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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H9 F4 N3 O4'
_chemical_formula_sum            'C18 H9 F4 N3 O4'
_chemical_formula_weight         407.28

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.1325(14)
_cell_length_b                   11.657(2)
_cell_length_c                   11.979(2)
_cell_angle_alpha                61.83(3)
_cell_angle_beta                 86.14(3)
_cell_angle_gamma                76.85(3)
_cell_volume                     854.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      1.9305
_cell_measurement_theta_max      27.4294

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6665
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2983
_reflns_number_gt                2370
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1458P)²+0.6436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2983
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.1067
_refine_ls_wR_factor_ref         0.2900
_refine_ls_wR_factor_gt          0.2711
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 1.1851(3) -0.0849(2) 0.5887(2) 0.0465(7) Uani 1 1 d . . .
F2 F 0.8129(3) 0.0931(2) 0.9060(2) 0.0453(7) Uani 1 1 d . . .
F3 F 1.0863(4) 0.1747(2) 0.5094(2) 0.0463(7) Uani 1 1 d . . .
O3 O 0.7174(5) 0.6237(3) 0.7846(3) 0.0541(9) Uani 1 1 d . . .
F1 F 0.9215(4) -0.1664(2) 0.9852(2) 0.0478(7) Uani 1 1 d . . .
C5 C 1.0377(6) 0.0947(4) 0.6276(4) 0.0373(9) Uani 1 1 d . . .
C11 C 0.5873(6) 0.8052(4) 0.8228(4) 0.0390(10) Uani 1 1 d . . .
C12 C 0.5037(6) 0.8546(4) 0.9033(4) 0.0417(10) Uani 1 1 d . . .
H12 H 0.4900 0.7948 0.9897 0.050 Uiso 1 1 calc R . .
C3 C 0.9079(6) 0.0544(4) 0.8254(4) 0.0379(9) Uani 1 1 d . . .
O2 O 0.8709(5) 0.3297(3) 0.7443(3) 0.0481(8) Uani 1 1 d . . .
N3 N 1.1046(6) -0.2738(4) 0.8434(4) 0.0487(10) Uani 1 1 d . . .
C6 C 1.0933(6) -0.0417(4) 0.6686(4) 0.0361(9) Uani 1 1 d . . .
C14 C 0.4631(6) 1.0810(4) 0.7322(4) 0.0394(10) Uani 1 1 d . . .
C10 C 0.6606(7) 0.6585(4) 0.8743(4) 0.0460(11) Uani 1 1 d . . .
C4 C 0.9454(6) 0.1471(4) 0.7038(4) 0.0369(9) Uani 1 1 d . . .
C13 C 0.4392(6) 0.9919(4) 0.8586(4) 0.0386(10) Uani 1 1 d . . .
H13 H 0.3790 1.0249 0.9141 0.046 Uiso 1 1 calc R . .
O4 O 0.6670(6) 0.5799(3) 0.9865(3) 0.0630(10) Uani 1 1 d . . .
C1 C 1.0563(6) -0.1335(4) 0.7903(4) 0.0367(9) Uani 1 1 d . . .
C15 C 0.5461(6) 1.0298(4) 0.6509(4) 0.0409(10) Uani 1 1 d . . .
H15 H 0.5605 1.0892 0.5645 0.049 Uiso 1 1 calc R . .
C16 C 0.6076(6) 0.8933(4) 0.6951(4) 0.0421(10) Uani 1 1 d . . .
H16 H 0.6633 0.8595 0.6392 0.051 Uiso 1 1 calc R . .
O1 O 0.8511(5) 0.3724(3) 0.5430(3) 0.0569(9) Uani 1 1 d . . .
C17 C 0.4056(7) 1.2216(4) 0.6874(4) 0.0464(11) Uani 1 1 d . . .
C2 C 0.9635(6) -0.0813(4) 0.8668(4) 0.0379(9) Uani 1 1 d . . .
C7 C 0.8838(6) 0.2955(4) 0.6526(4) 0.0427(10) Uani 1 1 d . . .
N2 N 1.1840(6) -0.3246(4) 0.7769(4) 0.0544(10) Uani 1 1 d . . .
C8 C 0.8072(8) 0.4715(4) 0.7052(5) 0.0546(12) Uani 1 1 d . . .
H8A H 0.6828 0.5086 0.6558 0.066 Uiso 1 1 calc R . .
H8B H 0.9037 0.5205 0.6524 0.066 Uiso 1 1 calc R . .
C9 C 0.7855(8) 0.4825(5) 0.8252(5) 0.0567(13) Uani 1 1 d . . .
H9A H 0.6912 0.4319 0.8791 0.068 Uiso 1 1 calc R . .
H9B H 0.9105 0.4477 0.8737 0.068 Uiso 1 1 calc R . .
C18 C 0.3560(8) 1.3380(5) 0.6502(5) 0.0625(14) Uani 1 1 d . . .
H18 H 0.3162 1.4315 0.6203 0.075 Uiso 1 1 calc R . .
N1 N 1.2557(8) -0.3895(5) 0.7334(5) 0.0770(15) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4 C6 1.350(4) . ?
F2 C3 1.334(4) . ?
F3 C5 1.352(4) . ?
O3 C10 1.326(5) . ?
O3 C9 1.448(5) . ?
F1 C2 1.355(5) . ?
C5 C4 1.379(6) . ?
C5 C6 1.389(6) . ?
C11 C12 1.382(6) . ?
C11 C16 1.404(6) . ?
C11 C10 1.489(6) . ?
C12 C13 1.396(6) . ?
C12 H12 0.9500 . ?
C3 C2 1.381(6) . ?
C3 C4 1.397(6) . ?
O2 C7 1.325(5) . ?
