#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/54/4515430.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_4515430
loop_
_publ_author_name
'Iijima, Kodai'
'Sanada, Ryo'
'Yoo, Dongho'
'Sato, Ryonosuke'
'Kawamoto, Tadashi'
'Mori, Takehiko'
_publ_section_title
;
 Carrier Charge Polarity in Mixed-Stack Charge-Transfer Crystals
 Containing Dithienobenzodithiophene.
;
_journal_issue                   12
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              10262
_journal_page_last               10269
_journal_paper_doi               10.1021/acsami.8b00416
_journal_volume                  10
_journal_year                    2018
_chemical_formula_moiety         'C14 H6 S4, C12 F4 N4'
_chemical_formula_sum            'C26 H6 F4 N4 S4'
_chemical_formula_weight         578.59
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                98.948(14)
_cell_angle_beta                 100.39(2)
_cell_angle_gamma                94.36(3)
_cell_formula_units_Z            1
_cell_length_a                   7.8417(16)
_cell_length_b                   7.8896(14)
_cell_length_c                   9.4489(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.30
_cell_measurement_theta_min      15.02
_cell_volume                     564.73(18)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        WinAFC
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3897
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_standards_decay_%        -0.251
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             290.00
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0561P)²+0.0504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                1966
_reflns_number_total             3284
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            am8b00416_si_005.cif
_cod_data_source_block           Cytidine_(Rigaku_Master_fo
_cod_original_cell_volume        564.73(19)
_cod_database_code               4515430
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.31921(9) 0.93699(9) 0.73381(8) 0.0425(2) Uani 1.0 2 d .
S2 S 0.40829(9) 0.43645(9) 0.79778(7) 0.03432(17) Uani 1.0 2 d .
F1 F -0.0480(2) 0.39104(19) 0.74924(16) 0.0409(4) Uani 1.0 2 d .
F2 F 0.0726(2) 0.18244(18) 0.55374(17) 0.0409(4) Uani 1.0 2 d .
N1 N -0.1838(4) 0.6595(4) 0.9586(3) 0.0585(8) Uani 1.0 2 d .
N2 N -0.2326(4) 1.0213(4) 0.6858(4) 0.0592(8) Uani 1.0 2 d .
C1 C 0.2672(4) 0.9107(4) 0.8990(4) 0.0479(8) Uani 1.0 2 d .
C2 C 0.2892(4) 0.7518(4) 0.9332(3) 0.0425(7) Uani 1.0 2 d .
C3 C 0.3518(4) 0.6469(4) 0.8216(3) 0.0337(6) Uani 1.0 2 d .
C4 C 0.3742(3) 0.7300(3) 0.7066(3) 0.0299(5) Uani 1.0 2 d .
C5 C 0.4380(3) 0.6258(3) 0.5922(3) 0.0269(5) Uani 1.0 2 d .
C6 C 0.4651(3) 0.4602(3) 0.6306(3) 0.0274(5) Uani 1.0 2 d .
C7 C 0.5272(3) 0.3348(3) 0.5391(3) 0.0288(5) Uani 1.0 2 d .
C8 C -0.0673(3) 0.6143(3) 0.6077(3) 0.0267(5) Uani 1.0 2 d .
C9 C -0.0244(3) 0.4449(3) 0.6275(3) 0.0284(5) Uani 1.0 2 d .
C10 C 0.0375(3) 0.3384(3) 0.5271(3) 0.0260(5) Uani 1.0 2 d .
C11 C -0.1311(3) 0.7226(3) 0.7099(3) 0.0300(5) Uani 1.0 2 d .
C12 C -0.1577(4) 0.6803(4) 0.8470(3) 0.0390(6) Uani 1.0 2 d .
C13 C -0.1826(4) 0.8895(4) 0.6908(4) 0.0396(6) Uani 1.0 2 d .
H1 H 0.2275 0.9974 0.9593 0.0574 Uiso 1.0 2 calc R
H2 H 0.2665 0.7167 1.0181 0.0510 Uiso 1.0 2 calc R
H7 H 0.5451 0.2275 0.5647 0.0345 Uiso 1.0 2 calc R
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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C4 90.67(15) yes . .
C3 S2 C6 90.67(13) yes . .
S1 C1 C2 113.9(3) yes . .
C1 C2 C3 110.6(3) yes . .
S2 C3 C2 134.2(3) yes . .
S2 C3 C4 112.7(2) yes . .
C2 C3 C4 113.2(3) yes . .
S1 C4 C3 111.6(2) yes . .
S1 C4 C5 134.3(2) yes . .
C3 C4 C5 114.1(3) yes . .
C4 C5 C6 109.5(3) yes . .
C4 C5 C7 129.9(3) yes . 2_666
C6 C5 C7 120.6(3) yes . 2_666
S2 C6 C5 113.07(18) yes . .
S2 C6 C7 125.6(2) yes . .
C5 C6 C7 121.3(3) yes . .
C5 C7 C6 118.1(3) yes 2_666 .
C9 C8 C10 114.4(2) yes . 2_566
C9 C8 C11 122.7(3) yes . .
