# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx
#TrackingRef 'web_deposit_cif_file_0_LiuYing_1355708768.shelx.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H10 F4 S4'
_chemical_formula_weight         526.58

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   3.8195(6)
_cell_length_b                   12.4465(14)
_cell_length_c                   21.229(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.170(8)
_cell_angle_gamma                90.00
_cell_volume                     1008.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3444
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9025
_exptl_absorpt_correction_T_max  0.9399
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 14.22
_diffrn_reflns_number            12663
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.86
_reflns_number_total             2377
_reflns_number_gt                2045
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'

_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)+(0.0451P)²+0.0749P] 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         2377
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.76159(10) 0.74224(3) 0.273404(17) 0.01515(11) Uani 1 1 d . . .
S2 S 0.48769(10) 0.69483(3) 0.134191(17) 0.01403(11) Uani 1 1 d . . .
F1 F 0.1567(3) 0.70970(7) 0.01788(4) 0.0260(2) Uani 1 1 d . . .
F2 F -0.1290(3) 0.65087(7) -0.08937(4) 0.0267(2) Uani 1 1 d . . .
C1 C 0.6969(4) 0.63448(12) 0.32573(7) 0.0143(3) Uani 1 1 d . . .
C2 C 0.7879(4) 0.63438(12) 0.38980(7) 0.0174(3) Uani 1 1 d . . .
H2 H 0.8981 0.6949 0.4093 0.021 Uiso 1 1 calc R . .
C3 C 0.7131(4) 0.54341(13) 0.42439(7) 0.0186(3) Uani 1 1 d . . .
H3 H 0.7710 0.5418 0.4683 0.022 Uiso 1 1 calc R . .
C4 C 0.5532(4) 0.45375(13) 0.39559(7) 0.0187(3) Uani 1 1 d . . .
H4 H 0.5037 0.3923 0.4202 0.022 Uiso 1 1 calc R . .
C5 C 0.4664(4) 0.45365(12) 0.33163(7) 0.0158(3) Uani 1 1 d . . .
H5 H 0.3600 0.3923 0.3124 0.019 Uiso 1 1 calc R . .
C6 C 0.5374(4) 0.54502(12) 0.29568(7) 0.0136(3) Uani 1 1 d . . .
C7 C 0.4692(4) 0.56555(12) 0.22929(7) 0.0131(3) Uani 1 1 d . . .
C8 C 0.5779(4) 0.66668(12) 0.21214(7) 0.0135(3) Uani 1 1 d . . .
C9 C 0.3124(4) 0.50801(12) 0.17785(7) 0.0137(3) Uani 1 1 d . . .
H9 H 0.2240 0.4370 0.1811 0.016 Uiso 1 1 calc R . .
C10 C 0.3024(4) 0.56651(11) 0.12273(7) 0.0130(3) Uani 1 1 d . . .
C11 C 0.1554(4) 0.53360(11) 0.06092(7) 0.0129(3) Uani 1 1 d . . .
C12 C 0.0825(4) 0.60429(12) 0.01079(7) 0.0155(3) Uani 1 1 d . . .
C13 C -0.0662(4) 0.57278(12) -0.04636(7) 0.0152(3) 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 C8 1.7318(15) . ?
S1 C1 1.7649(15) . ?
S2 C8 1.7137(15) . ?
S2 C10 1.7600(15) . ?
F1 C12 1.3495(17) . ?
F2 C13 1.3489(16) . ?
C1 C2 1.391(2) . ?
C1 C6 1.410(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.4463(19) . ?
C7 C8 1.379(2) . ?
C7 C9 1.4194(19) . ?
C9 C10 1.377(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.466(2) . ?
C11 C13 1.399(2) 3_565 ?
C11 C12 1.401(2) . ?
C12 C13 1.377(2) . ?
C13 C11 1.399(2) 3_565 ?

