#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/87/1548727.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1548727
loop_
_publ_author_name
'Fujii, Takuya'
'Yamakado, Hideo'
_publ_section_title
;
 The 2:1 charge-transfer complex of 4,6-dimethyldibenzothiophene and
 7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane
;
_journal_coeditor_code           IS4022
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x180077
_journal_paper_doi               10.1107/S2414314618000779
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          '2C14 H12 S, C12 F4 N4'
_chemical_formula_moiety         '2(C14 H12 S), C12 F4 N4'
_chemical_formula_sum            'C40 H24 F4 N4 S2'
_chemical_formula_weight         700.77
_chemical_name_common
;
Bis(4,6-dimethyldibenzothiophene)
7,7,8,8-tetracyano-2,3,5,6-tetrafluoroquinodimethane
;
_chemical_name_systematic
;Bis[6,10-dimethyl-8-thiatricyclo[7.4.0.0^2,7^]trideca-1(9),2,4,6,10,12-hexaene]
2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                113.400(2)
_cell_angle_beta                 90.010(3)
_cell_angle_gamma                108.607(3)
_cell_formula_units_Z            1
_cell_length_a                   7.570(2)
_cell_length_b                   10.206(3)
_cell_length_c                   11.549(4)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.69
_cell_volume                     767.8(4)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2008)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2016) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla et al., 2012)
;
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 28.445
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6222
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.245
_diffrn_reflns_theta_min         3.694
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(REQAB; Rigaku, 1998)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360.00
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0470P)²+0.4352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                2887
_reflns_number_total             3311
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            is4022sup1.cif
_cod_data_source_block           I
_cod_database_code               1548727
_cod_database_fobs_code          1548727
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
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_occupancy
S S1 0.50372(5) 0.19776(4) 0.00985(3) 0.01267(11) Uani d 1
F F1 0.66794(11) 0.46548(10) -0.11943(8) 0.01555(19) Uani d 1
F F2 0.73704(12) 0.60156(10) 0.13100(8) 0.0156(2) Uani d 1
N N1 1.37660(19) 0.69718(16) 0.40939(13) 0.0196(3) Uani d 1
N N2 0.8594(2) 0.75756(17) 0.42387(13) 0.0234(3) Uani d 1
C C1 1.0005(2) 0.24541(16) 0.16420(14) 0.0134(3) Uani d 1
H H1 1.106198 0.219533 0.132407 0.016 Uiso calc 1
C C2 1.0013(2) 0.31783(17) 0.29404(14) 0.0144(3) Uani d 1
