# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_y2452

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 F2 N2 O2 S'
_chemical_formula_weight         346.43
_chemical_absolute_configuration rm

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   10.7360(3)
_cell_length_b                   15.9895(3)
_cell_length_c                   11.2155(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.652(1)
_cell_angle_gamma                90.00
_cell_volume                     1834.64(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    17150
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.51

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_exptl_crystal_density_meas      1.254
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9046
_exptl_absorpt_correction_T_max  0.9118
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18032
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8090
_reflns_number_gt                7772
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens 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)+(0.0610P)²+0.1665P] 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     SHELXL
_refine_ls_extinction_coef       0.0072(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_number_reflns         8090
_refine_ls_number_parameters     436
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.56280(3) 0.23555(2) 0.62770(3) 0.02304(8) Uani 1 1 d . . .
F1 F 0.00737(14) 0.34799(12) -0.01006(12) 0.0729(5) Uani 1 1 d . . .
F2 F -0.17036(11) 0.40933(9) 0.08938(12) 0.0567(3) Uani 1 1 d . . .
O1 O 0.44491(13) 0.31573(10) 0.25321(11) 0.0437(3) Uani 1 1 d . . .
O2 O 0.45849(10) 0.17091(8) 0.57966(11) 0.0334(3) Uani 1 1 d . . .
N1 N 0.34048(12) 0.36795(8) 0.38705(11) 0.0243(2) Uani 1 1 d D . .
N2 N 0.62464(12) 0.26528(8) 0.51614(12) 0.0249(2) Uani 1 1 d . . .
C1 C 0.17375(17) 0.35472(11) 0.18144(15) 0.0339(3) Uani 1 1 d . . .
H1 H 0.2352 0.3326 0.1442 0.041 Uiso 1 1 calc R . .
C2 C 0.04511(18) 0.36703(13) 0.11159(16) 0.0411(4) Uani 1 1 d . . .
C3 C -0.04455(16) 0.39905(11) 0.16249(18) 0.0383(4) Uani 1 1 d . . .
C4 C -0.00947(17) 0.41954(12) 0.28701(17) 0.0359(4) Uani 1 1 d . . .
H4 H -0.0724 0.4412 0.3228 0.043 Uiso 1 1 calc R . .
C5 C 0.11899(15) 0.40825(10) 0.35995(15) 0.0297(3) Uani 1 1 d . . .
H5 H 0.1445 0.4229 0.4461 0.036 Uiso 1 1 calc R . .
C6 C 0.21118(14) 0.37556(9) 0.30769(13) 0.0240(3) Uani 1 1 d . . .
C7 C 0.44696(15) 0.34150(10) 0.35613(13) 0.0266(3) Uani 1 1 d . . .
C8 C 0.57536(14) 0.34841(9) 0.46446(13) 0.0235(3) Uani 1 1 d . . .
H8 H 0.5561 0.3810 0.5329 0.028 Uiso 1 1 calc R . .
C9 C 0.67866(16) 0.39733(10) 0.42399(15) 0.0309(3) Uani 1 1 d . . .
H9 H 0.7021 0.3649 0.3576 0.037 Uiso 1 1 calc R . .
C10 C 0.6226(2) 0.48190(13) 0.37049(19) 0.0432(4) Uani 1 1 d . . .
H10A H 0.6899 0.5141 0.3480 0.065 Uiso 1 1 calc R . .
H10B H 0.5944 0.5127 0.4333 0.065 Uiso 1 1 calc R . .
H10C H 0.5477 0.4732 0.2958 0.065 Uiso 1 1 calc R . .
C11 C 0.80111(17) 0.40899(12) 0.53545(18) 0.0376(4) Uani 1 1 d . . .
H11A H 0.8426 0.3546 0.5610 0.056 Uiso 1 1 calc R . .
H11B H 0.7770 0.4338 0.6052 0.056 Uiso 1 1 calc R . .
H11C H 0.8623 0.4461 0.5117 0.056 Uiso 1 1 calc R . .
C12 C 0.65247(19) 0.20299(12) 0.43112(17) 0.0381(4) Uani 1 1 d . . .
H12A H 0.6258 0.2251 0.3456 0.057 Uiso 1 1 calc R . .
H12B H 0.6038 0.1515 0.4339 0.057 Uiso 1 1 calc R . .
H12C H 0.7463 0.1908 0.4572 0.057 Uiso 1 1 calc R . .
C13 C 0.69563(14) 0.17883(10) 0.74210(15) 0.0290(3) Uani 1 1 d . . .
C14 C 0.81000(17) 0.23952(14) 0.78749(17) 0.0418(4) Uani 1 1 d . . .
H14A H 0.8768 0.2150 0.8588 0.063 Uiso 1 1 calc R . .
H14B H 0.7790 0.2921 0.8132 0.063 Uiso 1 1 calc R . .
H14C H 0.8477 0.2504 0.7196 0.063 Uiso 1 1 calc R . .
C15 C 0.63574(18) 0.16086(14) 0.84667(18) 0.0423(4) Uani 1 1 d . . .
H15A H 0.7011 0.1340 0.9168 0.063 Uiso 1 1 calc R . .
H15B H 0.5604 0.1236 0.8153 0.063 Uiso 1 1 calc R . .
H15C H 0.6073 0.2135 0.8750 0.063 Uiso 1 1 calc R . .
C16 C 0.7342(2) 0.09781(13) 0.6930(2) 0.0461(4) Uani 1 1 d . . .
H16A H 0.7882 0.0645 0.7630 0.069 Uiso 1 1 calc R . .
H16B H 0.7839 0.1102 0.6349 0.069 Uiso 1 1 calc R . .
H16C H 0.6553 0.0662 0.6492 0.069 Uiso 1 1 calc R . .
S1' S 0.38886(3) 0.38256(2) 0.74923(3) 0.02533(9) Uani 1 1 d . . .
F1' F -0.18220(11) 0.20240(10) 0.16554(12) 0.0571(3) Uani 1 1 d . . .
F2' F -0.05524(13) 0.10235(9) 0.05026(10) 0.0572(3) Uani 1 1 d . . .
O1' O 0.02360(12) 0.25327(10) 0.59987(12) 0.0434(3) Uani 1 1 d . . .
O2' O 0.35153(13) 0.42718(9) 0.62609(10) 0.0363(3) Uani 1 1 d . . .
N1' N 0.19269(12) 0.20853(8) 0.53385(12) 0.0246(2) Uani 1 1 d D . .
N2' N 0.25869(12) 0.34461(8) 0.78002(12) 0.0264(3) Uani 1 1 d . . .
C1' C -0.00380(15) 0.20612(11) 0.34970(16) 0.0300(3) Uani 1 1 d . . .
