#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:21:16 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/66/7246664.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_7246664
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         'C7 H4 N2 O S4'
_chemical_formula_sum            'C7 H4 N2 O S4'
_chemical_formula_weight         260.36
_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                111.186(8)
_cell_angle_beta                 108.771(8)
_cell_angle_gamma                97.407(8)
_cell_formula_units_Z            2
_cell_length_a                   7.0683(15)
_cell_length_b                   8.6879(17)
_cell_length_c                   9.462(2)
_cell_measurement_reflns_used    5845
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5007
_cell_measurement_theta_min      2.5169
_cell_measurement_wavelength     0.710730
_cell_volume                     492.78(18)
_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 0.974
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0455387
_diffrn_orient_matrix_UB_12      0.0763231
_diffrn_orient_matrix_UB_13      0.1201235
_diffrn_orient_matrix_UB_21      -0.1357554
_diffrn_orient_matrix_UB_22      0.0291001
_diffrn_orient_matrix_UB_23      -0.0236324
_diffrn_orient_matrix_UB_31      -0.0607496
_diffrn_orient_matrix_UB_32      -0.0992001
_diffrn_orient_matrix_UB_33      0.0168026
_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  0.0356
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5511
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.617
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0274
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²+0.0876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                2084
_reflns_number_total             2195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ce00257h2.cif
_cod_data_source_block           compound2a
_cod_depositor_comments
'Adding full bibliography for 7246664--7246672.cif.'
_cod_original_cell_volume        492.79(18)
_cod_database_code               7246664
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
O1 O 0.09263(17) 0.71625(15) 0.30243(15) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.1350(2) 0.60759(18) 0.34819(19) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.1676(2) 0.31768(17) 0.35686(17) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.2699(2) 0.43730(17) 0.51584(17) 0.0156(3) Uani 1 1 d . . . . .
N5 N 0.35465(17) 0.38028(14) 0.63313(14) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.3140(2) 0.21276(17) 0.55954(16) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.5429(2) 0.24146(18) 0.86499(17) 0.0190(3) Uani 1 1 d . . . . .
H7A H 0.650330 0.197959 0.923427 0.023 Uiso 1 1 calc R U . . .
H7B H 0.614911 0.347181 0.865223 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4027(2) 0.28669(17) 0.95937(17) 0.0212(3) Uani 1 1 d . . . . .
H8A H 0.485853 0.382384 1.069880 0.025 Uiso 1 1 calc R U . . .
H8B H 0.291356 0.325731 0.899060 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3089(2) 0.13904(18) 0.97841(17) 0.0214(3) Uani 1 1 d . . . . .
N10 N 0.2375(2) 0.02203(18) 0.99180(18) 0.0279(3) Uani 1 1 d . . . . .
S1 S 0.28080(5) 0.65105(4) 0.55741(4) 0.01860(12) Uani 1 1 d . . . . .
S2 S 0.05387(5) 0.38509(5) 0.20693(4) 0.02141(12) Uani 1 1 d . . . . .
S3 S 0.16909(5) 0.11578(4) 0.34681(4) 0.01824(11) Uani 1 1 d . . . . .
S4 S 0.40270(5) 0.08253(4) 0.65431(4) 0.01935(12) 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'
O O 0.0106 0.0060 '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
O1 C2 S1 124.06(12) . . ?
O1 C2 S2 121.70(12) . . ?
S1 C2 S2 114.23(8) . . ?
C4 C3 S3 109.73(10) . . ?
C4 C3 S2 118.51(11) . . ?
S3 C3 S2 131.70(9) . . ?
C3 C4 N5 117.44(12) . . ?
C3 C4 S1 117.99(10) . . ?
N5 C4 S1 124.56(10) . . ?
C6 N5 C4 108.36(12) . . ?
N5 C6 S4 125.61(10) . . ?
N5 C6 S3 116.33(10) . . ?
S4 C6 S3 117.99(8) . . ?
C8 C7 S4 113.22(9) . . ?
C8 C7 H7A 108.9 . . ?
S4 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
S4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 111.44(11) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N10 C9 C8 178.76(15) . . ?
C4 S1 C2 94.69(7) . . ?
C3 S2 C2 94.59(7) . . ?
C3 S3 C6 88.12(7) . . ?
C6 S4 C7 100.26(7) . . ?
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
O1 C2 1.2055(17) . ?
C2 S1 1.7805(16) . ?
C2 S2 1.7904(16) . ?
C3 C4 1.357(2) . ?
C3 S3 1.7237(14) . ?
C3 S2 1.7290(14) . ?
C4 N5 1.3719(17) . ?
C4 S1 1.7392(14) . ?
N5 C6 1.3102(17) . ?
C6 S4 1.7412(13) . ?
C6 S3 1.7423(14) . ?
C7 C8 1.533(2) . ?
C7 S4 1.8025(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.464(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N10 1.143(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
S3 C3 C4 N5 1.08(15) . . . . ?
S2 C3 C4 N5 178.52(9) . . . . ?
S3 C3 C4 S1 -177.85(7) . . . . ?
S2 C3 C4 S1 -0.41(15) . . . . ?
C3 C4 N5 C6 -0.15(16) . . . . ?
S1 C4 N5 C6 178.71(9) . . . . ?
C4 N5 C6 S4 175.81(9) . . . . ?
C4 N5 C6 S3 -0.89(14) . . . . ?
S4 C7 C8 C9 64.68(14) . . . . ?
C3 C4 S1 C2 0.28(12) . . . . ?
N5 C4 S1 C2 -178.57(11) . . . . ?
O1 C2 S1 C4 179.96(13) . . . . ?
S2 C2 S1 C4 -0.07(8) . . . . ?
C4 C3 S2 C2 0.30(12) . . . . ?
S3 C3 S2 C2 177.07(10) . . . . ?
O1 C2 S2 C3 179.87(13) . . . . ?
S1 C2 S2 C3 -0.09(8) . . . . ?
C4 C3 S3 C6 -1.24(10) . . . . ?
S2 C3 S3 C6 -178.22(11) . . . . ?
N5 C6 S3 C3 1.28(11) . . . . ?
S4 C6 S3 C3 -175.69(8) . . . . ?
N5 C6 S4 C7 2.15(13) . . . . ?
S3 C6 S4 C7 178.81(7) . . . . ?
C8 C7 S4 C6 83.22(10) . . . . ?
