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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  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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#  data retrieval see:
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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_dgr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 I N2 Rh'
_chemical_formula_weight         522.22

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'
I I -0.4742 1.8119 '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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   14.1979(10)
_cell_length_b                   8.3992(5)
_cell_length_c                   16.4769(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.840(3)
_cell_angle_gamma                90.00
_cell_volume                     1915.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            75888
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3360
_reflns_number_gt                3135
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.2000P)²+0.0000P] 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       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.1211
_refine_ls_wR_factor_ref         0.4370
_refine_ls_wR_factor_gt          0.4282
_refine_ls_goodness_of_fit_ref   2.309
_refine_ls_restrained_S_all      2.309
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.004

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
C1 C 0.3692(8) 0.2786(11) 0.4553(6) 0.029(2) Uani 1 1 d . . .
C2 C 0.3514(12) 0.1161(19) 0.5788(9) 0.053(3) Uani 1 1 d . . .
H2A H 0.3938 0.0580 0.6222 0.079 Uiso 1 1 calc R . .
H2B H 0.3041 0.0449 0.5473 0.079 Uiso 1 1 calc R . .
H2C H 0.3194 0.1983 0.6029 0.079 Uiso 1 1 calc R . .
C3 C 0.5057(8) 0.1932(17) 0.5347(8) 0.044(3) Uani 1 1 d . . .
H3 H 0.5491 0.1422 0.5774 0.052 Uiso 1 1 calc R . .
C4 C 0.5295(8) 0.2793(14) 0.4775(8) 0.044(3) Uani 1 1 d . . .
H4 H 0.5920 0.3004 0.4716 0.053 Uiso 1 1 calc R . .
C5 C 0.4260(9) 0.4483(10) 0.3653(7) 0.030(2) Uani 1 1 d . . .
C6 C 0.3277(8) 0.4874(12) 0.3438(6) 0.031(2) Uani 1 1 d . . .
C7 C 0.3023(10) 0.6098(15) 0.2846(8) 0.043(3) Uani 1 1 d . . .
H7 H 0.2382 0.6423 0.2695 0.051 Uiso 1 1 calc R . .
C8 C 0.3718(11) 0.6852(16) 0.2473(8) 0.048(3) Uani 1 1 d . . .
H8 H 0.3533 0.7662 0.2086 0.057 Uiso 1 1 calc R . .
C9 C 0.4703(12) 0.6353(14) 0.2700(11) 0.051(4) Uani 1 1 d . . .
H9 H 0.5160 0.6805 0.2444 0.061 Uiso 1 1 calc R . .
C10 C 0.4974(9) 0.5190(13) 0.3305(9) 0.043(3) Uani 1 1 d . . .
H10 H 0.5617 0.4884 0.3476 0.051 Uiso 1 1 calc R . .
C11 C 0.1874(12) 0.175(2) 0.3038(12) 0.062(5) Uani 1 1 d . . .
C12 C 0.1583(10) 0.1161(16) 0.3701(8) 0.048(3) Uani 1 1 d . . .
C13 C 0.0966(8) 0.2174(16) 0.3966(7) 0.041(3) Uani 1 1 d . . .
C14 C 0.0765(10) 0.3475(14) 0.3369(9) 0.044(3) Uani 1 1 d . . .
C15 C 0.1286(9) 0.315(2) 0.2739(8) 0.046(3) Uani 1 1 d . . .
C16 C 0.1102(15) 0.398(4) 0.1973(12) 0.093(6) Uani 1 1 d . . .
H16A H 0.0667 0.4848 0.1995 0.140 Uiso 1 1 calc R . .
H16B H 0.0816 0.3270 0.1531 0.140 Uiso 1 1 calc R . .
H16C H 0.1698 0.4391 0.1874 0.140 Uiso 1 1 calc R . .
C17 C 0.2500(13) 0.091(3) 0.2536(15) 0.089(6) Uani 1 1 d . . .
H17A H 0.2585 0.1589 0.2089 0.133 Uiso 1 1 calc R . .
H17B H 0.2194 -0.0062 0.2312 0.133 Uiso 1 1 calc R . .
H17C H 0.3119 0.0677 0.2889 0.133 Uiso 1 1 calc R . .
C18 C 0.1862(17) -0.0486(18) 0.4156(14) 0.080(6) Uani 1 1 d . . .
H18A H 0.2304 -0.1044 0.3893 0.120 Uiso 1 1 calc R . .
H18B H 0.1289 -0.1115 0.4120 0.120 Uiso 1 1 calc R . .
H18C H 0.2160 -0.0299 0.4730 0.120 Uiso 1 1 calc R . .
C19 C 0.0467(14) 0.212(3) 0.4695(12) 0.082(5) Uani 1 1 d . . .
H19A H 0.0084 0.3063 0.4692 0.123 Uiso 1 1 calc R . .
H19B H 0.0945 0.2062 0.5208 0.123 Uiso 1 1 calc R . .
H19C H 0.0057 0.1199 0.4643 0.123 Uiso 1 1 calc R . .
C20 C 0.0137(14) 0.508(3) 0.3424(18) 0.108(9) Uani 1 1 d . . .
H20A H -0.0139 0.5027 0.3905 0.162 Uiso 1 1 calc R . .
H20B H -0.0371 0.5169 0.2932 0.162 Uiso 1 1 calc R . .
H20C H 0.0550 0.5997 0.3467 0.162 Uiso 1 1 calc R . .
I1 I 0.22199(11) 0.54888(14) 0.51159(9) 0.0844(8) Uani 1 1 d . . .
N1 N 0.4469(8) 0.3328(10) 0.4277(7) 0.034(2) Uani 1 1 d . . .
N2 N 0.4077(7) 0.1882(12) 0.5234(6) 0.033(2) Uani 1 1 d . . .
Rh1 Rh 0.23766(5) 0.35068(7) 0.39432(4) 0.0238(7) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.362(15) . ?
C1 N2 1.364(15) . ?
C1 Rh1 2.008(11) . ?
C2 N2 1.470(18) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.29(2) . ?
C3 N2 1.363(16) . ?
C3 H3 0.9300 . ?
C4 N1 1.350(16) . ?
C4 H4 0.9300 . ?
C5 N1 1.397(15) . ?
C5 C6 1.401(16) . ?
C5 C10 1.403(16) . ?
C6 C7 1.407(16) . ?
C6 Rh1 2.030(11) . ?
C7 C8 1.422(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.43(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.39(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.34(2) . ?
C11 C15 1.47(3) . ?
C11 C17 1.51(2) . ?
C11 Rh1 2.108(13) . ?
C12 C13 1.36(2) . ?
C12 C18 1.58(2) . ?
C12 Rh1 2.261(11) . ?
C13 C14 1.455(18) . ?
C13 C19 1.52(2) . ?
C13 Rh1 2.302(11) . ?
C14 C15 1.43(2) . ?
C14 C20 1.63(3) . ?
C14 Rh1 2.274(13) . ?
C15 C16 1.41(3) . ?
C15 Rh1 2.249(13) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
I1 Rh1 2.5972(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 104.7(9) . . ?
N1 C1 Rh1 117.7(7) . . ?
N2 C1 Rh1 137.6(8) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N2 110.0(11) . . ?
C4 C3 H3 125.0 . . ?
N2 C3 H3 125.0 . . ?
C3 C4 N1 107.2(11) . . ?
C3 C4 H4 126.4 . . ?
N1 C4 H4 126.4 . . ?
N1 C5 C6 112.7(10) . . ?
N1 C5 C10 122.7(11) . . ?
C6 C5 C10 124.5(11) . . ?
C5 C6 C7 115.8(10) . . ?
C5 C6 Rh1 116.5(7) . . ?
C7 C6 Rh1 127.6(9) . . ?
C6 C7 C8 121.9(12) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C9 119.3(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.6(12) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 118.8(12) . . ?
C9 C10 H10 120.6 . . ?
C5 C10 H10 120.6 . . ?
C12 C11 C15 108.3(14) . . ?
C12 C11 C17 127(2) . . ?
C15 C11 C17 123.2(19) . . ?
C12 C11 Rh1 78.4(8) . . ?
C15 C11 Rh1 75.6(8) . . ?
C17 C11 Rh1 124.3(10) . . ?
C11 C12 C13 111.6(14) . . ?
C11 C12 C18 128.0(17) . . ?
C13 C12 C18 120.4(14) . . ?
C11 C12 Rh1 66.0(7) . . ?
C13 C12 Rh1 74.3(7) . . ?
C18 C12 Rh1 128.1(9) . . ?
C12 C13 C14 107.3(11) . . ?
C12 C13 C19 132.7(15) . . ?
C14 C13 C19 119.9(15) . . ?
C12 C13 Rh1 71.0(7) . . ?
C14 C13 Rh1 70.4(7) . . ?
C19 C13 Rh1 125.9(11) . . ?
C15 C14 C13 107.0(11) . . ?
C15 C14 C20 125.1(14) . . ?
C13 C14 C20 127.7(15) . . ?
C15 C14 Rh1 70.6(8) . . ?
C13 C14 Rh1 72.5(7) . . ?
C20 C14 Rh1 118.6(12) . . ?
C16 C15 C14 122.1(17) . . ?
C16 C15 C11 132.5(17) . . ?
C14 C15 C11 104.9(13) . . ?
C16 C15 Rh1 132.6(13) . . ?
C14 C15 Rh1 72.5(7) . . ?
C11 C15 Rh1 65.2(8) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 N1 C1 110.2(10) . . ?
C4 N1 C5 133.8(11) . . ?
C1 N1 C5 115.0(10) . . ?
C3 N2 C1 107.8(11) . . ?
C3 N2 C2 127.4(11) . . ?
C1 N2 C2 124.4(10) . . ?
C1 Rh1 C6 77.0(4) . . ?
C1 Rh1 C11 105.9(6) . . ?
C6 Rh1 C11 104.6(6) . . ?
C1 Rh1 C15 141.5(5) . . ?
C6 Rh1 C15 94.9(5) . . ?
C11 Rh1 C15 39.2(7) . . ?
C1 Rh1 C12 101.3(5) . . ?
C6 Rh1 C12 139.0(5) . . ?
C11 Rh1 C12 35.6(6) . . ?
C15 Rh1 C12 60.7(5) . . ?
C1 Rh1 C14 160.5(4) . . ?
C6 Rh1 C14 120.2(5) . . ?
C11 Rh1 C14 63.0(6) . . ?
C15 Rh1 C14 36.9(5) . . ?
C12 Rh1 C14 60.0(5) . . ?
C1 Rh1 C13 124.1(4) . . ?
C6 Rh1 C13 155.7(4) . . ?
C11 Rh1 C13 60.8(6) . . ?
C15 Rh1 C13 61.3(5) . . ?
C12 Rh1 C13 34.7(5) . . ?
C14 Rh1 C13 37.1(5) . . ?
C1 Rh1 I1 92.6(3) . . ?
C6 Rh1 I1 96.2(3) . . ?
C11 Rh1 I1 154.7(4) . . ?
C15 Rh1 I1 125.8(4) . . ?
C12 Rh1 I1 124.6(4) . . ?
C14 Rh1 I1 94.1(3) . . ?
C13 Rh1 I1 94.6(3) . . ?

