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

#######################################################################
#
#                 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_double5_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F6 N5 O6 S4'
_chemical_formula_weight         585.50

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'
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'
O O 0.0106 0.0060 '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
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4770(3)
_cell_length_b                   10.1380(3)
_cell_length_c                   12.6490(4)
_cell_angle_alpha                88.7192(17)
_cell_angle_beta                 78.5886(16)
_cell_angle_gamma                83.6975(17)
_cell_volume                     1059.12(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    452
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9032
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 Kappa APEX II'
_diffrn_measurement_method       'Omega and phi scan'
_diffrn_standards_number         3
_diffrn_standards_interval_time  90
_diffrn_standards_decay_%        0
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16882
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4339
_reflns_number_gt                3639
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_structure_solution    'Direct Method'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    Mercury
_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)+(0.0166P)²+2.2024P] 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         4339
_refine_ls_number_parameters     317
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.212
_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 0.00754(12) 0.40239(9) 0.61928(7) 0.0418(2) Uani 1 1 d U . .
S2 S 0.33418(11) 0.45447(8) 0.17808(7) 0.0361(2) Uani 1 1 d U . .
C1 C 0.1513(4) 0.2432(3) 0.4819(2) 0.0313(7) Uani 1 1 d U . .
N1 N 0.0855(4) 0.3651(3) 0.4940(2) 0.0368(6) Uani 1 1 d U . .
N2 N 0.2222(4) 0.1881(3) 0.3830(2) 0.0365(7) Uani 1 1 d U . .
H2A H 0.2391 0.1031 0.3778 0.044 Uiso 1 1 calc R . .
C2 C 0.2675(4) 0.2635(3) 0.2918(2) 0.0304(7) Uani 1 1 d U . .
N3 N 0.2922(3) 0.3872(3) 0.2964(2) 0.0345(6) Uani 1 1 d U . .
C3 C 0.1420(4) 0.1677(3) 0.5807(3) 0.0325(7) Uani 1 1 d U . .
C4 C 0.1970(5) 0.0384(4) 0.6016(3) 0.0467(9) Uani 1 1 d U . .
H4B H 0.2510 -0.0178 0.5458 0.056 Uiso 1 1 calc R . .
C5 C 0.1701(5) -0.0055(4) 0.7066(3) 0.0539(10) Uani 1 1 d U . .
H5B H 0.2077 -0.0919 0.7224 0.065 Uiso 1 1 calc R . .
C6 C 0.0878(5) 0.0779(4) 0.7890(3) 0.0464(9) Uani 1 1 d U . .
H6B H 0.0687 0.0465 0.8595 0.056 Uiso 1 1 calc R . .
C7 C 0.0346(5) 0.2045(4) 0.7680(3) 0.0419(8) Uani 1 1 d U . .
H7A H -0.0207 0.2610 0.8232 0.050 Uiso 1 1 calc R . .
N4 N 0.0643(3) 0.2471(3) 0.6636(2) 0.0340(6) Uani 1 1 d U . .
C8 C 0.2870(4) 0.2108(3) 0.1843(2) 0.0279(6) Uani 1 1 d U . .
C9 C 0.2716(4) 0.0865(3) 0.1476(3) 0.0371(8) Uani 1 1 d U . .
H9A H 0.2435 0.0184 0.1957 0.045 Uiso 1 1 calc R . .
C10 C 0.2988(5) 0.0659(4) 0.0382(3) 0.0453(9) Uani 1 1 d U . .
H10A H 0.2880 -0.0168 0.0116 0.054 Uiso 1 1 calc R . .
C11 C 0.3425(5) 0.1683(4) -0.0328(3) 0.0446(9) Uani 1 1 d U . .
H11A H 0.3631 0.1530 -0.1068 0.054 Uiso 1 1 calc R . .
C12 C 0.3552(4) 0.2902(4) 0.0046(3) 0.0379(8) Uani 1 1 d U . .
H12A H 0.3837 0.3590 -0.0428 0.046 Uiso 1 1 calc R . .
N5 N 0.3256(3) 0.3093(3) 0.1128(2) 0.0298(6) Uani 1 1 d U . .
S3 S 0.77378(11) 0.29541(9) 0.07515(7) 0.0389(2) Uani 1 1 d U . .
O1 O 0.9195(4) 0.2227(4) 0.0215(3) 0.0939(13) Uani 1 1 d U . .
O2 O 0.6639(4) 0.2159(3) 0.1402(3) 0.0603(8) Uani 1 1 d U . .
O3 O 0.6975(4) 0.3930(3) 0.0129(2) 0.0636(8) Uani 1 1 d U . .
C13 C 0.8398(5) 0.3941(4) 0.1723(4) 0.0517(10) Uani 1 1 d U . .
F1 F 0.9444(5) 0.4740(4) 0.1258(3) 0.1281(15) Uani 1 1 d U . .
F2 F 0.7219(4) 0.4670(4) 0.2294(3) 0.1306(17) Uani 1 1 d U . .
F3 F 0.9160(4) 0.3216(3) 0.2376(2) 0.0839(9) Uani 1 1 d U . .
S4 S 0.38283(14) 0.80223(10) 0.33145(8) 0.0505(3) Uani 1 1 d U . .
O4 O 0.5215(7) 0.8640(7) 0.2962(4) 0.172(3) Uani 1 1 d U . .
O5 O 0.2456(6) 0.8927(4) 0.3768(3) 0.1048(15) Uani 1 1 d U . .
O6 O 0.3417(4) 0.7149(3) 0.2589(3) 0.0711(9) Uani 1 1 d U . .
C14 C 0.4218(6) 0.7043(5) 0.4459(4) 0.0636(12) Uani 1 1 d U . .
F4 F 0.5524(7) 0.6220(5) 0.4135(4) 0.174(2) Uani 1 1 d U . .
F5 F 0.3080(6) 0.6421(5) 0.4886(4) 0.170(2) Uani 1 1 d U . .
F6 F 0.4625(4) 0.7747(3) 0.5196(2) 0.0883(9) Uani 1 1 d 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 N1 1.627(3) . ?
S1 N4 1.710(3) . ?
S2 N3 1.621(3) . ?
S2 N5 1.719(3) . ?
C1 N1 1.298(4) . ?
C1 N2 1.377(4) . ?
C1 C3 1.444(4) . ?
N2 C2 1.382(4) . ?
C2 N3 1.298(4) . ?
C2 C8 1.445(4) . ?
C3 N4 1.352(4) . ?
C3 C4 1.380(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.381(6) . ?
C6 C7 1.352(5) . ?
C7 N4 1.363(4) . ?
C8 N5 1.355(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.374(5) . ?
C10 C11 1.390(5) . ?
C11 C12 1.356(5) . ?
C12 N5 1.357(4) . ?
S3 O1 1.421(3) . ?
S3 O2 1.423(3) . ?
S3 O3 1.429(3) . ?
S3 C13 1.809(4) . ?
C13 F2 1.282(5) . ?
C13 F1 1.311(5) . ?
C13 F3 1.312(5) . ?
S4 O4 1.383(4) . ?
S4 O6 1.406(3) . ?
S4 O5 1.431(4) . ?
S4 C14 1.801(5) . ?
C14 F5 1.238(6) . ?
C14 F6 1.307(5) . ?
C14 F4 1.313(6) . ?

