# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_compound2a
_database_code_depnum_ccdc_archive 'CCDC 2245494'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 05 novembre 2021                                         #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H4 N2 O S4'
_chemical_formula_sum            'C7 H4 N2 O S4'
_chemical_formula_weight         260.36
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0683(15)
_cell_length_b                   8.6879(17)
_cell_length_c                   9.462(2)
_cell_angle_alpha                111.186(8)
_cell_angle_beta                 108.771(8)
_cell_angle_gamma                97.407(8)
_cell_volume                     492.79(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5845
_cell_measurement_theta_min      2.5169
_cell_measurement_theta_max      27.5007
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0455387
_diffrn_orient_matrix_UB_21      -0.1357554
_diffrn_orient_matrix_UB_31      -0.0607496
_diffrn_orient_matrix_UB_12      0.0763231
_diffrn_orient_matrix_UB_22      0.0291001
_diffrn_orient_matrix_UB_32      -0.0992001
_diffrn_orient_matrix_UB_13      0.1201235
_diffrn_orient_matrix_UB_23      -0.0236324
_diffrn_orient_matrix_UB_33      0.0168026


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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             264
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.926
_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  0.761
_exptl_absorpt_correction_T_max  0.920

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX3 2016.9-0        #
# Number of scans            :        4                                        #
# Total number of frames     :      291                                        #
# Total length of scans      :   291.00 (deg.)                                 #
# Rotation speed             :     5.00 sec./deg.                              #
# Total exposition time      :         24.2 min.                               #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega    5.0  1.00    34.0    97   97.0    1.9    4.5    0.0  315.5 150.0 #
#  2 Omega    5.0  1.00    34.0    97   97.0    1.9    4.5  216.0  315.5 150.0 #
#  3 Omega    5.0  1.00    34.0    97   97.0    1.9    4.5   72.0  315.5 150.0 #
#  4 Fast     1.0  1.00    34.0   180  180.0    0.0  360.0    0.0   54.7 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0453
_diffrn_reflns_av_r_equivalents  0.0356
_diffrn_reflns_number            5511
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.965
_reflns_number_total             2195
_reflns_number_gt                2084
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.0876P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2195
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.081

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09263(17) 0.71625(15) 0.30243(15) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.1350(2) 0.60759(18) 0.34819(19) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.1676(2) 0.31768(17) 0.35686(17) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.2699(2) 0.43730(17) 0.51584(17) 0.0156(3) Uani 1 1 d . . . . .
N5 N 0.35465(17) 0.38028(14) 0.63313(14) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.3140(2) 0.21276(17) 0.55954(16) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.5429(2) 0.24146(18) 0.86499(17) 0.0190(3) Uani 1 1 d . . . . .
H7A H 0.650330 0.197959 0.923427 0.023 Uiso 1 1 calc R U . . .
H7B H 0.614911 0.347181 0.865223 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4027(2) 0.28669(17) 0.95937(17) 0.0212(3) Uani 1 1 d . . . . .
H8A H 0.485853 0.382384 1.069880 0.025 Uiso 1 1 calc R U . . .
H8B H 0.291356 0.325731 0.899060 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3089(2) 0.13904(18) 0.97841(17) 0.0214(3) Uani 1 1 d . . . . .
N10 N 0.2375(2) 0.02203(18) 0.99180(18) 0.0279(3) Uani 1 1 d . . . . .
S1 S 0.28080(5) 0.65105(4) 0.55741(4) 0.01860(12) Uani 1 1 d . . . . .
S2 S 0.05387(5) 0.38509(5) 0.20693(4) 0.02141(12) Uani 1 1 d . . . . .
S3 S 0.16909(5) 0.11578(4) 0.34681(4) 0.01824(11) Uani 1 1 d . . . . .
S4 S 0.40270(5) 0.08253(4) 0.65431(4) 0.01935(12) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              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
O1 C2 1.2055(17) . ?
C2 S1 1.7805(16) . ?
C2 S2 1.7904(16) . ?
C3 C4 1.357(2) . ?
C3 S3 1.7237(14) . ?
C3 S2 1.7290(14) . ?
C4 N5 1.3719(17) . ?
C4 S1 1.7392(14) . ?
N5 C6 1.3102(17) . ?
C6 S4 1.7412(13) . ?
C6 S3 1.7423(14) . ?
C7 C8 1.533(2) . ?
C7 S4 1.8025(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.464(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N10 1.143(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 S1 124.06(12) . . ?
O1 C2 S2 121.70(12) . . ?
S1 C2 S2 114.23(8) . . ?
C4 C3 S3 109.73(10) . . ?
C4 C3 S2 118.51(11) . . ?
S3 C3 S2 131.70(9) . . ?
C3 C4 N5 117.44(12) . . ?
C3 C4 S1 117.99(10) . . ?
N5 C4 S1 124.56(10) . . ?
C6 N5 C4 108.36(12) . . ?
N5 C6 S4 125.61(10) . . ?
N5 C6 S3 116.33(10) . . ?
S4 C6 S3 117.99(8) . . ?
C8 C7 S4 113.22(9) . . ?
C8 C7 H7A 108.9 . . ?
S4 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
S4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 111.44(11) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N10 C9 C8 178.76(15) . . ?
C4 S1 C2 94.69(7) . . ?
C3 S2 C2 94.59(7) . . ?
C3 S3 C6 88.12(7) . . ?
C6 S4 C7 100.26(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S3 C3 C4 N5 1.08(15) . . . . ?
S2 C3 C4 N5 178.52(9) . . . . ?
S3 C3 C4 S1 -177.85(7) . . . . ?
S2 C3 C4 S1 -0.41(15) . . . . ?
C3 C4 N5 C6 -0.15(16) . . . . ?
S1 C4 N5 C6 178.71(9) . . . . ?
C4 N5 C6 S4 175.81(9) . . . . ?
C4 N5 C6 S3 -0.89(14) . . . . ?
S4 C7 C8 C9 64.68(14) . . . . ?
C3 C4 S1 C2 0.28(12) . . . . ?
N5 C4 S1 C2 -178.57(11) . . . . ?
O1 C2 S1 C4 179.96(13) . . . . ?
S2 C2 S1 C4 -0.07(8) . . . . ?
C4 C3 S2 C2 0.30(12) . . . . ?
S3 C3 S2 C2 177.07(10) . . . . ?
O1 C2 S2 C3 179.87(13) . . . . ?
S1 C2 S2 C3 -0.09(8) . . . . ?
C4 C3 S3 C6 -1.24(10) . . . . ?
S2 C3 S3 C6 -178.22(11) . . . . ?
N5 C6 S3 C3 1.28(11) . . . . ?
S4 C6 S3 C3 -175.69(8) . . . . ?
N5 C6 S4 C7 2.15(13) . . . . ?
S3 C6 S4 C7 178.81(7) . . . . ?
C8 C7 S4 C6 83.22(10) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .FCF SHELXL file: job.fcf
#...............................................................................

####################################################################### 
# 
# 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 2245497'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

_audit_creation_date             2017-10-10T16:53:29-00:00
_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            'C12 H10 N2 S8'
_chemical_formula_moiety         'C12 H10 N2 S8'
_chemical_formula_weight         438.7

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

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

_cell_length_a                   14.4980(13)
_cell_length_b                   7.5276(9)
_cell_length_c                   16.6742(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.731(5)
_cell_angle_gamma                90
_cell_volume                     1690.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4467
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.41
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

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

_exptl_absorpt_coefficient_mu    1.05
_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  0.802
_exptl_absorpt_correction_T_max  0.969

