#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233896.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_7233896
loop_
_publ_author_name
'Ming-Chou Chen'
'Sureshraju Vegiraju'
'Chi-Ming Huang'
'Peng-Yi Huang'
'Kumaresan Prabakaran'
'Shueh Lin Yau'
'Wei-Chih Chen'
'Wei-Tao Peng'
'Ito Chao'
'Choongik Kim'
'Yu-Tai Tao'
_publ_section_title
;
 Asymmetric fused thiophenes for field-effect transistors: crystal
 structure-film microstructure-transistor performance correlations
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8892
_journal_page_last               8902
_journal_paper_doi               10.1039/C4TC01454E
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C20 H7 F5 S3'
_chemical_formula_sum            'C20 H7 F5 S3'
_chemical_formula_weight         438.44
_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
_cell_angle_alpha                90
_cell_angle_beta                 91.667(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8734(2)
_cell_length_b                   36.1226(12)
_cell_length_c                   7.4967(2)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      42.86
_cell_measurement_theta_min      2.26
_cell_volume                     1589.85(9)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            30972
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.13
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.8174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       thin
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.644
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.0009(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.251
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+9.4012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.17
_refine_ls_wR_factor_ref         0.1789
_reflns_number_gt                3290
_reflns_number_total             3658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000004.cif
_cod_data_source_block           PCOD1000004
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7233896
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19240(17) 0.80837(3) 0.79638(14) 0.0132(2) Uani 1 1 d . . .
S2 S 0.77334(17) 0.75424(3) 0.99990(14) 0.0138(2) Uani 1 1 d . . .
S3 S 0.19663(17) 0.69917(3) 0.79654(14) 0.0126(2) Uani 1 1 d . . .
F1 F -0.0149(4) 0.63576(7) 0.6990(4) 0.0172(5) Uani 1 1 d . . .
F2 F -0.1020(4) 0.56406(7) 0.6682(4) 0.0191(6) Uani 1 1 d . . .
F3 F 0.2046(5) 0.51280(7) 0.7894(4) 0.0239(6) Uani 1 1 d . . .
F4 F 0.6068(4) 0.53593(7) 0.9459(4) 0.0211(6) Uani 1 1 d . . .
F5 F 0.6969(4) 0.60692(7) 0.9836(4) 0.0182(6) Uani 1 1 d . . .
C1 C 0.3352(7) 0.88187(12) 0.8404(5) 0.0137(8) Uani 1 1 d . . .
C2 C 0.1247(7) 0.89412(12) 0.7697(6) 0.0172(9) Uani 1 1 d . . .
C3 C 0.0776(8) 0.93164(13) 0.7533(6) 0.0194(9) Uani 1 1 d . . .
C4 C 0.2375(8) 0.95805(12) 0.8061(6) 0.0193(9) Uani 1 1 d . . .
C5 C 0.4480(8) 0.94615(13) 0.8776(6) 0.0196(9) Uani 1 1 d . . .
C6 C 0.4956(7) 0.90885(12) 0.8950(6) 0.0163(8) Uani 1 1 d . . .
C7 C 0.3891(7) 0.84242(12) 0.8619(5) 0.0142(8) Uani 1 1 d . . .
C8 C 0.5877(7) 0.82714(12) 0.9313(6) 0.0146(8) Uani 1 1 d . . .
C9 C 0.5799(7) 0.78829(12) 0.9312(5) 0.0134(8) Uani 1 1 d . . .
C10 C 0.3768(7) 0.77351(11) 0.8616(5) 0.0128(8) Uani 1 1 d . . .
C11 C 0.3775(7) 0.73430(11) 0.8640(6) 0.0132(8) Uani 1 1 d . . .
C12 C 0.5813(7) 0.72004(12) 0.9346(5) 0.0139(8) Uani 1 1 d . . .
C13 C 0.5926(7) 0.68106(12) 0.9348(5) 0.0133(8) Uani 1 1 d . . .
C14 C 0.3961(7) 0.66527(11) 0.8627(5) 0.0121(8) Uani 1 1 d . . .
C15 C 0.3463(7) 0.62585(12) 0.8428(5) 0.0129(8) Uani 1 1 d . . .
C16 C 0.1451(7) 0.61188(12) 0.7631(6) 0.0136(8) Uani 1 1 d . . .
C17 C 0.0965(7) 0.57482(12) 0.7457(6) 0.0153(8) Uani 1 1 d . . .
C18 C 0.2504(7) 0.54870(12) 0.8073(6) 0.0155(8) Uani 1 1 d . . .
C19 C 0.4533(7) 0.56066(12) 0.8869(6) 0.0163(8) Uani 1 1 d . . .
