# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_zkh-1
_audit_block_doi                 10.5517/ccdc.csd.cc2g89jl
_database_code_depnum_ccdc_archive 'CCDC 2272099'
loop_
_audit_author_name
_audit_author_address
'Kaihui Zhong '
;GUANGZHOU MEDICAL UNIVERSITY
China
;
_audit_update_record             
;
2023-06-24 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O S2'
_chemical_formula_sum            'C20 H16 O S2'
_chemical_formula_weight         336.45
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0077(5)
_cell_length_b                   11.6105(5)
_cell_length_c                   14.5031(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.121(4)
_cell_angle_gamma                90
_cell_volume                     1663.87(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4546
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      29.2630
_cell_measurement_theta_min      2.6650
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7621
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.258
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  19.00   1.00    2.09    --  -11.43 -99.00  30.00   27
  2  ω      2.00  86.00   1.00    2.09    --   12.05  38.00  60.00   84
  3  ω    -21.00  75.00   1.00    2.09    --   12.05  77.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0562623000
_diffrn_orient_matrix_UB_12      -0.0131105000
_diffrn_orient_matrix_UB_13      0.0346968000
_diffrn_orient_matrix_UB_21      0.0359194000
_diffrn_orient_matrix_UB_22      -0.0206344000
_diffrn_orient_matrix_UB_23      -0.0350449000
_diffrn_orient_matrix_UB_31      0.0264865000
_diffrn_orient_matrix_UB_32      0.0559437000
_diffrn_orient_matrix_UB_33      -0.0048025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2606
_reflns_number_total             2934
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.4559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0752
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.03291(4) 0.64413(4) 0.39933(3) 0.03054(13) Uani 1 1 d . . . . .
S2 S 0.19794(4) 0.77560(4) 0.27018(3) 0.03313(13) Uani 1 1 d . . . . .
O1 O 0.26714(12) 0.74397(10) 0.51053(8) 0.0367(3) Uani 1 1 d . . . . .
C1 C -0.04390(15) 0.55080(14) 0.30830(11) 0.0269(4) Uani 1 1 d . . . . .
C2 C -0.09953(15) 0.59333(15) 0.22097(11) 0.0317(4) Uani 1 1 d . . . . .
H2 H -0.096970 0.673556 0.208498 0.038 Uiso 1 1 calc R U . . .
C3 C -0.15872(16) 0.51805(16) 0.15224(12) 0.0365(4) Uani 1 1 d . . . . .
H3 H -0.194551 0.546578 0.091987 0.044 Uiso 1 1 calc R U . . .
C4 C -0.16585(18) 0.40196(17) 0.17089(13) 0.0411(4) Uani 1 1 d . . . . .
H4 H -0.206622 0.350734 0.123572 0.049 Uiso 1 1 calc R U . . .
C5 C -0.11377(19) 0.36020(15) 0.25826(13) 0.0417(5) Uani 1 1 d . . . . .
H5 H -0.120551 0.280454 0.271428 0.050 Uiso 1 1 calc R U . . .
C6 C -0.05175(17) 0.43407(14) 0.32669(12) 0.0328(4) Uani 1 1 d . . . . .
H6 H -0.014457 0.404787 0.386402 0.039 Uiso 1 1 calc R U . . .
C7 C 0.19511(15) 0.66545(14) 0.36012(11) 0.0269(4) Uani 1 1 d . . . . .
H7 H 0.221463 0.590609 0.333980 0.032 Uiso 1 1 calc R U . . .
C8 C 0.30114(16) 0.69413(13) 0.44441(11) 0.0261(4) Uani 1 1 d . . . . .
C9 C 0.44384(15) 0.65760(12) 0.44359(11) 0.0251(3) Uani 1 1 d . . . . .
C10 C 0.49028(16) 0.61611(14) 0.36414(11) 0.0302(4) Uani 1 1 d . . . . .
H10 H 0.431381 0.614667 0.305937 0.036 Uiso 1 1 calc R U . . .
