# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
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#  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 
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data_av_sd341
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 F3 N3 O3'
_chemical_formula_sum            'C15 H14 F3 N3 O3'
_chemical_formula_weight         341.29

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

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  'P 2ybc'
_symmetry_Int_Tables_number      14

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                   17.9524(3)
_cell_length_b                   6.20460(10)
_cell_length_c                   14.3442(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.1480(10)
_cell_angle_gamma                90.00
_cell_volume                     1509.37(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5832
_cell_measurement_theta_min      5.696
_cell_measurement_theta_max      59.928

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17011
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         29.99
_reflns_number_total             4381
_reflns_number_gt                3462
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms
were positioned geometrically and refined using a riding model, with C---H =
0.98 (methyl groups), 0.99\%A (methylene groups), 1.00\%A (methine groups) or
0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) = 1.5 times <i>U</i>~eq~(C)
(methyl groups) or with <i>U</i>~iso~(H) = 1.2 times <i>U</i>~eq~(C)
(methylene groups, aryl CH, methine groups). Torsion angles of all methyl
groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0626P)^2^+0.9729P] where P=(Fo^2^+2Fc^2^)/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         4381
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
N1 N 0.09734(7) 0.0124(2) 0.34928(8) 0.0184(2) Uani 1 1 d . . .
N2 N 0.23186(7) 0.2221(3) 0.18854(9) 0.0278(3) Uani 1 1 d . . .
N3 N 0.11988(7) 0.0485(2) 0.19769(8) 0.0185(2) Uani 1 1 d . . .
O1 O 0.33373(6) 0.32844(18) 0.33243(7) 0.0231(2) Uani 1 1 d . . .
O2 O 0.01155(7) -0.1268(2) 0.20860(8) 0.0299(3) Uani 1 1 d . . .
O3 O 0.18070(7) 0.1634(2) 0.48971(8) 0.0289(3) Uani 1 1 d . . .
F1 F 0.22639(8) 0.61957(19) 0.46271(10) 0.0488(3) Uani 1 1 d . . .
F2 F 0.32935(7) 0.7056(2) 0.42579(11) 0.0536(4) Uani 1 1 d . . .
F3 F 0.21733(7) 0.67715(17) 0.31189(9) 0.0446(3) Uani 1 1 d . . .
C1 C 0.07181(8) -0.0272(2) 0.24960(10) 0.0189(3) Uani 1 1 d . . .
C2 C 0.16328(8) 0.1366(2) 0.39928(10) 0.0183(3) Uani 1 1 d . . .
C3 C 0.20644(8) 0.2216(2) 0.34092(10) 0.0175(3) Uani 1 1 d . . .
C4 C 0.27999(8) 0.3505(2) 0.38627(10) 0.0201(3) Uani 1 1 d . . .
H4 H 0.3065 0.2925 0.4541 0.024 Uiso 1 1 calc R . .
C5 C 0.30047(9) 0.3623(3) 0.22980(11) 0.0242(3) Uani 1 1 d . . .
H5 H 0.2846 0.5167 0.2162 0.029 Uiso 1 1 calc R . .
C9 C 0.36247(9) 0.3047(3) 0.18349(11) 0.0263(3) Uani 1 1 d . . .
C10 C 0.38383(10) 0.4568(3) 0.12762(13) 0.0333(4) Uani 1 1 d . . .
H10 H 0.3597 0.5949 0.1186 0.040 Uiso 1 1 calc R . .
C11 C 0.44042(12) 0.4099(4) 0.08441(15) 0.0414(5) Uani 1 1 d . . .
H11 H 0.4547 0.5156 0.0454 0.050 Uiso 1 1 calc R . .
C12 C 0.47625(11) 0.2104(4) 0.09769(15) 0.0442(5) Uani 1 1 d . . .
H12 H 0.5155 0.1787 0.0685 0.053 Uiso 1 1 calc R . .
C13 C 0.45440(11) 0.0558(3) 0.15423(16) 0.0424(5) Uani 1 1 d . . .
H13 H 0.4786 -0.0823 0.1639 0.051 Uiso 1 1 calc R . .
C14 C 0.39690(10) 0.1047(3) 0.19653(14) 0.0350(4) Uani 1 1 d . . .
H14 H 0.3814 -0.0008 0.2346 0.042 Uiso 1 1 calc R . .
C6 C 0.18615(8) 0.1681(2) 0.24284(9) 0.0174(3) Uani 1 1 d . . .
C7 C 0.04742(10) -0.0746(3) 0.40317(12) 0.0290(3) Uani 1 1 d . . .
H7A H -0.0058 -0.0142 0.3759 0.043 Uiso 1 1 calc R . .
H7B H 0.0698 -0.0359 0.4731 0.043 Uiso 1 1 calc R . .
H7C H 0.0449 -0.2319 0.3966 0.043 Uiso 1 1 calc R . .
C8 C 0.26328(10) 0.5890(3) 0.39649(13) 0.0302(3) Uani 1 1 d . . .
C15 C 0.10187(10) -0.0247(3) 0.09560(11) 0.0313(4) Uani 1 1 d . . .
H15A H 0.0945 0.1006 0.0519 0.047 Uiso 1 1 calc R . .
H15B H 0.0535 -0.1109 0.0765 0.047 Uiso 1 1 calc R . .
H15C H 0.1456 -0.1126 0.0901 0.047 Uiso 1 1 calc R . .
H2 H 0.2116(13) 0.223(4) 0.1197(18) 0.044(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0214(5) 0.0212(6) 0.0153(5) 0.0020(4) 0.0095(4) -0.0005(4)
N2 0.0205(6) 0.0513(9) 0.0107(5) 0.0012(5) 0.0039(4) -0.0116(6)
N3 0.0188(5) 0.0250(6) 0.0115(5) -0.0017(4) 0.0048(4) -0.0036(4)
O1 0.0163(4) 0.0339(6) 0.0179(5) -0.0039(4) 0.0039(4) -0.0004(4)
O2 0.0279(6) 0.0366(6) 0.0261(6) -0.0052(5) 0.0103(5) -0.0137(5)
O3 0.0349(6) 0.0402(7) 0.0130(5) -0.0036(4) 0.0097(4) -0.0031(5)
F1 0.0676(8) 0.0377(6) 0.0580(8) -0.0158(5) 0.0436(7) -0.0032(6)
F2 0.0505(7) 0.0401(7) 0.0749(9) -0.0280(6) 0.0268(7) -0.0246(5)
F3 0.0561(7) 0.0274(5) 0.0525(7) 0.0062(5) 0.0210(6) 0.0142(5)
C1 0.0208(6) 0.0194(6) 0.0178(6) -0.0001(5) 0.0079(5) -0.0008(5)
C2 0.0222(6) 0.0196(6) 0.0137(6) 0.0002(5) 0.0066(5) 0.0035(5)
C3 0.0188(6) 0.0199(6) 0.0130(6) -0.0004(5) 0.0039(5) -0.0005(5)
C4 0.0196(6) 0.0246(7) 0.0149(6) -0.0032(5) 0.0042(5) -0.0010(5)
C5 0.0216(6) 0.0296(8) 0.0221(7) 0.0038(6) 0.0080(5) 0.0003(6)
C9 0.0194(6) 0.0384(9) 0.0212(7) -0.0037(6) 0.0067(5) -0.0053(6)
C10 0.0314(8) 0.0385(9) 0.0334(9) -0.0014(7) 0.0152(7) -0.0003(7)
C11 0.0423(10) 0.0527(12) 0.0391(10) 0.0020(9) 0.0268(8) -0.0080(9)
C12 0.0259(8) 0.0686(14) 0.0435(10) -0.0189(10) 0.0189(8) -0.0032(9)
C13 0.0320(9) 0.0415(10) 0.0469(11) -0.0098(9) 0.0036(8) 0.0079(8)
C14 0.0314(8) 0.0387(9) 0.0335(9) 0.0015(7) 0.0088(7) -0.0048(7)
C6 0.0164(6) 0.0225(6) 0.0124(6) 0.0022(5) 0.0036(5) -0.0003(5)
C7 0.0342(8) 0.0352(9) 0.0238(7) 0.0031(6) 0.0180(6) -0.0067(7)
C8 0.0331(8) 0.0269(8) 0.0346(9) -0.0091(7) 0.0163(7) -0.0057(6)
C15 0.0295(7) 0.0506(10) 0.0140(6) -0.0097(7) 0.0075(6) -0.0144(7)

#==============================================================================

# MOLECULAR GEOMETRY

_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
N1 C1 1.3729(17) . ?
N1 C2 1.3973(18) . ?
N1 C7 1.4652(17) . ?
N2 C6 1.3459(17) . ?
N2 C5 1.465(2) . ?
N2 H2 0.93(2) . ?
N3 C6 1.3711(17) . ?
N3 C1 1.3934(17) . ?
N3 C15 1.4643(18) . ?
O1 C5 1.4111(18) . ?
O1 C4 1.4263(17) . ?
O2 C1 1.2168(18) . ?
O3 C2 1.2418(16) . ?
F1 C8 1.3377(19) . ?
F2 C8 1.334(2) . ?
F3 C8 1.340(2) . ?
C2 C3 1.4160(18) . ?
C3 C6 1.3733(18) . ?
C3 C4 1.4976(19) . ?
C4 C8 1.527(2) . ?
C4 H4 1.0000 . ?
C5 C9 1.514(2) . ?
C5 H5 1.0000 . ?
C9 C14 1.372(3) . ?
C9 C10 1.372(2) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 124.78(11) . . ?
C1 N1 C7 115.50(12) . . ?
C2 N1 C7 119.61(12) . . ?
C6 N2 C5 120.36(12) . . ?
C6 N2 H2 120.9(14) . . ?
C5 N2 H2 114.0(14) . . ?
C6 N3 C1 121.57(11) . . ?
C6 N3 C15 120.85(11) . . ?
C1 N3 C15 117.24(12) . . ?
C5 O1 C4 114.87(11) . . ?
O2 C1 N1 122.30(12) . . ?
O2 C1 N3 121.41(13) . . ?
N1 C1 N3 116.27(12) . . ?
O3 C2 N1 119.39(12) . . ?
O3 C2 C3 124.65(13) . . ?
N1 C2 C3 115.95(11) . . ?
C6 C3 C2 120.19(12) . . ?
C6 C3 C4 118.29(12) . . ?
C2 C3 C4 121.17(12) . . ?
O1 C4 C3 111.73(11) . . ?
O1 C4 C8 109.52(12) . . ?
C3 C4 C8 112.73(12) . . ?
O1 C4 H4 107.5 . . ?
C3 C4 H4 107.5 . . ?
C8 C4 H4 107.5 . . ?
O1 C5 N2 110.19(12) . . ?
O1 C5 C9 107.59(12) . . ?
N2 C5 C9 108.92(13) . . ?
O1 C5 H5 110.0 . . ?
N2 C5 H5 110.0 . . ?
C9 C5 H5 110.0 . . ?
C14 C9 C10 120.16(15) . . ?
C14 C9 C5 121.12(15) . . ?
C10 C9 C5 118.73(16) . . ?
C9 C10 C11 120.27(18) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.31(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.40(16) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.63(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C9 C14 C13 120.22(17) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N2 C6 N3 117.43(12) . . ?
N2 C6 C3 121.70(12) . . ?
N3 C6 C3 120.81(12) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
F2 C8 F1 107.20(14) . . ?
F2 C8 F3 106.48(15) . . ?
F1 C8 F3 106.51(14) . . ?
F2 C8 C4 111.94(14) . . ?
F1 C8 C4 111.36(14) . . ?
F3 C8 C4 112.99(13) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O2 -175.94(14) . . . . ?
C7 N1 C1 O2 0.4(2) . . . . ?
C2 N1 C1 N3 5.6(2) . . . . ?
C7 N1 C1 N3 -178.03(13) . . . . ?
C6 N3 C1 O2 177.38(14) . . . . ?
C15 N3 C1 O2 -9.2(2) . . . . ?
C6 N3 C1 N1 -4.2(2) . . . . ?
C15 N3 C1 N1 169.19(13) . . . . ?
C1 N1 C2 O3 179.42(13) . . . . ?
C7 N1 C2 O3 3.2(2) . . . . ?
C1 N1 C2 C3 -1.3(2) . . . . ?
C7 N1 C2 C3 -177.53(13) . . . . ?
O3 C2 C3 C6 174.59(14) . . . . ?
N1 C2 C3 C6 -4.62(19) . . . . ?
O3 C2 C3 C4 1.5(2) . . . . ?
N1 C2 C3 C4 -177.72(12) . . . . ?
C5 O1 C4 C3 50.11(16) . . . . ?
C5 O1 C4 C8 -75.52(15) . . . . ?
C6 C3 C4 O1 -22.82(18) . . . . ?
C2 C3 C4 O1 150.41(13) . . . . ?
C6 C3 C4 C8 101.02(15) . . . . ?
C2 C3 C4 C8 -85.75(17) . . . . ?
C4 O1 C5 N2 -54.23(17) . . . . ?
C4 O1 C5 C9 -172.84(12) . . . . ?
C6 N2 C5 O1 32.2(2) . . . . ?
C6 N2 C5 C9 149.98(14) . . . . ?
O1 C5 C9 C14 56.48(19) . . . . ?
N2 C5 C9 C14 -62.95(19) . . . . ?
O1 C5 C9 C10 -123.64(16) . . . . ?
N2 C5 C9 C10 116.94(16) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C5 C9 C10 C11 179.85(16) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C10 C9 C14 C13 0.8(3) . . . . ?
C5 C9 C14 C13 -179.30(16) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C5 N2 C6 N3 175.68(13) . . . . ?
C5 N2 C6 C3 -7.2(2) . . . . ?
C1 N3 C6 N2 175.67(13) . . . . ?
C15 N3 C6 N2 2.5(2) . . . . ?
C1 N3 C6 C3 -1.5(2) . . . . ?
C15 N3 C6 C3 -174.62(14) . . . . ?
C2 C3 C6 N2 -170.99(14) . . . . ?
C4 C3 C6 N2 2.3(2) . . . . ?
C2 C3 C6 N3 6.1(2) . . . . ?
C4 C3 C6 N3 179.35(13) . . . . ?
O1 C4 C8 F2 -47.41(18) . . . . ?
C3 C4 C8 F2 -172.47(13) . . . . ?
O1 C4 C8 F1 -167.40(13) . . . . ?
C3 C4 C8 F1 67.55(17) . . . . ?
O1 C4 C8 F3 72.78(16) . . . . ?
C3 C4 C8 F3 -52.27(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 895395'
#######################################################################
#
#                 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_is_sd184
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 F3 N3 O3'
_chemical_formula_sum            'C16 H14 F3 N3 O3'
_chemical_formula_weight         353.30

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

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   7.6951(3)
_cell_length_b                   10.1134(5)
_cell_length_c                   10.9054(5)
_cell_angle_alpha                65.724(2)
_cell_angle_beta                 82.426(2)
_cell_angle_gamma                71.772(2)
_cell_volume                     734.82(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5156
_cell_measurement_theta_min      4.611
_cell_measurement_theta_max      61.974

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9371
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15164
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         28.99
_reflns_number_total             3881
_reflns_number_gt                3116
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0647P)^2^+0.1009P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3881
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
F1 F 0.35288(10) 0.92038(8) 0.38821(7) 0.03155(18) Uani 1 1 d . . .
F2 F 0.06395(10) 0.98677(8) 0.35918(8) 0.0358(2) Uani 1 1 d . . .
F3 F 0.25416(12) 0.91907(9) 0.21755(7) 0.0380(2) Uani 1 1 d . . .
N1 N 0.28296(13) 0.41049(11) 0.56136(10) 0.0226(2) Uani 1 1 d . . .
N2 N 0.18432(14) 0.39787(11) 0.37773(11) 0.0262(2) Uani 1 1 d . . .
N3 N 0.08371(14) 0.61422(13) 0.17956(10) 0.0288(2) Uani 1 1 d . . .
O1 O 0.39913(12) 0.70473(9) 0.85443(8) 0.02546(19) Uani 1 1 d . . .
O2 O -0.02170(14) 0.84245(11) 0.19479(9) 0.0367(2) Uani 1 1 d . . .
O3 O 0.13472(15) 0.37748(13) 0.18708(11) 0.0447(3) Uani 1 1 d . . .
C1 C 0.31078(14) 0.49241(12) 0.62466(11) 0.0203(2) Uani 1 1 d . . .
C2 C 0.28066(14) 0.65193(12) 0.56366(10) 0.0188(2) Uani 1 1 d . . .
C3 C 0.22044(14) 0.72481(12) 0.42794(11) 0.0195(2) Uani 1 1 d . . .
C4 C 0.17321(15) 0.64302(13) 0.36908(11) 0.0214(2) Uani 1 1 d . . .
C5 C 0.07023(16) 0.71224(14) 0.24159(12) 0.0258(2) Uani 1 1 d . . .
C6 C 0.13668(17) 0.45727(15) 0.24379(13) 0.0301(3) Uani 1 1 d . . .
C7 C 0.21431(14) 0.48419(13) 0.43936(11) 0.0215(2) Uani 1 1 d . . .
C8 C 0.0100(2) 0.67958(18) 0.04313(13) 0.0378(3) Uani 1 1 d . . .
H8A H -0.1122 0.6671 0.0474 0.057 Uiso 1 1 calc R . .
H8B H 0.0909 0.6277 -0.0107 0.057 Uiso 1 1 calc R . .
H8C H 0.0021 0.7876 0.0016 0.057 Uiso 1 1 calc R . .
C9 C 0.22922(17) 0.23338(14) 0.44943(14) 0.0320(3) Uani 1 1 d . . .
H9A H 0.3611 0.1885 0.4431 0.048 Uiso 1 1 calc R . .
H9B H 0.1628 0.1930 0.4091 0.048 Uiso 1 1 calc R . .
H9C H 0.1938 0.2085 0.5442 0.048 Uiso 1 1 calc R . .
C10 C 0.22029(16) 0.88790(13) 0.34717(11) 0.0236(2) Uani 1 1 d . . .
C11 C 0.30757(14) 0.72717(12) 0.64169(11) 0.0201(2) Uani 1 1 d . . .
H11 H 0.2831 0.8342 0.6040 0.024 Uiso 1 1 calc R . .
C12 C 0.36886(15) 0.64502(12) 0.77128(11) 0.0209(2) Uani 1 1 d . . .
C13 C 0.40656(16) 0.48576(13) 0.82926(11) 0.0256(2) Uani 1 1 d . . .
H13 H 0.4525 0.4302 0.9184 0.031 Uiso 1 1 calc R . .
C14 C 0.37740(16) 0.41212(13) 0.75808(11) 0.0246(2) Uani 1 1 d . . .
H14 H 0.4020 0.3051 0.7982 0.030 Uiso 1 1 calc R . .
C15 C 0.36316(18) 0.86623(13) 0.80444(12) 0.0266(2) Uani 1 1 d . . .
H15A H 0.2320 0.9170 0.7818 0.032 Uiso 1 1 calc R . .
H15B H 0.4366 0.9023 0.7224 0.032 Uiso 1 1 calc R . .
C16 C 0.4143(2) 0.90102(15) 0.91339(14) 0.0360(3) Uani 1 1 d . . .
H16A H 0.3394 0.8662 0.9935 0.054 Uiso 1 1 calc R . .
H16B H 0.3931 1.0105 0.8823 0.054 Uiso 1 1 calc R . .
H16C H 0.5439 0.8491 0.9357 0.054 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0403(4) 0.0295(4) 0.0288(4) -0.0071(3) -0.0053(3) -0.0191(3)
F2 0.0370(4) 0.0237(4) 0.0433(4) -0.0148(3) -0.0051(3) -0.0002(3)
F3 0.0631(5) 0.0371(4) 0.0188(3) -0.0097(3) 0.0021(3) -0.0235(4)
N1 0.0223(5) 0.0227(5) 0.0282(5) -0.0151(4) 0.0008(4) -0.0068(4)
N2 0.0253(5) 0.0283(5) 0.0352(5) -0.0222(4) -0.0003(4) -0.0079(4)
N3 0.0285(5) 0.0416(6) 0.0268(5) -0.0220(5) -0.0001(4) -0.0125(4)
O1 0.0347(4) 0.0239(4) 0.0221(4) -0.0113(3) -0.0058(3) -0.0087(3)
O2 0.0430(5) 0.0353(5) 0.0306(5) -0.0155(4) -0.0132(4) -0.0008(4)
O3 0.0531(6) 0.0527(6) 0.0498(6) -0.0397(5) -0.0026(5) -0.0160(5)
C1 0.0195(5) 0.0207(5) 0.0237(5) -0.0120(4) 0.0021(4) -0.0062(4)
C2 0.0173(5) 0.0214(5) 0.0207(5) -0.0113(4) 0.0003(4) -0.0053(4)
C3 0.0189(5) 0.0204(5) 0.0218(5) -0.0117(4) 0.0002(4) -0.0044(4)
C4 0.0197(5) 0.0260(5) 0.0231(5) -0.0148(4) 0.0008(4) -0.0057(4)
C5 0.0253(5) 0.0343(6) 0.0245(5) -0.0178(5) -0.0003(4) -0.0090(5)
C6 0.0248(6) 0.0429(7) 0.0371(7) -0.0292(6) 0.0030(5) -0.0119(5)
C7 0.0182(5) 0.0253(5) 0.0289(6) -0.0184(5) 0.0033(4) -0.0072(4)
C8 0.0419(7) 0.0587(9) 0.0266(6) -0.0242(6) -0.0009(5) -0.0222(7)
C9 0.0289(6) 0.0292(6) 0.0485(8) -0.0257(6) -0.0010(5) -0.0077(5)
C10 0.0293(6) 0.0238(5) 0.0205(5) -0.0105(4) -0.0029(4) -0.0074(4)
C11 0.0215(5) 0.0198(5) 0.0216(5) -0.0103(4) -0.0006(4) -0.0060(4)
C12 0.0215(5) 0.0234(5) 0.0226(5) -0.0131(4) -0.0001(4) -0.0071(4)
C13 0.0303(6) 0.0232(5) 0.0218(5) -0.0078(4) -0.0042(4) -0.0056(4)
C14 0.0295(6) 0.0188(5) 0.0248(5) -0.0081(4) -0.0018(4) -0.0059(4)
C15 0.0359(6) 0.0223(5) 0.0254(5) -0.0116(4) -0.0038(4) -0.0089(5)
C16 0.0513(8) 0.0318(6) 0.0337(7) -0.0178(5) -0.0094(6) -0.0132(6)

#==============================================================================

# MOLECULAR GEOMETRY

_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
F1 C10 1.3417(13) . ?
F2 C10 1.3333(14) . ?
F3 C10 1.3241(13) . ?
N1 C7 1.3147(15) . ?
N1 C1 1.3524(14) . ?
N2 C6 1.3823(16) . ?
N2 C7 1.3843(14) . ?
N2 C9 1.4629(16) . ?
N3 C5 1.3855(15) . ?
N3 C6 1.3902(17) . ?
N3 C8 1.4668(15) . ?
O1 C12 1.3546(13) . ?
O1 C15 1.4375(14) . ?
O2 C5 1.2061(15) . ?
O3 C6 1.2059(15) . ?
C1 C14 1.4156(15) . ?
C1 C2 1.4224(15) . ?
C2 C3 1.4208(14) . ?
C2 C11 1.4225(14) . ?
C3 C4 1.3837(14) . ?
C3 C10 1.5169(15) . ?
C4 C7 1.4148(16) . ?
C4 C5 1.4812(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.3693(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.4131(15) . ?
C13 C14 1.3540(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.4982(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 117.77(10) . . ?
C6 N2 C7 122.70(10) . . ?
C6 N2 C9 117.21(10) . . ?
C7 N2 C9 119.50(10) . . ?
C5 N3 C6 124.59(10) . . ?
C5 N3 C8 117.63(11) . . ?
C6 N3 C8 117.06(10) . . ?
C12 O1 C15 118.12(8) . . ?
N1 C1 C14 117.12(10) . . ?
N1 C1 C2 123.69(10) . . ?
C14 C1 C2 119.17(10) . . ?
C3 C2 C1 116.33(9) . . ?
C3 C2 C11 124.84(9) . . ?
C1 C2 C11 118.81(9) . . ?
C4 C3 C2 119.36(10) . . ?
C4 C3 C10 120.94(9) . . ?
C2 C3 C10 119.58(9) . . ?
C3 C4 C7 118.11(10) . . ?
C3 C4 C5 124.08(10) . . ?
C7 C4 C5 117.65(10) . . ?
O2 C5 N3 121.51(11) . . ?
O2 C5 C4 123.81(10) . . ?
N3 C5 C4 114.66(10) . . ?
O3 C6 N2 121.80(13) . . ?
O3 C6 N3 121.77(12) . . ?
N2 C6 N3 116.37(10) . . ?
N1 C7 N2 116.60(10) . . ?
N1 C7 C4 124.00(10) . . ?
N2 C7 C4 119.40(10) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F3 C10 F2 108.36(9) . . ?
F3 C10 F1 104.45(9) . . ?
F2 C10 F1 106.11(9) . . ?
F3 C10 C3 113.36(9) . . ?
F2 C10 C3 112.70(9) . . ?
F1 C10 C3 111.28(9) . . ?
C12 C11 C2 119.85(10) . . ?
C12 C11 H11 120.1 . . ?
C2 C11 H11 120.1 . . ?
O1 C12 C11 124.82(10) . . ?
O1 C12 C13 114.17(9) . . ?
C11 C12 C13 121.01(10) . . ?
C14 C13 C12 120.16(10) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C1 120.89(10) . . ?
C13 C14 H14 119.6 . . ?
C1 C14 H14 119.6 . . ?
O1 C15 C16 107.18(9) . . ?
O1 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O1 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
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 . . ?

