# 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_alpha-[EDT-TTF(SeMe)2](F2TCNQ)
_database_code_depnum_ccdc_archive 'CCDC 2247520'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;

_audit_creation_date             2023-03-29T14:29:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C10 H10 S6 Se2, C12 H2 F2 N4'
_chemical_formula_sum            'C22 H12 F2 N4 S6 Se2'
_chemical_formula_weight         720.64

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_Int_Tables_number      11
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   4.0174(5)
_cell_length_b                   24.7410(18)
_cell_length_c                   13.0728(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.086(5)
_cell_angle_gamma                90
_cell_volume                     1294.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      2.2694
_cell_measurement_theta_max      27.2205
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708

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

_exptl_absorpt_coefficient_mu    3.377
_shelx_estimated_absorpt_T_min   0.511
_shelx_estimated_absorpt_T_max   0.936
_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  0.886
_exptl_absorpt_correction_T_max  0.935

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5998  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.8045                          #
#------------------------------------------------------------------------------#


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

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_number            3013
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.924
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             3013
_reflns_number_gt                2342
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²+4.0886P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3013
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.049
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.096

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.675(2) 0.25 0.2972(5) 0.0258(15) Uani 1 2 d S T P . .
C2 C 0.4497(12) 0.2773(2) 0.4659(3) 0.0261(11) Uani 1 1 d . . . . .
C3 C 0.4239(17) 0.3906(2) 0.5287(5) 0.0471(16) Uani 1 1 d . . . . .
H3A H 0.375839 0.416867 0.579428 0.071 Uiso 1 1 calc R U . . .
H3B H 0.295583 0.398699 0.465015 0.071 Uiso 1 1 calc R U . . .
H3C H 0.657709 0.391759 0.51871 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8031(19) 0.25 0.2028(5) 0.0256(16) Uani 1 2 d S T P . .
C5 C 1.0074(12) 0.22278(19) 0.0299(3) 0.0247(11) Uani 1 1 d . . . . .
C6 C 0.943(2) 0.2222(2) -0.1775(5) 0.070(3) Uani 1 1 d . . . . .
H6A H 1.058322 0.211127 -0.236075 0.084 Uiso 1 1 calc R U . . .
H6B H 0.711781 0.211128 -0.191825 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4128(13) 0.54999(17) 1.0388(4) 0.0265(11) Uani 1 1 d . . . . .
H7 H 0.355414 0.583801 1.062896 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5751(13) 0.54627(18) 0.9529(4) 0.0251(10) Uani 1 1 d . . . . .
C9 C 0.6716(13) 0.49758(19) 0.9070(3) 0.0246(11) Uani 1 1 d . . . . .
C10 C 0.8429(14) 0.49482(19) 0.8175(3) 0.0276(11) Uani 1 1 d . . . . .
C11 C 0.9354(13) 0.4443(2) 0.7775(4) 0.0292(12) Uani 1 1 d . . . . .
C12 C 0.9360(13) 0.5395(2) 0.7598(4) 0.0336(13) Uani 1 1 d . . . . .
