# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1494114'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;
_audit_creation_date             2016-07-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H17 F3 O2 S2'
_chemical_formula_sum            'C18 H17 F3 O2 S2'
_chemical_formula_weight         386.44
_chemical_absolute_configuration unk
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y, z+1/2'
4 'x+1/2, -y, z'

_cell_length_a                   11.2567(7)
_cell_length_b                   11.6409(7)
_cell_length_c                   27.0758(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3548.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5832
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.475
_cell_measurement_theta_min      2.517
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_detailssadabs 
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0873 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.7859.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24851
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.50
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3554
_reflns_number_total             5803
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5803
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0902
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0605P)²+1.6653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1446
_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. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.28(11) 0.72(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C25(H25), C31(H31)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C32(H32), C33(H33),
  C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.25787(13) -0.40844(14) -0.02745(6) 0.0390(4) Uani 1 d . . .
S2 S -0.47931(17) -0.29363(18) 0.09652(8) 0.0612(6) Uani 1 d . . .
F1 F -0.4694(8) -0.0817(5) 0.0765(5) 0.206(5) Uani 1 d . . .
F2 F -0.6395(5) -0.1428(5) 0.0976(3) 0.142(3) Uani 1 d . . .
F3 F -0.5666(7) -0.1769(10) 0.0279(3) 0.214(6) Uani 1 d . . .
O1 O -0.1488(3) -0.4577(4) -0.00973(17) 0.0502(13) Uani 1 d . . .
O2 O -0.2549(4) -0.2931(3) -0.04685(18) 0.0527(13) Uani 1 d . . .
C1 C -0.0296(7) -0.2916(8) 0.1412(3) 0.064(2) Uani 1 d . . .
H1 H 0.0396 -0.2867 0.1599 0.076 Uiso 1 calc . . R
C2 C -0.0596(7) -0.2044(8) 0.1100(4) 0.066(3) Uani 1 d . . .
H2 H -0.0116 -0.1397 0.1072 0.079 Uiso 1 calc . . R
C3 C -0.1619(6) -0.2140(6) 0.0829(3) 0.052(2) Uani 1 d . . .
H3 H -0.1828 -0.1542 0.0618 0.062 Uiso 1 calc . . R
C4 C -0.2360(6) -0.3099(5) 0.0856(3) 0.0391(17) Uani 1 d . . .
C5 C -0.2061(6) -0.3986(6) 0.1185(3) 0.0421(17) Uani 1 d . . .
C6 C -0.1009(6) -0.3863(6) 0.1453(3) 0.0515(19) Uani 1 d . . .
H6 H -0.0784 -0.4449 0.1667 0.062 Uiso 1 calc . . R
C7 C -0.3482(6) -0.3099(5) 0.0563(2) 0.0439(19) Uani 1 d . . .
H7 H -0.3454 -0.2406 0.0358 0.053 Uiso 1 calc . . R
C8 C -0.3700(5) -0.4102(5) 0.0207(2) 0.0382(17) Uani 1 d . . .
H8 H -0.4445 -0.3913 0.0038 0.046 Uiso 1 calc . . R
C9 C -0.3896(6) -0.5296(5) 0.0422(3) 0.0416(17) Uani 1 d . . .
H9A H -0.3970 -0.5835 0.0150 0.050 Uiso 1 calc . . R
H9B H -0.4647 -0.5295 0.0598 0.050 Uiso 1 calc . . R
C10 C -0.2935(6) -0.5735(5) 0.0771(3) 0.051(2) Uani 1 d . . .
H10A H -0.3123 -0.6521 0.0861 0.061 Uiso 1 calc . . R
H10B H -0.2184 -0.5745 0.0596 0.061 Uiso 1 calc . . R
C11 C -0.2785(6) -0.5039(6) 0.1239(3) 0.053(2) Uani 1 d . . .
H11A H -0.3566 -0.4823 0.1358 0.063 Uiso 1 calc . . R
H11B H -0.2421 -0.5524 0.1488 0.063 Uiso 1 calc . . R
C12 C -0.3178(5) -0.5002(6) -0.0729(2) 0.0366(17) Uani 1 d . . .
C13 C -0.4202(6) -0.4675(6) -0.0977(3) 0.049(2) Uani 1 d . . .
H13 H -0.4556 -0.3969 -0.0912 0.059 Uiso 1 calc . . R
C14 C -0.4683(6) -0.5406(6) -0.1318(3) 0.056(2) Uani 1 d . . .
