# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_1_gl91311
_database_code_depnum_ccdc_archive 'CCDC 2347751'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2024-04-12 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 1,4,7,10-tetrafluorodibenzo[c,g][1,2,5,6]tetrathiocine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 F4 S4'
_chemical_formula_sum            'C12 H4 F4 S4'
_chemical_formula_weight         352.39

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   4.7996(11)
_cell_length_b                   11.340(3)
_cell_length_c                   12.006(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.465(9)
_cell_angle_gamma                90
_cell_volume                     653.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1501
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   0.582
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7293
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6275
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.394
_diffrn_reflns_theta_max         25.119
_diffrn_reflns_theta_full        25.119
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1164
_reflns_number_gt                805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0980P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1164
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.7510(2) 0.62756(10) 0.45329(9) 0.0571(4) Uani 1 1 d . . . . .
S2 S 0.4688(2) 0.47365(11) 0.65925(9) 0.0589(5) Uani 1 1 d . . . . .
F1 F 0.0408(6) 0.6118(3) 0.7705(2) 0.0945(11) Uani 1 1 d . . . . .
F2 F 0.5178(7) 0.8643(2) 0.4418(3) 0.0918(10) Uani 1 1 d . . . . .
C1 C 0.2054(13) 0.8523(5) 0.5889(6) 0.0815(16) Uani 1 1 d . . . . .
H1 H 0.154293 0.930390 0.576827 0.098 Uiso 1 1 calc R U . . .
C2 C 0.4006(10) 0.8003(4) 0.5241(4) 0.0628(12) Uani 1 1 d . . . . .
C3 C 0.4864(8) 0.6847(4) 0.5395(3) 0.0488(10) Uani 1 1 d . . . . .
C4 C 0.3660(8) 0.6185(3) 0.6259(3) 0.0481(10) Uani 1 1 d . . . . .
C5 C 0.1634(9) 0.6744(5) 0.6894(4) 0.0629(13) Uani 1 1 d . . . . .
C6 C 0.0854(10) 0.7887(6) 0.6720(5) 0.0790(17) Uani 1 1 d . . . . .
H2 H -0.049383 0.823097 0.716758 0.095 Uiso 1 1 calc R U . . .


_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 C3 1.768(4) . ?
S1 S2 2.0572(16) 3_666 ?
S2 C4 1.761(4) . ?
F1 C5 1.344(5) . ?
F2 C2 1.352(5) . ?
C1 C2 1.358(8) . ?
C1 C6 1.362(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(6) . ?
C3 C4 1.408(6) . ?
C4 C5 1.393(6) . ?
C5 C6 1.364(8) . ?
C6 H2 0.9300 . ?

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 S1 S2 102.83(14) . 3_666 ?
C4 S2 S1 103.30(13) . 3_666 ?
C2 C1 C6 119.2(5) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
F2 C2 C1 118.6(5) . . ?
F2 C2 C3 118.7(4) . . ?
C1 C2 C3 122.6(5) . . ?
C2 C3 C4 118.6(4) . . ?
C2 C3 S1 118.8(3) . . ?
C4 C3 S1 122.5(3) . . ?
C5 C4 C3 116.9(4) . . ?
C5 C4 S2 119.7(4) . . ?
C3 C4 S2 123.3(3) . . ?
F1 C5 C6 119.4(4) . . ?
F1 C5 C4 117.9(5) . . ?
C6 C5 C4 122.7(5) . . ?
C1 C6 C5 119.8(5) . . ?
C1 C6 H2 120.1 . . ?
C5 C6 H2 120.1 . . ?