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6339  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      0.006963
_diffrn_orient_matrix_ub_12      -0.129571
_diffrn_orient_matrix_ub_13      0.01422
_diffrn_orient_matrix_ub_21      -0.059166
_diffrn_orient_matrix_ub_22      -0.025745
_diffrn_orient_matrix_ub_23      -0.053369
_diffrn_orient_matrix_ub_31      0.044321
_diffrn_orient_matrix_ub_32      -0.014013
_diffrn_orient_matrix_ub_33      -0.033432
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.041
_diffrn_reflns_number            14546
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         27.494
_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             3876
_reflns_number_gt                2851
_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)+(0.0352P)²+1.4800P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3876
_refine_ls_number_parameters     230
_refine_ls_number_restraints     10
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.06
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 '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 0.63725(18) 0.3375(3) 0.51260(16) 0.0278(6) Uani 1 1 d . . . . .
S1A S 0.65488(15) 0.2347(5) 0.6119(2) 0.0321(4) Uani 0.8925(15) 1 d D . P A 1
S2A S 0.73830(17) 0.4546(3) 0.50519(14) 0.0312(3) Uani 0.8925(15) 1 d D . P A 1
S3A S 0.93993(6) 0.44247(13) 0.66558(6) 0.0322(2) Uani 0.8925(15) 1 d D . P A 1
S7A S 1.02988(7) 0.29243(15) 0.84948(6) 0.0498(3) Uani 0.8925(15) 1 d . . P A 1
C2A C 0.8167(2) 0.3969(6) 0.6091(2) 0.0269(9) Uani 0.8925(15) 1 d D . P A 1
C3A C 0.7806(3) 0.2943(5) 0.6579(2) 0.0265(8) Uani 0.8925(15) 1 d D . P A 1
C4A C 0.9311(3) 0.3205(4) 0.75187(18) 0.0310(7) Uani 0.8925(15) 1 d D . P A 1
C5A C 1.1345(3) 0.3625(6) 0.8236(2) 0.0570(11) Uani 0.8925(15) 1 d . . P A 1
H5A1 H 1.1377 0.2935 0.7756 0.068 Uiso 0.8925(15) 1 calc R U P A 1
H5A2 H 1.1277 0.4868 0.8073 0.068 Uiso 0.8925(15) 1 calc R U P A 1
C6A C 1.2275(3) 0.3350(7) 0.9020(2) 0.0813(14) Uani 0.8925(15) 1 d . . P A 1
H6A H 1.2284 0.417 0.9464 0.122 Uiso 0.8925(15) 1 calc R U P A 1
H6B H 1.2845 0.3551 0.887 0.122 Uiso 0.8925(15) 1 calc R U P A 1
H6C H 1.2289 0.2156 0.9226 0.122 Uiso 0.8925(15) 1 calc R U P A 1
N1A N 0.8436(2) 0.2524(4) 0.7394(2) 0.0317(8) Uani 0.8925(15) 1 d D . P A 1
S1B S 0.7453(17) 0.473(3) 0.4989(12) 0.0321(4) Uani 0.1075(15) 1 d D . P A 2
S2B S 0.6684(16) 0.237(4) 0.619(2) 0.0312(3) Uani 0.1075(15) 1 d D . P A 2
S3B S 0.8783(8) 0.2736(15) 0.7521(6) 0.0322(2) Uani 0.1075(15) 1 d D . P A 2
S7B S 1.0804(6) 0.4420(12) 0.7792(5) 0.0498(3) Uani 0.1075(15) 1 d . . P A 2
C2B C 0.7865(17) 0.328(6) 0.6554(13) 0.0269(9) Uani 0.1075(15) 1 d D . P A 2
C3B C 0.8248(13) 0.383(5) 0.5971(15) 0.0265(8) Uani 0.1075(15) 1 d D . P A 2
C4B C 0.9562(12) 0.397(3) 0.7153(11) 0.0310(7) Uani 0.1075(15) 1 d D . P A 2
C5B C 1.112(2) 0.291(5) 0.860(2) 0.0570(11) Uani 0.1075(15) 1 d . . P A 2
H5B1 H 1.0785 0.3124 0.8995 0.068 Uiso 0.1075(15) 1 calc R U P A 2
H5B2 H 1.0999 0.1705 0.8382 0.068 Uiso 0.1075(15) 1 calc R U P A 2
C6B C 1.2275(3) 0.3350(7) 0.9020(2) 0.0813(14) Uani 0.1075(15) 1 d . . P A 2
H6B1 H 1.249 0.3869 0.8593 0.122 Uiso 0.1075(15) 1 calc R U P A 2
H6B2 H 1.2639 0.2275 0.9234 0.122 Uiso 0.1075(15) 1 calc R U P A 2
H6B3 H 1.2392 0.4171 0.9488 0.122 Uiso 0.1075(15) 1 calc R U P A 2
N1B N 0.9153(16) 0.458(4) 0.6368(13) 0.0317(8) Uani 0.1075(15) 1 d D . P A 2
C7 C 0.54840(19) 0.3327(3) 0.44719(17) 0.0284(6) Uani 1 1 d . . . . .
C8 C 0.36973(19) 0.2631(4) 0.35368(17) 0.0296(6) Uani 1 1 d . . . . .
C9 C 0.4041(2) 0.3592(4) 0.30198(17) 0.0325(6) Uani 1 1 d . . . . .
C10 C 0.2544(2) 0.3173(4) 0.20856(18) 0.0370(7) Uani 1 1 d . . . . .
C11 C 0.0585(2) 0.2120(5) 0.1371(2) 0.0536(9) Uani 1 1 d . . . . .
H11A H 0.0789 0.0901 0.153 0.064 Uiso 1 1 calc R U . . .
H11B H 0.0492 0.2692 0.1857 0.064 Uiso 1 1 calc R U . . .
C12 C -0.0375(3) 0.2150(6) 0.0597(2) 0.0711(12) Uani 1 1 d . . . . .
H12A H -0.0579 0.3358 0.0448 0.107 Uiso 1 1 calc R U . . .
H12B H -0.0878 0.1529 0.0731 0.107 Uiso 1 1 calc R U . . .
H12C H -0.0279 0.1581 0.0118 0.107 Uiso 1 1 calc R U . . .
S4 S 0.52592(5) 0.43966(10) 0.34764(5) 0.03654(18) Uani 1 1 d . . . . .
S5 S 0.44572(5) 0.22563(10) 0.45959(4) 0.03243(17) Uani 1 1 d . . . . .
S6 S 0.24830(5) 0.20450(10) 0.29856(5) 0.03772(19) Uani 1 1 d . . . . .
S8 S 0.15350(6) 0.32765(14) 0.11130(5) 0.0569(3) Uani 1 1 d . . . . .
N2 N 0.33914(18) 0.3914(3) 0.21830(15) 0.0399(6) 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
C1 C7 1.345(4) . ?
C1 S2A 1.753(3) . ?
C1 S1A 1.759(4) . ?
C1 S2B 1.83(3) . ?
C1 S1B 1.95(2) . ?
S1A C3A 1.755(3) . ?
S2A C2A 1.739(3) . ?
S3A C2A 1.717(3) . ?
S3A C4A 1.751(3) . ?
S7A C4A 1.737(3) . ?
S7A C5A 1.802(4) . ?
C2A C3A 1.359(4) . ?
C3A N1A 1.364(4) . ?
C4A N1A 1.311(4) . ?
C5A C6A 1.504(5) . ?
C5A H5A1 0.97 . ?
C5A H5A2 0.97 . ?
C6A H6A 0.96 . ?
C6A H6B 0.96 . ?
C6A H6C 0.96 . ?
S1B C3B 1.753(11) . ?
S2B C2B 1.732(10) . ?
S3B C2B 1.718(10) . ?
S3B C4B 1.740(10) . ?
S7B C5B 1.69(4) . ?
S7B C4B 1.752(17) . ?
C2B C3B 1.349(10) . ?
C3B N1B 1.358(11) . ?
C4B N1B 1.304(10) . ?
C5B C6B 1.59(3) . ?
C5B H5B1 0.97 . ?
C5B H5B2 0.97 . ?
C6B H6B1 0.96 . ?
C6B H6B2 0.96 . ?
C6B H6B3 0.96 . ?
C7 S4 1.763(3) . ?
C7 S5 1.771(3) . ?
C8 C9 1.354(4) . ?
C8 S6 1.715(3) . ?
C8 S5 1.724(3) . ?
C9 N2 1.386(3) . ?
C9 S4 1.752(3) . ?
C10 N2 1.303(4) . ?
C10 S8 1.738(3) . ?
C10 S6 1.755(3) . ?
C11 C12 1.508(5) . ?
C11 S8 1.810(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 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
C7 C1 S2A 122.1(2) . . ?
C7 C1 S1A 120.9(2) . . ?
S2A C1 S1A 116.99(16) . . ?
C7 C1 S2B 126.5(6) . . ?
C7 C1 S1B 119.2(6) . . ?
S2B C1 S1B 114.2(6) . . ?
C3A S1A C1 93.69(15) . . ?
C2A S2A C1 93.41(14) . . ?
C2A S3A C4A 88.17(16) . . ?
C4A S7A C5A 102.44(17) . . ?
C3A C2A S3A 109.8(3) . . ?
C3A C2A S2A 118.9(2) . . ?
S3A C2A S2A 131.3(2) . . ?
C2A C3A N1A 117.6(3) . . ?
C2A C3A S1A 116.8(2) . . ?
N1A C3A S1A 125.5(2) . . ?
N1A C4A S7A 121.0(3) . . ?
N1A C4A S3A 115.8(2) . . ?
S7A C4A S3A 123.2(2) . . ?
C6A C5A S7A 108.4(3) . . ?
C6A C5A H5A1 110 . . ?
S7A C5A H5A1 110 . . ?
C6A C5A H5A2 110 . . ?
S7A C5A H5A2 110 . . ?
H5A1 C5A H5A2 108.4 . . ?
C5A C6A H6A 109.5 . . ?
C5A C6A H6B 109.5 . . ?
H6A C6A H6B 109.5 . . ?
C5A C6A H6C 109.5 . . ?
H6A C6A H6C 109.5 . . ?
H6B C6A H6C 109.5 . . ?
C4A N1A C3A 108.6(3) . . ?
C3B S1B C1 88.1(7) . . ?
C2B S2B C1 91.8(10) . . ?
C2B S3B C4B 85.4(11) . . ?
C5B S7B C4B 105.7(13) . . ?
C3B C2B S3B 111.5(17) . . ?
C3B C2B S2B 119.2(11) . . ?
S3B C2B S2B 123.7(16) . . ?
C2B C3B N1B 111.0(18) . . ?
C2B C3B S1B 119.2(11) . . ?
N1B C3B S1B 118(2) . . ?
N1B C4B S3B 115.5(12) . . ?
N1B C4B S7B 121.6(12) . . ?
S3B C4B S7B 122.9(10) . . ?
C6B C5B S7B 98(2) . . ?
C6B C5B H5B1 112.1 . . ?
S7B C5B H5B1 112.1 . . ?
C6B C5B H5B2 112.1 . . ?
S7B C5B H5B2 112.1 . . ?
H5B1 C5B H5B2 109.7 . . ?
C5B C6B H6B1 109.5 . . ?
C5B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C5B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
C4B N1B C3B 109.8(11) . . ?
C1 C7 S4 122.6(2) . . ?
C1 C7 S5 120.8(2) . . ?
S4 C7 S5 116.57(15) . . ?
C9 C8 S6 110.1(2) . . ?
C9 C8 S5 119.6(2) . . ?
S6 C8 S5 130.30(16) . . ?
C8 C9 N2 117.5(2) . . ?
C8 C9 S4 117.2(2) . . ?
N2 C9 S4 125.2(2) . . ?
N2 C10 S8 121.7(2) . . ?
N2 C10 S6 116.4(2) . . ?
S8 C10 S6 121.87(17) . . ?
C12 C11 S8 109.4(3) . . ?
C12 C11 H11A 109.8 . . ?
S8 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
S8 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 S4 C7 93.24(12) . . ?
C8 S5 C7 92.97(12) . . ?
C8 S6 C10 88.10(13) . . ?
C10 S8 C11 102.01(14) . . ?
C10 N2 C9 108.0(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
C7 C1 S1A C3A 179.4(3) . . . . ?
S2A C1 S1A C3A -3.8(3) . . . . ?
C7 C1 S2A C2A 179.8(3) . . . . ?
S1A C1 S2A C2A 2.9(3) . . . . ?
C4A S3A C2A C3A -1.0(3) . . . . ?
C4A S3A C2A S2A -179.3(3) . . . . ?
C1 S2A C2A C3A -0.5(4) . . . . ?
C1 S2A C2A S3A 177.7(3) . . . . ?
S3A C2A C3A N1A 1.9(5) . . . . ?
S2A C2A C3A N1A -179.5(3) . . . . ?
S3A C2A C3A S1A 179.4(3) . . . . ?
S2A C2A C3A S1A -2.1(5) . . . . ?
C1 S1A C3A C2A 3.4(4) . . . . ?
C1 S1A C3A N1A -179.4(4) . . . . ?
C5A S7A C4A N1A 167.0(3) . . . . ?
C5A S7A C4A S3A -14.3(3) . . . . ?
C2A S3A C4A N1A -0.1(3) . . . . ?
C2A S3A C4A S7A -179.0(2) . . . . ?
C4A S7A C5A C6A -176.8(3) . . . . ?
S7A C4A N1A C3A -180.0(3) . . . . ?
S3A C4A N1A C3A 1.2(4) . . . . ?
C2A C3A N1A C4A -2.0(5) . . . . ?
S1A C3A N1A C4A -179.2(3) . . . . ?
C7 C1 S2B C2B -175.2(16) . . . . ?
S1B C1 S2B C2B 2(2) . . . . ?
C4B S3B C2B C3B 18(3) . . . . ?
C4B S3B C2B S2B 171(3) . . . . ?
C1 S2B C2B C3B -20(4) . . . . ?
C1 S2B C2B S3B -171(3) . . . . ?
S3B C2B C3B N1B -29(4) . . . . ?
S2B C2B C3B N1B 177(3) . . . . ?
S3B C2B C3B S1B -172(3) . . . . ?
S2B C2B C3B S1B 34(5) . . . . ?
C1 S1B C3B C2B -25(3) . . . . ?
C1 S1B C3B N1B -165(3) . . . . ?
C2B S3B C4B N1B -4(3) . . . . ?
C2B S3B C4B S7B 175(2) . . . . ?
C5B S7B C4B N1B -163(3) . . . . ?
C5B S7B C4B S3B 19(2) . . . . ?
C4B S7B C5B C6B 172.9(15) . . . . ?
S3B C4B N1B C3B -11(4) . . . . ?
S7B C4B N1B C3B 170(2) . . . . ?
C2B C3B N1B C4B 25(4) . . . . ?
S1B C3B N1B C4B 168(3) . . . . ?
S2A C1 C7 S4 1.2(4) . . . . ?
S1A C1 C7 S4 177.9(2) . . . . ?
S2B C1 C7 S4 178.3(15) . . . . ?
S1B C1 C7 S4 1.7(10) . . . . ?
S2A C1 C7 S5 -175.72(18) . . . . ?
S1A C1 C7 S5 1.0(4) . . . . ?
S2B C1 C7 S5 1.4(15) . . . . ?
S1B C1 C7 S5 -175.3(10) . . . . ?
S6 C8 C9 N2 -0.1(3) . . . . ?
S5 C8 C9 N2 -177.7(2) . . . . ?
S6 C8 C9 S4 177.60(14) . . . . ?
S5 C8 C9 S4 0.0(3) . . . . ?
C8 C9 S4 C7 3.8(2) . . . . ?
N2 C9 S4 C7 -178.7(2) . . . . ?
C1 C7 S4 C9 176.6(2) . . . . ?
S5 C7 S4 C9 -6.34(17) . . . . ?
C9 C8 S5 C7 -3.8(2) . . . . ?
S6 C8 S5 C7 179.2(2) . . . . ?
C1 C7 S5 C8 -176.5(2) . . . . ?
S4 C7 S5 C8 6.35(17) . . . . ?
C9 C8 S6 C10 -0.1(2) . . . . ?
S5 C8 S6 C10 177.1(2) . . . . ?
N2 C10 S6 C8 0.2(2) . . . . ?
S8 C10 S6 C8 179.6(2) . . . . ?
N2 C10 S8 C11 -178.0(3) . . . . ?
S6 C10 S8 C11 2.7(2) . . . . ?
C12 C11 S8 C10 177.6(3) . . . . ?
S8 C10 N2 C9 -179.7(2) . . . . ?
S6 C10 N2 C9 -0.3(3) . . . . ?
C8 C9 N2 C10 0.3(4) . . . . ?
S4 C9 N2 C10 -177.2(2) . . . . ?