H14 H -0.5388 -0.5217 -0.1478 0.068 Uiso 1 calc . . R
C15 C -0.4112(7) -0.6431(6) -0.1424(3) 0.056(2) Uani 1 d . . .
H15 H -0.4422 -0.6910 -0.1667 0.067 Uiso 1 calc . . R
C16 C -0.3128(6) -0.6747(6) -0.1186(3) 0.0520(19) Uani 1 d . . .
H16 H -0.2775 -0.7449 -0.1259 0.062 Uiso 1 calc . . R
C17 C -0.2623(6) -0.6038(5) -0.0829(3) 0.0433(18) Uani 1 d . . .
H17 H -0.1934 -0.6253 -0.0664 0.052 Uiso 1 calc . . R
C18 C -0.5418(12) -0.1716(9) 0.0747(5) 0.107(4) Uani 1 d . . .
S3 S -0.18753(15) -0.19638(16) 0.25440(8) 0.0560(5) Uani 1 d . . .
S4 S 0.03417(13) -0.08753(14) 0.37931(6) 0.0386(4) Uani 1 d . . .
F4 F -0.2852(5) -0.3190(6) 0.3233(3) 0.149(3) Uani 1 d . . .
F5 F -0.3465(5) -0.3454(5) 0.2494(3) 0.129(2) Uani 1 d . . .
F6 F -0.1761(6) -0.4123(4) 0.2716(3) 0.143(3) Uani 1 d . . .
O3 O 0.0370(4) -0.2038(3) 0.39827(17) 0.0511(13) Uani 1 d . . .
O4 O 0.1432(3) -0.0390(4) 0.36198(16) 0.0493(13) Uani 1 d . . .
C19 C -0.1785(6) 0.0421(6) 0.4828(3) 0.057(2) Uani 1 d . . .
H19 H -0.2484 0.0212 0.4987 0.068 Uiso 1 calc . . R
C20 C -0.1240(7) 0.1448(6) 0.4942(3) 0.054(2) Uani 1 d . . .
H20 H -0.1575 0.1931 0.5177 0.065 Uiso 1 calc . . R
C21 C -0.0216(6) 0.1761(6) 0.4711(3) 0.055(2) Uani 1 d . . .
H21 H 0.0154 0.2450 0.4793 0.066 Uiso 1 calc . . R
C22 C 0.0266(5) 0.1064(6) 0.4360(3) 0.0445(18) Uani 1 d . . .
H22 H 0.0957 0.1281 0.4197 0.053 Uiso 1 calc . . R
C23 C -0.0280(5) 0.0029(5) 0.4249(2) 0.0311(15) Uani 1 d . . .
C24 C -0.1297(6) -0.0289(6) 0.4482(3) 0.0440(19) Uani 1 d . . .
H24 H -0.1658 -0.0985 0.4405 0.053 Uiso 1 calc . . R
C25 C -0.0773(5) -0.0847(5) 0.3320(2) 0.0340(16) Uani 1 d . . .
H25 H -0.1524 -0.1007 0.3489 0.041 Uiso 1 calc . . R
C26 C -0.0924(5) 0.0350(5) 0.3090(3) 0.0436(17) Uani 1 d . . .
H26A H -0.1676 0.0357 0.2914 0.052 Uiso 1 calc . . R
H26B H -0.0990 0.0900 0.3357 0.052 Uiso 1 calc . . R
C27 C 0.0017(6) 0.0781(6) 0.2740(3) 0.0472(19) Uani 1 d . . .
H27A H 0.0770 0.0801 0.2913 0.057 Uiso 1 calc . . R
H27B H -0.0178 0.1563 0.2646 0.057 Uiso 1 calc . . R
C28 C 0.0170(6) 0.0064(6) 0.2268(3) 0.0518(19) Uani 1 d . . .
H28A H -0.0610 -0.0142 0.2144 0.062 Uiso 1 calc . . R
H28B H 0.0553 0.0535 0.2019 0.062 Uiso 1 calc . . R
C29 C 0.0895(5) -0.1032(6) 0.2338(2) 0.0402(17) Uani 1 d . . .
C30 C 0.0548(5) -0.1885(5) 0.2664(2) 0.0352(16) Uani 1 d . . .
C31 C -0.0580(5) -0.1864(5) 0.2966(2) 0.0343(16) Uani 1 d . . .
