#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:10:46 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/75/7237539.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_7237539
loop_
_publ_author_name
'Sato, Ryonosuke'
'Kawamoto, Tadashi'
'Mori, Takehiko'
_publ_section_title
;
 Asymmetrical hole/electron transport in donor--acceptor mixed-stack
 cocrystals
;
_journal_issue                   3
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              567
_journal_paper_doi               10.1039/C8TC05190A
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C16 H10 S4, C12 H4 N4'
_chemical_formula_sum            'C28 H14 N4 S4'
_chemical_formula_weight         534.69
_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
_audit_update_record
;
2018-08-15 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                109.60(4)
_cell_angle_beta                 109.29(5)
_cell_angle_gamma                98.00(4)
_cell_formula_units_Z            1
_cell_length_a                   7.861(4)
_cell_length_b                   8.890(3)
_cell_length_c                   10.291(8)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    297
_cell_measurement_theta_max      12.49
_cell_measurement_theta_min      11.04
_cell_volume                     613.7(7)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        WinAFC
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297
_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  0.0684
_diffrn_reflns_av_unetI/netI     0.1356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4191
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.534
_diffrn_standards_decay_%        0.855
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             274.00
_exptl_crystal_size_max          0.794
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0821P)²+0.0943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1650
_reflns_number_total             3571
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8tc05190a2.cif
_cod_data_source_block           (4T)(TCNQ)
_cod_database_code               7237539
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 -0.03021(16) 0.22433(16) 0.71140(13) 0.0585(4) Uani 1 1 d . .
S2 S 0.42066(14) 0.29611(13) 0.56093(11) 0.0425(3) Uani 1 1 d . .
N1 N 0.4078(5) 0.0445(5) 0.1334(4) 0.0579(10) Uani 1 1 d . .
N2 N 0.0285(5) 0.3451(5) 0.1563(4) 0.0573(10) Uani 1 1 d . .
C1 C 0.3689(5) 0.1568(5) 0.1156(4) 0.0385(8) Uani 1 1 d . .
C2 C 0.1556(5) 0.3255(5) 0.1296(4) 0.0385(8) Uani 1 1 d . .
C3 C 0.3139(4) 0.2978(4) 0.0967(4) 0.0304(7) Uani 1 1 d . .
C4 C 0.4067(5) 0.3976(4) 0.0484(3) 0.0273(7) Uani 1 1 d . .
C5 C 0.5638(5) 0.3639(4) 0.0141(4) 0.0296(7) Uani 1 1 d . .
H5 H 0.604542 0.273537 0.024316 0.036 Uiso 1 1 calc R U
C6 C 0.3473(5) 0.5382(4) 0.0326(4) 0.0300(7) Uani 1 1 d . .
H6 H 0.246069 0.561964 0.054833 0.036 Uiso 1 1 calc R U
C7 C -0.0301(7) 0.0543(6) 0.7526(5) 0.0667(15) Uani 1 1 d . .
H7 H -0.117264 0.012282 0.783632 0.080 Uiso 1 1 calc R U
C8 C 0.1053(7) -0.0122(6) 0.7363(5) 0.0605(13) Uani 1 1 d . .
H8 H 0.123973 -0.105326 0.754887 0.073 Uiso 1 1 calc R U
C9 C 0.2181(5) 0.0726(5) 0.6878(4) 0.0414(9) Uani 1 1 d . .
H9 H 0.318912 0.041323 0.669642 0.050 Uiso 1 1 calc R U
C10 C 0.1637(5) 0.2066(5) 0.6700(4) 0.0365(9) Uani 1 1 d . .
C11 C 0.2431(5) 0.3262(5) 0.6219(4) 0.0404(9) Uani 1 1 d . .
C12 C 0.1986(5) 0.4675(5) 0.6165(4) 0.0434(9) Uani 1 1 d . .
H12 H 0.106630 0.505007 0.645421 0.052 Uiso 1 1 calc R U
C13 C 0.3060(5) 0.5504(5) 0.5629(4) 0.0415(9) Uani 1 1 d . .
H13 H 0.291169 0.647956 0.551767 0.050 Uiso 1 1 calc R U
C14 C 0.4335(5) 0.4748(5) 0.5287(4) 0.0339(8) Uani 1 1 d . .
