# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1432097'
_audit_update_record             
;
2015-10-19 deposited with the CCDC.
2015-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        DSF
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 F6 N2 O P S2'
_chemical_formula_weight         476.43

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'
P P 0.1023 0.0942 '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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.645(5)
_cell_length_b                   11.246(5)
_cell_length_c                   12.326(5)
_cell_angle_alpha                95.390(5)
_cell_angle_beta                 105.282(5)
_cell_angle_gamma                93.459(5)
_cell_volume                     1013.7(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    327(2)
_cell_measurement_reflns_used    2643
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.57

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8877
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      327(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7154
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3522
_reflns_number_gt                2618
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1140P)²+1.7411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3522
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2238
_refine_ls_wR_factor_gt          0.2026
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
S1 S 0.49472(15) 0.08188(10) 0.70315(9) 0.0487(4) Uani 1 1 d . . .
S2 S -0.01514(15) -0.06987(10) 0.26935(10) 0.0514(4) Uani 1 1 d . . .
P1 P 0.7809(2) 0.30151(13) 0.25573(12) 0.0749(5) Uani 1 1 d . . .
C4 C -0.1212(6) -0.2124(4) 0.2160(4) 0.0482(10) Uani 1 1 d . . .
N2 N 0.4323(5) 0.2601(3) 0.5888(3) 0.0497(9) Uani 1 1 d . . .
C10 C 0.3852(6) 0.1418(4) 0.5807(3) 0.0443(10) Uani 1 1 d . . .
N1 N -0.2391(5) -0.2343(4) 0.1138(3) 0.0598(10) Uani 1 1 d . . .
C11 C 0.5569(6) 0.3085(4) 0.6911(4) 0.0487(10) Uani 1 1 d . . .
C8 C 0.2200(6) -0.0468(4) 0.4842(4) 0.0485(10) Uani 1 1 d . . .
H8 H 0.2743 -0.0823 0.5484 0.058 Uiso 1 1 calc R . .
C7 C 0.1024(6) -0.1219(4) 0.3955(4) 0.0473(10) Uani 1 1 d . . .
C12 C 0.6058(6) 0.2218(4) 0.7635(4) 0.0470(10) Uani 1 1 d . . .
F4 F 0.9192(7) 0.2260(4) 0.3298(4) 0.144(2) Uani 1 1 d . . .
C6 C 0.0573(6) -0.2434(4) 0.3914(4) 0.0527(11) Uani 1 1 d . . .
H6 H 0.1063 -0.2866 0.4513 0.063 Uiso 1 1 calc R . .
C9 C 0.2645(6) 0.0728(4) 0.4875(4) 0.0489(10) Uani 1 1 d . . .
H9 H 0.2119 0.1107 0.4245 0.059 Uiso 1 1 calc R . .
C5 C -0.0645(6) -0.2960(4) 0.2935(4) 0.0541(11) Uani 1 1 d . . .
H5 H -0.1048 -0.3771 0.2799 0.065 Uiso 1 1 calc R . .
C16 C 0.7288(6) 0.2510(5) 0.8699(4) 0.0584(12) Uani 1 1 d . . .
H16 H 0.7609 0.1929 0.9187 0.070 Uiso 1 1 calc R . .
F6 F 0.7324(8) 0.1987(5) 0.1565(4) 0.147(2) Uani 1 1 d . . .
C13 C 0.6296(7) 0.4260(5) 0.7222(5) 0.0642(13) Uani 1 1 d . . .
H13 H 0.5968 0.4845 0.6739 0.077 Uiso 1 1 calc R . .
C3 C -0.3200(7) -0.3570(5) 0.0737(5) 0.0673(14) Uani 1 1 d . . .
H3A H -0.2264 -0.4075 0.0654 0.101 Uiso 1 1 calc R . .
H3B H -0.4084 -0.3580 0.0019 0.101 Uiso 1 1 calc R . .
H3C H -0.3782 -0.3859 0.1275 0.101 Uiso 1 1 calc R . .
C15 C 0.8010(7) 0.3678(5) 0.9006(5) 0.0670(14) Uani 1 1 d . . .
H15 H 0.8831 0.3892 0.9712 0.080 Uiso 1 1 calc R . .
C21 C 0.3577(9) 0.3339(5) 0.5001(5) 0.0761(16) Uani 1 1 d . . .
H21A H 0.4207 0.3247 0.4424 0.114 Uiso 1 1 calc R . .
H21B H 0.3724 0.4165 0.5316 0.114 Uiso 1 1 calc R . .
H21C H 0.2306 0.3095 0.4678 0.114 Uiso 1 1 calc R . .
C2 C -0.2991(8) -0.1406(5) 0.0418(5) 0.0775(16) Uani 1 1 d . . .
H2A H -0.2585 -0.0664 0.0915 0.093 Uiso 1 1 calc R . .
H2B H -0.4307 -0.1485 0.0262 0.093 Uiso 1 1 calc R . .
C14 C 0.7534(8) 0.4541(5) 0.8280(5) 0.0704(15) Uani 1 1 d . . .
H14 H 0.8052 0.5325 0.8504 0.084 Uiso 1 1 calc R . .
F2 F 0.9202(12) 0.3573(9) 0.2069(7) 0.250(4) Uani 1 1 d . . .
F1 F 0.6362(11) 0.3713(6) 0.1848(5) 0.217(4) Uani 1 1 d . . .
F3 F 0.8280(13) 0.4018(5) 0.3543(5) 0.218(4) Uani 1 1 d . . .
F5 F 0.6373(10) 0.2432(8) 0.3049(7) 0.206(3) Uani 1 1 d . . .
C1 C -0.2600(17) -0.111(2) -0.0829(15) 0.297(15) Uani 1 1 d . . .
H1A H -0.3325 -0.1638 -0.1479 0.356 Uiso 1 1 calc R . .
H1B H -0.2677 -0.0275 -0.0964 0.356 Uiso 1 1 calc R . .
O1 O -0.104(3) -0.1378(10) -0.0474(9) 0.306(8) Uani 1 1 d . . .
H1 H -0.0931 -0.2022 -0.0808 0.459 Uiso 1 1 calc R . .