C11 C 0.62199(17) 0.57705(15) 0.36995(12) 0.0336(4) Uani 1 1 d . . . . .
H11 H 0.653421 0.549181 0.315646 0.040 Uiso 1 1 calc R U . . .
C12 C 0.70798(16) 0.57845(14) 0.45455(12) 0.0317(4) Uani 1 1 d . . . . .
H12 H 0.797877 0.550365 0.458595 0.038 Uiso 1 1 calc R U . . .
C13 C 0.66290(16) 0.62082(14) 0.53329(12) 0.0318(4) Uani 1 1 d . . . . .
H13 H 0.722300 0.622581 0.591278 0.038 Uiso 1 1 calc R U . . .
C14 C 0.53211(16) 0.66049(13) 0.52792(11) 0.0282(4) Uani 1 1 d . . . . .
H14 H 0.502029 0.690008 0.582186 0.034 Uiso 1 1 calc R U . . .
C15 C 0.17692(16) 0.90502(14) 0.33172(11) 0.0298(4) Uani 1 1 d . . . . .
C16 C 0.28957(18) 0.97223(15) 0.36260(12) 0.0367(4) Uani 1 1 d . . . . .
H16 H 0.376839 0.947353 0.353198 0.044 Uiso 1 1 calc R U . . .
C17 C 0.2745(2) 1.07551(16) 0.40710(13) 0.0441(5) Uani 1 1 d . . . . .
H17 H 0.351576 1.121897 0.427996 0.053 Uiso 1 1 calc R U . . .
C18 C 0.1479(2) 1.11156(16) 0.42133(13) 0.0447(5) Uani 1 1 d . . . . .
H18 H 0.137948 1.182577 0.452060 0.054 Uiso 1 1 calc R U . . .
C19 C 0.0359(2) 1.04438(16) 0.39089(13) 0.0433(5) Uani 1 1 d . . . . .
H19 H -0.050996 1.068977 0.401222 0.052 Uiso 1 1 calc R U . . .
C20 C 0.04956(17) 0.94161(15) 0.34549(12) 0.0367(4) Uani 1 1 d . . . . .
H20 H -0.027929 0.896100 0.323751 0.044 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 C1 1.7851(16) . ?
S1 C7 1.8200(15) . ?
S2 C7 1.8302(16) . ?
S2 C15 1.7771(17) . ?
O1 C8 1.2140(19) . ?
C1 C2 1.391(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.523(2) . ?
C8 C9 1.492(2) . ?
C9 C10 1.395(2) . ?
C9 C14 1.391(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 C20 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?

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 C7 98.76(7) . . ?
C15 S2 C7 102.50(7) . . ?
C2 C1 S1 121.42(12) . . ?
C6 C1 S1 118.83(12) . . ?
C6 C1 C2 119.72(15) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.65(16) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.32(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.01(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.18(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.09(16) . . ?
C5 C6 H6 120.0 . . ?
S1 C7 S2 115.66(9) . . ?
S1 C7 H7 107.6 . . ?
S2 C7 H7 107.6 . . ?
C8 C7 S1 108.74(10) . . ?
C8 C7 S2 109.37(10) . . ?
C8 C7 H7 107.6 . . ?
O1 C8 C7 119.43(14) . . ?
O1 C8 C9 122.04(14) . . ?
C9 C8 C7 118.52(13) . . ?
C10 C9 C8 123.34(14) . . ?
C14 C9 C8 117.49(14) . . ?
C14 C9 C10 119.10(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.12(15) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.20(15) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.89(15) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.23(15) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.45(15) . . ?
C13 C14 H14 119.8 . . ?
C16 C15 S2 118.91(13) . . ?
C16 C15 C20 119.99(16) . . ?
C20 C15 S2 121.04(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.77(17) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.25(18) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.93(18) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.34(18) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.72(17) . . ?
C19 C20 H20 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
S1 C1 C2 C3 -179.76(12) . . . . ?
S1 C1 C6 C5 178.35(13) . . . . ?
