
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F N3 O3, C8 H5 O4'
_chemical_formula_sum            'C24 H24 F N3 O7'
_chemical_formula_weight         485.46

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.998(12)
_cell_length_b                   9.624(13)
_cell_length_c                   13.044(18)
_cell_angle_alpha                94.09(3)
_cell_angle_beta                 106.38(3)
_cell_angle_gamma                91.93(3)
_cell_volume                     1079(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2252
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.72

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6088
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3768
_reflns_number_gt                3007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1518P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3768
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.2131
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2729(3) 0.5994(2) 0.20409(18) 0.0411(5) Uani 1 1 d . . .
H1A H 0.2966 0.6862 0.1771 0.049 Uiso 1 1 calc R . .
H1B H 0.1707 0.5635 0.1609 0.049 Uiso 1 1 calc R . .
C2 C 0.3894(3) 0.4971(2) 0.19368(18) 0.0388(5) Uani 1 1 d . . .
H2A H 0.3853 0.4785 0.1188 0.047 Uiso 1 1 calc R . .
H2B H 0.4929 0.5350 0.2325 0.047 Uiso 1 1 calc R . .
C3 C 0.3662(3) 0.3970(2) 0.34790(17) 0.0423(5) Uani 1 1 d . . .
H3A H 0.4694 0.4351 0.3871 0.051 Uiso 1 1 calc R . .
H3B H 0.3480 0.3100 0.3768 0.051 Uiso 1 1 calc R . .
C4 C 0.2490(3) 0.4972(2) 0.36171(18) 0.0428(5) Uani 1 1 d . . .
H4A H 0.1453 0.4561 0.3274 0.051 Uiso 1 1 calc R . .
H4B H 0.2594 0.5173 0.4374 0.051 Uiso 1 1 calc R . .
C5 C 0.4234(2) 0.2531(2) 0.20809(16) 0.0324(5) Uani 1 1 d . . .
C6 C 0.3686(2) 0.1226(2) 0.22453(18) 0.0381(5) Uani 1 1 d . . .
C7 C 0.4272(3) 0.0046(2) 0.19862(17) 0.0380(5) Uani 1 1 d . . .
H7 H 0.3866 -0.0804 0.2115 0.046 Uiso 1 1 calc R . .
C8 C 0.5472(2) 0.0076(2) 0.15306(16) 0.0323(5) Uani 1 1 d . . .
C9 C 0.6021(2) 0.1351(2) 0.13200(15) 0.0307(5) Uani 1 1 d . . .
C10 C 0.5401(2) 0.25628(19) 0.16079(16) 0.0332(5) Uani 1 1 d . . .
H10 H 0.5791 0.3418 0.1475 0.040 Uiso 1 1 calc R . .
N3 N 0.72122(19) 0.14034(17) 0.08536(13) 0.0346(4) Uani 1 1 d . . .
C12 C 0.7844(3) 0.0242(2) 0.06358(17) 0.0402(5) Uani 1 1 d . . .
H12 H 0.8667 0.0309 0.0339 0.048 Uiso 1 1 calc R . .
C13 C 0.7368(2) -0.1031(2) 0.08171(16) 0.0381(5) Uani 1 1 d . . .
C14 C 0.6130(2) -0.1186(2) 0.12634(16) 0.0362(5) Uani 1 1 d . . .
C15 C 0.8165(3) -0.2227(3) 0.0513(2) 0.0520(6) Uani 1 1 d . . .
C16 C 0.7804(3) 0.2718(2) 0.05961(18) 0.0410(5) Uani 1 1 d . . .
H16A H 0.6942 0.3302 0.0334 0.049 Uiso 1 1 calc R . .
H16B H 0.8282 0.2535 0.0024 0.049 Uiso 1 1 calc R . .
C17 C 0.8952(3) 0.3485(3) 0.1521(2) 0.0566(7) Uani 1 1 d . . .
H17A H 0.8495 0.3651 0.2098 0.085 Uiso 1 1 calc R . .
H17B H 0.9264 0.4360 0.1314 0.085 Uiso 1 1 calc R . .
H17C H 0.9842 0.2941 0.1754 0.085 Uiso 1 1 calc R . .
C18 C 0.6506(3) 0.7764(3) 0.41537(18) 0.0483(6) Uani 1 1 d . . .
C19 C 0.7436(2) 0.9021(2) 0.40562(15) 0.0360(5) Uani 1 1 d . . .
C20 C 0.6890(3) 1.0261(3) 0.43424(18) 0.0455(6) Uani 1 1 d . . .
H20 H 0.6016 1.0238 0.4588 0.055 Uiso 1 1 calc R . .
C21 C 0.7571(3) 1.1515(3) 0.42822(19) 0.0516(6) Uani 1 1 d . . .
H21 H 0.7187 1.2334 0.4502 0.062 Uiso 1 1 calc R . .
C22 C 0.8819(3) 1.1563(3) 0.3898(2) 0.0524(6) Uani 1 1 d . . .
H22 H 0.9290 1.2419 0.3843 0.063 Uiso 1 1 calc R . .
C23 C 0.9384(3) 1.0363(2) 0.35918(17) 0.0448(6) Uani 1 1 d . . .
H23 H 1.0230 1.0410 0.3316 0.054 Uiso 1 1 calc R . .
C24 C 0.8737(2) 0.9079(2) 0.36802(16) 0.0355(5) Uani 1 1 d . . .
C25 C 0.9589(3) 0.7893(3) 0.33681(18) 0.0458(6) Uani 1 1 d . . .
F1 F 0.24978(17) 0.11725(14) 0.26669(13) 0.0612(5) Uani 1 1 d . . .
N1 N 0.2717(2) 0.62588(17) 0.31433(15) 0.0397(5) Uani 1 1 d . . .
H1N H 0.1950 0.6824 0.3172 0.048 Uiso 1 1 calc R . .
H2N H 0.3622 0.6699 0.3527 0.048 Uiso 1 1 calc R . .
N2 N 0.3563(2) 0.37108(16) 0.23621(14) 0.0355(4) Uani 1 1 d . . .
O1 O 0.9204(3) -0.2141(2) 0.01307(19) 0.0759(6) Uani 1 1 d . . .
O2 O 0.7618(3) -0.34424(18) 0.06858(16) 0.0661(6) Uani 1 1 d . . .
H2 H 0.6862 -0.3333 0.0911 0.099 Uiso 1 1 calc R . .
O3 O 0.5617(2) -0.23399(15) 0.14267(14) 0.0504(5) Uani 1 1 d . . .
O4 O 0.5203(2) 0.7904(2) 0.42335(16) 0.0666(6) Uani 1 1 d . . .
O5 O 0.7072(2) 0.6584(2) 0.41692(18) 0.0705(6) Uani 1 1 d . . .
O6 O 0.9333(2) 0.66784(19) 0.36049(18) 0.0690(6) Uani 1 1 d . . .
H6 H 0.8555 0.6657 0.3815 0.103 Uiso 1 1 calc R . .
O7 O 1.0574(2) 0.8126(2) 0.29327(16) 0.0683(6) 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
C1 N1 1.446(3) . ?
C1 C2 1.489(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.426(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.437(3) . ?
C3 C4 1.492(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.456(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.361(3) . ?
C5 N2 1.378(3) . ?
C5 C6 1.386(3) . ?
C6 C7 1.330(3) . ?
C6 F1 1.334(3) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 C14 1.432(3) . ?
C9 N3 1.374(3) . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
N3 C12 1.320(3) . ?
N3 C16 1.453(3) . ?
C12 C13 1.343(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.403(3) . ?