H31 H -0.0582 -0.2563 0.3168 0.041 Uiso 1 calc . . R
C32 C 0.1928(6) -0.1178(6) 0.2064(3) 0.0485(18) Uani 1 d . . .
H32 H 0.2159 -0.0607 0.1844 0.058 Uiso 1 calc . . R
C33 C 0.2617(7) -0.2146(7) 0.2112(3) 0.061(2) Uani 1 d . . .
H33 H 0.3300 -0.2231 0.1922 0.073 Uiso 1 calc . . R
C34 C 0.2297(7) -0.2984(7) 0.2440(3) 0.056(2) Uani 1 d . . .
H34 H 0.2768 -0.3634 0.2478 0.067 Uiso 1 calc . . R
C35 C 0.1281(6) -0.2862(6) 0.2712(3) 0.052(2) Uani 1 d . . .
H35 H 0.1069 -0.3436 0.2933 0.062 Uiso 1 calc . . R
C36 C -0.2529(9) -0.3216(8) 0.2779(5) 0.089(3) Uani 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 O1 1.437(4) . ?
S1 O2 1.443(4) . ?
S1 C8 1.814(6) . ?
S1 C12 1.763(6) . ?
S2 C7 1.844(6) . ?
S2 C18 1.692(10) . ?
F1 C18 1.328(14) . ?
F2 C18 1.307(10) . ?
F3 C18 1.300(15) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(11) . ?
C1 C6 1.368(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(8) . ?
C4 C5 1.404(9) . ?
C4 C7 1.492(9) . ?
C5 C6 1.395(9) . ?
C5 C11 1.480(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.535(8) . ?
C8 H8 0.9800 . ?
C8 C9 1.523(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.512(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.388(8) . ?
C12 C17 1.385(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.333(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.392(9) . ?
C17 H17 0.9300 . ?
S3 C31 1.856(6) . ?
S3 C36 1.753(10) . ?
S4 O3 1.448(4) . ?
S4 O4 1.430(4) . ?
S4 C23 1.767(6) . ?
S4 C25 1.793(6) . ?
F4 C36 1.283(12) . ?
F5 C36 1.336(10) . ?
F6 C36 1.375(11) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(9) . ?
C19 C24 1.366(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.360(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.362(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(8) . ?
C23 C24 1.357(8) . ?
C24 H24 0.9300 . ?
C25 H25 0.9800 . ?
C25 C26 1.536(8) . ?
C25 C31 1.539(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.507(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.536(10) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.527(9) . ?
C29 C30 1.386(9) . ?
C29 C32 1.389(9) . ?
C30 C31 1.511(8) . ?
C30 C35 1.410(9) . ?
C31 H31 0.9800 . ?
C32 H32 0.9300 . ?
C32 C33 1.374(9) . ?
C33 H33 0.9300 . ?
C33 C34 1.368(10) . ?
C34 H34 0.9300 . ?
C34 C35 1.367(9) . ?
C35 H35 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
O1 S1 O2 118.2(3) . . ?
O1 S1 C8 110.5(3) . . ?
O1 S1 C12 108.5(3) . . ?
O2 S1 C8 106.8(3) . . ?
O2 S1 C12 108.6(3) . . ?
C12 S1 C8 103.2(3) . . ?
C18 S2 C7 102.3(5) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.3(8) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(8) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.6(8) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 118.6(6) . . ?
C3 C4 C7 118.5(6) . . ?
C5 C4 C7 122.7(6) . . ?
C4 C5 C11 122.6(6) . . ?
C6 C5 C4 117.2(6) . . ?
C6 C5 C11 120.1(7) . . ?
C1 C6 C5 122.6(7) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
S2 C7 H7 106.0 . . ?
C4 C7 S2 111.3(5) . . ?
C4 C7 H7 106.0 . . ?
C4 C7 C8 118.0(5) . . ?
C8 C7 S2 108.7(4) . . ?
C8 C7 H7 106.0 . . ?
S1 C8 H8 105.0 . . ?
C7 C8 S1 109.4(4) . . ?
C7 C8 H8 105.0 . . ?
C9 C8 S1 112.7(4) . . ?
C9 C8 C7 118.5(5) . . ?
C9 C8 H8 105.0 . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C8 C9 C10 116.1(5) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.8(6) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C5 C11 C10 115.1(6) . . ?
C5 C11 H11A 108.5 . . ?