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
N2 C3 C4 N1 0.3(13) . . . . ?
N1 C5 C6 C7 176.5(10) . . . . ?
C10 C5 C6 C7 -1.9(15) . . . . ?
N1 C5 C6 Rh1 -8.0(11) . . . . ?
C10 C5 C6 Rh1 173.6(8) . . . . ?
C5 C6 C7 C8 1.9(18) . . . . ?
Rh1 C6 C7 C8 -173.0(10) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C7 C8 C9 C10 -3(2) . . . . ?
C8 C9 C10 C5 2.7(18) . . . . ?
N1 C5 C10 C9 -178.6(10) . . . . ?
C6 C5 C10 C9 -0.4(16) . . . . ?
C15 C11 C12 C13 -10.1(15) . . . . ?
C17 C11 C12 C13 -175.2(12) . . . . ?
Rh1 C11 C12 C13 60.3(9) . . . . ?
C15 C11 C12 C18 169.0(12) . . . . ?
C17 C11 C12 C18 4(2) . . . . ?
Rh1 C11 C12 C18 -120.6(13) . . . . ?
C15 C11 C12 Rh1 -70.5(9) . . . . ?
C17 C11 C12 Rh1 124.4(15) . . . . ?
C11 C12 C13 C14 5.9(14) . . . . ?
C18 C12 C13 C14 -173.3(12) . . . . ?
Rh1 C12 C13 C14 61.4(8) . . . . ?
C11 C12 C13 C19 -177.2(15) . . . . ?
C18 C12 C13 C19 4(2) . . . . ?
Rh1 C12 C13 C19 -121.7(16) . . . . ?
C11 C12 C13 Rh1 -55.5(9) . . . . ?
C18 C12 C13 Rh1 125.3(11) . . . . ?
C12 C13 C14 C15 0.8(13) . . . . ?
C19 C13 C14 C15 -176.5(13) . . . . ?
Rh1 C13 C14 C15 62.6(9) . . . . ?
C12 C13 C14 C20 -174.9(16) . . . . ?
C19 C13 C14 C20 8(2) . . . . ?
Rh1 C13 C14 C20 -113.1(16) . . . . ?
C12 C13 C14 Rh1 -61.8(8) . . . . ?
C19 C13 C14 Rh1 120.9(13) . . . . ?
C13 C14 C15 C16 166.4(16) . . . . ?
C20 C14 C15 C16 -18(3) . . . . ?
Rh1 C14 C15 C16 -129.8(17) . . . . ?
C13 C14 C15 C11 -6.4(14) . . . . ?
C20 C14 C15 C11 169.4(15) . . . . ?
Rh1 C14 C15 C11 57.4(8) . . . . ?
C13 C14 C15 Rh1 -63.9(9) . . . . ?
C20 C14 C15 Rh1 112.0(16) . . . . ?
C12 C11 C15 C16 -161.7(18) . . . . ?
C17 C11 C15 C16 4(3) . . . . ?
Rh1 C11 C15 C16 126.0(19) . . . . ?
C12 C11 C15 C14 10.1(15) . . . . ?
C17 C11 C15 C14 175.8(12) . . . . ?
Rh1 C11 C15 C14 -62.3(9) . . . . ?
C12 C11 C15 Rh1 72.4(9) . . . . ?
C17 C11 C15 Rh1 -121.9(13) . . . . ?
C3 C4 N1 C1 0.3(12) . . . . ?
C3 C4 N1 C5 167.8(11) . . . . ?
N2 C1 N1 C4 -0.7(11) . . . . ?
Rh1 C1 N1 C4 177.3(7) . . . . ?
N2 C1 N1 C5 -170.8(8) . . . . ?
Rh1 C1 N1 C5 7.2(11) . . . . ?
C6 C5 N1 C4 -166.4(11) . . . . ?
C10 C5 N1 C4 12.0(17) . . . . ?
C6 C5 N1 C1 0.6(12) . . . . ?
C10 C5 N1 C1 179.1(9) . . . . ?
C4 C3 N2 C1 -0.7(14) . . . . ?
C4 C3 N2 C2 -173.9(12) . . . . ?
N1 C1 N2 C3 0.8(12) . . . . ?
Rh1 C1 N2 C3 -176.5(9) . . . . ?
N1 C1 N2 C2 174.3(11) . . . . ?
Rh1 C1 N2 C2 -3.1(18) . . . . ?
N1 C1 Rh1 C6 -8.8(7) . . . . ?
N2 C1 Rh1 C6 168.3(11) . . . . ?
N1 C1 Rh1 C11 92.9(9) . . . . ?
N2 C1 Rh1 C11 -90.0(12) . . . . ?
N1 C1 Rh1 C15 72.7(10) . . . . ?
N2 C1 Rh1 C15 -110.3(12) . . . . ?
N1 C1 Rh1 C12 129.3(8) . . . . ?
N2 C1 Rh1 C12 -53.6(11) . . . . ?
N1 C1 Rh1 C14 145.3(13) . . . . ?
N2 C1 Rh1 C14 -37.6(19) . . . . ?
N1 C1 Rh1 C13 158.0(7) . . . . ?
N2 C1 Rh1 C13 -24.9(13) . . . . ?
N1 C1 Rh1 I1 -104.6(7) . . . . ?
N2 C1 Rh1 I1 72.5(10) . . . . ?
C5 C6 Rh1 C1 9.0(7) . . . . ?
C7 C6 Rh1 C1 -176.1(11) . . . . ?
C5 C6 Rh1 C11 -94.3(9) . . . . ?
C7 C6 Rh1 C11 80.6(12) . . . . ?
C5 C6 Rh1 C15 -132.8(8) . . . . ?
C7 C6 Rh1 C15 42.0(11) . . . . ?
C5 C6 Rh1 C12 -83.4(10) . . . . ?
C7 C6 Rh1 C12 91.4(12) . . . . ?
C5 C6 Rh1 C14 -161.3(7) . . . . ?
C7 C6 Rh1 C14 13.6(12) . . . . ?
C5 C6 Rh1 C13 -143.7(10) . . . . ?
C7 C6 Rh1 C13 31.2(17) . . . . ?
C5 C6 Rh1 I1 100.2(7) . . . . ?
C7 C6 Rh1 I1 -84.9(10) . . . . ?
C12 C11 Rh1 C1 87.4(10) . . . . ?
C15 C11 Rh1 C1 -160.1(7) . . . . ?
C17 C11 Rh1 C1 -39(2) . . . . ?
C12 C11 Rh1 C6 167.8(9) . . . . ?
C15 C11 Rh1 C6 -79.7(8) . . . . ?
C17 C11 Rh1 C6 41(2) . . . . ?
C12 C11 Rh1 C15 -112.5(13) . . . . ?
C17 C11 Rh1 C15 121(2) . . . . ?
C15 C11 Rh1 C12 112.5(13) . . . . ?
C17 C11 Rh1 C12 -127(3) . . . . ?
C12 C11 Rh1 C14 -75.4(10) . . . . ?
C15 C11 Rh1 C14 37.1(8) . . . . ?
C17 C11 Rh1 C14 158(2) . . . . ?
C12 C11 Rh1 C13 -33.2(9) . . . . ?
C15 C11 Rh1 C13 79.3(8) . . . . ?
C17 C11 Rh1 C13 -160(2) . . . . ?
C12 C11 Rh1 I1 -48(2) . . . . ?
C15 C11 Rh1 I1 64.6(17) . . . . ?
C17 C11 Rh1 I1 -174.7(15) . . . . ?
C16 C15 Rh1 C1 -94(2) . . . . ?
C14 C15 Rh1 C1 148.0(7) . . . . ?
C11 C15 Rh1 C1 31.8(12) . . . . ?
C16 C15 Rh1 C6 -19(2) . . . . ?
C14 C15 Rh1 C6 -136.7(8) . . . . ?
C11 C15 Rh1 C6 107.1(9) . . . . ?
C16 C15 Rh1 C11 -126(2) . . . . ?
C14 C15 Rh1 C11 116.2(12) . . . . ?
C16 C15 Rh1 C12 -164(2) . . . . ?
C14 C15 Rh1 C12 78.1(9) . . . . ?
C11 C15 Rh1 C12 -38.1(9) . . . . ?
C16 C15 Rh1 C14 118(2) . . . . ?
C11 C15 Rh1 C14 -116.2(12) . . . . ?
C16 C15 Rh1 C13 156(2) . . . . ?
C14 C15 Rh1 C13 38.2(8) . . . . ?
C11 C15 Rh1 C13 -78.0(9) . . . . ?
C16 C15 Rh1 I1 82(2) . . . . ?
C14 C15 Rh1 I1 -35.4(10) . . . . ?
C11 C15 Rh1 I1 -151.6(8) . . . . ?
C11 C12 Rh1 C1 -101.5(11) . . . . ?
C13 C12 Rh1 C1 135.6(7) . . . . ?
C18 C12 Rh1 C1 19.1(16) . . . . ?
C11 C12 Rh1 C6 -18.2(14) . . . . ?
C13 C12 Rh1 C6 -141.1(7) . . . . ?
C18 C12 Rh1 C6 102.3(16) . . . . ?
C13 C12 Rh1 C11 -122.9(13) . . . . ?
C18 C12 Rh1 C11 121(2) . . . . ?
C11 C12 Rh1 C15 42.0(11) . . . . ?
C13 C12 Rh1 C15 -80.9(8) . . . . ?
C18 C12 Rh1 C15 162.5(18) . . . . ?
C11 C12 Rh1 C14 84.6(11) . . . . ?
C13 C12 Rh1 C14 -38.3(7) . . . . ?
C18 C12 Rh1 C14 -154.8(18) . . . . ?
C11 C12 Rh1 C13 122.9(13) . . . . ?
C18 C12 Rh1 C13 -116.6(18) . . . . ?
C11 C12 Rh1 I1 157.4(10) . . . . ?
C13 C12 Rh1 I1 34.4(8) . . . . ?
C18 C12 Rh1 I1 -82.1(16) . . . . ?
C15 C14 Rh1 C1 -98.2(16) . . . . ?
C13 C14 Rh1 C1 17.6(17) . . . . ?
C20 C14 Rh1 C1 141.6(15) . . . . ?
C15 C14 Rh1 C6 52.3(10) . . . . ?
C13 C14 Rh1 C6 168.1(7) . . . . ?
C20 C14 Rh1 C6 -67.9(15) . . . . ?
C15 C14 Rh1 C11 -39.5(10) . . . . ?
C13 C14 Rh1 C11 76.4(9) . . . . ?
C20 C14 Rh1 C11 -159.7(16) . . . . ?
C13 C14 Rh1 C15 115.8(11) . . . . ?
C20 C14 Rh1 C15 -120.2(17) . . . . ?
C15 C14 Rh1 C12 -80.0(9) . . . . ?
C13 C14 Rh1 C12 35.8(7) . . . . ?
C20 C14 Rh1 C12 159.8(15) . . . . ?
C15 C14 Rh1 C13 -115.8(11) . . . . ?
C20 C14 Rh1 C13 124.0(16) . . . . ?
C15 C14 Rh1 I1 151.9(8) . . . . ?
C13 C14 Rh1 I1 -92.2(7) . . . . ?
C20 C14 Rh1 I1 31.7(13) . . . . ?
C12 C13 Rh1 C1 -55.9(8) . . . . ?
C14 C13 Rh1 C1 -173.0(7) . . . . ?
C19 C13 Rh1 C1 73.6(17) . . . . ?
C12 C13 Rh1 C6 91.5(12) . . . . ?
C14 C13 Rh1 C6 -25.6(14) . . . . ?
C19 C13 Rh1 C6 -139.0(15) . . . . ?
C12 C13 Rh1 C11 34.1(9) . . . . ?
C14 C13 Rh1 C11 -83.0(9) . . . . ?
C19 C13 Rh1 C11 163.6(18) . . . . ?
C12 C13 Rh1 C15 79.1(8) . . . . ?
C14 C13 Rh1 C15 -38.0(8) . . . . ?
C19 C13 Rh1 C15 -151.3(17) . . . . ?
C14 C13 Rh1 C12 -117.1(10) . . . . ?
C19 C13 Rh1 C12 129.5(18) . . . . ?
C12 C13 Rh1 C14 117.1(10) . . . . ?
C19 C13 Rh1 C14 -113.3(18) . . . . ?
C12 C13 Rh1 I1 -152.2(7) . . . . ?
C14 C13 Rh1 I1 90.7(7) . . . . ?
C19 C13 Rh1 I1 -22.6(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         7.647
_refine_diff_density_min         -5.107
_refine_diff_density_rms         0.473
_database_code_depnum_ccdc_archive 'CCDC 1020425'
#######################################################################
#
#                 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_dgy