O2 C8 1.454(5) . ?
N3 N2 1.240(5) . ?
N3 C1 1.410(5) . ?
C6 C1 1.394(6) . ?
C14 C13 1.401(6) . ?
C14 C15 1.402(6) . ?
C14 C17 1.427(6) . ?
C10 O4 1.215(6) . ?
C4 C7 1.501(6) . ?
C13 H13 0.9500 . ?
C1 C2 1.382(6) . ?
C15 C16 1.387(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O1 C7 1.191(5) . ?
C17 C18 1.182(7) . ?
N2 N1 1.125(6) . ?
C8 C9 1.497(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C18 H18 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
C10 O3 C9 116.8(4) . . ?
F3 C5 C4 121.2(4) . . ?
F3 C5 C6 116.2(4) . . ?
C4 C5 C6 122.5(4) . . ?
C12 C11 C16 119.9(4) . . ?
C12 C11 C10 119.2(4) . . ?
C16 C11 C10 120.8(4) . . ?
C11 C12 C13 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
F2 C3 C2 116.8(4) . . ?
F2 C3 C4 121.5(4) . . ?
C2 C3 C4 121.7(4) . . ?
C7 O2 C8 116.1(3) . . ?
N2 N3 C1 118.8(4) . . ?
F4 C6 C5 118.9(3) . . ?
F4 C6 C1 120.0(4) . . ?
C5 C6 C1 121.2(4) . . ?
C13 C14 C15 118.9(4) . . ?
C13 C14 C17 120.5(4) . . ?
C15 C14 C17 120.6(4) . . ?
O4 C10 O3 124.1(4) . . ?
O4 C10 C11 123.2(4) . . ?
O3 C10 C11 112.7(4) . . ?
C5 C4 C3 116.0(4) . . ?
C5 C4 C7 120.0(4) . . ?
C3 C4 C7 123.9(4) . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C2 C1 C6 116.4(4) . . ?
C2 C1 N3 116.8(4) . . ?
C6 C1 N3 126.8(4) . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 119.7(4) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C18 C17 C14 179.3(5) . . ?
F1 C2 C3 119.1(4) . . ?
F1 C2 C1 118.7(4) . . ?
C3 C2 C1 122.2(4) . . ?
O1 C7 O2 124.6(4) . . ?
O1 C7 C4 123.8(4) . . ?
O2 C7 C4 111.7(4) . . ?
N1 N2 N3 168.9(5) . . ?
O2 C8 C9 105.8(4) . . ?
O2 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O2 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
O3 C9 C8 105.0(4) . . ?
O3 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
O3 C9 H9B 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C17 C18 H18 180.0 . . ?

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
C16 C11 C12 C13 0.0(6) . . . . ?
C10 C11 C12 C13 178.0(4) . . . . ?
F3 C5 C6 F4 -1.9(5) . . . . ?
C4 C5 C6 F4 -179.2(3) . . . . ?
F3 C5 C6 C1 177.9(3) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C9 O3 C10 O4 1.8(7) . . . . ?
C9 O3 C10 C11 -178.1(4) . . . . ?
C12 C11 C10 O4 -6.9(7) . . . . ?
C16 C11 C10 O4 171.0(4) . . . . ?
C12 C11 C10 O3 173.0(4) . . . . ?
C16 C11 C10 O3 -9.0(6) . . . . ?
F3 C5 C4 C3 -178.1(3) . . . . ?
C6 C5 C4 C3 -0.9(6) . . . . ?
F3 C5 C4 C7 4.6(6) . . . . ?
C6 C5 C4 C7 -178.2(4) . . . . ?
F2 C3 C4 C5 -177.4(3) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
F2 C3 C4 C7 -0.2(6) . . . . ?
C2 C3 C4 C7 178.3(4) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C15 C14 C13 C12 2.3(6) . . . . ?
C17 C14 C13 C12 -177.1(4) . . . . ?
F4 C6 C1 C2 179.3(3) . . . . ?
C5 C6 C1 C2 -0.5(6) . . . . ?
F4 C6 C1 N3 -0.3(6) . . . . ?
C5 C6 C1 N3 179.9(4) . . . . ?
N2 N3 C1 C2 178.4(4) . . . . ?
N2 N3 C1 C6 -2.0(7) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C17 C14 C15 C16 178.0(4) . . . . ?
C14 C15 C16 C11 -0.2(6) . . . . ?
C12 C11 C16 C15 1.0(6) . . . . ?
C10 C11 C16 C15 -177.0(4) . . . . ?
C13 C14 C17 C18 -79(42) . . . . ?
C15 C14 C17 C18 102(42) . . . . ?
F2 C3 C2 F1 -0.7(6) . . . . ?
C4 C3 C2 F1 -179.3(3) . . . . ?
F2 C3 C2 C1 177.5(3) . . . . ?
C4 C3 C2 C1 -1.1(6) . . . . ?
C6 C1 C2 F1 179.0(3) . . . . ?
N3 C1 C2 F1 -1.4(5) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
N3 C1 C2 C3 -179.6(4) . . . . ?
C8 O2 C7 O1 1.7(7) . . . . ?
C8 O2 C7 C4 -178.5(4) . . . . ?
C5 C4 C7 O1 25.1(7) . . . . ?
C3 C4 C7 O1 -152.0(5) . . . . ?
C5 C4 C7 O2 -154.8(4) . . . . ?
C3 C4 C7 O2 28.2(6) . . . . ?
C1 N3 N2 N1 180(3) . . . . ?
C7 O2 C8 C9 174.4(4) . . . . ?
C10 O3 C9 C8 170.8(4) . . . . ?
