# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2445804'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;

_audit_creation_date             2019-02-27T15:18:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C5 H6 S3 Se'
_chemical_formula_moiety         'C5 H6 S3 Se'
_chemical_formula_weight         241.24

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   5.2291(6)
_cell_length_b                   20.848(3)
_cell_length_c                   7.6487(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.668(4)
_cell_angle_gamma                90
_cell_volume                     833.78(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1655
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.07
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.902

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5144  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_number            5896
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.954
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_coverage         0
_reflns_number_total             1887
_reflns_number_gt                1352
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+1.8484P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1887
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.1

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?


# END of CIF
_chemical_name_systematic        
4,5-bis(methylseleno)-4',5'-bis(methylthio)-tetrathiafulvalene
_chemical_name_common            (MeSe)2(MeS)2TTF
_chemical_melting_point          371-373
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2445807'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;

_audit_creation_date             2019-11-20T15:57:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H15 F N4 S6 Se2'
_chemical_formula_moiety         'C10 H12 S6 Se2, C12 H3 F N4'
_chemical_formula_weight         704.66

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3729(6)
_cell_length_b                   11.2809(8)
_cell_length_c                   14.7350(11)
_cell_angle_alpha                80.600(2)
_cell_angle_beta                 84.314(3)
_cell_angle_gamma                83.533(2)
_cell_volume                     1359.72(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3466
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.01
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.749

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5782  0.7455                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.7756                          #
#------------------------------------------------------------------------------# 

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.079373
_diffrn_orient_matrix_ub_12      0.072275
_diffrn_orient_matrix_ub_13      0.005068
_diffrn_orient_matrix_ub_21      0.053197
_diffrn_orient_matrix_ub_22      0.016373
_diffrn_orient_matrix_ub_23      0.053906
_diffrn_orient_matrix_ub_31      0.073594
_diffrn_orient_matrix_ub_32      0.051578
_diffrn_orient_matrix_ub_33      -0.04281
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.055
_diffrn_reflns_number            13768
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             6193
_reflns_number_gt                3789
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+2.8099P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6193
_refine_ls_number_parameters     338
_refine_ls_number_restraints     9
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.078

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.3018(5) 0.4753(4) 0.7584(3) 0.0343(10) Uani 1 1 d . . . . .
C2 C 0.5063(5) 0.2862(4) 0.7545(3) 0.0335(10) Uani 1 1 d . . . . .
C3 C 0.4830(5) 0.3277(4) 0.6653(3) 0.0367(10) Uani 1 1 d . . . . .
C4 C 0.5244(8) 0.0727(5) 0.8855(5) 0.085(2) Uani 1 1 d . . . . .
H4A H 0.4781 0.1259 0.9278 0.128 Uiso 1 1 calc R U . . .
H4B H 0.5909 0.0073 0.9175 0.128 Uiso 1 1 calc R U . . .
H4C H 0.4398 0.0411 0.8601 0.128 Uiso 1 1 calc R U . . .
C5 C 0.4791(9) 0.1246(5) 0.5775(5) 0.082(2) Uani 1 1 d . . . . .
H5A H 0.489 0.083 0.6393 0.122 Uiso 1 1 calc R U . . .
H5B H 0.5307 0.0744 0.5343 0.122 Uiso 1 1 calc R U . . .
H5C H 0.367 0.1428 0.567 0.122 Uiso 1 1 calc R U . . .
C6 C 0.1936(5) 0.5643(4) 0.7853(3) 0.0369(10) Uani 1 1 d . . . . .
C7 C -0.0083(5) 0.7547(4) 0.7891(4) 0.0434(11) Uani 1 1 d . . . . .
C8 C 0.0143(6) 0.7124(4) 0.8775(4) 0.0453(12) Uani 1 1 d . . . . .
C9 C -0.0338(9) 0.9498(5) 0.6394(4) 0.093(2) Uani 1 1 d . . . . .
H9A H 0.0769 0.9559 0.6483 0.139 Uiso 1 1 calc R U . . .
H9B H -0.084 1.0281 0.6159 0.139 Uiso 1 1 calc R U . . .
H9C H -0.0387 0.8955 0.5962 0.139 Uiso 1 1 calc R U . . .
C10 C 0.1131(7) 0.8588(5) 0.9915(4) 0.0718(17) Uani 1 1 d . . . . .
H10A H 0.201 0.7984 1.006 0.108 Uiso 1 1 calc R U . . .
H10B H 0.0908 0.9069 1.0402 0.108 Uiso 1 1 calc R U . . .
H10C H 0.1416 0.9096 0.9347 0.108 Uiso 1 1 calc R U . . .
C11 C 0.8930(6) 0.3928(4) 0.6980(3) 0.0416(11) Uani 1 1 d . . . . .
C12 C 0.8131(6) 0.4783(5) 0.6318(3) 0.0459(12) Uani 1 1 d . . . . .
H12 H 0.8345 0.4707 0.5698 0.055 Uiso 0.469(13) 1 calc R U P . .
C13 C 0.7066(6) 0.5709(4) 0.6547(3) 0.0456(12) Uani 1 1 d D . . . .
H13 H 0.6583 0.6254 0.6086 0.055 Uiso 0.902(12) 1 calc R U P . .
C14 C 0.6686(6) 0.5849(4) 0.7490(3) 0.0433(11) Uani 1 1 d . . . . .
C15 C 0.7507(6) 0.5001(4) 0.8160(3) 0.0448(12) Uani 1 1 d D . . . .
H15 H 0.73 0.5073 0.8781 0.054 Uiso 0.740(12) 1 calc R U P . .
C16 C 0.8577(6) 0.4097(4) 0.7915(3) 0.0451(12) Uani 1 1 d D . . . .
H16 H 0.9098 0.357 0.8372 0.054 Uiso 0.888(12) 1 calc R U P . .
C17 C 1.0005(6) 0.2964(5) 0.6737(3) 0.0462(12) Uani 1 1 d . . . . .
C18 C 1.0395(7) 0.2754(5) 0.5818(4) 0.0545(13) Uani 1 1 d . . . . .
C19 C 1.0783(6) 0.2119(5) 0.7427(4) 0.0524(13) Uani 1 1 d . . . . .
C20 C 0.5574(6) 0.6769(4) 0.7748(4) 0.0477(12) Uani 1 1 d . . . . .
C21 C 0.4744(6) 0.7624(5) 0.7076(4) 0.0547(14) Uani 1 1 d . . . . .
C22 C 0.5193(7) 0.6947(5) 0.8676(5) 0.0631(15) Uani 1 1 d . . . . .
N1 N 1.0754(7) 0.2533(5) 0.5094(4) 0.0839(17) Uani 1 1 d . . . . .
N2 N 1.1409(6) 0.1432(5) 0.7961(4) 0.0740(15) Uani 1 1 d . . . . .
N3 N 0.4085(6) 0.8302(5) 0.6550(4) 0.0763(15) Uani 1 1 d . . . . .
N4 N 0.4910(8) 0.7105(6) 0.9410(4) 0.101(2) Uani 1 1 d . . . . .
S1 S 0.40227(14) 0.36723(10) 0.83706(8) 0.0401(3) Uani 1 1 d . . . . .
S2 S 0.35303(15) 0.45986(10) 0.64363(8) 0.0401(3) Uani 1 1 d . . . . .
S3 S 0.08930(14) 0.67054(10) 0.70667(8) 0.0420(3) Uani 1 1 d . . . . .
S4 S 0.13468(15) 0.57668(11) 0.90073(8) 0.0454(3) Uani 1 1 d . . . . .
S5A S 0.64743(9) 0.15610(7) 0.79212(5) 0.0495(3) Uani 0.5460(18) 1 d . . P . .
S5B S -0.14069(10) 0.89187(7) 0.75082(7) 0.0689(3) Uani 0.4540(18) 1 d . . P .
.
S6A S 0.57685(10) 0.26732(7) 0.56207(5) 0.0532(3) Uani 0.5460(18) 1 d . . P . .
S6B S -0.07221(10) 0.78311(7) 0.97903(6) 0.0613(3) Uani 0.4540(18) 1 d . . P .
.
Se1A Se -0.14069(10) 0.89187(7) 0.75082(7) 0.0689(3) Uani 0.5460(18) 1 d . . P
. .
Se1B Se 0.64743(9) 0.15610(7) 0.79212(5) 0.0495(3) Uani 0.4540(18) 1 d . . P .
.
Se2A Se -0.07221(10) 0.78311(7) 0.97903(6) 0.0613(3) Uani 0.5460(18) 1 d . . P
. .
Se2B Se 0.57685(10) 0.26732(7) 0.56207(5) 0.0532(3) Uani 0.4540(18) 1 d . . P .
.
F1 F 0.8431(7) 0.4694(5) 0.5422(4) 0.0609(17) Uani 0.531(7) 1 d . . P . .
F2 F 0.654(3) 0.650(2) 0.5899(16) 0.0609(17) Uani 0.100(6) 1 d D . P . .
F3 F 0.7276(15) 0.5137(10) 0.9041(7) 0.0609(17) Uani 0.259(6) 1 d D . P . .
F4 F 0.922(3) 0.343(2) 0.8604(14) 0.0609(17) Uani 0.114(6) 1 d D . P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C6 1.356(6) . ?
C1 S2 1.735(4) . ?
C1 S1 1.743(4) . ?
C2 C3 1.346(6) . ?
C2 S1 1.746(4) . ?
C2 S5A 1.825(4) . ?
C3 S2 1.748(4) . ?
C3 S6A 1.838(4) . ?
C4 S5A 1.831(6) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 S6A 1.858(6) . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C6 S3 1.747(4) . ?
C6 S4 1.747(5) . ?
C7 C8 1.336(7) . ?
C7 S3 1.747(5) . ?
C7 S5B 1.842(5) . ?
C8 S4 1.740(5) . ?
C8 S6B 1.856(5) . ?
C9 S5B 1.847(7) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 S6B 1.891(6) . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C11 C17 1.401(7) . ?
C11 C12 1.416(6) . ?
C11 C16 1.419(7) . ?
C12 C13 1.358(7) . ?
C12 H12 0.93 . ?
C13 C14 1.425(7) . ?
C13 H13 0.93 . ?
C14 C20 1.389(7) . ?
C14 C15 1.429(7) . ?
C15 C16 1.350(7) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 C18 1.413(8) . ?
C17 C19 1.429(7) . ?
C18 N1 1.138(7) . ?
C19 N2 1.134(6) . ?
C20 C22 1.415(8) . ?
C20 C21 1.438(7) . ?
C21 N3 1.134(6) . ?
C22 N4 1.122(7) . ?

