#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:21:16 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246668.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_7246668
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         'C12 H10 N2 S8'
_chemical_formula_sum            'C12 H10 N2 S8'
_chemical_formula_weight         438.70
_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                84.691(2)
_cell_angle_beta                 79.633(2)
_cell_angle_gamma                85.606(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0133(3)
_cell_length_b                   10.3719(7)
_cell_length_c                   14.1989(9)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4865
_cell_measurement_theta_min      2.3622
_cell_measurement_wavelength     0.710730
_cell_volume                     865.76(9)
_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      296(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0887763
_diffrn_orient_matrix_UB_12      -0.0676398
_diffrn_orient_matrix_UB_13      0.0421465
_diffrn_orient_matrix_UB_21      0.0070186
_diffrn_orient_matrix_UB_22      -0.0520441
_diffrn_orient_matrix_UB_23      -0.0564498
_diffrn_orient_matrix_UB_31      0.1440739
_diffrn_orient_matrix_UB_32      -0.0461256
_diffrn_orient_matrix_UB_33      0.0140165
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.551
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.829
_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    1.683
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+0.5693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                3494
_reflns_number_total             3918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ce00257h2.cif
_cod_data_source_block           TTFSCH2CH2CN
_cod_depositor_comments
'Adding full bibliography for 7246664--7246672.cif.'
_cod_database_code               7246668
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
N1 N 1.2695(4) -0.1206(3) 0.48755(18) 0.0749(7) Uani 1 1 d . . . . .
C2 C 1.2140(4) -0.0917(3) 0.5633(2) 0.0548(6) Uani 1 1 d . . . . .
C3 C 1.1435(4) -0.0591(3) 0.66347(19) 0.0551(6) Uani 1 1 d . . . . .
H3A H 1.144897 -0.137807 0.705969 0.066 Uiso 1 1 calc R U . . .
H3B H 0.989777 -0.020525 0.671980 0.066 Uiso 1 1 calc R U . . .
C4 C 1.2978(4) 0.0342(2) 0.69022(17) 0.0460(5) Uani 1 1 d . . . . .
H4A H 1.287009 0.115242 0.650890 0.055 Uiso 1 1 calc R U . . .
H4B H 1.453018 -0.001486 0.676437 0.055 Uiso 1 1 calc R U . . .
C5 C 0.9874(3) 0.17035(17) 0.81467(13) 0.0311(4) Uani 1 1 d . . . . .
N6 N 0.8967(3) 0.21064(15) 0.73957(12) 0.0349(3) Uani 1 1 d . . . . .
C7 C 0.7057(3) 0.28875(17) 0.76989(13) 0.0305(4) Uani 1 1 d . . . . .
C8 C 0.6537(3) 0.30664(17) 0.86453(13) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.3458(3) 0.43846(17) 0.79089(12) 0.0285(3) Uani 1 1 d . . . . .
C10 C 0.1617(3) 0.51613(17) 0.77961(12) 0.0290(4) Uani 1 1 d . . . . .
C11 C -0.1640(3) 0.65058(17) 0.71176(13) 0.0294(4) Uani 1 1 d . . . . .
C12 C -0.2070(3) 0.66409(17) 0.80636(13) 0.0293(4) Uani 1 1 d . . . . .
C13 C -0.2235(5) 0.6628(3) 0.52185(17) 0.0631(7) Uani 1 1 d . . . . .
H13A H -0.075625 0.692995 0.497330 0.095 Uiso 1 1 calc R U . . .
H13B H -0.322690 0.689909 0.476832 0.095 Uiso 1 1 calc R U . . .
H13C H -0.213577 0.569785 0.531192 0.095 Uiso 1 1 calc R U . . .
C14 C -0.3125(4) 0.8804(2) 0.9064(2) 0.0539(6) Uani 1 1 d . . . . .
H14A H -0.208743 0.843466 0.947051 0.081 Uiso 1 1 calc R U . . .
H14B H -0.426807 0.935153 0.942242 0.081 Uiso 1 1 calc R U . . .
H14C H -0.231935 0.930803 0.852713 0.081 Uiso 1 1 calc R U . . .
S1 S 1.22977(9) 0.06617(5) 0.81499(4) 0.04398(14) Uani 1 1 d . . . . .
S2 S 0.85133(8) 0.22382(5) 0.92469(3) 0.03612(12) Uani 1 1 d . . . . .
S3 S 0.41542(8) 0.40272(5) 0.90690(3) 0.03471(12) Uani 1 1 d . . . . .
S4 S 0.52517(8) 0.36562(5) 0.69537(3) 0.03517(12) Uani 1 1 d . . . . .
S5 S -0.01657(8) 0.58444(5) 0.87628(3) 0.03500(12) Uani 1 1 d . . . . .
S6 S 0.07745(8) 0.55431(5) 0.66771(3) 0.03803(13) Uani 1 1 d . . . . .
S7 S -0.44399(8) 0.75250(5) 0.86367(4) 0.03644(12) Uani 1 1 d . . . . .
S8 S -0.33239(10) 0.72883(6) 0.63352(4) 0.04928(16) 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
N1 C2 C3 177.9(3) . . ?
C2 C3 C4 111.5(2) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 S1 112.65(16) . . ?
C3 C4 H4A 109.1 . . ?
