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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_FCAH11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C4 H4 N O4 S), 2(C4 H5 F N3 O), H2 O'
_chemical_formula_sum            'C16 H20 F2 N8 O11 S2'
_chemical_formula_weight         602.52

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           ?
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.3596(11)
_cell_length_b                   5.8523(3)
_cell_length_c                   32.3137(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.987(4)
_cell_angle_gamma                90.00
_cell_volume                     4792.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5540
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      29.1270
_cell_measurement_theta_min      3.2020
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
; 
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_number            25239
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         26.36
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?

_reflns_number_total             4908
_reflns_number_gt                3737
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_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)+(0.0490P)²+4.6200P] 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_number_reflns         4908
_refine_ls_number_parameters     387
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_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 0.65182(2) 0.86240(11) 0.526660(18) 0.02898(16) Uani 1 1 d . . .
S2 S 0.49281(3) 0.51570(13) 0.650993(19) 0.03709(18) Uani 1 1 d . . .
F1 F 0.33224(6) 0.5267(3) 0.54768(5) 0.0466(4) Uani 1 1 d . . .
F2 F 0.36989(6) 0.2622(2) 0.79262(4) 0.0383(4) Uani 1 1 d . . .
O1 O 0.63114(7) 1.0652(3) 0.55216(5) 0.0317(4) Uani 1 1 d . . .
O2 O 0.60598(7) 0.7628(3) 0.49897(5) 0.0445(5) Uani 1 1 d . . .
O3 O 0.68725(8) 0.9750(3) 0.50720(6) 0.0496(5) Uani 1 1 d . . .
O4 O 0.68333(7) 0.4959(3) 0.62236(5) 0.0352(4) Uani 1 1 d . . .
O5 O 0.48060(7) 0.5202(3) 0.59943(5) 0.0399(5) Uani 1 1 d . . .
O6 O 0.53984(7) 0.6456(4) 0.66702(6) 0.0517(6) Uani 1 1 d . . .
O7 O 0.49535(9) 0.2787(4) 0.66161(6) 0.0595(6) Uani 1 1 d . . .
O8 O 0.38197(7) 0.9037(3) 0.64776(5) 0.0369(4) Uani 1 1 d . . .
O9 O 0.24034(7) 0.5178(3) 0.67548(5) 0.0355(4) Uani 1 1 d . . .
O10 O 0.30297(7) 1.0443(3) 0.71084(5) 0.0337(4) Uani 1 1 d . . .
O11 O 0.54470(10) -0.0043(4) 0.73412(12) 0.0750(8) Uani 1 1 d D . .
H11A H 0.5464(19) -0.107(6) 0.7174(12) 0.113 Uiso 1 1 d D . .
H11B H 0.521(3) -0.023(15) 0.746(3) 0.113 Uiso 0.50 1 d PD . .
H11C H 0.528(3) 0.073(5) 0.7138(17) 0.113 Uiso 0.50 1 d PD . .
N1 N 0.68383(7) 0.6954(3) 0.56285(6) 0.0273(4) Uani 1 1 d . . .
N2 N 0.44340(8) 0.6269(4) 0.66122(6) 0.0361(5) Uani 1 1 d . . .
N3 N 0.29620(8) 0.3495(3) 0.64194(6) 0.0291(5) Uani 1 1 d D . .
H3 H 0.3025(10) 0.245(3) 0.6610(6) 0.035 Uiso 1 1 d D . .
N4 N 0.25199(8) 0.6835(3) 0.61547(6) 0.0239(4) Uani 1 1 d . . .
H4 H 0.2287(10) 0.788(4) 0.6164(7) 0.029 Uiso 1 1 d . . .
N5 N 0.26547(9) 0.8691(4) 0.55637(6) 0.0295(5) Uani 1 1 d . . .
H5A H 0.2427(11) 0.975(5) 0.5574(8) 0.035 Uiso 1 1 d . . .
H5B H 0.2826(10) 0.884(4) 0.5346(8) 0.035 Uiso 1 1 d . . .