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
C7 N1 C1 C14 177.37(10) . . . . ?
C7 N1 C1 C2 -4.04(16) . . . . ?
N1 C1 C2 C3 -0.90(15) . . . . ?
C14 C1 C2 C3 177.67(10) . . . . ?
N1 C1 C2 C11 177.53(10) . . . . ?
C14 C1 C2 C11 -3.90(15) . . . . ?
C1 C2 C3 C4 7.93(15) . . . . ?
C11 C2 C3 C4 -170.39(10) . . . . ?
C1 C2 C3 C10 -168.22(10) . . . . ?
C11 C2 C3 C10 13.45(16) . . . . ?
C2 C3 C4 C7 -9.89(15) . . . . ?
C10 C3 C4 C7 166.22(10) . . . . ?
C2 C3 C4 C5 165.50(10) . . . . ?
C10 C3 C4 C5 -18.40(16) . . . . ?
C6 N3 C5 O2 -159.16(12) . . . . ?
C8 N3 C5 O2 10.76(17) . . . . ?
C6 N3 C5 C4 19.53(16) . . . . ?
C8 N3 C5 C4 -170.54(10) . . . . ?
C3 C4 C5 O2 -19.71(19) . . . . ?
C7 C4 C5 O2 155.69(12) . . . . ?
C3 C4 C5 N3 161.63(10) . . . . ?
C7 C4 C5 N3 -22.97(15) . . . . ?
C7 N2 C6 O3 169.98(11) . . . . ?
C9 N2 C6 O3 -1.16(18) . . . . ?
C7 N2 C6 N3 -12.64(17) . . . . ?
C9 N2 C6 N3 176.21(10) . . . . ?
C5 N3 C6 O3 175.12(12) . . . . ?
C8 N3 C6 O3 5.15(18) . . . . ?
C5 N3 C6 N2 -2.25(17) . . . . ?
C8 N3 C6 N2 -172.23(10) . . . . ?
C1 N1 C7 N2 -178.94(9) . . . . ?
C1 N1 C7 C4 2.01(16) . . . . ?
C6 N2 C7 N1 -170.94(10) . . . . ?
C9 N2 C7 N1 0.02(16) . . . . ?
C6 N2 C7 C4 8.15(17) . . . . ?
C9 N2 C7 C4 179.11(10) . . . . ?
C3 C4 C7 N1 4.98(16) . . . . ?
C5 C4 C7 N1 -170.70(10) . . . . ?
C3 C4 C7 N2 -174.04(10) . . . . ?
C5 C4 C7 N2 10.28(15) . . . . ?
C4 C3 C10 F3 -28.71(15) . . . . ?
C2 C3 C10 F3 147.39(10) . . . . ?
C4 C3 C10 F2 94.84(12) . . . . ?
C2 C3 C10 F2 -89.07(12) . . . . ?
C4 C3 C10 F1 -146.09(10) . . . . ?
C2 C3 C10 F1 30.00(14) . . . . ?
C3 C2 C11 C12 -179.00(10) . . . . ?
C1 C2 C11 C12 2.72(15) . . . . ?
C15 O1 C12 C11 0.60(16) . . . . ?
C15 O1 C12 C13 -179.53(10) . . . . ?
C2 C11 C12 O1 -179.99(10) . . . . ?
C2 C11 C12 C13 0.16(16) . . . . ?
O1 C12 C13 C14 178.25(10) . . . . ?
C11 C12 C13 C14 -1.88(17) . . . . ?
C12 C13 C14 C1 0.63(18) . . . . ?
N1 C1 C14 C13 -179.08(10) . . . . ?
C2 C1 C14 C13 2.27(17) . . . . ?
C12 O1 C15 C16 -177.87(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 895396'
#######################################################################
#
#                 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_is_sd194
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Cl F2 N3 O3'
_chemical_formula_sum            'C15 H12 Cl F2 N3 O3'
_chemical_formula_weight         355.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   8.6849(7)
_cell_length_b                   9.3993(4)
_cell_length_c                   10.0441(4)
_cell_angle_alpha                115.546(2)
_cell_angle_beta                 101.079(2)
_cell_angle_gamma                98.711(3)
_cell_volume                     700.09(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5561
_cell_measurement_theta_min      4.966
_cell_measurement_theta_max      62.026

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8803
_exptl_absorpt_correction_T_max  0.9360
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15923
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         30.99
_reflns_number_total             4451
_reflns_number_gt                3595
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0610P)^2^+0.0485P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4451
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
Cl1 Cl 0.63311(4) 0.66887(4) 0.46454(3) 0.02869(10) Uani 1 1 d . . .
N1 N 0.66734(11) 0.35324(12) -0.11959(11) 0.01745(19) Uani 1 1 d . . .
N2 N 0.85860(11) 0.57168(12) -0.08627(11) 0.01732(19) Uani 1 1 d . . .
N3 N 0.98722(12) 0.80121(12) 0.15645(11) 0.0193(2) Uani 1 1 d . . .
O1 O 0.46215(11) 0.06913(10) -0.31785(10) 0.02491(19) Uani 1 1 d . . .
O2 O 0.88990(11) 0.83780(11) 0.35899(10) 0.0265(2) Uani 1 1 d . . .
O3 O 1.05216(11) 0.78379(11) -0.05675(10) 0.0257(2) Uani 1 1 d . . .
F1 F 0.73103(10) 0.41380(10) 0.39265(9) 0.03133(19) Uani 1 1 d . . .
F2 F 0.91003(9) 0.62310(10) 0.44207(8) 0.02740(17) Uani 1 1 d . . .
C1 C 0.97145(13) 0.72144(14) -0.00027(13) 0.0184(2) Uani 1 1 d . . .
C2 C 0.76753(13) 0.49682(14) -0.02333(12) 0.0157(2) Uani 1 1 d . . .
C3 C 0.57144(13) 0.27974(14) -0.06315(13) 0.0171(2) Uani 1 1 d . . .
C4 C 0.45485(14) 0.12768(14) -0.17105(13) 0.0194(2) Uani 1 1 d . . .
C5 C 0.34712(14) 0.05340(15) -0.12218(14) 0.0221(2) Uani 1 1 d . . .
H5 H 0.2688 -0.0469 -0.1940 0.027 Uiso 1 1 calc R . .
C6 C 0.35280(14) 0.12598(15) 0.03441(14) 0.0225(2) Uani 1 1 d . . .
H6 H 0.2742 0.0759 0.0660 0.027 Uiso 1 1 calc R . .
C7 C 0.46718(14) 0.26547(15) 0.14195(14) 0.0216(2) Uani 1 1 d . . .
H7 H 0.4702 0.3094 0.2474 0.026 Uiso 1 1 calc R . .
C8 C 0.58266(13) 0.34597(14) 0.09656(13) 0.0174(2) Uani 1 1 d . . .
C9 C 0.70740(13) 0.49187(14) 0.19828(13) 0.0170(2) Uani 1 1 d . . .
C10 C 0.79135(13) 0.57629(14) 0.13831(12) 0.0163(2) Uani 1 1 d . . .
C11 C 0.89191(13) 0.74736(14) 0.23041(13) 0.0187(2) Uani 1 1 d . . .
C12 C 0.82616(14) 0.49406(15) -0.25370(13) 0.0224(2) Uani 1 1 d . . .
H12A H 0.8976 0.5618 -0.2809 0.034 Uiso 1 1 calc R . .
H12B H 0.7123 0.4826 -0.3016 0.034 Uiso 1 1 calc R . .
H12C H 0.8468 0.3858 -0.2908 0.034 Uiso 1 1 calc R . .
C13 C 0.34714(17) -0.08161(15) -0.43023(15) 0.0274(3) Uani 1 1 d . . .
H13A H 0.3627 -0.1679 -0.4031 0.041 Uiso 1 1 calc R . .
H13B H 0.3631 -0.1107 -0.5318 0.041 Uiso 1 1 calc R . .
H13C H 0.2366 -0.0697 -0.4329 0.041 Uiso 1 1 calc R . .
C14 C 0.75236(14) 0.54613(15) 0.37023(13) 0.0213(2) Uani 1 1 d . . .
C15 C 1.09620(16) 0.96708(16) 0.24408(15) 0.0268(3) Uani 1 1 d . . .
H15A H 1.2079 0.9624 0.2427 0.040 Uiso 1 1 calc R . .
H15B H 1.0914 1.0157 0.3508 0.040 Uiso 1 1 calc R . .
H15C H 1.0622 1.0340 0.1973 0.040 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.02873(16) 0.03072(18) 0.02200(15) 0.00716(13) 0.01313(12) 0.00460(12)
N1 0.0184(4) 0.0178(5) 0.0167(4) 0.0087(4) 0.0063(3) 0.0032(4)
N2 0.0186(4) 0.0191(5) 0.0142(4) 0.0085(4) 0.0055(3) 0.0015(4)
N3 0.0207(4) 0.0176(5) 0.0167(4) 0.0076(4) 0.0051(4) -0.0005(4)
O1 0.0300(4) 0.0188(4) 0.0174(4) 0.0043(3) 0.0067(3) -0.0035(3)
O2 0.0327(5) 0.0213(4) 0.0180(4) 0.0045(3) 0.0093(4) -0.0006(4)
O3 0.0271(4) 0.0264(5) 0.0231(4) 0.0130(4) 0.0098(4) -0.0019(4)
F1 0.0448(5) 0.0282(4) 0.0238(4) 0.0181(3) 0.0060(3) 0.0041(3)
F2 0.0215(3) 0.0381(4) 0.0207(4) 0.0151(3) 0.0032(3) 0.0032(3)
C1 0.0177(5) 0.0192(5) 0.0185(5) 0.0098(4) 0.0051(4) 0.0031(4)
C2 0.0156(4) 0.0174(5) 0.0158(5) 0.0090(4) 0.0056(4) 0.0046(4)
C3 0.0175(5) 0.0177(5) 0.0185(5) 0.0101(4) 0.0066(4) 0.0047(4)
C4 0.0214(5) 0.0171(5) 0.0189(5) 0.0081(4) 0.0062(4) 0.0042(4)
C5 0.0207(5) 0.0193(6) 0.0253(6) 0.0113(5) 0.0058(4) 0.0013(4)
C6 0.0215(5) 0.0231(6) 0.0279(6) 0.0155(5) 0.0112(5) 0.0037(4)
C7 0.0233(5) 0.0236(6) 0.0225(5) 0.0135(5) 0.0104(5) 0.0062(4)
C8 0.0192(5) 0.0179(5) 0.0183(5) 0.0102(4) 0.0076(4) 0.0061(4)
C9 0.0194(5) 0.0180(5) 0.0156(5) 0.0089(4) 0.0065(4) 0.0056(4)
C10 0.0170(5) 0.0177(5) 0.0149(5) 0.0084(4) 0.0052(4) 0.0041(4)
C11 0.0181(5) 0.0202(5) 0.0171(5) 0.0094(4) 0.0044(4) 0.0025(4)
C12 0.0240(5) 0.0265(6) 0.0144(5) 0.0088(5) 0.0064(4) 0.0019(5)
C13 0.0340(6) 0.0164(6) 0.0219(6) 0.0041(5) 0.0060(5) -0.0017(5)
C14 0.0240(5) 0.0227(6) 0.0178(5) 0.0110(5) 0.0068(4) 0.0028(4)
C15 0.0276(6) 0.0213(6) 0.0232(6) 0.0082(5) 0.0055(5) -0.0065(5)

#==============================================================================

# MOLECULAR GEOMETRY

_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
Cl1 C14 1.7599(13) . ?
N1 C2 1.3072(14) . ?
N1 C3 1.3555(13) . ?
N2 C1 1.3771(14) . ?
N2 C2 1.3884(13) . ?
N2 C12 1.4619(14) . ?
N3 C1 1.3880(14) . ?
N3 C11 1.3881(13) . ?
N3 C15 1.4665(15) . ?
O1 C4 1.3519(14) . ?
O1 C13 1.4276(14) . ?
O2 C11 1.2072(14) . ?
O3 C1 1.2132(13) . ?
F1 C14 1.3491(14) . ?
F2 C14 1.3375(13) . ?
C2 C10 1.4194(15) . ?
C3 C8 1.4250(15) . ?
C3 C4 1.4306(16) . ?
C4 C5 1.3703(15) . ?
C5 C6 1.4057(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3580(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4246(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.4193(15) . ?
C9 C10 1.3891(14) . ?
C9 C14 1.5220(15) . ?
C10 C11 1.4783(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 117.92(9) . . ?
C1 N2 C2 123.53(9) . . ?
C1 N2 C12 117.55(9) . . ?
C2 N2 C12 118.78(9) . . ?
C1 N3 C11 125.36(9) . . ?
C1 N3 C15 115.99(9) . . ?
C11 N3 C15 117.92(10) . . ?
C4 O1 C13 116.89(9) . . ?
O3 C1 N2 122.68(10) . . ?
O3 C1 N3 120.74(10) . . ?
N2 C1 N3 116.57(9) . . ?
N1 C2 N2 116.35(9) . . ?
N1 C2 C10 124.50(9) . . ?
N2 C2 C10 119.13(10) . . ?
N1 C3 C8 123.24(10) . . ?
N1 C3 C4 117.44(10) . . ?
C8 C3 C4 119.32(9) . . ?
O1 C4 C5 125.23(11) . . ?
O1 C4 C3 114.76(9) . . ?
C5 C4 C3 120.01(10) . . ?
C4 C5 C6 119.85(11) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 122.03(10) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 119.99(11) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 125.02(10) . . ?
C9 C8 C3 116.41(9) . . ?
C7 C8 C3 118.54(10) . . ?
C10 C9 C8 119.47(10) . . ?
C10 C9 C14 121.65(10) . . ?
C8 C9 C14 118.77(9) . . ?
C9 C10 C2 117.38(10) . . ?
C9 C10 C11 123.91(10) . . ?
C2 C10 C11 118.51(9) . . ?
O2 C11 N3 121.14(10) . . ?
O2 C11 C10 123.69(10) . . ?
N3 C11 C10 115.14(10) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F2 C14 F1 103.77(9) . . ?
F2 C14 C9 113.00(9) . . ?
F1 C14 C9 109.69(10) . . ?
F2 C14 Cl1 109.51(8) . . ?
F1 C14 Cl1 107.60(8) . . ?
C9 C14 Cl1 112.77(8) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 O3 178.62(11) . . . . ?
C12 N2 C1 O3 -5.74(17) . . . . ?
C2 N2 C1 N3 -2.59(16) . . . . ?
C12 N2 C1 N3 173.05(10) . . . . ?
C11 N3 C1 O3 174.41(11) . . . . ?
C15 N3 C1 O3 4.46(17) . . . . ?
C11 N3 C1 N2 -4.41(17) . . . . ?
C15 N3 C1 N2 -174.36(10) . . . . ?
C3 N1 C2 N2 -177.22(9) . . . . ?
C3 N1 C2 C10 4.69(17) . . . . ?
C1 N2 C2 N1 -178.81(10) . . . . ?
C12 N2 C2 N1 5.60(15) . . . . ?
C1 N2 C2 C10 -0.61(16) . . . . ?
C12 N2 C2 C10 -176.20(10) . . . . ?
C2 N1 C3 C8 -4.46(16) . . . . ?
C2 N1 C3 C4 176.01(10) . . . . ?
C13 O1 C4 C5 0.47(18) . . . . ?
C13 O1 C4 C3 -179.39(10) . . . . ?
N1 C3 C4 O1 4.35(15) . . . . ?
C8 C3 C4 O1 -175.19(10) . . . . ?
N1 C3 C4 C5 -175.52(10) . . . . ?
C8 C3 C4 C5 4.94(17) . . . . ?
O1 C4 C5 C6 179.37(11) . . . . ?
C3 C4 C5 C6 -0.77(18) . . . . ?
C4 C5 C6 C7 -2.91(19) . . . . ?
C5 C6 C7 C8 2.26(19) . . . . ?
C6 C7 C8 C9 -179.96(11) . . . . ?
C6 C7 C8 C3 1.99(17) . . . . ?
N1 C3 C8 C9 -3.24(16) . . . . ?
C4 C3 C8 C9 176.28(10) . . . . ?
N1 C3 C8 C7 174.98(10) . . . . ?
C4 C3 C8 C7 -5.50(16) . . . . ?
C7 C8 C9 C10 -167.18(11) . . . . ?
C3 C8 C9 C10 10.90(16) . . . . ?
C7 C8 C9 C14 16.42(17) . . . . ?
C3 C8 C9 C14 -165.49(10) . . . . ?
C8 C9 C10 C2 -10.86(16) . . . . ?
C14 C9 C10 C2 165.43(10) . . . . ?
C8 C9 C10 C11 163.80(10) . . . . ?
C14 C9 C10 C11 -19.91(17) . . . . ?
N1 C2 C10 C9 2.97(17) . . . . ?
N2 C2 C10 C9 -175.07(10) . . . . ?
N1 C2 C10 C11 -171.99(10) . . . . ?
N2 C2 C10 C11 9.97(15) . . . . ?
C1 N3 C11 O2 -164.58(12) . . . . ?
C15 N3 C11 O2 5.20(17) . . . . ?
C1 N3 C11 C10 13.30(16) . . . . ?
C15 N3 C11 C10 -176.93(10) . . . . ?
C9 C10 C11 O2 -12.42(18) . . . . ?
C2 C10 C11 O2 162.19(11) . . . . ?
C9 C10 C11 N3 169.77(10) . . . . ?
C2 C10 C11 N3 -15.62(15) . . . . ?
C10 C9 C14 F2 -29.06(15) . . . . ?
C8 C9 C14 F2 147.25(10) . . . . ?
C10 C9 C14 F1 -144.31(11) . . . . ?
C8 C9 C14 F1 32.00(14) . . . . ?
C10 C9 C14 Cl1 95.79(11) . . . . ?
C8 C9 C14 Cl1 -87.90(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 895397'
#######################################################################
#
#                 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_is_sd206
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 F7 N3 O3, C H Cl3'
_chemical_formula_sum            'C18 H13 Cl3 F7 N3 O3'
_chemical_formula_weight         558.66

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_Int_Tables_number      11

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

_cell_length_a                   12.2256(8)
_cell_length_b                   6.8967(4)
_cell_length_c                   12.7724(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.776(3)
_cell_angle_gamma                90.00
_cell_volume                     1071.45(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4220
_cell_measurement_theta_min      5.907
_cell_measurement_theta_max      60.628

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10034
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0229
_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       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         28.00
_reflns_number_total             2781
_reflns_number_gt                2118
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0821P)^2^+0.4737P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2781
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
O3 O 0.78279(17) 0.2060(4) 0.20869(17) 0.0319(10) Uani 0.50 1 d P . .
N1 N 1.10447(15) 0.2500 0.30481(15) 0.0266(5) Uani 1 2 d S . .
N2 N 1.07953(16) 0.2500 0.48001(15) 0.0255(4) Uani 1 2 d S . .
N3 N 0.95685(17) 0.2500 0.17222(15) 0.0271(5) Uani 1 2 d S . .
O1 O 1.13403(16) 0.2500 0.13250(15) 0.0454(6) Uani 1 2 d S . .
O2 O 1.05263(15) 0.2500 0.84994(13) 0.0331(4) Uani 1 2 d S . .
F1 F 0.6921(2) 0.4404(4) 0.49188(17) 0.0372(6) Uani 0.50 1 d P . .
F2 F 0.7086(3) 0.4505(5) 0.3276(3) 0.0289(7) Uani 0.50 1 d P . .
F3 F 0.6247(2) 0.1032(5) 0.4977(2) 0.0519(7) Uani 0.50 1 d P . .
F4 F 0.6957(4) 0.0001(6) 0.3604(3) 0.0439(10) Uani 0.50 1 d P . .
F5 F 0.4878(3) 0.3444(7) 0.3708(3) 0.0692(11) Uani 0.50 1 d P . .
F6 F 0.4718(2) 0.0352(7) 0.3446(3) 0.0631(9) Uani 0.50 1 d P . .
F7 F 0.54791(16) 0.2500 0.23472(16) 0.0769(8) Uani 1 2 d S . .
C1 C 1.0696(2) 0.2500 0.19927(19) 0.0307(6) Uani 1 2 d S . .
C2 C 1.03327(18) 0.2500 0.38325(18) 0.0242(5) Uani 1 2 d S . .
C3 C 1.01426(18) 0.2500 0.55987(18) 0.0238(5) Uani 1 2 d S . .
C4 C 1.06889(19) 0.2500 0.66269(18) 0.0245(5) Uani 1 2 d S . .
H4 H 1.1469 0.2500 0.6729 0.029 Uiso 1 2 calc SR . .
C5 C 1.0089(2) 0.2500 0.74782(18) 0.0265(5) Uani 1 2 d S . .
C6 C 0.8927(2) 0.2500 0.73200(19) 0.0313(6) Uani 1 2 d S . .
H6 H 0.8517 0.2500 0.7913 0.038 Uiso 1 2 calc SR . .
C7 C 0.8386(2) 0.2500 0.6341(2) 0.0332(6) Uani 1 2 d S . .
H7 H 0.7605 0.2500 0.6261 0.040 Uiso 1 2 calc SR . .
C8 C 0.89688(19) 0.2500 0.54226(19) 0.0313(6) Uani 1 2 d S . .
C9 C 0.8499(2) 0.2825(8) 0.4360(2) 0.0217(15) Uani 0.50 1 d P . .
C10 C 0.91761(18) 0.2500 0.35447(18) 0.0242(5) Uani 1 2 d S . .
C11 C 0.87735(19) 0.2500 0.24211(18) 0.0250(5) Uani 1 2 d S . .
C12 C 0.9196(2) 0.2500 0.05898(19) 0.0346(6) Uani 1 2 d S . .
H12A H 0.9707 0.3266 0.0213 0.052 Uiso 0.50 1 calc PR . .
H12B H 0.8459 0.3069 0.0477 0.052 Uiso 0.50 1 calc PR . .
H12C H 0.9175 0.1165 0.0326 0.052 Uiso 0.50 1 calc PR . .
C13 C 1.22425(19) 0.2500 0.3327(2) 0.0362(7) Uani 1 2 d S . .
H13A H 1.2410 0.3049 0.4033 0.054 Uiso 0.50 1 calc PR . .
H13B H 1.2596 0.3284 0.2817 0.054 Uiso 0.50 1 calc PR . .
H13C H 1.2519 0.1167 0.3317 0.054 Uiso 0.50 1 calc PR . .
C14 C 1.1698(2) 0.2500 0.8708(2) 0.0350(6) Uani 1 2 d S . .
H14A H 1.1992 0.1276 0.8465 0.052 Uiso 0.50 1 calc PR . .
H14B H 1.1901 0.2639 0.9466 0.052 Uiso 0.50 1 calc PR . .
H14C H 1.2004 0.3584 0.8336 0.052 Uiso 0.50 1 calc PR . .
C15 C 0.7263(3) 0.3308(6) 0.4122(3) 0.0263(7) Uani 0.50 1 d P . .
C16 C 0.6479(3) 0.1543(6) 0.4002(3) 0.0318(8) Uani 0.50 1 d P . .
C17 C 0.5363(3) 0.1887(8) 0.3358(4) 0.0443(12) Uani 0.50 1 d P . .
C18A C 0.5925(19) 0.2500 0.9386(17) 0.094(8) Uani 0.57(3) 2 d SP . 1
H18A H 0.5882 0.2500 1.0164 0.113 Uiso 0.57(3) 2 calc SPR . 1
Cl1A Cl 0.6490(4) 0.0479(9) 0.9134(4) 0.0880(16) Uani 0.50 1 d P . 1
Cl2A Cl 0.4618(6) 0.2500 0.8845(16) 0.125(3) Uani 0.57(3) 2 d SP . 1
C18B C 0.5861(18) 0.2500 0.9383(10) 0.046(5) Uani 0.43(3) 2 d SP . 2
H18B H 0.5721 0.2500 1.0141 0.055 Uiso 0.43(3) 2 calc SPR . 2
Cl1B Cl 0.6724(3) 0.0385(7) 0.9045(2) 0.0447(5) Uani 0.50 1 d P . 2
Cl2B Cl 0.4574(7) 0.2500 0.8491(12) 0.118(3) Uani 0.43(3) 2 d SP . 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0249(9) 0.041(3) 0.0291(10) -0.0053(11) -0.0023(8) -0.0036(10)
N1 0.0190(9) 0.0384(12) 0.0231(9) 0.000 0.0049(7) 0.000
N2 0.0210(9) 0.0332(12) 0.0229(9) 0.000 0.0049(7) 0.000
N3 0.0275(10) 0.0338(12) 0.0198(9) 0.000 0.0017(7) 0.000
O1 0.0308(9) 0.0787(17) 0.0282(9) 0.000 0.0094(7) 0.000
O2 0.0355(9) 0.0437(12) 0.0204(8) 0.000 0.0039(7) 0.000
F1 0.0305(11) 0.0465(15) 0.0347(11) -0.0132(11) 0.0044(9) 0.0115(11)
F2 0.0253(13) 0.0284(18) 0.0325(16) 0.0066(13) 0.0007(11) 0.0046(12)
F3 0.0357(13) 0.075(2) 0.0455(14) 0.0136(14) 0.0080(11) -0.0173(14)
F4 0.0345(16) 0.032(2) 0.066(3) -0.0004(16) 0.0084(17) -0.0034(14)
F5 0.0287(15) 0.084(3) 0.093(3) -0.030(2) -0.0055(15) 0.0231(17)
F6 0.0287(14) 0.084(3) 0.076(2) 0.003(2) -0.0003(12) -0.0218(17)
F7 0.0416(10) 0.140(3) 0.0453(11) 0.000 -0.0114(8) 0.000
C1 0.0290(12) 0.0387(15) 0.0250(11) 0.000 0.0054(9) 0.000
C2 0.0200(10) 0.0277(13) 0.0254(11) 0.000 0.0041(8) 0.000
C3 0.0217(10) 0.0270(12) 0.0233(10) 0.000 0.0048(8) 0.000
C4 0.0230(10) 0.0265(12) 0.0242(11) 0.000 0.0030(8) 0.000
C5 0.0347(12) 0.0229(12) 0.0219(10) 0.000 0.0020(9) 0.000
C6 0.0324(12) 0.0383(15) 0.0249(11) 0.000 0.0110(9) 0.000
C7 0.0236(11) 0.0465(17) 0.0303(12) 0.000 0.0071(9) 0.000
C8 0.0220(11) 0.0466(17) 0.0258(11) 0.000 0.0041(9) 0.000
C9 0.0178(11) 0.021(5) 0.0266(12) -0.0014(13) 0.0019(9) 0.0008(12)
C10 0.0203(10) 0.0288(13) 0.0236(10) 0.000 0.0020(8) 0.000
C11 0.0259(11) 0.0238(12) 0.0251(11) 0.000 0.0020(8) 0.000
C12 0.0362(13) 0.0465(17) 0.0211(11) 0.000 0.0028(9) 0.000
C13 0.0182(10) 0.061(2) 0.0303(12) 0.000 0.0047(9) 0.000
C14 0.0383(14) 0.0402(16) 0.0256(11) 0.000 -0.0006(10) 0.000
C15 0.0249(17) 0.0289(16) 0.0253(14) -0.0015(13) 0.0028(11) 0.0067(14)
C16 0.0200(16) 0.038(2) 0.0378(18) -0.0011(16) 0.0047(13) -0.0040(15)
C17 0.0218(16) 0.056(3) 0.054(2) -0.007(2) -0.0020(15) -0.0031(18)
C18A 0.074(11) 0.091(16) 0.125(14) 0.000 0.052(9) 0.000
Cl1A 0.072(2) 0.0593(15) 0.125(3) -0.0130(18) -0.0256(17) 0.0149(17)
Cl2A 0.039(2) 0.134(4) 0.208(8) 0.000 0.046(3) 0.000
C18B 0.067(12) 0.042(10) 0.029(5) 0.000 0.012(6) 0.000
Cl1B 0.0425(10) 0.0418(11) 0.0491(8) -0.0046(7) 0.0017(6) 0.0049(9)
Cl2B 0.044(3) 0.134(5) 0.166(6) 0.000 -0.037(5) 0.000