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
C6 C1 C2 F2 179.9(4) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
F2 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
F2 C2 C3 S1 1.5(6) . . . . ?
C1 C2 C3 S1 -177.8(4) . . . . ?
S2 S1 C3 C2 -102.3(3) 3_666 . . . ?
S2 S1 C3 C4 79.9(3) 3_666 . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
S1 C3 C4 C5 178.7(3) . . . . ?
C2 C3 C4 S2 -176.6(3) . . . . ?
S1 C3 C4 S2 1.2(5) . . . . ?
S1 S2 C4 C5 99.7(3) 3_666 . . . ?
S1 S2 C4 C3 -82.8(3) 3_666 . . . ?
C3 C4 C5 F1 178.3(3) . . . . ?
S2 C4 C5 F1 -4.0(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
S2 C4 C5 C6 176.3(4) . . . . ?
C2 C1 C6 C5 0.4(8) . . . . ?
F1 C5 C6 C1 -179.0(4) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.072


####################################################################### 
# 
# 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_2_gl81252
_database_code_depnum_ccdc_archive 'CCDC 2347752'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2024-04-12 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 perfluorodiindeno[5,6-c:5',6'-g][1,2,5,6]tetrathiocine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 F16 S4'
_chemical_formula_sum            'C18 F16 S4'
_chemical_formula_weight         648.42

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   16.0085(7)
_cell_length_b                   11.8439(4)
_cell_length_c                   10.6197(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.983(2)
_cell_angle_gamma                90
_cell_volume                     2012.32(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5407
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.02

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.628
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12137
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         26.043
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1989
_reflns_number_gt                1746
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_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+4.6389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1989
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.48314(3) 0.54440(5) 0.34195(5) 0.02615(16) Uani 1 1 d . . . . .
S2 S 0.45043(3) 0.28572(5) 0.18733(6) 0.02672(16) Uani 1 1 d . . . . .
F1 F 0.06457(11) 0.48538(16) 0.33962(19) 0.0575(5) Uani 1 1 d . . . . .
F2 F 0.04607(11) 0.37916(17) 0.5023(2) 0.0676(6) Uani 1 1 d . . . . .
F3 F 0.18723(11) 0.44302(16) 0.60940(14) 0.0497(4) Uani 1 1 d . . . . .
F4 F 0.27930(9) 0.22451(12) 0.19732(14) 0.0352(3) Uani 1 1 d . . . . .
F5 F 0.14383(10) 0.22326(13) 0.42075(18) 0.0494(4) Uani 1 1 d . . . . .
F6 F 0.10438(9) 0.29771(14) 0.24222(15) 0.0442(4) Uani 1 1 d . . . . .
F7 F 0.15727(9) 0.59237(13) 0.50081(15) 0.0434(4) Uani 1 1 d . . . . .
F8 F 0.33939(8) 0.60054(12) 0.47891(13) 0.0341(3) Uani 1 1 d . . . . .
C1 C 0.10317(15) 0.4157(2) 0.4243(3) 0.0375(6) Uani 1 1 d . . . . .
C2 C 0.17447(15) 0.4823(2) 0.4897(2) 0.0304(5) Uani 1 1 d . . . . .
C3 C 0.24869(14) 0.45594(19) 0.4114(2) 0.0245(5) Uani 1 1 d . . . . .
C4 C 0.32543(14) 0.50681(19) 0.4097(2) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.38955(13) 0.46449(19) 0.3378(2) 0.0226(5) Uani 1 1 d . . . . .
C6 C 0.37518(13) 0.36338(19) 0.2693(2) 0.0227(5) Uani 1 1 d . . . . .
C7 C 0.29495(14) 0.31708(19) 0.2671(2) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.23262(13) 0.3616(2) 0.3370(2) 0.0252(5) Uani 1 1 d . . . . .
C9 C 0.14511(14) 0.3196(2) 0.3513(2) 0.0303(5) Uani 1 1 d . . . . .


