# 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
#  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_try

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H4.50 Cl0.25 F0.75 N0.50 O1.25 S0.50'
_chemical_formula_weight         130.73

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'
Cl Cl 0.1484 0.1585 '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

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

_cell_length_a                   8.6089(17)
_cell_length_b                   8.8898(18)
_cell_length_c                   15.632(3)
_cell_angle_alpha                98.35(3)
_cell_angle_beta                 96.13(3)
_cell_angle_gamma                104.16(3)
_cell_volume                     1135.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3730
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .140
_exptl_crystal_size_min          .13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .9221
_exptl_absorpt_correction_T_max  .9484

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9323
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.46
_reflns_number_total             5129
_reflns_number_gt                4475
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.1052P)²+1.8334P] 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         5129
_refine_ls_number_parameters     298
_refine_ls_number_restraints     12
_refine_ls_R_factor_ref          0.0884
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.2084
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.163
_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 0.49457(10) 0.51261(10) 0.13348(6) 0.0261(2) Uani 1 1 d . . .
S2 S 0.07140(11) 0.91578(11) 0.25947(7) 0.0338(3) Uani 1 1 d . . .
O2 O 0.5989(3) 0.4473(3) 0.08250(17) 0.0323(6) Uani 1 1 d . . .
O1 O 0.5083(3) 0.6771(3) 0.15134(18) 0.0317(6) Uani 1 1 d . . .
O3 O 0.1144(4) 1.0636(4) 0.2297(2) 0.0461(8) Uani 1 1 d . . .
O4 O -0.0967(4) 0.8346(4) 0.2350(3) 0.0624(11) Uani 1 1 d . . .
O5 O 0.1789(4) 0.8180(4) 0.2469(3) 0.0598(10) Uani 1 1 d . . .
N1 N 0.5379(4) 0.4668(3) 0.23326(19) 0.0281(6) Uani 1 1 d . . .
N2 N 0.5832(3) 0.3251(3) 0.23204(19) 0.0267(6) Uani 1 1 d . . .
Cl1 Cl 0.3174(3) 0.7448(2) 0.55108(8) 0.0841(6) Uani 1 1 d . . .
C2 C 0.2582(4) 0.2778(4) 0.0294(2) 0.0290(7) Uani 1 1 d . . .
H2A H 0.3432 0.2375 0.0098 0.035 Uiso 1 1 calc R . .
C3 C 0.0978(5) 0.2023(4) -0.0048(2) 0.0318(8) Uani 1 1 d . . .
H3A H 0.0731 0.1098 -0.0482 0.038 Uiso 1 1 calc R . .
C1 C 0.2926(4) 0.4129(4) 0.0925(2) 0.0256(7) Uani 1 1 d . . .
C6 C 0.1699(4) 0.4752(4) 0.1215(2) 0.0301(7) Uani 1 1 d . . .
H6A H 0.1947 0.5682 0.1645 0.036 Uiso 1 1 calc R . .
C4 C -0.0276(4) 0.2611(4) 0.0240(2) 0.0312(8) Uani 1 1 d . . .
C5 C 0.0121(4) 0.3985(5) 0.0864(2) 0.0324(8) Uani 1 1 d . . .
H5A H -0.0724 0.4406 0.1052 0.039 Uiso 1 1 calc R . .
C7 C -0.2005(5) 0.1791(5) -0.0133(3) 0.0424(10) Uani 1 1 d . . .
H7A H -0.2718 0.2364 0.0138 0.064 Uiso 1 1 calc R . .
H7B H -0.2266 0.0712 -0.0014 0.064 Uiso 1 1 calc R . .
H7C H -0.2161 0.1762 -0.0766 0.064 Uiso 1 1 calc R . .
C12 C 0.4685(4) 0.1860(4) 0.2081(2) 0.0301(7) Uani 1 1 d . . .
H12A H 0.3577 0.1850 0.1964 0.036 Uiso 1 1 calc R . .
C8 C 0.7442(4) 0.3353(4) 0.2513(2) 0.0311(8) Uani 1 1 d . . .
C9 C 0.7888(5) 0.1957(5) 0.2414(3) 0.0349(8) Uani 1 1 d . . .
H9A H 0.9002 0.1980 0.2525 0.042 Uiso 1 1 calc R . .
C11 C 0.5116(5) 0.0468(4) 0.2006(3) 0.0339(8) Uani 1 1 d . . .
H11A H 0.4317 -0.0514 0.1855 0.041 Uiso 1 1 calc R . .
C10 C 0.6743(5) 0.0526(5) 0.2157(3) 0.0362(8) Uani 1 1 d . . .
H10A H 0.7074 -0.0423 0.2083 0.043 Uiso 1 1 calc R . .
C13 C 0.8601(5) 0.4931(5) 0.2848(3) 0.0423(10) Uani 1 1 d . . .
H13A H 0.8012 0.5746 0.2865 0.063 Uiso 1 1 calc R . .
H13B H 0.9422 0.5131 0.2460 0.063 Uiso 1 1 calc R . .
H13C H 0.9129 0.4950 0.3438 0.063 Uiso 1 1 calc R . .
