Access to Substituted Dihydrothiopyrano[2,3-b]indoles via Sequential Rearrangements During S-Alkylation and Au-Catalyzed Hydroarylation on Indoline-2-thiones.
Jha, Mukund; Shelke, Ganesh M.; Cameron, T. Stanley; Kumar, Anil; The Journal of organic chemistry 80 (2015) 5272–5278; doi:10.1021/jo5025943

data_4030964
_publ_section_title
;
 Access to Substituted Dihydrothiopyrano[2,3-b]indoles via Sequential
 Rearrangements During S-Alkylation and Au-Catalyzed Hydroarylation on
 Indoline-2-thiones.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5272
_journal_page_last               5278
_journal_paper_doi               10.1021/jo5025943
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C20 H18 N S '
_chemical_formula_sum            'C20 H18 N S'
_chemical_formula_weight         304.43
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.8800(16)
_cell_length_b                   10.855(3)
_cell_length_c                   16.771(3)
_cell_measurement_reflns_used    2194
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      2.2
_cell_volume                     1616.6(6)
_computing_cell_refinement       PROCESS
_computing_data_collection       PROCESS
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_ambient_temperature      296.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-UNKNOWN'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3458
_diffrn_reflns_theta_full        26.84
_diffrn_reflns_theta_max         26.84
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            faint-yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blobs
_exptl_crystal_F_000             644.00
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.30
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1471 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.12100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     94
_refine_ls_number_reflns         495
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
    Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
    21914.0000    30640.1000    9474.9600
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                495
_reflns_number_total             3455
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo5025943_si_002.cif
_cod_data_source_block           '__Compound_k4'
_cod_depositor_comments          'Adding full bibliography for 4030964.cif.'
_cod_original_formula_sum        'C20 H18 N S '
_cod_database_code               4030964