# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_ku42
_database_code_depnum_ccdc_archive 'CCDC 926314'
_audit_update_record             
;
2013-02-25 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;
#TrackingRef 'ku42.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 F6 O2 S2'
_chemical_formula_weight         428.40

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'
O O 0.0106 0.0060 '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)/c

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

_cell_length_a                   9.9685(7)
_cell_length_b                   10.8630(7)
_cell_length_c                   15.8102(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9010(10)
_cell_angle_gamma                90.00
_cell_volume                     1691.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5075
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8295
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_process_details   
;
SADABS; Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_standards_number         176
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            16114
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2982
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0515P)²+1.0695P] 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         2982
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.27839(15) 0.99077(14) 1.07034(10) 0.0148(3) Uani 1 1 d . . .
C2 C 0.36934(16) 0.87685(15) 1.05963(10) 0.0173(3) Uani 1 1 d . . .
H2 H 0.4454 0.9084 1.0312 0.021 Uiso 1 1 calc R . .
C3 C 0.43350(16) 0.83754(15) 1.14804(11) 0.0189(3) Uani 1 1 d . . .
H3 H 0.4565 0.7545 1.1624 0.023 Uiso 1 1 calc R . .
C4 C 0.45498(17) 0.92860(15) 1.20388(11) 0.0180(3) Uani 1 1 d . . .
C5 C 0.28980(16) 0.79273(15) 0.99654(10) 0.0157(3) Uani 1 1 d . . .
C6 C 0.28407(17) 0.65632(16) 0.99958(10) 0.0188(4) Uani 1 1 d . . .
C7 C 0.17621(17) 0.62199(15) 0.92162(11) 0.0202(4) Uani 1 1 d . . .
C8 C 0.15860(17) 0.73983(16) 0.86608(11) 0.0208(4) Uani 1 1 d . . .
C9 C 0.22055(16) 0.84013(15) 0.92387(10) 0.0162(3) Uani 1 1 d . . .
C10 C 0.22595(16) 1.17423(15) 0.96481(10) 0.0180(3) Uani 1 1 d . . .
C11 C 0.24420(15) 1.05289(15) 0.98400(10) 0.0152(3) Uani 1 1 d . . .
C12 C 0.21060(15) 0.97303(15) 0.91045(10) 0.0162(3) Uani 1 1 d . . .
C13 C 0.16989(16) 1.03674(16) 0.83591(11) 0.0184(3) Uani 1 1 d . . .
C14 C 0.14800(16) 0.95778(16) 1.10596(11) 0.0196(4) Uani 1 1 d . . .
H14A H 0.1011 1.0335 1.1182 0.029 Uiso 1 1 calc R . .
H14B H 0.1713 0.9100 1.1588 0.029 Uiso 1 1 calc R . .
H14C H 0.0885 0.9088 1.0636 0.029 Uiso 1 1 calc R . .
C15 C 0.52387(19) 0.93264(16) 1.29456(11) 0.0252(4) Uani 1 1 d . . .
H15A H 0.5518 0.8493 1.3135 0.038 Uiso 1 1 calc R . .
H15B H 0.4610 0.9654 1.3309 0.038 Uiso 1 1 calc R . .
H15C H 0.6040 0.9858 1.2989 0.038 Uiso 1 1 calc R . .
C16 C 0.12348(18) 0.99223(17) 0.74627(11) 0.0236(4) Uani 1 1 d . . .
H16A H 0.1785 0.9213 0.7344 0.035 Uiso 1 1 calc R . .
H16B H 0.1338 1.0585 0.7057 0.035 Uiso 1 1 calc R . .
H16C H 0.0278 0.9678 0.7401 0.035 Uiso 1 1 calc R . .
C17 C 0.24331(18) 1.28626(15) 1.02093(11) 0.0229(4) Uani 1 1 d . . .
H17A H 0.2284 1.2641 1.0789 0.034 Uiso 1 1 calc R . .
H17B H 0.1773 1.3491 0.9976 0.034 Uiso 1 1 calc R . .
H17C H 0.3355 1.3187 1.0230 0.034 Uiso 1 1 calc R . .
F1 F 0.24731(11) 0.61310(9) 1.07340(6) 0.0275(3) Uani 1 1 d . . .
F2 F 0.40484(10) 0.60236(9) 0.99336(7) 0.0281(3) Uani 1 1 d . . .
F3 F 0.05839(10) 0.59310(11) 0.94822(7) 0.0313(3) Uani 1 1 d . . .
F4 F 0.21331(12) 0.52461(10) 0.87818(7) 0.0312(3) Uani 1 1 d . . .
F5 F 0.02622(10) 0.75888(10) 0.83383(7) 0.0281(3) Uani 1 1 d . . .
F6 F 0.22307(11) 0.72360(10) 0.79692(6) 0.0280(3) Uani 1 1 d . . .
O1 O 0.31881(12) 1.13650(11) 1.21183(7) 0.0221(3) Uani 1 1 d . . .
O2 O 0.49713(11) 1.13140(11) 1.11975(7) 0.0204(3) Uani 1 1 d . . .
S1 S 0.39099(4) 1.06827(4) 1.15509(2) 0.01547(13) Uani 1 1 d . . .
S2 S 0.17347(4) 1.19238(4) 0.85595(3) 0.01995(13) 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
C1 C11 1.514(2) . ?
C1 C14 1.537(2) . ?
C1 C2 1.559(2) . ?
C1 S1 1.8163(16) . ?
C2 C5 1.488(2) . ?
C2 C3 1.506(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.321(2) . ?
C3 H3 0.9500 . ?
C4 C15 1.491(2) . ?
C4 S1 1.7752(16) . ?
C5 C9 1.348(2) . ?
C5 C6 1.484(2) . ?
C6 F2 1.356(2) . ?
C6 F1 1.360(2) . ?
C6 C7 1.551(2) . ?
C7 F4 1.344(2) . ?
C7 F3 1.345(2) . ?
C7 C8 1.547(2) . ?
C8 F5 1.355(2) . ?
C8 F6 1.363(2) . ?
C8 C9 1.493(2) . ?
C9 C12 1.460(2) . ?
C10 C11 1.358(2) . ?
C10 C17 1.500(2) . ?
C10 S2 1.7309(16) . ?
C11 C12 1.448(2) . ?
C12 C13 1.373(2) . ?
C13 C16 1.501(2) . ?
C13 S2 1.7195(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O1 S1 1.4392(12) . ?
O2 S1 1.4440(12) . ?