C5 C11 H11B 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 S1 119.3(5) . . ?
C17 C12 S1 119.5(5) . . ?
C17 C12 C13 121.2(6) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.1(6) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(7) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(7) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(6) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 118.0(6) . . ?
C12 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
F1 C18 S2 113.2(11) . . ?
F2 C18 S2 113.5(8) . . ?
F2 C18 F1 107.3(10) . . ?
F3 C18 S2 113.0(10) . . ?
F3 C18 F1 101.8(11) . . ?
F3 C18 F2 107.2(12) . . ?
C36 S3 C31 99.1(4) . . ?
O3 S4 C23 108.5(3) . . ?
O3 S4 C25 106.6(3) . . ?
O4 S4 O3 117.8(3) . . ?
O4 S4 C23 109.5(3) . . ?
O4 S4 C25 111.0(3) . . ?
C23 S4 C25 102.2(3) . . ?
C20 C19 H19 120.0 . . ?
C24 C19 H19 120.0 . . ?
C24 C19 C20 119.9(7) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.5(7) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(6) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(6) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 S4 119.6(5) . . ?
C24 C23 S4 119.7(5) . . ?
C24 C23 C22 120.7(6) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 C19 119.5(6) . . ?
C23 C24 H24 120.2 . . ?
S4 C25 H25 105.4 . . ?
C26 C25 S4 112.6(4) . . ?
C26 C25 H25 105.4 . . ?
C26 C25 C31 117.4(5) . . ?
C31 C25 S4 109.4(4) . . ?
C31 C25 H25 105.4 . . ?
C25 C26 H26A 107.7 . . ?
C25 C26 H26B 107.7 . . ?
H26A C26 H26B 107.1 . . ?
C27 C26 C25 118.6(5) . . ?
C27 C26 H26A 107.7 . . ?
C27 C26 H26B 107.7 . . ?
C26 C27 H27A 108.6 . . ?
C26 C27 H27B 108.6 . . ?
C26 C27 C28 114.8(6) . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C27 C28 H28A 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 C27 114.3(6) . . ?
C29 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C30 C29 C28 121.8(6) . . ?
C30 C29 C32 119.2(6) . . ?
C32 C29 C28 118.9(6) . . ?
C29 C30 C31 124.8(6) . . ?
C29 C30 C35 118.1(6) . . ?
C35 C30 C31 117.1(6) . . ?
S3 C31 H31 106.9 . . ?
C25 C31 S3 108.7(4) . . ?
C25 C31 H31 106.9 . . ?
C30 C31 S3 109.0(4) . . ?
C30 C31 C25 117.9(5) . . ?
C30 C31 H31 106.9 . . ?
C29 C32 H32 119.2 . . ?
C33 C32 C29 121.5(7) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 120.1 . . ?
C34 C33 C32 119.8(7) . . ?
C34 C33 H33 120.1 . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.7(7) . . ?
C35 C34 H34 120.1 . . ?
C30 C35 H35 119.2 . . ?
C34 C35 C30 121.6(7) . . ?
C34 C35 H35 119.2 . . ?
F4 C36 S3 116.6(8) . . ?
F4 C36 F5 109.6(9) . . ?
F4 C36 F6 108.5(10) . . ?
F5 C36 S3 107.1(8) . . ?
F5 C36 F6 105.3(8) . . ?
F6 C36 S3 109.2(7) . . ?

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 C8 C9 C10 75.0(7) . . . . ?
S1 C12 C13 C14 -178.0(6) . . . . ?
S1 C12 C17 C16 179.3(5) . . . . ?
S2 C7 C8 S1 167.8(3) . . . . ?
S2 C7 C8 C9 -61.2(6) . . . . ?
O1 S1 C8 C7 79.6(5) . . . . ?
O1 S1 C8 C9 -54.4(5) . . . . ?
O1 S1 C12 C13 -176.3(5) . . . . ?
O1 S1 C12 C17 4.1(6) . . . . ?
O2 S1 C8 C7 -50.2(5) . . . . ?
O2 S1 C8 C9 175.8(4) . . . . ?
O2 S1 C12 C13 -46.6(6) . . . . ?
O2 S1 C12 C17 133.8(5) . . . . ?
C1 C2 C3 C4 -0.6(11) . . . . ?
C2 C1 C6 C5 -0.3(12) . . . . ?
C2 C3 C4 C5 1.8(10) . . . . ?