C13 C15 1.465(3) . ?
C14 O3 1.243(3) . ?
C15 O1 1.180(3) . ?
C15 O2 1.313(3) . ?
C16 C17 1.479(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O4 1.217(3) . ?
C18 O5 1.259(3) . ?
C18 C19 1.482(3) . ?
C19 C20 1.372(3) . ?
C19 C24 1.392(3) . ?
C20 C21 1.352(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.491(3) . ?
C25 O7 1.203(3) . ?
C25 O6 1.261(3) . ?
N1 H1N 0.9000 . ?
N1 H2N 0.9000 . ?
O2 H2 0.8200 . ?
O6 H6 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 111.52(17) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N2 C2 C1 108.97(19) . . ?
N2 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 110.18(18) . . ?
N2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 109.84(19) . . ?
N1 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 N2 123.31(18) . . ?
C10 C5 C6 116.71(18) . . ?
N2 C5 C6 119.95(19) . . ?
C7 C6 F1 119.39(18) . . ?
C7 C6 C5 123.1(2) . . ?
F1 C6 C5 117.52(18) . . ?
C6 C7 C8 120.36(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 118.55(19) . . ?
C7 C8 C14 120.92(19) . . ?
C9 C8 C14 120.5(2) . . ?
N3 C9 C8 119.51(18) . . ?
N3 C9 C10 120.63(19) . . ?
C8 C9 C10 119.8(2) . . ?
C5 C10 C9 121.42(19) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 N3 C9 119.76(19) . . ?
C12 N3 C16 118.82(19) . . ?
C9 N3 C16 121.41(17) . . ?
N3 C12 C13 123.9(2) . . ?
N3 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C12 C13 C14 120.17(19) . . ?
C12 C13 C15 117.6(2) . . ?
C14 C13 C15 122.2(2) . . ?
O3 C14 C13 123.03(19) . . ?
O3 C14 C8 120.9(2) . . ?
C13 C14 C8 116.08(19) . . ?
O1 C15 O2 121.2(2) . . ?
O1 C15 C13 124.3(2) . . ?
O2 C15 C13 114.5(2) . . ?
N3 C16 C17 113.2(2) . . ?
N3 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 121.3(2) . . ?
O4 C18 C19 118.5(2) . . ?
O5 C18 C19 120.2(2) . . ?
C20 C19 C24 117.7(2) . . ?
C20 C19 C18 114.6(2) . . ?
C24 C19 C18 127.7(2) . . ?
C21 C20 C19 122.8(2) . . ?
C21 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 120.0(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 121.6(2) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C19 118.7(2) . . ?
C23 C24 C25 113.2(2) . . ?
C19 C24 C25 128.1(2) . . ?
O7 C25 O6 120.6(2) . . ?
O7 C25 C24 118.9(2) . . ?
O6 C25 C24 120.4(2) . . ?
C1 N1 C4 111.65(17) . . ?
C1 N1 H1N 109.3 . . ?
C4 N1 H1N 109.3 . . ?
C1 N1 H2N 109.3 . . ?
C4 N1 H2N 109.3 . . ?
H1N N1 H2N 108.0 . . ?
C5 N2 C2 117.09(18) . . ?
C5 N2 C3 116.36(16) . . ?
C2 N2 C3 110.27(17) . . ?
C15 O2 H2 109.5 . . ?
C25 O6 H6 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 57.4(2) . . . . ?
N2 C3 C4 N1 -56.9(2) . . . . ?
C10 C5 C6 C7 1.6(3) . . . . ?
N2 C5 C6 C7 179.55(19) . . . . ?
C10 C5 C6 F1 -177.25(19) . . . . ?
N2 C5 C6 F1 0.7(3) . . . . ?
F1 C6 C7 C8 178.6(2) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
C6 C7 C8 C14 179.01(19) . . . . ?
C7 C8 C9 N3 -179.33(18) . . . . ?
C14 C8 C9 N3 -0.2(3) . . . . ?
C7 C8 C9 C10 2.6(3) . . . . ?
C14 C8 C9 C10 -178.34(17) . . . . ?
N2 C5 C10 C9 -178.74(17) . . . . ?
C6 C5 C10 C9 -0.8(3) . . . . ?
N3 C9 C10 C5 -179.29(18) . . . . ?
C8 C9 C10 C5 -1.2(3) . . . . ?
C8 C9 N3 C12 -1.6(3) . . . . ?
C10 C9 N3 C12 176.45(17) . . . . ?
C8 C9 N3 C16 178.63(17) . . . . ?
C10 C9 N3 C16 -3.3(3) . . . . ?
C9 N3 C12 C13 1.8(3) . . . . ?
C16 N3 C12 C13 -178.47(19) . . . . ?
N3 C12 C13 C14 0.0(3) . . . . ?
N3 C12 C13 C15 178.79(19) . . . . ?
C12 C13 C14 O3 178.33(19) . . . . ?
C15 C13 C14 O3 -0.4(3) . . . . ?
C12 C13 C14 C8 -1.8(3) . . . . ?
C15 C13 C14 C8 179.46(18) . . . . ?
C7 C8 C14 O3 0.8(3) . . . . ?
C9 C8 C14 O3 -178.25(18) . . . . ?
C7 C8 C14 C13 -179.01(18) . . . . ?
C9 C8 C14 C13 1.9(3) . . . . ?
C12 C13 C15 O1 0.9(4) . . . . ?
C14 C13 C15 O1 179.6(2) . . . . ?
C12 C13 C15 O2 -178.4(2) . . . . ?
C14 C13 C15 O2 0.4(3) . . . . ?
C12 N3 C16 C17 -96.8(2) . . . . ?
C9 N3 C16 C17 83.0(3) . . . . ?
O4 C18 C19 C20 16.1(3) . . . . ?
O5 C18 C19 C20 -162.8(2) . . . . ?
O4 C18 C19 C24 -161.5(2) . . . . ?
O5 C18 C19 C24 19.6(3) . . . . ?
C24 C19 C20 C21 -0.6(3) . . . . ?
C18 C19 C20 C21 -178.5(2) . . . . ?
C19 C20 C21 C22 1.8(4) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C22 C23 C24 -1.2(4) . . . . ?
C22 C23 C24 C19 2.4(3) . . . . ?
C22 C23 C24 C25 -176.3(2) . . . . ?
C20 C19 C24 C23 -1.5(3) . . . . ?
C18 C19 C24 C23 176.11(19) . . . . ?
C20 C19 C24 C25 177.00(19) . . . . ?
C18 C19 C24 C25 -5.4(3) . . . . ?
C23 C24 C25 O7 -10.7(3) . . . . ?
C19 C24 C25 O7 170.7(2) . . . . ?
C23 C24 C25 O6 165.8(2) . . . . ?
C19 C24 C25 O6 -12.7(3) . . . . ?
C2 C1 N1 C4 -54.4(2) . . . . ?
C3 C4 N1 C1 53.5(2) . . . . ?
C10 C5 N2 C2 13.2(3) . . . . ?
C6 C5 N2 C2 -164.63(19) . . . . ?
C10 C5 N2 C3 -120.2(2) . . . . ?
C6 C5 N2 C3 61.9(3) . . . . ?
C1 C2 N2 C5 162.85(18) . . . . ?
C1 C2 N2 C3 -61.0(2) . . . . ?
C4 C3 N2 C5 -161.76(18) . . . . ?
C4 C3 N2 C2 61.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1N O6 0.90 2.57 3.293(6) 138 1_455 yes
N1 H1N O7 0.90 1.78 2.653(5) 164 1_455 yes
O2 H2 O3 0.82 1.74 2.503(5) 154 . yes
N1 H2N O4 0.90 1.80 2.683(5) 168 . yes
O6 H6 O5 0.82 1.54 2.358(5) 177 . yes
C3 H3B F1 0.97 2.26 2.872(5) 120 . yes
C4 H4B O5 0.97 2.59 3.277(6) 128 2_666 yes
C16 H16B O1 0.97 2.37 3.150(6) 137 2_755 yes
C23 H23 F1 0.93 2.52 3.435(6) 166 1_665 yes