####################################################################### 
# 
# 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_compound2f
_database_code_depnum_ccdc_archive 'CCDC 2245496'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13 juin 2022                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C5 H3 N O S4'
_chemical_formula_sum            'C5 H3 N O S4'
_chemical_formula_weight         221.32
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1900(18)
_cell_length_b                   10.0186(17)
_cell_length_c                   8.6765(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.049(7)
_cell_angle_gamma                90
_cell_volume                     791.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1698
_cell_measurement_theta_min      2.2371
_cell_measurement_theta_max      27.4745
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0112708
_diffrn_orient_matrix_UB_21      0.1043468
_diffrn_orient_matrix_UB_31      0.0324131
_diffrn_orient_matrix_UB_12      -0.0108403
_diffrn_orient_matrix_UB_22      0.0283568
_diffrn_orient_matrix_UB_32      -0.0950578
_diffrn_orient_matrix_UB_13      -0.1156474
_diffrn_orient_matrix_UB_23      0.0005073
_diffrn_orient_matrix_UB_33      0.0133397


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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             448
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.132
_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  0.536
_exptl_absorpt_correction_T_max  0.873

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        3                                        #
# Total number of frames [*] :      281                                        #
# Total length of scans  [*] :   281.00 (deg.)                                 #
# Rotation speed         [*] :    15.00 sec./deg.                              #
# Total exposition time  [*] :      1 h  10.2 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Phi     15.0  1.00    34.0   184  184.0    0.1    1.9  204.0  -24.0 150.0 #
#  3 Omega   15.0  1.00    34.0    97   97.0    0.1    2.7   72.0  -44.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0358
_diffrn_reflns_av_r_equivalents  ?
_diffrn_reflns_number            1775
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.970
_reflns_number_total             1775
_reflns_number_gt                1607
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+0.8314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1775
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.094

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
S1 S 0.21995(9) 0.08906(8) 0.47419(9) 0.0245(2) Uani 1 1 d . . . . .
S2 S 0.45028(8) 0.22293(8) 0.69897(8) 0.0227(2) Uani 1 1 d . . . . .
S3 S 0.31291(8) 0.49258(8) 0.56213(8) 0.02150(19) Uani 1 1 d . . . . .
S4 S 0.07220(9) 0.59865(8) 0.31234(9) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.4226(3) -0.0374(2) 0.6619(3) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.3744(3) 0.0702(3) 0.6204(4) 0.0232(6) Uani 1 1 d . . . . .
C3 C 0.3259(3) 0.3221(3) 0.5827(3) 0.0193(6) Uani 1 1 d . . . . .
C4 C 0.2219(3) 0.2630(3) 0.4782(3) 0.0198(6) Uani 1 1 d . . . . .
N5 N 0.1307(3) 0.3438(2) 0.3814(3) 0.0198(5) Uani 1 1 d . . . . .
C6 C 0.1664(3) 0.4676(3) 0.4138(3) 0.0204(6) Uani 1 1 d . . . . .
C7 C 0.1527(4) 0.7411(3) 0.4147(4) 0.0292(7) Uani 1 1 d . . . . .
H7A H 0.133408 0.737990 0.522942 0.044 Uiso 1 1 calc R U . . .
H7B H 0.109792 0.822573 0.364948 0.044 Uiso 1 1 calc R U . . .
H7C H 0.259001 0.740931 0.412497 0.044 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              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
S1 C4 1.743(3) . ?
S1 C2 1.776(3) . ?
S2 C3 1.729(3) . ?
S2 C2 1.777(3) . ?
S3 C3 1.720(3) . ?
S3 C6 1.746(3) . ?
S4 C6 1.742(3) . ?
S4 C7 1.786(3) . ?
O1 C2 1.202(4) . ?
C3 C4 1.358(4) . ?
C4 N5 1.366(4) . ?
N5 C6 1.303(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
C4 S1 C2 95.01(15) . . ?
C3 S2 C2 94.54(14) . . ?
C3 S3 C6 88.25(14) . . ?
C6 S4 C7 102.08(15) . . ?
O1 C2 S1 122.2(3) . . ?
O1 C2 S2 123.3(2) . . ?
S1 C2 S2 114.46(17) . . ?
C4 C3 S3 109.3(2) . . ?
C4 C3 S2 119.0(2) . . ?
S3 C3 S2 131.47(17) . . ?
C3 C4 N5 117.8(3) . . ?
C3 C4 S1 116.9(2) . . ?
N5 C4 S1 125.2(2) . . ?
C6 N5 C4 108.5(2) . . ?
N5 C6 S4 121.1(2) . . ?
N5 C6 S3 116.1(2) . . ?
S4 C6 S3 122.81(18) . . ?
S4 C7 H7A 109.5 . . ?
S4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
S4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C4 S1 C2 O1 -178.8(3) . . . . ?
C4 S1 C2 S2 1.1(2) . . . . ?
C3 S2 C2 O1 179.5(3) . . . . ?
C3 S2 C2 S1 -0.5(2) . . . . ?
C6 S3 C3 C4 0.3(2) . . . . ?
C6 S3 C3 S2 175.6(2) . . . . ?
C2 S2 C3 C4 -0.7(3) . . . . ?
C2 S2 C3 S3 -175.7(2) . . . . ?
S3 C3 C4 N5 -0.1(4) . . . . ?
S2 C3 C4 N5 -176.2(2) . . . . ?
S3 C3 C4 S1 177.72(16) . . . . ?
S2 C3 C4 S1 1.7(4) . . . . ?
C2 S1 C4 C3 -1.7(3) . . . . ?
C2 S1 C4 N5 176.0(3) . . . . ?
C3 C4 N5 C6 -0.2(4) . . . . ?
S1 C4 N5 C6 -177.8(2) . . . . ?
C4 N5 C6 S4 -179.9(2) . . . . ?
C4 N5 C6 S3 0.4(4) . . . . ?
C7 S4 C6 N5 174.6(3) . . . . ?
C7 S4 C6 S3 -5.8(2) . . . . ?
C3 S3 C6 N5 -0.4(3) . . . . ?
C3 S3 C6 S4 180.0(2) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: twin5.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: twin5.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR compound2f                                                 #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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 2245495'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

_audit_creation_date             2018-04-18T09:57:49-00:00
_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 N2 O S4'
_chemical_formula_moiety         'C5 N2 O S4'
_chemical_formula_weight         232.31

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.606(4)
_cell_length_b                   3.8452(7)
_cell_length_c                   20.687(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.669(9)
_cell_angle_gamma                90
_cell_volume                     1558.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2487
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.4
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.98
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

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

_exptl_absorpt_coefficient_mu    1.158
_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  0.959
_exptl_absorpt_correction_T_max  0.977

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5286  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#


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

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.028689
_diffrn_orient_matrix_ub_12      -0.11989
_diffrn_orient_matrix_ub_13      -0.033979
_diffrn_orient_matrix_ub_21      -0.010731
_diffrn_orient_matrix_ub_22      -0.188083
_diffrn_orient_matrix_ub_23      0.031502
_diffrn_orient_matrix_ub_31      -0.04081
_diffrn_orient_matrix_ub_32      0.133735
_diffrn_orient_matrix_ub_33      0.013843
_diffrn_measurement_device_type  'D8 VENTURE 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  0.0567
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_number            5045
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.966
_reflns_Friedel_coverage         0
_reflns_number_total             1704
_reflns_number_gt                1399
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (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                                       #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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)+29.7939P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1704
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.15

#----------------------------------------------------------------------------#
#                   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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
S3 S 0.42653(6) 0.2953(3) 0.54213(5) 0.0112(3) Uani 1 1 d . . . . .
S4 S 0.33707(7) 0.0153(4) 0.42806(5) 0.0140(3) Uani 1 1 d . . . . .
S2 S 0.42875(7) 0.3443(3) 0.69364(5) 0.0132(3) Uani 1 1 d . . . . .
S1 S 0.28961(7) 0.0138(3) 0.68495(6) 0.0139(3) Uani 1 1 d . . . . .
O1 O 0.3557(2) 0.1794(11) 0.79374(16) 0.0208(9) Uani 1 1 d . . . . .
N1 N 0.3065(2) 0.0097(11) 0.55237(18) 0.0112(8) Uani 1 1 d . . . . .
C3 C 0.3938(3) 0.2482(12) 0.6179(2) 0.0114(10) Uani 1 1 d . . . . .
C2 C 0.3312(3) 0.0951(12) 0.6133(2) 0.0103(10) Uani 1 1 d . . . . .
N2 N 0.4620(2) 0.3025(13) 0.3854(2) 0.0211(10) Uani 1 1 d . . . . .
C5 C 0.4112(3) 0.1847(13) 0.4015(2) 0.0136(10) Uani 1 1 d . . . . .
C1 C 0.3578(3) 0.1772(13) 0.7356(2) 0.0144(10) Uani 1 1 d . . . . .
C4 C 0.3519(3) 0.1023(12) 0.5114(2) 0.0111(10) 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
S3 C3 1.720(5) . ?
S3 C4 1.744(5) . ?
S4 C5 1.699(6) . ?
S4 C4 1.772(5) . ?
S2 C3 1.732(5) . ?
S2 C1 1.780(5) . ?
S1 C2 1.740(5) . ?
S1 C1 1.788(5) . ?
O1 C1 1.206(6) . ?
N1 C4 1.295(6) . ?
N1 C2 1.377(6) . ?
C3 C2 1.362(7) . ?
N2 C5 1.151(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
C3 S3 C4 87.4(2) . . ?
C5 S4 C4 97.2(2) . . ?
C3 S2 C1 94.0(2) . . ?
C2 S1 C1 94.3(2) . . ?
C4 N1 C2 107.7(4) . . ?
C2 C3 S3 110.0(4) . . ?
C2 C3 S2 119.2(4) . . ?
S3 C3 S2 130.8(3) . . ?
C3 C2 N1 117.3(4) . . ?
C3 C2 S1 117.5(4) . . ?
N1 C2 S1 125.2(4) . . ?
N2 C5 S4 178.0(4) . . ?
O1 C1 S2 122.3(4) . . ?
O1 C1 S1 122.7(4) . . ?
S2 C1 S1 115.0(3) . . ?
N1 C4 S3 117.6(3) . . ?
N1 C4 S4 119.2(4) . . ?
S3 C4 S4 123.1(3) . . ?

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
C4 S3 C3 C2 0.0(4) . . . . ?
C4 S3 C3 S2 176.9(4) . . . . ?
C1 S2 C3 C2 0.0(4) . . . . ?
C1 S2 C3 S3 -176.6(4) . . . . ?
S3 C3 C2 N1 0.0(6) . . . . ?
S2 C3 C2 N1 -177.3(3) . . . . ?
S3 C3 C2 S1 178.6(3) . . . . ?
S2 C3 C2 S1 1.3(6) . . . . ?
C4 N1 C2 C3 -0.1(6) . . . . ?
C4 N1 C2 S1 -178.5(4) . . . . ?
C1 S1 C2 C3 -1.8(4) . . . . ?
C1 S1 C2 N1 176.7(4) . . . . ?
C3 S2 C1 O1 179.8(5) . . . . ?
C3 S2 C1 S1 -1.2(3) . . . . ?
C2 S1 C1 O1 -179.3(5) . . . . ?
C2 S1 C1 S2 1.8(3) . . . . ?
C2 N1 C4 S3 0.1(5) . . . . ?
C2 N1 C4 S4 177.9(3) . . . . ?
C3 S3 C4 N1 -0.1(4) . . . . ?
C3 S3 C4 S4 -177.8(3) . . . . ?
C5 S4 C4 N1 -179.3(4) . . . . ?
C5 S4 C4 S3 -1.6(4) . . . . ?