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
N1 S1 N4 92.81(14) . . ?
N3 S2 N5 92.93(13) . . ?
N1 C1 N2 123.3(3) . . ?
N1 C1 C3 114.7(3) . . ?
N2 C1 C3 122.1(3) . . ?
C1 N1 S1 112.7(2) . . ?
C1 N2 C2 122.9(3) . . ?
N3 C2 N2 122.6(3) . . ?
N3 C2 C8 115.1(3) . . ?
N2 C2 C8 122.2(3) . . ?
C2 N3 S2 112.6(2) . . ?
N4 C3 C4 119.3(3) . . ?
N4 C3 C1 108.5(3) . . ?
C4 C3 C1 132.2(3) . . ?
C5 C4 C3 118.5(4) . . ?
C4 C5 C6 120.5(4) . . ?
C7 C6 C5 120.6(3) . . ?
C6 C7 N4 118.1(3) . . ?
C3 N4 C7 122.9(3) . . ?
C3 N4 S1 111.3(2) . . ?
C7 N4 S1 125.8(3) . . ?
N5 C8 C9 119.9(3) . . ?
N5 C8 C2 108.2(3) . . ?
C9 C8 C2 131.9(3) . . ?
C10 C9 C8 118.4(3) . . ?
C9 C10 C11 120.1(3) . . ?
C12 C11 C10 120.7(3) . . ?
C11 C12 N5 118.4(3) . . ?
C8 N5 C12 122.5(3) . . ?
C8 N5 S2 111.1(2) . . ?
C12 N5 S2 126.4(2) . . ?
O1 S3 O2 114.0(2) . . ?
O1 S3 O3 116.8(2) . . ?
O2 S3 O3 113.61(18) . . ?
O1 S3 C13 103.5(2) . . ?
O2 S3 C13 103.6(2) . . ?
O3 S3 C13 103.06(19) . . ?
F2 C13 F1 106.7(4) . . ?
F2 C13 F3 108.3(4) . . ?
F1 C13 F3 104.4(4) . . ?
F2 C13 S3 112.2(3) . . ?
F1 C13 S3 112.0(3) . . ?
F3 C13 S3 112.7(3) . . ?
O4 S4 O6 116.9(3) . . ?
O4 S4 O5 113.1(4) . . ?
O6 S4 O5 110.8(2) . . ?
O4 S4 C14 105.0(3) . . ?
O6 S4 C14 106.7(2) . . ?
O5 S4 C14 103.1(2) . . ?
F5 C14 F6 108.9(5) . . ?
F5 C14 F4 110.1(5) . . ?
F6 C14 F4 103.1(4) . . ?
F5 C14 S4 113.8(4) . . ?
F6 C14 S4 112.6(3) . . ?
F4 C14 S4 107.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.232
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986942'
#######################################################################
#
#                 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_jb009