C14 C 0.4799(5) 0.5304(5) 0.3105(2) 0.0319(8) Uani 1 1 d . . .
C17 C 0.3798(7) 0.6618(7) 0.4574(3) 0.0549(13) Uani 1 1 d . . .
C19 C 0.3600(5) 0.4381(5) 0.3473(3) 0.0424(9) Uani 1 1 d . . .
H19A H 0.3121 0.3306 0.3218 0.051 Uiso 1 1 calc R . .
C15 C 0.5517(6) 0.6878(5) 0.3469(3) 0.0457(10) Uani 1 1 d . . .
H15A H 0.6353 0.7490 0.3215 0.055 Uiso 1 1 calc R . .
C16 C 0.4994(7) 0.7542(6) 0.4209(3) 0.0575(13) Uani 1 1 d . . .
H16A H 0.5454 0.8620 0.4461 0.069 Uiso 1 1 calc R . .
C18 C 0.3110(7) 0.5055(7) 0.4223(3) 0.0558(12) Uani 1 1 d . . .
H18A H 0.2302 0.4437 0.4490 0.067 Uiso 1 1 calc R . .
C20 C 0.0900(9) 0.9692(8) 0.3750(4) 0.0755(18) Uani 1 1 d . . .
F1 F 0.2393(7) 1.0444(6) 0.4098(3) 0.132(2) Uani 1 1 d U . .
F3 F -0.0034(8) 1.0616(7) 0.3970(3) 0.1324(19) Uani 1 1 d U . .
F2 F 0.0497(7) 0.8415(6) 0.4129(3) 0.1056(15) 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 O1 1.422(3) . ?
S1 O2 1.433(3) . ?
S1 N1 1.695(3) . ?
S1 C1 1.750(4) . ?
S2 O5 1.426(3) . ?
S2 O4 1.433(3) . ?
S2 O3 1.434(3) . ?
S2 C20 1.779(6) . ?
N1 N2 1.405(4) . ?
N1 C14 1.448(5) . ?
N2 C12 1.354(5) . ?
N2 C8 1.364(4) . ?
Cl1 C17 1.739(5) . ?
C2 C1 1.386(5) . ?
C2 C3 1.388(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(5) . ?
C3 H3A 0.9500 . ?
C1 C6 1.394(5) . ?
C6 C5 1.375(5) . ?
C6 H6A 0.9500 . ?
C4 C5 1.392(5) . ?
C4 C7 1.499(5) . ?
C5 H5A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C12 C11 1.369(5) . ?
C12 H12A 0.9500 . ?
C8 C9 1.379(5) . ?
C8 C13 1.492(5) . ?
C9 C10 1.381(6) . ?
C9 H9A 0.9500 . ?
C11 C10 1.382(6) . ?
C11 H11A 0.9500 . ?
C10 H10A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.386(6) . ?
C14 C15 1.390(6) . ?
C17 C18 1.375(8) . ?
C17 C16 1.381(8) . ?
C19 C18 1.391(6) . ?
C19 H19A 0.9500 . ?
C15 C16 1.390(7) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C18 H18A 0.9500 . ?
C20 F1 1.311(8) . ?
C20 F3 1.319(7) . ?
C20 F2 1.343(8) . ?

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
O1 S1 O2 122.50(16) . . ?
O1 S1 N1 104.02(16) . . ?
O2 S1 N1 103.37(15) . . ?
O1 S1 C1 108.81(16) . . ?
O2 S1 C1 109.36(17) . . ?
N1 S1 C1 107.70(16) . . ?
O5 S2 O4 114.4(2) . . ?
O5 S2 O3 115.9(2) . . ?
O4 S2 O3 113.2(2) . . ?
O5 S2 C20 104.3(3) . . ?
O4 S2 C20 102.9(3) . . ?
O3 S2 C20 104.2(3) . . ?
N2 N1 C14 118.4(3) . . ?
N2 N1 S1 114.9(2) . . ?
C14 N1 S1 123.2(2) . . ?
C12 N2 C8 123.0(3) . . ?
C12 N2 N1 119.4(3) . . ?
C8 N2 N1 117.5(3) . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 S1 119.5(3) . . ?
C6 C1 S1 119.0(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 H6A 120.8 . . ?
C1 C6 H6A 120.8 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C7 121.1(4) . . ?
C3 C4 C7 120.3(4) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C12 C11 120.3(3) . . ?
N2 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
N2 C8 C9 116.9(3) . . ?
N2 C8 C13 119.2(3) . . ?
C9 C8 C13 123.9(3) . . ?
C8 C9 C10 121.0(4) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11A 120.8 . . ?
C10 C11 H11A 120.8 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 121.5(4) . . ?
C19 C14 N1 121.5(4) . . ?
C15 C14 N1 117.0(4) . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 Cl1 119.4(4) . . ?
C16 C17 Cl1 119.1(4) . . ?
C14 C19 C18 118.8(4) . . ?
C14 C19 H19A 120.6 . . ?
C18 C19 H19A 120.6 . . ?
C14 C15 C16 119.0(5) . . ?
C14 C15 H15A 120.5 . . ?
C16 C15 H15A 120.5 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C17 C18 C19 119.8(5) . . ?
