# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014


data_aa

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F0.04 N O S'
_chemical_formula_weight         75.88

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   10.499(16)
_cell_length_b                   11.042(16)
_cell_length_c                   16.30(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1889(5)
_cell_formula_units_Z            24
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             921
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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            11518
_diffrn_reflns_av_R_equivalents  0.2128
_diffrn_reflns_av_sigmaI/netI    0.1399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3707
_reflns_number_gt                2959
_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)+(0.0700P)²+0.0000P] 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   0.04(12)
_refine_ls_number_reflns         3707
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8009(4) 0.4471(4) 0.2911(3) 0.0530(10) Uani 1 1 d . . .
H1 H 0.8041 0.5312 0.2945 0.064 Uiso 1 1 calc R . .
C2 C 0.8511(4) 0.2719(3) 0.2598(3) 0.0488(9) Uani 1 1 d . . .
C3 C 0.7673(4) 0.0714(3) 0.2910(3) 0.0449(9) Uani 1 1 d . . .
C4 C 0.6968(4) 0.1584(3) 0.3271(2) 0.0427(9) Uani 1 1 d . . .
C5 C 0.5851(4) 0.1420(3) 0.3802(2) 0.0442(9) Uani 1 1 d . . .
C6 C 0.5872(5) 0.1816(5) 0.4612(3) 0.0755(15) Uani 1 1 d . . .
H6 H 0.6579 0.2228 0.4812 0.091 Uiso 1 1 calc R . .
C7 C 0.4836(7) 0.1596(6) 0.5122(4) 0.094(2) Uani 1 1 d . . .
H7 H 0.4850 0.1861 0.5663 0.113 Uiso 1 1 calc R . .
C8 C 0.3779(6) 0.0981(5) 0.4822(4) 0.0780(16) Uani 1 1 d . . .
H8 H 0.3086 0.0834 0.5163 0.094 Uiso 1 1 calc R . .
C9 C 0.3758(5) 0.0585(5) 0.4012(4) 0.0782(15) Uani 1 1 d . . .
H9 H 0.3051 0.0173 0.3812 0.094 Uiso 1 1 calc R . .
C10 C 0.4795(4) 0.0804(5) 0.3502(3) 0.0639(12) Uani 1 1 d . . .
H10 H 0.4781 0.0539 0.2961 0.077 Uiso 1 1 calc R . .
C11 C 0.7579(4) -0.0609(3) 0.3105(3) 0.0459(9) Uani 1 1 d . . .
H11 H 0.6860 -0.0703 0.3482 0.055 Uiso 1 1 calc R . .
C12 C 0.7302(5) -0.1388(4) 0.2374(3) 0.0634(12) Uani 1 1 d . . .
C13 C 0.9659(5) -0.1313(4) 0.5037(3) 0.0648(12) Uani 1 1 d . . .
C14 C 0.9562(8) -0.2136(9) 0.5794(4) 0.129(3) Uani 1 1 d . . .
H14A H 0.9759 -0.2954 0.5641 0.194 Uiso 1 1 calc R . .
H14B H 0.8713 -0.2101 0.6011 0.194 Uiso 1 1 calc R . .
H14C H 1.0154 -0.1867 0.6204 0.194 Uiso 1 1 calc R . .
C15 C 1.0996(5) -0.1330(6) 0.4675(4) 0.0938(19) Uani 1 1 d . . .
H15A H 1.1585 -0.0995 0.5064 0.141 Uiso 1 1 calc R . .
H15B H 1.1011 -0.0857 0.4181 0.141 Uiso 1 1 calc R . .
H15C H 1.1235 -0.2149 0.4552 0.141 Uiso 1 1 calc R . .
C16 C 0.9212(10) -0.0031(6) 0.5212(5) 0.129(3) Uani 1 1 d . . .
H16A H 0.9227 0.0432 0.4713 0.194 Uiso 1 1 calc R . .
H16B H 0.9766 0.0337 0.5608 0.194 Uiso 1 1 calc R . .
H16C H 0.8359 -0.0052 0.5424 0.194 Uiso 1 1 calc R . .
F1 F 0.8156(4) -0.1306(3) 0.1780(2) 0.0933(11) Uani 1 1 d . . .
F2 F 0.7200(4) -0.2538(2) 0.2572(2) 0.0931(11) Uani 1 1 d . . .
F3 F 0.6199(4) -0.1079(3) 0.2026(2) 0.0930(10) Uani 1 1 d . . .
N1 N 0.7428(3) 0.2705(2) 0.30731(19) 0.0420(7) Uani 1 1 d . . .
N2 N 0.7129(3) 0.3853(3) 0.3281(2) 0.0503(8) Uani 1 1 d . . .
N3 N 0.8885(3) 0.3831(3) 0.2471(2) 0.0532(9) Uani 1 1 d . . .
N4 N 0.8708(3) -0.1024(3) 0.3539(2) 0.0463(8) Uani 1 1 d . . .
H4 H 0.9453 -0.0779 0.3395 0.056 Uiso 1 1 calc R . .
O1 O 0.9019(5) -0.3146(3) 0.4085(3) 0.0887(13) Uani 1 1 d . . .
S1 S 0.89357(11) 0.12763(9) 0.23260(8) 0.0563(3) Uani 1 1 d . . .
S2 S 0.85364(10) -0.19684(9) 0.43082(7) 0.0511(3) 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
C1 N2 1.297(6) . ?
C1 N3 1.365(6) . ?
C1 H1 0.9300 . ?
C2 N3 1.305(5) . ?
C2 N1 1.376(5) . ?
C2 S1 1.713(4) . ?
C3 C4 1.348(5) . ?
C3 C11 1.498(6) . ?
C3 S1 1.745(4) . ?
C4 N1 1.367(5) . ?
C4 C5 1.468(6) . ?
C5 C6 1.390(7) . ?
C5 C10 1.390(6) . ?
C6 C7 1.390(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N4 1.455(5) . ?
C11 C12 1.497(7) . ?
C11 H11 0.9800 . ?
C12 F2 1.315(5) . ?
C12 F1 1.323(7) . ?
C12 F3 1.333(6) . ?
C13 C16 1.518(8) . ?
C13 C15 1.523(8) . ?
C13 C14 1.535(8) . ?
C13 S2 1.823(5) . ?
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 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.349(5) . ?
N4 S2 1.640(4) . ?
N4 H4 0.8600 . ?
O1 S2 1.442(4) . ?

