# 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
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#  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_compound1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 F4 N2 O4'
_chemical_formula_sum            'C14 H10 F4 N2 O4'
_chemical_formula_weight         346.24

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                   8.1577(6)
_cell_length_b                   10.1407(8)
_cell_length_c                   18.2913(14)
_cell_angle_alpha                95.2070(10)
_cell_angle_beta                 94.8800(10)
_cell_angle_gamma                98.6630(10)
_cell_volume                     1482.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9552
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         28.32
_reflns_number_total             6797
_reflns_number_gt                4693
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0977P)²+0.1442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6797
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.43014(19) 0.70571(13) 0.19653(8) 0.0625(4) Uani 1 1 d . . .
F1 F 0.5069(2) 0.55995(15) 0.08079(7) 0.0643(4) Uani 1 1 d . . .
F4 F 0.6128(2) 0.22378(13) 0.23099(8) 0.0650(4) Uani 1 1 d . . .
F3 F 0.5470(2) 0.37242(15) 0.34732(8) 0.0654(4) Uani 1 1 d . . .
O5 O 0.5487(2) 0.6395(2) 0.39875(9) 0.0636(5) Uani 1 1 d . . .
H5 H 0.5179 0.6848 0.4328 0.080 Uiso 1 1 calc . . .
O8 O 0.7288(2) 0.36592(15) 0.05510(9) 0.0545(4) Uani 1 1 d . . .
H8 H 0.7498 0.3169 0.0201 0.080 Uiso 1 1 calc . . .
C28 C 0.4879(2) 0.5449(2) 0.27633(11) 0.0402(5) Uani 1 1 d . . .
C27 C 0.6098(3) 0.3033(2) 0.08712(12) 0.0428(5) Uani 1 1 d . . .
C26 C 0.5711(3) 0.3442(2) 0.22094(12) 0.0438(5) Uani 1 1 d . . .
O7 O 0.5410(2) 0.19071(17) 0.06992(11) 0.0692(6) Uani 1 1 d . . .
C25 C 0.5362(3) 0.4214(2) 0.28230(11) 0.0427(5) Uani 1 1 d . . .
O6 O 0.3150(2) 0.6744(2) 0.33838(10) 0.0663(5) Uani 1 1 d . . .
C24 C 0.5653(2) 0.3887(2) 0.15266(11) 0.0398(5) Uani 1 1 d . . .
C23 C 0.5179(3) 0.5122(2) 0.14649(11) 0.0430(5) Uani 1 1 d . . .
C22 C 0.4402(3) 0.6268(2) 0.34181(12) 0.0431(5) Uani 1 1 d . . .
C21 C 0.4773(3) 0.5877(2) 0.20717(12) 0.0431(5) Uani 1 1 d . . .
F5 F 0.89689(19) 0.57113(15) 0.43076(7) 0.0642(4) Uani 1 1 d . . .
F8 F 1.0552(2) 0.52619(15) 0.14989(7) 0.0659(4) Uani 1 1 d . . .
F6 F 0.9711(2) 0.34137(15) 0.37234(9) 0.0741(5) Uani 1 1 d . . .
O4 O 0.7665(2) 0.84115(16) 0.31120(9) 0.0572(5) Uani 1 1 d . . .
H4 H 0.7465 0.9120 0.3310 0.080 Uiso 1 1 calc . . .
F7 F 0.9708(2) 0.75365(14) 0.20644(8) 0.0721(5) Uani 1 1 d . . .
O3 O 0.9497(2) 0.85425(17) 0.41046(10) 0.0627(5) Uani 1 1 d . . .
C20 C 0.8823(3) 0.7993(2) 0.35205(12) 0.0423(5) Uani 1 1 d . . .
C19 C 0.9721(3) 0.4425(2) 0.33072(13) 0.0447(5) Uani 1 1 d . . .
O2 O 0.9504(2) 0.23286(19) 0.17727(12) 0.0766(6) Uani 1 1 d . . .
H2 H 0.9811 0.1632 0.1617 0.080 Uiso 1 1 calc . . .
C8 C 1.0112(2) 0.42653(19) 0.25916(12) 0.0416(5) Uani 1 1 d . . .
C7 C 0.9656(3) 0.6513(2) 0.24801(12) 0.0432(5) Uani 1 1 d . . .
C16 C 0.9248(2) 0.66822(19) 0.31943(11) 0.0377(4) Uani 1 1 d . . .
C15 C 0.9319(2) 0.5617(2) 0.36093(11) 0.0420(5) Uani 1 1 d . . .
C14 C 1.0086(3) 0.5337(2) 0.21827(11) 0.0433(5) Uani 1 1 d . . .
C13 C 1.0593(3) 0.2968(2) 0.22693(13) 0.0472(5) Uani 1 1 d . . .
O1 O 1.1847(3) 0.2603(2) 0.24842(16) 0.0979(8) Uani 1 1 d . . .
N3 N 0.5407(2) 0.20529(18) 0.49254(10) 0.0455(4) Uani 1 1 d . . .
N4 N 0.6530(2) 0.03910(17) 0.38786(10) 0.0450(4) Uani 1 1 d . . .
C2 C 0.4385(3) 0.1457(2) 0.43485(11) 0.0414(5) Uani 1 1 d . . .
C1 C 0.4963(3) 0.0616(2) 0.38078(11) 0.0414(5) Uani 1 1 d . . .
C10 C 0.7533(3) 0.1005(2) 0.44633(13) 0.0502(5) Uani 1 1 d . . .
H10A H 0.8633 0.0859 0.4519 0.060 Uiso 1 1 calc R . .
C9 C 0.6985(3) 0.1838(2) 0.49811(13) 0.0501(5) Uani 1 1 d . . .
H9A H 0.7720 0.2263 0.5379 0.060 Uiso 1 1 calc R . .
C18 C 0.3846(3) -0.0055(3) 0.31447(14) 0.0627(7) Uani 1 1 d . . .
H18A H 0.4458 -0.0583 0.2839 0.094 Uiso 1 1 calc R . .
H18B H 0.3444 0.0614 0.2869 0.094 Uiso 1 1 calc R . .
H18C H 0.2920 -0.0625 0.3300 0.094 Uiso 1 1 calc R . .
C17 C 0.2630(3) 0.1720(3) 0.43014(15) 0.0632(7) Uani 1 1 d . . .
H17A H 0.2484 0.2314 0.4722 0.095 Uiso 1 1 calc R . .
H17B H 0.1884 0.0890 0.4293 0.095 Uiso 1 1 calc R . .
H17C H 0.2392 0.2127 0.3859 0.095 Uiso 1 1 calc R . .
N2 N 0.1507(2) 0.80726(18) 0.03648(10) 0.0466(4) Uani 1 1 d . . .
N1 N 0.0377(2) 1.01105(17) 0.11600(10) 0.0436(4) Uani 1 1 d . . .
C6 C -0.0695(3) 0.90734(19) 0.08264(11) 0.0382(4) Uani 1 1 d . . .
C5 C -0.0116(3) 0.80331(19) 0.04130(11) 0.0399(4) Uani 1 1 d . . .
C4 C 0.1994(3) 1.0135(2) 0.11088(13) 0.0505(5) Uani 1 1 d . . .
H4A H 0.2753 1.0856 0.1345 0.061 Uiso 1 1 calc R . .
C3 C 0.2560(3) 0.9115(2) 0.07131(14) 0.0551(6) Uani 1 1 d . . .
H3A H 0.3699 0.9150 0.0687 0.066 Uiso 1 1 calc R . .
C12 C -0.1274(3) 0.6852(2) 0.00199(15) 0.0620(7) Uani 1 1 d . . .
H12A H -0.0642 0.6255 -0.0228 0.093 Uiso 1 1 calc R . .
H12B H -0.2032 0.7153 -0.0335 0.093 Uiso 1 1 calc R . .
H12C H -0.1891 0.6390 0.0370 0.093 Uiso 1 1 calc R . .
C11 C -0.2506(3) 0.9060(3) 0.09267(15) 0.0578(6) Uani 1 1 d . . .
H11A H -0.2634 0.9861 0.1224 0.087 Uiso 1 1 calc R . .
H11B H -0.2913 0.8290 0.1166 0.087 Uiso 1 1 calc R . .
H11C H -0.3128 0.9022 0.0453 0.087 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
F2 C21 1.337(2) . ?
F1 C23 1.337(3) . ?
F4 C26 1.340(2) . ?
F3 C25 1.331(3) . ?
O5 C22 1.292(3) . ?
O5 H5 0.8200 . ?
O8 C27 1.291(3) . ?
O8 H8 0.8200 . ?
C28 C21 1.374(3) . ?
C28 C25 1.379(3) . ?
C28 C22 1.507(3) . ?
C27 O7 1.196(3) . ?
C27 C24 1.517(3) . ?
C26 C24 1.366(3) . ?
C26 C25 1.384(3) . ?
O6 C22 1.193(3) . ?
C24 C23 1.376(3) . ?
C23 C21 1.383(3) . ?
F5 C15 1.331(2) . ?
F8 C14 1.337(2) . ?
F6 C19 1.331(3) . ?
O4 C20 1.300(3) . ?
O4 H4 0.8200 . ?
F7 C7 1.339(3) . ?
O3 C20 1.206(3) . ?
C20 C16 1.507(3) . ?
C19 C8 1.374(3) . ?
C19 C15 1.379(3) . ?
O2 C13 1.272(3) . ?
O2 H2 0.8200 . ?
C8 C14 1.376(3) . ?
C8 C13 1.512(3) . ?
C7 C14 1.372(3) . ?
C7 C16 1.378(3) . ?
C16 C15 1.381(3) . ?
C13 O1 1.187(3) . ?
N3 C2 1.325(3) . ?
N3 C9 1.335(3) . ?
N4 C1 1.330(3) . ?
N4 C10 1.333(3) . ?
C2 C1 1.405(3) . ?
C2 C17 1.493(3) . ?
C1 C18 1.496(3) . ?
C10 C9 1.360(3) . ?
C10 H10A 0.9300 . ?
C9 H9A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N2 C5 1.329(3) . ?
N2 C3 1.331(3) . ?
N1 C6 1.326(3) . ?
N1 C4 1.327(3) . ?
C6 C5 1.405(3) . ?
C6 C11 1.503(3) . ?
C5 C12 1.493(3) . ?
C4 C3 1.368(3) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C22 O5 H5 109.5 . . ?
C27 O8 H8 109.5 . . ?
C21 C28 C25 117.06(18) . . ?
C21 C28 C22 121.13(19) . . ?
C25 C28 C22 121.73(19) . . ?
O7 C27 O8 126.11(19) . . ?
O7 C27 C24 121.78(19) . . ?
O8 C27 C24 112.09(17) . . ?
F4 C26 C24 120.84(18) . . ?
F4 C26 C25 117.48(19) . . ?
C24 C26 C25 121.67(19) . . ?
F3 C25 C28 120.53(18) . . ?
F3 C25 C26 118.38(19) . . ?
C28 C25 C26 121.1(2) . . ?
C26 C24 C23 117.40(18) . . ?
C26 C24 C27 120.22(18) . . ?
C23 C24 C27 122.38(19) . . ?
F1 C23 C24 120.08(18) . . ?
F1 C23 C21 118.80(19) . . ?
C24 C23 C21 121.1(2) . . ?
O6 C22 O5 125.81(19) . . ?
O6 C22 C28 121.26(19) . . ?
O5 C22 C28 112.92(17) . . ?
F2 C21 C28 120.82(18) . . ?
F2 C21 C23 117.56(19) . . ?
C28 C21 C23 121.60(19) . . ?
C20 O4 H4 109.5 . . ?
O3 C20 O4 125.89(19) . . ?
O3 C20 C16 121.58(18) . . ?
O4 C20 C16 112.52(17) . . ?
F6 C19 C8 120.02(19) . . ?
F6 C19 C15 118.5(2) . . ?
C8 C19 C15 121.5(2) . . ?
C13 O2 H2 109.5 . . ?
C19 C8 C14 117.71(18) . . ?
C19 C8 C13 121.2(2) . . ?
C14 C8 C13 121.03(19) . . ?
F7 C7 C14 118.02(19) . . ?
F7 C7 C16 119.80(18) . . ?
C14 C7 C16 122.1(2) . . ?
C7 C16 C15 116.99(18) . . ?
C7 C16 C20 121.55(19) . . ?
C15 C16 C20 121.39(18) . . ?
F5 C15 C19 118.50(19) . . ?
F5 C15 C16 120.54(18) . . ?
C19 C15 C16 120.95(19) . . ?
F8 C14 C7 119.1(2) . . ?
F8 C14 C8 120.12(17) . . ?
C7 C14 C8 120.70(19) . . ?
O1 C13 O2 125.4(2) . . ?
O1 C13 C8 121.8(2) . . ?
O2 C13 C8 112.77(18) . . ?
C2 N3 C9 118.78(17) . . ?
C1 N4 C10 118.29(17) . . ?
N3 C2 C1 120.25(18) . . ?
N3 C2 C17 117.48(19) . . ?
C1 C2 C17 122.3(2) . . ?
N4 C1 C2 120.25(19) . . ?
N4 C1 C18 118.26(18) . . ?
C2 C1 C18 121.5(2) . . ?
N4 C10 C9 121.6(2) . . ?
N4 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
N3 C9 C10 120.8(2) . . ?
N3 C9 H9A 119.6 . . ?
C10 C9 H9A 119.6 . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C17 H17A 109.5 . . ?
C2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 N2 C3 118.67(17) . . ?
C6 N1 C4 119.12(17) . . ?
N1 C6 C5 120.01(18) . . ?
N1 C6 C11 117.23(18) . . ?
C5 C6 C11 122.75(19) . . ?
N2 C5 C6 120.23(19) . . ?
N2 C5 C12 117.72(18) . . ?
C6 C5 C12 122.05(19) . . ?
N1 C4 C3 120.9(2) . . ?
N1 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
N2 C3 C4 121.1(2) . . ?
N2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 982115'
#######################################################################
#
#                 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_compound2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 F4 N2 O4'
_chemical_formula_weight         346.24

