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_7250075
_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 H19 F N2 O6 S'
_chemical_formula_sum            'C21 H19 F N2 O6 S'
_chemical_formula_weight         446.44
_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.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.322(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4340(9)
_cell_length_b                   11.5074(6)
_cell_length_c                   20.8088(11)
_cell_measurement_reflns_used    4769
_cell_measurement_temperature    292.69(10)
_cell_measurement_theta_max      28.4880
_cell_measurement_theta_min      4.0490
_cell_volume                     4078.5(4)
_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_environment      air
_diffrn_ambient_temperature      292.69(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.869
_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     -3.00  71.00   1.00   11.50    --   16.13  64.00 -61.00   74
  2  \w    -42.00 -16.00   1.00   11.50    --  -16.83 -64.00 162.00   26
  3  \w     19.00  49.00   1.00   11.50    --  -16.83  64.00 -61.00   30
  4  \w     39.00  65.00   1.00   11.50    --   16.13 178.00-180.00   26
  5  \w     51.00  78.00   1.00   11.50    --   16.13 178.00  60.00   27
  6  \w     40.00  87.00   1.00   11.50    --   16.13 178.00 -90.00   47
  7  \w      2.00  54.00   1.00   11.50    --   16.13 -99.00 120.00   52
  8  \w    -37.00 -12.00   1.00   11.50    --  -16.83 -77.00  90.00   25
  9  \w    -30.00   8.00   1.00   11.50    --  -16.83 -77.00 -60.00   38
;
_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      -0.0273214000
_diffrn_orient_matrix_UB_12      -0.0300920000
_diffrn_orient_matrix_UB_13      0.0147378000
_diffrn_orient_matrix_UB_21      -0.0109375000
_diffrn_orient_matrix_UB_22      -0.0349470000
_diffrn_orient_matrix_UB_23      -0.0285792000
_diffrn_orient_matrix_UB_31      0.0294580000
_diffrn_orient_matrix_UB_32      -0.0408997000
_diffrn_orient_matrix_UB_33      0.0136396000
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13124
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.879
_diffrn_reflns_theta_min         3.433
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34827
_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    1.454
_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         0.276
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+2.8288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3608
_reflns_number_total             4670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05637j4.cif
_cod_data_source_block           xry-1-20231106_auto
_cod_database_code               7250075
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.902
_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:
 C00J(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00L(H00L), C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00U(H00U), C00V(H00V)
2.d Idealised Me refined as rotating group:
 C00P(H00C,H00D,H00E), C00S(H00F,H00G,H00H)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              98270
_shelx_hkl_checksum              90441
_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 2.151
_oxdiff_exptl_absorpt_empirical_full_min 0.535