#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/54/4515427.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_4515427
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 H2 F2 N4'
_chemical_formula_sum            'C26 H8 F2 N4 S4'
_chemical_formula_weight         542.61
_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                101.11(6)
_cell_angle_beta                 99.66(5)
_cell_angle_gamma                96.12(6)
_cell_formula_units_Z            1
_cell_length_a                   7.689(5)
_cell_length_b                   7.978(6)
_cell_length_c                   9.302(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.28
_cell_measurement_theta_min      15.20
_cell_volume                     546.3(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0202
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2451
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_standards_decay_%        -0.200
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             274.00
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0960P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                1197
_reflns_number_total             1921
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            am8b00416_si_004.cif
_cod_data_source_block           Cytidine_(Rigaku_Master_fo
_cod_database_code               4515427
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 0.04623(16) 0.67226(16) 0.27189(14) 0.0360(4) Uani 1.0 2 d .
S2 S 0.54975(15) 0.58131(14) 0.19203(12) 0.0302(4) Uani 1.0 2 d .
F1 F 0.1804(4) 0.0804(4) 0.5505(4) 0.0472(8) Uani 1.0 2 d .
N1 N -0.0338(7) 0.2068(7) 0.2908(6) 0.0570(13) Uani 1.0 2 d .
N2 N 0.3631(7) 0.1428(7) 0.0279(6) 0.0559(13) Uani 1.0 2 d .
C1 C 0.0662(7) 0.7195(6) 0.1018(6) 0.0389(13) Uani 1.0 2 d .
C2 C 0.2223(7) 0.6947(6) 0.0626(6) 0.0350(12) Uani 1.0 2 d .
C3 C 0.3350(6) 0.6348(6) 0.1721(5) 0.0260(10) Uani 1.0 2 d .
C4 C 0.2569(6) 0.6166(6) 0.2934(5) 0.0282(10) Uani 1.0 2 d .
C5 C 0.3672(6) 0.5574(5) 0.4080(5) 0.0239(10) Uani 1.0 2 d .
C6 C 0.5346(6) 0.5317(6) 0.3655(5) 0.0246(10) Uani 1.0 2 d .
C7 C 0.6661(6) 0.4728(6) 0.4561(5) 0.0265(10) Uani 1.0 2 d .
C8 C 0.3864(6) 0.0588(5) 0.3881(5) 0.0255(10) Uani 1.0 2 d .
C9 C 0.3377(6) 0.0389(6) 0.5275(5) 0.0245(10) Uani 1.0 2 d .
C10 C 0.4424(6) -0.0150(6) 0.6341(5) 0.0271(10) Uani 1.0 2 d .
C11 C 0.2754(6) 0.1153(6) 0.2789(6) 0.0288(10) Uani 1.0 2 d .
C12 C 0.1032(7) 0.1635(6) 0.2909(6) 0.0369(12) Uani 1.0 2 d .
C13 C 0.3288(7) 0.1300(7) 0.1396(6) 0.0368(12) Uani 1.0 2 d .
H1 H -0.0238 0.7587 0.0425 0.0467 Uiso 1.0 2 calc R
H2 H 0.2531 0.7145 -0.0259 0.0420 Uiso 1.0 2 calc R
H7 H 0.7735 0.4539 0.4269 0.0318 Uiso 1.0 2 calc R
H10 H 0.4043 -0.0240 0.7225 0.0325 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 90.4(3) yes . .
C3 S2 C6 90.8(3) yes . .
S1 C1 C2 114.0(4) yes . .
C1 C2 C3 111.6(5) yes . .
S2 C3 C2 135.1(4) yes . .
S2 C3 C4 112.4(4) yes . .
C2 C3 C4 112.6(5) yes . .
S1 C4 C3 111.4(4) yes . .
S1 C4 C5 134.1(4) yes . .
C3 C4 C5 114.5(4) yes . .
C4 C5 C6 109.4(4) yes . .
C4 C5 C7 130.1(5) yes . 2_666
C6 C5 C7 120.5(4) yes . 2_666
S2 C6 C5 112.9(4) yes . .
S2 C6 C7 125.7(4) yes . .
C5 C6 C7 121.3(5) yes . .
C5 C7 C6 118.1(5) yes 2_666 .
C9 C8 C10 116.3(4) yes . 2_656
C9 C8 C11 122.9(5) yes . .
C10 C8 C11 120.8(5) yes 2_656 .
F1 C9 C8 117.1(4) yes . .
F1 C9 C10 119.0(5) yes . .
C8 C9 C10 123.9(5) yes . .
C8 C10 C9 119.8(5) yes 2_656 .
C8 C11 C12 125.1(5) yes . .
C8 C11 C13 120.9(5) yes . .
C12 C11 C13 114.1(5) yes . .
N1 C12 C11 174.7(7) yes . .
