#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:30:40 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301040 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/38/7063840.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_7063840
loop_
_publ_author_name
'Beau, Maxime'
'Jeon, Ie-Rang'
'Jeannin, Olivier'
'Guizouarn, Thierry'
'Fourmigué, Marc'
_publ_section_title
;
 Activation of chalcogen bonding in tetrathiafulvalene derivatives with
 Se/S differentiation
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11501
_journal_page_last               11508
_journal_paper_doi               10.1039/D5NJ01745A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C5 H6 S3 Se'
_chemical_formula_sum            'C5 H6 S3 Se'
_chemical_formula_weight         241.24
_chemical_melting_point          372.0(10)
_chemical_name_common            (MeSe)2(MeS)2TTF
_chemical_name_systematic
4,5-bis(methylseleno)-4',5'-bis(methylthio)-tetrathiafulvalene
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2019-02-27T15:18:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.668(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2291(6)
_cell_length_b                   20.848(3)
_cell_length_c                   7.6487(10)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.84
_cell_measurement_wavelength     0.71073
_cell_volume                     833.78(19)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.123654
_diffrn_orient_matrix_UB_12      0.035699
_diffrn_orient_matrix_UB_13      -0.020909
_diffrn_orient_matrix_UB_21      0.084095
_diffrn_orient_matrix_UB_22      -0.008835
_diffrn_orient_matrix_UB_23      0.115599
_diffrn_orient_matrix_UB_31      0.119227
_diffrn_orient_matrix_UB_32      -0.030794
_diffrn_orient_matrix_UB_33      -0.057405
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5896
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         1.954
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.166
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.830
_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    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.1
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0139P)²+1.8484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0
_reflns_number_gt                1352
_reflns_number_total             1887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj01745a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '371-373' was changed to
'372.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7063840--7063845.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063840
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S4 S 0.308(2) 0.1344(7) 0.250(2) 0.038(4) Uani 0.5 1 d . . P A 1
S3 S 0.538(4) 0.2014(8) -0.135(3) 0.054(5) Uani 0.5 1 d . . P B 1
C4 C 0.8206(11) 0.2553(3) -0.0858(9) 0.0556(17) Uani 0.5 1 d . . P B 1
H4A H 0.7894 0.2971 -0.1346 0.083 Uiso 0.5 1 calc R U P B 1
H4B H 0.8443 0.2589 0.0385 0.083 Uiso 0.5 1 calc R U P B 1
H4C H 0.9716 0.2374 -0.1365 0.083 Uiso 0.5 1 calc R U P B 1
C5 C 0.3290(15) 0.0888(4) 0.4513(9) 0.087(3) Uani 0.5 1 d . . P A 1
H5A H 0.1992 0.1031 0.53 0.13 Uiso 0.5 1 calc R U P A 1
H5B H 0.3043 0.0441 0.4262 0.13 Uiso 0.5 1 calc R U P A 1
H5C H 0.4944 0.095 0.5043 0.13 Uiso 0.5 1 calc R U P A 1
Se4 Se 0.3086(10) 0.1375(3) 0.2476(9) 0.0418(17) Uani 0.5 1 d . . P A 2
Se3 Se 0.5276(13) 0.2043(3) -0.1201(12) 0.0396(11) Uani 0.5 1 d . . P B 2
C4B C 0.8206(11) 0.2553(3) -0.0858(9) 0.0556(17) Uani 0.5 1 d . . P B 2
H4B1 H 0.7875 0.2979 -0.1278 0.083 Uiso 0.5 1 calc R U P B 2
H4B2 H 0.8628 0.2569 0.0366 0.083 Uiso 0.5 1 calc R U P B 2
H4B3 H 0.9609 0.2371 -0.1486 0.083 Uiso 0.5 1 calc R U P B 2
C5B C 0.3290(15) 0.0888(4) 0.4513(9) 0.087(3) Uani 0.5 1 d . . P A 2
H5B1 H 0.2019 0.1033 0.5319 0.13 Uiso 0.5 1 calc R U P A 2
H5B2 H 0.2996 0.0445 0.4236 0.13 Uiso 0.5 1 calc R U P A 2
H5B3 H 0.4958 0.0936 0.5033 0.13 Uiso 0.5 1 calc R U P A 2
S2 S 0.6995(3) 0.02778(6) 0.18108(17) 0.0355(3) Uani 1 1 d . . . . .
