# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(3T)(TCNQ)
_database_code_depnum_ccdc_archive 'CCDC 1862143'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H12 N4 S3'
_chemical_formula_moiety         'C12 H4 N4, C12 H8 S3'
_chemical_formula_weight         452.57
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
_space_group_IT_number           5
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.970(5)
_cell_length_b                   12.704(4)
_cell_length_c                   7.754(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.29(3)
_cell_angle_gamma                90.0000
_cell_volume                     1059.7(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30
_cell_measurement_theta_min      12.55
_cell_measurement_theta_max      16.28
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.810
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464.00
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.967

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            1697
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_theta_max         28.496
_diffrn_reflns_theta_min         2.679
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.522
_diffrn_reflns_point_group_measured_fraction_full 0.524
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -1.718
_reflns_number_total             1407
_reflns_number_gt                747
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.0972
_refine_ls_number_restraints     89
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1407
_refine_ls_number_parameters     173
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.1(3)

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.1836(4) 0.5811(3) 0.6521(7) 0.0620(12) Uani 0.5 1 d D . P A 1
S2A S 0.500000 0.4224(4) 0.500000 0.0424(12) Uani 0.5 2 d DS T P A 1
C8A C 0.282(4) 0.486(2) 0.602(11) 0.052(4) Uani 0.5 1 d D . P A 1
C9A C 0.2500(16) 0.3812(9) 0.638(2) 0.0620(16) Uani 0.5 1 d D . P A 1
H9A H 0.293300 0.319946 0.623530 0.074 Uiso 0.5 1 calc R U P A 1
C10A C 0.1320(15) 0.3904(11) 0.705(2) 0.075(2) Uani 0.5 1 d D . P A 1
H10A H 0.086063 0.332505 0.728195 0.090 Uiso 0.5 1 calc R U P A 1
C11A C 0.0962(13) 0.496(2) 0.729(3) 0.063(3) Uani 0.5 1 d D . P A 1
H11A H 0.030339 0.514907 0.781903 0.075 Uiso 0.5 1 calc R U P A 1
C12A C 0.3969(15) 0.5163(9) 0.550(4) 0.0493(15) Uani 0.5 1 d D . P A 1
C13A C 0.4376(15) 0.6161(9) 0.531(2) 0.0562(12) Uani 0.5 1 d D . P A 1
H13A H 0.395334 0.676568 0.553300 0.067 Uiso 0.5 1 calc R U P A 1
S1B S 0.1858(6) 0.4011(4) 0.6501(8) 0.0772(16) Uani 0.5 1 d D . P B 2
S2B S 0.500000 0.5633(6) 0.500000 0.0625(18) Uani 0.5 2 d DS T P B 2
C8B C 0.289(4) 0.495(3) 0.615(11) 0.052(4) Uani 0.5 1 d D . P B 2
C9B C 0.2438(15) 0.5988(10) 0.635(2) 0.0620(16) Uani 0.5 1 d D . P B 2
H9B H 0.281521 0.661929 0.614687 0.074 Uiso 0.5 1 calc R U P B 2
C10B C 0.1243(16) 0.5851(11) 0.695(2) 0.075(2) Uani 0.5 1 d D . P B 2
H10B H 0.082118 0.641235 0.733741 0.090 Uiso 0.5 1 calc R U P B 2
C11B C 0.0791(13) 0.4800(18) 0.690(3) 0.063(3) Uani 0.5 1 d D . P B 2
H11B H 0.000734 0.459924 0.706558 0.075 Uiso 0.5 1 calc R U P B 2
C12B C 0.4008(15) 0.4681(9) 0.550(4) 0.0493(15) Uani 0.5 1 d D . P B 2
C13B C 0.4485(14) 0.3688(10) 0.527(2) 0.0562(12) Uani 0.5 1 d D . P B 2
H13B H 0.408522 0.307092 0.548531 0.067 Uiso 0.5 1 calc R U P B 2
N1 N 0.1559(8) 0.3232(7) 0.1704(12) 0.078(2) Uani 1 1 d . . . . .
N2 N 0.1598(8) 0.6611(7) 0.1653(13) 0.086(3) Uani 1 1 d . . . . .
C1 C 0.2110(8) 0.3961(8) 0.1443(13) 0.060(2) Uani 1 1 d . . . . .
C2 C 0.2105(8) 0.5859(8) 0.1407(12) 0.058(2) Uani 1 1 d . . . . .
C3 C 0.2728(3) 0.4927(9) 0.1111(3) 0.0488(7) Uani 1 1 d . . . . .
C4 C 0.3856(3) 0.4878(8) 0.0557(3) 0.0453(8) Uani 1 1 d . . . . .
C5 C 0.4457(6) 0.3946(5) 0.0242(10) 0.050(2) Uani 1 1 d . . . . .
H5 H 0.407621 0.330519 0.037854 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4448(6) 0.5890(6) 0.0281(8) 0.0478(18) Uani 1 1 d . . . . .
H6 H 0.407250 0.652161 0.048812 0.057 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C11A 1.630(18) . ?
S1A C8A 1.71(2) . ?
S2A C12A 1.739(9) 2_656 ?
S2A C12A 1.739(9) . ?
C8A C9A 1.42(3) . ?
C8A C12A 1.446(13) . ?
C9A C10A 1.488(11) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.42(3) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
C12A C13A 1.361(11) . ?
C13A C13A 1.54(3) 2_656 ?
C13A H13A 0.9300 . ?
S1B C11B 1.616(17) . ?
S1B C8B 1.70(2) . ?
S2B C12B 1.722(10) 2_656 ?
S2B C12B 1.722(10) . ?
C8B C9B 1.43(3) . ?
C8B C12B 1.451(13) . ?
C9B C10B 1.486(12) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.42(2) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
C12B C13B 1.392(11) . ?
C13B C13B 1.28(3) 2_656 ?
C13B H13B 0.9300 . ?
N1 C1 1.145(11) . ?
N2 C2 1.140(12) . ?
C1 C3 1.449(13) . ?
C2 C3 1.409(13) . ?
C3 C4 1.389(5) . ?
C4 C5 1.399(10) . ?
C4 C6 1.475(10) . ?
C5 C5 1.318(13) 2_655 ?
C5 H5 0.9300 . ?
C6 C6 1.366(12) 2_655 ?
C6 H6 0.9300 . ?