C20 C 0.4967(7) 0.59779(12) 0.9026(5) 0.0132(8) Uani 1 1 d . . .
H2 H 0.022(8) 0.8756(13) 0.726(6) 0.004(11) Uiso 1 1 d . . .
H3 H -0.052(8) 0.9376(12) 0.704(6) 0.002(10) Uiso 1 1 d . . .
H4 H 0.221(8) 0.9851(14) 0.813(6) 0.009(11) Uiso 1 1 d . . .
H5 H 0.584(12) 0.9653(19) 0.930(9) 0.05(2) Uiso 1 1 d . . .
H6 H 0.628(10) 0.9021(15) 0.948(8) 0.022(14) Uiso 1 1 d . . .
H8 H 0.704(9) 0.8420(14) 0.979(7) 0.015(12) Uiso 1 1 d . . .
H13 H 0.720(9) 0.6670(15) 0.984(7) 0.019(13) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
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
C10 S1 C7 91.7(2) . .
C12 S2 C9 90.4(2) . .
C11 S3 C14 91.7(2) . .
C2 C1 C6 117.8(4) . .
C2 C1 C7 122.2(4) . .
C6 C1 C7 120.0(4) . .
C3 C2 C1 120.9(4) . .
C3 C2 H2 122(3) . .
C1 C2 H2 117(3) . .
C4 C3 C2 120.9(4) . .
C4 C3 H3 122(3) . .
C2 C3 H3 117(3) . .
C3 C4 C5 118.7(4) . .
C3 C4 H4 129(3) . .
C5 C4 H4 112(3) . .
C6 C5 C4 120.6(4) . .
C6 C5 H5 115(4) . .
C4 C5 H5 124(4) . .
C5 C6 C1 121.0(4) . .
C5 C6 H6 119(4) . .
C1 C6 H6 120(4) . .
C8 C7 C1 127.4(4) . .
C8 C7 S1 111.7(3) . .
C1 C7 S1 120.9(3) . .
C7 C8 C9 111.9(4) . .
C7 C8 H8 121(3) . .
C9 C8 H8 127(3) . .
C10 C9 C8 114.2(4) . .
C10 C9 S2 112.6(3) . .
C8 C9 S2 133.2(3) . .
C9 C10 C11 112.1(4) . .
C9 C10 S1 110.5(3) . .
C11 C10 S1 137.4(3) . .
C12 C11 C10 112.1(4) . .
C12 C11 S3 110.8(3) . .
C10 C11 S3 137.0(3) . .
C11 C12 C13 114.2(4) . .
C11 C12 S2 112.9(3) . .
C13 C12 S2 132.9(3) . .
C14 C13 C12 111.9(4) . .
C14 C13 H13 124(3) . .
C12 C13 H13 124(3) . .
C13 C14 C15 127.2(4) . .
C13 C14 S3 111.4(3) . .
C15 C14 S3 121.4(3) . .
C16 C15 C20 112.9(4) . .
C16 C15 C14 123.9(4) . .
C20 C15 C14 123.2(4) . .
F1 C16 C17 116.6(4) . .
F1 C16 C15 119.3(4) . .
C17 C16 C15 124.1(4) . .
F2 C17 C16 119.8(4) . .
F2 C17 C18 119.9(4) . .
C16 C17 C18 120.2(4) . .
F3 C18 C17 120.4(4) . .
F3 C18 C19 121.0(4) . .
C17 C18 C19 118.6(4) . .
F4 C19 C20 120.3(4) . .
F4 C19 C18 119.9(4) . .
C20 C19 C18 119.8(4) . .
F5 C20 C19 115.8(4) . .
F5 C20 C15 119.8(4) . .
C19 C20 C15 124.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C10 1.722(4) .
S1 C7 1.748(4) .
S2 C12 1.734(4) .
S2 C9 1.742(4) .
S3 C11 1.721(4) .
S3 C14 1.756(4) .
F1 C16 1.353(5) .
F2 C17 1.345(5) .
F3 C18 1.331(5) .
F4 C19 1.335(5) .
F5 C20 1.349(5) .
C1 C2 1.402(6) .
C1 C6 1.408(6) .
C1 C7 1.468(6) .
C2 C3 1.388(6) .
C2 H2 0.96(5) .
C3 C4 1.388(6) .
C3 H3 0.86(5) .
C4 C5 1.401(6) .
C4 H4 0.98(5) .
C5 C6 1.381(6) .
C5 H5 1.12(7) .
C6 H6 0.90(6) .
C7 C8 1.379(6) .
C8 C9 1.404(6) .
C8 H8 0.93(5) .
C9 C10 1.395(6) .
