# 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 2022

####################################################################### 
# 
# 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_ChenC-37
_database_code_depnum_ccdc_archive 'CCDC 2105559'
loop_
_audit_author_name
_audit_author_address
'Yaxing Wu'
;Tsinghua University
China
;
_audit_update_record             
;
2021-12-04 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H6 F6 S'
_chemical_formula_sum            'C16 H6 F6 S'
_chemical_formula_weight         344.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4232(4)
_cell_length_b                   19.3491(8)
_cell_length_c                   14.9248(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.331(5)
_cell_angle_gamma                90
_cell_volume                     2647.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5388
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      74.7

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.194
_exptl_absorpt_coefficient_mu    2.840
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.430
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlaS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_reflns_number            17966
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.806
_diffrn_reflns_theta_max         75.405
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5371
_reflns_number_gt                3927
_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       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0010P)²+4.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_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         5371
_refine_ls_number_parameters     429
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0912
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1818
_refine_ls_goodness_of_fit_ref   1.507
_refine_ls_restrained_S_all      1.509
_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 0.7270(3) 0.64340(10) 0.73180(19) 0.0330(5) Uani 0.65 1 d D . P A 1
C4 C 0.5743(15) 0.6639(7) 0.6494(11) 0.0291(10) Uani 0.65 1 d D . P A 1
H4A H 0.5463 0.7093 0.6348 0.035 Uiso 0.65 1 calc R U P A 1
S1' S 0.5935(6) 0.6795(2) 0.6589(5) 0.0291(10) Uani 0.35 1 d D . P A 2
C4' C 0.718(3) 0.6256(10) 0.7236(17) 0.0330(5) Uani 0.35 1 d D . P A 2
H4B H 0.8004 0.6423 0.7645 0.040 Uiso 0.35 1 calc R U P A 2
S2 S 0.7596(2) 0.75397(9) 0.20980(18) 0.0350(5) Uani 0.75 1 d D . P B 3
C20 C 0.6052(17) 0.7335(8) 0.1294(14) 0.0346(16) Uani 0.75 1 d D . P B 3
H20A H 0.5884 0.6896 0.1041 0.042 Uiso 0.75 1 calc R U P B 3
S2' S 0.6254(13) 0.7192(5) 0.1400(10) 0.0346(16) Uani 0.25 1 d D . P B 4
C20' C 0.745(3) 0.7708(15) 0.213(3) 0.0350(5) Uani 0.25 1 d D . P B 4
H20B H 0.8316 0.7547 0.2503 0.042 Uiso 0.25 1 calc R U P B 4
F1 F 0.7831(5) 0.31715(18) 0.7942(3) 0.0646(11) Uani 1 1 d . . . . .
F2 F 1.0354(4) 0.3481(2) 0.9149(2) 0.0581(10) Uani 1 1 d . . . . .
F3 F 1.1185(4) 0.4821(2) 0.9408(3) 0.0617(11) Uani 1 1 d . . . . .
F4 F 0.0636(4) 0.50689(17) 0.4175(2) 0.0482(8) Uani 1 1 d . . . . .
F5 F -0.0245(3) 0.62966(19) 0.3390(2) 0.0496(8) Uani 1 1 d . . . . .
F6 F 0.1411(4) 0.74394(19) 0.3903(3) 0.0577(10) Uani 1 1 d . . . . .
F7 F 1.1236(4) 0.9111(2) 0.4444(2) 0.0582(10) Uani 1 1 d . . . . .
F8 F 1.0443(4) 1.04533(19) 0.4186(2) 0.0529(9) Uani 1 1 d . . . . .
F9 F 0.7964(4) 1.07781(17) 0.2946(3) 0.0593(10) Uani 1 1 d . . . . .
F10 F 0.1119(4) 0.6502(2) -0.0750(3) 0.0602(10) Uani 1 1 d . . . . .
F11 F -0.0179(4) 0.7649(2) -0.1592(2) 0.0583(10) Uani 1 1 d . . . . .
F12 F 0.1072(4) 0.88966(19) -0.1128(3) 0.0553(9) Uani 1 1 d . . . . .
