#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:10:46 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/75/7237540.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_7237540
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 F4 N4'
_chemical_formula_sum            'C28 H10 F4 N4 S4'
_chemical_formula_weight         606.65
_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                90.88(5)
_cell_angle_beta                 129.50(4)
_cell_angle_gamma                104.63(4)
_cell_formula_units_Z            1
_cell_length_a                   9.092(5)
_cell_length_b                   9.151(4)
_cell_length_c                   10.403(6)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    297
_cell_measurement_theta_max      15.10
_cell_measurement_theta_min      12.68
_cell_volume                     628.0(8)
_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 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  0.0931
_diffrn_reflns_av_unetI/netI     0.1410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2801
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.611
_diffrn_standards_decay_%        -2.678
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             306.00
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.022
_refine_diff_density_max         1.57
_refine_diff_density_min         -0.92
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1817
_refine_ls_R_factor_gt           0.0920
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1664P)²+1.4094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2479
_refine_ls_wR_factor_ref         0.3086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1164
_reflns_number_total             2210
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8tc05190a2.cif
_cod_data_source_block           (4T)(F4TCNQ)
_cod_original_cell_volume        628.0(7)
_cod_database_code               7237540
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
F1 F 0.1336(7) 0.4909(6) -0.1176(6) 0.0435(12) Uani 1 1 d . .
F2 F 0.7051(7) 0.3274(6) 0.2170(6) 0.0471(13) Uani 1 1 d . .
N1 N -0.0202(12) 0.2661(10) 0.0216(11) 0.060(2) Uani 1 1 d . .
N2 N 0.4789(14) 0.1243(11) 0.3115(12) 0.067(3) Uani 1 1 d . .
C1 C 0.1286(13) 0.2854(9) 0.0537(11) 0.040(2) Uani 1 1 d . .
C2 C 0.4178(14) 0.2045(10) 0.2242(11) 0.043(2) Uani 1 1 d . .
C3 C 0.3237(12) 0.3033(9) 0.1096(10) 0.0338(18) Uani 1 1 d . .
C4 C 0.4106(11) 0.3986(9) 0.0565(9) 0.0327(18) Uani 1 1 d . .
C5 C 0.3137(11) 0.4952(9) -0.0586(10) 0.0320(18) Uani 1 1 d . .
C6 C 0.6015(12) 0.4106(9) 0.1107(9) 0.0325(18) Uani 1 1 d . .
S2 S 0.2580(3) 0.3932(3) 0.5030(3) 0.0413(7) Uani 1 1 d D .
C11 C 0.3367(12) 0.2728(9) 0.6441(10) 0.039(2) Uani 1 1 d D .
C12 C 0.5233(13) 0.2720(10) 0.7106(11) 0.047(2) Uani 1 1 d D .
H12 H 0.589383 0.211247 0.785640 0.056 Uiso 1 1 calc R U
C13 C 0.6033(14) 0.3706(10) 0.6548(11) 0.046(2) Uani 1 1 d D .
H13 H 0.730213 0.384094 0.690668 0.055 Uiso 1 1 calc R U
C14 C 0.4807(12) 0.4462(9) 0.5430(10) 0.0351(19) Uani 1 1 d D .
S1 S 0.2844(5) 0.0573(3) 0.8034(4) 0.0691(10) Uani 1 1 d D .
C10 C 0.2024(12) 0.1849(8) 0.6715(9) 0.037(2) Uani 1 1 d D .
C9 C 0.0078(11) 0.1898(9) 0.6080(10) 0.0397(14) Uani 1 1 d D .
H9 H -0.062367 0.251229 0.536779 0.048 Uiso 1 1 calc R U
C8 C -0.0540(12) 0.0834(9) 0.6751(10) 0.0397(14) Uani 1 1 d D .
H8 H -0.176134 0.065900 0.649688 0.048 Uiso 1 1 calc R U
C7 C 0.0722(15) 0.0104(11) 0.7761(12) 0.062(3) Uani 1 1 d D .
H7 H 0.046740 -0.060943 0.827956 0.074 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)
;
F F 0.0171 0.0103
;
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
N1 C1 C3 174.0(9) . .
N2 C2 C3 175.2(9) . .
C4 C3 C1 124.6(7) . .
C4 C3 C2 123.3(7) . .