H H2 1.107384 0.340458 0.351784 0.017 Uiso calc 1
C C3 0.8466(2) 0.35811(16) 0.34113(14) 0.0149(3) Uani d 1
H H3 0.850956 0.408757 0.430689 0.018 Uiso calc 1
C C4 0.6867(2) 0.32626(16) 0.26081(14) 0.0135(3) Uani d 1
C C5 0.6874(2) 0.25106(16) 0.12964(14) 0.0123(3) Uani d 1
C C6 0.6322(2) 0.12100(16) -0.10872(14) 0.0120(3) Uani d 1
C C7 0.5684(2) 0.05155(16) -0.24017(14) 0.0134(3) Uani d 1
C C8 0.6910(2) -0.00336(16) -0.31948(14) 0.0150(3) Uani d 1
H H8 0.652923 -0.051750 -0.409160 0.018 Uiso calc 1
C C9 0.8694(2) 0.01070(17) -0.27078(14) 0.0151(3) Uani d 1
H H9 0.949518 -0.027864 -0.327803 0.018 Uiso calc 1
C C10 0.9300(2) 0.08007(16) -0.14069(14) 0.0134(3) Uani d 1
H H10 1.050959 0.089629 -0.108152 0.016 Uiso calc 1
C C11 0.8102(2) 0.13592(16) -0.05784(14) 0.0119(3) Uani d 1
C C12 0.8422(2) 0.21067(15) 0.08018(13) 0.0116(3) Uani d 1
C C13 0.5213(2) 0.36983(18) 0.31136(15) 0.0174(3) Uani d 1
H H13A 0.514343 0.452297 0.290378 0.026 Uiso calc 1
H H13B 0.536587 0.404189 0.404152 0.026 Uiso calc 1
H H13C 0.405198 0.281435 0.272533 0.026 Uiso calc 1
C C14 0.3773(2) 0.03761(17) -0.29078(15) 0.0167(3) Uani d 1
H H14A 0.371282 0.139434 -0.266854 0.025 Uiso calc 1
H H14B 0.280501 -0.018362 -0.254580 0.025 Uiso calc 1
H H14C 0.355357 -0.017344 -0.383911 0.025 Uiso calc 1
C C15 0.83036(19) 0.48166(16) -0.06107(14) 0.0114(3) Uani d 1
C C16 0.86612(19) 0.55144(16) 0.06696(14) 0.0117(3) Uani d 1
C C17 1.03840(19) 0.57591(15) 0.13883(13) 0.0113(3) Uani d 1
C C18 1.0752(2) 0.64812(16) 0.26997(14) 0.0131(3) Uani d 1
C C19 1.2464(2) 0.67300(16) 0.34279(14) 0.0146(3) Uani d 1
C C20 0.9484(2) 0.70676(17) 0.35044(14) 0.0156(3) 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 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)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 S1 C6 . 91.18(7) n
C2 C1 C12 . 119.20(13) n
C2 C1 H1 . 120.4 n
C12 C1 H1 . 120.4 n
C1 C2 C3 . 120.50(14) n
C1 C2 H2 . 119.7 n
C3 C2 H2 . 119.7 n
C4 C3 C2 . 122.11(14) n
C4 C3 H3 . 118.9 n
C2 C3 H3 . 118.9 n
C3 C4 C5 . 116.59(13) n
C3 C4 C13 . 122.05(13) n
C5 C4 C13 . 121.35(13) n
C4 C5 C12 . 122.23(13) n
C4 C5 S1 . 125.29(11) n
C12 C5 S1 . 112.48(11) n
C7 C6 C11 . 122.66(13) n
C7 C6 S1 . 124.90(11) n
C11 C6 S1 . 112.45(11) n
C8 C7 C6 . 116.35(13) n
C8 C7 C14 . 122.58(14) n
C6 C7 C14 . 121.07(13) n
C7 C8 C9 . 121.94(14) n
C7 C8 H8 . 119.0 n
C9 C8 H8 . 119.0 n
C10 C9 C8 . 120.80(13) n
C10 C9 H9 . 119.6 n
C8 C9 H9 . 119.6 n
C9 C10 C11 . 118.93(13) n
C9 C10 H10 . 120.5 n
C11 C10 H10 . 120.5 n
C10 C11 C6 . 119.32(13) n
C10 C11 C12 . 128.65(13) n
C6 C11 C12 . 112.03(12) n
C1 C12 C5 . 119.36(13) n
C1 C12 C11 . 128.77(13) n
C5 C12 C11 . 111.87(13) n
C4 C13 H13A . 109.5 n
C4 C13 H13B . 109.5 n
H13A C13 H13B . 109.5 n
C4 C13 H13C . 109.5 n
H13A C13 H13C . 109.5 n
H13B C13 H13C . 109.5 n
C7 C14 H14A . 109.5 n
C7 C14 H14B . 109.5 n
H14A C14 H14B . 109.5 n