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
N2 C1 N3 116.9(4) . . ?
N2 C1 H1 121.6 . . ?
N3 C1 H1 121.6 . . ?
N3 C2 N1 110.4(3) . . ?
N3 C2 S1 139.1(3) . . ?
N1 C2 S1 110.5(3) . . ?
C4 C3 C11 124.5(4) . . ?
C4 C3 S1 113.7(3) . . ?
C11 C3 S1 120.8(3) . . ?
C3 C4 N1 110.4(3) . . ?
C3 C4 C5 127.4(3) . . ?
N1 C4 C5 122.2(3) . . ?
C6 C5 C10 120.0(4) . . ?
C6 C5 C4 120.5(4) . . ?
C10 C5 C4 119.4(4) . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.0(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 120.0(5) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
N4 C11 C12 111.3(4) . . ?
N4 C11 C3 110.9(3) . . ?
C12 C11 C3 113.9(4) . . ?
N4 C11 H11 106.8 . . ?
C12 C11 H11 106.8 . . ?
C3 C11 H11 106.8 . . ?
F2 C12 F1 107.4(4) . . ?
F2 C12 F3 106.3(4) . . ?
F1 C12 F3 105.0(4) . . ?
F2 C12 C11 112.1(4) . . ?
F1 C12 C11 114.3(4) . . ?
F3 C12 C11 111.1(4) . . ?
C16 C13 C15 111.6(6) . . ?
C16 C13 C14 112.4(6) . . ?
C15 C13 C14 111.4(5) . . ?
C16 C13 S2 107.0(4) . . ?
C15 C13 S2 109.8(4) . . ?
C14 C13 S2 104.3(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 N1 C4 135.2(3) . . ?
N2 N1 C2 108.9(3) . . ?
C4 N1 C2 115.8(3) . . ?
C1 N2 N1 102.2(3) . . ?
C2 N3 C1 101.6(3) . . ?
C11 N4 S2 118.9(3) . . ?
C11 N4 H4 120.6 . . ?
S2 N4 H4 120.6 . . ?
C2 S1 C3 89.56(19) . . ?
O1 S2 N4 110.0(2) . . ?
O1 S2 C13 107.2(3) . . ?
N4 S2 C13 100.1(2) . . ?