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                   7.8250(4)
_cell_length_b                   9.0424(4)
_cell_length_c                   11.6340(4)
_cell_angle_alpha                92.810(3)
_cell_angle_beta                 105.233(4)
_cell_angle_gamma                115.272(5)
_cell_volume                     705.88(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5580
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         29.87
_reflns_number_total             3339
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0844P)²+0.4383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3339
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1871
_refine_ls_wR_factor_gt          0.1626
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.0236(3) 0.3129(2) 0.32272(15) 0.0560(5) Uani 1 1 d . . .
F2 F 0.0481(3) 0.1784(2) 0.51868(15) 0.0601(5) Uani 1 1 d . . .
F3 F -0.4960(3) 0.4067(2) 0.38402(15) 0.0579(5) Uani 1 1 d . . .
F4 F -0.4682(3) 0.2751(3) 0.58259(15) 0.0643(6) Uani 1 1 d . . .
O1 O -0.2551(4) 0.5708(2) 0.24056(16) 0.0516(6) Uani 1 1 d . . .
H1 H -0.2695 0.6000 0.1745 0.080 Uiso 1 1 calc . . .
O2 O -0.2069(4) 0.1992(3) 0.75813(18) 0.0581(6) Uani 1 1 d . . .
H2 H -0.2008 0.1437 0.8113 0.080 Uiso 1 1 calc . . .
O3 O -0.2775(4) 0.3458(2) 0.13705(16) 0.0546(6) Uani 1 1 d . . .
C1 C -0.2596(4) 0.4254(3) 0.2286(2) 0.0370(6) Uani 1 1 d . . .
C2 C -0.2388(4) 0.3618(3) 0.3465(2) 0.0342(6) Uani 1 1 d . . .
C3 C -0.3580(4) 0.3541(3) 0.4171(2) 0.0392(6) Uani 1 1 d . . .
C4 C -0.2111(4) 0.2211(3) 0.5563(2) 0.0395(6) Uani 1 1 d . . .
C5 C -0.1022(4) 0.3022(3) 0.3850(2) 0.0380(6) Uani 1 1 d . . .
C9 C -0.0883(4) 0.2321(3) 0.4874(2) 0.0388(6) Uani 1 1 d . . .
C7 C -0.3443(4) 0.2838(3) 0.5204(2) 0.0421(6) Uani 1 1 d . . .
O4 O -0.2034(6) -0.0040(3) 0.6480(2) 0.0966(11) Uani 1 1 d . . .
C21 C -0.2073(5) 0.1257(4) 0.6598(2) 0.0484(7) Uani 1 1 d . . .
N1 N 0.7332(3) 0.7420(3) 0.05931(17) 0.0359(5) Uani 1 1 d . . .
N2 N 0.7593(4) 0.9773(3) -0.0868(2) 0.0426(6) Uani 1 1 d . . .
C10 C 0.7108(4) 0.8756(3) 0.0921(2) 0.0357(6) Uani 1 1 d . . .
C11 C 0.7776(4) 0.8437(3) -0.1192(2) 0.0415(6) Uani 1 1 d . . .
H11 H 0.7978 0.8287 -0.1933 0.080 Uiso 1 1 calc . . .
C12 C 0.7677(4) 0.7245(3) -0.0458(2) 0.0374(6) Uani 1 1 d . . .
C13 C 0.7257(4) 0.9930(3) 0.0176(2) 0.0409(6) Uani 1 1 d . . .
H13 H 0.7116 1.0855 0.0419 0.080 Uiso 1 1 calc . . .
C6 C 0.6720(5) 0.8943(4) 0.2095(3) 0.0525(8) Uani 1 1 d . . .
H6A H 0.6688 0.8024 0.2485 0.080 Uiso 1 1 calc . . .
H6B H 0.5463 0.8960 0.1946 0.080 Uiso 1 1 calc . . .
H6C H 0.7759 0.9964 0.2610 0.080 Uiso 1 1 calc . . .
C8 C 0.7944(6) 0.5776(4) -0.0817(3) 0.0562(8) Uani 1 1 d . . .
H8A H 0.7809 0.5096 -0.0205 0.080 Uiso 1 1 calc . . .
H8B H 0.9244 0.6144 -0.0901 0.080 Uiso 1 1 calc . . .
H8C H 0.6951 0.5139 -0.1575 0.080 Uiso 1 1 calc . . .


_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 C5 1.343(3) . ?
F2 C9 1.329(3) . ?
F3 C3 1.334(3) . ?
F4 C7 1.333(3) . ?
O1 C1 1.299(3) . ?
O1 H1 0.8200 . ?
O2 C21 1.293(3) . ?
O2 H2 0.8200 . ?
O3 C1 1.197(3) . ?
C1 C2 1.509(3) . ?
C2 C5 1.378(4) . ?
C2 C3 1.380(4) . ?
C3 C7 1.388(3) . ?
C4 C7 1.372(4) . ?
C4 C9 1.381(4) . ?
C4 C21 1.517(3) . ?
C5 C9 1.377(3) . ?
O4 C21 1.188(4) . ?
N1 C12 1.336(3) . ?
N1 C10 1.344(3) . ?
N2 C13 1.322(3) . ?
N2 C11 1.325(4) . ?
C10 C13 1.389(3) . ?
C10 C6 1.492(4) . ?
C11 C12 1.397(3) . ?
C11 H11 0.9300 . ?
C12 C8 1.487(4) . ?
C13 H13 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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 O1 H1 109.5 . . ?
C21 O2 H2 109.5 . . ?
O3 C1 O1 126.3(2) . . ?
O3 C1 C2 121.3(2) . . ?
O1 C1 C2 112.4(2) . . ?
C5 C2 C3 117.3(2) . . ?
C5 C2 C1 120.1(2) . . ?
C3 C2 C1 122.5(2) . . ?
F3 C3 C2 120.5(2) . . ?
F3 C3 C7 118.5(2) . . ?
C2 C3 C7 120.9(2) . . ?
C7 C4 C9 118.0(2) . . ?
C7 C4 C21 123.0(3) . . ?
C9 C4 C21 118.8(2) . . ?
F1 C5 C9 118.1(2) . . ?
F1 C5 C2 119.9(2) . . ?
C9 C5 C2 121.9(2) . . ?
F2 C9 C5 118.1(2) . . ?
F2 C9 C4 121.3(2) . . ?
C5 C9 C4 120.6(2) . . ?
F4 C7 C4 120.7(2) . . ?
F4 C7 C3 118.0(2) . . ?
C4 C7 C3 121.3(2) . . ?
O4 C21 O2 125.1(2) . . ?
O4 C21 C4 121.0(2) . . ?
O2 C21 C4 113.9(2) . . ?
C12 N1 C10 118.8(2) . . ?
C13 N2 C11 117.5(2) . . ?
N1 C10 C13 119.9(2) . . ?
N1 C10 C6 118.5(2) . . ?
C13 C10 C6 121.6(2) . . ?
N2 C11 C12 122.2(2) . . ?
N2 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
N1 C12 C11 119.5(2) . . ?
N1 C12 C8 118.8(2) . . ?
C11 C12 C8 121.6(2) . . ?
N2 C13 C10 122.1(2) . . ?
N2 C13 H13 118.9 . . ?
C10 C13 H13 118.9 . . ?
C10 C6 H6A 109.5 . . ?
C10 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C10 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C8 H8A 109.5 . . ?
C12 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C12 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.821
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 982116'
#######################################################################
#
#                 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_compound3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 F4 N10 O4'
_chemical_formula_weight         488.39