C2 C3 C4 C7 177.3(6) . . . . ?
C3 C4 C5 C6 -2.2(9) . . . . ?
C3 C4 C5 C11 -179.6(6) . . . . ?
C3 C4 C7 S2 -108.1(6) . . . . ?
C3 C4 C7 C8 125.1(6) . . . . ?
C4 C5 C6 C1 1.5(10) . . . . ?
C4 C5 C11 C10 59.1(9) . . . . ?
C4 C7 C8 S1 -64.2(7) . . . . ?
C4 C7 C8 C9 66.8(7) . . . . ?
C5 C4 C7 S2 67.2(7) . . . . ?
C5 C4 C7 C8 -59.5(8) . . . . ?
C6 C1 C2 C3 -0.2(12) . . . . ?
C6 C5 C11 C10 -118.3(7) . . . . ?
C7 S2 C18 F1 -58.2(12) . . . . ?
C7 S2 C18 F2 179.1(10) . . . . ?
C7 S2 C18 F3 56.8(11) . . . . ?
C7 C4 C5 C6 -177.5(6) . . . . ?
C7 C4 C5 C11 5.1(10) . . . . ?
C7 C8 C9 C10 -54.5(8) . . . . ?
C8 S1 C12 C13 66.5(6) . . . . ?
C8 S1 C12 C17 -113.1(5) . . . . ?
C8 C9 C10 C11 63.1(8) . . . . ?
C9 C10 C11 C5 -81.2(8) . . . . ?
C11 C5 C6 C1 179.0(7) . . . . ?
C12 S1 C8 C7 -164.5(4) . . . . ?
C12 S1 C8 C9 61.4(5) . . . . ?
C12 C13 C14 C15 -2.7(11) . . . . ?
C13 C12 C17 C16 -0.3(10) . . . . ?
C13 C14 C15 C16 2.8(12) . . . . ?
C14 C15 C16 C17 -1.6(12) . . . . ?
C15 C16 C17 C12 0.3(10) . . . . ?
C17 C12 C13 C14 1.6(10) . . . . ?
C18 S2 C7 C4 120.4(7) . . . . ?
C18 S2 C7 C8 -107.9(7) . . . . ?
S4 C23 C24 C19 -179.0(5) . . . . ?
S4 C25 C26 C27 74.1(7) . . . . ?
S4 C25 C31 S3 170.7(3) . . . . ?
S4 C25 C31 C30 -64.6(6) . . . . ?
O3 S4 C23 C22 133.6(5) . . . . ?
O3 S4 C23 C24 -47.3(6) . . . . ?
O3 S4 C25 C26 178.8(4) . . . . ?
O3 S4 C25 C31 -48.7(5) . . . . ?
O4 S4 C23 C22 3.7(6) . . . . ?
O4 S4 C23 C24 -177.2(5) . . . . ?
O4 S4 C25 C26 -51.7(5) . . . . ?
O4 S4 C25 C31 80.9(4) . . . . ?
C19 C20 C21 C22 1.0(11) . . . . ?
C20 C19 C24 C23 -0.5(11) . . . . ?
C20 C21 C22 C23 -1.3(11) . . . . ?
C21 C22 C23 S4 179.9(5) . . . . ?
C21 C22 C23 C24 0.8(10) . . . . ?
C22 C23 C24 C19 0.1(10) . . . . ?
C23 S4 C25 C26 65.0(5) . . . . ?
C23 S4 C25 C31 -162.5(4) . . . . ?
C24 C19 C20 C21 -0.1(11) . . . . ?
C25 S4 C23 C22 -114.0(5) . . . . ?
C25 S4 C23 C24 65.1(6) . . . . ?
C25 C26 C27 C28 62.4(8) . . . . ?
C26 C25 C31 S3 -59.3(6) . . . . ?
C26 C25 C31 C30 65.4(7) . . . . ?
C26 C27 C28 C29 -79.3(7) . . . . ?
C27 C28 C29 C30 59.7(8) . . . . ?
C27 C28 C29 C32 -120.4(7) . . . . ?
C28 C29 C30 C31 2.8(9) . . . . ?
C28 C29 C30 C35 -178.9(6) . . . . ?
C28 C29 C32 C33 179.9(6) . . . . ?
C29 C30 C31 S3 66.2(7) . . . . ?
C29 C30 C31 C25 -58.3(8) . . . . ?
C29 C30 C35 C34 -1.0(10) . . . . ?
