# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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/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_tr1
_audit_block_doi                 10.5517/cczfthp
_database_code_depnum_ccdc_archive 'CCDC 907013'
_audit_update_record             
;
2012-10-22 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;
#TrackingRef '14828_web_deposit_cif_file_0_SATISHMALWAL_1350888681.TR1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 F O2 S'
_chemical_formula_weight         262.29

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'
O O 0.0106 0.0060 '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)/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                   11.4383(13)
_cell_length_b                   11.6596(15)
_cell_length_c                   9.4849(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.523(3)
_cell_angle_gamma                90.00
_cell_volume                     1224.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4142
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.21

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.052
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9509
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         28.35
_reflns_number_total             3047
_reflns_number_gt                2601
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0458P)²+0.0000P] 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         3047
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.491
_refine_ls_restrained_S_all      1.491
_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 0.04847(3) 0.71378(3) 0.23033(4) 0.02145(12) Uani 1 1 d . . .
F1 F 0.33485(9) 0.23805(8) 0.41120(12) 0.0415(3) Uani 1 1 d . . .
O1 O -0.05544(9) 0.66723(9) 0.12770(11) 0.0311(3) Uani 1 1 d . . .
O2 O 0.06138(9) 0.68973(10) 0.38296(11) 0.0308(3) Uani 1 1 d . . .
C1 C 0.29879(13) 0.34358(12) 0.35629(17) 0.0282(3) Uani 1 1 d . . .
C2 C 0.23340(12) 0.35240(12) 0.21429(16) 0.0263(3) Uani 1 1 d . . .
H11 H 0.2118 0.2875 0.1567 0.032 Uiso 1 1 calc R . .
C3 C 0.20032(11) 0.46139(12) 0.15897(15) 0.0222(3) Uani 1 1 d . . .
H10 H 0.1568 0.4696 0.0626 0.027 Uiso 1 1 calc R . .
C4 C 0.23140(12) 0.55836(11) 0.24570(15) 0.0217(3) Uani 1 1 d . . .
C5 C 0.18838(12) 0.67438(11) 0.18339(14) 0.0207(3) Uani 1 1 d . . .
H9 H 0.1724 0.6701 0.0771 0.025 Uiso 1 1 calc R . .
C6 C 0.26606(12) 0.77846(11) 0.23465(15) 0.0206(3) Uani 1 1 d . . .
C7 C 0.39152(13) 0.78086(12) 0.26736(18) 0.0273(3) Uani 1 1 d . . .
H6 H 0.4347 0.7148 0.2583 0.033 Uiso 1 1 calc R . .
C8 C 0.45186(12) 0.88279(14) 0.31372(18) 0.0307(3) Uani 1 1 d . . .
H5 H 0.5357 0.8851 0.3350 0.037 Uiso 1 1 calc R . .
C9 C 0.38794(12) 0.98086(13) 0.32842(16) 0.0273(3) Uani 1 1 d . . .
H1 H 0.4294 1.0484 0.3605 0.033 Uiso 1 1 calc R . .
C10 C 0.29665(14) 0.54496(13) 0.39047(16) 0.0307(3) Uani 1 1 d . . .
H3 H 0.3170 0.6090 0.4500 0.037 Uiso 1 1 calc R . .
C11 C 0.33118(15) 0.43686(14) 0.44562(17) 0.0336(4) Uani 1 1 d . . .
H2 H 0.3755 0.4276 0.5415 0.040 Uiso 1 1 calc R . .
C12 C 0.06591(11) 0.86434(12) 0.20867(15) 0.0222(3) Uani 1 1 d . . .
H7 H 0.0304 0.8882 0.1092 0.027 Uiso 1 1 calc R . .
H8 H 0.0297 0.9079 0.2739 0.027 Uiso 1 1 calc R . .
C13 C 0.20162(11) 0.87820(11) 0.24804(14) 0.0195(3) Uani 1 1 d . . .
C14 C 0.26267(12) 0.97971(12) 0.29592(15) 0.0232(3) Uani 1 1 d . . .
H4 H 0.2201 1.0459 0.3060 0.028 Uiso 1 1 calc R . .


