#Supplementary Material (ESI) for Chemical Communications
#This journal is © The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Luis P.N. Rebelo'
_publ_contact_author_address     
;
ITQB, UNL, Av. Rep\'ublica, Ap. 127,
2780-901 Oeiras, Portugal
;

_publ_contact_author_email       luis.rebelo@itqb.unl.pt

loop_
_publ_author_name
_publ_author_address
J.Lachwa
;
ITQB, UNL, Av. Rep\'ublica, Ap. 127,
2780-901 Oeiras, Portugal
;
I.Bento
;
ITQB, UNL, Av. Rep\'ublica, Ap. 127,
2780-901 Oeiras, Portugal
;
M.T.Duarte
;
Centro de Qu\'imica Estrutural,
Complexo I, IST, 1049-001 Lisboa, Portugal
;
J.N.C.Lopes
;
Centro de Qu\'imica Estrutural,
Complexo I, IST, 1049-001 Lisboa, Portugal'
;
L.P.N.Rebelo
;
ITQB, UNL, Av. Rep\'ublica, Ap. 127,
2780-901 Oeiras, Portugal
;

data_ib0015
_database_code_depnum_ccdc_archive 'CCDC 299700'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H11 N2 1+, C2 F6 N O4 S2 1-, C6 H6'
_chemical_formula_sum            'C14 H17 F6 N3 O4 S2'
_chemical_formula_weight         469.43

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.348(3)
_cell_length_b                   10.922(3)
_cell_length_c                   13.743(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.753(3)
_cell_angle_gamma                90.00
_cell_volume                     1989.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    11061
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.78

