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_7250074
_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         'C17 H20 N2 O6 S'
_chemical_formula_sum            'C17 H20 N2 O6 S'
_chemical_formula_weight         380.424
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-10-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-21 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.500(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6709(3)
_cell_length_b                   13.3145(3)
_cell_length_c                   11.2685(3)
_cell_measurement_reflns_used    6302
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.2910
_cell_measurement_theta_min      4.9890
_cell_volume                     1780.68(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.139a (Rigaku OD, 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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9859
_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    -65.00 -40.00   1.00    1.00    --  -35.37-178.00   0.00   25
  2  \w    -95.00 -41.00   1.00    1.00    --  -35.37-178.00 150.00   54
  3  \w   -104.00  34.00   1.00    1.00    --  -35.37   0.00-120.00  138
  4  \w     64.00 108.00   1.00    1.00    --   35.37 178.00  60.00   44
  5  \w     44.00  71.00   1.00    1.00    --   35.37 -99.00  30.00   27
  6  \w     59.00  86.00   1.00    1.00    --   35.37-178.00-180.00   27
  7  \w     28.00 102.00   1.00    1.00    --   35.37  57.00  60.00   74
  8  \w     39.00  73.00   1.00    1.00    --   35.37 -99.00-120.00   34
  9  \w     11.00  73.00   1.00    1.00    --   35.37 -99.00 150.00   62
 10  \w     63.00  88.00   1.00    1.00    --   35.37-178.00 -90.00   25
 11  \w     12.00  37.00   1.00    1.00    --   35.37 -99.00  30.00   25
 12  \w     92.00 146.00   1.00    2.22    --  106.81  45.00  90.00   54
 13  \w     65.00 108.00   1.00    2.22    --  106.81-111.00-150.00   43
 14  \w     38.00 118.00   1.00    2.22    --  106.81 -45.00  90.00   80
 15  \w     60.00  89.00   1.00    2.22    --  106.81 -61.00  90.00   29
 16  \w     78.00 105.00   1.00    2.22    --  106.81 -77.00-150.00   27
 17  \w    122.00 171.00   1.00    2.22    --  106.81 111.00   0.00   49
 18  \w     47.00 108.00   1.00    2.22    --  106.81-111.00 120.00   61
 19  \w     41.00  99.00   1.00    2.22    --  106.81 -45.00-120.00   58
 20  \w     68.00 108.00   1.00    2.22    --  106.81-111.00 -30.00   40
 21  \w    107.00 174.00   1.00    2.22    --  106.81  77.00  30.00   67
 22  \w     38.00 124.00   1.00    2.22    --  106.81 -45.00 -60.00   86
 23  \w    135.00 170.00   1.00    2.22    --  106.81  77.00-120.00   35
 24  \w     62.00 107.00   1.00    2.22    --  106.81-111.00  30.00   45
 25  \w     50.00 165.00   1.00    2.22    --  106.81   0.00-150.00  115
 26  \w     42.00  71.00   1.00    2.22    --  106.81 -94.00  60.00   29
;
_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      -0.0135041000
_diffrn_orient_matrix_UB_12      -0.0935122000
_diffrn_orient_matrix_UB_13      0.0738848000
_diffrn_orient_matrix_UB_21      -0.1113490000
_diffrn_orient_matrix_UB_22      -0.0256439000
_diffrn_orient_matrix_UB_23      -0.1073037000
_diffrn_orient_matrix_UB_31      0.0653744000
_diffrn_orient_matrix_UB_32      -0.0630617000
_diffrn_orient_matrix_UB_33      -0.0658914000
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9859
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10782
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9859
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         71.30
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61715
_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    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             804.204
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.3597
_refine_diff_density_min         -0.6017
_refine_diff_density_rms         0.0769
_refine_ls_d_res_high            0.8139
_refine_ls_d_res_low             11.8684
_refine_ls_goodness_of_fit_ref   1.0476
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0476
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.6203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3067
_reflns_number_total             3421
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4gc05637j7.cif
_cod_data_source_block           XRY-20241018-1_auto
_cod_original_cell_volume        1780.67(8)
_cod_database_code               7250074
_chemical_oxdiff_formula         'S1 C1 N1 O1'
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C21(H21a,H21b)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C15(H15), C25(H25), C20(H20)
2.d Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C22(H22a,H22b,H22c), C1(H1a,H1b,H1c)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 1.627
_oxdiff_exptl_absorpt_empirical_full_min 0.638