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 F3 N2 O3 S'
_chemical_formula_weight         484.48

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   '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                   16.032(7)
_cell_length_b                   8.837(3)
_cell_length_c                   31.193(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.528(17)
_cell_angle_gamma                90.00
_cell_volume                     4297(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3546
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.42

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      203(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20735
_diffrn_reflns_av_R_equivalents  0.2360
_diffrn_reflns_av_sigmaI/netI    0.1950
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         24.42
_reflns_number_total             3546
_reflns_number_gt                1757
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0839P)²+25.7466P] 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       0.0000(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3546
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2068
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.2297
_refine_ls_wR_factor_gt          0.1916
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          1.297
_refine_ls_shift/su_mean         0.004

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
C1 C 0.5153(4) 0.3204(8) 0.5766(2) 0.0282(18) Uani 1 1 d . . .
C2 C 0.4007(4) 0.5118(9) 0.5612(2) 0.042(2) Uani 1 1 d . . .
H2A H 0.3643 0.5518 0.5347 0.063 Uiso 1 1 calc R . .
H2B H 0.4341 0.5922 0.5774 0.063 Uiso 1 1 calc R . .
H2C H 0.3660 0.4663 0.5789 0.063 Uiso 1 1 calc R . .
C3 C 0.4478(5) 0.3515(10) 0.5049(3) 0.045(2) Uani 1 1 d . . .
H3 H 0.4101 0.3891 0.4799 0.054 Uiso 1 1 calc R . .
C4 C 0.5045(5) 0.2421(9) 0.5064(2) 0.039(2) Uani 1 1 d . . .
H4 H 0.5140 0.1895 0.4822 0.046 Uiso 1 1 calc R . .
C5 C 0.6080(4) 0.1090(9) 0.5685(3) 0.037(2) Uani 1 1 d . . .
C6 C 0.6391(4) 0.0116(9) 0.5414(2) 0.0353(19) Uani 1 1 d . . .
H6 H 0.6217 0.0212 0.5109 0.042 Uiso 1 1 calc R . .
C7 C 0.6961(5) -0.0999(10) 0.5600(2) 0.050(2) Uani 1 1 d . . .
H7 H 0.7168 -0.1655 0.5416 0.060 Uiso 1 1 calc R . .
C8 C 0.7244(4) -0.1181(10) 0.6066(3) 0.053(2) Uani 1 1 d . . .
H8 H 0.7623 -0.1950 0.6186 0.064 Uiso 1 1 calc R . .
C9 C 0.6949(4) -0.0213(8) 0.6326(3) 0.041(2) Uani 1 1 d . . .
H9 H 0.7132 -0.0299 0.6631 0.050 Uiso 1 1 calc R . .
C10 C 0.6344(4) 0.0977(9) 0.6137(2) 0.0326(19) Uani 1 1 d . . .
C11 C 0.6027(4) 0.2114(8) 0.6409(2) 0.0213(16) Uani 1 1 d . . .
C12 C 0.5467(4) 0.3218(8) 0.6234(2) 0.0231(17) Uani 1 1 d . . .
C13 C 0.5177(3) 0.4441(7) 0.64978(19) 0.0186(16) Uani 1 1 d . . .
C14 C 0.4596(4) 0.4165(8) 0.6759(2) 0.0265(17) Uani 1 1 d . . .
H14 H 0.4403 0.3184 0.6785 0.032 Uiso 1 1 calc R . .
C15 C 0.4302(4) 0.5338(9) 0.6981(2) 0.0346(19) Uani 1 1 d . . .
H15 H 0.3914 0.5140 0.7154 0.042 Uiso 1 1 calc R . .
C16 C 0.4583(4) 0.6800(9) 0.6945(2) 0.038(2) Uani 1 1 d . . .
H16 H 0.4381 0.7588 0.7091 0.045 Uiso 1 1 calc R . .
C17 C 0.5167(4) 0.7080(9) 0.6692(2) 0.037(2) Uani 1 1 d . . .
H17 H 0.5356 0.8064 0.6667 0.044 Uiso 1 1 calc R . .
C18 C 0.5473(4) 0.5917(8) 0.6476(2) 0.0294(18) Uani 1 1 d . . .
H18 H 0.5880 0.6119 0.6314 0.035 Uiso 1 1 calc R . .
C19 C 0.6397(4) 0.2018(7) 0.6900(2) 0.0206(16) Uani 1 1 d . . .
C20 C 0.5965(4) 0.1227(8) 0.7167(2) 0.0279(18) Uani 1 1 d . . .
H20 H 0.5431 0.0803 0.7044 0.033 Uiso 1 1 calc R . .
C21 C 0.6318(4) 0.1067(8) 0.7610(2) 0.0316(18) Uani 1 1 d . . .
H21 H 0.6021 0.0542 0.7786 0.038 Uiso 1 1 calc R . .
C22 C 0.7118(4) 0.1685(8) 0.7796(2) 0.0291(18) Uani 1 1 d . . .
H22 H 0.7363 0.1562 0.8095 0.035 Uiso 1 1 calc R . .
C23 C 0.7540(4) 0.2478(9) 0.7535(2) 0.0360(19) Uani 1 1 d . . .
H23 H 0.8071 0.2906 0.7660 0.043 Uiso 1 1 calc R . .
C24 C 0.7191(4) 0.2656(8) 0.7086(2) 0.0310(18) Uani 1 1 d . . .
H24 H 0.7485 0.3197 0.6912 0.037 Uiso 1 1 calc R . .
C25 C 0.7825(4) 0.3903(10) 0.5810(3) 0.039(2) Uani 1 1 d . . .
N1 N 0.5489(4) 0.2175(7) 0.55107(17) 0.0343(17) Uani 1 1 d . . .
N2 N 0.4562(4) 0.4012(7) 0.5501(2) 0.0379(16) Uani 1 1 d . . .
O1 O 0.8895(3) 0.5551(6) 0.63481(15) 0.0494(16) Uani 1 1 d . . .
O2 O 0.9373(3) 0.4281(6) 0.57481(14) 0.0420(14) Uani 1 1 d . . .
O3 O 0.8378(3) 0.6374(6) 0.55884(17) 0.0550(16) Uani 1 1 d . . .
F1 F 0.8021(3) 0.2687(5) 0.60693(14) 0.0547(13) Uani 1 1 d . . .
F2 F 0.7128(2) 0.4539(5) 0.59082(14) 0.0577(14) Uani 1 1 d . . .
F3 F 0.7587(3) 0.3376(6) 0.53974(14) 0.0624(15) Uani 1 1 d . . .
S1 S 0.87293(11) 0.5177(2) 0.58843(6) 0.0362(6) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N2 1.315(8) . ?
C1 N1 1.396(9) . ?
C1 C12 1.428(8) . ?
C2 N2 1.418(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.320(10) . ?
C3 N2 1.450(9) . ?
C3 H3 0.9300 . ?
C4 N1 1.424(9) . ?
C4 H4 0.9300 . ?
C5 N1 1.369(9) . ?
C5 C10 1.375(9) . ?
C5 C6 1.380(9) . ?
C6 C7 1.377(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.429(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.338(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.458(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.482(9) . ?
C11 C12 1.352(9) . ?
C11 C19 1.509(8) . ?
C12 C13 1.497(9) . ?
C13 C18 1.394(9) . ?
C13 C14 1.396(8) . ?
C14 C15 1.389(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.388(8) . ?
C19 C20 1.390(8) . ?
C20 C21 1.374(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.390(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(9) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 F1 1.337(8) . ?
C25 F3 1.338(8) . ?
C25 F2 1.347(8) . ?
C25 S1 1.807(7) . ?
O1 S1 1.447(5) . ?
O2 S1 1.441(5) . ?
O3 S1 1.431(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 108.2(6) . . ?
N2 C1 C12 131.9(7) . . ?
N1 C1 C12 119.8(6) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N2 106.3(7) . . ?
C4 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
C3 C4 N1 109.2(7) . . ?
C3 C4 H4 125.4 . . ?
N1 C4 H4 125.4 . . ?
N1 C5 C10 118.5(7) . . ?
N1 C5 C6 120.6(7) . . ?
C10 C5 C6 120.9(8) . . ?
C7 C6 C5 119.2(8) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 122.1(8) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 118.1(8) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C10 120.8(8) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 118.9(7) . . ?
C5 C10 C11 118.3(7) . . ?
C9 C10 C11 122.8(6) . . ?
C12 C11 C10 122.7(6) . . ?
C12 C11 C19 121.2(6) . . ?
C10 C11 C19 116.0(6) . . ?
C11 C12 C1 116.7(6) . . ?
C11 C12 C13 124.1(6) . . ?
C1 C12 C13 119.2(6) . . ?
C18 C13 C14 118.2(6) . . ?
C18 C13 C12 119.7(6) . . ?
C14 C13 C12 122.0(6) . . ?
C15 C14 C13 120.7(7) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.2(7) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.4(7) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.8(7) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.6(6) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C24 C19 C20 119.4(6) . . ?
C24 C19 C11 120.3(5) . . ?
C20 C19 C11 120.2(5) . . ?
C21 C20 C19 120.6(6) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.2(6) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.3(6) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C19 C24 C23 119.2(6) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
F1 C25 F3 106.0(7) . . ?
F1 C25 F2 106.7(6) . . ?
F3 C25 F2 107.4(6) . . ?
F1 C25 S1 110.8(5) . . ?
F3 C25 S1 112.3(5) . . ?
F2 C25 S1 113.2(6) . . ?
C5 N1 C1 123.6(6) . . ?
C5 N1 C4 129.5(6) . . ?
C1 N1 C4 106.7(6) . . ?
C1 N2 C2 128.5(6) . . ?
C1 N2 C3 109.6(7) . . ?
C2 N2 C3 121.7(6) . . ?
O3 S1 O2 114.7(3) . . ?
O3 S1 O1 115.4(3) . . ?
O2 S1 O1 116.3(3) . . ?
O3 S1 C25 101.2(4) . . ?
O2 S1 C25 103.2(3) . . ?
O1 S1 C25 102.9(3) . . ?