####################################################################### 
# 
# 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_TTFSCH2CH2CN
_database_code_depnum_ccdc_archive 'CCDC 2245498'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 31 mars 2022                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H10 N2 S8'
_chemical_formula_sum            'C12 H10 N2 S8'
_chemical_formula_weight         438.70
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0133(3)
_cell_length_b                   10.3719(7)
_cell_length_c                   14.1989(9)
_cell_angle_alpha                84.691(2)
_cell_angle_beta                 79.633(2)
_cell_angle_gamma                85.606(2)
_cell_volume                     865.76(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.3622
_cell_measurement_theta_max      27.4865
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0887763
_diffrn_orient_matrix_UB_21      0.0070186
_diffrn_orient_matrix_UB_31      0.1440739
_diffrn_orient_matrix_UB_12      -0.0676398
_diffrn_orient_matrix_UB_22      -0.0520441
_diffrn_orient_matrix_UB_32      -0.0461256
_diffrn_orient_matrix_UB_13      0.0421465
_diffrn_orient_matrix_UB_23      -0.0564498
_diffrn_orient_matrix_UB_33      0.0140165


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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             448
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.026
_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  0.829
_exptl_absorpt_correction_T_max  0.921

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        5                                        #
# Total number of frames [*] :      554                                        #
# Total length of scans  [*] :   554.00 (deg.)                                 #
# Rotation speed         [*] :    80.00 sec./deg.                              #
# Total exposition time  [*] :     12 h  18.7 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     8.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7   0.0 #
#  2 Fast@    8.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7   0.0 #
#  3 Phi     80.0  1.00    34.0   360  360.0    0.1    2.4    0.0  -44.5   0.0 #
#  4 Omega   80.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5   0.0 #
#  5 Omega   80.0  1.00    34.0    97   97.0    0.1    2.7  144.0  -44.5   0.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0236
_diffrn_reflns_av_r_equivalents  0.0269
_diffrn_reflns_number            17937
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_reflns_number_total             3918
_reflns_number_gt                3494
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.5693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3918
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.054

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.2695(4) -0.1206(3) 0.48755(18) 0.0749(7) Uani 1 1 d . . . . .
C2 C 1.2140(4) -0.0917(3) 0.5633(2) 0.0548(6) Uani 1 1 d . . . . .
C3 C 1.1435(4) -0.0591(3) 0.66347(19) 0.0551(6) Uani 1 1 d . . . . .
H3A H 1.144897 -0.137807 0.705969 0.066 Uiso 1 1 calc R U . . .
H3B H 0.989777 -0.020525 0.671980 0.066 Uiso 1 1 calc R U . . .
C4 C 1.2978(4) 0.0342(2) 0.69022(17) 0.0460(5) Uani 1 1 d . . . . .
H4A H 1.287009 0.115242 0.650890 0.055 Uiso 1 1 calc R U . . .
H4B H 1.453018 -0.001486 0.676437 0.055 Uiso 1 1 calc R U . . .
C5 C 0.9874(3) 0.17035(17) 0.81467(13) 0.0311(4) Uani 1 1 d . . . . .
N6 N 0.8967(3) 0.21064(15) 0.73957(12) 0.0349(3) Uani 1 1 d . . . . .
C7 C 0.7057(3) 0.28875(17) 0.76989(13) 0.0305(4) Uani 1 1 d . . . . .
C8 C 0.6537(3) 0.30664(17) 0.86453(13) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.3458(3) 0.43846(17) 0.79089(12) 0.0285(3) Uani 1 1 d . . . . .
C10 C 0.1617(3) 0.51613(17) 0.77961(12) 0.0290(4) Uani 1 1 d . . . . .
C11 C -0.1640(3) 0.65058(17) 0.71176(13) 0.0294(4) Uani 1 1 d . . . . .
C12 C -0.2070(3) 0.66409(17) 0.80636(13) 0.0293(4) Uani 1 1 d . . . . .
C13 C -0.2235(5) 0.6628(3) 0.52185(17) 0.0631(7) Uani 1 1 d . . . . .
H13A H -0.075625 0.692995 0.497330 0.095 Uiso 1 1 calc R U . . .
H13B H -0.322690 0.689909 0.476832 0.095 Uiso 1 1 calc R U . . .
H13C H -0.213577 0.569785 0.531192 0.095 Uiso 1 1 calc R U . . .
C14 C -0.3125(4) 0.8804(2) 0.9064(2) 0.0539(6) Uani 1 1 d . . . . .
H14A H -0.208743 0.843466 0.947051 0.081 Uiso 1 1 calc R U . . .
H14B H -0.426807 0.935153 0.942242 0.081 Uiso 1 1 calc R U . . .
H14C H -0.231935 0.930803 0.852713 0.081 Uiso 1 1 calc R U . . .
S1 S 1.22977(9) 0.06617(5) 0.81499(4) 0.04398(14) Uani 1 1 d . . . . .
S2 S 0.85133(8) 0.22382(5) 0.92469(3) 0.03612(12) Uani 1 1 d . . . . .
S3 S 0.41542(8) 0.40272(5) 0.90690(3) 0.03471(12) Uani 1 1 d . . . . .
S4 S 0.52517(8) 0.36562(5) 0.69537(3) 0.03517(12) Uani 1 1 d . . . . .
S5 S -0.01657(8) 0.58444(5) 0.87628(3) 0.03500(12) Uani 1 1 d . . . . .
S6 S 0.07745(8) 0.55431(5) 0.66771(3) 0.03803(13) Uani 1 1 d . . . . .
S7 S -0.44399(8) 0.75250(5) 0.86367(4) 0.03644(12) Uani 1 1 d . . . . .
S8 S -0.33239(10) 0.72883(6) 0.63352(4) 0.04928(16) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              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
N1 C2 1.128(4) . ?
C2 C3 1.472(4) . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 S1 1.801(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N6 1.304(2) . ?
C5 S2 1.7460(19) . ?
C5 S1 1.7468(18) . ?
N6 C7 1.380(2) . ?
C7 C8 1.351(3) . ?
C7 S4 1.7489(18) . ?
C8 S2 1.7184(17) . ?
C8 S3 1.7291(18) . ?
C9 C10 1.343(2) . ?
C9 S4 1.7641(18) . ?
C9 S3 1.7712(18) . ?
C10 S5 1.7519(18) . ?
C10 S6 1.7552(18) . ?
C11 C12 1.340(3) . ?
C11 S8 1.7409(18) . ?
C11 S6 1.7499(17) . ?
C12 S7 1.7474(17) . ?
C12 S5 1.7585(18) . ?
C13 S8 1.781(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 S7 1.798(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 C3 177.9(3) . . ?
C2 C3 C4 111.5(2) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 S1 112.65(16) . . ?
C3 C4 H4A 109.1 . . ?
S1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
S1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N6 C5 S2 116.82(13) . . ?
N6 C5 S1 125.81(14) . . ?
S2 C5 S1 117.37(11) . . ?
C5 N6 C7 107.80(16) . . ?
C8 C7 N6 117.43(16) . . ?
C8 C7 S4 117.50(13) . . ?
N6 C7 S4 125.07(14) . . ?
C7 C8 S2 110.19(13) . . ?
C7 C8 S3 119.54(14) . . ?
S2 C8 S3 130.27(11) . . ?
C10 C9 S4 123.44(14) . . ?
C10 C9 S3 119.76(14) . . ?
S4 C9 S3 116.79(10) . . ?
C9 C10 S5 122.40(14) . . ?
C9 C10 S6 122.78(14) . . ?
S5 C10 S6 114.80(10) . . ?
C12 C11 S8 122.39(14) . . ?
C12 C11 S6 117.23(13) . . ?
S8 C11 S6 120.33(11) . . ?
C11 C12 S7 123.71(14) . . ?
C11 C12 S5 117.57(13) . . ?
S7 C12 S5 118.71(10) . . ?
S8 C13 H13A 109.5 . . ?
S8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S7 C14 H14A 109.5 . . ?
S7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 S1 C4 100.78(10) . . ?
C8 S2 C5 87.76(9) . . ?
C8 S3 C9 92.88(8) . . ?
C7 S4 C9 93.27(8) . . ?
C10 S5 C12 95.01(8) . . ?
C11 S6 C10 95.39(8) . . ?
C12 S7 C14 101.12(10) . . ?
C11 S8 C13 103.92(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 S1 -175.41(18) . . . . ?
S2 C5 N6 C7 -0.3(2) . . . . ?
S1 C5 N6 C7 178.71(14) . . . . ?
C5 N6 C7 C8 -0.1(2) . . . . ?
C5 N6 C7 S4 -179.77(14) . . . . ?
N6 C7 C8 S2 0.5(2) . . . . ?
S4 C7 C8 S2 -179.84(10) . . . . ?
N6 C7 C8 S3 -179.61(13) . . . . ?
S4 C7 C8 S3 0.1(2) . . . . ?
S4 C9 C10 S5 178.66(10) . . . . ?
S3 C9 C10 S5 -0.2(2) . . . . ?
S4 C9 C10 S6 0.1(2) . . . . ?
S3 C9 C10 S6 -178.85(10) . . . . ?
S8 C11 C12 S7 4.1(2) . . . . ?
S6 C11 C12 S7 -178.12(10) . . . . ?
S8 C11 C12 S5 -177.57(10) . . . . ?
S6 C11 C12 S5 0.2(2) . . . . ?
N6 C5 S1 C4 -1.3(2) . . . . ?
S2 C5 S1 C4 177.66(12) . . . . ?
C3 C4 S1 C5 -75.63(18) . . . . ?
C7 C8 S2 C5 -0.51(15) . . . . ?
S3 C8 S2 C5 179.60(15) . . . . ?
N6 C5 S2 C8 0.49(16) . . . . ?
S1 C5 S2 C8 -178.61(12) . . . . ?
C7 C8 S3 C9 -0.85(17) . . . . ?
S2 C8 S3 C9 179.03(14) . . . . ?
C10 C9 S3 C8 -179.66(16) . . . . ?
S4 C9 S3 C8 1.36(12) . . . . ?
C8 C7 S4 C9 0.77(16) . . . . ?
N6 C7 S4 C9 -179.59(16) . . . . ?
C10 C9 S4 C7 179.72(17) . . . . ?
S3 C9 S4 C7 -1.34(12) . . . . ?
C9 C10 S5 C12 -178.75(17) . . . . ?
S6 C10 S5 C12 -0.05(12) . . . . ?
C11 C12 S5 C10 -0.11(17) . . . . ?
S7 C12 S5 C10 178.33(11) . . . . ?
C12 C11 S6 C10 -0.23(17) . . . . ?
S8 C11 S6 C10 177.63(12) . . . . ?
C9 C10 S6 C11 178.84(17) . . . . ?
S5 C10 S6 C11 0.14(12) . . . . ?
C11 C12 S7 C14 -115.80(19) . . . . ?
S5 C12 S7 C14 65.87(14) . . . . ?
C12 C11 S8 C13 -173.04(19) . . . . ?
S6 C11 S8 C13 9.22(17) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job2.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job2.hkl
#...............................................................................


