# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1047559'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 F3 N S'
_chemical_formula_sum            'C17 H18 F3 N S'
_chemical_formula_weight         325.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.11670(10)
_cell_length_b                   7.92950(10)
_cell_length_c                   11.3854(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.727(7)
_cell_angle_gamma                90
_cell_volume                     792.25(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9396
_cell_measurement_theta_min      6.90
_cell_measurement_theta_max      68.30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10973
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.892
_diffrn_reflns_theta_max         68.255
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2783
_reflns_number_gt                2403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2783
_refine_ls_number_parameters     206
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.109
_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_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 0.44614(11) 0.25987(19) 0.36720(9) 0.0680(4) Uani 1 1 d . . . . .
F1 F 0.3662(3) 0.4713(4) 0.0393(2) 0.0775(8) Uani 1 1 d . . . . .
F2 F 0.5784(3) 0.4638(4) 0.1757(3) 0.0728(7) Uani 1 1 d . . . . .
F3 F 0.3825(3) 0.5793(3) 0.2125(3) 0.0854(9) Uani 1 1 d . . . . .
N1 N 0.4157(5) -0.0322(5) 0.1669(6) 0.0886(14) Uani 1 1 d D . . . .
H1N H 0.445(7) -0.036(11) 0.247(3) 0.106 Uiso 1 1 d D U . . .
H2N H 0.328(4) -0.077(9) 0.158(6) 0.106 Uiso 1 1 d D U . . .
C18 C 0.7139(5) 0.2403(11) 0.5373(4) 0.0895(18) Uani 1 1 d . . . . .
H1A H 0.6844 0.1297 0.5594 0.107 Uiso 1 1 calc R U . . .
H1B H 0.6670 0.3234 0.5781 0.107 Uiso 1 1 calc R U . . .
C1 C 1.1968(6) 0.2895(7) 0.6808(5) 0.0843(16) Uani 1 1 d . . . . .
H1 H 1.3016 0.2988 0.7139 0.101 Uiso 1 1 calc R U . . .
C2 C 1.1390(5) 0.2063(7) 0.5715(5) 0.0771(13) Uani 1 1 d . . . . .
H2 H 1.2046 0.1627 0.5293 0.093 Uiso 1 1 calc R U . . .
C3 C 0.9842(5) 0.1884(6) 0.5255(4) 0.0648(11) Uani 1 1 d . . . . .
H3 H 0.9458 0.1290 0.4533 0.078 Uiso 1 1 calc R U . . .
C4 C 0.8852(4) 0.2567(6) 0.5844(3) 0.0593(9) Uani 1 1 d . . . . .
C5 C 0.6525(4) 0.2622(8) 0.4042(4) 0.0698(11) Uani 1 1 d . . . . .
H5A H 0.6879 0.1716 0.3615 0.084 Uiso 1 1 calc R U . . .
H5B H 0.6873 0.3684 0.3790 0.084 Uiso 1 1 calc R U . . .
C6 C 0.3814(4) 0.2781(5) 0.2014(3) 0.0462(7) Uani 1 1 d . . . . .
C7 C 0.2058(3) 0.2742(5) 0.1664(3) 0.0419(7) Uani 1 1 d . . . . .
C8 C 0.1253(4) 0.3507(5) 0.2391(4) 0.0539(9) Uani 1 1 d . . . . .
H8 H 0.1775 0.4006 0.3125 0.065 Uiso 1 1 calc R U . . .
C9 C -0.0330(5) 0.3531(6) 0.2031(4) 0.0619(10) Uani 1 1 d . . . . .
H9 H -0.0860 0.4058 0.2521 0.074 Uiso 1 1 calc R U . . .
C10 C -0.1118(4) 0.2786(6) 0.0958(4) 0.0619(10) Uani 1 1 d . . . . .
H10 H -0.2178 0.2797 0.0725 0.074 Uiso 1 1 calc R U . . .
C11 C 1.1004(7) 0.3575(7) 0.7398(5) 0.0863(17) Uani 1 1 d . . . . .
H11 H 1.1389 0.4153 0.8127 0.104 Uiso 1 1 calc R U . . .
C12 C 0.9462(7) 0.3412(7) 0.6921(4) 0.0772(13) Uani 1 1 d . . . . .
