#------------------------------------------------------------------------------
#$Date: 2019-11-04 08:45:47 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/36/4033689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4033689
loop_
_publ_author_name
'Prochnow, Thaís'
'Maroneze, Adriano'
'Back, Davi Fernando'
'Zeni, Gilson'
_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° φ & ω 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/[σ²(Fo²)+(0.0704P)²+0.0000P] where P=(Fo²+2Fc²)/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     >2σ(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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S12 S 0.07920(4) 0.33033(9) 0.51611(3) 0.01510(15) Uani 1 1 d .
S14 S 0.32041(3) 0.38112(9) 0.52118(3) 0.01506(15) Uani 1 1 d .
N7 N 0.21740(11) 0.5674(3) 0.57921(10) 0.0137(4) Uani 1 1 d .
C13 C 0.13502(14) 0.0876(4) 0.42278(12) 0.0132(4) Uani 1 1 d .
C8 C 0.14014(14) 0.5558(4) 0.57919(12) 0.0151(4) Uani 1 1 d .
C11 C 0.15761(14) 0.2655(4) 0.48747(12) 0.0130(4) Uani 1 1 d .
C19 C 0.08079(15) -0.1031(4) 0.41523(13) 0.0174(5) Uani 1 1 d .
H19 H 0.061 -0.1215 0.4535 0.021 Uiso 1 1 calc R
C10 C 0.22658(14) 0.4037(3) 0.52655(12) 0.0136(4) Uani 1 1 d .
C15 C 0.16284(15) 0.1123(4) 0.36484(12) 0.0164(4) Uani 1 1 d .
H15 H 0.1993 0.2413 0.3683 0.02 Uiso 1 1 calc R
C9 C 0.13397(15) 0.7323(4) 0.62667(12) 0.0182(5) Uani 1 1 d .
H9 H 0.0876 0.7632 0.6364 0.022 Uiso 1 1 calc R
C17 C 0.08325(15) -0.2406(4) 0.29608(13) 0.0195(5) Uani 1 1 d .
H17 H 0.0657 -0.3515 0.2531 0.023 Uiso 1 1 calc R
C16 C 0.13704(15) -0.0513(4) 0.30278(12) 0.0181(5) Uani 1 1 d .
H16 H 0.1564 -0.0339 0.2642 0.022 Uiso 1 1 calc R
C4 C 0.26362(15) 0.7564(4) 0.62920(12) 0.0160(4) Uani 1 1 d .
C18 C 0.05550(15) -0.2655(4) 0.35303(13) 0.0204(5) Uani 1 1 d .
H18 H 0.019 -0.3947 0.3492 0.024 Uiso 1 1 calc R
C3 C 0.34348(16) 0.8430(4) 0.64984(13) 0.0214(5) Uani 1 1 d .
H3 H 0.378 0.7688 0.6303 0.026 Uiso 1 1 calc R
C21 C 0.38946(15) 0.6491(4) 0.44575(14) 0.0184(5) Uani 1 1 d .
H21A H 0.3958 0.4931 0.4232 0.022 Uiso 1 1 calc R
H21B H 0.4389 0.6708 0.4978 0.022 Uiso 1 1 calc R
C5 C 0.21110(16) 0.8607(4) 0.65879(13) 0.0183(5) Uani 1 1 d .
C22 C 0.38579(15) 0.8560(4) 0.39059(14) 0.0209(5) Uani 1 1 d .
H22A H 0.3386 0.8282 0.3374 0.025 Uiso 1 1 calc R
H22B H 0.3756 1.0107 0.4112 0.025 Uiso 1 1 calc R
C23 C 0.46670(16) 0.8755(4) 0.38357(16) 0.0275(6) Uani 1 1 d .
H23A H 0.4622 1.009 0.3477 0.041 Uiso 1 1 calc R
H23B H 0.4765 0.7234 0.3625 0.041 Uiso 1 1 calc R
H23C H 0.5133 0.9067 0.436 0.041 Uiso 1 1 calc R
C20 C 0.31139(15) 0.6400(4) 0.45727(13) 0.0176(5) Uani 1 1 d .
H20A H 0.2613 0.6215 0.4054 0.021 Uiso 1 1 calc R
H20B H 0.3058 0.7921 0.4821 0.021 Uiso 1 1 calc R
C2 C 0.37082(17) 1.0417(4) 0.70011(14) 0.0266(5) Uani 1 1 d .
H2 H 0.425 1.1057 0.7151 0.032 Uiso 1 1 calc R
C6 C 0.24097(17) 1.0612(4) 0.70937(13) 0.0242(5) Uani 1 1 d .
H6 H 0.2072 1.1351 0.7298 0.029 Uiso 1 1 calc R
C1 C 0.31927(18) 1.1503(4) 0.72926(14) 0.0271(6) Uani 1 1 d .
H1 H 0.3391 1.2873 0.7632 0.032 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.003 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 S12 C11 90.86(10)
C10 S14 C20 100.85(10)
C8 N7 C4 108.61(16)
C8 N7 C10 114.26(18)
C4 N7 C10 136.94(18)
C19 C13 C15 118.31(19)
C19 C13 C11 119.96(17)
C15 C13 C11 121.62(19)
C9 C8 N7 110.5(2)
C9 C8 S12 138.87(18)
N7 C8 S12 110.59(14)
C10 C11 C13 131.68(18)
C10 C11 S12 112.33(15)
C13 C11 S12 115.83(16)
C18 C19 C13 121.13(19)
C11 C10 N7 111.89(18)
C11 C10 S14 126.81(15)
N7 C10 S14 121.17(16)
C16 C15 C13 120.0(2)
C8 C9 C5 106.21(19)
C18 C17 C16 119.1(2)
C15 C16 C17 121.08(19)
C3 C4 N7 131.65(18)
C3 C4 C5 122.6(2)
N7 C4 C5 105.78(19)
C19 C18 C17 120.3(2)
C2 C3 C4 117.4(2)
C20 C21 C22 111.70(18)
C6 C5 C4 118.2(2)
C6 C5 C9 132.8(2)
C4 C5 C9 108.92(19)
C23 C22 C21 111.59(19)
C21 C20 S14 108.26(15)
C3 C2 C1 120.9(2)
C1 C6 C5 119.7(2)
C6 C1 C2 121.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S12 C8 1.727(2)
S12 C11 1.7666(19)
S14 C10 1.743(2)
S14 C20 1.832(2)
N7 C8 1.393(3)
N7 C4 1.399(3)
N7 C10 1.412(2)
C13 C19 1.398(3)
C13 C15 1.408(2)
C13 C11 1.476(3)
C8 C9 1.365(3)
C11 C10 1.354(3)
C19 C18 1.383(3)
C15 C16 1.385(3)
C9 C5 1.424(3)
C17 C18 1.390(3)
C17 C16 1.390(3)
C4 C3 1.391(3)
C4 C5 1.424(3)
C3 C2 1.387(3)
C21 C20 1.520(3)
C21 C22 1.530(3)
C5 C6 1.401(3)
C22 C23 1.527(3)
C2 C1 1.413(3)
C6 C1 1.373(4)