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   4.8860(12)
_cell_length_b                   11.475(3)
_cell_length_c                   17.771(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.010(10)
_cell_angle_gamma                90.00
_cell_volume                     996.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6184
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         28.26
_reflns_number_total             2405
_reflns_number_gt                1922
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0878P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2405
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.06701(19) 0.38972(8) 0.56027(5) 0.0445(3) Uani 1 1 d . . .
O1 O 0.2914(3) 0.68406(10) 0.65729(6) 0.0473(3) Uani 1 1 d . . .
F2 F 0.2484(2) 0.32163(9) 0.43004(5) 0.0507(3) Uani 1 1 d . . .
N1 N -0.3013(3) 0.52353(11) 0.91579(7) 0.0408(3) Uani 1 1 d . . .
N2 N -0.0181(3) 0.56933(11) 0.81601(7) 0.0401(3) Uani 1 1 d . . .
H2 H 0.0519 0.5498 0.7734 0.080 Uiso 1 1 calc . . .
N3 N -0.0320(3) 0.69886(12) 0.91735(8) 0.0473(4) Uani 1 1 d . . .
C1 C 0.2847(3) 0.44512(13) 0.53246(7) 0.0334(3) Uani 1 1 d . . .
C2 C 0.3798(3) 0.40948(12) 0.46374(8) 0.0342(3) Uani 1 1 d . . .
O2 O 0.2191(3) 0.50005(10) 0.69023(6) 0.0526(4) Uani 1 1 d . . .
C3 C 0.4013(3) 0.53718(12) 0.57078(7) 0.0336(3) Uani 1 1 d . . .
C4 C 0.2956(3) 0.57795(13) 0.64597(8) 0.0372(4) Uani 1 1 d . . .
N4 N -0.2918(3) 0.64346(13) 1.01738(8) 0.0549(4) Uani 1 1 d . . .
H4A H -0.2391 0.7049 1.0410 0.066 Uiso 1 1 calc R . .
H4B H -0.4025 0.5954 1.0386 0.066 Uiso 1 1 calc R . .
N5 N 0.2205(3) 0.73937(13) 0.81131(8) 0.0529(4) Uani 1 1 d . . .
H5A H 0.2747 0.8042 0.8305 0.063 Uiso 1 1 calc R . .
H5B H 0.2745 0.7193 0.7671 0.063 Uiso 1 1 calc R . .
C5 C -0.2009(3) 0.49920(12) 0.84980(8) 0.0369(3) Uani 1 1 d . . .
C6 C -0.2032(4) 0.62307(13) 0.94892(9) 0.0414(4) Uani 1 1 d . . .
C7 C -0.2824(4) 0.39208(15) 0.80966(10) 0.0489(4) Uani 1 1 d . . .
H7A H -0.1893 0.3884 0.7622 0.080 Uiso 1 1 calc . . .
H7B H -0.4766 0.3929 0.8013 0.080 Uiso 1 1 calc . . .
H7C H -0.2345 0.3253 0.8394 0.080 Uiso 1 1 calc . . .
C8 C 0.0557(3) 0.67128(13) 0.84938(9) 0.0403(4) 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
F1 C1 1.3341(17) . ?
O1 C4 1.2344(19) . ?
F2 C2 1.3369(17) . ?
N1 C5 1.3013(19) . ?
N1 C6 1.371(2) . ?
N2 C5 1.3439(19) . ?
N2 C8 1.360(2) . ?
N2 H2 0.8600 . ?
N3 C8 1.320(2) . ?
N3 C6 1.331(2) . ?
C1 C2 1.369(2) . ?
C1 C3 1.380(2) . ?
C2 C3 1.377(2) 3_666 ?
O2 C4 1.2480(19) . ?
C3 C2 1.377(2) 3_666 ?
C3 C4 1.5068(18) . ?
N4 C6 1.312(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 C8 1.310(2) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
C5 C7 1.476(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
C5 N1 C6 115.71(13) . . ?
C5 N2 C8 119.77(12) . . ?
C5 N2 H2 120.1 . . ?
C8 N2 H2 120.1 . . ?
C8 N3 C6 115.66(14) . . ?
F1 C1 C2 117.30(14) . . ?
F1 C1 C3 120.74(12) . . ?
C2 C1 C3 121.92(14) . . ?
F2 C2 C1 117.50(13) . . ?
F2 C2 C3 120.58(12) . 3_666 ?
C1 C2 C3 121.90(14) . 3_666 ?
C2 C3 C1 116.17(13) 3_666 . ?
C2 C3 C4 121.55(13) 3_666 . ?
C1 C3 C4 122.27(13) . . ?
O1 C4 O2 126.79(13) . . ?
O1 C4 C3 117.17(12) . . ?
O2 C4 C3 116.04(13) . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N1 C5 N2 121.64(14) . . ?
N1 C5 C7 120.84(14) . . ?
N2 C5 C7 117.52(13) . . ?
N4 C6 N3 118.79(15) . . ?
N4 C6 N1 115.54(14) . . ?
N3 C6 N1 125.67(14) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C8 N3 121.94(15) . . ?
N5 C8 N2 116.80(13) . . ?
N3 C8 N2 121.26(14) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 982117'
#######################################################################
#
#                 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_compound4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H22 F8 N10 O8'
_chemical_formula_weight         850.62

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                   7.6570(4)
_cell_length_b                   10.0492(8)
_cell_length_c                   11.3387(4)
_cell_angle_alpha                89.108(4)
_cell_angle_beta                 86.461(3)
_cell_angle_gamma                83.070(5)
_cell_volume                     864.42(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6912
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         29.57
_reflns_number_total             4007
_reflns_number_gt                2987
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0648P)²+0.2625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4007
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.23544(15) 0.05779(13) 0.32524(9) 0.0367(3) Uani 1 1 d . . .
F3 F -0.70184(16) -0.51846(14) 0.61840(11) 0.0432(3) Uani 1 1 d . . .
F4 F -0.94499(17) -0.67203(13) 0.68357(10) 0.0402(3) Uani 1 1 d . . .
F2 F -0.05132(16) -0.03939(14) 0.26946(9) 0.0404(3) Uani 1 1 d . . .
O1 O -0.35747(18) -0.20660(16) 0.50513(12) 0.0374(4) Uani 1 1 d . . .
H1 H -0.4481 -0.2333 0.4849 0.080 Uiso 1 1 calc . . .
N3 N -0.5958(2) -0.15099(18) -0.06210(13) 0.0344(4) Uani 1 1 d . . .
O2 O -0.6583(2) -0.27731(17) 0.50958(12) 0.0432(4) Uani 1 1 d . . .
O3 O -0.4045(2) -0.06054(17) 0.35712(13) 0.0431(4) Uani 1 1 d . . .
O4 O -0.6904(2) -0.31114(19) 0.32026(12) 0.0481(5) Uani 1 1 d . . .
N4 N -0.6798(2) -0.36443(18) -0.11705(13) 0.0336(4) Uani 1 1 d . . .
C10 C -0.0299(2) -0.0196(2) 0.38444(15) 0.0266(4) Uani 1 1 d . . .
C2 C -0.7264(3) -0.3281(2) 0.42605(16) 0.0293(4) Uani 1 1 d . . .
C3 C -0.8488(2) -0.5058(2) 0.55896(15) 0.0277(4) Uani 1 1 d . . .
C15 C -0.9777(3) -0.5856(2) 0.59328(15) 0.0270(4) Uani 1 1 d . . .
N5 N -0.6713(2) -0.30959(18) 0.08093(13) 0.0327(4) Uani 1 1 d . . .
C16 C -0.8677(2) -0.4170(2) 0.46400(15) 0.0260(4) Uani 1 1 d . . .
C17 C -0.3202(2) -0.1078(2) 0.43790(16) 0.0286(4) Uani 1 1 d . . .
C1 C 0.1199(2) 0.0320(2) 0.41342(16) 0.0267(4) Uani 1 1 d . . .
C9 C -0.1546(2) -0.05366(19) 0.46993(15) 0.0257(4) Uani 1 1 d . . .
N1 N -0.6241(3) -0.2060(2) -0.25411(14) 0.0466(5) Uani 1 1 d . . .
H1A H -0.5946 -0.1289 -0.2754 0.056 Uiso 1 1 calc R . .
H1B H -0.6476 -0.2613 -0.3064 0.056 Uiso 1 1 calc R . .
C11 C -0.7012(2) -0.3957(2) -0.00575(16) 0.0288(4) Uani 1 1 d . . .
C12 C -0.6332(3) -0.2394(2) -0.14209(16) 0.0323(4) Uani 1 1 d . . .
C13 C -0.7596(3) -0.5263(2) 0.02857(17) 0.0311(4) Uani 1 1 d . . .
C14 C -0.6130(3) -0.1901(2) 0.04993(16) 0.0314(4) Uani 1 1 d . . .
N2 N -0.5728(3) -0.1131(2) 0.13504(14) 0.0413(5) Uani 1 1 d . . .
H2A H -0.5912 -0.1529 0.2046 0.080 Uiso 1 1 calc . . .
H2B H -0.6402 -0.0346 0.1331 0.080 Uiso 1 1 calc . . .
H2C H -0.4600 -0.1000 0.1248 0.080 Uiso 1 1 calc . . .
C6 C -0.7896(3) -0.6133(2) -0.06049(19) 0.0407(5) Uani 1 1 d . . .
H6 H -0.7701 -0.5893 -0.1393 0.080 Uiso 1 1 calc . . .
C7 C -0.7885(4) -0.5639(2) 0.1459(2) 0.0457(6) Uani 1 1 d . . .
H7 H -0.7675 -0.5071 0.2061 0.080 Uiso 1 1 calc . . .
C4 C -0.8484(4) -0.6852(3) 0.1730(2) 0.0581(7) Uani 1 1 d . . .
H4 H -0.8694 -0.7093 0.2517 0.080 Uiso 1 1 calc . . .
C8 C -0.8773(4) -0.7711(3) 0.0846(3) 0.0544(7) Uani 1 1 d . . .
H8 H -0.9165 -0.8532 0.1038 0.080 Uiso 1 1 calc . . .
C5 C -0.8482(3) -0.7353(3) -0.0318(2) 0.0507(6) Uani 1 1 d . . .
H5 H -0.8681 -0.7932 -0.0914 0.080 Uiso 1 1 calc . . .


_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 C1 1.337(2) . ?
F3 C3 1.339(2) . ?
F4 C15 1.348(2) . ?
F2 C10 1.345(2) . ?
O1 C17 1.291(2) . ?
O1 H1 0.8200 . ?
N3 C14 1.327(2) . ?
N3 C12 1.346(3) . ?
O2 C2 1.253(2) . ?
O3 C17 1.211(2) . ?
O4 C2 1.228(2) . ?
N4 C11 1.301(2) . ?
N4 C12 1.368(3) . ?
C10 C1 1.374(3) . ?
C10 C9 1.387(2) . ?
C2 C16 1.522(2) . ?
C3 C15 1.380(3) . ?
C3 C16 1.391(3) . ?
C15 C16 1.382(3) 2_346 ?
N5 C14 1.365(3) . ?
N5 C11 1.367(3) . ?
C16 C15 1.382(3) 2_346 ?
C17 C9 1.505(3) . ?
C1 C9 1.391(3) 2_556 ?
C9 C1 1.391(3) 2_556 ?
N1 C12 1.308(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C11 C13 1.476(3) . ?
C13 C7 1.389(3) . ?
C13 C6 1.393(3) . ?
C14 N2 1.319(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C6 C5 1.383(3) . ?
C6 H6 0.9300 . ?
C7 C4 1.377(4) . ?
C7 H7 0.9300 . ?
C4 C8 1.378(4) . ?
C4 H4 0.9300 . ?
C8 C5 1.375(4) . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?