C17 C18 H18A 120.1 . . ?
C19 C18 H18A 120.1 . . ?
F1 C20 F3 107.6(6) . . ?
F1 C20 F2 106.4(5) . . ?
F3 C20 F2 108.3(6) . . ?
F1 C20 S2 111.6(6) . . ?
F3 C20 S2 111.3(4) . . ?
F2 C20 S2 111.4(4) . . ?

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
O1 S1 N1 N2 -160.5(2) . . . . ?
O2 S1 N1 N2 -31.6(3) . . . . ?
C1 S1 N1 N2 84.1(3) . . . . ?
O1 S1 N1 C14 41.0(3) . . . . ?
O2 S1 N1 C14 169.9(3) . . . . ?
C1 S1 N1 C14 -74.4(3) . . . . ?
C14 N1 N2 C12 84.7(4) . . . . ?
S1 N1 N2 C12 -74.9(4) . . . . ?
C14 N1 N2 C8 -98.5(4) . . . . ?
S1 N1 N2 C8 102.0(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C3 C2 C1 C6 -0.7(5) . . . . ?
C3 C2 C1 S1 -178.0(3) . . . . ?
O1 S1 C1 C2 145.2(3) . . . . ?
O2 S1 C1 C2 9.1(3) . . . . ?
N1 S1 C1 C2 -102.6(3) . . . . ?
O1 S1 C1 C6 -32.1(3) . . . . ?
O2 S1 C1 C6 -168.3(3) . . . . ?
N1 S1 C1 C6 80.1(3) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
S1 C1 C6 C5 177.7(3) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C4 C7 179.9(3) . . . . ?
C1 C6 C5 C4 0.7(6) . . . . ?
C3 C4 C5 C6 -1.5(6) . . . . ?
C7 C4 C5 C6 179.8(4) . . . . ?
C8 N2 C12 C11 -1.2(5) . . . . ?
N1 N2 C12 C11 175.5(3) . . . . ?
C12 N2 C8 C9 3.1(5) . . . . ?
N1 N2 C8 C9 -173.7(3) . . . . ?
C12 N2 C8 C13 -174.6(4) . . . . ?
N1 N2 C8 C13 8.7(5) . . . . ?
N2 C8 C9 C10 -1.9(6) . . . . ?
C13 C8 C9 C10 175.6(4) . . . . ?
N2 C12 C11 C10 -1.8(6) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C12 C11 C10 C9 2.9(6) . . . . ?
N2 N1 C14 C19 -49.8(5) . . . . ?
S1 N1 C14 C19 107.9(4) . . . . ?
N2 N1 C14 C15 129.2(4) . . . . ?
S1 N1 C14 C15 -73.0(4) . . . . ?
C15 C14 C19 C18 0.1(6) . . . . ?
N1 C14 C19 C18 179.1(4) . . . . ?
C19 C14 C15 C16 -1.2(6) . . . . ?
N1 C14 C15 C16 179.7(4) . . . . ?
C18 C17 C16 C15 -0.1(8) . . . . ?
Cl1 C17 C16 C15 178.9(4) . . . . ?
C14 C15 C16 C17 1.2(7) . . . . ?
C16 C17 C18 C19 -1.1(8) . . . . ?
Cl1 C17 C18 C19 179.9(4) . . . . ?
C14 C19 C18 C17 1.0(7) . . . . ?
O5 S2 C20 F1 59.5(5) . . . . ?
O4 S2 C20 F1 179.2(4) . . . . ?
O3 S2 C20 F1 -62.5(5) . . . . ?
O5 S2 C20 F3 179.7(5) . . . . ?
O4 S2 C20 F3 -60.6(6) . . . . ?
O3 S2 C20 F3 57.7(6) . . . . ?
O5 S2 C20 F2 -59.3(6) . . . . ?
O4 S2 C20 F2 60.3(5) . . . . ?
O3 S2 C20 F2 178.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.095
_database_code_depnum_ccdc_archive 'CCDC 1008472'
#######################################################################
#
#                 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_try

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 F6 N2 O P'
_chemical_formula_weight         420.29

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   13.927(3)
_cell_length_b                   10.771(2)
_cell_length_c                   24.361(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.49(3)
_cell_angle_gamma                90.00
_cell_volume                     3647.6(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6313
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .28
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .9407
_exptl_absorpt_correction_T_max  .9592

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12641
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4173
_reflns_number_gt                3707
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0424P)²+4.0300P] 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         4173
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0567
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
P1 P 0.09817(4) 0.15932(4) 0.41843(2) 0.02884(14) Uani 1 1 d . . .
F4 F 0.06282(10) 0.29983(11) 0.40943(6) 0.0488(3) Uani 1 1 d . . .
F2 F 0.07686(10) 0.13127(13) 0.35437(5) 0.0489(3) Uani 1 1 d . . .
F1 F 0.13468(11) 0.02041(11) 0.42684(5) 0.0519(4) Uani 1 1 d . . .
F5 F 0.11905(12) 0.18731(13) 0.48197(5) 0.0598(4) Uani 1 1 d . . .
