# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_newc
_database_code_depnum_ccdc_archive 'CCDC 1474460'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H6 F26 S2'
_chemical_formula_weight         876.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   53.119(8)
_cell_length_b                   5.8356(6)
_cell_length_c                   9.0022(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.343(15)
_cell_angle_gamma                90.00
_cell_volume                     2778.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1664
_cell_measurement_theta_min      4.9300
_cell_measurement_theta_max      73.6025


_exptl_crystal_description       'triangular shard'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.095
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    3.632
_exptl_absorpt_correction_T_min  0.63507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9621
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_h_max       65
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.02
_diffrn_reflns_theta_max         73.76
_reflns_number_total             2742
_reflns_number_gt                1755
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL

_refine_special_details          
;
Large thermal parameters for terminal CF3 group. SIMU, DELU and ISOR
used to damp down the motion. 

Attempts to model this as disorder
were unsatisfactory - different parts of the F atoms refined to give same
positions. Thus the current model was adopted. 

 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 > 2σ(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)+(0.0926P)²+2.8229P] 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         2742
_refine_ls_number_parameters     244
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1630
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.080
_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 0.72710(2) 0.53770(18) 0.44787(13) 0.0325(3) Uani 1 1 d . . .
F1 F 0.65077(5) 0.1994(5) 0.8925(3) 0.0423(7) Uani 1 1 d . . .
F2 F 0.64953(5) 0.5281(4) 0.7738(3) 0.0403(7) Uani 1 1 d . . .
F3 F 0.62792(5) -0.0150(4) 0.6561(4) 0.0424(7) Uani 1 1 d . . .
F4 F 0.63025(5) 0.2889(5) 0.5173(3) 0.0462(8) Uani 1 1 d . . .
F5 F 0.60109(5) 0.2560(6) 0.8487(4) 0.0536(8) Uani 1 1 d . . .
F6 F 0.60119(5) 0.5298(5) 0.6855(4) 0.0541(9) Uani 1 1 d . . .
F7 F 0.57741(5) -0.0262(5) 0.6474(4) 0.0565(9) Uani 1 1 d . . .
F8 F 0.58067(5) 0.2199(6) 0.4695(4) 0.0573(9) Uani 1 1 d . . .
F9 F 0.55088(6) 0.2957(8) 0.7942(4) 0.0809(13) Uani 1 1 d . . .
F10 F 0.55268(6) 0.5269(5) 0.6077(6) 0.0775(14) Uani 1 1 d . . .
F11 F 0.52689(7) -0.0156(7) 0.6090(7) 0.0957(16) Uani 1 1 d U . .
F12 F 0.50890(6) 0.3092(6) 0.6027(5) 0.0711(11) Uani 1 1 d U . .
F13 F 0.52965(7) 0.2045(10) 0.4249(5) 0.0959(15) Uani 1 1 d U . .
C1 C 0.74767(8) 0.1536(7) 0.5402(5) 0.0315(10) Uani 1 1 d . . .
C2 C 0.72354(8) 0.1514(7) 0.5978(5) 0.0303(10) Uani 1 1 d . . .
C3 C 0.71012(8) 0.3550(7) 0.5558(5) 0.0303(10) Uani 1 1 d . . .
C4 C 0.68646(8) 0.3997(8) 0.6037(5) 0.0323(10) Uani 1 1 d . . .
H4 H 0.6776 0.5363 0.5747 0.039 Uiso 1 1 calc R . .
C5 C 0.67615(8) 0.2410(7) 0.6943(5) 0.0312(10) Uani 1 1 d . . .
C6 C 0.68876(8) 0.0355(8) 0.7341(5) 0.0343(10) Uani 1 1 d . . .
H6 H 0.6810 -0.0735 0.7937 0.041 Uiso 1 1 calc R . .
C7 C 0.71219(8) -0.0098(7) 0.6880(5) 0.0309(10) Uani 1 1 d . . .
H7 H 0.7207 -0.1483 0.7166 0.037 Uiso 1 1 calc R . .
C8 C 0.65152(8) 0.2963(8) 0.7552(5) 0.0335(10) Uani 1 1 d . . .
C9 C 0.62774(8) 0.2146(8) 0.6564(5) 0.0330(10) Uani 1 1 d . . .
C10 C 0.60206(8) 0.3026(8) 0.7032(6) 0.0345(10) Uani 1 1 d . . .
C11 C 0.57842(8) 0.1965(8) 0.6143(6) 0.0361(11) Uani 1 1 d . . .
C12 C 0.55298(9) 0.3079(9) 0.6487(7) 0.0446(12) Uani 1 1 d U . .
C13 C 0.52923(9) 0.1965(10) 0.5695(8) 0.0511(13) Uani 1 1 d U . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.740(4) 7_656 ?
S1 C3 1.748(4) . ?
F1 C8 1.363(5) . ?
F2 C8 1.368(5) . ?
F3 C9 1.340(5) . ?
F4 C9 1.344(5) . ?
F5 C10 1.343(6) . ?
F6 C10 1.336(5) . ?
F7 C11 1.335(5) . ?
F8 C11 1.328(6) . ?
F9 C12 1.327(7) . ?
F10 C12 1.330(6) . ?
F11 C13 1.297(7) . ?
F12 C13 1.322(6) . ?
F13 C13 1.305(7) . ?
C1 C1 1.373(9) 7_656 ?
C1 C2 1.427(6) . ?
C1 S1 1.740(4) 7_656 ?
C2 C7 1.414(6) . ?
C2 C3 1.419(6) . ?
C3 C4 1.391(6) . ?
C4 C5 1.380(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(6) . ?
C5 C8 1.500(6) . ?
C6 C7 1.374(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.551(6) . ?
C9 C10 1.552(6) . ?
C10 C11 1.554(6) . ?
C11 C12 1.556(6) . ?
C12 C13 1.534(7) . ?