_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 1.4403(10) . ?
S1 O2 1.4453(10) . ?
S1 C12 1.7844(15) . ?
S1 C5 1.8242(13) . ?
F1 C1 1.3593(17) . ?
C1 C2 1.371(2) . ?
C1 C11 1.371(2) . ?
C2 C3 1.3906(19) . ?
C2 H11 0.9300 . ?
C3 C4 1.3910(18) . ?
C3 H10 0.9300 . ?
C4 C10 1.397(2) . ?
C4 C5 1.5085(19) . ?
C5 C6 1.5105(18) . ?
C5 H9 0.9800 . ?
C6 C7 1.3903(18) . ?
C6 C13 1.3996(18) . ?
C7 C8 1.389(2) . ?
C7 H6 0.9300 . ?
C8 C9 1.383(2) . ?
C8 H5 0.9300 . ?
C9 C14 1.3881(18) . ?
C9 H1 0.9300 . ?
C10 C11 1.384(2) . ?
C10 H3 0.9300 . ?
C11 H2 0.9300 . ?
C12 C13 1.5113(17) . ?
C12 H7 0.9700 . ?
C12 H8 0.9700 . ?
C13 C14 1.3913(18) . ?
C14 H4 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 117.62(7) . . ?
O1 S1 C12 112.96(6) . . ?
O2 S1 C12 108.66(7) . . ?
O1 S1 C5 111.46(6) . . ?
O2 S1 C5 108.67(6) . . ?
C12 S1 C5 95.13(6) . . ?
F1 C1 C2 118.87(14) . . ?
F1 C1 C11 118.18(14) . . ?
C2 C1 C11 122.95(14) . . ?
C1 C2 C3 117.98(13) . . ?
C1 C2 H11 121.0 . . ?
C3 C2 H11 121.0 . . ?
C2 C3 C4 120.97(13) . . ?
C2 C3 H10 119.5 . . ?
C4 C3 H10 119.5 . . ?
C3 C4 C10 118.98(13) . . ?
C3 C4 C5 119.16(12) . . ?
C10 C4 C5 121.78(12) . . ?
C4 C5 C6 119.12(11) . . ?
C4 C5 S1 110.49(9) . . ?
C6 C5 S1 101.56(9) . . ?
C4 C5 H9 108.4 . . ?
C6 C5 H9 108.4 . . ?
S1 C5 H9 108.4 . . ?
C7 C6 C13 120.04(12) . . ?
C7 C6 C5 125.37(12) . . ?
C13 C6 C5 114.59(12) . . ?
C8 C7 C6 119.41(13) . . ?
C8 C7 H6 120.3 . . ?
C6 C7 H6 120.3 . . ?
C9 C8 C7 120.39(13) . . ?
C9 C8 H5 119.8 . . ?
C7 C8 H5 119.8 . . ?
C8 C9 C14 120.80(13) . . ?
C8 C9 H1 119.6 . . ?
C14 C9 H1 119.6 . . ?
C11 C10 C4 120.32(14) . . ?
C11 C10 H3 119.8 . . ?
C4 C10 H3 119.8 . . ?
C1 C11 C10 118.78(15) . . ?
C1 C11 H2 120.6 . . ?
C10 C11 H2 120.6 . . ?
C13 C12 S1 102.38(9) . . ?
C13 C12 H7 111.3 . . ?
S1 C12 H7 111.3 . . ?
C13 C12 H8 111.3 . . ?
S1 C12 H8 111.3 . . ?
H7 C12 H8 109.2 . . ?
C14 C13 C6 120.25(12) . . ?
C14 C13 C12 124.88(12) . . ?
C6 C13 C12 114.86(12) . . ?
C9 C14 C13 119.10(13) . . ?
C9 C14 H4 120.4 . . ?
C13 C14 H4 120.4 . . ?

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 C3 -178.21(11) . . . . ?
C11 C1 C2 C3 0.9(2) . . . . ?
C1 C2 C3 C4 -0.78(19) . . . . ?
C2 C3 C4 C10 -0.11(19) . . . . ?
C2 C3 C4 C5 -177.01(11) . . . . ?
C3 C4 C5 C6 -148.25(12) . . . . ?
C10 C4 C5 C6 34.94(18) . . . . ?
C3 C4 C5 S1 94.82(12) . . . . ?
C10 C4 C5 S1 -81.99(15) . . . . ?
O1 S1 C5 C4 -85.50(11) . . . . ?
O2 S1 C5 C4 45.69(11) . . . . ?
C12 S1 C5 C4 157.37(10) . . . . ?
O1 S1 C5 C6 147.16(9) . . . . ?
O2 S1 C5 C6 -81.65(10) . . . . ?
C12 S1 C5 C6 30.02(10) . . . . ?
C4 C5 C6 C7 37.12(19) . . . . ?
S1 C5 C6 C7 158.65(13) . . . . ?
C4 C5 C6 C13 -143.02(12) . . . . ?
S1 C5 C6 C13 -21.49(14) . . . . ?
C13 C6 C7 C8 0.2(2) . . . . ?
C5 C6 C7 C8 -179.93(14) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C14 -0.6(2) . . . . ?
C3 C4 C10 C11 0.9(2) . . . . ?
C5 C4 C10 C11 177.76(13) . . . . ?
F1 C1 C11 C10 179.03(13) . . . . ?
C2 C1 C11 C10 -0.1(2) . . . . ?
C4 C10 C11 C1 -0.9(2) . . . . ?
O1 S1 C12 C13 -146.04(9) . . . . ?
O2 S1 C12 C13 81.56(10) . . . . ?
C5 S1 C12 C13 -30.13(10) . . . . ?
C7 C6 C13 C14 -0.9(2) . . . . ?
C5 C6 C13 C14 179.27(12) . . . . ?
C7 C6 C13 C12 179.76(13) . . . . ?
C5 C6 C13 C12 -0.11(17) . . . . ?
S1 C12 C13 C14 -157.12(12) . . . . ?
S1 C12 C13 C6 22.22(14) . . . . ?
C8 C9 C14 C13 0.0(2) . . . . ?
C6 C13 C14 C9 0.8(2) . . . . ?
C12 C13 C14 C9 -179.93(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.051


