#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/30/4003018.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_4003018
loop_
_publ_author_name
'Usta, Hakan'
'Kim, Dojeon'
'Ozdemir, Resul'
'Zorlu, Yunus'
'Kim, Sanghyo'
'Ruiz Delgado, M. Carmen'
'Harbuzaru, Alexandra'
'Kim, Seonhyoung'
'Demirel, Gökhan'
'Hong, Jongin'
'Ha, Young-Geun'
'Cho, Kilwon'
'Facchetti, Antonio'
'Kim, Myung-Gil'
_publ_section_title
;
 High Electron Mobility in [1]Benzothieno[3,2-b][1]benzothiophene-Based
 Field-Effect Transistors: Toward n-Type BTBTs
;
_journal_issue                   14
_journal_name_full               'Chemistry of Materials'
_journal_page_first              5254
_journal_paper_doi               10.1021/acs.chemmater.9b01614
_journal_volume                  31
_journal_year                    2019
_chemical_formula_moiety         'C28 H6 F10 O2 S2'
_chemical_formula_sum            'C28 H6 F10 O2 S2'
_chemical_formula_weight         628.45
_chemical_name_common            'Organic compound'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 96.283(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   43.611(3)
_cell_length_b                   7.3973(5)
_cell_length_c                   7.1455(5)
_cell_measurement_reflns_used    123
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      21.5479
_cell_measurement_theta_min      0.9397
_cell_volume                     2291.3(3)
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16026
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+3.0227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                1700
_reflns_number_total             2027
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm9b01614_si_002.cif
_cod_data_source_block           I
_cod_database_code               4003018
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.39804(5) 0.2819(3) 0.2274(3) 0.0306(5) Uani d . . 1
C C2 0.40969(6) 0.1172(4) 0.2893(3) 0.0366(6) Uani d . . 1
C C3 0.43998(6) 0.0931(4) 0.3602(4) 0.0454(7) Uani d . . 1
C C4 0.45955(6) 0.2392(5) 0.3695(4) 0.0503(8) Uani d . . 1
C C5 0.44878(6) 0.4049(4) 0.3087(4) 0.0471(7) Uani d . . 1
C C6 0.41855(6) 0.4256(4) 0.2376(3) 0.0366(6) Uani d . . 1
C C7 0.33956(5) 0.2781(3) 0.2584(3) 0.0269(5) Uani d . . 1
C C8 0.30972(5) 0.3119(3) 0.1784(3) 0.0276(5) Uani d . . 1
H H8 0.3059 0.3477 0.0533 0.033 Uiso calc U R 1
C C9 0.28568(5) 0.2913(3) 0.2884(3) 0.0251(5) Uani d . . 1
C C10 0.29105(5) 0.2354(3) 0.4783(3) 0.0242(5) Uani d . . 1
C C11 0.32124(5) 0.2027(3) 0.5564(3) 0.0308(5) Uani d . . 1
H H11 0.3252 0.166 0.6812 0.037 Uiso calc U R 1
C C12 0.34494(5) 0.2251(3) 0.4479(3) 0.0314(5) Uani d . . 1
H H12 0.3651 0.2048 0.5009 0.038 Uiso calc U R 1
C C13 0.36505(5) 0.3077(3) 0.1406(3) 0.0311(5) Uani d . . 1
C C14 0.26262(5) 0.2268(3) 0.5601(3) 0.0243(5) Uani d . . 1
F F1 0.39115(4) -0.0288(2) 0.2798(2) 0.0556(5) Uani d . . 1
F F2 0.45033(4) -0.0699(3) 0.4154(3) 0.0725(6) Uani d . . 1
F F3 0.48901(4) 0.2194(3) 0.4392(3) 0.0804(7) Uani d . . 1
F F4 0.46784(4) 0.5475(3) 0.3180(3) 0.0809(6) Uani d . . 1
F F5 0.40888(4) 0.5897(2) 0.1814(2) 0.0532(4) Uani d . . 1
O O1 0.36073(4) 0.3554(3) -0.0223(2) 0.0482(5) Uani d . . 1