#==============================================================================

# MOLECULAR GEOMETRY

_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
O3 O3 0.607(5) 4_565 ?
O3 C11 1.229(3) . ?
N1 C1 1.372(3) . ?
N1 C2 1.392(3) . ?
N1 C13 1.472(3) . ?
N2 C2 1.306(3) . ?
N2 C3 1.357(3) . ?
N3 C11 1.384(3) . ?
N3 C1 1.387(3) . ?
N3 C12 1.472(3) . ?
O1 C1 1.218(3) . ?
O2 C5 1.359(3) . ?
O2 C14 1.431(3) . ?
F1 F3 0.888(3) 4_565 ?
F1 C15 1.366(4) . ?
F1 C16 1.401(4) 4_565 ?
F1 F4 1.733(5) 4_565 ?
F2 F4 0.575(3) 4_565 ?
F2 C15 1.360(5) . ?
F2 C16 1.440(5) 4_565 ?
F3 F1 0.888(3) 4_565 ?
F3 C16 1.351(4) . ?
F3 C15 1.793(4) 4_565 ?
F4 F2 0.575(3) 4_565 ?
F4 C16 1.338(6) . ?
F4 C15 1.374(6) 4_565 ?
F4 F1 1.733(5) 4_565 ?
F5 C17 0.811(5) 4_565 ?
F5 F6 0.909(5) 4_565 ?
F5 F5 1.302(9) 4_565 ?
F5 C17 1.326(6) . ?
F6 F5 0.909(5) 4_565 ?
F6 C17 1.332(6) . ?
F7 C17 1.379(5) 4_565 ?
F7 C17 1.379(5) . ?
C2 C10 1.425(3) . ?
C3 C4 1.412(3) . ?
C3 C8 1.430(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(4) . ?
C6 C7 1.355(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.432(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.437(4) . ?
C8 C9 1.437(4) 4_565 ?
C9 C9 0.449(11) 4_565 ?
C9 C10 1.412(3) . ?
C9 C15 1.548(4) . ?
C9 C15 1.702(5) 4_565 ?
C10 C9 1.412(3) 4_565 ?
C10 C11 1.470(3) . ?
C11 O3 1.229(3) 4_565 ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 0.960(4) 4_565 ?
C15 C15 1.114(8) 4_565 ?
C15 F4 1.374(6) 4_565 ?
C15 C16 1.547(5) . ?
C15 C9 1.702(5) 4_565 ?
C15 F3 1.793(4) 4_565 ?
C16 C15 0.960(5) 4_565 ?
C16 C16 1.320(8) 4_565 ?
C16 F1 1.401(4) 4_565 ?
C16 F2 1.440(5) 4_565 ?
C16 C17 1.540(5) . ?
C16 C17 1.867(6) 4_565 ?
C17 F5 0.811(5) 4_565 ?
C17 C17 0.846(10) 4_565 ?
C17 C16 1.867(6) 4_565 ?
C18A Cl1A 1.602(12) 4_565 ?
C18A Cl1A 1.602(12) . ?
C18A Cl2A 1.68(2) . ?
C18A H18A 1.0000 . ?
C18B Cl2B 1.85(2) . ?
C18B Cl1B 1.876(14) 4_565 ?
C18B Cl1B 1.876(14) . ?
C18B H18B 1.0000 . ?

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
O3 O3 C11 75.72(13) 4_565 . ?
C1 N1 C2 123.5(2) . . ?
C1 N1 C13 116.18(19) . . ?
C2 N1 C13 120.32(19) . . ?
C2 N2 C3 118.7(2) . . ?
C11 N3 C1 125.7(2) . . ?
C11 N3 C12 117.8(2) . . ?
C1 N3 C12 116.48(19) . . ?
C5 O2 C14 117.94(19) . . ?
F3 F1 C15 103.3(3) 4_565 . ?
F3 F1 C16 68.2(3) 4_565 4_565 ?
C15 F1 C16 40.6(2) . 4_565 ?
F3 F1 F4 106.0(3) 4_565 4_565 ?
C15 F1 F4 51.0(2) . 4_565 ?
C16 F1 F4 49.2(2) 4_565 4_565 ?
F4 F2 C15 79.2(7) 4_565 . ?
F4 F2 C16 68.2(7) 4_565 4_565 ?
C15 F2 C16 40.0(2) . 4_565 ?
F1 F3 C16 74.2(3) 4_565 . ?
F1 F3 C15 47.8(2) 4_565 4_565 ?
C16 F3 C15 31.78(19) . 4_565 ?
F2 F4 C16 88.2(8) 4_565 . ?
F2 F4 C15 76.5(7) 4_565 4_565 ?
C16 F4 C15 41.4(2) . 4_565 ?
F2 F4 F1 127.1(8) 4_565 4_565 ?
C16 F4 F1 52.4(2) . 4_565 ?
C15 F4 F1 50.6(2) 4_565 4_565 ?
C17 F5 F6 101.3(8) 4_565 4_565 ?
C17 F5 F5 73.7(5) 4_565 4_565 ?
F6 F5 F5 156.0(4) 4_565 4_565 ?
C17 F5 C17 37.8(5) 4_565 . ?
F6 F5 C17 134.7(6) 4_565 . ?
F5 F5 C17 35.9(3) 4_565 . ?
F5 F6 C17 36.6(4) 4_565 . ?
C17 F7 C17 35.7(4) 4_565 . ?
O1 C1 N1 121.9(2) . . ?
O1 C1 N3 121.5(2) . . ?
N1 C1 N3 116.6(2) . . ?
N2 C2 N1 116.0(2) . . ?
N2 C2 C10 124.6(2) . . ?
N1 C2 C10 119.4(2) . . ?
N2 C3 C4 116.1(2) . . ?
N2 C3 C8 122.6(2) . . ?
C4 C3 C8 121.3(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
O2 C5 C4 124.8(2) . . ?
O2 C5 C6 115.4(2) . . ?
C4 C5 C6 119.8(2) . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 116.4(2) . . ?
C3 C8 C9 116.6(2) . . ?
C7 C8 C9 126.1(2) . . ?
C3 C8 C9 116.6(2) . 4_565 ?
C7 C8 C9 126.1(2) . 4_565 ?
C9 C8 C9 18.0(4) . 4_565 ?
C9 C9 C10 80.9(2) 4_565 . ?
C9 C9 C8 81.0(2) 4_565 . ?
C10 C9 C8 117.6(2) . . ?
C9 C9 C15 102.4(2) 4_565 . ?
C10 C9 C15 121.5(2) . . ?
C8 C9 C15 120.6(2) . . ?
C9 C9 C15 62.7(2) 4_565 4_565 ?
C10 C9 C15 111.8(3) . 4_565 ?
C8 C9 C15 111.1(3) . 4_565 ?
C15 C9 C15 39.7(3) . 4_565 ?
C9 C10 C9 18.3(4) . 4_565 ?
C9 C10 C2 116.7(2) . . ?
C9 C10 C2 116.7(2) 4_565 . ?
C9 C10 C11 123.8(2) . . ?
C9 C10 C11 123.8(2) 4_565 . ?
C2 C10 C11 118.6(2) . . ?
O3 C11 O3 28.6(3) . 4_565 ?
O3 C11 N3 118.2(2) . . ?
O3 C11 N3 118.2(2) 4_565 . ?
O3 C11 C10 123.4(2) . . ?
O3 C11 C10 123.4(2) 4_565 . ?
N3 C11 C10 116.2(2) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C15 96.2(3) 4_565 4_565 ?
C16 C15 F2 74.5(3) 4_565 . ?
C15 C15 F2 127.4(2) 4_565 . ?
C16 C15 F1 71.7(3) 4_565 . ?
C15 C15 F1 123.6(2) 4_565 . ?
F2 C15 F1 102.7(3) . . ?
C16 C15 F4 67.3(4) 4_565 4_565 ?
C15 C15 F4 148.1(2) 4_565 4_565 ?
F2 C15 F4 24.27(16) . 4_565 ?
F1 C15 F4 78.5(3) . 4_565 ?
C16 C15 C16 58.0(4) 4_565 . ?
C15 C15 C16 38.11(19) 4_565 . ?
F2 C15 C16 110.6(3) . . ?
F1 C15 C16 106.1(3) . . ?
F4 C15 C16 119.0(3) 4_565 . ?
C16 C15 C9 173.3(5) 4_565 . ?
C15 C15 C9 77.6(2) 4_565 . ?
F2 C15 C9 111.1(3) . . ?
F1 C15 C9 109.8(3) . . ?
F4 C15 C9 119.3(4) 4_565 . ?
C16 C15 C9 115.7(3) . . ?
C16 C15 C9 158.7(5) 4_565 4_565 ?
C15 C15 C9 62.7(2) 4_565 4_565 ?
F2 C15 C9 119.2(3) . 4_565 ?
F1 C15 C9 117.0(3) . 4_565 ?
F4 C15 C9 132.0(3) 4_565 4_565 ?
C16 C15 C9 100.8(3) . 4_565 ?
C9 C15 C9 14.9(4) . 4_565 ?
C16 C15 F3 47.9(3) 4_565 4_565 ?
C15 C15 F3 104.71(17) 4_565 4_565 ?
F2 C15 F3 105.4(3) . 4_565 ?
F1 C15 F3 28.82(15) . 4_565 ?
F4 C15 F3 84.6(3) 4_565 4_565 ?
C16 C15 F3 78.5(2) . 4_565 ?
C9 C15 F3 131.1(2) . 4_565 ?
C9 C15 F3 131.7(2) 4_565 4_565 ?
C15 C16 C16 83.8(3) 4_565 4_565 ?
C15 C16 F4 71.3(4) 4_565 . ?
C16 C16 F4 142.6(2) 4_565 . ?
C15 C16 F3 100.4(4) 4_565 . ?
C16 C16 F3 105.1(2) 4_565 . ?
F4 C16 F3 106.4(4) . . ?
C15 C16 F1 67.8(3) 4_565 4_565 ?
C16 C16 F1 117.8(2) 4_565 4_565 ?
F4 C16 F1 78.5(3) . 4_565 ?
F3 C16 F1 37.61(17) . 4_565 ?
C15 C16 F2 65.5(3) 4_565 4_565 ?
C16 C16 F2 120.1(2) 4_565 4_565 ?
F4 C16 F2 23.52(17) . 4_565 ?
F3 C16 F2 129.2(4) . 4_565 ?
F1 C16 F2 97.1(3) 4_565 4_565 ?
C15 C16 C17 152.3(5) 4_565 . ?
C16 C16 C17 81.1(2) 4_565 . ?
F4 C16 C17 108.4(4) . . ?
F3 C16 C17 106.0(3) . . ?
F1 C16 C17 140.0(3) 4_565 . ?
F2 C16 C17 102.7(3) 4_565 . ?
C15 C16 C15 45.7(4) 4_565 . ?
C16 C16 C15 38.11(19) 4_565 . ?
F4 C16 C15 111.9(3) . . ?
F3 C16 C15 107.4(3) . . ?
F1 C16 C15 95.8(3) 4_565 . ?
F2 C16 C15 96.0(2) 4_565 . ?
C17 C16 C15 116.0(4) . . ?
C15 C16 C17 132.9(4) 4_565 4_565 ?
C16 C16 C17 54.55(19) 4_565 4_565 ?
F4 C16 C17 128.4(4) . 4_565 ?
F3 C16 C17 110.2(3) . 4_565 ?
F1 C16 C17 147.4(3) 4_565 4_565 ?
F2 C16 C17 114.1(3) 4_565 4_565 ?
C17 C16 C17 26.6(3) . 4_565 ?
C15 C16 C17 90.3(3) . 4_565 ?
F5 C17 C17 106.3(5) 4_565 4_565 ?
F5 C17 F5 70.4(6) 4_565 . ?
C17 C17 F5 35.9(3) 4_565 . ?
F5 C17 F6 42.0(5) 4_565 . ?
C17 C17 F6 142.6(3) 4_565 . ?
F5 C17 F6 109.0(4) . . ?
F5 C17 F7 138.8(5) 4_565 . ?
C17 C17 F7 72.1(2) 4_565 . ?
F5 C17 F7 99.1(4) . . ?
F6 C17 F7 116.2(3) . . ?
F5 C17 C16 108.6(5) 4_565 . ?
C17 C17 C16 98.9(2) 4_565 . ?
F5 C17 C16 110.3(4) . . ?
F6 C17 C16 109.5(4) . . ?
F7 C17 C16 112.3(3) . . ?
F5 C17 C16 117.5(6) 4_565 4_565 ?
C17 C17 C16 54.55(19) 4_565 4_565 ?
F5 C17 C16 73.3(3) . 4_565 ?
F6 C17 C16 146.8(4) . 4_565 ?
F7 C17 C16 95.5(3) . 4_565 ?
C16 C17 C16 44.3(3) . 4_565 ?
Cl1A C18A Cl1A 120.9(14) 4_565 . ?
Cl1A C18A Cl2A 109.2(9) 4_565 . ?
Cl1A C18A Cl2A 109.2(9) . . ?
Cl1A C18A H18A 105.4 4_565 . ?
Cl1A C18A H18A 105.4 . . ?
Cl2A C18A H18A 105.4 . . ?
Cl2B C18B Cl1B 108.8(6) . 4_565 ?
Cl2B C18B Cl1B 108.8(6) . . ?
Cl1B C18B Cl1B 102.1(10) 4_565 . ?
Cl2B C18B H18B 112.2 . . ?
Cl1B C18B H18B 112.2 4_565 . ?
Cl1B C18B H18B 112.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 180.0 . . . . ?
C13 N1 C1 O1 0.0 . . . . ?
C2 N1 C1 N3 0.0 . . . . ?
C13 N1 C1 N3 180.0 . . . . ?
C11 N3 C1 O1 180.0 . . . . ?
C12 N3 C1 O1 0.0 . . . . ?
C11 N3 C1 N1 0.0 . . . . ?
C12 N3 C1 N1 180.0 . . . . ?
C3 N2 C2 N1 180.0 . . . . ?
C3 N2 C2 C10 0.0 . . . . ?
C1 N1 C2 N2 180.0 . . . . ?
C13 N1 C2 N2 0.0 . . . . ?
C1 N1 C2 C10 0.0 . . . . ?
C13 N1 C2 C10 180.0 . . . . ?
C2 N2 C3 C4 180.0 . . . . ?
C2 N2 C3 C8 0.0 . . . . ?
N2 C3 C4 C5 180.0 . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C14 O2 C5 C4 0.0 . . . . ?
C14 O2 C5 C6 180.0 . . . . ?
C3 C4 C5 O2 180.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
O2 C5 C6 C7 180.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
N2 C3 C8 C7 180.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
N2 C3 C8 C9 -10.1(2) . . . . ?
C4 C3 C8 C9 169.9(2) . . . . ?
N2 C3 C8 C9 10.1(2) . . . 4_565 ?
C4 C3 C8 C9 -169.9(2) . . . 4_565 ?
C6 C7 C8 C3 0.0 . . . . ?
C6 C7 C8 C9 -168.9(3) . . . . ?
C6 C7 C8 C9 168.9(3) . . . 4_565 ?
C3 C8 C9 C9 94.54(12) . . . 4_565 ?
C7 C8 C9 C9 -96.61(17) . . . 4_565 ?
C3 C8 C9 C10 19.9(5) . . . . ?
C7 C8 C9 C10 -171.3(2) . . . . ?
C9 C8 C9 C10 -74.7(4) 4_565 . . . ?
C3 C8 C9 C15 -166.3(3) . . . . ?
C7 C8 C9 C15 2.6(5) . . . . ?
C9 C8 C9 C15 99.2(4) 4_565 . . . ?
C3 C8 C9 C15 150.5(2) . . . 4_565 ?
C7 C8 C9 C15 -40.6(4) . . . 4_565 ?
C9 C8 C9 C15 56.0(3) 4_565 . . 4_565 ?
C8 C9 C10 C9 74.8(4) . . . 4_565 ?
C15 C9 C10 C9 -99.0(4) . . . 4_565 ?
C15 C9 C10 C9 -55.6(3) 4_565 . . 4_565 ?
C9 C9 C10 C2 -94.65(12) 4_565 . . . ?
C8 C9 C10 C2 -19.9(5) . . . . ?
C15 C9 C10 C2 166.3(3) . . . . ?
C15 C9 C10 C2 -150.2(2) 4_565 . . . ?
C9 C9 C10 C11 96.19(16) 4_565 . . . ?
C8 C9 C10 C11 171.0(2) . . . . ?
C15 C9 C10 C11 -2.8(5) . . . . ?
C15 C9 C10 C11 40.6(4) 4_565 . . . ?
N2 C2 C10 C9 10.2(2) . . . . ?
N1 C2 C10 C9 -169.8(2) . . . . ?
N2 C2 C10 C9 -10.2(2) . . . 4_565 ?
N1 C2 C10 C9 169.8(2) . . . 4_565 ?
N2 C2 C10 C11 180.0 . . . . ?
N1 C2 C10 C11 0.0 . . . . ?
O3 O3 C11 N3 -97.85(10) 4_565 . . . ?
O3 O3 C11 C10 99.65(12) 4_565 . . . ?
C1 N3 C11 O3 -163.74(15) . . . . ?
C12 N3 C11 O3 16.26(15) . . . . ?
C1 N3 C11 O3 163.74(15) . . . 4_565 ?
C12 N3 C11 O3 -16.26(15) . . . 4_565 ?
C1 N3 C11 C10 0.0 . . . . ?
C12 N3 C11 C10 180.0 . . . . ?
C9 C10 C11 O3 -28.2(3) . . . . ?
C9 C10 C11 O3 -6.2(3) 4_565 . . . ?
C2 C10 C11 O3 162.82(16) . . . . ?
C9 C10 C11 O3 6.2(3) . . . 4_565 ?
C9 C10 C11 O3 28.2(3) 4_565 . . 4_565 ?
C2 C10 C11 O3 -162.82(16) . . . 4_565 ?
C9 C10 C11 N3 169.0(3) . . . . ?
C9 C10 C11 N3 -169.0(3) 4_565 . . . ?
C2 C10 C11 N3 0.0 . . . . ?
F4 F2 C15 C16 68.9(8) 4_565 . . 4_565 ?
F4 F2 C15 C15 154.8(7) 4_565 . . 4_565 ?
C16 F2 C15 C15 85.9(3) 4_565 . . 4_565 ?
F4 F2 C15 F1 2.3(8) 4_565 . . . ?
C16 F2 C15 F1 -66.6(3) 4_565 . . . ?
C16 F2 C15 F4 -68.9(8) 4_565 . . 4_565 ?
F4 F2 C15 C16 115.2(8) 4_565 . . . ?
C16 F2 C15 C16 46.3(4) 4_565 . . . ?
F4 F2 C15 C9 -114.9(8) 4_565 . . . ?
C16 F2 C15 C9 176.1(5) 4_565 . . . ?
F4 F2 C15 C9 -128.8(8) 4_565 . . 4_565 ?
C16 F2 C15 C9 162.3(5) 4_565 . . 4_565 ?
F4 F2 C15 F3 32.0(8) 4_565 . . 4_565 ?
C16 F2 C15 F3 -37.0(3) 4_565 . . 4_565 ?
F3 F1 C15 C16 30.3(4) 4_565 . . 4_565 ?
F4 F1 C15 C16 -69.7(4) 4_565 . . 4_565 ?
F3 F1 C15 C15 -54.9(3) 4_565 . . 4_565 ?
C16 F1 C15 C15 -85.1(3) 4_565 . . 4_565 ?
F4 F1 C15 C15 -154.8(3) 4_565 . . 4_565 ?
F3 F1 C15 F2 98.9(4) 4_565 . . . ?
C16 F1 C15 F2 68.7(4) 4_565 . . . ?
F4 F1 C15 F2 -1.0(4) 4_565 . . . ?
F3 F1 C15 F4 99.9(4) 4_565 . . 4_565 ?
C16 F1 C15 F4 69.7(4) 4_565 . . 4_565 ?
F3 F1 C15 C16 -17.2(4) 4_565 . . . ?
C16 F1 C15 C16 -47.5(4) 4_565 . . . ?
F4 F1 C15 C16 -117.1(3) 4_565 . . . ?
F3 F1 C15 C9 -142.8(4) 4_565 . . . ?
C16 F1 C15 C9 -173.1(5) 4_565 . . . ?
F4 F1 C15 C9 117.3(4) 4_565 . . . ?
F3 F1 C15 C9 -128.6(4) 4_565 . . 4_565 ?
C16 F1 C15 C9 -158.8(5) 4_565 . . 4_565 ?
F4 F1 C15 C9 131.5(4) 4_565 . . 4_565 ?
C16 F1 C15 F3 -30.3(4) 4_565 . . 4_565 ?
F4 F1 C15 F3 -99.9(4) 4_565 . . 4_565 ?
C9 C9 C15 C16 21(3) 4_565 . . 4_565 ?
C10 C9 C15 C16 107(3) . . . 4_565 ?
C8 C9 C15 C16 -66(4) . . . 4_565 ?
C15 C9 C15 C16 21(3) 4_565 . . 4_565 ?
C9 C9 C15 C15 0.000(1) 4_565 . . 4_565 ?
C10 C9 C15 C15 86.8(4) . . . 4_565 ?
C8 C9 C15 C15 -86.8(4) . . . 4_565 ?
C9 C9 C15 F2 -125.5(3) 4_565 . . . ?
C10 C9 C15 F2 -38.7(6) . . . . ?
C8 C9 C15 F2 147.6(4) . . . . ?
C15 C9 C15 F2 -125.5(3) 4_565 . . . ?
C9 C9 C15 F1 121.5(2) 4_565 . . . ?
C10 C9 C15 F1 -151.7(4) . . . . ?
C8 C9 C15 F1 34.7(5) . . . . ?
C15 C9 C15 F1 121.5(2) 4_565 . . . ?
C9 C9 C15 F4 -150.9(3) 4_565 . . 4_565 ?
C10 C9 C15 F4 -64.1(5) . . . 4_565 ?
C8 C9 C15 F4 122.3(4) . . . 4_565 ?
C15 C9 C15 F4 -150.9(3) 4_565 . . 4_565 ?
C9 C9 C15 C16 1.6(3) 4_565 . . . ?
C10 C9 C15 C16 88.4(5) . . . . ?
C8 C9 C15 C16 -85.2(5) . . . . ?
C15 C9 C15 C16 1.6(3) 4_565 . . . ?
C10 C9 C15 C9 86.8(4) . . . 4_565 ?
C8 C9 C15 C9 -86.8(4) . . . 4_565 ?
C15 C9 C15 C9 0.000(1) 4_565 . . 4_565 ?
C9 C9 C15 F3 98.8(4) 4_565 . . 4_565 ?
C10 C9 C15 F3 -174.4(3) . . . 4_565 ?
C8 C9 C15 F3 12.0(7) . . . 4_565 ?
C15 C9 C15 F3 98.8(4) 4_565 . . 4_565 ?
F2 F4 C16 C15 -71.5(8) 4_565 . . 4_565 ?
F1 F4 C16 C15 70.2(3) 4_565 . . 4_565 ?
F2 F4 C16 C16 -20.6(10) 4_565 . . 4_565 ?
C15 F4 C16 C16 50.9(4) 4_565 . . 4_565 ?
F1 F4 C16 C16 121.1(4) 4_565 . . 4_565 ?
F2 F4 C16 F3 -167.1(8) 4_565 . . . ?
C15 F4 C16 F3 -95.6(4) 4_565 . . . ?
F1 F4 C16 F3 -25.4(2) 4_565 . . . ?
F2 F4 C16 F1 -141.7(8) 4_565 . . 4_565 ?
C15 F4 C16 F1 -70.2(3) 4_565 . . 4_565 ?
C15 F4 C16 F2 71.5(8) 4_565 . . 4_565 ?
F1 F4 C16 F2 141.7(8) 4_565 . . 4_565 ?
F2 F4 C16 C17 79.2(8) 4_565 . . . ?
C15 F4 C16 C17 150.7(5) 4_565 . . . ?
F1 F4 C16 C17 -139.1(4) 4_565 . . . ?
F2 F4 C16 C15 -50.1(9) 4_565 . . . ?
C15 F4 C16 C15 21.5(2) 4_565 . . . ?
F1 F4 C16 C15 91.7(3) 4_565 . . . ?
F2 F4 C16 C17 59.0(9) 4_565 . . 4_565 ?
C15 F4 C16 C17 130.5(5) 4_565 . . 4_565 ?
F1 F4 C16 C17 -159.3(4) 4_565 . . 4_565 ?
F1 F3 C16 C15 -29.8(4) 4_565 . . 4_565 ?
F1 F3 C16 C16 -116.2(3) 4_565 . . 4_565 ?
C15 F3 C16 C16 -86.4(4) 4_565 . . 4_565 ?
F1 F3 C16 F4 43.6(4) 4_565 . . . ?
C15 F3 C16 F4 73.4(4) 4_565 . . . ?
C15 F3 C16 F1 29.8(4) 4_565 . . 4_565 ?
F1 F3 C16 F2 37.0(5) 4_565 . . 4_565 ?
C15 F3 C16 F2 66.8(4) 4_565 . . 4_565 ?
F1 F3 C16 C17 158.9(4) 4_565 . . . ?
C15 F3 C16 C17 -171.3(6) 4_565 . . . ?
F1 F3 C16 C15 -76.5(4) 4_565 . . . ?
C15 F3 C16 C15 -46.7(4) 4_565 . . . ?
F1 F3 C16 C17 -173.4(4) 4_565 . . 4_565 ?
C15 F3 C16 C17 -143.6(5) 4_565 . . 4_565 ?
C16 C15 C16 C15 180.0 4_565 . . 4_565 ?
F2 C15 C16 C15 124.8(3) . . . 4_565 ?
F1 C15 C16 C15 -124.5(2) . . . 4_565 ?
F4 C15 C16 C15 150.0(2) 4_565 . . 4_565 ?
C9 C15 C16 C15 -2.5(4) . . . 4_565 ?
C9 C15 C16 C15 -2.1(4) 4_565 . . 4_565 ?
F3 C15 C16 C15 -132.8(2) 4_565 . . 4_565 ?
C15 C15 C16 C16 180.0 4_565 . . 4_565 ?
F2 C15 C16 C16 -55.2(3) . . . 4_565 ?
F1 C15 C16 C16 55.5(2) . . . 4_565 ?
F4 C15 C16 C16 -30.0(2) 4_565 . . 4_565 ?
C9 C15 C16 C16 177.5(4) . . . 4_565 ?
C9 C15 C16 C16 177.9(4) 4_565 . . 4_565 ?
F3 C15 C16 C16 47.2(2) 4_565 . . 4_565 ?
C16 C15 C16 F4 151.1(2) 4_565 . . . ?
C15 C15 C16 F4 -28.9(2) 4_565 . . . ?
F2 C15 C16 F4 95.9(4) . . . . ?
F1 C15 C16 F4 -153.4(3) . . . . ?
F4 C15 C16 F4 121.1(4) 4_565 . . . ?
C9 C15 C16 F4 -31.5(4) . . . . ?
C9 C15 C16 F4 -31.1(4) 4_565 . . . ?
F3 C15 C16 F4 -161.8(3) 4_565 . . . ?
C16 C15 C16 F3 -92.4(4) 4_565 . . . ?
C15 C15 C16 F3 87.6(4) 4_565 . . . ?
F2 C15 C16 F3 -147.6(3) . . . . ?
F1 C15 C16 F3 -36.9(4) . . . . ?
F4 C15 C16 F3 -122.4(4) 4_565 . . . ?
C9 C15 C16 F3 85.0(3) . . . . ?
C9 C15 C16 F3 85.4(3) 4_565 . . . ?
F3 C15 C16 F3 -45.3(3) 4_565 . . . ?
C16 C15 C16 F1 -129.1(2) 4_565 . . 4_565 ?
C15 C15 C16 F1 50.9(2) 4_565 . . 4_565 ?
F2 C15 C16 F1 175.8(3) . . . 4_565 ?
F1 C15 C16 F1 -73.5(3) . . . 4_565 ?
F4 C15 C16 F1 -159.0(3) 4_565 . . 4_565 ?
C9 C15 C16 F1 48.4(3) . . . 4_565 ?
C9 C15 C16 F1 48.8(3) 4_565 . . 4_565 ?
F3 C15 C16 F1 -81.9(2) 4_565 . . 4_565 ?
C16 C15 C16 F2 133.1(2) 4_565 . . 4_565 ?
C15 C15 C16 F2 -46.9(2) 4_565 . . 4_565 ?
F2 C15 C16 F2 78.0(3) . . . 4_565 ?
F1 C15 C16 F2 -171.3(3) . . . 4_565 ?
F4 C15 C16 F2 103.2(4) 4_565 . . 4_565 ?
C9 C15 C16 F2 -49.4(3) . . . 4_565 ?
C9 C15 C16 F2 -49.0(3) 4_565 . . 4_565 ?
F3 C15 C16 F2 -179.7(3) 4_565 . . 4_565 ?
C16 C15 C16 C17 25.9(5) 4_565 . . . ?
C15 C15 C16 C17 -154.1(5) 4_565 . . . ?
F2 C15 C16 C17 -29.3(4) . . . . ?
F1 C15 C16 C17 81.4(4) . . . . ?
F4 C15 C16 C17 -4.1(5) 4_565 . . . ?
C9 C15 C16 C17 -156.7(3) . . . . ?
C9 C15 C16 C17 -156.2(3) 4_565 . . . ?
F3 C15 C16 C17 73.0(3) 4_565 . . . ?
C16 C15 C16 C17 18.9(4) 4_565 . . 4_565 ?
C15 C15 C16 C17 -161.1(4) 4_565 . . 4_565 ?
F2 C15 C16 C17 -36.3(3) . . . 4_565 ?
F1 C15 C16 C17 74.4(3) . . . 4_565 ?
F4 C15 C16 C17 -11.1(4) 4_565 . . 4_565 ?
C9 C15 C16 C17 -163.7(3) . . . 4_565 ?
C9 C15 C16 C17 -163.2(2) 4_565 . . 4_565 ?
F3 C15 C16 C17 66.0(2) 4_565 . . 4_565 ?
C17 F5 C17 F5 180.000(3) 4_565 . . 4_565 ?
F6 F5 C17 F5 -145.5(5) 4_565 . . 4_565 ?
F6 F5 C17 C17 34.5(5) 4_565 . . 4_565 ?
F5 F5 C17 C17 180.000(3) 4_565 . . 4_565 ?
C17 F5 C17 F6 -163.1(3) 4_565 . . . ?
F6 F5 C17 F6 -128.6(7) 4_565 . . . ?
F5 F5 C17 F6 16.9(3) 4_565 . . . ?
C17 F5 C17 F7 -41.2(5) 4_565 . . . ?
F6 F5 C17 F7 -6.8(7) 4_565 . . . ?
F5 F5 C17 F7 138.8(5) 4_565 . . . ?
C17 F5 C17 C16 76.7(6) 4_565 . . . ?
F6 F5 C17 C16 111.1(7) 4_565 . . . ?
F5 F5 C17 C16 -103.3(6) 4_565 . . . ?
C17 F5 C17 C16 51.8(4) 4_565 . . 4_565 ?
F6 F5 C17 C16 86.2(6) 4_565 . . 4_565 ?
F5 F5 C17 C16 -128.2(4) 4_565 . . 4_565 ?
F5 F6 C17 C17 -40.5(6) 4_565 . . 4_565 ?
F5 F6 C17 F5 -24.1(4) 4_565 . . . ?
F5 F6 C17 F7 -135.0(7) 4_565 . . . ?
F5 F6 C17 C16 96.6(6) 4_565 . . . ?
F5 F6 C17 C16 64.3(8) 4_565 . . 4_565 ?
C17 F7 C17 F5 94.6(10) 4_565 . . 4_565 ?
C17 F7 C17 F5 24.0(3) 4_565 . . . ?
C17 F7 C17 F6 140.5(3) 4_565 . . . ?
C17 F7 C17 C16 -92.5(3) 4_565 . . . ?
C17 F7 C17 C16 -50.0(2) 4_565 . . 4_565 ?
C15 C16 C17 F5 -168.7(10) 4_565 . . 4_565 ?
C16 C16 C17 F5 -110.7(6) 4_565 . . 4_565 ?
F4 C16 C17 F5 106.6(6) . . . 4_565 ?
F3 C16 C17 F5 -7.4(7) . . . 4_565 ?
F1 C16 C17 F5 12.6(9) 4_565 . . 4_565 ?
F2 C16 C17 F5 130.3(6) 4_565 . . 4_565 ?
C15 C16 C17 F5 -126.5(6) . . . 4_565 ?
C17 C16 C17 F5 -110.7(6) 4_565 . . 4_565 ?
C15 C16 C17 C17 -58.1(10) 4_565 . . 4_565 ?
C16 C16 C17 C17 0.0 4_565 . . 4_565 ?
F4 C16 C17 C17 -142.8(2) . . . 4_565 ?
F3 C16 C17 C17 103.3(3) . . . 4_565 ?
F1 C16 C17 C17 123.3(5) 4_565 . . 4_565 ?
F2 C16 C17 C17 -119.1(2) 4_565 . . 4_565 ?
C15 C16 C17 C17 -15.8(3) . . . 4_565 ?
C15 C16 C17 F5 -93.3(10) 4_565 . . . ?
C16 C16 C17 F5 -35.3(4) 4_565 . . . ?
F4 C16 C17 F5 -178.0(4) . . . . ?
F3 C16 C17 F5 68.0(5) . . . . ?
F1 C16 C17 F5 88.0(6) 4_565 . . . ?
F2 C16 C17 F5 -154.3(4) 4_565 . . . ?
C15 C16 C17 F5 -51.1(5) . . . . ?
C17 C16 C17 F5 -35.3(4) 4_565 . . . ?
C15 C16 C17 F6 146.7(9) 4_565 . . . ?
C16 C16 C17 F6 -155.2(4) 4_565 . . . ?
F4 C16 C17 F6 62.0(5) . . . . ?
F3 C16 C17 F6 -51.9(5) . . . . ?
F1 C16 C17 F6 -32.0(7) 4_565 . . . ?
F2 C16 C17 F6 85.7(4) 4_565 . . . ?
C15 C16 C17 F6 -171.1(3) . . . . ?
C17 C16 C17 F6 -155.2(4) 4_565 . . . ?
C15 C16 C17 F7 16.2(11) 4_565 . . . ?
C16 C16 C17 F7 74.2(3) 4_565 . . . ?
F4 C16 C17 F7 -68.5(4) . . . . ?
F3 C16 C17 F7 177.5(3) . . . . ?
F1 C16 C17 F7 -162.5(4) 4_565 . . . ?
F2 C16 C17 F7 -44.8(4) 4_565 . . . ?
C15 C16 C17 F7 58.4(4) . . . . ?
C17 C16 C17 F7 74.2(3) 4_565 . . . ?
C15 C16 C17 C16 -58.1(10) 4_565 . . 4_565 ?
F4 C16 C17 C16 -142.8(2) . . . 4_565 ?
F3 C16 C17 C16 103.3(3) . . . 4_565 ?
F1 C16 C17 C16 123.3(5) 4_565 . . 4_565 ?
F2 C16 C17 C16 -119.1(2) 4_565 . . 4_565 ?
C15 C16 C17 C16 -15.8(3) . . . 4_565 ?
C17 C16 C17 C16 0.000(1) 4_565 . . 4_565 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 895398'
#######################################################################
#
#                 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_is_sd228
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 F3 N3 O2'
_chemical_formula_sum            'C16 H16 F3 N3 O2'
_chemical_formula_weight         339.32