N6 N 0.30240(8) 0.7937(4) 0.76438(6) 0.0295(5) Uani 1 1 d . . .
H6A H 0.2828(10) 0.881(5) 0.7745(8) 0.035 Uiso 1 1 d . . .
N7 N 0.35450(7) 0.7269(3) 0.71866(6) 0.0239(4) Uani 1 1 d . . .
H7 H 0.3666(10) 0.776(4) 0.6971(8) 0.029 Uiso 1 1 d . . .
N8 N 0.40707(9) 0.4042(4) 0.72567(7) 0.0328(5) Uani 1 1 d . . .
H8D H 0.4191(11) 0.466(5) 0.7052(9) 0.039 Uiso 1 1 d . . .
H8E H 0.4175(10) 0.282(5) 0.7374(8) 0.039 Uiso 1 1 d D . .
C1 C 0.66404(9) 0.6520(4) 0.59635(7) 0.0259(5) Uani 1 1 d . . .
C2 C 0.62266(9) 0.7961(4) 0.60426(7) 0.0296(5) Uani 1 1 d . . .
H2 H 0.6054 0.7476 0.6242 0.036 Uiso 1 1 calc R . .
C3 C 0.60851(9) 0.9945(4) 0.58414(7) 0.0288(5) Uani 1 1 d . . .
C4 C 0.57136(11) 1.1646(5) 0.59249(9) 0.0433(7) Uani 1 1 d . . .
H4A H 0.5432 1.1884 0.5667 0.065 Uiso 1 1 calc R . .
H4B H 0.5896 1.3061 0.6012 0.065 Uiso 1 1 calc R . .
H4C H 0.5570 1.1100 0.6149 0.065 Uiso 1 1 calc R . .
C5 C 0.41829(9) 0.8031(4) 0.63696(7) 0.0291(5) Uani 1 1 d . . .
C6 C 0.43087(10) 0.8583(4) 0.59682(7) 0.0322(6) Uani 1 1 d . . .
H6 H 0.4189 0.9960 0.5833 0.039 Uiso 1 1 calc R . .
C7 C 0.45850(10) 0.7207(5) 0.57905(7) 0.0322(6) Uani 1 1 d . . .
C8 C 0.46835(11) 0.7389(5) 0.53606(7) 0.0431(7) Uani 1 1 d . . .
H8A H 0.5055 0.7250 0.5391 0.065 Uiso 1 1 calc R . .
H8B H 0.4561 0.8845 0.5235 0.065 Uiso 1 1 calc R . .
H8C H 0.4498 0.6191 0.5177 0.065 Uiso 1 1 calc R . .
C9 C 0.32010(9) 0.3504(4) 0.60942(8) 0.0310(6) Uani 1 1 d . . .
H9 H 0.3433 0.2340 0.6075 0.037 Uiso 1 1 calc R . .
C10 C 0.31013(10) 0.5177(4) 0.58056(8) 0.0294(5) Uani 1 1 d . . .
C11 C 0.27511(9) 0.6977(4) 0.58311(7) 0.0242(5) Uani 1 1 d . . .
C12 C 0.26151(9) 0.5145(4) 0.64628(7) 0.0261(5) Uani 1 1 d . . .
C13 C 0.31872(9) 0.5927(4) 0.78526(7) 0.0287(5) Uani 1 1 d . . .
H13 H 0.3061 0.5488 0.8083 0.034 Uiso 1 1 calc R . .
C14 C 0.35229(9) 0.4611(4) 0.77289(7) 0.0257(5) Uani 1 1 d . . .
C15 C 0.37297(9) 0.5259(4) 0.73843(7) 0.0241(5) Uani 1 1 d . . .
C16 C 0.31853(9) 0.8672(4) 0.73028(7) 0.0247(5) 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
S1 O2 1.4159(19) . ?
S1 O3 1.423(2) . ?
S1 N1 1.5783(19) . ?
S1 O1 1.6226(17) . ?