O2 C8 C9 O3 -178.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 998247'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 F4 N3 O4'
_chemical_formula_sum            'C19 H11 F4 N3 O4'
_chemical_formula_weight         421.31

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.8306(12)
_cell_length_b                   9.969(2)
_cell_length_c                   15.544(3)
_cell_angle_alpha                71.39(3)
_cell_angle_beta                 87.46(3)
_cell_angle_gamma                86.71(3)
_cell_volume                     854.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3211
_cell_measurement_theta_min      2.1621
_cell_measurement_theta_max      27.4801

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7703
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11287
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3914
_reflns_number_gt                3736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.3799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3914
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.80286(13) 0.51058(9) 0.55319(6) 0.02085(19) Uani 1 1 d . . .
F2 F 0.63190(14) 0.76872(8) 0.47759(6) 0.02187(19) Uani 1 1 d . . .
F3 F -0.04233(13) 0.65952(9) 0.66059(6) 0.02007(19) Uani 1 1 d . . .
F4 F 0.12465(14) 0.39904(9) 0.73756(6) 0.0229(2) Uani 1 1 d . . .
O1 O 0.72033(18) 0.24276(11) 0.65111(7) 0.0255(2) Uani 1 1 d . . .
O2 O 0.37135(19) 0.23965(12) 0.98437(8) 0.0318(3) Uani 1 1 d . . .
O3 O 0.50849(18) 0.23723(11) 0.77691(7) 0.0235(2) Uani 1 1 d . . .
O4 O 0.72398(17) 0.30061(11) 0.92290(7) 0.0228(2) Uani 1 1 d . . .
N1 N 0.1723(2) 0.85408(12) 0.52773(8) 0.0205(3) Uani 1 1 d . . .
N2 N 0.2720(2) 0.94414(12) 0.46362(8) 0.0202(3) Uani 1 1 d . . .
N3 N 0.3320(2) 1.03770(13) 0.40686(9) 0.0272(3) Uani 1 1 d . . .
C1 C 0.2863(2) 0.72145(14) 0.56548(9) 0.0164(3) Uani 1 1 d . . .
C2 C 0.5045(2) 0.67828(14) 0.54150(9) 0.0168(3) Uani 1 1 d . . .
C3 C 0.5934(2) 0.54216(14) 0.58199(9) 0.0168(3) Uani 1 1 d . . .
C4 C 0.4746(2) 0.44210(14) 0.65018(9) 0.0171(3) Uani 1 1 d . . .
C5 C 0.2573(2) 0.48719(14) 0.67476(9) 0.0172(3) Uani 1 1 d . . .
C6 C 0.1676(2) 0.62271(14) 0.63414(9) 0.0168(3) Uani 1 1 d . . .
C7 C 0.5819(2) 0.29661(15) 0.69151(10) 0.0200(3) Uani 1 1 d . . .
C8 C 0.6073(3) 0.09518(15) 0.82379(11) 0.0270(3) Uani 1 1 d . . .
H8A H 0.6353 0.0427 0.7797 0.032 Uiso 1 1 calc R . .
H8B H 0.4962 0.0428 0.8708 0.032 Uiso 1 1 calc R . .
C9 C 0.8304(3) 0.10207(16) 0.86781(10) 0.0260(3) Uani 1 1 d . . .
H9A H 0.9320 0.1655 0.8217 0.031 Uiso 1 1 calc R . .
H9B H 0.9068 0.0063 0.8865 0.031 Uiso 1 1 calc R . .
C10 C 0.8091(3) 0.15363(16) 0.94988(10) 0.0268(3) Uani 1 1 d . . .
H10A H 0.7023 0.0943 0.9957 0.032 Uiso 1 1 calc R . .
H10B H 0.9611 0.1449 0.9776 0.032 Uiso 1 1 calc R . .
C11 C 0.5011(2) 0.32754(16) 0.93896(10) 0.0227(3) Uani 1 1 d . . .
C12 C 0.4337(2) 0.47938(16) 0.89307(9) 0.0205(3) Uani 1 1 d . . .
C13 C 0.2112(2) 0.52818(16) 0.90739(10) 0.0241(3) Uani 1 1 d . . .
H13 H 0.1076 0.4658 0.9475 0.029 Uiso 1 1 calc R . .
C14 C 0.1406(2) 0.66748(17) 0.86319(11) 0.0249(3) Uani 1 1 d . . .
H14 H -0.0098 0.7011 0.8744 0.030 Uiso 1 1 calc R . .
C15 C 0.2900(2) 0.75850(16) 0.80224(10) 0.0217(3) Uani 1 1 d . . .
C16 C 0.5147(2) 0.70902(16) 0.78882(10) 0.0222(3) Uani 1 1 d . . .
H16 H 0.6186 0.7710 0.7486 0.027 Uiso 1 1 calc R . .
C17 C 0.5854(2) 0.57035(16) 0.83395(10) 0.0211(3) Uani 1 1 d . . .
H17 H 0.7375 0.5372 0.8246 0.025 Uiso 1 1 calc R . .
C18 C 0.2110(2) 0.89930(17) 0.75019(11) 0.0251(3) Uani 1 1 d . . .
C19 C 0.1433(3) 1.01345(18) 0.70476(12) 0.0305(3) Uani 1 1 d . . .
H19 H 0.0891 1.1048 0.6684 0.037 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.3374(15) . ?
F2 C2 1.3386(16) . ?
F3 C6 1.3427(15) . ?
F4 C5 1.3369(16) . ?
O1 C7 1.2060(18) . ?
O2 C11 1.2135(19) . ?
O3 C7 1.3317(18) . ?
O3 C8 1.4673(17) . ?
O4 C11 1.3405(17) . ?
O4 C10 1.4534(18) . ?
N1 N2 1.2551(18) . ?
N1 C1 1.4047(17) . ?
N2 N3 1.1205(18) . ?
