#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234778.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_7234778
loop_
_publ_author_name
'Christian Ruzie'
'Jolanta Karpinska'
'Anne Laurent'
'Lionel Sanguinet'
'Simon Hunter'
'Thomas D. Anthopoulos'
'Vincent Lemaur'
'Jerome Cornil'
'Alan R. Kennedy'
'Oliver Fenwick'
'Paolo Samori'
'Guillaume Schweicher'
'Basab Chattopadhyay'
'Yves Henri Geerts'
_publ_section_title
;
 Design, synthesis, chemical stability, packing, cyclic voltammetry,
 ionisation potential, and charge transport of
 [1]benzothieno[3,2-b][1]benzothiophene derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4863
_journal_page_last               4879
_journal_paper_doi               10.1039/C6TC01409G
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C30 H30 F10 O2 S2'
_chemical_formula_weight         676.66
_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_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                90.00
_cell_angle_beta                 93.482(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   23.0898(13)
_cell_length_b                   5.6492(3)
_cell_length_c                   11.3886(8)
_cell_measurement_reflns_used    4858
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.1616
_cell_measurement_theta_min      3.1026
_cell_volume                     1482.77(16)
_computing_cell_refinement       CrysalisPro
_computing_data_collection       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13089
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.23
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'chip from large prism'
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0452
_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)+(0.0437P)²+1.0360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                2882
_reflns_number_total             3683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-4863.cif
_cod_data_source_block           belg_cr892
_cod_original_cell_volume        1482.77(15)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7234778
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 0.50624(2) 0.28314(8) 0.11929(4) 0.02439(14) Uani 1 1 d . . .
F1 F 0.15450(6) -0.2677(3) 0.89229(14) 0.0650(5) Uani 1 1 d . . .
F2 F 0.10202(6) -0.4276(2) 0.74882(15) 0.0543(4) Uani 1 1 d . . .
F3 F 0.04736(7) -0.3798(3) 0.94876(17) 0.0747(6) Uani 1 1 d . . .
F4 F 0.00934(6) -0.1663(3) 0.81100(15) 0.0563(4) Uani 1 1 d . . .
F5 F 0.06161(8) -0.0053(4) 0.95007(16) 0.0837(7) Uani 1 1 d . . .
O1 O 0.31354(6) 0.0882(2) 0.31819(12) 0.0260(3) Uani 1 1 d . . .
C1 C 0.52027(8) 0.0876(3) 0.00672(16) 0.0204(4) Uani 1 1 d . . .
C2 C 0.44316(8) 0.1273(3) 0.14705(16) 0.0202(4) Uani 1 1 d . . .
C3 C 0.43427(7) -0.0720(3) 0.07424(16) 0.0202(4) Uani 1 1 d . . .
C4 C 0.38526(8) -0.2139(3) 0.08765(17) 0.0242(4) Uani 1 1 d . . .
H4 H 0.3785 -0.3501 0.0399 0.029 Uiso 1 1 calc R . .
C5 C 0.34718(8) -0.1535(3) 0.17060(17) 0.0248(4) Uani 1 1 d . . .
H5 H 0.3141 -0.2498 0.1801 0.030 Uiso 1 1 calc R . .
C6 C 0.35624(8) 0.0485(3) 0.24191(16) 0.0225(4) Uani 1 1 d . . .
C7 C 0.40438(8) 0.1905(3) 0.23211(16) 0.0217(4) Uani 1 1 d . . .
H7 H 0.4110 0.3254 0.2809 0.026 Uiso 1 1 calc R . .
C8 C 0.31751(8) 0.2975(3) 0.38914(17) 0.0245(4) Uani 1 1 d . . .
H8A H 0.3235 0.4382 0.3395 0.029 Uiso 1 1 calc R . .
H8B H 0.3506 0.2852 0.4484 0.029 Uiso 1 1 calc R . .