H1' H -0.0515 0.2395 0.3908 0.036 Uiso 1 1 calc R . .
C2' C -0.06081(17) 0.17890(11) 0.22853(16) 0.0358(4) Uani 1 1 d . . .
C3' C 0.00554(19) 0.12979(12) 0.16815(15) 0.0386(4) Uani 1 1 d . . .
C4' C 0.1342(2) 0.10800(12) 0.22777(16) 0.0391(4) Uani 1 1 d . . .
H4' H 0.1811 0.0745 0.1860 0.047 Uiso 1 1 calc R . .
C5' C 0.19371(16) 0.13533(11) 0.34836(14) 0.0316(3) Uani 1 1 d . . .
H5' H 0.2823 0.1210 0.3894 0.038 Uiso 1 1 calc R . .
C6' C 0.12512(14) 0.18362(9) 0.41025(13) 0.0243(3) Uani 1 1 d . . .
C7' C 0.13968(14) 0.23966(10) 0.61990(14) 0.0277(3) Uani 1 1 d . . .
C8' C 0.23763(14) 0.25415(9) 0.75055(14) 0.0252(3) Uani 1 1 d . . .
H8' H 0.3233 0.2297 0.7503 0.030 Uiso 1 1 calc R . .
C9' C 0.19473(17) 0.20905(10) 0.85246(16) 0.0320(3) Uani 1 1 d . . .
H9' H 0.1165 0.2386 0.8626 0.038 Uiso 1 1 calc R . .
C10' C 0.1570(2) 0.11812(12) 0.8164(2) 0.0473(5) Uani 1 1 d . . .
H10D H 0.1252 0.0920 0.8808 0.071 Uiso 1 1 calc R . .
H10E H 0.2336 0.0875 0.8096 0.071 Uiso 1 1 calc R . .
H10F H 0.0879 0.1166 0.7358 0.071 Uiso 1 1 calc R . .
C11' C 0.3028(2) 0.21238(12) 0.97631(16) 0.0412(4) Uani 1 1 d . . .
H11D H 0.3278 0.2707 0.9976 0.062 Uiso 1 1 calc R . .
H11E H 0.3787 0.1810 0.9694 0.062 Uiso 1 1 calc R . .
H11F H 0.2717 0.1876 1.0420 0.062 Uiso 1 1 calc R . .
C12' C 0.14330(17) 0.39770(10) 0.76661(17) 0.0356(4) Uani 1 1 d . . .
H12D H 0.0663 0.3623 0.7565 0.053 Uiso 1 1 calc R . .
H12E H 0.1293 0.4336 0.6929 0.053 Uiso 1 1 calc R . .
H12F H 0.1574 0.4325 0.8415 0.053 Uiso 1 1 calc R . .
C13' C 0.44893(17) 0.46783(11) 0.86359(14) 0.0332(4) Uani 1 1 d . . .
C14' C 0.4670(3) 0.43406(15) 0.99412(17) 0.0549(6) Uani 1 1 d . . .
H14D H 0.5145 0.4751 1.0562 0.082 Uiso 1 1 calc R . .
H14E H 0.5168 0.3818 1.0054 0.082 Uiso 1 1 calc R . .
H14F H 0.3812 0.4235 1.0051 0.082 Uiso 1 1 calc R . .
C15' C 0.5823(2) 0.48658(15) 0.8450(2) 0.0493(5) Uani 1 1 d . . .
H15D H 0.6290 0.5280 0.9069 0.074 Uiso 1 1 calc R . .
H15E H 0.5691 0.5087 0.7606 0.074 Uiso 1 1 calc R . .
H15F H 0.6338 0.4350 0.8558 0.074 Uiso 1 1 calc R . .
C16' C 0.3632(2) 0.54562(12) 0.8340(2) 0.0446(4) Uani 1 1 d . . .
H16D H 0.4134 0.5941 0.8762 0.067 Uiso 1 1 calc R . .
H16E H 0.2868 0.5377 0.8634 0.067 Uiso 1 1 calc R . .
H16F H 0.3342 0.5551 0.7434 0.067 Uiso 1 1 calc R . .
H1N H 0.3505(19) 0.3843(13) 0.4618(11) 0.034(5) Uiso 1 1 d D . .
H1'N H 0.2762(10) 0.2027(14) 0.554(2) 0.038(5) Uiso 1 1 d 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 1.4989(12) . ?
S1 N2 1.6541(13) . ?
S1 C13 1.8419(15) . ?
F1 C2 1.335(2) . ?
F2 C3 1.3608(18) . ?
O1 C7 1.2196(19) . ?
N1 C7 1.359(2) . ?
N1 C6 1.4088(18) . ?
N1 H1N 0.853(9) . ?
N2 C12 1.471(2) . ?
N2 C8 1.4821(19) . ?
C1 C2 1.380(2) . ?
C1 C6 1.390(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.359(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.5404(19) . ?
C8 C9 1.534(2) . ?
C8 H8 1.0000 . ?
C9 C11 1.526(2) . ?
C9 C10 1.527(2) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C16 1.514(3) . ?
C13 C15 1.526(2) . ?
C13 C14 1.526(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
S1' O2' 1.4971(12) . ?
S1' N2' 1.6532(14) . ?
S1' C13' 1.8490(16) . ?
F1' C2' 1.334(2) . ?
F2' C3' 1.3577(19) . ?
O1' C7' 1.2169(19) . ?
N1' C7' 1.3551(19) . ?
N1' C6' 1.4130(18) . ?
N1' H1'N 0.860(9) . ?
N2' C12' 1.471(2) . ?
N2' C8' 1.4858(19) . ?
C1' C2' 1.381(2) . ?
C1' C6' 1.391(2) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.369(3) . ?
C3' C4' 1.384(3) . ?
C4' C5' 1.380(2) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.389(2) . ?
C5' H5' 0.9500 . ?
C7' C8' 1.540(2) . ?
C8' C9' 1.536(2) . ?
C8' H8' 1.0000 . ?
C9' C11' 1.517(2) . ?
C9' C10' 1.530(2) . ?
C9' H9' 1.0000 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' C14' 1.517(2) . ?
C13' C16' 1.523(3) . ?
C13' C15' 1.537(3) . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 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
O2 S1 N2 110.72(7) . . ?
O2 S1 C13 104.31(7) . . ?
N2 S1 C13 105.36(7) . . ?
C7 N1 C6 127.57(12) . . ?
C7 N1 H1N 118.7(14) . . ?
C6 N1 H1N 113.7(14) . . ?
C12 N2 C8 118.19(13) . . ?
C12 N2 S1 120.18(11) . . ?
C8 N2 S1 112.09(9) . . ?
C2 C1 C6 118.33(16) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
F1 C2 C3 118.74(16) . . ?
F1 C2 C1 119.27(18) . . ?