_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.082





#==============END



data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F N3 O3, C8 H5 O4'
_chemical_formula_sum            'C24 H24 F N3 O7'
_chemical_formula_weight         485.46

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   13.9940(17)
_cell_length_b                   13.6288(18)
_cell_length_c                   22.537(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4298.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2631
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.47

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2032
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26842
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4914
_reflns_number_gt                2777
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0824P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4914
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1332
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38336(18) 0.9762(2) 0.39932(11) 0.0333(7) Uani 1 1 d . . .
H1A H 0.3646 1.0348 0.4208 0.040 Uiso 1 1 calc R . .
H1B H 0.3350 0.9264 0.4062 0.040 Uiso 1 1 calc R . .
C2 C 0.38745(18) 0.9991(2) 0.33390(10) 0.0284(7) Uani 1 1 d . . .
H2A H 0.3242 1.0168 0.3199 0.034 Uiso 1 1 calc R . .
H2B H 0.4296 1.0545 0.3272 0.034 Uiso 1 1 calc R . .
C3 C 0.51865(17) 0.8877(2) 0.32007(11) 0.0287(7) Uani 1 1 d . . .
H3A H 0.5614 0.9428 0.3138 0.034 Uiso 1 1 calc R . .
H3B H 0.5421 0.8326 0.2971 0.034 Uiso 1 1 calc R . .
C4 C 0.51655(19) 0.8608(2) 0.38564(11) 0.0300(7) Uani 1 1 d . . .
H4A H 0.4783 0.8021 0.3909 0.036 Uiso 1 1 calc R . .
H4B H 0.5810 0.8464 0.3989 0.036 Uiso 1 1 calc R . .
C5 C 0.40369(16) 0.9125(2) 0.23981(11) 0.0226(6) Uani 1 1 d . . .
C6 C 0.30800(17) 0.9131(2) 0.22035(11) 0.0264(6) Uani 1 1 d . . .
C7 C 0.28304(17) 0.9108(2) 0.16249(11) 0.0266(6) Uani 1 1 d . . .
H7 H 0.2189 0.9140 0.1519 0.032 Uiso 1 1 calc R . .
C8 C 0.35303(17) 0.9034(2) 0.11848(10) 0.0234(6) Uani 1 1 d . . .
C9 C 0.44915(16) 0.8980(2) 0.13606(11) 0.0216(6) Uani 1 1 d . . .
C10 C 0.47319(16) 0.9042(2) 0.19677(11) 0.0237(6) Uani 1 1 d . . .
H10 H 0.5371 0.9025 0.2079 0.028 Uiso 1 1 calc R . .
C11 C 0.32617(17) 0.8994(2) 0.05649(11) 0.0265(6) Uani 1 1 d . . .
C12 C 0.40209(17) 0.8888(2) 0.01515(11) 0.0259(6) Uani 1 1 d . . .
C13 C 0.49415(18) 0.8819(2) 0.03508(11) 0.0260(6) Uani 1 1 d . . .
H13 H 0.5423 0.8735 0.0071 0.031 Uiso 1 1 calc R . .
N3 N 0.51945(13) 0.88657(17) 0.09226(8) 0.0237(5) Uani 1 1 d . . .
C15 C 0.62128(17) 0.8727(2) 0.10795(12) 0.0324(7) Uani 1 1 d . . .
H15A H 0.6387 0.9190 0.1388 0.039 Uiso 1 1 calc R . .
H15B H 0.6606 0.8864 0.0735 0.039 Uiso 1 1 calc R . .
C16 C 0.6408(2) 0.7707(3) 0.12910(15) 0.0565(10) Uani 1 1 d . . .
H16A H 0.6029 0.7574 0.1637 0.085 Uiso 1 1 calc R . .
H16B H 0.7073 0.7644 0.1388 0.085 Uiso 1 1 calc R . .
H16C H 0.6247 0.7248 0.0984 0.085 Uiso 1 1 calc R . .
C17 C 0.38194(19) 0.8830(2) -0.04904(12) 0.0313(7) Uani 1 1 d . . .
C18 C 0.32360(17) 0.8461(2) 0.70525(11) 0.0244(6) Uani 1 1 d . . .
C19 C 0.22440(18) 0.8411(2) 0.71105(12) 0.0301(7) Uani 1 1 d . . .
H19 H 0.1966 0.8387 0.7485 0.036 Uiso 1 1 calc R . .
C20 C 0.16778(18) 0.8397(2) 0.66104(12) 0.0344(7) Uani 1 1 d . . .
H20 H 0.1017 0.8361 0.6649 0.041 Uiso 1 1 calc R . .
C21 C 0.20844(18) 0.8435(2) 0.60501(12) 0.0308(7) Uani 1 1 d . . .
H21 H 0.1695 0.8412 0.5716 0.037 Uiso 1 1 calc R . .
C22 C 0.30703(18) 0.8506(2) 0.59833(11) 0.0248(6) Uani 1 1 d . . .
C23 C 0.36367(17) 0.8503(2) 0.64896(10) 0.0243(6) Uani 1 1 d . . .
H23 H 0.4298 0.8531 0.6451 0.029 Uiso 1 1 calc R . .
C24 C 0.3501(2) 0.8574(2) 0.53696(11) 0.0306(7) Uani 1 1 d . . .
C25 C 0.38812(19) 0.8488(2) 0.75791(12) 0.0306(7) Uani 1 1 d . . .
F1 F 0.23723(10) 0.91455(15) 0.26164(7) 0.0444(5) Uani 1 1 d . . .
N1 N 0.47643(15) 0.94084(18) 0.42255(9) 0.0286(5) Uani 1 1 d . . .
H1C H 0.5181 0.9912 0.4235 0.034 Uiso 1 1 calc R . .
H1D H 0.4685 0.9191 0.4599 0.034 Uiso 1 1 calc R . .
N2 N 0.42246(14) 0.91360(18) 0.30068(9) 0.0249(5) Uani 1 1 d . . .
O1 O 0.23911(12) 0.90578(17) 0.04102(8) 0.0410(6) Uani 1 1 d . . .
O2 O 0.29181(14) 0.8912(2) -0.06367(8) 0.0490(6) Uani 1 1 d . . .
H2 H 0.2588 0.8907 -0.0336 0.074 Uiso 1 1 calc R . .
O3 O 0.44330(14) 0.87391(17) -0.08748(8) 0.0401(6) Uani 1 1 d . . .
O4 O 0.34191(14) 0.8601(2) 0.80836(8) 0.0494(7) Uani 1 1 d . . .
H4 H 0.3804 0.8655 0.8356 0.074 Uiso 1 1 calc R . .
O5 O 0.47365(13) 0.8421(2) 0.75458(9) 0.0510(7) Uani 1 1 d . . .
O6 O 0.30198(15) 0.83405(18) 0.49404(8) 0.0508(6) Uani 1 1 d . . .
O7 O 0.43639(13) 0.89000(16) 0.53470(8) 0.0363(5) 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
C1 N1 1.484(3) . ?
C1 C2 1.508(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.469(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.459(3) . ?
C3 C4 1.523(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.482(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.378(3) . ?
C5 N2 1.397(3) . ?
C5 C6 1.409(3) . ?
C6 C7 1.350(3) . ?
C6 F1 1.359(3) . ?
C7 C8 1.398(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.404(3) . ?
C8 C11 1.448(3) . ?
C9 N3 1.402(3) . ?
C9 C10 1.411(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.270(3) . ?
C11 C12 1.420(3) . ?