_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 C5 1.771(2) . ?
S1 S1 2.0441(11) 2_655 ?
S2 C6 1.769(2) . ?
S2 S2 2.0358(11) 2_655 ?
F1 C1 1.354(3) . ?
F2 C1 1.327(3) . ?
F3 C2 1.362(3) . ?
F4 C7 1.342(3) . ?
F5 C9 1.359(3) . ?
F6 C9 1.335(3) . ?
F7 C2 1.338(3) . ?
F8 C4 1.346(3) . ?
C1 C2 1.534(4) . ?
C1 C9 1.544(4) . ?
C2 C3 1.506(3) . ?
C3 C4 1.369(3) . ?
C3 C8 1.387(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.416(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.370(3) . ?
C8 C9 1.499(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 S1 103.13(8) . 2_655 ?
C6 S2 S2 101.95(8) . 2_655 ?
F2 C1 F1 107.8(2) . . ?
F2 C1 C2 113.7(2) . . ?
F1 C1 C2 107.6(2) . . ?
F2 C1 C9 113.2(2) . . ?
F1 C1 C9 108.2(2) . . ?
C2 C1 C9 106.09(19) . . ?
F7 C2 F3 106.0(2) . . ?
F7 C2 C3 114.8(2) . . ?
F3 C2 C3 110.38(19) . . ?
F7 C2 C1 112.9(2) . . ?
F3 C2 C1 109.4(2) . . ?
C3 C2 C1 103.4(2) . . ?
C4 C3 C8 119.7(2) . . ?
C4 C3 C2 129.9(2) . . ?
C8 C3 C2 110.3(2) . . ?
F8 C4 C3 119.17(19) . . ?
F8 C4 C5 118.98(19) . . ?
C3 C4 C5 121.8(2) . . ?
C4 C5 C6 118.42(19) . . ?
C4 C5 S1 115.62(17) . . ?
C6 C5 S1 125.96(16) . . ?
C7 C6 C5 118.29(19) . . ?
C7 C6 S2 115.44(17) . . ?
C5 C6 S2 126.26(16) . . ?
F4 C7 C8 119.2(2) . . ?
F4 C7 C6 118.95(19) . . ?
C8 C7 C6 121.8(2) . . ?
C7 C8 C3 119.6(2) . . ?
C7 C8 C9 128.9(2) . . ?
C3 C8 C9 111.4(2) . . ?
F6 C9 F5 107.0(2) . . ?
F6 C9 C8 114.01(19) . . ?
F5 C9 C8 111.42(19) . . ?
F6 C9 C1 111.8(2) . . ?
F5 C9 C1 109.4(2) . . ?
C8 C9 C1 103.3(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
F2 C1 C2 F7 -87.1(3) . . . . ?
F1 C1 C2 F7 32.1(3) . . . . ?
C9 C1 C2 F7 147.8(2) . . . . ?
F2 C1 C2 F3 30.6(3) . . . . ?
F1 C1 C2 F3 149.9(2) . . . . ?
C9 C1 C2 F3 -94.5(2) . . . . ?
F2 C1 C2 C3 148.2(2) . . . . ?
F1 C1 C2 C3 -92.5(2) . . . . ?
C9 C1 C2 C3 23.1(2) . . . . ?
F7 C2 C3 C4 43.0(3) . . . . ?
F3 C2 C3 C4 -76.7(3) . . . . ?
C1 C2 C3 C4 166.4(2) . . . . ?
F7 C2 C3 C8 -140.2(2) . . . . ?
F3 C2 C3 C8 100.1(2) . . . . ?
C1 C2 C3 C8 -16.8(3) . . . . ?
C8 C3 C4 F8 177.73(19) . . . . ?
C2 C3 C4 F8 -5.8(4) . . . . ?
C8 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 C5 174.5(2) . . . . ?
F8 C4 C5 C6 177.52(19) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
F8 C4 C5 S1 -2.2(3) . . . . ?
C3 C4 C5 S1 177.54(18) . . . . ?
S1 S1 C5 C4 -137.67(16) 2_655 . . . ?
S1 S1 C5 C6 42.6(2) 2_655 . . . ?
C4 C5 C6 C7 6.2(3) . . . . ?
S1 C5 C6 C7 -174.02(17) . . . . ?
C4 C5 C6 S2 -172.11(17) . . . . ?
S1 C5 C6 S2 7.6(3) . . . . ?
S2 S2 C6 C7 -134.38(16) 2_655 . . . ?
S2 S2 C6 C5 44.0(2) 2_655 . . . ?
C5 C6 C7 F4 176.58(19) . . . . ?
S2 C6 C7 F4 -4.9(3) . . . . ?
C5 C6 C7 C8 -5.3(3) . . . . ?
S2 C6 C7 C8 173.21(18) . . . . ?
F4 C7 C8 C3 178.7(2) . . . . ?
C6 C7 C8 C3 0.6(3) . . . . ?
F4 C7 C8 C9 1.7(4) . . . . ?
C6 C7 C8 C9 -176.4(2) . . . . ?
C4 C3 C8 C7 3.1(3) . . . . ?
C2 C3 C8 C7 -174.0(2) . . . . ?
C4 C3 C8 C9 -179.3(2) . . . . ?
C2 C3 C8 C9 3.5(3) . . . . ?
C7 C8 C9 F6 -50.0(3) . . . . ?
C3 C8 C9 F6 132.8(2) . . . . ?
C7 C8 C9 F5 71.2(3) . . . . ?
C3 C8 C9 F5 -106.0(2) . . . . ?
C7 C8 C9 C1 -171.5(2) . . . . ?
C3 C8 C9 C1 11.3(3) . . . . ?
F2 C1 C9 F6 90.4(3) . . . . ?
F1 C1 C9 F6 -29.0(3) . . . . ?
C2 C1 C9 F6 -144.2(2) . . . . ?
F2 C1 C9 F5 -27.9(3) . . . . ?
F1 C1 C9 F5 -147.2(2) . . . . ?
C2 C1 C9 F5 97.6(2) . . . . ?
F2 C1 C9 C8 -146.6(2) . . . . ?
F1 C1 C9 C8 94.0(2) . . . . ?
C2 C1 C9 C8 -21.2(2) . . . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_17_gl942f
_database_code_depnum_ccdc_archive 'CCDC 2351030'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
 1,4,8,11-tetrafluorodibenzo[d,g][1,2,3,6]tetrathiocine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 F4 S4'
_chemical_formula_sum            'C12 H4 F4 S4'
_chemical_formula_weight         352.39

