#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:21:16 +0200 (Mon 05 de Jun de 2023) $
#$Revision: 284253 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/66/7246672.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_7246672
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 F4 N4, 2(C9 H6 I N S7)'
_chemical_formula_sum            'C30 H12 F4 I2 N6 S14'
_chemical_formula_weight         1235.10
_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                77.886(5)
_cell_angle_beta                 87.003(5)
_cell_angle_gamma                72.421(5)
_cell_formula_units_Z            1
_cell_length_a                   7.2339(10)
_cell_length_b                   10.7451(15)
_cell_length_c                   13.7344(19)
_cell_measurement_reflns_used    9209
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4836
_cell_measurement_theta_min      2.7718
_cell_measurement_wavelength     0.710730
_cell_volume                     995.0(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 0.987
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0523077
_diffrn_orient_matrix_UB_12      0.0304538
_diffrn_orient_matrix_UB_13      -0.0697699
_diffrn_orient_matrix_UB_21      -0.1137390
_diffrn_orient_matrix_UB_22      -0.0333288
_diffrn_orient_matrix_UB_23      0.0213773
_diffrn_orient_matrix_UB_31      -0.0732001
_diffrn_orient_matrix_UB_32      0.0889130
_diffrn_orient_matrix_UB_33      0.0148830
_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  0.0549
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20058
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.031
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.061
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.118
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0456P)²+0.9942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                3913
_reflns_number_total             4514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ce00257h2.cif
_cod_data_source_block           TTFI2TCNQF4
_cod_depositor_comments
'Adding full bibliography for 7246664--7246672.cif.'
_cod_database_code               7246672
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
I1A I -0.15486(4) 0.13159(3) 0.87901(2) 0.02814(11) Uani 0.9604(9) 1 d . . P A 1
I1B I -0.0860(12) 0.1674(8) 0.8980(5) 0.02814(11) Uani 0.0396(9) 1 d . . P A 2
S1 S 0.84750(15) 0.23742(11) 0.15013(8) 0.0303(2) Uani 1 1 d . . . . .
S2 S 0.53616(14) 0.09533(10) 0.07110(7) 0.0260(2) Uani 1 1 d . . . . .
S3 S 0.63417(13) 0.21590(9) 0.34147(6) 0.02006(19) Uani 1 1 d . . . . .
S4 S 0.36437(13) 0.09492(9) 0.27304(6) 0.02060(19) Uani 1 1 d . . . . .
S5 S 0.42818(13) 0.21473(9) 0.55062(6) 0.01911(19) Uani 1 1 d . . . . .
S6 S 0.14808(13) 0.09160(9) 0.48545(6) 0.02036(19) Uani 1 1 d . . . . .
S7 S 0.19839(14) 0.21475(10) 0.74982(6) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.7430(7) 0.4160(5) 0.1168(4) 0.0458(12) Uani 1 1 d . . . . .
H1A H 0.629503 0.437556 0.073482 0.069 Uiso 1 1 calc R U . . .
H1B H 0.839260 0.455895 0.081583 0.069 Uiso 1 1 calc R U . . .
H1C H 0.703487 0.451656 0.177278 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6601(5) 0.1914(4) 0.2191(3) 0.0217(7) Uani 1 1 d . . . . .
C3 C 0.5355(5) 0.1360(4) 0.1878(2) 0.0198(7) Uani 1 1 d . . . . .
C4 C 0.3209(7) 0.2206(5) 0.0143(3) 0.0419(11) Uani 1 1 d . . . . .
H4A H 0.208615 0.187133 0.029658 0.063 Uiso 1 1 calc R U . . .
H4B H 0.337100 0.240733 -0.058025 0.063 Uiso 1 1 calc R U . . .
H4C H 0.300370 0.301769 0.040491 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4364(5) 0.1552(3) 0.3673(3) 0.0186(7) Uani 1 1 d . . . . .
C6 C 0.3466(5) 0.1530(3) 0.4584(2) 0.0179(7) Uani 1 1 d . . . . .
C7 C 0.2471(5) 0.1873(4) 0.6317(2) 0.0189(7) Uani 1 1 d . . . . .
C8 C 0.1190(5) 0.1301(4) 0.6035(3) 0.0199(7) Uani 1 1 d . . . . .
