# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1455891'
_audit_update_record             
;
2016-02-26 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 F3 N O4 S'
_chemical_formula_weight         387.37

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.3925(8)
_cell_length_b                   9.5682(9)
_cell_length_c                   10.9216(10)
_cell_angle_alpha                73.528(8)
_cell_angle_beta                 66.260(9)
_cell_angle_gamma                85.458(7)
_cell_volume                     860.90(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    2108
_cell_measurement_theta_min      2.9733
_cell_measurement_theta_max      29.0505

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_T_min  0.52057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            7934
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         29.115
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3951
_reflns_number_gt                2797
_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       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_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)+(0.0609P)²+0.1792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3951
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.66160(8) 0.33433(7) 0.69478(6) 0.0535(2) Uani 1 1 d . . . . .
O1 O 1.00062(18) 0.32942(18) 0.81839(16) 0.0533(4) Uani 1 1 d . . . . .
O2 O 0.82045(18) 0.41674(17) 0.64663(16) 0.0479(4) Uani 1 1 d . . . . .
F2 F 0.6620(2) 0.4554(2) 0.44661(19) 0.0946(6) Uani 1 1 d . . . . .
N1 N 0.7585(2) 0.26690(19) 0.98741(18) 0.0449(5) Uani 1 1 d . . . . .
F3 F 0.5351(3) 0.2550(2) 0.5544(2) 0.0985(6) Uani 1 1 d . . . . .
O3 O 0.6778(3) 0.1882(2) 0.7609(2) 0.0864(7) Uani 1 1 d . . . . .
C9 C 0.8368(2) 0.5237(2) 0.8691(2) 0.0399(5) Uani 1 1 d . . . . .
F1 F 0.7825(3) 0.2597(3) 0.4639(2) 0.1179(8) Uani 1 1 d . . . . .
O4 O 0.5352(2) 0.4165(2) 0.7546(2) 0.0766(6) Uani 1 1 d . . . . .
C10 C 0.8322(2) 0.6167(2) 0.7424(2) 0.0377(5) Uani 1 1 d . . . . .
C5 C 0.8333(3) 0.7710(2) 0.7227(2) 0.0459(5) Uani 1 1 d . . . . .
C11 C 0.8705(3) 0.3643(2) 0.8882(2) 0.0406(5) Uani 1 1 d . . . . .
C1 C 0.8282(2) 0.5704(2) 0.6314(2) 0.0411(5) Uani 1 1 d . . . . .
C6 C 0.8295(3) 0.8261(3) 0.8304(3) 0.0556(6) Uani 1 1 d . . . . .
H6 H 0.8279 0.9263 0.8183 0.067 Uiso 1 1 calc R U . . .
C15 C 0.6029(3) 0.3011(3) 1.0758(2) 0.0478(6) Uani 1 1 d . . . . .
H15A H 0.5249 0.2543 1.0618 0.057 Uiso 1 1 calc R U . . .
H15B H 0.5904 0.4056 1.0507 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6624(4) 0.3270(3) 0.5282(3) 0.0650(8) Uani 1 1 d . . . . .
C8 C 0.8341(3) 0.5848(3) 0.9697(2) 0.0493(6) Uani 1 1 d . . . . .
H8 H 0.8364 0.5241 1.0521 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8411(3) 0.6637(3) 0.5067(2) 0.0525(6) Uani 1 1 d . . . . .
H2 H 0.8452 0.6278 0.4347 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7673(3) 0.0514(3) 1.1702(3) 0.0593(7) Uani 1 1 d . . . . .
H13A H 0.8475 0.0942 1.1847 0.071 Uiso 1 1 calc R U . . .
H13B H 0.7783 -0.0534 1.1917 0.071 Uiso 1 1 calc R U . . .
C16 C 0.5805(3) 0.2478(3) 1.2270(2) 0.0527(6) Uani 1 1 d . . . . .
H16A H 0.4755 0.2661 1.2855 0.063 Uiso 1 1 calc R U . . .