C1 C6 1.389(2) . ?
C1 C2 1.3928(18) . ?
C2 C3 1.3818(19) . ?
C3 C4 1.392(2) . ?
C4 C5 1.3977(18) . ?
C4 C7 1.4983(19) . ?
C5 C6 1.3788(19) . ?
C8 C9 1.512(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.491(2) . ?
C12 C17 1.392(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.4037(19) . ?
C15 C18 1.439(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.187(2) . ?
C19 H19 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
C7 O3 C8 116.00(12) . . ?
C11 O4 C10 118.06(12) . . ?
N2 N1 C1 117.73(11) . . ?
N3 N2 N1 169.27(14) . . ?
C6 C1 C2 116.63(12) . . ?
C6 C1 N1 116.20(12) . . ?
C2 C1 N1 127.17(13) . . ?
F2 C2 C3 118.59(11) . . ?
F2 C2 C1 120.13(12) . . ?
C3 C2 C1 121.27(13) . . ?
F1 C3 C2 116.64(12) . . ?
F1 C3 C4 120.93(12) . . ?
C2 C3 C4 122.42(12) . . ?
C3 C4 C5 115.84(12) . . ?
C3 C4 C7 119.60(12) . . ?
C5 C4 C7 124.56(13) . . ?
F4 C5 C6 116.95(12) . . ?
F4 C5 C4 121.16(12) . . ?
C6 C5 C4 121.87(13) . . ?
F3 C6 C5 119.04(12) . . ?
F3 C6 C1 119.02(12) . . ?
C5 C6 C1 121.93(12) . . ?
O1 C7 O3 125.18(13) . . ?
O1 C7 C4 122.85(13) . . ?
O3 C7 C4 111.97(12) . . ?
O3 C8 C9 111.52(12) . . ?
O3 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
O3 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 115.68(13) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
O4 C10 C9 110.06(12) . . ?
O4 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
O4 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
O2 C11 O4 124.43(14) . . ?
O2 C11 C12 124.56(13) . . ?
O4 C11 C12 111.01(13) . . ?
C17 C12 C13 120.03(14) . . ?
C17 C12 C11 121.18(13) . . ?
C13 C12 C11 118.73(13) . . ?
C14 C13 C12 120.14(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.18(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.35(14) . . ?
C14 C15 C18 120.35(13) . . ?
C16 C15 C18 120.23(14) . . ?
C17 C16 C15 120.26(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.00(13) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C19 C18 C15 177.49(16) . . ?
C18 C19 H19 180.0 . . ?

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
C1 N1 N2 N3 -179(100) . . . . ?
N2 N1 C1 C6 -177.84(12) . . . . ?
N2 N1 C1 C2 2.0(2) . . . . ?
C6 C1 C2 F2 -178.22(11) . . . . ?
N1 C1 C2 F2 1.9(2) . . . . ?
C6 C1 C2 C3 2.34(19) . . . . ?
N1 C1 C2 C3 -177.52(12) . . . . ?
F2 C2 C3 F1 -0.46(18) . . . . ?
C1 C2 C3 F1 178.98(11) . . . . ?
F2 C2 C3 C4 178.77(11) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
F1 C3 C4 C5 179.91(11) . . . . ?
C2 C3 C4 C5 0.72(19) . . . . ?
F1 C3 C4 C7 -0.44(18) . . . . ?
C2 C3 C4 C7 -179.64(12) . . . . ?
C3 C4 C5 F4 178.02(11) . . . . ?
C7 C4 C5 F4 -1.6(2) . . . . ?
C3 C4 C5 C6 -0.36(19) . . . . ?
C7 C4 C5 C6 -179.98(12) . . . . ?
F4 C5 C6 F3 1.41(18) . . . . ?
C4 C5 C6 F3 179.84(11) . . . . ?
F4 C5 C6 C1 -177.37(11) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C2 C1 C6 F3 179.22(11) . . . . ?
N1 C1 C6 F3 -0.90(18) . . . . ?
C2 C1 C6 C5 -2.00(19) . . . . ?
N1 C1 C6 C5 177.88(12) . . . . ?
C8 O3 C7 O1 0.1(2) . . . . ?
C8 O3 C7 C4 -178.97(11) . . . . ?
C3 C4 C7 O1 -27.4(2) . . . . ?
C5 C4 C7 O1 152.19(14) . . . . ?
C3 C4 C7 O3 151.70(12) . . . . ?
C5 C4 C7 O3 -28.69(18) . . . . ?
C7 O3 C8 C9 86.75(15) . . . . ?
O3 C8 C9 C10 70.43(17) . . . . ?
C11 O4 C10 C9 101.11(15) . . . . ?
C8 C9 C10 O4 -65.20(16) . . . . ?
C10 O4 C11 O2 9.5(2) . . . . ?
C10 O4 C11 C12 -170.02(11) . . . . ?
O2 C11 C12 C17 -172.78(14) . . . . ?
O4 C11 C12 C17 6.79(19) . . . . ?
O2 C11 C12 C13 4.6(2) . . . . ?
O4 C11 C12 C13 -175.85(12) . . . . ?
C17 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 -177.70(13) . . . . ?
C12 C13 C14 C15 1.8(2) . . . . ?
C13 C14 C15 C16 -2.4(2) . . . . ?
C13 C14 C15 C18 174.45(13) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C18 C15 C16 C17 -175.26(13) . . . . ?
C15 C16 C17 C12 -0.1(2) . . . . ?
C13 C12 C17 C16 -0.5(2) . . . . ?
C11 C12 C17 C16 176.83(13) . . . . ?
C14 C15 C18 C19 -88(4) . . . . ?
