# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_41
_database_code_depnum_ccdc_archive 'CCDC 1827463'
_audit_update_record             
;
2018-03-05 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2017-02-07
_audit_creation_method           'by CrystalStructure 4.2'


_chemical_formula_sum            'C17 H10 F3 N O3 S'
_chemical_formula_moiety         'C17 H10 F3 N O3 S'
_chemical_formula_weight         365.33
_chemical_melting_point          ?
_chemical_absolute_configuration ' ad '

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.66599(6)
_cell_length_b                   8.61364(10)
_cell_length_c                   31.0135(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1513.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12159
_cell_measurement_theta_min      5.09
_cell_measurement_theta_max      75.30
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744.00
_exptl_absorpt_coefficient_mu    2.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  0.787

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            16368
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_theta_max         75.514
_diffrn_reflns_theta_min         2.850
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3066
_reflns_number_gt                3065
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.996

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1124
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     227
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1049P)²+0.3931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.77
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.080(4)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(15)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
S18 S 0.17099(12) 0.23806(9) 0.75758(2) 0.0277(3) Uani 1 1 d . . . . .
F1 F -0.0296(3) 0.85729(19) 0.85323(5) 0.0252(4) Uani 1 1 d . . . . .
F2 F 0.2616(4) 1.01533(18) 0.86058(5) 0.0300(4) Uani 1 1 d . . . . .
F3 F 0.2791(3) 0.83395(19) 0.81273(5) 0.0279(4) Uani 1 1 d . . . . .
O2 O -0.1611(3) 0.7748(2) 0.96594(6) 0.0214(4) Uani 1 1 d . . . . .
O7 O 0.0545(3) 0.35985(18) 0.88678(5) 0.0142(4) Uani 1 1 d . . . . .
O15 O 0.6653(3) 0.5698(2) 0.84358(6) 0.0205(4) Uani 1 1 d . . . . .
N1 N -0.0388(4) 0.5735(2) 0.92465(6) 0.0122(4) Uani 1 1 d . . . . .
C2 C -0.0132(4) 0.7212(3) 0.94189(7) 0.0138(5) Uani 1 1 d . . . . .
C3 C 0.2189(5) 0.7979(3) 0.93082(8) 0.0177(5) Uani 1 1 d . . . . .
H3A H 0.3368 0.7675 0.9528 0.021 Uiso 1 1 calc R U . . .
H3B H 0.1979 0.9118 0.9328 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3192(4) 0.7595(3) 0.88619(7) 0.0147(5) Uani 1 1 d . . . . .
H4 H 0.4925 0.7815 0.8868 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2860(4) 0.5909(3) 0.87340(7) 0.0128(5) Uani 1 1 d . . . . .
C6 C 0.1118(4) 0.5122(3) 0.89284(7) 0.0117(5) Uani 1 1 d . . . . .
C8 C -0.1399(4) 0.3282(3) 0.91275(7) 0.0134(5) Uani 1 1 d . . . . .
C9 C -0.2577(5) 0.1888(3) 0.91518(8) 0.0201(5) Uani 1 1 d . . . . .
H9 H -0.2120 0.1007 0.8988 0.024 Uiso 1 1 calc R U . . .
C10 C -0.4497(5) 0.1861(3) 0.94355(8) 0.0221(5) Uani 1 1 d . . . . .