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   8.5186(3)
_cell_length_b                   9.1302(3)
_cell_length_c                   19.1613(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.8670(10)
_cell_angle_gamma                90.00
_cell_volume                     1479.61(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      4.948
_cell_measurement_theta_max      62.050

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_T_max  0.9627
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex-X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16967
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         31.03
_reflns_number_total             4698
_reflns_number_gt                4099
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex v2.0-2'
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (except H1) were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0625P)^2^+0.3210P] where P=(Fo^2^+2Fc^2^)/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         4698
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1077
_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

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
F1 F 0.22225(8) 0.37254(7) 0.35382(3) 0.03136(15) Uani 1 1 d . . .
F2 F 0.41754(8) 0.43747(7) 0.42928(4) 0.03259(15) Uani 1 1 d . . .
F3 F 0.45348(8) 0.28253(8) 0.34822(4) 0.03691(17) Uani 1 1 d . . .
N1 N 0.29187(10) -0.14399(9) 0.32795(4) 0.02419(17) Uani 1 1 d . . .
N2 N 0.03383(9) -0.05763(8) 0.33378(4) 0.02071(15) Uani 1 1 d . . .
N3 N -0.01193(9) 0.13504(9) 0.40876(4) 0.02093(15) Uani 1 1 d . . .
O1 O 0.50496(9) -0.03439(10) 0.39096(5) 0.03533(19) Uani 1 1 d . . .
O2 O 0.08078(10) -0.25294(8) 0.26495(4) 0.02916(17) Uani 1 1 d . . .
C1 C 0.36140(12) -0.03486(11) 0.37375(5) 0.02407(18) Uani 1 1 d . . .
C2 C 0.13261(12) -0.15730(10) 0.30600(5) 0.02197(17) Uani 1 1 d . . .
C3 C 0.09411(11) 0.04986(9) 0.37986(4) 0.01904(16) Uani 1 1 d . . .
C4 C 0.03539(10) 0.22167(9) 0.46843(4) 0.01865(16) Uani 1 1 d . . .
C5 C -0.07974(11) 0.27722(10) 0.50781(5) 0.02061(17) Uani 1 1 d . . .
C6 C -0.02913(12) 0.36016(10) 0.56695(5) 0.02248(18) Uani 1 1 d . . .
H6 H -0.1061 0.3997 0.5937 0.027 Uiso 1 1 calc R . .
C7 C 0.13031(12) 0.38775(10) 0.58864(5) 0.02199(17) Uani 1 1 d . . .
C8 C 0.24130(11) 0.33125(10) 0.54846(5) 0.02119(17) Uani 1 1 d . . .
H8 H 0.3505 0.3486 0.5624 0.025 Uiso 1 1 calc R . .
C9 C 0.19510(10) 0.24934(9) 0.48797(4) 0.01869(16) Uani 1 1 d . . .
C10 C 0.31445(10) 0.19691(10) 0.44117(5) 0.01986(16) Uani 1 1 d . . .
H10 H 0.4136 0.1677 0.4712 0.024 Uiso 1 1 calc R . .
C11 C 0.25320(11) 0.06794(10) 0.39753(5) 0.02080(17) Uani 1 1 d . . .
C12 C 0.39543(14) -0.25243(12) 0.30028(6) 0.0338(2) Uani 1 1 d . . .
H12A H 0.3733 -0.3496 0.3184 0.051 Uiso 1 1 calc R . .
H12B H 0.5061 -0.2267 0.3151 0.051 Uiso 1 1 calc R . .
H12C H 0.3761 -0.2533 0.2488 0.051 Uiso 1 1 calc R . .
C13 C -0.13714(12) -0.07135(11) 0.31390(5) 0.02509(19) Uani 1 1 d . . .
H13A H -0.1583 -0.1528 0.2808 0.038 Uiso 1 1 calc R . .
H13B H -0.1783 0.0197 0.2917 0.038 Uiso 1 1 calc R . .
H13C H -0.1891 -0.0902 0.3560 0.038 Uiso 1 1 calc R . .
C14 C -0.25264(11) 0.24906(12) 0.48601(6) 0.0274(2) Uani 1 1 d . . .
H14A H -0.2836 0.2916 0.4394 0.041 Uiso 1 1 calc R . .
H14B H -0.3149 0.2940 0.5201 0.041 Uiso 1 1 calc R . .
H14C H -0.2720 0.1432 0.4842 0.041 Uiso 1 1 calc R . .
C15 C 0.17906(14) 0.47557(11) 0.65435(5) 0.0295(2) Uani 1 1 d . . .
H15A H 0.1266 0.5712 0.6505 0.044 Uiso 1 1 calc R . .
H15B H 0.2939 0.4895 0.6600 0.044 Uiso 1 1 calc R . .
H15C H 0.1483 0.4230 0.6952 0.044 Uiso 1 1 calc R . .
C16 C 0.35160(11) 0.32182(11) 0.39317(5) 0.02402(18) Uani 1 1 d . . .
H1 H -0.1100(18) 0.1209(16) 0.3960(8) 0.033(3) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0326(3) 0.0338(3) 0.0270(3) 0.0060(2) 0.0007(2) 0.0008(3)
F2 0.0353(3) 0.0280(3) 0.0351(3) -0.0056(2) 0.0065(3) -0.0113(3)
F3 0.0377(4) 0.0409(4) 0.0365(3) -0.0048(3) 0.0221(3) -0.0030(3)
N1 0.0288(4) 0.0209(4) 0.0237(4) -0.0036(3) 0.0067(3) 0.0036(3)
N2 0.0242(4) 0.0181(3) 0.0194(3) -0.0013(3) 0.0009(3) -0.0010(3)
N3 0.0177(3) 0.0231(3) 0.0215(3) -0.0039(3) 0.0006(3) 0.0008(3)
O1 0.0235(3) 0.0385(4) 0.0439(4) -0.0130(3) 0.0035(3) 0.0074(3)
O2 0.0411(4) 0.0222(3) 0.0243(3) -0.0057(3) 0.0047(3) -0.0033(3)
C1 0.0251(4) 0.0235(4) 0.0240(4) -0.0028(3) 0.0044(3) 0.0034(3)
C2 0.0310(5) 0.0177(4) 0.0178(4) 0.0012(3) 0.0053(3) -0.0001(3)
C3 0.0226(4) 0.0172(3) 0.0173(3) 0.0000(3) 0.0022(3) 0.0006(3)
C4 0.0203(4) 0.0182(4) 0.0175(3) -0.0003(3) 0.0022(3) 0.0010(3)
C5 0.0207(4) 0.0202(4) 0.0216(4) 0.0026(3) 0.0056(3) 0.0022(3)
C6 0.0273(4) 0.0198(4) 0.0218(4) 0.0012(3) 0.0090(3) 0.0028(3)
C7 0.0300(4) 0.0186(4) 0.0178(4) -0.0003(3) 0.0049(3) -0.0003(3)
C8 0.0237(4) 0.0208(4) 0.0189(4) -0.0013(3) 0.0017(3) -0.0006(3)
C9 0.0195(4) 0.0187(4) 0.0182(4) -0.0004(3) 0.0032(3) 0.0012(3)
C10 0.0180(4) 0.0216(4) 0.0201(4) -0.0031(3) 0.0023(3) 0.0006(3)
C11 0.0208(4) 0.0203(4) 0.0215(4) -0.0035(3) 0.0034(3) 0.0015(3)
C12 0.0384(6) 0.0289(5) 0.0358(5) -0.0088(4) 0.0116(4) 0.0076(4)
C13 0.0251(4) 0.0226(4) 0.0261(4) 0.0001(3) -0.0026(3) -0.0033(3)
C14 0.0200(4) 0.0323(5) 0.0309(5) 0.0014(4) 0.0066(4) 0.0016(4)
C15 0.0407(6) 0.0259(4) 0.0226(4) -0.0069(3) 0.0070(4) -0.0039(4)
C16 0.0230(4) 0.0262(4) 0.0238(4) -0.0040(3) 0.0065(3) -0.0026(3)