S2 O6 1.425(2) . ?
S2 O7 1.426(2) . ?
S2 N2 1.571(2) . ?
S2 O5 1.6079(17) . ?
F1 C10 1.346(3) . ?
F2 C14 1.347(3) . ?
O1 C3 1.391(3) . ?
O4 C1 1.251(3) . ?
O5 C7 1.392(3) . ?
O8 C5 1.252(3) . ?
O9 C12 1.221(3) . ?
O10 C16 1.222(3) . ?
O11 H11A 0.817(10) . ?
O11 H11B 0.825(10) . ?
O11 H11C 0.821(10) . ?
N1 C1 1.349(3) . ?
N2 C5 1.353(3) . ?
N3 C12 1.364(3) . ?
N3 C9 1.366(3) . ?
N3 H3 0.851(10) . ?
N4 C11 1.350(3) . ?
N4 C12 1.377(3) . ?
N4 H4 0.87(3) . ?
N5 C11 1.302(3) . ?
N5 H5A 0.87(3) . ?
N5 H5B 0.94(3) . ?
N6 C16 1.355(3) . ?
N6 C13 1.365(3) . ?
N6 H6A 0.85(3) . ?
N7 C15 1.363(3) . ?
N7 C16 1.382(3) . ?
N7 H7 0.89(3) . ?
N8 C15 1.300(3) . ?
N8 H8D 0.89(3) . ?
N8 H8E 0.82(3) . ?
C1 C2 1.456(3) . ?
C2 C3 1.333(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.472(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.461(3) . ?
C6 C7 1.319(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.486(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.327(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.418(3) . ?
C13 C14 1.316(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.420(3) . ?

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
O2 S1 O3 117.45(12) . . ?
O2 S1 N1 113.72(12) . . ?
O3 S1 N1 109.40(11) . . ?
O2 S1 O1 105.94(10) . . ?
O3 S1 O1 103.82(11) . . ?
N1 S1 O1 105.21(9) . . ?
O6 S2 O7 116.95(13) . . ?
O6 S2 N2 113.04(13) . . ?
O7 S2 N2 109.83(13) . . ?
O6 S2 O5 105.88(11) . . ?
O7 S2 O5 104.37(12) . . ?
N2 S2 O5 105.69(10) . . ?
C3 O1 S1 115.62(15) . . ?
C7 O5 S2 116.25(15) . . ?
H11A O11 H11B 113(7) . . ?
H11A O11 H11C 89(6) . . ?
H11B O11 H11C 97(9) . . ?
C1 N1 S1 117.73(16) . . ?
C5 N2 S2 119.72(17) . . ?
C12 N3 C9 122.7(2) . . ?
C12 N3 H3 116.0(18) . . ?
C9 N3 H3 121.3(18) . . ?
C11 N4 C12 125.0(2) . . ?
C11 N4 H4 117.1(16) . . ?
C12 N4 H4 117.9(16) . . ?
C11 N5 H5A 122.3(18) . . ?
C11 N5 H5B 121.4(16) . . ?
H5A N5 H5B 116(2) . . ?
C16 N6 C13 123.3(2) . . ?
C16 N6 H6A 118.6(19) . . ?
C13 N6 H6A 117.9(18) . . ?
C15 N7 C16 124.6(2) . . ?
C15 N7 H7 119.1(16) . . ?
C16 N7 H7 116.2(16) . . ?
C15 N8 H8D 115.6(18) . . ?
C15 N8 H8E 120(2) . . ?
H8D N8 H8E 124(3) . . ?
O4 C1 N1 120.1(2) . . ?
O4 C1 C2 119.4(2) . . ?
N1 C1 C2 120.4(2) . . ?
C3 C2 C1 122.8(2) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 O1 120.1(2) . . ?
C2 C3 C4 127.6(2) . . ?
O1 C3 C4 112.2(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O8 C5 N2 119.1(2) . . ?
O8 C5 C6 121.4(2) . . ?