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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                   4.4346(4)
_cell_length_b                   29.235(3)
_cell_length_c                   10.3338(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.540(4)
_cell_angle_gamma                90
_cell_volume                     1317.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4516
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.751
_shelx_estimated_absorpt_T_min   0.585
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13123
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.896
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3042
_reflns_number_gt                2357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.7257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.56989(17) 0.59640(3) 0.58386(6) 0.0558(2) Uani 1 1 d . . . . .
S2 S 0.78062(16) 0.55046(2) 0.48020(7) 0.05060(19) Uani 1 1 d . . . . .
S3 S 0.47621(16) 0.53290(2) 0.31439(7) 0.04984(19) Uani 1 1 d . . . . .
S4 S 0.27549(13) 0.64188(2) 0.29570(6) 0.04441(17) Uani 1 1 d . . . . .
F1 F 0.7985(5) 0.50774(6) 0.10393(18) 0.0765(5) Uani 1 1 d . . . . .
F2 F 0.3984(5) 0.68199(6) 0.04468(19) 0.0841(6) Uani 1 1 d . . . . .
F3 F 1.0286(5) 0.65682(8) 0.73551(18) 0.0933(7) Uani 1 1 d . . . . .
F4 F 0.5796(5) 0.73075(6) 0.2611(2) 0.0881(6) Uani 1 1 d . . . . .
C1 C 1.0143(7) 0.71694(12) 0.5838(4) 0.0702(9) Uani 1 1 d . . . . .
H1A H 1.158826 0.732777 0.643869 0.084 Uiso 1 1 calc R U . . .
C2 C 0.9123(7) 0.67457(12) 0.6158(3) 0.0601(8) Uani 1 1 d . . . . .
C3 C 0.6953(5) 0.64953(9) 0.5302(2) 0.0439(6) Uani 1 1 d . . . . .
C4 C 0.5639(5) 0.57002(8) 0.1905(2) 0.0373(5) Uani 1 1 d . . . . .
C5 C 0.7030(6) 0.55175(10) 0.0925(3) 0.0497(6) Uani 1 1 d . . . . .
C6 C 0.9017(7) 0.73547(11) 0.4635(4) 0.0676(9) Uani 1 1 d . . . . .
H6A H 0.969460 0.763869 0.440109 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6876(6) 0.71151(9) 0.3782(3) 0.0531(7) Uani 1 1 d . . . . .
C8 C 0.5784(5) 0.66870(8) 0.4069(2) 0.0393(5) Uani 1 1 d . . . . .
C9 C 0.7431(7) 0.57556(12) -0.0170(3) 0.0608(8) Uani 1 1 d . . . . .
H9A H 0.838514 0.562030 -0.080344 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6402(7) 0.61957(12) -0.0314(3) 0.0615(8) Uani 1 1 d . . . . .
H10A H 0.660895 0.636383 -0.105663 0.074 Uiso 1 1 calc R U . . .
C11 C 0.5059(6) 0.63870(9) 0.0653(3) 0.0504(6) Uani 1 1 d . . . . .
C12 C 0.4682(5) 0.61583(8) 0.1781(2) 0.0373(5) Uani 1 1 d . . . . .


