#------------------------------------------------------------------------------
#$Date: 2019-11-10 01:43:04 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225580 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/54/4515426.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_4515426
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, C10 H8 N4'
_chemical_formula_sum            'C24 H14 N4 S4'
_chemical_formula_weight         486.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.145(12)
_cell_angle_beta                 96.07(2)
_cell_angle_gamma                94.06(3)
_cell_formula_units_Z            1
_cell_length_a                   7.730(3)
_cell_length_b                   7.8084(13)
_cell_length_c                   9.4033(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      16.73
_cell_measurement_theta_min      12.58
_cell_volume                     533.1(2)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        WinAFC
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/1 (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 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  0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2632
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.666
_diffrn_standards_decay_%        0.439
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             250.00
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.21
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1944
_refine_ls_R_factor_gt           0.0832
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1448P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1009
_reflns_number_total             2101
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            am8b00416_si_006.cif
_cod_data_source_block           Cytidine_(Rigaku_Master_for_Mo)
_cod_original_cell_volume        533.1(3)
_cod_database_code               4515426
loop_
_space_group_symop_id
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.7015(3) 0.0092(3) 0.2589(2) 0.0533(7) Uani 1 1 d . .
S2 S 0.5720(2) 0.4826(3) 0.17600(19) 0.0456(6) Uani 1 1 d . .
N1 N 0.1392(7) 0.2335(7) 0.2985(6) 0.0365(13) Uani 1 1 d . .
N2 N 0.2287(9) -0.0428(9) 0.3467(8) 0.0576(18) Uani 1 1 d . .
C1 C 0.7449(11) -0.0044(12) 0.0809(10) 0.062(2) Uani 1 1 d . .
H1 H 0.790096 -0.103455 0.018309 0.074 Uiso 1 1 calc R U
C2 C 0.7082(10) 0.1401(14) 0.0397(9) 0.063(2) Uani 1 1 d . .
H2 H 0.723573 0.152116 -0.053606 0.075 Uiso 1 1 calc R U
C3 C 0.6428(9) 0.2725(10) 0.1569(7) 0.0448(18) Uani 1 1 d . .
C4 C 0.6323(8) 0.2201(9) 0.2840(7) 0.0369(16) Uani 1 1 d . .
C5 C 0.5674(8) 0.3526(8) 0.4034(7) 0.0292(14) Uani 1 1 d . .
C6 C 0.5278(8) 0.5059(9) 0.3605(7) 0.0325(15) Uani 1 1 d . .
C7 C 0.4623(8) 0.6532(9) 0.4532(7) 0.0339(15) Uani 1 1 d . .
H7 H 0.438799 0.752376 0.422378 0.041 Uiso 1 1 calc R U
C8 C 0.0710(8) 0.3594(8) 0.3984(7) 0.0315(14) Uani 1 1 d . .
C9 C 0.0260(8) 0.5175(8) 0.3547(7) 0.0308(14) Uani 1 1 d . .
C10 C 0.0411(8) 0.3516(8) 0.5449(7) 0.0310(14) Uani 1 1 d . .
H11 H 0.069804 0.250521 0.570767 0.037 Uiso 1 1 calc R U
C11 C 0.1846(9) 0.0871(9) 0.3321(7) 0.0391(16) Uani 1 1 d . .
C12 C 0.0554(9) 0.5221(9) 0.1993(7) 0.0388(16) Uani 1 1 d . .
H12A H 0.031240 0.637480 0.190252 0.047 Uiso 1 1 calc R U
H12B H -0.021213 0.427477 0.123967 0.047 Uiso 1 1 calc R U
H12C H 0.174773 0.504322 0.185057 0.047 Uiso 1 1 calc R U
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)
;
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C4 90.6(4) . .
C3 S2 C6 91.0(3) . .
C8 N1 C11 119.2(6) . .
C2 C1 S1 114.2(6) . .
C2 C1 H1 122.9 . .