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
C17 O1 H1 109.5 . . ?
C14 N3 C12 115.37(18) . . ?
C11 N4 C12 116.47(17) . . ?
F2 C10 C1 117.92(16) . . ?
F2 C10 C9 120.18(16) . . ?
C1 C10 C9 121.89(16) . . ?
O4 C2 O2 126.11(17) . . ?
O4 C2 C16 119.26(16) . . ?
O2 C2 C16 114.63(15) . . ?
F3 C3 C15 117.86(17) . . ?
F3 C3 C16 120.63(16) . . ?
C15 C3 C16 121.49(17) . . ?
F4 C15 C3 117.27(16) . . ?
F4 C15 C16 120.16(16) . 2_346 ?
C3 C15 C16 122.52(17) . 2_346 ?
C14 N5 C11 119.25(16) . . ?
C15 C16 C3 115.98(16) 2_346 . ?
C15 C16 C2 122.24(17) 2_346 . ?
C3 C16 C2 121.78(17) . . ?
O3 C17 O1 126.00(18) . . ?
O3 C17 C9 121.55(17) . . ?
O1 C17 C9 112.45(16) . . ?
F1 C1 C10 117.64(16) . . ?
F1 C1 C9 120.43(16) . 2_556 ?
C10 C1 C9 121.91(16) . 2_556 ?
C10 C9 C1 116.20(16) . 2_556 ?
C10 C9 C17 121.80(16) . . ?
C1 C9 C17 121.99(16) 2_556 . ?
C12 N1 H1A 120.0 . . ?
C12 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N4 C11 N5 121.34(18) . . ?
N4 C11 C13 119.76(18) . . ?
N5 C11 C13 118.90(16) . . ?
N1 C12 N3 118.75(19) . . ?
N1 C12 N4 115.68(18) . . ?
N3 C12 N4 125.56(17) . . ?
C7 C13 C6 119.3(2) . . ?
C7 C13 C11 122.3(2) . . ?
C6 C13 C11 118.41(18) . . ?
N2 C14 N3 120.20(19) . . ?
N2 C14 N5 118.05(17) . . ?
N3 C14 N5 121.75(18) . . ?
C14 N2 H2A 109.5 . . ?
C14 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C14 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 C6 C13 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C13 C6 H6 120.0 . . ?
C4 C7 C13 120.0(2) . . ?
C4 C7 H7 120.0 . . ?
C13 C7 H7 120.0 . . ?
C7 C4 C8 120.6(2) . . ?
C7 C4 H4 119.7 . . ?
C8 C4 H4 119.7 . . ?
C5 C8 C4 120.0(2) . . ?
C5 C8 H8 120.0 . . ?
C4 C8 H8 120.0 . . ?
C8 C5 C6 120.1(2) . . ?
C8 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.824
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 982118'
#######################################################################
#
#                 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_compound5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H30 F12 N6 O12'
_chemical_formula_sum            'C48 H30 F12 N6 O12'
_chemical_formula_weight         1110.78

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.889(2)
_cell_length_b                   9.7001(8)
_cell_length_c                   19.7288(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.1980(10)
_cell_angle_gamma                90.00
_cell_volume                     4284.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2256
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13375
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.33
_reflns_number_total             5219
_reflns_number_gt                2698
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.1112P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5219
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1658
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.16058(6) 0.06763(14) 0.43750(10) 0.0436(4) Uani 1 1 d . . .
F2 F 0.13515(6) 0.32804(14) 0.40867(11) 0.0479(4) Uani 1 1 d . . .
O1 O 0.17081(8) 0.57834(17) 0.39730(12) 0.0431(5) Uani 1 1 d . . .
O4 O 0.26088(8) 0.62835(16) 0.52047(12) 0.0437(5) Uani 1 1 d . . .
C21 C 0.19280(10) 0.2937(2) 0.45366(16) 0.0295(5) Uani 1 1 d . . .
C2 C 0.21997(10) 0.5461(2) 0.46440(15) 0.0287(5) Uani 1 1 d . . .
C3 C 0.20619(10) 0.1543(2) 0.46917(15) 0.0292(5) Uani 1 1 d . . .
C14 C 0.23602(10) 0.3933(2) 0.48399(15) 0.0265(5) Uani 1 1 d . . .
F5 F 0.03521(6) 0.69394(15) 0.10141(11) 0.0517(5) Uani 1 1 d . . .
F3 F -0.17078(6) 0.58908(14) -0.07042(11) 0.0536(5) Uani 1 1 d . . .
F4 F -0.19527(6) 0.84817(15) -0.09380(11) 0.0524(5) Uani 1 1 d . . .
F6 F 0.01058(6) 0.95194(14) 0.07610(10) 0.0495(5) Uani 1 1 d . . .
O3 O -0.15959(8) 1.10006(17) -0.09669(12) 0.0459(5) Uani 1 1 d . . .
O6 O -0.09307(8) 0.39328(18) -0.01921(13) 0.0504(6) Uani 1 1 d . . .
O2 O 0.00001(8) 0.43891(18) 0.09437(13) 0.0556(6) Uani 1 1 d . . .
C25 C -0.12428(11) 0.6750(2) -0.03304(16) 0.0316(6) Uani 1 1 d . . .
O5 O -0.06738(8) 1.14715(17) 0.02273(13) 0.0520(6) Uani 1 1 d . . .
H5 H -0.0787 1.2273 0.0088 0.080 Uiso 1 1 calc . . .
C6 C -0.02277(10) 0.7270(2) 0.05179(16) 0.0309(6) Uani 1 1 d . . .
C17 C -0.05077(11) 0.4733(2) 0.03254(16) 0.0299(6) Uani 1 1 d . . .
C20 C -0.13752(10) 0.8146(2) -0.04624(16) 0.0315(6) Uani 1 1 d . . .
C1 C -0.09351(10) 0.9146(2) -0.01157(15) 0.0283(5) Uani 1 1 d . . .
C10 C -0.11033(11) 1.0655(2) -0.03259(16) 0.0325(6) Uani 1 1 d . . .
C11 C -0.03572(10) 0.8662(2) 0.03833(15) 0.0300(6) Uani 1 1 d . . .
C12 C -0.06618(11) 0.6265(2) 0.01668(15) 0.0282(5) Uani 1 1 d . . .
N1 N 0.04811(9) 0.5608(2) 0.29255(13) 0.0351(5) Uani 1 1 d . . .
H1 H 0.0843 0.5313 0.3245 0.080 Uiso 1 1 calc . . .
C13 C 0.03102(10) 0.6987(2) 0.27751(16) 0.0293(5) Uani 1 1 d . . .
C4 C 0.06409(11) 0.8195(2) 0.30704(17) 0.0366(6) Uani 1 1 d . . .
H4 H 0.1056 0.8194 0.3440 0.080 Uiso 1 1 calc . . .
C15 C 0.0000 0.4826(3) 0.2500 0.0356(8) Uani 1 2 d S . .
C16 C 0.03134(12) 0.9394(2) 0.27800(18) 0.0439(7) Uani 1 1 d . . .
H16 H 0.0514 1.0234 0.2961 0.080 Uiso 1 1 calc . . .
C7 C 0.0000 0.3288(4) 0.2500 0.0514(11) Uani 1 2 d S . .
H7A H -0.0404 0.2958 0.2141 0.077 Uiso 0.50 1 calc P . .
H7B H 0.0213 0.2958 0.3087 0.077 Uiso 0.50 1 calc P . .
H7C H 0.0191 0.2958 0.2272 0.077 Uiso 0.50 1 calc P . .
N2 N 0.12131(9) 0.4404(2) 0.20163(13) 0.0348(5) Uani 1 1 d . . .
H2 H 0.0853 0.4711 0.1672 0.080 Uiso 1 1 calc . . .
N3 N 0.21739(9) 0.4359(2) 0.28959(13) 0.0343(5) Uani 1 1 d . . .
H3 H 0.2539 0.4633 0.3216 0.080 Uiso 1 1 calc . . .
C18 C 0.19937(11) 0.2994(2) 0.27916(16) 0.0321(6) Uani 1 1 d . . .
C19 C 0.13722(11) 0.3032(2) 0.22236(16) 0.0325(6) Uani 1 1 d . . .
C8 C 0.13491(12) 0.0612(3) 0.23236(18) 0.0401(6) Uani 1 1 d . . .
H8 H 0.1141 -0.0212 0.2175 0.080 Uiso 1 1 calc . . .
C9 C 0.19765(12) 0.0591(3) 0.29026(17) 0.0396(6) Uani 1 1 d . . .
H9 H 0.2172 -0.0251 0.3126 0.080 Uiso 1 1 calc . . .
C22 C 0.10344(12) 0.1830(3) 0.19698(17) 0.0381(6) Uani 1 1 d . . .
H22 H 0.0619 0.1848 0.1583 0.080 Uiso 1 1 calc . . .
C23 C 0.23110(11) 0.1774(2) 0.31503(17) 0.0372(6) Uani 1 1 d . . .
H23 H 0.2726 0.1757 0.3537 0.080 Uiso 1 1 calc . . .
C24 C 0.17013(11) 0.5171(3) 0.24305(16) 0.0367(6) Uani 1 1 d . . .
C5 C 0.17097(12) 0.6699(3) 0.23961(18) 0.0472(7) Uani 1 1 d . . .
H5A H 0.2116 0.7015 0.2750 0.080 Uiso 1 1 calc . . .
H5B H 0.1520 0.7080 0.2614 0.080 Uiso 1 1 calc . . .
H5C H 0.1499 0.6990 0.1802 0.080 Uiso 1 1 calc . . .