_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 C3 1.772(3) . ?
S1 S2 2.0470(10) . ?
S2 S3 2.0434(10) . ?
S3 C4 1.774(2) . ?
S4 C12 1.779(2) . ?
S4 C8 1.782(2) . ?
F1 C5 1.353(3) . ?
F2 C11 1.355(3) . ?
F3 C2 1.354(4) . ?
F4 C7 1.341(3) . ?
C1 C6 1.364(5) . ?
C1 C2 1.379(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.390(4) . ?
C3 C8 1.402(4) . ?
C4 C5 1.386(3) . ?
C4 C12 1.404(3) . ?
C5 C9 1.368(4) . ?
C6 C7 1.365(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.393(4) . ?
C9 C10 1.364(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(3) . ?

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 S1 S2 102.24(8) . . ?
S3 S2 S1 107.99(4) . . ?
C4 S3 S2 104.65(8) . . ?
C12 S4 C8 103.25(10) . . ?
C6 C1 C2 119.6(3) . . ?
C6 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
F3 C2 C1 118.4(3) . . ?
F3 C2 C3 118.9(3) . . ?
C1 C2 C3 122.7(3) . . ?
C2 C3 C8 117.7(3) . . ?
C2 C3 S1 118.9(2) . . ?
C8 C3 S1 123.34(19) . . ?
C5 C4 C12 117.9(2) . . ?
C5 C4 S3 118.49(19) . . ?
C12 C4 S3 123.15(17) . . ?
F1 C5 C9 118.0(2) . . ?
F1 C5 C4 118.5(2) . . ?
C9 C5 C4 123.5(3) . . ?
C1 C6 C7 118.7(3) . . ?
C1 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
F4 C7 C6 117.3(3) . . ?
F4 C7 C8 119.2(3) . . ?
C6 C7 C8 123.4(3) . . ?
C7 C8 C3 117.9(2) . . ?
C7 C8 S4 120.5(2) . . ?
C3 C8 S4 121.34(19) . . ?
C5 C9 C10 118.6(3) . . ?
C5 C9 H9A 120.7 . . ?
C10 C9 H9A 120.7 . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
F2 C11 C10 117.0(2) . . ?
F2 C11 C12 119.4(2) . . ?
C10 C11 C12 123.6(3) . . ?
C11 C12 C4 117.2(2) . . ?
C11 C12 S4 121.12(19) . . ?
C4 C12 S4 121.41(17) . . ?