C9 C 0.26106(8) 0.3192(3) 0.44924(17) 0.0256(4) Uani 1 1 d . . .
H9A H 0.2285 0.3191 0.3885 0.031 Uiso 1 1 calc R . .
H9B H 0.2606 0.4731 0.4907 0.031 Uiso 1 1 calc R . .
C10 C 0.25115(8) 0.1226(3) 0.53709(16) 0.0221(4) Uani 1 1 d . . .
H10A H 0.2837 0.1213 0.5979 0.027 Uiso 1 1 calc R . .
H10B H 0.2510 -0.0317 0.4959 0.027 Uiso 1 1 calc R . .
C11 C 0.19428(8) 0.1517(3) 0.59662(18) 0.0254(4) Uani 1 1 d . . .
H11A H 0.1625 0.1762 0.5356 0.030 Uiso 1 1 calc R . .
H11B H 0.1967 0.2948 0.6468 0.030 Uiso 1 1 calc R . .
C12 C 0.17967(8) -0.0606(3) 0.67179(16) 0.0229(4) Uani 1 1 d . . .
H12A H 0.2120 -0.0892 0.7312 0.028 Uiso 1 1 calc R . .
H12B H 0.1755 -0.2028 0.6212 0.028 Uiso 1 1 calc R . .
C13 C 0.12366(8) -0.0230(4) 0.73425(17) 0.0254(4) Uani 1 1 d . . .
H13A H 0.1273 0.1229 0.7823 0.031 Uiso 1 1 calc R . .
H13B H 0.0912 0.0000 0.6746 0.031 Uiso 1 1 calc R . .
C14 C 0.10986(9) -0.2253(4) 0.81159(19) 0.0311(5) Uani 1 1 d . . .
C15 C 0.05619(10) -0.1941(5) 0.8815(2) 0.0432(6) Uani 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'
O O 0.0106 0.0060 '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 0.0000 0.0000 '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
C1 S1 C2 90.46(9) . .
C6 O1 C8 117.96(14) . .
C1 C1 C3 113.9(2) 3_655 3_655
C1 C1 S1 112.74(19) 3_655 .
C3 C1 S1 133.36(13) 3_655 .
C7 C2 C3 122.27(16) . .
C7 C2 S1 124.76(14) . .
C3 C2 S1 112.97(14) . .
C4 C3 C2 118.89(17) . .
C4 C3 C1 131.20(17) . 3_655
C2 C3 C1 109.90(15) . 3_655
C5 C4 C3 119.21(17) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 121.28(17) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
O1 C6 C7 124.69(17) . .
O1 C6 C5 114.23(16) . .
C7 C6 C5 121.08(17) . .
C6 C7 C2 117.26(17) . .
C6 C7 H7 121.4 . .
C2 C7 H7 121.4 . .
O1 C8 C9 107.14(15) . .
O1 C8 H8A 110.3 . .
C9 C8 H8A 110.3 . .
O1 C8 H8B 110.3 . .
C9 C8 H8B 110.3 . .
H8A C8 H8B 108.5 . .
C8 C9 C10 113.99(16) . .
C8 C9 H9A 108.8 . .
C10 C9 H9A 108.8 . .
C8 C9 H9B 108.8 . .
C10 C9 H9B 108.8 . .
H9A C9 H9B 107.6 . .
C9 C10 C11 112.48(15) . .
C9 C10 H10A 109.1 . .
C11 C10 H10A 109.1 . .
C9 C10 H10B 109.1 . .
C11 C10 H10B 109.1 . .
H10A C10 H10B 107.8 . .
C10 C11 C12 113.06(15) . .
C10 C11 H11A 109.0 . .
C12 C11 H11A 109.0 . .
C10 C11 H11B 109.0 . .
C12 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C11 C12 C13 112.01(15) . .
C11 C12 H12A 109.2 . .
C13 C12 H12A 109.2 . .
C11 C12 H12B 109.2 . .