C29 C32 C33 C34 -0.9(10) . . . . ?
C30 C29 C32 C33 -0.3(9) . . . . ?
C31 S3 C36 F4 60.1(9) . . . . ?
C31 S3 C36 F5 -176.7(8) . . . . ?
C31 S3 C36 F6 -63.2(8) . . . . ?
C31 C25 C26 C27 -54.3(8) . . . . ?
C31 C30 C35 C34 177.4(6) . . . . ?
C32 C29 C30 C31 -177.0(6) . . . . ?
C32 C29 C30 C35 1.2(9) . . . . ?
C32 C33 C34 C35 1.1(11) . . . . ?
C33 C34 C35 C30 -0.2(11) . . . . ?
C35 C30 C31 S3 -112.1(5) . . . . ?
C35 C30 C31 C25 123.4(6) . . . . ?
C36 S3 C31 C25 -109.0(6) . . . . ?
C36 S3 C31 C30 121.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.28(11)
2 0.72(11)

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1494115'
_audit_update_record             
;
2016-07-18 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;
_audit_creation_date             2016-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 F3 O2 S2'
_chemical_formula_sum            'C12 H13 F3 O2 S2'
_chemical_formula_weight         310.34
_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                   5.6786(6)
_cell_length_b                   8.4547(9)
_cell_length_c                   15.2755(16)
_cell_angle_alpha                95.353(8)
_cell_angle_beta                 96.231(8)
_cell_angle_gamma                102.129(8)
_cell_volume                     707.68(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1063
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.681
_cell_measurement_theta_min      2.482
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6401
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.479
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1403
_reflns_number_total             2475
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.1544
_refine_ls_R_factor_gt           0.0978
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.706
_refine_ls_shift/su_mean         0.038
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1871P)²+1.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2709
_refine_ls_wR_factor_ref         0.3262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-F6
 1.45 with sigma of 0.01
 F1-C12
 1.45 with sigma of 0.01
 C12-F3
 1.45 with sigma of 0.01
 F3-F6
 2.35 with sigma of 0.01
 F3-F1
 2.35 with sigma of 0.01
 C12-F8
 1.45 with sigma of 0.01
 F8-F6
 2.35 with sigma of 0.01
 F1-F8
 2.35 with sigma of 0.01
 F8-F3
 2.35 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
S1 \\sim S1A \\sim F1 \\sim F3 \\sim F6 \\sim F8 \\sim C11 \\sim C11A \\sim
C12: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.08
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.08
4. Others
 Fixed Sof: S1(0.5) S1A(0.5) F1(0.25) F2(0.25) F3(0.5) F4(0.5) F5(0.25)
 F6(0.25) F7(0.5) F8(0.5) H10(0.6) H10A(0.4) C11(0.4) H11A(0.4) H11B(0.4)
 C11A(0.6) H11C(0.6) H11D(0.6)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C10(H10A)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.4177(14) 0.6870(7) 0.2512(4) 0.0995(15) Uani 0.5 1 d . U P A 1
S1A S 0.1253(11) 0.6333(7) 0.3081(4) 0.0977(15) Uani 0.5 1 d . U P A 2
S2 S -0.2890(3) 0.02147(19) 0.13189(11) 0.0509(6) Uani 1 1 d . . . . .
F1 F 0.394(6) 0.724(2) 0.2719(9) 0.109(2) Uani 0.25 1 d D U P A 2
F2 F 0.593(5) 0.742(3) 0.3342(17) 0.117(2) Uani 0.25 1 d . U P . .
F3 F 0.528(2) 0.7233(14) 0.4233(7) 0.123(2) Uani 0.5 1 d D U P A 2
F4 F 0.472(3) 0.6232(17) 0.4337(9) 0.129(3) Uani 0.5 1 d . U P . .
F5 F 0.172(4) 0.667(3) 0.3884(17) 0.103(3) Uani 0.25 1 d . U P . .
F6 F 0.1429(19) 0.588(3) 0.3457(16) 0.104(2) Uani 0.25 1 d D U P A 1
F7 F 0.350(2) 0.4585(15) 0.3560(9) 0.114(3) Uani 0.5 1 d . U P A .
F8 F 0.499(2) 0.4930(13) 0.3219(8) 0.115(2) Uani 0.5 1 d D U P A 2
O1 O -0.5325(8) 0.0438(7) 0.1178(3) 0.0661(14) Uani 1 1 d . . . . .