F6 F -0.00898(10) 0.11990(14) 0.42876(7) 0.0614(4) Uani 1 1 d . . .
F3 F 0.20473(9) 0.20056(14) 0.40672(7) 0.0610(4) Uani 1 1 d . . .
C1 C 0.16211(13) 0.40755(17) 0.16782(7) 0.0266(4) Uani 1 1 d . . .
C6 C 0.22707(14) 0.48541(19) 0.19481(8) 0.0328(4) Uani 1 1 d . . .
H6A H 0.2552 0.5525 0.1762 0.039 Uiso 1 1 calc R . .
C5 C 0.25051(16) 0.4630(2) 0.25034(9) 0.0420(5) Uani 1 1 d . . .
H5A H 0.2952 0.5155 0.2701 0.050 Uiso 1 1 calc R . .
C2 C 0.12056(15) 0.30863(19) 0.19305(9) 0.0376(5) Uani 1 1 d . . .
H2A H 0.0766 0.2555 0.1730 0.045 Uiso 1 1 calc R . .
C4 C 0.20937(17) 0.3653(2) 0.27691(9) 0.0445(5) Uani 1 1 d . . .
H4A H 0.2257 0.3509 0.3148 0.053 Uiso 1 1 calc R . .
C3 C 0.14437(17) 0.2882(2) 0.24852(9) 0.0451(5) Uani 1 1 d . . .
H3A H 0.1159 0.2211 0.2670 0.054 Uiso 1 1 calc R . .
C7 C 0.05014(12) 0.61484(17) 0.12496(7) 0.0259(4) Uani 1 1 d . . .
C12 C 0.06953(14) 0.74029(18) 0.11711(8) 0.0320(4) Uani 1 1 d . . .
H12A H 0.1150 0.7648 0.0917 0.038 Uiso 1 1 calc R . .
C8 C -0.01737(14) 0.57806(19) 0.16174(8) 0.0333(4) Uani 1 1 d . . .
H8A H -0.0306 0.4926 0.1672 0.040 Uiso 1 1 calc R . .
C11 C 0.02217(16) 0.8291(2) 0.14650(9) 0.0403(5) Uani 1 1 d . . .
H11A H 0.0360 0.9147 0.1417 0.048 Uiso 1 1 calc R . .
C10 C -0.04495(16) 0.7933(2) 0.18267(9) 0.0446(6) Uani 1 1 d . . .
H10A H -0.0777 0.8545 0.2026 0.053 Uiso 1 1 calc R . .
C9 C -0.06498(15) 0.6689(2) 0.19018(8) 0.0432(5) Uani 1 1 d . . .
H9A H -0.1117 0.6453 0.2150 0.052 Uiso 1 1 calc R . .
N2 N 0.13844(10) 0.46049(13) 0.00444(6) 0.0243(3) Uani 1 1 d . . .
C13 C 0.09700(12) 0.52358(16) 0.08997(7) 0.0241(3) Uani 1 1 d . . .
C18 C 0.10446(14) 0.34430(17) -0.00299(8) 0.0317(4) Uani 1 1 d . . .
H18A H 0.0541 0.3143 0.0181 0.038 Uiso 1 1 calc R . .
C14 C 0.20882(14) 0.5077(2) -0.02449(8) 0.0340(4) Uani 1 1 d . . .
H14A H 0.2299 0.5908 -0.0185 0.041 Uiso 1 1 calc R . .
C17 C 0.14391(17) 0.2698(2) -0.04159(9) 0.0456(6) Uani 1 1 d . . .
H17A H 0.1210 0.1875 -0.0475 0.055 Uiso 1 1 calc R . .
C16 C 0.21723(19) 0.3158(3) -0.07172(9) 0.0548(7) Uani 1 1 d . . .
H16A H 0.2448 0.2651 -0.0985 0.066 Uiso 1 1 calc R . .
C15 C 0.24994(17) 0.4348(3) -0.06275(9) 0.0497(6) Uani 1 1 d . . .
H15A H 0.3008 0.4664 -0.0830 0.060 Uiso 1 1 calc R . .
N1 N 0.09134(11) 0.54584(13) 0.03817(6) 0.0258(3) Uani 1 1 d . . .
O1 O 0.14027(10) 0.42073(12) 0.11048(5) 0.0301(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F6 1.5863(14) . ?
P1 F5 1.5863(14) . ?
P1 F1 1.5894(13) . ?
P1 F3 1.5915(14) . ?
P1 F2 1.5996(13) . ?
P1 F4 1.6024(13) . ?
C1 C6 1.372(3) . ?
C1 C2 1.375(3) . ?
C1 O1 1.418(2) . ?
C6 C5 1.393(3) . ?
C6 H6A 0.9500 . ?
C5 C4 1.378(3) . ?
C5 H5A 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2A 0.9500 . ?
C4 C3 1.382(3) . ?
C4 H4A 0.9500 . ?
C3 H3A 0.9500 . ?
C7 C12 1.393(3) . ?
C7 C8 1.395(3) . ?
C7 C13 1.479(2) . ?
C12 C11 1.386(3) . ?
C12 H12A 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8A 0.9500 . ?
C11 C10 1.378(3) . ?
