Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade Cyclization of N-Alkynylindoles.
Prochnow, Thaís; Maroneze, Adriano; Back, Davi Fernando; Zeni, Gilson; The Journal of organic chemistry 84 (2019) 2891–2900; doi:10.1021/acs.joc.9b00052

data_4033689
_publ_section_title
;
 Synthesis of 3-(Organochalcogen) Chalcogenazolo Indoles via Cascade
 Cyclization of N-Alkynylindoles.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2891
_journal_page_last               2900
_journal_paper_doi               10.1021/acs.joc.9b00052
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C20 H19 N S2'
_chemical_formula_sum            'C20 H19 N S2'
_chemical_formula_weight         337.48
_chemical_melting_point          ?
_chemical_name_common            'butylthio phenylthyoazolo indole'
_chemical_name_systematic
;
        3-(butylthio)-2-phenylthyoazolo[3,2-a]indole
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2018-04-03T10:38:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 117.213(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0117(9)
_cell_length_b                   5.5154(3)
_cell_length_c                   18.9813(8)
_cell_measurement_reflns_used    8214
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.03
_cell_measurement_theta_min      2.728
_cell_volume                     1676.92(15)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20516
_diffrn_reflns_theta_full        22.09
_diffrn_reflns_theta_max         22.09
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.58
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.139
_reflns_number_gt                3337
_reflns_number_total             4229
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo9b00052_si_003.cif
_cod_data_source_block           test33
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1676.92(14)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4033689