#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/92/2229294.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229294
loop_
_publ_author_name
'Liang, Zuo-Qin'
'Tao, Xu-Tang'
_publ_section_title
;
 [(Dibenzo[b,d]thiophen-4-yl)tellanyl]methanethiol
;
_journal_coeditor_code           XU5144
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o519
_journal_paper_doi               10.1107/S160053681100273X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C13 H10 S2 Te'
_chemical_formula_sum            'C13 H10 S2 Te'
_chemical_formula_weight         357.93
_chemical_name_common
;
[(Dibenzo[b,d]thiophen-4-yl)tellanyl]methanethiol
;
_chemical_name_systematic
;
{8-thiatricyclo[7.4.0.0^2,7^]trideca-1(9),2(7),3,5,10,12-hexaen-6-
yltellanyl}methanethiol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.49518(12)
_cell_length_b                   12.1422(3)
_cell_length_c                   19.0529(5)
_cell_measurement_reflns_used    3403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7797
_cell_measurement_theta_min      3.5150
_cell_volume                     1271.28(5)
_computing_cell_refinement       'CrysAlis PRO CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5117
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.5150
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.637
_exptl_absorpt_correction_T_max  0.495
_exptl_absorpt_correction_T_min  0.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.548
_refine_ls_abs_structure_details 'Flack (1983), 975 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                2248
_reflns_number_total             2509
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5144.cif
_cod_data_source_block           I
_cod_original_cell_volume        1271.27(6)
_cod_database_code               2229294
_cod_database_fobs_code          2229294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Te Te1 0.65007(6) 0.83287(3) 0.120133(19) 0.05366(13) Uani d . 1 . .
S S1 0.8260(2) 0.97156(10) -0.03248(6) 0.0466(3) Uani d . 1 . .
S S2 1.0630(4) 0.65872(16) 0.17855(9) 0.0778(5) Uani d . 1 . .
H H2 0.9995 0.5698 0.1991 0.093 Uiso calc R 1 . .
C C12 0.9348(8) 0.9486(4) 0.1106(2) 0.0401(10) Uani d . 1 . .
C C8 1.1849(8) 1.0679(3) 0.0346(2) 0.0373(9) Uani d . 1 . .
C C4 1.3695(10) 1.1778(4) -0.0677(3) 0.0486(11) Uani d . 1 . .
H H4 1.4968 1.2065 -0.0412 0.058 Uiso calc R 1 . .
C C9 1.3274(10) 1.0953(4) 0.0922(3) 0.0466(11) Uani d . 1 . .
H H9 1.4611 1.1415 0.0868 0.056 Uiso calc R 1 . .
C C2 1.1594(11) 1.1620(5) -0.1780(3) 0.0551(12) Uani d . 1 . .
H H2A 1.1483 1.1809 -0.2252 0.066 Uiso calc R 1 . .
C C13 0.8876(11) 0.6962(4) 0.1038(3) 0.0570(15) Uani d . 1 . .
H H13A 0.7910 0.6332 0.0895 0.068 Uiso calc R 1 . .
H H13B 0.9975 0.7137 0.0656 0.068 Uiso calc R 1 . .
C C3 1.3448(11) 1.2056(4) -0.1376(3) 0.0545(12) Uani d . 1 . .
H H3 1.4548 1.2543 -0.1579 0.065 Uiso calc R 1 . .
C C6 1.0149(8) 1.0623(4) -0.0788(2) 0.0394(10) Uani d . 1 . .
C C7 0.9883(8) 0.9950(4) 0.0445(2) 0.0381(10) Uani d . 1 . .
C C11 1.0743(9) 0.9798(4) 0.1662(3) 0.0471(12) Uani d . 1 . .
H H11 1.0404 0.9519 0.2105 0.057 Uiso calc R 1 . .
C C1 0.9912(9) 1.0912(4) -0.1496(3) 0.0486(12) Uani d . 1 . .
H H1 0.8648 1.0631 -0.1767 0.058 Uiso calc R 1 . .
C C10 1.2698(10) 1.0539(5) 0.1574(3) 0.0534(13) Uani d . 1 . .
H H10 1.3611 1.0750 0.1962 0.064 Uiso calc R 1 . .
C C5 1.2002(7) 1.1060(4) -0.0370(2) 0.0380(10) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Te1 C13 H13A . . 108.6 ?
Te1 C13 H13B . . 108.6 ?
S2 C13 Te1 . . 114.5(3) ?
S2 C13 H13A . . 108.6 ?
S2 C13 H13B . . 108.6 ?
C12 Te1 C13 . . 93.0(2) ?
C12 C7 S1 . . 125.5(3) ?
C12 C11 H11 . . 119.5 ?
C12 C11 C10 . . 121.0(5) ?
C8 C9 H9 . . 120.1 ?
C8 C7 S1 . . 112.5(3) ?
C8 C7 C12 . . 122.0(4) ?
C4 C3 C2 . . 121.0(5) ?
C4 C3 H3 . . 119.5 ?
