# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1026641'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H14 F10 S2'
_chemical_formula_sum            'C38 H14 F10 S2'
_chemical_formula_weight         724.61

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.862(3)
_cell_length_b                   7.7560(16)
_cell_length_c                   27.693(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2977.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6653
_cell_measurement_theta_min      1.4690
_cell_measurement_theta_max      25.3507

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5647
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14172
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2615
_reflns_number_gt                2205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0196P)²+6.7028P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2615
_refine_ls_number_parameters     245
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.1122
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.378
_refine_ls_restrained_S_all      1.420
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5718(3) -0.0200(5) 0.36926(11) 0.0351(11) Uani 0.556(7) 1 d PDU A 1
C17 C 0.6546(12) 0.2589(16) 0.3875(3) 0.031(5) Uani 0.556(7) 1 d PDU A 1
H17 H 0.6823 0.3702 0.3840 0.038 Uiso 0.556(7) 1 calc PR A 1
S1' S 0.6690(4) 0.3144(7) 0.38661(15) 0.0388(14) Uani 0.444(7) 1 d PDU A 2
C17' C 0.5946(15) 0.0271(18) 0.3750(4) 0.045(8) Uani 0.444(7) 1 d PDU A 2
H17A H 0.5698 -0.0730 0.3596 0.054 Uiso 0.444(7) 1 calc PR A 2
F1 F 0.6526(3) 0.0561(4) 0.11842(12) 0.0564(10) Uani 1 1 d . . .
F2 F 0.6755(3) 0.1659(5) 0.02820(12) 0.0659(12) Uani 1 1 d . . .
F3 F 0.6137(3) 0.4845(6) 0.00176(12) 0.0692(12) Uani 1 1 d . . .
F4 F 0.5246(3) 0.6887(5) 0.06817(14) 0.0752(14) Uani 1 1 d . . .
F5 F 0.4987(3) 0.5765(4) 0.15883(12) 0.0512(10) Uani 1 1 d . . .
C1 C 0.6197(4) 0.2129(7) 0.10706(19) 0.0351(14) Uani 1 1 d . . .
C2 C 0.6322(4) 0.2686(8) 0.06076(19) 0.0412(15) Uani 1 1 d . . .
C3 C 0.6009(5) 0.4285(9) 0.0473(2) 0.0454(16) Uani 1 1 d . . .
C4 C 0.5570(5) 0.5311(8) 0.0810(2) 0.0467(16) Uani 1 1 d . . .
C5 C 0.5445(4) 0.4732(8) 0.1272(2) 0.0369(14) Uani 1 1 d . . .
C6 C 0.5771(3) 0.3126(7) 0.14288(18) 0.0271(12) Uani 1 1 d . . .
C7 C 0.5794(4) 0.2667(6) 0.19557(18) 0.0281(12) Uani 1 1 d . . .
C8 C 0.6710(4) 0.2673(6) 0.21713(19) 0.0277(12) Uani 1 1 d . . .
C9 C 0.7566(4) 0.3106(7) 0.19114(19) 0.0343(13) Uani 1 1 d . . .
H9 H 0.7511 0.3500 0.1588 0.041 Uiso 1 1 calc R . .
C10 C 0.8445(4) 0.2973(7) 0.2110(2) 0.0385(14) Uani 1 1 d . . .
H10 H 0.9000 0.3316 0.1933 0.046 Uiso 1 1 calc R . .
C11 C 0.8546(4) 0.2317(8) 0.2586(2) 0.0386(15) Uani 1 1 d . . .
H11 H 0.9172 0.2117 0.2714 0.046 Uiso 1 1 calc R . .
C12 C 0.7765(4) 0.1977(7) 0.2858(2) 0.0359(14) Uani 1 1 d . . .
H12 H 0.7847 0.1556 0.3177 0.043 Uiso 1 1 calc R . .
C13 C 0.6807(4) 0.2240(7) 0.26732(19) 0.0303(13) Uani 1 1 d . . .
C14 C 0.5984(4) 0.2156(6) 0.29650(18) 0.0276(12) Uani 1 1 d . A .
C15 C 0.5048(4) 0.2390(6) 0.27615(17) 0.0254(12) Uani 1 1 d . . .
C16 C 0.6114(4) 0.1757(6) 0.34783(18) 0.0296(12) Uani 1 1 d D . .
C18 C 0.6558(5) 0.1741(8) 0.4325(2) 0.0515(17) Uani 1 1 d D . .
H18 H 0.6814 0.2163 0.4620 0.062 Uiso 1 1 calc R A 1
C19 C 0.6139(5) 0.0236(9) 0.4249(2) 0.0500(17) Uani 1 1 d D A .
H19 H 0.6077 -0.0581 0.4503 0.060 Uiso 1 1 calc R B 1


_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 C19 1.682(6) . ?
S1 C16 1.720(5) . ?
C17 C16 1.407(9) . ?
C17 C18 1.408(9) . ?