C3 C2 C1 121.98(16) . . ?
C2 C3 F2 119.49(17) . . ?
C2 C3 C4 120.46(15) . . ?
F2 C3 C4 120.05(17) . . ?
C3 C4 C5 119.14(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.43(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.65(14) . . ?
C1 C6 N1 123.23(14) . . ?
C5 C6 N1 117.09(13) . . ?
O1 C7 N1 124.87(14) . . ?
O1 C7 C8 121.72(14) . . ?
N1 C7 C8 113.41(12) . . ?
N2 C8 C9 111.63(12) . . ?
N2 C8 C7 111.84(12) . . ?
C9 C8 C7 110.95(12) . . ?
N2 C8 H8 107.4 . . ?
C9 C8 H8 107.4 . . ?
C7 C8 H8 107.4 . . ?
C11 C9 C10 110.64(15) . . ?
C11 C9 C8 109.90(13) . . ?
C10 C9 C8 109.50(14) . . ?
C11 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C8 C9 H9 108.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C13 C15 110.11(16) . . ?
C16 C13 C14 112.62(15) . . ?
C15 C13 C14 110.32(15) . . ?
C16 C13 S1 114.03(12) . . ?
C15 C13 S1 102.15(11) . . ?
C14 C13 S1 107.10(11) . . ?
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 . . ?
O2' S1' N2' 111.15(7) . . ?
O2' S1' C13' 103.18(8) . . ?
N2' S1' C13' 105.36(7) . . ?
C7' N1' C6' 126.92(12) . . ?
C7' N1' H1'N 118.5(15) . . ?
C6' N1' H1'N 114.6(15) . . ?
C12' N2' C8' 118.19(13) . . ?
C12' N2' S1' 120.39(11) . . ?
C8' N2' S1' 113.08(10) . . ?
C2' C1' C6' 118.51(16) . . ?
C2' C1' H1' 120.7 . . ?
C6' C1' H1' 120.7 . . ?
F1' C2' C3' 118.08(16) . . ?
F1' C2' C1' 120.17(17) . . ?
C3' C2' C1' 121.71(15) . . ?
F2' C3' C2' 119.90(16) . . ?
F2' C3' C4' 120.25(17) . . ?
C2' C3' C4' 119.86(15) . . ?
C5' C4' C3' 119.45(17) . . ?
C5' C4' H4' 120.3 . . ?
C3' C4' H4' 120.3 . . ?
C4' C5' C6' 120.49(15) . . ?
C4' C5' H5' 119.8 . . ?
C6' C5' H5' 119.8 . . ?
C5' C6' C1' 119.95(14) . . ?
C5' C6' N1' 117.04(13) . . ?
C1' C6' N1' 123.00(14) . . ?
O1' C7' N1' 124.19(14) . . ?
O1' C7' C8' 120.95(14) . . ?
N1' C7' C8' 114.82(12) . . ?
N2' C8' C9' 110.57(12) . . ?
N2' C8' C7' 111.84(12) . . ?
C9' C8' C7' 111.42(13) . . ?
N2' C8' H8' 107.6 . . ?
C9' C8' H8' 107.6 . . ?
C7' C8' H8' 107.6 . . ?
C11' C9' C10' 110.06(16) . . ?
C11' C9' C8' 110.26(14) . . ?
C10' C9' C8' 111.39(14) . . ?
C11' C9' H9' 108.3 . . ?
C10' C9' H9' 108.3 . . ?
C8' C9' H9' 108.3 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C9' C11' H11D 109.5 . . ?
C9' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C9' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N2' C12' H12D 109.5 . . ?
N2' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
N2' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C14' C13' C16' 113.13(17) . . ?
C14' C13' C15' 110.39(18) . . ?
C16' C13' C15' 109.73(16) . . ?
C14' C13' S1' 108.82(12) . . ?
C16' C13' S1' 112.99(12) . . ?
C15' C13' S1' 101.14(12) . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C13' C15' H15D 109.5 . . ?
C13' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C13' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C13' C16' H16D 109.5 . . ?
C13' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C13' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C12 -41.95(14) . . . . ?
C13 S1 N2 C12 70.26(14) . . . . ?
O2 S1 N2 C8 103.72(10) . . . . ?
C13 S1 N2 C8 -144.07(10) . . . . ?
C6 C1 C2 F1 179.51(18) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
F1 C2 C3 F2 1.3(3) . . . . ?
C1 C2 C3 F2 -179.55(18) . . . . ?
F1 C2 C3 C4 -179.86(19) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
F2 C3 C4 C5 179.71(16) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 N1 -178.09(16) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 N1 178.41(15) . . . . ?
C7 N1 C6 C1 1.0(2) . . . . ?
C7 N1 C6 C5 -176.91(15) . . . . ?
C6 N1 C7 O1 -4.0(3) . . . . ?
C6 N1 C7 C8 174.94(13) . . . . ?
C12 N2 C8 C9 -66.41(17) . . . . ?
S1 N2 C8 C9 147.17(10) . . . . ?
C12 N2 C8 C7 58.58(18) . . . . ?
S1 N2 C8 C7 -87.84(12) . . . . ?
O1 C7 C8 N2 -73.3(2) . . . . ?
N1 C7 C8 N2 107.75(15) . . . . ?
O1 C7 C8 C9 52.0(2) . . . . ?
N1 C7 C8 C9 -126.89(14) . . . . ?
N2 C8 C9 C11 -58.79(17) . . . . ?
C7 C8 C9 C11 175.73(14) . . . . ?
N2 C8 C9 C10 179.48(14) . . . . ?
C7 C8 C9 C10 54.00(17) . . . . ?
O2 S1 C13 C16 50.34(15) . . . . ?
N2 S1 C13 C16 -66.32(15) . . . . ?
O2 S1 C13 C15 -68.41(13) . . . . ?
N2 S1 C13 C15 174.93(12) . . . . ?
O2 S1 C13 C14 175.63(12) . . . . ?
N2 S1 C13 C14 58.96(13) . . . . ?
O2' S1' N2' C12' -48.48(14) . . . . ?
C13' S1' N2' C12' 62.61(13) . . . . ?
O2' S1' N2' C8' 99.20(11) . . . . ?
C13' S1' N2' C8' -149.71(11) . . . . ?
C6' C1' C2' F1' -176.93(16) . . . . ?
C6' C1' C2' C3' 1.0(3) . . . . ?
F1' C2' C3' F2' -3.9(3) . . . . ?
C1' C2' C3' F2' 178.12(17) . . . . ?
F1' C2' C3' C4' 176.35(18) . . . . ?
C1' C2' C3' C4' -1.6(3) . . . . ?
F2' C3' C4' C5' -178.95(17) . . . . ?