_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 1.339(3) . ?
F2 C21 1.343(3) . ?
O1 C2 1.221(3) . ?
O4 C2 1.267(3) . ?
C21 C14 1.381(3) . ?
C21 C3 1.386(3) . ?
C2 C14 1.528(3) . ?
C3 C14 1.380(3) 7_556 ?
C14 C3 1.380(3) 7_556 ?
F5 C6 1.340(3) . ?
F3 C25 1.338(3) . ?
F4 C20 1.338(3) . ?
F6 C11 1.333(2) . ?
O3 C10 1.209(3) . ?
O6 C17 1.250(3) . ?
O2 C17 1.220(3) . ?
C25 C12 1.385(3) . ?
C25 C20 1.386(3) . ?
O5 C10 1.283(3) . ?
O5 H5 0.8200 . ?
C6 C12 1.380(3) . ?
C6 C11 1.381(3) . ?
C17 C12 1.526(3) . ?
C20 C1 1.387(3) . ?
C1 C11 1.378(3) . ?
C1 C10 1.516(3) . ?
N1 C15 1.318(3) . ?
N1 C13 1.391(3) . ?
N1 H1 0.8600 . ?
C13 C4 1.386(3) . ?
C13 C13 1.390(5) 2 ?
C4 C16 1.375(3) . ?
C4 H4 0.9300 . ?
C15 N1 1.318(3) 2 ?
C15 C7 1.492(5) . ?
C16 C16 1.404(5) 2 ?
C16 H16 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N2 C24 1.325(3) . ?
N2 C19 1.383(3) . ?
N2 H2 0.8600 . ?
N3 C24 1.321(3) . ?
N3 C18 1.389(3) . ?
N3 H3 0.8600 . ?
C18 C23 1.386(3) . ?
C18 C19 1.392(4) . ?
C19 C22 1.394(3) . ?
C8 C22 1.381(4) . ?
C8 C9 1.405(4) . ?
C8 H8 0.9300 . ?
C9 C23 1.376(3) . ?
C9 H9 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C5 1.485(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
F2 C21 C14 121.1(2) . . ?
F2 C21 C3 116.4(2) . . ?
C14 C21 C3 122.5(2) . . ?
O1 C2 O4 126.1(2) . . ?
O1 C2 C14 118.8(2) . . ?
O4 C2 C14 115.1(2) . . ?
F1 C3 C14 121.3(2) . 7_556 ?
F1 C3 C21 117.0(2) . . ?
C14 C3 C21 121.7(2) 7_556 . ?
C3 C14 C21 115.8(2) 7_556 . ?
C3 C14 C2 122.6(2) 7_556 . ?
C21 C14 C2 121.5(2) . . ?
F3 C25 C12 121.6(2) . . ?
F3 C25 C20 116.3(2) . . ?
C12 C25 C20 122.1(2) . . ?
C10 O5 H5 109.5 . . ?
F5 C6 C12 121.2(2) . . ?
F5 C6 C11 115.8(2) . . ?
C12 C6 C11 123.0(2) . . ?
O2 C17 O6 125.7(2) . . ?
O2 C17 C12 118.8(2) . . ?
O6 C17 C12 115.4(2) . . ?
F4 C20 C25 116.3(2) . . ?
F4 C20 C1 121.6(2) . . ?
C25 C20 C1 122.1(2) . . ?
C11 C1 C20 115.7(2) . . ?
C11 C1 C10 124.0(2) . . ?
C20 C1 C10 120.3(2) . . ?
O3 C10 O5 125.8(2) . . ?
O3 C10 C1 121.0(2) . . ?
O5 C10 C1 113.1(2) . . ?
F6 C11 C1 121.4(2) . . ?
F6 C11 C6 116.7(2) . . ?
C1 C11 C6 121.9(2) . . ?
C6 C12 C25 115.2(2) . . ?
C6 C12 C17 122.0(2) . . ?
C25 C12 C17 122.8(2) . . ?
C15 N1 C13 109.1(2) . . ?
C15 N1 H1 125.4 . . ?
C13 N1 H1 125.4 . . ?
C4 C13 C13 122.29(14) . 2 ?
C4 C13 N1 131.7(2) . . ?
C13 C13 N1 105.98(13) 2 . ?
C16 C4 C13 115.5(2) . . ?
C16 C4 H4 122.3 . . ?
C13 C4 H4 122.3 . . ?
N1 C15 N1 109.7(3) . 2 ?
N1 C15 C7 125.13(15) . . ?
N1 C15 C7 125.13(15) 2 . ?
C4 C16 C16 122.23(15) . 2 ?
C4 C16 H16 118.9 . . ?
C16 C16 H16 118.9 2 . ?
C15 C7 H7A 109.5 . . ?
C15 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C15 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C24 N2 C19 109.5(2) . . ?
C24 N2 H2 125.3 . . ?
C19 N2 H2 125.3 . . ?
C24 N3 C18 109.9(2) . . ?
C24 N3 H3 125.1 . . ?
C18 N3 H3 125.1 . . ?
C23 C18 N3 132.3(2) . . ?
C23 C18 C19 122.2(2) . . ?
N3 C18 C19 105.5(2) . . ?
N2 C19 C18 106.4(2) . . ?
N2 C19 C22 132.2(2) . . ?
C18 C19 C22 121.4(2) . . ?
C22 C8 C9 121.5(2) . . ?
C22 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C23 C9 C8 122.1(2) . . ?
C23 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C8 C22 C19 116.5(2) . . ?
C8 C22 H22 121.8 . . ?
C19 C22 H22 121.8 . . ?
C9 C23 C18 116.2(2) . . ?
C9 C23 H23 121.9 . . ?
C18 C23 H23 121.9 . . ?
N3 C24 N2 108.9(2) . . ?
N3 C24 C5 126.0(2) . . ?
N2 C24 C5 125.1(2) . . ?
C24 C5 H5A 109.5 . . ?
C24 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C24 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 982119'
#######################################################################
#
#                 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_compound6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 F4 N2 O4'
_chemical_formula_sum            'C13 H9 F4 N2 O4'
_chemical_formula_weight         333.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.3027(6)
_cell_length_b                   9.6227(7)
_cell_length_c                   9.7417(7)
_cell_angle_alpha                94.022(6)
_cell_angle_beta                 109.536(7)
_cell_angle_gamma                90.479(6)
_cell_volume                     643.20(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4750
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         29.28
_reflns_number_total             2956
_reflns_number_gt                2222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0452P)²+0.2137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.40138(18) 0.23164(12) 0.64770(12) 0.0432(3) Uani 1 1 d . . .
F3 F 0.02019(18) -0.07494(12) 0.14349(12) 0.0462(3) Uani 1 1 d . . .
F4 F 0.06340(18) 0.19581(12) 0.13900(12) 0.0453(3) Uani 1 1 d . . .
F2 F 0.3482(2) -0.03726(12) 0.65413(12) 0.0519(4) Uani 1 1 d . . .
O1 O 0.2830(2) -0.28731(14) 0.48459(17) 0.0460(4) Uani 1 1 d . . .
O4 O 0.2279(2) 0.45554(14) 0.48375(16) 0.0462(4) Uani 1 1 d . . .
H4 H 0.2466 0.5378 0.4740 0.080 Uiso 1 1 calc . . .
C6 C 0.1803(3) -0.06800(18) 0.39950(19) 0.0274(4) Uani 1 1 d . . .
C2 C 0.3027(3) 0.15923(18) 0.52115(19) 0.0284(4) Uani 1 1 d . . .
C3 C 0.2346(2) 0.22434(18) 0.39287(19) 0.0267(4) Uani 1 1 d . . .
C5 C 0.1115(3) -0.00168(18) 0.27104(19) 0.0284(4) Uani 1 1 d . . .
C1 C 0.2771(3) 0.01704(19) 0.52374(19) 0.0302(4) Uani 1 1 d . . .
C4 C 0.1382(3) 0.13972(19) 0.26796(18) 0.0284(4) Uani 1 1 d . . .
O3 O 0.3150(2) 0.41854(15) 0.28607(17) 0.0486(4) Uani 1 1 d . . .
C8 C 0.2654(3) 0.37846(19) 0.3827(2) 0.0310(4) Uani 1 1 d . . .
C7 C 0.1455(3) -0.22421(19) 0.4012(2) 0.0326(4) Uani 1 1 d . . .
O2 O -0.0133(2) -0.27330(15) 0.32187(19) 0.0549(5) Uani 1 1 d . . .
N2 N 0.3891(2) 0.68144(16) 0.93643(17) 0.0319(4) Uani 1 1 d . . .
N1 N 0.2010(2) 0.51078(17) 0.8143(2) 0.0415(4) Uani 1 1 d . . .
H1 H 0.1341 0.4538 0.7427 0.080 Uiso 1 1 calc . . .
C12 C 0.5252(3) 0.8030(2) 0.9714(3) 0.0410(5) Uani 1 1 d . . .
H12A H 0.5798 0.8088 0.8937 0.080 Uiso 1 1 calc . . .
H12B H 0.6313 0.7899 1.0608 0.080 Uiso 1 1 calc . . .
C13 C 0.4299(3) 0.9376(2) 0.9898(2) 0.0344(4) Uani 1 1 d . . .
H13A H 0.3876 0.9363 1.0740 0.080 Uiso 1 1 calc . . .
H13B H 0.3161 0.9469 0.9043 0.080 Uiso 1 1 calc . . .
C11 C 0.3090(3) 0.6180(2) 0.8042(2) 0.0388(5) Uani 1 1 d . . .
H11 H 0.3258 0.6443 0.7191 0.080 Uiso 1 1 calc . . .
C9 C 0.3296(3) 0.6121(2) 1.0333(2) 0.0379(5) Uani 1 1 d . . .
H9 H 0.3638 0.6349 1.1333 0.080 Uiso 1 1 calc . . .
C10 C 0.2127(3) 0.5053(2) 0.9564(3) 0.0415(5) Uani 1 1 d . . .
H10 H 0.1511 0.4396 0.9931 0.080 Uiso 1 1 calc . . .


_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 1.3421(19) . ?
F3 C5 1.3418(19) . ?
F4 C4 1.3450(19) . ?
F2 C1 1.346(2) . ?
O1 C7 1.253(2) . ?
O4 C8 1.294(2) . ?
O4 H4 0.8200 . ?
C6 C1 1.383(2) . ?
C6 C5 1.387(2) . ?
C6 C7 1.525(2) . ?
C2 C3 1.379(2) . ?
C2 C1 1.383(2) . ?
C3 C4 1.385(2) . ?
C3 C8 1.513(2) . ?
C5 C4 1.377(3) . ?
O3 C8 1.201(2) . ?
C7 O2 1.227(2) . ?
N2 C11 1.324(2) . ?
N2 C9 1.372(3) . ?
N2 C12 1.473(2) . ?
N1 C11 1.322(3) . ?
N1 C10 1.363(3) . ?
N1 H1 0.8600 . ?
C12 C13 1.503(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C13 1.529(3) 2_677 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11 0.9300 . ?
C9 C10 1.340(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?

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
C8 O4 H4 109.5 . . ?
C1 C6 C5 115.68(15) . . ?
C1 C6 C7 123.14(16) . . ?
C5 C6 C7 121.16(16) . . ?
F1 C2 C3 120.90(15) . . ?
F1 C2 C1 117.60(15) . . ?
C3 C2 C1 121.48(16) . . ?
C2 C3 C4 116.31(15) . . ?
C2 C3 C8 123.70(16) . . ?
C4 C3 C8 119.95(15) . . ?
F3 C5 C4 117.46(15) . . ?
F3 C5 C6 120.58(15) . . ?
C4 C5 C6 121.93(16) . . ?
F2 C1 C2 117.26(15) . . ?
F2 C1 C6 120.23(15) . . ?
C2 C1 C6 122.50(16) . . ?
F4 C4 C5 117.96(15) . . ?
F4 C4 C3 119.94(15) . . ?
C5 C4 C3 122.09(16) . . ?
O3 C8 O4 126.47(18) . . ?
O3 C8 C3 120.58(18) . . ?
O4 C8 C3 112.92(16) . . ?
O2 C7 O1 127.64(17) . . ?
O2 C7 C6 116.53(17) . . ?
O1 C7 C6 115.83(16) . . ?
C11 N2 C9 108.67(16) . . ?
C11 N2 C12 124.62(17) . . ?
C9 N2 C12 126.66(17) . . ?
C11 N1 C10 108.96(17) . . ?
C11 N1 H1 125.5 . . ?
C10 N1 H1 125.5 . . ?
N2 C12 C13 112.68(16) . . ?
N2 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C13 111.1(2) . 2_677 ?
C12 C13 H13A 109.4 . . ?
C13 C13 H13A 109.4 2_677 . ?
C12 C13 H13B 109.4 . . ?
C13 C13 H13B 109.4 2_677 . ?
H13A C13 H13B 108.0 . . ?
N1 C11 N2 108.21(18) . . ?
N1 C11 H11 125.9 . . ?
N2 C11 H11 125.9 . . ?
C10 C9 N2 106.88(18) . . ?
C10 C9 H9 126.6 . . ?
N2 C9 H9 126.6 . . ?
C9 C10 N1 107.28(17) . . ?
C9 C10 H10 126.4 . . ?
N1 C10 H10 126.4 . . ?

