#------------------------------------------------------------------------------
#$Date: 2022-06-18 01:38:19 +0300 (Sat, 18 Jun 2022) $
#$Revision: 276086 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/50/7245082.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_7245082
loop_
_publ_author_name
'Nishimoto, Hiroshi'
'Kadoya, Tomofumi'
'Miyake, Rikyu'
'Oda, Takeshi'
'Nishida, Jun-ichi'
'Kubo, Kazuya'
'Tajima, Hiroyuki'
'Kawase, Takeshi'
'Yamada, Jun-ichi'
_publ_section_title
;
 An isotropic three-dimensional organic semiconductor
 2-(thiopyran-4-ylidene)-1,3-benzodithiole (TP-BT): asymmetric molecular
 design to suppress access resistance
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00644H
_journal_year                    2022
_chemical_formula_moiety         'C12 H8 O S2'
_chemical_formula_sum            'C12 H8 O S2'
_chemical_formula_weight         232.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-01-11 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.417(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.9198(16)
_cell_length_b                   7.670(2)
_cell_length_c                   22.977(6)
_cell_measurement_reflns_used    3131
_cell_measurement_temperature    293
_cell_measurement_theta_max      30.17
_cell_measurement_theta_min      2.80
_cell_volume                     1036.7(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17838
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.802
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.44
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1115P)²+1.0852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.1985
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2126
_reflns_number_total             2376
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d2ce00644h2.cif
_cod_data_source_block           V210919e
_cod_database_code               7245082
_shelxl_version_number           2014-3
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97597(13) 0.03689(11) 0.75598(4) 0.0477(3) Uani 1 1 d . . . . .
S2 S 0.57139(13) 0.22727(12) 0.78702(4) 0.0515(3) Uani 1 1 d . . . . .
O13 O 0.4585(6) 0.1635(5) 0.55431(12) 0.0774(9) Uani 1 1 d . . . . .
C1 C 0.7177(5) 0.1383(4) 0.73211(13) 0.0418(6) Uani 1 1 d . . . . .
C2 C 0.7710(6) 0.2332(5) 0.90229(16) 0.0530(8) Uani 1 1 d . . . . .
H2 H 0.6423 0.2918 0.9116 0.064 Uiso 1 1 calc R U . . .
C3 C 0.7488(6) 0.0658(4) 0.62769(15) 0.0486(7) Uani 1 1 d . . . . .
H3 H 0.8861 0.0073 0.6362 0.058 Uiso 1 1 calc R U . . .
C4 C 0.6332(5) 0.1436(4) 0.67534(13) 0.0447(7) Uani 1 1 d . . . . .
C5 C 0.4140(5) 0.2239(4) 0.65411(15) 0.0467(7) Uani 1 1 d . . . . .
H5 H 0.3229 0.2705 0.6807 0.056 Uiso 1 1 calc R U . . .
C6 C 0.9763(5) 0.0980(4) 0.83082(14) 0.0435(7) Uani 1 1 d . . . . .
C7 C 1.1507(6) 0.0576(4) 0.87303(14) 0.0473(7) Uani 1 1 d . . . . .
H7 H 1.2769 -0.0024 0.8628 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7884(6) 0.1853(4) 0.84495(14) 0.0458(7) Uani 1 1 d . . . . .
C9 C 0.3461(7) 0.2300(5) 0.59760(17) 0.0617(9) Uani 1 1 d . . . . .
H9 H 0.2082 0.2851 0.5863 0.074 Uiso 1 1 calc R U . . .
C10 C 0.9442(7) 0.1944(5) 0.94585(16) 0.0620(9) Uani 1 1 d . . . . .
H10 H 0.9321 0.2259 0.9845 0.074 Uiso 1 1 calc R U . . .
C11 C 1.1402(6) 0.1060(5) 0.93114(16) 0.0592(9) Uani 1 1 d . . . . .
H11 H 1.2596 0.0807 0.9597 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6556(7) 0.0802(5) 0.57288(16) 0.0609(9) Uani 1 1 d . . . . .