_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 C10 1.739(4) . ?
S1 C12 1.742(5) . ?
S2 C4 1.739(4) . ?
S2 C7 1.751(4) . ?
P1 F2 1.489(6) . ?
P1 F1 1.526(5) . ?
P1 F5 1.530(6) . ?
P1 F3 1.530(5) . ?
P1 F6 1.554(5) . ?
P1 F4 1.555(4) . ?
C4 N1 1.333(6) . ?
C4 C5 1.408(7) . ?
N2 C10 1.345(6) . ?
N2 C11 1.402(6) . ?
N2 C21 1.452(6) . ?
C10 C9 1.401(6) . ?
N1 C2 1.459(7) . ?
N1 C3 1.462(6) . ?
C11 C13 1.381(6) . ?
C11 C12 1.385(6) . ?
C8 C9 1.361(7) . ?
C8 C7 1.389(6) . ?
C8 H8 0.9300 . ?
C7 C6 1.382(6) . ?
C12 C16 1.394(6) . ?
C6 C5 1.372(6) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C16 C15 1.372(7) . ?
C16 H16 0.9300 . ?
C13 C14 1.390(8) . ?
C13 H13 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C15 C14 1.381(8) . ?
C15 H15 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C2 C1 1.70(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C14 H14 0.9300 . ?
C1 O1 1.22(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O1 H1 0.8200 . ?