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.
_exptl_absorpt_correction_T_max  0.
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.88560
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'synchrotron, beamline ID29'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  'scanner ADSC'
_diffrn_measurement_method       '3 deg oscillations, exposure time 100ms'
_diffrn_detector_area_resol_mean 'not applicable'
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11061
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.78
_reflns_number_total             2382
_reflns_number_gt                2064
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'MOSFLM (Leslie, 1992)'
_computing_data_reduction        'SCALA (CCP4 suite, 1994)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1068P)^2^+0.2582P] where P=(Fo^2^+2Fc^2^)/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         2382
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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
F1 F 0.44709(14) 0.07343(18) 0.10079(15) 0.0427(6) Uani 1 1 d . . .
F2 F 0.40660(16) 0.1019(2) -0.05362(14) 0.0561(7) Uani 1 1 d . . .
F3 F 0.30259(15) 0.01438(17) 0.03239(14) 0.0427(6) Uani 1 1 d . . .
C1 C 0.3718(2) 0.1022(3) 0.0328(2) 0.0306(9) Uani 1 1 d . . .
S1 S 0.31877(6) 0.25177(7) 0.05443(5) 0.0202(3) Uani 1 1 d . . .
O1 O 0.40275(16) 0.3326(2) 0.05233(15) 0.0339(6) Uani 1 1 d . . .
O2 O 0.23490(16) 0.26267(18) -0.01937(14) 0.0250(6) Uani 1 1 d . . .
N1 N 0.29458(19) 0.2424(2) 0.16353(17) 0.0192(6) Uani 1 1 d . . .
S2 S 0.18898(6) 0.20486(7) 0.19482(5) 0.0189(3) Uani 1 1 d . . .
O3 O 0.12483(16) 0.13654(19) 0.12457(16) 0.0299(6) Uani 1 1 d . . .
O4 O 0.20209(16) 0.1638(2) 0.29326(15) 0.0314(6) Uani 1 1 d . . .
C2 C 0.1261(3) 0.3520(3) 0.2012(3) 0.0374(10) Uani 1 1 d . . .
F4 F 0.03786(15) 0.3372(2) 0.23472(17) 0.0591(7) Uani 1 1 d . . .
F5 F 0.17960(18) 0.42722(19) 0.26110(19) 0.0660(8) Uani 1 1 d . . .
F6 F 0.1103(2) 0.4029(2) 0.11387(19) 0.0785(9) Uani 1 1 d . . .
N2 N 0.50005(18) 0.3998(2) 0.35872(18) 0.0188(6) Uani 1 1 d . . .
C3 C 0.4798(2) 0.4361(3) 0.2662(2) 0.0222(8) Uani 1 1 d . . .
H3 H 0.4286 0.4056 0.2210 0.027 Uiso 1 1 calc R . .
N3 N 0.54485(18) 0.5231(2) 0.24885(17) 0.0199(6) Uani 1 1 d . . .
C4 C 0.6085(2) 0.5433(3) 0.3331(2) 0.0218(8) Uani 1 1 d . . .
H4 H 0.6611 0.5996 0.3414 0.026 Uiso 1 1 calc R . .
C5 C 0.5805(2) 0.4663(3) 0.4016(2) 0.0223(8) Uani 1 1 d . . .
H5 H 0.6103 0.4594 0.4660 0.027 Uiso 1 1 calc R . .
C6 C 0.5505(2) 0.5816(3) 0.1538(2) 0.0301(9) Uani 1 1 d . . .
H6A H 0.6093 0.5529 0.1267 0.045 Uiso 1 1 calc R . .
H6B H 0.5545 0.6688 0.1622 0.045 Uiso 1 1 calc R . .
H6C H 0.4913 0.5615 0.1101 0.045 Uiso 1 1 calc R . .
C7 C 0.4456(3) 0.3035(3) 0.4056(2) 0.0289(8) Uani 1 1 d . . .
H7A H 0.3743 0.3086 0.3821 0.035 Uiso 1 1 calc R . .
H7B H 0.4533 0.3168 0.4758 0.035 Uiso 1 1 calc R . .
C8 C 0.4837(3) 0.1785(3) 0.3845(3) 0.0357(9) Uani 1 1 d . . .
H8A H 0.4688 0.1613 0.3158 0.053 Uiso 1 1 calc R . .
H8B H 0.4514 0.1188 0.4215 0.053 Uiso 1 1 calc R . .
H8C H 0.5553 0.1753 0.4027 0.053 Uiso 1 1 calc R . .
C9 C 0.1675(3) 0.2240(3) 0.5608(3) 0.0376(10) Uani 1 1 d . . .
H9 H 0.1239 0.2605 0.5114 0.045 Uiso 1 1 calc R . .
C10 C 0.1606(3) 0.2525(3) 0.6573(3) 0.0369(10) Uani 1 1 d . . .
H10 H 0.1126 0.3085 0.6730 0.044 Uiso 1 1 calc R . .
C11 C 0.2241(3) 0.1987(3) 0.7298(3) 0.0330(9) Uani 1 1 d . . .
H11 H 0.2195 0.2182 0.7950 0.040 Uiso 1 1 calc R . .
C12 C 0.2947(3) 0.1159(3) 0.7065(3) 0.0352(9) Uani 1 1 d . . .
H12 H 0.3374 0.0781 0.7559 0.042 Uiso 1 1 calc R . .
C13 C 0.3023(3) 0.0889(3) 0.6099(3) 0.0403(10) Uani 1 1 d . . .
H13 H 0.3512 0.0341 0.5942 0.048 Uiso 1 1 calc R . .
C14 C 0.2386(3) 0.1418(3) 0.5372(3) 0.0380(9) Uani 1 1 d . . .
H14 H 0.2433 0.1224 0.4720 0.046 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0290(12) 0.0489(13) 0.0485(13) 0.0004(10) -0.0022(10) 0.0176(10)
F2 0.0675(16) 0.0711(16) 0.0335(13) -0.0082(11) 0.0209(12) 0.0297(13)
F3 0.0471(13) 0.0230(11) 0.0552(14) -0.0128(9) -0.0053(10) 0.0077(10)
C1 0.027(2) 0.038(2) 0.026(2) -0.0057(16) 0.0029(18) 0.0064(18)
S1 0.0211(6) 0.0224(5) 0.0168(5) -0.0012(3) 0.0015(4) -0.0021(3)
O1 0.0332(14) 0.0420(14) 0.0276(13) 0.0011(11) 0.0075(11) -0.0163(12)
O2 0.0279(14) 0.0289(13) 0.0170(13) 0.0010(9) -0.0029(10) 0.0017(10)
N1 0.0170(15) 0.0244(15) 0.0158(15) 0.0001(11) -0.0005(11) -0.0012(11)
S2 0.0211(5) 0.0159(5) 0.0199(5) -0.0008(3) 0.0029(4) -0.0019(3)
O3 0.0301(13) 0.0337(13) 0.0255(13) -0.0102(10) 0.0023(10) -0.0152(11)
O4 0.0362(14) 0.0383(14) 0.0206(13) 0.0075(11) 0.0070(10) -0.0026(11)
C2 0.038(2) 0.034(2) 0.042(2) -0.005(2) 0.0123(19) 0.0045(19)
F4 0.0350(14) 0.0661(15) 0.0799(17) -0.0114(13) 0.0220(12) 0.0163(12)
F5 0.0747(17) 0.0322(13) 0.097(2) -0.0358(13) 0.0366(15) -0.0104(12)
F6 0.122(2) 0.0542(15) 0.0645(17) 0.0296(13) 0.0325(16) 0.0620(15)
N2 0.0254(15) 0.0126(13) 0.0180(15) -0.0006(11) 0.0011(12) 0.0001(11)
C3 0.0218(18) 0.0174(17) 0.027(2) -0.0084(15) -0.0008(14) -0.0003(15)
N3 0.0232(15) 0.0165(14) 0.0199(15) 0.0007(11) 0.0018(12) 0.0026(12)
C4 0.0191(18) 0.0189(17) 0.0273(19) -0.0007(15) 0.0022(15) 0.0014(14)
C5 0.0220(18) 0.0224(18) 0.0217(17) 0.0006(15) -0.0013(14) 0.0065(14)
C6 0.037(2) 0.0267(19) 0.027(2) 0.0063(16) 0.0056(16) 0.0040(16)
C7 0.037(2) 0.0236(18) 0.0274(19) 0.0040(15) 0.0078(16) -0.0036(16)
C8 0.040(2) 0.0219(18) 0.045(2) 0.0043(17) 0.0026(18) -0.0050(17)
C9 0.030(2) 0.037(2) 0.041(2) 0.0165(18) -0.0144(18) -0.0094(18)
C10 0.027(2) 0.029(2) 0.055(3) -0.0046(19) 0.007(2) -0.0071(16)
C11 0.033(2) 0.043(2) 0.025(2) -0.0069(17) 0.0123(18) -0.0187(19)
C12 0.033(2) 0.042(2) 0.028(2) 0.0156(17) -0.0090(17) -0.0064(18)
C13 0.038(2) 0.043(2) 0.040(2) -0.0034(18) 0.0065(18) 0.0052(18)
C14 0.047(2) 0.046(2) 0.021(2) -0.0006(17) 0.0048(18) -0.010(2)