H12 H 0.7325 0.0281 0.5443 0.073 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C6 95.29(14) . . ?
C1 S2 C8 95.45(14) . . ?
C12 O13 C9 114.9(3) . . ?
C4 C1 S2 121.9(2) . . ?
C4 C1 S1 122.4(2) . . ?
S2 C1 S1 115.73(17) . . ?
C8 C2 C10 120.3(3) . . ?
C8 C2 H2 119.9 . . ?
C10 C2 H2 119.9 . . ?
C12 C3 C4 119.5(3) . . ?
C12 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C1 C4 C5 123.6(3) . . ?
C1 C4 C3 123.6(3) . . ?
C5 C4 C3 112.8(3) . . ?
C9 C5 C4 120.2(3) . . ?
C9 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C8 C6 C7 120.7(3) . . ?
C8 C6 S1 116.4(2) . . ?
C7 C6 S1 122.9(3) . . ?
C6 C7 C11 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C11 C7 H7 119.8 . . ?
C6 C8 C2 120.4(3) . . ?
C6 C8 S2 116.8(2) . . ?
C2 C8 S2 122.8(3) . . ?
C5 C9 O13 126.1(4) . . ?
C5 C9 H9 117.0 . . ?
O13 C9 H9 117.0 . . ?
C2 C10 C11 119.4(3) . . ?
C2 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C7 C11 C10 118.8(3) . . ?
C7 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C3 C12 O13 126.3(4) . . ?
C3 C12 H12 116.9 . . ?
O13 C12 H12 116.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.748(3) . ?
S1 C6 1.782(3) . ?
S2 C1 1.747(3) . ?
S2 C8 1.773(3) . ?
O13 C12 1.357(5) . ?
O13 C9 1.357(5) . ?
C1 C4 1.344(4) . ?
C2 C8 1.383(5) . ?
C2 C10 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C12 1.322(5) . ?
C3 C4 1.480(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.470(5) . ?
C5 C9 1.316(5) . ?
C5 H5 0.9300 . ?
C6 C8 1.368(5) . ?
C6 C7 1.370(4) . ?
C7 C11 1.394(5) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.417(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 S2 C1 C4 -176.2(3) . . . . ?
C8 S2 C1 S1 5.6(2) . . . . ?
C6 S1 C1 C4 176.1(3) . . . . ?
C6 S1 C1 S2 -5.79(19) . . . . ?
S2 C1 C4 C5 0.3(4) . . . . ?
S1 C1 C4 C5 178.4(2) . . . . ?
S2 C1 C4 C3 -178.3(2) . . . . ?
S1 C1 C4 C3 -0.3(4) . . . . ?
C12 C3 C4 C1 -178.6(3) . . . . ?
C12 C3 C4 C5 2.6(4) . . . . ?
C1 C4 C5 C9 177.4(3) . . . . ?
C3 C4 C5 C9 -3.8(4) . . . . ?
C1 S1 C6 C8 3.7(3) . . . . ?
C1 S1 C6 C7 -177.8(3) . . . . ?
C8 C6 C7 C11 -0.4(5) . . . . ?
S1 C6 C7 C11 -178.8(3) . . . . ?
C7 C6 C8 C2 -0.5(5) . . . . ?
S1 C6 C8 C2 178.1(3) . . . . ?
C7 C6 C8 S2 -179.0(2) . . . . ?
S1 C6 C8 S2 -0.4(3) . . . . ?
C10 C2 C8 C6 0.4(5) . . . . ?
C10 C2 C8 S2 178.9(3) . . . . ?
C1 S2 C8 C6 -3.1(3) . . . . ?
C1 S2 C8 C2 178.5(3) . . . . ?
C4 C5 C9 O13 1.8(6) . . . . ?
C12 O13 C9 C5 1.7(6) . . . . ?
C8 C2 C10 C11 0.4(6) . . . . ?
C6 C7 C11 C10 1.3(5) . . . . ?
C2 C10 C11 C7 -1.2(6) . . . . ?
C4 C3 C12 O13 0.9(6) . . . . ?
C9 O13 C12 C3 -3.1(6) . . . . ?