C7 C14 H14C . 109.5 n
H14A C14 H14C . 109.5 n
H14B C14 H14C . 109.5 n
F1 C15 C16 . 118.90(12) n
F1 C15 C17 2_765 118.30(12) n
C16 C15 C17 2_765 122.80(13) n
F2 C16 C15 . 118.70(13) n
F2 C16 C17 . 118.20(12) n
C15 C16 C17 . 123.10(13) n
C18 C17 C16 . 123.02(13) n
C18 C17 C15 2_765 122.88(13) n
C16 C17 C15 2_765 114.10(13) n
C17 C18 C20 . 124.50(13) n
C17 C18 C19 . 123.55(13) n
C20 C18 C19 . 111.96(13) n
N1 C19 C18 . 174.55(15) n
N2 C20 C18 . 173.74(16) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 . 1.7500(15) n
S1 C6 . 1.7520(15) n
F1 C15 . 1.3322(17) n
F2 C16 . 1.3350(15) n
N1 C19 . 1.148(2) n
N2 C20 . 1.147(2) n
C1 C2 . 1.383(2) n
C1 C12 . 1.400(2) n
C1 H1 . 0.9500 n
C2 C3 . 1.402(2) n
C2 H2 . 0.9500 n
C3 C4 . 1.393(2) n
C3 H3 . 0.9500 n
C4 C5 . 1.401(2) n
C4 C13 . 1.5015(19) n
C5 C12 . 1.4105(19) n
C6 C7 . 1.402(2) n
C6 C11 . 1.408(2) n
C7 C8 . 1.393(2) n
C7 C14 . 1.502(2) n
C8 C9 . 1.405(2) n
C8 H8 . 0.9500 n
C9 C10 . 1.384(2) n
C9 H9 . 0.9500 n
C10 C11 . 1.4003(19) n
C10 H10 . 0.9500 n
C11 C12 . 1.448(2) n
C13 H13A . 0.9800 n
C13 H13B . 0.9800 n
C13 H13C . 0.9800 n
C14 H14A . 0.9800 n
C14 H14B . 0.9800 n
C14 H14C . 0.9800 n
C15 C16 . 1.344(2) n
C15 C17 2_765 1.4466(19) n
C16 C17 . 1.442(2) n
C17 C18 . 1.377(2) n
C18 C20 . 1.438(2) n
C18 C19 . 1.439(2) n
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
_geom_torsion_publ_flag
C12 C1 C2 C3 . . -0.9(2) n
C1 C2 C3 C4 . . 0.7(2) n
C2 C3 C4 C5 . . 0.2(2) n
C2 C3 C4 C13 . . -179.84(13) n
C3 C4 C5 C12 . . -0.7(2) n
C13 C4 C5 C12 . . 179.28(13) n
C3 C4 C5 S1 . . 179.65(11) n
C13 C4 C5 S1 . . -0.3(2) n
C6 S1 C5 C4 . . 179.43(13) n
C6 S1 C5 C12 . . -0.22(11) n
C5 S1 C6 C7 . . 179.85(13) n
C5 S1 C6 C11 . . 0.00(11) n
C11 C6 C7 C8 . . 0.2(2) n
S1 C6 C7 C8 . . -179.66(11) n
C11 C6 C7 C14 . . 179.91(13) n
S1 C6 C7 C14 . . 0.1(2) n
C6 C7 C8 C9 . . -0.4(2) n
C14 C7 C8 C9 . . 179.90(14) n
C7 C8 C9 C10 . . 0.2(2) n
C8 C9 C10 C11 . . 0.2(2) n
C9 C10 C11 C6 . . -0.4(2) n
C9 C10 C11 C12 . . 179.42(14) n
C7 C6 C11 C10 . . 0.2(2) n
S1 C6 C11 C10 . . -179.95(11) n
C7 C6 C11 C12 . . -179.64(12) n
S1 C6 C11 C12 . . 0.22(15) n
C2 C1 C12 C5 . . 0.4(2) n
C2 C1 C12 C11 . . -179.92(13) n
C4 C5 C12 C1 . . 0.5(2) n
S1 C5 C12 C1 . . -179.87(11) n
C4 C5 C12 C11 . . -179.28(13) n
S1 C5 C12 C11 . . 0.39(15) n
C10 C11 C12 C1 . . 0.1(2) n
C6 C11 C12 C1 . . 179.90(14) n
C10 C11 C12 C5 . . 179.81(14) n
C6 C11 C12 C5 . . -0.39(17) n
F1 C15 C16 F2 . . 0.2(2) n
C17 C15 C16 F2 2_765 . 179.72(12) n
F1 C15 C16 C17 . . -179.32(12) n
C17 C15 C16 C17 2_765 . 0.2(2) n
F2 C16 C17 C18 . . 0.1(2) n
C15 C16 C17 C18 . . 179.65(13) n
F2 C16 C17 C15 . 2_765 -179.71(11) n
C15 C16 C17 C15 . 2_765 -0.2(2) n
C16 C17 C18 C20 . . 0.2(2) n
C15 C17 C18 C20 2_765 . -179.97(13) n
C16 C17 C18 C19 . . 179.89(13) n
C15 C17 C18 C19 2_765 . -0.3(2) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139051744