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
C6 C1 S2 123.1(3) . . ?
C6 C1 S1 122.4(3) . . ?
S2 C1 S1 114.4(2) . . ?
C3 C2 S1 117.3(3) . . ?
C3 C2 S5A 123.6(3) . . ?
S1 C2 S5A 119.0(2) . . ?
C2 C3 S2 116.3(3) . . ?
C2 C3 S6A 128.5(3) . . ?
S2 C3 S6A 115.1(2) . . ?
S5A C4 H4A 109.5 . . ?
S5A C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S5A C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S6A C5 H5A 109.5 . . ?
S6A C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S6A C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 S3 122.5(3) . . ?
C1 C6 S4 123.5(3) . . ?
S3 C6 S4 113.9(2) . . ?
C8 C7 S3 117.1(4) . . ?
C8 C7 S5B 123.9(4) . . ?
S3 C7 S5B 119.0(3) . . ?
C7 C8 S4 117.3(4) . . ?
C7 C8 S6B 126.5(4) . . ?
S4 C8 S6B 116.3(3) . . ?
S5B C9 H9A 109.5 . . ?
S5B C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S5B C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S6B C10 H10A 109.5 . . ?
S6B C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S6B C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C11 C12 122.6(4) . . ?
C17 C11 C16 121.3(4) . . ?
C12 C11 C16 116.1(5) . . ?
C13 C12 C11 123.1(5) . . ?
C13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C20 C14 C13 121.7(4) . . ?
C20 C14 C15 121.5(5) . . ?
C13 C14 C15 116.8(4) . . ?
C16 C15 C14 121.8(5) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C11 121.8(5) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
C11 C17 C18 123.6(5) . . ?
C11 C17 C19 120.8(5) . . ?
C18 C17 C19 115.6(5) . . ?
N1 C18 C17 176.6(6) . . ?
N2 C19 C17 178.5(6) . . ?
C14 C20 C22 123.1(5) . . ?
C14 C20 C21 121.6(5) . . ?
C22 C20 C21 115.3(5) . . ?
N3 C21 C20 179.5(7) . . ?
N4 C22 C20 178.7(8) . . ?
C1 S1 C2 95.6(2) . . ?
C1 S2 C3 96.2(2) . . ?
C7 S3 C6 95.4(2) . . ?
C8 S4 C6 95.5(2) . . ?
C2 S5A C4 101.4(2) . . ?
C7 S5B C9 101.4(3) . . ?
C3 S6A C5 99.1(2) . . ?
C8 S6B C10 95.8(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
S1 C2 C3 S2 1.0(5) . . . . ?
S5A C2 C3 S2 -175.6(2) . . . . ?
S1 C2 C3 S6A 178.1(3) . . . . ?
S5A C2 C3 S6A 1.5(6) . . . . ?
S2 C1 C6 S3 2.0(6) . . . . ?
S1 C1 C6 S3 -178.4(3) . . . . ?
S2 C1 C6 S4 177.1(3) . . . . ?
S1 C1 C6 S4 -3.4(6) . . . . ?
S3 C7 C8 S4 -1.3(6) . . . . ?
S5B C7 C8 S4 176.4(3) . . . . ?
S3 C7 C8 S6B 179.4(3) . . . . ?
S5B C7 C8 S6B -2.9(7) . . . . ?
C17 C11 C12 C13 178.9(4) . . . . ?
C16 C11 C12 C13 -0.9(7) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C20 -178.5(4) . . . . ?
C12 C13 C14 C15 1.8(7) . . . . ?
C20 C14 C15 C16 179.3(5) . . . . ?
C13 C14 C15 C16 -0.9(7) . . . . ?
C14 C15 C16 C11 -0.9(7) . . . . ?
C17 C11 C16 C15 -178.0(4) . . . . ?
C12 C11 C16 C15 1.8(7) . . . . ?
C12 C11 C17 C18 0.1(7) . . . . ?
C16 C11 C17 C18 179.8(5) . . . . ?
C12 C11 C17 C19 -179.8(5) . . . . ?
C16 C11 C17 C19 0.0(7) . . . . ?
C13 C14 C20 C22 -178.7(5) . . . . ?
C15 C14 C20 C22 1.0(8) . . . . ?
C13 C14 C20 C21 0.4(7) . . . . ?
C15 C14 C20 C21 -179.9(5) . . . . ?
C6 C1 S1 C2 177.6(4) . . . . ?
S2 C1 S1 C2 -2.8(3) . . . . ?
C3 C2 S1 C1 1.1(4) . . . . ?
S5A C2 S1 C1 177.9(3) . . . . ?
C6 C1 S2 C3 -177.2(4) . . . . ?
S1 C1 S2 C3 3.3(3) . . . . ?
C2 C3 S2 C1 -2.6(4) . . . . ?
S6A C3 S2 C1 180.0(2) . . . . ?
C8 C7 S3 C6 -4.3(4) . . . . ?
S5B C7 S3 C6 177.8(3) . . . . ?
C1 C6 S3 C7 -176.1(4) . . . . ?
S4 C6 S3 C7 8.4(3) . . . . ?
C7 C8 S4 C6 6.3(4) . . . . ?
S6B C8 S4 C6 -174.4(3) . . . . ?
C1 C6 S4 C8 175.6(4) . . . . ?
S3 C6 S4 C8 -9.0(3) . . . . ?
C3 C2 S5A C4 -133.9(4) . . . . ?
S1 C2 S5A C4 49.5(4) . . . . ?
C8 C7 S5B C9 147.3(5) . . . . ?
S3 C7 S5B C9 -35.1(4) . . . . ?
C2 C3 S6A C5 69.3(5) . . . . ?
S2 C3 S6A C5 -113.6(3) . . . . ?
C7 C8 S6B C10 -97.9(5) . . . . ?
S4 C8 S6B C10 82.8(3) . . . . ?


# END of CIF
_chemical_name_common            '[(MeSe)2(MeS)2TTF][TCNQF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2445806'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;

_audit_creation_date             2019-06-19T16:06:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H16 N4 S6 Se2'
_chemical_formula_moiety         'C10 H12 S6 Se2, C12 H4 N4'
_chemical_formula_weight         686.67

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0186(8)
_cell_length_b                   9.4175(9)
_cell_length_c                   17.3009(16)
_cell_angle_alpha                98.667(3)
_cell_angle_beta                 93.154(3)
_cell_angle_gamma                91.170(4)
_cell_volume                     1289.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8357
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      29.77
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_T_max  0.967

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5833  0.7460                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.094398
_diffrn_orient_matrix_ub_12      0.071886
_diffrn_orient_matrix_ub_13      0.002442
_diffrn_orient_matrix_ub_21      0.069101
_diffrn_orient_matrix_ub_22      -0.057026
_diffrn_orient_matrix_ub_23      0.03341
_diffrn_orient_matrix_ub_31      0.043898
_diffrn_orient_matrix_ub_32      -0.055923
_diffrn_orient_matrix_ub_33      -0.048044
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_number            22431
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         30.159
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_reflns_Friedel_coverage         0
_reflns_number_total             6693
_reflns_number_gt                5043
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+2.4397P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6693
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.106

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C -0.0865(4) 0.4282(3) 0.31875(17) 0.0159(6) Uani 1 1 d . . . . .
C2 C -0.3423(4) 0.2845(3) 0.24683(17) 0.0162(6) Uani 1 1 d . . . . .
C3 C -0.2087(4) 0.2202(3) 0.21438(17) 0.0155(6) Uani 1 1 d . . . . .
C6 C 0.0173(4) 0.5153(3) 0.37153(17) 0.0160(6) Uani 1 1 d . . . . .
C7 C 0.2670(4) 0.6414(3) 0.45688(17) 0.0164(6) Uani 1 1 d . . . . .
C8 C 0.1313(4) 0.7039(3) 0.48779(17) 0.0158(6) Uani 1 1 d . . . . .
C11 C -0.3704(4) 0.3743(3) 0.05522(17) 0.0169(6) Uani 1 1 d . . . . .
C12 C -0.4371(4) 0.4858(3) 0.10952(17) 0.0175(6) Uani 1 1 d . . . . .
H12 H -0.5547 0.4905 0.1131 0.021 Uiso 1 1 calc R U . . .
C13 C -0.3364(4) 0.5844(3) 0.15574(18) 0.0172(6) Uani 1 1 d . . . . .
H13 H -0.3843 0.6579 0.1907 0.021 Uiso 1 1 calc R U . . .
C14 C -0.1579(4) 0.5793(3) 0.15261(17) 0.0168(6) Uani 1 1 d . . . . .
C15 C -0.0910(4) 0.4717(3) 0.09590(18) 0.0183(6) Uani 1 1 d . . . . .
H15 H 0.0264 0.469 0.091 0.022 Uiso 1 1 calc R U . . .
C16 C -0.1925(4) 0.3740(3) 0.04934(18) 0.0179(6) Uani 1 1 d . . . . .
H16 H -0.1452 0.304 0.0121 0.022 Uiso 1 1 calc R U . . .
C17 C -0.4728(4) 0.2691(3) 0.00955(18) 0.0180(6) Uani 1 1 d . . . . .
C18 C -0.6507(4) 0.2658(3) 0.01305(18) 0.0196(6) Uani 1 1 d . . . . .
C19 C -0.4046(4) 0.1593(4) -0.0446(2) 0.0262(7) Uani 1 1 d . . . . .
C20 C -0.0525(4) 0.6717(3) 0.20448(18) 0.0186(6) Uani 1 1 d . . . . .
C21 C -0.1142(4) 0.7802(4) 0.26149(19) 0.0210(7) Uani 1 1 d . . . . .
C22 C 0.1254(4) 0.6654(4) 0.20477(19) 0.0237(7) Uani 1 1 d . . . . .
N1 N -0.7938(3) 0.2637(3) 0.01346(17) 0.0269(6) Uani 1 1 d . . . . .
N2 N -0.3482(4) 0.0728(4) -0.0881(2) 0.0424(9) Uani 1 1 d . . . . .
N3 N -0.1617(4) 0.8672(3) 0.30803(18) 0.0311(7) Uani 1 1 d . . . . .
N4 N 0.2686(4) 0.6608(4) 0.2069(2) 0.0366(8) Uani 1 1 d . . . . .
S1 S -0.30362(9) 0.43519(8) 0.31861(4) 0.01786(16) Uani 1 1 d . . . . .
S2 S -0.01195(9) 0.29598(8) 0.24811(4) 0.01713(16) Uani 1 1 d . . . . .
S3 S 0.23445(9) 0.50519(9) 0.37621(4) 0.01787(16) Uani 1 1 d . . . . .
S4 S -0.06286(9) 0.64109(8) 0.44415(4) 0.01713(16) Uani 1 1 d . . . . .
C4A C -0.5653(4) 0.0732(4) 0.2762(2) 0.0319(8) Uani 0.6889(12) 1 d . . P A 1
H4A1 H -0.4843 0.0001 0.2592 0.048 Uiso 0.6889(12) 1 calc R U P A 1
H4A2 H -0.6782 0.0297 0.2695 0.048 Uiso 0.6889(12) 1 calc R U P A 1
H4A3 H -0.5402 0.1121 0.3315 0.048 Uiso 0.6889(12) 1 calc R U P A 1
C5A C -0.0090(4) 0.0276(4) 0.1225(2) 0.0304(8) Uani 0.6889(12) 1 d . . P A 1
H5A1 H 0.045 0.1097 0.1042 0.046 Uiso 0.6889(12) 1 calc R U P A 1
H5A2 H -0.0015 -0.0583 0.0832 0.046 Uiso 0.6889(12) 1 calc R U P A 1
H5A3 H 0.0473 0.0114 0.172 0.046 Uiso 0.6889(12) 1 calc R U P A 1
C9A C 0.5058(5) 0.8317(4) 0.4157(2) 0.0376(9) Uani 0.6889(12) 1 d . . P A 1
H9A1 H 0.4687 0.7829 0.3633 0.056 Uiso 0.6889(12) 1 calc R U P A 1
H9A2 H 0.6226 0.8645 0.4157 0.056 Uiso 0.6889(12) 1 calc R U P A 1
H9A3 H 0.4359 0.9146 0.4302 0.056 Uiso 0.6889(12) 1 calc R U P A 1
C10A C -0.0853(4) 0.8880(4) 0.5809(2) 0.0262(8) Uani 0.6889(12) 1 d . . P A 1
H10A H -0.1344 0.9138 0.5319 0.039 Uiso 0.6889(12) 1 calc R U P A 1
H10B H -0.0998 0.9665 0.6239 0.039 Uiso 0.6889(12) 1 calc R U P A 1
H10C H -0.141 0.8004 0.592 0.039 Uiso 0.6889(12) 1 calc R U P A 1
S5A S -0.5521(6) 0.2209(4) 0.21602(19) 0.0205(5) Uani 0.6889(12) 1 d . . P A 1
S6A S -0.2210(5) 0.0639(6) 0.1370(3) 0.0205(5) Uani 0.6889(12) 1 d . . P A 1
Se1A Se 0.48630(17) 0.70050(9) 0.49021(4) 0.01692(15) Uani 0.6889(12) 1 d . . P
A 1
Se2A Se 0.14404(15) 0.8562(2) 0.57103(17) 0.01692(15) Uani 0.6889(12) 1 d . . P
A 1
C4B C -0.5653(4) 0.0732(4) 0.2762(2) 0.0319(8) Uani 0.3111(12) 1 d . . P A 2
H4B1 H -0.4592 0.0238 0.2703 0.048 Uiso 0.3111(12) 1 calc R U P A 2
H4B2 H -0.6576 0.0071 0.2541 0.048 Uiso 0.3111(12) 1 calc R U P A 2
H4B3 H -0.5803 0.1053 0.3319 0.048 Uiso 0.3111(12) 1 calc R U P A 2
C5B C -0.0090(4) 0.0276(4) 0.1225(2) 0.0304(8) Uani 0.3111(12) 1 d . . P A 2
H5B1 H 0.0088 0.0237 0.0666 0.046 Uiso 0.3111(12) 1 calc R U P A 2
H5B2 H 0.0205 -0.0643 0.1389 0.046 Uiso 0.3111(12) 1 calc R U P A 2
H5B3 H 0.0615 0.105 0.1528 0.046 Uiso 0.3111(12) 1 calc R U P A 2
C9B C 0.5058(5) 0.8317(4) 0.4157(2) 0.0376(9) Uani 0.3111(12) 1 d . . P A 2
H9B1 H 0.5145 0.7885 0.3609 0.056 Uiso 0.3111(12) 1 calc R U P A 2
H9B2 H 0.6043 0.8939 0.4331 0.056 Uiso 0.3111(12) 1 calc R U P A 2
H9B3 H 0.405 0.8889 0.4203 0.056 Uiso 0.3111(12) 1 calc R U P A 2
C10B C -0.0853(4) 0.8880(4) 0.5809(2) 0.0262(8) Uani 0.3111(12) 1 d . . P A 2
H10D H -0.1119 0.9834 0.5684 0.039 Uiso 0.3111(12) 1 calc R U P A 2
H10E H -0.1145 0.8816 0.6345 0.039 Uiso 0.3111(12) 1 calc R U P A 2
H10F H -0.1491 0.8145 0.5443 0.039 Uiso 0.3111(12) 1 calc R U P A 2
Se1B Se -0.5628(5) 0.2307(3) 0.22379(17) 0.01692(15) Uani 0.3111(12) 1 d . . P
A 2
Se2B Se -0.2358(4) 0.0633(5) 0.1401(3) 0.01692(15) Uani 0.3111(12) 1 d . . P A
2
S5B S 0.4935(11) 0.6908(6) 0.4762(2) 0.0205(5) Uani 0.3111(12) 1 d . . P A 2
S6B S 0.1600(9) 0.8566(13) 0.5715(10) 0.0205(5) Uani 0.3111(12) 1 d . . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C6 1.365(4) . ?
C1 S1 1.744(3) . ?
C1 S2 1.747(3) . ?
C2 C3 1.349(4) . ?
C2 S1 1.750(3) . ?
C2 S5A 1.799(5) . ?
C2 Se1B 1.835(5) . ?
C3 S2 1.751(3) . ?
C3 Se2B 1.807(6) . ?
C3 S6A 1.831(6) . ?
C6 S3 1.744(3) . ?
C6 S4 1.751(3) . ?
C7 C8 1.346(4) . ?
C7 S3 1.752(3) . ?
C7 S5B 1.865(9) . ?
C7 Se1A 1.867(3) . ?
C8 S4 1.744(3) . ?
C8 Se2A 1.870(4) . ?
C8 S6B 1.882(16) . ?
C11 C17 1.393(4) . ?
C11 C12 1.432(4) . ?
C11 C16 1.436(4) . ?
C12 C13 1.352(4) . ?
C12 H12 0.95 . ?
C13 C14 1.437(4) . ?
C13 H13 0.95 . ?
C14 C20 1.389(4) . ?
C14 C15 1.434(4) . ?
C15 C16 1.353(4) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C19 1.426(4) . ?
C17 C18 1.431(4) . ?
C18 N1 1.148(4) . ?
C19 N2 1.142(4) . ?
C20 C21 1.425(4) . ?
C20 C22 1.429(4) . ?
C21 N3 1.145(4) . ?
C22 N4 1.149(4) . ?
C4A S5A 1.863(6) . ?
C4A H4A1 0.98 . ?
C4A H4A2 0.98 . ?
C4A H4A3 0.98 . ?
C5A S6A 1.765(6) . ?
C5A H5A1 0.98 . ?
C5A H5A2 0.98 . ?
C5A H5A3 0.98 . ?
C9A Se1A 1.926(4) . ?
C9A H9A1 0.98 . ?
C9A H9A2 0.98 . ?
C9A H9A3 0.98 . ?
C10A Se2A 1.882(4) . ?
C10A H10A 0.98 . ?
C10A H10B 0.98 . ?
C10A H10C 0.98 . ?
C4B Se1B 1.851(5) . ?
C4B H4B1 0.98 . ?
C4B H4B2 0.98 . ?
C4B H4B3 0.98 . ?
C5B Se2B 1.889(5) . ?
C5B H5B1 0.98 . ?
C5B H5B2 0.98 . ?
C5B H5B3 0.98 . ?
C9B S5B 1.815(7) . ?
C9B H9B1 0.98 . ?
C9B H9B2 0.98 . ?
C9B H9B3 0.98 . ?
C10B S6B 2.007(10) . ?
C10B H10D 0.98 . ?
C10B H10E 0.98 . ?
C10B H10F 0.98 . ?

