Modular synthesis of sulfilimines <i>via</i> NFSI-mediated S-arylation of sulfenamides with naphthols, phenols and indoles.
Dong, Fucong; Liu, He; Xiong, Xiaodong; Organic & biomolecular chemistry 24 (2026) 1515–1521; doi:10.1039/d5ob01861g

data_7160984
_publ_section_title
;
 Modular synthesis of sulfilimines <i>via</i> NFSI-mediated S-arylation of
 sulfenamides with naphthols, phenols and indoles.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1515
_journal_page_last               1521
_journal_paper_doi               10.1039/d5ob01861g
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C22 H23 N O2 S'
_chemical_formula_sum            'C22 H23 N O2 S'
_chemical_formula_weight         365.47
_chemical_name_systematic        1
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-10-10 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                104.852(6)
_cell_angle_beta                 96.426(6)
_cell_angle_gamma                106.540(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4970(7)
_cell_length_b                   9.5185(7)
_cell_length_c                   11.6945(8)
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5550
_cell_measurement_theta_min      3.9270
_cell_volume                     959.85(13)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.832
_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    -82.00 -55.00   1.00    1.17    --  -16.23-178.00 -90.00   27
  2  \w    -82.00 -43.00   1.00    1.17    --  -16.23 -37.00-120.00   39
  3  \w     -9.00  23.00   1.00    1.17    --   17.17  77.00  30.00   32
  4  \w    -10.00  24.00   1.00    1.17    --   17.17  77.00-180.00   34
  5  \w    -36.00  43.00   1.00    1.17    --   17.17 -77.00  60.00   79
  6  \w    -42.00  33.00   1.00    1.17    --   17.17 -57.00 -60.00   75
  7  \w    -49.00  34.00   1.00    1.17    --   17.17 -57.00-180.00   83
  8  \w      8.00  34.00   1.00    1.17    --   17.17  77.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0518842000
_diffrn_orient_matrix_UB_12      -0.0175613000
_diffrn_orient_matrix_UB_13      0.0375787000
_diffrn_orient_matrix_UB_21      0.0578522000
_diffrn_orient_matrix_UB_22      -0.0023257000
_diffrn_orient_matrix_UB_23      0.0427209000
_diffrn_orient_matrix_UB_31      0.0168205000
_diffrn_orient_matrix_UB_32      0.0796093000
_diffrn_orient_matrix_UB_33      0.0293848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8403
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.459
_diffrn_reflns_theta_min         3.388
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57260
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.1548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3558
_reflns_number_total             4431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01861g2.cif
_cod_data_source_block           219nf_auto
_cod_database_code               7160984
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C15(H15), C16(H16), C6(H6), C3(H3), C13(H13), C11(H11),
 C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              45538
_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 1.654
_oxdiff_exptl_absorpt_empirical_full_min 0.522