C1 C 0.6914(5) 0.5578(2) 0.7131(3) 0.0276(9) Uani 1 1 d D . . . .
C2 C 0.5662(5) 0.5483(2) 0.6451(3) 0.0265(9) Uani 1 1 d . . . . .
H2A H 0.5296 0.5048 0.6255 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4987(5) 0.6105(2) 0.6077(3) 0.0268(9) Uani 1 1 d D . . . .
C5 C 0.7812(5) 0.5032(3) 0.7672(3) 0.0276(9) Uani 1 1 d . . . . .
C6 C 0.7382(6) 0.4344(3) 0.7570(3) 0.0348(11) Uani 1 1 d . . . . .
H6A H 0.6508 0.4225 0.7167 0.042 Uiso 1 1 calc R U . . .
C7 C 0.8252(7) 0.3834(3) 0.8068(4) 0.0427(13) Uani 1 1 d . . . . .
C8 C 0.9538(6) 0.3985(3) 0.8685(4) 0.0391(12) Uani 1 1 d . . . . .
C9 C 0.9939(6) 0.4673(3) 0.8800(4) 0.0414(13) Uani 1 1 d . . . . .
C10 C 0.9106(6) 0.5185(3) 0.8302(4) 0.0397(12) Uani 1 1 d . . . . .
H10A H 0.9413 0.5642 0.8388 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3629(5) 0.6154(2) 0.5365(3) 0.0258(9) Uani 1 1 d . . . . .
C12 C 0.2756(5) 0.5573(2) 0.5093(3) 0.0291(10) Uani 1 1 d . . . . .
H12A H 0.3044 0.5146 0.5360 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1479(5) 0.5629(3) 0.4438(3) 0.0334(11) Uani 1 1 d . . . . .
C14 C 0.1013(6) 0.6262(3) 0.4036(3) 0.0348(11) Uani 1 1 d . . . . .
C15 C 0.1859(6) 0.6827(3) 0.4298(4) 0.0380(12) Uani 1 1 d . . . . .
C16 C 0.3151(5) 0.6791(3) 0.4952(4) 0.0338(11) Uani 1 1 d . . . . .
H16A H 0.3707 0.7188 0.5121 0.041 Uiso 1 1 calc R U . . .
C17 C 0.7018(5) 0.8380(2) 0.2117(3) 0.0290(10) Uani 1 1 d D . . . .
C18 C 0.5666(5) 0.8463(2) 0.1520(3) 0.0274(9) Uani 1 1 d . . . . .
H18A H 0.5171 0.8883 0.1432 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5111(5) 0.7848(2) 0.1056(3) 0.0313(10) Uani 1 1 d D . . . .
C21 C 0.7909(5) 0.8921(2) 0.2675(3) 0.0272(9) Uani 1 1 d . . . . .
C22 C 0.9183(5) 0.8753(3) 0.3331(3) 0.0342(11) Uani 1 1 d . . . . .
H22A H 0.9468 0.8294 0.3434 0.041 Uiso 1 1 calc R U . . .
C23 C 1.0012(6) 0.9273(3) 0.3824(3) 0.0391(12) Uani 1 1 d . . . . .
C24 C 0.9626(6) 0.9955(3) 0.3701(3) 0.0382(12) Uani 1 1 d . . . . .
C25 C 0.8363(6) 1.0115(3) 0.3062(4) 0.0405(12) Uani 1 1 d . . . . .
C26 C 0.7508(6) 0.9622(3) 0.2554(3) 0.0344(11) Uani 1 1 d . . . . .
H26A H 0.6662 0.9748 0.2128 0.041 Uiso 1 1 calc R U . . .
C27 C 0.3717(5) 0.7792(3) 0.0364(3) 0.0308(10) Uani 1 1 d . . . . .
C28 C 0.3055(6) 0.7150(3) 0.0126(4) 0.0392(12) Uani 1 1 d . . . . .
H28A H 0.3495 0.6749 0.0402 0.047 Uiso 1 1 calc R U . . .
C29 C 0.1754(6) 0.7113(3) -0.0516(4) 0.0424(13) Uani 1 1 d . . . . .