C16 C15 C18 C19 88(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 998248'
#######################################################################
#
#                 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_sa2826

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 F4 N3 O4'
_chemical_formula_sum            'C22 H17 F4 N3 O4'
_chemical_formula_weight         463.39

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.653(4)
_cell_length_b                   9.661(8)
_cell_length_c                   18.613(14)
_cell_angle_alpha                93.602(15)
_cell_angle_beta                 91.807(14)
_cell_angle_gamma                96.604(14)
_cell_volume                     1006.9(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3625
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      27.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'

_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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13144
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4589
_reflns_number_gt                3902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0675P)²+0.4040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4589
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1598
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.9242(2) 0.03366(15) 0.17215(8) 0.0533(4) Uani 1 1 d . . .
F2 F -0.6760(2) -0.04017(14) 0.28128(8) 0.0497(4) Uani 1 1 d . . .
F3 F -0.0550(2) 0.31414(13) 0.23746(7) 0.0436(3) Uani 1 1 d . . .
F4 F -0.3051(2) 0.38133(14) 0.12611(7) 0.0461(3) Uani 1 1 d . . .
O1 O -0.2680(4) -0.0233(2) 0.35433(11) 0.0697(6) Uani 1 1 d . . .
O2 O -0.0344(3) 0.17762(16) 0.35285(8) 0.0430(4) Uani 1 1 d . . .
O3 O 1.0988(3) 0.35002(16) 0.67819(9) 0.0441(4) Uani 1 1 d . . .
O4 O 1.4088(3) 0.51455(18) 0.67144(10) 0.0526(4) Uani 1 1 d . . .
N1 N -0.7782(4) 0.2351(2) 0.08970(12) 0.0570(6) Uani 1 1 d . . .
N2 N -0.7266(4) 0.3323(2) 0.04979(11) 0.0496(5) Uani 1 1 d . . .
N3 N -0.7215(5) 0.4112(3) 0.00815(13) 0.0673(7) Uani 1 1 d . . .
C1 C -0.6229(4) 0.2089(2) 0.14563(12) 0.0410(5) Uani 1 1 d . . .
C2 C -0.7070(4) 0.1024(2) 0.18752(12) 0.0404(5) Uani 1 1 d . . .
C3 C -0.5758(4) 0.0643(2) 0.24555(12) 0.0389(5) Uani 1 1 d . . .
C4 C -0.3519(4) 0.1337(2) 0.26590(11) 0.0359(5) Uani 1 1 d . . .
C5 C -0.2696(4) 0.2410(2) 0.22361(11) 0.0348(4) Uani 1 1 d . . .
C6 C -0.3973(4) 0.2781(2) 0.16499(11) 0.0360(4) Uani 1 1 d . . .
C7 C -0.2168(4) 0.0867(2) 0.32896(12) 0.0406(5) Uani 1 1 d . . .
C8 C 0.1014(4) 0.1353(2) 0.41395(12) 0.0407(5) Uani 1 1 d . . .
H8A H 0.1734 0.0494 0.4001 0.049 Uiso 1 1 calc R . .
H8B H -0.0048 0.1159 0.4543 0.049 Uiso 1 1 calc R . .
C9 C 0.2931(4) 0.2520(2) 0.43665(12) 0.0409(5) Uani 1 1 d . . .
H9A H 0.2192 0.3366 0.4521 0.049 Uiso 1 1 calc R . .
H9B H 0.3928 0.2744 0.3952 0.049 Uiso 1 1 calc R . .
C10 C 0.4495(4) 0.2114(2) 0.49851(12) 0.0409(5) Uani 1 1 d . . .
H10A H 0.3474 0.1857 0.5390 0.049 Uiso 1 1 calc R . .
H10B H 0.5250 0.1280 0.4822 0.049 Uiso 1 1 calc R . .
C11 C 0.6430(4) 0.3267(2) 0.52547(12) 0.0402(5) Uani 1 1 d . . .
H11A H 0.5685 0.4113 0.5402 0.048 Uiso 1 1 calc R . .
H11B H 0.7495 0.3499 0.4857 0.048 Uiso 1 1 calc R . .
C12 C 0.7906(4) 0.2856(2) 0.58897(12) 0.0403(5) Uani 1 1 d . . .
H12A H 0.6836 0.2606 0.6284 0.048 Uiso 1 1 calc R . .
H12B H 0.8676 0.2020 0.5739 0.048 Uiso 1 1 calc R . .
C13 C 0.9785(4) 0.4001(2) 0.61650(13) 0.0440(5) Uani 1 1 d . . .
H13A H 1.0932 0.4227 0.5786 0.053 Uiso 1 1 calc R . .
H13B H 0.9052 0.4854 0.6310 0.053 Uiso 1 1 calc R . .
C14 C 1.3115(4) 0.4167(2) 0.69990(12) 0.0385(5) Uani 1 1 d . . .
C15 C 1.4117(4) 0.3541(2) 0.76395(11) 0.0367(5) Uani 1 1 d . . .
C16 C 1.2836(4) 0.2462(2) 0.79662(12) 0.0384(5) Uani 1 1 d . . .
H16 H 1.1298 0.2089 0.7777 0.046 Uiso 1 1 calc R . .
C17 C 1.3788(4) 0.1930(2) 0.85643(12) 0.0418(5) Uani 1 1 d . . .
H17 H 1.2885 0.1204 0.8793 0.050 Uiso 1 1 calc R . .
C18 C 1.6071(4) 0.2447(2) 0.88402(12) 0.0414(5) Uani 1 1 d . . .
C19 C 1.7358(4) 0.3524(2) 0.85053(13) 0.0432(5) Uani 1 1 d . . .
H19 H 1.8911 0.3886 0.8686 0.052 Uiso 1 1 calc R . .