C2' C3' C4' C5' 0.8(3) . . . . ?
C3' C4' C5' C6' 0.7(3) . . . . ?
C4' C5' C6' C1' -1.3(2) . . . . ?
C4' C5' C6' N1' 179.49(16) . . . . ?
C2' C1' C6' C5' 0.5(2) . . . . ?
C2' C1' C6' N1' 179.66(15) . . . . ?
C7' N1' C6' C5' -164.94(16) . . . . ?
C7' N1' C6' C1' 15.8(2) . . . . ?
C6' N1' C7' O1' -2.7(3) . . . . ?
C6' N1' C7' C8' 175.02(14) . . . . ?
C12' N2' C8' C9' -72.20(17) . . . . ?
S1' N2' C8' C9' 139.35(11) . . . . ?
C12' N2' C8' C7' 52.59(18) . . . . ?
S1' N2' C8' C7' -95.86(13) . . . . ?
O1' C7' C8' N2' -72.0(2) . . . . ?
N1' C7' C8' N2' 110.24(15) . . . . ?
O1' C7' C8' C9' 52.3(2) . . . . ?
N1' C7' C8' C9' -125.44(15) . . . . ?
N2' C8' C9' C11' -64.21(17) . . . . ?
C7' C8' C9' C11' 170.75(13) . . . . ?
N2' C8' C9' C10' 173.29(15) . . . . ?
C7' C8' C9' C10' 48.26(19) . . . . ?
O2' S1' C13' C14' 169.67(15) . . . . ?
N2' S1' C13' C14' 53.02(16) . . . . ?
O2' S1' C13' C16' 43.13(14) . . . . ?
N2' S1' C13' C16' -73.53(14) . . . . ?
O2' S1' C13' C15' -74.08(14) . . . . ?
N2' S1' C13' C15' 169.26(12) . . . . ?

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
N1 H1N O2' 0.853(9) 1.963(10) 2.8116(16) 173(2) .
N1' H1'N O2 0.860(9) 1.958(10) 2.8071(16) 169(2) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1003514'
#######################################################################
#
#                 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_y2445

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 F2 N2 O2 S'
_chemical_formula_weight         346.43
_chemical_absolute_configuration rm

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.3912(5)
_cell_length_b                   10.6576(4)
_cell_length_c                   18.9928(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.820(2)
_cell_angle_gamma                90.00
_cell_volume                     1894.22(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    17333,CELMIN=6.05,CELMAX=55.01
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.56

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      1.215
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8938
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18610
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8181
_reflns_number_gt                7735
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_cell_refinement       'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_data_reduction        'Rapid Auto Version 3.0 (Rigaku 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens 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)+(0.0569P)²+0.1746P] 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     SHELXL
_refine_ls_extinction_coef       0.0109(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_number_reflns         8181
_refine_ls_number_parameters     524
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.997
_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 0.50909(3) 0.46742(4) 0.984265(17) 0.03373(9) Uani 1 1 d . . .
F1 F 0.31707(14) -0.12521(13) 0.74559(7) 0.0694(3) Uani 1 1 d . . .
F2 F 0.06354(14) -0.09191(12) 0.67001(6) 0.0607(3) Uani 1 1 d . . .
O1 O 0.06636(14) 0.36193(13) 0.89348(8) 0.0586(4) Uani 1 1 d . . .
O2 O 0.54794(13) 0.59569(13) 1.01235(7) 0.0495(3) Uani 1 1 d . . .
N1 N 0.21333(14) 0.19294(12) 0.90800(7) 0.0365(3) Uani 1 1 d . . .
N2 N 0.33669(11) 0.46782(13) 0.95873(6) 0.0322(2) Uani 1 1 d . . .
C1 C 0.26376(18) 0.03179(16) 0.82607(10) 0.0434(4) Uani 1 1 d . . .
H1 H 0.3534 0.0189 0.8521 0.052 Uiso 1 1 calc R . .
C2 C 0.22549(19) -0.03833(18) 0.76731(9) 0.0475(4) Uani 1 1 d . . .
C3 C 0.09674(19) -0.02115(18) 0.72883(8) 0.0458(4) Uani 1 1 d . . .
C4 C 0.00204(18) 0.06638(17) 0.74945(9) 0.0435(4) Uani 1 1 d . . .
H4 H -0.0878 0.0770 0.7232 0.052 Uiso 1 1 calc R . .
C5 C 0.03784(16) 0.13971(15) 0.80894(9) 0.0388(3) Uani 1 1 d . . .
H5 H -0.0271 0.2011 0.8233 0.047 Uiso 1 1 calc R . .
C6 C 0.16918(15) 0.12267(16) 0.84732(8) 0.0351(3) Uani 1 1 d . . .
C7 C 0.16533(15) 0.30755(15) 0.92553(9) 0.0373(3) Uani 1 1 d . . .
C8 C 0.25154(15) 0.36895(15) 0.98872(8) 0.0337(3) Uani 1 1 d . . .
H8 H 0.3190 0.3046 1.0106 0.040 Uiso 1 1 calc R . .
C9 C 0.15716(19) 0.4145(2) 1.04566(11) 0.0523(4) Uani 1 1 d . . .
H9 H 0.0913 0.4810 1.0248 0.063 Uiso 1 1 calc R . .
C10 C 0.0681(3) 0.3064(3) 1.07012(15) 0.0773(7) Uani 1 1 d . . .
H10A H 0.1307 0.2457 1.0962 0.093 Uiso 1 1 calc R . .
H10B H 0.0184 0.2653 1.0290 0.093 Uiso 1 1 calc R . .
H10C H -0.0021 0.3386 1.1010 0.093 Uiso 1 1 calc R . .
C11 C 0.2513(3) 0.4712(3) 1.10719(11) 0.0736(6) Uani 1 1 d . . .
H11A H 0.3186 0.4077 1.1270 0.088 Uiso 1 1 calc R . .
H11B H 0.1911 0.4997 1.1438 0.088 Uiso 1 1 calc R . .
H11C H 0.3045 0.5426 1.0902 0.088 Uiso 1 1 calc R . .
C12 C 0.2670(2) 0.58427(17) 0.93329(12) 0.0530(5) Uani 1 1 d . . .
H12A H 0.2227 0.5716 0.8852 0.064 Uiso 1 1 calc R . .
H12B H 0.3383 0.6514 0.9331 0.064 Uiso 1 1 calc R . .
H12C H 0.1935 0.6076 0.9645 0.064 Uiso 1 1 calc R . .
C13 C 0.59714(18) 0.4554(2) 0.90159(9) 0.0491(4) Uani 1 1 d . . .
C14 C 0.5439(3) 0.3334(2) 0.86607(11) 0.0649(6) Uani 1 1 d . . .