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
C6 C1 C2 F3 179.7(3) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
F3 C2 C3 C8 180.0(2) . . . . ?
C1 C2 C3 C8 0.1(4) . . . . ?
F3 C2 C3 S1 2.3(3) . . . . ?
C1 C2 C3 S1 -177.6(2) . . . . ?
S2 S1 C3 C2 -106.7(2) . . . . ?
S2 S1 C3 C8 75.70(19) . . . . ?
S2 S3 C4 C5 108.85(19) . . . . ?
S2 S3 C4 C12 -78.67(19) . . . . ?
C12 C4 C5 F1 179.5(2) . . . . ?
S3 C4 C5 F1 -7.6(3) . . . . ?
C12 C4 C5 C9 -2.1(4) . . . . ?
S3 C4 C5 C9 170.8(2) . . . . ?
C2 C1 C6 C7 0.6(5) . . . . ?
C1 C6 C7 F4 179.5(3) . . . . ?
C1 C6 C7 C8 -0.5(4) . . . . ?
F4 C7 C8 C3 -179.9(2) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
F4 C7 C8 S4 -5.3(3) . . . . ?
C6 C7 C8 S4 174.7(2) . . . . ?
C2 C3 C8 C7 0.1(3) . . . . ?
S1 C3 C8 C7 177.66(18) . . . . ?
C2 C3 C8 S4 -174.41(18) . . . . ?
S1 C3 C8 S4 3.2(3) . . . . ?
C12 S4 C8 C7 82.7(2) . . . . ?
C12 S4 C8 C3 -102.96(19) . . . . ?
F1 C5 C9 C10 178.2(3) . . . . ?
C4 C5 C9 C10 -0.2(4) . . . . ?
C5 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 F2 -177.9(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
F2 C11 C12 C4 175.6(2) . . . . ?
C10 C11 C12 C4 -2.4(4) . . . . ?
F2 C11 C12 S4 1.0(4) . . . . ?
C10 C11 C12 S4 -177.0(2) . . . . ?
C5 C4 C12 C11 3.2(3) . . . . ?
S3 C4 C12 C11 -169.28(19) . . . . ?
C5 C4 C12 S4 177.82(18) . . . . ?
S3 C4 C12 S4 5.3(3) . . . . ?
C8 S4 C12 C11 -91.4(2) . . . . ?
C8 S4 C12 C4 94.3(2) . . . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_7_2s1516
_database_code_depnum_ccdc_archive 'CCDC 2351029'
loop_
_audit_author_name
_audit_author_address
'Irina Bagryanskaya'
;Institute of Organic Chemistry, Novosibirsk 
Russia
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(1,1,2,2,3,3,4,7-octafluoro-2,3-dihydro-1H-indene-5,6-diyl) bis(benzylsulfane)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 F8 S2'
_chemical_formula_sum            'C23 H14 F8 S2'
_chemical_formula_weight         506.46

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0063(5)
_cell_length_b                   9.1070(5)
_cell_length_c                   13.7547(7)
_cell_angle_alpha                101.990(2)
_cell_angle_beta                 101.874(2)
_cell_angle_gamma                93.494(2)
_cell_volume                     1073.59(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4717
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.03

