# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1584174'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F3 O4 S'
_chemical_formula_weight         318.26

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                   13.1925(12)
_cell_length_b                   13.3019(12)
_cell_length_c                   7.7183(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.7570(10)
_cell_angle_gamma                90.00
_cell_volume                     1330.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3770
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      30.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_T_max  0.9439
_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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6611
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2334
_reflns_number_gt                2072
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.5528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2334
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_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 0.25118(4) 0.60935(4) 0.14251(8) 0.0474(2) Uani 1 1 d . . .
C1 C 0.53546(17) 0.77789(18) 0.3820(3) 0.0456(5) Uani 1 1 d . . .
C2 C 0.44664(16) 0.82677(17) 0.3067(3) 0.0435(5) Uani 1 1 d . . .
H2 H 0.4442 0.8966 0.3046 0.052 Uiso 1 1 calc R . .
C3 C 0.35981(15) 0.77035(16) 0.2332(3) 0.0388(5) Uani 1 1 d . . .
C4 C 0.25967(15) 0.80365(16) 0.1459(3) 0.0393(5) Uani 1 1 d . . .
C5 C 0.19478(16) 0.72533(16) 0.0898(3) 0.0411(5) Uani 1 1 d . . .
C6 C 0.36560(15) 0.66449(16) 0.2422(3) 0.0412(5) Uani 1 1 d . . .
C7 C 0.45551(18) 0.61605(17) 0.3231(3) 0.0481(6) Uani 1 1 d . . .
H7 H 0.4580 0.5463 0.3308 0.058 Uiso 1 1 calc R . .
C8 C 0.54011(16) 0.67272(18) 0.3911(3) 0.0480(5) Uani 1 1 d . . .
H8 H 0.6011 0.6413 0.4437 0.058 Uiso 1 1 calc R . .
C9 C 0.62954(18) 0.8388(2) 0.4478(3) 0.0566(6) Uani 1 1 d . . .
C10 C 0.23538(17) 0.91290(17) 0.1263(3) 0.0444(5) Uani 1 1 d . . .
C11 C 0.1190(3) 1.0397(2) 0.1691(5) 0.0796(9) Uani 1 1 d . . .
H11A H 0.1693 1.0794 0.2455 0.119 Uiso 1 1 calc R . .
H11B H 0.0530 1.0473 0.2027 0.119 Uiso 1 1 calc R . .
H11C H 0.1147 1.0617 0.0495 0.119 Uiso 1 1 calc R . .
C12 C 0.08993(17) 0.72999(18) -0.0155(3) 0.0457(5) Uani 1 1 d . . .
C13 C -0.0594(2) 0.6368(3) -0.1248(5) 0.0841(10) Uani 1 1 d . . .
H13A H -0.1048 0.6830 -0.0815 0.126 Uiso 1 1 calc R . .
H13B H -0.0861 0.5698 -0.1224 0.126 Uiso 1 1 calc R . .
H13C H -0.0547 0.6543 -0.2437 0.126 Uiso 1 1 calc R . .
F1 F 0.61004(15) 0.92454(17) 0.5257(3) 0.0964(7) Uani 1 1 d . . .
F2 F 0.67514(14) 0.87094(16) 0.3187(2) 0.0880(6) Uani 1 1 d . . .
F3 F 0.69886(16) 0.79262(17) 0.5628(4) 0.1250(10) Uani 1 1 d . . .
O1 O 0.29024(16) 0.97264(13) 0.0745(3) 0.0684(5) Uani 1 1 d . . .
O2 O 0.14933(13) 0.93527(13) 0.1833(2) 0.0591(5) Uani 1 1 d . . .
O3 O 0.05342(14) 0.80177(14) -0.0973(3) 0.0672(5) Uani 1 1 d . . .
O4 O 0.04142(12) 0.64177(14) -0.0151(2) 0.0581(5) 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 C6 1.725(2) . ?
S1 C5 1.728(2) . ?
C1 C2 1.371(3) . ?
C1 C8 1.402(3) . ?
C1 C9 1.490(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C3 C6 1.411(3) . ?
C3 C4 1.437(3) . ?
C4 C5 1.367(3) . ?
C4 C10 1.490(3) . ?
C5 C12 1.469(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.368(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 F3 1.303(3) . ?
C9 F2 1.327(3) . ?
C9 F1 1.336(3) . ?