#==============================================================================

# MOLECULAR GEOMETRY

_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
F1 C16 1.3411(12) . ?
F2 C16 1.3478(11) . ?
F3 C16 1.3426(11) . ?
N1 C2 1.3769(13) . ?
N1 C1 1.4105(12) . ?
N1 C12 1.4668(12) . ?
N2 C3 1.3776(11) . ?
N2 C2 1.3880(12) . ?
N2 C13 1.4661(12) . ?
N3 C3 1.3591(11) . ?
N3 C4 1.4089(11) . ?
N3 H1 0.852(15) . ?
O1 C1 1.2279(12) . ?
O2 C2 1.2220(11) . ?
C1 C11 1.4278(12) . ?
C3 C11 1.3670(12) . ?
C4 C9 1.3904(12) . ?
C4 C5 1.4020(12) . ?
C5 C6 1.3881(13) . ?
C5 C14 1.5042(13) . ?
C6 C7 1.3950(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.3881(13) . ?
C7 C15 1.5085(13) . ?
C8 C9 1.3959(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.5116(12) . ?
C10 C11 1.5013(12) . ?
C10 C16 1.5219(13) . ?
C10 H10 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 125.27(8) . . ?
C2 N1 C12 116.31(8) . . ?
C1 N1 C12 118.41(9) . . ?
C3 N2 C2 121.08(8) . . ?
C3 N2 C13 120.66(8) . . ?
C2 N2 C13 118.25(8) . . ?
C3 N3 C4 120.82(7) . . ?
C3 N3 H1 118.2(10) . . ?
C4 N3 H1 119.6(10) . . ?
O1 C1 N1 120.01(9) . . ?
O1 C1 C11 124.90(9) . . ?
N1 C1 C11 115.08(8) . . ?
O2 C2 N1 121.78(9) . . ?
O2 C2 N2 121.76(9) . . ?
N1 C2 N2 116.45(8) . . ?
N3 C3 C11 121.16(8) . . ?
N3 C3 N2 116.99(8) . . ?
C11 C3 N2 121.82(8) . . ?
C9 C4 C5 120.95(8) . . ?
C9 C4 N3 119.76(8) . . ?
C5 C4 N3 119.29(8) . . ?
C6 C5 C4 117.89(8) . . ?
C6 C5 C14 121.22(8) . . ?
C4 C5 C14 120.89(8) . . ?
C5 C6 C7 122.55(8) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C8 C7 C6 118.11(8) . . ?
C8 C7 C15 121.51(9) . . ?
C6 C7 C15 120.38(9) . . ?
C7 C8 C9 121.10(8) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 119.38(8) . . ?
C4 C9 C10 119.25(7) . . ?
C8 C9 C10 121.29(8) . . ?
C11 C10 C9 111.42(7) . . ?
C11 C10 C16 109.55(7) . . ?
C9 C10 C16 108.93(7) . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C16 C10 H10 109.0 . . ?
C3 C11 C1 120.02(8) . . ?
C3 C11 C10 120.06(8) . . ?
C1 C11 C10 119.92(8) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 F3 106.40(8) . . ?
F1 C16 F2 106.38(8) . . ?
F3 C16 F2 106.09(8) . . ?
F1 C16 C10 112.47(8) . . ?
F3 C16 C10 112.62(8) . . ?
F2 C16 C10 112.38(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 178.78(9) . . . . ?
C12 N1 C1 O1 -1.82(14) . . . . ?
C2 N1 C1 C11 -0.36(13) . . . . ?
C12 N1 C1 C11 179.04(9) . . . . ?
C1 N1 C2 O2 178.39(9) . . . . ?
C12 N1 C2 O2 -1.02(13) . . . . ?
C1 N1 C2 N2 -2.51(13) . . . . ?
C12 N1 C2 N2 178.08(8) . . . . ?
C3 N2 C2 O2 -179.81(8) . . . . ?
C13 N2 C2 O2 1.39(13) . . . . ?
C3 N2 C2 N1 1.09(12) . . . . ?
C13 N2 C2 N1 -177.71(8) . . . . ?
C4 N3 C3 C11 -14.06(13) . . . . ?
C4 N3 C3 N2 164.12(8) . . . . ?
C2 N2 C3 N3 -174.84(8) . . . . ?
C13 N2 C3 N3 3.94(12) . . . . ?
C2 N2 C3 C11 3.33(13) . . . . ?
C13 N2 C3 C11 -177.90(8) . . . . ?
C3 N3 C4 C9 15.85(13) . . . . ?
C3 N3 C4 C5 -163.32(8) . . . . ?
C9 C4 C5 C6 -0.20(13) . . . . ?
N3 C4 C5 C6 178.96(8) . . . . ?
C9 C4 C5 C14 179.09(8) . . . . ?
N3 C4 C5 C14 -1.75(13) . . . . ?
C4 C5 C6 C7 -0.93(13) . . . . ?
C14 C5 C6 C7 179.78(8) . . . . ?
C5 C6 C7 C8 0.97(13) . . . . ?
C5 C6 C7 C15 -178.51(9) . . . . ?
C6 C7 C8 C9 0.12(13) . . . . ?
C15 C7 C8 C9 179.60(9) . . . . ?
C5 C4 C9 C8 1.24(13) . . . . ?
N3 C4 C9 C8 -177.91(8) . . . . ?
C5 C4 C9 C10 -175.54(8) . . . . ?
N3 C4 C9 C10 5.31(12) . . . . ?
C7 C8 C9 C4 -1.21(13) . . . . ?
C7 C8 C9 C10 175.51(8) . . . . ?
C4 C9 C10 C11 -25.25(11) . . . . ?
C8 C9 C10 C11 158.03(8) . . . . ?
C4 C9 C10 C16 95.72(9) . . . . ?
C8 C9 C10 C16 -80.99(10) . . . . ?
N3 C3 C11 C1 171.73(8) . . . . ?
N2 C3 C11 C1 -6.36(13) . . . . ?
N3 C3 C11 C10 -9.06(13) . . . . ?
N2 C3 C11 C10 172.85(8) . . . . ?
O1 C1 C11 C3 -174.34(10) . . . . ?
N1 C1 C11 C3 4.75(13) . . . . ?
O1 C1 C11 C10 6.45(15) . . . . ?
N1 C1 C11 C10 -174.47(8) . . . . ?
C9 C10 C11 C3 27.46(11) . . . . ?
C16 C10 C11 C3 -93.15(10) . . . . ?
C9 C10 C11 C1 -153.32(8) . . . . ?
C16 C10 C11 C1 86.06(10) . . . . ?
C11 C10 C16 F1 64.30(10) . . . . ?
C9 C10 C16 F1 -57.81(10) . . . . ?
C11 C10 C16 F3 -55.92(10) . . . . ?
C9 C10 C16 F3 -178.03(7) . . . . ?
C11 C10 C16 F2 -175.67(7) . . . . ?
C9 C10 C16 F2 62.22(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        31.03
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 895399'
#######################################################################
#
#                 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_is_sd283
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 F3 N3 O3'
_chemical_formula_sum            'C16 H14 F3 N3 O3'
_chemical_formula_weight         353.30

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

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   7.4835(3)
_cell_length_b                   8.5920(3)
_cell_length_c                   11.4002(4)
_cell_angle_alpha                92.445(2)
_cell_angle_beta                 104.160(2)
_cell_angle_gamma                93.761(2)
_cell_volume                     707.90(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7592
_cell_measurement_theta_min      4.760
_cell_measurement_theta_max      60.939

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9349
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15295
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4101
_reflns_number_gt                3515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (except H1) were positioned geometrically and refined using a
riding model, with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0526P)^2^+0.2092P] where P=(Fo^2^+2Fc^2^)/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         4101
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.67860(15) 0.80569(12) 0.35001(10) 0.0221(2) Uani 1 1 d . . .
C2 C 0.52217(14) 0.73219(11) 0.26315(9) 0.0189(2) Uani 1 1 d . . .
C3 C 0.39565(14) 0.83615(11) 0.18124(9) 0.0188(2) Uani 1 1 d . . .
C4 C 0.30087(14) 0.74579(12) 0.06422(9) 0.0193(2) Uani 1 1 d . . .
C5 C 0.22738(15) 0.81636(14) -0.04346(10) 0.0246(2) Uani 1 1 d . . .
H5 H 0.2346 0.9270 -0.0448 0.029 Uiso 1 1 calc R . .
C6 C 0.14399(16) 0.72516(15) -0.14822(11) 0.0294(3) Uani 1 1 d . . .
H6 H 0.0926 0.7744 -0.2205 0.035 Uiso 1 1 calc R . .
C7 C 0.13408(16) 0.56180(15) -0.14949(11) 0.0288(3) Uani 1 1 d . . .
H7 H 0.0765 0.5005 -0.2218 0.035 Uiso 1 1 calc R . .
C8 C 0.20963(15) 0.49085(13) -0.04347(10) 0.0237(2) Uani 1 1 d . . .
C9 C 0.22460(16) 0.32238(13) -0.01556(11) 0.0275(2) Uani 1 1 d . . .
H9A H 0.2824 0.2667 -0.0728 0.033 Uiso 1 1 calc R . .
H9B H 0.1012 0.2695 -0.0203 0.033 Uiso 1 1 calc R . .
C10 C 0.34705(17) 0.32760(12) 0.11426(11) 0.0271(2) Uani 1 1 d . . .
H10A H 0.2898 0.2594 0.1651 0.033 Uiso 1 1 calc R . .
H10B H 0.4706 0.2927 0.1145 0.033 Uiso 1 1 calc R . .
C11 C 0.28950(14) 0.58447(12) 0.06134(10) 0.0195(2) Uani 1 1 d . . .
C12 C 0.48878(14) 0.57078(11) 0.25681(9) 0.0183(2) Uani 1 1 d . . .
C13 C 0.72725(16) 0.55677(13) 0.44349(10) 0.0250(2) Uani 1 1 d . . .
C14 C 0.24854(16) 0.88690(12) 0.24617(11) 0.0240(2) Uani 1 1 d . . .
C15 C 0.51966(19) 0.32615(13) 0.37135(12) 0.0314(3) Uani 1 1 d . . .
H15A H 0.3842 0.3151 0.3498 0.047 Uiso 1 1 calc R . .
H15B H 0.5661 0.3066 0.4571 0.047 Uiso 1 1 calc R . .
H15C H 0.5660 0.2506 0.3214 0.047 Uiso 1 1 calc R . .
C16 C 0.94460(18) 0.78444(15) 0.52106(12) 0.0323(3) Uani 1 1 d . . .
H16A H 0.9044 0.8523 0.5794 0.048 Uiso 1 1 calc R . .
H16B H 1.0216 0.8468 0.4794 0.048 Uiso 1 1 calc R . .
H16C H 1.0164 0.7035 0.5639 0.048 Uiso 1 1 calc R . .
F1 F 0.14480(10) 0.76422(8) 0.26912(7) 0.03193(18) Uani 1 1 d . . .
F2 F 0.32496(11) 0.96594(9) 0.35260(7) 0.0374(2) Uani 1 1 d . . .
F3 F 0.13181(11) 0.98034(9) 0.17980(8) 0.03634(19) Uani 1 1 d . . .
H1 H 0.579(3) 0.994(2) 0.2195(18) 0.056(5) Uiso 1 1 d . . .
N1 N 0.36213(13) 0.49537(10) 0.16059(8) 0.02008(18) Uani 1 1 d . . .
N2 N 0.58401(13) 0.48608(10) 0.34987(8) 0.02193(19) Uani 1 1 d . . .
N3 N 0.78193(13) 0.71048(11) 0.43188(9) 0.0242(2) Uani 1 1 d . . .
O1 O 0.73105(13) 0.94661(10) 0.35547(8) 0.0315(2) Uani 1 1 d . . .
O2 O 0.48744(12) 0.97434(9) 0.15499(8) 0.02621(18) Uani 1 1 d . . .
O3 O 0.79992(14) 0.48553(11) 0.53032(8) 0.0356(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0240(5) 0.0200(5) 0.0219(5) -0.0009(4) 0.0054(4) 0.0024(4)
C2 0.0216(5) 0.0155(4) 0.0195(5) 0.0009(4) 0.0052(4) 0.0017(3)
C3 0.0211(5) 0.0134(4) 0.0221(5) 0.0019(3) 0.0060(4) -0.0001(3)
C4 0.0182(5) 0.0199(5) 0.0204(5) 0.0017(4) 0.0060(4) 0.0007(3)
C5 0.0224(5) 0.0264(5) 0.0257(5) 0.0056(4) 0.0065(4) 0.0031(4)
C6 0.0244(6) 0.0412(7) 0.0223(5) 0.0053(5) 0.0042(4) 0.0037(5)
C7 0.0218(5) 0.0402(7) 0.0228(5) -0.0062(5) 0.0054(4) -0.0034(4)
C8 0.0185(5) 0.0257(5) 0.0272(5) -0.0055(4) 0.0089(4) -0.0041(4)
C9 0.0272(6) 0.0227(5) 0.0330(6) -0.0095(4) 0.0123(5) -0.0056(4)
C10 0.0296(6) 0.0149(5) 0.0366(6) -0.0045(4) 0.0092(5) 0.0002(4)
C11 0.0183(5) 0.0198(5) 0.0215(5) 0.0000(4) 0.0073(4) 0.0001(3)
C12 0.0199(5) 0.0162(4) 0.0210(5) 0.0015(4) 0.0088(4) 0.0023(3)
C13 0.0293(6) 0.0257(5) 0.0227(5) 0.0027(4) 0.0095(4) 0.0103(4)
C14 0.0272(5) 0.0182(5) 0.0275(5) 0.0006(4) 0.0078(4) 0.0040(4)
C15 0.0439(7) 0.0187(5) 0.0361(6) 0.0094(5) 0.0168(6) 0.0047(5)
C16 0.0291(6) 0.0349(6) 0.0273(6) -0.0060(5) -0.0037(5) 0.0071(5)
F1 0.0334(4) 0.0277(4) 0.0406(4) 0.0038(3) 0.0207(3) 0.0006(3)
F2 0.0411(4) 0.0365(4) 0.0347(4) -0.0141(3) 0.0117(3) 0.0050(3)
F3 0.0345(4) 0.0298(4) 0.0476(5) 0.0080(3) 0.0114(3) 0.0161(3)
N1 0.0232(4) 0.0130(4) 0.0247(4) -0.0003(3) 0.0079(4) -0.0003(3)
N2 0.0274(5) 0.0167(4) 0.0242(4) 0.0048(3) 0.0096(4) 0.0056(3)
N3 0.0248(5) 0.0246(5) 0.0211(4) -0.0011(4) 0.0015(4) 0.0045(4)
O1 0.0334(5) 0.0203(4) 0.0343(5) -0.0028(3) -0.0019(4) -0.0042(3)
O2 0.0293(4) 0.0173(4) 0.0304(4) 0.0064(3) 0.0049(3) -0.0043(3)
O3 0.0433(5) 0.0365(5) 0.0278(4) 0.0102(4) 0.0058(4) 0.0161(4)

#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2422(13) . ?
C1 N3 1.3905(14) . ?
C1 C2 1.4256(15) . ?
C2 C12 1.3886(13) . ?
C2 C3 1.5218(14) . ?
C3 O2 1.4124(12) . ?
C3 C4 1.5040(14) . ?
C3 C14 1.5441(15) . ?
C4 C11 1.3816(14) . ?
C4 C5 1.3978(15) . ?
C5 C6 1.3860(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4000(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3877(17) . ?
C7 H7 0.9500 . ?
C8 C11 1.3919(14) . ?
C8 C9 1.5007(16) . ?
C9 C10 1.5354(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.5014(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.4104(14) . ?
C12 N1 1.3680(14) . ?
C12 N2 1.3881(13) . ?
C13 O3 1.2175(14) . ?
C13 N3 1.3783(15) . ?
C13 N2 1.3988(15) . ?
C14 F1 1.3408(13) . ?
C14 F2 1.3415(13) . ?
C14 F3 1.3418(13) . ?
C15 N2 1.4764(14) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N3 1.4687(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O2 H1 0.87(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
O1 C1 N3 118.21(10) . . ?
O1 C1 C2 124.81(10) . . ?
N3 C1 C2 116.95(9) . . ?
C12 C2 C1 119.72(10) . . ?
C12 C2 C3 122.41(9) . . ?
C1 C2 C3 117.87(9) . . ?
O2 C3 C4 108.95(8) . . ?
O2 C3 C2 113.86(9) . . ?
C4 C3 C2 109.55(8) . . ?
O2 C3 C14 106.81(8) . . ?
C4 C3 C14 109.16(9) . . ?
C2 C3 C14 108.39(9) . . ?
C11 C4 C5 117.83(10) . . ?
C11 C4 C3 118.70(9) . . ?
C5 C4 C3 123.44(9) . . ?
C6 C5 C4 120.13(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.23(11) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 118.98(10) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C11 118.90(11) . . ?
C7 C8 C9 132.02(10) . . ?
C11 C8 C9 109.08(10) . . ?
C8 C9 C10 104.43(9) . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
C10 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N1 C10 C9 105.38(9) . . ?
N1 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
N1 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C4 C11 C8 122.91(10) . . ?
C4 C11 N1 124.96(9) . . ?
C8 C11 N1 112.09(9) . . ?
N1 C12 N2 120.02(9) . . ?
N1 C12 C2 120.60(9) . . ?
N2 C12 C2 119.37(9) . . ?
O3 C13 N3 121.96(11) . . ?
O3 C13 N2 121.50(11) . . ?
N3 C13 N2 116.54(10) . . ?
F1 C14 F2 107.05(9) . . ?
F1 C14 F3 106.68(9) . . ?
F2 C14 F3 106.73(9) . . ?
F1 C14 C3 111.96(8) . . ?
F2 C14 C3 112.01(9) . . ?
F3 C14 C3 112.05(9) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 N1 C11 117.17(8) . . ?
C12 N1 C10 128.95(9) . . ?
C11 N1 C10 107.71(9) . . ?
C12 N2 C13 121.63(9) . . ?
C12 N2 C15 122.79(10) . . ?
C13 N2 C15 114.48(10) . . ?
C13 N3 C1 123.51(10) . . ?
C13 N3 C16 118.45(10) . . ?
C1 N3 C16 117.51(10) . . ?
C3 O2 H1 103.3(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
O1 C1 C2 C12 172.64(11) . . . . ?
N3 C1 C2 C12 -5.41(15) . . . . ?
O1 C1 C2 C3 -8.17(17) . . . . ?
N3 C1 C2 C3 173.78(9) . . . . ?
C12 C2 C3 O2 -149.87(10) . . . . ?
C1 C2 C3 O2 30.96(13) . . . . ?
C12 C2 C3 C4 -27.61(13) . . . . ?
C1 C2 C3 C4 153.23(9) . . . . ?
C12 C2 C3 C14 91.42(11) . . . . ?
C1 C2 C3 C14 -87.75(11) . . . . ?
O2 C3 C4 C11 145.72(9) . . . . ?
C2 C3 C4 C11 20.57(13) . . . . ?
C14 C3 C4 C11 -97.98(11) . . . . ?
O2 C3 C4 C5 -32.50(14) . . . . ?
C2 C3 C4 C5 -157.66(10) . . . . ?
C14 C3 C4 C5 83.80(12) . . . . ?
C11 C4 C5 C6 0.93(16) . . . . ?
C3 C4 C5 C6 179.17(10) . . . . ?
C4 C5 C6 C7 -1.10(17) . . . . ?
C5 C6 C7 C8 -0.04(18) . . . . ?
C6 C7 C8 C11 1.29(16) . . . . ?
C6 C7 C8 C9 -178.77(11) . . . . ?
C7 C8 C9 C10 172.44(12) . . . . ?
C11 C8 C9 C10 -7.62(12) . . . . ?
C8 C9 C10 N1 11.05(11) . . . . ?
C5 C4 C11 C8 0.36(16) . . . . ?
C3 C4 C11 C8 -177.96(9) . . . . ?
C5 C4 C11 N1 177.73(10) . . . . ?
C3 C4 C11 N1 -0.60(15) . . . . ?
C7 C8 C11 C4 -1.49(16) . . . . ?
C9 C8 C11 C4 178.56(10) . . . . ?
C7 C8 C11 N1 -179.16(10) . . . . ?
C9 C8 C11 N1 0.89(12) . . . . ?
C1 C2 C12 N1 -167.46(10) . . . . ?
C3 C2 C12 N1 13.39(15) . . . . ?
C1 C2 C12 N2 13.16(15) . . . . ?
C3 C2 C12 N2 -166.00(9) . . . . ?
O2 C3 C14 F1 176.28(9) . . . . ?
C4 C3 C14 F1 58.63(12) . . . . ?
C2 C3 C14 F1 -60.64(11) . . . . ?
O2 C3 C14 F2 -63.45(11) . . . . ?
C4 C3 C14 F2 178.90(9) . . . . ?
C2 C3 C14 F2 59.62(11) . . . . ?
O2 C3 C14 F3 56.46(11) . . . . ?
C4 C3 C14 F3 -61.19(11) . . . . ?
C2 C3 C14 F3 179.54(8) . . . . ?
N2 C12 N1 C11 -171.27(9) . . . . ?
C2 C12 N1 C11 9.35(14) . . . . ?
N2 C12 N1 C10 -22.57(16) . . . . ?
C2 C12 N1 C10 158.05(10) . . . . ?
C4 C11 N1 C12 -16.20(15) . . . . ?
C8 C11 N1 C12 161.42(9) . . . . ?
C4 C11 N1 C10 -171.11(10) . . . . ?
C8 C11 N1 C10 6.51(12) . . . . ?
C9 C10 N1 C12 -161.88(10) . . . . ?
C9 C10 N1 C11 -10.90(11) . . . . ?
N1 C12 N2 C13 173.56(9) . . . . ?
C2 C12 N2 C13 -7.06(15) . . . . ?
N1 C12 N2 C15 -19.06(15) . . . . ?
C2 C12 N2 C15 160.32(10) . . . . ?
O3 C13 N2 C12 173.62(10) . . . . ?
N3 C13 N2 C12 -6.66(15) . . . . ?
O3 C13 N2 C15 5.26(16) . . . . ?
N3 C13 N2 C15 -175.02(9) . . . . ?
O3 C13 N3 C1 -165.28(11) . . . . ?
N2 C13 N3 C1 15.01(16) . . . . ?
O3 C13 N3 C16 6.18(17) . . . . ?
N2 C13 N3 C16 -173.54(10) . . . . ?
O1 C1 N3 C13 172.72(10) . . . . ?
C2 C1 N3 C13 -9.09(16) . . . . ?
O1 C1 N3 C16 1.19(16) . . . . ?
C2 C1 N3 C16 179.38(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 895400'
#######################################################################
#
#                 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_is_sd284
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl F3 N3 O2'
_chemical_formula_sum            'C16 H13 Cl F3 N3 O2'
_chemical_formula_weight         371.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   19.9679(8)
_cell_length_b                   20.1167(8)
_cell_length_c                   16.4722(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.103(2)
_cell_angle_gamma                90.00
_cell_volume                     6172.9(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      4.840
_cell_measurement_theta_max      53.869

