Regioselective Functionalization of Sulfenamides: S-Arylation with Cyclic Diaryl λ3 -Bromanes and λ3 -Chloranes
Chen, Jiahong; Huang, Yuanyuan; Wang, Nan; Wang, Mengke; Huang, Weichun; Wu, Xin-Xing; Xu, Xiao-Ping; Zi, You; Chemical Communications  (2025) –; doi:10.1039/D5CC05327G

data_7135180
_publ_section_title
;
 Regioselective Functionalization of Sulfenamides: S-Arylation with Cyclic
 Diaryl \l3 -Bromanes and \l3 -Chloranes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC05327G
_journal_year                    2025
_chemical_formula_moiety         'C26 H19 Br2 N O S'
_chemical_formula_sum            'C26 H19 Br2 N O S'
_chemical_formula_weight         553.30
_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             2025-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-06-18 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                78.4350(10)
_cell_angle_beta                 79.2600(10)
_cell_angle_gamma                79.2680(10)
_cell_formula_units_Z            2
_cell_length_a                   8.23180(10)
_cell_length_b                   10.86210(10)
_cell_length_c                   13.1254(2)
_cell_measurement_reflns_used    11480
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.3060
_cell_measurement_theta_min      4.1920
_cell_volume                     1116.05(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.944
_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     42.00 115.00   0.50    0.05    --  104.39-125.00  30.00  146
  2  \w     75.00 117.00   0.50    0.05    --  104.39-125.00 -30.00   84
  3  \w     36.00 111.00   0.50    0.05    --  104.39-125.00-150.00  150
  4  \w     83.00 108.00   0.50    0.05    --  104.39 -94.00-150.00   50
  5  \w     54.00 108.00   0.50    0.05    --  104.39 -94.00-180.00  108
  6  \w     32.00  75.00   0.50    0.05    --  104.39 -94.00-150.00   86
  7  \w    -19.00  64.00   0.50    0.05    --   46.55 -91.00   7.00  166
  8  \w     48.00  87.00   0.50    0.05    --  104.39 -91.00   7.00   78
  9  \w    100.00 125.00   0.50    0.05    --  104.39 -91.00   7.00   50
 10  \w     81.00 106.00   0.50    0.05    --  104.39 -77.00 -90.00   50
 11  \w     32.00  61.00   0.50    0.05    --  104.39 -61.00 -90.00   58
 12  \w     44.00  73.00   0.50    0.05    --  104.39 -61.00  60.00   58
 13  \w     79.00 165.00   0.50    0.05    --  104.39 125.00-120.00  172
 14  \w     82.00 141.00   0.50    0.05    --  104.39  91.00 121.00  118
 15  \w     76.00 102.00   0.50    0.05    --  104.39 125.00 150.00   52
 16  \w    119.00 144.00   0.50    0.05    --  104.39 125.00 150.00   50
 17  \w    -24.00  20.00   0.50    0.05    --  -46.55  19.00  30.00   88
 18  \w    -38.00  25.00   0.50    0.05    --  -46.55  37.00-150.00  126
 19  \w    -66.00 -32.00   0.50    0.05    -- -102.00  61.00 -30.00   68
 20  \w    -38.00  21.00   0.50    0.05    --  -46.55  37.00  90.00  118
 21  \w    -25.00  29.00   0.50    0.05    --  -46.55  19.00 150.00  108
 22  \w     -6.00  24.00   0.50    0.05    --  -46.55  91.00 121.00   60
 23  \w    -72.00 -46.00   0.50    0.05    --  -46.55  91.00 121.00   52
 24  \w   -110.00 -37.00   0.50    0.05    -- -102.00 125.00  30.00  146
 25  \w   -104.00 -79.00   0.50    0.05    -- -102.00  91.00 121.00   50
 26  \w   -163.00 -91.00   0.50    0.05    -- -102.00 -45.00  30.00  144
 27  \w   -173.00-143.00   0.50    0.05    -- -102.00 -45.00  60.00   60
 28  \w   -142.00-117.00   0.50    0.05    -- -102.00 -45.00  60.00   50
 29  \w   -146.00 -95.00   0.50    0.05    -- -102.00 -45.00-120.00  102
 30  \w   -106.00 -80.00   0.50    0.05    --  -46.55-125.00   0.00   52
 31  \w   -113.00 -74.00   0.50    0.05    --  -46.55-125.00 150.00   78
 32  \w   -156.00 -81.00   0.50    0.05    -- -102.00-125.00 150.00  150
 33  \w   -175.00 -81.00   0.50    0.05    -- -102.00 -94.00 120.00  188
 34  \w   -155.00 -78.00   0.50    0.05    -- -102.00 -91.00   7.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0133384000
_diffrn_orient_matrix_UB_12      0.1401558000
_diffrn_orient_matrix_UB_13      -0.0473360000
_diffrn_orient_matrix_UB_21      -0.0594901000
_diffrn_orient_matrix_UB_22      -0.0164514000
_diffrn_orient_matrix_UB_23      -0.1003336000
_diffrn_orient_matrix_UB_31      -0.1829120000
_diffrn_orient_matrix_UB_32      0.0394592000
_diffrn_orient_matrix_UB_33      0.0489691000
_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  0.0203
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11932
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.400
_diffrn_reflns_theta_min         4.205
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
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    1.646
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.451
_refine_diff_density_min         -1.037
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0433P)^2^+1.2034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             4427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05327g2.cif
_cod_data_source_block           cjh-525-zy-nt_0617_auto
_cod_database_code               7135180
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.552
_shelx_estimated_absorpt_t_min   0.431
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              75568
_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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.788