####################################################################### 
# 
# 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_TTFHTCNQF4
_database_code_depnum_ccdc_archive 'CCDC 2245501'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 10 juin 2022                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 N S7, C12 F4 N4'
_chemical_formula_sum            'C21 H7 F4 N5 S7'
_chemical_formula_weight         629.74
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1063(15)
_cell_length_b                   12.405(3)
_cell_length_c                   13.462(4)
_cell_angle_alpha                100.797(12)
_cell_angle_beta                 91.933(13)
_cell_angle_gamma                92.390(9)
_cell_volume                     1163.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7034
_cell_measurement_theta_min      2.4818
_cell_measurement_theta_max      27.4706
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0478139
_diffrn_orient_matrix_UB_21      -0.0486759
_diffrn_orient_matrix_UB_31      0.1233306
_diffrn_orient_matrix_UB_12      0.0273702
_diffrn_orient_matrix_UB_22      -0.0699787
_diffrn_orient_matrix_UB_32      -0.0334504
_diffrn_orient_matrix_UB_13      0.0713491
_diffrn_orient_matrix_UB_23      0.0190151
_diffrn_orient_matrix_UB_33      -0.0166024


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

_exptl_crystal_description       board
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             632
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.735
_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  0.846
_exptl_absorpt_correction_T_max  0.985

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        4                                        #
# Total number of frames [*] :      554                                        #
# Total length of scans  [*] :   554.00 (deg.)                                 #
# Rotation speed         [*] :    20.00 sec./deg.                              #
# Total exposition time  [*] :      3 h   4.7 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     2.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Phi     20.0  1.00    34.0   360  360.0    0.1    2.4    0.0  -44.5 150.0 #
#  3 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5 150.0 #
#  4 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7  144.0  -44.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0470
_diffrn_reflns_av_r_equivalents  0.0589
_diffrn_reflns_number            24703
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             5303
_reflns_number_gt                4361
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+1.6956P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5303
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.073

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
S1 S 0.83472(10) 0.65361(6) 0.68280(5) 0.02400(16) Uani 1 1 d . . . . .
S2 S 0.93768(11) 0.86343(6) 0.86452(5) 0.02805(17) Uani 1 1 d . . . . .
S3 S 0.77929(9) 0.81724(5) 0.54626(5) 0.01781(14) Uani 1 1 d . . . . .
S4 S 0.87202(10) 1.00411(5) 0.70796(5) 0.02041(15) Uani 1 1 d . . . . .
S5 S 0.70130(9) 0.98495(5) 0.39262(5) 0.01844(14) Uani 1 1 d . . . . .
S6 S 0.80330(10) 1.17035(5) 0.56275(5) 0.02109(15) Uani 1 1 d . . . . .
S7A S 0.62929(14) 1.16753(8) 0.26381(7) 0.0230(2) Uani 0.865(3) 1 d . . P A 1
N9A N 0.7216(5) 1.3070(3) 0.4311(3) 0.0230(2) Uani 0.865(3) 1 d . . P A 1
C10A C 0.6674(5) 1.2991(3) 0.3351(3) 0.0264(8) Uani 0.865(3) 1 d . . P A 1
H10A H 0.650170 1.362472 0.306269 0.032 Uiso 0.865(3) 1 calc R U P A 1
N9B N 0.628(4) 1.145(2) 0.2869(18) 0.0230(2) Uani 0.135(3) 1 d . . P A 2
S7B S 0.6900(8) 1.3202(5) 0.4070(5) 0.0230(2) Uani 0.135(3) 1 d . . P A 2
C10B C 0.623(3) 1.250(2) 0.2920(19) 0.0264(8) Uani 0.135(3) 1 d . . P A 2
H10B H 0.584990 1.283242 0.236879 0.032 Uiso 0.135(3) 1 calc R U P A 2
C1 C 0.7748(5) 0.5775(2) 0.5578(2) 0.0324(7) Uani 1 1 d . . . . .
H1A H 0.653937 0.600717 0.533906 0.049 Uiso 1 1 calc R U . . .
H1B H 0.764536 0.498835 0.559468 0.049 Uiso 1 1 calc R U . . .
H1C H 0.873118 0.591412 0.511827 0.049 Uiso 1 1 calc R U . . .
C2 C 0.8354(3) 0.7880(2) 0.66419(18) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.8754(4) 0.8760(2) 0.74079(19) 0.0200(5) Uani 1 1 d . . . . .
C4 C 0.7668(4) 0.9445(3) 0.9366(2) 0.0329(7) Uani 1 1 d . . . . .
H4A H 0.779326 1.020385 0.925671 0.049 Uiso 1 1 calc R U . . .
H4B H 0.788577 0.943532 1.008670 0.049 Uiso 1 1 calc R U . . .
H4C H 0.639661 0.913841 0.914615 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8034(3) 0.9580(2) 0.58404(18) 0.0163(5) Uani 1 1 d . . . . .
C6 C 0.7745(3) 1.0306(2) 0.51895(18) 0.0165(5) Uani 1 1 d . . . . .
C7 C 0.6868(4) 1.1171(2) 0.36965(19) 0.0197(5) Uani 1 1 d . . . . .
C8 C 0.7297(4) 1.2023(2) 0.4483(2) 0.0203(5) Uani 1 1 d . . . . .
C11 C 0.4760(4) 0.7102(2) 0.18133(19) 0.0199(5) Uani 1 1 d . . . . .
C12 C 0.5196(4) 0.6871(2) 0.2795(2) 0.0227(6) Uani 1 1 d . . . . .
N13 N 0.5524(4) 0.6739(2) 0.36021(18) 0.0344(6) Uani 1 1 d . . . . .
C14 C 0.5170(4) 0.8215(2) 0.1755(2) 0.0247(6) Uani 1 1 d . . . . .
N15 N 0.5576(4) 0.9133(2) 0.17911(19) 0.0338(6) Uani 1 1 d . . . . .
C16 C 0.3879(3) 0.6309(2) 0.10312(18) 0.0177(5) Uani 1 1 d . . . . .
C17 C 0.3212(4) 0.6544(2) 0.00933(19) 0.0184(5) Uani 1 1 d . . . . .
C18 C 0.2337(4) 0.5769(2) -0.06448(18) 0.0180(5) Uani 1 1 d . . . . .
C19 C 0.2047(3) 0.4653(2) -0.05704(18) 0.0168(5) Uani 1 1 d . . . . .
C20 C 0.2749(3) 0.4421(2) 0.03578(18) 0.0175(5) Uani 1 1 d . . . . .
C21 C 0.3588(4) 0.5194(2) 0.11034(18) 0.0184(5) Uani 1 1 d . . . . .
F22 F 0.3441(2) 0.75705(13) -0.00747(12) 0.0258(4) Uani 1 1 d . . . . .
F23 F 0.1738(2) 0.60865(13) -0.14977(11) 0.0253(4) Uani 1 1 d . . . . .
F24 F 0.2625(2) 0.33794(13) 0.05063(11) 0.0260(4) Uani 1 1 d . . . . .
F25 F 0.4255(2) 0.48576(13) 0.19354(11) 0.0246(3) Uani 1 1 d . . . . .
C26 C 0.1192(4) 0.3834(2) -0.13419(19) 0.0198(5) Uani 1 1 d . . . . .
C27 C 0.0550(4) 0.4033(2) -0.2307(2) 0.0240(6) Uani 1 1 d . . . . .
N28 N -0.0012(4) 0.4103(2) -0.30970(19) 0.0356(6) Uani 1 1 d . . . . .
C29 C 0.0676(4) 0.2750(2) -0.12010(19) 0.0217(6) Uani 1 1 d . . . . .
N30 N 0.0194(4) 0.1873(2) -0.11338(18) 0.0299(6) 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
S1 C2 1.732(3) . ?
S1 C1 1.797(3) . ?
S2 C3 1.746(3) . ?
S2 C4 1.801(3) . ?
S3 C5 1.725(3) . ?
S3 C2 1.731(3) . ?
S4 C5 1.706(3) . ?
S4 C3 1.728(3) . ?
S5 C7 1.731(3) . ?
S5 C6 1.743(3) . ?
S6 C6 1.725(3) . ?
S6 C8 1.731(3) . ?
S7A C7 1.704(3) . ?
S7A C10A 1.737(4) . ?
N9A C10A 1.322(5) . ?
N9A C8 1.365(4) . ?
C10A H10A 0.9500 . ?
N9B C7 1.29(2) . ?
N9B C10B 1.30(3) . ?
S7B C10B 1.67(3) . ?
S7B C8 1.690(6) . ?
C10B H10B 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.367(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.385(4) . ?
C7 C8 1.364(4) . ?
C11 C16 1.409(4) . ?
C11 C14 1.417(4) . ?
C11 C12 1.431(4) . ?
C12 N13 1.146(4) . ?
C14 N15 1.154(4) . ?
C16 C21 1.411(4) . ?
C16 C17 1.419(3) . ?
C17 F22 1.339(3) . ?
C17 C18 1.359(4) . ?
C18 F23 1.343(3) . ?
C18 C19 1.414(4) . ?
C19 C26 1.411(4) . ?
C19 C20 1.413(3) . ?
C20 F24 1.344(3) . ?
C20 C21 1.354(4) . ?
C21 F25 1.345(3) . ?
C26 C29 1.427(4) . ?
C26 C27 1.431(4) . ?
C27 N28 1.143(4) . ?
C29 N30 1.148(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 102.01(13) . . ?
C3 S2 C4 102.18(13) . . ?
C5 S3 C2 95.47(12) . . ?
C5 S4 C3 96.10(13) . . ?
C7 S5 C6 93.08(13) . . ?
C6 S6 C8 93.51(13) . . ?
C7 S7A C10A 88.32(15) . . ?
C10A N9A C8 106.7(3) . . ?
N9A C10A S7A 117.0(3) . . ?
N9A C10A H10A 121.5 . . ?
S7A C10A H10A 121.5 . . ?
C7 N9B C10B 114(2) . . ?
C10B S7B C8 91.0(9) . . ?
N9B C10B S7B 112.0(19) . . ?
N9B C10B H10B 124.0 . . ?
S7B C10B H10B 124.0 . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 S3 116.5(2) . . ?
C3 C2 S1 122.6(2) . . ?
S3 C2 S1 120.86(15) . . ?
C2 C3 S4 116.2(2) . . ?
C2 C3 S2 123.4(2) . . ?
S4 C3 S2 120.38(16) . . ?
S2 C4 H4A 109.5 . . ?
S2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S4 121.1(2) . . ?
C6 C5 S3 123.22(19) . . ?
S4 C5 S3 115.62(15) . . ?
C5 C6 S6 120.27(19) . . ?
C5 C6 S5 121.7(2) . . ?
S6 C6 S5 118.01(15) . . ?
N9B C7 C8 115.3(12) . . ?
C8 C7 S7A 109.5(2) . . ?
N9B C7 S5 126.8(12) . . ?
C8 C7 S5 117.8(2) . . ?
S7A C7 S5 132.78(17) . . ?
C7 C8 N9A 118.5(3) . . ?
C7 C8 S7B 107.7(3) . . ?
C7 C8 S6 117.6(2) . . ?
N9A C8 S6 123.8(2) . . ?
S7B C8 S6 134.7(3) . . ?
C16 C11 C14 125.0(2) . . ?
C16 C11 C12 122.1(2) . . ?
C14 C11 C12 112.7(2) . . ?
N13 C12 C11 176.6(3) . . ?
N15 C14 C11 174.0(3) . . ?
C11 C16 C21 123.0(2) . . ?
C11 C16 C17 123.7(2) . . ?
C21 C16 C17 113.3(2) . . ?
F22 C17 C18 118.3(2) . . ?
F22 C17 C16 119.0(2) . . ?
C18 C17 C16 122.7(2) . . ?
F23 C18 C17 117.7(2) . . ?
F23 C18 C19 118.5(2) . . ?
C17 C18 C19 123.8(2) . . ?
C26 C19 C20 122.4(2) . . ?
C26 C19 C18 124.5(2) . . ?
C20 C19 C18 113.1(2) . . ?
F24 C20 C21 117.8(2) . . ?
F24 C20 C19 118.9(2) . . ?
C21 C20 C19 123.3(2) . . ?
F25 C21 C20 117.3(2) . . ?
F25 C21 C16 118.8(2) . . ?
C20 C21 C16 123.7(2) . . ?
C19 C26 C29 123.4(2) . . ?
C19 C26 C27 123.7(2) . . ?
C29 C26 C27 112.5(2) . . ?
N28 C27 C26 174.3(3) . . ?
N30 C29 C26 176.2(3) . . ?