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 C3 90.5(2) 7_656 . ?
C1 C1 C2 114.3(5) 7_656 . ?
C1 C1 S1 112.5(5) 7_656 7_656 ?
C2 C1 S1 133.2(3) . 7_656 ?
C7 C2 C3 118.7(4) . . ?
C7 C2 C1 131.3(4) . . ?
C3 C2 C1 110.0(4) . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 S1 125.9(3) . . ?
C2 C3 S1 112.7(3) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 C8 118.7(4) . . ?
C6 C5 C8 120.1(4) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 119.5(4) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
F1 C8 F2 106.9(4) . . ?
F1 C8 C5 110.0(4) . . ?
F2 C8 C5 109.7(4) . . ?
F1 C8 C9 107.5(4) . . ?
F2 C8 C9 107.8(3) . . ?
C5 C8 C9 114.6(4) . . ?
F3 C9 F4 108.7(4) . . ?
F3 C9 C8 107.6(4) . . ?
F4 C9 C8 106.8(4) . . ?
F3 C9 C10 109.7(4) . . ?
F4 C9 C10 108.2(4) . . ?
C8 C9 C10 115.6(4) . . ?
F6 C10 F5 108.3(4) . . ?
F6 C10 C9 108.5(4) . . ?
F5 C10 C9 108.2(4) . . ?
F6 C10 C11 108.5(4) . . ?
F5 C10 C11 108.6(4) . . ?
C9 C10 C11 114.6(4) . . ?
F8 C11 F7 109.2(4) . . ?
F8 C11 C10 108.8(4) . . ?
F7 C11 C10 108.7(4) . . ?
F8 C11 C12 108.1(4) . . ?
F7 C11 C12 108.0(4) . . ?
C10 C11 C12 114.0(4) . . ?
F9 C12 F10 109.0(5) . . ?
F9 C12 C13 107.1(5) . . ?
F10 C12 C13 106.9(4) . . ?
F9 C12 C11 109.2(4) . . ?
F10 C12 C11 109.5(4) . . ?
C13 C12 C11 115.0(5) . . ?
F11 C13 F13 108.6(6) . . ?
F11 C13 F12 108.2(5) . . ?
F13 C13 F12 107.3(5) . . ?
F11 C13 C12 111.9(5) . . ?
F13 C13 C12 111.0(5) . . ?
F12 C13 C12 109.8(5) . . ?