C4 C5 C8 . . 129.2(4) ?
C9 C8 C7 . . 118.5(4) ?
C9 C8 C5 . . 129.6(4) ?
C9 C10 C11 . . 121.0(5) ?
C9 C10 H10 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C2 C1 C6 . . 118.3(5) ?
C2 C1 H1 . . 120.9 ?
C13 S2 H2 . . 109.5 ?
H13A C13 H13B . . 107.6 ?
C3 C4 H4 . . 120.4 ?
C3 C4 C5 . . 119.3(5) ?
C3 C2 H2A . . 119.4 ?
C6 C1 H1 . . 120.9 ?
C6 C5 C8 . . 112.0(4) ?
C6 C5 C4 . . 118.8(4) ?
C7 S1 C6 . . 91.0(2) ?
C7 C12 Te1 . . 119.8(3) ?
C7 C8 C5 . . 111.9(4) ?
C11 C12 Te1 . . 122.4(4) ?
C11 C12 C7 . . 117.8(4) ?
C11 C10 H10 . . 119.5 ?
C1 C2 H2A . . 119.4 ?
C1 C2 C3 . . 121.1(5) ?
C1 C6 S1 . . 126.0(4) ?
C10 C9 C8 . . 119.7(5) ?
C10 C9 H9 . . 120.1 ?
C10 C11 H11 . . 119.5 ?
C5 C4 H4 . . 120.4 ?
C5 C6 S1 . . 112.5(4) ?
C5 C6 C1 . . 121.5(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Te1 C12 . 2.111(5) ?
Te1 C13 . 2.134(5) ?
S1 C6 . 1.753(5) ?
S1 C7 . 1.739(5) ?
S2 H2 . 1.2000 ?
S2 C13 . 1.778(6) ?
C12 C7 . 1.412(7) ?
C12 C11 . 1.360(7) ?
C8 C9 . 1.389(6) ?
C8 C7 . 1.409(6) ?
C8 C5 . 1.443(6) ?
C4 H4 . 0.9300 ?
C4 C3 . 1.381(8) ?
C4 C5 . 1.403(7) ?
C9 H9 . 0.9300 ?
C9 C10 . 1.376(8) ?
C2 H2A . 0.9300 ?
C2 C3 . 1.382(8) ?
C2 C1 . 1.374(8) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C3 H3 . 0.9300 ?
C6 C1 . 1.399(7) ?
C6 C5 . 1.397(6) ?
C11 H11 . 0.9300 ?
C11 C10 . 1.411(8) ?
C1 H1 . 0.9300 ?
C10 H10 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13A Cg 3_465 0.97 2.90 3.846(6) 166
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Te1 C12 C7 S1 . . . . 4.0(5) ?
Te1 C12 C7 C8 . . . . -176.4(3) ?
Te1 C12 C11 C10 . . . . 177.3(4) ?
S1 C6 C1 C2 . . . . -178.6(4) ?
S1 C6 C5 C8 . . . . -1.9(5) ?
S1 C6 C5 C4 . . . . 178.4(4) ?
C12 Te1 C13 S2 . . . . 78.3(3) ?
C12 C11 C10 C9 . . . . -1.0(8) ?
C8 C9 C10 C11 . . . . 2.9(8) ?
C9 C8 C7 S1 . . . . 178.9(3) ?
C9 C8 C7 C12 . . . . -0.7(6) ?
C9 C8 C5 C4 . . . . 2.6(8) ?
C9 C8 C5 C6 . . . . -177.2(4) ?
C13 Te1 C12 C7 . . . . 91.8(4) ?
C13 Te1 C12 C11 . . . . -87.1(4) ?
C3 C4 C5 C8 . . . . -178.2(5) ?
C3 C4 C5 C6 . . . . 1.6(7) ?
C3 C2 C1 C6 . . . . -1.2(8) ?
C6 S1 C7 C12 . . . . 178.1(4) ?
C6 S1 C7 C8 . . . . -1.5(3) ?
C7 S1 C6 C1 . . . . -177.9(4) ?
C7 S1 C6 C5 . . . . 1.9(3) ?
C7 C12 C11 C10 . . . . -1.6(7) ?
C7 C8 C9 C10 . . . . -1.9(7) ?
C7 C8 C5 C4 . . . . -179.5(5) ?
C7 C8 C5 C6 . . . . 0.7(5) ?
C11 C12 C7 S1 . . . . -177.0(3) ?
C11 C12 C7 C8 . . . . 2.5(6) ?
C1 C2 C3 C4 . . . . 1.1(8) ?
C1 C6 C5 C8 . . . . 178.0(4) ?
C1 C6 C5 C4 . . . . -1.8(7) ?
C5 C8 C9 C10 . . . . 175.8(5) ?
C5 C8 C7 S1 . . . . 0.7(5) ?
C5 C8 C7 C12 . . . . -178.9(4) ?
C5 C4 C3 C2 . . . . -1.3(8) ?
C5 C6 C1 C2 . . . . 1.6(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656504