N2 C5 C6 119.3(2) . . ?
C7 C6 C5 122.6(2) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 O5 121.2(2) . . ?
C6 C7 C8 128.5(2) . . ?
O5 C7 C8 110.2(2) . . ?
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 . . ?
C10 C9 N3 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
N3 C9 H9 120.0 . . ?
C9 C10 F1 122.6(2) . . ?
C9 C10 C11 120.9(2) . . ?
F1 C10 C11 116.6(2) . . ?
N5 C11 N4 120.9(2) . . ?
N5 C11 C10 123.0(2) . . ?
N4 C11 C10 116.1(2) . . ?
O9 C12 N3 123.5(2) . . ?
O9 C12 N4 121.1(2) . . ?
N3 C12 N4 115.3(2) . . ?
C14 C13 N6 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
N6 C13 H13 120.0 . . ?
C13 C14 F2 122.3(2) . . ?
C13 C14 C15 121.2(2) . . ?
F2 C14 C15 116.5(2) . . ?
N8 C15 N7 120.9(2) . . ?
N8 C15 C14 123.4(2) . . ?
N7 C15 C14 115.7(2) . . ?
O10 C16 N6 123.4(2) . . ?
O10 C16 N7 121.5(2) . . ?
N6 C16 N7 115.1(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
O2 S1 O1 C3 74.09(17) . . . . ?
O3 S1 O1 C3 -161.58(16) . . . . ?
N1 S1 O1 C3 -46.65(18) . . . . ?
O6 S2 O5 C7 -77.28(19) . . . . ?
O7 S2 O5 C7 158.71(19) . . . . ?
N2 S2 O5 C7 42.9(2) . . . . ?
O2 S1 N1 C1 -75.1(2) . . . . ?
O3 S1 N1 C1 151.41(18) . . . . ?
O1 S1 N1 C1 40.4(2) . . . . ?
O6 S2 N2 C5 79.0(2) . . . . ?
O7 S2 N2 C5 -148.4(2) . . . . ?
O5 S2 N2 C5 -36.3(2) . . . . ?
S1 N1 C1 O4 169.23(18) . . . . ?
S1 N1 C1 C2 -15.1(3) . . . . ?
O4 C1 C2 C3 164.5(2) . . . . ?
N1 C1 C2 C3 -11.3(4) . . . . ?
C1 C2 C3 O1 4.1(3) . . . . ?
C1 C2 C3 C4 -173.3(2) . . . . ?
S1 O1 C3 C2 27.0(3) . . . . ?
S1 O1 C3 C4 -155.15(17) . . . . ?
S2 N2 C5 O8 -173.62(19) . . . . ?
S2 N2 C5 C6 11.8(3) . . . . ?
O8 C5 C6 C7 -162.0(3) . . . . ?
N2 C5 C6 C7 12.5(4) . . . . ?
C5 C6 C7 O5 -4.6(4) . . . . ?
C5 C6 C7 C8 171.3(3) . . . . ?
S2 O5 C7 C6 -25.3(3) . . . . ?
S2 O5 C7 C8 158.08(18) . . . . ?
C12 N3 C9 C10 0.5(3) . . . . ?
N3 C9 C10 F1 -179.5(2) . . . . ?
N3 C9 C10 C11 0.5(4) . . . . ?
C12 N4 C11 N5 -177.0(2) . . . . ?
C12 N4 C11 C10 2.5(3) . . . . ?
C9 C10 C11 N5 177.7(2) . . . . ?
F1 C10 C11 N5 -2.3(3) . . . . ?
C9 C10 C11 N4 -1.9(3) . . . . ?
F1 C10 C11 N4 178.2(2) . . . . ?
C9 N3 C12 O9 -179.0(2) . . . . ?
C9 N3 C12 N4 0.1(3) . . . . ?
C11 N4 C12 O9 177.4(2) . . . . ?
C11 N4 C12 N3 -1.7(3) . . . . ?
C16 N6 C13 C14 0.9(3) . . . . ?