C12 C13 1.368(3) . ?
C12 C17 1.476(3) . ?
C13 N3 1.338(3) . ?
C13 H13 0.9300 . ?
N3 C15 1.480(3) . ?
C15 C16 1.495(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.226(3) . ?
C17 O2 1.308(3) . ?
C18 C23 1.388(3) . ?
C18 C19 1.396(3) . ?
C18 C25 1.492(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.389(3) . ?
C22 C24 1.511(4) . ?
C23 H23 0.9300 . ?
C24 O6 1.221(3) . ?
C24 O7 1.288(3) . ?
C25 O5 1.203(3) . ?
C25 O4 1.317(3) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
O2 H2 0.8200 . ?
O4 H4 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 112.3(2) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 110.3(2) . . ?
N2 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C4 109.3(2) . . ?
N2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
N2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C3 112.0(2) . . ?
N1 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C10 C5 N2 124.0(2) . . ?
C10 C5 C6 116.9(2) . . ?
N2 C5 C6 119.0(2) . . ?
C7 C6 F1 118.2(2) . . ?
C7 C6 C5 123.1(2) . . ?
F1 C6 C5 118.6(2) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 118.4(2) . . ?
C7 C8 C11 120.4(2) . . ?
C9 C8 C11 121.3(2) . . ?
N3 C9 C8 118.6(2) . . ?
N3 C9 C10 121.4(2) . . ?
C8 C9 C10 119.9(2) . . ?
C5 C10 C9 121.3(2) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
O1 C11 C12 123.0(2) . . ?
O1 C11 C8 120.7(2) . . ?
C12 C11 C8 116.3(2) . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 C17 119.9(2) . . ?
C11 C12 C17 120.4(2) . . ?
N3 C13 C12 124.2(2) . . ?
N3 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
C13 N3 C9 119.8(2) . . ?
C13 N3 C15 118.6(2) . . ?
C9 N3 C15 121.4(2) . . ?
N3 C15 C16 111.8(2) . . ?
N3 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N3 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 120.4(2) . . ?
O3 C17 C12 124.3(2) . . ?
O2 C17 C12 115.2(2) . . ?
C23 C18 C19 119.3(2) . . ?
C23 C18 C25 118.8(2) . . ?
C19 C18 C25 121.9(2) . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 118.5(2) . . ?
C23 C22 C24 121.6(2) . . ?
C21 C22 C24 119.9(2) . . ?
C18 C23 C22 121.3(2) . . ?
C18 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
O6 C24 O7 125.1(2) . . ?
O6 C24 C22 119.3(2) . . ?
O7 C24 C22 115.5(2) . . ?
O5 C25 O4 123.5(2) . . ?
O5 C25 C18 123.4(2) . . ?
O4 C25 C18 113.1(2) . . ?
C4 N1 C1 111.9(2) . . ?
C4 N1 H1C 109.2 . . ?
C1 N1 H1C 109.2 . . ?
C4 N1 H1D 109.2 . . ?
C1 N1 H1D 109.2 . . ?
H1C N1 H1D 107.9 . . ?
C5 N2 C3 117.7(2) . . ?
C5 N2 C2 116.5(2) . . ?
C3 N2 C2 110.3(2) . . ?
C17 O2 H2 109.5 . . ?
C25 O4 H4 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 54.7(3) . . . . ?
N2 C3 C4 N1 -56.4(3) . . . . ?
C10 C5 C6 C7 -3.3(4) . . . . ?
N2 C5 C6 C7 -179.0(3) . . . . ?
C10 C5 C6 F1 175.6(3) . . . . ?
N2 C5 C6 F1 -0.1(4) . . . . ?
F1 C6 C7 C8 -176.2(3) . . . . ?
C5 C6 C7 C8 2.6(5) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C6 C7 C8 C11 179.1(3) . . . . ?
C7 C8 C9 N3 177.4(3) . . . . ?
C11 C8 C9 N3 -1.2(4) . . . . ?
C7 C8 C9 C10 -2.7(4) . . . . ?
C11 C8 C9 C10 178.7(3) . . . . ?
N2 C5 C10 C9 176.4(3) . . . . ?
C6 C5 C10 C9 0.9(4) . . . . ?
N3 C9 C10 C5 -178.1(3) . . . . ?
C8 C9 C10 C5 2.0(4) . . . . ?
C7 C8 C11 O1 2.4(4) . . . . ?
C9 C8 C11 O1 -179.0(3) . . . . ?
C7 C8 C11 C12 -178.0(3) . . . . ?
C9 C8 C11 C12 0.6(4) . . . . ?
O1 C11 C12 C13 -179.7(3) . . . . ?
C8 C11 C12 C13 0.7(4) . . . . ?
O1 C11 C12 C17 -1.0(5) . . . . ?
C8 C11 C12 C17 179.4(3) . . . . ?
C11 C12 C13 N3 -1.4(5) . . . . ?
C17 C12 C13 N3 179.9(3) . . . . ?
C12 C13 N3 C9 0.8(4) . . . . ?
C12 C13 N3 C15 176.7(3) . . . . ?
C8 C9 N3 C13 0.6(4) . . . . ?
C10 C9 N3 C13 -179.3(3) . . . . ?
C8 C9 N3 C15 -175.3(3) . . . . ?
C10 C9 N3 C15 4.8(4) . . . . ?
C13 N3 C15 C16 -99.5(3) . . . . ?
C9 N3 C15 C16 76.4(3) . . . . ?
C13 C12 C17 O3 -1.4(5) . . . . ?
C11 C12 C17 O3 179.9(3) . . . . ?
C13 C12 C17 O2 -179.4(3) . . . . ?
C11 C12 C17 O2 1.9(4) . . . . ?
C23 C18 C19 C20 0.5(4) . . . . ?
C25 C18 C19 C20 179.4(3) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C19 C20 C21 C22 -1.2(5) . . . . ?
C20 C21 C22 C23 2.2(4) . . . . ?
C20 C21 C22 C24 -178.3(3) . . . . ?
C19 C18 C23 C22 0.6(4) . . . . ?
C25 C18 C23 C22 -178.4(3) . . . . ?
C21 C22 C23 C18 -1.9(4) . . . . ?
C24 C22 C23 C18 178.6(3) . . . . ?
C23 C22 C24 O6 162.5(3) . . . . ?
C21 C22 C24 O6 -17.0(4) . . . . ?
C23 C22 C24 O7 -18.7(4) . . . . ?
C21 C22 C24 O7 161.9(3) . . . . ?
C23 C18 C25 O5 -9.6(5) . . . . ?
C19 C18 C25 O5 171.4(3) . . . . ?
C23 C18 C25 O4 169.8(3) . . . . ?
C19 C18 C25 O4 -9.1(4) . . . . ?
C3 C4 N1 C1 50.8(3) . . . . ?
C2 C1 N1 C4 -50.0(3) . . . . ?
C10 C5 N2 C3 -10.9(4) . . . . ?
C6 C5 N2 C3 164.5(3) . . . . ?
C10 C5 N2 C2 123.6(3) . . . . ?
C6 C5 N2 C2 -61.0(3) . . . . ?
C4 C3 N2 C5 -161.7(2) . . . . ?
C4 C3 N2 C2 61.3(3) . . . . ?
C1 C2 N2 C5 161.5(2) . . . . ?
C1 C2 N2 C3 -60.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1C O7 0.90 1.98 2.783(4) 147 5_676 yes
N1 H1D O7 0.90 1.79 2.681(3) 170 . yes
O2 H2 O1 0.82 1.71 2.484(3) 156 . yes
O4 H4 O3 0.82 1.95 2.748(3) 164 1_556 yes
C1 H1A O2 0.97 2.43 3.159(4) 131 2_575 yes
C1 H1B O6 0.97 2.39 3.098(4) 129 . yes
C2 H2A F1 0.97 2.27 2.899(4) 122 . yes
C4 H4A O3 0.97 2.50 3.415(5) 158 7_576 yes
C15 H15B O6 0.97 2.59 3.457(4) 148 6_656 yes
C20 H20 O5 0.93 2.55 3.317(4) 140 6_557 yes