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
C8 N9A C10A S7A -1.0(4) . . . . ?
C7 S7A C10A N9A 0.7(3) . . . . ?
C7 N9B C10B S7B -2(3) . . . . ?
C8 S7B C10B N9B 1.0(19) . . . . ?
C5 S3 C2 C3 0.3(2) . . . . ?
C5 S3 C2 S1 178.86(16) . . . . ?
C1 S1 C2 C3 -179.8(2) . . . . ?
C1 S1 C2 S3 1.7(2) . . . . ?
S3 C2 C3 S4 -2.1(3) . . . . ?
S1 C2 C3 S4 179.32(14) . . . . ?
S3 C2 C3 S2 -179.25(14) . . . . ?
S1 C2 C3 S2 2.2(3) . . . . ?
C5 S4 C3 C2 2.8(2) . . . . ?
C5 S4 C3 S2 -179.98(16) . . . . ?
C4 S2 C3 C2 -125.0(2) . . . . ?
C4 S2 C3 S4 58.0(2) . . . . ?
C3 S4 C5 C6 179.0(2) . . . . ?
C3 S4 C5 S3 -2.58(17) . . . . ?
C2 S3 C5 C6 -179.9(2) . . . . ?
C2 S3 C5 S4 1.67(16) . . . . ?
S4 C5 C6 S6 -1.2(3) . . . . ?
S3 C5 C6 S6 -179.52(14) . . . . ?
S4 C5 C6 S5 -179.11(14) . . . . ?
S3 C5 C6 S5 2.6(3) . . . . ?
C8 S6 C6 C5 -175.9(2) . . . . ?
C8 S6 C6 S5 2.13(17) . . . . ?
C7 S5 C6 C5 176.8(2) . . . . ?
C7 S5 C6 S6 -1.16(17) . . . . ?
C10B N9B C7 C8 1(3) . . . . ?
C10B N9B C7 S5 176.6(15) . . . . ?
C10A S7A C7 C8 -0.2(2) . . . . ?
C10A S7A C7 S5 -179.5(2) . . . . ?
C6 S5 C7 N9B -175.9(15) . . . . ?
C6 S5 C7 C8 -0.7(2) . . . . ?
C6 S5 C7 S7A 178.6(2) . . . . ?
S7A C7 C8 N9A -0.4(3) . . . . ?
S5 C7 C8 N9A 179.1(2) . . . . ?
N9B C7 C8 S7B -0.6(14) . . . . ?
S5 C7 C8 S7B -176.3(3) . . . . ?
N9B C7 C8 S6 178.1(13) . . . . ?
S7A C7 C8 S6 -177.07(14) . . . . ?
S5 C7 C8 S6 2.4(3) . . . . ?
C10A N9A C8 C7 0.9(4) . . . . ?
C10A N9A C8 S6 177.3(2) . . . . ?
C10B S7B C8 C7 -0.2(8) . . . . ?
C10B S7B C8 S6 -178.6(8) . . . . ?
C6 S6 C8 C7 -2.6(2) . . . . ?
C6 S6 C8 N9A -179.1(3) . . . . ?
C6 S6 C8 S7B 175.6(4) . . . . ?
C14 C11 C16 C21 176.5(2) . . . . ?
C12 C11 C16 C21 -8.8(4) . . . . ?
C14 C11 C16 C17 -2.9(4) . . . . ?
C12 C11 C16 C17 171.7(2) . . . . ?
C11 C16 C17 F22 0.8(4) . . . . ?
C21 C16 C17 F22 -178.7(2) . . . . ?
C11 C16 C17 C18 -178.9(2) . . . . ?
C21 C16 C17 C18 1.6(4) . . . . ?
F22 C17 C18 F23 -0.6(3) . . . . ?
C16 C17 C18 F23 179.1(2) . . . . ?
F22 C17 C18 C19 178.5(2) . . . . ?
C16 C17 C18 C19 -1.8(4) . . . . ?
F23 C18 C19 C26 1.1(4) . . . . ?
C17 C18 C19 C26 -178.0(2) . . . . ?
F23 C18 C19 C20 179.6(2) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C26 C19 C20 F24 1.1(4) . . . . ?
C18 C19 C20 F24 -177.5(2) . . . . ?
C26 C19 C20 C21 179.4(2) . . . . ?
C18 C19 C20 C21 0.9(4) . . . . ?
F24 C20 C21 F25 0.7(3) . . . . ?
C19 C20 C21 F25 -177.6(2) . . . . ?
F24 C20 C21 C16 177.4(2) . . . . ?
C19 C20 C21 C16 -1.0(4) . . . . ?
C11 C16 C21 F25 -3.2(4) . . . . ?
C17 C16 C21 F25 176.3(2) . . . . ?
C11 C16 C21 C20 -179.8(2) . . . . ?
C17 C16 C21 C20 -0.3(4) . . . . ?
C20 C19 C26 C29 10.7(4) . . . . ?
C18 C19 C26 C29 -170.9(2) . . . . ?
C20 C19 C26 C27 -176.9(2) . . . . ?
C18 C19 C26 C27 1.4(4) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................


####################################################################### 
# 
# 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_TTFH
_database_code_depnum_ccdc_archive 'CCDC 2245499'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 31 mars 2022                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 N S7'
_chemical_formula_sum            'C9 H7 N S7'
_chemical_formula_weight         353.58
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.906(2)
_cell_length_b                   8.704(3)
_cell_length_c                   11.633(3)
_cell_angle_alpha                100.130(10)
_cell_angle_beta                 101.742(10)
_cell_angle_gamma                113.220(10)
_cell_volume                     690.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9357
_cell_measurement_theta_min      2.6563
_cell_measurement_theta_max      27.4637
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0176094
_diffrn_orient_matrix_UB_21      0.1382699
_diffrn_orient_matrix_UB_31      -0.0375923
_diffrn_orient_matrix_UB_12      -0.1070335
_diffrn_orient_matrix_UB_22      0.0640294
_diffrn_orient_matrix_UB_32      -0.0381026
_diffrn_orient_matrix_UB_13      -0.0262470
_diffrn_orient_matrix_UB_23      0.0514971
_diffrn_orient_matrix_UB_33      0.0710428


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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             360
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.116
_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  0.648
_exptl_absorpt_correction_T_max  0.765

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        5                                        #
# Total number of frames [*] :      597                                        #
# Total length of scans  [*] :   597.00 (deg.)                                 #
# Rotation speed         [*] :     5.00 sec./deg.                              #
# Total exposition time  [*] :         49.8 min.                               #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7   0.0 #
#  2 Phi      5.0  1.00    34.0   360  360.0    0.1    2.4    0.0  -44.5   0.0 #
#  3 Omega    5.0  1.00    34.0    43   43.0   19.8   18.7  252.3  -56.1   0.0 #
#  4 Omega    5.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5   0.0 #
#  5 Omega    5.0  1.00    34.0    97   97.0    0.1    2.7   72.0  -44.5   0.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0249
_diffrn_reflns_av_r_equivalents  0.0303
_diffrn_reflns_number            14575
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.955
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.975
_reflns_number_total             3075
_reflns_number_gt                2738
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0283P)²+0.2722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019_2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.023(5)
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.4490(3) 0.7234(3) 1.00034(17) 0.0575(5) Uani 1 1 d . . . . .
H1 H 0.473417 0.805760 1.072224 0.069 Uiso 1 1 calc R U . . .
N2 N 0.5844(2) 0.7289(2) 0.95201(13) 0.0502(4) Uani 1 1 d . . . . .
C3 C 0.5058(2) 0.5923(2) 0.84743(14) 0.0376(3) Uani 1 1 d . . . . .
C4 C 0.3139(2) 0.48451(19) 0.81786(13) 0.0357(3) Uani 1 1 d . . . . .
C5 C 0.4280(2) 0.35886(19) 0.65182(14) 0.0352(3) Uani 1 1 d . . . . .
C6 C 0.4314(2) 0.26080(19) 0.54996(13) 0.0336(3) Uani 1 1 d . . . . .
C7 C 0.3459(2) 0.02825(19) 0.34673(13) 0.0332(3) Uani 1 1 d . . . . .
C8 C 0.0843(3) -0.0777(3) 0.11884(19) 0.0739(7) Uani 1 1 d . . . . .
H8A H 0.011390 -0.033831 0.159433 0.111 Uiso 1 1 calc R U . . .
H8B H -0.001780 -0.171234 0.046617 0.111 Uiso 1 1 calc R U . . .
H8C H 0.175096 0.014202 0.096289 0.111 Uiso 1 1 calc R U . . .
C9 C 0.5344(2) 0.13599(19) 0.37140(13) 0.0324(3) Uani 1 1 d . . . . .
C10 C 0.9050(2) 0.2845(3) 0.35341(18) 0.0523(4) Uani 1 1 d . . . . .
H10A H 0.898967 0.393543 0.359173 0.078 Uiso 1 1 calc R U . . .
H10B H 0.992410 0.278126 0.308413 0.078 Uiso 1 1 calc R U . . .
H10C H 0.949920 0.276374 0.434182 0.078 Uiso 1 1 calc R U . . .
S1 S 0.22156(7) 0.55590(6) 0.92488(4) 0.04997(14) Uani 1 1 d . . . . .
S2 S 0.20916(6) 0.30538(5) 0.68989(4) 0.04515(13) Uani 1 1 d . . . . .
S3 S 0.63273(6) 0.54434(6) 0.75193(4) 0.04615(13) Uani 1 1 d . . . . .
S4 S 0.64209(5) 0.31015(5) 0.50575(4) 0.04131(13) Uani 1 1 d . . . . .
S5 S 0.22870(5) 0.07381(5) 0.45180(4) 0.04086(12) Uani 1 1 d . . . . .
S6 S 0.21232(6) -0.15700(5) 0.22064(4) 0.04139(13) Uani 1 1 d . . . . .
S7 S 0.67070(6) 0.10925(6) 0.27628(4) 0.05318(15) 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
C1 N2 1.295(2) . ?
C1 S1 1.723(2) . ?
C1 H1 0.9300 . ?
N2 C3 1.371(2) . ?
C3 C4 1.361(2) . ?
C3 S3 1.7426(16) . ?
C4 S1 1.7100(15) . ?
C4 S2 1.7310(15) . ?
C5 C6 1.345(2) . ?
C5 S3 1.7588(15) . ?
C5 S2 1.7761(15) . ?
C6 S5 1.7511(15) . ?
C6 S4 1.7562(15) . ?
C7 C9 1.345(2) . ?
C7 S6 1.7497(15) . ?
C7 S5 1.7580(15) . ?
C8 S6 1.804(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 S7 1.7416(15) . ?
C9 S4 1.7530(15) . ?
C10 S7 1.7827(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N2 C1 S1 116.70(13) . . ?
N2 C1 H1 121.7 . . ?
S1 C1 H1 121.7 . . ?
C1 N2 C3 108.46(15) . . ?
C4 C3 N2 116.88(14) . . ?
C4 C3 S3 117.85(11) . . ?
N2 C3 S3 125.25(12) . . ?
C3 C4 S1 109.42(11) . . ?
C3 C4 S2 118.79(11) . . ?
S1 C4 S2 131.75(9) . . ?
C6 C5 S3 123.07(12) . . ?
C6 C5 S2 120.21(12) . . ?
S3 C5 S2 116.71(8) . . ?
C5 C6 S5 123.09(12) . . ?
C5 C6 S4 122.26(12) . . ?
S5 C6 S4 114.65(8) . . ?
C9 C7 S6 124.67(11) . . ?
C9 C7 S5 117.33(11) . . ?
S6 C7 S5 117.96(8) . . ?
S6 C8 H8A 109.5 . . ?
S6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
S6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 S7 122.95(12) . . ?
C7 C9 S4 117.14(11) . . ?
S7 C9 S4 119.91(8) . . ?
S7 C10 H10A 109.5 . . ?
S7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 S1 C1 88.54(8) . . ?
C4 S2 C5 93.11(7) . . ?
C3 S3 C5 93.50(7) . . ?
C9 S4 C6 95.51(7) . . ?
C6 S5 C7 95.35(7) . . ?
C7 S6 C8 101.38(9) . . ?
C9 S7 C10 103.49(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
S1 C1 N2 C3 0.2(2) . . . . ?
C1 N2 C3 C4 -0.5(2) . . . . ?
C1 N2 C3 S3 -179.20(15) . . . . ?
N2 C3 C4 S1 0.5(2) . . . . ?
S3 C3 C4 S1 179.36(9) . . . . ?
N2 C3 C4 S2 -177.62(13) . . . . ?
S3 C3 C4 S2 1.2(2) . . . . ?
S3 C5 C6 S5 178.77(9) . . . . ?
S2 C5 C6 S5 -2.0(2) . . . . ?
S3 C5 C6 S4 -0.7(2) . . . . ?
S2 C5 C6 S4 178.50(9) . . . . ?
S6 C7 C9 S7 2.4(2) . . . . ?
S5 C7 C9 S7 -179.73(8) . . . . ?
S6 C7 C9 S4 -177.86(8) . . . . ?
S5 C7 C9 S4 -0.03(18) . . . . ?
C3 C4 S1 C1 -0.34(14) . . . . ?
S2 C4 S1 C1 177.51(14) . . . . ?
N2 C1 S1 C4 0.09(18) . . . . ?
C3 C4 S2 C5 -1.81(15) . . . . ?
S1 C4 S2 C5 -179.49(13) . . . . ?
C6 C5 S2 C4 -177.36(14) . . . . ?
S3 C5 S2 C4 1.87(11) . . . . ?
C4 C3 S3 C5 0.15(15) . . . . ?
N2 C3 S3 C5 178.86(16) . . . . ?
C6 C5 S3 C3 177.81(15) . . . . ?
S2 C5 S3 C3 -1.40(11) . . . . ?
C7 C9 S4 C6 -0.96(14) . . . . ?
S7 C9 S4 C6 178.75(10) . . . . ?
C5 C6 S4 C9 -178.90(14) . . . . ?
S5 C6 S4 C9 1.61(10) . . . . ?
C5 C6 S5 C7 178.90(15) . . . . ?
S4 C6 S5 C7 -1.62(10) . . . . ?
C9 C7 S5 C6 1.00(14) . . . . ?
S6 C7 S5 C6 178.98(9) . . . . ?
C9 C7 S6 C8 -101.21(16) . . . . ?
S5 C7 S6 C8 80.97(12) . . . . ?
C7 C9 S7 C10 -179.57(14) . . . . ?
S4 C9 S7 C10 0.74(12) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................