C20 C 1.6383(4) 0.4067(2) 0.79122(13) 0.0417(5) Uani 1 1 d . . .
H20 H 1.7266 0.4806 0.7688 0.050 Uiso 1 1 calc R . .
C21 C 1.7043(4) 0.1848(3) 0.94557(13) 0.0477(6) Uani 1 1 d . . .
C22 C 1.7724(5) 0.1288(3) 0.99596(15) 0.0598(7) Uani 1 1 d . . .
H22 H 1.8268 0.0840 1.0363 0.072 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.340(3) . ?
F2 C3 1.326(3) . ?
F3 C5 1.341(2) . ?
F4 C6 1.336(2) . ?
O1 C7 1.198(3) . ?
O2 C7 1.322(3) . ?
O2 C8 1.458(3) . ?
O3 C14 1.335(3) . ?
O3 C13 1.453(3) . ?
O4 C14 1.199(3) . ?
N1 N2 1.248(3) . ?
N1 C1 1.395(3) . ?
N2 N3 1.119(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.387(3) . ?
C4 C7 1.503(3) . ?
C5 C6 1.378(3) . ?
C8 C9 1.501(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.528(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.496(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.494(3) . ?
C15 C16 1.384(3) . ?
C15 C20 1.390(3) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(3) . ?
C18 C21 1.437(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.187(4) . ?
C22 H22 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
C7 O2 C8 114.86(17) . . ?
C14 O3 C13 117.66(17) . . ?
N2 N1 C1 121.2(2) . . ?
N3 N2 N1 166.9(3) . . ?
C2 C1 N1 115.1(2) . . ?
C2 C1 C6 116.6(2) . . ?
N1 C1 C6 128.3(2) . . ?
F1 C2 C1 119.2(2) . . ?
F1 C2 C3 118.5(2) . . ?
C1 C2 C3 122.3(2) . . ?
F2 C3 C2 116.51(19) . . ?
F2 C3 C4 121.9(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 115.6(2) . . ?
C5 C4 C7 125.24(19) . . ?
C3 C4 C7 119.17(19) . . ?
F3 C5 C6 115.80(18) . . ?
F3 C5 C4 120.93(19) . . ?
C6 C5 C4 123.26(19) . . ?
F4 C6 C5 119.92(18) . . ?
F4 C6 C1 119.40(19) . . ?
C5 C6 C1 120.7(2) . . ?
O1 C7 O2 123.5(2) . . ?
O1 C7 C4 123.1(2) . . ?
O2 C7 C4 113.32(18) . . ?
O2 C8 C9 108.22(17) . . ?
O2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 C10 110.78(18) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 113.43(18) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 112.43(18) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.49(18) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O3 C13 C12 106.95(18) . . ?
O3 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
O3 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
O4 C14 O3 124.0(2) . . ?
O4 C14 C15 124.6(2) . . ?
O3 C14 C15 111.45(18) . . ?
C16 C15 C20 119.6(2) . . ?
C16 C15 C14 121.5(2) . . ?
C20 C15 C14 118.9(2) . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 C21 121.6(2) . . ?
C17 C18 C21 119.5(2) . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C22 C21 C18 175.8(3) . . ?
C21 C22 H22 180.0 . . ?

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
C1 N1 N2 N3 -178.6(11) . . . . ?
N2 N1 C1 C2 177.2(2) . . . . ?
N2 N1 C1 C6 -1.6(4) . . . . ?
N1 C1 C2 F1 0.1(3) . . . . ?
C6 C1 C2 F1 178.98(19) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
F1 C2 C3 F2 0.9(3) . . . . ?
C1 C2 C3 F2 -179.7(2) . . . . ?
F1 C2 C3 C4 -178.13(19) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
F2 C3 C4 C5 -179.91(19) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
F2 C3 C4 C7 1.7(3) . . . . ?
C2 C3 C4 C7 -179.40(19) . . . . ?
C3 C4 C5 F3 -179.14(18) . . . . ?
C7 C4 C5 F3 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C7 C4 C5 C6 178.2(2) . . . . ?
F3 C5 C6 F4 0.0(3) . . . . ?
C4 C5 C6 F4 -179.02(19) . . . . ?
F3 C5 C6 C1 -179.99(19) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C2 C1 C6 F4 179.36(19) . . . . ?
N1 C1 C6 F4 -1.9(4) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
N1 C1 C6 C5 178.1(2) . . . . ?
C8 O2 C7 O1 -0.7(3) . . . . ?
C8 O2 C7 C4 -179.87(17) . . . . ?
C5 C4 C7 O1 -163.3(2) . . . . ?
C3 C4 C7 O1 15.0(4) . . . . ?
C5 C4 C7 O2 15.8(3) . . . . ?
C3 C4 C7 O2 -165.88(19) . . . . ?
C7 O2 C8 C9 -177.27(19) . . . . ?
O2 C8 C9 C10 -177.38(18) . . . . ?
C8 C9 C10 C11 -178.4(2) . . . . ?
C9 C10 C11 C12 177.86(19) . . . . ?
C10 C11 C12 C13 -178.9(2) . . . . ?
C14 O3 C13 C12 162.32(19) . . . . ?
C11 C12 C13 O3 177.75(18) . . . . ?
C13 O3 C14 O4 -0.3(3) . . . . ?
C13 O3 C14 C15 179.55(17) . . . . ?
O4 C14 C15 C16 176.2(2) . . . . ?
O3 C14 C15 C16 -3.6(3) . . . . ?
O4 C14 C15 C20 -3.5(3) . . . . ?
O3 C14 C15 C20 176.71(19) . . . . ?
C20 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C17 -178.6(2) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C16 C17 C18 C21 -178.5(2) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C21 C18 C19 C20 179.4(2) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C14 C15 C20 C19 179.51(19) . . . . ?