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
N2 C3 C4 N1 0.7(7) . . . . ?
N1 C5 C6 C7 -177.6(6) . . . . ?
C10 C5 C6 C7 1.2(10) . . . . ?
C5 C6 C7 C8 -0.2(10) . . . . ?
C6 C7 C8 C9 -1.0(11) . . . . ?
C7 C8 C9 C10 1.0(10) . . . . ?
N1 C5 C10 C9 177.7(6) . . . . ?
C6 C5 C10 C9 -1.1(9) . . . . ?
N1 C5 C10 C11 -4.8(9) . . . . ?
C6 C5 C10 C11 176.3(6) . . . . ?
C8 C9 C10 C5 0.0(9) . . . . ?
C8 C9 C10 C11 -177.4(6) . . . . ?
C5 C10 C11 C12 2.5(9) . . . . ?
C9 C10 C11 C12 179.9(6) . . . . ?
C5 C10 C11 C19 -174.8(5) . . . . ?
C9 C10 C11 C19 2.5(8) . . . . ?
C10 C11 C12 C1 2.9(8) . . . . ?
C19 C11 C12 C1 -179.8(5) . . . . ?
C10 C11 C12 C13 -176.0(5) . . . . ?
C19 C11 C12 C13 1.2(9) . . . . ?
N2 C1 C12 C11 173.3(6) . . . . ?
N1 C1 C12 C11 -6.1(8) . . . . ?
N2 C1 C12 C13 -7.7(10) . . . . ?
N1 C1 C12 C13 172.9(5) . . . . ?
C11 C12 C13 C18 107.5(7) . . . . ?
C1 C12 C13 C18 -71.5(7) . . . . ?
C11 C12 C13 C14 -74.4(7) . . . . ?
C1 C12 C13 C14 106.7(7) . . . . ?
C18 C13 C14 C15 1.9(8) . . . . ?
C12 C13 C14 C15 -176.4(5) . . . . ?
C13 C14 C15 C16 -0.1(9) . . . . ?
C14 C15 C16 C17 -0.8(10) . . . . ?
C15 C16 C17 C18 -0.2(10) . . . . ?
C16 C17 C18 C13 2.1(9) . . . . ?
C14 C13 C18 C17 -2.8(8) . . . . ?
C12 C13 C18 C17 175.4(5) . . . . ?
C12 C11 C19 C24 -95.6(7) . . . . ?
C10 C11 C19 C24 81.9(8) . . . . ?
C12 C11 C19 C20 87.5(8) . . . . ?
C10 C11 C19 C20 -95.0(7) . . . . ?
C24 C19 C20 C21 -0.4(10) . . . . ?
C11 C19 C20 C21 176.6(6) . . . . ?
C19 C20 C21 C22 -0.5(10) . . . . ?
C20 C21 C22 C23 1.2(10) . . . . ?
C21 C22 C23 C24 -1.0(11) . . . . ?
C20 C19 C24 C23 0.6(10) . . . . ?
C11 C19 C24 C23 -176.3(6) . . . . ?
C22 C23 C24 C19 0.1(11) . . . . ?
C10 C5 N1 C1 1.7(9) . . . . ?
C6 C5 N1 C1 -179.4(6) . . . . ?
C10 C5 N1 C4 -172.4(6) . . . . ?
C6 C5 N1 C4 6.5(10) . . . . ?
N2 C1 N1 C5 -175.5(6) . . . . ?
C12 C1 N1 C5 4.0(9) . . . . ?
N2 C1 N1 C4 -0.3(7) . . . . ?
C12 C1 N1 C4 179.2(5) . . . . ?
C3 C4 N1 C5 174.5(6) . . . . ?
C3 C4 N1 C1 -0.3(7) . . . . ?
N1 C1 N2 C2 175.1(6) . . . . ?
C12 C1 N2 C2 -4.3(12) . . . . ?
N1 C1 N2 C3 0.7(7) . . . . ?
C12 C1 N2 C3 -178.7(6) . . . . ?
C4 C3 N2 C1 -0.9(8) . . . . ?
C4 C3 N2 C2 -175.8(6) . . . . ?
F1 C25 S1 O3 -179.1(5) . . . . ?
F3 C25 S1 O3 62.6(6) . . . . ?
F2 C25 S1 O3 -59.2(6) . . . . ?
F1 C25 S1 O2 62.0(6) . . . . ?
F3 C25 S1 O2 -56.3(6) . . . . ?
F2 C25 S1 O2 -178.1(5) . . . . ?
F1 C25 S1 O1 -59.5(6) . . . . ?
F3 C25 S1 O1 -177.8(6) . . . . ?
F2 C25 S1 O1 60.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 1020426'
#######################################################################
#
#                 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_dgi

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 F6 N2 P'
_chemical_formula_weight         480.38

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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

_cell_length_a                   9.6965(13)
_cell_length_b                   14.8468(17)
_cell_length_c                   30.235(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4352.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    117(2)
_cell_measurement_reflns_used    3584
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.41

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      117(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13392
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         24.41
_reflns_number_total             3584
_reflns_number_gt                2689
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0887P)²+4.9376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3584
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1782
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.2216(3) -0.0992(2) 0.67747(10) 0.0298(7) Uani 1 1 d . . .
C2 C 0.0485(4) 0.0228(2) 0.69502(12) 0.0420(8) Uani 1 1 d . . .
H2A H 0.0090 0.0460 0.7218 0.063 Uiso 1 1 calc R . .
H2B H -0.0234 -0.0005 0.6764 0.063 Uiso 1 1 calc R . .
H2C H 0.0961 0.0702 0.6798 0.063 Uiso 1 1 calc R . .
C3 C 0.1933(4) -0.0650(2) 0.74820(11) 0.0414(8) Uani 1 1 d . . .
H3 H 0.1581 -0.0387 0.7737 0.050 Uiso 1 1 calc R . .
C4 C 0.2974(4) -0.1237(2) 0.74656(10) 0.0373(8) Uani 1 1 d . . .
H4 H 0.3471 -0.1462 0.7704 0.045 Uiso 1 1 calc R . .
C5 C 0.4201(3) -0.1972(2) 0.68301(11) 0.0321(7) Uani 1 1 d . . .
C6 C 0.4236(3) -0.2011(2) 0.63676(11) 0.0334(7) Uani 1 1 d . . .
C7 C 0.5302(3) -0.2529(2) 0.61732(13) 0.0421(8) Uani 1 1 d . . .
H7 H 0.5347 -0.2581 0.5867 0.051 Uiso 1 1 calc R . .
C8 C 0.6272(4) -0.2957(2) 0.64309(13) 0.0467(9) Uani 1 1 d . . .
H8 H 0.6977 -0.3285 0.6299 0.056 Uiso 1 1 calc R . .
C9 C 0.6195(4) -0.2897(2) 0.68878(13) 0.0455(9) Uani 1 1 d . . .
H9 H 0.6855 -0.3186 0.7060 0.055 Uiso 1 1 calc R . .
C10 C 0.5163(4) -0.2418(2) 0.70904(12) 0.0399(8) Uani 1 1 d . . .
H10 H 0.5109 -0.2393 0.7397 0.048 Uiso 1 1 calc R . .
C11 C 0.3188(3) -0.1567(2) 0.61077(10) 0.0308(7) Uani 1 1 d . . .
C12 C 0.2163(3) -0.1084(2) 0.63047(10) 0.0312(7) Uani 1 1 d . . .
C13 C 0.0987(4) -0.0689(2) 0.60536(10) 0.0365(8) Uani 1 1 d . . .
C14 C -0.0316(4) -0.1064(3) 0.60989(14) 0.0514(10) Uani 1 1 d . . .
H14 H -0.0442 -0.1557 0.6284 0.062 Uiso 1 1 calc R . .
C15 C -0.1430(5) -0.0711(3) 0.58710(17) 0.0735(15) Uani 1 1 d . . .
H15 H -0.2301 -0.0966 0.5903 0.088 Uiso 1 1 calc R . .
C16 C -0.1244(6) 0.0020(3) 0.55961(17) 0.0808(17) Uani 1 1 d . . .
H16 H -0.1992 0.0263 0.5445 0.097 Uiso 1 1 calc R . .
C17 C 0.0040(6) 0.0389(3) 0.55457(14) 0.0688(14) Uani 1 1 d . . .
H17 H 0.0161 0.0875 0.5355 0.083 Uiso 1 1 calc R . .
C18 C 0.1169(5) 0.0047(2) 0.57756(11) 0.0495(10) Uani 1 1 d . . .
H18 H 0.2035 0.0307 0.5743 0.059 Uiso 1 1 calc R . .
C19 C 0.3237(3) -0.1688(2) 0.56192(10) 0.0338(7) Uani 1 1 d . . .
C21 C 0.2440(4) -0.2335(3) 0.54144(11) 0.0478(9) Uani 1 1 d . . .
H21 H 0.1819 -0.2673 0.5580 0.057 Uiso 1 1 calc R . .
C22 C 0.2559(5) -0.2485(3) 0.49649(12) 0.0602(11) Uani 1 1 d . . .
H22 H 0.2015 -0.2923 0.4831 0.072 Uiso 1 1 calc R . .
C23 C 0.3463(4) -0.1999(3) 0.47149(12) 0.0532(10) Uani 1 1 d . . .
H23 H 0.3549 -0.2114 0.4414 0.064 Uiso 1 1 calc R . .
C24 C 0.4243(4) -0.1341(3) 0.49106(13) 0.0522(10) Uani 1 1 d . . .
H24 H 0.4843 -0.0997 0.4740 0.063 Uiso 1 1 calc R . .
C25 C 0.4143(4) -0.1184(2) 0.53631(12) 0.0449(9) Uani 1 1 d . . .
H25 H 0.4683 -0.0741 0.5494 0.054 Uiso 1 1 calc R . .
N1 N 0.1463(3) -0.04981(17) 0.70576(8) 0.0343(6) Uani 1 1 d . . .
N2 N 0.3170(3) -0.14448(17) 0.70204(8) 0.0314(6) Uani 1 1 d . . .
F1 F 0.4644(4) 0.0210(2) 0.66065(14) 0.1279(14) Uani 1 1 d . . .
F2 F 0.5403(3) 0.1488(2) 0.62804(9) 0.0834(9) Uani 1 1 d . . .
F3 F 0.5857(3) 0.12134(19) 0.70019(10) 0.0839(9) Uani 1 1 d . . .
F4 F 0.4403(4) 0.2274(2) 0.68192(10) 0.1026(11) Uani 1 1 d . . .
F5 F 0.3645(3) 0.1008(3) 0.71265(8) 0.1042(12) Uani 1 1 d . . .
F6 F 0.3175(3) 0.1278(3) 0.64163(9) 0.1150(14) Uani 1 1 d . . .
P1 P 0.45290(10) 0.12375(7) 0.66967(3) 0.0464(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.342(4) . ?
C1 N2 1.364(4) . ?
C1 C12 1.429(4) . ?
C2 N1 1.472(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.335(5) . ?
C3 N1 1.380(4) . ?
C3 H3 0.9300 . ?
C4 N2 1.394(4) . ?
C4 H4 0.9300 . ?
C5 C10 1.389(5) . ?
C5 N2 1.394(4) . ?
C5 C6 1.400(5) . ?
C6 C7 1.415(5) . ?
C6 C11 1.445(4) . ?
C7 C8 1.377(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.363(4) . ?
C11 C19 1.489(4) . ?
C12 C13 1.490(4) . ?
C13 C14 1.387(5) . ?
C13 C18 1.390(5) . ?
C14 C15 1.385(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C21 1.380(5) . ?
C19 C25 1.389(5) . ?
C21 C22 1.382(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
F1 P1 1.553(3) . ?
F2 P1 1.562(3) . ?
F3 P1 1.585(3) . ?
F4 P1 1.587(3) . ?
F5 P1 1.594(3) . ?
F6 P1 1.564(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 106.9(3) . . ?
N1 C1 C12 131.8(3) . . ?
N2 C1 C12 121.2(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 108.8(3) . . ?
C4 C3 H3 125.6 . . ?
N1 C3 H3 125.6 . . ?
C3 C4 N2 106.5(3) . . ?
C3 C4 H4 126.8 . . ?
N2 C4 H4 126.8 . . ?
C10 C5 N2 121.0(3) . . ?
C10 C5 C6 122.0(3) . . ?
N2 C5 C6 116.9(3) . . ?
C5 C6 C7 117.1(3) . . ?
C5 C6 C11 120.5(3) . . ?
C7 C6 C11 122.4(3) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C5 118.9(3) . . ?
C9 C10 H10 120.5 . . ?
C5 C10 H10 120.5 . . ?
C12 C11 C6 121.1(3) . . ?
C12 C11 C19 121.4(3) . . ?
C6 C11 C19 117.5(3) . . ?
C11 C12 C1 117.3(3) . . ?
C11 C12 C13 122.8(3) . . ?
C1 C12 C13 119.8(3) . . ?
C14 C13 C18 119.4(3) . . ?
C14 C13 C12 119.3(3) . . ?
C18 C13 C12 121.3(3) . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.7(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.9(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 119.3(4) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C21 C19 C25 118.6(3) . . ?
C21 C19 C11 120.7(3) . . ?
C25 C19 C11 120.6(3) . . ?
C19 C21 C22 120.4(4) . . ?
C19 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.9(4) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.5(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C19 C25 C24 120.1(4) . . ?
C19 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C1 N1 C3 108.9(3) . . ?
C1 N1 C2 127.6(3) . . ?
C3 N1 C2 122.5(3) . . ?
C1 N2 C4 108.9(3) . . ?
C1 N2 C5 122.6(3) . . ?
C4 N2 C5 128.4(3) . . ?
F1 P1 F2 93.0(2) . . ?
F1 P1 F6 90.2(2) . . ?
F2 P1 F6 90.54(16) . . ?
F1 P1 F3 91.3(2) . . ?
F2 P1 F3 91.92(16) . . ?
F6 P1 F3 177.09(19) . . ?
F1 P1 F4 176.6(2) . . ?
F2 P1 F4 89.98(17) . . ?
F6 P1 F4 91.4(2) . . ?
F3 P1 F4 87.05(18) . . ?
F1 P1 F5 88.4(2) . . ?
F2 P1 F5 178.49(19) . . ?
F6 P1 F5 89.93(15) . . ?
F3 P1 F5 87.56(15) . . ?
F4 P1 F5 88.58(19) . . ?

