Electrochemical selective incorporation of SO2 to synthesize fused-ring framework compounds
Lei, Zhi-Long; Tan, Dan; Qin, Jin-Tao; Meng, Xiu-Jin; Cui, Fei-Hu; Tang, Hai-Tao; Pan, Ying-Ming; Green Chemistry 27 (2025) 6825–6830; doi:10.1039/D5GC01138H

data_7250421
_publ_section_title
;
 Electrochemical selective incorporation of SO2 to synthesize fused-ring
 framework compounds
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              6825
_journal_page_last               6830
_journal_paper_doi               10.1039/D5GC01138H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C13 H16 N2 O5 S2'
_chemical_formula_sum            'C13 H16 N2 O5 S2'
_chemical_formula_weight         344.40
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-12-19 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.27430(10)
_cell_length_b                   24.3447(3)
_cell_length_c                   11.0893(2)
_cell_measurement_reflns_used    14429
_cell_measurement_temperature    295.81(10)
_cell_measurement_theta_max      76.9980
_cell_measurement_theta_min      3.6220
_cell_volume                     3021.34(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.115a 64-bit (release 15-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.115a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.81(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.950
_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   -100.00 -71.00   0.50    0.13    --  -47.70-125.00  90.00   58
  2  \w   -117.00 -78.00   0.50    0.13    --  -47.70-126.00  48.00   78
  3  \w   -113.00 -78.00   0.50    0.13    --  -47.70-125.00 -60.00   70
  4  \w   -112.00 -87.00   0.50    0.13    --  -47.70-144.00-119.00   50
  5  \w   -117.00 -70.00   0.50    0.13    --  -47.70-125.00-180.00   94
  6  \w   -126.00 -70.00   0.50    0.30    --  -91.75 -77.00 -30.00  112
  7  \w    -23.00  28.00   0.50    0.13    --  -47.70  19.00 -90.00  102
  8  \w    -47.00 -22.00   0.50    0.13    --  -47.70 144.00 -65.00   50
  9  \w   -103.00 -63.00   0.50    0.13    --  -47.70 144.00 -65.00   80
 10  \w    -87.00 -62.00   0.50    0.30    --  -91.75 144.00 -65.00   50
 11  \w    -81.00 -23.00   0.50    0.30    --  -91.75 125.00 -90.00  116
 12  \w    -81.00 -56.00   0.50    0.30    --  -91.75 126.00 125.00   50
 13  \w     -7.00  25.00   0.50    0.13    --  -47.70  19.00 -30.00   64
 14  \w     99.00 174.00   0.50    0.30    --  107.74  19.00 120.00  150
 15  \w     79.00 158.00   0.50    0.30    --  107.74 144.00 -65.00  158
 16  \w    100.00 174.00   0.50    0.30    --  107.74  19.00  60.00  148
 17  \w     35.00  65.00   0.50    0.30    --  107.74 -57.00  90.00   60
 18  \w     35.00 104.00   0.50    0.30    --  107.74 -77.00  60.00  138
 19  \w     35.00  64.00   0.50    0.30    --  107.74 -57.00-180.00   58
 20  \w     46.00 102.00   0.50    0.30    --  107.74 -99.00-120.00  112
 21  \w     76.00 104.00   0.50    0.30    --  107.74 -99.00 -90.00   56
 22  \w    103.00 129.00   0.50    0.30    --  107.74-144.00-119.00   52
 23  \w     38.00 115.00   0.50    0.30    --  107.74-126.00  48.00  154
 24  \w     39.00  64.00   0.50    0.13    --   47.70-126.00  48.00   50
 25  \w     51.00  79.00   0.50    0.13    --   47.70-144.00-119.00   56
 26  \w   -108.00 -72.00   0.50    0.30    --  -91.75-144.00-119.00   72
 27  \w   -137.00-112.00   0.50    0.30    --  -91.75 -99.00-180.00   50
 28  \w   -140.00-115.00   0.50    0.30    --  -91.75-126.00  48.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0938546000
_diffrn_orient_matrix_UB_12      0.0028743000
_diffrn_orient_matrix_UB_13      -0.0898075000
_diffrn_orient_matrix_UB_21      0.0023199000
_diffrn_orient_matrix_UB_22      0.0630468000
_diffrn_orient_matrix_UB_23      0.0113346000
_diffrn_orient_matrix_UB_31      0.1006835000
_diffrn_orient_matrix_UB_32      -0.0041653000
_diffrn_orient_matrix_UB_33      0.1068405000
_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  0.0576
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23617
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.389
_diffrn_reflns_theta_min         3.631
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.438
_exptl_absorpt_correction_T_max  0.618
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.115a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         6084
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0686
_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^)+(0.0834P)^2^+4.2351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5028
_reflns_number_total             6084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc01138h2.cif
_cod_data_source_block           20240408-pym-lzl-221_auto
_cod_depositor_comments
'Adding full bibliography for 7250420--7250421.cif.'
_cod_database_code               7250421
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H N O S'
_shelx_estimated_absorpt_t_max   0.645
_shelx_estimated_absorpt_t_min   0.546
_diffrn_oxdiff_digest_frames
;
013d750926503b8250941c014730d50aa202338be24
;
_diffrn_oxdiff_digest_hkl
;
4394a08121ad04d5837beb42bc5924cd5f8b34
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Restrained distances
 C8-C11B
 with sigma of 0.02
 C10-C11B
 with sigma of 0.02
 C11B-C12B
 with sigma of 0.02
 C12B-S2
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Sof(O8B)=Sof(O9B)=Sof(O10B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24B)=Sof(C25B)=
 Sof(H25C)=Sof(H25D)=Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(O8A)=Sof(O9A)=Sof(O10A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(H25A)=Sof(H25B)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12C)=Sof(H12D)=1-FVAR(2)
 Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C11B(H11B)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12B(H12C,H12D)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              60725
_shelx_hkl_checksum              3996
_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 4.287
_oxdiff_exptl_absorpt_empirical_full_min 0.560