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6821
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11516
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_max         26.197
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4246
_reflns_number_gt                3359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.5881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4246
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.48373(7) 0.60768(7) 0.24713(5) 0.04097(19) Uani 1 1 d . . . . .
S2 S 0.60984(7) 0.38617(8) 0.07540(5) 0.0450(2) Uani 1 1 d . . . . .
F1 F 0.61242(18) 0.56687(16) 0.45391(11) 0.0486(4) Uani 1 1 d . . . . .
F2 F 0.82443(19) 0.18462(17) 0.16638(11) 0.0518(4) Uani 1 1 d . . . . .
F3 F 1.06332(17) 0.2011(2) 0.37149(14) 0.0622(5) Uani 1 1 d . . . . .
F4 F 0.8758(2) 0.02745(16) 0.34018(13) 0.0584(4) Uani 1 1 d . . . . .
F7 F 0.7003(2) 0.3028(2) 0.55425(13) 0.0713(6) Uani 1 1 d . . . . .
F8 F 0.9003(2) 0.46348(19) 0.57972(12) 0.0713(6) Uani 1 1 d . . . . .
F5 F 0.8542(3) 0.0902(2) 0.52115(16) 0.0838(6) Uani 1 1 d . . . . .
C23 C 0.8319(3) 0.6831(3) 0.0323(2) 0.0542(7) Uani 1 1 d . . . . .
H23A H 0.750235 0.667412 -0.026051 0.065 Uiso 1 1 calc R U . . .
C6 C 0.9152(3) 0.2111(3) 0.49720(19) 0.0434(6) Uani 1 1 d . . . . .
C17 C 0.7872(3) 0.4098(3) 0.03159(18) 0.0457(6) Uani 1 1 d . . . . .
H17A H 0.853688 0.333076 0.050883 0.055 Uiso 1 1 calc R U . . .
H17B H 0.762639 0.392143 -0.043722 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4752(4) 0.9921(4) 0.3355(2) 0.0622(8) Uani 1 1 d . . . . .
H12A H 0.497406 0.967160 0.400262 0.075 Uiso 1 1 calc R U . . .
C19 C 0.9929(3) 0.5894(4) 0.1603(2) 0.0571(8) Uani 1 1 d . . . . .
H19A H 1.024021 0.508664 0.190976 0.069 Uiso 1 1 calc R U . . .
C16 C 0.4853(4) 0.9446(3) 0.1626(3) 0.0613(8) Uani 1 1 d . . . . .
H16A H 0.515663 0.886068 0.105714 0.074 Uiso 1 1 calc R U . . .
C22 C 0.9088(4) 0.8254(4) 0.0723(3) 0.0730(10) Uani 1 1 d . . . . .
H22A H 0.880068 0.906681 0.041571 0.088 Uiso 1 1 calc R U . . .
C20 C 1.0686(4) 0.7334(5) 0.2001(2) 0.0742(11) Uani 1 1 d . . . . .
H20A H 1.150631 0.751019 0.258417 0.089 Uiso 1 1 calc R U . . .
C21 C 1.0263(4) 0.8494(5) 0.1562(3) 0.0784(11) Uani 1 1 d . . . . .
H21A H 1.078606 0.947738 0.184083 0.094 Uiso 1 1 calc R U . . .
C13 C 0.3953(4) 1.1154(4) 0.3220(4) 0.0852(13) Uani 1 1 d . . . . .
H13A H 0.364600 1.175957 0.377964 0.102 Uiso 1 1 calc R U . . .
C14 C 0.3614(4) 1.1490(4) 0.2285(5) 0.0895(15) Uani 1 1 d . . . . .
H14A H 0.305925 1.232273 0.218878 0.107 Uiso 1 1 calc R U . . .
C15 C 0.4060(4) 1.0651(5) 0.1507(3) 0.0812(12) Uani 1 1 d . . . . .
H15A H 0.382367 1.089427 0.085684 0.097 Uiso 1 1 calc R U . . .
C10 C 0.6129(4) 0.7762(3) 0.2669(4) 0.0787(11) Uani 1 1 d . . . . .
H10A H 0.679675 0.797299 0.336161 0.094 Uiso 1 1 calc R U . . .
H10B H 0.678219 0.761656 0.216683 0.094 Uiso 1 1 calc R U . . .
F6 F 1.0552(2) 0.2485(3) 0.55552(15) 0.0879(7) Uani 1 1 d . . . . .
C9 C 0.6635(3) 0.4738(2) 0.38123(16) 0.0319(5) Uani 1 1 d . . . . .
C1 C 0.6181(2) 0.4820(2) 0.27975(17) 0.0304(5) Uani 1 1 d . . . . .
C8 C 0.7602(3) 0.3713(2) 0.40949(16) 0.0312(5) Uani 1 1 d . . . . .
C2 C 0.6749(3) 0.3846(2) 0.20506(16) 0.0319(5) Uani 1 1 d . . . . .
C3 C 0.7722(3) 0.2826(2) 0.23590(17) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.8154(2) 0.2759(2) 0.33708(17) 0.0311(5) Uani 1 1 d . . . . .
C18 C 0.8714(3) 0.5625(3) 0.07540(17) 0.0391(5) Uani 1 1 d . . . . .
C11 C 0.5215(3) 0.9069(3) 0.2548(2) 0.0445(6) Uani 1 1 d . . . . .
C7 C 0.8159(3) 0.3429(3) 0.51362(17) 0.0406(6) Uani 1 1 d . . . . .
C5 C 0.9195(3) 0.1747(3) 0.38273(19) 0.0390(5) Uani 1 1 d . . . . .


