Iodine-mediated synthesis of indole-fused benzothiazepinones through intramolecular C2-amidation of amide-tethered C3-sulfenylindoles.
Singh, Gargi; Arockiaraj, Mariyaraj; Rajeshkumar, Venkatachalam; Organic & biomolecular chemistry 23 (2025) 7766–7772; doi:10.1039/d5ob00842e

data_7160666
_publ_section_title
;
 Iodine-mediated synthesis of indole-fused benzothiazepinones through
 intramolecular C2-amidation of amide-tethered C3-sulfenylindoles.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7766
_journal_page_last               7772
_journal_paper_doi               10.1039/d5ob00842e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C24 H20 N2 O S'
_chemical_formula_sum            'C24 H20 N2 O S'
_chemical_formula_weight         384.48
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-02-22 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.766(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1153(13)
_cell_length_b                   13.8051(16)
_cell_length_c                   16.4582(19)
_cell_measurement_reflns_used    4768
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      51.310
_cell_measurement_theta_min      4.677
_cell_volume                     2002.7(4)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15883
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.430
_diffrn_reflns_theta_min         1.953
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.592
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.592
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0590
_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^)+(0.1900P)^2^+6.6190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.2175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3221
_reflns_number_total             4773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00842e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160666.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160666
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              85276