Thiosuccinimide enabled S-N bond formation to access <i>N</i>-sulfenylated sulfonamide derivatives with synthetic diversity.
Wang, Peifeng; Li, Shan; Wen, Huiling; Lei, Yin; Huang, Shujuan; Wang, Zixiu; Su, Jialong; Guan, Wenxiang; Lei, Jian; Organic & biomolecular chemistry 22 (2024) 990–997; doi:10.1039/d3ob01848b

data_7159740
_publ_section_title
;
 Thiosuccinimide enabled S-N bond formation to access
 <i>N</i>-sulfenylated sulfonamide derivatives with synthetic diversity.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              990
_journal_page_last               997
_journal_paper_doi               10.1039/d3ob01848b
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H14 N2 O2 S2'
_chemical_formula_sum            'C13 H14 N2 O2 S2'
_chemical_formula_weight         294.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-14
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-30 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9499(3)
_cell_length_b                   13.8952(10)
_cell_length_c                   20.1686(16)
_cell_measurement_reflns_used    1431
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.7900
_cell_measurement_theta_min      4.3570
_cell_volume                     1387.19(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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      0.00  59.00   1.00    1.00    --   40.23 -38.00 -90.00   59
  2  \w     74.00 102.00   1.00    1.50    --  108.83 -94.00 -60.00   28
  3  \w     38.00  78.00   1.00    1.00    --   40.23 -99.00  60.00   40
  4  \w     29.00  59.00   1.00    1.50    --  108.83 -94.00 -60.00   30
  5  \w     28.00 106.00   1.00    1.50    --  108.83 -94.00-150.00   78
  6  \w     27.00 131.00   1.00    1.50    --  108.83 -15.00-150.00  104
  7  \w    145.00 174.00   1.00    1.50    --  108.83  45.00-150.00   29
  8  \w     46.00 112.00   1.00    1.00    --   40.23  38.00  60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547036000
_diffrn_orient_matrix_UB_12      0.0036972000
_diffrn_orient_matrix_UB_13      -0.0750842000
_diffrn_orient_matrix_UB_21      -0.3055441000
_diffrn_orient_matrix_UB_22      -0.0099286000
_diffrn_orient_matrix_UB_23      0.0133321000
_diffrn_orient_matrix_UB_31      -0.0257536000
_diffrn_orient_matrix_UB_32      0.1103125000
_diffrn_orient_matrix_UB_33      0.0039295000
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2903
_diffrn_reflns_point_group_measured_fraction_full 0.835
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         4.384
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details
;
 Flack x determined using 449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2049
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.1028
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1841P)^2^+6.9228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2746
_refine_ls_wR_factor_ref         0.2893
_reflns_Friedel_coverage         0.416
_reflns_Friedel_fraction_full    0.608
_reflns_Friedel_fraction_max     0.608
_reflns_number_gt                1764
_reflns_number_total             2049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01848b2.cif
_cod_data_source_block           lj-2
_cod_depositor_comments          'Adding full bibliography for 7159740.cif.'
_cod_original_cell_volume        1387.21(17)
_cod_database_code               7159740
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(S1)
3. Rigid body (RIGU) restrains
 N2, S2, O2, O1, C11, C12, C10, H12, C13, H10, C9, C8, H13, H9, N1, S1, H1, C1,
  C14, C6, H14, C3, H6, C5, H3, C4, H5, C7, H7A, H7B, H7C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.007
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C10(H10), N1(H1), C9(H9), C14(H14), C3(H3), C6(H6), C5(H5)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4584
_olex2_date_sample_data_collection 2023-08-14
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.587