####################################################################### 
# 
# 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_TTFSCN
_database_code_depnum_ccdc_archive 'CCDC 2245500'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 juillet 2022                                          #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H6 N2 S8'
_chemical_formula_sum            'C10 H6 N2 S8'
_chemical_formula_weight         410.65
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4506(12)
_cell_length_b                   8.1175(12)
_cell_length_c                   13.345(2)
_cell_angle_alpha                73.335(5)
_cell_angle_beta                 87.672(6)
_cell_angle_gamma                81.049(6)
_cell_volume                     763.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      2.6755
_cell_measurement_theta_max      27.4777
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0991019
_diffrn_orient_matrix_UB_21      -0.0431816
_diffrn_orient_matrix_UB_31      0.0823164
_diffrn_orient_matrix_UB_12      0.0431682
_diffrn_orient_matrix_UB_22      -0.0515944
_diffrn_orient_matrix_UB_32      -0.1113232
_diffrn_orient_matrix_UB_13      0.0290533
_diffrn_orient_matrix_UB_23      0.0725361
_diffrn_orient_matrix_UB_33      0.0036183


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

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             416
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.156
_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  0.817
_exptl_absorpt_correction_T_max  0.933

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        7                                        #
# Total number of frames [*] :      748                                        #
# Total length of scans  [*] :   748.00 (deg.)                                 #
# Rotation speed         [*] :    20.00 sec./deg.                              #
# Total exposition time  [*] :      4 h   9.3 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     2.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    2.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7  144.0  -44.5 150.0 #
#  4 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7  216.0  -44.5 150.0 #
#  5 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5 150.0 #
#  6 Omega   20.0  1.00    34.0    97   97.0    0.1    2.7   72.0  -44.5 150.0 #
#  7 Phi     20.0  1.00    34.0   360  360.0    0.1    2.4    0.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0268
_diffrn_reflns_av_r_equivalents  0.0316
_diffrn_reflns_number            21489
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3500
_reflns_number_gt                3295
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.4935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.074

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
S1 S 0.17329(7) 0.38867(6) 0.91077(3) 0.03072(12) Uani 1 1 d . . . . .
S2 S -0.01076(6) 0.77948(6) 0.77444(3) 0.02682(11) Uani 1 1 d . . . . .
S3 S 0.26384(6) 0.31316(5) 0.70524(3) 0.02323(11) Uani 1 1 d . . . . .
S4 S 0.11998(6) 0.67194(5) 0.58155(3) 0.02216(11) Uani 1 1 d . . . . .
S5 S 0.40587(6) 0.21670(5) 0.49642(3) 0.02383(11) Uani 1 1 d . . . . .
S6 S 0.26659(6) 0.58308(5) 0.36905(3) 0.02267(11) Uani 1 1 d . . . . .
S7 S 0.40936(6) 0.46109(5) 0.17392(3) 0.02265(11) Uani 1 1 d . . . . .
S8 S 0.60004(6) 0.15137(6) 0.10859(3) 0.02810(12) Uani 1 1 d . . . . .
C1 C -0.0295(4) 0.9739(3) 0.66777(18) 0.0462(6) Uani 1 1 d . . . . .
H1A H 0.090566 0.988692 0.636816 0.069 Uiso 1 1 calc R U . . .
H1B H -0.077112 1.074010 0.693250 0.069 Uiso 1 1 calc R U . . .
H1C H -0.112279 0.965668 0.614775 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0152(3) 0.2362(3) 0.93832(15) 0.0347(4) Uani 1 1 d . . . . .
H2A H -0.106239 0.297346 0.914350 0.052 Uiso 1 1 calc R U . . .
H2B H 0.012792 0.180420 1.013839 0.052 Uiso 1 1 calc R U . . .
H2C H 0.052717 0.147559 0.901847 0.052 Uiso 1 1 calc R U . . .
C3 C 0.0995(2) 0.6219(2) 0.71789(12) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.1664(2) 0.4597(2) 0.77420(12) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.2339(2) 0.4656(2) 0.58143(12) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.2948(2) 0.4269(2) 0.49319(12) 0.0195(3) Uani 1 1 d . . . . .
C7 C 0.3679(2) 0.4374(2) 0.30399(12) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.4328(2) 0.2704(2) 0.36093(12) 0.0202(3) Uani 1 1 d . . . . .
N9 N 0.51641(18) 0.15837(18) 0.30672(10) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.5099(2) 0.2465(2) 0.20714(13) 0.0224(3) Uani 1 1 d . . . . .
C11 C 0.4369(2) 0.0246(2) 0.11354(14) 0.0286(4) Uani 1 1 d . . . . .
N12 N 0.3325(2) -0.0651(3) 0.11756(15) 0.0416(4) 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
S1 C4 1.7471(16) . ?
S1 C2 1.7918(19) . ?
S2 C3 1.7484(16) . ?
S2 C1 1.788(2) . ?
S3 C5 1.7554(16) . ?
S3 C4 1.7592(16) . ?
S4 C3 1.7525(16) . ?
S4 C5 1.7568(16) . ?
S5 C8 1.7451(16) . ?
S5 C6 1.7660(16) . ?
S6 C7 1.7263(16) . ?
S6 C6 1.7711(16) . ?
S7 C7 1.7113(15) . ?
S7 C10 1.7234(17) . ?
S8 C11 1.6979(18) . ?
S8 C10 1.7681(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.343(2) . ?
C5 C6 1.347(2) . ?
C7 C8 1.372(2) . ?
C8 N9 1.380(2) . ?
N9 C10 1.315(2) . ?
C11 N12 1.135(2) . ?

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
C4 S1 C2 101.52(8) . . ?
C3 S2 C1 102.80(9) . . ?
C5 S3 C4 94.91(8) . . ?
C3 S4 C5 95.16(7) . . ?
C8 S5 C6 93.29(7) . . ?
C7 S6 C6 93.19(7) . . ?
C7 S7 C10 88.25(8) . . ?
C11 S8 C10 97.09(8) . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S1 C2 H2A 109.5 . . ?
S1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 S2 122.96(12) . . ?
C4 C3 S4 117.40(12) . . ?
S2 C3 S4 119.62(9) . . ?
C3 C4 S1 124.38(12) . . ?
C3 C4 S3 117.47(12) . . ?
S1 C4 S3 118.06(10) . . ?
C6 C5 S3 122.35(13) . . ?
C6 C5 S4 122.69(13) . . ?
S3 C5 S4 114.96(9) . . ?
C5 C6 S5 121.21(13) . . ?
C5 C6 S6 121.81(13) . . ?
S5 C6 S6 116.99(9) . . ?
C8 C7 S7 109.63(11) . . ?
C8 C7 S6 118.93(12) . . ?
S7 C7 S6 131.43(10) . . ?
C7 C8 N9 117.45(14) . . ?
C7 C8 S5 117.58(12) . . ?
N9 C8 S5 124.97(12) . . ?
C10 N9 C8 106.74(14) . . ?
N9 C10 S7 117.93(12) . . ?
N9 C10 S8 122.06(13) . . ?
S7 C10 S8 120.01(10) . . ?
N12 C11 S8 177.58(18) . . ?

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
C1 S2 C3 C4 169.51(16) . . . . ?
C1 S2 C3 S4 -12.45(13) . . . . ?
C5 S4 C3 C4 -0.95(14) . . . . ?
C5 S4 C3 S2 -179.10(9) . . . . ?
S2 C3 C4 S1 -6.5(2) . . . . ?
S4 C3 C4 S1 175.44(9) . . . . ?
S2 C3 C4 S3 176.97(8) . . . . ?
S4 C3 C4 S3 -1.11(18) . . . . ?
C2 S1 C4 C3 112.95(16) . . . . ?
C2 S1 C4 S3 -70.52(12) . . . . ?
C5 S3 C4 C3 2.54(14) . . . . ?
C5 S3 C4 S1 -174.23(9) . . . . ?
C4 S3 C5 C6 176.56(14) . . . . ?
C4 S3 C5 S4 -3.10(10) . . . . ?
C3 S4 C5 C6 -177.00(14) . . . . ?
C3 S4 C5 S3 2.66(10) . . . . ?
S3 C5 C6 S5 1.3(2) . . . . ?
S4 C5 C6 S5 -179.08(8) . . . . ?
S3 C5 C6 S6 -179.03(8) . . . . ?
S4 C5 C6 S6 0.6(2) . . . . ?
C8 S5 C6 C5 178.62(14) . . . . ?
C8 S5 C6 S6 -1.09(10) . . . . ?
C7 S6 C6 C5 -178.37(14) . . . . ?
C7 S6 C6 S5 1.34(10) . . . . ?
C10 S7 C7 C8 -0.10(12) . . . . ?
C10 S7 C7 S6 178.91(13) . . . . ?
C6 S6 C7 C8 -1.15(14) . . . . ?
C6 S6 C7 S7 179.90(12) . . . . ?
S7 C7 C8 N9 0.51(18) . . . . ?
S6 C7 C8 N9 -178.65(11) . . . . ?
S7 C7 C8 S5 179.78(8) . . . . ?
S6 C7 C8 S5 0.62(18) . . . . ?
C6 S5 C8 C7 0.30(14) . . . . ?
C6 S5 C8 N9 179.51(14) . . . . ?
C7 C8 N9 C10 -0.72(19) . . . . ?
S5 C8 N9 C10 -179.93(12) . . . . ?
C8 N9 C10 S7 0.63(17) . . . . ?
C8 N9 C10 S8 -179.27(11) . . . . ?
C7 S7 C10 N9 -0.33(13) . . . . ?
C7 S7 C10 S8 179.57(10) . . . . ?
C11 S8 C10 N9 72.40(15) . . . . ?
C11 S8 C10 S7 -107.49(11) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................