C30 C 0.1086(6) 0.7692(3) -0.0954(4) 0.0395(12) Uani 1 1 d . . . . .
C31 C 0.1730(6) 0.8329(3) -0.0709(4) 0.0359(11) Uani 1 1 d . . . . .
C32 C 0.3024(5) 0.8380(3) -0.0065(3) 0.0339(11) Uani 1 1 d . . . . .
H32A H 0.3444 0.8812 0.0087 0.041 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 1.700(5) . ?
S1 C4 1.710(9) . ?
C4 C3 1.326(14) . ?
C4 H4A 0.9300 . ?
S1' C3 1.688(5) . ?
S1' C4' 1.694(10) . ?
C4' C1 1.34(2) . ?
C4' H4B 0.9300 . ?
S2 C20 1.705(10) . ?
S2 C17 1.718(4) . ?
C20 C19 1.323(16) . ?
C20 H20A 0.9300 . ?
S2' C19 1.666(7) . ?
S2' C20' 1.699(10) . ?
C20' C17 1.36(3) . ?
C20' H20B 0.9300 . ?
F1 C7 1.343(7) . ?
F2 C8 1.333(6) . ?
F3 C9 1.339(6) . ?
F4 C13 1.347(6) . ?
F5 C14 1.345(6) . ?
F6 C15 1.347(6) . ?
F7 C23 1.338(6) . ?
F8 C24 1.338(6) . ?
F9 C25 1.337(6) . ?
F10 C29 1.336(6) . ?
F11 C30 1.345(6) . ?
F12 C31 1.342(6) . ?
C1 C2 1.380(6) . ?
C1 C5 1.472(7) . ?
C2 C3 1.415(6) . ?
C2 H2A 0.9300 . ?
C3 C11 1.465(6) . ?
C5 C10 1.389(7) . ?
C5 C6 1.391(7) . ?
C6 C7 1.384(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(8) . ?
C8 C9 1.383(8) . ?
C9 C10 1.372(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.397(7) . ?
C11 C16 1.404(7) . ?
C12 C13 1.369(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.390(7) . ?
C14 C15 1.357(8) . ?
C15 C16 1.376(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.385(6) . ?
C17 C21 1.473(7) . ?
C18 C19 1.416(7) . ?
C18 H18A 0.9300 . ?
C19 C27 1.476(7) . ?
C21 C22 1.401(6) . ?
C21 C26 1.410(7) . ?
C22 C23 1.377(8) . ?
C22 H22A 0.9300 . ?
C23 C24 1.370(8) . ?
C24 C25 1.377(8) . ?
C25 C26 1.361(7) . ?
C26 H26A 0.9300 . ?
C27 C32 1.392(7) . ?
C27 C28 1.398(7) . ?
C28 C29 1.372(7) . ?
C28 H28A 0.9300 . ?
C29 C30 1.374(9) . ?
C30 C31 1.386(8) . ?
C31 C32 1.371(7) . ?
C32 H32A 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
C1 S1 C4 90.4(5) . . ?
C3 C4 S1 115.5(9) . . ?
C3 C4 H4A 122.3 . . ?
S1 C4 H4A 122.3 . . ?
C3 S1' C4' 89.8(9) . . ?
C1 C4' S1' 116.8(14) . . ?
C1 C4' H4B 121.6 . . ?
S1' C4' H4B 121.6 . . ?
C20 S2 C17 90.5(6) . . ?
C19 C20 S2 115.2(10) . . ?
C19 C20 H20A 122.4 . . ?
S2 C20 H20A 122.4 . . ?
C19 S2' C20' 92.1(13) . . ?
C17 C20' S2' 113.6(19) . . ?
C17 C20' H20B 123.2 . . ?
S2' C20' H20B 123.2 . . ?
C4' C1 C2 108.8(8) . . ?
C4' C1 C5 124.8(8) . . ?
C2 C1 C5 126.4(4) . . ?
C2 C1 S1 110.7(3) . . ?
C5 C1 S1 122.8(4) . . ?
C1 C2 C3 114.0(4) . . ?
C1 C2 H2A 123.0 . . ?
C3 C2 H2A 123.0 . . ?