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          124
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N5 S'
_chemical_formula_weight         255.30

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'
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   P2(1)/c

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

_cell_length_a                   13.6633(4)
_cell_length_b                   3.84480(10)
_cell_length_c                   22.7022(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.326(2)
_cell_angle_gamma                90.00
_cell_volume                     1144.52(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.27

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9209
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26465
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.31
_reflns_number_total             2799
_reflns_number_gt                2174
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0627P)²+0.4490P] 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         2799
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
S1 S 0.24362(3) 0.93676(13) 0.48907(2) 0.02969(15) Uani 1 1 d . . .
N1 N 0.36015(11) 1.1022(4) 0.52424(7) 0.0264(3) Uani 1 1 d . . .
N2 N 0.30199(11) 1.2051(5) 0.61157(6) 0.0314(4) Uani 1 1 d . . .
H2A H 0.3233 1.3822 0.6459 0.038 Uiso 1 1 d R . .
N3 N 0.16113(11) 1.1046(4) 0.52495(7) 0.0270(3) Uani 1 1 d . . .
N4 N 0.48210(12) 1.4656(5) 0.67036(7) 0.0319(4) Uani 1 1 d . . .
N5 N 0.17702(12) 1.4802(4) 0.67041(7) 0.0298(4) Uani 1 1 d . . .
C1 C 0.37503(13) 1.2132(5) 0.57919(7) 0.0232(4) Uani 1 1 d . . .
C2 C 0.19895(13) 1.2156(5) 0.57968(7) 0.0239(4) Uani 1 1 d . . .
C3 C 0.47518(13) 1.3603(5) 0.61325(7) 0.0229(4) Uani 1 1 d . . .
C4 C 0.55446(14) 1.3814(5) 0.58665(8) 0.0269(4) Uani 1 1 d . . .
H4A H 0.5464 1.3020 0.5459 0.032 Uiso 1 1 calc R . .
C5 C 0.64555(15) 1.5213(6) 0.62103(9) 0.0334(4) Uani 1 1 d . . .
H5A H 0.7013 1.5448 0.6040 0.040 Uiso 1 1 calc R . .
C6 C 0.65488(15) 1.6269(6) 0.68055(9) 0.0342(5) Uani 1 1 d . . .
H6A H 0.7174 1.7189 0.7054 0.041 Uiso 1 1 calc R . .
C7 C 0.57173(15) 1.5959(6) 0.70296(9) 0.0364(5) Uani 1 1 d . . .
H7A H 0.5783 1.6711 0.7437 0.044 Uiso 1 1 calc R . .
C8 C 0.13077(13) 1.3687(5) 0.61360(7) 0.0231(4) Uani 1 1 d . . .
C9 C 0.02638(14) 1.3879(5) 0.58651(8) 0.0275(4) Uani 1 1 d . . .
H9A H -0.0032 1.3029 0.5461 0.033 Uiso 1 1 calc R . .
C10 C -0.03322(15) 1.5342(5) 0.62002(9) 0.0326(4) Uani 1 1 d . . .
H10A H -0.1049 1.5549 0.6028 0.039 Uiso 1 1 calc R . .
C11 C 0.01289(16) 1.6504(5) 0.67905(9) 0.0334(4) Uani 1 1 d . . .