C10 O1 1.193(3) . ?
C10 O2 1.326(3) . ?
C11 O2 1.444(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O3 1.195(3) . ?
C12 O4 1.337(3) . ?
C13 O4 1.439(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C6 S1 C5 91.60(10) . . ?
C2 C1 C8 121.4(2) . . ?
C2 C1 C9 118.6(2) . . ?
C8 C1 C9 120.0(2) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C6 118.89(19) . . ?
C2 C3 C4 129.6(2) . . ?
C6 C3 C4 111.55(18) . . ?
C5 C4 C3 112.37(18) . . ?
C5 C4 C10 126.96(19) . . ?
C3 C4 C10 120.67(19) . . ?
C4 C5 C12 127.8(2) . . ?
C4 C5 S1 112.90(16) . . ?
C12 C5 S1 119.18(17) . . ?
C7 C6 C3 121.19(19) . . ?
C7 C6 S1 127.24(17) . . ?
C3 C6 S1 111.57(15) . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C1 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C1 C8 H8 119.8 . . ?
F3 C9 F2 107.7(2) . . ?
F3 C9 F1 105.4(2) . . ?
F2 C9 F1 102.4(2) . . ?
F3 C9 C1 114.2(2) . . ?
F2 C9 C1 112.6(2) . . ?
F1 C9 C1 113.6(2) . . ?
O1 C10 O2 124.9(2) . . ?
O1 C10 C4 123.5(2) . . ?
O2 C10 C4 111.50(19) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 123.8(2) . . ?
O3 C12 C5 124.8(2) . . ?
O4 C12 C5 111.32(19) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 O2 C11 115.6(2) . . ?
C12 O4 C13 115.4(2) . . ?

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 C1 C2 C3 -1.8(3) . . . . ?
C9 C1 C2 C3 175.6(2) . . . . ?
C1 C2 C3 C6 1.4(3) . . . . ?
C1 C2 C3 C4 -179.0(2) . . . . ?
C2 C3 C4 C5 179.3(2) . . . . ?
C6 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C4 C10 -1.4(3) . . . . ?
C6 C3 C4 C10 178.23(18) . . . . ?
C3 C4 C5 C12 -175.0(2) . . . . ?
C10 C4 C5 C12 5.8(4) . . . . ?
C3 C4 C5 S1 0.8(2) . . . . ?
C10 C4 C5 S1 -178.47(17) . . . . ?
C6 S1 C5 C4 -0.25(18) . . . . ?
C6 S1 C5 C12 175.92(18) . . . . ?
C2 C3 C6 C7 0.3(3) . . . . ?
C4 C3 C6 C7 -179.4(2) . . . . ?
C2 C3 C6 S1 -179.43(16) . . . . ?
C4 C3 C6 S1 0.9(2) . . . . ?
C5 S1 C6 C7 179.9(2) . . . . ?
C5 S1 C6 C3 -0.39(17) . . . . ?
C3 C6 C7 C8 -1.5(3) . . . . ?
S1 C6 C7 C8 178.15(17) . . . . ?
C6 C7 C8 C1 1.1(3) . . . . ?
C2 C1 C8 C7 0.6(3) . . . . ?
C9 C1 C8 C7 -176.8(2) . . . . ?
C2 C1 C9 F3 159.8(3) . . . . ?
C8 C1 C9 F3 -22.8(4) . . . . ?
C2 C1 C9 F2 -76.9(3) . . . . ?
C8 C1 C9 F2 100.4(3) . . . . ?
C2 C1 C9 F1 38.9(3) . . . . ?
C8 C1 C9 F1 -143.7(2) . . . . ?
C5 C4 C10 O1 -132.9(3) . . . . ?
C3 C4 C10 O1 47.9(3) . . . . ?
C5 C4 C10 O2 50.9(3) . . . . ?
C3 C4 C10 O2 -128.3(2) . . . . ?
C4 C5 C12 O3 15.8(4) . . . . ?
S1 C5 C12 O3 -159.8(2) . . . . ?
C4 C5 C12 O4 -167.1(2) . . . . ?
S1 C5 C12 O4 17.4(3) . . . . ?
O1 C10 O2 C11 4.1(4) . . . . ?
C4 C10 O2 C11 -179.8(2) . . . . ?
O3 C12 O4 C13 1.3(4) . . . . ?
C5 C12 O4 C13 -175.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.068