C4 C3 C2 109.4(6) . . ?
C4 C3 C11 125.1(6) . . ?
C2 C3 C11 125.5(4) . . ?
C2 C3 S1' 110.5(4) . . ?
C11 C3 S1' 124.0(4) . . ?
C10 C5 C6 117.7(5) . . ?
C10 C5 C1 121.5(5) . . ?
C6 C5 C1 120.8(4) . . ?
C7 C6 C5 120.2(5) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
F1 C7 C8 118.9(5) . . ?
F1 C7 C6 119.0(5) . . ?
C8 C7 C6 122.1(5) . . ?
F2 C8 C7 120.5(5) . . ?
F2 C8 C9 122.1(5) . . ?
C7 C8 C9 117.4(5) . . ?
F3 C9 C10 121.0(6) . . ?
F3 C9 C8 117.5(5) . . ?
C10 C9 C8 121.5(5) . . ?
C9 C10 C5 121.1(5) . . ?
C9 C10 H10A 119.5 . . ?
C5 C10 H10A 119.5 . . ?
C12 C11 C16 118.1(4) . . ?
C12 C11 C3 121.0(4) . . ?
C16 C11 C3 120.9(4) . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
F4 C13 C12 120.5(5) . . ?
F4 C13 C14 118.5(4) . . ?
C12 C13 C14 121.0(5) . . ?
F5 C14 C15 121.9(5) . . ?
F5 C14 C13 119.4(5) . . ?
C15 C14 C13 118.7(5) . . ?
F6 C15 C14 118.6(5) . . ?
F6 C15 C16 119.5(5) . . ?
C14 C15 C16 121.9(5) . . ?
C15 C16 C11 119.8(5) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?
C20' C17 C18 110.3(9) . . ?
C20' C17 C21 122.7(9) . . ?
C18 C17 C21 127.0(4) . . ?
C18 C17 S2 110.3(3) . . ?
C21 C17 S2 122.6(4) . . ?
C17 C18 C19 113.5(4) . . ?
C17 C18 H18A 123.3 . . ?
C19 C18 H18A 123.3 . . ?
C20 C19 C18 110.5(6) . . ?
C20 C19 C27 124.5(7) . . ?
C18 C19 C27 124.9(4) . . ?
C18 C19 S2' 110.5(5) . . ?
C27 C19 S2' 124.6(5) . . ?
C22 C21 C26 118.3(4) . . ?
C22 C21 C17 121.1(4) . . ?
C26 C21 C17 120.6(4) . . ?
C23 C22 C21 119.6(5) . . ?
C23 C22 H22A 120.2 . . ?
C21 C22 H22A 120.2 . . ?
F7 C23 C22 119.4(5) . . ?
F7 C23 C24 118.5(5) . . ?
C22 C23 C24 122.1(5) . . ?
F8 C24 C25 120.6(5) . . ?
F8 C24 C23 121.3(5) . . ?
C25 C24 C23 118.0(5) . . ?
F9 C25 C26 119.1(5) . . ?
F9 C25 C24 118.5(5) . . ?
C26 C25 C24 122.3(5) . . ?
C25 C26 C21 119.7(5) . . ?
C25 C26 H26A 120.1 . . ?
C21 C26 H26A 120.1 . . ?
C32 C27 C28 118.3(5) . . ?
C32 C27 C19 120.6(4) . . ?
C28 C27 C19 121.1(5) . . ?
C29 C28 C27 119.9(5) . . ?
C29 C28 H28A 120.0 . . ?
C27 C28 H28A 120.0 . . ?
F10 C29 C30 117.9(5) . . ?
F10 C29 C28 120.2(6) . . ?
C30 C29 C28 121.8(5) . . ?
F11 C30 C29 121.3(5) . . ?
F11 C30 C31 120.3(5) . . ?
C29 C30 C31 118.3(5) . . ?
F12 C31 C32 120.6(5) . . ?
F12 C31 C30 118.5(5) . . ?
C32 C31 C30 120.9(5) . . ?
C31 C32 C27 120.7(5) . . ?
C31 C32 H32A 119.6 . . ?
C27 C32 H32A 119.6 . . ?

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.098

