# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1048606'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 F4 N O4 S'
_chemical_formula_sum            'C17 H21 F4 N O4 S'
_chemical_formula_weight         411.41
_chemical_absolute_configuration ad

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'
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'
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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.7459(6)
_cell_length_b                   9.8069(8)
_cell_length_c                   25.6020(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1944.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4632
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.67

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9334
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13219
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4465
_reflns_number_gt                3793
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0184P)²+0.4486P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     289
_refine_ls_number_restraints     172
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0695
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.002
_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
C10 C -0.0164(3) 0.69493(16) 0.15164(7) 0.0427(4) Uani 0.55(3) 1 d PDU A 1
H10 H 0.0105 0.7919 0.1473 0.051 Uiso 0.55(3) 1 calc PR A 1
C12 C -0.2090(11) 0.6832(10) 0.1452(4) 0.0579(17) Uani 0.55(3) 1 d PDU A 1
F2 F -0.2616(12) 0.7421(13) 0.1013(4) 0.103(3) Uani 0.55(3) 1 d PDU A 1
F3 F -0.2627(12) 0.5559(7) 0.1418(5) 0.090(2) Uani 0.55(3) 1 d PDU A 1
F4 F -0.2938(12) 0.7425(15) 0.1830(5) 0.107(2) Uani 0.55(3) 1 d PDU A 1
C10' C -0.0164(3) 0.69493(16) 0.15164(7) 0.0427(4) Uani 0.45(3) 1 d PDU A 2
H10' H 0.0091 0.7921 0.1472 0.051 Uiso 0.45(3) 1 calc PR A 2
C12' C -0.2118(13) 0.6809(12) 0.1467(5) 0.059(2) Uani 0.45(3) 1 d PDU A 2
F2' F -0.2709(14) 0.6955(18) 0.0984(3) 0.091(3) Uani 0.45(3) 1 d PDU A 2
F3' F -0.2705(13) 0.5632(8) 0.1637(8) 0.091(3) Uani 0.45(3) 1 d PDU A 2
F4' F -0.2911(14) 0.7747(9) 0.1752(5) 0.080(2) Uani 0.45(3) 1 d PDU A 2
C1 C 0.0430(3) 0.66573(18) 0.05375(7) 0.0482(5) Uani 1 1 d . A .
C2 C 0.0902(3) 0.61971(18) 0.10996(7) 0.0437(5) Uani 1 1 d . . .
C3 C 0.0874(3) 0.46357(18) 0.10927(7) 0.0471(5) Uani 1 1 d . A .
H3A H 0.2013 0.4266 0.1161 0.056 Uiso 1 1 calc R . .
H3B H 0.0074 0.4283 0.1351 0.056 Uiso 1 1 calc R . .
C4 C 0.0284(2) 0.42911(17) 0.05461(6) 0.0386(4) Uani 1 1 d . . .
C5 C 0.0016(3) 0.54356(17) 0.02425(6) 0.0403(4) Uani 1 1 d . A .
C6 C -0.0547(3) 0.53428(18) -0.02769(7) 0.0425(4) Uani 1 1 d . . .
H6 H -0.0745 0.6123 -0.0474 0.051 Uiso 1 1 calc R A .
C7 C -0.0796(3) 0.40808(18) -0.04843(7) 0.0413(4) Uani 1 1 d . A .
C8 C -0.0439(2) 0.28898(18) -0.01845(7) 0.0404(4) Uani 1 1 d . . .
C9 C 0.0070(3) 0.29979(16) 0.03313(7) 0.0404(4) Uani 1 1 d . A .
H9 H 0.0266 0.2221 0.0531 0.049 Uiso 1 1 calc R . .
C11 C 0.2656(3) 0.66503(19) 0.28183(8) 0.0514(5) Uani 1 1 d . . .
C13 C 0.3633(4) 0.5581(2) 0.25009(10) 0.0749(7) Uani 1 1 d . . .
H13A H 0.4228 0.6018 0.2218 0.112 Uiso 1 1 calc R . .
H13B H 0.2831 0.4926 0.2364 0.112 Uiso 1 1 calc R . .
H13C H 0.4454 0.5127 0.2721 0.112 Uiso 1 1 calc R . .
C14 C 0.1421(4) 0.6005(2) 0.32033(8) 0.0727(7) Uani 1 1 d . . .
H14A H 0.0680 0.5377 0.3023 0.109 Uiso 1 1 calc R . .
H14B H 0.0734 0.6702 0.3365 0.109 Uiso 1 1 calc R . .
H14C H 0.2064 0.5526 0.3466 0.109 Uiso 1 1 calc R . .
C15 C 0.3884(4) 0.7619(3) 0.30950(12) 0.0958(10) Uani 1 1 d . . .
H15A H 0.4576 0.7118 0.3340 0.144 Uiso 1 1 calc R . .
H15B H 0.3232 0.8302 0.3278 0.144 Uiso 1 1 calc R . .
H15C H 0.4620 0.8051 0.2843 0.144 Uiso 1 1 calc R . .
C16 C -0.1909(3) 0.4975(2) -0.12747(8) 0.0651(7) Uani 1 1 d . A .
H16A H -0.2754 0.5493 -0.1085 0.098 Uiso 1 1 calc R . .
H16B H -0.2392 0.4680 -0.1601 0.098 Uiso 1 1 calc R . .
H16C H -0.0914 0.5533 -0.1340 0.098 Uiso 1 1 calc R . .
C17 C -0.0289(4) 0.04568(19) -0.01731(9) 0.0659(7) Uani 1 1 d . . .
H17A H 0.0877 0.0469 -0.0046 0.099 Uiso 1 1 calc R A .
H17B H -0.0438 -0.0300 -0.0407 0.099 Uiso 1 1 calc R . .
H17C H -0.1070 0.0366 0.0116 0.099 Uiso 1 1 calc R . .
F1 F 0.25960(16) 0.66488(12) 0.11852(4) 0.0588(3) Uani 1 1 d . A .
N1 N 0.0372(3) 0.66059(16) 0.20398(6) 0.0491(4) Uani 1 1 d . . .
H1 H 0.009(3) 0.585(2) 0.2163(8) 0.059 Uiso 1 1 d . . .
O1 O 0.0486(3) 0.78326(14) 0.04000(5) 0.0721(5) Uani 1 1 d . . .
O2 O 0.0299(2) 0.85943(15) 0.27038(6) 0.0718(5) Uani 1 1 d . . .
O3 O -0.1415(2) 0.38143(13) -0.09743(5) 0.0545(4) Uani 1 1 d . . .
O4 O -0.06437(19) 0.17055(12) -0.04457(5) 0.0531(4) Uani 1 1 d . A .
S1 S 0.14657(7) 0.77714(4) 0.237036(18) 0.04762(12) Uani 1 1 d . A .


