#------------------------------------------------------------------------------
#$Date: 2019-11-10 01:43:25 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/54/4515428.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_4515428
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 H4 N4'
_chemical_formula_sum            'C26 H10 N4 S4'
_chemical_formula_weight         506.63
_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                101.154(15)
_cell_angle_beta                 99.186(13)
_cell_angle_gamma                95.844(13)
_cell_formula_units_Z            1
_cell_length_a                   7.5661(10)
_cell_length_b                   7.9740(15)
_cell_length_c                   9.2855(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.48
_cell_measurement_theta_min      15.06
_cell_volume                     537.47(16)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0201
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3723
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_standards_decay_%        0.581
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             258.00
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.360
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0480P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                1870
_reflns_number_total             3137
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            am8b00416_si_003.cif
_cod_data_source_block           Cytidine_(Rigaku_Master_fo
_cod_database_code               4515428
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 0.96045(8) 0.32379(9) 0.72442(7) 0.03385(18) Uani 1.0 2 d .
S2 S 0.45130(8) 0.42097(8) 0.80966(6) 0.02782(16) Uani 1.0 2 d .
N1 N 1.0375(4) -0.1959(4) 0.6949(4) 0.0548(7) Uani 1.0 2 d .
N2 N 0.6351(4) -0.1411(4) 0.9733(3) 0.0517(7) Uani 1.0 2 d .
C1 C 0.9427(4) 0.2787(4) 0.8962(3) 0.0372(7) Uani 1.0 2 d .
C2 C 0.7826(4) 0.3043(4) 0.9375(3) 0.0325(6) Uani 1.0 2 d .
C3 C 0.6682(4) 0.3634(3) 0.8260(3) 0.0263(5) Uani 1.0 2 d .
C4 C 0.7462(3) 0.3799(3) 0.7038(3) 0.0247(5) Uani 1.0 2 d .
C5 C 0.6343(3) 0.4406(3) 0.5904(3) 0.0225(5) Uani 1.0 2 d .
C6 C 0.4658(3) 0.4691(3) 0.6353(3) 0.0217(5) Uani 1.0 2 d .
C7 C 0.3322(3) 0.5297(3) 0.5464(3) 0.0239(5) Uani 1.0 2 d .
C8 C 0.6124(3) -0.0572(3) 0.6122(3) 0.0247(5) Uani 1.0 2 d .
C9 C 0.6703(3) -0.0402(3) 0.4743(3) 0.0275(5) Uani 1.0 2 d .
C10 C 0.4372(4) -0.0142(3) 0.6321(3) 0.0283(6) Uani 1.0 2 d .
C11 C 0.7231(4) -0.1133(3) 0.7213(3) 0.0280(5) Uani 1.0 2 d .
C12 C 0.8982(4) -0.1577(4) 0.7052(3) 0.0343(6) Uani 1.0 2 d .
C13 C 0.6703(4) -0.1281(4) 0.8607(3) 0.0334(6) Uani 1.0 2 d .
H1 H 1.0348 0.2403 0.9550 0.0447 Uiso 1.0 2 calc R
H2 H 0.7513 0.2859 1.0266 0.0390 Uiso 1.0 2 calc R
H7 H 0.2238 0.5498 0.5772 0.0287 Uiso 1.0 2 calc R
H12 H 0.7834 -0.0673 0.4589 0.0330 Uiso 1.0 2 calc R
H13 H 0.3972 -0.0242 0.7201 0.0340 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
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 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)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 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)
;
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 90.86(13) yes . .
C3 S2 C6 90.65(12) yes . .
S1 C1 C2 113.8(2) yes . .
C1 C2 C3 110.8(3) yes . .
S2 C3 C2 134.2(2) yes . .
S2 C3 C4 112.50(19) yes . .
C2 C3 C4 113.3(3) yes . .
S1 C4 C3 111.22(19) yes . .
S1 C4 C5 134.3(2) yes . .
C3 C4 C5 114.4(3) yes . .
C4 C5 C6 109.5(3) yes . .
C4 C5 C7 130.0(3) yes . 2_666
C6 C5 C7 120.6(2) yes . 2_666
S2 C6 C5 112.96(18) yes . .
S2 C6 C7 125.49(19) yes . .
C5 C6 C7 121.5(3) yes . .
C5 C7 C6 117.9(3) yes 2_666 .
C9 C8 C10 118.0(3) yes . .
C9 C8 C11 120.7(3) yes . .
C10 C8 C11 121.3(3) yes . .
C8 C9 C10 120.9(3) yes . 2_656
C8 C10 C9 121.1(3) yes . 2_656
C8 C11 C12 122.8(3) yes . .
C8 C11 C13 121.9(3) yes . .
C12 C11 C13 115.3(3) yes . .
N1 C12 C11 178.2(4) yes . .
N2 C13 C11 177.3(3) yes . .