H10 H -0.5385 0.0931 0.9465 0.026 Uiso 1 1 calc R U . . .
C11 C -0.5143(5) 0.3154(3) 0.96758(8) 0.0198(5) Uani 1 1 d . . . . .
H11 H -0.6455 0.3083 0.9866 0.024 Uiso 1 1 calc R U . . .
C12 C -0.3913(4) 0.4562(3) 0.96461(7) 0.0154(5) Uani 1 1 d . . . . .
H12 H -0.4352 0.5448 0.9810 0.018 Uiso 1 1 calc R U . . .
C13 C -0.2018(4) 0.4584(3) 0.93640(7) 0.0121(5) Uani 1 1 d . . . . .
C14 C 0.2071(5) 0.8663(3) 0.85271(8) 0.0189(5) Uani 1 1 d . . . . .
C15 C 0.4608(4) 0.5202(3) 0.84414(7) 0.0131(5) Uani 1 1 d . . . . .
C16 C 0.3917(4) 0.3933(3) 0.81453(7) 0.0132(5) Uani 1 1 d . . . . .
C17 C 0.1760(4) 0.3853(3) 0.79437(7) 0.0158(5) Uani 1 1 d . . . . .
H17 H 0.0470 0.4527 0.8001 0.019 Uiso 1 1 calc R U . . .
C19 C 0.4495(5) 0.1800(3) 0.76829(8) 0.0198(5) Uani 1 1 d . . . . .
H19 H 0.5263 0.0946 0.7549 0.024 Uiso 1 1 calc R U . . .
C20 C 0.5520(4) 0.2770(3) 0.80010(8) 0.0179(5) Uani 1 1 d . . . . .
H20 H 0.7088 0.2658 0.8105 0.021 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
S18 C19 1.688(3) . ?
S18 C17 1.706(2) . ?
F1 C14 1.343(3) . ?
F2 C14 1.343(3) . ?
F3 C14 1.335(3) . ?
O2 C2 1.214(3) . ?
O7 C6 1.365(3) . ?
O7 C8 1.391(3) . ?
O15 C15 1.235(3) . ?
N1 C2 1.387(3) . ?
N1 C13 1.403(3) . ?
N1 C6 1.407(3) . ?
C2 C3 1.511(3) . ?
C3 C4 1.533(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(3) . ?
C4 C14 1.525(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.340(3) . ?
C5 C15 1.475(3) . ?
C8 C9 1.375(3) . ?
C8 C13 1.386(3) . ?
C9 C10 1.399(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C15 C16 1.480(3) . ?
C16 C17 1.375(3) . ?
C16 C20 1.425(3) . ?
C17 H17 0.9500 . ?
C19 C20 1.417(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C19 S18 C17 94.20(13) . . ?
C6 O7 C8 107.29(18) . . ?
C2 N1 C13 128.06(19) . . ?
C2 N1 C6 123.4(2) . . ?
C13 N1 C6 108.44(18) . . ?
O2 C2 N1 120.9(2) . . ?
O2 C2 C3 125.0(2) . . ?
N1 C2 C3 113.9(2) . . ?
C2 C3 C4 115.70(19) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C14 110.32(19) . . ?
C5 C4 C3 113.35(19) . . ?
C14 C4 C3 109.3(2) . . ?
C5 C4 H4 107.9 . . ?
C14 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
C6 C5 C15 124.2(2) . . ?
C6 C5 C4 117.2(2) . . ?
C15 C5 C4 118.2(2) . . ?
C5 C6 O7 126.8(2) . . ?
C5 C6 N1 124.9(2) . . ?
O7 C6 N1 108.24(19) . . ?
C9 C8 C13 123.7(2) . . ?
C9 C8 O7 125.9(2) . . ?
C13 C8 O7 110.4(2) . . ?
C8 C9 C10 115.3(2) . . ?
C8 C9 H9 122.4 . . ?
C10 C9 H9 122.4 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 116.0(2) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C12 C13 C8 121.3(2) . . ?
C12 C13 N1 133.2(2) . . ?
C8 C13 N1 105.52(19) . . ?
F3 C14 F2 107.3(2) . . ?
F3 C14 F1 107.7(2) . . ?
F2 C14 F1 106.4(2) . . ?
F3 C14 C4 112.3(2) . . ?
F2 C14 C4 110.9(2) . . ?
F1 C14 C4 111.9(2) . . ?
O15 C15 C5 119.7(2) . . ?
O15 C15 C16 119.7(2) . . ?
C5 C15 C16 120.6(2) . . ?
C17 C16 C20 112.9(2) . . ?
C17 C16 C15 123.7(2) . . ?
C20 C16 C15 123.1(2) . . ?
C16 C17 S18 110.88(19) . . ?
C16 C17 H17 124.6 . . ?
S18 C17 H17 124.6 . . ?
C20 C19 S18 110.21(18) . . ?
C20 C19 H19 124.9 . . ?
S18 C19 H19 124.9 . . ?
C19 C20 C16 111.8(2) . . ?
C19 C20 H20 124.1 . . ?
C16 C20 H20 124.1 . . ?