C11 H11A 0.9500 . ?
C10 C9 1.383(3) . ?
C10 H10A 0.9500 . ?
C9 H9A 0.9500 . ?
N2 C14 1.342(2) . ?
N2 C18 1.346(2) . ?
N2 N1 1.4199(19) . ?
C13 N1 1.282(2) . ?
C13 O1 1.343(2) . ?
C18 C17 1.376(3) . ?
C18 H18A 0.9500 . ?
C14 C15 1.371(3) . ?
C14 H14A 0.9500 . ?
C17 C16 1.385(4) . ?
C17 H17A 0.9500 . ?
C16 C15 1.374(4) . ?
C16 H16A 0.9500 . ?
C15 H15A 0.9500 . ?

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
F6 P1 F5 90.83(9) . . ?
F6 P1 F1 91.40(9) . . ?
F5 P1 F1 90.86(7) . . ?
F6 P1 F3 178.60(9) . . ?
F5 P1 F3 90.24(9) . . ?
F1 P1 F3 89.50(8) . . ?
F6 P1 F2 89.07(9) . . ?
F5 P1 F2 179.85(9) . . ?
F1 P1 F2 89.25(7) . . ?
F3 P1 F2 89.86(9) . . ?
F6 P1 F4 89.45(8) . . ?
F5 P1 F4 89.46(8) . . ?
F1 P1 F4 179.10(9) . . ?
F3 P1 F4 89.65(8) . . ?
F2 P1 F4 90.44(7) . . ?
C6 C1 C2 122.86(18) . . ?
C6 C1 O1 120.43(16) . . ?
C2 C1 O1 116.54(17) . . ?
C1 C6 C5 117.91(19) . . ?
C1 C6 H6A 121.0 . . ?
C5 C6 H6A 121.0 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C12 C7 C8 120.49(17) . . ?
C12 C7 C13 118.00(16) . . ?
C8 C7 C13 121.32(17) . . ?
C11 C12 C7 119.75(19) . . ?
C11 C12 H12A 120.1 . . ?
C7 C12 H12A 120.1 . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C10 C9 120.39(19) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C14 N2 C18 122.94(17) . . ?
C14 N2 N1 115.88(15) . . ?
C18 N2 N1 120.58(15) . . ?
N1 C13 O1 121.32(16) . . ?
N1 C13 C7 116.12(15) . . ?
O1 C13 C7 122.52(15) . . ?
N2 C18 C17 118.8(2) . . ?
N2 C18 H18A 120.6 . . ?
C17 C18 H18A 120.6 . . ?
N2 C14 C15 119.3(2) . . ?
N2 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C13 N1 N2 116.46(14) . . ?
C13 O1 C1 120.89(14) . . ?

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
C2 C1 C6 C5 -0.7(3) . . . . ?
O1 C1 C6 C5 -175.80(16) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
O1 C1 C2 C3 176.38(17) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C13 C7 C12 C11 175.73(17) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C13 C7 C8 C9 -174.65(17) . . . . ?
C7 C12 C11 C10 -1.0(3) . . . . ?
C12 C11 C10 C9 0.5(3) . . . . ?
C11 C10 C9 C8 0.5(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C12 C7 C13 N1 -48.8(2) . . . . ?
C8 C7 C13 N1 126.19(19) . . . . ?
C12 C7 C13 O1 133.48(18) . . . . ?
C8 C7 C13 O1 -51.5(2) . . . . ?
C14 N2 C18 C17 0.6(3) . . . . ?
N1 N2 C18 C17 171.31(16) . . . . ?
C18 N2 C14 C15 -1.3(3) . . . . ?
N1 N2 C14 C15 -172.41(17) . . . . ?
N2 C18 C17 C16 0.0(3) . . . . ?
C18 C17 C16 C15 0.1(3) . . . . ?
N2 C14 C15 C16 1.4(3) . . . . ?
C17 C16 C15 C14 -0.8(3) . . . . ?
O1 C13 N1 N2 -3.9(2) . . . . ?
C7 C13 N1 N2 178.31(14) . . . . ?
C14 N2 N1 C13 -118.98(18) . . . . ?
C18 N2 N1 C13 69.6(2) . . . . ?
N1 C13 O1 C1 168.22(16) . . . . ?
C7 C13 O1 C1 -14.2(2) . . . . ?
C6 C1 O1 C13 -64.5(2) . . . . ?
C2 C1 O1 C13 120.06(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 1008473'
#######################################################################
#
#                 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_p-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 F6 N2 O2 P S'
_chemical_formula_weight         484.40

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'
P P 0.1023 0.0942 '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                   15.338(3)
_cell_length_b                   10.040(2)
_cell_length_c                   14.189(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.34(3)
_cell_angle_gamma                90.00
_cell_volume                     2178.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5992
_cell_measurement_theta_min      1.33
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .43
_exptl_crystal_size_min          .26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .8729
_exptl_absorpt_correction_T_max  .9282


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16984
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4971
_reflns_number_gt                4725
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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)+(0.0849P)²+2.0400P] 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         4971
_refine_ls_number_parameters     337
_refine_ls_number_restraints     216
_refine_ls_R_factor_ref          0.0811
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.2033
_refine_ls_wR_factor_gt          0.2007
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.410
_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 0.34666(5) -0.30494(10) 0.92980(7) 0.0455(3) Uani 1 1 d . . .