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3040
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8142
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            55556
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         26.99
_reflns_number_total             13379
_reflns_number_gt                10025
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were positioned geometrically and refined using a riding model,
with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0529P)^2^+1.5951P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13379
_refine_ls_number_parameters     909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
Cl1 Cl 1.07316(3) 0.50079(3) 0.67032(4) 0.04114(14) Uani 1 1 d . . .
F1 F 0.63895(6) 0.69493(5) 0.65684(8) 0.0346(3) Uani 1 1 d . . .
F2 F 0.71777(7) 0.76460(5) 0.65601(8) 0.0372(3) Uani 1 1 d . . .
F3 F 0.63659(6) 0.73577(6) 0.53478(8) 0.0384(3) Uani 1 1 d . . .
N1 N 0.82860(8) 0.55697(7) 0.61276(10) 0.0229(3) Uani 1 1 d . . .
N2 N 0.75658(8) 0.47926(7) 0.64386(11) 0.0262(4) Uani 1 1 d . . .
N3 N 0.64020(8) 0.50487(7) 0.63942(11) 0.0286(4) Uani 1 1 d . . .
O1 O 0.58435(7) 0.59469(7) 0.56142(9) 0.0342(3) Uani 1 1 d . . .
O2 O 0.69182(8) 0.40496(6) 0.68883(10) 0.0376(4) Uani 1 1 d . . .
C1 C 0.64012(10) 0.56631(9) 0.60116(13) 0.0264(4) Uani 1 1 d . . .
C2 C 0.71199(9) 0.59161(8) 0.61006(12) 0.0219(4) Uani 1 1 d . . .
C3 C 0.72861(10) 0.65765(8) 0.60315(12) 0.0217(4) Uani 1 1 d . . .
C4 C 0.79429(10) 0.67424(8) 0.59267(12) 0.0218(4) Uani 1 1 d . . .
C5 C 0.81398(10) 0.73969(9) 0.57590(12) 0.0263(4) Uani 1 1 d . . .
H5 H 0.7831 0.7762 0.5736 0.032 Uiso 1 1 calc R . .
C6 C 0.87668(11) 0.74982(9) 0.56326(12) 0.0297(4) Uani 1 1 d . . .
H6 H 0.8893 0.7936 0.5524 0.036 Uiso 1 1 calc R . .
C7 C 0.92362(11) 0.69677(10) 0.56587(13) 0.0300(4) Uani 1 1 d . . .
H7 H 0.9674 0.7056 0.5574 0.036 Uiso 1 1 calc R . .
C8 C 0.90719(10) 0.63272(9) 0.58039(12) 0.0259(4) Uani 1 1 d . . .
C9 C 0.84190(10) 0.62067(8) 0.59470(11) 0.0223(4) Uani 1 1 d . . .
C10 C 0.76704(10) 0.54387(8) 0.62079(11) 0.0212(4) Uani 1 1 d . . .
C11 C 0.69684(10) 0.45954(9) 0.66033(13) 0.0275(4) Uani 1 1 d . . .
C12 C 0.67932(10) 0.71272(9) 0.61164(13) 0.0262(4) Uani 1 1 d . . .
C13 C 0.95716(10) 0.57626(10) 0.58018(13) 0.0307(4) Uani 1 1 d . . .
H13A H 0.9882 0.5901 0.5480 0.037 Uiso 1 1 calc R . .
H13B H 0.9285 0.5375 0.5497 0.037 Uiso 1 1 calc R . .
C14 C 1.00359(11) 0.55629(10) 0.67182(14) 0.0333(5) Uani 1 1 d . . .
H14A H 0.9736 0.5343 0.7004 0.040 Uiso 1 1 calc R . .
H14B H 1.0252 0.5965 0.7059 0.040 Uiso 1 1 calc R . .
C15 C 0.81442(11) 0.43023(9) 0.65897(15) 0.0361(5) Uani 1 1 d . . .
H15A H 0.7946 0.3853 0.6550 0.054 Uiso 1 1 calc R . .
H15B H 0.8508 0.4370 0.7170 0.054 Uiso 1 1 calc R . .
H15C H 0.8365 0.4358 0.6150 0.054 Uiso 1 1 calc R . .
C16 C 0.57204(11) 0.48083(11) 0.64284(17) 0.0411(5) Uani 1 1 d . . .
H16A H 0.5439 0.5186 0.6506 0.062 Uiso 1 1 calc R . .
H16B H 0.5815 0.4500 0.6918 0.062 Uiso 1 1 calc R . .
H16C H 0.5451 0.4578 0.5884 0.062 Uiso 1 1 calc R . .
Cl2 Cl 0.55477(3) 0.84777(2) 0.63058(4) 0.03987(14) Uani 1 1 d . . .
F4 F 0.13616(6) 0.65229(5) 0.64368(7) 0.0311(3) Uani 1 1 d . . .
F5 F 0.13285(7) 0.60573(6) 0.52451(8) 0.0432(3) Uani 1 1 d . . .
F6 F 0.21580(7) 0.58269(5) 0.64702(9) 0.0405(3) Uani 1 1 d . . .
N4 N 0.31968(8) 0.78542(7) 0.57436(10) 0.0216(3) Uani 1 1 d . . .
N5 N 0.24892(8) 0.86682(7) 0.59879(10) 0.0245(3) Uani 1 1 d . . .
N6 N 0.13261(8) 0.84507(7) 0.59649(10) 0.0248(3) Uani 1 1 d . . .
O3 O 0.07919(7) 0.74739(6) 0.54405(9) 0.0300(3) Uani 1 1 d . . .
O4 O 0.18058(8) 0.94880(6) 0.62378(10) 0.0374(4) Uani 1 1 d . . .
C17 C 0.13438(10) 0.77920(9) 0.57361(11) 0.0224(4) Uani 1 1 d . . .
C18 C 0.20635(9) 0.75292(8) 0.58377(11) 0.0193(4) Uani 1 1 d . . .
C19 C 0.22370(10) 0.68630(8) 0.58371(11) 0.0205(4) Uani 1 1 d . . .
C20 C 0.28845(9) 0.66777(8) 0.57223(11) 0.0216(4) Uani 1 1 d . . .
C21 C 0.31037(11) 0.60122(9) 0.56452(13) 0.0288(4) Uani 1 1 d . . .
H21 H 0.2813 0.5650 0.5687 0.035 Uiso 1 1 calc R . .
C22 C 0.37275(11) 0.58941(10) 0.55122(14) 0.0339(5) Uani 1 1 d . . .
H22 H 0.3870 0.5448 0.5474 0.041 Uiso 1 1 calc R . .
C23 C 0.41644(11) 0.64147(10) 0.54295(13) 0.0327(5) Uani 1 1 d . . .
H23 H 0.4595 0.6315 0.5335 0.039 Uiso 1 1 calc R . .
C24 C 0.39817(10) 0.70649(9) 0.54829(12) 0.0258(4) Uani 1 1 d . . .
C25 C 0.33387(9) 0.72039(8) 0.56419(11) 0.0215(4) Uani 1 1 d . . .
C26 C 0.25947(9) 0.79998(8) 0.58467(11) 0.0204(4) Uani 1 1 d . . .
C27 C 0.18746(10) 0.89062(9) 0.60836(12) 0.0259(4) Uani 1 1 d . . .
C28 C 0.17597(10) 0.63233(9) 0.59874(12) 0.0247(4) Uani 1 1 d . . .
C29 C 0.44609(10) 0.76267(10) 0.54151(13) 0.0286(4) Uani 1 1 d . . .
H29A H 0.4165 0.7997 0.5075 0.034 Uiso 1 1 calc R . .
H29B H 0.4780 0.7471 0.5113 0.034 Uiso 1 1 calc R . .
C30 C 0.49048(11) 0.78622(11) 0.63214(14) 0.0348(5) Uani 1 1 d . . .
H30A H 0.5159 0.7478 0.6675 0.042 Uiso 1 1 calc R . .
H30B H 0.4583 0.8051 0.6600 0.042 Uiso 1 1 calc R . .
C31 C 0.30645(11) 0.91418(9) 0.60577(15) 0.0343(5) Uani 1 1 d . . .
H31A H 0.2911 0.9591 0.6143 0.051 Uiso 1 1 calc R . .
H31B H 0.3172 0.9130 0.5523 0.051 Uiso 1 1 calc R . .
H31C H 0.3495 0.9022 0.6554 0.051 Uiso 1 1 calc R . .
C32 C 0.06202(11) 0.87222(10) 0.58738(15) 0.0367(5) Uani 1 1 d . . .
H32A H 0.0681 0.9161 0.6149 0.055 Uiso 1 1 calc R . .
H32B H 0.0383 0.8424 0.6157 0.055 Uiso 1 1 calc R . .
H32C H 0.0325 0.8763 0.5255 0.055 Uiso 1 1 calc R . .
Cl3 Cl 1.02350(3) 0.63267(3) 0.28434(4) 0.04743(15) Uani 1 1 d . . .
F7 F 0.64119(7) 0.89446(6) 0.30370(8) 0.0443(3) Uani 1 1 d . . .
F8 F 0.65589(6) 0.85176(5) 0.42978(8) 0.0352(3) Uani 1 1 d . . .
F9 F 0.73069(7) 0.92132(5) 0.41755(9) 0.0431(3) Uani 1 1 d . . .
N7 N 0.82522(8) 0.70933(7) 0.35473(10) 0.0253(3) Uani 1 1 d . . .
N8 N 0.74339(9) 0.63202(7) 0.36286(11) 0.0283(4) Uani 1 1 d . . .
N9 N 0.63011(9) 0.66164(7) 0.36397(11) 0.0280(4) Uani 1 1 d . . .
O7 O 0.88235(7) 0.11507(6) 0.58270(9) 0.0296(3) Uani 1 1 d . . .
O8 O 0.82172(8) -0.09793(6) 0.61206(10) 0.0386(4) Uani 1 1 d . . .
C33 C 0.63766(10) 0.72800(9) 0.34565(12) 0.0236(4) Uani 1 1 d . . .
C34 C 0.71115(9) 0.74868(8) 0.35605(11) 0.0205(4) Uani 1 1 d . . .
C35 C 0.73356(10) 0.81398(8) 0.35864(11) 0.0211(4) Uani 1 1 d . . .
C36 C 0.80042(10) 0.82871(9) 0.35006(12) 0.0236(4) Uani 1 1 d . . .
C37 C 0.82527(11) 0.89340(9) 0.33982(13) 0.0307(4) Uani 1 1 d . . .
H37 H 0.7959 0.9311 0.3373 0.037 Uiso 1 1 calc R . .
C38 C 0.89075(12) 0.90139(11) 0.33363(15) 0.0387(5) Uani 1 1 d . . .
H38 H 0.9059 0.9446 0.3247 0.046 Uiso 1 1 calc R . .
C39 C 0.93652(12) 0.84710(11) 0.34007(15) 0.0408(5) Uani 1 1 d . . .
H39 H 0.9830 0.8547 0.3386 0.049 Uiso 1 1 calc R . .
C40 C 0.91568(11) 0.78383(10) 0.34846(14) 0.0334(5) Uani 1 1 d . . .
C41 C 0.84521(10) 0.77340(9) 0.34963(12) 0.0254(4) Uani 1 1 d . . .
C42 C 0.76142(10) 0.69827(8) 0.35655(12) 0.0218(4) Uani 1 1 d . . .
C43 C 0.68113(11) 0.61274(9) 0.37306(14) 0.0314(5) Uani 1 1 d . . .
C44 C 0.68933(11) 0.87002(9) 0.37657(13) 0.0275(4) Uani 1 1 d . . .
C45 C 0.96616(11) 0.72568(11) 0.35816(14) 0.0371(5) Uani 1 1 d . . .
H45A H 1.0164 0.7413 0.3845 0.044 Uiso 1 1 calc R . .
H45B H 0.9579 0.6922 0.3976 0.044 Uiso 1 1 calc R . .
C46 C 0.95480(12) 0.69425(12) 0.27171(15) 0.0422(5) Uani 1 1 d . . .
H46A H 0.9569 0.7287 0.2297 0.051 Uiso 1 1 calc R . .
H46B H 0.9069 0.6731 0.2488 0.051 Uiso 1 1 calc R . .
C47 C 0.79530(12) 0.57973(10) 0.36428(16) 0.0413(6) Uani 1 1 d . . .
H47A H 0.7701 0.5372 0.3473 0.062 Uiso 1 1 calc R . .
H47B H 0.8314 0.5760 0.4231 0.062 Uiso 1 1 calc R . .
H47C H 0.8190 0.5911 0.3234 0.062 Uiso 1 1 calc R . .
C48 C 0.55893(11) 0.63921(11) 0.35988(15) 0.0390(5) Uani 1 1 d . . .
H48A H 0.5315 0.6232 0.3010 0.058 Uiso 1 1 calc R . .
H48B H 0.5334 0.6764 0.3742 0.058 Uiso 1 1 calc R . .
H48C H 0.5645 0.6031 0.4017 0.058 Uiso 1 1 calc R . .
Cl4 Cl 0.44390(3) 0.00076(3) 0.59769(5) 0.04996(17) Uani 1 1 d . . .
F10 F 0.83367(6) 0.26200(5) 0.73423(7) 0.0274(2) Uani 1 1 d . . .
F11 F 0.90326(5) 0.19067(5) 0.71318(7) 0.0284(3) Uani 1 1 d . . .
F12 F 0.83355(6) 0.24838(5) 0.60501(7) 0.0330(3) Uani 1 1 d . . .
N10 N 0.68000(8) 0.06341(7) 0.65918(10) 0.0226(3) Uani 1 1 d . . .
N11 N 0.74900(8) -0.01640(7) 0.62823(10) 0.0257(4) Uani 1 1 d . . .
N12 N 0.85500(9) 0.00902(7) 0.60359(11) 0.0265(4) Uani 1 1 d . . .
O5 O 0.58588(7) 0.76448(6) 0.32068(9) 0.0315(3) Uani 1 1 d . . .
O6 O 0.67015(9) 0.55541(7) 0.38785(12) 0.0492(4) Uani 1 1 d . . .
C49 C 0.84611(9) 0.07714(8) 0.60711(11) 0.0221(4) Uani 1 1 d . . .
C50 C 0.78873(9) 0.09860(8) 0.63861(11) 0.0196(4) Uani 1 1 d . . .
C51 C 0.77833(9) 0.16357(8) 0.66050(11) 0.0190(4) Uani 1 1 d . . .
C52 C 0.71334(9) 0.18081(8) 0.67234(11) 0.0206(4) Uani 1 1 d . . .
C53 C 0.69110(10) 0.24710(9) 0.68166(12) 0.0252(4) Uani 1 1 d . . .
H53 H 0.7202 0.2837 0.6789 0.030 Uiso 1 1 calc R . .
C54 C 0.62856(11) 0.25771(9) 0.69441(13) 0.0302(4) Uani 1 1 d . . .
H54 H 0.6141 0.3020 0.6996 0.036 Uiso 1 1 calc R . .
C55 C 0.58447(11) 0.20473(10) 0.70015(13) 0.0305(4) Uani 1 1 d . . .
H55 H 0.5422 0.2137 0.7120 0.037 Uiso 1 1 calc R . .
C56 C 0.60177(10) 0.14031(9) 0.68891(12) 0.0255(4) Uani 1 1 d . . .
C57 C 0.66598(9) 0.12783(8) 0.67264(11) 0.0213(4) Uani 1 1 d . . .
C58 C 0.73762(9) 0.05028(8) 0.64192(11) 0.0203(4) Uani 1 1 d . . .
C59 C 0.80923(10) -0.03925(9) 0.61557(12) 0.0260(4) Uani 1 1 d . . .
C60 C 0.83752(10) 0.21581(8) 0.67745(11) 0.0214(4) Uani 1 1 d . . .
C61 C 0.55262(11) 0.08382(10) 0.69062(14) 0.0311(4) Uani 1 1 d . . .
H61A H 0.5228 0.0970 0.7247 0.037 Uiso 1 1 calc R . .
H61B H 0.5815 0.0446 0.7190 0.037 Uiso 1 1 calc R . .
C62 C 0.50490(11) 0.06642(11) 0.59882(15) 0.0402(5) Uani 1 1 d . . .
H62A H 0.5350 0.0525 0.5654 0.048 Uiso 1 1 calc R . .
H62B H 0.4773 0.1062 0.5702 0.048 Uiso 1 1 calc R . .
C63 C 0.69496(11) -0.06551(9) 0.63015(15) 0.0346(5) Uani 1 1 d . . .
H63A H 0.6505 -0.0583 0.5803 0.052 Uiso 1 1 calc R . .
H63B H 0.6855 -0.0605 0.6842 0.052 Uiso 1 1 calc R . .
H63C H 0.7130 -0.1104 0.6273 0.052 Uiso 1 1 calc R . .
C64 C 0.91543(12) -0.01550(10) 0.58112(16) 0.0376(5) Uani 1 1 d . . .
H64A H 0.9382 -0.0530 0.6190 0.056 Uiso 1 1 calc R . .
H64B H 0.9506 0.0203 0.5891 0.056 Uiso 1 1 calc R . .
H64C H 0.8978 -0.0301 0.5203 0.056 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0305(3) 0.0374(3) 0.0585(4) 0.0078(2) 0.0196(2) 0.0096(2)
F1 0.0392(7) 0.0307(6) 0.0439(7) 0.0037(5) 0.0270(6) 0.0091(5)
F2 0.0432(7) 0.0230(5) 0.0495(8) -0.0103(5) 0.0216(6) -0.0003(5)
F3 0.0418(7) 0.0390(7) 0.0333(7) 0.0097(5) 0.0123(5) 0.0213(5)
N1 0.0192(8) 0.0210(7) 0.0289(9) -0.0010(6) 0.0092(6) 0.0019(6)
N2 0.0245(9) 0.0170(7) 0.0380(9) 0.0029(6) 0.0121(7) 0.0026(6)
N3 0.0219(9) 0.0249(8) 0.0404(10) 0.0011(7) 0.0129(7) -0.0026(6)
O1 0.0196(7) 0.0386(8) 0.0434(9) 0.0071(6) 0.0104(6) 0.0063(6)
O2 0.0411(9) 0.0219(7) 0.0524(10) 0.0044(6) 0.0200(7) -0.0045(6)
C1 0.0243(10) 0.0257(9) 0.0312(11) -0.0010(8) 0.0125(8) 0.0015(7)
C2 0.0201(9) 0.0213(8) 0.0246(9) 0.0001(7) 0.0084(7) 0.0025(7)
C3 0.0217(10) 0.0202(8) 0.0229(9) 0.0015(7) 0.0079(7) 0.0035(7)
C4 0.0224(10) 0.0201(8) 0.0226(9) -0.0003(7) 0.0076(7) -0.0005(7)
C5 0.0292(11) 0.0215(9) 0.0264(10) 0.0001(7) 0.0078(8) -0.0020(7)
C6 0.0328(12) 0.0270(10) 0.0275(10) 0.0005(8) 0.0087(8) -0.0077(8)
C7 0.0238(11) 0.0393(11) 0.0278(10) 0.0015(8) 0.0103(8) -0.0061(8)
C8 0.0199(10) 0.0322(10) 0.0265(10) -0.0006(8) 0.0095(7) -0.0003(8)
C9 0.0208(9) 0.0240(9) 0.0215(9) -0.0012(7) 0.0068(7) 0.0005(7)
C10 0.0208(9) 0.0168(8) 0.0251(9) -0.0009(7) 0.0073(7) 0.0013(7)
C11 0.0269(11) 0.0227(9) 0.0330(11) -0.0016(8) 0.0108(8) -0.0049(7)
C12 0.0276(11) 0.0225(9) 0.0297(10) 0.0027(7) 0.0119(8) 0.0049(7)
C13 0.0207(10) 0.0387(11) 0.0362(11) -0.0028(9) 0.0146(8) 0.0015(8)
C14 0.0248(11) 0.0354(11) 0.0391(12) -0.0037(9) 0.0107(9) 0.0043(8)
C15 0.0349(12) 0.0230(9) 0.0532(14) 0.0054(9) 0.0194(10) 0.0083(8)
C16 0.0271(12) 0.0396(12) 0.0612(16) 0.0061(11) 0.0213(11) -0.0066(9)
Cl2 0.0308(3) 0.0332(3) 0.0573(4) -0.0016(2) 0.0179(2) -0.0076(2)
F4 0.0388(7) 0.0266(5) 0.0367(7) -0.0004(5) 0.0240(5) -0.0061(5)
F5 0.0469(8) 0.0492(7) 0.0357(7) -0.0180(6) 0.0176(6) -0.0291(6)
F6 0.0468(8) 0.0244(6) 0.0575(8) 0.0126(5) 0.0273(6) 0.0017(5)
N4 0.0191(8) 0.0207(7) 0.0246(8) 0.0016(6) 0.0074(6) -0.0010(6)
N5 0.0217(8) 0.0165(7) 0.0362(9) -0.0007(6) 0.0116(7) -0.0023(6)
N6 0.0220(8) 0.0240(8) 0.0313(9) 0.0044(6) 0.0129(7) 0.0031(6)
O3 0.0201(7) 0.0354(7) 0.0338(8) -0.0016(6) 0.0089(6) -0.0055(6)
O4 0.0397(9) 0.0215(7) 0.0536(10) -0.0016(6) 0.0198(7) 0.0043(6)
C17 0.0221(10) 0.0260(9) 0.0208(9) 0.0031(7) 0.0097(7) -0.0002(7)
C18 0.0188(9) 0.0203(8) 0.0183(8) -0.0003(6) 0.0061(7) -0.0029(7)
C19 0.0219(9) 0.0206(8) 0.0184(9) -0.0002(7) 0.0066(7) -0.0036(7)
C20 0.0198(9) 0.0217(8) 0.0218(9) -0.0001(7) 0.0056(7) -0.0001(7)
C21 0.0289(11) 0.0232(9) 0.0333(11) -0.0025(8) 0.0100(8) -0.0006(8)
C22 0.0322(12) 0.0262(10) 0.0429(12) -0.0034(9) 0.0130(9) 0.0070(8)
C23 0.0251(11) 0.0367(11) 0.0374(12) -0.0032(9) 0.0126(9) 0.0050(8)
C24 0.0200(10) 0.0320(10) 0.0256(10) -0.0013(8) 0.0084(8) -0.0002(7)
C25 0.0184(9) 0.0228(8) 0.0207(9) -0.0001(7) 0.0041(7) -0.0011(7)
C26 0.0200(9) 0.0187(8) 0.0214(9) 0.0025(7) 0.0059(7) -0.0016(7)
C27 0.0265(10) 0.0224(9) 0.0288(10) 0.0021(7) 0.0100(8) 0.0013(7)
C28 0.0265(10) 0.0212(8) 0.0277(10) -0.0028(7) 0.0113(8) -0.0038(7)
C29 0.0198(10) 0.0360(10) 0.0332(11) 0.0016(8) 0.0133(8) -0.0004(8)
C30 0.0220(11) 0.0467(12) 0.0349(12) 0.0019(9) 0.0093(8) -0.0102(9)
C31 0.0308(11) 0.0199(9) 0.0537(14) -0.0023(9) 0.0170(10) -0.0093(8)
C32 0.0281(11) 0.0376(11) 0.0507(14) 0.0030(10) 0.0221(10) 0.0070(9)
Cl3 0.0390(3) 0.0468(3) 0.0639(4) -0.0048(3) 0.0275(3) 0.0068(2)
F7 0.0511(8) 0.0404(7) 0.0402(7) 0.0105(5) 0.0152(6) 0.0284(6)
F8 0.0427(7) 0.0295(6) 0.0430(7) -0.0030(5) 0.0269(6) 0.0048(5)
F9 0.0536(8) 0.0238(6) 0.0604(9) -0.0149(5) 0.0306(7) -0.0056(5)
N7 0.0222(9) 0.0238(8) 0.0300(9) -0.0011(6) 0.0093(7) 0.0042(6)
N8 0.0274(9) 0.0163(7) 0.0402(10) -0.0011(6) 0.0109(7) 0.0030(6)
N9 0.0239(9) 0.0260(8) 0.0354(9) 0.0024(7) 0.0120(7) -0.0036(6)
O7 0.0306(8) 0.0286(7) 0.0368(8) 0.0005(6) 0.0210(6) -0.0030(6)
O8 0.0399(9) 0.0194(7) 0.0557(10) -0.0013(6) 0.0162(7) 0.0062(6)
C33 0.0222(10) 0.0240(9) 0.0246(10) -0.0011(7) 0.0084(7) 0.0006(7)
C34 0.0190(9) 0.0202(8) 0.0212(9) -0.0005(7) 0.0060(7) 0.0026(7)
C35 0.0215(9) 0.0193(8) 0.0214(9) -0.0003(7) 0.0063(7) 0.0034(7)
C36 0.0221(10) 0.0242(9) 0.0237(9) -0.0022(7) 0.0073(7) -0.0005(7)
C37 0.0333(12) 0.0230(9) 0.0358(11) -0.0005(8) 0.0124(9) -0.0026(8)
C38 0.0396(13) 0.0352(11) 0.0435(13) -0.0001(9) 0.0175(10) -0.0128(9)
C39 0.0281(12) 0.0495(13) 0.0479(14) -0.0037(10) 0.0174(10) -0.0115(10)
C40 0.0242(11) 0.0410(11) 0.0360(12) -0.0035(9) 0.0120(9) -0.0008(9)
C41 0.0206(10) 0.0267(9) 0.0283(10) -0.0014(7) 0.0079(8) 0.0000(7)
C42 0.0204(10) 0.0196(8) 0.0240(9) -0.0017(7) 0.0064(7) 0.0016(7)
C43 0.0328(12) 0.0217(9) 0.0373(12) 0.0021(8) 0.0096(9) -0.0010(8)
C44 0.0309(11) 0.0203(9) 0.0329(11) 0.0010(8) 0.0132(8) 0.0047(8)
C45 0.0205(11) 0.0572(14) 0.0329(11) 0.0002(10) 0.0088(8) 0.0033(9)
C46 0.0322(13) 0.0542(14) 0.0363(13) -0.0021(10) 0.0078(10) 0.0041(10)
C47 0.0424(14) 0.0229(10) 0.0585(15) -0.0033(9) 0.0179(11) 0.0114(9)
C48 0.0269(12) 0.0427(12) 0.0484(14) 0.0096(10) 0.0147(10) -0.0073(9)
Cl4 0.0348(3) 0.0341(3) 0.0871(5) -0.0171(3) 0.0294(3) -0.0134(2)
F10 0.0278(6) 0.0212(5) 0.0330(6) -0.0068(4) 0.0106(5) -0.0056(4)
F11 0.0185(6) 0.0288(5) 0.0364(6) -0.0020(5) 0.0080(5) -0.0024(4)
F12 0.0405(7) 0.0303(6) 0.0283(6) 0.0070(5) 0.0124(5) -0.0117(5)
N10 0.0219(8) 0.0199(7) 0.0262(8) -0.0020(6) 0.0090(6) -0.0026(6)
N11 0.0259(9) 0.0161(7) 0.0353(9) -0.0022(6) 0.0115(7) -0.0017(6)
N12 0.0264(9) 0.0223(8) 0.0340(9) -0.0001(6) 0.0147(7) 0.0037(6)
O5 0.0203(7) 0.0332(7) 0.0390(8) 0.0011(6) 0.0082(6) 0.0050(6)
O6 0.0519(11) 0.0237(7) 0.0744(12) 0.0093(7) 0.0256(9) -0.0038(7)
C49 0.0205(10) 0.0236(9) 0.0218(9) -0.0006(7) 0.0070(7) 0.0002(7)
C50 0.0186(9) 0.0201(8) 0.0199(9) 0.0016(7) 0.0065(7) 0.0002(7)
C51 0.0187(9) 0.0173(8) 0.0200(9) 0.0018(6) 0.0057(7) -0.0025(6)
C52 0.0196(9) 0.0198(8) 0.0221(9) -0.0007(7) 0.0069(7) 0.0000(7)
C53 0.0228(10) 0.0200(8) 0.0305(10) -0.0017(7) 0.0067(8) 0.0011(7)
C54 0.0284(11) 0.0226(9) 0.0384(12) -0.0053(8) 0.0107(9) 0.0050(8)
C55 0.0214(10) 0.0365(11) 0.0355(11) -0.0043(8) 0.0126(8) 0.0027(8)
C56 0.0199(10) 0.0282(9) 0.0285(10) -0.0027(8) 0.0088(8) -0.0021(7)
C57 0.0187(9) 0.0219(8) 0.0228(9) -0.0014(7) 0.0067(7) -0.0016(7)
C58 0.0197(9) 0.0172(8) 0.0231(9) -0.0005(7) 0.0068(7) -0.0011(7)
C59 0.0266(10) 0.0210(9) 0.0285(10) -0.0012(7) 0.0076(8) 0.0013(7)
C60 0.0214(10) 0.0201(8) 0.0234(9) 0.0006(7) 0.0091(7) -0.0022(7)
C61 0.0244(11) 0.0339(10) 0.0410(12) -0.0006(9) 0.0191(9) -0.0041(8)
C62 0.0268(12) 0.0449(12) 0.0512(14) -0.0060(10) 0.0170(10) -0.0137(9)
C63 0.0349(12) 0.0195(9) 0.0505(13) -0.0024(8) 0.0167(10) -0.0088(8)
C64 0.0342(12) 0.0324(11) 0.0541(14) -0.0020(10) 0.0253(10) 0.0088(9)