F1 F 0.6468(9) 0.59309(11) 0.9052(2) 0.0380(8) Uani 1 1 d . . . . .
N1 N 1.0179(15) 0.4037(2) 0.7444(4) 0.0490(13) Uani 1 1 d . . . . .
N2 N 1.0202(16) 0.5740(2) 0.7083(4) 0.0535(15) Uani 1 1 d . . . . .
S1 S 0.5869(3) 0.30899(5) 0.35937(9) 0.0292(3) Uani 1 1 d . . . . .
S2 S 0.8793(4) 0.19097(5) 0.13843(9) 0.0303(3) Uani 1 1 d . . . . .
S3 S 1.1121(4) 0.18199(6) -0.07047(9) 0.0340(3) Uani 1 1 d . . . . .
Se1 Se 0.30849(16) 0.31949(2) 0.57450(4) 0.03674(17) 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 C4 1.379(9) . ?
C1 S1 1.722(4) . ?
C1 S1 1.722(4) 4_565 ?
C2 C2 1.350(10) 4_565 ?
C2 S1 1.730(5) . ?
C2 Se1 1.890(5) . ?
C3 Se1 1.929(6) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C4 S2 1.726(4) . ?
C4 S2 1.726(4) 4_565 ?
C5 C5 1.347(9) 4_565 ?
C5 S3 1.736(5) . ?
C5 S2 1.740(5) . ?
C6 C6 1.375(12) 4_565 ?
C6 S3 1.800(6) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.350(6) . ?
C7 C9 1.430(6) 3_667 ?
C7 H7 0.93 . ?
C8 F1 1.359(5) . ?
C8 C9 1.415(7) . ?
C9 C10 1.411(6) . ?
C10 C12 1.407(7) . ?
C10 C11 1.417(7) . ?
C11 N1 1.154(6) . ?
C12 N2 1.156(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
C4 C1 S1 122.08(19) . . ?
C4 C1 S1 122.08(19) . 4_565 ?
S1 C1 S1 115.8(4) . 4_565 ?
C2 C2 S1 116.96(16) 4_565 . ?
C2 C2 Se1 123.54(15) 4_565 . ?
S1 C2 Se1 119.5(3) . . ?
Se1 C3 H3A 109.5 . . ?
Se1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Se1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 S2 122.18(19) . . ?
C1 C4 S2 122.18(19) . 4_565 ?
S2 C4 S2 115.6(4) . 4_565 ?
C5 C5 S3 125.53(16) 4_565 . ?
C5 C5 S2 116.89(16) 4_565 . ?
S3 C5 S2 117.5(3) . . ?
C6 C6 S3 123.6(2) 4_565 . ?
C6 C6 H6A 106.4 4_565 . ?
S3 C6 H6A 106.4 . . ?
C6 C6 H6B 106.4 4_565 . ?
S3 C6 H6B 106.4 . . ?
H6A C6 H6B 106.5 . . ?
C8 C7 C9 120.6(4) . 3_667 ?
C8 C7 H7 119.7 . . ?
C9 C7 H7 119.7 3_667 . ?
C7 C8 F1 117.5(4) . . ?
C7 C8 C9 125.5(4) . . ?
F1 C8 C9 117.0(4) . . ?
C10 C9 C8 124.4(4) . . ?
C10 C9 C7 121.7(4) . 3_667 ?
C8 C9 C7 113.8(4) . 3_667 ?
C12 C10 C9 125.4(4) . . ?
C12 C10 C11 113.9(4) . . ?
C9 C10 C11 120.8(4) . . ?
N1 C11 C10 178.3(6) . . ?
N2 C12 C10 175.8(6) . . ?
C1 S1 C2 95.1(2) . . ?
C4 S2 C5 95.3(2) . . ?
C5 S3 C6 99.5(3) . . ?
C2 Se1 C3 100.0(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
S1 C1 C4 S2 -177.9(5) . . . . ?
S1 C1 C4 S2 1.1(10) 4_565 . . . ?
S1 C1 C4 S2 -1.1(10) . . . 4_565 ?
S1 C1 C4 S2 177.9(5) 4_565 . . 4_565 ?
C9 C7 C8 F1 179.8(5) 3_667 . . . ?
C9 C7 C8 C9 1.2(9) 3_667 . . . ?
C7 C8 C9 C10 -179.6(5) . . . . ?
F1 C8 C9 C10 1.8(8) . . . . ?
C7 C8 C9 C7 -1.1(9) . . . 3_667 ?
F1 C8 C9 C7 -179.8(4) . . . 3_667 ?
C8 C9 C10 C12 -1.5(9) . . . . ?
C7 C9 C10 C12 -179.8(5) 3_667 . . . ?
C8 C9 C10 C11 178.9(5) . . . . ?
C7 C9 C10 C11 0.5(8) 3_667 . . . ?
C4 C1 S1 C2 -179.4(6) . . . . ?
S1 C1 S1 C2 1.6(5) 4_565 . . . ?
C2 C2 S1 C1 -1.0(3) 4_565 . . . ?
Se1 C2 S1 C1 179.2(4) . . . . ?
C1 C4 S2 C5 177.0(6) . . . . ?
S2 C4 S2 C5 0.0(5) 4_565 . . . ?
C5 C5 S2 C4 0.0(3) 4_565 . . . ?
S3 C5 S2 C4 -178.1(4) . . . . ?
C5 C5 S3 C6 -36.0(3) 4_565 . . . ?
S2 C5 S3 C6 141.9(4) . . . . ?
C6 C6 S3 C5 35.0(3) 4_565 . . . ?
C2 C2 Se1 C3 173.9(2) 4_565 . . . ?
S1 C2 Se1 C3 -6.2(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_beta-[EDT-TTF(SeMe)2](F2TCNQ)
_database_code_depnum_ccdc_archive 'CCDC 2247521'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;