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
C7 S1 C10 90.5(2) . .
C14 S2 C11 91.87(19) . .
N1 C1 C3 177.3(4) . .
N2 C2 C3 178.8(4) . .
C4 C3 C2 123.0(3) . .
C4 C3 C1 122.3(3) . .
C2 C3 C1 114.8(3) . .
C3 C4 C6 120.2(3) . .
C3 C4 C5 121.2(3) . .
C6 C4 C5 118.6(3) . .
C6 C5 C4 120.6(3) 2_665 .
C6 C5 H5 119.7 2_665 .
C4 C5 H5 119.7 . .
C5 C6 C4 120.7(3) 2_665 .
C5 C6 H6 119.6 2_665 .
C4 C6 H6 119.6 . .
C8 C7 S1 113.6(3) . .
C8 C7 H7 123.2 . .
S1 C7 H7 123.2 . .
C7 C8 C9 112.6(4) . .
C7 C8 H8 123.7 . .
C9 C8 H8 123.7 . .
C10 C9 C8 112.6(4) . .
C10 C9 H9 123.7 . .
C8 C9 H9 123.7 . .
C9 C10 C11 129.8(3) . .
C9 C10 S1 110.6(3) . .
C11 C10 S1 119.5(3) . .
C12 C11 C10 129.6(3) . .
C12 C11 S2 110.8(3) . .
C10 C11 S2 119.7(3) . .
C11 C12 C13 113.0(4) . .
C11 C12 H12 123.5 . .
C13 C12 H12 123.5 . .
C14 C13 C12 113.7(4) . .
C14 C13 H13 123.2 . .
C12 C13 H13 123.2 . .
C13 C14 C14 128.6(4) . 2_666
C13 C14 S2 110.7(3) . .
C14 C14 S2 120.7(4) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.701(5) .
S1 C10 1.727(4) .
S2 C14 1.725(4) .
S2 C11 1.727(4) .
N1 C1 1.137(5) .
N2 C2 1.141(5) .
C1 C3 1.433(5) .
C2 C3 1.425(5) .
C3 C4 1.387(4) .
C4 C6 1.434(5) .
C4 C5 1.435(4) .
C5 C6 1.345(4) 2_665
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.319(7) .
C7 H7 0.9300 .
C8 C9 1.401(5) .
C8 H8 0.9300 .
C9 C10 1.367(5) .
C9 H9 0.9300 .
C10 C11 1.462(5) .
C11 C12 1.363(6) .
C12 C13 1.403(5) .
C12 H12 0.9300 .
C13 C14 1.357(5) .
C13 H13 0.9300 .
C14 C14 1.448(6) 2_666
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_4
C2 C3 C4 C6 1.4(5) .
C1 C3 C4 C6 -179.4(3) .
C2 C3 C4 C5 -179.0(3) .
C1 C3 C4 C5 0.2(5) .
C3 C4 C5 C6 -180.0(3) 2_665
C6 C4 C5 C6 -0.3(5) 2_665
C3 C4 C6 C5 180.0(3) 2_665
C5 C4 C6 C5 0.3(5) 2_665
C10 S1 C7 C8 -0.2(4) .
S1 C7 C8 C9 -0.3(5) .
C7 C8 C9 C10 0.7(5) .
C8 C9 C10 C11 180.0(4) .
C8 C9 C10 S1 -0.9(4) .
C7 S1 C10 C9 0.6(3) .
C7 S1 C10 C11 179.9(3) .
C9 C10 C11 C12 -173.8(4) .
S1 C10 C11 C12 7.1(5) .
C9 C10 C11 S2 6.1(5) .
S1 C10 C11 S2 -173.02(19) .
C14 S2 C11 C12 0.0(3) .
C14 S2 C11 C10 -179.9(3) .
C10 C11 C12 C13 -179.8(3) .
S2 C11 C12 C13 0.3(4) .
C11 C12 C13 C14 -0.7(5) .
C12 C13 C14 C14 -180.0(4) 2_666
C12 C13 C14 S2 0.7(4) .
C11 S2 C14 C13 -0.4(3) .
C11 S2 C14 C14 -179.8(4) 2_666