_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
C10 N1 1.442(2) . ?
C10 C12 1.505(9) . ?
C10 C2 1.538(3) . ?
C10 H10 0.9800 . ?
C12 F4 1.308(9) . ?
C12 F3 1.318(9) . ?
C12 F2 1.327(9) . ?
C12' F3' 1.315(11) . ?
C12' F4' 1.325(11) . ?
C12' F2' 1.327(10) . ?
C1 O1 1.206(2) . ?
C1 C5 1.452(2) . ?
C1 C2 1.552(3) . ?
C2 F1 1.402(2) . ?
C2 C3 1.532(2) . ?
C3 C4 1.510(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.381(2) . ?
C4 C9 1.392(2) . ?
C5 C6 1.402(2) . ?
C6 C7 1.360(3) . ?
C6 H6 0.9300 . ?
C7 O3 1.368(2) . ?
C7 C8 1.425(2) . ?
C8 O4 1.349(2) . ?
C8 C9 1.382(2) . ?
C9 H9 0.9300 . ?
C11 C14 1.513(3) . ?
C11 C15 1.520(3) . ?
C11 C13 1.527(3) . ?
C11 S1 1.837(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.426(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.436(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 S1 1.6555(17) . ?
N1 H1 0.83(2) . ?
O2 S1 1.4822(15) . ?

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
N1 C10 C12 111.7(4) . . ?
N1 C10 C2 112.22(16) . . ?
C12 C10 C2 114.8(4) . . ?
N1 C10 H10 105.8 . . ?
C12 C10 H10 105.8 . . ?
C2 C10 H10 105.8 . . ?
F4 C12 F3 108.2(8) . . ?
F4 C12 F2 106.2(8) . . ?
F3 C12 F2 105.1(7) . . ?
F4 C12 C10 112.5(7) . . ?
F3 C12 C10 113.1(7) . . ?
F2 C12 C10 111.3(7) . . ?
F3' C12' F4' 105.4(9) . . ?
F3' C12' F2' 106.5(9) . . ?
F4' C12' F2' 106.2(9) . . ?
O1 C1 C5 130.15(18) . . ?
O1 C1 C2 122.68(17) . . ?
C5 C1 C2 107.13(14) . . ?
F1 C2 C3 109.35(16) . . ?
F1 C2 C10 104.04(14) . . ?
C3 C2 C10 118.67(16) . . ?
F1 C2 C1 105.88(15) . . ?
C3 C2 C1 106.06(14) . . ?
C10 C2 C1 112.17(15) . . ?
C4 C3 C2 103.82(14) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C9 120.00(15) . . ?
C5 C4 C3 112.66(15) . . ?
C9 C4 C3 127.29(16) . . ?
C4 C5 C6 121.86(16) . . ?
C4 C5 C1 110.15(15) . . ?
C6 C5 C1 127.98(16) . . ?
C7 C6 C5 118.24(16) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 O3 125.54(16) . . ?
C6 C7 C8 120.54(16) . . ?
O3 C7 C8 113.91(15) . . ?
O4 C8 C9 124.95(15) . . ?
O4 C8 C7 114.57(14) . . ?
C9 C8 C7 120.47(16) . . ?
C8 C9 C4 118.77(16) . . ?
C8 C9 H9 120.6 . . ?
C4 C9 H9 120.6 . . ?
C14 C11 C15 110.7(2) . . ?
C14 C11 C13 111.89(18) . . ?
C15 C11 C13 111.5(2) . . ?
C14 C11 S1 109.86(17) . . ?
C15 C11 S1 103.35(14) . . ?
C13 C11 S1 109.12(15) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 N1 S1 117.45(12) . . ?
C10 N1 H1 118.8(15) . . ?
S1 N1 H1 123.7(15) . . ?
C7 O3 C16 115.85(15) . . ?
C8 O4 C17 118.07(14) . . ?
O2 S1 N1 110.99(10) . . ?
O2 S1 C11 105.81(9) . . ?
N1 S1 C11 99.37(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