H11A H -0.0266 1.7490 0.7032 0.040 Uiso 1 1 calc R . .
C12 C 0.11668(15) 1.6202(5) 0.70191(8) 0.0319(4) Uani 1 1 d . . .
H12A H 0.1478 1.7029 0.7423 0.038 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 N3 1.6930(16) . ?
S1 N1 1.6919(16) . ?
N1 C1 1.279(2) . ?
N2 C2 1.391(2) . ?
N2 C1 1.396(2) . ?
N3 C2 1.278(2) . ?
N4 C3 1.336(2) . ?
N4 C7 1.338(2) . ?
N5 C12 1.346(3) . ?
N5 C8 1.337(2) . ?
C1 C3 1.482(2) . ?
C2 C8 1.487(2) . ?
C3 C4 1.383(2) . ?
C4 C5 1.379(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.374(3) . ?
C8 C9 1.387(2) . ?
C9 C10 1.381(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.371(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
N3 S1 N1 107.16(8) . . ?
C1 N1 S1 117.13(13) . . ?
C2 N2 C1 119.61(14) . . ?
C2 N3 S1 116.96(13) . . ?
C3 N4 C7 117.03(16) . . ?
C12 N5 C8 116.53(16) . . ?
N1 C1 N2 124.38(16) . . ?
N1 C1 C3 120.43(15) . . ?
N2 C1 C3 115.19(14) . . ?
N3 C2 N2 124.75(16) . . ?
N3 C2 C8 119.67(15) . . ?
N2 C2 C8 115.59(15) . . ?
N4 C3 C4 123.75(16) . . ?
N4 C3 C1 115.16(15) . . ?
C4 C3 C1 121.08(15) . . ?
C3 C4 C5 117.96(16) . . ?
C6 C5 C4 119.25(18) . . ?
C5 C6 C7 118.54(18) . . ?
N4 C7 C6 123.45(17) . . ?
N5 C8 C9 123.96(17) . . ?
N5 C8 C2 115.56(15) . . ?
C9 C8 C2 120.48(15) . . ?
C10 C9 C8 118.00(17) . . ?
C9 C10 C11 119.10(18) . . ?
C12 C11 C10 118.66(18) . . ?
N5 C12 C11 123.74(17) . . ?

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
N3 S1 N1 C1 22.45(17) . . . . ?
N1 S1 N3 C2 -22.28(17) . . . . ?
S1 N1 C1 N2 0.2(3) . . . . ?
S1 N1 C1 C3 179.70(13) . . . . ?
C2 N2 C1 N1 -27.4(3) . . . . ?
C2 N2 C1 C3 153.06(17) . . . . ?
S1 N3 C2 N2 -0.6(3) . . . . ?
S1 N3 C2 C8 179.52(12) . . . . ?
C1 N2 C2 N3 27.7(3) . . . . ?
C1 N2 C2 C8 -152.44(17) . . . . ?
C7 N4 C3 C4 -0.5(3) . . . . ?
C7 N4 C3 C1 179.15(17) . . . . ?
N1 C1 C3 N4 -179.57(17) . . . . ?
N2 C1 C3 N4 0.0(2) . . . . ?
N1 C1 C3 C4 0.1(3) . . . . ?
N2 C1 C3 C4 179.60(17) . . . . ?
N4 C3 C4 C5 -0.4(3) . . . . ?
C1 C3 C4 C5 180.00(17) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C3 N4 C7 C6 0.3(3) . . . . ?
C5 C6 C7 N4 0.6(3) . . . . ?
C12 N5 C8 C9 -0.5(3) . . . . ?
C12 N5 C8 C2 179.90(16) . . . . ?
N3 C2 C8 N5 -179.56(17) . . . . ?
N2 C2 C8 N5 0.5(2) . . . . ?
N3 C2 C8 C9 0.8(3) . . . . ?
N2 C2 C8 C9 -179.11(16) . . . . ?
N5 C8 C9 C10 0.7(3) . . . . ?
C2 C8 C9 C10 -179.67(17) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C8 N5 C12 C11 0.4(3) . . . . ?
C10 C11 C12 N5 -0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 986943'
#######################################################################
#
#                 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_jb014