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
N1 C3 C4 N2 0.9(4) . . . . ?
C10 C5 C6 C7 0.0(5) . . . . ?
N2 C5 C6 C7 178.6(3) . . . . ?
C10 C5 C6 C11 177.6(3) . . . . ?
N2 C5 C6 C11 -3.8(4) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C11 C6 C7 C8 -178.9(3) . . . . ?
C6 C7 C8 C9 1.3(5) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C8 C9 C10 C5 -1.4(5) . . . . ?
N2 C5 C10 C9 -177.2(3) . . . . ?
C6 C5 C10 C9 1.3(5) . . . . ?
C5 C6 C11 C12 1.6(5) . . . . ?
C7 C6 C11 C12 179.0(3) . . . . ?
C5 C6 C11 C19 -176.0(3) . . . . ?
C7 C6 C11 C19 1.4(5) . . . . ?
C6 C11 C12 C1 3.6(4) . . . . ?
C19 C11 C12 C1 -178.9(3) . . . . ?
C6 C11 C12 C13 -173.9(3) . . . . ?
C19 C11 C12 C13 3.6(5) . . . . ?
N1 C1 C12 C11 172.5(3) . . . . ?
N2 C1 C12 C11 -6.6(4) . . . . ?
N1 C1 C12 C13 -9.9(5) . . . . ?
N2 C1 C12 C13 171.0(3) . . . . ?
C11 C12 C13 C14 108.4(4) . . . . ?
C1 C12 C13 C14 -69.0(4) . . . . ?
C11 C12 C13 C18 -71.7(4) . . . . ?
C1 C12 C13 C18 110.9(4) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 0.6(7) . . . . ?
C15 C16 C17 C18 -1.2(7) . . . . ?
C14 C13 C18 C17 -0.4(5) . . . . ?
C12 C13 C18 C17 179.7(3) . . . . ?
C16 C17 C18 C13 1.1(6) . . . . ?
C12 C11 C19 C21 -81.3(4) . . . . ?
C6 C11 C19 C21 96.3(4) . . . . ?
C12 C11 C19 C25 102.3(4) . . . . ?
C6 C11 C19 C25 -80.1(4) . . . . ?
C25 C19 C21 C22 0.9(5) . . . . ?
C11 C19 C21 C22 -175.6(4) . . . . ?
C19 C21 C22 C23 0.1(6) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C22 C23 C24 C25 1.7(6) . . . . ?
C21 C19 C25 C24 -0.5(5) . . . . ?
C11 C19 C25 C24 176.0(3) . . . . ?
C23 C24 C25 C19 -0.8(6) . . . . ?
N2 C1 N1 C3 -0.8(3) . . . . ?
C12 C1 N1 C3 -179.9(3) . . . . ?
N2 C1 N1 C2 167.7(3) . . . . ?
C12 C1 N1 C2 -11.5(5) . . . . ?
C4 C3 N1 C1 -0.1(4) . . . . ?
C4 C3 N1 C2 -169.2(3) . . . . ?
N1 C1 N2 C4 1.3(3) . . . . ?
C12 C1 N2 C4 -179.4(3) . . . . ?
N1 C1 N2 C5 -174.9(3) . . . . ?
C12 C1 N2 C5 4.4(4) . . . . ?
C3 C4 N2 C1 -1.4(4) . . . . ?
C3 C4 N2 C5 174.6(3) . . . . ?
C10 C5 N2 C1 179.5(3) . . . . ?
C6 C5 N2 C1 0.9(4) . . . . ?
C10 C5 N2 C4 4.0(5) . . . . ?
C6 C5 N2 C4 -174.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.41
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 1020427'
#######################################################################
#
#                 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_dg8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 F3 N2 O3 S'
_chemical_formula_weight         534.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   8.7315(4)
_cell_length_b                   9.0652(5)
_cell_length_c                   16.3291(8)
_cell_angle_alpha                83.644(4)
_cell_angle_beta                 88.973(3)
_cell_angle_gamma                71.500(4)
_cell_volume                     1217.97(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3178
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.98

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9358
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7319
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         22.98
_reflns_number_total             3178
_reflns_number_gt                2761
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0515P)²+0.9099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.2997(3) 0.5751(3) 0.33230(14) 0.0250(5) Uani 1 1 d . . .
C2 C 0.3770(3) 0.8166(3) 0.28446(16) 0.0397(6) Uani 1 1 d . . .
H2A H 0.4150 0.8872 0.3117 0.060 Uiso 1 1 calc R . .
H2B H 0.2767 0.8735 0.2561 0.060 Uiso 1 1 calc R . .
H2C H 0.4555 0.7684 0.2455 0.060 Uiso 1 1 calc R . .
C3 C 0.3523(3) 0.7052(3) 0.43004(14) 0.0286(6) Uani 1 1 d . . .
C4 C 0.3987(3) 0.8091(3) 0.47266(16) 0.0388(7) Uani 1 1 d . . .
H4 H 0.4376 0.8851 0.4453 0.047 Uiso 1 1 calc R . .
C5 C 0.3846(3) 0.7950(3) 0.55718(17) 0.0430(7) Uani 1 1 d . . .
H5 H 0.4134 0.8631 0.5878 0.052 Uiso 1 1 calc R . .
C6 C 0.3275(3) 0.6792(3) 0.59680(16) 0.0411(7) Uani 1 1 d . . .
H6 H 0.3191 0.6722 0.6539 0.049 Uiso 1 1 calc R . .
C7 C 0.2830(3) 0.5747(3) 0.55524(15) 0.0359(6) Uani 1 1 d . . .
H7 H 0.2458 0.4980 0.5831 0.043 Uiso 1 1 calc R . .
C8 C 0.2959(3) 0.5883(3) 0.46944(14) 0.0284(6) Uani 1 1 d . . .
C9 C 0.2006(3) 0.3820(3) 0.41050(14) 0.0254(5) Uani 1 1 d . . .
C10 C 0.1703(3) 0.3064(3) 0.48545(15) 0.0347(6) Uani 1 1 d . . .
H10 H 0.1912 0.3385 0.5351 0.042 Uiso 1 1 calc R . .
C11 C 0.1090(3) 0.1836(3) 0.48494(16) 0.0381(7) Uani 1 1 d . . .
H11 H 0.0897 0.1327 0.5348 0.046 Uiso 1 1 calc R . .
C12 C 0.0758(3) 0.1347(3) 0.41219(16) 0.0366(6) Uani 1 1 d . . .
H12 H 0.0323 0.0533 0.4132 0.044 Uiso 1 1 calc R . .
C13 C 0.1071(3) 0.2064(3) 0.33855(15) 0.0314(6) Uani 1 1 d . . .
H13 H 0.0848 0.1728 0.2896 0.038 Uiso 1 1 calc R . .
C14 C 0.1725(3) 0.3304(3) 0.33577(14) 0.0261(5) Uani 1 1 d . . .
C15 C 0.2178(3) 0.3976(3) 0.25866(14) 0.0267(6) Uani 1 1 d . . .
C16 C 0.2843(3) 0.5157(3) 0.25648(14) 0.0262(5) Uani 1 1 d . . .
C17 C 0.3449(3) 0.5782(3) 0.17809(14) 0.0278(6) Uani 1 1 d . . .
C18 C 0.2379(3) 0.6739(3) 0.11825(15) 0.0357(6) Uani 1 1 d . . .
H18 H 0.1273 0.6986 0.1262 0.043 Uiso 1 1 calc R . .
C19 C 0.2948(4) 0.7330(3) 0.04648(16) 0.0470(7) Uani 1 1 d . . .
H19 H 0.2222 0.7985 0.0068 0.056 Uiso 1 1 calc R . .
C20 C 0.4575(4) 0.6955(3) 0.03360(17) 0.0490(8) Uani 1 1 d . . .
H20 H 0.4952 0.7340 -0.0151 0.059 Uiso 1 1 calc R . .
C21 C 0.5650(4) 0.6008(4) 0.09290(19) 0.0533(8) Uani 1 1 d . . .
H21 H 0.6754 0.5765 0.0845 0.064 Uiso 1 1 calc R . .
C22 C 0.5096(3) 0.5415(3) 0.16503(17) 0.0435(7) Uani 1 1 d . . .
H22 H 0.5828 0.4770 0.2048 0.052 Uiso 1 1 calc R . .
C23 C 0.1979(3) 0.3285(3) 0.18252(15) 0.0325(6) Uani 1 1 d . . .
C24 C 0.0622(4) 0.3933(3) 0.13234(17) 0.0489(8) Uani 1 1 d . . .
H24 H -0.0167 0.4841 0.1447 0.059 Uiso 1 1 calc R . .
C25 C 0.0432(5) 0.3237(4) 0.06372(19) 0.0621(9) Uani 1 1 d . . .
H25 H -0.0486 0.3679 0.0303 0.075 Uiso 1 1 calc R . .
C26 C 0.1585(5) 0.1902(4) 0.04463(18) 0.0598(9) Uani 1 1 d . . .
H26 H 0.1455 0.1445 -0.0019 0.072 Uiso 1 1 calc R . .
C27 C 0.2936(4) 0.1240(4) 0.09449(19) 0.0519(8) Uani 1 1 d . . .
H27 H 0.3714 0.0326 0.0820 0.062 Uiso 1 1 calc R . .
C28 C 0.3141(3) 0.1931(3) 0.16343(16) 0.0393(7) Uani 1 1 d . . .
H28 H 0.4060 0.1485 0.1968 0.047 Uiso 1 1 calc R . .