O2 O -0.2472(10) -0.1384(6) 0.1074(4) 0.0766(16) Uani 1 1 d . . . . .
C1 C -0.1806(11) 0.0802(7) 0.2457(4) 0.0505(16) Uani 1 1 d . . . . .
C2 C -0.2955(14) 0.1746(10) 0.2954(5) 0.068(2) Uani 1 1 d . . . . .
H2 H -0.4285 0.2096 0.2694 0.082 Uiso 1 1 calc R . . . .
C3 C -0.2137(16) 0.2179(11) 0.3841(6) 0.077(2) Uani 1 1 d . . . . .
H3 H -0.2903 0.2833 0.4183 0.092 Uiso 1 1 calc R . . . .
C4 C -0.0241(19) 0.1661(12) 0.4214(5) 0.085(3) Uani 1 1 d . . . . .
H4 H 0.0259 0.1929 0.4819 0.102 Uiso 1 1 calc R . . . .
C5 C 0.0986(16) 0.0740(11) 0.3721(6) 0.081(2) Uani 1 1 d . . . . .
H5 H 0.2325 0.0410 0.3988 0.097 Uiso 1 1 calc R . . . .
C6 C 0.0201(13) 0.0306(9) 0.2816(5) 0.0649(19) Uani 1 1 d . . . . .
H6 H 0.1014 -0.0302 0.2466 0.078 Uiso 1 1 calc R . . . .
C7 C -0.0988(11) 0.1582(8) 0.0754(4) 0.0496(16) Uani 1 1 d . . . . .
H7A H 0.0651 0.1410 0.0859 0.060 Uiso 1 1 calc R . . . .
H7B H -0.1529 0.1326 0.0123 0.060 Uiso 1 1 calc R . . . .
C8 C -0.0916(11) 0.3347(8) 0.1015(4) 0.0478(15) Uani 1 1 d . . . . .
C9 C -0.2978(15) 0.4023(11) 0.0626(6) 0.079(2) Uani 1 1 d . . . . .
H9A H -0.2887 0.5085 0.0930 0.118 Uiso 1 1 calc GR . . . .
H9B H -0.4492 0.3315 0.0692 0.118 Uiso 1 1 calc GR . . . .
H9C H -0.2876 0.4103 0.0008 0.118 Uiso 1 1 calc GR . . . .
C10 C 0.0967(14) 0.4226(8) 0.1564(5) 0.065(2) Uani 1 1 d . . . . .
H10 H 0.2071 0.3652 0.1796 0.078 Uiso 0.6 1 calc R . P B 1
H10A H 0.2287 0.3769 0.1715 0.078 Uiso 0.4 1 calc R . P C 2
C11 C 0.104(8) 0.600(6) 0.196(3) 0.094(2) Uani 0.4 1 d . U P A 2
H11A H -0.0417 0.6309 0.1713 0.113 Uiso 0.4 1 calc R . P A 2
H11B H 0.2417 0.6721 0.1778 0.113 Uiso 0.4 1 calc R . P A 2
C11A C 0.154(5) 0.596(4) 0.185(2) 0.094(2) Uani 0.6 1 d . U P A 1
H11C H 0.0222 0.6186 0.2161 0.113 Uiso 0.6 1 calc R . P A 1
H11D H 0.1503 0.6505 0.1323 0.113 Uiso 0.6 1 calc R . P A 1
C12 C 0.3992(18) 0.6272(11) 0.3465(6) 0.1088(15) Uani 1 1 d D U . A 2


_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 F2 1.50(3) . ?
S1 C11A 1.70(3) . ?
S1A F1 1.73(3) . ?
S1A F5 1.22(2) . ?
S1A C11 1.69(4) . ?
S1A C12 1.615(12) . ?
S2 O1 1.431(5) . ?
S2 O2 1.443(5) . ?
S2 C1 1.768(7) . ?
S2 C7 1.764(7) . ?
F1 F2 1.37(3) . ?
F1 C12 1.466(9) . ?
F2 F3 1.46(3) . ?
F2 C12 1.35(2) . ?
F3 F4 0.874(15) . ?
F3 C12 1.398(8) . ?
F4 F7 1.714(19) . ?
F4 C12 1.356(17) . ?
F5 F6 0.86(2) . ?
F5 C12 1.58(2) . ?
F6 F7 1.77(2) . ?