C1 C3 C2 112.0(6) . .
C3 C4 C6 123.2(7) . .
C3 C4 C5 122.5(7) . .
C6 C4 C5 114.3(6) . .
F1 C5 C6 118.5(7) . 2_665
F1 C5 C4 118.7(6) . .
C6 C5 C4 122.8(7) 2_665 .
F2 C6 C5 117.4(7) . 2_665
F2 C6 C4 119.7(6) . .
C5 C6 C4 122.9(7) 2_665 .
C14 S2 C11 91.6(4) . .
C12 C11 C10 129.7(7) . .
C12 C11 S2 110.4(6) . .
C10 C11 S2 119.9(6) . .
C11 C12 C13 113.0(8) . .
C11 C12 H12 123.5 . .
C13 C12 H12 123.5 . .
C14 C13 C12 114.1(8) . .
C14 C13 H13 122.9 . .
C12 C13 H13 122.9 . .
C13 C14 C14 127.1(9) . 2_666
C13 C14 S2 110.8(6) . .
C14 C14 S2 122.0(8) 2_666 .
C7 S1 C10 90.1(4) . .
C9 C10 C11 130.3(7) . .
C9 C10 S1 112.5(5) . .
C11 C10 S1 117.2(6) . .
C8 C9 C10 106.9(7) . .
C8 C9 H9 126.5 . .
C10 C9 H9 126.5 . .
C7 C8 C9 115.9(7) . .
C7 C8 H8 122.0 . .
C9 C8 H8 122.0 . .
C8 C7 S1 114.5(6) . .
C8 C7 H7 122.8 . .
S1 C7 H7 122.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C5 1.322(9) .
F2 C6 1.323(8) .
N1 C1 1.129(10) .
N2 C2 1.121(11) .
C1 C3 1.431(11) .
C2 C3 1.448(12) .
C3 C4 1.383(10) .
C4 C6 1.414(10) .
C4 C5 1.441(10) .
C5 C6 1.357(10) 2_665
S2 C14 1.713(8) .
S2 C11 1.729(7) .
C11 C12 1.368(11) .
C11 C10 1.474(11) .
C12 C13 1.379(11) .
C12 H12 0.9300 .
C13 C14 1.356(11) .
C13 H13 0.9300 .
C14 C14 1.465(14) 2_666
S1 C7 1.693(9) .
S1 C10 1.729(7) .
C10 C9 1.457(11) .
C9 C8 1.412(10) .
C9 H9 0.9300 .
C8 C7 1.320(12) .
C8 H8 0.9300 .
C7 H7 0.9300 .
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
C1 C3 C4 C6 -178.2(8) .
C2 C3 C4 C6 -0.8(12) .
C1 C3 C4 C5 2.1(12) .
C2 C3 C4 C5 179.6(8) .
C3 C4 C5 F1 -1.0(11) .
C6 C4 C5 F1 179.4(6) .
C3 C4 C5 C6 179.7(8) 2_665
C6 C4 C5 C6 0.1(12) 2_665
C3 C4 C6 F2 0.2(12) .
C5 C4 C6 F2 179.8(7) .
C3 C4 C6 C5 -179.7(8) 2_665
C5 C4 C6 C5 -0.1(12) 2_665
C14 S2 C11 C12 -2.5(7) .
C14 S2 C11 C10 179.8(6) .
C10 C11 C12 C13 180.0(8) .
S2 C11 C12 C13 2.6(10) .
C11 C12 C13 C14 -1.3(11) .
C12 C13 C14 C14 -177.7(10) 2_666
C12 C13 C14 S2 -0.6(10) .
C11 S2 C14 C13 1.8(7) .
C11 S2 C14 C14 179.0(9) 2_666
C12 C11 C10 C9 176.8(9) .
S2 C11 C10 C9 -6.0(11) .
C12 C11 C10 S1 -1.4(11) .
S2 C11 C10 S1 175.8(5) .
C7 S1 C10 C9 0.4(6) .
C7 S1 C10 C11 178.9(6) .
C11 C10 C9 C8 -179.1(7) .
S1 C10 C9 C8 -0.8(8) .
C10 C9 C8 C7 1.0(10) .
C9 C8 C7 S1 -0.8(10) .
C10 S1 C7 C8 0.2(8) .