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
C6 C1 S1 122.8(2) . . ?
C6 C1 S2 122.5(2) . . ?
S1 C1 S2 114.64(16) . . ?
C3 C2 S1 117.3(2) . . ?
C3 C2 S5A 121.5(2) . . ?
S1 C2 S5A 121.23(19) . . ?
C3 C2 Se1B 126.8(2) . . ?
S1 C2 Se1B 115.89(18) . . ?
C2 C3 S2 116.7(2) . . ?
C2 C3 Se2B 120.6(3) . . ?
S2 C3 Se2B 122.7(2) . . ?
C2 C3 S6A 124.5(3) . . ?
S2 C3 S6A 118.8(2) . . ?
C1 C6 S3 123.9(2) . . ?
C1 C6 S4 121.0(2) . . ?
S3 C6 S4 114.94(16) . . ?
C8 C7 S3 117.6(2) . . ?
C8 C7 S5B 130.7(3) . . ?
S3 C7 S5B 111.2(2) . . ?
C8 C7 Se1A 123.9(2) . . ?
S3 C7 Se1A 118.43(16) . . ?
C7 C8 S4 116.9(2) . . ?
C7 C8 Se2A 123.0(2) . . ?
S4 C8 Se2A 119.97(17) . . ?
C7 C8 S6B 119.2(3) . . ?
S4 C8 S6B 123.9(3) . . ?
C17 C11 C12 121.8(3) . . ?
C17 C11 C16 120.6(3) . . ?
C12 C11 C16 117.6(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C20 C14 C15 120.7(3) . . ?
C20 C14 C13 121.4(3) . . ?
C15 C14 C13 117.9(3) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C11 C17 C19 121.1(3) . . ?
C11 C17 C18 122.5(3) . . ?
C19 C17 C18 116.3(3) . . ?
N1 C18 C17 177.9(4) . . ?
N2 C19 C17 179.0(4) . . ?
C14 C20 C21 122.3(3) . . ?
C14 C20 C22 122.6(3) . . ?
C21 C20 C22 115.0(3) . . ?
N3 C21 C20 179.0(4) . . ?
N4 C22 C20 178.4(4) . . ?
C1 S1 C2 95.50(14) . . ?
C1 S2 C3 95.63(14) . . ?
C6 S3 C7 95.07(14) . . ?
C8 S4 C6 95.47(14) . . ?
S5A C4A H4A1 109.5 . . ?
S5A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
S5A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
S6A C5A H5A1 109.5 . . ?
S6A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
S6A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
Se1A C9A H9A1 109.5 . . ?
Se1A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
Se1A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
Se2A C10A H10A 109.5 . . ?
Se2A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
Se2A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2 S5A C4A 98.3(2) . . ?
C5A S6A C3 102.9(2) . . ?
C7 Se1A C9A 94.66(15) . . ?
C8 Se2A C10A 99.53(15) . . ?
Se1B C4B H4B1 109.5 . . ?
Se1B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
Se1B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
Se2B C5B H5B1 109.5 . . ?
Se2B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
Se2B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
S5B C9B H9B1 109.5 . . ?
S5B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
S5B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
S6B C10B H10D 109.5 . . ?
S6B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
S6B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C2 Se1B C4B 97.4(2) . . ?
C3 Se2B C5B 99.1(2) . . ?
C9B S5B C7 98.5(4) . . ?
C8 S6B C10B 94.8(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
S1 C2 C3 S2 -0.1(4) . . . . ?
S5A C2 C3 S2 178.4(2) . . . . ?
Se1B C2 C3 S2 180.0(2) . . . . ?
S1 C2 C3 Se2B 179.7(2) . . . . ?
Se1B C2 C3 Se2B -0.2(4) . . . . ?
S1 C2 C3 S6A -178.6(3) . . . . ?
S5A C2 C3 S6A -0.1(4) . . . . ?
S1 C1 C6 S3 176.81(17) . . . . ?
S2 C1 C6 S3 -0.8(4) . . . . ?
S1 C1 C6 S4 0.4(4) . . . . ?
S2 C1 C6 S4 -177.14(17) . . . . ?
S3 C7 C8 S4 0.3(4) . . . . ?
S5B C7 C8 S4 170.8(3) . . . . ?
Se1A C7 C8 S4 175.71(17) . . . . ?
S3 C7 C8 Se2A -177.22(18) . . . . ?
Se1A C7 C8 Se2A -1.8(4) . . . . ?
S3 C7 C8 S6B -177.2(5) . . . . ?
S5B C7 C8 S6B -6.7(6) . . . . ?
C17 C11 C12 C13 177.5(3) . . . . ?
C16 C11 C12 C13 -2.3(5) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C20 -174.2(3) . . . . ?
C12 C13 C14 C15 3.5(4) . . . . ?
C20 C14 C15 C16 174.7(3) . . . . ?
C13 C14 C15 C16 -3.0(5) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C17 C11 C16 C15 -177.0(3) . . . . ?
C12 C11 C16 C15 2.9(5) . . . . ?
C12 C11 C17 C19 179.6(3) . . . . ?
C16 C11 C17 C19 -0.5(5) . . . . ?
C12 C11 C17 C18 0.6(5) . . . . ?
C16 C11 C17 C18 -179.5(3) . . . . ?
C15 C14 C20 C21 179.8(3) . . . . ?
C13 C14 C20 C21 -2.5(5) . . . . ?
C15 C14 C20 C22 -0.2(5) . . . . ?
C13 C14 C20 C22 177.5(3) . . . . ?
C6 C1 S1 C2 -173.0(3) . . . . ?
S2 C1 S1 C2 4.8(2) . . . . ?
C3 C2 S1 C1 -2.8(3) . . . . ?
S5A C2 S1 C1 178.6(2) . . . . ?
Se1B C2 S1 C1 177.1(2) . . . . ?
C6 C1 S2 C3 173.0(3) . . . . ?
S1 C1 S2 C3 -4.8(2) . . . . ?
C2 C3 S2 C1 3.0(3) . . . . ?
Se2B C3 S2 C1 -176.8(3) . . . . ?
S6A C3 S2 C1 -178.4(3) . . . . ?
C1 C6 S3 C7 -178.2(3) . . . . ?
S4 C6 S3 C7 -1.6(2) . . . . ?
C8 C7 S3 C6 0.8(3) . . . . ?
S5B C7 S3 C6 -171.5(3) . . . . ?
Se1A C7 S3 C6 -174.86(19) . . . . ?
C7 C8 S4 C6 -1.3(3) . . . . ?
Se2A C8 S4 C6 176.4(2) . . . . ?
S6B C8 S4 C6 176.1(5) . . . . ?
C1 C6 S4 C8 178.4(3) . . . . ?
S3 C6 S4 C8 1.8(2) . . . . ?
C3 C2 S5A C4A 82.5(3) . . . . ?
S1 C2 S5A C4A -99.0(2) . . . . ?
C2 C3 S6A C5A -178.0(3) . . . . ?
S2 C3 S6A C5A 3.5(4) . . . . ?
C8 C7 Se1A C9A -91.5(3) . . . . ?
S3 C7 Se1A C9A 83.8(2) . . . . ?
C7 C8 Se2A C10A 179.1(3) . . . . ?
S4 C8 Se2A C10A 1.6(2) . . . . ?
C3 C2 Se1B C4B 75.5(3) . . . . ?
S1 C2 Se1B C4B -104.5(2) . . . . ?
C2 C3 Se2B C5B -178.9(3) . . . . ?
S2 C3 Se2B C5B 0.8(3) . . . . ?
C8 C7 S5B C9B -80.6(4) . . . . ?
S3 C7 S5B C9B 90.3(3) . . . . ?
C7 C8 S6B C10B 179.2(3) . . . . ?
S4 C8 S6B C10B 1.8(7) . . . . ?