C10 C8 C11 122.9(3) yes 2_566 .
F1 C9 C8 118.3(2) yes . .
F1 C9 C10 118.9(3) yes . .
C8 C9 C10 122.8(3) yes . .
F2 C10 C8 118.3(2) yes . 2_566
F2 C10 C9 118.9(3) yes . .
C8 C10 C9 122.8(3) yes 2_566 .
C8 C11 C12 124.0(3) yes . .
C8 C11 C13 124.2(3) yes . .
C12 C11 C13 111.9(3) yes . .
N1 C12 C11 174.4(4) yes . .
N2 C13 C11 173.5(4) yes . .
S1 C1 H1 123.037 no . .
C2 C1 H1 123.026 no . .
C1 C2 H2 124.684 no . .
C3 C2 H2 124.683 no . .
C5 C7 H7 120.943 no 2_666 .
C6 C7 H7 120.955 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
S1 C1 1.721(4) yes .
S1 C4 1.713(3) yes .
S2 C3 1.742(3) yes .
S2 C6 1.750(3) yes .
F1 C9 1.325(3) yes .
F2 C10 1.333(3) yes .
N1 C12 1.143(5) yes .
N2 C13 1.144(4) yes .
C1 C2 1.358(5) yes .
C2 C3 1.419(4) yes .
C3 C4 1.384(4) yes .
C4 C5 1.440(4) yes .
C5 C6 1.430(4) yes .
C5 C7 1.393(4) yes 2_666
C6 C7 1.386(4) yes .
C8 C9 1.435(4) yes .
C8 C10 1.435(4) yes 2_566
C8 C11 1.377(4) yes .
C9 C10 1.349(4) yes .
C11 C12 1.433(4) yes .
C11 C13 1.435(4) yes .
C1 H1 0.930 no .
C2 H2 0.930 no .
C7 H7 0.930 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
S1 C7 3.535(3) no 2_666
F1 F2 2.634(3) no .
F1 N1 3.055(4) no .
F1 C11 2.807(3) no .
F1 C12 2.595(4) no .
F2 N2 3.080(4) no 2_566
F2 C11 2.814(4) no 2_566
F2 C13 2.606(4) no 2_566
N1 C8 3.568(4) no .
N1 C13 3.336(5) no .
N2 C8 3.575(4) no .
N2 C12 3.331(5) no .
C5 C5 2.785(4) no 2_666
C6 C6 2.775(4) no 2_666
C7 C7 2.859(4) no 2_666
C8 C8 2.903(4) no 2_566
C9 C9 2.764(4) no 2_566
C9 C12 2.954(4) no .
C10 C10 2.763(4) no 2_566
C10 C13 2.962(4) no 2_566
S1 F2 3.2852(19) no 1_565
S2 F1 3.508(2) no .
S2 F2 3.4402(18) no .
S2 N1 3.492(3) no 1_655
S2 N1 3.282(4) no 2_567
S2 C9 3.493(3) no .
S2 C10 3.457(3) no .
F1 S2 3.508(2) no .
F1 N1 3.119(4) no 2_567
F1 N2 3.076(3) no 1_545
F1 C3 3.494(3) no .
F1 C7 3.514(3) no 1_455
F2 S1 3.2852(19) no 1_545
F2 S2 3.4402(18) no .
F2 F2 2.965(2) no 2_556
F2 N2 3.164(4) no 1_545
F2 C6 3.532(3) no .
F2 C13 3.491(4) no 1_545
N1 S2 3.492(3) no 1_455
N1 S2 3.282(4) no 2_567
N1 F1 3.119(4) no 2_567
N2 F1 3.076(3) no 1_565
N2 F2 3.164(4) no 1_565
N2 C7 3.524(4) no 1_465
C1 C11 3.406(4) no .
C1 C12 3.586(5) no .
C2 C11 3.548(4) no .
C2 C12 3.434(4) no .
C3 F1 3.494(3) no .
C3 C8 3.502(4) no .
C3 C9 3.321(4) no .
C4 C8 3.433(4) no .
C4 C9 3.600(4) no .
C4 C10 3.520(4) no 2_566
C5 C8 3.416(3) no 2_566
C5 C9 3.475(4) no 2_566
C5 C11 3.351(4) no 1_655
C5 C12 3.571(4) no 1_655
C5 C13 3.392(4) no 1_655
C6 F2 3.532(3) no .
C6 C8 3.452(3) no 2_566
C6 C10 3.340(4) no .
C6 C11 3.541(4) no 1_655
C6 C12 3.447(4) no 1_655
C7 F1 3.514(3) no 1_655
C7 N2 3.524(4) no 1_645
C7 C9 3.474(4) no 1_655
C7 C11 3.494(4) no 2_566
C7 C13 3.334(4) no 2_566
C8 C3 3.502(4) no .
C8 C4 3.433(4) no .
C8 C5 3.416(3) no 2_566
C8 C6 3.452(3) no 2_566
C9 S2 3.493(3) no .
C9 C3 3.321(4) no .
C9 C4 3.600(4) no .
C9 C5 3.475(4) no 2_566
C9 C7 3.474(4) no 1_455
C10 S2 3.457(3) no .