N6 C13 C14 F2 179.5(2) . . . . ?
N6 C13 C14 C15 1.2(3) . . . . ?
C16 N7 C15 N8 -179.6(2) . . . . ?
C16 N7 C15 C14 0.8(3) . . . . ?
C13 C14 C15 N8 178.4(2) . . . . ?
F2 C14 C15 N8 0.0(3) . . . . ?
C13 C14 C15 N7 -2.0(3) . . . . ?
F2 C14 C15 N7 179.63(18) . . . . ?
C13 N6 C16 O10 178.1(2) . . . . ?
C13 N6 C16 N7 -2.0(3) . . . . ?
C15 N7 C16 O10 -179.0(2) . . . . ?
C15 N7 C16 N6 1.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N8 H8E O11 0.82(3) 2.03(3) 2.848(3) 171(3) 2_656
N8 H8D N2 0.89(3) 1.95(3) 2.838(3) 175(3) .
N7 H7 O8 0.89(3) 1.90(3) 2.785(3) 171(2) .
N6 H6A O9 0.85(3) 2.04(3) 2.824(3) 152(2) 4_556
N5 H5A N1 0.87(3) 2.06(3) 2.927(3) 173(3) 3_455
N4 H4 O4 0.87(3) 1.75(3) 2.625(3) 176(2) 3_455
N3 H3 O10 0.851(10) 1.991(12) 2.822(2) 165(3) 1_545
O11 H11A O6 0.817(10) 2.151(13) 2.960(4) 171(5) 1_545
O11 H11C O7 0.821(10) 2.057(17) 2.872(4) 171(9) .
O11 H11B O11 0.825(10) 2.01(3) 2.818(6) 166(9) 2_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 992732'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FCFCAH

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 F2 N7 O6 S'
_chemical_formula_sum            'C12 H13 F2 N7 O6 S'
_chemical_formula_weight         421.35

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.2613(2)
_cell_length_b                   10.5289(3)
_cell_length_c                   11.6662(4)
_cell_angle_alpha                66.8180(11)
_cell_angle_beta                 82.0220(12)
_cell_angle_gamma                78.5670(12)
_cell_volume                     801.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8668
_exptl_absorpt_correction_T_max  0.9517
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26053
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3270
_reflns_number_gt                2996
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0485P)²+0.3374P] 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_number_reflns         3270
_refine_ls_number_parameters     269
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.046
_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
S1 S 0.67223(5) 0.18926(3) 0.57615(3) 0.02003(11) Uani 1 1 d U . .
F1 F 0.81797(14) 0.73340(9) 0.55540(7) 0.0300(2) Uani 1 1 d U . .
F2 F 0.82126(13) 0.56825(9) 0.41381(7) 0.0282(2) Uani 1 1 d U . .
O1 O 0.70149(15) 0.40797(10) 1.03439(9) 0.0248(2) Uani 1 1 d U . .
O2 O 0.94487(14) 0.88695(9) -0.06567(8) 0.0216(2) Uani 1 1 d U . .
O3 O 0.51432(14) 0.08990(10) 0.60165(9) 0.0240(2) Uani 1 1 d U . .
O4 O 0.59298(14) 0.19222(10) 0.89245(9) 0.0235(2) Uani 1 1 d U . .
O5 O 0.85072(15) 0.10256(11) 0.57391(10) 0.0289(2) Uani 1 1 d U . .
O6 O 0.62351(16) 0.30056(11) 0.46060(9) 0.0299(3) Uani 1 1 d U . .
N1 N 0.69574(16) 0.44404(12) 0.82950(10) 0.0185(2) Uani 1 1 d U . .
H1A H 0.660(2) 0.3591(18) 0.8515(15) 0.022 Uiso 1 1 d . . .
N2 N 0.79261(16) 0.60710(11) 0.88737(10) 0.0185(2) Uani 1 1 d U . .
H2A H 0.810(2) 0.6321(17) 0.9471(16) 0.022 Uiso 1 1 d . . .