# END of CIF
_chemical_name_common            '[(MeSe)2(MeS)2TTF][TCNQ]'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2445809'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;

_audit_creation_date             2019-07-08T10:13:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C10 H12 Cl O4 S6 Se2'
_chemical_formula_moiety         '	C10 H12 S6 Se2, Cl O4'
_chemical_formula_weight         581.93

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6170(8)
_cell_length_b                   10.9542(12)
_cell_length_c                   12.8890(14)
_cell_angle_alpha                110.984(3)
_cell_angle_beta                 97.116(4)
_cell_angle_gamma                101.161(3)
_cell_volume                     962.96(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.99
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    2.007
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             570

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_T_max  0.831

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4339  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.071279
_diffrn_orient_matrix_ub_12      0.056489
_diffrn_orient_matrix_ub_13      -0.024091
_diffrn_orient_matrix_ub_21      -0.014955
_diffrn_orient_matrix_ub_22      -0.061098
_diffrn_orient_matrix_ub_23      -0.081418
_diffrn_orient_matrix_ub_31      -0.115915
_diffrn_orient_matrix_ub_32      -0.057537
_diffrn_orient_matrix_ub_33      0.004144
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_number            23609
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             4423
_reflns_number_gt                3356
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+2.5804P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4423
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.099

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
O O 0.0106 0.006 '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'
Cl Cl 0.1484 0.1585 '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_
_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
C1 C 0.8382(6) 0.0661(4) 0.4034(3) 0.0317(9) Uani 1 1 d . . . . .
C2 C 0.8223(6) 0.0237(5) 0.1931(4) 0.0405(10) Uani 1 1 d . . . . .
C3 C 0.9225(6) 0.1539(5) 0.2525(4) 0.0397(10) Uani 1 1 d . . . . .
C6 C 0.8057(6) 0.0509(4) 0.5019(3) 0.0319(9) Uani 1 1 d . . . . .
C7 C 0.7699(6) 0.0853(4) 0.7047(3) 0.0354(9) Uani 1 1 d . . . . .
C8 C 0.6772(6) -0.0438(4) 0.6397(4) 0.0345(9) Uani 1 1 d . . . . .
O1 O 0.7748(6) 0.5839(5) 0.3699(3) 0.0741(12) Uani 1 1 d . . . . .
O2 O 0.5575(16) 0.6374(12) 0.2649(9) 0.0884(15) Uani 0.548(11) 1 d . . P . .
O3 O 0.777(2) 0.5301(11) 0.1784(12) 0.0884(15) Uani 0.548(11) 1 d . . P . .
O4 O 0.5392(18) 0.4123(11) 0.2331(9) 0.0884(15) Uani 0.548(11) 1 d . . P . .
S1 S 0.75234(16) -0.06666(12) 0.27284(9) 0.0397(3) Uani 1 1 d . . . . .
S2 S 0.96319(16) 0.21219(11) 0.39902(9) 0.0371(3) Uani 1 1 d . . . . .
S5 S 0.88313(16) 0.17802(11) 0.63586(9) 0.0369(3) Uani 1 1 d . . . . .
S6 S 0.67966(15) -0.10134(11) 0.49566(9) 0.0359(2) Uani 1 1 d . . . . .
C4A C 0.663(2) -0.2348(19) 0.0202(15) 0.100(6) Uani 0.709(2) 1 d . . P A 1
H4A1 H 0.6316 -0.2872 -0.0603 0.15 Uiso 0.709(2) 1 calc R U P A 1
H4A2 H 0.7466 -0.2708 0.0557 0.15 Uiso 0.709(2) 1 calc R U P A 1
H4A3 H 0.5547 -0.2387 0.0508 0.15 Uiso 0.709(2) 1 calc R U P A 1
C5A C 1.111(9) 0.418(7) 0.303(7) 0.068(5) Uani 0.709(2) 1 d . . P A 1
H5A1 H 1.1702 0.4822 0.2757 0.103 Uiso 0.709(2) 1 calc R U P A 1
H5A2 H 1.0116 0.4472 0.3353 0.103 Uiso 0.709(2) 1 calc R U P A 1
H5A3 H 1.1973 0.411 0.3604 0.103 Uiso 0.709(2) 1 calc R U P A 1
C9A C 0.814(5) 0.337(3) 0.8852(19) 0.065(3) Uani 0.709(2) 1 d . . P A 1
H9A1 H 0.8321 0.3903 0.9651 0.098 Uiso 0.709(2) 1 calc R U P A 1
H9A2 H 0.9124 0.3723 0.8559 0.098 Uiso 0.709(2) 1 calc R U P A 1
H9A3 H 0.7 0.3411 0.8465 0.098 Uiso 0.709(2) 1 calc R U P A 1
C10A C 0.456(3) -0.3255(8) 0.5528(18) 0.047(2) Uani 0.709(2) 1 d . . P A 1
H10A H 0.3926 -0.3997 0.5682 0.071 Uiso 0.709(2) 1 calc R U P A 1
H10B H 0.3719 -0.3021 0.506 0.071 Uiso 0.709(2) 1 calc R U P A 1
H10C H 0.5512 -0.3514 0.5139 0.071 Uiso 0.709(2) 1 calc R U P A 1
S3 S 0.774(4) -0.056(3) 0.0482(17) 0.068(2) Uani 0.709(2) 1 d . . P A 1
S4 S 1.024(4) 0.257(3) 0.1883(18) 0.0573(19) Uani 0.709(2) 1 d . . P A 1
Se1A Se 0.8059(4) 0.15445(14) 0.8618(2) 0.0514(4) Uani 0.709(2) 1 d . . P A 1
Se2A Se 0.5659(7) -0.1680(5) 0.6974(4) 0.0419(4) Uani 0.709(2) 1 d . . P A 1
C4B C 0.609(7) -0.187(5) 0.010(4) 0.100(6) Uani 0.291(2) 1 d . . P A 2
H4B1 H 0.5642 -0.236 -0.07 0.15 Uiso 0.291(2) 1 calc R U P A 2
H4B2 H 0.6644 -0.2418 0.0413 0.15 Uiso 0.291(2) 1 calc R U P A 2
H4B3 H 0.5096 -0.1654 0.046 0.15 Uiso 0.291(2) 1 calc R U P A 2
C5B C 1.13(2) 0.429(19) 0.298(18) 0.068(5) Uani 0.291(2) 1 d . . P A 2
H5B1 H 1.1775 0.4942 0.2681 0.103 Uiso 0.291(2) 1 calc R U P A 2
H5B2 H 1.0454 0.4623 0.3444 0.103 Uiso 0.291(2) 1 calc R U P A 2
H5B3 H 1.2274 0.4156 0.3433 0.103 Uiso 0.291(2) 1 calc R U P A 2
C9B C 0.790(13) 0.344(9) 0.905(6) 0.065(3) Uani 0.291(2) 1 d . . P A 2
H9B1 H 0.8132 0.3887 0.9862 0.098 Uiso 0.291(2) 1 calc R U P A 2
H9B2 H 0.8752 0.3937 0.876 0.098 Uiso 0.291(2) 1 calc R U P A 2
H9B3 H 0.6673 0.3413 0.8733 0.098 Uiso 0.291(2) 1 calc R U P A 2
C10B C 0.459(9) -0.292(3) 0.568(5) 0.047(2) Uani 0.291(2) 1 d . . P A 2
H10D H 0.3899 -0.3624 0.5853 0.071 Uiso 0.291(2) 1 calc R U P A 2
H10E H 0.3784 -0.2656 0.5213 0.071 Uiso 0.291(2) 1 calc R U P A 2
H10F H 0.5501 -0.3237 0.5281 0.071 Uiso 0.291(2) 1 calc R U P A 2
Se1B Se 0.749(4) -0.059(3) 0.0320(17) 0.068(2) Uani 0.291(2) 1 d . . P A 2
Se2B Se 1.001(4) 0.259(3) 0.1733(18) 0.0573(19) Uani 0.291(2) 1 d . . P A 2
S3B S 0.815(3) 0.1830(14) 0.8679(16) 0.0514(4) Uani 0.291(2) 1 d . . P A 2
S4B S 0.559(5) -0.162(3) 0.686(2) 0.0419(4) Uani 0.291(2) 1 d . . P A 2
Cl1 Cl 0.66474(19) 0.53527(13) 0.25845(11) 0.0549(3) Uani 1 1 d . . . . .
O4A O 0.509(2) 0.5762(15) 0.2606(11) 0.0884(15) Uani 0.452(11) 1 d . . P . .
O3A O 0.626(2) 0.3874(14) 0.2219(11) 0.0884(15) Uani 0.452(11) 1 d . . P . .
O2A O 0.769(3) 0.5766(14) 0.1865(15) 0.0884(15) Uani 0.452(11) 1 d . . P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C6 1.384(6) . ?
C1 S2 1.720(4) . ?
C1 S1 1.726(4) . ?
C2 C3 1.362(7) . ?
C2 S3 1.71(2) . ?
C2 S1 1.726(5) . ?
C2 Se1B 1.90(2) . ?
C3 S2 1.728(5) . ?
C3 S4 1.74(3) . ?
C3 Se2B 1.85(2) . ?
C6 S6 1.724(4) . ?
C6 S5 1.725(4) . ?
C7 C8 1.349(6) . ?
C7 S5 1.749(4) . ?
C7 Se1A 1.852(5) . ?
C7 S3B 1.937(19) . ?
C8 S6 1.738(4) . ?
C8 S4B 1.75(3) . ?
C8 Se2A 1.885(6) . ?
O1 Cl1 1.425(4) . ?
O2 O4A 0.679(12) . ?
O2 Cl1 1.493(12) . ?
O3 Cl1 1.411(14) . ?
O4 O3A 0.774(15) . ?
O4 Cl1 1.394(10) . ?
O4 O4A 1.767(19) . ?
C4A S3 1.86(4) . ?
C4A H4A1 0.96 . ?
C4A H4A2 0.96 . ?
C4A H4A3 0.96 . ?
C5A S4 1.78(8) . ?
C5A H5A1 0.96 . ?
C5A H5A2 0.96 . ?
C5A H5A3 0.96 . ?
C9A Se1A 1.90(3) . ?
C9A H9A1 0.96 . ?
C9A H9A2 0.96 . ?
C9A H9A3 0.96 . ?
C10A Se2A 1.975(17) . ?
C10A H10A 0.96 . ?
C10A H10B 0.96 . ?
C10A H10C 0.96 . ?
C4B Se1B 1.50(7) . ?
C4B H4B1 0.96 . ?
C4B H4B2 0.96 . ?
C4B H4B3 0.96 . ?
C5B Se2B 1.9(2) . ?
C5B H5B1 0.96 . ?
C5B H5B2 0.96 . ?
C5B H5B3 0.96 . ?
C9B S3B 1.71(9) . ?
C9B H9B1 0.96 . ?
C9B H9B2 0.96 . ?
C9B H9B3 0.96 . ?
C10B S4B 1.63(6) . ?
C10B H10D 0.96 . ?
C10B H10E 0.96 . ?
C10B H10F 0.96 . ?
Cl1 O4A 1.346(15) . ?
Cl1 O2A 1.426(17) . ?
Cl1 O3A 1.472(14) . ?