F7 F8 1.045(15) . ?
F7 C12 1.418(15) . ?
F8 C12 1.410(8) . ?
C1 C2 1.361(10) . ?
C1 C6 1.372(9) . ?
C2 C3 1.374(11) . ?
C3 C4 1.336(12) . ?
C4 C5 1.375(13) . ?
C5 C6 1.395(11) . ?
C7 C8 1.499(9) . ?
C8 C9 1.498(9) . ?
C8 C10 1.325(10) . ?
C10 C11 1.56(4) . ?
C10 C11A 1.45(3) . ?

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
F2 S1 C11A 158.7(14) . . ?
F5 S1A F1 102.4(13) . . ?
F5 S1A C11 172(2) . . ?
F5 S1A C12 66.2(12) . . ?
C11 S1A F1 69.2(16) . . ?
C12 S1A F1 51.9(6) . . ?
C12 S1A C11 106.6(16) . . ?
O1 S2 O2 118.2(3) . . ?
O1 S2 C1 107.4(3) . . ?
O1 S2 C7 110.0(3) . . ?
O2 S2 C1 108.5(3) . . ?
O2 S2 C7 106.8(3) . . ?
C7 S2 C1 105.2(3) . . ?
F2 F1 S1A 113.2(14) . . ?
F2 F1 C12 56.8(12) . . ?
C12 F1 S1A 60.0(10) . . ?
F1 F2 F3 113(2) . . ?
C12 F2 F1 65.2(13) . . ?
C12 F2 F3 59.4(11) . . ?
F4 F3 F2 115.8(17) . . ?
F4 F3 C12 68.9(11) . . ?
C12 F3 F2 56.3(10) . . ?
F3 F4 F7 126.5(16) . . ?
F3 F4 C12 74.1(12) . . ?
C12 F4 F7 53.5(7) . . ?
S1A F5 C12 68.9(12) . . ?
F5 F6 F7 113(2) . . ?
F4 F7 F6 75.3(10) . . ?
F8 F7 F4 88.4(12) . . ?
F8 F7 C12 67.9(8) . . ?
C12 F7 F4 50.3(7) . . ?
F7 F8 C12 68.7(9) . . ?
C2 C1 S2 119.5(5) . . ?
C2 C1 C6 121.6(7) . . ?
C6 C1 S2 118.9(5) . . ?
C1 C2 C3 119.5(8) . . ?
C4 C3 C2 120.1(8) . . ?
C3 C4 C5 121.4(8) . . ?
C4 C5 C6 119.3(8) . . ?
C1 C6 C5 118.0(8) . . ?
C8 C7 S2 114.8(4) . . ?
C7 C8 C9 117.7(6) . . ?
C10 C8 C7 118.6(6) . . ?
C10 C8 C9 123.6(6) . . ?
C8 C10 C11 122(2) . . ?
C8 C10 C11A 128.8(15) . . ?
C10 C11 S1A 116(3) . . ?
C10 C11A S1 121(2) . . ?
F1 C12 S1A 68.1(15) . . ?
F1 C12 F5 99.0(16) . . ?
F2 C12 S1A 121.9(14) . . ?
F2 C12 F1 58.0(15) . . ?
F2 C12 F3 64.3(12) . . ?
F2 C12 F4 95.6(13) . . ?
F2 C12 F5 123.6(16) . . ?
F2 C12 F7 136.8(15) . . ?
F2 C12 F8 95.8(14) . . ?
F3 C12 S1A 123.3(8) . . ?
F3 C12 F1 110.7(9) . . ?
F3 C12 F5 82.8(11) . . ?
F3 C12 F7 112.5(10) . . ?
F3 C12 F8 112.7(8) . . ?
F4 C12 S1A 123.2(10) . . ?
F4 C12 F1 147.7(11) . . ?
F4 C12 F3 37.0(7) . . ?
F4 C12 F5 79.6(13) . . ?
F4 C12 F7 76.2(10) . . ?
F4 C12 F8 91.5(10) . . ?
F5 C12 S1A 44.8(10) . . ?
F7 C12 S1A 96.5(8) . . ?
F7 C12 F1 135.4(11) . . ?
F7 C12 F5 97.0(12) . . ?
F8 C12 S1A 121.4(7) . . ?
F8 C12 F1 108.2(8) . . ?
F8 C12 F5 140.1(12) . . ?
F8 C12 F7 43.4(7) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