O1 O 0.37441(16) -0.1864(3) 0.9791(2) 0.0551(7) Uani 1 1 d . . .
O2 O 0.40893(17) -0.4006(3) 0.9033(2) 0.0662(9) Uani 1 1 d . . .
N1 N 0.29317(18) -0.2563(3) 0.82988(19) 0.0415(7) Uani 1 1 d . . .
H1A H 0.3069 -0.2849 0.7758 0.050 Uiso 1 1 d R . .
N2 N 0.32573(18) 0.0233(3) 0.8309(2) 0.0443(7) Uani 1 1 d . . .
C1 C 0.2681(2) -0.3843(3) 0.9936(2) 0.0389(7) Uani 1 1 d . . .
C2 C 0.2466(3) -0.5162(4) 0.9746(3) 0.0491(9) Uani 1 1 d . . .
H2A H 0.2795 -0.5673 0.9335 0.059 Uiso 1 1 calc R . .
C3 C 0.1771(3) -0.5721(4) 1.0162(3) 0.0512(9) Uani 1 1 d . . .
H3A H 0.1628 -0.6628 1.0040 0.061 Uiso 1 1 calc R . .
C4 C 0.1274(2) -0.4991(4) 1.0755(2) 0.0438(8) Uani 1 1 d . . .
C5 C 0.1511(2) -0.3689(4) 1.0953(2) 0.0407(7) Uani 1 1 d . . .
H5A H 0.1190 -0.3190 1.1378 0.049 Uiso 1 1 calc R . .
C6 C 0.2207(2) -0.3090(3) 1.0548(2) 0.0394(7) Uani 1 1 d . . .
H6A H 0.2358 -0.2189 1.0683 0.047 Uiso 1 1 calc R . .
C7 C 0.0491(3) -0.5611(5) 1.1164(3) 0.0607(11) Uani 1 1 d . . .
H7A H 0.0164 -0.4922 1.1476 0.091 Uiso 1 1 calc R . .
H7B H 0.0688 -0.6294 1.1626 0.091 Uiso 1 1 calc R . .
H7C H 0.0114 -0.6019 1.0656 0.091 Uiso 1 1 calc R . .
C8 C 0.22296(19) -0.1640(3) 0.8383(2) 0.0357(7) Uani 1 1 d . . .
C9 C 0.1375(2) -0.2069(4) 0.8456(2) 0.0387(7) Uani 1 1 d . . .
H9A H 0.1243 -0.2993 0.8423 0.046 Uiso 1 1 calc R . .
C10 C 0.0717(2) -0.1158(4) 0.8574(2) 0.0413(8) Uani 1 1 d . . .
H10A H 0.0136 -0.1469 0.8611 0.050 Uiso 1 1 calc R . .
C11 C 0.0884(2) 0.0203(4) 0.8642(2) 0.0421(8) Uani 1 1 d . . .
C12 C 0.1733(2) 0.0632(4) 0.8553(2) 0.0410(7) Uani 1 1 d . . .
H12A H 0.1864 0.1557 0.8582 0.049 Uiso 1 1 calc R . .
C13 C 0.23901(19) -0.0275(3) 0.8421(2) 0.0361(7) Uani 1 1 d . . .
C14 C 0.0171(3) 0.1184(4) 0.8791(3) 0.0567(10) Uani 1 1 d . . .
H14A H -0.0391 0.0821 0.8534 0.085 Uiso 1 1 calc R . .
H14B H 0.0290 0.2020 0.8468 0.085 Uiso 1 1 calc R . .
H14C H 0.0147 0.1353 0.9469 0.085 Uiso 1 1 calc R . .
C15 C 0.3685(3) 0.0875(5) 0.9037(3) 0.0620(12) Uani 1 1 d . . .
H15A H 0.3417 0.1006 0.9612 0.074 Uiso 1 1 calc R . .
C16 C 0.4517(3) 0.1339(6) 0.8933(5) 0.092(2) Uani 1 1 d . . .
H16A H 0.4830 0.1796 0.9438 0.111 Uiso 1 1 calc R . .
C17 C 0.4895(3) 0.1137(7) 0.8094(6) 0.106(2) Uani 1 1 d . . .
H17A H 0.5474 0.1437 0.8025 0.127 Uiso 1 1 calc R . .
C18 C 0.4440(3) 0.0507(6) 0.7362(5) 0.0934(19) Uani 1 1 d . . .
H18A H 0.4694 0.0386 0.6778 0.112 Uiso 1 1 calc R . .
C19 C 0.3607(3) 0.0047(5) 0.7474(3) 0.0625(11) Uani 1 1 d . . .
H19A H 0.3284 -0.0396 0.6970 0.075 Uiso 1 1 calc R . .