S1 C7 C8 O1 -29.82(18) . . . . ?
S1 C7 C8 C9 148.96(11) . . . . ?
S2 C7 C8 O1 97.34(15) . . . . ?
S2 C7 C8 C9 -83.88(15) . . . . ?
S2 C15 C16 C17 177.29(13) . . . . ?
S2 C15 C20 C19 -177.90(13) . . . . ?
O1 C8 C9 C10 -170.03(15) . . . . ?
O1 C8 C9 C14 13.1(2) . . . . ?
C1 S1 C7 S2 82.56(10) . . . . ?
C1 S1 C7 C8 -153.96(11) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C7 S1 C1 C2 -78.78(14) . . . . ?
C7 S1 C1 C6 103.37(13) . . . . ?
C7 S2 C15 C16 100.93(14) . . . . ?
C7 S2 C15 C20 -81.85(14) . . . . ?
C7 C8 C9 C10 11.2(2) . . . . ?
C7 C8 C9 C14 -165.64(14) . . . . ?
C8 C9 C10 C11 -175.96(15) . . . . ?
C8 C9 C14 C13 175.76(14) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C9 C14 C13 -1.2(2) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C9 0.5(2) . . . . ?
C14 C9 C10 C11 0.9(2) . . . . ?
C15 S2 C7 S1 68.81(10) . . . . ?
C15 S2 C7 C8 -54.34(12) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C15 C20 C19 -0.7(2) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C15 1.0(3) . . . . ?
C20 C15 C16 C17 0.0(3) . . . . ?

_olex2_date_sample_data_collection 2023-05-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.269
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_zkh-2
_audit_block_doi                 10.5517/ccdc.csd.cc2g8b14
_database_code_depnum_ccdc_archive 'CCDC 2272115'
loop_
_audit_author_name
_audit_author_address
'Kaihui Zhong'
;GUANGZHOU MEDICAL UNIVERSITY
China
;
_audit_update_record             
;
2023-06-24 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F5 O2 S2'
_chemical_formula_sum            'C16 H11 F5 O2 S2'
_chemical_formula_weight         394.37
_chemical_melting_point          ?
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'
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'

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

_cell_length_a                   9.0497(5)
_cell_length_b                   9.8617(6)
_cell_length_c                   17.5484(11)
_cell_angle_alpha                92.637(5)
_cell_angle_beta                 91.848(5)
_cell_angle_gamma                95.942(5)
_cell_volume                     1554.97(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4524
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      29.2520
_cell_measurement_theta_min      2.4940
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9482
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.079
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  39.00   1.00    2.00    --   11.90 -57.00 120.00   95
  2  ω    -15.00  77.00   1.00    2.00    --   11.90  77.00  30.00   92
  3  ω    -11.00  84.00   1.00    2.00    --   11.90  57.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372823000
_diffrn_orient_matrix_UB_12      -0.0260910000
_diffrn_orient_matrix_UB_13      -0.0345985000
_diffrn_orient_matrix_UB_21      -0.0231117000
_diffrn_orient_matrix_UB_22      0.0652737000
_diffrn_orient_matrix_UB_23      -0.0062662000
_diffrn_orient_matrix_UB_31      0.0655307000
_diffrn_orient_matrix_UB_32      0.0173397000
_diffrn_orient_matrix_UB_33      -0.0200789000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4377
_reflns_number_total             5463
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+5.9498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1752
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.56068(14) 0.25620(13) 0.53303(7) 0.0226(3) Uani 1 1 d . . . . .
S2 S 0.61898(14) 0.20870(13) 0.37082(7) 0.0232(3) Uani 1 1 d . . . . .
F1 F 0.8035(3) -0.0565(3) 0.40153(18) 0.0355(8) Uani 1 1 d . . . . .
F2 F 1.0037(4) -0.1187(3) 0.29804(16) 0.0358(8) Uani 1 1 d . . . . .
F3 F 1.2471(4) 0.0569(3) 0.27781(17) 0.0376(8) Uani 1 1 d . . . . .