C29 C -0.1903(4) 0.9981(4) 0.19531(18) 0.0568(9) Uani 1 1 d . . .
N1 N 0.3521(2) 0.6949(2) 0.34584(12) 0.0275(5) Uani 1 1 d . . .
N2 N 0.2625(2) 0.5078(2) 0.40644(11) 0.0249(5) Uani 1 1 d . . .
O1 O -0.2973(2) 0.8871(3) 0.32610(12) 0.0626(6) Uani 1 1 d . . .
O2 O -0.1374(3) 0.7075(3) 0.23403(16) 0.0740(7) Uani 1 1 d . . .
O3 O -0.0099(2) 0.8398(3) 0.31598(12) 0.0537(6) Uani 1 1 d . . .
F1 F -0.3117(3) 1.0038(3) 0.14623(12) 0.0986(9) Uani 1 1 d . . .
F2 F -0.2248(3) 1.1356(2) 0.22525(14) 0.1013(8) Uani 1 1 d . . .
F3 F -0.0626(3) 0.9850(2) 0.14806(12) 0.0816(7) Uani 1 1 d . . .
S1 S -0.15455(8) 0.83889(8) 0.27727(4) 0.0403(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.346(3) . ?
C1 N2 1.375(3) . ?
C1 C16 1.428(3) . ?
C2 N1 1.472(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.388(3) . ?
C3 C4 1.391(4) . ?
C3 C8 1.395(4) . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(3) . ?
C7 H7 0.9300 . ?
C8 N2 1.410(3) . ?
C9 C10 1.398(3) . ?
C9 N2 1.403(3) . ?
C9 C14 1.407(3) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.409(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.442(3) . ?
C15 C16 1.367(3) . ?
C15 C23 1.489(3) . ?
C16 C17 1.499(3) . ?
C17 C18 1.382(3) . ?
C17 C22 1.387(3) . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.381(4) . ?
C23 C28 1.385(4) . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.375(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 F1 1.325(4) . ?
C29 F3 1.326(3) . ?
C29 F2 1.332(4) . ?
C29 S1 1.809(3) . ?
O1 S1 1.441(2) . ?
O2 S1 1.417(2) . ?
O3 S1 1.425(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 109.07(19) . . ?
N1 C1 C16 129.3(2) . . ?
N2 C1 C16 121.6(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 129.1(2) . . ?
N1 C3 C8 108.2(2) . . ?
C4 C3 C8 122.7(2) . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 122.9(3) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 117.4(3) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C7 119.4(2) . . ?
C3 C8 N2 105.96(19) . . ?
C7 C8 N2 134.6(2) . . ?
C10 C9 N2 122.2(2) . . ?
C10 C9 C14 120.1(2) . . ?
N2 C9 C14 117.7(2) . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 118.5(2) . . ?
C9 C14 C15 120.4(2) . . ?
C13 C14 C15 121.0(2) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 C23 121.4(2) . . ?
C14 C15 C23 117.8(2) . . ?
C15 C16 C1 117.9(2) . . ?
C15 C16 C17 121.7(2) . . ?
C1 C16 C17 120.4(2) . . ?
C18 C17 C22 119.2(2) . . ?
C18 C17 C16 120.6(2) . . ?
C22 C17 C16 120.2(2) . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C24 C23 C28 119.3(2) . . ?
C24 C23 C15 121.2(2) . . ?
C28 C23 C15 119.5(2) . . ?
C23 C24 C25 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 120.5(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C23 C28 C27 120.0(3) . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
F1 C29 F3 106.8(2) . . ?
F1 C29 F2 108.0(3) . . ?
F3 C29 F2 106.7(3) . . ?
F1 C29 S1 111.6(3) . . ?
F3 C29 S1 112.2(2) . . ?
F2 C29 S1 111.3(2) . . ?
C1 N1 C3 108.69(19) . . ?
C1 N1 C2 127.7(2) . . ?
C3 N1 C2 122.7(2) . . ?
C1 N2 C9 121.34(19) . . ?
C1 N2 C8 108.10(19) . . ?
C9 N2 C8 130.55(19) . . ?
O2 S1 O3 114.64(14) . . ?
O2 S1 O1 116.13(15) . . ?
O3 S1 O1 114.74(12) . . ?
O2 S1 C29 102.86(15) . . ?
O3 S1 C29 103.13(15) . . ?
O1 S1 C29 102.70(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
N1 C3 C4 C5 179.1(2) . . . . ?
C8 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
N1 C3 C8 C7 -179.39(19) . . . . ?
C4 C3 C8 C7 0.8(3) . . . . ?
N1 C3 C8 N2 0.2(2) . . . . ?
C4 C3 C8 N2 -179.7(2) . . . . ?
C6 C7 C8 C3 0.0(3) . . . . ?
C6 C7 C8 N2 -179.4(2) . . . . ?
N2 C9 C10 C11 179.9(2) . . . . ?
C14 C9 C10 C11 -1.6(3) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C10 C9 C14 C13 2.7(3) . . . . ?
N2 C9 C14 C13 -178.64(19) . . . . ?
C10 C9 C14 C15 -174.0(2) . . . . ?
N2 C9 C14 C15 4.6(3) . . . . ?
C12 C13 C14 C9 -1.8(3) . . . . ?
C12 C13 C14 C15 174.9(2) . . . . ?
C9 C14 C15 C16 -2.0(3) . . . . ?
C13 C14 C15 C16 -178.6(2) . . . . ?
C9 C14 C15 C23 174.8(2) . . . . ?
C13 C14 C15 C23 -1.8(3) . . . . ?
C14 C15 C16 C1 -3.0(3) . . . . ?
C23 C15 C16 C1 -179.7(2) . . . . ?
C14 C15 C16 C17 174.8(2) . . . . ?
C23 C15 C16 C17 -1.9(3) . . . . ?
N1 C1 C16 C15 -175.9(2) . . . . ?
N2 C1 C16 C15 5.5(3) . . . . ?
N1 C1 C16 C17 6.2(3) . . . . ?
N2 C1 C16 C17 -172.38(19) . . . . ?
C15 C16 C17 C18 74.5(3) . . . . ?
C1 C16 C17 C18 -107.7(3) . . . . ?
C15 C16 C17 C22 -106.0(3) . . . . ?
C1 C16 C17 C22 71.8(3) . . . . ?
C22 C17 C18 C19 -0.4(4) . . . . ?
C16 C17 C18 C19 179.1(2) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C17 -0.4(5) . . . . ?
C18 C17 C22 C21 0.2(4) . . . . ?
C16 C17 C22 C21 -179.4(2) . . . . ?
C16 C15 C23 C24 -86.8(3) . . . . ?
C14 C15 C23 C24 96.4(3) . . . . ?
C16 C15 C23 C28 96.0(3) . . . . ?
C14 C15 C23 C28 -80.8(3) . . . . ?
C28 C23 C24 C25 -0.1(4) . . . . ?
C15 C23 C24 C25 -177.4(3) . . . . ?
C23 C24 C25 C26 -0.1(5) . . . . ?
C24 C25 C26 C27 0.6(5) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C24 C23 C28 C27 0.0(4) . . . . ?
C15 C23 C28 C27 177.3(2) . . . . ?
C26 C27 C28 C23 0.5(4) . . . . ?
N2 C1 N1 C3 1.1(2) . . . . ?
C16 C1 N1 C3 -177.5(2) . . . . ?
N2 C1 N1 C2 -168.0(2) . . . . ?
C16 C1 N1 C2 13.3(4) . . . . ?
C4 C3 N1 C1 179.0(2) . . . . ?
C8 C3 N1 C1 -0.8(2) . . . . ?
C4 C3 N1 C2 -11.2(3) . . . . ?
C8 C3 N1 C2 169.0(2) . . . . ?
N1 C1 N2 C9 178.31(17) . . . . ?
C16 C1 N2 C9 -2.9(3) . . . . ?
N1 C1 N2 C8 -1.0(2) . . . . ?
C16 C1 N2 C8 177.77(19) . . . . ?
C10 C9 N2 C1 176.39(19) . . . . ?
C14 C9 N2 C1 -2.2(3) . . . . ?
C10 C9 N2 C8 -4.4(3) . . . . ?
C14 C9 N2 C8 176.96(19) . . . . ?
C3 C8 N2 C1 0.5(2) . . . . ?
C7 C8 N2 C1 180.0(2) . . . . ?
C3 C8 N2 C9 -178.7(2) . . . . ?
C7 C8 N2 C9 0.7(4) . . . . ?
F1 C29 S1 O2 53.4(2) . . . . ?
F3 C29 S1 O2 -66.4(3) . . . . ?
F2 C29 S1 O2 174.1(2) . . . . ?
F1 C29 S1 O3 172.86(19) . . . . ?
F3 C29 S1 O3 53.1(3) . . . . ?
F2 C29 S1 O3 -66.4(3) . . . . ?
F1 C29 S1 O1 -67.6(2) . . . . ?
F3 C29 S1 O1 172.6(2) . . . . ?
F2 C29 S1 O1 53.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        22.98
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 1020428'
#######################################################################
#
#                 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_dgou