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
C6 C1 S2 124.5(3) . . ?
C6 C1 S1 120.4(3) . . ?
S2 C1 S1 115.0(2) . . ?
C3 C2 S3 124.4(12) . . ?
C3 C2 S1 116.2(3) . . ?
S3 C2 S1 119.3(12) . . ?
C3 C2 Se1B 124.4(11) . . ?
S1 C2 Se1B 119.3(11) . . ?
C2 C3 S2 116.9(3) . . ?
C2 C3 S4 123.3(9) . . ?
S2 C3 S4 119.6(8) . . ?
C2 C3 Se2B 119.0(8) . . ?
S2 C3 Se2B 124.1(8) . . ?
C1 C6 S6 120.3(3) . . ?
C1 C6 S5 123.9(3) . . ?
S6 C6 S5 115.8(2) . . ?
C8 C7 S5 116.7(3) . . ?
C8 C7 Se1A 122.0(3) . . ?
S5 C7 Se1A 120.7(3) . . ?
C8 C7 S3B 129.8(6) . . ?
S5 C7 S3B 113.4(5) . . ?
C7 C8 S6 117.0(3) . . ?
C7 C8 S4B 126.8(11) . . ?
S6 C8 S4B 116.3(11) . . ?
C7 C8 Se2A 124.1(3) . . ?
S6 C8 Se2A 118.7(3) . . ?
O4A O2 Cl1 64.3(19) . . ?
O3A O4 Cl1 80.0(15) . . ?
O3A O4 O4A 128.0(17) . . ?
Cl1 O4 O4A 48.6(5) . . ?
C2 S1 C1 95.9(2) . . ?
C1 S2 C3 95.7(2) . . ?
C6 S5 C7 95.0(2) . . ?
C6 S6 C8 95.3(2) . . ?
S3 C4A H4A1 109.5 . . ?
S3 C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
S3 C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
S4 C5A H5A1 109.5 . . ?
S4 C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
S4 C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
Se1A C9A H9A1 109.5 . . ?
Se1A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
Se1A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
Se2A C10A H10A 109.5 . . ?
Se2A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
Se2A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2 S3 C4A 104.0(16) . . ?
C3 S4 C5A 103(2) . . ?
C7 Se1A C9A 97.7(7) . . ?
C8 Se2A C10A 99.3(6) . . ?
Se1B C4B H4B1 109.5 . . ?
Se1B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
Se1B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
Se2B C5B H5B1 109.5 . . ?
Se2B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
Se2B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
S3B C9B H9B1 109.5 . . ?
S3B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
S3B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
S4B C10B H10D 109.5 . . ?
S4B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
S4B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C4B Se1B C2 104(2) . . ?
C3 Se2B C5B 101(5) . . ?
C9B S3B C7 112(3) . . ?
C10B S4B C8 104(2) . . ?
O4A Cl1 O4 80.3(7) . . ?
O4A Cl1 O3 126.9(8) . . ?
O4 Cl1 O3 113.4(6) . . ?
O4A Cl1 O1 111.2(6) . . ?
O4 Cl1 O1 111.0(5) . . ?
O3 Cl1 O1 110.2(6) . . ?
O4A Cl1 O2A 112.0(8) . . ?
O4 Cl1 O2A 128.8(8) . . ?
O3 Cl1 O2A 20.3(8) . . ?
O1 Cl1 O2A 109.6(7) . . ?
O4A Cl1 O3A 111.0(7) . . ?
O4 Cl1 O3A 31.2(6) . . ?
O3 Cl1 O3A 90.1(6) . . ?
O1 Cl1 O3A 102.9(6) . . ?
O2A Cl1 O3A 109.6(7) . . ?
O4A Cl1 O2 27.1(5) . . ?
O4 Cl1 O2 107.1(6) . . ?
O3 Cl1 O2 110.5(6) . . ?
O1 Cl1 O2 104.2(5) . . ?
O2A Cl1 O2 91.6(7) . . ?
O3A Cl1 O2 137.1(7) . . ?
O2 O4A Cl1 89(2) . . ?
O2 O4A O4 139(2) . . ?
Cl1 O4A O4 51.1(6) . . ?
O4 O3A Cl1 68.8(15) . . ?

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 C2 C3 S2 -177.3(13) . . . . ?
S1 C2 C3 S2 -1.0(5) . . . . ?
Se1B C2 C3 S2 176.4(12) . . . . ?
S3 C2 C3 S4 -2.6(18) . . . . ?
S1 C2 C3 S4 173.7(11) . . . . ?
S1 C2 C3 Se2B -179.3(10) . . . . ?
Se1B C2 C3 Se2B -1.9(16) . . . . ?
S2 C1 C6 S6 -179.5(2) . . . . ?
S1 C1 C6 S6 0.3(5) . . . . ?
S2 C1 C6 S5 1.1(6) . . . . ?
S1 C1 C6 S5 -179.1(2) . . . . ?
S5 C7 C8 S6 -0.7(5) . . . . ?
Se1A C7 C8 S6 -171.8(3) . . . . ?
S3B C7 C8 S6 -175.3(9) . . . . ?
S5 C7 C8 S4B 177.5(14) . . . . ?
S3B C7 C8 S4B 2.9(18) . . . . ?
S5 C7 C8 Se2A 173.4(3) . . . . ?
Se1A C7 C8 Se2A 2.3(6) . . . . ?
C3 C2 S1 C1 3.8(4) . . . . ?
S3 C2 S1 C1 -179.7(13) . . . . ?
Se1B C2 S1 C1 -173.7(11) . . . . ?
C6 C1 S1 C2 174.8(4) . . . . ?
S2 C1 S1 C2 -5.4(3) . . . . ?
C6 C1 S2 C3 -175.2(4) . . . . ?
S1 C1 S2 C3 5.0(3) . . . . ?
C2 C3 S2 C1 -2.4(4) . . . . ?
S4 C3 S2 C1 -177.3(11) . . . . ?
Se2B C3 S2 C1 175.8(11) . . . . ?
C1 C6 S5 C7 174.6(4) . . . . ?
S6 C6 S5 C7 -4.8(3) . . . . ?
C8 C7 S5 C6 3.3(4) . . . . ?
Se1A C7 S5 C6 174.5(3) . . . . ?
S3B C7 S5 C6 178.8(8) . . . . ?
C1 C6 S6 C8 -174.9(4) . . . . ?
S5 C6 S6 C8 4.5(3) . . . . ?
C7 C8 S6 C6 -2.3(4) . . . . ?
S4B C8 S6 C6 179.3(13) . . . . ?
Se2A C8 S6 C6 -176.7(3) . . . . ?
C3 C2 S3 C4A 172.5(9) . . . . ?
S1 C2 S3 C4A -4(2) . . . . ?
C2 C3 S4 C5A 173(3) . . . . ?
S2 C3 S4 C5A -12(3) . . . . ?
C8 C7 Se1A C9A -150.1(10) . . . . ?
S5 C7 Se1A C9A 39.2(10) . . . . ?
C7 C8 Se2A C10A 178.2(7) . . . . ?
S6 C8 Se2A C10A -7.8(7) . . . . ?
C2 C3 Se2B C5B 179(6) . . . . ?
S2 C3 Se2B C5B 1(6) . . . . ?
C7 C8 S4B C10B 174(2) . . . . ?
S6 C8 S4B C10B -8(3) . . . . ?
O3A O4 Cl1 O4A 170.8(16) . . . . ?
O3A O4 Cl1 O3 44.6(16) . . . . ?
O4A O4 Cl1 O3 -126.2(9) . . . . ?
O3A O4 Cl1 O1 -80.1(15) . . . . ?
O4A O4 Cl1 O1 109.1(6) . . . . ?
O3A O4 Cl1 O2A 60(2) . . . . ?
O4A O4 Cl1 O2A -110.6(11) . . . . ?
O4A O4 Cl1 O3A -170.8(16) . . . . ?
O3A O4 Cl1 O2 166.8(14) . . . . ?
O4A O4 Cl1 O2 -4.0(8) . . . . ?
O4A O2 Cl1 O4 8.7(18) . . . . ?
O4A O2 Cl1 O3 132.7(18) . . . . ?
O4A O2 Cl1 O1 -108.9(17) . . . . ?
O4A O2 Cl1 O2A 140.3(17) . . . . ?
O4A O2 Cl1 O3A 19(2) . . . . ?
Cl1 O2 O4A O4 -10(2) . . . . ?
O4 Cl1 O4A O2 -171.6(18) . . . . ?
O3 Cl1 O4A O2 -59(2) . . . . ?
O1 Cl1 O4A O2 79.6(17) . . . . ?
O2A Cl1 O4A O2 -43.5(18) . . . . ?
O3A Cl1 O4A O2 -166.5(16) . . . . ?
O3 Cl1 O4A O4 112.1(8) . . . . ?
O1 Cl1 O4A O4 -108.9(5) . . . . ?
O2A Cl1 O4A O4 128.1(8) . . . . ?
O3A Cl1 O4A O4 5.1(9) . . . . ?
O2 Cl1 O4A O4 171.6(18) . . . . ?
O3A O4 O4A O2 1(4) . . . . ?
Cl1 O4 O4A O2 13(3) . . . . ?
O3A O4 O4A Cl1 -12(2) . . . . ?
O4A O4 O3A Cl1 8.8(15) . . . . ?
O4A Cl1 O3A O4 -9.7(17) . . . . ?
O3 Cl1 O3A O4 -139.9(15) . . . . ?
O1 Cl1 O3A O4 109.3(15) . . . . ?
O2A Cl1 O3A O4 -134.1(17) . . . . ?
O2 Cl1 O3A O4 -19(2) . . . . ?


# END of CIF
_chemical_name_systematic        
"4,5-bis(methylseleno)-4',5'-bis(methylthio)-tetrathiafulvalenium, perchlorate"
_chemical_name_common            '[(MeSe)2(MeS)2TTF][ClO4]'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2445808'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;

_audit_creation_date             2019-07-08T10:30:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C22 H12 F2 N4 S6 Se2'
_chemical_formula_moiety         'C10 H12 S6 Se2, C12 F2 N4'
_chemical_formula_weight         720.64

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3766(7)
_cell_length_b                   11.2683(9)
_cell_length_c                   14.7324(11)
_cell_angle_alpha                80.619(3)
_cell_angle_beta                 84.373(3)
_cell_angle_gamma                83.538(3)
_cell_volume                     1358.76(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6420
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.908

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4878  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.084118
_diffrn_orient_matrix_ub_12      -0.051256
_diffrn_orient_matrix_ub_13      0.036455
_diffrn_orient_matrix_ub_21      0.069109
_diffrn_orient_matrix_ub_22      0.06858
_diffrn_orient_matrix_ub_23      -0.011049
_diffrn_orient_matrix_ub_31      -0.051758
_diffrn_orient_matrix_ub_32      0.028968
_diffrn_orient_matrix_ub_33      0.057564
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.067
_diffrn_reflns_number            22300
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.406
_diffrn_reflns_theta_max         27.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             6273
_reflns_number_gt                3669
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+4.9749P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6273
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.631
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.1