F1 F 0.1917(3) -0.9624(6) 0.0855(3) 0.099(3) Uani 0.474(6) 1 d PD A 1
F3 F 0.2882(3) -0.8414(5) 0.2710(3) 0.093(3) Uani 0.474(6) 1 d PDU A 1
F2 F 0.1874(3) -0.9997(5) 0.2405(3) 0.094(3) Uani 0.474(6) 1 d PD A 1
F5 F 0.2926(3) -0.8044(6) 0.1160(4) 0.096(3) Uani 0.474(6) 1 d PD A 1
F4 F 0.1652(3) -0.7943(5) 0.1826(4) 0.106(3) Uani 0.474(6) 1 d PD A 1
F6 F 0.3147(3) -1.0097(5) 0.1739(4) 0.122(4) Uani 0.474(6) 1 d PD A 1
F1' F 0.1593(3) -0.8874(4) 0.1011(3) 0.081(2) Uani 0.526(6) 1 d PD A 2
F3' F 0.3079(3) -0.9197(6) 0.2661(3) 0.115(3) Uani 0.526(6) 1 d PD A 2
F2' F 0.2122(4) -1.0569(4) 0.1898(3) 0.090(2) Uani 0.526(6) 1 d PD A 2
F5' F 0.2549(3) -0.7500(4) 0.1775(4) 0.105(3) Uani 0.526(6) 1 d PDU A 2
F4' F 0.1651(3) -0.8731(5) 0.2585(3) 0.099(3) Uani 0.526(6) 1 d PD A 2
F6' F 0.3020(3) -0.9339(6) 0.1087(3) 0.138(4) Uani 0.526(6) 1 d PDU A 2
P1 P 0.23515(8) -0.90329(10) 0.18024(7) 0.0559(3) Uani 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 1.425(3) . ?
S1 O1 1.429(3) . ?
S1 N1 1.657(3) . ?
S1 C1 1.753(3) . ?
N1 C8 1.432(4) . ?
N1 H1A 0.8602 . ?
N2 C15 1.346(5) . ?
N2 C19 1.349(5) . ?
N2 C13 1.444(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.395(5) . ?
C2 C3 1.377(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(5) . ?
C4 C7 1.506(5) . ?
C5 C6 1.387(5) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.390(4) . ?
C8 C13 1.393(5) . ?
C9 C10 1.382(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.393(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.386(5) . ?
C11 C14 1.499(5) . ?
C12 C13 1.381(5) . ?
C12 H12A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.378(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.378(10) . ?
C16 H16A 0.9500 . ?
C17 C18 1.363(10) . ?
C17 H17A 0.9500 . ?
C18 C19 1.378(6) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
F1 P1 1.571(4) . ?
F3 P1 1.596(4) . ?
F2 P1 1.517(4) . ?
F5 P1 1.648(4) . ?
F4 P1 1.535(4) . ?
F6 P1 1.630(4) . ?
F1' P1 1.563(4) . ?
F3' P1 1.596(4) . ?
F2' P1 1.590(4) . ?
F5' P1 1.569(4) . ?
F4' P1 1.630(4) . ?
F6' P1 1.527(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
O2 S1 O1 120.64(18) . . ?
O2 S1 N1 105.74(18) . . ?
O1 S1 N1 106.45(17) . . ?
O2 S1 C1 109.33(19) . . ?
O1 S1 C1 108.45(17) . . ?
N1 S1 C1 105.12(15) . . ?
C8 N1 S1 116.5(2) . . ?
C8 N1 H1A 121.8 . . ?
S1 N1 H1A 121.7 . . ?
C15 N2 C19 122.5(3) . . ?
C15 N2 C13 118.9(3) . . ?
C19 N2 C13 118.6(3) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 S1 119.7(3) . . ?
C6 C1 S1 119.1(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 121.3(4) . . ?
C3 C4 C7 120.4(4) . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 H6A 120.8 . . ?
C1 C6 H6A 120.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 117.8(3) . . ?
C9 C8 N1 121.7(3) . . ?
C13 C8 N1 120.5(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 121.7(3) . . ?
C9 C10 H10A 119.1 . . ?
C11 C10 H10A 119.1 . . ?
C12 C11 C10 117.9(3) . . ?
C12 C11 C14 120.6(3) . . ?
C10 C11 C14 121.5(3) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C8 121.7(3) . . ?
C12 C13 N2 118.0(3) . . ?
C8 C13 N2 120.3(3) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 118.8(5) . . ?
N2 C15 H15A 120.6 . . ?
C16 C15 H15A 120.6 . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C18 C17 C16 120.1(5) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 119.6(6) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
N2 C19 C18 119.3(5) . . ?
N2 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?
F2 P1 F6' 128.6(3) . . ?
F2 P1 F4 94.24(17) . . ?
F6' P1 F4 131.6(2) . . ?
F2 P1 F1' 96.0(3) . . ?
F6' P1 F1' 92.49(15) . . ?
F4 P1 F1' 57.3(2) . . ?
F2 P1 F5' 137.9(3) . . ?
F6' P1 F5' 92.29(16) . . ?
F4 P1 F5' 55.8(3) . . ?
F1' P1 F5' 90.95(15) . . ?
F2 P1 F1 92.82(17) . . ?
F6' P1 F1 67.5(3) . . ?
F4 P1 F1 92.07(16) . . ?