N9 N -0.0217(5) 0.1047(3) 0.6718(2) 0.0204(6) Uani 1 1 d . . . . .
C10 C 0.0114(5) 0.1455(4) 0.7517(3) 0.0225(8) Uani 1 1 d . . . . .
C11 C 0.7613(5) 0.4756(4) 0.6722(3) 0.0205(7) Uani 1 1 d . . . . .
C12 C 0.7894(6) 0.5139(4) 0.7623(3) 0.0270(8) Uani 1 1 d . . . . .
N13 N 0.8029(6) 0.5407(4) 0.8370(3) 0.0384(9) Uani 1 1 d . . . . .
C14 C 0.6019(5) 0.4207(4) 0.6774(3) 0.0219(7) Uani 1 1 d . . . . .
N15 N 0.4765(5) 0.3767(4) 0.6877(2) 0.0305(8) Uani 1 1 d . . . . .
C16 C 0.8773(5) 0.4878(3) 0.5871(3) 0.0182(7) Uani 1 1 d . . . . .
C17 C 0.8576(5) 0.4414(3) 0.5003(3) 0.0196(7) Uani 1 1 d . . . . .
C18 C 0.9702(5) 0.4527(4) 0.4192(2) 0.0195(7) Uani 1 1 d . . . . .
F19 F 0.7203(3) 0.3809(2) 0.49894(16) 0.0278(5) Uani 1 1 d . . . . .
F20 F 0.9394(3) 0.4017(2) 0.34238(15) 0.0268(5) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C2 S1 C1 101.1(2) . . ?
C3 S2 C4 101.16(19) . . ?
C5 S3 C2 95.26(17) . . ?
C5 S4 C3 94.95(17) . . ?
C7 S5 C6 92.87(16) . . ?
C8 S6 C6 93.34(16) . . ?
C7 S7 C10 87.90(17) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 S3 116.6(3) . . ?
C3 C2 S1 126.3(3) . . ?
S3 C2 S1 117.0(2) . . ?
C2 C3 S2 125.8(3) . . ?
C2 C3 S4 117.3(3) . . ?
S2 C3 S4 116.9(2) . . ?
S2 C4 H4A 109.5 . . ?
S2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S4 122.7(3) . . ?
C6 C5 S3 121.5(3) . . ?
S4 C5 S3 115.8(2) . . ?
C5 C6 S6 121.9(3) . . ?
C5 C6 S5 120.3(3) . . ?
S6 C6 S5 117.8(2) . . ?
C8 C7 S7 110.1(3) . . ?
C8 C7 S5 119.0(3) . . ?
S7 C7 S5 130.9(2) . . ?
C7 C8 N9 117.8(3) . . ?
C7 C8 S6 117.0(3) . . ?
N9 C8 S6 125.3(3) . . ?
C10 N9 C8 105.4(3) . . ?
N9 C10 S7 118.8(3) . . ?
N9 C10 I1A 122.6(3) . . ?
S7 C10 I1A 118.64(19) . . ?
N9 C10 I1B 144.3(4) . . ?
S7 C10 I1B 96.8(3) . . ?
C16 C11 C12 124.4(3) . . ?
C16 C11 C14 123.1(3) . . ?
C12 C11 C14 112.6(3) . . ?
N13 C12 C11 175.5(4) . . ?
N15 C14 C11 175.9(4) . . ?
C11 C16 C17 124.3(3) . . ?
C11 C16 C18 122.8(3) . 2_766 ?
C17 C16 C18 112.9(3) . 2_766 ?
F19 C17 C18 118.0(3) . . ?
F19 C17 C16 118.0(3) . . ?
C18 C17 C16 124.0(3) . . ?
F20 C18 C17 118.1(3) . . ?
F20 C18 C16 118.8(3) . 2_766 ?
C17 C18 C16 123.1(3) . 2_766 ?
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
I1A C10 2.074(3) . ?
I1B C10 2.130(7) . ?
S1 C2 1.747(4) . ?
S1 C1 1.804(5) . ?
S2 C3 1.747(3) . ?
S2 C4 1.807(5) . ?
S3 C5 1.735(3) . ?
S3 C2 1.746(4) . ?
S4 C5 1.730(3) . ?
S4 C3 1.750(4) . ?
S5 C7 1.728(4) . ?
