
_diffrn_orient_matrix_UB_32      -0.0980572000
_diffrn_orient_matrix_UB_33      0.0276833000
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10581
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.304
_diffrn_reflns_theta_min         4.653
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.139a (Rigaku Oxford Diffraction, 2024)
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    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0697P)^2^+1.8462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3053
_reflns_number_total             3974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05637j5.cif
_cod_data_source_block           xry-20201015_auto
_cod_database_code               7250077
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.626
_shelx_estimated_absorpt_t_min   0.480
_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. Uiso/Uaniso restraints and constraints
Uanis(O00J) \\sim Ueq, Uanis(O00G) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C00F(H00F)
3.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B)
3.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00H(H00H), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T)
3.d Idealised Me refined as rotating group:
 C00S(H00D,H00E,H00G), C00U(H00I,H00J,H00N), C00V(H00S,H00U,H00V)
;
_shelx_res_checksum              34943
_shelx_hkl_checksum              29143
_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 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.684