N2 C13 C11 176.9(6) yes . .
S1 C1 H1 122.997 no . .
C2 C1 H1 122.992 no . .
C1 C2 H2 124.188 no . .
C3 C2 H2 124.182 no . .
C5 C7 H7 120.932 no 2_666 .
C6 C7 H7 120.940 no . .
C8 C10 H10 120.101 no 2_656 .
C9 C10 H10 120.098 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 1.723(6) yes .
S1 C4 1.715(5) yes .
S2 C3 1.738(5) yes .
S2 C6 1.753(5) yes .
F1 C9 1.328(6) yes .
N1 C12 1.143(8) yes .
N2 C13 1.135(8) yes .
C1 C2 1.335(8) yes .
C2 C3 1.413(7) yes .
C3 C4 1.389(7) yes .
C4 C5 1.433(7) yes .
C5 C6 1.432(7) yes .
C5 C7 1.391(7) yes 2_666
C6 C7 1.387(7) yes .
C8 C9 1.441(7) yes .
C8 C10 1.436(7) yes 2_656
C8 C11 1.389(7) yes .
C9 C10 1.336(7) yes .
C11 C12 1.434(7) yes .
C11 C13 1.445(8) yes .
C1 H1 0.930 no .
C2 H2 0.930 no .
C7 H7 0.930 no .
C10 H10 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 3.526(5) no 2_666
F1 N1 3.086(7) no .
F1 C11 2.800(7) no .
F1 C12 2.616(7) no .
N1 C8 3.591(7) no .
N1 C13 3.387(8) no .
N2 C8 3.521(8) no .
N2 C12 3.400(8) no .
C5 C5 2.787(7) no 2_666
C6 C6 2.771(7) no 2_666
C7 C7 2.860(7) no 2_666
C8 C8 2.854(7) no 2_656
C9 C9 2.741(7) no 2_656
C9 C12 2.997(7) no .
C10 C10 2.828(7) no 2_656
C10 C13 2.866(8) no 2_656
S1 F1 3.178(4) no 2_566
S2 S2 3.481(3) no 2_665
S2 F1 3.460(4) no 2_666
S2 N2 3.573(6) no .
S2 N2 3.370(6) no 2_665
S2 C9 3.518(5) no 2_666
S2 C10 3.515(5) no 2_666
F1 S1 3.178(4) no 2_566
F1 S2 3.460(4) no 2_666
F1 F1 2.850(5) no 2_556
F1 N1 3.164(7) no 2_556
F1 C6 3.470(6) no 2_666
F1 C12 3.463(7) no 2_556
N1 F1 3.164(7) no 2_556
N1 C10 3.581(8) no 2_556
N2 S2 3.573(6) no .
N2 S2 3.370(6) no 2_665
N2 N2 3.290(8) no 2_655
C1 C1 3.595(7) no 2_565
C1 C11 3.362(7) no 1_565
C1 C12 3.597(7) no 1_565
C1 C13 3.583(8) no 1_565
C2 C11 3.508(7) no 1_565
C2 C13 3.388(7) no 1_565
C3 C8 3.530(6) no 1_565
C3 C10 3.336(6) no 2_666
C4 C8 3.460(7) no 1_565
C4 C9 3.571(7) no 1_565
C5 C8 3.447(6) no 2_666
C5 C10 3.578(6) no 1_565
C5 C11 3.454(7) no .
C5 C12 3.430(7) no .
C6 F1 3.470(6) no 2_666
C6 C8 3.538(6) no 2_666
C6 C9 3.366(7) no 2_666
C6 C11 3.560(7) no .
C6 C13 3.521(7) no .
C7 C10 3.560(7) no 2_656
C7 C12 3.461(7) no 2_666
C8 C3 3.530(6) no 1_545
C8 C4 3.460(7) no 1_545
C8 C5 3.447(6) no 2_666
C8 C6 3.538(6) no 2_666
C9 S2 3.518(5) no 2_666
C9 C4 3.571(7) no 1_545
C9 C6 3.366(7) no 2_666
C10 S2 3.515(5) no 2_666
C10 N1 3.581(8) no 2_556
C10 C3 3.336(6) no 2_666
C10 C5 3.578(6) no 1_545
C10 C7 3.560(7) no 2_656
C11 C1 3.362(7) no 1_545
C11 C2 3.508(7) no 1_545
C11 C5 3.454(7) no .
C11 C6 3.560(7) no .
C12 F1 3.463(7) no 2_556
C12 C1 3.597(7) no 1_545
C12 C5 3.430(7) no .
C12 C7 3.461(7) no 2_666
C13 C1 3.583(8) no 1_545
C13 C2 3.388(7) no 1_545
C13 C6 3.521(7) no .
S1 H2 3.4697 no .