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.077




#==============END

data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F N3 O3, C8 H5 O4, 0.5(C8 H6 O4)'
_chemical_formula_sum            'C28 H27 F N3 O9'
_chemical_formula_weight         568.53

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                   9.8768(19)
_cell_length_b                   10.2489(19)
_cell_length_c                   13.674(3)
_cell_angle_alpha                89.319(4)
_cell_angle_beta                 74.752(4)
_cell_angle_gamma                71.679(4)
_cell_volume                     1263.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3144
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7289
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4654
_reflns_number_gt                3537
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1652P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4654
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.2300
_refine_ls_wR_factor_gt          0.1782
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7846(3) 0.9736(3) 0.02128(18) 0.0361(6) Uani 1 1 d . . .
H1A H 0.6792 1.0212 0.0335 0.043 Uiso 1 1 calc R . .
H1B H 0.8373 1.0200 -0.0298 0.043 Uiso 1 1 calc R . .
C2 C 0.8285(3) 0.9793(3) 0.11838(17) 0.0342(6) Uani 1 1 d . . .
H2A H 0.9343 0.9339 0.1062 0.041 Uiso 1 1 calc R . .
H2B H 0.8055 1.0745 0.1425 0.041 Uiso 1 1 calc R . .
C3 C 0.7852(3) 0.7647(3) 0.16135(18) 0.0353(6) Uani 1 1 d . . .
H3A H 0.7311 0.7198 0.2128 0.042 Uiso 1 1 calc R . .
H3B H 0.8904 0.7191 0.1524 0.042 Uiso 1 1 calc R . .
C4 C 0.7484(3) 0.7514(3) 0.06240(17) 0.0334(6) Uani 1 1 d . . .
H4A H 0.7817 0.6548 0.0386 0.040 Uiso 1 1 calc R . .
H4B H 0.6417 0.7868 0.0736 0.040 Uiso 1 1 calc R . .
C5 C 0.7269(3) 0.9410(2) 0.29826(16) 0.0245(5) Uani 1 1 d . . .
C6 C 0.6693(3) 1.0800(2) 0.33966(18) 0.0265(5) Uani 1 1 d . . .
C7 C 0.6414(3) 1.1165(2) 0.43905(17) 0.0263(5) Uani 1 1 d . . .
H7 H 0.6080 1.2093 0.4618 0.032 Uiso 1 1 calc R . .
C8 C 0.6625(2) 1.0147(2) 0.50863(16) 0.0240(5) Uani 1 1 d . . .
C9 C 0.7160(2) 0.8758(2) 0.47132(16) 0.0242(5) Uani 1 1 d . . .
C10 C 0.7511(3) 0.8409(2) 0.36661(17) 0.0262(5) Uani 1 1 d . . .
H10 H 0.7914 0.7485 0.3425 0.031 Uiso 1 1 calc R . .
C11 C 0.6311(3) 1.0552(3) 0.61585(18) 0.0278(6) Uani 1 1 d . . .
C12 C 0.6550(3) 0.9447(3) 0.67970(17) 0.0295(6) Uani 1 1 d . . .
C13 C 0.7066(3) 0.8107(3) 0.63910(17) 0.0304(6) Uani 1 1 d . . .
H13 H 0.7201 0.7411 0.6833 0.037 Uiso 1 1 calc R . .
C14 C 0.6340(3) 0.9711(3) 0.78995(19) 0.0372(7) Uani 1 1 d . . .
C15 C 0.7953(3) 0.6248(3) 0.5059(2) 0.0395(7) Uani 1 1 d . . .
H15A H 0.8386 0.5727 0.5561 0.047 Uiso 1 1 calc R . .
H15B H 0.8727 0.6095 0.4425 0.047 Uiso 1 1 calc R . .
C16 C 0.6738(4) 0.5724(3) 0.4906(2) 0.0518(8) Uani 1 1 d . . .
H16A H 0.5993 0.5832 0.5541 0.078 Uiso 1 1 calc R . .
H16B H 0.7155 0.4768 0.4667 0.078 Uiso 1 1 calc R . .
H16C H 0.6299 0.6243 0.4415 0.078 Uiso 1 1 calc R . .
C17 C 0.8089(3) 0.3885(3) 0.12855(19) 0.0310(6) Uani 1 1 d . . .
C18 C 0.6437(3) 0.4267(2) 0.14637(17) 0.0272(5) Uani 1 1 d . . .
C19 C 0.5445(3) 0.5164(3) 0.22808(19) 0.0339(6) Uani 1 1 d . . .
H19 H 0.5804 0.5580 0.2711 0.041 Uiso 1 1 calc R . .
C20 C 0.3936(3) 0.5445(3) 0.24607(19) 0.0345(6) Uani 1 1 d . . .
H20 H 0.3289 0.6056 0.3006 0.041 Uiso 1 1 calc R . .
C21 C 0.3374(3) 0.4822(2) 0.18339(17) 0.0269(5) Uani 1 1 d . . .
C22 C 0.4361(3) 0.3939(3) 0.10046(19) 0.0326(6) Uani 1 1 d . . .
H22 H 0.4003 0.3527 0.0571 0.039 Uiso 1 1 calc R . .
C23 C 0.5882(3) 0.3672(3) 0.08223(19) 0.0329(6) Uani 1 1 d . . .
H23 H 0.6532 0.3088 0.0264 0.039 Uiso 1 1 calc R . .
C24 C 0.0219(3) 0.8456(3) 0.67598(19) 0.0359(6) Uani 1 1 d . . .
C25 C 0.0105(3) 0.9241(3) 0.58434(19) 0.0334(6) Uani 1 1 d . . .
C26 C 0.0515(3) 0.8570(3) 0.4872(2) 0.0343(6) Uani 1 1 d . . .
H26 H 0.0853 0.7612 0.4791 0.041 Uiso 1 1 calc R . .
C27 C -0.0420(3) 1.0670(3) 0.5966(2) 0.0345(6) Uani 1 1 d . . .
H27 H -0.0708 1.1118 0.6611 0.041 Uiso 1 1 calc R . .
C31 C 0.1744(3) 0.5060(3) 0.20908(19) 0.0320(6) Uani 1 1 d . . .
F1 F 0.63525(19) 1.18195(15) 0.27702(11) 0.0414(4) Uani 1 1 d . . .
N1 N 0.8197(2) 0.8281(2) -0.01662(14) 0.0312(5) Uani 1 1 d . . .
H1C H 0.7877 0.8263 -0.0723 0.037 Uiso 1 1 calc R . .
H1D H 0.9186 0.7866 -0.0344 0.037 Uiso 1 1 calc R . .
N2 N 0.7465(2) 0.9097(2) 0.19523(14) 0.0287(5) Uani 1 1 d . . .
N3 N 0.7386(2) 0.7737(2) 0.54014(14) 0.0286(5) Uani 1 1 d . . .
O1 O 0.5862(2) 1.17997(19) 0.64887(13) 0.0369(5) Uani 1 1 d . . .
O2 O 0.6042(3) 1.1003(2) 0.82158(14) 0.0485(6) Uani 1 1 d . . .
H2 H 0.5705 1.1511 0.7810 0.073 Uiso 1 1 calc R . .
O3 O 0.6468(3) 0.8795(3) 0.84782(14) 0.0528(6) Uani 1 1 d . . .
O4 O 0.8888(2) 0.3085(2) 0.05327(16) 0.0526(6) Uani 1 1 d . . .
O5 O 0.8561(2) 0.43927(19) 0.19240(14) 0.0367(5) Uani 1 1 d . . .
O6 O 0.1344(2) 0.4436(2) 0.14349(15) 0.0466(6) Uani 1 1 d . . .
H6 H 0.0463 0.4515 0.1653 0.070 Uiso 1 1 calc R . .
O7 O 0.0869(2) 0.5733(3) 0.28465(17) 0.0624(7) Uani 1 1 d . . .
O8 O 0.0816(3) 0.7102(2) 0.65401(15) 0.0568(6) Uani 1 1 d . . .
H8 H 0.0973 0.6726 0.7051 0.085 Uiso 1 1 calc R . .
O9 O -0.0168(3) 0.8986(2) 0.76128(15) 0.0522(6) 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
C1 N1 1.488(3) . ?
C1 C2 1.509(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.472(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.461(3) . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.486(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.387(3) . ?
C5 N2 1.398(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.346(3) . ?
C6 F1 1.359(3) . ?
C7 C8 1.408(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(3) . ?
C8 C11 1.453(3) . ?
C9 N3 1.404(3) . ?
C9 C10 1.404(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.260(3) . ?
C11 C12 1.420(4) . ?
C12 C13 1.372(4) . ?
C12 C14 1.483(3) . ?
C13 N3 1.337(3) . ?
C13 H13 0.9300 . ?
C14 O3 1.218(3) . ?
C14 O2 1.315(4) . ?
C15 N3 1.484(3) . ?