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
C11 C1 C14 110.44(13) . . ?
C11 C1 C2 108.04(13) . . ?
C14 C1 C2 113.20(13) . . ?
C11 C1 S1 119.07(11) . . ?
C14 C1 S1 107.39(11) . . ?
C2 C1 S1 98.32(10) . . ?
C5 C2 C3 123.63(14) . . ?
C5 C2 C1 107.57(13) . . ?
C3 C2 C1 107.14(13) . . ?
C5 C2 H2 105.8 . . ?
C3 C2 H2 105.8 . . ?
C1 C2 H2 105.8 . . ?
C4 C3 C2 114.18(15) . . ?
C4 C3 H3 122.9 . . ?
C2 C3 H3 122.9 . . ?
C3 C4 C15 131.86(16) . . ?
C3 C4 S1 109.84(13) . . ?
C15 C4 S1 118.26(12) . . ?
C9 C5 C6 113.08(14) . . ?
C9 C5 C2 119.10(15) . . ?
C6 C5 C2 127.64(14) . . ?
F2 C6 F1 105.85(13) . . ?
F2 C6 C5 112.97(14) . . ?
F1 C6 C5 112.92(14) . . ?
F2 C6 C7 110.64(13) . . ?
F1 C6 C7 110.70(14) . . ?
C5 C6 C7 103.88(13) . . ?
F4 C7 F3 107.39(14) . . ?
F4 C7 C8 112.17(14) . . ?
F3 C7 C8 110.05(14) . . ?
F4 C7 C6 112.57(14) . . ?
F3 C7 C6 109.84(13) . . ?
C8 C7 C6 104.83(13) . . ?
F5 C8 F6 105.70(13) . . ?
F5 C8 C9 113.92(14) . . ?
F6 C8 C9 112.56(14) . . ?
F5 C8 C7 111.00(14) . . ?
F6 C8 C7 108.79(14) . . ?
C9 C8 C7 104.87(13) . . ?
C5 C9 C12 121.06(15) . . ?
C5 C9 C8 110.59(14) . . ?
C12 C9 C8 128.33(15) . . ?
C11 C10 C17 130.98(15) . . ?
C11 C10 S2 110.00(13) . . ?
C17 C10 S2 119.02(12) . . ?
C10 C11 C12 113.30(14) . . ?
C10 C11 C1 129.63(15) . . ?
C12 C11 C1 116.68(14) . . ?
C13 C12 C11 112.85(15) . . ?
C13 C12 C9 128.87(15) . . ?
C11 C12 C9 118.26(14) . . ?
C12 C13 C16 130.93(16) . . ?
C12 C13 S2 110.03(13) . . ?
C16 C13 S2 119.03(12) . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 S1 O2 117.62(7) . . ?
O1 S1 C4 110.49(8) . . ?
O2 S1 C4 109.79(7) . . ?
O1 S1 C1 112.77(7) . . ?
O2 S1 C1 109.93(7) . . ?
C4 S1 C1 93.66(8) . . ?
C13 S2 C10 93.76(8) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.059