F4 F 1.2789(3) 0.3065(3) 0.35195(17) 0.0340(7) Uani 1 1 d . . . . .
F5 F 1.0815(3) 0.3714(3) 0.45587(17) 0.0328(7) Uani 1 1 d . . . . .
O1 O 0.8731(4) 0.2105(4) 0.55953(19) 0.0301(8) Uani 1 1 d . . . . .
O2 O 0.4133(4) 0.2634(4) 0.5010(2) 0.0347(9) Uani 1 1 d . . . . .
C1 C 0.9381(6) 0.1594(5) 0.4323(3) 0.0224(11) Uani 1 1 d . . . . .
C2 C 0.9211(6) 0.0349(5) 0.3908(3) 0.0242(11) Uani 1 1 d . . . . .
C3 C 1.0239(6) 0.0002(5) 0.3391(3) 0.0259(11) Uani 1 1 d . . . . .
C4 C 1.1454(6) 0.0911(5) 0.3268(3) 0.0246(11) Uani 1 1 d . . . . .
C5 C 1.1648(6) 0.2154(5) 0.3664(3) 0.0261(11) Uani 1 1 d . . . . .
C6 C 1.0611(6) 0.2468(5) 0.4189(3) 0.0217(11) Uani 1 1 d . . . . .
C7 C 0.8279(6) 0.1952(5) 0.4915(3) 0.0219(11) Uani 1 1 d . . . . .
C8 C 0.6835(5) 0.2133(5) 0.4652(3) 0.0215(10) Uani 1 1 d . . . . .
C9 C 0.6294(6) 0.4125(6) 0.5800(3) 0.0309(12) Uani 1 1 d . . . . .
H9A H 0.627511 0.485877 0.544278 0.046 Uiso 1 1 calc R U . . .
H9B H 0.731810 0.407536 0.598715 0.046 Uiso 1 1 calc R U . . .
H9C H 0.567194 0.431146 0.623143 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5581(7) 0.1374(6) 0.6052(3) 0.0337(13) Uani 1 1 d . . . . .
H10A H 0.498218 0.167446 0.647084 0.051 Uiso 1 1 calc R U . . .
H10B H 0.659921 0.131042 0.624460 0.051 Uiso 1 1 calc R U . . .
H10C H 0.514836 0.047727 0.584221 0.051 Uiso 1 1 calc R U . . .
C11 C 0.6566(5) 0.3794(5) 0.3413(3) 0.0217(11) Uani 1 1 d . . . . .
C12 C 0.7602(6) 0.4744(5) 0.3798(3) 0.0248(11) Uani 1 1 d . . . . .
H12 H 0.812644 0.450613 0.424199 0.030 Uiso 1 1 calc R U . . .
C13 C 0.7863(6) 0.6050(6) 0.3524(3) 0.0294(12) Uani 1 1 d . . . . .
H13 H 0.856018 0.670954 0.378739 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7115(6) 0.6389(6) 0.2873(3) 0.0306(12) Uani 1 1 d . . . . .
H14 H 0.730261 0.727678 0.268639 0.037 Uiso 1 1 calc R U . . .
C15 C 0.6100(6) 0.5439(6) 0.2498(3) 0.0329(13) Uani 1 1 d . . . . .
H15 H 0.560165 0.567043 0.204462 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5790(6) 0.4147(5) 0.2770(3) 0.0250(11) Uani 1 1 d . . . . .
H16 H 0.505466 0.350899 0.251821 0.030 Uiso 1 1 calc R U . . .
S3 S 0.14936(14) 0.23516(13) 0.13316(7) 0.0236(3) Uani 1 1 d . . . . .
S4 S 0.06406(14) 0.24284(14) -0.02984(7) 0.0246(3) Uani 1 1 d . . . . .
F6 F 0.5531(4) -0.0791(3) 0.20552(17) 0.0415(8) Uani 1 1 d . . . . .