S5 C6 1.749(3) . ?
S6 C8 1.743(4) . ?
S6 C6 1.746(3) . ?
S7 C7 1.709(3) . ?
S7 C10 1.726(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.351(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.378(5) . ?
C7 C8 1.367(5) . ?
C8 N9 1.396(5) . ?
N9 C10 1.322(5) . ?
C11 C16 1.408(5) . ?
C11 C12 1.426(5) . ?
C11 C14 1.438(5) . ?
C12 N13 1.139(5) . ?
C14 N15 1.134(5) . ?
C16 C17 1.414(5) . ?
C16 C18 1.424(5) 2_766 ?
C17 F19 1.345(4) . ?
C17 C18 1.352(5) . ?
C18 F20 1.343(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
C5 S3 C2 C3 -1.5(3) . . . . ?
C5 S3 C2 S1 179.8(2) . . . . ?
C1 S1 C2 C3 103.5(4) . . . . ?
C1 S1 C2 S3 -78.0(3) . . . . ?
S3 C2 C3 S2 -177.4(2) . . . . ?
S1 C2 C3 S2 1.0(5) . . . . ?
S3 C2 C3 S4 -0.2(4) . . . . ?
S1 C2 C3 S4 178.3(2) . . . . ?
C4 S2 C3 C2 -108.7(4) . . . . ?
C4 S2 C3 S4 74.1(3) . . . . ?
C5 S4 C3 C2 1.9(3) . . . . ?
C5 S4 C3 S2 179.3(2) . . . . ?
C3 S4 C5 C6 178.5(3) . . . . ?
C3 S4 C5 S3 -2.9(2) . . . . ?
C2 S3 C5 C6 -178.6(3) . . . . ?
C2 S3 C5 S4 2.8(2) . . . . ?
S4 C5 C6 S6 -1.2(5) . . . . ?
S3 C5 C6 S6 -179.74(19) . . . . ?
S4 C5 C6 S5 179.6(2) . . . . ?
S3 C5 C6 S5 1.1(5) . . . . ?
C8 S6 C6 C5 -177.4(3) . . . . ?
C8 S6 C6 S5 1.8(2) . . . . ?
C7 S5 C6 C5 177.0(3) . . . . ?
C7 S5 C6 S6 -2.2(2) . . . . ?
C10 S7 C7 C8 0.5(3) . . . . ?
C10 S7 C7 S5 -177.1(3) . . . . ?
C6 S5 C7 C8 1.9(3) . . . . ?
C6 S5 C7 S7 179.3(3) . . . . ?
S7 C7 C8 N9 -0.1(4) . . . . ?
S5 C7 C8 N9 177.8(3) . . . . ?
S7 C7 C8 S6 -178.91(19) . . . . ?
S5 C7 C8 S6 -1.0(4) . . . . ?
C6 S6 C8 C7 -0.5(3) . . . . ?
C6 S6 C8 N9 -179.2(3) . . . . ?
C7 C8 N9 C10 -0.5(4) . . . . ?
S6 C8 N9 C10 178.2(3) . . . . ?
C8 N9 C10 S7 1.0(4) . . . . ?
C8 N9 C10 I1A -179.8(2) . . . . ?
C8 N9 C10 I1B 178.8(5) . . . . ?
C7 S7 C10 N9 -0.9(3) . . . . ?
C7 S7 C10 I1A 179.8(2) . . . . ?
C7 S7 C10 I1B -179.7(3) . . . . ?
C12 C11 C16 C17 175.5(4) . . . . ?
C14 C11 C16 C17 -3.6(6) . . . . ?
C12 C11 C16 C18 -3.6(6) . . . 2_766 ?
C14 C11 C16 C18 177.3(3) . . . 2_766 ?
C11 C16 C17 F19 -0.5(5) . . . . ?
C18 C16 C17 F19 178.7(3) 2_766 . . . ?
C11 C16 C17 C18 -179.5(4) . . . . ?
C18 C16 C17 C18 -0.4(6) 2_766 . . . ?
F19 C17 C18 F20 -0.5(5) . . . . ?
C16 C17 C18 F20 178.5(3) . . . . ?
F19 C17 C18 C16 -178.6(3) . . . 2_766 ?
C16 C17 C18 C16 0.4(6) . . . 2_766 ?