N3 N 0.89379(17) 0.80741(11) 0.74135(11) 0.0220(3) Uani 1 1 d U . .
H3A H 0.9162 0.8309 0.8020 0.026 Uiso 1 1 calc R . .
H3B H 0.9160 0.8619 0.6629 0.026 Uiso 1 1 calc R . .
N4 N 0.85485(15) 0.68625(11) 0.07872(10) 0.0172(2) Uani 1 1 d U . .
N5 N 0.94782(16) 0.85181(12) 0.13833(10) 0.0184(2) Uani 1 1 d U . .
H5A H 0.984(2) 0.9333(19) 0.1133(15) 0.022 Uiso 1 1 d . . .
N6 N 0.75923(17) 0.48769(12) 0.23033(11) 0.0205(2) Uani 1 1 d U . .
H6A H 0.734(2) 0.4412(18) 0.3013(17) 0.025 Uiso 1 1 d . . .
H6B H 0.737(2) 0.4638(18) 0.1734(17) 0.025 Uiso 1 1 d . . .
N7 N 0.64352(17) 0.24393(12) 0.68509(11) 0.0217(3) Uani 1 1 d U . .
C1 C 0.72730(18) 0.48073(13) 0.92400(12) 0.0183(3) Uani 1 1 d U . .
C2 C 0.82746(18) 0.69172(13) 0.76766(12) 0.0183(3) Uani 1 1 d U . .
C3 C 0.78800(19) 0.64746(14) 0.67454(12) 0.0199(3) Uani 1 1 d U . .
C4 C 0.72368(19) 0.52627(14) 0.70667(12) 0.0193(3) Uani 1 1 d U . .
H4 H 0.6975 0.4977 0.6437 0.023 Uiso 1 1 calc R . .
C5 C 0.91597(18) 0.81033(13) 0.04648(12) 0.0169(3) Uani 1 1 d U . .
C6 C 0.81965(18) 0.60798(13) 0.19929(12) 0.0172(3) Uani 1 1 d U . .
C7 C 0.85211(19) 0.65308(14) 0.29403(12) 0.0191(3) Uani 1 1 d U . .
C8 C 0.91699(19) 0.77388(14) 0.26198(12) 0.0194(3) Uani 1 1 d U . .
H8 H 0.9410 0.8046 0.3241 0.023 Uiso 1 1 calc R . .
C9 C 0.59020(18) 0.15839(13) 0.80170(12) 0.0183(3) Uani 1 1 d U . .
C10 C 0.51492(18) 0.03163(13) 0.82011(12) 0.0183(3) Uani 1 1 d U . .
H10 H 0.4954 -0.0339 0.9027 0.022 Uiso 1 1 calc R . .
C11 C 0.47323(18) 0.00580(13) 0.72454(12) 0.0191(3) Uani 1 1 d U . .
C12 C 0.3698(2) -0.10541(15) 0.73081(14) 0.0261(3) Uani 1 1 d U . .
H12A H 0.3421 -0.1637 0.8185 0.039 Uiso 1 1 calc R . .
H12B H 0.4473 -0.1636 0.6885 0.039 Uiso 1 1 calc R . .
H12C H 0.2516 -0.0623 0.6897 0.039 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 O6 1.4282(10) . ?
S1 O5 1.4332(11) . ?
S1 N7 1.5637(12) . ?
S1 O3 1.6229(10) . ?
F1 C3 1.3423(14) . ?
F2 C7 1.3455(15) . ?
O1 C1 1.2222(16) . ?
O2 C5 1.2516(15) . ?
O3 C11 1.3839(15) . ?
O4 C9 1.2466(16) . ?
N1 C4 1.3625(17) . ?
N1 C1 1.3630(17) . ?
N1 H1A 0.907(18) . ?
N2 C2 1.3491(17) . ?
N2 C1 1.3871(17) . ?
N2 H2A 0.866(18) . ?
N3 C2 1.3065(17) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C6 1.3394(16) . ?