S S1 0.25354(2) 0.16903(8) 0.78205(7) 0.0282(2) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C2 C1 C6 . . 116.7(2)
C2 C1 C13 . . 123.0(2)
C6 C1 C13 . . 120.2(2)
F1 C2 C3 . . 117.6(2)
F1 C2 C1 . . 119.8(2)
C3 C2 C1 . . 122.7(2)
F2 C3 C2 . . 120.5(3)
F2 C3 C4 . . 120.6(2)
C2 C3 C4 . . 118.9(3)
F3 C4 C5 . . 120.0(3)
F3 C4 C3 . . 120.0(3)
C5 C4 C3 . . 120.0(2)
F4 C5 C4 . . 120.0(2)
F4 C5 C6 . . 119.8(3)
C4 C5 C6 . . 120.1(3)
F5 C6 C5 . . 118.3(2)
F5 C6 C1 . . 120.1(2)
C5 C6 C1 . . 121.6(3)
C8 C7 C12 . . 119.9(2)
C8 C7 C13 . . 117.9(2)
C12 C7 C13 . . 122.1(2)
C7 C8 C9 . . 118.7(2)
C7 C8 H8 . . 120.6
C9 C8 H8 . . 120.6
C8 C9 C10 . . 121.4(2)
C8 C9 S1 . 7_556 126.38(17)
C10 C9 S1 . 7_556 112.25(16)
C11 C10 C9 . . 119.0(2)
C11 C10 C14 . . 130.7(2)
C9 C10 C14 . . 110.24(19)
C12 C11 C10 . . 119.4(2)
C12 C11 H11 . . 120.3
C10 C11 H11 . . 120.3
C11 C12 C7 . . 121.5(2)
C11 C12 H12 . . 119.2
C7 C12 H12 . . 119.2
O1 C13 C7 . . 122.8(2)
O1 C13 C1 . . 118.1(2)
C7 C13 C1 . . 119.10(19)
C14 C14 C10 7_556 . 114.0(2)
C14 C14 S1 7_556 . 112.9(2)
C10 C14 S1 . . 133.02(17)
C14 S1 C9 . 7_556 90.54(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.375(4)
C1 C6 . 1.386(3)
C1 C13 . 1.515(3)
C2 F1 . 1.347(3)
C2 C3 . 1.374(4)
C3 F2 . 1.332(3)
C3 C4 . 1.374(4)
C4 F3 . 1.334(3)
C4 C5 . 1.367(4)
C5 F4 . 1.341(3)
C5 C6 . 1.368(4)
C6 F5 . 1.333(3)
C7 C8 . 1.385(3)
C7 C12 . 1.405(3)
C7 C13 . 1.483(3)
C8 C9 . 1.386(3)
C8 H8 . 0.93
C9 C10 . 1.413(3)
C9 S1 7_556 1.754(2)
C10 C11 . 1.394(3)
C10 C14 . 1.429(3)
C11 C12 . 1.368(3)
C11 H11 . 0.93
C12 H12 . 0.93
C13 O1 . 1.211(3)
C14 C14 7_556 1.364(4)
C14 S1 . 1.729(2)
S1 C9 7_556 1.754(2)
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_4
_geom_torsion
C6 C1 C2 F1 . . -178.7(2)
C13 C1 C2 F1 . . -2.3(4)
C6 C1 C2 C3 . . 0.7(4)
C13 C1 C2 C3 . . 177.0(2)
F1 C2 C3 F2 . . 0.6(4)
C1 C2 C3 F2 . . -178.8(2)
F1 C2 C3 C4 . . 179.2(2)
C1 C2 C3 C4 . . -0.2(4)
F2 C3 C4 F3 . . -1.9(4)
C2 C3 C4 F3 . . 179.5(2)
F2 C3 C4 C5 . . 178.6(3)
C2 C3 C4 C5 . . 0.0(4)
F3 C4 C5 F4 . . 0.4(4)
C3 C4 C5 F4 . . 179.9(3)
F3 C4 C5 C6 . . -179.8(3)
C3 C4 C5 C6 . . -0.3(4)
F4 C5 C6 F5 . . -0.8(4)
C4 C5 C6 F5 . . 179.4(2)
F4 C5 C6 C1 . . -179.3(2)
C4 C5 C6 C1 . . 0.9(4)
C2 C1 C6 F5 . . -179.5(2)
C13 C1 C6 F5 . . 4.0(3)
C2 C1 C6 C5 . . -1.0(4)
C13 C1 C6 C5 . . -177.5(2)
C12 C7 C8 C9 . . -0.4(3)
C13 C7 C8 C9 . . -177.7(2)
C7 C8 C9 C10 . . -0.6(3)
C7 C8 C9 S1 . 7_556 178.61(17)
C8 C9 C10 C11 . . 0.8(3)
S1 C9 C10 C11 7_556 . -178.48(17)
C8 C9 C10 C14 . . 179.4(2)
S1 C9 C10 C14 7_556 . 0.1(2)
C9 C10 C11 C12 . . -0.1(3)
C14 C10 C11 C12 . . -178.3(2)
C10 C11 C12 C7 . . -0.9(4)
C8 C7 C12 C11 . . 1.1(4)
C13 C7 C12 C11 . . 178.3(2)
C8 C7 C13 O1 . . -1.9(4)
C12 C7 C13 O1 . . -179.1(2)
C8 C7 C13 C1 . . 176.7(2)
C12 C7 C13 C1 . . -0.6(3)
C2 C1 C13 O1 . . -116.0(3)
C6 C1 C13 O1 . . 60.3(3)
C2 C1 C13 C7 . . 65.4(3)
C6 C1 C13 C7 . . -118.3(2)
C11 C10 C14 C14 . 7_556 178.3(3)
C9 C10 C14 C14 . 7_556 0.0(3)
C11 C10 C14 S1 . . -1.7(4)
C9 C10 C14 S1 . . 179.95(18)
C14 C14 S1 C9 7_556 7_556 0.0(2)
C10 C14 S1 C9 . 7_556 180.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327430
