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_7250078
_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 H19 F3 N2 O6 S, C H2 Cl2'
_chemical_formula_sum            'C23 H21 Cl2 F3 N2 O6 S'
_chemical_formula_weight         581.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 113.464(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0694(16)
_cell_length_b                   9.9654(8)
_cell_length_c                   17.9448(17)
_cell_measurement_reflns_used    5628
_cell_measurement_temperature    292.38(10)
_cell_measurement_theta_max      26.8800
_cell_measurement_theta_min      3.9890
_cell_volume                     2636.0(5)
_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      292.38(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.873
_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     16.00  41.00   1.00    7.68    --   16.29  63.00 -33.00   25
  2  \w    -36.00 -10.00   1.00    7.68    --   16.29 -63.00-170.00   26
  3  \w    -59.00  -6.00   1.00    7.68    --  -16.91 -63.00-170.00   53
  4  \w     39.00  84.00   1.00    7.68    --   16.29 178.00-150.00   45
  5  \w     -6.00  54.00   1.00    7.68    --   16.29 -99.00 -30.00   60
  6  \w     28.00  53.00   1.00    7.68    --   16.29 -99.00  30.00   25
  7  \w     -3.00  36.00   1.00    7.68    --   16.29  38.00-180.00   39
  8  \w     42.00  84.00   1.00    7.68    --   16.29  38.00-180.00   42
  9  \w    -30.00  10.00   1.00    7.68    --  -16.91 -77.00 120.00   40
;
_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      -0.0250146000
_diffrn_orient_matrix_UB_12      -0.0123946000
_diffrn_orient_matrix_UB_13      0.0241243000
_diffrn_orient_matrix_UB_21      -0.0255586000
_diffrn_orient_matrix_UB_22      -0.0499691000
_diffrn_orient_matrix_UB_23      -0.0278826000
_diffrn_orient_matrix_UB_31      0.0321825000
_diffrn_orient_matrix_UB_32      -0.0492762000
_diffrn_orient_matrix_UB_33      0.0221891000
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19250
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.192
_diffrn_reflns_theta_min         3.438
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41185
_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    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0075(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6226
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0746
_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^)+(0.1151P)^2^+2.0244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4386
_reflns_number_total             6226
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05637j3.cif
_cod_data_source_block           xry-20231107_auto
_cod_database_code               7250078
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.893
_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. Restrained distances
 F00X-C00Y \\sim F00Y-C00Y
 with sigma of 0.02
 C00Y-F00Z \\sim C00Y-F0
 with sigma of 0.02
 C00Y-F010 \\sim C00Y-F1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1 \\sim F00Z \\sim F0 \\sim F00X \\sim F00Y \\sim F010: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(F00X) \\sim Ueq, Uanis(F00Z) \\sim Ueq, Uanis(F010) \\sim Ueq, Uanis(F0)
\\sim Ueq, Uanis(F00Y) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(F0)=Sof(F00Y)=Sof(F1)=1-FVAR(1)
 Sof(F00X)=Sof(F00Z)=Sof(F010)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00F(H00F)
5.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S),
 C00T(H00T), C00V(H00V), C00W(H00W)
5.d Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00E), C00Q(H00G,H00H,H00I)
5.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              54523
_shelx_hkl_checksum              7859
_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 2.367
_oxdiff_exptl_absorpt_empirical_full_min 0.495