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C -0.1925(6) 0.4355(5) 0.2139(4) 0.0380(12) Uani 1 1 d . . . . .
C2 C -0.0137(7) 0.2873(5) 0.1224(4) 0.0459(14) Uani 1 1 d . . . . .
C3 C 0.0083(7) 0.2449(5) 0.2116(4) 0.0442(14) Uani 1 1 d . . . . .
C6 C -0.3020(6) 0.5245(5) 0.2415(3) 0.0361(12) Uani 1 1 d . . . . .
C7 C -0.4829(6) 0.6720(5) 0.3346(4) 0.0368(12) Uani 1 1 d . . . . .
C8 C -0.5050(6) 0.7149(5) 0.2451(4) 0.0357(12) Uani 1 1 d . . . . .
C11 C 1.3318(7) 0.4150(5) 0.2512(4) 0.0437(14) Uani 1 1 d . . . . .
C12 C 1.4436(7) 0.3230(5) 0.2260(4) 0.0493(15) Uani 1 1 d . . . . .
C13 C 1.4813(8) 0.3050(7) 0.1323(6) 0.0633(18) Uani 1 1 d . . . . .
C14 C 1.5256(8) 0.2366(6) 0.2925(5) 0.0557(16) Uani 1 1 d . . . . .
C15 C 1.2497(8) 0.5005(6) 0.1849(4) 0.0455(14) Uani 1 1 d . . . . .
C16 C 1.1431(7) 0.5894(6) 0.2083(4) 0.0471(14) Uani 1 1 d . . . . .
C17 C 1.1075(7) 0.6065(5) 0.3025(4) 0.0434(13) Uani 1 1 d . . . . .
C18 C 1.1881(7) 0.5210(5) 0.3677(4) 0.0436(14) Uani 1 1 d . . . . .
C19 C 1.2920(7) 0.4300(5) 0.3446(4) 0.0444(14) Uani 1 1 d . . . . .
C20 C 0.9996(7) 0.7027(6) 0.3260(4) 0.0471(14) Uani 1 1 d . . . . .
C21 C 0.9220(7) 0.7880(6) 0.2578(5) 0.0526(15) Uani 1 1 d . . . . .
C22 C 0.9614(8) 0.7244(6) 0.4184(5) 0.0557(16) Uani 1 1 d . . . . .
F1A F 1.2716(12) 0.4876(9) 0.1015(7) 0.128(2) Uani 0.658(5) 1 d . . P . .
F2A F 1.1593(12) 0.5311(9) 0.4554(7) 0.128(2) Uani 0.658(5) 1 d . . P . .
F1B F 1.343(2) 0.3648(17) 0.3963(13) 0.128(2) Uani 0.342(5) 1 d . . P . .
F2B F 1.083(2) 0.6528(17) 0.1487(13) 0.128(2) Uani 0.342(5) 1 d . . P . .
N1 N 1.5102(9) 0.2883(8) 0.0586(5) 0.100(3) Uani 1 1 d . . . . .
N2 N 1.5916(8) 0.1688(6) 0.3452(5) 0.0783(19) Uani 1 1 d . . . . .
N3 N 0.9252(9) 0.7468(6) 0.4909(5) 0.087(2) Uani 1 1 d . . . . .
N4 N 0.8594(7) 0.8574(6) 0.2047(5) 0.0750(18) Uani 1 1 d . . . . .
S1 S -0.13513(18) 0.42310(13) 0.09917(10) 0.0458(4) Uani 1 1 d . . . . .
S2 S -0.08948(17) 0.32927(12) 0.29340(10) 0.0424(4) Uani 1 1 d . . . . .
S3 S -0.35270(18) 0.53995(12) 0.35635(9) 0.0412(3) Uani 1 1 d . . . . .
S4 S -0.40194(17) 0.63283(12) 0.16294(9) 0.0403(3) Uani 1 1 d . . . . .
C4A C -0.111(3) 0.1281(15) 0.0165(13) 0.0639(15) Uani 0.536(2) 1 d . . P A 1
H4A1 H -0.0947 0.0838 -0.0346 0.096 Uiso 0.536(2) 1 calc R U P A 1
H4A2 H -0.12 0.0727 0.0732 0.096 Uiso 0.536(2) 1 calc R U P A 1
H4A3 H -0.2081 0.1819 0.011 0.096 Uiso 0.536(2) 1 calc R U P A 1
C5A C 0.0578(19) 0.0561(17) 0.3627(14) 0.0639(15) Uani 0.536(2) 1 d . . P A 1
H5A1 H 0.1177 -0.0175 0.3881 0.096 Uiso 0.536(2) 1 calc R U P A 1
H5A2 H 0.0658 0.1176 0.3997 0.096 Uiso 0.536(2) 1 calc R U P A 1
H5A3 H -0.0533 0.0427 0.3624 0.096 Uiso 0.536(2) 1 calc R U P A 1
C9A C -0.460(2) 0.8635(14) 0.4305(12) 0.0639(15) Uani 0.536(2) 1 d . . P A 1
H9A1 H -0.4939 0.9039 0.4826 0.096 Uiso 0.536(2) 1 calc R U P A 1
H9A2 H -0.3458 0.8396 0.4299 0.096 Uiso 0.536(2) 1 calc R U P A 1
H9A3 H -0.4821 0.9173 0.3747 0.096 Uiso 0.536(2) 1 calc R U P A 1
C10A C -0.531(2) 0.9164(15) 0.1053(11) 0.0639(15) Uani 0.536(2) 1 d . . P A 1
H10A H -0.5906 0.9915 0.0824 0.096 Uiso 0.536(2) 1 calc R U P A 1
H10B H -0.4236 0.9308 0.1145 0.096 Uiso 0.536(2) 1 calc R U P A 1
H10C H -0.5271 0.8617 0.0613 0.096 Uiso 0.536(2) 1 calc R U P A 1
Se1A Se 0.0698(5) 0.2204(4) 0.01604(17) 0.0537(6) Uani 0.536(2) 1 d . . P A 1
Se2A Se 0.1410(5) 0.1054(3) 0.24360(19) 0.0580(7) Uani 0.536(2) 1 d . . P A 1
S5A S -0.562(4) 0.737(4) 0.438(3) 0.0513(15) Uani 0.536(2) 1 d . . P A 1
S6A S -0.631(2) 0.8502(19) 0.2149(15) 0.0443(10) Uani 0.536(2) 1 d . . P A 1
C4B C -0.113(3) 0.1554(18) -0.0016(16) 0.0639(15) Uani 0.464(2) 1 d . . P A 2
H4B1 H -0.0834 0.1071 -0.0498 0.096 Uiso 0.464(2) 1 calc R U P A 2
H4B2 H -0.1691 0.1087 0.0496 0.096 Uiso 0.464(2) 1 calc R U P A 2
H4B3 H -0.182 0.2256 -0.0244 0.096 Uiso 0.464(2) 1 calc R U P A 2
C5B C 0.008(2) 0.042(2) 0.3589(17) 0.0639(15) Uani 0.464(2) 1 d . . P A 2
H5B1 H 0.0675 -0.0262 0.3926 0.096 Uiso 0.464(2) 1 calc R U P A 2
H5B2 H -0.0373 0.0967 0.4002 0.096 Uiso 0.464(2) 1 calc R U P A 2
H5B3 H -0.0776 0.014 0.3313 0.096 Uiso 0.464(2) 1 calc R U P A 2
C9B C -0.500(3) 0.8865(17) 0.4146(14) 0.0639(15) Uani 0.464(2) 1 d . . P A 2
H9B1 H -0.5415 0.9315 0.4633 0.096 Uiso 0.464(2) 1 calc R U P A 2
H9B2 H -0.3848 0.8759 0.4122 0.096 Uiso 0.464(2) 1 calc R U P A 2
H9B3 H -0.5336 0.9297 0.3567 0.096 Uiso 0.464(2) 1 calc R U P A 2
C10B C -0.511(2) 0.9419(17) 0.1282(13) 0.0639(15) Uani 0.464(2) 1 d . . P A 2
H10D H -0.5709 1.0143 0.1008 0.096 Uiso 0.464(2) 1 calc R U P A 2
H10E H -0.4322 0.9625 0.1646 0.096 Uiso 0.464(2) 1 calc R U P A 2
H10F H -0.4574 0.8996 0.0805 0.096 Uiso 0.464(2) 1 calc R U P A 2
S5B S 0.0808(18) 0.2054(12) 0.0388(7) 0.0537(6) Uani 0.464(2) 1 d . . P A 2
S6B S 0.1414(16) 0.1185(11) 0.2689(7) 0.0580(7) Uani 0.464(2) 1 d . . P A 2
Se1B Se -0.5829(19) 0.7308(17) 0.4376(14) 0.0513(15) Uani 0.464(2) 1 d . . P A
2
Se2B Se -0.6540(9) 0.8412(8) 0.2048(6) 0.0443(10) Uani 0.464(2) 1 d . . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C6 1.367(7) . ?
C1 S1 1.734(6) . ?
C1 S2 1.749(5) . ?
C2 C3 1.346(8) . ?
C2 S5B 1.736(14) . ?
C2 S1 1.744(6) . ?
C2 Se1A 1.888(7) . ?
C3 S2 1.741(6) . ?
C3 Se2A 1.842(6) . ?
C3 S6B 1.849(13) . ?
C6 S3 1.735(5) . ?
C6 S4 1.741(5) . ?
C7 C8 1.352(7) . ?
C7 S3 1.748(5) . ?
C7 S5A 1.83(4) . ?
C7 Se1B 1.84(2) . ?
C8 S4 1.745(5) . ?
C8 S6A 1.77(2) . ?
C8 Se2B 1.845(10) . ?
C11 C12 1.388(8) . ?
C11 C19 1.417(8) . ?
C11 C15 1.425(8) . ?
C12 C13 1.428(10) . ?
C12 C14 1.432(9) . ?
C13 N1 1.130(9) . ?
C14 N2 1.134(8) . ?
C15 F1A 1.253(10) . ?
C15 C16 1.330(8) . ?
C16 F2B 1.155(17) . ?
C16 C17 1.430(8) . ?
C17 C20 1.398(8) . ?
C17 C18 1.409(8) . ?
C18 F2A 1.312(10) . ?
C18 C19 1.334(8) . ?
C19 F1B 1.053(18) . ?
C20 C22 1.422(9) . ?
C20 C21 1.424(9) . ?
C21 N4 1.134(8) . ?
C22 N3 1.141(8) . ?
C4A Se1A 1.93(2) . ?
C4A H4A1 0.96 . ?
C4A H4A2 0.96 . ?
C4A H4A3 0.96 . ?
C5A Se2A 1.84(2) . ?
C5A H5A1 0.96 . ?
C5A H5A2 0.96 . ?
C5A H5A3 0.96 . ?
C9A S5A 1.73(4) . ?
C9A H9A1 0.96 . ?
C9A H9A2 0.96 . ?
C9A H9A3 0.96 . ?
C10A S6A 1.83(3) . ?
C10A H10A 0.96 . ?
C10A H10B 0.96 . ?
C10A H10C 0.96 . ?
C4B S5B 1.95(3) . ?
C4B H4B1 0.96 . ?
C4B H4B2 0.96 . ?
C4B H4B3 0.96 . ?
C5B S6B 1.82(3) . ?
C5B H5B1 0.96 . ?
C5B H5B2 0.96 . ?
C5B H5B3 0.96 . ?
C9B Se1B 1.92(3) . ?
C9B H9B1 0.96 . ?
C9B H9B2 0.96 . ?
C9B H9B3 0.96 . ?
C10B Se2B 1.90(2) . ?
C10B H10D 0.96 . ?
C10B H10E 0.96 . ?
C10B H10F 0.96 . ?