C19 C18 C21 C22 -170(4) . . . . ?
C17 C18 C21 C22 9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 998250'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 F4 N3 O4'
_chemical_formula_sum            'C20 H13 F4 N3 O4'
_chemical_formula_weight         435.33

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.5088(15)
_cell_length_b                   10.929(2)
_cell_length_c                   12.823(3)
_cell_angle_alpha                112.78(3)
_cell_angle_beta                 93.81(3)
_cell_angle_gamma                105.56(3)
_cell_volume                     917.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3428
_cell_measurement_theta_min      1.7550
_cell_measurement_theta_max      27.4815

_exptl_crystal_description       rod
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8119
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4156
_reflns_number_gt                3814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.4981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4156
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.18816(14) 0.86130(10) 0.83245(8) 0.0238(2) Uani 1 1 d . . .
F2 F 0.20114(14) 0.62651(10) 0.83836(8) 0.0240(2) Uani 1 1 d . . .
F3 F -0.27564(15) 0.37194(10) 0.50021(9) 0.0266(2) Uani 1 1 d . . .
F4 F -0.28409(15) 0.60993(11) 0.49620(9) 0.0272(3) Uani 1 1 d . . .
O1 O 0.44983(18) 0.25686(12) 1.25386(10) 0.0256(3) Uani 1 1 d . . .
O2 O 0.29639(17) 0.10660(12) 1.07368(10) 0.0201(3) Uani 1 1 d . . .
O3 O 0.02348(17) 0.36357(12) 0.77397(10) 0.0197(3) Uani 1 1 d . . .
O4 O -0.07973(19) 0.24060(12) 0.58249(10) 0.0264(3) Uani 1 1 d . . .
N1 N -0.0379(2) 0.87682(15) 0.67110(12) 0.0229(3) Uani 1 1 d . . .
N2 N -0.1241(2) 0.88290(15) 0.58652(12) 0.0218(3) Uani 1 1 d . . .
N3 N -0.1903(2) 0.91097(16) 0.52150(14) 0.0299(4) Uani 1 1 d . . .
C1 C -0.0447(2) 0.74354(17) 0.66287(14) 0.0184(3) Uani 1 1 d . . .
C2 C 0.0745(2) 0.74011(16) 0.74889(13) 0.0181(3) Uani 1 1 d . . .
C3 C 0.0781(2) 0.61552(17) 0.75144(13) 0.0175(3) Uani 1 1 d . . .
C4 C -0.0368(2) 0.48614(16) 0.66868(14) 0.0175(3) Uani 1 1 d . . .
C5 C -0.1569(2) 0.49000(17) 0.58277(14) 0.0191(3) Uani 1 1 d . . .
C6 C -0.1617(2) 0.61474(17) 0.58044(14) 0.0197(3) Uani 1 1 d . . .
C7 C -0.0350(2) 0.34874(17) 0.66788(14) 0.0185(3) Uani 1 1 d . . .
C8 C 0.0483(2) 0.24056(16) 0.78398(14) 0.0189(3) Uani 1 1 d . . .
H8A H 0.1297 0.2020 0.7313 0.023 Uiso 1 1 calc R . .
H8B H -0.0749 0.1669 0.7648 0.023 Uiso 1 1 calc R . .
C9 C 0.1402(2) 0.29062(17) 0.90841(14) 0.0199(3) Uani 1 1 d . . .
H9B H 0.0612 0.3351 0.9598 0.024 Uiso 1 1 calc R . .
H9A H 0.2646 0.3620 0.9252 0.024 Uiso 1 1 calc R . .
C10 C 0.1657(2) 0.16893(16) 0.93304(14) 0.0189(3) Uani 1 1 d . . .
H10B H 0.0409 0.1022 0.9245 0.023 Uiso 1 1 calc R . .
H10A H 0.2342 0.1184 0.8770 0.023 Uiso 1 1 calc R . .
C11 C 0.2752(2) 0.22498(17) 1.05404(14) 0.0195(3) Uani 1 1 d . . .
H11A H 0.4004 0.2915 1.0630 0.023 Uiso 1 1 calc R . .
H11B H 0.2068 0.2749 1.1106 0.023 Uiso 1 1 calc R . .
C12 C 0.3897(2) 0.13917(17) 1.17889(14) 0.0184(3) Uani 1 1 d . . .
C13 C 0.4081(2) 0.01271(17) 1.19228(14) 0.0185(3) Uani 1 1 d . . .
C14 C 0.3488(2) -0.12006(17) 1.10091(14) 0.0185(3) Uani 1 1 d . . .
H14 H 0.2957 -0.1325 1.0267 0.022 Uiso 1 1 calc R . .
C15 C 0.3675(2) -0.23439(17) 1.11836(14) 0.0189(3) Uani 1 1 d . . .
H15 H 0.3266 -0.3248 1.0560 0.023 Uiso 1 1 calc R . .
C16 C 0.4464(2) -0.21675(17) 1.22754(14) 0.0191(3) Uani 1 1 d . . .
C17 C 0.5064(2) -0.08261(18) 1.31875(15) 0.0215(3) Uani 1 1 d . . .
H17 H 0.5597 -0.0697 1.3930 0.026 Uiso 1 1 calc R . .
C18 C 0.4884(2) 0.03154(18) 1.30110(15) 0.0214(3) Uani 1 1 d . . .
H18 H 0.5306 0.1223 1.3630 0.026 Uiso 1 1 calc R . .
C19 C 0.4669(2) -0.33467(18) 1.24624(14) 0.0205(3) Uani 1 1 d . . .
C20 C 0.4871(2) -0.43133(18) 1.26190(15) 0.0237(4) Uani 1 1 d . . .