_audit_creation_date             2023-03-29T14:42:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C10 H10 S6 Se2, C12 H2 F2 N4'
_chemical_formula_sum            'C22 H12 F2 N4 S6 Se2'
_chemical_formula_weight         720.64

#----------------------------------------------------------------------------#
#                   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                   16.3862(16)
_cell_length_b                   20.785(2)
_cell_length_c                   7.6276(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.272(6)
_cell_angle_gamma                90
_cell_volume                     2556.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2416
_cell_measurement_theta_min      2.8871
_cell_measurement_theta_max      24.9101
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416

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

_exptl_absorpt_coefficient_mu    3.42
_shelx_estimated_absorpt_T_min   0.47
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_T_max  0.828

#-------------------------------- Remark --------------------------------------#
# TWINABS output:                                                              #
# HKLF 5 dataset constructed from all observations involving domain 1          #
#  4457  Corrected reflections written to file MD939_0m_5.hkl                  #
# Reflections merged according to point-group 2/m                              #
# Single reflections that also occur in composites omitted                     #
# Minimum and maximum apparent transmission:  0.544560  0.745553               #
# Additional spherical absorption correction applied with mu*r =  0.2000       #
#------------------------------------------------------------------------------#

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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0841
_diffrn_reflns_number            2902
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             2902
_reflns_number_gt                1929
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+5.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2902
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.097
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.55
_refine_diff_density_rms         0.115