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
C8 S1 C1 89.87(7) . . ?
C8 S2 C10 90.74(7) . . ?
C2 C1 C6 121.96(14) . . ?
C2 C1 S1 125.48(12) . . ?
C6 C1 S1 112.56(11) . . ?
C3 C2 C1 118.04(14) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 120.98(14) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.83(14) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.26(14) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.91(14) . . ?
C5 C6 C7 129.98(14) . . ?
C1 C6 C7 111.11(13) . . ?
C8 C7 C9 112.33(13) . . ?
C8 C7 C6 111.95(13) . . ?
C9 C7 C6 135.71(14) . . ?
C7 C8 S2 112.96(11) . . ?
C7 C8 S1 114.52(11) . . ?
S2 C8 S1 132.46(9) . . ?
C10 C9 C7 112.59(13) . . ?
C10 C9 H9 123.7 . . ?
C7 C9 H9 123.7 . . ?
C9 C10 C11 127.59(14) . . ?
C9 C10 S2 111.36(11) . . ?
C11 C10 S2 121.04(11) . . ?
C13 C11 C12 112.76(13) 3_565 . ?
C13 C11 C10 122.96(13) 3_565 . ?
C12 C11 C10 124.27(13) . . ?
F1 C12 C13 116.94(13) . . ?
F1 C12 C11 119.41(13) . . ?
C13 C12 C11 123.64(13) . . ?
F2 C13 C12 116.61(13) . . ?
F2 C13 C11 119.80(13) . 3_565 ?
C12 C13 C11 123.59(14) . 3_565 ?

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
C8 S1 C1 C2 179.88(14) . . . . ?
C8 S1 C1 C6 -0.30(11) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
S1 C1 C2 C3 178.93(11) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 -179.08(14) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
S1 C1 C6 C5 -179.34(11) . . . . ?
C2 C1 C6 C7 179.92(13) . . . . ?
S1 C1 C6 C7 0.10(15) . . . . ?
C5 C6 C7 C8 179.60(15) . . . . ?
C1 C6 C7 C8 0.23(18) . . . . ?
C5 C6 C7 C9 1.0(3) . . . . ?
C1 C6 C7 C9 -178.32(16) . . . . ?
C9 C7 C8 S2 0.86(17) . . . . ?
C6 C7 C8 S2 -178.04(10) . . . . ?
C9 C7 C8 S1 178.43(10) . . . . ?
C6 C7 C8 S1 -0.48(17) . . . . ?
C10 S2 C8 C7 -0.82(12) . . . . ?
C10 S2 C8 S1 -177.82(12) . . . . ?
C1 S1 C8 C7 0.45(12) . . . . ?
C1 S1 C8 S2 177.41(12) . . . . ?
C8 C7 C9 C10 -0.42(19) . . . . ?
C6 C7 C9 C10 178.13(15) . . . . ?
C7 C9 C10 C11 -178.95(13) . . . . ?
C7 C9 C10 S2 -0.20(16) . . . . ?
C8 S2 C10 C9 0.57(11) . . . . ?
C8 S2 C10 C11 179.42(12) . . . . ?
C9 C10 C11 C13 -13.7(2) . . . 3_565 ?
S2 C10 C11 C13 167.64(12) . . . 3_565 ?
C9 C10 C11 C12 164.93(15) . . . . ?
S2 C10 C11 C12 -13.7(2) . . . . ?
C13 C11 C12 F1 -179.66(13) 3_565 . . . ?
C10 C11 C12 F1 1.6(2) . . . . ?
C13 C11 C12 C13 1.0(3) 3_565 . . . ?
C10 C11 C12 C13 -177.79(14) . . . . ?
F1 C12 C13 F2 -1.1(2) . . . . ?
C11 C12 C13 F2 178.25(13) . . . . ?
F1 C12 C13 C11 179.54(14) . . . 3_565 ?
C11 C12 C13 C11 -1.1(3) . . . 3_565 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 915956'