S1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
S1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N6 C5 S2 116.82(13) . . ?
N6 C5 S1 125.81(14) . . ?
S2 C5 S1 117.37(11) . . ?
C5 N6 C7 107.80(16) . . ?
C8 C7 N6 117.43(16) . . ?
C8 C7 S4 117.50(13) . . ?
N6 C7 S4 125.07(14) . . ?
C7 C8 S2 110.19(13) . . ?
C7 C8 S3 119.54(14) . . ?
S2 C8 S3 130.27(11) . . ?
C10 C9 S4 123.44(14) . . ?
C10 C9 S3 119.76(14) . . ?
S4 C9 S3 116.79(10) . . ?
C9 C10 S5 122.40(14) . . ?
C9 C10 S6 122.78(14) . . ?
S5 C10 S6 114.80(10) . . ?
C12 C11 S8 122.39(14) . . ?
C12 C11 S6 117.23(13) . . ?
S8 C11 S6 120.33(11) . . ?
C11 C12 S7 123.71(14) . . ?
C11 C12 S5 117.57(13) . . ?
S7 C12 S5 118.71(10) . . ?
S8 C13 H13A 109.5 . . ?
S8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S7 C14 H14A 109.5 . . ?
S7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 S1 C4 100.78(10) . . ?
C8 S2 C5 87.76(9) . . ?
C8 S3 C9 92.88(8) . . ?
C7 S4 C9 93.27(8) . . ?
C10 S5 C12 95.01(8) . . ?
C11 S6 C10 95.39(8) . . ?
C12 S7 C14 101.12(10) . . ?
C11 S8 C13 103.92(10) . . ?
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
N1 C2 1.128(4) . ?
C2 C3 1.472(4) . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 S1 1.801(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N6 1.304(2) . ?
C5 S2 1.7460(19) . ?
C5 S1 1.7468(18) . ?
N6 C7 1.380(2) . ?
C7 C8 1.351(3) . ?
C7 S4 1.7489(18) . ?
C8 S2 1.7184(17) . ?
C8 S3 1.7291(18) . ?
C9 C10 1.343(2) . ?
C9 S4 1.7641(18) . ?
C9 S3 1.7712(18) . ?
C10 S5 1.7519(18) . ?
C10 S6 1.7552(18) . ?
C11 C12 1.340(3) . ?
C11 S8 1.7409(18) . ?
C11 S6 1.7499(17) . ?
C12 S7 1.7474(17) . ?
C12 S5 1.7585(18) . ?
C13 S8 1.781(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 S7 1.798(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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 S1 -175.41(18) . . . . ?
S2 C5 N6 C7 -0.3(2) . . . . ?
S1 C5 N6 C7 178.71(14) . . . . ?
C5 N6 C7 C8 -0.1(2) . . . . ?
C5 N6 C7 S4 -179.77(14) . . . . ?
N6 C7 C8 S2 0.5(2) . . . . ?
S4 C7 C8 S2 -179.84(10) . . . . ?
N6 C7 C8 S3 -179.61(13) . . . . ?
S4 C7 C8 S3 0.1(2) . . . . ?
S4 C9 C10 S5 178.66(10) . . . . ?
S3 C9 C10 S5 -0.2(2) . . . . ?
S4 C9 C10 S6 0.1(2) . . . . ?
S3 C9 C10 S6 -178.85(10) . . . . ?
S8 C11 C12 S7 4.1(2) . . . . ?
S6 C11 C12 S7 -178.12(10) . . . . ?
S8 C11 C12 S5 -177.57(10) . . . . ?
S6 C11 C12 S5 0.2(2) . . . . ?
N6 C5 S1 C4 -1.3(2) . . . . ?
S2 C5 S1 C4 177.66(12) . . . . ?
C3 C4 S1 C5 -75.63(18) . . . . ?
C7 C8 S2 C5 -0.51(15) . . . . ?
S3 C8 S2 C5 179.60(15) . . . . ?
N6 C5 S2 C8 0.49(16) . . . . ?
S1 C5 S2 C8 -178.61(12) . . . . ?
C7 C8 S3 C9 -0.85(17) . . . . ?
S2 C8 S3 C9 179.03(14) . . . . ?
C10 C9 S3 C8 -179.66(16) . . . . ?
S4 C9 S3 C8 1.36(12) . . . . ?
C8 C7 S4 C9 0.77(16) . . . . ?
N6 C7 S4 C9 -179.59(16) . . . . ?
C10 C9 S4 C7 179.72(17) . . . . ?
S3 C9 S4 C7 -1.34(12) . . . . ?
C9 C10 S5 C12 -178.75(17) . . . . ?
S6 C10 S5 C12 -0.05(12) . . . . ?
C11 C12 S5 C10 -0.11(17) . . . . ?
S7 C12 S5 C10 178.33(11) . . . . ?
C12 C11 S6 C10 -0.23(17) . . . . ?
S8 C11 S6 C10 177.63(12) . . . . ?
C9 C10 S6 C11 178.84(17) . . . . ?
S5 C10 S6 C11 0.14(12) . . . . ?
C11 C12 S7 C14 -115.80(19) . . . . ?
S5 C12 S7 C14 65.87(14) . . . . ?
C12 C11 S8 C13 -173.04(19) . . . . ?
S6 C11 S8 C13 9.22(17) . . . . ?
