#------------------------------------------------------------------------------
#$Date: 2019-11-24 11:10:46 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/75/7237541.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_7237541
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 H2 F2 N4'
_chemical_formula_sum            'C28 H12 F2 N4 S4'
_chemical_formula_weight         570.67
_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                109.866(3)
_cell_angle_beta                 109.641(3)
_cell_angle_gamma                97.879(4)
_cell_formula_units_Z            1
_cell_length_a                   7.9104(5)
_cell_length_b                   8.8995(6)
_cell_length_c                   10.3989(7)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    270
_cell_measurement_theta_max      67.92
_cell_measurement_theta_min      4.96
_cell_volume                     621.80(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_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      270
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6806
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        63.513
_diffrn_reflns_theta_max         63.513
_diffrn_reflns_theta_min         4.960
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.873
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             290.00
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.026
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.1030
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1979P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2908
_refine_ls_wR_factor_ref         0.3315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1162
_reflns_number_total             2011
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8tc05190a2.cif
_cod_data_source_block           (4T)(F2TCNQ)
_cod_original_cell_volume        621.80(7)
_cod_database_code               7237541
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 0.2231(5) 0.5895(4) 0.0804(4) 0.0605(11) Uani 1 1 d . .
N1 N 0.4045(9) 0.0413(7) 0.1268(7) 0.0759(19) Uani 1 1 d . .
N2 N 0.0389(7) 0.3385(7) 0.1777(6) 0.0660(16) Uani 1 1 d . .
C1 C 0.3679(9) 0.1563(8) 0.1123(7) 0.0550(17) Uani 1 1 d . .
C2 C 0.1634(9) 0.3285(7) 0.1437(7) 0.0507(15) Uani 1 1 d . .
C3 C 0.3146(8) 0.3003(7) 0.0996(7) 0.0463(14) Uani 1 1 d . .
C4 C 0.4056(8) 0.3983(6) 0.0513(6) 0.0424(14) Uani 1 1 d . .
C5 C 0.5536(8) 0.3579(7) 0.0101(6) 0.0476(15) Uani 1 1 d . .
H5 H 0.590070 0.264536 0.015938 0.057 Uiso 1 1 calc R U
C6 C 0.3587(8) 0.5448(7) 0.0376(6) 0.0461(15) Uani 1 1 d . .
S2 S 0.4179(2) 0.2959(2) 0.55855(19) 0.0602(7) Uani 1 1 d D .
C11 C 0.2460(8) 0.3316(8) 0.6226(7) 0.0560(17) Uani 1 1 d D .
C12 C 0.2043(9) 0.4727(8) 0.6176(7) 0.0584(17) Uani 1 1 d D .
H12 H 0.113206 0.511308 0.645812 0.070 Uiso 1 1 calc R U
C13 C 0.3117(9) 0.5542(9) 0.5658(7) 0.0609(18) Uani 1 1 d D .
H13 H 0.301088 0.653429 0.557207 0.073 Uiso 1 1 calc R U
C14 C 0.4324(8) 0.4739(7) 0.5297(6) 0.0518(16) Uani 1 1 d D .
S1 S -0.0206(3) 0.2365(3) 0.7162(2) 0.0815(9) Uani 1 1 d D .
C10 C 0.1615(8) 0.2103(7) 0.6680(6) 0.0550(17) Uani 1 1 d D .
C9 C 0.2127(7) 0.0665(6) 0.6833(5) 0.0401(13) Uani 1 1 d D .
H9 H 0.307567 0.027773 0.661653 0.048 Uiso 1 1 calc R U
C8 C 0.0998(11) -0.0049(9) 0.7348(8) 0.080(2) Uani 1 1 d D .
H8 H 0.112449 -0.098486 0.753966 0.096 Uiso 1 1 calc R U
C7 C -0.0277(11) 0.0696(9) 0.7549(8) 0.081(2) Uani 1 1 d D .
H7 H -0.114052 0.032364 0.787736 0.097 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 0.0181 0.0091
;
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 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
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 176.2(7) . .
N2 C2 C3 174.7(6) . .
C4 C3 C1 121.1(5) . .