H14A H 0.4429 0.3424 0.8491 0.078 Uiso 1 1 calc R . .
H14B H 0.5545 0.2645 0.9003 0.078 Uiso 1 1 calc R . .
H14C H 0.6001 0.3151 0.8261 0.078 Uiso 1 1 calc R . .
C15 C 0.5710(3) 0.5694(3) 0.85550(13) 0.0736(7) Uani 1 1 d . . .
H15A H 0.6384 0.5698 0.8188 0.088 Uiso 1 1 calc R . .
H15B H 0.5845 0.6453 0.8844 0.088 Uiso 1 1 calc R . .
H15C H 0.4730 0.5672 0.8333 0.088 Uiso 1 1 calc R . .
C16 C 0.7553(2) 0.4453(3) 0.92779(16) 0.0838(8) Uani 1 1 d . . .
H16A H 0.7687 0.3756 0.9613 0.101 Uiso 1 1 calc R . .
H16B H 0.7866 0.5237 0.9512 0.101 Uiso 1 1 calc R . .
H16C H 0.8119 0.4301 0.8876 0.101 Uiso 1 1 calc R . .
S1' S 0.39593(4) 0.61787(4) 0.517469(19) 0.04002(10) Uani 1 1 d D . .
O1' O 0.30548(13) 0.70702(12) 0.29526(6) 0.0448(3) Uani 1 1 d . A .
O2' O 0.44109(15) 0.49559(14) 0.55082(7) 0.0570(3) Uani 1 1 d . B .
N2' N 0.40324(17) 0.60456(13) 0.43202(7) 0.0442(3) Uani 1 1 d . A .
F1' F 0.20227(18) 1.30047(12) 0.28646(10) 0.0768(6) Uani 0.870(4) 1 d PD A 1
F2' F -0.0438(3) 1.2111(3) 0.2175(2) 0.0683(12) Uani 0.870(4) 1 d PD A 1
N1' N 0.3461(3) 0.89006(19) 0.35664(19) 0.0387(16) Uani 0.870(4) 1 d PD A 1
H1N' H 0.4000 0.9248 0.3915 0.046 Uiso 0.870(4) 1 calc PR A 1
C1' C 0.2708(3) 1.0960(2) 0.32078(17) 0.0424(4) Uani 0.870(4) 1 d PD A 1
H1' H 0.3550 1.1280 0.3456 0.051 Uiso 0.870(4) 1 calc PR A 1
C2' C 0.1734(3) 1.1757(2) 0.2861(2) 0.0495(5) Uani 0.870(4) 1 d PD A 1
C3' C 0.0497(2) 1.1306(2) 0.25093(13) 0.0451(5) Uani 0.870(4) 1 d PD A 1
C4' C 0.0228(2) 1.0050(2) 0.24975(12) 0.0502(6) Uani 0.870(4) 1 d PD A 1
H4' H -0.0631 0.9739 0.2260 0.060 Uiso 0.870(4) 1 calc PR A 1
C5' C 0.1205(3) 0.9227(3) 0.2831(2) 0.0469(10) Uani 0.870(4) 1 d PD A 1
H5' H 0.1023 0.8350 0.2813 0.056 Uiso 0.870(4) 1 calc PR A 1
C6' C 0.2437(2) 0.9669(2) 0.31896(13) 0.0353(3) Uani 0.870(4) 1 d PD A 1
F1" F -0.1139(4) 0.9646(4) 0.2364(5) 0.067(3) Uani 0.130(4) 1 d PD A 2
F2" F -0.0594(15) 1.2144(11) 0.2283(12) 0.042(4) Uani 0.130(4) 1 d PD A 2
N1" N 0.3438(13) 0.8902(5) 0.3535(9) 0.036(10) Uani 0.130(4) 1 d PD A 2
H1N" H 0.4025 0.9231 0.3871 0.043 Uiso 0.130(4) 1 calc PR A 2
C1" C 0.1139(7) 0.9301(7) 0.2945(5) 0.043(9) Uani 0.130(4) 1 d PD A 2
H1" H 0.0941 0.8429 0.2972 0.052 Uiso 0.130(4) 1 calc PR A 2
C2" C 0.0138(5) 1.0112(7) 0.2633(5) 0.0495(5) Uani 0.130(4) 1 d PD A 2
C3" C 0.0415(10) 1.1378(7) 0.2592(9) 0.0451(5) Uani 0.130(4) 1 d PD A 2
C4" C 0.1696(12) 1.1845(8) 0.2864(12) 0.0502(6) Uani 0.130(4) 1 d PD A 2
H4" H 0.1886 1.2718 0.2836 0.060 Uiso 0.130(4) 1 calc PR A 2
C5" C 0.2721(11) 1.1046(8) 0.3180(11) 0.0469(10) Uani 0.130(4) 1 d PD A 2
H5" H 0.3614 1.1373 0.3369 0.056 Uiso 0.130(4) 1 calc PR A 2
C6" C 0.2455(9) 0.9780(7) 0.3222(7) 0.0353(3) Uani 0.130(4) 1 d PD A 2
C7' C 0.36792(17) 0.76679(13) 0.34334(8) 0.0357(3) Uani 1 1 d D . .
C8' C 0.47780(17) 0.70498(15) 0.39657(8) 0.0370(3) Uani 1 1 d . A .
H8' H 0.5088 0.7693 0.4330 0.044 Uiso 1 1 calc R . .
C9' C 0.6107(2) 0.6602(2) 0.36294(9) 0.0500(4) Uani 1 1 d . . .
H9' H 0.5822 0.5937 0.3274 0.060 Uiso 1 1 calc R A .
C10' C 0.6786(2) 0.7687(2) 0.32545(11) 0.0585(5) Uani 1 1 d . A .
H10D H 0.6090 0.8034 0.2893 0.070 Uiso 1 1 calc R . .
H10E H 0.7623 0.7382 0.3031 0.070 Uiso 1 1 calc R . .
H10F H 0.7081 0.8341 0.3599 0.070 Uiso 1 1 calc R . .
C11' C 0.7164(3) 0.6043(3) 0.41968(12) 0.0765(7) Uani 1 1 d . A .
H11D H 0.8041 0.5802 0.3986 0.092 Uiso 1 1 calc R . .
H11E H 0.6740 0.5300 0.4400 0.092 Uiso 1 1 calc R . .
H11F H 0.7390 0.6666 0.4569 0.092 Uiso 1 1 calc R . .
C12' C 0.3690(3) 0.48566(18) 0.39604(10) 0.0615(5) Uani 1 1 d . . .
H12D H 0.2893 0.4982 0.3600 0.074 Uiso 1 1 calc R B .
H12E H 0.3421 0.4234 0.4305 0.074 Uiso 1 1 calc R . .