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
_geom_angle_publ_flag
C11A S1A C8A 93.5(14) . . ?
C12A S2A C12A 93.3(8) 2_656 . ?
C9A C8A C12A 124.4(18) . . ?
C9A C8A S1A 115.0(9) . . ?
C12A C8A S1A 120(2) . . ?
C8A C9A C10A 105.1(10) . . ?
C8A C9A H9A 127.5 . . ?
C10A C9A H9A 127.5 . . ?
C11A C10A C9A 113.6(11) . . ?
C11A C10A H10A 123.2 . . ?
C9A C10A H10A 123.2 . . ?
C10A C11A S1A 112.3(10) . . ?
C10A C11A H11A 123.8 . . ?
S1A C11A H11A 123.8 . . ?
C13A C12A C8A 126.6(14) . . ?
C13A C12A S2A 112.0(8) . . ?
C8A C12A S2A 121.4(14) . . ?
C12A C13A C13A 111.3(7) . 2_656 ?
C12A C13A H13A 124.3 . . ?
C13A C13A H13A 124.3 2_656 . ?
C11B S1B C8B 97.3(14) . . ?
C12B S2B C12B 90.8(9) 2_656 . ?
C9B C8B C12B 126(2) . . ?
C9B C8B S1B 111.8(8) . . ?
C12B C8B S1B 122(2) . . ?
C8B C9B C10B 105.9(11) . . ?
C8B C9B H9B 127.1 . . ?
C10B C9B H9B 127.1 . . ?
C11B C10B C9B 115.1(11) . . ?
C11B C10B H10B 122.5 . . ?
C9B C10B H10B 122.5 . . ?
C10B C11B S1B 109.1(10) . . ?
C10B C11B H11B 125.5 . . ?
S1B C11B H11B 125.5 . . ?
C13B C12B C8B 128.4(15) . . ?
C13B C12B S2B 109.6(8) . . ?
C8B C12B S2B 121.9(14) . . ?
C13B C13B C12B 115.0(7) 2_656 . ?
C13B C13B H13B 122.5 2_656 . ?
C12B C13B H13B 122.5 . . ?
N1 C1 C3 176.0(9) . . ?
N2 C2 C3 179.7(9) . . ?
C4 C3 C2 125.4(9) . . ?
C4 C3 C1 119.5(9) . . ?
C2 C3 C1 115.1(2) . . ?
C3 C4 C5 124.8(8) . . ?
C3 C4 C6 116.7(9) . . ?
C5 C4 C6 118.5(2) . . ?
C5 C5 C4 122.2(4) 2_655 . ?
C5 C5 H5 118.9 2_655 . ?
C4 C5 H5 118.9 . . ?
C6 C6 C4 119.3(4) 2_655 . ?
C6 C6 H6 120.4 2_655 . ?
C4 C6 H6 120.4 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11A S1A C8A C9A 2(6) . . . . ?
C11A S1A C8A C12A -171(6) . . . . ?
C12A C8A C9A C10A 174(6) . . . . ?
S1A C8A C9A C10A 2(6) . . . . ?
C8A C9A C10A C11A -6(4) . . . . ?
C9A C10A C11A S1A 8(2) . . . . ?
C8A S1A C11A C10A -5(3) . . . . ?
C9A C8A C12A C13A -173(5) . . . . ?
S1A C8A C12A C13A -1(9) . . . . ?
C9A C8A C12A S2A 8(10) . . . . ?
S1A C8A C12A S2A 179(4) . . . . ?
C12A S2A C12A C13A -0.3(12) 2_656 . . . ?
C12A S2A C12A C8A 179(5) 2_656 . . . ?
C8A C12A C13A C13A -179(5) . . . 2_656 ?
S2A C12A C13A C13A 1(3) . . . 2_656 ?
C11B S1B C8B C9B 1(6) . . . . ?
C11B S1B C8B C12B -172(6) . . . . ?
C12B C8B C9B C10B 177(6) . . . . ?
S1B C8B C9B C10B 5(6) . . . . ?
C8B C9B C10B C11B -9(4) . . . . ?
C9B C10B C11B S1B 10(2) . . . . ?
C8B S1B C11B C10B -6(3) . . . . ?
C9B C8B C12B C13B -180(5) . . . . ?
S1B C8B C12B C13B -8(9) . . . . ?
C9B C8B C12B S2B 4(10) . . . . ?
S1B C8B C12B S2B 175(4) . . . . ?
C12B S2B C12B C13B 0.2(11) 2_656 . . . ?
C12B S2B C12B C8B 178(5) 2_656 . . . ?
C8B C12B C13B C13B -178(5) . . . 2_656 ?
S2B C12B C13B C13B -1(3) . . . 2_656 ?
C2 C3 C4 C5 -179.0(7) . . . . ?
C1 C3 C4 C5 1.6(7) . . . . ?
C2 C3 C4 C6 0.7(7) . . . . ?
C1 C3 C4 C6 -178.7(6) . . . . ?
C3 C4 C5 C5 -178.3(8) . . . 2_655 ?
C6 C4 C5 C5 1.9(9) . . . 2_655 ?
C3 C4 C6 C6 -179.3(7) . . . 2_655 ?
C5 C4 C6 C6 0.5(7) . . . 2_655 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(4T)(TCNQ)
_database_code_depnum_ccdc_archive 'CCDC 1862144'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H14 N4 S4'
_chemical_formula_moiety         'C16 H10 S4, C12 H4 N4'
_chemical_formula_weight         534.69
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.861(4)
_cell_length_b                   8.890(3)
_cell_length_c                   10.291(8)
_cell_angle_alpha                109.60(4)
_cell_angle_beta                 109.29(5)
_cell_angle_gamma                98.00(4)
_cell_volume                     613.7(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    34
_cell_measurement_theta_min      11.04
_cell_measurement_theta_max      12.49
_cell_measurement_temperature    297
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.794
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             274.00
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  0.973