S1 H7 3.2968 no 2_666
S2 H2 3.1990 no .
S2 H7 2.9549 no .
F1 H10 2.4724 no .
N2 H10 3.0501 no 2_656
C3 H1 3.1567 no .
C4 H1 3.3530 no .
C4 H2 3.2097 no .
C4 H7 2.8071 no 2_666
C5 H7 3.3006 no .
C6 H7 3.2960 no 2_666
C8 H10 3.2857 no .
C9 H10 3.2935 no 2_656
C11 H10 2.6427 no 2_656
C13 H10 2.5448 no 2_656
H1 H2 2.3645 no .
S1 H7 3.2734 no 1_455
S2 H2 3.2245 no 2_665
S2 H10 3.4335 no 2_666
N1 H1 3.2627 no 2_565
N1 H2 2.9562 no 2_565
N1 H7 2.8240 no 1_455
N1 H7 3.5461 no 2_666
N1 H10 3.0311 no 2_556
N2 H1 2.8139 no 2_565
N2 H2 3.3505 no 1_545
N2 H2 3.0518 no 2_665
N2 H10 2.9793 no 1_554
C3 H10 3.3855 no 2_666
C7 H10 3.5863 no 2_656
C11 H1 3.5667 no 1_545
C12 H1 3.5235 no 1_545
C12 H1 3.2501 no 2_565
C12 H7 3.5454 no 2_666
C13 H1 2.9750 no 2_565
C13 H2 3.3191 no 1_545
H1 N1 3.2627 no 2_565
H1 N2 2.8139 no 2_565
H1 C11 3.5667 no 1_565
H1 C12 3.5235 no 1_565
H1 C12 3.2501 no 2_565
H1 C13 2.9750 no 2_565
H2 S2 3.2245 no 2_665
H2 N1 2.9562 no 2_565
H2 N2 3.3505 no 1_565
H2 N2 3.0518 no 2_665
H2 C13 3.3191 no 1_565
H7 S1 3.2734 no 1_655
H7 N1 2.8240 no 1_655
H7 N1 3.5461 no 2_666
H7 C12 3.5454 no 2_666
H7 H7 3.4651 no 2_766
H7 H10 3.4767 no 2_656
H10 S2 3.4335 no 2_666
H10 N1 3.0311 no 2_556
H10 N2 2.9793 no 1_556
H10 C3 3.3855 no 2_666
H10 C7 3.5863 no 2_656
H10 H7 3.4767 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 -0.2(3) no . . .
C1 S1 C4 C5 179.4(4) no . . .
C4 S1 C1 C2 0.1(3) no . . .
C3 S2 C6 C5 -0.5(3) no . . .
C3 S2 C6 C7 179.2(3) no . . .
C6 S2 C3 C2 179.4(4) no . . .
C6 S2 C3 C4 0.5(3) no . . .
S1 C1 C2 C3 0.0(5) no . . .
C1 C2 C3 S2 -179.0(4) no . . .
C1 C2 C3 C4 -0.1(5) no . . .
S2 C3 C4 S1 179.4(2) no . . .
S2 C3 C4 C5 -0.3(5) no . . .
C2 C3 C4 S1 0.2(5) no . . .
C2 C3 C4 C5 -179.5(3) no . . .
S1 C4 C5 C6 -179.6(3) no . . .
S1 C4 C5 C7 -0.5(7) no . . 2_666
C3 C4 C5 C6 -0.0(5) no . . .
C3 C4 C5 C7 179.1(4) no . . 2_666
C4 C5 C6 S2 0.4(4) no . . .
C4 C5 C6 C7 -179.3(3) no . . .
C4 C5 C7 C6 179.5(4) no . 2_666 2_666
C6 C5 C7 C6 -1.4(6) no . 2_666 2_666
C7 C5 C6 S2 -178.8(3) no 2_666 . .
C7 C5 C6 C7 1.5(6) no 2_666 . .
S2 C6 C7 C5 178.9(3) no . . 2_666
C5 C6 C7 C5 -1.4(6) no . . 2_666
C9 C8 C10 C9 -0.7(5) no . 2_656 2_656
C10 C8 C9 F1 179.4(3) no 2_656 . .
C10 C8 C9 C10 0.7(6) no 2_656 . .
C9 C8 C11 C12 1.2(6) no . . .
C9 C8 C11 C13 -178.8(3) no . . .
C11 C8 C9 F1 -1.2(6) no . . .
C11 C8 C9 C10 -179.8(4) no . . .
C10 C8 C11 C12 -179.4(4) no 2_656 . .
C10 C8 C11 C13 0.6(6) no 2_656 . .
C11 C8 C10 C9 179.9(4) no . 2_656 2_656
F1 C9 C10 C8 -179.4(3) no . . 2_656
C8 C9 C10 C8 -0.8(6) no . . 2_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345695
