# 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_sad_a
_database_code_depnum_ccdc_archive 'CCDC 1552163'
_audit_update_record             
;
2017-05-24 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 F5 N O2 S'
_chemical_formula_sum            'C14 H16 F5 N O2 S'
_chemical_formula_weight         357.34

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   13.9735(8)
_cell_length_b                   11.3828(6)
_cell_length_c                   10.4133(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.6450(10)
_cell_angle_gamma                90
_cell_volume                     1559.91(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      30.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was 
used for absorption correction. 
Krause, L., Herbst-Irmer, R., 
Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(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 D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36503
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.096
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4765
_reflns_number_gt                3519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 v.2016.9-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V.8.37A (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V.8.37A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Xshell v.6.3.1 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v.2016.9-0 (Bruker AXS Inc., 2016)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.8770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4765
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_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
C1 C 0.84203(12) 0.26137(15) 0.39078(16) 0.0230(3) Uani 1 1 d . . . . .
H1 H 0.805148 0.223912 0.441024 0.028 Uiso 1 1 calc R U . . .
C2 C 0.88838(13) 0.19419(15) 0.31723(17) 0.0263(3) Uani 1 1 d . . . . .
H2 H 0.883531 0.110953 0.317686 0.032 Uiso 1 1 calc R U . . .
C3 C 0.94162(12) 0.24831(16) 0.24328(17) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.973521 0.202259 0.193145 0.033 Uiso 1 1 calc R U . . .
C4 C 0.94841(13) 0.36926(17) 0.24228(19) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.984317 0.406467 0.190599 0.038 Uiso 1 1 calc R U . . .
C5 C 0.90286(13) 0.43645(15) 0.31665(19) 0.0290(4) Uani 1 1 d . . . . .
H5 H 0.908374 0.519631 0.316512 0.035 Uiso 1 1 calc R U . . .
C6 C 0.84922(11) 0.38303(14) 0.39138(15) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.79978(13) 0.45543(16) 0.47197(17) 0.0272(4) Uani 1 1 d . . . . .
H7A H 0.788517 0.407057 0.544612 0.033 Uiso 1 1 calc R U . . .
H7B H 0.844037 0.522433 0.515270 0.033 Uiso 1 1 calc R U . . .
C8 C 0.64313(11) 0.55120(13) 0.44566(14) 0.0166(3) Uani 1 1 d . . . . .
H8 H 0.661273 0.525786 0.542870 0.020 Uiso 1 1 calc R U . . .
C9 C 0.52900(11) 0.54029(13) 0.36726(14) 0.0171(3) Uani 1 1 d . . . . .
C10 C 0.42579(11) 0.72977(14) 0.32744(16) 0.0208(3) Uani 1 1 d . . . . .
H10A H 0.365214 0.681344 0.280709 0.025 Uiso 1 1 calc R U . . .
H10B H 0.428417 0.794895 0.265708 0.025 Uiso 1 1 calc R U . . .
C11 C 0.41674(13) 0.77917(16) 0.45642(17) 0.0277(4) Uani 1 1 d . . . . .
H11 H 0.421991 0.726649 0.529377 0.033 Uiso 1 1 calc R U . . .
C12 C 0.40202(18) 0.89063(19) 0.4739(2) 0.0440(5) Uani 1 1 d . . . . .
H12A H 0.396478 0.945099 0.402589 0.053 Uiso 1 1 calc R U . . .
H12B H 0.396855 0.917138 0.557788 0.053 Uiso 1 1 calc R U . . .
C13 C 0.62446(10) 0.68709(13) 0.42789(14) 0.0158(3) Uani 1 1 d . . . . .
H13 H 0.636035 0.729186 0.516127 0.019 Uiso 1 1 calc R U . . .
C14 C 0.67071(11) 0.74985(13) 0.33365(15) 0.0182(3) Uani 1 1 d . . . . .
H14A H 0.621479 0.809072 0.280190 0.022 Uiso 1 1 calc R U . . .
H14B H 0.680683 0.691790 0.268492 0.022 Uiso 1 1 calc R U . . .
F1 F 0.73705(8) 0.91713(9) 0.48153(12) 0.0389(3) Uani 1 1 d . . . . .
F2 F 0.77517(8) 0.90366(10) 0.28757(11) 0.0376(3) Uani 1 1 d . . . . .
F3 F 0.85331(7) 0.73320(10) 0.36051(11) 0.0333(2) Uani 1 1 d . . . . .
F4 F 0.81613(7) 0.74561(9) 0.55226(10) 0.0303(2) Uani 1 1 d . . . . .
F5 F 0.89373(7) 0.89039(10) 0.48824(11) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.51703(9) 0.65798(11) 0.35645(12) 0.0166(2) Uani 1 1 d . . . . .
O1 O 0.70411(8) 0.49772(10) 0.38005(10) 0.0198(2) Uani 1 1 d . . . . .
O2 O 0.46893(8) 0.45990(10) 0.33058(11) 0.0235(2) Uani 1 1 d . . . . .
S1 S 0.79069(3) 0.82255(3) 0.41791(4) 0.02054(9) 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 C2 1.387(2) . ?
C1 C6 1.388(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.500(2) . ?
C7 O1 1.4403(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.3982(16) . ?
C8 C9 1.533(2) . ?
C8 C13 1.569(2) . ?
C8 H8 1.0000 . ?
C9 O2 1.2133(18) . ?
C9 N1 1.3500(19) . ?
C10 N1 1.4580(18) . ?
C10 C11 1.500(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.308(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C13 N1 1.4716(18) . ?
C13 C14 1.5224(19) . ?
C13 H13 1.0000 . ?
C14 S1 1.8101(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
F1 S1 1.5792(11) . ?
F2 S1 1.5949(11) . ?
F3 S1 1.5838(11) . ?
F4 S1 1.5863(10) . ?
F5 S1 1.5800(10) . ?