C15 C16 1.520(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.241(3) . ?
C17 O5 1.276(3) . ?
C17 C18 1.505(3) . ?
C18 C23 1.384(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.392(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(3) . ?
C21 C31 1.495(3) . ?
C22 C23 1.393(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O9 1.205(3) . ?
C24 O8 1.328(3) . ?
C24 C25 1.491(4) . ?
C25 C27 1.388(4) . ?
C25 C26 1.401(4) . ?
C26 C27 1.386(4) 2_576 ?
C26 H26 0.9300 . ?
C27 C26 1.386(4) 2_576 ?
C27 H27 0.9300 . ?
C31 O7 1.210(3) . ?
C31 O6 1.314(3) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
O2 H2 0.8200 . ?
O6 H6 0.8200 . ?
O8 H8 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 110.4(2) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 108.8(2) . . ?
N2 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 110.6(2) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 111.4(2) . . ?
N1 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C10 C5 N2 123.0(2) . . ?
C10 C5 C6 116.3(2) . . ?
N2 C5 C6 120.5(2) . . ?
C7 C6 F1 117.8(2) . . ?
C7 C6 C5 123.3(2) . . ?
F1 C6 C5 118.8(2) . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 C11 121.8(2) . . ?
C7 C8 C11 119.8(2) . . ?
C8 C9 N3 118.7(2) . . ?
C8 C9 C10 120.1(2) . . ?
N3 C9 C10 121.1(2) . . ?
C5 C10 C9 121.6(2) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
O1 C11 C12 122.9(2) . . ?
O1 C11 C8 121.7(2) . . ?
C12 C11 C8 115.3(2) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 C14 118.7(2) . . ?
C11 C12 C14 120.9(2) . . ?
N3 C13 C12 124.3(2) . . ?
N3 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
O3 C14 O2 121.5(2) . . ?
O3 C14 C12 122.8(3) . . ?
O2 C14 C12 115.7(2) . . ?
N3 C15 C16 112.1(2) . . ?
N3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O5 125.0(2) . . ?
O4 C17 C18 117.3(2) . . ?
O5 C17 C18 117.7(2) . . ?
C23 C18 C19 118.8(2) . . ?
C23 C18 C17 119.4(2) . . ?
C19 C18 C17 121.8(2) . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 118.8(2) . . ?
C20 C21 C31 119.5(2) . . ?
C22 C21 C31 121.6(2) . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C18 C23 C22 120.7(2) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
O9 C24 O8 123.0(2) . . ?
O9 C24 C25 123.9(3) . . ?
O8 C24 C25 113.1(2) . . ?
C27 C25 C26 119.8(2) . . ?
C27 C25 C24 118.6(2) . . ?
C26 C25 C24 121.6(2) . . ?
C27 C26 C25 120.2(2) 2_576 . ?
C27 C26 H26 119.9 2_576 . ?
C25 C26 H26 119.9 . . ?
C26 C27 C25 120.0(2) 2_576 . ?
C26 C27 H27 120.0 2_576 . ?
C25 C27 H27 120.0 . . ?
O7 C31 O6 122.7(2) . . ?
O7 C31 C21 123.4(2) . . ?
O6 C31 C21 113.9(2) . . ?
C4 N1 C1 111.01(18) . . ?
C4 N1 H1C 109.4 . . ?
C1 N1 H1C 109.4 . . ?
C4 N1 H1D 109.4 . . ?
C1 N1 H1D 109.4 . . ?
H1C N1 H1D 108.0 . . ?
C5 N2 C3 117.25(19) . . ?
C5 N2 C2 119.34(18) . . ?
C3 N2 C2 110.28(19) . . ?
C13 N3 C9 119.5(2) . . ?
C13 N3 C15 118.9(2) . . ?
C9 N3 C15 121.56(19) . . ?
C14 O2 H2 109.5 . . ?
C31 O6 H6 109.5 . . ?
C24 O8 H8 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -59.7(3) . . . . ?
N2 C3 C4 N1 54.8(3) . . . . ?
C10 C5 C6 C7 1.4(4) . . . . ?
N2 C5 C6 C7 176.8(2) . . . . ?
C10 C5 C6 F1 -176.1(2) . . . . ?
N2 C5 C6 F1 -0.8(3) . . . . ?
F1 C6 C7 C8 174.5(2) . . . . ?
C5 C6 C7 C8 -3.0(4) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C6 C7 C8 C11 -179.6(2) . . . . ?
C7 C8 C9 N3 179.5(2) . . . . ?
C11 C8 C9 N3 0.4(3) . . . . ?
C7 C8 C9 C10 1.8(3) . . . . ?
C11 C8 C9 C10 -177.3(2) . . . . ?
N2 C5 C10 C9 -173.4(2) . . . . ?
C6 C5 C10 C9 1.8(3) . . . . ?
C8 C9 C10 C5 -3.4(4) . . . . ?
N3 C9 C10 C5 179.0(2) . . . . ?
C9 C8 C11 O1 178.4(2) . . . . ?
C7 C8 C11 O1 -0.7(4) . . . . ?
C9 C8 C11 C12 -1.4(3) . . . . ?
C7 C8 C11 C12 179.6(2) . . . . ?
O1 C11 C12 C13 -178.8(2) . . . . ?
C8 C11 C12 C13 0.9(3) . . . . ?
O1 C11 C12 C14 -2.6(4) . . . . ?
C8 C11 C12 C14 177.2(2) . . . . ?
C11 C12 C13 N3 0.5(4) . . . . ?
C14 C12 C13 N3 -175.7(2) . . . . ?
C13 C12 C14 O3 -7.2(4) . . . . ?
C11 C12 C14 O3 176.5(2) . . . . ?
C13 C12 C14 O2 171.0(2) . . . . ?
C11 C12 C14 O2 -5.3(4) . . . . ?
O4 C17 C18 C23 3.0(3) . . . . ?
O5 C17 C18 C23 -176.2(2) . . . . ?
O4 C17 C18 C19 -179.4(2) . . . . ?
O5 C17 C18 C19 1.3(3) . . . . ?
C23 C18 C19 C20 0.9(4) . . . . ?
C17 C18 C19 C20 -176.6(2) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C22 -1.8(4) . . . . ?
C19 C20 C21 C31 175.4(2) . . . . ?
C20 C21 C22 C23 1.1(4) . . . . ?
C31 C21 C22 C23 -176.0(2) . . . . ?
C19 C18 C23 C22 -1.6(4) . . . . ?
C17 C18 C23 C22 176.0(2) . . . . ?
C21 C22 C23 C18 0.6(4) . . . . ?
O9 C24 C25 C27 2.8(4) . . . . ?
O8 C24 C25 C27 -176.3(2) . . . . ?
O9 C24 C25 C26 -177.3(3) . . . . ?
O8 C24 C25 C26 3.6(4) . . . . ?
C27 C25 C26 C27 1.0(4) . . . 2_576 ?
C24 C25 C26 C27 -178.8(2) . . . 2_576 ?
C26 C25 C27 C26 -1.0(4) . . . 2_576 ?
C24 C25 C27 C26 178.8(2) . . . 2_576 ?
C20 C21 C31 O7 -2.9(4) . . . . ?
C22 C21 C31 O7 174.2(3) . . . . ?
C20 C21 C31 O6 179.0(2) . . . . ?
C22 C21 C31 O6 -4.0(4) . . . . ?
C3 C4 N1 C1 -52.8(3) . . . . ?
C2 C1 N1 C4 55.6(3) . . . . ?
C10 C5 N2 C3 3.9(3) . . . . ?
C6 C5 N2 C3 -171.2(2) . . . . ?
C10 C5 N2 C2 -133.6(3) . . . . ?
C6 C5 N2 C2 51.4(3) . . . . ?
C4 C3 N2 C5 159.3(2) . . . . ?
C4 C3 N2 C2 -59.6(3) . . . . ?
C1 C2 N2 C5 -157.9(2) . . . . ?
C1 C2 N2 C3 61.9(3) . . . . ?
C12 C13 N3 C9 -1.6(4) . . . . ?
C12 C13 N3 C15 179.3(2) . . . . ?
C8 C9 N3 C13 1.1(3) . . . . ?
C10 C9 N3 C13 178.8(2) . . . . ?
C8 C9 N3 C15 -179.9(2) . . . . ?
C10 C9 N3 C15 -2.2(4) . . . . ?
C16 C15 N3 C13 98.6(3) . . . . ?
C16 C15 N3 C9 -80.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1C O3 0.90 1.93 2.776(3) 155 1_554 yes
N1 H1D O4 0.90 1.79 2.688(3) 172 2_765 yes
O2 H2 O1 0.82 1.80 2.522(3) 146 . yes
O6 H6 O5 0.82 1.86 2.667(3) 167 1_455 yes
O8 H8 O5 0.82 1.86 2.673(3) 171 2_666 yes
C2 H2B F1 0.97 2.16 2.846(3) 126 . yes
C4 H4A O6 0.97 2.52 3.198(3) 127 2_665 yes
C4 H4B O2 0.97 2.39 3.283(4) 152 2_676 yes
C15 H15B O7 0.97 2.53 3.497(4) 176 1_655 yes
C16 H16B O8 0.96 2.52 3.370(4) 148 2_666 yes