S1 S 0.8889(3) 0.08716(6) -0.14260(18) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.9180(9) 0.0239(2) 0.0065(6) 0.0277(11) Uani 1 1 d . . . . .
C3 C 0.5640(9) 0.1013(2) 0.1188(6) 0.0279(11) Uani 1 1 d . . . . .
C2 C 0.6534(9) 0.1286(2) -0.0283(7) 0.0333(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 0 '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'
Se Se -0.0929 2.2259 '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
C5 S4 C3 103.5(7) . . ?
C2 S3 C4 98.8(9) . . ?
S3 C4 H4A 109.5 . . ?
S3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S4 C5 H5A 109.5 . . ?
S4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 Se4 C5B 101.0(4) . . ?
C2 Se3 C4B 98.3(4) . . ?
Se3 C4B H4B1 109.5 . . ?
Se3 C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
Se3 C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
Se4 C5B H5B1 109.5 . . ?
Se4 C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
Se4 C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C3 S2 C1 95.6(2) . . ?
C2 S1 C1 95.9(2) . . ?
C1 C1 S1 124.9(5) 3_755 . ?
C1 C1 S2 121.2(5) 3_755 . ?
S1 C1 S2 113.9(2) . . ?
C2 C3 S2 116.9(3) . . ?
C2 C3 S4 124.5(6) . . ?
S2 C3 S4 118.6(6) . . ?
C2 C3 Se4 122.5(4) . . ?
S2 C3 Se4 120.6(3) . . ?
C3 C2 S1 117.6(4) . . ?
C3 C2 S3 127.4(9) . . ?
S1 C2 S3 114.9(8) . . ?
C3 C2 Se3 123.5(5) . . ?
S1 C2 Se3 118.8(4) . . ?
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
S4 C5 1.808(18) . ?
S4 C3 1.819(11) . ?
S3 C2 1.822(17) . ?
S3 C4 1.890(17) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
Se4 C3 1.832(6) . ?
Se4 C5B 1.861(10) . ?
Se3 C2 1.846(8) . ?
Se3 C4B 1.880(8) . ?
C4B H4B1 0.96 . ?
C4B H4B2 0.96 . ?
C4B H4B3 0.96 . ?
C5B H5B1 0.96 . ?
C5B H5B2 0.96 . ?
C5B H5B3 0.96 . ?
S2 C3 1.753(5) . ?
S2 C1 1.769(4) . ?
S1 C2 1.747(5) . ?
S1 C1 1.750(4) . ?
C1 C1 1.318(8) 3_755 ?
C3 C2 1.349(6) . ?
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 S1 C1 C1 -177.3(6) . . . 3_755 ?
C2 S1 C1 S2 3.8(3) . . . . ?
C3 S2 C1 C1 177.7(6) . . . 3_755 ?
C3 S2 C1 S1 -3.3(3) . . . . ?
C1 S2 C3 C2 1.3(4) . . . . ?
C1 S2 C3 S4 179.3(6) . . . . ?
C1 S2 C3 Se4 -179.9(4) . . . . ?
C5 S4 C3 C2 -166.6(6) . . . . ?
C5 S4 C3 S2 15.6(9) . . . . ?
C5B Se4 C3 C2 -167.5(5) . . . . ?
C5B Se4 C3 S2 13.8(5) . . . . ?
S2 C3 C2 S1 1.2(6) . . . . ?
S4 C3 C2 S1 -176.7(6) . . . . ?
Se4 C3 C2 S1 -177.6(3) . . . . ?
S2 C3 C2 S3 175.5(8) . . . . ?
S4 C3 C2 S3 -2.3(11) . . . . ?
S2 C3 C2 Se3 177.7(4) . . . . ?
Se4 C3 C2 Se3 -1.1(7) . . . . ?
C1 S1 C2 C3 -3.0(5) . . . . ?
C1 S1 C2 S3 -178.1(7) . . . . ?
C1 S1 C2 Se3 -179.7(4) . . . . ?
C4 S3 C2 C3 110.1(9) . . . . ?
C4 S3 C2 S1 -75.4(11) . . . . ?
C4B Se3 C2 C3 113.7(6) . . . . ?
C4B Se3 C2 S1 -69.9(5) . . . . ?