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 F3 N2 O3 S'
_chemical_formula_weight         486.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca '

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

_cell_length_a                   18.9839(19)
_cell_length_b                   10.2711(10)
_cell_length_c                   22.667(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4419.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    106(2)
_cell_measurement_reflns_used    3627
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.40

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      106(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            63554
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         24.40
_reflns_number_total             3627
_reflns_number_gt                2563
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0512P)²+3.6904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3627
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
C1 C 0.11140(13) 0.3644(3) 0.11160(11) 0.0168(6) Uani 1 1 d . . .
C2 C 0.08975(16) 0.3909(3) 0.22076(11) 0.0267(7) Uani 1 1 d . . .
H2A H 0.0795 0.4634 0.2461 0.040 Uiso 1 1 calc R . .
H2B H 0.1330 0.3508 0.2330 0.040 Uiso 1 1 calc R . .
H2C H 0.0522 0.3285 0.2231 0.040 Uiso 1 1 calc R . .
C3 C 0.07412(13) 0.5593(3) 0.14147(11) 0.0188(6) Uani 1 1 d . . .
C4 C 0.05178(14) 0.6652(3) 0.17504(13) 0.0247(7) Uani 1 1 d . . .
H4 H 0.0504 0.6619 0.2160 0.030 Uiso 1 1 calc R . .
C5 C 0.03183(14) 0.7748(3) 0.14455(13) 0.0280(7) Uani 1 1 d . . .
H5 H 0.0165 0.8474 0.1654 0.034 Uiso 1 1 calc R . .
C6 C 0.03398(14) 0.7799(3) 0.08297(13) 0.0258(7) Uani 1 1 d . . .
H6 H 0.0204 0.8562 0.0640 0.031 Uiso 1 1 calc R . .
C7 C 0.05559(13) 0.6752(3) 0.04951(12) 0.0215(7) Uani 1 1 d . . .
H7 H 0.0567 0.6792 0.0085 0.026 Uiso 1 1 calc R . .
C8 C 0.07580(13) 0.5629(2) 0.07989(12) 0.0174(6) Uani 1 1 d . . .
C9 C 0.11032(13) 0.3858(3) 0.00526(11) 0.0173(6) Uani 1 1 d . . .
C10 C 0.10505(14) 0.4622(3) -0.04536(11) 0.0210(7) Uani 1 1 d . . .
H10 H 0.0927 0.5495 -0.0422 0.025 Uiso 1 1 calc R . .
C11 C 0.11804(14) 0.4092(3) -0.09978(12) 0.0246(7) Uani 1 1 d . . .
H11 H 0.1147 0.4608 -0.1334 0.029 Uiso 1 1 calc R . .
C12 C 0.13622(14) 0.2785(3) -0.10500(12) 0.0249(7) Uani 1 1 d . . .
H12 H 0.1456 0.2430 -0.1419 0.030 Uiso 1 1 calc R . .
C13 C 0.14025(13) 0.2021(3) -0.05556(11) 0.0224(7) Uani 1 1 d . . .
H13 H 0.1513 0.1143 -0.0596 0.027 Uiso 1 1 calc R . .
C14 C 0.12806(13) 0.2529(3) 0.00123(11) 0.0171(6) Uani 1 1 d . . .
C15 C 0.13828(13) 0.1758(3) 0.05365(11) 0.0180(6) Uani 1 1 d . . .
C16 C 0.13487(13) 0.2335(3) 0.10823(11) 0.0175(6) Uani 1 1 d . . .
C17 C 0.16067(14) 0.1634(3) 0.16229(11) 0.0186(6) Uani 1 1 d . . .
C18 C 0.11966(15) 0.0719(3) 0.19139(11) 0.0226(7) Uani 1 1 d . . .
H18 H 0.0737 0.0567 0.1789 0.027 Uiso 1 1 calc R . .
C19 C 0.14660(15) 0.0031(3) 0.23891(12) 0.0288(7) Uani 1 1 d . . .
H19 H 0.1191 -0.0593 0.2577 0.035 Uiso 1 1 calc R . .
C20 C 0.21451(16) 0.0276(3) 0.25829(12) 0.0293(7) Uani 1 1 d . . .
H20 H 0.2326 -0.0184 0.2902 0.035 Uiso 1 1 calc R . .
C21 C 0.25557(15) 0.1200(3) 0.23038(12) 0.0277(7) Uani 1 1 d . . .
H21 H 0.3009 0.1371 0.2438 0.033 Uiso 1 1 calc R . .
C22 C 0.22875(14) 0.1874(3) 0.18205(12) 0.0233(7) Uani 1 1 d . . .
H22 H 0.2565 0.2489 0.1629 0.028 Uiso 1 1 calc R . .
C23 C 0.15654(14) 0.0337(3) 0.04801(12) 0.0224(7) Uani 1 1 d . . .
H23A H 0.1310 -0.0028 0.0148 0.027 Uiso 1 1 calc R . .
H23B H 0.1413 -0.0115 0.0833 0.027 Uiso 1 1 calc R . .
C24 C 0.23541(14) 0.0105(3) 0.03904(13) 0.0312(7) Uani 1 1 d . . .
H24A H 0.2442 -0.0813 0.0357 0.047 Uiso 1 1 calc R . .
H24B H 0.2609 0.0446 0.0722 0.047 Uiso 1 1 calc R . .
H24C H 0.2506 0.0535 0.0037 0.047 Uiso 1 1 calc R . .
C25 C -0.16087(15) 0.1932(3) 0.10987(12) 0.0236(7) Uani 1 1 d . . .
N1 N 0.09678(11) 0.4368(2) 0.15966(9) 0.0190(5) Uani 1 1 d . . .
N2 N 0.09903(11) 0.4379(2) 0.06198(9) 0.0165(5) Uani 1 1 d . . .
O1 O -0.06248(12) 0.1192(3) 0.17921(9) 0.0592(8) Uani 1 1 d . . .
O2 O -0.04628(11) 0.0862(2) 0.07462(10) 0.0476(6) Uani 1 1 d . . .
O3 O -0.03963(10) 0.30150(19) 0.11521(10) 0.0356(5) Uani 1 1 d . . .
F1 F -0.19603(8) 0.08130(15) 0.11699(8) 0.0366(5) Uani 1 1 d . . .
F2 F -0.18837(9) 0.27868(17) 0.14726(8) 0.0432(5) Uani 1 1 d . . .
F3 F -0.17495(8) 0.23472(18) 0.05544(7) 0.0394(5) Uani 1 1 d . . .
S1 S -0.06631(4) 0.17268(7) 0.12138(3) 0.0226(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.348(3) . ?
C1 N2 1.374(3) . ?
C1 C16 1.419(4) . ?
C2 N1 1.469(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.392(3) . ?
C3 C4 1.394(4) . ?
C3 C8 1.397(4) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(4) . ?
C7 H7 0.9300 . ?
C8 N2 1.417(3) . ?
C9 C10 1.394(4) . ?
C9 C14 1.408(4) . ?
C9 N2 1.409(3) . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.408(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.441(4) . ?
C15 C16 1.373(3) . ?
C15 C23 1.505(4) . ?
C16 C17 1.503(4) . ?
C17 C18 1.387(4) . ?
C17 C22 1.390(4) . ?
C18 C19 1.386(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.530(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 F2 1.327(3) . ?
C25 F3 1.333(3) . ?
C25 F1 1.339(3) . ?
C25 S1 1.826(3) . ?
O1 S1 1.423(2) . ?
O2 S1 1.434(2) . ?
O3 S1 1.424(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 108.9(2) . . ?
N1 C1 C16 129.1(2) . . ?
N2 C1 C16 122.0(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 129.6(2) . . ?
N1 C3 C8 108.2(2) . . ?
C4 C3 C8 122.1(3) . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 117.1(3) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C7 C8 C3 120.5(2) . . ?
C7 C8 N2 133.8(2) . . ?
C3 C8 N2 105.6(2) . . ?
C10 C9 C14 120.6(2) . . ?
C10 C9 N2 121.7(2) . . ?
C14 C9 N2 117.6(2) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C9 117.3(2) . . ?
C13 C14 C15 121.8(2) . . ?
C9 C14 C15 120.8(2) . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 C23 120.4(2) . . ?
C14 C15 C23 119.6(2) . . ?
C15 C16 C1 118.2(2) . . ?
C15 C16 C17 120.8(2) . . ?
C1 C16 C17 120.8(2) . . ?
C18 C17 C22 119.3(2) . . ?
C18 C17 C16 122.0(2) . . ?
C22 C17 C16 118.7(2) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 120.3(3) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C15 C23 C24 112.8(2) . . ?
C15 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C15 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
F2 C25 F3 107.5(2) . . ?
F2 C25 F1 107.1(2) . . ?
F3 C25 F1 106.6(2) . . ?
F2 C25 S1 111.83(19) . . ?
F3 C25 S1 111.49(18) . . ?
F1 C25 S1 111.94(19) . . ?
C1 N1 C3 108.8(2) . . ?
C1 N1 C2 127.1(2) . . ?
C3 N1 C2 122.8(2) . . ?
C1 N2 C9 120.8(2) . . ?
C1 N2 C8 108.4(2) . . ?
C9 N2 C8 130.8(2) . . ?
O1 S1 O3 115.54(15) . . ?
O1 S1 O2 115.35(16) . . ?
O3 S1 O2 114.11(14) . . ?
O1 S1 C25 103.08(13) . . ?
O3 S1 C25 103.20(12) . . ?
O2 S1 C25 103.09(12) . . ?

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
N1 C3 C4 C5 -179.6(3) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C3 -0.3(4) . . . . ?
C6 C7 C8 N2 178.4(3) . . . . ?
N1 C3 C8 C7 -180.0(2) . . . . ?
C4 C3 C8 C7 0.8(4) . . . . ?
N1 C3 C8 N2 1.0(3) . . . . ?
C4 C3 C8 N2 -178.3(2) . . . . ?
C14 C9 C10 C11 -0.9(4) . . . . ?
N2 C9 C10 C11 178.4(2) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C9 1.0(4) . . . . ?
C12 C13 C14 C15 -174.5(2) . . . . ?
C10 C9 C14 C13 0.2(4) . . . . ?
N2 C9 C14 C13 -179.1(2) . . . . ?
C10 C9 C14 C15 175.7(2) . . . . ?
N2 C9 C14 C15 -3.6(3) . . . . ?
C13 C14 C15 C16 171.4(2) . . . . ?
C9 C14 C15 C16 -3.9(4) . . . . ?
C13 C14 C15 C23 -5.3(4) . . . . ?
C9 C14 C15 C23 179.4(2) . . . . ?
C14 C15 C16 C1 8.8(4) . . . . ?
C23 C15 C16 C1 -174.5(2) . . . . ?
C14 C15 C16 C17 -166.5(2) . . . . ?
C23 C15 C16 C17 10.2(4) . . . . ?
N1 C1 C16 C15 172.4(2) . . . . ?
N2 C1 C16 C15 -6.6(4) . . . . ?
N1 C1 C16 C17 -12.3(4) . . . . ?
N2 C1 C16 C17 168.7(2) . . . . ?
C15 C16 C17 C18 -81.4(3) . . . . ?
C1 C16 C17 C18 103.4(3) . . . . ?
C15 C16 C17 C22 95.9(3) . . . . ?
C1 C16 C17 C22 -79.3(3) . . . . ?
C22 C17 C18 C19 -1.4(4) . . . . ?
C16 C17 C18 C19 176.0(2) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C18 C17 C22 C21 0.3(4) . . . . ?
C16 C17 C22 C21 -177.1(2) . . . . ?
C20 C21 C22 C17 0.8(4) . . . . ?
C16 C15 C23 C24 -92.7(3) . . . . ?
C14 C15 C23 C24 84.0(3) . . . . ?
N2 C1 N1 C3 0.3(3) . . . . ?
C16 C1 N1 C3 -178.8(3) . . . . ?
N2 C1 N1 C2 167.6(2) . . . . ?
C16 C1 N1 C2 -11.6(4) . . . . ?
C4 C3 N1 C1 178.4(3) . . . . ?
C8 C3 N1 C1 -0.8(3) . . . . ?
C4 C3 N1 C2 10.4(4) . . . . ?
C8 C3 N1 C2 -168.8(2) . . . . ?
N1 C1 N2 C9 179.8(2) . . . . ?
C16 C1 N2 C9 -0.9(4) . . . . ?
N1 C1 N2 C8 0.3(3) . . . . ?
C16 C1 N2 C8 179.5(2) . . . . ?
C10 C9 N2 C1 -173.4(2) . . . . ?
C14 C9 N2 C1 5.9(3) . . . . ?
C10 C9 N2 C8 6.0(4) . . . . ?
C14 C9 N2 C8 -174.7(2) . . . . ?
C7 C8 N2 C1 -179.7(3) . . . . ?
C3 C8 N2 C1 -0.8(3) . . . . ?
C7 C8 N2 C9 0.9(5) . . . . ?
C3 C8 N2 C9 179.8(2) . . . . ?
F2 C25 S1 O1 64.0(2) . . . . ?
F3 C25 S1 O1 -175.6(2) . . . . ?
F1 C25 S1 O1 -56.3(2) . . . . ?
F2 C25 S1 O3 -56.6(2) . . . . ?
F3 C25 S1 O3 63.7(2) . . . . ?
F1 C25 S1 O3 -176.90(18) . . . . ?
F2 C25 S1 O2 -175.7(2) . . . . ?
F3 C25 S1 O2 -55.3(2) . . . . ?
F1 C25 S1 O2 64.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.40
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 1020429'
#######################################################################
#
#                 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_dgout

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 F3 N2 O3 S'
_chemical_formula_weight         508.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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)/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                   14.0991(12)
_cell_length_b                   7.9225(7)
_cell_length_c                   21.8819(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.609(2)
_cell_angle_gamma                90.00
_cell_volume                     2402.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4124
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.78

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            67165
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         24.78
_reflns_number_total             4124
_reflns_number_gt                2592
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.1190P)²+5.6955P] 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       0.0000(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4124
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1404
_refine_ls_R_factor_gt           0.0901
_refine_ls_wR_factor_ref         0.2672
_refine_ls_wR_factor_gt          0.2288
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          2.215
_refine_ls_shift/su_mean         0.007