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
C11 C3 C4 N1 169.2(4) . . . . ?
S1 C3 C4 N1 0.8(4) . . . . ?
C11 C3 C4 C5 -11.3(7) . . . . ?
S1 C3 C4 C5 -179.7(3) . . . . ?
C3 C4 C5 C6 118.0(5) . . . . ?
N1 C4 C5 C6 -62.5(6) . . . . ?
C3 C4 C5 C10 -58.5(6) . . . . ?
N1 C4 C5 C10 121.0(5) . . . . ?
C10 C5 C6 C7 0.0(8) . . . . ?
C4 C5 C6 C7 -176.5(5) . . . . ?
C5 C6 C7 C8 0.0(10) . . . . ?
C6 C7 C8 C9 0.0(10) . . . . ?
C7 C8 C9 C10 0.0(9) . . . . ?
C8 C9 C10 C5 0.0(8) . . . . ?
C6 C5 C10 C9 0.0(7) . . . . ?
C4 C5 C10 C9 176.5(4) . . . . ?
C4 C3 C11 N4 -109.6(5) . . . . ?
S1 C3 C11 N4 58.1(5) . . . . ?
C4 C3 C11 C12 123.9(5) . . . . ?
S1 C3 C11 C12 -68.4(5) . . . . ?
N4 C11 C12 F2 55.0(6) . . . . ?
C3 C11 C12 F2 -178.7(4) . . . . ?
N4 C11 C12 F1 -67.5(5) . . . . ?
C3 C11 C12 F1 58.7(5) . . . . ?
N4 C11 C12 F3 173.8(4) . . . . ?
C3 C11 C12 F3 -59.9(5) . . . . ?
C3 C4 N1 N2 -177.0(4) . . . . ?
C5 C4 N1 N2 3.4(7) . . . . ?
C3 C4 N1 C2 -3.0(5) . . . . ?
C5 C4 N1 C2 177.4(4) . . . . ?
N3 C2 N1 N2 -2.3(5) . . . . ?
S1 C2 N1 N2 179.5(3) . . . . ?
N3 C2 N1 C4 -177.9(4) . . . . ?
S1 C2 N1 C4 3.9(5) . . . . ?
N3 C1 N2 N1 -0.3(5) . . . . ?
C4 N1 N2 C1 175.8(4) . . . . ?
C2 N1 N2 C1 1.5(4) . . . . ?
N1 C2 N3 C1 2.0(5) . . . . ?
S1 C2 N3 C1 179.4(5) . . . . ?
N2 C1 N3 C2 -1.1(5) . . . . ?
C12 C11 N4 S2 -93.2(4) . . . . ?
C3 C11 N4 S2 138.9(3) . . . . ?
N3 C2 S1 C3 179.8(6) . . . . ?
N1 C2 S1 C3 -2.8(3) . . . . ?
C4 C3 S1 C2 1.2(3) . . . . ?
C11 C3 S1 C2 -167.7(4) . . . . ?
C11 N4 S2 O1 110.1(3) . . . . ?
C11 N4 S2 C13 -137.3(3) . . . . ?
C16 C13 S2 O1 175.0(5) . . . . ?
C15 C13 S2 O1 53.7(5) . . . . ?
C14 C13 S2 O1 -65.7(5) . . . . ?
C16 C13 S2 N4 60.3(5) . . . . ?
C15 C13 S2 N4 -61.0(4) . . . . ?
C14 C13 S2 N4 179.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 948095'