H16B H 0.6524 0.3013 1.2424 0.063 Uiso 1 1 calc R U . . .
C7 C 0.8280(3) 0.7357(3) 0.9518(3) 0.0583(7) Uani 1 1 d . . . . .
H7 H 0.8230 0.7738 1.0229 0.070 Uiso 1 1 calc R U . . .
C14 C 0.6083(3) 0.0858(3) 1.2669(3) 0.0614(7) Uani 1 1 d . . . . .
H14A H 0.6011 0.0556 1.3618 0.074 Uiso 1 1 calc R U . . .
H14B H 0.5284 0.0316 1.2623 0.074 Uiso 1 1 calc R U . . .
C12 C 0.7883(3) 0.1108(3) 1.0196(3) 0.0571(7) Uani 1 1 d . . . . .
H12A H 0.8937 0.0954 0.9594 0.068 Uiso 1 1 calc R U . . .
H12B H 0.7173 0.0586 1.0021 0.068 Uiso 1 1 calc R U . . .
C4 C 0.8401(3) 0.8664(3) 0.5947(3) 0.0555(6) Uani 1 1 d . . . . .
H4 H 0.8391 0.9666 0.5830 0.067 Uiso 1 1 calc R U . . .
C3 C 0.8480(3) 0.8145(3) 0.4887(3) 0.0606(7) Uani 1 1 d . . . . .
H3 H 0.8581 0.8792 0.4038 0.073 Uiso 1 1 calc R U . . .


_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 O4 1.4050(19) . ?
S1 O3 1.4074(19) . ?
S1 O2 1.5633(17) . ?
S1 C17 1.838(3) . ?
O1 C11 1.231(2) . ?
O2 C1 1.436(3) . ?
F2 C17 1.298(3) . ?
N1 C11 1.347(3) . ?
N1 C15 1.464(3) . ?
N1 C12 1.466(3) . ?
F3 C17 1.315(3) . ?
C9 C8 1.374(3) . ?
C9 C10 1.433(3) . ?
C9 C11 1.505(3) . ?
F1 C17 1.298(3) . ?
C10 C1 1.418(3) . ?
C10 C5 1.431(3) . ?
C5 C6 1.406(3) . ?
C5 C4 1.416(3) . ?
C1 C2 1.364(3) . ?
C6 C7 1.358(3) . ?
C6 H6 0.9300 . ?
C15 C16 1.514(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C8 C7 1.400(3) . ?
C8 H8 0.9300 . ?
C2 C3 1.404(4) . ?
C2 H2 0.9300 . ?
C13 C12 1.514(3) . ?
C13 C14 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 C14 1.518(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C7 H7 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 C3 1.357(4) . ?
C4 H4 0.9300 . ?
C3 H3 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
O4 S1 O3 122.76(15) . . ?
O4 S1 O2 111.47(10) . . ?
O3 S1 O2 106.90(12) . . ?
O4 S1 C17 107.90(14) . . ?
O3 S1 C17 103.82(13) . . ?
O2 S1 C17 101.76(12) . . ?
C1 O2 S1 121.16(13) . . ?
C11 N1 C15 126.00(18) . . ?
C11 N1 C12 120.56(19) . . ?
C15 N1 C12 113.40(19) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 C11 117.54(19) . . ?
C10 C9 C11 122.55(19) . . ?
C1 C10 C5 115.7(2) . . ?
C1 C10 C9 126.0(2) . . ?
C5 C10 C9 118.3(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 C10 119.4(2) . . ?
C4 C5 C10 119.8(2) . . ?
O1 C11 N1 123.2(2) . . ?
O1 C11 C9 118.9(2) . . ?
N1 C11 C9 117.74(18) . . ?
C2 C1 C10 123.6(2) . . ?
C2 C1 O2 117.6(2) . . ?
C10 C1 O2 118.64(18) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C15 C16 109.72(18) . . ?