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
C2 C1 C6 120.39(15) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.03(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.99(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.04(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.47(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.08(14) . . ?
C1 C6 C7 120.28(15) . . ?
C5 C6 C7 120.64(15) . . ?
O1 C7 C6 108.11(12) . . ?
O1 C7 H7A 110.1 . . ?
C6 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O1 C8 C9 113.60(11) . . ?
O1 C8 C13 118.43(11) . . ?
C9 C8 C13 85.13(10) . . ?
O1 C8 H8 112.3 . . ?
C9 C8 H8 112.3 . . ?
C13 C8 H8 112.3 . . ?
O2 C9 N1 131.98(14) . . ?
O2 C9 C8 135.60(14) . . ?
N1 C9 C8 92.39(12) . . ?
N1 C10 C11 110.84(13) . . ?
N1 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 123.54(16) . . ?
C12 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
N1 C13 C14 111.21(11) . . ?
N1 C13 C8 86.48(10) . . ?
C14 C13 C8 116.66(11) . . ?
N1 C13 H13 113.3 . . ?
C14 C13 H13 113.3 . . ?
C8 C13 H13 113.3 . . ?
C13 C14 S1 115.27(10) . . ?
C13 C14 H14A 108.5 . . ?
S1 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
S1 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C9 N1 C10 130.44(13) . . ?
C9 N1 C13 96.00(11) . . ?
C10 N1 C13 130.61(12) . . ?
C8 O1 C7 113.74(11) . . ?
F1 S1 F5 87.67(6) . . ?
F1 S1 F3 175.14(6) . . ?
F5 S1 F3 87.47(6) . . ?
F1 S1 F4 90.21(6) . . ?
F5 S1 F4 87.82(6) . . ?
F3 S1 F4 89.42(6) . . ?
F1 S1 F2 90.82(7) . . ?
F5 S1 F2 87.34(6) . . ?
F3 S1 F2 89.14(6) . . ?
F4 S1 F2 175.00(6) . . ?
F1 S1 C14 91.27(6) . . ?
F5 S1 C14 177.81(7) . . ?
F3 S1 C14 93.59(6) . . ?
F4 S1 C14 94.10(6) . . ?
F2 S1 C14 90.76(6) . . ?

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
C6 C1 C2 C3 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C1 C6 C7 -179.48(14) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -179.98(16) . . . . ?
C1 C6 C7 O1 -98.69(17) . . . . ?
C5 C6 C7 O1 81.42(19) . . . . ?
O1 C8 C9 O2 62.4(2) . . . . ?
C13 C8 C9 O2 -178.68(17) . . . . ?
O1 C8 C9 N1 -119.68(12) . . . . ?
C13 C8 C9 N1 -0.73(10) . . . . ?
N1 C10 C11 C12 128.6(2) . . . . ?
O1 C8 C13 N1 114.92(13) . . . . ?
C9 C8 C13 N1 0.67(9) . . . . ?
O1 C8 C13 C14 2.91(18) . . . . ?
C9 C8 C13 C14 -111.33(12) . . . . ?
N1 C13 C14 S1 165.10(10) . . . . ?
C8 C13 C14 S1 -97.95(13) . . . . ?
O2 C9 N1 C10 17.1(3) . . . . ?
C8 C9 N1 C10 -160.93(14) . . . . ?
O2 C9 N1 C13 178.85(15) . . . . ?
C8 C9 N1 C13 0.78(11) . . . . ?
C11 C10 N1 C9 99.06(18) . . . . ?
C11 C10 N1 C13 -56.7(2) . . . . ?
C14 C13 N1 C9 116.52(13) . . . . ?
C8 C13 N1 C9 -0.76(11) . . . . ?
C14 C13 N1 C10 -81.82(17) . . . . ?
C8 C13 N1 C10 160.90(14) . . . . ?
C9 C8 O1 C7 -150.86(13) . . . . ?
C13 C8 O1 C7 111.61(15) . . . . ?
C6 C7 O1 C8 170.59(13) . . . . ?
C13 C14 S1 F1 -68.98(12) . . . . ?
C13 C14 S1 F3 110.99(11) . . . . ?
C13 C14 S1 F4 21.31(12) . . . . ?
C13 C14 S1 F2 -159.83(11) . . . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.062

