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_7250076
_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 Br N2 O6 S'
_chemical_formula_sum            'C21 H19 Br N2 O6 S'
_chemical_formula_weight         507.35
_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             2024-10-15
_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                 98.1950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2458(2)
_cell_length_b                   12.0306(2)
_cell_length_c                   21.0605(3)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2620
_cell_measurement_theta_min      4.2350
_cell_volume                     4324.96(11)
_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 0.998
_diffrn_measured_fraction_theta_max 0.975
_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    -83.00 -58.00   1.00    1.00    --  -35.62 -25.00 -82.00   25
  2  \w    -61.00  32.00   1.00    1.00    --  -35.62  25.00  81.00   93
  3  \w     81.00 106.00   1.00    1.00    --   35.62  25.00  81.00   25
  4  \w     -7.00  33.00   1.00    1.00    --   35.62 -25.00 -82.00   40
  5  \w    106.00 154.00   1.00    1.36    --  106.81  25.00  81.00   48
  6  \w     37.00 124.00   1.00    1.36    --  106.81 -25.00 -82.00   87
  7  \w   -103.00 -20.00   1.00    1.00    --  -35.62 -57.00 -90.00   83
  8  \w    -97.00 -56.00   1.00    1.00    --  -35.62-178.00 150.00   41
  9  \w   -108.00 -42.00   1.00    1.00    --  -35.62-178.00  90.00   66
 10  \w     78.00 104.00   1.00    1.00    --   35.62 178.00 -90.00   26
 11  \w     43.00 115.00   1.00    1.36    --  106.81 -30.00 150.00   72
 12  \w    107.00 172.00   1.00    1.36    --  106.81  45.00 -30.00   65
 13  \w     46.00  97.00   1.00    1.36    --  106.81-111.00  60.00   51
 14  \w    106.00 174.00   1.00    1.36    --  106.81  77.00  90.00   68
 15  \w     56.00 133.00   1.00    1.36    --  106.81 -77.00 150.00   77
 16  \w    118.00 144.00   1.00    1.36    --  106.81 111.00   0.00   26
 17  \w     49.00  97.00   1.00    1.36    --  106.81-111.00 -30.00   48
;
_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      -0.0178537000
_diffrn_orient_matrix_UB_12      -0.0429064000
_diffrn_orient_matrix_UB_13      -0.0694911000
_diffrn_orient_matrix_UB_21      -0.0883059000
_diffrn_orient_matrix_UB_22      0.0016808000
_diffrn_orient_matrix_UB_23      0.0046986000
_diffrn_orient_matrix_UB_31      -0.0051885000
_diffrn_orient_matrix_UB_32      0.1206285000
_diffrn_orient_matrix_UB_33      -0.0247708000
_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  0.0186
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9126
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.399
_diffrn_reflns_theta_min         4.242
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72837
_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    1.558
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0604P)^2^+2.4295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3674
_reflns_number_total             4114
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05637j6.cif
_cod_data_source_block           xry-2-20231206_auto
_cod_database_code               7250076
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'S1 Br1 C1 N1 O1'
_shelx_estimated_absorpt_t_max   0.391
_shelx_estimated_absorpt_t_min   0.249
_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. Others
 Sof(Br)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00I(H00I)
3.b Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B)
3.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00S(H00S), C00U(H00U), C00V(H00V)
3.d Idealised Me refined as rotating group:
 C00R(H00C,H00D,H00E), C00T(H00F,H00G,H00H)
3.e Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_shelx_res_checksum              11629
_shelx_hkl_checksum              73955
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.734