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
C6 C1 S1 123.7(4) . . ?
C6 C1 S2 121.6(4) . . ?
S1 C1 S2 114.6(3) . . ?
C3 C2 S5B 118.5(5) . . ?
C3 C2 S1 117.0(4) . . ?
S5B C2 S1 124.4(5) . . ?
C3 C2 Se1A 129.0(4) . . ?
S1 C2 Se1A 114.0(3) . . ?
C2 C3 S2 117.1(4) . . ?
C2 C3 Se2A 120.6(4) . . ?
S2 C3 Se2A 122.3(4) . . ?
C2 C3 S6B 132.9(5) . . ?
S2 C3 S6B 109.7(4) . . ?
C1 C6 S3 123.4(4) . . ?
C1 C6 S4 122.1(4) . . ?
S3 C6 S4 114.5(3) . . ?
C8 C7 S3 116.5(4) . . ?
C8 C7 S5A 129.2(15) . . ?
S3 C7 S5A 114.2(14) . . ?
C8 C7 Se1B 127.8(7) . . ?
S3 C7 Se1B 115.6(7) . . ?
C7 C8 S4 116.9(4) . . ?
C7 C8 S6A 120.4(8) . . ?
S4 C8 S6A 122.7(8) . . ?
C7 C8 Se2B 124.8(5) . . ?
S4 C8 Se2B 117.8(4) . . ?
C12 C11 C19 122.1(5) . . ?
C12 C11 C15 122.3(6) . . ?
C19 C11 C15 115.6(5) . . ?
C11 C12 C13 122.6(6) . . ?
C11 C12 C14 122.4(6) . . ?
C13 C12 C14 115.0(6) . . ?
N1 C13 C12 178.5(9) . . ?
N2 C14 C12 179.4(8) . . ?
F1A C15 C16 118.4(7) . . ?
F1A C15 C11 118.8(7) . . ?
C16 C15 C11 122.7(5) . . ?
F2B C16 C15 116.7(11) . . ?
F2B C16 C17 122.0(11) . . ?
C15 C16 C17 121.4(5) . . ?
C20 C17 C18 123.6(5) . . ?
C20 C17 C16 120.9(5) . . ?
C18 C17 C16 115.6(5) . . ?
F2A C18 C19 118.4(6) . . ?
F2A C18 C17 118.5(7) . . ?
C19 C18 C17 123.2(5) . . ?
F1B C19 C18 120.2(12) . . ?
F1B C19 C11 118.3(12) . . ?
C18 C19 C11 121.5(5) . . ?
C17 C20 C22 123.1(6) . . ?
C17 C20 C21 121.8(6) . . ?
C22 C20 C21 115.1(6) . . ?
N4 C21 C20 178.7(7) . . ?
N3 C22 C20 176.4(8) . . ?
C1 S1 C2 95.4(3) . . ?
C3 S2 C1 95.2(3) . . ?
C6 S3 C7 96.1(2) . . ?
C6 S4 C8 95.9(2) . . ?
Se1A C4A H4A1 109.5 . . ?
Se1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
Se1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
Se2A C5A H5A1 109.5 . . ?
Se2A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
Se2A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
S5A C9A H9A1 109.5 . . ?
S5A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
S5A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
S6A C10A H10A 109.5 . . ?
S6A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
S6A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2 Se1A C4A 94.1(7) . . ?
C3 Se2A C5A 101.0(6) . . ?
C9A S5A C7 104(2) . . ?
C8 S6A C10A 102.6(13) . . ?
S5B C4B H4B1 109.5 . . ?
S5B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
S5B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
S6B C5B H5B1 109.5 . . ?
S6B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
S6B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
Se1B C9B H9B1 109.5 . . ?
Se1B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
Se1B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
Se2B C10B H10D 109.5 . . ?
Se2B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
Se2B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C2 S5B C4B 97.4(10) . . ?
C5B S6B C3 103.8(10) . . ?
C7 Se1B C9B 97.8(10) . . ?
C8 Se2B C10B 98.5(8) . . ?

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
S5B C2 C3 S2 -179.6(7) . . . . ?
S1 C2 C3 S2 1.0(7) . . . . ?
Se1A C2 C3 S2 -179.2(4) . . . . ?
S1 C2 C3 Se2A -177.5(3) . . . . ?
Se1A C2 C3 Se2A 2.2(9) . . . . ?
S5B C2 C3 S6B 7.6(12) . . . . ?
S1 C2 C3 S6B -171.7(7) . . . . ?
S1 C1 C6 S3 -177.3(3) . . . . ?
S2 C1 C6 S3 -1.3(7) . . . . ?
S1 C1 C6 S4 2.5(7) . . . . ?
S2 C1 C6 S4 178.5(3) . . . . ?
S3 C7 C8 S4 0.3(6) . . . . ?
S5A C7 C8 S4 176.7(15) . . . . ?
Se1B C7 C8 S4 -175.7(7) . . . . ?
S3 C7 C8 S6A -178.5(7) . . . . ?
S5A C7 C8 S6A -2.1(18) . . . . ?
S3 C7 C8 Se2B 172.3(4) . . . . ?
Se1B C7 C8 Se2B -3.8(10) . . . . ?
C19 C11 C12 C13 178.2(6) . . . . ?
C15 C11 C12 C13 -1.9(9) . . . . ?
C19 C11 C12 C14 0.5(9) . . . . ?
C15 C11 C12 C14 -179.6(6) . . . . ?
C12 C11 C15 F1A 4.6(10) . . . . ?
C19 C11 C15 F1A -175.5(7) . . . . ?
C12 C11 C15 C16 -179.6(6) . . . . ?
C19 C11 C15 C16 0.4(9) . . . . ?
F1A C15 C16 F2B -3.7(15) . . . . ?
C11 C15 C16 F2B -179.5(12) . . . . ?
F1A C15 C16 C17 177.6(7) . . . . ?
C11 C15 C16 C17 1.8(10) . . . . ?
F2B C16 C17 C20 -1.0(15) . . . . ?
C15 C16 C17 C20 177.7(6) . . . . ?
F2B C16 C17 C18 179.2(13) . . . . ?
C15 C16 C17 C18 -2.2(9) . . . . ?
C20 C17 C18 F2A 0.8(10) . . . . ?
C16 C17 C18 F2A -179.4(7) . . . . ?
C20 C17 C18 C19 -179.4(6) . . . . ?
C16 C17 C18 C19 0.5(9) . . . . ?
F2A C18 C19 F1B 4.3(16) . . . . ?
C17 C18 C19 F1B -175.5(14) . . . . ?
F2A C18 C19 C11 -178.5(7) . . . . ?
C17 C18 C19 C11 1.6(9) . . . . ?
C12 C11 C19 F1B -4.9(16) . . . . ?
C15 C11 C19 F1B 175.2(14) . . . . ?
C12 C11 C19 C18 177.9(6) . . . . ?
C15 C11 C19 C18 -2.0(8) . . . . ?
C18 C17 C20 C22 0.5(9) . . . . ?
C16 C17 C20 C22 -179.3(6) . . . . ?
C18 C17 C20 C21 179.3(6) . . . . ?
C16 C17 C20 C21 -0.6(9) . . . . ?
C6 C1 S1 C2 -175.4(5) . . . . ?
S2 C1 S1 C2 8.4(4) . . . . ?
C3 C2 S1 C1 -5.7(5) . . . . ?
S5B C2 S1 C1 175.0(8) . . . . ?
Se1A C2 S1 C1 174.5(4) . . . . ?
C2 C3 S2 C1 4.2(5) . . . . ?
Se2A C3 S2 C1 -177.3(4) . . . . ?
S6B C3 S2 C1 178.6(6) . . . . ?
C6 C1 S2 C3 175.7(5) . . . . ?
S1 C1 S2 C3 -8.0(4) . . . . ?
C1 C6 S3 C7 176.9(5) . . . . ?
S4 C6 S3 C7 -2.9(4) . . . . ?
C8 C7 S3 C6 1.6(5) . . . . ?
S5A C7 S3 C6 -175.4(13) . . . . ?
Se1B C7 S3 C6 178.1(6) . . . . ?
C1 C6 S4 C8 -176.8(5) . . . . ?
S3 C6 S4 C8 3.0(4) . . . . ?
C7 C8 S4 C6 -2.0(5) . . . . ?
S6A C8 S4 C6 176.7(8) . . . . ?
Se2B C8 S4 C6 -174.6(4) . . . . ?
C3 C2 Se1A C4A 90.5(8) . . . . ?
S1 C2 Se1A C4A -89.8(5) . . . . ?
C2 C3 Se2A C5A -155.8(7) . . . . ?
S2 C3 Se2A C5A 25.8(7) . . . . ?
C8 C7 S5A C9A -69(2) . . . . ?
S3 C7 S5A C9A 107.0(19) . . . . ?
C7 C8 S6A C10A 146.1(8) . . . . ?
S4 C8 S6A C10A -32.7(11) . . . . ?
C3 C2 S5B C4B 112.3(7) . . . . ?
S1 C2 S5B C4B -68.4(9) . . . . ?
C2 C3 S6B C5B -132.8(10) . . . . ?
S2 C3 S6B C5B 54.1(9) . . . . ?
C8 C7 Se1B C9B -63.8(11) . . . . ?
S3 C7 Se1B C9B 120.1(8) . . . . ?
C7 C8 Se2B C10B 124.2(7) . . . . ?
S4 C8 Se2B C10B -64.0(6) . . . . ?


# END of CIF
_chemical_name_common            '[(MeSe)2(MeS)2TTF][TCNQF2]'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2445805'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2025-04-22 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;

_audit_creation_date             2019-02-27T15:45:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C10 H12 S6 Se2'
_chemical_formula_moiety         'C10 H12 S6 Se2'
_chemical_formula_weight         482.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.9738(7)
_cell_length_b                   7.8363(4)
_cell_length_c                   16.0601(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.820(2)
_cell_angle_gamma                90
_cell_volume                     1692.02(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.36
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.306
_exptl_absorpt_correction_T_max  0.816

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4386  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.044023
_diffrn_orient_matrix_ub_12      -0.088601
_diffrn_orient_matrix_ub_13      -0.015051
_diffrn_orient_matrix_ub_21      0.003481
_diffrn_orient_matrix_ub_22      0.068489
_diffrn_orient_matrix_ub_23      -0.051632
_diffrn_orient_matrix_ub_31      0.059851
_diffrn_orient_matrix_ub_32      0.061188
_diffrn_orient_matrix_ub_33      0.035999
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_number            33321
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3871
_reflns_number_gt                2705
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+5.0664P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3871
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.1