F7 F 0.7991(4) 0.1029(4) 0.22267(17) 0.0435(9) Uani 1 1 d . . . . .
F8 F 0.8132(3) 0.3383(4) 0.14738(17) 0.0380(8) Uani 1 1 d . . . . .
F9 F 0.5949(3) 0.3808(3) 0.04596(17) 0.0336(7) Uani 1 1 d . . . . .
F10 F 0.3308(4) -0.0358(3) 0.10594(18) 0.0364(8) Uani 1 1 d . . . . .
O3 O 0.3725(4) 0.1958(4) -0.05565(19) 0.0310(9) Uani 1 1 d . . . . .
O4 O -0.0792(4) 0.2533(5) 0.0020(2) 0.0413(10) Uani 1 1 d . . . . .
C17 C 0.6979(6) 0.2424(6) 0.1347(3) 0.0269(12) Uani 1 1 d . . . . .
C18 C 0.6877(6) 0.1270(6) 0.1745(3) 0.0291(12) Uani 1 1 d . . . . .
C19 C 0.5633(6) 0.0339(5) 0.1650(3) 0.0278(12) Uani 1 1 d . . . . .
C20 C 0.4503(6) 0.0571(5) 0.1139(3) 0.0279(12) Uani 1 1 d . . . . .
C21 C 0.4582(5) 0.1732(5) 0.0720(3) 0.0225(11) Uani 1 1 d . . . . .
C22 C 0.5838(6) 0.2647(5) 0.0829(3) 0.0245(11) Uani 1 1 d . . . . .
C23 C 0.3394(6) 0.1971(5) 0.0128(3) 0.0212(11) Uani 1 1 d . . . . .
C24 C 0.1979(6) 0.2186(5) 0.0386(3) 0.0224(11) Uani 1 1 d . . . . .
C25 C 0.1203(7) 0.3893(6) -0.0793(3) 0.0338(13) Uani 1 1 d . . . . .
H25A H 0.045351 0.401396 -0.119293 0.051 Uiso 1 1 calc R U . . .
H25B H 0.215732 0.378774 -0.102606 0.051 Uiso 1 1 calc R U . . .
H25C H 0.131314 0.469456 -0.043648 0.051 Uiso 1 1 calc R U . . .
C26 C 0.0557(7) 0.1103(6) -0.1009(3) 0.0366(14) Uani 1 1 d . . . . .
H26A H 0.032375 0.022422 -0.077834 0.055 Uiso 1 1 calc R U . . .
H26B H 0.151850 0.111628 -0.125166 0.055 Uiso 1 1 calc R U . . .
H26C H -0.021868 0.123090 -0.139449 0.055 Uiso 1 1 calc R U . . .
C27 C 0.1826(5) 0.4132(5) 0.1581(3) 0.0209(10) Uani 1 1 d . . . . .
C28 C 0.2731(5) 0.5038(5) 0.1171(3) 0.0226(11) Uani 1 1 d . . . . .
H28 H 0.319625 0.472157 0.072929 0.027 Uiso 1 1 calc R U . . .
C29 C 0.2951(6) 0.6404(5) 0.1410(3) 0.0280(12) Uani 1 1 d . . . . .
H29 H 0.355053 0.702329 0.112048 0.034 Uiso 1 1 calc R U . . .
C30 C 0.2315(6) 0.6881(6) 0.2060(3) 0.0298(12) Uani 1 1 d . . . . .
H30 H 0.248978 0.781563 0.222646 0.036 Uiso 1 1 calc R U . . .
C31 C 0.1415(6) 0.5968(6) 0.2467(3) 0.0295(12) Uani 1 1 d . . . . .
H31 H 0.097050 0.628711 0.291508 0.035 Uiso 1 1 calc R U . . .
C32 C 0.1154(6) 0.4615(6) 0.2235(3) 0.0277(12) Uani 1 1 d . . . . .
H32 H 0.052271 0.400794 0.251558 0.033 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 O2 1.440(4) . ?
S1 C8 1.722(5) . ?