C4 C3 C2 125.7(5) . .
C1 C3 C2 113.1(5) . .
C3 C4 C5 120.8(5) . .
C3 C4 C6 123.4(5) . .
C5 C4 C6 115.8(5) . .
C6 C5 C4 120.1(5) 2_665 .
C6 C5 H5 120.0 2_665 .
C4 C5 H5 120.0 . .
F1 C6 C5 118.6(5) . 2_665
F1 C6 C4 117.3(5) . .
C5 C6 C4 124.1(5) 2_665 .
C14 S2 C11 91.0(3) . .
C12 C11 C10 129.4(6) . .
C12 C11 S2 110.9(5) . .
C10 C11 S2 119.7(5) . .
C11 C12 C13 113.2(6) . .
C11 C12 H12 123.4 . .
C13 C12 H12 123.4 . .
C14 C13 C12 112.8(6) . .
C14 C13 H13 123.6 . .
C12 C13 H13 123.6 . .
C13 C14 C14 126.8(7) . 2_666
C13 C14 S2 112.1(4) . .
C14 C14 S2 121.1(6) 2_666 .
C7 S1 C10 91.4(4) . .
C9 C10 C11 129.8(6) . .
C9 C10 S1 110.5(4) . .
C11 C10 S1 119.7(5) . .
C8 C9 C10 109.5(5) . .
C8 C9 H9 125.3 . .
C10 C9 H9 125.3 . .
C7 C8 C9 114.6(7) . .
C7 C8 H8 122.7 . .
C9 C8 H8 122.7 . .
C8 C7 S1 114.0(6) . .
C8 C7 H7 123.0 . .
S1 C7 H7 123.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C6 1.350(6) .
N1 C1 1.145(8) .
N2 C2 1.157(7) .
C1 C3 1.436(8) .
C2 C3 1.442(8) .
C3 C4 1.379(7) .
C4 C5 1.426(7) .
C4 C6 1.442(7) .
C5 C6 1.355(8) 2_665
C5 H5 0.9300 .
S2 C14 1.705(6) .
S2 C11 1.726(6) .
C11 C12 1.355(9) .
C11 C10 1.482(9) .
C12 C13 1.393(8) .
C12 H12 0.9300 .
C13 C14 1.345(8) .
C13 H13 0.9300 .
C14 C14 1.497(11) 2_666
S1 C7 1.663(8) .
S1 C10 1.697(6) .
C10 C9 1.436(7) .
C9 C8 1.373(8) .
C9 H9 0.9300 .
C8 C7 1.316(10) .
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 C5 1.0(9) .
C2 C3 C4 C5 -179.9(5) .
C1 C3 C4 C6 -179.5(5) .
C2 C3 C4 C6 -0.4(10) .
C3 C4 C5 C6 179.8(5) 2_665
C6 C4 C5 C6 0.3(9) 2_665
C3 C4 C6 F1 2.6(9) .
C5 C4 C6 F1 -177.9(5) .
C3 C4 C6 C5 -179.8(6) 2_665
C5 C4 C6 C5 -0.3(10) 2_665
C14 S2 C11 C12 1.0(5) .
C14 S2 C11 C10 178.8(5) .
C10 C11 C12 C13 -178.8(6) .
S2 C11 C12 C13 -1.3(7) .
C11 C12 C13 C14 0.9(8) .
C12 C13 C14 C14 179.8(8) 2_666
C12 C13 C14 S2 -0.1(7) .
C11 S2 C14 C13 -0.5(5) .
C11 S2 C14 C14 179.6(7) 2_666
C12 C11 C10 C9 -175.4(6) .
S2 C11 C10 C9 7.3(9) .
C12 C11 C10 S1 2.7(9) .
S2 C11 C10 S1 -174.6(3) .
C7 S1 C10 C9 0.3(4) .
C7 S1 C10 C11 -178.1(5) .
C11 C10 C9 C8 177.3(6) .
S1 C10 C9 C8 -0.9(6) .
C10 C9 C8 C7 1.3(9) .
C9 C8 C7 S1 -1.1(9) .
C10 S1 C7 C8 0.4(6) .