_diffrn_measured_fraction_theta_max 0.844
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 982120'
#######################################################################
#
#                 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_compound7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 F4 N3 O6'
_chemical_formula_weight         381.25

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   6.1044(4)
_cell_length_b                   12.0203(6)
_cell_length_c                   20.6007(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.195(5)
_cell_angle_gamma                90.00
_cell_volume                     1499.71(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7007
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         29.60
_reflns_number_total             3515
_reflns_number_gt                2088
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0365P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
F2 F 0.8111(2) 0.37827(11) 0.07321(7) 0.0507(4) Uani 1 1 d . . .
F1 F 0.8680(2) 0.42779(11) -0.04777(7) 0.0470(4) Uani 1 1 d . . .
O2 O 0.5220(3) 0.65953(13) -0.15105(8) 0.0492(5) Uani 1 1 d . . .
O1 O 0.6534(3) 0.49217(12) -0.16926(8) 0.0400(4) Uani 1 1 d . . .
C11 C 0.6828(3) 0.46427(17) -0.02567(11) 0.0311(5) Uani 1 1 d . . .
C12 C 0.5709(4) 0.56223(18) -0.13419(11) 0.0328(5) Uani 1 1 d . . .
C16 C 0.6524(4) 0.43796(16) 0.03756(12) 0.0319(5) Uani 1 1 d . . .
C18 C 0.5322(3) 0.52816(16) -0.06574(11) 0.0291(5) Uani 1 1 d . . .
N1 N 0.0752(3) 0.37821(13) 0.24739(9) 0.0293(4) Uani 1 1 d . . .
H1 H 0.1521 0.4093 0.2202 0.035 Uiso 1 1 calc R . .
O8 O -0.1105(2) 0.53893(12) 0.25430(8) 0.0413(4) Uani 1 1 d . . .
N2 N 0.0001(3) 0.22296(14) 0.30624(9) 0.0311(4) Uani 1 1 d . . .
H2 H 0.0319 0.1560 0.3188 0.037 Uiso 1 1 calc R . .
N3 N 0.2879(3) 0.22148(14) 0.24336(10) 0.0396(5) Uani 1 1 d . . .
H3A H 0.3204 0.1543 0.2553 0.048 Uiso 1 1 calc R . .
H3B H 0.3641 0.2552 0.2170 0.048 Uiso 1 1 calc R . .
O6 O -0.2782(3) 0.67333(15) 0.34753(11) 0.0615(6) Uani 1 1 d G . .
H6A H -0.1917 0.7286 0.3550 0.092 Uiso 1 1 d G . .
H6B H -0.2284 0.6300 0.3202 0.092 Uiso 1 1 d G . .
C14 C 0.1229(3) 0.27218(16) 0.26525(11) 0.0288(5) Uani 1 1 d . . .
C15 C -0.1762(3) 0.27566(17) 0.32919(11) 0.0305(5) Uani 1 1 d . . .
C17 C -0.0905(3) 0.43979(17) 0.27030(11) 0.0307(5) Uani 1 1 d . . .
C20 C -0.2229(4) 0.38114(17) 0.31130(11) 0.0333(5) Uani 1 1 d . . .
H20 H -0.3433 0.4165 0.3258 0.040 Uiso 1 1 calc R . .
C26 C -0.2986(4) 0.20905(18) 0.37416(12) 0.0405(6) Uani 1 1 d . . .
H26A H -0.3546 0.1424 0.3524 0.061 Uiso 1 1 calc R . .
H26B H -0.4193 0.2522 0.3864 0.061 Uiso 1 1 calc R . .
H26C H -0.2005 0.1897 0.4126 0.061 Uiso 1 1 calc R . .
F3 F 0.3047(2) 0.82803(10) 0.05511(7) 0.0528(4) Uani 1 1 d . . .
F4 F 0.6009(2) 0.78629(10) -0.02391(7) 0.0534(4) Uani 1 1 d . . .
O3 O 0.1756(3) 0.99341(17) 0.13927(10) 0.0653(6) Uani 1 1 d . . .
C21 C 0.4018(4) 0.91511(18) 0.02911(12) 0.0354(6) Uani 1 1 d . . .
C22 C 0.5565(4) 0.89339(17) -0.01219(11) 0.0352(6) Uani 1 1 d . . .
C24 C 0.3401(3) 1.02258(18) 0.04254(11) 0.0324(5) Uani 1 1 d . . .
C25 C 0.1752(4) 1.0444(2) 0.08937(13) 0.0412(6) Uani 1 1 d . . .
O4 O 0.0374(3) 1.12358(17) 0.06952(9) 0.0623(5) Uani 1 1 d . . .
H4 H -0.0473 1.1339 0.0968 0.093 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
F2 C16 1.347(2) . ?
F1 C11 1.344(2) . ?
O2 C12 1.246(2) . ?
O1 C12 1.255(3) . ?
C11 C16 1.376(3) . ?
C11 C18 1.388(3) . ?
C12 C18 1.515(3) . ?
C16 C18 1.392(3) 3_665 ?
C18 C16 1.392(3) 3_665 ?
N1 C14 1.348(2) . ?
N1 C17 1.383(3) . ?
O8 C17 1.238(2) . ?
N2 C14 1.335(3) . ?
N2 C15 1.382(3) . ?
N3 C14 1.305(3) . ?
C15 C20 1.341(3) . ?
C15 C26 1.494(3) . ?
C17 C20 1.426(3) . ?
F3 C21 1.346(2) . ?
F4 C22 1.344(2) . ?
O3 C25 1.197(3) . ?
C21 C22 1.373(3) . ?
C21 C24 1.383(3) . ?
C22 C24 1.381(3) 3_675 ?
C24 C22 1.381(3) 3_675 ?
C24 C25 1.502(3) . ?
C25 O4 1.301(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C11 C16 117.7(2) . . ?
F1 C11 C18 120.1(2) . . ?
C16 C11 C18 122.2(2) . . ?
O2 C12 O1 124.7(2) . . ?
O2 C12 C18 116.97(19) . . ?
O1 C12 C18 118.34(19) . . ?
F2 C16 C11 117.74(19) . . ?
F2 C16 C18 119.5(2) . 3_665 ?
C11 C16 C18 122.7(2) . 3_665 ?
C11 C18 C16 115.1(2) . 3_665 ?
C11 C18 C12 122.30(19) . . ?
C16 C18 C12 122.5(2) 3_665 . ?
C14 N1 C17 123.72(18) . . ?
C14 N2 C15 122.40(18) . . ?
N3 C14 N2 122.02(19) . . ?
N3 C14 N1 119.8(2) . . ?
N2 C14 N1 118.17(19) . . ?
C20 C15 N2 119.2(2) . . ?
C20 C15 C26 124.9(2) . . ?
N2 C15 C26 115.95(18) . . ?
O8 C17 N1 118.42(19) . . ?
O8 C17 C20 126.1(2) . . ?
N1 C17 C20 115.49(18) . . ?
C15 C20 C17 120.9(2) . . ?
F3 C21 C22 118.0(2) . . ?
F3 C21 C24 120.2(2) . . ?
C22 C21 C24 121.8(2) . . ?
F4 C22 C21 117.6(2) . . ?
F4 C22 C24 120.4(2) . 3_675 ?
C21 C22 C24 122.01(19) . 3_675 ?
C22 C24 C21 116.2(2) 3_675 . ?
C22 C24 C25 122.9(2) 3_675 . ?
C21 C24 C25 120.8(2) . . ?
O3 C25 O4 125.2(2) . . ?
O3 C25 C24 122.2(2) . . ?
O4 C25 C24 112.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.832
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 982121'
#######################################################################
#
#                 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_compound8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 F8 N4 O9'
_chemical_formula_weight         760.55