F1' P1 F1 34.8(2) . . ?
F5' P1 F1 114.8(2) . . ?
F2 P1 F2' 38.1(2) . . ?
F6' P1 F2' 91.48(16) . . ?
F4 P1 F2' 122.0(2) . . ?
F1' P1 F2' 90.15(15) . . ?
F5' P1 F2' 176.0(2) . . ?
F1 P1 F2' 67.9(2) . . ?
F2 P1 F3 91.85(16) . . ?
F6' P1 F3 106.7(3) . . ?
F4 P1 F3 91.12(17) . . ?
F1' P1 F3 147.8(2) . . ?
F5' P1 F3 63.3(2) . . ?
F1 P1 F3 174.1(2) . . ?
F2' P1 F3 114.3(2) . . ?
F2 P1 F3' 81.0(3) . . ?
F6' P1 F3' 91.21(16) . . ?
F4 P1 F3' 120.4(3) . . ?
F1' P1 F3' 176.2(2) . . ?
F5' P1 F3' 89.70(15) . . ?
F1 P1 F3' 147.2(3) . . ?
F2' P1 F3' 88.95(14) . . ?
F3 P1 F3' 30.7(2) . . ?
F2 P1 F6 90.49(16) . . ?
F6' P1 F6 44.7(3) . . ?
F4 P1 F6 175.2(2) . . ?
F1' P1 F6 123.2(2) . . ?
F5' P1 F6 119.7(3) . . ?
F1 P1 F6 88.63(16) . . ?
F2' P1 F6 62.6(3) . . ?
F3 P1 F6 87.78(15) . . ?
F3' P1 F6 59.4(3) . . ?
F2 P1 F4' 50.5(2) . . ?
F6' P1 F4' 178.6(2) . . ?
F4 P1 F4' 49.8(2) . . ?
F1' P1 F4' 88.70(15) . . ?
F5' P1 F4' 88.46(15) . . ?
F1 P1 F4' 113.2(3) . . ?
F2' P1 F4' 87.75(15) . . ?
F3 P1 F4' 72.6(3) . . ?
F3' P1 F4' 87.60(14) . . ?
F6 P1 F4' 133.9(2) . . ?
F2 P1 F5 176.4(2) . . ?
F6' P1 F5 48.7(2) . . ?
F4 P1 F5 89.22(15) . . ?
F1' P1 F5 86.6(3) . . ?
F5' P1 F5 44.2(2) . . ?
F1 P1 F5 87.97(15) . . ?
F2' P1 F5 139.7(2) . . ?
F3 P1 F5 87.15(16) . . ?
F3' P1 F5 96.4(3) . . ?
F6 P1 F5 86.03(15) . . ?
F4' P1 F5 132.2(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 N1 C8 176.8(3) . . . . ?
O1 S1 N1 C8 -53.7(3) . . . . ?
C1 S1 N1 C8 61.2(3) . . . . ?
O2 S1 C1 C2 -30.6(3) . . . . ?
O1 S1 C1 C2 -163.9(3) . . . . ?
N1 S1 C1 C2 82.5(3) . . . . ?
O2 S1 C1 C6 157.0(3) . . . . ?
O1 S1 C1 C6 23.7(3) . . . . ?
N1 S1 C1 C6 -89.9(3) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
S1 C1 C2 C3 -171.6(3) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 -2.5(6) . . . . ?
C2 C3 C4 C7 177.2(4) . . . . ?
C3 C4 C5 C6 2.5(5) . . . . ?
C7 C4 C5 C6 -177.1(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
S1 C1 C6 C5 171.7(2) . . . . ?
S1 N1 C8 C9 -91.5(3) . . . . ?
S1 N1 C8 C13 86.8(3) . . . . ?
C13 C8 C9 C10 -0.9(5) . . . . ?
N1 C8 C9 C10 177.4(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C9 C10 C11 C12 2.3(5) . . . . ?
C9 C10 C11 C14 -178.7(3) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C14 C11 C12 C13 179.6(3) . . . . ?
C11 C12 C13 C8 -0.7(5) . . . . ?
C11 C12 C13 N2 178.5(3) . . . . ?
C9 C8 C13 C12 1.8(5) . . . . ?
N1 C8 C13 C12 -176.5(3) . . . . ?
C9 C8 C13 N2 -177.3(3) . . . . ?
N1 C8 C13 N2 4.4(4) . . . . ?
C15 N2 C13 C12 64.8(5) . . . . ?
C19 N2 C13 C12 -115.0(4) . . . . ?
C15 N2 C13 C8 -116.0(4) . . . . ?
C19 N2 C13 C8 64.2(5) . . . . ?
C19 N2 C15 C16 -1.3(7) . . . . ?
C13 N2 C15 C16 179.0(4) . . . . ?
N2 C15 C16 C17 -0.1(9) . . . . ?
C15 C16 C17 C18 1.5(10) . . . . ?
C16 C17 C18 C19 -1.5(10) . . . . ?
C15 N2 C19 C18 1.2(7) . . . . ?
C13 N2 C19 C18 -179.0(5) . . . . ?
C17 C18 C19 N2 0.2(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 1008474'