C13 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C14 C13 C12 112.72(16) . .
C14 C13 H13A 109.0 . .
C12 C13 H13A 109.0 . .
C14 C13 H13B 109.0 . .
C12 C13 H13B 109.0 . .
H13A C13 H13B 107.8 . .
F2 C14 F1 106.23(18) . .
F2 C14 C13 111.21(18) . .
F1 C14 C13 110.75(17) . .
F2 C14 C15 106.66(18) . .
F1 C14 C15 105.93(18) . .
C13 C14 C15 115.50(18) . .
F4 C15 F3 107.35(19) . .
F4 C15 F5 108.0(2) . .
F3 C15 F5 108.1(2) . .
F4 C15 C14 111.1(2) . .
F3 C15 C14 111.7(2) . .
F5 C15 C14 110.53(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7375(19) .
S1 C2 1.7471(18) .
F1 C14 1.360(2) .
F2 C14 1.354(3) .
F3 C15 1.322(3) .
F4 C15 1.317(3) .
F5 C15 1.324(3) .
O1 C6 1.372(2) .
O1 C8 1.432(2) .
C1 C1 1.365(3) 3_655
C1 C3 1.441(3) 3_655
C2 C7 1.405(3) .
C2 C3 1.406(2) .
C3 C4 1.403(2) .
C3 C1 1.441(3) 3_655
C4 C5 1.372(3) .
C4 H4 0.9500 .
C5 C6 1.409(3) .
C5 H5 0.9500 .
C6 C7 1.381(3) .
C7 H7 0.9500 .
C8 C9 1.513(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.521(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.523(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.523(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.528(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.489(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.523(3) .
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
C2 S1 C1 C1 -1.12(19) . . . 3_655
C2 S1 C1 C3 179.29(19) . . . 3_655
C1 S1 C2 C7 -178.06(17) . . . .
C1 S1 C2 C3 1.66(14) . . . .
C7 C2 C3 C4 -0.5(3) . . . .
S1 C2 C3 C4 179.72(14) . . . .
C7 C2 C3 C1 177.98(16) . . . 3_655
S1 C2 C3 C1 -1.75(19) . . . 3_655
C2 C3 C4 C5 0.5(3) . . . .
C1 C3 C4 C5 -177.68(19) 3_655 . . .
C3 C4 C5 C6 0.3(3) . . . .
C8 O1 C6 C7 3.0(3) . . . .
C8 O1 C6 C5 -176.39(16) . . . .
C4 C5 C6 O1 178.31(17) . . . .
C4 C5 C6 C7 -1.1(3) . . . .
O1 C6 C7 C2 -178.35(16) . . . .
C5 C6 C7 C2 1.0(3) . . . .
C3 C2 C7 C6 -0.2(3) . . . .
S1 C2 C7 C6 179.48(14) . . . .
C6 O1 C8 C9 170.91(15) . . . .
O1 C8 C9 C10 65.8(2) . . . .
C8 C9 C10 C11 179.42(16) . . . .
C9 C10 C11 C12 172.00(16) . . . .
C10 C11 C12 C13 177.80(16) . . . .
C11 C12 C13 C14 -177.91(17) . . . .
C12 C13 C14 F2 -61.3(2) . . . .
C12 C13 C14 F1 56.6(2) . . . .
C12 C13 C14 C15 176.99(18) . . . .
F2 C14 C15 F4 -63.2(2) . . . .
F1 C14 C15 F4 -176.1(2) . . . .
C13 C14 C15 F4 60.9(3) . . . .
F2 C14 C15 F3 56.6(3) . . . .
F1 C14 C15 F3 -56.3(3) . . . .
C13 C14 C15 F3 -179.3(2) . . . .
F2 C14 C15 F5 177.0(2) . . . .
F1 C14 C15 F5 64.1(3) . . . .
C13 C14 C15 F5 -58.9(3) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132595503