S1 C1 H1 122.9 . .
C1 C2 C3 111.4(8) . .
C1 C2 H2 124.3 . .
C3 C2 H2 124.3 . .
C4 C3 C2 112.5(8) . .
C4 C3 S2 113.0(5) . .
C2 C3 S2 134.5(7) . .
C3 C4 C5 113.2(6) . .
C3 C4 S1 111.3(5) . .
C5 C4 S1 135.5(5) . .
C7 C5 C6 119.6(6) 2_666 .
C7 C5 C4 129.4(6) 2_666 .
C6 C5 C4 111.0(5) . .
C7 C6 C5 123.4(6) . .
C7 C6 S2 124.8(5) . .
C5 C6 S2 111.8(5) . .
C6 C7 C5 117.1(6) . 2_666
C6 C7 H7 121.5 . .
C5 C7 H7 121.5 2_666 .
N1 C8 C10 124.3(6) . .
N1 C8 C9 116.3(6) . .
C10 C8 C9 119.4(5) . .
C10 C9 C8 117.4(6) 2_566 .
C10 C9 C12 123.8(6) 2_566 .
C8 C9 C12 118.7(5) . .
C9 C10 C8 123.2(6) 2_566 .
C9 C10 H11 118.4 2_566 .
C8 C10 H11 118.4 . .
N2 C11 N1 173.1(7) . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.714(9) .
S1 C4 1.721(7) .
S2 C3 1.728(8) .
S2 C6 1.760(6) .
N1 C8 1.315(8) .
N1 C11 1.337(9) .
N2 C11 1.137(9) .
C1 C2 1.341(12) .
C1 H1 0.9300 .
C2 C3 1.422(10) .
C2 H2 0.9300 .
C3 C4 1.387(10) .
C4 C5 1.433(8) .
C5 C7 1.405(9) 2_666
C5 C6 1.420(9) .
C6 C7 1.375(9) .
C7 H7 0.9300 .
C8 C10 1.439(9) .
C8 C9 1.470(9) .
C9 C10 1.335(9) 2_566
C9 C12 1.513(8) .
C10 H11 0.9300 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_4
C4 S1 C1 C2 -0.7(7) . .
S1 C1 C2 C3 0.7(10) . .
C1 C2 C3 C4 -0.2(10) . .
C1 C2 C3 S2 -179.6(6) . .
C6 S2 C3 C4 0.5(5) . .
C6 S2 C3 C2 179.9(8) . .
C2 C3 C4 C5 179.7(6) . .
S2 C3 C4 C5 -0.7(7) . .
C2 C3 C4 S1 -0.3(8) . .
S2 C3 C4 S1 179.2(4) . .
C1 S1 C4 C3 0.6(5) . .
C1 S1 C4 C5 -179.5(7) . .
C3 C4 C5 C7 179.4(6) . 2_666
S1 C4 C5 C7 -0.6(12) . 2_666
C3 C4 C5 C6 0.6(8) . .
S1 C4 C5 C6 -179.4(5) . .
C7 C5 C6 C7 0.7(11) 2_666 .
C4 C5 C6 C7 179.6(6) . .
C7 C5 C6 S2 -179.1(5) 2_666 .
C4 C5 C6 S2 -0.2(7) . .
C3 S2 C6 C7 180.0(6) . .
C3 S2 C6 C5 -0.2(5) . .
C5 C6 C7 C5 -0.7(11) . 2_666
S2 C6 C7 C5 179.1(5) . 2_666
C11 N1 C8 C10 0.1(10) . .
C11 N1 C8 C9 179.3(6) . .
N1 C8 C9 C10 -179.0(6) . 2_566
C10 C8 C9 C10 0.2(10) . 2_566
N1 C8 C9 C12 1.8(9) . .
C10 C8 C9 C12 -179.0(5) . .
N1 C8 C10 C9 179.0(6) . 2_566
C9 C8 C10 C9 -0.2(11) . 2_566