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
C10 S1 C12 90.9(2) . . ?
C4 S2 C7 91.3(2) . . ?
F2 P1 F1 90.1(6) . . ?
F2 P1 F5 179.4(5) . . ?
F1 P1 F5 89.9(5) . . ?
F2 P1 F3 90.5(5) . . ?
F1 P1 F3 91.9(4) . . ?
F5 P1 F3 90.1(5) . . ?
F2 P1 F6 90.1(4) . . ?
F1 P1 F6 88.4(3) . . ?
F5 P1 F6 89.3(4) . . ?
F3 P1 F6 179.3(4) . . ?
F2 P1 F4 93.3(5) . . ?
F1 P1 F4 176.6(4) . . ?
F5 P1 F4 86.8(4) . . ?
F3 P1 F4 88.7(3) . . ?
F6 P1 F4 90.9(3) . . ?
N1 C4 C5 126.8(4) . . ?
N1 C4 S2 121.9(4) . . ?
C5 C4 S2 111.3(3) . . ?
C10 N2 C11 115.0(4) . . ?
C10 N2 C21 123.1(4) . . ?
C11 N2 C21 121.9(4) . . ?
N2 C10 C9 125.9(4) . . ?
N2 C10 S1 111.2(3) . . ?
C9 C10 S1 122.9(3) . . ?
C4 N1 C2 123.1(4) . . ?
C4 N1 C3 118.8(4) . . ?
C2 N1 C3 118.0(4) . . ?
C13 C11 C12 120.8(4) . . ?
C13 C11 N2 127.6(4) . . ?
C12 C11 N2 111.6(4) . . ?
C9 C8 C7 127.3(4) . . ?
C9 C8 H8 116.4 . . ?
C7 C8 H8 116.4 . . ?
C6 C7 C8 127.6(4) . . ?
C6 C7 S2 109.9(3) . . ?
C8 C7 S2 122.6(4) . . ?
C11 C12 C16 120.9(4) . . ?
C11 C12 S1 111.3(3) . . ?
C16 C12 S1 127.9(4) . . ?
C5 C6 C7 115.7(4) . . ?
C5 C6 H6 122.1 . . ?
C7 C6 H6 122.1 . . ?
C8 C9 C10 123.5(4) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C6 C5 C4 111.8(4) . . ?
C6 C5 H5 124.1 . . ?
C4 C5 H5 124.1 . . ?
C15 C16 C12 118.2(5) . . ?
C15 C16 H16 120.9 . . ?
C12 C16 H16 120.9 . . ?
C11 C13 C14 117.8(5) . . ?
C11 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C2 C1 131.2(9) . . ?
N1 C2 H2A 104.4 . . ?
C1 C2 H2A 104.4 . . ?
N1 C2 H2B 104.4 . . ?
C1 C2 H2B 104.4 . . ?
H2A C2 H2B 105.6 . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O1 C1 C2 88.7(16) . . ?
O1 C1 H1A 113.9 . . ?
C2 C1 H1A 113.9 . . ?
O1 C1 H1B 113.9 . . ?
C2 C1 H1B 113.9 . . ?
H1A C1 H1B 111.1 . . ?
C1 O1 H1 109.5 . . ?

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
C7 S2 C4 N1 179.7(4) . . . . ?
C7 S2 C4 C5 -0.7(3) . . . . ?
C11 N2 C10 C9 -179.6(4) . . . . ?
C21 N2 C10 C9 1.7(7) . . . . ?
C11 N2 C10 S1 0.3(5) . . . . ?
C21 N2 C10 S1 -178.3(4) . . . . ?
C12 S1 C10 N2 -0.4(3) . . . . ?
C12 S1 C10 C9 179.5(4) . . . . ?
C5 C4 N1 C2 175.9(5) . . . . ?
S2 C4 N1 C2 -4.5(7) . . . . ?
C5 C4 N1 C3 -0.8(7) . . . . ?
S2 C4 N1 C3 178.7(3) . . . . ?
C10 N2 C11 C13 179.5(5) . . . . ?
C21 N2 C11 C13 -1.9(8) . . . . ?
C10 N2 C11 C12 0.0(5) . . . . ?
C21 N2 C11 C12 178.7(4) . . . . ?
C9 C8 C7 C6 179.7(4) . . . . ?
C9 C8 C7 S2 -1.3(7) . . . . ?
C4 S2 C7 C6 0.3(3) . . . . ?
C4 S2 C7 C8 -178.9(4) . . . . ?
C13 C11 C12 C16 0.4(7) . . . . ?
N2 C11 C12 C16 180.0(4) . . . . ?
C13 C11 C12 S1 -179.9(4) . . . . ?
N2 C11 C12 S1 -0.4(5) . . . . ?
C10 S1 C12 C11 0.4(3) . . . . ?
C10 S1 C12 C16 -179.9(4) . . . . ?
C8 C7 C6 C5 179.3(4) . . . . ?
S2 C7 C6 C5 0.2(5) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
N2 C10 C9 C8 -179.3(4) . . . . ?
S1 C10 C9 C8 0.7(6) . . . . ?
C7 C6 C5 C4 -0.7(6) . . . . ?
N1 C4 C5 C6 -179.5(5) . . . . ?
S2 C4 C5 C6 0.9(5) . . . . ?
C11 C12 C16 C15 -0.5(7) . . . . ?
S1 C12 C16 C15 179.9(4) . . . . ?
C12 C11 C13 C14 0.2(7) . . . . ?
N2 C11 C13 C14 -179.3(5) . . . . ?
C12 C16 C15 C14 -0.1(8) . . . . ?
C4 N1 C2 C1 111.8(8) . . . . ?
C3 N1 C2 C1 -71.5(9) . . . . ?
C16 C15 C14 C13 0.7(8) . . . . ?
C11 C13 C14 C15 -0.8(8) . . . . ?
N1 C2 C1 O1 -38.5(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.073