S1 C9 1.759(5) . ?
S1 C10 1.764(5) . ?
S2 C8 1.736(5) . ?
S2 C11 1.786(5) . ?
F1 C2 1.345(6) . ?
F2 C3 1.341(6) . ?
F3 C4 1.337(5) . ?
F4 C5 1.335(6) . ?
F5 C6 1.356(5) . ?
O1 C7 1.246(6) . ?
C1 C2 1.390(7) . ?
C1 C6 1.369(7) . ?
C1 C7 1.520(6) . ?
C2 C3 1.378(7) . ?
C3 C4 1.374(7) . ?
C4 C5 1.373(7) . ?
C5 C6 1.383(7) . ?
C7 C8 1.403(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.390(7) . ?
C11 C16 1.387(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(8) . ?
C16 H16 0.9500 . ?
S3 C24 1.735(5) . ?
S3 C27 1.782(5) . ?
S4 O4 1.440(4) . ?
S4 C24 1.721(5) . ?
S4 C25 1.758(6) . ?
S4 C26 1.759(5) . ?
F6 C19 1.346(6) . ?
F7 C18 1.342(6) . ?
F8 C17 1.339(6) . ?
F9 C22 1.338(6) . ?
F10 C20 1.342(6) . ?
O3 C23 1.247(6) . ?
C17 C18 1.360(8) . ?
C17 C22 1.394(7) . ?
C18 C19 1.377(8) . ?
C19 C20 1.382(7) . ?
C20 C21 1.385(7) . ?
C21 C22 1.379(7) . ?
C21 C23 1.515(7) . ?
C23 C24 1.406(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.390(7) . ?
C27 C32 1.403(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.380(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.389(8) . ?
C31 H31 0.9500 . ?
C31 C32 1.371(7) . ?
C32 H32 0.9500 . ?

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
O2 S1 C8 112.5(2) . . ?
O2 S1 C9 110.6(3) . . ?
O2 S1 C10 110.9(3) . . ?
C8 S1 C9 109.2(2) . . ?
C8 S1 C10 109.0(3) . . ?
C9 S1 C10 104.3(3) . . ?
C8 S2 C11 105.3(2) . . ?
C2 C1 C7 121.6(4) . . ?
C6 C1 C2 117.0(4) . . ?
C6 C1 C7 121.4(4) . . ?
F1 C2 C1 120.2(4) . . ?
F1 C2 C3 118.2(5) . . ?
C3 C2 C1 121.6(5) . . ?
F2 C3 C2 120.8(5) . . ?
F2 C3 C4 119.4(4) . . ?
C4 C3 C2 119.7(5) . . ?
F3 C4 C3 119.9(5) . . ?
F3 C4 C5 120.0(5) . . ?
C5 C4 C3 120.1(5) . . ?
F4 C5 C4 120.2(5) . . ?
F4 C5 C6 120.7(5) . . ?
C4 C5 C6 119.0(5) . . ?
F5 C6 C1 119.7(4) . . ?
F5 C6 C5 117.7(4) . . ?
C1 C6 C5 122.6(5) . . ?
O1 C7 C1 117.8(4) . . ?
O1 C7 C8 124.7(4) . . ?
C8 C7 C1 117.4(4) . . ?
S1 C8 S2 116.3(3) . . ?
C7 C8 S1 116.8(3) . . ?
C7 C8 S2 126.8(4) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 S2 122.3(4) . . ?
C16 C11 S2 117.3(4) . . ?
C16 C11 C12 120.3(5) . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 120.3 . . ?
C15 C16 C11 119.3(5) . . ?
C15 C16 H16 120.3 . . ?
C24 S3 C27 105.1(2) . . ?
O4 S4 C24 112.3(2) . . ?
O4 S4 C25 110.5(3) . . ?
O4 S4 C26 111.3(3) . . ?
C24 S4 C25 109.6(3) . . ?
C24 S4 C26 109.4(3) . . ?
C25 S4 C26 103.3(3) . . ?