####################################################################### 
# 
# 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_TTFI2TCNQF4
_database_code_depnum_ccdc_archive 'CCDC 2245502'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 10 juin 2022                                             #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 F4 N4, 2(C9 H6 I N S7)'
_chemical_formula_sum            'C30 H12 F4 I2 N6 S14'
_chemical_formula_weight         1235.10
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2339(10)
_cell_length_b                   10.7451(15)
_cell_length_c                   13.7344(19)
_cell_angle_alpha                77.886(5)
_cell_angle_beta                 87.003(5)
_cell_angle_gamma                72.421(5)
_cell_volume                     995.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9209
_cell_measurement_theta_min      2.7718
_cell_measurement_theta_max      27.4836
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0523077
_diffrn_orient_matrix_UB_21      -0.1137390
_diffrn_orient_matrix_UB_31      -0.0732001
_diffrn_orient_matrix_UB_12      0.0304538
_diffrn_orient_matrix_UB_22      -0.0333288
_diffrn_orient_matrix_UB_32      0.0889130
_diffrn_orient_matrix_UB_13      -0.0697699
_diffrn_orient_matrix_UB_23      0.0213773
_diffrn_orient_matrix_UB_33      0.0148830


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

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.061
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             600
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.370
_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  0.809
_exptl_absorpt_correction_T_max  0.954

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2021.10-0       #
# Number of scans            :        4                                        #
# Total number of frames [*] :      554                                        #
# Total length of scans  [*] :   554.00 (deg.)                                 #
# Rotation speed         [*] :    12.00 sec./deg.                              #
# Total exposition time  [*] :      1 h  50.8 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Phi     12.0  1.00    34.0   360  360.0    0.1    2.4    0.0  -44.5 150.0 #
#  3 Omega   12.0  1.00    34.0    97   97.0    0.1    2.7    0.0  -44.5 150.0 #
#  4 Omega   12.0  1.00    34.0    97   97.0    0.1    2.7  144.0  -44.5 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0450
_diffrn_reflns_av_r_equivalents  0.0549
_diffrn_reflns_number            20058
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             4514
_reflns_number_gt                3913
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2021)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.9942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4514
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.118
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.127

#------------------------------------------------------------------------------#
#               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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I -0.15486(4) 0.13159(3) 0.87901(2) 0.02814(11) Uani 0.9604(9) 1 d . . P A
1
I1B I -0.0860(12) 0.1674(8) 0.8980(5) 0.02814(11) Uani 0.0396(9) 1 d . . P A 2
S1 S 0.84750(15) 0.23742(11) 0.15013(8) 0.0303(2) Uani 1 1 d . . . . .
S2 S 0.53616(14) 0.09533(10) 0.07110(7) 0.0260(2) Uani 1 1 d . . . . .
S3 S 0.63417(13) 0.21590(9) 0.34147(6) 0.02006(19) Uani 1 1 d . . . . .
S4 S 0.36437(13) 0.09492(9) 0.27304(6) 0.02060(19) Uani 1 1 d . . . . .
S5 S 0.42818(13) 0.21473(9) 0.55062(6) 0.01911(19) Uani 1 1 d . . . . .
S6 S 0.14808(13) 0.09160(9) 0.48545(6) 0.02036(19) Uani 1 1 d . . . . .
S7 S 0.19839(14) 0.21475(10) 0.74982(6) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.7430(7) 0.4160(5) 0.1168(4) 0.0458(12) Uani 1 1 d . . . . .
H1A H 0.629503 0.437556 0.073482 0.069 Uiso 1 1 calc R U . . .
H1B H 0.839260 0.455895 0.081583 0.069 Uiso 1 1 calc R U . . .
H1C H 0.703487 0.451656 0.177278 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6601(5) 0.1914(4) 0.2191(3) 0.0217(7) Uani 1 1 d . . . . .
C3 C 0.5355(5) 0.1360(4) 0.1878(2) 0.0198(7) Uani 1 1 d . . . . .
C4 C 0.3209(7) 0.2206(5) 0.0143(3) 0.0419(11) Uani 1 1 d . . . . .
H4A H 0.208615 0.187133 0.029658 0.063 Uiso 1 1 calc R U . . .
H4B H 0.337100 0.240733 -0.058025 0.063 Uiso 1 1 calc R U . . .
H4C H 0.300370 0.301769 0.040491 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4364(5) 0.1552(3) 0.3673(3) 0.0186(7) Uani 1 1 d . . . . .
C6 C 0.3466(5) 0.1530(3) 0.4584(2) 0.0179(7) Uani 1 1 d . . . . .
C7 C 0.2471(5) 0.1873(4) 0.6317(2) 0.0189(7) Uani 1 1 d . . . . .
C8 C 0.1190(5) 0.1301(4) 0.6035(3) 0.0199(7) Uani 1 1 d . . . . .
N9 N -0.0217(5) 0.1047(3) 0.6718(2) 0.0204(6) Uani 1 1 d . . . . .
C10 C 0.0114(5) 0.1455(4) 0.7517(3) 0.0225(8) Uani 1 1 d . . . . .
C11 C 0.7613(5) 0.4756(4) 0.6722(3) 0.0205(7) Uani 1 1 d . . . . .
C12 C 0.7894(6) 0.5139(4) 0.7623(3) 0.0270(8) Uani 1 1 d . . . . .
N13 N 0.8029(6) 0.5407(4) 0.8370(3) 0.0384(9) Uani 1 1 d . . . . .
C14 C 0.6019(5) 0.4207(4) 0.6774(3) 0.0219(7) Uani 1 1 d . . . . .
N15 N 0.4765(5) 0.3767(4) 0.6877(2) 0.0305(8) Uani 1 1 d . . . . .
C16 C 0.8773(5) 0.4878(3) 0.5871(3) 0.0182(7) Uani 1 1 d . . . . .
C17 C 0.8576(5) 0.4414(3) 0.5003(3) 0.0196(7) Uani 1 1 d . . . . .
C18 C 0.9702(5) 0.4527(4) 0.4192(2) 0.0195(7) Uani 1 1 d . . . . .
F19 F 0.7203(3) 0.3809(2) 0.49894(16) 0.0278(5) Uani 1 1 d . . . . .
F20 F 0.9394(3) 0.4017(2) 0.34238(15) 0.0268(5) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              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
I1A C10 2.074(3) . ?
I1B C10 2.130(7) . ?
S1 C2 1.747(4) . ?
S1 C1 1.804(5) . ?
S2 C3 1.747(3) . ?
S2 C4 1.807(5) . ?
S3 C5 1.735(3) . ?
S3 C2 1.746(4) . ?
S4 C5 1.730(3) . ?
S4 C3 1.750(4) . ?
S5 C7 1.728(4) . ?
S5 C6 1.749(3) . ?
S6 C8 1.743(4) . ?
S6 C6 1.746(3) . ?
S7 C7 1.709(3) . ?
S7 C10 1.726(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.351(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.378(5) . ?
C7 C8 1.367(5) . ?
C8 N9 1.396(5) . ?
N9 C10 1.322(5) . ?
C11 C16 1.408(5) . ?
C11 C12 1.426(5) . ?
C11 C14 1.438(5) . ?
C12 N13 1.139(5) . ?
C14 N15 1.134(5) . ?
C16 C17 1.414(5) . ?
C16 C18 1.424(5) 2_766 ?
C17 F19 1.345(4) . ?
C17 C18 1.352(5) . ?
C18 F20 1.343(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 101.1(2) . . ?
C3 S2 C4 101.16(19) . . ?
C5 S3 C2 95.26(17) . . ?
C5 S4 C3 94.95(17) . . ?
C7 S5 C6 92.87(16) . . ?
C8 S6 C6 93.34(16) . . ?
C7 S7 C10 87.90(17) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 S3 116.6(3) . . ?
C3 C2 S1 126.3(3) . . ?
S3 C2 S1 117.0(2) . . ?
C2 C3 S2 125.8(3) . . ?
C2 C3 S4 117.3(3) . . ?
S2 C3 S4 116.9(2) . . ?
S2 C4 H4A 109.5 . . ?
S2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 S4 122.7(3) . . ?
C6 C5 S3 121.5(3) . . ?
S4 C5 S3 115.8(2) . . ?
C5 C6 S6 121.9(3) . . ?
C5 C6 S5 120.3(3) . . ?
S6 C6 S5 117.8(2) . . ?
C8 C7 S7 110.1(3) . . ?
C8 C7 S5 119.0(3) . . ?
S7 C7 S5 130.9(2) . . ?
C7 C8 N9 117.8(3) . . ?
C7 C8 S6 117.0(3) . . ?
N9 C8 S6 125.3(3) . . ?
C10 N9 C8 105.4(3) . . ?
N9 C10 S7 118.8(3) . . ?
N9 C10 I1A 122.6(3) . . ?
S7 C10 I1A 118.64(19) . . ?
N9 C10 I1B 144.3(4) . . ?
S7 C10 I1B 96.8(3) . . ?
C16 C11 C12 124.4(3) . . ?
C16 C11 C14 123.1(3) . . ?
C12 C11 C14 112.6(3) . . ?
N13 C12 C11 175.5(4) . . ?
N15 C14 C11 175.9(4) . . ?
C11 C16 C17 124.3(3) . . ?
C11 C16 C18 122.8(3) . 2_766 ?
C17 C16 C18 112.9(3) . 2_766 ?
F19 C17 C18 118.0(3) . . ?
F19 C17 C16 118.0(3) . . ?
C18 C17 C16 124.0(3) . . ?
F20 C18 C17 118.1(3) . . ?
F20 C18 C16 118.8(3) . 2_766 ?
C17 C18 C16 123.1(3) . 2_766 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 S3 C2 C3 -1.5(3) . . . . ?
C5 S3 C2 S1 179.8(2) . . . . ?
C1 S1 C2 C3 103.5(4) . . . . ?
C1 S1 C2 S3 -78.0(3) . . . . ?
S3 C2 C3 S2 -177.4(2) . . . . ?
S1 C2 C3 S2 1.0(5) . . . . ?
S3 C2 C3 S4 -0.2(4) . . . . ?
S1 C2 C3 S4 178.3(2) . . . . ?
C4 S2 C3 C2 -108.7(4) . . . . ?
C4 S2 C3 S4 74.1(3) . . . . ?
C5 S4 C3 C2 1.9(3) . . . . ?
C5 S4 C3 S2 179.3(2) . . . . ?
C3 S4 C5 C6 178.5(3) . . . . ?
C3 S4 C5 S3 -2.9(2) . . . . ?
C2 S3 C5 C6 -178.6(3) . . . . ?
C2 S3 C5 S4 2.8(2) . . . . ?
S4 C5 C6 S6 -1.2(5) . . . . ?
S3 C5 C6 S6 -179.74(19) . . . . ?
S4 C5 C6 S5 179.6(2) . . . . ?
S3 C5 C6 S5 1.1(5) . . . . ?
C8 S6 C6 C5 -177.4(3) . . . . ?
C8 S6 C6 S5 1.8(2) . . . . ?
C7 S5 C6 C5 177.0(3) . . . . ?
C7 S5 C6 S6 -2.2(2) . . . . ?
C10 S7 C7 C8 0.5(3) . . . . ?
C10 S7 C7 S5 -177.1(3) . . . . ?
C6 S5 C7 C8 1.9(3) . . . . ?
C6 S5 C7 S7 179.3(3) . . . . ?
S7 C7 C8 N9 -0.1(4) . . . . ?
S5 C7 C8 N9 177.8(3) . . . . ?
S7 C7 C8 S6 -178.91(19) . . . . ?
S5 C7 C8 S6 -1.0(4) . . . . ?
C6 S6 C8 C7 -0.5(3) . . . . ?
C6 S6 C8 N9 -179.2(3) . . . . ?
C7 C8 N9 C10 -0.5(4) . . . . ?
S6 C8 N9 C10 178.2(3) . . . . ?
C8 N9 C10 S7 1.0(4) . . . . ?
C8 N9 C10 I1A -179.8(2) . . . . ?
C8 N9 C10 I1B 178.8(5) . . . . ?
C7 S7 C10 N9 -0.9(3) . . . . ?
C7 S7 C10 I1A 179.8(2) . . . . ?
C7 S7 C10 I1B -179.7(3) . . . . ?
C12 C11 C16 C17 175.5(4) . . . . ?
C14 C11 C16 C17 -3.6(6) . . . . ?
C12 C11 C16 C18 -3.6(6) . . . 2_766 ?
C14 C11 C16 C18 177.3(3) . . . 2_766 ?
C11 C16 C17 F19 -0.5(5) . . . . ?
C18 C16 C17 F19 178.7(3) 2_766 . . . ?
C11 C16 C17 C18 -179.5(4) . . . . ?
C18 C16 C17 C18 -0.4(6) 2_766 . . . ?
F19 C17 C18 F20 -0.5(5) . . . . ?
C16 C17 C18 F20 178.5(3) . . . . ?
F19 C17 C18 C16 -178.6(3) . . . 2_766 ?
C16 C17 C18 C16 0.4(6) . . . 2_766 ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR TTFI2TCNQF4                                            #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################