_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.098




#==============END



data_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 F N3 O3, C8 H6 N O4, H2 O'
_chemical_formula_sum            'C24 H27 F N4 O8'
_chemical_formula_weight         518.50

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

_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                   9.5670(8)
_cell_length_b                   8.1152(6)
_cell_length_c                   30.906(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.476(2)
_cell_angle_gamma                90.00
_cell_volume                     2397.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2.59
_cell_measurement_theta_min      27.89
_cell_measurement_theta_max      4433

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13418
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4437
_reflns_number_gt                3450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1092P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4437
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1442(2) 0.6489(3) 0.18723(7) 0.0417(5) Uani 1 1 d . . .
H1A H 0.1196 0.6847 0.2159 0.050 Uiso 1 1 calc R . .
H1B H 0.0594 0.6454 0.1689 0.050 Uiso 1 1 calc R . .
C2 C 0.2459(2) 0.7684(2) 0.16890(7) 0.0390(5) Uani 1 1 d . . .
H2A H 0.2022 0.8759 0.1661 0.047 Uiso 1 1 calc R . .
H2B H 0.3269 0.7786 0.1887 0.047 Uiso 1 1 calc R . .
C3 C 0.3547(2) 0.5513(2) 0.12912(7) 0.0391(5) Uani 1 1 d . . .
H3A H 0.4383 0.5548 0.1480 0.047 Uiso 1 1 calc R . .
H3B H 0.3815 0.5164 0.1006 0.047 Uiso 1 1 calc R . .
C4 C 0.2521(2) 0.4296(2) 0.14662(6) 0.0409(5) Uani 1 1 d . . .
H4A H 0.1706 0.4219 0.1269 0.049 Uiso 1 1 calc R . .
H4B H 0.2952 0.3215 0.1487 0.049 Uiso 1 1 calc R . .
C5 C 0.3640(2) 0.8334(2) 0.10312(6) 0.0326(4) Uani 1 1 d . . .
C6 C 0.3004(2) 0.9857(2) 0.09176(6) 0.0359(5) Uani 1 1 d . . .
C7 C 0.3650(2) 1.1046(2) 0.06931(6) 0.0358(5) Uani 1 1 d . . .
H7 H 0.3194 1.2035 0.0631 0.043 Uiso 1 1 calc R . .
C8 C 0.5016(2) 1.0780(2) 0.05539(6) 0.0341(5) Uani 1 1 d . . .
C9 C 0.5657(2) 0.9264(2) 0.06473(6) 0.0345(5) Uani 1 1 d . . .
C10 C 0.4961(2) 0.8072(2) 0.08859(6) 0.0365(5) Uani 1 1 d . . .
H10 H 0.5405 0.7074 0.0948 0.044 Uiso 1 1 calc R . .
N4 N 0.69955(18) 0.8963(2) 0.05045(6) 0.0426(4) Uani 1 1 d . . .
C12 C 0.7656(2) 1.0136(3) 0.02878(7) 0.0488(6) Uani 1 1 d . . .
H12 H 0.8554 0.9910 0.0201 0.059 Uiso 1 1 calc R . .
C13 C 0.7097(2) 1.1643(3) 0.01862(7) 0.0455(5) Uani 1 1 d . . .
C14 C 0.5728(2) 1.2052(3) 0.03172(7) 0.0420(5) Uani 1 1 d . . .
C15 C 0.7725(2) 0.7392(3) 0.06060(9) 0.0576(7) Uani 1 1 d . . .
H15A H 0.8443 0.7216 0.0399 0.069 Uiso 1 1 calc R . .
H15B H 0.7061 0.6492 0.0577 0.069 Uiso 1 1 calc R . .
C16 C 0.8392(4) 0.7377(4) 0.10603(11) 0.0889(10) Uani 1 1 d . . .
H16A H 0.9101 0.8212 0.1084 0.133 Uiso 1 1 calc R . .
H16B H 0.8805 0.6318 0.1118 0.133 Uiso 1 1 calc R . .
H16C H 0.7690 0.7591 0.1266 0.133 Uiso 1 1 calc R . .
C17 C 0.7927(3) 1.2805(4) -0.00636(8) 0.0600(7) Uani 1 1 d . . .
C18 C 0.66110(18) 0.0875(2) 0.19538(6) 0.0279(4) Uani 1 1 d . . .
C19 C 0.78752(19) 0.0435(2) 0.21884(6) 0.0289(4) Uani 1 1 d . . .
C20 C 0.91609(18) 0.0981(2) 0.20202(6) 0.0278(4) Uani 1 1 d . . .
C21 C 0.91435(19) 0.1826(2) 0.16328(6) 0.0341(5) Uani 1 1 d . . .
H21 H 0.9990 0.2152 0.1523 0.041 Uiso 1 1 calc R . .
C22 C 0.7915(2) 0.2209(3) 0.14014(6) 0.0415(5) Uani 1 1 d . . .
H22 H 0.7935 0.2757 0.1138 0.050 Uiso 1 1 calc R . .
C23 C 0.6663(2) 0.1760(3) 0.15699(6) 0.0356(5) Uani 1 1 d . . .
H23 H 0.5831 0.2056 0.1423 0.043 Uiso 1 1 calc R . .
C24 C 0.52357(19) 0.0462(2) 0.21253(6) 0.0304(4) Uani 1 1 d . . .
C25 C 1.05538(18) 0.0703(2) 0.22549(6) 0.0298(4) Uani 1 1 d . . .
F1 F 0.16720(13) 1.01197(15) 0.10294(4) 0.0516(4) Uani 1 1 d . . .
N1 N 0.20854(17) 0.4818(2) 0.18987(5) 0.0329(4) Uani 1 1 d . . .
H1C H 0.2834 0.4835 0.2085 0.040 Uiso 1 1 calc R . .
H1D H 0.1463 0.4093 0.1998 0.040 Uiso 1 1 calc R . .
N2 N 0.29173(17) 0.71507(19) 0.12631(5) 0.0348(4) Uani 1 1 d . . .