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
C1 C 0.6422(4) 0.5981(7) 0.6784(4) 0.0420(13) Uani 1 1 d . . . . .
C2 C 0.6563(5) 0.6244(8) 0.5229(4) 0.0488(15) Uani 1 1 d . . . . .
C3 C 0.7154(4) 0.4942(8) 0.5576(4) 0.0517(16) Uani 1 1 d . . . . .
C6 C 0.5976(4) 0.5923(7) 0.7415(3) 0.0384(12) Uani 1 1 d . . . . .
C7 C 0.5108(4) 0.4721(6) 0.8511(3) 0.0340(12) Uani 1 1 d . . . . .
C8 C 0.4590(4) 0.6120(7) 0.8187(3) 0.0346(12) Uani 1 1 d . . . . .
S1 S 0.60954(13) 0.7486(2) 0.59431(11) 0.0549(4) Uani 1 1 d . . . . .
S2 S 0.73669(11) 0.4585(2) 0.66936(11) 0.0530(4) Uani 1 1 d . . . . .
S3 S 0.62347(11) 0.4386(2) 0.82465(10) 0.0473(4) Uani 1 1 d . . . . .
S4 S 0.50798(11) 0.74180(18) 0.75232(10) 0.0439(4) Uani 1 1 d . . . . .
Se1 Se 0.4849(4) 0.3251(8) 0.9316(4) 0.0583(14) Uani 0.521(3) 1 d . . P A 1
Se2 Se 0.3486(2) 0.6898(5) 0.85109(16) 0.0320(9) Uani 0.521(3) 1 d . . P A 1
S5 S 0.6330(13) 0.714(3) 0.4126(10) 0.110(7) Uani 0.521(3) 1 d . . P A 1
S6 S 0.7759(11) 0.372(2) 0.4961(10) 0.127(7) Uani 0.521(3) 1 d . . P A 1
C4 C 0.5089(6) 0.7975(12) 0.3921(5) 0.108(11) Uani 0.521(3) 1 d . . P A 1
H4A H 0.4893 0.8477 0.3354 0.162 Uiso 0.521(3) 1 calc R U P A 1
H4B H 0.4638 0.7068 0.3953 0.162 Uiso 0.521(3) 1 calc R U P A 1
H4C H 0.5072 0.8828 0.4346 0.162 Uiso 0.521(3) 1 calc R U P A 1
C5 C 0.7055(6) 0.1656(9) 0.4850(5) 0.087(9) Uani 0.521(3) 1 d . . P A 1
H5A H 0.7325 0.0866 0.4517 0.13 Uiso 0.521(3) 1 calc R U P A 1
H5B H 0.7113 0.1187 0.5414 0.13 Uiso 0.521(3) 1 calc R U P A 1
H5C H 0.6366 0.1858 0.4563 0.13 Uiso 0.521(3) 1 calc R U P A 1
C9 C 0.4980(6) 0.1170(10) 0.8796(5) 0.083(5) Uani 0.521(3) 1 d . . P A 1
H9A H 0.4862 0.0254 0.9152 0.124 Uiso 0.521(3) 1 calc R U P A 1
H9B H 0.4505 0.1112 0.8238 0.124 Uiso 0.521(3) 1 calc R U P A 1
H9C H 0.564 0.1074 0.8729 0.124 Uiso 0.521(3) 1 calc R U P A 1
C10 C 0.2666(6) 0.7404(10) 0.7409(5) 0.083(5) Uani 0.521(3) 1 d . . P A 1
H10A H 0.2041 0.7837 0.7458 0.124 Uiso 0.521(3) 1 calc R U P A 1
H10B H 0.2981 0.8248 0.714 0.124 Uiso 0.521(3) 1 calc R U P A 1
H10C H 0.2554 0.6387 0.7063 0.124 Uiso 0.521(3) 1 calc R U P A 1
Se1B Se 0.6263(5) 0.6727(10) 0.4077(3) 0.0677(10) Uani 0.479(3) 1 d . . P A 2
Se2B Se 0.7867(3) 0.3550(5) 0.5010(2) 0.0518(7) Uani 0.479(3) 1 d . . P A 2
S5B S 0.4749(7) 0.3265(16) 0.9294(8) 0.027(2) Uani 0.479(3) 1 d . . P A 2
S6B S 0.3494(10) 0.6838(18) 0.8506(8) 0.074(5) Uani 0.479(3) 1 d . . P A 2
C4B C 0.5089(6) 0.7975(12) 0.3921(5) 0.065(6) Uiso 0.479(3) 1 d . . P A 2
H4B1 H 0.4849 0.8313 0.3326 0.097 Uiso 0.479(3) 1 calc R U P A 2
H4B2 H 0.4597 0.7282 0.4076 0.097 Uiso 0.479(3) 1 calc R U P A 2
H4B3 H 0.5216 0.8972 0.4282 0.097 Uiso 0.479(3) 1 calc R U P A 2
C5B C 0.7055(6) 0.1656(9) 0.4850(5) 0.065(6) Uiso 0.479(3) 1 d . . P A 2
H5B1 H 0.7322 0.0786 0.4557 0.097 Uiso 0.479(3) 1 calc R U P A 2
H5B2 H 0.7019 0.1235 0.5402 0.097 Uiso 0.479(3) 1 calc R U P A 2
H5B3 H 0.64 0.1961 0.4508 0.097 Uiso 0.479(3) 1 calc R U P A 2
C9B C 0.4980(6) 0.1170(10) 0.8796(5) 0.065(4) Uiso 0.479(3) 1 d . . P A 2
H9B1 H 0.4828 0.0242 0.9128 0.097 Uiso 0.479(3) 1 calc R U P A 2
H9B2 H 0.4563 0.1102 0.8212 0.097 Uiso 0.479(3) 1 calc R U P A 2
H9B3 H 0.5665 0.1104 0.8794 0.097 Uiso 0.479(3) 1 calc R U P A 2
C10B C 0.2666(6) 0.7404(10) 0.7409(5) 0.065(4) Uiso 0.479(3) 1 d . . P A 2
H10D H 0.204 0.7816 0.7467 0.097 Uiso 0.479(3) 1 calc R U P A 2
H10E H 0.2978 0.8275 0.7154 0.097 Uiso 0.479(3) 1 calc R U P A 2
H10F H 0.2557 0.641 0.7046 0.097 Uiso 0.479(3) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C6 1.327(7) . ?
C1 S2 1.751(5) . ?
C1 S1 1.757(6) . ?
C2 C3 1.335(9) . ?
C2 S1 1.760(6) . ?
C2 Se1B 1.822(8) . ?
C2 S5 1.850(17) . ?
C3 S6 1.749(15) . ?
C3 S2 1.760(6) . ?
C3 Se2B 1.872(7) . ?
C6 S4 1.758(5) . ?
C6 S3 1.762(6) . ?
C7 C8 1.339(7) . ?
C7 S3 1.759(5) . ?
C7 Se1 1.840(8) . ?
C7 S5B 1.864(13) . ?
C8 S4 1.743(5) . ?
C8 S6B 1.830(14) . ?
C8 Se2 1.859(6) . ?
Se1 C9 1.864(10) . ?
Se2 C10 1.870(8) . ?
S5 C4 1.80(2) . ?
S6 C5 1.879(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 . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
Se1B C4B 1.868(11) . ?
Se2B C5B 1.844(9) . ?
S5B C9B 1.892(14) . ?
S6B C10B 1.878(15) . ?
C4B H4B1 0.96 . ?
C4B H4B2 0.96 . ?
C4B H4B3 0.96 . ?
C5B H5B1 0.96 . ?
C5B H5B2 0.96 . ?
C5B H5B3 0.96 . ?
C9B H9B1 0.96 . ?
C9B H9B2 0.96 . ?
C9B H9B3 0.96 . ?
C10B H10D 0.96 . ?
C10B H10E 0.96 . ?
C10B H10F 0.96 . ?

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
C6 C1 S2 124.3(5) . . ?
C6 C1 S1 122.2(4) . . ?
S2 C1 S1 113.5(3) . . ?
C3 C2 S1 116.6(5) . . ?
C3 C2 Se1B 121.8(5) . . ?
S1 C2 Se1B 121.5(4) . . ?
C3 C2 S5 128.0(7) . . ?
S1 C2 S5 114.5(7) . . ?
C2 C3 S6 121.4(7) . . ?
C2 C3 S2 117.4(4) . . ?
S6 C3 S2 121.1(7) . . ?
C2 C3 Se2B 126.4(5) . . ?
S2 C3 Se2B 116.0(4) . . ?
C1 C6 S4 123.3(4) . . ?
C1 C6 S3 124.1(4) . . ?
S4 C6 S3 112.7(3) . . ?
C8 C7 S3 117.0(4) . . ?
C8 C7 Se1 126.6(4) . . ?
S3 C7 Se1 115.9(3) . . ?
C8 C7 S5B 123.1(5) . . ?
S3 C7 S5B 119.6(4) . . ?
C7 C8 S4 117.0(4) . . ?
C7 C8 S6B 123.3(6) . . ?
S4 C8 S6B 119.3(5) . . ?
C7 C8 Se2 124.2(4) . . ?
S4 C8 Se2 118.3(3) . . ?
C1 S1 C2 93.7(3) . . ?
C1 S2 C3 93.7(3) . . ?
C7 S3 C6 93.9(2) . . ?
C8 S4 C6 94.6(3) . . ?
C7 Se1 C9 99.8(4) . . ?
C8 Se2 C10 98.4(3) . . ?
C4 S5 C2 102.8(9) . . ?
C3 S6 C5 101.7(8) . . ?
S5 C4 H4A 109.5 . . ?
S5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S6 C5 H5A 109.5 . . ?
S6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Se1 C9 H9A 109.5 . . ?
Se1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
Se1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Se2 C10 H10A 109.5 . . ?
Se2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
Se2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 Se1B C4B 101.3(4) . . ?
C5B Se2B C3 98.5(3) . . ?
C7 S5B C9B 97.9(6) . . ?
C8 S6B C10B 99.1(6) . . ?
Se1B C4B H4B1 109.5 . . ?
Se1B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
Se1B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
Se2B C5B H5B1 109.5 . . ?
Se2B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
Se2B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
S5B C9B H9B1 109.5 . . ?
S5B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
S5B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
S6B C10B H10D 109.5 . . ?
S6B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
S6B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?

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
S1 C2 C3 S6 -174.1(6) . . . . ?
S5 C2 C3 S6 -5.1(13) . . . . ?
S1 C2 C3 S2 1.7(7) . . . . ?
Se1B C2 C3 S2 -178.8(4) . . . . ?
S5 C2 C3 S2 170.8(8) . . . . ?
S1 C2 C3 Se2B -173.0(4) . . . . ?
Se1B C2 C3 Se2B 6.5(9) . . . . ?
S2 C1 C6 S4 176.2(3) . . . . ?
S1 C1 C6 S4 -4.6(7) . . . . ?
S2 C1 C6 S3 -2.1(7) . . . . ?
S1 C1 C6 S3 177.1(3) . . . . ?
S3 C7 C8 S4 1.4(6) . . . . ?
Se1 C7 C8 S4 172.9(4) . . . . ?
S5B C7 C8 S4 175.5(5) . . . . ?
S3 C7 C8 S6B -171.4(6) . . . . ?
S5B C7 C8 S6B 2.8(9) . . . . ?
S3 C7 C8 Se2 -170.5(3) . . . . ?
Se1 C7 C8 Se2 1.1(7) . . . . ?
C6 C1 S1 C2 -157.2(5) . . . . ?
S2 C1 S1 C2 22.1(4) . . . . ?
C3 C2 S1 C1 -14.4(5) . . . . ?
Se1B C2 S1 C1 166.1(5) . . . . ?
S5 C2 S1 C1 175.1(7) . . . . ?
C6 C1 S2 C3 157.9(5) . . . . ?
S1 C1 S2 C3 -21.4(4) . . . . ?
C2 C3 S2 C1 12.0(5) . . . . ?
S6 C3 S2 C1 -172.2(7) . . . . ?
Se2B C3 S2 C1 -172.8(4) . . . . ?
C8 C7 S3 C6 -13.8(4) . . . . ?
Se1 C7 S3 C6 173.7(4) . . . . ?
S5B C7 S3 C6 171.8(5) . . . . ?
C1 C6 S3 C7 -160.4(5) . . . . ?
S4 C6 S3 C7 21.1(3) . . . . ?
C7 C8 S4 C6 11.9(5) . . . . ?
S6B C8 S4 C6 -175.0(6) . . . . ?
Se2 C8 S4 C6 -175.8(3) . . . . ?
C1 C6 S4 C8 160.8(5) . . . . ?
S3 C6 S4 C8 -20.7(3) . . . . ?
C8 C7 Se1 C9 134.0(5) . . . . ?
S3 C7 Se1 C9 -54.3(4) . . . . ?
C7 C8 Se2 C10 -135.8(5) . . . . ?
S4 C8 Se2 C10 52.5(4) . . . . ?
C3 C2 S5 C4 151.3(8) . . . . ?
S1 C2 S5 C4 -39.4(11) . . . . ?
C2 C3 S6 C5 -108.6(9) . . . . ?
S2 C3 S6 C5 75.8(9) . . . . ?
C3 C2 Se1B C4B 158.2(6) . . . . ?
S1 C2 Se1B C4B -22.3(6) . . . . ?
C2 C3 Se2B C5B -103.3(6) . . . . ?
S2 C3 Se2B C5B 82.0(4) . . . . ?
C8 C7 S5B C9B 137.1(6) . . . . ?
S3 C7 S5B C9B -48.8(7) . . . . ?
C7 C8 S6B C10B -136.6(6) . . . . ?
S4 C8 S6B C10B 50.7(8) . . . . ?


# END of CIF
_chemical_name_systematic        
4,5-bis(methylseleno)-4',5'-bis(methylthio)-tetrathiafulvalene
_chemical_name_common            (MeSe)2(MeS)2TTF