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5 0.5672(3) 0.75 0.0406(19) Uani 1 2 d S T P . .
C2 C 0.5420(3) 0.6856(2) 0.7695(7) 0.0323(11) Uani 1 1 d . . . . .
C3 C 0.7098(3) 0.7313(3) 0.7707(11) 0.070(2) Uani 1 1 d . . . . .
H3A H 0.730232 0.698982 0.857466 0.105 Uiso 1 1 calc R U . . .
H3B H 0.748688 0.766154 0.779595 0.105 Uiso 1 1 calc R U . . .
H3C H 0.702823 0.712905 0.653459 0.105 Uiso 1 1 calc R U . . .
C4 C 0.5 0.5012(3) 0.75 0.0444(19) Uani 1 2 d S T P . .
C5 C 0.4584(3) 0.3827(2) 0.7322(7) 0.0363(12) Uani 1 1 d . . . . .
C6 C 0.4605(4) 0.2521(2) 0.6871(9) 0.0585(17) Uani 1 1 d . . . . .
H6A H 0.431949 0.21204 0.701354 0.07 Uiso 1 1 calc R U . . .
H6B H 0.472448 0.252637 0.567072 0.07 Uiso 1 1 calc R U . . .
C7 C 0.4655(3) 0.9433(2) 0.4403(7) 0.0286(11) Uani 1 1 d . . . . .
C8 C 0.5369(3) 0.9420(2) 0.5602(6) 0.0279(10) Uani 1 1 d . . . . .
H8 H 0.56066 0.902565 0.597594 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5761(3) 0.9994(2) 0.6301(6) 0.0262(10) Uani 1 1 d . . . . .
C10 C 0.6486(3) 0.9987(2) 0.7581(6) 0.0293(10) Uani 1 1 d . . . . .
C11 C 0.6859(3) 0.9395(3) 0.8236(7) 0.0382(12) Uani 1 1 d . . . . .
C12 C 0.6910(3) 1.0546(3) 0.8376(8) 0.0420(13) Uani 1 1 d . . . . .
F1 F 0.43234(19) 0.88635(13) 0.3778(4) 0.0463(8) Uani 1 1 d . . . . .
N1 N 0.7164(3) 0.8926(2) 0.8802(7) 0.0590(15) Uani 1 1 d . . . . .
N2 N 0.7274(3) 1.0961(3) 0.9099(8) 0.0705(17) Uani 1 1 d . . . . .
S1 S 0.59060(7) 0.61158(6) 0.7916(2) 0.0434(4) Uani 1 1 d . . . . .
S2 S 0.40931(7) 0.45685(6) 0.7120(3) 0.0539(4) Uani 1 1 d . . . . .
S3 S 0.39125(9) 0.31724(6) 0.7081(3) 0.0547(4) Uani 1 1 d . . . . .
Se1 Se 0.60476(3) 0.76281(2) 0.81377(8) 0.03985(18) 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 C4 1.373(9) . ?
C1 S1 1.728(4) . ?
C1 S1 1.728(4) 2_656 ?
C2 C2 1.355(9) 2_656 ?
C2 S1 1.728(4) . ?
C2 Se1 1.903(4) . ?
C3 Se1 1.924(6) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C4 S2 1.728(4) 2_656 ?
C4 S2 1.728(4) . ?
C5 C5 1.340(9) 2_656 ?
C5 S2 1.733(5) . ?
C5 S3 1.739(5) . ?
C6 C6 1.468(12) 2_656 ?
C6 S3 1.792(6) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.350(6) . ?
C7 F1 1.353(5) . ?
C7 C9 1.428(6) 5_676 ?
C8 C9 1.414(6) . ?
C8 H8 0.93 . ?
C9 C10 1.398(6) . ?
C10 C11 1.424(7) . ?
C10 C12 1.431(7) . ?
C11 N1 1.145(6) . ?
C12 N2 1.135(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
C4 C1 S1 122.24(19) . . ?
C4 C1 S1 122.24(19) . 2_656 ?
S1 C1 S1 115.5(4) . 2_656 ?
C2 C2 S1 117.00(14) 2_656 . ?
C2 C2 Se1 122.32(14) 2_656 . ?
S1 C2 Se1 120.6(2) . . ?
Se1 C3 H3A 109.5 . . ?
Se1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Se1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 S2 122.2(2) . 2_656 ?
C1 C4 S2 122.2(2) . . ?
S2 C4 S2 115.6(4) 2_656 . ?
C5 C5 S2 117.21(15) 2_656 . ?
C5 C5 S3 128.51(16) 2_656 . ?
S2 C5 S3 114.3(3) . . ?
C6 C6 S3 116.1(4) 2_656 . ?
C6 C6 H6A 108.3 2_656 . ?
S3 C6 H6A 108.3 . . ?
C6 C6 H6B 108.3 2_656 . ?
S3 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 F1 117.8(4) . . ?
C8 C7 C9 124.7(4) . 5_676 ?
F1 C7 C9 117.5(4) . 5_676 ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 121.8(4) . . ?
C10 C9 C7 124.1(4) . 5_676 ?
C8 C9 C7 114.1(4) . 5_676 ?
C9 C10 C11 120.8(4) . . ?
C9 C10 C12 125.1(5) . . ?
C11 C10 C12 114.0(4) . . ?
N1 C11 C10 178.3(6) . . ?
N2 C12 C10 175.2(6) . . ?
C2 S1 C1 95.2(2) . . ?
C4 S2 C5 95.0(3) . . ?
C5 S3 C6 101.6(3) . . ?
C2 Se1 C3 98.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C4 S2 -1.08(10) . . . 2_656 ?
S1 C1 C4 S2 178.92(10) 2_656 . . 2_656 ?
S1 C1 C4 S2 178.92(10) . . . . ?
S1 C1 C4 S2 -1.08(10) 2_656 . . . ?
F1 C7 C8 C9 179.1(4) . . . . ?
C9 C7 C8 C9 1.4(8) 5_676 . . . ?
C7 C8 C9 C10 178.1(5) . . . . ?
C7 C8 C9 C7 -1.2(7) . . . 5_676 ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C7 C9 C10 C11 179.2(4) 5_676 . . . ?
C8 C9 C10 C12 -178.7(5) . . . . ?
C7 C9 C10 C12 0.6(8) 5_676 . . . ?
C2 C2 S1 C1 -0.2(6) 2_656 . . . ?
Se1 C2 S1 C1 175.9(3) . . . . ?
C4 C1 S1 C2 -179.95(19) . . . . ?
S1 C1 S1 C2 0.05(19) 2_656 . . . ?
C1 C4 S2 C5 179.90(19) . . . . ?
S2 C4 S2 C5 -0.10(19) 2_656 . . . ?
C5 C5 S2 C4 0.4(7) 2_656 . . . ?
S3 C5 S2 C4 178.8(3) . . . . ?
C5 C5 S3 C6 -13.9(8) 2_656 . . . ?
S2 C5 S3 C6 167.8(3) . . . . ?
C6 C6 S3 C5 44.6(7) 2_656 . . . ?