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
C1 C1 C2 C7 -177.9(5) 7_656 . . . ?
S1 C1 C2 C7 1.4(8) 7_656 . . . ?
C1 C1 C2 C3 0.1(7) 7_656 . . . ?
S1 C1 C2 C3 179.3(4) 7_656 . . . ?
C7 C2 C3 C4 1.1(6) . . . . ?
C1 C2 C3 C4 -177.1(4) . . . . ?
C7 C2 C3 S1 178.7(3) . . . . ?
C1 C2 C3 S1 0.5(5) . . . . ?
C1 S1 C3 C4 176.8(4) 7_656 . . . ?
C1 S1 C3 C2 -0.7(3) 7_656 . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
S1 C3 C4 C5 -177.1(3) . . . . ?
C3 C4 C5 C6 -1.9(7) . . . . ?
C3 C4 C5 C8 175.6(4) . . . . ?
C4 C5 C6 C7 2.3(7) . . . . ?
C8 C5 C6 C7 -175.2(4) . . . . ?
C5 C6 C7 C2 -0.8(7) . . . . ?
C3 C2 C7 C6 -0.8(6) . . . . ?
C1 C2 C7 C6 177.0(4) . . . . ?
C4 C5 C8 F1 -147.6(4) . . . . ?
C6 C5 C8 F1 29.9(6) . . . . ?
C4 C5 C8 F2 -30.4(6) . . . . ?
C6 C5 C8 F2 147.2(4) . . . . ?
C4 C5 C8 C9 91.1(5) . . . . ?
C6 C5 C8 C9 -91.4(5) . . . . ?
F1 C8 C9 F3 -56.3(5) . . . . ?
F2 C8 C9 F3 -171.2(4) . . . . ?
C5 C8 C9 F3 66.3(5) . . . . ?
F1 C8 C9 F4 -172.8(3) . . . . ?
F2 C8 C9 F4 72.3(5) . . . . ?
C5 C8 C9 F4 -50.2(5) . . . . ?
F1 C8 C9 C10 66.7(5) . . . . ?
F2 C8 C9 C10 -48.2(5) . . . . ?
C5 C8 C9 C10 -170.6(4) . . . . ?
F3 C9 C10 F6 -172.7(4) . . . . ?
F4 C9 C10 F6 -54.3(5) . . . . ?
C8 C9 C10 F6 65.4(5) . . . . ?
F3 C9 C10 F5 70.0(5) . . . . ?
F4 C9 C10 F5 -171.5(4) . . . . ?
C8 C9 C10 F5 -51.9(5) . . . . ?
F3 C9 C10 C11 -51.3(5) . . . . ?
F4 C9 C10 C11 67.1(5) . . . . ?
C8 C9 C10 C11 -173.3(4) . . . . ?
F6 C10 C11 F8 69.3(5) . . . . ?
F5 C10 C11 F8 -173.2(4) . . . . ?
C9 C10 C11 F8 -52.1(5) . . . . ?
F6 C10 C11 F7 -171.9(4) . . . . ?
F5 C10 C11 F7 -54.4(5) . . . . ?
C9 C10 C11 F7 66.7(5) . . . . ?
F6 C10 C11 C12 -51.4(6) . . . . ?
F5 C10 C11 C12 66.0(5) . . . . ?
C9 C10 C11 C12 -172.8(4) . . . . ?
F8 C11 C12 F9 -177.2(4) . . . . ?
F7 C11 C12 F9 64.9(5) . . . . ?
C10 C11 C12 F9 -56.0(6) . . . . ?
F8 C11 C12 F10 -57.9(6) . . . . ?
F7 C11 C12 F10 -175.9(4) . . . . ?
C10 C11 C12 F10 63.2(6) . . . . ?
F8 C11 C12 C13 62.4(6) . . . . ?
F7 C11 C12 C13 -55.6(6) . . . . ?
C10 C11 C12 C13 -176.4(4) . . . . ?
F9 C12 C13 F11 -59.5(6) . . . . ?
F10 C12 C13 F11 -176.2(5) . . . . ?
C11 C12 C13 F11 62.0(7) . . . . ?
F9 C12 C13 F13 179.1(5) . . . . ?
F10 C12 C13 F13 62.4(6) . . . . ?
C11 C12 C13 F13 -59.4(7) . . . . ?
F9 C12 C13 F12 60.6(6) . . . . ?
F10 C12 C13 F12 -56.1(7) . . . . ?
C11 C12 C13 F12 -177.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.101