#==============================================================================

# MOLECULAR GEOMETRY

_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
Cl1 C14 1.789(2) . ?
F1 C12 1.328(2) . ?
F2 C12 1.345(2) . ?
F3 C12 1.330(2) . ?
N1 C10 1.310(2) . ?
N1 C9 1.363(2) . ?
N2 C11 1.374(2) . ?
N2 C10 1.391(2) . ?
N2 C15 1.470(2) . ?
N3 C1 1.387(2) . ?
N3 C11 1.396(2) . ?
N3 C16 1.465(3) . ?
O1 C1 1.212(2) . ?
O2 C11 1.212(2) . ?
C1 C2 1.479(3) . ?
C2 C3 1.384(2) . ?
C2 C10 1.422(2) . ?
C3 C4 1.423(3) . ?
C3 C12 1.522(2) . ?
C4 C5 1.429(2) . ?
C4 C9 1.430(2) . ?
C5 C6 1.357(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.427(3) . ?
C8 C13 1.513(3) . ?
C13 C14 1.514(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
Cl2 C30 1.791(2) . ?
F4 C28 1.328(2) . ?
F5 C28 1.328(2) . ?
F6 C28 1.344(2) . ?
N4 C26 1.307(2) . ?
N4 C25 1.362(2) . ?
N5 C27 1.378(2) . ?
N5 C26 1.393(2) . ?
N5 C31 1.465(2) . ?
N6 C17 1.381(2) . ?
N6 C27 1.387(2) . ?
N6 C32 1.468(2) . ?
O3 C17 1.214(2) . ?
O4 C27 1.216(2) . ?
C17 C18 1.483(3) . ?
C18 C19 1.384(2) . ?
C18 C26 1.418(2) . ?
C19 C20 1.422(3) . ?
C19 C28 1.523(2) . ?
C20 C21 1.428(2) . ?
C20 C25 1.431(2) . ?
C21 C22 1.361(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.401(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.369(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.427(3) . ?
C24 C29 1.511(3) . ?
C29 C30 1.512(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Cl3 C46 1.804(2) . ?
F7 C44 1.333(2) . ?
F8 C44 1.331(2) . ?
F9 C44 1.342(2) . ?
N7 C42 1.304(2) . ?
N7 C41 1.361(2) . ?
N8 C43 1.369(3) . ?
N8 C42 1.394(2) . ?
N8 C47 1.471(2) . ?
N9 C43 1.385(2) . ?
N9 C33 1.389(2) . ?
N9 C48 1.469(3) . ?
O7 C49 1.215(2) . ?
O8 C59 1.212(2) . ?
C33 O5 1.213(2) . ?
C33 C34 1.475(3) . ?
C34 C35 1.383(2) . ?
C34 C42 1.425(2) . ?
C35 C36 1.423(3) . ?
C35 C44 1.525(2) . ?
C36 C37 1.424(3) . ?
C36 C41 1.429(3) . ?
C37 C38 1.357(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.403(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.362(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.430(3) . ?
C40 C45 1.515(3) . ?
C43 O6 1.215(2) . ?
C45 C46 1.499(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
Cl4 C62 1.792(2) . ?
F10 C60 1.340(2) . ?
F11 C60 1.330(2) . ?
F12 C60 1.338(2) . ?
N10 C58 1.308(2) . ?
N10 C57 1.361(2) . ?
N11 C59 1.372(2) . ?
N11 C58 1.392(2) . ?
N11 C63 1.472(2) . ?
N12 C49 1.386(2) . ?
N12 C59 1.395(2) . ?
N12 C64 1.469(3) . ?
C49 C50 1.482(3) . ?
C50 C51 1.391(2) . ?
C50 C58 1.425(2) . ?
C51 C52 1.423(2) . ?
C51 C60 1.530(2) . ?
C52 C57 1.426(2) . ?
C52 C53 1.431(2) . ?
C53 C54 1.356(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.407(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.371(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.423(3) . ?
C56 C61 1.509(3) . ?
C61 C62 1.510(3) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C9 118.36(15) . . ?
C11 N2 C10 123.39(15) . . ?
C11 N2 C15 117.26(15) . . ?
C10 N2 C15 119.14(16) . . ?
C1 N3 C11 124.23(16) . . ?
C1 N3 C16 117.56(16) . . ?
C11 N3 C16 117.15(16) . . ?
O1 C1 N3 121.03(18) . . ?
O1 C1 C2 124.14(17) . . ?
N3 C1 C2 114.78(16) . . ?
C3 C2 C10 117.46(16) . . ?
C3 C2 C1 125.10(16) . . ?
C10 C2 C1 117.31(15) . . ?
C2 C3 C4 119.60(16) . . ?
C2 C3 C12 120.61(17) . . ?
C4 C3 C12 119.70(15) . . ?
C3 C4 C5 124.70(16) . . ?
C3 C4 C9 117.04(15) . . ?
C5 C4 C9 118.17(17) . . ?
C6 C5 C4 120.09(17) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.42(17) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.20(19) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 118.59(17) . . ?
C7 C8 C13 120.38(18) . . ?
C9 C8 C13 121.03(16) . . ?
N1 C9 C8 117.21(16) . . ?
N1 C9 C4 122.25(17) . . ?
C8 C9 C4 120.51(16) . . ?
N1 C10 N2 117.03(15) . . ?
N1 C10 C2 124.28(16) . . ?
N2 C10 C2 118.67(16) . . ?
O2 C11 N2 122.47(18) . . ?
O2 C11 N3 120.96(18) . . ?
N2 C11 N3 116.53(16) . . ?
F1 C12 F3 108.48(16) . . ?
F1 C12 F2 104.32(15) . . ?
F3 C12 F2 106.97(14) . . ?
F1 C12 C3 113.49(15) . . ?
F3 C12 C3 112.39(15) . . ?
F2 C12 C3 110.70(15) . . ?
C8 C13 C14 111.39(16) . . ?
C8 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C8 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 Cl1 110.59(15) . . ?
C13 C14 H14A 109.5 . . ?
Cl1 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
Cl1 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 N4 C25 118.26(15) . . ?
C27 N5 C26 123.27(15) . . ?
C27 N5 C31 118.07(15) . . ?
C26 N5 C31 118.64(15) . . ?
C17 N6 C27 125.14(16) . . ?
C17 N6 C32 116.55(15) . . ?
C27 N6 C32 116.68(15) . . ?
O3 C17 N6 120.41(17) . . ?
O3 C17 C18 124.05(16) . . ?
N6 C17 C18 115.48(15) . . ?
C19 C18 C26 117.38(16) . . ?
C19 C18 C17 125.29(16) . . ?
C26 C18 C17 117.00(15) . . ?
C18 C19 C20 119.58(16) . . ?
C18 C19 C28 121.24(16) . . ?
C20 C19 C28 119.15(15) . . ?
C19 C20 C21 125.44(16) . . ?
C19 C20 C25 117.09(15) . . ?
C21 C20 C25 117.42(17) . . ?
C22 C21 C20 120.36(18) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 121.55(18) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 121.22(19) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 118.48(17) . . ?
C23 C24 C29 121.29(18) . . ?
C25 C24 C29 120.17(16) . . ?
N4 C25 C24 116.84(16) . . ?
N4 C25 C20 122.17(17) . . ?
C24 C25 C20 120.94(16) . . ?
N4 C26 N5 116.07(15) . . ?
N4 C26 C18 124.67(16) . . ?
N5 C26 C18 119.25(16) . . ?
O4 C27 N5 122.04(17) . . ?
O4 C27 N6 121.51(18) . . ?
N5 C27 N6 116.42(15) . . ?
F4 C28 F5 108.37(15) . . ?
F4 C28 F6 103.89(15) . . ?
F5 C28 F6 107.14(14) . . ?
F4 C28 C19 114.22(14) . . ?
F5 C28 C19 111.95(15) . . ?
F6 C28 C19 110.75(15) . . ?
C24 C29 C30 108.86(16) . . ?
C24 C29 H29A 109.9 . . ?
C30 C29 H29A 109.9 . . ?
C24 C29 H29B 109.9 . . ?
C30 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
C29 C30 Cl2 111.77(14) . . ?
C29 C30 H30A 109.3 . . ?
Cl2 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
Cl2 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
N5 C31 H31A 109.5 . . ?
N5 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N5 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N6 C32 H32A 109.5 . . ?
N6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C42 N7 C41 118.28(15) . . ?
C43 N8 C42 123.38(15) . . ?
C43 N8 C47 117.46(16) . . ?
C42 N8 C47 119.04(17) . . ?
C43 N9 C33 124.97(17) . . ?
C43 N9 C48 116.65(16) . . ?
C33 N9 C48 117.65(16) . . ?
O5 C33 N9 120.62(17) . . ?
O5 C33 C34 124.06(16) . . ?
N9 C33 C34 115.29(15) . . ?
C35 C34 C42 117.15(16) . . ?
C35 C34 C33 124.66(16) . . ?
C42 C34 C33 118.00(15) . . ?
C34 C35 C36 119.94(16) . . ?
C34 C35 C44 120.30(17) . . ?
C36 C35 C44 119.64(15) . . ?
C35 C36 C37 125.54(17) . . ?
C35 C36 C41 116.71(16) . . ?
C37 C36 C41 117.74(18) . . ?
C38 C37 C36 120.21(19) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C37 C38 C39 121.40(19) . . ?
C37 C38 H38 119.3 . . ?
C39 C38 H38 119.3 . . ?
C40 C39 C38 121.4(2) . . ?
C40 C39 H39 119.3 . . ?
C38 C39 H39 119.3 . . ?
C39 C40 C41 118.47(19) . . ?
C39 C40 C45 121.1(2) . . ?
C41 C40 C45 120.41(18) . . ?
N7 C41 C36 122.62(17) . . ?
N7 C41 C40 116.86(17) . . ?
C36 C41 C40 120.44(17) . . ?
N7 C42 N8 116.45(15) . . ?
N7 C42 C34 124.78(16) . . ?
N8 C42 C34 118.72(16) . . ?
O6 C43 N8 122.06(19) . . ?
O6 C43 N9 121.1(2) . . ?
N8 C43 N9 116.77(16) . . ?
F8 C44 F7 108.95(16) . . ?
F8 C44 F9 104.17(16) . . ?
F7 C44 F9 106.44(15) . . ?
F8 C44 C35 112.73(14) . . ?
F7 C44 C35 112.25(16) . . ?
F9 C44 C35 111.81(16) . . ?
C46 C45 C40 110.99(17) . . ?
C46 C45 H45A 109.4 . . ?
C40 C45 H45A 109.4 . . ?
C46 C45 H45B 109.4 . . ?
C40 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
C45 C46 Cl3 109.36(15) . . ?
C45 C46 H46A 109.8 . . ?
Cl3 C46 H46A 109.8 . . ?
C45 C46 H46B 109.8 . . ?
Cl3 C46 H46B 109.8 . . ?
H46A C46 H46B 108.3 . . ?
N8 C47 H47A 109.5 . . ?
N8 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
N8 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N9 C48 H48A 109.5 . . ?
N9 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N9 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C58 N10 C57 118.46(15) . . ?
C59 N11 C58 123.41(15) . . ?
C59 N11 C63 117.90(15) . . ?
C58 N11 C63 118.66(16) . . ?
C49 N12 C59 125.59(16) . . ?
C49 N12 C64 118.15(16) . . ?
C59 N12 C64 116.18(15) . . ?
O7 C49 N12 120.44(17) . . ?
O7 C49 C50 124.08(16) . . ?
N12 C49 C50 115.44(15) . . ?
C51 C50 C58 117.08(16) . . ?
C51 C50 C49 124.80(16) . . ?
C58 C50 C49 118.00(15) . . ?
C50 C51 C52 119.54(15) . . ?
C50 C51 C60 121.00(16) . . ?
C52 C51 C60 119.36(15) . . ?
C51 C52 C57 117.20(15) . . ?
C51 C52 C53 125.13(16) . . ?
C57 C52 C53 117.66(17) . . ?
C54 C53 C52 120.14(17) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C55 121.64(17) . . ?
C53 C54 H54 119.2 . . ?
C55 C54 H54 119.2 . . ?
C56 C55 C54 120.84(19) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 H55 119.6 . . ?
C55 C56 C57 118.69(17) . . ?
C55 C56 C61 120.82(18) . . ?
C57 C56 C61 120.46(16) . . ?
N10 C57 C56 116.79(15) . . ?
N10 C57 C52 122.38(16) . . ?
C56 C57 C52 120.82(16) . . ?
N10 C58 N11 115.94(15) . . ?
N10 C58 C50 124.69(15) . . ?
N11 C58 C50 119.35(16) . . ?
O8 C59 N11 122.71(18) . . ?
O8 C59 N12 120.96(18) . . ?
N11 C59 N12 116.29(15) . . ?
F11 C60 F12 108.24(15) . . ?
F11 C60 F10 104.50(13) . . ?
F12 C60 F10 106.44(13) . . ?
F11 C60 C51 113.20(13) . . ?
F12 C60 C51 112.31(14) . . ?
F10 C60 C51 111.64(15) . . ?
C56 C61 C62 109.64(17) . . ?
C56 C61 H61A 109.7 . . ?
C62 C61 H61A 109.7 . . ?
C56 C61 H61B 109.7 . . ?
C62 C61 H61B 109.7 . . ?
H61A C61 H61B 108.2 . . ?
C61 C62 Cl4 111.26(16) . . ?
C61 C62 H62A 109.4 . . ?
Cl4 C62 H62A 109.4 . . ?
C61 C62 H62B 109.4 . . ?
Cl4 C62 H62B 109.4 . . ?
H62A C62 H62B 108.0 . . ?
N11 C63 H63A 109.5 . . ?
N11 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
N11 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
N12 C64 H64A 109.5 . . ?
N12 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
N12 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N3 C1 O1 157.81(19) . . . . ?
C16 N3 C1 O1 -10.1(3) . . . . ?
C11 N3 C1 C2 -19.8(3) . . . . ?
C16 N3 C1 C2 172.33(17) . . . . ?
O1 C1 C2 C3 24.1(3) . . . . ?
N3 C1 C2 C3 -158.40(18) . . . . ?
O1 C1 C2 C10 -151.52(19) . . . . ?
N3 C1 C2 C10 26.0(2) . . . . ?
C10 C2 C3 C4 10.2(3) . . . . ?
C1 C2 C3 C4 -165.38(17) . . . . ?
C10 C2 C3 C12 -166.41(16) . . . . ?
C1 C2 C3 C12 18.0(3) . . . . ?
C2 C3 C4 C5 173.23(17) . . . . ?
C12 C3 C4 C5 -10.1(3) . . . . ?
C2 C3 C4 C9 -3.4(3) . . . . ?
C12 C3 C4 C9 173.27(16) . . . . ?
C3 C4 C5 C6 -177.19(17) . . . . ?
C9 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C6 C7 C8 C13 178.10(18) . . . . ?
C10 N1 C9 C8 -175.81(16) . . . . ?
C10 N1 C9 C4 6.2(3) . . . . ?
C7 C8 C9 N1 -177.17(17) . . . . ?
C13 C8 C9 N1 3.5(3) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C13 C8 C9 C4 -178.49(17) . . . . ?
C3 C4 C9 N1 -5.2(3) . . . . ?
C5 C4 C9 N1 178.00(17) . . . . ?
C3 C4 C9 C8 176.89(16) . . . . ?
C5 C4 C9 C8 0.1(3) . . . . ?
C9 N1 C10 N2 -176.61(15) . . . . ?
C9 N1 C10 C2 1.4(3) . . . . ?
C11 N2 C10 N1 175.44(17) . . . . ?
C15 N2 C10 N1 0.9(3) . . . . ?
C11 N2 C10 C2 -2.7(3) . . . . ?
C15 N2 C10 C2 -177.28(17) . . . . ?
C3 C2 C10 N1 -9.7(3) . . . . ?
C1 C2 C10 N1 166.25(17) . . . . ?
C3 C2 C10 N2 168.30(16) . . . . ?
C1 C2 C10 N2 -15.8(2) . . . . ?
C10 N2 C11 O2 -172.33(18) . . . . ?
C15 N2 C11 O2 2.3(3) . . . . ?
C10 N2 C11 N3 10.0(3) . . . . ?
C15 N2 C11 N3 -175.28(17) . . . . ?
C1 N3 C11 O2 -175.46(19) . . . . ?
C16 N3 C11 O2 -7.5(3) . . . . ?
C1 N3 C11 N2 2.2(3) . . . . ?
C16 N3 C11 N2 170.12(18) . . . . ?
C2 C3 C12 F1 24.3(2) . . . . ?
C4 C3 C12 F1 -152.34(16) . . . . ?
C2 C3 C12 F3 -99.3(2) . . . . ?
C4 C3 C12 F3 84.1(2) . . . . ?
C2 C3 C12 F2 141.17(17) . . . . ?
C4 C3 C12 F2 -35.4(2) . . . . ?
C7 C8 C13 C14 100.0(2) . . . . ?
C9 C8 C13 C14 -80.6(2) . . . . ?
C8 C13 C14 Cl1 -169.24(14) . . . . ?
C27 N6 C17 O3 -161.81(18) . . . . ?
C32 N6 C17 O3 3.1(3) . . . . ?
C27 N6 C17 C18 15.3(3) . . . . ?
C32 N6 C17 C18 -179.75(16) . . . . ?
O3 C17 C18 C19 -18.1(3) . . . . ?
N6 C17 C18 C19 164.83(17) . . . . ?
O3 C17 C18 C26 155.06(18) . . . . ?
N6 C17 C18 C26 -22.0(2) . . . . ?
C26 C18 C19 C20 -8.8(2) . . . . ?
C17 C18 C19 C20 164.38(16) . . . . ?
C26 C18 C19 C28 169.14(16) . . . . ?
C17 C18 C19 C28 -17.7(3) . . . . ?
C18 C19 C20 C21 -175.20(17) . . . . ?
C28 C19 C20 C21 6.8(3) . . . . ?
C18 C19 C20 C25 2.1(2) . . . . ?
C28 C19 C20 C25 -175.89(15) . . . . ?
C19 C20 C21 C22 178.13(18) . . . . ?
C25 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C22 C23 C24 C29 178.54(18) . . . . ?
C26 N4 C25 C24 176.64(16) . . . . ?
C26 N4 C25 C20 -5.7(2) . . . . ?
C23 C24 C25 N4 176.12(17) . . . . ?
C29 C24 C25 N4 -1.3(2) . . . . ?
C23 C24 C25 C20 -1.6(3) . . . . ?
C29 C24 C25 C20 -178.96(16) . . . . ?
C19 C20 C25 N4 5.5(2) . . . . ?
C21 C20 C25 N4 -176.98(16) . . . . ?
C19 C20 C25 C24 -176.95(16) . . . . ?
C21 C20 C25 C24 0.6(3) . . . . ?
C25 N4 C26 N5 177.16(15) . . . . ?
C25 N4 C26 C18 -1.8(3) . . . . ?
C27 N5 C26 N4 178.06(16) . . . . ?
C31 N5 C26 N4 -3.3(2) . . . . ?
C27 N5 C26 C18 -2.9(3) . . . . ?
C31 N5 C26 C18 175.68(17) . . . . ?
C19 C18 C26 N4 9.1(3) . . . . ?
C17 C18 C26 N4 -164.63(16) . . . . ?
C19 C18 C26 N5 -169.78(16) . . . . ?
C17 C18 C26 N5 16.5(2) . . . . ?
C26 N5 C27 O4 177.28(18) . . . . ?
C31 N5 C27 O4 -1.4(3) . . . . ?
C26 N5 C27 N6 -4.9(3) . . . . ?
C31 N5 C27 N6 176.49(17) . . . . ?
C17 N6 C27 O4 175.84(18) . . . . ?
C32 N6 C27 O4 10.9(3) . . . . ?
C17 N6 C27 N5 -2.0(3) . . . . ?
C32 N6 C27 N5 -166.93(17) . . . . ?
C18 C19 C28 F4 -25.1(2) . . . . ?
C20 C19 C28 F4 152.82(16) . . . . ?
C18 C19 C28 F5 98.5(2) . . . . ?
C20 C19 C28 F5 -83.6(2) . . . . ?
C18 C19 C28 F6 -141.99(17) . . . . ?
C20 C19 C28 F6 35.9(2) . . . . ?
C23 C24 C29 C30 -98.5(2) . . . . ?
C25 C24 C29 C30 78.8(2) . . . . ?
C24 C29 C30 Cl2 174.69(14) . . . . ?
C43 N9 C33 O5 164.25(19) . . . . ?
C48 N9 C33 O5 -5.6(3) . . . . ?
C43 N9 C33 C34 -13.8(3) . . . . ?
C48 N9 C33 C34 176.36(17) . . . . ?
O5 C33 C34 C35 15.8(3) . . . . ?
N9 C33 C34 C35 -166.21(17) . . . . ?
O5 C33 C34 C42 -158.94(18) . . . . ?
N9 C33 C34 C42 19.0(2) . . . . ?
C42 C34 C35 C36 8.3(2) . . . . ?
C33 C34 C35 C36 -166.48(17) . . . . ?
C42 C34 C35 C44 -167.71(16) . . . . ?
C33 C34 C35 C44 17.5(3) . . . . ?
C34 C35 C36 C37 171.00(18) . . . . ?
C44 C35 C36 C37 -13.0(3) . . . . ?
C34 C35 C36 C41 -7.4(3) . . . . ?
C44 C35 C36 C41 168.65(16) . . . . ?
C35 C36 C37 C38 178.95(19) . . . . ?
C41 C36 C37 C38 -2.7(3) . . . . ?
C36 C37 C38 C39 -2.2(3) . . . . ?
C37 C38 C39 C40 3.3(3) . . . . ?
C38 C39 C40 C41 0.7(3) . . . . ?
C38 C39 C40 C45 -178.1(2) . . . . ?
C42 N7 C41 C36 2.8(3) . . . . ?
C42 N7 C41 C40 179.52(17) . . . . ?
C35 C36 C41 N7 1.7(3) . . . . ?
C37 C36 C41 N7 -176.78(18) . . . . ?
C35 C36 C41 C40 -174.86(17) . . . . ?
C37 C36 C41 C40 6.6(3) . . . . ?
C39 C40 C41 N7 177.55(19) . . . . ?
C45 C40 C41 N7 -3.6(3) . . . . ?
C39 C40 C41 C36 -5.7(3) . . . . ?
C45 C40 C41 C36 173.13(18) . . . . ?
C41 N7 C42 N8 -179.25(16) . . . . ?
C41 N7 C42 C34 -1.9(3) . . . . ?
C43 N8 C42 N7 174.13(17) . . . . ?
C47 N8 C42 N7 -1.8(3) . . . . ?
C43 N8 C42 C34 -3.4(3) . . . . ?
C47 N8 C42 C34 -179.41(17) . . . . ?
C35 C34 C42 N7 -3.7(3) . . . . ?
C33 C34 C42 N7 171.41(17) . . . . ?
C35 C34 C42 N8 173.61(16) . . . . ?
C33 C34 C42 N8 -11.3(2) . . . . ?
C42 N8 C43 O6 -171.82(19) . . . . ?
C47 N8 C43 O6 4.2(3) . . . . ?
C42 N8 C43 N9 9.5(3) . . . . ?
C47 N8 C43 N9 -174.51(18) . . . . ?
C33 N9 C43 O6 -178.9(2) . . . . ?
C48 N9 C43 O6 -9.0(3) . . . . ?
C33 N9 C43 N8 -0.1(3) . . . . ?
C48 N9 C43 N8 169.78(18) . . . . ?
C34 C35 C44 F8 32.7(2) . . . . ?
C36 C35 C44 F8 -143.32(17) . . . . ?
C34 C35 C44 F7 -90.8(2) . . . . ?
C36 C35 C44 F7 93.2(2) . . . . ?
C34 C35 C44 F9 149.67(17) . . . . ?
C36 C35 C44 F9 -26.4(2) . . . . ?
C39 C40 C45 C46 -94.3(3) . . . . ?
C41 C40 C45 C46 86.9(3) . . . . ?
C40 C45 C46 Cl3 172.54(15) . . . . ?
C59 N12 C49 O7 -168.55(18) . . . . ?
C64 N12 C49 O7 8.2(3) . . . . ?
C59 N12 C49 C50 9.1(3) . . . . ?
C64 N12 C49 C50 -174.15(16) . . . . ?
O7 C49 C50 C51 -13.3(3) . . . . ?
N12 C49 C50 C51 169.09(16) . . . . ?
O7 C49 C50 C58 162.66(17) . . . . ?
N12 C49 C50 C58 -14.9(2) . . . . ?
C58 C50 C51 C52 -9.1(2) . . . . ?
C49 C50 C51 C52 166.89(16) . . . . ?
C58 C50 C51 C60 167.14(15) . . . . ?
C49 C50 C51 C60 -16.8(3) . . . . ?
C50 C51 C52 C57 8.4(2) . . . . ?
C60 C51 C52 C57 -167.96(15) . . . . ?
C50 C51 C52 C53 -169.92(17) . . . . ?
C60 C51 C52 C53 13.8(3) . . . . ?
C51 C52 C53 C54 -178.66(17) . . . . ?
C57 C52 C53 C54 3.1(3) . . . . ?
C52 C53 C54 C55 1.0(3) . . . . ?
C53 C54 C55 C56 -3.1(3) . . . . ?
C54 C55 C56 C57 1.0(3) . . . . ?
C54 C55 C56 C61 -176.93(18) . . . . ?
C58 N10 C57 C56 178.34(16) . . . . ?
C58 N10 C57 C52 -2.8(3) . . . . ?
C55 C56 C57 N10 -178.02(17) . . . . ?
C61 C56 C57 N10 -0.1(3) . . . . ?
C55 C56 C57 C52 3.1(3) . . . . ?
C61 C56 C57 C52 -178.95(17) . . . . ?
C51 C52 C57 N10 -2.3(3) . . . . ?
C53 C52 C57 N10 176.10(17) . . . . ?
C51 C52 C57 C56 176.48(16) . . . . ?
C53 C52 C57 C56 -5.1(3) . . . . ?
C57 N10 C58 N11 -179.63(15) . . . . ?
C57 N10 C58 C50 2.0(3) . . . . ?
C59 N11 C58 N10 -175.23(16) . . . . ?
C63 N11 C58 N10 2.7(2) . . . . ?
C59 N11 C58 C50 3.2(3) . . . . ?
C63 N11 C58 C50 -178.80(16) . . . . ?
C51 C50 C58 N10 4.0(3) . . . . ?
C49 C50 C58 N10 -172.27(16) . . . . ?
C51 C50 C58 N11 -174.30(16) . . . . ?
C49 C50 C58 N11 9.4(2) . . . . ?
C58 N11 C59 O8 172.72(18) . . . . ?
C63 N11 C59 O8 -5.3(3) . . . . ?
C58 N11 C59 N12 -9.5(3) . . . . ?
C63 N11 C59 N12 172.50(17) . . . . ?
C49 N12 C59 O8 -179.34(18) . . . . ?
C64 N12 C59 O8 3.9(3) . . . . ?
C49 N12 C59 N11 2.9(3) . . . . ?
C64 N12 C59 N11 -173.92(17) . . . . ?
C50 C51 C60 F11 -33.0(2) . . . . ?
C52 C51 C60 F11 143.31(16) . . . . ?
C50 C51 C60 F12 89.99(19) . . . . ?
C52 C51 C60 F12 -93.73(19) . . . . ?
C50 C51 C60 F10 -150.55(16) . . . . ?
C52 C51 C60 F10 25.7(2) . . . . ?
C55 C56 C61 C62 95.9(2) . . . . ?
C57 C56 C61 C62 -82.0(2) . . . . ?
C56 C61 C62 Cl4 -178.57(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.053