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.0755(4)
_cell_length_b                   36.884(2)
_cell_length_c                   9.7005(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.508(3)
_cell_angle_gamma                90.00
_cell_volume                     3241.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19041
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         29.75
_reflns_number_total             7709
_reflns_number_gt                4995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0435P)²+1.4720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7709
_refine_ls_number_parameters     486
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.33780(14) 0.00835(4) 0.14495(12) 0.0462(4) Uani 1 1 d . . .
F2 F 0.26998(16) 0.00268(4) -0.12132(12) 0.0519(4) Uani 1 1 d . . .
F3 F -0.07239(16) 0.08573(4) 0.18866(12) 0.0557(4) Uani 1 1 d . . .
O1 O 0.06045(16) 0.04843(5) 0.40734(13) 0.0399(4) Uani 1 1 d . . .
O2 O 0.13242(18) 0.04449(5) -0.33930(13) 0.0449(4) Uani 1 1 d . . .
H2 H 0.1038 0.0427 -0.4209 0.080 Uiso 1 1 calc . . .
F4 F -0.13165(16) 0.08231(5) -0.07844(13) 0.0630(5) Uani 1 1 d . . .
N2 N -0.36282(18) 0.08226(5) -0.38855(16) 0.0298(4) Uani 1 1 d . . .
O3 O 0.30090(17) 0.05136(5) 0.37482(14) 0.0435(4) Uani 1 1 d . . .
O4 O -0.10384(18) 0.03301(5) -0.30079(14) 0.0442(4) Uani 1 1 d . . .
N3 N -0.61539(19) 0.14348(5) -0.45711(17) 0.0333(4) Uani 1 1 d . . .
C5 C 0.1849(2) 0.02411(6) -0.04667(18) 0.0296(5) Uani 1 1 d . . .
C6 C 0.2193(2) 0.02664(6) 0.09365(19) 0.0285(5) Uani 1 1 d . . .
C7 C 0.1709(2) 0.04897(6) 0.33420(18) 0.0286(5) Uani 1 1 d . . .
C8 C 0.0223(2) 0.03918(6) -0.26237(19) 0.0311(5) Uani 1 1 d . . .
C9 C 0.0154(2) 0.06464(6) 0.11534(19) 0.0323(5) Uani 1 1 d . . .
C1 C -0.0173(2) 0.06269(7) -0.02504(19) 0.0349(5) Uani 1 1 d . . .
C2 C 0.1343(2) 0.04671(6) 0.17900(18) 0.0257(4) Uani 1 1 d . . .
C3 C -0.5454(2) 0.08576(6) -0.2092(2) 0.0295(5) Uani 1 1 d . . .
C4 C -0.7179(2) 0.12452(7) -0.3683(2) 0.0365(5) Uani 1 1 d . . .
H4A H -0.7554 0.1031 -0.4164 0.080 Uiso 1 1 calc . . .
H4B H -0.8013 0.1403 -0.3546 0.080 Uiso 1 1 calc . . .
C10 C -0.2907(2) 0.11323(7) -0.3426(2) 0.0366(5) Uani 1 1 d . . .
H10 H -0.3156 0.1276 -0.2687 0.080 Uiso 1 1 calc . . .
C11 C -0.5531(2) 0.17599(7) -0.4355(2) 0.0376(5) Uani 1 1 d . . .
C12 C 0.0663(2) 0.04206(6) -0.10990(18) 0.0295(5) Uani 1 1 d . . .
C13 C -0.6499(2) 0.11321(6) -0.2277(2) 0.0311(5) Uani 1 1 d . . .
C14 C -0.2934(2) 0.06892(7) -0.4954(2) 0.0368(5) Uani 1 1 d . . .
N4 N -0.4771(2) 0.18354(6) -0.5444(2) 0.0468(5) Uani 1 1 d . . .
H4 H -0.4267 0.2030 -0.5550 0.080 Uiso 1 1 calc . . .
C15 C -0.4894(2) 0.06435(6) -0.3275(2) 0.0338(5) Uani 1 1 d . . .
H15A H -0.4596 0.0404 -0.2949 0.080 Uiso 1 1 calc . . .
H15B H -0.5687 0.0613 -0.3983 0.080 Uiso 1 1 calc . . .
C16 C -0.4935(3) 0.07647(7) -0.0756(2) 0.0402(6) Uani 1 1 d . . .
H16 H -0.4226 0.0584 -0.0626 0.080 Uiso 1 1 calc . . .
C17 C -0.7031(3) 0.12994(7) -0.1124(2) 0.0451(6) Uani 1 1 d . . .
H17 H -0.7745 0.1480 -0.1242 0.080 Uiso 1 1 calc . . .
N1 N -0.1834(2) 0.09135(6) -0.51805(19) 0.0462(5) Uani 1 1 d . . .
H1 H -0.1236 0.0889 -0.5829 0.080 Uiso 1 1 calc . . .
C18 C -0.5464(3) 0.09383(8) 0.0380(2) 0.0507(7) Uani 1 1 d . . .
H18 H -0.5105 0.0876 0.1267 0.080 Uiso 1 1 calc . . .
C19 C -0.5783(3) 0.13046(7) -0.5844(2) 0.0435(6) Uani 1 1 d . . .
H19 H -0.6078 0.1086 -0.6252 0.080 Uiso 1 1 calc . . .
C20 C -0.1783(3) 0.11899(8) -0.4234(2) 0.0462(6) Uani 1 1 d . . .
H20 H -0.1105 0.1379 -0.4167 0.080 Uiso 1 1 calc . . .
C21 C -0.4912(3) 0.15564(8) -0.6370(3) 0.0525(7) Uani 1 1 d . . .
H21 H -0.4480 0.1544 -0.7214 0.080 Uiso 1 1 calc . . .
C24 C -0.6518(3) 0.12023(8) 0.0193(2) 0.0560(7) Uani 1 1 d . . .
H24 H -0.6888 0.1316 0.0954 0.080 Uiso 1 1 calc . . .
C22 C -0.3299(3) 0.03515(8) -0.5702(2) 0.0545(7) Uani 1 1 d . . .
H22A H -0.2638 0.0320 -0.6429 0.080 Uiso 1 1 calc . . .
H22B H -0.4296 0.0364 -0.6092 0.080 Uiso 1 1 calc . . .
H22C H -0.3202 0.0150 -0.5076 0.080 Uiso 1 1 calc . . .
C23 C -0.5647(3) 0.19977(8) -0.3142(3) 0.0566(7) Uani 1 1 d . . .
H23A H -0.6253 0.1883 -0.2492 0.080 Uiso 1 1 calc . . .
H23B H -0.6082 0.2225 -0.3430 0.080 Uiso 1 1 calc . . .
H23C H -0.4680 0.2040 -0.2714 0.080 Uiso 1 1 calc . . .
F5 F 0.21809(16) 0.22836(4) 0.92089(13) 0.0537(4) Uani 1 1 d . . .
F6 F 0.25467(15) 0.21513(4) 1.19032(13) 0.0545(4) Uani 1 1 d . . .
F7 F -0.25018(16) 0.17261(4) 0.91028(13) 0.0552(4) Uani 1 1 d . . .
F8 F -0.21132(16) 0.15920(5) 1.18016(14) 0.0575(4) Uani 1 1 d . . .
C25 C 0.1090(2) 0.21156(6) 0.9823(2) 0.0340(5) Uani 1 1 d . . .
O7 O 0.0470(2) 0.19528(5) 0.67732(15) 0.0542(5) Uani 1 1 d . . .
C26 C 0.0220(2) 0.18699(6) 1.19191(19) 0.0325(5) Uani 1 1 d . . .
O8 O -0.1495(2) 0.22919(5) 0.71698(15) 0.0565(5) Uani 1 1 d . . .
C30 C -0.1038(2) 0.17636(7) 1.1165(2) 0.0358(5) Uani 1 1 d . . .
C31 C -0.1237(2) 0.18358(6) 0.9775(2) 0.0355(5) Uani 1 1 d . . .
C32 C 0.1287(2) 0.20467(6) 1.1224(2) 0.0342(5) Uani 1 1 d . . .
C29 C 0.0421(2) 0.17860(7) 1.3447(2) 0.0355(5) Uani 1 1 d . . .
C28 C -0.0181(2) 0.20147(6) 0.90679(19) 0.0331(5) Uani 1 1 d . . .
C27 C -0.0440(3) 0.20979(7) 0.7525(2) 0.0385(6) Uani 1 1 d . . .
O5 O 0.0261(3) 0.20641(5) 1.41996(16) 0.0770(7) Uani 1 1 d . . .
H5 H 0.0371 0.2006 1.5016 0.080 Uiso 1 1 calc . . .
O6 O 0.0657(3) 0.14850(6) 1.38568(17) 0.0663(6) Uani 1 1 d . . .
O1W O 0.7026(2) 0.24106(7) 0.4511(2) 0.0713(6) Uani 1 1 d D . .
H1WA H 0.743(4) 0.2459(12) 0.381(2) 0.125(17) Uiso 1 1 d D . .
H1WB H 0.765(3) 0.2381(11) 0.516(2) 0.111(15) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.339(2) . ?
F2 C5 1.347(2) . ?
F3 C9 1.347(2) . ?
O1 C7 1.263(2) . ?
O2 C8 1.298(2) . ?
O2 H2 0.8200 . ?
F4 C1 1.343(2) . ?
N2 C14 1.340(3) . ?
N2 C10 1.377(3) . ?
N2 C15 1.480(3) . ?
O3 C7 1.224(2) . ?
O4 C8 1.204(3) . ?
N3 C11 1.337(3) . ?
N3 C19 1.386(3) . ?
N3 C4 1.482(3) . ?
C5 C12 1.376(3) . ?
C5 C6 1.381(3) . ?
C6 C2 1.381(3) . ?
C7 C2 1.524(2) . ?
C8 C12 1.512(3) . ?
C9 C1 1.378(3) . ?
C9 C2 1.378(3) . ?
C1 C12 1.382(3) . ?
C3 C13 1.391(3) . ?
C3 C16 1.394(3) . ?
C3 C15 1.507(3) . ?
C4 C13 1.521(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 C20 1.342(3) . ?
C10 H10 0.9300 . ?
C11 N4 1.326(3) . ?
C11 C23 1.477(3) . ?
C13 C17 1.390(3) . ?
C14 N1 1.325(3) . ?
C14 C22 1.469(4) . ?
N4 C21 1.367(3) . ?
N4 H4 0.8600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C24 1.380(4) . ?
C17 H17 0.9300 . ?
N1 C20 1.371(3) . ?
N1 H1 0.8600 . ?
C18 C24 1.369(4) . ?
C18 H18 0.9300 . ?
C19 C21 1.340(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C24 H24 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
F5 C25 1.338(2) . ?
F6 C32 1.341(2) . ?
F7 C31 1.347(2) . ?
F8 C30 1.345(2) . ?
C25 C28 1.379(3) . ?
C25 C32 1.383(3) . ?
O7 C27 1.255(3) . ?
C26 C30 1.375(3) . ?
C26 C32 1.377(3) . ?
C26 C29 1.514(3) . ?
O8 C27 1.227(3) . ?
C30 C31 1.375(3) . ?
C31 C28 1.380(3) . ?
C29 O6 1.194(3) . ?
C29 O5 1.273(3) . ?
C28 C27 1.531(3) . ?
O5 H5 0.8200 . ?
O1W H1WA 0.812(18) . ?
O1W H1WB 0.831(17) . ?