F8 C17 C18 120.6(5) . . ?
F8 C17 C22 119.5(5) . . ?
C18 C17 C22 119.8(5) . . ?
F7 C18 C17 120.1(5) . . ?
F7 C18 C19 119.9(5) . . ?
C17 C18 C19 120.0(5) . . ?
F6 C19 C18 119.6(5) . . ?
F6 C19 C20 120.6(5) . . ?
C18 C19 C20 119.8(5) . . ?
F10 C20 C19 118.3(5) . . ?
F10 C20 C21 120.3(5) . . ?
C19 C20 C21 121.4(5) . . ?
C20 C21 C23 122.3(5) . . ?
C22 C21 C20 117.4(5) . . ?
C22 C21 C23 120.1(4) . . ?
F9 C22 C17 118.6(5) . . ?
F9 C22 C21 119.9(5) . . ?
C21 C22 C17 121.5(5) . . ?
O3 C23 C21 118.3(4) . . ?
O3 C23 C24 124.0(5) . . ?
C24 C23 C21 117.6(4) . . ?
S4 C24 S3 116.9(3) . . ?
C23 C24 S3 126.1(4) . . ?
C23 C24 S4 116.8(4) . . ?
S4 C25 H25A 109.5 . . ?
S4 C25 H25B 109.5 . . ?
S4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
S4 C26 H26A 109.5 . . ?
S4 C26 H26B 109.5 . . ?
S4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 S3 123.3(4) . . ?
C28 C27 C32 119.4(5) . . ?
C32 C27 S3 117.3(4) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.7(4) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.1(5) . . ?
C30 C29 H29 119.4 . . ?
C29 C30 H30 120.6 . . ?
C29 C30 C31 118.8(5) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.3(5) . . ?
C32 C31 H31 119.4 . . ?
C27 C32 H32 120.2 . . ?
C31 C32 C27 119.7(5) . . ?
C31 C32 H32 120.2 . . ?

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
S2 C11 C12 C13 178.5(4) . . . . ?
S2 C11 C16 C15 -176.8(4) . . . . ?
F1 C2 C3 F2 3.0(7) . . . . ?
F1 C2 C3 C4 -180.0(4) . . . . ?
F2 C3 C4 F3 -4.3(7) . . . . ?
F2 C3 C4 C5 177.6(4) . . . . ?
F3 C4 C5 F4 5.1(7) . . . . ?
F3 C4 C5 C6 -177.6(4) . . . . ?
F4 C5 C6 F5 -1.3(7) . . . . ?
F4 C5 C6 C1 176.2(4) . . . . ?
O1 C7 C8 S1 -1.5(7) . . . . ?
O1 C7 C8 S2 173.7(4) . . . . ?
O2 S1 C8 S2 8.3(4) . . . . ?
O2 S1 C8 C7 -176.1(4) . . . . ?
C1 C2 C3 F2 -178.1(4) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C1 C7 C8 S1 -179.1(3) . . . . ?
C1 C7 C8 S2 -4.0(7) . . . . ?
C2 C1 C6 F5 178.0(4) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C1 C7 O1 114.9(5) . . . . ?
C2 C1 C7 C8 -67.2(6) . . . . ?
C2 C3 C4 F3 178.7(4) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 F4 -176.8(4) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 F5 -178.5(4) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C6 C1 C2 F1 179.4(4) . . . . ?
C6 C1 C2 C3 0.6(7) . . . . ?
C6 C1 C7 O1 -63.1(6) . . . . ?
C6 C1 C7 C8 114.7(5) . . . . ?
C7 C1 C2 F1 1.3(7) . . . . ?
C7 C1 C2 C3 -177.5(5) . . . . ?
C7 C1 C6 F5 -3.9(7) . . . . ?
C7 C1 C6 C5 178.6(4) . . . . ?
C8 S2 C11 C12 19.4(5) . . . . ?
C8 S2 C11 C16 -161.4(4) . . . . ?
C9 S1 C8 S2 -114.9(3) . . . . ?