C17 H17 0.9500 . ?
S1' C18 1.683(7) . ?
S1' C16 1.717(6) . ?
C17' C16 1.396(9) . ?
C17' C19 1.408(9) . ?
C17' H17A 0.9500 . ?
F1 C1 1.337(6) . ?
F2 C2 1.344(6) . ?
F3 C3 1.345(6) . ?
F4 C4 1.349(6) . ?
F5 C5 1.345(6) . ?
C1 C2 1.364(7) . ?
C1 C6 1.389(7) . ?
C2 C3 1.366(8) . ?
C3 C4 1.369(9) . ?
C4 C5 1.368(8) . ?
C5 C6 1.394(7) . ?
C6 C7 1.502(7) . ?
C7 C8 1.403(7) . ?
C7 C15 1.422(7) 3_655 ?
C8 C9 1.428(7) . ?
C8 C13 1.436(7) . ?
C9 C10 1.342(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.419(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.345(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.437(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(7) . ?
C14 C15 1.426(7) . ?
C14 C16 1.466(7) . ?
C15 C7 1.422(7) 3_655 ?
C15 C15 1.454(10) 3_655 ?
C18 C19 1.321(9) . ?
C18 H18 0.9500 . ?
C19 H19 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
C19 S1 C16 91.6(4) . . ?
C16 C17 C18 118.8(8) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C18 S1' C16 90.9(4) . . ?
C16 C17' C19 120.9(10) . . ?
C16 C17' H17A 119.6 . . ?
C19 C17' H17A 119.6 . . ?
F1 C1 C2 117.7(5) . . ?
F1 C1 C6 118.9(5) . . ?
C2 C1 C6 123.3(5) . . ?
F2 C2 C1 120.0(6) . . ?
F2 C2 C3 119.8(5) . . ?
C1 C2 C3 120.2(5) . . ?
F3 C3 C2 120.5(6) . . ?
F3 C3 C4 120.6(6) . . ?
C2 C3 C4 118.9(5) . . ?
F4 C4 C5 120.1(6) . . ?
F4 C4 C3 119.7(6) . . ?
C5 C4 C3 120.2(6) . . ?
F5 C5 C4 118.3(5) . . ?
F5 C5 C6 118.9(5) . . ?
C4 C5 C6 122.9(5) . . ?
C1 C6 C5 114.4(5) . . ?
C1 C6 C7 123.5(5) . . ?
C5 C6 C7 121.4(5) . . ?
C8 C7 C15 120.6(5) . 3_655 ?
C8 C7 C6 115.6(4) . . ?
C15 C7 C6 123.6(5) 3_655 . ?
C7 C8 C9 122.6(5) . . ?
C7 C8 C13 119.7(5) . . ?
C9 C8 C13 117.7(5) . . ?
C10 C9 C8 122.0(5) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 119.9(5) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.2(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C8 119.5(5) . . ?
C14 C13 C12 122.8(5) . . ?
C8 C13 C12 117.7(5) . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 C16 118.0(5) . . ?
C15 C14 C16 121.5(5) . . ?
C7 C15 C14 123.2(5) 3_655 . ?
C7 C15 C15 118.2(6) 3_655 3_655 ?
C14 C15 C15 118.5(6) . 3_655 ?
C17' C16 C17 91.6(7) . . ?
C17' C16 C14 132.5(6) . . ?
C17 C16 C14 135.5(6) . . ?
C17' C16 S1' 105.0(6) . . ?
C17 C16 S1' 13.4(5) . . ?
C14 C16 S1' 122.1(4) . . ?
C17' C16 S1 14.5(6) . . ?
C17 C16 S1 105.7(5) . . ?
C14 C16 S1 118.8(4) . . ?
S1' C16 S1 119.1(4) . . ?
C19 C18 C17 105.4(7) . . ?
C19 C18 S1' 120.0(5) . . ?
C17 C18 S1' 14.5(4) . . ?
C19 C18 H18 127.3 . . ?
C17 C18 H18 127.3 . . ?
S1' C18 H18 112.8 . . ?
C18 C19 C17' 102.9(8) . . ?
C18 C19 S1 118.4(5) . . ?
C17' C19 S1 16.0(6) . . ?
C18 C19 H19 120.8 . . ?
C17' C19 H19 136.2 . . ?
S1 C19 H19 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 0.6(9) . . . . ?
C6 C1 C2 F2 178.9(5) . . . . ?
F1 C1 C2 C3 -179.4(5) . . . . ?
C6 C1 C2 C3 -1.1(10) . . . . ?
F2 C2 C3 F3 -0.5(9) . . . . ?
C1 C2 C3 F3 179.5(6) . . . . ?
F2 C2 C3 C4 180.0(6) . . . . ?
C1 C2 C3 C4 0.0(10) . . . . ?
F3 C3 C4 F4 1.2(10) . . . . ?
C2 C3 C4 F4 -179.3(6) . . . . ?