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          'dec > 275'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 F6 N5 O6 S3'
_chemical_formula_weight         555.46

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'

_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                   9.1987(3)
_cell_length_b                   9.8364(3)
_cell_length_c                   11.7652(4)
_cell_angle_alpha                94.5844(16)
_cell_angle_beta                 102.6573(17)
_cell_angle_gamma                92.0173(17)
_cell_volume                     1033.82(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6909
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.35

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.458
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6426
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with four batch runs at phi = 0.00 deg 
 (600 frames), at phi = 90.00 deg (600 frames), at phi = 180.00 deg 
 (600 frames), and at phi = 270.00 deg (600 frames). 
 A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor 
 crystal and diffractometer stability. Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14565
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5084
_reflns_number_gt                3959
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0689P)²+0.3850P] 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         5084
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_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 0.72869(7) 1.00552(6) -0.35389(5) 0.03224(15) Uani 1 1 d . . . . .
S2 S 0.15484(6) 0.82582(6) 0.64836(5) 0.02829(14) Uani 1 1 d . . . . .
S3 S 0.29734(6) 0.68556(5) 0.14030(5) 0.02520(14) Uani 1 1 d . . . . .
F1 F 0.4253(2) 0.8619(2) 0.7765(2) 0.0811(7) Uani 1 1 d . . . . .
F2 F 0.3446(3) 0.6534(2) 0.7430(2) 0.0834(7) Uani 1 1 d . . . . .
F3 F 0.4081(2) 0.7574(3) 0.6059(2) 0.0895(8) Uani 1 1 d . . . . .
F4 F 0.5023(3) 0.8604(3) 0.1135(3) 0.1075(9) Uani 1 1 d . . . . .
F5 F 0.5851(2) 0.6732(3) 0.17787(19) 0.1004(10) Uani 1 1 d . . . . .
F6 F 0.4803(3) 0.6792(3) 0.00057(18) 0.0850(7) Uani 1 1 d . . . . .
O1 O 0.1758(3) 0.9469(2) 0.59373(19) 0.0611(6) Uani 1 1 d . . . . .
O2 O 0.0826(2) 0.7097(2) 0.57301(15) 0.0455(5) Uani 1 1 d . . . . .
O3 O 0.1035(2) 0.8487(2) 0.75507(16) 0.0467(5) Uani 1 1 d . . . . .
O4 O 0.3162(2) 0.73890(19) 0.26005(16) 0.0433(4) Uani 1 1 d . . . . .
O5 O 0.2864(3) 0.53875(17) 0.12342(17) 0.0518(5) Uani 1 1 d . . . . .
O6 O 0.19263(19) 0.75048(18) 0.05581(16) 0.0385(4) Uani 1 1 d . . . . .
N2 N 0.8150(2) 0.77643(18) -0.10545(15) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.7680(2) 0.97060(19) -0.21720(16) 0.0276(4) Uani 1 1 d . . . . .
N4 N 0.7239(2) 0.83616(18) -0.40650(15) 0.0249(4) Uani 1 1 d . . . . .
N3 N 0.8289(2) 0.97870(19) 0.02155(16) 0.0304(4) Uani 1 1 d . . . . .
