Iodine-Catalyzed Synthesis of 3-Arylthioindoles Employing a 1-Aryltriazene/CS2 Combination as a New Sulfenylation Source
Pandey, Anand Kumar; Chand, Shiv; Singh, Rahul; Kumar, Saurabh; Singh, Krishna Nand; ACS Omega  (2020) –; doi:10.1021/acsomega.0c00472

data_4517515
_publ_section_title
;
 Iodine-Catalyzed Synthesis of 3-Arylthioindoles Employing a
 1-Aryltriazene/CS2 Combination as a New Sulfenylation Source
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.0c00472
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H13 N S'
_chemical_formula_sum            'C15 H13 N S'
_chemical_formula_weight         239.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.056(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7317(6)
_cell_length_b                   6.1983(4)
_cell_length_c                   11.9174(7)
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.48
_cell_volume                     605.88(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9512
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_min         3.547
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1061 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0464P)^2^+0.3761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2659
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c00472_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4517515
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              2337
_shelx_hkl_checksum              40886