C10 C4 3.520(4) no 2_566
C10 C6 3.340(4) no .
C11 C1 3.406(4) no .
C11 C2 3.548(4) no .
C11 C5 3.351(4) no 1_455
C11 C6 3.541(4) no 1_455
C11 C7 3.494(4) no 2_566
C12 C1 3.586(5) no .
C12 C2 3.434(4) no .
C12 C5 3.571(4) no 1_455
C12 C6 3.447(4) no 1_455
C13 F2 3.491(4) no 1_565
C13 C5 3.392(4) no 1_455
C13 C7 3.334(4) no 2_566
S1 H2 3.4857 no .
S1 H7 3.3056 no 2_666
S2 H2 3.1991 no .
S2 H7 2.9512 no .
C3 H1 3.1682 no .
C4 H1 3.3567 no .
C4 H2 3.2196 no .
C4 H7 2.8118 no 2_666
C5 H7 3.2977 no .
C6 H7 3.2975 no 2_666
H1 H2 2.3942 no .
S1 H7 3.5335 no 1_565
S2 H2 3.2425 no 2_667
F1 H2 3.1953 no 2_567
F1 H7 3.3993 no 1_455
N1 H1 2.7620 no 2_577
N1 H2 3.4569 no .
N1 H2 3.0397 no 2_567
N2 H1 3.3727 no 2_577
N2 H2 3.2747 no 2_577
N2 H7 2.6988 no 1_465
N2 H7 3.3453 no 2_566
C9 H7 3.5741 no 1_455
C12 H1 3.0394 no 2_577
C12 H2 3.3956 no .
C13 H1 3.3763 no 2_577
C13 H7 3.3455 no 2_566
H1 N1 2.7620 no 2_577
H1 N2 3.3727 no 2_577
H1 C12 3.0394 no 2_577
H1 C13 3.3763 no 2_577
H2 S2 3.2425 no 2_667
H2 F1 3.1953 no 2_567
H2 N1 3.4569 no .
H2 N1 3.0397 no 2_567
H2 N2 3.2747 no 2_577
H2 C12 3.3956 no .
H7 S1 3.5335 no 1_545
H7 F1 3.3993 no 1_655
H7 N2 2.6988 no 1_645
H7 N2 3.3453 no 2_566
H7 C9 3.5741 no 1_655
H7 C13 3.3455 no 2_566
H7 H7 3.5800 no 2_656
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C4 C3 0.14(17) no . . .
C1 S1 C4 C5 -179.7(3) no . . .
C4 S1 C1 C2 -0.3(2) no . . .
C3 S2 C6 C5 -1.10(15) no . . .
C3 S2 C6 C7 -179.90(18) no . . .
C6 S2 C3 C2 -179.0(3) no . . .
C6 S2 C3 C4 0.43(16) no . . .
S1 C1 C2 C3 0.3(3) no . . .
C1 C2 C3 S2 179.2(3) no . . .
C1 C2 C3 C4 -0.2(3) no . . .
S2 C3 C4 S1 -179.54(12) no . . .
S2 C3 C4 C5 0.3(3) no . . .
C2 C3 C4 S1 0.0(3) no . . .
C2 C3 C4 C5 179.90(18) no . . .
S1 C4 C5 C6 178.70(17) no . . .
S1 C4 C5 C7 -1.3(4) no . . 2_666
C3 C4 C5 C6 -1.2(3) no . . .
C3 C4 C5 C7 178.88(19) no . . 2_666
C4 C5 C6 S2 1.5(3) no . . .
C4 C5 C6 C7 -179.69(17) no . . .
C4 C5 C7 C6 179.69(19) no . 2_666 2_666
C6 C5 C7 C6 -0.3(3) no . 2_666 2_666
C7 C5 C6 S2 -178.57(17) no 2_666 . .
C7 C5 C6 C7 0.3(3) no 2_666 . .
S2 C6 C7 C5 178.42(14) no . . 2_666
C5 C6 C7 C5 -0.3(3) no . . 2_666
C9 C8 C10 F2 -179.41(17) no . 2_566 2_566
C9 C8 C10 C9 0.5(3) no . 2_566 2_566
C10 C8 C9 F1 179.98(17) no 2_566 . .
C10 C8 C9 C10 -0.5(3) no 2_566 . .
C9 C8 C11 C12 1.4(4) no . . .
C9 C8 C11 C13 -177.11(18) no . . .
C11 C8 C9 F1 0.3(3) no . . .
C11 C8 C9 C10 179.78(19) no . . .
C10 C8 C11 C12 -178.30(18) no 2_566 . .
C10 C8 C11 C13 3.2(4) no 2_566 . .
C11 C8 C10 F2 0.3(3) no . 2_566 2_566
C11 C8 C10 C9 -179.78(19) no . 2_566 2_566
F1 C9 C10 F2 0.1(3) no . . .
F1 C9 C10 C8 -179.94(17) no . . 2_566
C8 C9 C10 F2 -179.37(18) no . . .
C8 C9 C10 C8 0.6(4) no . . 2_566
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345697