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
C13 N1 C2 O2 -11.4(4) . . . . ?
C6 N1 C2 O2 172.4(2) . . . . ?
C13 N1 C2 C3 163.8(2) . . . . ?
C6 N1 C2 C3 -12.4(3) . . . . ?
O2 C2 C3 C4 -150.9(2) . . . . ?
N1 C2 C3 C4 34.1(3) . . . . ?
C2 C3 C4 C5 -39.4(3) . . . . ?
C2 C3 C4 C14 84.1(2) . . . . ?
C14 C4 C5 C6 -100.0(3) . . . . ?
C3 C4 C5 C6 22.9(3) . . . . ?
C14 C4 C5 C15 86.2(3) . . . . ?
C3 C4 C5 C15 -150.8(2) . . . . ?
C15 C5 C6 O7 -5.4(4) . . . . ?
C4 C5 C6 O7 -178.7(2) . . . . ?
C15 C5 C6 N1 172.1(2) . . . . ?
C4 C5 C6 N1 -1.2(3) . . . . ?
C8 O7 C6 C5 -178.8(2) . . . . ?
C8 O7 C6 N1 3.4(2) . . . . ?
C2 N1 C6 C5 -4.7(4) . . . . ?
C13 N1 C6 C5 178.4(2) . . . . ?
C2 N1 C6 O7 173.13(19) . . . . ?
C13 N1 C6 O7 -3.7(2) . . . . ?
C6 O7 C8 C9 177.8(2) . . . . ?
C6 O7 C8 C13 -2.0(3) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
O7 C8 C9 C10 -179.5(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C11 C12 C13 N1 -179.9(2) . . . . ?
C9 C8 C13 C12 -0.1(4) . . . . ?
O7 C8 C13 C12 179.74(19) . . . . ?
C9 C8 C13 N1 179.9(2) . . . . ?
O7 C8 C13 N1 -0.3(3) . . . . ?
C2 N1 C13 C12 5.7(4) . . . . ?
C6 N1 C13 C12 -177.6(2) . . . . ?
C2 N1 C13 C8 -174.2(2) . . . . ?
C6 N1 C13 C8 2.4(2) . . . . ?
C5 C4 C14 F3 -51.8(3) . . . . ?
C3 C4 C14 F3 -177.11(19) . . . . ?
C5 C4 C14 F2 -171.9(2) . . . . ?
C3 C4 C14 F2 62.8(3) . . . . ?
C5 C4 C14 F1 69.5(3) . . . . ?
C3 C4 C14 F1 -55.8(3) . . . . ?
C6 C5 C15 O15 -145.7(2) . . . . ?
C4 C5 C15 O15 27.6(3) . . . . ?
C6 C5 C15 C16 36.1(3) . . . . ?
C4 C5 C15 C16 -150.6(2) . . . . ?
O15 C15 C16 C17 -142.1(2) . . . . ?
C5 C15 C16 C17 36.1(3) . . . . ?
O15 C15 C16 C20 30.3(4) . . . . ?
C5 C15 C16 C20 -151.6(2) . . . . ?
C20 C16 C17 S18 -0.8(3) . . . . ?
C15 C16 C17 S18 172.30(18) . . . . ?
C19 S18 C17 C16 1.19(19) . . . . ?
C17 S18 C19 C20 -1.3(2) . . . . ?
S18 C19 C20 C16 1.0(3) . . . . ?
C17 C16 C20 C19 -0.2(3) . . . . ?
C15 C16 C20 C19 -173.3(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