_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
F1 C1 1.327(4) . ?
F2 C1 1.326(3) . ?
F3 C1 1.331(4) . ?
C1 S1 1.818(3) . ?
S1 O2 1.424(2) . ?
S1 O1 1.430(2) . ?
S1 N1 1.574(2) . ?
N1 S2 1.576(3) . ?
S2 O4 1.416(2) . ?
S2 O3 1.424(2) . ?
S2 C2 1.820(4) . ?
C2 F5 1.313(4) . ?
C2 F6 1.318(4) . ?
C2 F4 1.324(4) . ?
N2 C3 1.329(4) . ?
N2 C5 1.371(4) . ?
N2 C7 1.469(4) . ?
C3 N3 1.327(4) . ?
C3 H3 0.9300 . ?
N3 C4 1.371(4) . ?
N3 C6 1.464(4) . ?
C4 C5 1.348(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.497(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C14 1.372(5) . ?
C9 C10 1.376(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(5) . ?
C13 H13 0.9300 . ?
C14 H14 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
F2 C1 F1 108.3(3) . . ?
F2 C1 F3 108.1(3) . . ?
F1 C1 F3 107.5(3) . . ?
F2 C1 S1 109.4(2) . . ?
F1 C1 S1 112.0(2) . . ?
F3 C1 S1 111.4(2) . . ?
O2 S1 O1 119.10(13) . . ?
O2 S1 N1 116.85(13) . . ?
O1 S1 N1 107.96(13) . . ?
O2 S1 C1 104.31(14) . . ?
O1 S1 C1 103.34(15) . . ?
N1 S1 C1 102.97(14) . . ?
S1 N1 S2 124.56(16) . . ?
O4 S2 O3 118.60(13) . . ?
O4 S2 N1 109.21(13) . . ?
O3 S2 N1 115.93(13) . . ?
O4 S2 C2 103.82(16) . . ?
O3 S2 C2 104.57(16) . . ?
N1 S2 C2 102.47(15) . . ?
F5 C2 F6 108.9(3) . . ?
F5 C2 F4 107.4(3) . . ?
F6 C2 F4 108.4(3) . . ?
F5 C2 S2 111.3(3) . . ?
F6 C2 S2 110.7(2) . . ?
F4 C2 S2 110.1(2) . . ?
C3 N2 C5 108.3(3) . . ?
C3 N2 C7 125.3(3) . . ?
C5 N2 C7 126.4(3) . . ?
N3 C3 N2 108.8(3) . . ?
N3 C3 H3 125.6 . . ?
N2 C3 H3 125.6 . . ?
C3 N3 C4 108.5(2) . . ?
C3 N3 C6 125.1(3) . . ?
C4 N3 C6 126.3(3) . . ?
C5 C4 N3 107.1(3) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
C4 C5 N2 107.3(3) . . ?
C4 C5 H5 126.3 . . ?
N2 C5 H5 126.3 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 111.8(3) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 120.1(3) . . ?
C14 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.78
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.091