_database_code_depnum_ccdc_archive 'CCDC 895401'
#######################################################################
#
#                 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_is_sd402
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 F3 N3 O2'
_chemical_formula_sum            'C23 H22 F3 N3 O2'
_chemical_formula_weight         429.44

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   8.6107(7)
_cell_length_b                   11.0873(10)
_cell_length_c                   11.3982(10)
_cell_angle_alpha                102.613(5)
_cell_angle_beta                 91.556(6)
_cell_angle_gamma                106.607(5)
_cell_volume                     1012.95(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6022
_cell_measurement_theta_min      4.717
_cell_measurement_theta_max      62.885

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28093
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         32.50
_reflns_number_total             7309
_reflns_number_gt                4879
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms were positioned geometrically and refined using a
riding model, with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with <i>U</i>~iso~(H) =
1.5 times <i>U</i>~eq~(C) (methyl groups) or with <i>U</i>~iso~(H) = 1.2 times
<i>U</i>~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0641P)^2^+0.2302P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7309
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.77279(14) 0.03506(12) 0.37197(10) 0.0184(2) Uani 1 1 d . . .
C2 C 0.75752(15) 0.00392(12) 0.48511(11) 0.0204(2) Uani 1 1 d . . .
C3 C 0.63174(16) -0.10431(13) 0.49434(11) 0.0231(3) Uani 1 1 d . . .
H3 H 0.6216 -0.1264 0.5703 0.028 Uiso 1 1 calc R . .
C4 C 0.52031(15) -0.18146(12) 0.39724(12) 0.0227(2) Uani 1 1 d . . .
C5 C 0.53376(15) -0.14668(12) 0.28707(11) 0.0211(2) Uani 1 1 d . . .
H5 H 0.4568 -0.1959 0.2202 0.025 Uiso 1 1 calc R . .
C6 C 0.65902(14) -0.04047(11) 0.27423(10) 0.0183(2) Uani 1 1 d . . .
C7 C 0.67975(14) -0.00542(11) 0.15321(10) 0.0191(2) Uani 1 1 d . . .
H7 H 0.5693 -0.0291 0.1091 0.023 Uiso 1 1 calc R . .
C8 C 0.75657(14) 0.14264(11) 0.17545(10) 0.0180(2) Uani 1 1 d . . .
C9 C 0.78202(15) 0.18600(12) 0.05848(11) 0.0211(2) Uani 1 1 d . . .
C10 C 1.05578(15) 0.32576(12) 0.14252(11) 0.0209(2) Uani 1 1 d . . .
C11 C 0.90629(14) 0.18133(11) 0.26365(10) 0.0176(2) Uani 1 1 d . . .
C12 C 0.87407(17) 0.08353(14) 0.59363(11) 0.0271(3) Uani 1 1 d . . .
H12A H 0.8402 0.1594 0.6305 0.041 Uiso 1 1 calc R . .
H12B H 0.9840 0.1121 0.5686 0.041 Uiso 1 1 calc R . .
H12C H 0.8739 0.0310 0.6525 0.041 Uiso 1 1 calc R . .
C13 C 0.39022(18) -0.30087(14) 0.41018(14) 0.0326(3) Uani 1 1 d . . .
H13A H 0.3034 -0.2753 0.4532 0.049 Uiso 1 1 calc R . .
H13B H 0.4377 -0.3492 0.4558 0.049 Uiso 1 1 calc R . .
H13C H 0.3450 -0.3557 0.3299 0.049 Uiso 1 1 calc R . .
C14 C 0.77662(16) -0.08465(13) 0.07986(11) 0.0253(3) Uani 1 1 d . . .
C15 C 0.94263(18) 0.32438(14) -0.05873(12) 0.0289(3) Uani 1 1 d . . .
H15A H 0.9132 0.2516 -0.1299 0.043 Uiso 1 1 calc R . .
H15B H 1.0553 0.3769 -0.0595 0.043 Uiso 1 1 calc R . .
H15C H 0.8698 0.3778 -0.0601 0.043 Uiso 1 1 calc R . .
C16 C 1.18957(17) 0.31682(16) 0.32878(13) 0.0339(3) Uani 1 1 d . . .
H16A H 1.2876 0.3338 0.2857 0.051 Uiso 1 1 calc R . .
H16B H 1.1895 0.2503 0.3730 0.051 Uiso 1 1 calc R . .
H16C H 1.1885 0.3967 0.3858 0.051 Uiso 1 1 calc R . .
C17 C 0.62981(15) 0.20831(12) 0.23615(12) 0.0216(2) Uani 1 1 d . . .
H17A H 0.5235 0.1685 0.1870 0.026 Uiso 1 1 calc R . .
H17B H 0.6154 0.1898 0.3170 0.026 Uiso 1 1 calc R . .
C18 C 0.67754(15) 0.35317(12) 0.25003(11) 0.0220(2) Uani 1 1 d . . .
C19 C 0.59881(17) 0.40516(14) 0.17499(14) 0.0299(3) Uani 1 1 d . . .
H19 H 0.5155 0.3492 0.1149 0.036 Uiso 1 1 calc R . .
C20 C 0.6406(2) 0.53817(15) 0.18702(15) 0.0375(4) Uani 1 1 d . . .
H20 H 0.5847 0.5724 0.1359 0.045 Uiso 1 1 calc R . .
C21 C 0.76265(19) 0.62082(14) 0.27262(14) 0.0337(3) Uani 1 1 d . . .
H21 H 0.7918 0.7117 0.2799 0.040 Uiso 1 1 calc R . .
C22 C 0.84254(18) 0.57062(14) 0.34800(13) 0.0298(3) Uani 1 1 d . . .
H22 H 0.9273 0.6271 0.4067 0.036 Uiso 1 1 calc R . .
C23 C 0.79890(16) 0.43794(13) 0.33786(12) 0.0256(3) Uani 1 1 d . . .
H23 H 0.8523 0.4044 0.3913 0.031 Uiso 1 1 calc R . .
F1 F 0.70255(11) -0.21160(8) 0.06352(8) 0.0367(2) Uani 1 1 d . . .
F2 F 0.79554(13) -0.06385(9) -0.03089(8) 0.0446(3) Uani 1 1 d . . .
F3 F 0.92656(10) -0.06291(9) 0.13201(9) 0.0413(2) Uani 1 1 d . . .
N1 N 0.90889(12) 0.13727(10) 0.35853(9) 0.0202(2) Uani 1 1 d . . .
N2 N 1.04438(12) 0.27136(10) 0.24153(9) 0.0206(2) Uani 1 1 d . . .
N3 N 0.92705(12) 0.27468(10) 0.05115(9) 0.0203(2) Uani 1 1 d . . .
O1 O 1.17508(12) 0.41220(10) 0.13375(9) 0.0332(2) Uani 1 1 d . . .
O2 O 0.67335(12) 0.14990(10) -0.02268(9) 0.0324(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0184(5) 0.0180(5) 0.0194(5) 0.0074(4) 0.0015(4) 0.0041(4)
C2 0.0225(6) 0.0213(6) 0.0202(5) 0.0082(5) 0.0019(4) 0.0082(5)
C3 0.0267(6) 0.0258(6) 0.0215(6) 0.0128(5) 0.0063(5) 0.0096(5)
C4 0.0236(6) 0.0189(6) 0.0280(6) 0.0113(5) 0.0070(5) 0.0054(5)
C5 0.0212(6) 0.0169(6) 0.0245(6) 0.0071(5) 0.0018(4) 0.0026(4)
C6 0.0188(5) 0.0172(5) 0.0199(5) 0.0075(4) 0.0024(4) 0.0044(4)
C7 0.0183(5) 0.0167(5) 0.0196(5) 0.0064(4) -0.0001(4) -0.0001(4)
C8 0.0171(5) 0.0172(5) 0.0191(5) 0.0079(4) 0.0008(4) 0.0015(4)
C9 0.0212(6) 0.0196(6) 0.0211(5) 0.0076(5) 0.0008(4) 0.0022(5)
C10 0.0211(6) 0.0179(6) 0.0226(6) 0.0063(4) 0.0033(4) 0.0028(4)
C11 0.0166(5) 0.0152(5) 0.0196(5) 0.0045(4) 0.0008(4) 0.0023(4)
C12 0.0306(7) 0.0300(7) 0.0208(6) 0.0083(5) -0.0022(5) 0.0081(6)
C13 0.0341(7) 0.0259(7) 0.0356(7) 0.0157(6) 0.0063(6) -0.0009(6)
C14 0.0297(7) 0.0201(6) 0.0225(6) 0.0055(5) 0.0038(5) 0.0015(5)
C15 0.0349(7) 0.0276(7) 0.0232(6) 0.0140(5) 0.0037(5) 0.0015(6)
C16 0.0218(6) 0.0400(8) 0.0327(7) 0.0160(6) -0.0069(5) -0.0069(6)
C17 0.0180(5) 0.0203(6) 0.0279(6) 0.0106(5) 0.0034(5) 0.0042(4)
C18 0.0210(6) 0.0215(6) 0.0260(6) 0.0095(5) 0.0074(5) 0.0070(5)
C19 0.0272(7) 0.0269(7) 0.0375(7) 0.0121(6) -0.0005(6) 0.0079(5)
C20 0.0406(9) 0.0308(8) 0.0487(9) 0.0195(7) 0.0018(7) 0.0149(7)
C21 0.0393(8) 0.0210(7) 0.0438(8) 0.0122(6) 0.0130(7) 0.0092(6)
C22 0.0338(7) 0.0233(7) 0.0291(7) 0.0041(5) 0.0062(6) 0.0048(5)
C23 0.0304(7) 0.0237(6) 0.0240(6) 0.0086(5) 0.0051(5) 0.0078(5)
F1 0.0478(5) 0.0169(4) 0.0389(5) 0.0020(3) 0.0100(4) 0.0028(4)
F2 0.0715(7) 0.0406(5) 0.0269(4) 0.0129(4) 0.0219(4) 0.0195(5)
F3 0.0278(5) 0.0424(5) 0.0484(5) -0.0047(4) 0.0020(4) 0.0140(4)
N1 0.0184(5) 0.0195(5) 0.0209(5) 0.0066(4) -0.0005(4) 0.0017(4)
N2 0.0169(5) 0.0209(5) 0.0215(5) 0.0073(4) -0.0003(4) -0.0001(4)
N3 0.0221(5) 0.0190(5) 0.0190(5) 0.0084(4) 0.0029(4) 0.0019(4)
O1 0.0285(5) 0.0292(5) 0.0353(5) 0.0148(4) 0.0014(4) -0.0067(4)
O2 0.0288(5) 0.0370(6) 0.0268(5) 0.0172(4) -0.0071(4) -0.0036(4)

#==============================================================================

# MOLECULAR GEOMETRY

_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 C6 1.4024(16) . ?
C1 C2 1.4061(16) . ?
C1 N1 1.4168(15) . ?
C2 C3 1.3937(18) . ?
C2 C12 1.5052(18) . ?
C3 C4 1.3918(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3902(17) . ?
C4 C13 1.5087(18) . ?
C5 C6 1.3890(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5144(16) . ?
C7 C14 1.5173(18) . ?
C7 C8 1.5444(17) . ?
C7 H7 1.0000 . ?
C8 C11 1.5106(16) . ?
C8 C9 1.5140(16) . ?
C8 C17 1.5734(17) . ?
C9 O2 1.2119(15) . ?
C9 N3 1.3685(15) . ?
C10 O1 1.2118(15) . ?
C10 N2 1.3843(15) . ?
C10 N3 1.3982(16) . ?
C11 N1 1.2823(15) . ?
C11 N2 1.3863(15) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 F1 1.3374(15) . ?
C14 F2 1.3380(15) . ?
C14 F3 1.3402(16) . ?
C15 N3 1.4692(15) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N2 1.4695(16) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.5106(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.3894(19) . ?
C18 C23 1.3959(19) . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.3878(19) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.29(11) . . ?
C6 C1 N1 121.89(10) . . ?
C2 C1 N1 118.71(11) . . ?
C3 C2 C1 118.15(11) . . ?
C3 C2 C12 120.39(11) . . ?
C1 C2 C12 121.45(11) . . ?
C4 C3 C2 122.95(11) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C5 C4 C3 118.13(11) . . ?
C5 C4 C13 120.75(12) . . ?
C3 C4 C13 121.11(11) . . ?
C6 C5 C4 120.41(12) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.01(11) . . ?
C5 C6 C7 120.91(11) . . ?
C1 C6 C7 118.06(10) . . ?
C6 C7 C14 109.17(10) . . ?
C6 C7 C8 108.59(10) . . ?
C14 C7 C8 114.45(10) . . ?
C6 C7 H7 108.2 . . ?
C14 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C11 C8 C9 115.81(9) . . ?
C11 C8 C7 107.84(10) . . ?
C9 C8 C7 112.01(10) . . ?
C11 C8 C17 108.46(10) . . ?
C9 C8 C17 104.88(10) . . ?
C7 C8 C17 107.48(9) . . ?
O2 C9 N3 121.17(11) . . ?
O2 C9 C8 120.88(11) . . ?
N3 C9 C8 117.77(10) . . ?
O1 C10 N2 121.19(12) . . ?
O1 C10 N3 121.13(11) . . ?
N2 C10 N3 117.65(10) . . ?
N1 C11 N2 119.36(11) . . ?
N1 C11 C8 122.87(10) . . ?
N2 C11 C8 117.74(10) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F1 C14 F2 105.74(11) . . ?
F1 C14 F3 106.23(11) . . ?
F2 C14 F3 106.28(11) . . ?
F1 C14 C7 111.16(10) . . ?
F2 C14 C7 113.42(11) . . ?
F3 C14 C7 113.43(11) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C8 114.22(9) . . ?
C18 C17 H17A 108.7 . . ?
C8 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C8 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C23 118.34(12) . . ?
C19 C18 C17 119.96(12) . . ?
C23 C18 C17 121.70(11) . . ?
C20 C19 C18 120.67(14) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.50(14) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.58(13) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.09(14) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.80(13) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C11 N1 C1 118.07(10) . . ?
C10 N2 C11 124.49(10) . . ?
C10 N2 C16 116.15(10) . . ?
C11 N2 C16 119.34(10) . . ?
C9 N3 C10 124.88(10) . . ?
C9 N3 C15 116.63(10) . . ?
C10 N3 C15 118.38(10) . . ?

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
C6 C1 C2 C3 2.05(17) . . . . ?
N1 C1 C2 C3 -174.10(11) . . . . ?
C6 C1 C2 C12 -178.63(12) . . . . ?
N1 C1 C2 C12 5.22(18) . . . . ?
C1 C2 C3 C4 -0.73(19) . . . . ?
C12 C2 C3 C4 179.94(12) . . . . ?
C2 C3 C4 C5 -1.46(19) . . . . ?
C2 C3 C4 C13 177.48(13) . . . . ?
C3 C4 C5 C6 2.32(18) . . . . ?
C13 C4 C5 C6 -176.63(12) . . . . ?
C4 C5 C6 C1 -1.02(18) . . . . ?
C4 C5 C6 C7 177.05(11) . . . . ?
C2 C1 C6 C5 -1.22(18) . . . . ?
N1 C1 C6 C5 174.81(11) . . . . ?
C2 C1 C6 C7 -179.34(11) . . . . ?
N1 C1 C6 C7 -3.31(17) . . . . ?
C5 C6 C7 C14 -84.52(14) . . . . ?
C1 C6 C7 C14 93.60(13) . . . . ?
C5 C6 C7 C8 150.08(11) . . . . ?
C1 C6 C7 C8 -31.80(14) . . . . ?
C6 C7 C8 C11 51.27(12) . . . . ?
C14 C7 C8 C11 -70.97(12) . . . . ?
C6 C7 C8 C9 179.84(10) . . . . ?
C14 C7 C8 C9 57.60(14) . . . . ?
C6 C7 C8 C17 -65.48(12) . . . . ?
C14 C7 C8 C17 172.28(10) . . . . ?
C11 C8 C9 O2 173.13(12) . . . . ?
C7 C8 C9 O2 48.90(16) . . . . ?
C17 C8 C9 O2 -67.37(15) . . . . ?
C11 C8 C9 N3 -11.73(16) . . . . ?
C7 C8 C9 N3 -135.97(11) . . . . ?
C17 C8 C9 N3 107.77(12) . . . . ?
C9 C8 C11 N1 -170.28(11) . . . . ?
C7 C8 C11 N1 -43.91(15) . . . . ?
C17 C8 C11 N1 72.20(14) . . . . ?
C9 C8 C11 N2 11.65(16) . . . . ?
C7 C8 C11 N2 138.02(11) . . . . ?
C17 C8 C11 N2 -105.87(11) . . . . ?
C6 C7 C14 F1 58.49(13) . . . . ?
C8 C7 C14 F1 -179.58(10) . . . . ?
C6 C7 C14 F2 177.48(10) . . . . ?
C8 C7 C14 F2 -60.59(14) . . . . ?
C6 C7 C14 F3 -61.14(13) . . . . ?
C8 C7 C14 F3 60.79(14) . . . . ?
C11 C8 C17 C18 70.84(13) . . . . ?
C9 C8 C17 C18 -53.46(13) . . . . ?
C7 C8 C17 C18 -172.81(10) . . . . ?
C8 C17 C18 C19 106.04(13) . . . . ?
C8 C17 C18 C23 -74.61(15) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
C17 C18 C19 C20 179.64(13) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C19 C20 C21 C22 -0.8(2) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C21 C22 C23 C18 1.7(2) . . . . ?
C19 C18 C23 C22 -1.56(19) . . . . ?
C17 C18 C23 C22 179.08(12) . . . . ?
N2 C11 N1 C1 -173.09(11) . . . . ?
C8 C11 N1 C1 8.87(17) . . . . ?
C6 C1 N1 C11 17.11(17) . . . . ?
C2 C1 N1 C11 -166.84(11) . . . . ?
O1 C10 N2 C11 173.50(12) . . . . ?
N3 C10 N2 C11 -8.50(18) . . . . ?
O1 C10 N2 C16 -4.93(19) . . . . ?
N3 C10 N2 C16 173.08(11) . . . . ?
N1 C11 N2 C10 -179.87(11) . . . . ?
C8 C11 N2 C10 -1.73(17) . . . . ?
N1 C11 N2 C16 -1.49(18) . . . . ?
C8 C11 N2 C16 176.65(12) . . . . ?
O2 C9 N3 C10 177.02(12) . . . . ?
C8 C9 N3 C10 1.90(18) . . . . ?
O2 C9 N3 C15 0.77(18) . . . . ?
C8 C9 N3 C15 -174.35(11) . . . . ?
O1 C10 N3 C9 -173.55(12) . . . . ?
N2 C10 N3 C9 8.44(18) . . . . ?
O1 C10 N3 C15 2.63(19) . . . . ?
N2 C10 N3 C15 -175.37(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        32.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.054


_database_code_depnum_ccdc_archive 'CCDC 934983'