C10 C11 1.417(6) .
C11 C12 1.393(6) .
C12 C13 1.410(6) .
C13 C14 1.383(5) .
C13 H13 0.97(6) .
C14 C15 1.460(6) .
C15 C16 1.403(6) .
C15 C20 1.409(6) .
C16 C17 1.374(6) .
C17 C18 1.377(6) .
C18 C19 1.386(6) .
C19 C20 1.370(6) .
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
C6 C1 C2 C3 0.4(7) . . . .
C7 C1 C2 C3 179.1(4) . . . .
C1 C2 C3 C4 0.1(7) . . . .
C2 C3 C4 C5 -0.4(7) . . . .
C3 C4 C5 C6 0.1(7) . . . .
C4 C5 C6 C1 0.5(7) . . . .
C2 C1 C6 C5 -0.7(7) . . . .
C7 C1 C6 C5 -179.4(4) . . . .
C2 C1 C7 C8 -179.2(4) . . . .
C6 C1 C7 C8 -0.5(7) . . . .
C2 C1 C7 S1 1.0(6) . . . .
C6 C1 C7 S1 179.6(3) . . . .
C10 S1 C7 C8 -0.1(3) . . . .
C10 S1 C7 C1 179.8(4) . . . .
C1 C7 C8 C9 -179.9(4) . . . .
S1 C7 C8 C9 0.0(5) . . . .
C7 C8 C9 C10 0.2(5) . . . .
C7 C8 C9 S2 180.0(3) . . . .
C12 S2 C9 C10 0.1(3) . . . .
C12 S2 C9 C8 -179.6(4) . . . .
C8 C9 C10 C11 179.8(4) . . . .
S2 C9 C10 C11 0.0(5) . . . .
C8 C9 C10 S1 -0.3(5) . . . .
S2 C9 C10 S1 179.9(2) . . . .
C7 S1 C10 C9 0.2(3) . . . .
C7 S1 C10 C11 -180.0(5) . . . .
C9 C10 C11 C12 -0.2(5) . . . .
S1 C10 C11 C12 180.0(4) . . . .
C9 C10 C11 S3 -177.8(4) . . . .
S1 C10 C11 S3 2.5(8) . . . .
C14 S3 C11 C12 -0.2(3) . . . .
C14 S3 C11 C10 177.3(5) . . . .
C10 C11 C12 C13 -178.2(4) . . . .
S3 C11 C12 C13 0.0(5) . . . .
C10 C11 C12 S2 0.3(5) . . . .
S3 C11 C12 S2 178.5(2) . . . .
C9 S2 C12 C11 -0.3(3) . . . .
C9 S2 C12 C13 177.9(4) . . . .
C11 C12 C13 C14 0.4(5) . . . .
S2 C12 C13 C14 -177.8(3) . . . .
C12 C13 C14 C15 -179.3(4) . . . .
C12 C13 C14 S3 -0.5(5) . . . .
C11 S3 C14 C13 0.4(3) . . . .
C11 S3 C14 C15 179.3(3) . . . .
C13 C14 C15 C16 -178.0(4) . . . .
S3 C14 C15 C16 3.3(6) . . . .
C13 C14 C15 C20 2.1(7) . . . .
S3 C14 C15 C20 -176.6(3) . . . .
C20 C15 C16 F1 -179.8(4) . . . .
C14 C15 C16 F1 0.3(6) . . . .
C20 C15 C16 C17 0.6(6) . . . .
C14 C15 C16 C17 -179.3(4) . . . .
F1 C16 C17 F2 0.0(6) . . . .
C15 C16 C17 F2 179.6(4) . . . .
F1 C16 C17 C18 179.9(4) . . . .
C15 C16 C17 C18 -0.5(7) . . . .
F2 C17 C18 F3 0.5(6) . . . .
C16 C17 C18 F3 -179.5(4) . . . .
F2 C17 C18 C19 -179.9(4) . . . .
C16 C17 C18 C19 0.2(7) . . . .
F3 C18 C19 F4 0.4(7) . . . .
C17 C18 C19 F4 -179.2(4) . . . .
F3 C18 C19 C20 179.6(4) . . . .
C17 C18 C19 C20 0.0(7) . . . .
F4 C19 C20 F5 -1.6(6) . . . .
C18 C19 C20 F5 179.3(4) . . . .
F4 C19 C20 C15 179.4(4) . . . .
C18 C19 C20 C15 0.2(7) . . . .
C16 C15 C20 F5 -179.5(4) . . . .
C14 C15 C20 F5 0.4(6) . . . .
C16 C15 C20 C19 -0.4(6) . . . .
C14 C15 C20 C19 179.5(4) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102431616