H12F H 0.4528 0.4557 0.3735 0.074 Uiso 1 1 calc R . .
C13' C 0.2016(4) 0.6252(8) 0.5256(6) 0.0509(18) Uani 0.58(4) 1 d PD B 1
C14' C 0.1397(11) 0.7326(10) 0.4793(9) 0.068(3) Uani 0.58(4) 1 d PD B 1
H14D H 0.1468 0.7117 0.4294 0.082 Uiso 0.58(4) 1 calc PR B 1
H14E H 0.1935 0.8096 0.4910 0.082 Uiso 0.58(4) 1 calc PR B 1
H14F H 0.0392 0.7451 0.4877 0.082 Uiso 0.58(4) 1 calc PR B 1
C15' C 0.1267(9) 0.5030(9) 0.5080(6) 0.062(2) Uani 0.58(4) 1 d PD B 1
H15D H 0.0329 0.5032 0.5271 0.074 Uiso 0.58(4) 1 calc PR B 1
H15E H 0.1841 0.4335 0.5289 0.074 Uiso 0.58(4) 1 calc PR B 1
H15F H 0.1143 0.4926 0.4566 0.074 Uiso 0.58(4) 1 calc PR B 1
C16' C 0.1966(12) 0.6561(13) 0.6037(7) 0.084(3) Uani 0.58(4) 1 d PD B 1
H16D H 0.2494 0.7339 0.6147 0.100 Uiso 0.58(4) 1 calc PR B 1
H16E H 0.2402 0.5875 0.6324 0.100 Uiso 0.58(4) 1 calc PR B 1
H16F H 0.0970 0.6667 0.6144 0.100 Uiso 0.58(4) 1 calc PR B 1
C13" C 0.2098(7) 0.6299(10) 0.5405(10) 0.058(3) Uani 0.42(4) 1 d PD B 2
C14" C 0.157(2) 0.7510(14) 0.5042(13) 0.081(4) Uani 0.42(4) 1 d PD B 2
H14G H 0.1616 0.7430 0.4531 0.097 Uiso 0.42(4) 1 calc PR B 2
H14H H 0.2169 0.8212 0.5220 0.097 Uiso 0.42(4) 1 calc PR B 2
H14I H 0.0577 0.7665 0.5144 0.097 Uiso 0.42(4) 1 calc PR B 2
C15" C 0.1196(17) 0.5186(15) 0.5171(13) 0.094(6) Uani 0.42(4) 1 d PD B 2
H15G H 0.0248 0.5270 0.5346 0.113 Uiso 0.42(4) 1 calc PR B 2
H15H H 0.1652 0.4416 0.5362 0.113 Uiso 0.42(4) 1 calc PR B 2
H15I H 0.1099 0.5145 0.4654 0.113 Uiso 0.42(4) 1 calc PR B 2
C16" C 0.221(2) 0.6430(16) 0.6206(10) 0.102(5) Uani 0.42(4) 1 d PD B 2
H16G H 0.3135 0.6807 0.6366 0.122 Uiso 0.42(4) 1 calc PR B 2
H16H H 0.2137 0.5600 0.6422 0.122 Uiso 0.42(4) 1 calc PR B 2
H16I H 0.1437 0.6968 0.6346 0.122 Uiso 0.42(4) 1 calc PR B 2
H1N H 0.293(2) 0.1654(17) 0.9301(10) 0.036(4) Uiso 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 1.5012(13) . ?
S1 N2 1.6506(11) . ?
S1 C13 1.8397(16) . ?
F1 C2 1.352(2) . ?
F2 C3 1.362(2) . ?
O1 C7 1.2145(18) . ?
N1 C7 1.353(2) . ?
N1 C6 1.407(2) . ?
N1 H1N 0.88(2) . ?
N2 C12 1.466(2) . ?
N2 C8 1.4666(19) . ?
C1 C2 1.366(3) . ?
C1 C6 1.397(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(2) . ?
C3 C4 1.369(3) . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.537(2) . ?
C8 C9 1.534(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.519(3) . ?
C9 C11 1.529(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.505(3) . ?
C13 C14 1.530(3) . ?
C13 C16 1.530(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
S1' O2' 1.4948(13) . ?
S1' N2' 1.6363(13) . ?
S1' C13" 1.841(3) . ?
S1' C13' 1.846(3) . ?
O1' C7' 1.2222(18) . ?
N2' C12' 1.463(2) . ?
N2' C8' 1.472(2) . ?
F1' C2' 1.357(3) . ?
F2' C3' 1.347(2) . ?
N1' C7' 1.357(2) . ?
N1' C6' 1.4113(17) . ?
N1' H1N' 0.8800 . ?
C1' C2' 1.375(3) . ?
C1' C6' 1.399(3) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.377(3) . ?
C3' C4' 1.362(3) . ?
C4' C5' 1.384(3) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.376(3) . ?
C5' H5' 0.9500 . ?
F1" C2" 1.357(4) . ?
F2" C3" 1.347(3) . ?
N1" C7' 1.352(3) . ?
N1" C6" 1.411(2) . ?
N1" H1N" 0.8800 . ?
C1" C2" 1.375(4) . ?
C1" C6" 1.399(4) . ?
C1" H1" 0.9500 . ?
C2" C3" 1.378(4) . ?
C3" C4" 1.362(4) . ?
C4" C5" 1.384(4) . ?
C4" H4" 0.9500 . ?
C5" C6" 1.375(4) . ?
C5" H5" 0.9500 . ?
C7' C8' 1.531(2) . ?
C8' C9' 1.526(2) . ?
C8' H8' 1.0000 . ?
C9' C11' 1.524(3) . ?
C9' C10' 1.525(3) . ?
C9' H9' 1.0000 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' H12D 0.9800 . ?
C12' H12E 0.9800 . ?
C12' H12F 0.9800 . ?
C13' C15' 1.505(5) . ?
C13' C16' 1.525(6) . ?
C13' C14' 1.528(5) . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' H16D 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16F 0.9800 . ?
C13" C15" 1.503(6) . ?
C13" C16" 1.523(6) . ?
C13" C14" 1.527(5) . ?
C14" H14G 0.9800 . ?
C14" H14H 0.9800 . ?
C14" H14I 0.9800 . ?
C15" H15G 0.9800 . ?
C15" H15H 0.9800 . ?
C15" H15I 0.9800 . ?
C16" H16G 0.9800 . ?
C16" H16H 0.9800 . ?
C16" H16I 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
O2 S1 N2 107.77(7) . . ?
O2 S1 C13 104.69(8) . . ?
N2 S1 C13 104.45(7) . . ?
C7 N1 C6 126.90(13) . . ?
C7 N1 H1N 118.2(12) . . ?
C6 N1 H1N 113.3(12) . . ?
C12 N2 C8 119.57(12) . . ?
