Unveiling a PhSeSePh/I2-Mediated Radical Cyclisation of 2-Alkynyl-N-alkyl-N-tosylanilines: Access to 3-Sulfonyl Indoles via 1,3 Tosyl-Relocation
., Nidhi; ., Muskan; Panda, Debanik; Verma, Akhilesh K.; Chemical Communications  (2026) –; doi:10.1039/D6CC00419A

data_7135676
_publ_section_title
;
 Unveiling a PhSeSePh/I<sub>2</sub>-mediated radical cyclisation of
 2-alkynyl-<i>N</i>-alkyl-<i>N</i>-tosylanilines: access to 3-sulfonyl
 indoles <i>via</i> 1,3 tosyl-relocation.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7957
_journal_page_last               7960
_journal_paper_doi               10.1039/d6cc00419a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C25 H24 Br N O2 S'
_chemical_formula_sum            'C25 H24 Br N O2 S'
_chemical_formula_weight         482.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-10-14 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.479(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0627(6)
_cell_length_b                   14.3169(7)
_cell_length_c                   12.8459(7)
_cell_measurement_reflns_used    6135
_cell_measurement_temperature    168(20)
_cell_measurement_theta_max      29.5500
_cell_measurement_theta_min      3.3070
_cell_volume                     2216.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      168(20)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.800
_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    -18.00  60.00   0.50    4.00    --   -5.22  38.00 -30.00  156
  2  \w    -74.00 -17.00   0.50    4.00    --   -5.22 -38.00 150.00  114
  3  \w    -15.00  76.00   0.50    4.00    --    5.38  77.00  90.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0436610000
_diffrn_orient_matrix_UB_12      -0.0003769000
_diffrn_orient_matrix_UB_13      -0.0352442000
_diffrn_orient_matrix_UB_21      0.0014180000
_diffrn_orient_matrix_UB_22      -0.0494758000
_diffrn_orient_matrix_UB_23      0.0020735000
_diffrn_orient_matrix_UB_31      -0.0395461000
_diffrn_orient_matrix_UB_32      -0.0020962000
_diffrn_orient_matrix_UB_33      -0.0424706000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17367
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.945
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_refine_diff_density_max         1.798
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+1.7531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3869
_reflns_number_total             5625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00419a2.cif
_cod_data_source_block           nps-ms1-lt_auto
_cod_depositor_comments          'Adding full bibliography for 7135676.cif.'
_cod_database_code               7135676
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O S Se'
_chemical_oxdiff_usercomment     18-04-2024
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All Br(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br1(0.75) Br2(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C00P(H00K,H00O), C00T(H00U,H00V)
3.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R)
3.c Idealised Me refined as rotating group:
 C00O(H00A,H00D,H00E), C00S(H00P,H00S,H00T)
;
_shelx_res_checksum              25454
_shelx_hkl_checksum              66259
_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 5.832
_oxdiff_exptl_absorpt_empirical_full_min 0.658