_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 C1 1.770(2) . ?
S1 C10 1.806(3) . ?
S2 C2 1.762(2) . ?
S2 C17 1.835(3) . ?
F1 C9 1.347(2) . ?
F2 C3 1.347(3) . ?
F3 C5 1.349(3) . ?
F4 C5 1.345(3) . ?
F7 C7 1.345(3) . ?
F8 C7 1.345(3) . ?
F5 C6 1.332(3) . ?
C23 C22 1.378(4) . ?
C23 C18 1.384(4) . ?
C6 F6 1.329(3) . ?
C6 C7 1.547(3) . ?
C6 C5 1.549(4) . ?
C17 C18 1.486(4) . ?
C12 C11 1.371(4) . ?
C12 C13 1.394(5) . ?
C19 C20 1.387(5) . ?
C19 C18 1.394(4) . ?
C16 C11 1.363(4) . ?
C16 C15 1.365(5) . ?
C22 C21 1.365(5) . ?
C20 C21 1.358(6) . ?
C13 C14 1.362(6) . ?
C14 C15 1.329(6) . ?
C10 C11 1.506(4) . ?
C9 C8 1.376(3) . ?
C9 C1 1.391(3) . ?
C1 C2 1.413(3) . ?
C8 C4 1.375(3) . ?
C8 C7 1.498(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.492(3) . ?

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
C1 S1 C10 99.22(12) . . ?
C2 S2 C17 103.28(11) . . ?
C22 C23 C18 121.3(3) . . ?
F6 C6 F5 107.9(2) . . ?
F6 C6 C7 111.0(2) . . ?
F5 C6 C7 110.4(2) . . ?
F6 C6 C5 110.9(2) . . ?
F5 C6 C5 109.9(2) . . ?
C7 C6 C5 106.78(18) . . ?
C18 C17 S2 112.55(17) . . ?
C11 C12 C13 119.7(3) . . ?
C20 C19 C18 120.3(3) . . ?
C11 C16 C15 121.0(3) . . ?
C21 C22 C23 119.9(3) . . ?
C21 C20 C19 120.4(3) . . ?
C20 C21 C22 120.3(3) . . ?
C14 C13 C12 119.9(3) . . ?
C15 C14 C13 119.9(3) . . ?
C14 C15 C16 121.1(4) . . ?
C11 C10 S1 109.1(2) . . ?
F1 C9 C8 118.77(19) . . ?
F1 C9 C1 120.08(18) . . ?
C8 C9 C1 121.2(2) . . ?
C9 C1 C2 119.02(19) . . ?
C9 C1 S1 119.02(17) . . ?
C2 C1 S1 121.90(16) . . ?
C4 C8 C9 120.04(19) . . ?
C4 C8 C7 111.58(19) . . ?
C9 C8 C7 128.4(2) . . ?
C3 C2 C1 118.47(19) . . ?
C3 C2 S2 121.89(17) . . ?
C1 C2 S2 119.47(16) . . ?
F2 C3 C4 118.35(19) . . ?
F2 C3 C2 120.1(2) . . ?
C4 C3 C2 121.6(2) . . ?
C8 C4 C3 119.74(19) . . ?
C8 C4 C5 112.02(19) . . ?
C3 C4 C5 128.2(2) . . ?
C23 C18 C19 117.7(3) . . ?
C23 C18 C17 120.7(2) . . ?
C19 C18 C17 121.6(3) . . ?
C16 C11 C12 118.5(3) . . ?
C16 C11 C10 120.1(3) . . ?
C12 C11 C10 121.4(3) . . ?
F7 C7 F8 107.7(2) . . ?
F7 C7 C8 112.0(2) . . ?
F8 C7 C8 112.9(2) . . ?
F7 C7 C6 109.8(2) . . ?
F8 C7 C6 109.7(2) . . ?
C8 C7 C6 104.76(19) . . ?
F4 C5 F3 106.00(19) . . ?
F4 C5 C4 112.9(2) . . ?
F3 C5 C4 112.05(19) . . ?
F4 C5 C6 110.94(19) . . ?
F3 C5 C6 110.4(2) . . ?
C4 C5 C6 104.68(18) . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060