C12 N2 S1 119.92(11) . . ?
C8 N2 S1 115.94(9) . . ?
C2 C1 C6 119.05(15) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
F1 C2 C1 119.59(16) . . ?
F1 C2 C3 118.94(17) . . ?
C1 C2 C3 121.46(16) . . ?
F2 C3 C4 120.18(16) . . ?
F2 C3 C2 119.60(17) . . ?
C4 C3 C2 120.23(16) . . ?
C3 C4 C5 119.78(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.69(16) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.77(15) . . ?
C5 C6 N1 123.16(15) . . ?
C1 C6 N1 117.06(13) . . ?
O1 C7 N1 124.35(15) . . ?
O1 C7 C8 121.26(15) . . ?
N1 C7 C8 114.33(12) . . ?
N2 C8 C9 114.38(14) . . ?
N2 C8 C7 105.75(12) . . ?
C9 C8 C7 112.82(13) . . ?
N2 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C10 C9 C11 111.3(2) . . ?
C10 C9 C8 109.96(17) . . ?
C11 C9 C8 109.43(14) . . ?
C10 C9 H9 108.7 . . ?
C11 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 113.47(18) . . ?
C15 C13 C16 110.6(2) . . ?
C14 C13 C16 110.9(2) . . ?
C15 C13 S1 112.15(14) . . ?
C14 C13 S1 106.37(12) . . ?
C16 C13 S1 102.76(14) . . ?
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 . . ?
O2' S1' N2' 108.10(8) . . ?
O2' S1' C13" 101.6(4) . . ?
N2' S1' C13" 111.2(6) . . ?
O2' S1' C13' 104.4(3) . . ?
N2' S1' C13' 102.2(4) . . ?
C13" S1' C13' 9.1(6) . . ?
C12' N2' C8' 120.69(14) . . ?
C12' N2' S1' 120.84(12) . . ?
C8' N2' S1' 116.85(11) . . ?
C7' N1' C6' 125.1(2) . . ?
C7' N1' H1N' 117.5 . . ?
C6' N1' H1N' 117.5 . . ?
C2' C1' C6' 118.9(2) . . ?
C2' C1' H1' 120.5 . . ?
C6' C1' H1' 120.5 . . ?
F1' C2' C1' 118.6(2) . . ?
F1' C2' C3' 120.3(2) . . ?
C1' C2' C3' 121.09(19) . . ?
F2' C3' C4' 120.3(2) . . ?
F2' C3' C2' 119.7(2) . . ?
C4' C3' C2' 119.94(17) . . ?
C3' C4' C5' 120.0(2) . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C6' C5' C4' 120.5(2) . . ?
C6' C5' H5' 119.8 . . ?
C4' C5' H5' 119.8 . . ?
C5' C6' C1' 119.52(16) . . ?
C5' C6' N1' 124.1(2) . . ?
C1' C6' N1' 116.3(2) . . ?
C7' N1" C6" 134.2(6) . . ?
C7' N1" H1N" 112.9 . . ?
C6" N1" H1N" 112.9 . . ?
C2" C1" C6" 118.9(4) . . ?
C2" C1" H1" 120.5 . . ?
C6" C1" H1" 120.5 . . ?
F1" C2" C1" 118.9(5) . . ?
F1" C2" C3" 120.2(5) . . ?
C1" C2" C3" 120.9(4) . . ?
F2" C3" C4" 120.6(5) . . ?
F2" C3" C2" 119.2(5) . . ?
C4" C3" C2" 120.1(3) . . ?
C3" C4" C5" 120.0(4) . . ?
C3" C4" H4" 120.0 . . ?
C5" C4" H4" 120.0 . . ?
C6" C5" C4" 120.4(5) . . ?
C6" C5" H5" 119.8 . . ?
C4" C5" H5" 119.8 . . ?
C5" C6" C1" 119.7(3) . . ?
C5" C6" N1" 124.0(5) . . ?
C1" C6" N1" 116.3(5) . . ?
O1' C7' N1" 122.6(4) . . ?
O1' C7' N1' 124.98(17) . . ?
N1" C7' N1' 2.6(7) . . ?
O1' C7' C8' 121.56(13) . . ?
N1" C7' C8' 115.8(4) . . ?
N1' C7' C8' 113.43(15) . . ?
N2' C8' C9' 113.67(14) . . ?
N2' C8' C7' 107.13(13) . . ?
C9' C8' C7' 112.82(13) . . ?
N2' C8' H8' 107.7 . . ?
C9' C8' H8' 107.7 . . ?
C7' C8' H8' 107.7 . . ?
C11' C9' C10' 110.7(2) . . ?
C11' C9' C8' 109.48(15) . . ?
C10' C9' C8' 110.33(15) . . ?
C11' C9' H9' 108.8 . . ?
C10' C9' H9' 108.8 . . ?
C8' C9' H9' 108.8 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C9' C11' H11D 109.5 . . ?
C9' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C9' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
N2' C12' H12D 109.5 . . ?
N2' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
N2' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C15' C13' C16' 110.6(4) . . ?
C15' C13' C14' 111.9(4) . . ?
C16' C13' C14' 110.9(4) . . ?
C15' C13' S1' 113.1(5) . . ?
C16' C13' S1' 101.6(5) . . ?
C14' C13' S1' 108.3(5) . . ?
C15" C13" C16" 111.0(4) . . ?
C15" C13" C14" 112.3(4) . . ?
C16" C13" C14" 111.5(5) . . ?
C15" C13" S1' 113.4(8) . . ?
C16" C13" S1' 104.8(9) . . ?
C14" C13" S1' 103.4(9) . . ?
C13" C14" H14G 109.5 . . ?
C13" C14" H14H 109.5 . . ?
H14G C14" H14H 109.5 . . ?
C13" C14" H14I 109.5 . . ?
H14G C14" H14I 109.5 . . ?
H14H C14" H14I 109.5 . . ?
C13" C15" H15G 109.5 . . ?
C13" C15" H15H 109.5 . . ?
H15G C15" H15H 109.5 . . ?
C13" C15" H15I 109.5 . . ?
H15G C15" H15I 109.5 . . ?
H15H C15" H15I 109.5 . . ?
C13" C16" H16G 109.5 . . ?
C13" C16" H16H 109.5 . . ?
H16G C16" H16H 109.5 . . ?
C13" C16" H16I 109.5 . . ?
H16G C16" H16I 109.5 . . ?
H16H C16" H16I 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N2 C12 29.62(15) . . . . ?
C13 S1 N2 C12 -81.33(15) . . . . ?
O2 S1 N2 C8 -126.30(11) . . . . ?
C13 S1 N2 C8 122.76(12) . . . . ?
C6 C1 C2 F1 178.97(16) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
F1 C2 C3 F2 0.3(3) . . . . ?