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
C8 O2 H2 109.5 . . ?
C14 N2 C10 108.59(18) . . ?
C14 N2 C15 123.98(19) . . ?
C10 N2 C15 127.30(16) . . ?
C11 N3 C19 109.09(18) . . ?
C11 N3 C4 127.35(18) . . ?
C19 N3 C4 123.40(19) . . ?
F2 C5 C12 120.09(16) . . ?
F2 C5 C6 117.86(18) . . ?
C12 C5 C6 122.03(18) . . ?
F1 C6 C5 117.39(17) . . ?
F1 C6 C2 120.85(16) . . ?
C5 C6 C2 121.75(18) . . ?
O3 C7 O1 127.07(17) . . ?
O3 C7 C2 118.03(17) . . ?
O1 C7 C2 114.90(17) . . ?
O4 C8 O2 126.98(17) . . ?
O4 C8 C12 120.35(18) . . ?
O2 C8 C12 112.66(18) . . ?
F3 C9 C1 116.93(18) . . ?
F3 C9 C2 120.82(16) . . ?
C1 C9 C2 122.23(18) . . ?
F4 C1 C9 117.91(18) . . ?
F4 C1 C12 120.44(17) . . ?
C9 C1 C12 121.63(19) . . ?
C9 C2 C6 116.05(16) . . ?
C9 C2 C7 122.26(17) . . ?
C6 C2 C7 121.69(17) . . ?
C13 C3 C16 119.15(19) . . ?
C13 C3 C15 122.84(18) . . ?
C16 C3 C15 118.0(2) . . ?
N3 C4 C13 114.60(17) . . ?
N3 C4 H4A 108.6 . . ?
C13 C4 H4A 108.6 . . ?
N3 C4 H4B 108.6 . . ?
C13 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C20 C10 N2 107.8(2) . . ?
C20 C10 H10 126.1 . . ?
N2 C10 H10 126.1 . . ?
N4 C11 N3 107.4(2) . . ?
N4 C11 C23 125.1(2) . . ?
N3 C11 C23 127.4(2) . . ?
C5 C12 C1 116.29(16) . . ?
C5 C12 C8 123.70(18) . . ?
C1 C12 C8 119.98(18) . . ?
C17 C13 C3 119.2(2) . . ?
C17 C13 C4 117.3(2) . . ?
C3 C13 C4 123.44(18) . . ?
N1 C14 N2 107.1(2) . . ?
N1 C14 C22 126.7(2) . . ?
N2 C14 C22 126.2(2) . . ?
C11 N4 C21 109.5(2) . . ?
C11 N4 H4 125.3 . . ?
C21 N4 H4 125.3 . . ?
N2 C15 C3 112.12(18) . . ?
N2 C15 H15A 109.2 . . ?
C3 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C3 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C18 C16 C3 120.8(2) . . ?
C18 C16 H16 119.6 . . ?
C3 C16 H16 119.6 . . ?
C24 C17 C13 121.0(2) . . ?
C24 C17 H17 119.5 . . ?
C13 C17 H17 119.5 . . ?
C14 N1 C20 110.40(18) . . ?
C14 N1 H1 124.8 . . ?
C20 N1 H1 124.8 . . ?
C24 C18 C16 119.8(2) . . ?
C24 C18 H18 120.1 . . ?
C16 C18 H18 120.1 . . ?
C21 C19 N3 106.3(2) . . ?
C21 C19 H19 126.9 . . ?
N3 C19 H19 126.9 . . ?
C10 C20 N1 106.1(2) . . ?
C10 C20 H20 126.9 . . ?
N1 C20 H20 126.9 . . ?
C19 C21 N4 107.8(2) . . ?
C19 C21 H21 126.1 . . ?
N4 C21 H21 126.1 . . ?
C18 C24 C17 120.0(2) . . ?
C18 C24 H24 120.0 . . ?
C17 C24 H24 120.0 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F5 C25 C28 120.37(18) . . ?
F5 C25 C32 117.9(2) . . ?
C28 C25 C32 121.7(2) . . ?
C30 C26 C32 117.39(18) . . ?
C30 C26 C29 120.60(19) . . ?
C32 C26 C29 122.0(2) . . ?
F8 C30 C26 119.48(18) . . ?
F8 C30 C31 119.1(2) . . ?
C26 C30 C31 121.4(2) . . ?
F7 C31 C30 118.2(2) . . ?
F7 C31 C28 120.02(18) . . ?
C30 C31 C28 121.7(2) . . ?
F6 C32 C26 119.95(18) . . ?
F6 C32 C25 118.99(19) . . ?
C26 C32 C25 121.1(2) . . ?
O6 C29 O5 125.6(2) . . ?
O6 C29 C26 121.6(2) . . ?
O5 C29 C26 112.7(2) . . ?
C25 C28 C31 116.66(18) . . ?
C25 C28 C27 122.6(2) . . ?
C31 C28 C27 120.7(2) . . ?
O8 C27 O7 127.94(19) . . ?
O8 C27 C28 117.53(19) . . ?
O7 C27 C28 114.5(2) . . ?
C29 O5 H5 109.5 . . ?
H1WA O1W H1WB 110(3) . . ?

_diffrn_measured_fraction_theta_max 0.834
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 982122'
#######################################################################
#
#                 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_compound9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 F8 N4 O8'
_chemical_formula_sum            'C32 H22 F8 N4 O8'
_chemical_formula_weight         742.54

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

_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                   7.1153(5)
_cell_length_b                   8.4148(6)
_cell_length_c                   14.4196(13)
_cell_angle_alpha                99.8950(10)
_cell_angle_beta                 97.073(2)
_cell_angle_gamma                111.8780(10)
_cell_volume                     772.54(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             378
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4968
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.25
_reflns_number_total             3540
_reflns_number_gt                2728
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0900P)²+0.1419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.61505(19) 0.97023(17) 0.42851(9) 0.0569(4) Uani 1 1 d . . .
F2 F 1.2650(2) 1.28150(17) 0.63969(10) 0.0612(4) Uani 1 1 d . . .
O3 O 1.5658(2) 1.17948(18) 0.81609(10) 0.0520(4) Uani 1 1 d . . .
O1 O 0.7968(2) 1.34957(18) 0.53077(10) 0.0498(4) Uani 1 1 d . . .
O2 O 0.8759(3) 1.2907(2) 0.67218(10) 0.0514(4) Uani 1 1 d . . .
C1 C 0.9345(3) 1.1335(2) 0.53762(12) 0.0327(4) Uani 1 1 d . . .
C2 C 0.8610(3) 1.2713(2) 0.58312(12) 0.0359(4) Uani 1 1 d . . .
O4 O 1.7473(3) 1.44701(19) 0.79522(11) 0.0573(4) Uani 1 1 d . . .
C3 C 1.1292(3) 1.1418(2) 0.57125(12) 0.0364(4) Uani 1 1 d . . .
C4 C 0.8070(3) 0.9891(2) 0.46486(12) 0.0347(4) Uani 1 1 d . . .
F5 F 1.3848(4) 1.5370(3) 0.82264(9) 0.0996(7) Uani 1 1 d . . .
F6 F 1.7430(3) 1.3262(3) 1.02970(10) 0.1079(8) Uani 1 1 d . . .
C5 C 1.5674(3) 1.4279(2) 0.92194(12) 0.0366(4) Uani 1 1 d . . .
C6 C 1.6283(3) 1.3382(2) 0.83725(13) 0.0383(4) Uani 1 1 d . . .
C7 C 1.4439(4) 1.5175(3) 0.91007(13) 0.0481(5) Uani 1 1 d . . .
C8 C 1.6227(4) 1.4125(3) 1.01338(14) 0.0515(6) Uani 1 1 d . . .
N2 N 0.1113(2) 0.10095(19) 0.26866(10) 0.0345(3) Uani 1 1 d . . .
N1 N 0.2236(3) 0.3510(2) 0.37068(11) 0.0390(4) Uani 1 1 d . . .
H1 H 0.2297 0.4481 0.4046 0.080 Uiso 1 1 calc . . .
C9 C 0.3101(3) 0.1359(3) 0.31271(14) 0.0418(4) Uani 1 1 d . . .
H9 H 0.3820 0.0647 0.3008 0.080 Uiso 1 1 calc . . .
C10 C -0.0093(3) -0.0252(2) 0.09299(13) 0.0380(4) Uani 1 1 d . . .
C11 C -0.0220(3) -0.0560(2) 0.19251(13) 0.0418(4) Uani 1 1 d . . .
H11A H -0.1642 -0.0906 0.2004 0.080 Uiso 1 1 calc . . .
H11B H 0.0182 -0.1523 0.1992 0.080 Uiso 1 1 calc . . .
C12 C 0.0615(3) 0.2348(2) 0.30512(12) 0.0352(4) Uani 1 1 d . . .
C13 C -0.1369(3) 0.2499(3) 0.27823(18) 0.0546(5) Uani 1 1 d . . .
H13A H -0.2278 0.1490 0.2284 0.080 Uiso 1 1 calc . . .
H13B H -0.1128 0.3549 0.2553 0.080 Uiso 1 1 calc . . .
H13C H -0.1992 0.2555 0.3334 0.080 Uiso 1 1 calc . . .
C14 C -0.1793(3) -0.0265(3) 0.03387(15) 0.0465(5) Uani 1 1 d . . .
H14 H -0.3008 -0.0442 0.0564 0.080 Uiso 1 1 calc . . .
C15 C 0.1704(3) 0.0020(3) 0.05737(15) 0.0480(5) Uani 1 1 d . . .
H15 H 0.2862 0.0037 0.0960 0.080 Uiso 1 1 calc . . .
C16 C 0.3807(3) 0.2930(3) 0.37641(14) 0.0443(5) Uani 1 1 d . . .
H16 H 0.5108 0.3511 0.4166 0.080 Uiso 1 1 calc . . .


_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 C4 1.341(2) . ?
F2 C3 1.345(2) . ?
O3 C6 1.208(2) . ?
O1 C2 1.234(2) . ?
O2 C2 1.252(2) . ?
C1 C4 1.381(2) . ?
C1 C3 1.382(3) . ?
C1 C2 1.524(2) . ?
O4 C6 1.289(2) . ?
C3 C4 1.387(2) 2_776 ?
C4 C3 1.387(2) 2_776 ?
F5 C7 1.336(2) . ?
F6 C8 1.337(2) . ?
C5 C7 1.368(3) . ?
C5 C8 1.371(3) . ?
C5 C6 1.519(2) . ?
C7 C8 1.380(3) 2_887 ?
C8 C7 1.380(3) 2_887 ?
N2 C12 1.345(2) . ?
N2 C9 1.377(2) . ?
N2 C11 1.470(2) . ?
N1 C12 1.324(2) . ?
N1 C16 1.375(2) . ?
N1 H1 0.8600 . ?
C9 C16 1.348(3) . ?
C9 H9 0.9300 . ?
C10 C14 1.386(3) . ?
C10 C15 1.391(3) . ?
C10 C11 1.509(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.475(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.372(3) 2 ?
C14 H14 0.9300 . ?
C15 C14 1.372(3) 2 ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C4 C1 C3 116.53(15) . . ?
C4 C1 C2 122.02(16) . . ?
C3 C1 C2 121.35(16) . . ?
O1 C2 O2 127.95(16) . . ?
O1 C2 C1 118.50(15) . . ?
O2 C2 C1 113.55(15) . . ?
F2 C3 C1 120.06(15) . . ?
F2 C3 C4 117.91(17) . 2_776 ?
C1 C3 C4 122.01(16) . 2_776 ?
F1 C4 C1 120.37(15) . . ?
F1 C4 C3 118.17(16) . 2_776 ?
C1 C4 C3 121.45(17) . 2_776 ?
C7 C5 C8 116.83(16) . . ?
C7 C5 C6 121.86(16) . . ?
C8 C5 C6 121.17(16) . . ?
O3 C6 O4 126.84(16) . . ?
O3 C6 C5 119.69(17) . . ?
O4 C6 C5 113.47(15) . . ?
F5 C7 C5 119.63(17) . . ?
F5 C7 C8 119.04(17) . 2_887 ?
C5 C7 C8 121.33(18) . 2_887 ?
F6 C8 C5 119.72(17) . . ?
F6 C8 C7 118.43(18) . 2_887 ?
C5 C8 C7 121.85(18) . 2_887 ?
C12 N2 C9 109.03(15) . . ?
C12 N2 C11 125.91(16) . . ?
C9 N2 C11 125.05(15) . . ?
C12 N1 C16 109.76(15) . . ?
C12 N1 H1 125.1 . . ?
C16 N1 H1 125.1 . . ?
C16 C9 N2 106.93(16) . . ?
C16 C9 H9 126.5 . . ?
N2 C9 H9 126.5 . . ?
C14 C10 C15 118.23(18) . . ?
C14 C10 C11 120.43(18) . . ?
C15 C10 C11 121.33(17) . . ?
N2 C11 C10 112.59(15) . . ?
N2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 N2 107.32(16) . . ?
N1 C12 C13 125.96(17) . . ?
N2 C12 C13 126.72(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 120.83(19) 2 . ?
C15 C14 H14 119.6 2 . ?
C10 C14 H14 119.6 . . ?
C14 C15 C10 120.94(19) 2 . ?
C14 C15 H15 119.5 2 . ?
C10 C15 H15 119.5 . . ?
C9 C16 N1 106.95(17) . . ?
C9 C16 H16 126.5 . . ?
N1 C16 H16 126.5 . . ?

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 982123'
