#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:21:16 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246671.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_7246671
loop_
_publ_author_name
'Kharraz, Haia'
'Hachem, Hadi'
'Le Gal, Yann'
'Roisnel, Thierry'
'Jeannin, Olivier'
'Barrière, Frédéric'
'Guizouarn, Thierry'
'Lorcy, Dominique'
_publ_section_title
;
 Non-covalent interactions in neutral and oxidized tetrathiafulvalenes
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              2946
_journal_page_last               2958
_journal_paper_doi               10.1039/D3CE00257H
_journal_volume                  25
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H6 N2 S8'
_chemical_formula_sum            'C10 H6 N2 S8'
_chemical_formula_weight         410.65
_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     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                73.335(5)
_cell_angle_beta                 87.672(6)
_cell_angle_gamma                81.049(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4506(12)
_cell_length_b                   8.1175(12)
_cell_length_c                   13.345(2)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4777
_cell_measurement_theta_min      2.6755
_cell_measurement_wavelength     0.710730
_cell_volume                     763.8(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0991019
_diffrn_orient_matrix_UB_12      0.0431682
_diffrn_orient_matrix_UB_13      0.0290533
_diffrn_orient_matrix_UB_21      -0.0431816
_diffrn_orient_matrix_UB_22      -0.0515944
_diffrn_orient_matrix_UB_23      0.0725361
_diffrn_orient_matrix_UB_31      0.0823164
_diffrn_orient_matrix_UB_32      -0.1113232
_diffrn_orient_matrix_UB_33      0.0036183
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0268
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21489
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.649
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    1.156
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0453P)²+0.4935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                3295
_reflns_number_total             3500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ce00257h2.cif
_cod_data_source_block           TTFSCN
_cod_depositor_comments
'Adding full bibliography for 7246664--7246672.cif.'
_cod_database_code               7246671
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17329(7) 0.38867(6) 0.91077(3) 0.03072(12) Uani 1 1 d . . . . .
S2 S -0.01076(6) 0.77948(6) 0.77444(3) 0.02682(11) Uani 1 1 d . . . . .
S3 S 0.26384(6) 0.31316(5) 0.70524(3) 0.02323(11) Uani 1 1 d . . . . .
S4 S 0.11998(6) 0.67194(5) 0.58155(3) 0.02216(11) Uani 1 1 d . . . . .
S5 S 0.40587(6) 0.21670(5) 0.49642(3) 0.02383(11) Uani 1 1 d . . . . .
S6 S 0.26659(6) 0.58308(5) 0.36905(3) 0.02267(11) Uani 1 1 d . . . . .
S7 S 0.40936(6) 0.46109(5) 0.17392(3) 0.02265(11) Uani 1 1 d . . . . .
S8 S 0.60004(6) 0.15137(6) 0.10859(3) 0.02810(12) Uani 1 1 d . . . . .
C1 C -0.0295(4) 0.9739(3) 0.66777(18) 0.0462(6) Uani 1 1 d . . . . .
H1A H 0.090566 0.988692 0.636816 0.069 Uiso 1 1 calc R U . . .
H1B H -0.077112 1.074010 0.693250 0.069 Uiso 1 1 calc R U . . .
H1C H -0.112279 0.965668 0.614775 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0152(3) 0.2362(3) 0.93832(15) 0.0347(4) Uani 1 1 d . . . . .
H2A H -0.106239 0.297346 0.914350 0.052 Uiso 1 1 calc R U . . .
H2B H 0.012792 0.180420 1.013839 0.052 Uiso 1 1 calc R U . . .
H2C H 0.052717 0.147559 0.901847 0.052 Uiso 1 1 calc R U . . .
C3 C 0.0995(2) 0.6219(2) 0.71789(12) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.1664(2) 0.4597(2) 0.77420(12) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.2339(2) 0.4656(2) 0.58143(12) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.2948(2) 0.4269(2) 0.49319(12) 0.0195(3) Uani 1 1 d . . . . .
C7 C 0.3679(2) 0.4374(2) 0.30399(12) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.4328(2) 0.2704(2) 0.36093(12) 0.0202(3) Uani 1 1 d . . . . .
N9 N 0.51641(18) 0.15837(18) 0.30672(10) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.5099(2) 0.2465(2) 0.20714(13) 0.0224(3) Uani 1 1 d . . . . .
C11 C 0.4369(2) 0.0246(2) 0.11354(14) 0.0286(4) Uani 1 1 d . . . . .
N12 N 0.3325(2) -0.0651(3) 0.11756(15) 0.0416(4) 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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables 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
_geom_angle_publ_flag
C4 S1 C2 101.52(8) . . ?
C3 S2 C1 102.80(9) . . ?
C5 S3 C4 94.91(8) . . ?
C3 S4 C5 95.16(7) . . ?
C8 S5 C6 93.29(7) . . ?
C7 S6 C6 93.19(7) . . ?