H3B H 0.8071 1.0322 -0.0356 0.036 Uiso 1 1 calc R U . . .
H3C H 0.8456 1.0137 0.0947 0.036 Uiso 1 1 calc R U . . .
N5 N 0.8588(2) 0.62520(19) 0.07004(16) 0.0270(4) Uani 1 1 d . . . . .
H5B H 0.8270 0.5950 -0.0040 0.032 Uiso 1 1 calc R U . . .
C1 C 0.7806(2) 0.8391(2) -0.20593(18) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.8364(2) 0.8460(2) -0.00248(18) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.7519(2) 0.7560(2) -0.31668(17) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.7450(3) 0.6150(2) -0.3395(2) 0.0287(5) Uani 1 1 d . . . . .
H4A H 0.7652 0.5577 -0.2772 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7087(3) 0.5602(2) -0.4532(2) 0.0359(5) Uani 1 1 d . . . . .
H5A H 0.7033 0.4639 -0.4707 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6796(3) 0.6462(3) -0.5439(2) 0.0363(5) Uani 1 1 d . . . . .
H6A H 0.6542 0.6078 -0.6229 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6873(3) 0.7835(3) -0.52016(19) 0.0329(5) Uani 1 1 d . . . . .
H7A H 0.6675 0.8420 -0.5816 0.039 Uiso 1 1 calc R U . . .
C8 C 0.8744(2) 0.7603(2) 0.09773(18) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.9236(2) 0.8084(3) 0.21279(19) 0.0295(5) Uani 1 1 d . . . . .
H9A H 0.9352 0.9039 0.2347 0.035 Uiso 1 1 calc R U . . .
C10 C 0.9565(3) 0.7161(3) 0.2973(2) 0.0343(5) Uani 1 1 d . . . . .
H10A H 0.9912 0.7487 0.3773 0.041 Uiso 1 1 calc R U . . .
C11 C 0.9390(3) 0.5782(3) 0.2655(2) 0.0352(5) Uani 1 1 d . . . . .
H11A H 0.9611 0.5147 0.3228 0.042 Uiso 1 1 calc R U . . .
C12 C 0.8889(3) 0.5335(3) 0.1490(2) 0.0334(5) Uani 1 1 d . . . . .
H12A H 0.8759 0.4385 0.1249 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3426(3) 0.7724(3) 0.6978(3) 0.0465(7) Uani 1 1 d . . . . .
C14 C 0.4758(3) 0.7279(4) 0.1063(3) 0.0496(7) 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 N1 1.6362(19) . ?
S1 N4 1.7258(19) . ?
S2 O1 1.424(2) . ?
S2 O2 1.4347(19) . ?
S2 O3 1.4394(18) . ?
S2 C13 1.808(3) . ?
S3 O6 1.4313(18) . ?
S3 O4 1.4348(19) . ?
S3 O5 1.4388(17) . ?
S3 C14 1.815(3) . ?
F1 C13 1.314(3) . ?
F2 C13 1.323(4) . ?
F3 C13 1.349(4) . ?
F4 C14 1.311(4) . ?
F5 C14 1.322(3) . ?
F6 C14 1.307(4) . ?
N2 C2 1.314(3) . ?
N2 C1 1.358(3) . ?
N1 C1 1.318(3) . ?
N4 C3 1.354(3) . ?
N4 C7 1.360(3) . ?
N3 C2 1.321(3) . ?
N5 C8 1.338(3) . ?
N5 C12 1.339(3) . ?
C1 C3 1.449(3) . ?
C2 C8 1.490(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.367(3) . ?
C5 C6 1.400(4) . ?
C6 C7 1.354(3) . ?
C8 C9 1.369(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.373(4) . ?
C11 C12 1.376(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
N1 S1 N4 93.18(9) . . ?
O1 S2 O2 116.54(13) . . ?
O1 S2 O3 114.16(13) . . ?
O2 S2 O3 114.26(12) . . ?
O1 S2 C13 103.45(15) . . ?
O2 S2 C13 102.68(12) . . ?
O3 S2 C13 103.31(13) . . ?
O6 S3 O4 116.42(11) . . ?
O6 S3 O5 114.17(12) . . ?
O4 S3 O5 113.85(11) . . ?
