#------------------------------------------------------------------------------
#$Date: 2017-08-16 04:48:32 +0300 (Wed, 16 Aug 2017) $
#$Revision: 199786 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/05/7120568.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_7120568
loop_
_publ_author_name
'Wang, Chengyuan'
'Nakamura, Hiroshi'
'Sugino, Hiroyoshi'
'Takimiya, Kazuo'
_publ_section_title
;
 Methylthionated benzo[1,2-b:4,5-b′]dithiophenes: a model study to
 control packing structures and molecular orientation in thienoacene-based
 organic semiconductors
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04998F
_journal_year                    2017
_chemical_formula_moiety         'C12 H10 S4'
_chemical_formula_sum            'C12 H10 S4'
_chemical_formula_weight         282.45
_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'
_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_update_record
;
2017-06-27 deposited with the CCDC.
2017-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.6704(19)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.6642(3)
_cell_length_b                   5.65404(18)
_cell_length_c                   11.1188(4)
_cell_measurement_reflns_used    7247
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      4.58
_cell_volume                     607.29(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_min         4.577
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.900
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             292.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       0.0104(17)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0703P)²+0.0418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                973
_reflns_number_total             1110
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c7cc04998f2.cif
_cod_data_source_block           160314-syn-MeS-BDT
_cod_original_cell_volume        607.30(3)
_cod_database_code               7120568
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
S1 S 0.74202(6) 0.26453(9) 0.37780(5) 0.0447(3) Uani 1 1 d . .
S2 S 0.60362(6) 0.49959(10) 0.16800(5) 0.0481(3) Uani 1 1 d . .
C1 C 0.7392(2) 0.5001(3) 0.27521(19) 0.0382(5) Uani 1 1 d . .
C2 C 1.0464(2) 0.7135(4) 0.4461(2) 0.0403(5) Uani 1 1 d . .
H2 H 1.0783 0.8557 0.4108 0.048 Uiso 1 1 calc R U
C3 C 0.9320(2) 0.5926(4) 0.39689(17) 0.0373(5) Uani 1 1 d . .
C4 C 0.8447(2) 0.6564(4) 0.29477(18) 0.0396(5) Uani 1 1 d . .
H4 H 0.8591 0.7924 0.2465 0.048 Uiso 1 1 calc R U
C5 C 0.88827(19) 0.3797(4) 0.45247(18) 0.0370(5) Uani 1 1 d . .
C6 C 0.6407(3) 0.7635(4) 0.0855(2) 0.0549(7) Uani 1 1 d . .
H6A H 0.5707 0.7849 0.0209 0.066 Uiso 1 1 calc R U
H6B H 0.6394 0.8999 0.1398 0.066 Uiso 1 1 calc R U
H6C H 0.7324 0.7499 0.0507 0.066 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 0.0181 0.0091
;
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)
;
S S 0.3331 0.5567
;
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
C5 S1 C1 91.31(10) .
C1 S2 C6 100.99(11) .
C4 C1 S2 130.81(17) .
C4 C1 S1 113.08(16) .
S2 C1 S1 116.11(12) .
C5 C2 C3 118.1(2) 3_766
C5 C2 H2 121.0 3_766
C3 C2 H2 121.0 .
C2 C3 C5 119.01(18) .
C2 C3 C4 128.6(2) .
C5 C3 C4 112.33(17) .
C1 C4 C3 112.42(19) .
C1 C4 H4 123.8 .
C3 C4 H4 123.8 .
C2 C5 C3 122.89(18) 3_766
C2 C5 S1 126.24(17) 3_766
C3 C5 S1 110.84(15) .
S2 C6 H6A 109.5 .
S2 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
S2 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C5 1.744(2) .
S1 C1 1.753(2) .
S2 C1 1.746(2) .
S2 C6 1.793(2) .
C1 C4 1.362(3) .
C2 C5 1.380(3) 3_766
C2 C3 1.398(3) .
C2 H2 0.9500 .
C3 C5 1.423(3) .
C3 C4 1.441(3) .
C4 H4 0.9500 .
C5 C2 1.380(3) 3_766
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
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_4
C6 S2 C1 C4 0.9(2) . .
C6 S2 C1 S1 179.87(13) . .
C5 S1 C1 C4 0.97(17) . .
C5 S1 C1 S2 -178.17(12) . .
C5 C2 C3 C5 -0.3(3) 3_766 .
C5 C2 C3 C4 177.99(19) 3_766 .
S2 C1 C4 C3 177.89(15) . .
S1 C1 C4 C3 -1.1(2) . .
C2 C3 C4 C1 -177.7(2) . .
C5 C3 C4 C1 0.6(3) . .
C2 C3 C5 C2 0.3(3) . 3_766
C4 C3 C5 C2 -178.25(18) . 3_766
C2 C3 C5 S1 178.63(15) . .
C4 C3 C5 S1 0.1(2) . .
C1 S1 C5 C2 177.70(19) . 3_766
C1 S1 C5 C3 -0.58(16) . .