C7 S7 C10 88.25(8) . . ?
C11 S8 C10 97.09(8) . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S1 C2 H2A 109.5 . . ?
S1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 S2 122.96(12) . . ?
C4 C3 S4 117.40(12) . . ?
S2 C3 S4 119.62(9) . . ?
C3 C4 S1 124.38(12) . . ?
C3 C4 S3 117.47(12) . . ?
S1 C4 S3 118.06(10) . . ?
C6 C5 S3 122.35(13) . . ?
C6 C5 S4 122.69(13) . . ?
S3 C5 S4 114.96(9) . . ?
C5 C6 S5 121.21(13) . . ?
C5 C6 S6 121.81(13) . . ?
S5 C6 S6 116.99(9) . . ?
C8 C7 S7 109.63(11) . . ?
C8 C7 S6 118.93(12) . . ?
S7 C7 S6 131.43(10) . . ?
C7 C8 N9 117.45(14) . . ?
C7 C8 S5 117.58(12) . . ?
N9 C8 S5 124.97(12) . . ?
C10 N9 C8 106.74(14) . . ?
N9 C10 S7 117.93(12) . . ?
N9 C10 S8 122.06(13) . . ?
S7 C10 S8 120.01(10) . . ?
N12 C11 S8 177.58(18) . . ?
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 C4 1.7471(16) . ?
S1 C2 1.7918(19) . ?
S2 C3 1.7484(16) . ?
S2 C1 1.788(2) . ?
S3 C5 1.7554(16) . ?
S3 C4 1.7592(16) . ?
S4 C3 1.7525(16) . ?
S4 C5 1.7568(16) . ?
S5 C8 1.7451(16) . ?
S5 C6 1.7660(16) . ?
S6 C7 1.7263(16) . ?
S6 C6 1.7711(16) . ?
S7 C7 1.7113(15) . ?
S7 C10 1.7234(17) . ?
S8 C11 1.6979(18) . ?
S8 C10 1.7681(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.343(2) . ?
C5 C6 1.347(2) . ?
C7 C8 1.372(2) . ?
C8 N9 1.380(2) . ?
N9 C10 1.315(2) . ?
C11 N12 1.135(2) . ?
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 S2 C3 C4 169.51(16) . . . . ?
C1 S2 C3 S4 -12.45(13) . . . . ?
C5 S4 C3 C4 -0.95(14) . . . . ?
C5 S4 C3 S2 -179.10(9) . . . . ?
S2 C3 C4 S1 -6.5(2) . . . . ?
S4 C3 C4 S1 175.44(9) . . . . ?
S2 C3 C4 S3 176.97(8) . . . . ?
S4 C3 C4 S3 -1.11(18) . . . . ?
C2 S1 C4 C3 112.95(16) . . . . ?
C2 S1 C4 S3 -70.52(12) . . . . ?
C5 S3 C4 C3 2.54(14) . . . . ?
C5 S3 C4 S1 -174.23(9) . . . . ?
C4 S3 C5 C6 176.56(14) . . . . ?
C4 S3 C5 S4 -3.10(10) . . . . ?
C3 S4 C5 C6 -177.00(14) . . . . ?
C3 S4 C5 S3 2.66(10) . . . . ?
S3 C5 C6 S5 1.3(2) . . . . ?
S4 C5 C6 S5 -179.08(8) . . . . ?
S3 C5 C6 S6 -179.03(8) . . . . ?
S4 C5 C6 S6 0.6(2) . . . . ?
C8 S5 C6 C5 178.62(14) . . . . ?
C8 S5 C6 S6 -1.09(10) . . . . ?
C7 S6 C6 C5 -178.37(14) . . . . ?
C7 S6 C6 S5 1.34(10) . . . . ?
C10 S7 C7 C8 -0.10(12) . . . . ?
C10 S7 C7 S6 178.91(13) . . . . ?
C6 S6 C7 C8 -1.15(14) . . . . ?
C6 S6 C7 S7 179.90(12) . . . . ?
S7 C7 C8 N9 0.51(18) . . . . ?
S6 C7 C8 N9 -178.65(11) . . . . ?
S7 C7 C8 S5 179.78(8) . . . . ?
S6 C7 C8 S5 0.62(18) . . . . ?
C6 S5 C8 C7 0.30(14) . . . . ?
C6 S5 C8 N9 179.51(14) . . . . ?
C7 C8 N9 C10 -0.72(19) . . . . ?
S5 C8 N9 C10 -179.93(12) . . . . ?
C8 N9 C10 S7 0.63(17) . . . . ?
C8 N9 C10 S8 -179.27(11) . . . . ?
C7 S7 C10 N9 -0.33(13) . . . . ?
C7 S7 C10 S8 179.57(10) . . . . ?
C11 S8 C10 N9 72.40(15) . . . . ?
C11 S8 C10 S7 -107.49(11) . . . . ?