N1 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N1 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
F1 C17 F2 108.9(3) . . ?
F1 C17 F3 108.9(3) . . ?
F2 C17 F3 107.4(2) . . ?
F1 C17 S1 110.71(19) . . ?
F2 C17 S1 112.7(2) . . ?
F3 C17 S1 108.1(2) . . ?
C9 C8 C7 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C12 C13 C14 110.8(2) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C15 C16 C14 110.8(2) . . ?
C15 C16 H16A 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C13 C14 C16 111.0(2) . . ?
C13 C14 H14A 109.4 . . ?
C16 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C16 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N1 C12 C13 110.73(19) . . ?
N1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?

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
O4 S1 O2 C1 -16.21(19) . . . . ?
O3 S1 O2 C1 -152.86(16) . . . . ?
C17 S1 O2 C1 98.58(17) . . . . ?
C8 C9 C10 C1 -177.4(2) . . . . ?
C11 C9 C10 C1 12.7(3) . . . . ?
C8 C9 C10 C5 3.3(3) . . . . ?
C11 C9 C10 C5 -166.54(19) . . . . ?
C1 C10 C5 C6 176.9(2) . . . . ?
C9 C10 C5 C6 -3.8(3) . . . . ?
C1 C10 C5 C4 -3.8(3) . . . . ?
C9 C10 C5 C4 175.50(19) . . . . ?
C15 N1 C11 O1 178.8(2) . . . . ?
C12 N1 C11 O1 1.3(3) . . . . ?
C15 N1 C11 C9 2.8(3) . . . . ?
C12 N1 C11 C9 -174.76(19) . . . . ?
C8 C9 C11 O1 -103.7(2) . . . . ?
C10 C9 C11 O1 66.3(3) . . . . ?
C8 C9 C11 N1 72.5(3) . . . . ?
C10 C9 C11 N1 -117.5(2) . . . . ?
C5 C10 C1 C2 6.8(3) . . . . ?
C9 C10 C1 C2 -172.5(2) . . . . ?
C5 C10 C1 O2 -177.49(17) . . . . ?
C9 C10 C1 O2 3.2(3) . . . . ?
S1 O2 C1 C2 -87.2(2) . . . . ?
S1 O2 C1 C10 96.8(2) . . . . ?
C4 C5 C6 C7 -177.9(2) . . . . ?
C10 C5 C6 C7 1.4(4) . . . . ?
C11 N1 C15 C16 -119.1(2) . . . . ?
C12 N1 C15 C16 58.6(3) . . . . ?
O4 S1 C17 F1 176.2(2) . . . . ?
O3 S1 C17 F1 -52.1(3) . . . . ?
O2 S1 C17 F1 58.8(2) . . . . ?
O4 S1 C17 F2 53.9(3) . . . . ?
O3 S1 C17 F2 -174.4(2) . . . . ?
O2 S1 C17 F2 -63.4(2) . . . . ?
O4 S1 C17 F3 -64.6(2) . . . . ?
O3 S1 C17 F3 67.1(2) . . . . ?
O2 S1 C17 F3 178.02(18) . . . . ?
C10 C9 C8 C7 -0.4(3) . . . . ?
C11 C9 C8 C7 169.9(2) . . . . ?
C10 C1 C2 C3 -4.6(3) . . . . ?
O2 C1 C2 C3 179.6(2) . . . . ?
N1 C15 C16 C14 -56.2(3) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C9 C8 C7 C6 -2.0(4) . . . . ?
C12 C13 C14 C16 -53.5(3) . . . . ?
C15 C16 C14 C13 54.8(3) . . . . ?
C11 N1 C12 C13 120.0(2) . . . . ?
C15 N1 C12 C13 -57.8(3) . . . . ?
C14 C13 C12 N1 54.1(3) . . . . ?
C6 C5 C4 C3 178.2(2) . . . . ?
C10 C5 C4 C3 -1.0(4) . . . . ?
C5 C4 C3 C2 3.5(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