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      297
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            4191
_diffrn_reflns_av_unetI/netI     0.1356
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        0.855
_reflns_number_total             3571
_reflns_number_gt                1650
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1952
_refine_ls_wR_factor_gt          0.1530
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3571
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0821P)²+0.0943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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 ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(4T)(F4TCNQ)
_database_code_depnum_ccdc_archive 'CCDC 1862146'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H10 F4 N4 S4'
_chemical_formula_moiety         'C16 H10 S4, C12 F4 N4'
_chemical_formula_weight         606.65
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.092(5)
_cell_length_b                   9.151(4)
_cell_length_c                   10.403(6)
_cell_angle_alpha                90.88(5)
_cell_angle_beta                 129.50(4)
_cell_angle_gamma                104.63(4)
_cell_volume                     628.0(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    20
_cell_measurement_theta_min      12.68
_cell_measurement_theta_max      15.10
_cell_measurement_temperature    297
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.022
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             306.00
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      297
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            2801
_diffrn_reflns_av_unetI/netI     0.1410
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.611
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -2.678
_reflns_number_total             2210
_reflns_number_gt                1164
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1817
_refine_ls_R_factor_gt           0.0920
_refine_ls_wR_factor_ref         0.3086
_refine_ls_wR_factor_gt          0.2479
_refine_ls_number_restraints     20
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2210
_refine_ls_number_parameters     175
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1664P)²+1.4094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.57
_refine_diff_density_min         -0.92
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(4T)(F2TCNQ)
_database_code_depnum_ccdc_archive 'CCDC 1862145'
_audit_update_record             
;
2018-08-15 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H12 F2 N4 S4'
_chemical_formula_moiety         'C16 H10 S4, C12 H2 F2 N4'
_chemical_formula_weight         570.67
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.9104(5)
_cell_length_b                   8.8995(6)
_cell_length_c                   10.3989(7)
_cell_angle_alpha                109.866(3)
_cell_angle_beta                 109.641(3)
_cell_angle_gamma                97.879(4)
_cell_volume                     621.80(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2082
_cell_measurement_theta_min      4.96
_cell_measurement_theta_max      67.92
_cell_measurement_temperature    270
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.026
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290.00
_exptl_absorpt_coefficient_mu    3.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_T_max  0.904

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6806
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_theta_max         63.513
_diffrn_reflns_theta_min         4.960
_diffrn_reflns_theta_full        63.513
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2011
_reflns_number_gt                1162
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.1030
_refine_ls_wR_factor_ref         0.3315
_refine_ls_wR_factor_gt          0.2908
_refine_ls_number_restraints     25
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2011
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1979P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