C1 C2 C3 F2 179.11(16) . . . . ?
F1 C2 C3 C4 -179.83(16) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
F2 C3 C4 C5 -178.93(15) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 N1 180.00(14) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C1 C6 N1 -179.79(15) . . . . ?
C7 N1 C6 C5 -23.0(2) . . . . ?
C7 N1 C6 C1 157.32(16) . . . . ?
C6 N1 C7 O1 6.8(3) . . . . ?
C6 N1 C7 C8 -170.44(14) . . . . ?
C12 N2 C8 C9 -50.15(19) . . . . ?
S1 N2 C8 C9 105.86(13) . . . . ?
C12 N2 C8 C7 74.61(17) . . . . ?
S1 N2 C8 C7 -129.38(11) . . . . ?
O1 C7 C8 N2 -71.65(19) . . . . ?
N1 C7 C8 N2 105.71(14) . . . . ?
O1 C7 C8 C9 54.1(2) . . . . ?
N1 C7 C8 C9 -128.57(15) . . . . ?
N2 C8 C9 C10 176.97(16) . . . . ?
C7 C8 C9 C10 56.0(2) . . . . ?
N2 C8 C9 C11 -60.4(2) . . . . ?
C7 C8 C9 C11 178.63(18) . . . . ?
O2 S1 C13 C15 -47.89(18) . . . . ?
N2 S1 C13 C15 65.27(17) . . . . ?
O2 S1 C13 C14 -172.48(14) . . . . ?
N2 S1 C13 C14 -59.32(16) . . . . ?
O2 S1 C13 C16 70.96(17) . . . . ?
N2 S1 C13 C16 -175.88(16) . . . . ?
O2' S1' N2' C12' 34.41(18) . . . . ?
C13" S1' N2' C12' -76.3(4) . . . . ?
C13' S1' N2' C12' -75.4(3) . . . . ?
O2' S1' N2' C8' -131.17(13) . . . . ?
C13" S1' N2' C8' 118.1(4) . . . . ?
C13' S1' N2' C8' 119.1(3) . . . . ?
C6' C1' C2' F1' -178.2(3) . . . . ?
C6' C1' C2' C3' 1.1(3) . . . . ?
F1' C2' C3' F2' -0.8(4) . . . . ?
C1' C2' C3' F2' 179.9(2) . . . . ?
F1' C2' C3' C4' 178.8(3) . . . . ?
C1' C2' C3' C4' -0.5(3) . . . . ?
F2' C3' C4' C5' 178.8(3) . . . . ?
C2' C3' C4' C5' -0.8(4) . . . . ?
C3' C4' C5' C6' 1.4(5) . . . . ?
C4' C5' C6' C1' -0.8(5) . . . . ?
C4' C5' C6' N1' 177.5(2) . . . . ?
C2' C1' C6' C5' -0.5(3) . . . . ?
C2' C1' C6' N1' -178.85(19) . . . . ?
C7' N1' C6' C5' 25.3(5) . . . . ?
C7' N1' C6' C1' -156.4(3) . . . . ?
C6" C1" C2" F1" -180.0(3) . . . . ?
C6" C1" C2" C3" -0.1(6) . . . . ?
F1" C2" C3" F2" -0.1(5) . . . . ?
C1" C2" C3" F2" -179.9(3) . . . . ?
F1" C2" C3" C4" 179.9(3) . . . . ?
C1" C2" C3" C4" 0.0(6) . . . . ?
F2" C3" C4" C5" 180.0(3) . . . . ?
C2" C3" C4" C5" 0.0(6) . . . . ?
C3" C4" C5" C6" 0.0(6) . . . . ?
C4" C5" C6" C1" -0.1(6) . . . . ?
C4" C5" C6" N1" -180.0(3) . . . . ?
C2" C1" C6" C5" 0.2(6) . . . . ?
C2" C1" C6" N1" -179.9(3) . . . . ?
C7' N1" C6" C5" -151.6(16) . . . . ?
C7' N1" C6" C1" 28.5(17) . . . . ?
C6" N1" C7' O1' 6.2(18) . . . . ?
C6" N1" C7' N1' -152(20) . . . . ?
C6" N1" C7' C8' -173.1(10) . . . . ?
C6' N1' C7' O1' 2.9(4) . . . . ?
C6' N1' C7' N1" 25(19) . . . . ?
C6' N1' C7' C8' -175.3(2) . . . . ?
C12' N2' C8' C9' -49.1(2) . . . . ?
S1' N2' C8' C9' 116.53(14) . . . . ?
C12' N2' C8' C7' 76.2(2) . . . . ?
S1' N2' C8' C7' -118.15(12) . . . . ?
O1' C7' C8' N2' -59.92(19) . . . . ?
N1" C7' C8' N2' 119.4(9) . . . . ?
N1' C7' C8' N2' 118.4(2) . . . . ?
O1' C7' C8' C9' 65.9(2) . . . . ?
N1" C7' C8' C9' -114.8(9) . . . . ?
N1' C7' C8' C9' -115.8(2) . . . . ?
N2' C8' C9' C11' -59.7(2) . . . . ?
C7' C8' C9' C11' 178.05(18) . . . . ?
N2' C8' C9' C10' 178.17(15) . . . . ?
C7' C8' C9' C10' 55.9(2) . . . . ?
O2' S1' C13' C15' -43.4(6) . . . . ?
N2' S1' C13' C15' 69.1(6) . . . . ?
C13" S1' C13' C15' -116(4) . . . . ?
O2' S1' C13' C16' 75.1(5) . . . . ?
N2' S1' C13' C16' -172.3(5) . . . . ?
C13" S1' C13' C16' 2(4) . . . . ?
O2' S1' C13' C14' -168.0(6) . . . . ?
N2' S1' C13' C14' -55.4(6) . . . . ?
C13" S1' C13' C14' 119(4) . . . . ?
O2' S1' C13" C15" -55.4(8) . . . . ?
N2' S1' C13" C15" 59.4(8) . . . . ?
C13' S1' C13" C15" 54(4) . . . . ?
O2' S1' C13" C16" 65.8(6) . . . . ?
N2' S1' C13" C16" -179.4(6) . . . . ?
C13' S1' C13" C16" 175(4) . . . . ?
O2' S1' C13" C14" -177.3(7) . . . . ?
N2' S1' C13" C14" -62.5(7) . . . . ?
C13' S1' C13" C14" -68(4) . . . . ?

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
N1 H1N O2 0.88(2) 1.93(2) 2.7962(17) 172.5(18) 2_647
N1' H1N' O2' 0.88 1.93 2.785(2) 163.7 2_656
N1" H1N" O2' 0.88 1.96 2.833(8) 169.5 2_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 1003515'