S1 C1 H1 123.097 no . .
C2 C1 H1 123.100 no . .
C1 C2 H2 124.604 no . .
C3 C2 H2 124.605 no . .
C5 C7 H7 121.058 no 2_666 .
C6 C7 H7 121.059 no . .
C8 C9 H12 119.573 no . .
C10 C9 H12 119.565 no 2_656 .
C8 C10 H13 119.428 no . .
C9 C10 H13 119.433 no 2_656 .
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 1.724(3) yes .
S1 C4 1.716(3) yes .
S2 C3 1.740(3) yes .
S2 C6 1.752(3) yes .
N1 C12 1.140(4) yes .
N2 C13 1.140(5) yes .
C1 C2 1.351(4) yes .
C2 C3 1.424(4) yes .
C3 C4 1.382(4) yes .
C4 C5 1.434(4) yes .
C5 C6 1.429(4) yes .
C5 C7 1.393(4) yes 2_666
C6 C7 1.387(4) yes .
C8 C9 1.443(4) yes .
C8 C10 1.433(4) yes .
C8 C11 1.382(4) yes .
C9 C10 1.345(4) yes 2_656
C11 C12 1.429(4) yes .
C11 C13 1.437(4) yes .
C1 H1 0.930 no .
C2 H2 0.930 no .
C7 H7 0.930 no .
C9 H12 0.930 no .
C10 H13 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 3.533(3) no 2_666
N1 C8 3.525(4) no .
N1 C13 3.425(5) no .
N2 C8 3.525(4) no .
N2 C12 3.419(5) no .
C5 C5 2.786(4) no 2_666
C6 C6 2.768(4) no 2_666
C7 C7 2.863(4) no 2_666
C8 C8 2.826(4) no 2_656
C9 C9 2.809(4) no 2_656
C9 C12 2.893(4) no .
C10 C10 2.808(4) no 2_656
C10 C13 2.884(4) no .
S2 S2 3.4470(10) no 2_667
S2 N2 3.567(3) no 1_565
S2 N2 3.367(4) no 2_657
S2 C9 3.546(3) no 2_656
S2 C10 3.525(3) no .
N1 C7 3.531(4) no 1_645
N1 C9 3.508(4) no 2_756
N1 C10 3.403(4) no 1_655
N2 S2 3.567(3) no 1_545
N2 S2 3.367(4) no 2_657
N2 N2 3.212(5) no 2_657
N2 C1 3.588(4) no 2_757
N2 C2 3.576(4) no 2_657
C1 N2 3.588(4) no 2_757
C1 C11 3.359(4) no .
C1 C12 3.543(4) no .
C1 C13 3.590(4) no .
C2 N2 3.576(4) no 2_657
C2 C11 3.484(4) no .
C2 C13 3.373(4) no .
C3 C8 3.498(4) no .
C3 C10 3.345(3) no .
C4 C8 3.429(4) no .
C4 C9 3.543(4) no .
C5 C8 3.444(3) no 2_656
C5 C10 3.559(4) no 2_656
C5 C11 3.488(4) no 1_565
C5 C12 3.476(4) no 1_565
C6 C8 3.559(3) no 2_656
C6 C9 3.376(4) no 2_656
C6 C11 3.559(4) no 1_565
C6 C13 3.528(4) no 1_565
C7 N1 3.531(4) no 1_465
C7 C10 3.547(4) no 1_565
C7 C12 3.502(4) no 2_656
C8 C3 3.498(4) no .
C8 C4 3.429(4) no .
C8 C5 3.444(3) no 2_656
C8 C6 3.559(3) no 2_656
C9 S2 3.546(3) no 2_656
C9 N1 3.508(4) no 2_756
C9 C4 3.543(4) no .
C9 C6 3.376(4) no 2_656
C10 S2 3.525(3) no .
C10 N1 3.403(4) no 1_455
C10 C3 3.345(3) no .
C10 C5 3.559(4) no 2_656
C10 C7 3.547(4) no 1_545
C11 C1 3.359(4) no .
C11 C2 3.484(4) no .
C11 C5 3.488(4) no 1_545
C11 C6 3.559(4) no 1_545
C12 C1 3.543(4) no .
C12 C5 3.476(4) no 1_545
C12 C7 3.502(4) no 2_656
C13 C1 3.590(4) no .
C13 C2 3.373(4) no .
C13 C6 3.528(4) no 1_545
S1 H2 3.4808 no .
S1 H7 3.3064 no 2_666
S2 H2 3.2014 no .
S2 H7 2.9516 no .
N1 H12 3.0779 no .
N2 H13 3.0778 no .
C3 H1 3.1689 no .
C4 H1 3.3648 no .
C4 H2 3.2228 no .
C4 H7 2.8108 no 2_666
C5 H7 3.3001 no .