H12 H 0.8811 0.3883 0.7334 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4516(5) 0.1364(6) 0.1396(4) 0.0613(10) Uani 1 1 d . . . . .
H13A H 0.4173 0.1523 0.0520 0.074 Uiso 1 1 calc R U . . .
H13B H 0.5615 0.1492 0.1640 0.074 Uiso 1 1 calc R U . . .
C15 C -0.0340(4) 0.2030(6) 0.0239(4) 0.0639(11) Uani 1 1 d . . . . .
H15 H -0.0876 0.1526 -0.0488 0.077 Uiso 1 1 calc R U . . .
C16 C 0.1245(4) 0.2000(5) 0.0575(4) 0.0550(9) Uani 1 1 d . . . . .
H16 H 0.1761 0.1483 0.0070 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4274(4) 0.4473(5) 0.1584(4) 0.0551(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
S1 C5 1.813(4) . ?
S1 C6 1.824(4) . ?
F1 C17 1.333(5) . ?
F2 C17 1.344(5) . ?
F3 C17 1.333(5) . ?
N1 C13 1.431(6) . ?
N1 H1N 0.88(3) . ?
N1 H2N 0.85(3) . ?
C18 C5 1.477(6) . ?
C18 C4 1.514(6) . ?
C18 H1A 0.9700 . ?
C18 H1B 0.9700 . ?
C1 C11 1.354(8) . ?
C1 C2 1.380(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C12 1.375(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C17 1.525(6) . ?
C6 C7 1.541(4) . ?
C6 C13 1.552(6) . ?
C7 C8 1.387(5) . ?
C7 C16 1.391(5) . ?
C8 C9 1.390(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(7) . ?
C9 H9 0.9300 . ?
C10 C15 1.359(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.392(6) . ?
C15 H15 0.9300 . ?
C16 H16 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
C5 S1 C6 105.29(18) . . ?
C13 N1 H1N 103(6) . . ?
C13 N1 H2N 128(5) . . ?
H1N N1 H2N 96(7) . . ?
C5 C18 C4 114.9(4) . . ?
C5 C18 H1A 108.6 . . ?
C4 C18 H1A 108.6 . . ?
C5 C18 H1B 108.6 . . ?
C4 C18 H1B 108.6 . . ?
H1A C18 H1B 107.5 . . ?
C11 C1 C2 119.8(4) . . ?
C11 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C12 117.9(4) . . ?
C3 C4 C18 123.0(4) . . ?
C12 C4 C18 119.1(4) . . ?
C18 C5 S1 108.5(3) . . ?
C18 C5 H5A 110.0 . . ?
S1 C5 H5A 110.0 . . ?
C18 C5 H5B 110.0 . . ?
S1 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C17 C6 C7 106.9(3) . . ?
C17 C6 C13 108.0(3) . . ?
C7 C6 C13 113.2(3) . . ?
C17 C6 S1 111.2(3) . . ?
C7 C6 S1 106.8(2) . . ?
C13 C6 S1 110.7(3) . . ?
C8 C7 C16 118.5(3) . . ?
C8 C7 C6 121.2(3) . . ?
C16 C7 C6 120.3(3) . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C15 C10 C9 119.6(4) . . ?
C15 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C1 C11 C12 120.0(5) . . ?
C1 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C4 121.5(5) . . ?
C11 C12 H12 119.2 . . ?
C4 C12 H12 119.2 . . ?
N1 C13 C6 115.6(4) . . ?
N1 C13 H13A 108.4 . . ?
C6 C13 H13A 108.4 . . ?
N1 C13 H13B 108.4 . . ?
C6 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C10 C15 C16 121.0(4) . . ?
C10 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C7 C16 C15 120.0(4) . . ?
C7 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
F1 C17 F3 105.2(4) . . ?
F1 C17 F2 105.3(3) . . ?
F3 C17 F2 106.7(3) . . ?
F1 C17 C6 112.1(3) . . ?
F3 C17 C6 113.4(3) . . ?
F2 C17 C6 113.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N S1 0.88(3) 2.71(8) 3.210(5) 117(6) .
C5 H5B F2 0.97 2.38 2.971(6) 118.6 .

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3