N4 C5 1.3571(16) . ?
N5 C8 1.3622(17) . ?
N5 C5 1.3674(17) . ?
N5 H5A 0.874(18) . ?
N6 C6 1.3201(17) . ?
N6 H6A 0.796(18) . ?
N6 H6B 0.843(19) . ?
N7 C9 1.3561(17) . ?
C2 C3 1.4204(19) . ?
C3 C4 1.3409(19) . ?
C4 H4 0.9500 . ?
C6 C7 1.4257(18) . ?
C7 C8 1.3393(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4687(17) . ?
C10 C11 1.3319(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4855(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
O6 S1 O5 115.99(7) . . ?
O6 S1 N7 110.89(7) . . ?
O5 S1 N7 113.02(7) . . ?
O6 S1 O3 103.02(6) . . ?
O5 S1 O3 105.94(6) . . ?
N7 S1 O3 106.94(6) . . ?
C11 O3 S1 117.12(8) . . ?
C4 N1 C1 122.61(11) . . ?
C4 N1 H1A 120.3(10) . . ?
C1 N1 H1A 117.0(10) . . ?
C2 N2 C1 124.67(11) . . ?
C2 N2 H2A 119.3(11) . . ?
C1 N2 H2A 116.0(11) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C6 N4 C5 120.12(11) . . ?
C8 N5 C5 122.23(11) . . ?
C8 N5 H5A 121.5(11) . . ?
C5 N5 H5A 116.2(11) . . ?
C6 N6 H6A 121.4(13) . . ?
C6 N6 H6B 119.1(12) . . ?
H6A N6 H6B 119.2(17) . . ?
C9 N7 S1 119.20(9) . . ?
O1 C1 N1 123.00(12) . . ?
O1 C1 N2 121.30(12) . . ?
N1 C1 N2 115.70(11) . . ?
N3 C2 N2 120.72(12) . . ?
N3 C2 C3 123.01(12) . . ?
N2 C2 C3 116.27(11) . . ?
C4 C3 F1 123.10(12) . . ?
C4 C3 C2 120.60(12) . . ?
F1 C3 C2 116.30(11) . . ?
C3 C4 N1 120.13(12) . . ?
C3 C4 H4 119.9 . . ?
N1 C4 H4 119.9 . . ?
O2 C5 N4 121.22(12) . . ?
O2 C5 N5 119.44(11) . . ?
N4 C5 N5 119.33(11) . . ?
N6 C6 N4 119.99(12) . . ?
N6 C6 C7 120.10(12) . . ?
N4 C6 C7 119.89(11) . . ?
C8 C7 F2 122.56(12) . . ?
C8 C7 C6 119.80(12) . . ?
F2 C7 C6 117.60(11) . . ?
C7 C8 N5 118.58(12) . . ?
C7 C8 H8 120.7 . . ?
N5 C8 H8 120.7 . . ?
O4 C9 N7 119.91(12) . . ?
O4 C9 C10 119.76(11) . . ?
N7 C9 C10 120.15(12) . . ?
C11 C10 C9 122.01(12) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 O3 122.01(11) . . ?
C10 C11 C12 127.13(12) . . ?
O3 C11 C12 110.75(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6B O1 0.843(19) 1.990(19) 2.8322(15) 176.0(17) 1_554
N6 H6A O6 0.796(18) 2.044(19) 2.8174(15) 163.9(17) .
N5 H5A O2 0.874(18) 1.906(19) 2.7788(15) 176.9(16) 2_775
N3 H3B O5 0.88 2.31 2.9284(15) 127.8 1_565
N3 H3A O2 0.88 1.91 2.7834(15) 175.6 1_556
N2 H2A N4 0.866(18) 1.922(19) 2.7885(16) 178.3(16) 1_556
N1 H1A N7 0.907(18) 2.690(17) 3.2726(16) 122.9(12) .
N1 H1A O4 0.907(18) 1.781(18) 2.6879(14) 179.1(16) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 978203'