C6 H7 3.2966 no 2_666
C8 H12 3.2585 no 2_656
C8 H13 3.2651 no 2_656
C9 H13 3.3072 no .
C10 H12 3.3066 no .
C11 H12 2.6358 no .
C11 H13 2.6332 no .
C12 H12 2.5757 no .
C13 H13 2.5621 no .
H1 H2 2.3866 no .
H12 H13 2.2605 no 2_656
S1 H7 3.1905 no 1_655
S1 H12 3.5663 no .
S1 H12 3.3688 no 2_756
S2 H2 3.1975 no 2_667
S2 H12 3.4887 no 2_656
S2 H13 3.4516 no .
N1 H1 3.4595 no 2_757
N1 H2 3.0641 no 2_757
N1 H7 2.7402 no 1_645
N1 H7 3.5730 no 2_656
N1 H12 3.0783 no 2_756
N1 H13 2.8724 no 1_655
N2 H1 2.7168 no 2_757
N2 H2 3.3483 no .
N2 H2 3.0327 no 2_657
N2 H13 2.9563 no 2_657
C3 H13 3.4078 no .
C6 H12 3.4273 no 2_656
C7 H13 3.5592 no 1_565
C10 H7 3.5861 no 1_545
C11 H1 3.5866 no .
C12 H1 3.4985 no .
C12 H1 3.3180 no 2_757
C12 H12 3.5625 no 2_756
C13 H1 2.9132 no 2_757
C13 H2 3.3114 no .
H1 N1 3.4595 no 2_757
H1 N2 2.7168 no 2_757
H1 C11 3.5866 no .
H1 C12 3.4985 no .
H1 C12 3.3180 no 2_757
H1 C13 2.9132 no 2_757
H2 S2 3.1975 no 2_667
H2 N1 3.0641 no 2_757
H2 N2 3.3483 no .
H2 N2 3.0327 no 2_657
H2 C13 3.3114 no .
H7 S1 3.1905 no 1_455
H7 N1 2.7402 no 1_465
H7 N1 3.5730 no 2_656
H7 C10 3.5861 no 1_565
H7 H7 3.4077 no 2_566
H7 H13 3.4371 no 1_565
H12 S1 3.5663 no .
H12 S1 3.3688 no 2_756
H12 S2 3.4887 no 2_656
H12 N1 3.0783 no 2_756
H12 C6 3.4273 no 2_656
H12 C12 3.5625 no 2_756
H12 H12 3.2623 no 2_756
H13 S2 3.4516 no .
H13 N1 2.8724 no 1_455
H13 N2 2.9563 no 2_657
H13 C3 3.4078 no .
H13 C7 3.5592 no 1_545
H13 H7 3.4371 no 1_545
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 0.08(16) no . . .
C1 S1 C4 C5 179.3(2) no . . .
C4 S1 C1 C2 0.01(18) no . . .
C3 S2 C6 C5 0.27(14) no . . .
C3 S2 C6 C7 -179.40(17) no . . .
C6 S2 C3 C2 179.3(2) no . . .
C6 S2 C3 C4 -0.23(15) no . . .
S1 C1 C2 C3 -0.1(3) no . . .
C1 C2 C3 S2 -179.4(2) no . . .
C1 C2 C3 C4 0.2(3) no . . .
S2 C3 C4 S1 179.51(11) no . . .
S2 C3 C4 C5 0.1(3) no . . .
C2 C3 C4 S1 -0.1(3) no . . .
C2 C3 C4 C5 -179.52(17) no . . .
S1 C4 C5 C6 -179.12(16) no . . .
S1 C4 C5 C7 1.5(4) no . . 2_666
C3 C4 C5 C6 0.1(3) no . . .
C3 C4 C5 C7 -179.28(18) no . . 2_666
C4 C5 C6 S2 -0.2(3) no . . .
C4 C5 C6 C7 179.45(17) no . . .
C4 C5 C7 C6 -179.63(19) no . 2_666 2_666
C6 C5 C7 C6 1.1(3) no . 2_666 2_666
C7 C5 C6 S2 179.18(16) no 2_666 . .
C7 C5 C6 C7 -1.1(3) no 2_666 . .
S2 C6 C7 C5 -179.25(13) no . . 2_666
C5 C6 C7 C5 1.1(3) no . . 2_666
C9 C8 C10 C9 0.0(3) no . . 2_656
C10 C8 C9 C10 -0.0(3) no . . 2_656
C9 C8 C11 C12 -0.2(4) no . . .
C9 C8 C11 C13 178.74(18) no . . .
C11 C8 C9 C10 179.97(19) no . . 2_656
C10 C8 C11 C12 179.81(18) no . . .
C10 C8 C11 C13 -1.3(4) no . . .
C11 C8 C10 C9 -179.97(19) no . . 2_656
C8 C9 C10 C8 0.0(4) no . 2_656 2_656