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
C1 C 0.6907(3) -0.5389(6) 0.1630(2) 0.0413(11) Uani 1 1 d . . .
C2 C 0.5376(4) -0.3679(7) 0.1575(3) 0.0640(15) Uani 1 1 d . . .
H2A H 0.4771 -0.3866 0.1706 0.096 Uiso 1 1 calc R . .
H2B H 0.5266 -0.3504 0.1134 0.096 Uiso 1 1 calc R . .
H2C H 0.5683 -0.2699 0.1782 0.096 Uiso 1 1 calc R . .
C3 C 0.5738(4) -0.6518(7) 0.2043(2) 0.0590(14) Uani 1 1 d . . .
H3 H 0.5147 -0.6658 0.2169 0.071 Uiso 1 1 calc R . .
C4 C 0.6461(4) -0.7627(7) 0.2138(2) 0.0557(14) Uani 1 1 d . . .
H4 H 0.6470 -0.8664 0.2338 0.067 Uiso 1 1 calc R . .
C5 C 0.8108(3) -0.7602(6) 0.1844(2) 0.0425(11) Uani 1 1 d . . .
C6 C 0.8364(4) -0.9184(7) 0.2091(2) 0.0554(13) Uani 1 1 d . . .
H6 H 0.7944 -0.9793 0.2289 0.067 Uiso 1 1 calc R . .
C7 C 0.9236(4) -0.9827(7) 0.2039(3) 0.0630(15) Uani 1 1 d . . .
H7 H 0.9421 -1.0880 0.2208 0.076 Uiso 1 1 calc R . .
C8 C 0.9858(4) -0.8924(7) 0.1737(3) 0.0648(15) Uani 1 1 d . . .
H8 H 1.0451 -0.9384 0.1699 0.078 Uiso 1 1 calc R . .
C9 C 0.9603(4) -0.7372(6) 0.1495(2) 0.0513(12) Uani 1 1 d . . .
H9 H 1.0026 -0.6786 0.1293 0.062 Uiso 1 1 calc R . .
C10 C 0.8716(3) -0.6639(6) 0.1545(2) 0.0406(11) Uani 1 1 d . . .
C11 C 0.8406(3) -0.5000(6) 0.1286(2) 0.0394(11) Uani 1 1 d . . .
C12 C 0.7509(3) -0.4379(6) 0.13266(19) 0.0394(11) Uani 1 1 d . . .
C13 C 0.7181(3) -0.2781(6) 0.1080(2) 0.0438(11) Uani 1 1 d . . .
C14 C 0.6924(3) -0.1425(7) 0.0863(2) 0.0465(12) Uani 1 1 d . . .
C15 C 0.6636(3) 0.0172(6) 0.0597(2) 0.0468(12) Uani 1 1 d . . .
C16 C 0.7249(4) 0.1050(7) 0.0280(3) 0.0636(15) Uani 1 1 d . . .
H16 H 0.7843 0.0587 0.0246 0.076 Uiso 1 1 calc R . .
C17 C 0.6984(6) 0.2602(8) 0.0014(3) 0.0802(19) Uani 1 1 d . . .
H17 H 0.7396 0.3177 -0.0200 0.096 Uiso 1 1 calc R . .
C18 C 0.6118(6) 0.3286(8) 0.0066(3) 0.082(2) Uani 1 1 d . . .
H18 H 0.5943 0.4333 -0.0112 0.098 Uiso 1 1 calc R . .
C19 C 0.5503(5) 0.2460(8) 0.0376(3) 0.0799(19) Uani 1 1 d . . .
H19 H 0.4914 0.2945 0.0410 0.096 Uiso 1 1 calc R . .
C20 C 0.5759(4) 0.0880(7) 0.0643(3) 0.0630(15) Uani 1 1 d . . .
H20 H 0.5337 0.0308 0.0850 0.076 Uiso 1 1 calc R . .
C21 C 0.9061(3) -0.4001(6) 0.0955(2) 0.0434(11) Uani 1 1 d . . .
C22 C 0.8769(4) -0.3574(7) 0.0333(2) 0.0556(13) Uani 1 1 d . . .
H22 H 0.8162 -0.3899 0.0123 0.067 Uiso 1 1 calc R . .
C23 C 0.9370(5) -0.2674(8) 0.0025(3) 0.0736(18) Uani 1 1 d . . .
H23 H 0.9167 -0.2378 -0.0390 0.088 Uiso 1 1 calc R . .
C24 C 1.0267(5) -0.2217(8) 0.0331(4) 0.084(2) Uani 1 1 d . . .
H24 H 1.0673 -0.1611 0.0121 0.100 Uiso 1 1 calc R . .
C25 C 1.0574(4) -0.2642(8) 0.0943(4) 0.0730(17) Uani 1 1 d . . .
H25 H 1.1188 -0.2336 0.1147 0.088 Uiso 1 1 calc R . .
C26 C 0.9969(4) -0.3525(6) 0.1255(3) 0.0545(13) Uani 1 1 d . . .
H26 H 1.0174 -0.3802 0.1671 0.065 Uiso 1 1 calc R . .
C27 C 0.2961(6) 0.1135(10) 0.1527(4) 0.095(2) Uani 1 1 d . . .
N1 N 0.5996(3) -0.5144(5) 0.17334(18) 0.0500(11) Uani 1 1 d . . .
N2 N 0.7198(3) -0.6926(5) 0.18775(17) 0.0458(10) Uani 1 1 d . . .
O1 O 0.3382(4) 0.3794(9) 0.1044(3) 0.140(2) Uani 1 1 d . . .
O2 O 0.3486(3) 0.3747(6) 0.2164(2) 0.0874(14) Uani 1 1 d . . .
O3 O 0.1919(3) 0.3750(7) 0.1500(2) 0.1037(17) Uani 1 1 d . . .
F1 F 0.3852(3) 0.0549(6) 0.1621(2) 0.1190(16) Uani 1 1 d . . .
F2 F 0.2459(4) 0.0522(6) 0.1017(2) 0.1376(19) Uani 1 1 d . . .
F3 F 0.2528(4) 0.0489(8) 0.2003(3) 0.154(2) Uani 1 1 d . . .
S1 S 0.28973(11) 0.3358(2) 0.15844(9) 0.0818(6) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.358(6) . ?
C1 N2 1.365(6) . ?
C1 C12 1.418(6) . ?
C2 N1 1.456(7) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.333(7) . ?
C3 N1 1.367(6) . ?
C3 H3 0.9300 . ?
C4 N2 1.390(6) . ?
C4 H4 0.9300 . ?
C5 C10 1.397(6) . ?
C5 C6 1.386(7) . ?
C5 N2 1.405(6) . ?
C6 C7 1.355(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.401(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.452(6) . ?
C11 C12 1.375(6) . ?
C11 C21 1.499(6) . ?
C12 C13 1.420(7) . ?
C13 C14 1.203(7) . ?
C14 C15 1.420(7) . ?
C15 C16 1.390(7) . ?
C15 C20 1.378(7) . ?
C16 C17 1.383(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.359(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.379(7) . ?
C21 C22 1.390(7) . ?
C22 C23 1.375(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 F2 1.300(7) . ?
C27 F1 1.320(8) . ?
C27 F3 1.397(9) . ?
C27 S1 1.770(8) . ?
O1 S1 1.510(5) . ?
O2 S1 1.415(4) . ?
O3 S1 1.392(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 106.6(4) . . ?
N1 C1 C12 131.6(4) . . ?
N2 C1 C12 121.8(4) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 109.6(4) . . ?
C4 C3 H3 125.2 . . ?
N1 C3 H3 125.2 . . ?
C3 C4 N2 106.3(5) . . ?
C3 C4 H4 126.8 . . ?
N2 C4 H4 126.8 . . ?
C10 C5 C6 122.6(5) . . ?
C10 C5 N2 117.5(4) . . ?
C6 C5 N2 119.9(4) . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.4(5) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C9 116.3(4) . . ?
C5 C10 C11 120.4(4) . . ?
C9 C10 C11 123.3(4) . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 C21 119.9(4) . . ?
C10 C11 C21 119.5(4) . . ?
C11 C12 C1 117.8(4) . . ?
C11 C12 C13 122.2(4) . . ?
C1 C12 C13 120.0(4) . . ?
C14 C13 C12 178.3(5) . . ?
C13 C14 C15 178.7(5) . . ?
C16 C15 C20 118.7(5) . . ?
C16 C15 C14 119.5(5) . . ?
C20 C15 C14 121.8(5) . . ?
C17 C16 C15 120.7(6) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.8(6) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.9(6) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 119.9(6) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 120.0(6) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C26 C21 C22 118.7(4) . . ?
C26 C21 C11 121.0(4) . . ?
C22 C21 C11 120.2(4) . . ?
C23 C22 C21 120.5(5) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.7(6) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.7(6) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 119.7(6) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
F2 C27 F1 110.9(7) . . ?
F2 C27 F3 105.0(7) . . ?
F1 C27 F3 106.7(7) . . ?
F2 C27 S1 114.0(6) . . ?
F1 C27 S1 113.5(6) . . ?
F3 C27 S1 106.0(6) . . ?
C1 N1 C3 108.4(4) . . ?
C1 N1 C2 128.2(4) . . ?
C3 N1 C2 123.3(4) . . ?
C1 N2 C4 109.1(4) . . ?
C1 N2 C5 122.0(4) . . ?
C4 N2 C5 128.9(4) . . ?
O3 S1 O2 118.2(3) . . ?
O3 S1 O1 115.2(4) . . ?
O2 S1 O1 112.1(3) . . ?
O3 S1 C27 105.9(4) . . ?
O2 S1 C27 104.6(3) . . ?
O1 S1 C27 97.8(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
N1 C3 C4 N2 -0.1(6) . . . . ?
C10 C5 C6 C7 -0.2(7) . . . . ?
N2 C5 C6 C7 178.4(4) . . . . ?
C5 C6 C7 C8 -0.8(8) . . . . ?
C6 C7 C8 C9 0.9(9) . . . . ?
C7 C8 C9 C10 0.2(8) . . . . ?
C6 C5 C10 C9 1.2(7) . . . . ?
N2 C5 C10 C9 -177.5(4) . . . . ?
C6 C5 C10 C11 179.1(4) . . . . ?
N2 C5 C10 C11 0.4(6) . . . . ?
C8 C9 C10 C5 -1.1(7) . . . . ?
C8 C9 C10 C11 -179.0(4) . . . . ?
C5 C10 C11 C12 -0.6(6) . . . . ?
C9 C10 C11 C12 177.2(4) . . . . ?
C5 C10 C11 C21 -178.8(4) . . . . ?
C9 C10 C11 C21 -1.0(6) . . . . ?
C10 C11 C12 C1 0.2(6) . . . . ?
C21 C11 C12 C1 178.4(4) . . . . ?
C10 C11 C12 C13 179.9(4) . . . . ?
C21 C11 C12 C13 -1.9(6) . . . . ?
N1 C1 C12 C11 -178.8(4) . . . . ?
N2 C1 C12 C11 0.3(6) . . . . ?
N1 C1 C12 C13 1.5(7) . . . . ?
N2 C1 C12 C13 -179.5(4) . . . . ?
C11 C12 C13 C14 11(18) . . . . ?
C1 C12 C13 C14 -169(100) . . . . ?
C12 C13 C14 C15 13(38) . . . . ?
C13 C14 C15 C16 -21(26) . . . . ?
C13 C14 C15 C20 159(26) . . . . ?
C20 C15 C16 C17 -0.1(8) . . . . ?
C14 C15 C16 C17 179.6(5) . . . . ?
C15 C16 C17 C18 0.5(9) . . . . ?
C16 C17 C18 C19 -0.2(10) . . . . ?
C17 C18 C19 C20 -0.3(10) . . . . ?
C16 C15 C20 C19 -0.5(8) . . . . ?
C14 C15 C20 C19 179.8(5) . . . . ?
C18 C19 C20 C15 0.7(9) . . . . ?
C12 C11 C21 C26 122.5(5) . . . . ?
C10 C11 C21 C26 -59.3(6) . . . . ?
C12 C11 C21 C22 -59.1(6) . . . . ?
C10 C11 C21 C22 119.1(5) . . . . ?
C26 C21 C22 C23 -0.9(8) . . . . ?
C11 C21 C22 C23 -179.3(5) . . . . ?
C21 C22 C23 C24 0.9(9) . . . . ?
C22 C23 C24 C25 -0.2(10) . . . . ?
C23 C24 C25 C26 -0.6(10) . . . . ?
C24 C25 C26 C21 0.7(9) . . . . ?
C22 C21 C26 C25 0.0(7) . . . . ?
C11 C21 C26 C25 178.4(5) . . . . ?
N2 C1 N1 C3 0.2(5) . . . . ?
C12 C1 N1 C3 179.3(5) . . . . ?
N2 C1 N1 C2 178.1(4) . . . . ?
C12 C1 N1 C2 -2.8(8) . . . . ?
C4 C3 N1 C1 -0.1(6) . . . . ?
C4 C3 N1 C2 -178.1(5) . . . . ?
N1 C1 N2 C4 -0.2(5) . . . . ?
C12 C1 N2 C4 -179.5(4) . . . . ?
N1 C1 N2 C5 178.9(4) . . . . ?
C12 C1 N2 C5 -0.4(6) . . . . ?
C3 C4 N2 C1 0.2(6) . . . . ?
C3 C4 N2 C5 -178.8(4) . . . . ?
C10 C5 N2 C1 0.0(6) . . . . ?
C6 C5 N2 C1 -178.7(4) . . . . ?
C10 C5 N2 C4 178.9(4) . . . . ?
C6 C5 N2 C4 0.3(7) . . . . ?
F2 C27 S1 O3 54.4(8) . . . . ?
F1 C27 S1 O3 -177.5(6) . . . . ?
F3 C27 S1 O3 -60.6(5) . . . . ?
F2 C27 S1 O2 180.0(6) . . . . ?
F1 C27 S1 O2 -51.8(7) . . . . ?
F3 C27 S1 O2 65.0(5) . . . . ?
F2 C27 S1 O1 -64.7(7) . . . . ?
F1 C27 S1 O1 63.5(7) . . . . ?
F3 C27 S1 O1 -179.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.78
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.743
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 1020430'