H20 H 0.5031 -0.5083 1.2744 0.028 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.3431(19) . ?
F2 C3 1.3456(17) . ?
F3 C5 1.334(2) . ?
F4 C6 1.3463(17) . ?
O1 C12 1.207(2) . ?
O2 C12 1.3439(19) . ?
O2 C11 1.4562(17) . ?
O3 C7 1.3347(19) . ?
O3 C8 1.4571(18) . ?
O4 C7 1.202(2) . ?
N1 N2 1.2591(19) . ?
N1 C1 1.406(2) . ?
N2 N3 1.123(2) . ?
C1 C6 1.390(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.397(2) . ?
C4 C7 1.501(2) . ?
C5 C6 1.385(2) . ?
C8 C9 1.516(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.536(2) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 C11 1.511(2) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.497(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(2) . ?
C16 C19 1.443(2) . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.194(2) . ?
C20 H20 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
C12 O2 C11 115.22(13) . . ?
C7 O3 C8 116.51(13) . . ?
N2 N1 C1 117.54(14) . . ?
N3 N2 N1 168.82(17) . . ?
C6 C1 C2 116.29(14) . . ?
C6 C1 N1 127.20(14) . . ?
C2 C1 N1 116.47(15) . . ?
F1 C2 C3 118.97(13) . . ?
F1 C2 C1 119.14(14) . . ?
C3 C2 C1 121.89(15) . . ?
F2 C3 C2 116.04(14) . . ?
F2 C3 C4 121.71(14) . . ?
C2 C3 C4 122.24(14) . . ?
C3 C4 C5 115.71(14) . . ?
C3 C4 C7 123.70(14) . . ?
C5 C4 C7 120.58(14) . . ?
F3 C5 C6 117.11(14) . . ?
F3 C5 C4 120.71(14) . . ?
C6 C5 C4 122.17(15) . . ?
F4 C6 C5 118.66(15) . . ?
F4 C6 C1 119.66(14) . . ?
C5 C6 C1 121.68(14) . . ?
O4 C7 O3 125.05(15) . . ?
O4 C7 C4 124.03(14) . . ?
O3 C7 C4 110.92(14) . . ?
O3 C8 C9 105.69(13) . . ?
O3 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O3 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 C10 111.32(14) . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
H9B C9 H9A 108.0 . . ?
C11 C10 C9 109.68(13) . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
H10B C10 H10A 108.2 . . ?
O2 C11 C10 107.89(13) . . ?
O2 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 . . ?
O2 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O1 C12 O2 123.58(14) . . ?
O1 C12 C13 124.21(14) . . ?
O2 C12 C13 112.21(14) . . ?
C14 C13 C18 120.10(14) . . ?
C14 C13 C12 122.35(14) . . ?
C18 C13 C12 117.55(15) . . ?
C15 C14 C13 120.00(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.31(15) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.24(14) . . ?
C15 C16 C19 120.65(15) . . ?
C17 C16 C19 120.11(14) . . ?
C18 C17 C16 120.39(15) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 119.95(15) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C16 178.93(18) . . ?
C19 C20 H20 180.0 . . ?

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
C1 N1 N2 N3 -179.2(9) . . . . ?
N2 N1 C1 C6 -11.9(3) . . . . ?
N2 N1 C1 C2 170.36(15) . . . . ?
C6 C1 C2 F1 -178.62(15) . . . . ?
N1 C1 C2 F1 -0.6(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
N1 C1 C2 C3 178.76(16) . . . . ?
F1 C2 C3 F2 -1.4(2) . . . . ?
C1 C2 C3 F2 179.25(14) . . . . ?
F1 C2 C3 C4 179.33(15) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
F2 C3 C4 C5 -179.51(14) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
F2 C3 C4 C7 -0.1(3) . . . . ?
C2 C3 C4 C7 179.21(15) . . . . ?
C3 C4 C5 F3 -178.77(15) . . . . ?
C7 C4 C5 F3 1.8(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C7 C4 C5 C6 -179.67(16) . . . . ?
F3 C5 C6 F4 0.0(2) . . . . ?
C4 C5 C6 F4 -178.62(15) . . . . ?
F3 C5 C6 C1 179.58(15) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C2 C1 C6 F4 178.37(14) . . . . ?
N1 C1 C6 F4 0.6(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
N1 C1 C6 C5 -178.94(16) . . . . ?
C8 O3 C7 O4 5.1(2) . . . . ?
C8 O3 C7 C4 -174.59(12) . . . . ?
C3 C4 C7 O4 -153.64(18) . . . . ?
C5 C4 C7 O4 25.8(3) . . . . ?
C3 C4 C7 O3 26.1(2) . . . . ?
C5 C4 C7 O3 -154.52(15) . . . . ?
C7 O3 C8 C9 172.21(14) . . . . ?
O3 C8 C9 C10 177.07(13) . . . . ?
C8 C9 C10 C11 174.28(14) . . . . ?
C12 O2 C11 C10 -179.27(13) . . . . ?
C9 C10 C11 O2 -179.89(13) . . . . ?
C11 O2 C12 O1 1.3(2) . . . . ?
C11 O2 C12 C13 -179.30(13) . . . . ?
O1 C12 C13 C14 -175.19(17) . . . . ?
O2 C12 C13 C14 5.5(2) . . . . ?
O1 C12 C13 C18 4.7(3) . . . . ?
O2 C12 C13 C18 -174.69(14) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
C12 C13 C14 C15 -179.37(15) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C14 C15 C16 C19 -179.74(15) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C19 C16 C17 C18 179.49(16) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C12 C13 C18 C17 179.11(15) . . . . ?
C15 C16 C19 C20 110(10) . . . . ?
C17 C16 C19 C20 -70(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 998369'