C9 S1 C8 C7 60.7(5) . . . . ?
C10 S1 C8 S2 131.7(3) . . . . ?
C10 S1 C8 C7 -52.6(5) . . . . ?
C11 S2 C8 S1 86.9(3) . . . . ?
C11 S2 C8 C7 -88.3(5) . . . . ?
C11 C12 C13 C14 -0.8(8) . . . . ?
C12 C11 C16 C15 2.4(7) . . . . ?
C12 C13 C14 C15 0.6(8) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
C14 C15 C16 C11 -2.7(8) . . . . ?
C16 C11 C12 C13 -0.6(7) . . . . ?
S3 C27 C28 C29 -179.0(4) . . . . ?
S3 C27 C32 C31 177.8(4) . . . . ?
F6 C19 C20 F10 0.0(7) . . . . ?
F6 C19 C20 C21 179.6(4) . . . . ?
F7 C18 C19 F6 1.6(7) . . . . ?
F7 C18 C19 C20 -178.3(4) . . . . ?
F8 C17 C18 F7 -5.3(7) . . . . ?
F8 C17 C18 C19 175.2(4) . . . . ?
F8 C17 C22 F9 1.6(7) . . . . ?
F8 C17 C22 C21 -175.5(4) . . . . ?
F10 C20 C21 C22 179.9(4) . . . . ?
F10 C20 C21 C23 -3.7(7) . . . . ?
O3 C23 C24 S3 -174.5(4) . . . . ?
O3 C23 C24 S4 0.5(7) . . . . ?
O4 S4 C24 S3 -9.0(4) . . . . ?
O4 S4 C24 C23 175.5(4) . . . . ?
C17 C18 C19 F6 -179.0(4) . . . . ?
C17 C18 C19 C20 1.1(7) . . . . ?
C18 C17 C22 F9 178.3(4) . . . . ?
C18 C17 C22 C21 1.3(7) . . . . ?
C18 C19 C20 F10 179.9(4) . . . . ?
C18 C19 C20 C21 -0.5(7) . . . . ?
C19 C20 C21 C22 0.3(7) . . . . ?
C19 C20 C21 C23 176.7(4) . . . . ?
C20 C21 C22 F9 -177.7(4) . . . . ?
C20 C21 C22 C17 -0.7(7) . . . . ?
C20 C21 C23 O3 -112.3(5) . . . . ?
C20 C21 C23 C24 67.2(6) . . . . ?
C21 C23 C24 S3 6.0(7) . . . . ?
C21 C23 C24 S4 -179.0(3) . . . . ?
C22 C17 C18 F7 178.0(4) . . . . ?
C22 C17 C18 C19 -1.5(7) . . . . ?
C22 C21 C23 O3 64.0(6) . . . . ?
C22 C21 C23 C24 -116.4(5) . . . . ?
C23 C21 C22 F9 5.8(7) . . . . ?
C23 C21 C22 C17 -177.2(4) . . . . ?
C24 S3 C27 C28 -18.7(5) . . . . ?
C24 S3 C27 C32 162.7(4) . . . . ?
C25 S4 C24 S3 114.2(3) . . . . ?
C25 S4 C24 C23 -61.3(4) . . . . ?
C26 S4 C24 S3 -133.1(3) . . . . ?
C26 S4 C24 C23 51.4(5) . . . . ?
C27 S3 C24 S4 -85.1(3) . . . . ?
C27 S3 C24 C23 90.0(5) . . . . ?
C27 C28 C29 C30 1.6(8) . . . . ?
C28 C27 C32 C31 -0.9(7) . . . . ?
C28 C29 C30 C31 -1.4(8) . . . . ?
C29 C30 C31 C32 0.1(8) . . . . ?
C30 C31 C32 C27 1.0(8) . . . . ?
C32 C27 C28 C29 -0.4(7) . . . . ?

_olex2_date_sample_data_collection 2023-05-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 69.505
_oxdiff_exptl_absorpt_empirical_full_min 0.552