F3 C3 C4 C5 -179.8(6) . . . . ?
C2 C3 C4 C5 -0.3(10) . . . . ?
F4 C4 C5 F5 0.7(9) . . . . ?
C3 C4 C5 F5 -178.3(6) . . . . ?
F4 C4 C5 C6 -179.3(5) . . . . ?
C3 C4 C5 C6 1.7(10) . . . . ?
F1 C1 C6 C5 -179.4(5) . . . . ?
C2 C1 C6 C5 2.4(8) . . . . ?
F1 C1 C6 C7 10.0(8) . . . . ?
C2 C1 C6 C7 -168.2(5) . . . . ?
F5 C5 C6 C1 177.4(5) . . . . ?
C4 C5 C6 C1 -2.7(8) . . . . ?
F5 C5 C6 C7 -11.8(8) . . . . ?
C4 C5 C6 C7 168.2(5) . . . . ?
C1 C6 C7 C8 65.1(7) . . . . ?
C5 C6 C7 C8 -104.9(6) . . . . ?
C1 C6 C7 C15 -120.5(6) . . . 3_655 ?
C5 C6 C7 C15 69.6(7) . . . 3_655 ?
C15 C7 C8 C9 -173.9(5) 3_655 . . . ?
C6 C7 C8 C9 0.7(7) . . . . ?
C15 C7 C8 C13 5.7(8) 3_655 . . . ?
C6 C7 C8 C13 -179.6(5) . . . . ?
C7 C8 C9 C10 -174.5(5) . . . . ?
C13 C8 C9 C10 5.8(8) . . . . ?
C8 C9 C10 C11 2.7(9) . . . . ?
C9 C10 C11 C12 -6.3(9) . . . . ?
C10 C11 C12 C13 1.0(9) . . . . ?
C7 C8 C13 C14 -12.8(8) . . . . ?
C9 C8 C13 C14 166.9(5) . . . . ?
C7 C8 C13 C12 169.6(5) . . . . ?
C9 C8 C13 C12 -10.7(7) . . . . ?
C11 C12 C13 C14 -170.0(5) . . . . ?
C11 C12 C13 C8 7.5(8) . . . . ?
C8 C13 C14 C15 3.9(8) . . . . ?
C12 C13 C14 C15 -178.6(5) . . . . ?
C8 C13 C14 C16 -178.3(4) . . . . ?
C12 C13 C14 C16 -0.9(8) . . . . ?
C13 C14 C15 C7 -166.9(5) . . . 3_655 ?
C16 C14 C15 C7 15.5(8) . . . 3_655 ?
C13 C14 C15 C15 11.5(6) . . . 3_655 ?
C16 C14 C15 C15 -166.2(3) . . . 3_655 ?
C19 C17' C16 C17 6.2(19) . . . . ?
C19 C17' C16 C14 180.0(9) . . . . ?
C19 C17' C16 S1' 7(2) . . . . ?
C19 C17' C16 S1 -159(5) . . . . ?
C18 C17 C16 C17' -4.2(16) . . . . ?
C18 C17 C16 C14 -177.6(8) . . . . ?
C18 C17 C16 S1' -180(5) . . . . ?
C18 C17 C16 S1 -0.5(15) . . . . ?
C13 C14 C16 C17' -105.0(14) . . . . ?
C15 C14 C16 C17' 72.7(15) . . . . ?
C13 C14 C16 C17 66.0(13) . . . . ?
C15 C14 C16 C17 -116.2(12) . . . . ?
C13 C14 C16 S1' 66.6(7) . . . . ?
C15 C14 C16 S1' -115.7(6) . . . . ?
C13 C14 C16 S1 -110.8(5) . . . . ?
C15 C14 C16 S1 66.9(6) . . . . ?
C18 S1' C16 C17' -4.4(11) . . . . ?
C18 S1' C16 C17 0(4) . . . . ?
C18 S1' C16 C14 -178.0(5) . . . . ?
C18 S1' C16 S1 -0.6(5) . . . . ?
C19 S1 C16 C17' 15(4) . . . . ?
C19 S1 C16 C17 -0.3(8) . . . . ?
C19 S1 C16 C14 177.4(5) . . . . ?
C19 S1 C16 S1' -0.1(5) . . . . ?
C16 C17 C18 C19 1.2(16) . . . . ?
C16 C17 C18 S1' 180(5) . . . . ?
C16 S1' C18 C19 1.4(7) . . . . ?
C16 S1' C18 C17 0(3) . . . . ?
C17 C18 C19 C17' 2.6(13) . . . . ?
S1' C18 C19 C17' 2.2(12) . . . . ?
C17 C18 C19 S1 -1.4(10) . . . . ?
S1' C18 C19 S1 -1.8(9) . . . . ?
C16 C17' C19 C18 -6(2) . . . . ?
C16 C17' C19 S1 161(5) . . . . ?
C16 S1 C19 C18 1.1(6) . . . . ?
C16 S1 C19 C17' -13(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.060