O6 S3 C14 103.69(12) . . ?
O4 S3 C14 103.63(13) . . ?
O5 S3 C14 102.79(15) . . ?
C2 N2 C1 121.40(18) . . ?
C1 N1 S1 112.82(15) . . ?
C3 N4 C7 122.28(19) . . ?
C3 N4 S1 110.26(14) . . ?
C7 N4 S1 127.30(16) . . ?
C8 N5 C12 123.5(2) . . ?
N1 C1 N2 127.8(2) . . ?
N1 C1 C3 113.46(18) . . ?
N2 C1 C3 118.72(18) . . ?
N2 C2 N3 128.4(2) . . ?
N2 C2 C8 113.85(19) . . ?
N3 C2 C8 117.75(19) . . ?
N4 C3 C4 119.83(19) . . ?
N4 C3 C1 110.23(18) . . ?
C4 C3 C1 129.89(19) . . ?
C5 C4 C3 118.8(2) . . ?
C4 C5 C6 119.9(2) . . ?
C7 C6 C5 120.6(2) . . ?
C6 C7 N4 118.6(2) . . ?
N5 C8 C9 118.7(2) . . ?
N5 C8 C2 115.64(19) . . ?
C9 C8 C2 125.6(2) . . ?
C8 C9 C10 119.4(2) . . ?
C11 C10 C9 120.2(2) . . ?
C10 C11 C12 118.8(2) . . ?
N5 C12 C11 119.4(2) . . ?
F1 C13 F2 108.0(3) . . ?
F1 C13 F3 107.8(2) . . ?
F2 C13 F3 107.2(3) . . ?
F1 C13 S2 112.3(2) . . ?
F2 C13 S2 112.1(2) . . ?
F3 C13 S2 109.2(2) . . ?
F6 C14 F4 107.6(3) . . ?
F6 C14 F5 106.3(3) . . ?
F4 C14 F5 109.4(3) . . ?
F6 C14 S3 111.5(2) . . ?
F4 C14 S3 111.2(2) . . ?
F5 C14 S3 110.7(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
N4 S1 N1 C1 0.86(17) . . . . ?
N1 S1 N4 C3 0.47(16) . . . . ?
N1 S1 N4 C7 175.9(2) . . . . ?
S1 N1 C1 N2 178.60(18) . . . . ?
S1 N1 C1 C3 -1.9(2) . . . . ?
C2 N2 C1 N1 2.1(3) . . . . ?
C2 N2 C1 C3 -177.31(18) . . . . ?
C1 N2 C2 N3 0.2(3) . . . . ?
C1 N2 C2 C8 -179.52(18) . . . . ?
C7 N4 C3 C4 0.7(3) . . . . ?
S1 N4 C3 C4 176.34(16) . . . . ?
C7 N4 C3 C1 -177.2(2) . . . . ?
S1 N4 C3 C1 -1.5(2) . . . . ?
N1 C1 C3 N4 2.2(3) . . . . ?
N2 C1 C3 N4 -178.22(18) . . . . ?
N1 C1 C3 C4 -175.4(2) . . . . ?
N2 C1 C3 C4 4.2(3) . . . . ?
N4 C3 C4 C5 -0.5(3) . . . . ?
C1 C3 C4 C5 176.9(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 N4 0.0(4) . . . . ?
C3 N4 C7 C6 -0.4(3) . . . . ?
S1 N4 C7 C6 -175.31(18) . . . . ?
C12 N5 C8 C9 -0.1(3) . . . . ?
C12 N5 C8 C2 179.5(2) . . . . ?
N2 C2 C8 N5 -10.0(3) . . . . ?
N3 C2 C8 N5 170.27(19) . . . . ?
N2 C2 C8 C9 169.6(2) . . . . ?
N3 C2 C8 C9 -10.1(3) . . . . ?
N5 C8 C9 C10 0.3(3) . . . . ?
C2 C8 C9 C10 -179.3(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C8 N5 C12 C11 -0.1(3) . . . . ?
C10 C11 C12 N5 0.1(4) . . . . ?
O1 S2 C13 F1 63.5(3) . . . . ?
O2 S2 C13 F1 -174.9(2) . . . . ?
O3 S2 C13 F1 -55.8(3) . . . . ?
O1 S2 C13 F2 -174.8(2) . . . . ?
O2 S2 C13 F2 -53.1(2) . . . . ?
O3 S2 C13 F2 65.9(2) . . . . ?
O1 S2 C13 F3 -56.1(2) . . . . ?
O2 S2 C13 F3 65.5(2) . . . . ?
O3 S2 C13 F3 -175.4(2) . . . . ?
O6 S3 C14 F6 -61.4(2) . . . . ?
O4 S3 C14 F6 176.5(2) . . . . ?
O5 S3 C14 F6 57.7(2) . . . . ?
O6 S3 C14 F4 58.7(2) . . . . ?
O4 S3 C14 F4 -63.4(2) . . . . ?
O5 S3 C14 F4 177.8(2) . . . . ?
O6 S3 C14 F5 -179.6(2) . . . . ?
O4 S3 C14 F5 58.4(3) . . . . ?
O5 S3 C14 F5 -60.4(3) . . . . ?

_refine_diff_density_max         0.893
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 986944'