N3 N 0.78533(18) -0.0418(3) 0.25580(6) 0.0534(6) Uani 1 1 d . . .
H3C H 0.8624 -0.0646 0.2699 0.064 Uiso 1 1 calc R . .
H3D H 0.7069 -0.0738 0.2655 0.064 Uiso 1 1 calc R . .
O1 O 0.5165(2) 1.3431(2) 0.02387(6) 0.0615(5) Uani 1 1 d . . .
O2 O 0.7318(2) 1.4222(2) -0.01655(6) 0.0702(6) Uani 1 1 d . . .
H2 H 0.6583 1.4300 -0.0040 0.105 Uiso 1 1 calc R . .
O3 O 0.9108(2) 1.2511(3) -0.01728(7) 0.0784(6) Uani 1 1 d . . .
O4 O 0.41799(13) 0.11835(18) 0.19072(5) 0.0411(4) Uani 1 1 d . . .
H4 H 0.3449 0.0997 0.2028 0.062 Uiso 1 1 calc R . .
O5 O 0.50518(14) -0.04196(19) 0.24340(5) 0.0442(4) Uani 1 1 d . . .
O6 O 1.06222(14) -0.0258(2) 0.25735(5) 0.0474(4) Uani 1 1 d . . .
O7 O 1.15975(13) 0.14459(17) 0.21175(5) 0.0376(4) Uani 1 1 d . . .
O8 O 0.0360(4) 0.4035(4) 0.06313(9) 0.1515(15) Uani 1 1 d . . .
H8A H -0.0325 0.4026 0.0462 0.227 Uiso 1 1 d R . .
H8B H 0.1157 0.3976 0.0545 0.227 Uiso 1 1 d 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
C1 N1 1.490(3) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.470(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.460(2) . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.479(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.376(3) . ?
C5 N2 1.398(2) . ?
C5 C6 1.415(3) . ?
C6 F1 1.352(2) . ?
C6 C7 1.353(3) . ?
C7 C8 1.409(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(3) . ?
C8 C14 1.451(3) . ?
C9 N4 1.394(3) . ?
C9 C10 1.402(3) . ?
C10 H10 0.9300 . ?
N4 C12 1.338(3) . ?
N4 C15 1.480(3) . ?
C12 C13 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.427(3) . ?
C13 C17 1.473(3) . ?
C14 O1 1.261(3) . ?
C15 C16 1.517(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.216(3) . ?
C17 O2 1.321(4) . ?
C18 C23 1.390(3) . ?
C18 C19 1.428(3) . ?
C18 C24 1.478(2) . ?
C19 N3 1.336(2) . ?
C19 C20 1.426(2) . ?
C20 C21 1.379(3) . ?
C20 C25 1.506(3) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O5 1.212(2) . ?
C24 O4 1.326(2) . ?
C25 O6 1.256(2) . ?
C25 O7 1.256(2) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
O2 H2 0.8200 . ?
O4 H4 0.8200 . ?
O8 H8A 0.8201 . ?
O8 H8B 0.8202 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.58(16) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 111.77(17) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 C4 110.13(17) . . ?
N2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 110.45(16) . . ?
N1 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 N2 122.84(18) . . ?
C10 C5 C6 116.41(17) . . ?
N2 C5 C6 120.70(17) . . ?
F1 C6 C7 118.37(18) . . ?
F1 C6 C5 118.29(17) . . ?
C7 C6 C5 123.31(18) . . ?
C6 C7 C8 119.85(19) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 118.34(18) . . ?
C9 C8 C14 121.21(19) . . ?
C7 C8 C14 120.45(19) . . ?
N4 C9 C8 119.28(18) . . ?
N4 C9 C10 120.60(19) . . ?
C8 C9 C10 120.12(18) . . ?
C5 C10 C9 121.91(19) . . ?
C5 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 N4 C9 119.59(19) . . ?
C12 N4 C15 119.36(18) . . ?
C9 N4 C15 120.99(18) . . ?
N4 C12 C13 124.3(2) . . ?
N4 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 C17 118.7(2) . . ?
C14 C13 C17 121.5(2) . . ?
O1 C14 C13 122.8(2) . . ?
O1 C14 C8 121.5(2) . . ?
C13 C14 C8 115.8(2) . . ?
N4 C15 C16 112.3(2) . . ?
N4 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N4 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 120.7(2) . . ?
O3 C17 C13 123.2(3) . . ?
O2 C17 C13 116.1(2) . . ?
C23 C18 C19 120.14(16) . . ?
C23 C18 C24 119.23(17) . . ?
C19 C18 C24 120.57(16) . . ?
N3 C19 C20 121.19(17) . . ?
N3 C19 C18 121.28(16) . . ?
C20 C19 C18 117.50(16) . . ?
C21 C20 C19 119.51(17) . . ?
C21 C20 C25 118.01(16) . . ?
C19 C20 C25 122.47(16) . . ?
C20 C21 C22 122.55(17) . . ?
C20 C21 H21 118.7 . . ?
C22 C21 H21 118.7 . . ?
C23 C22 C21 118.60(18) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C18 121.59(18) . . ?
C22 C23 H23 119.2 . . ?
C18 C23 H23 119.2 . . ?
O5 C24 O4 121.85(16) . . ?
O5 C24 C18 125.32(17) . . ?
O4 C24 C18 112.83(16) . . ?
O6 C25 O7 123.24(17) . . ?
O6 C25 C20 119.06(16) . . ?
O7 C25 C20 117.71(17) . . ?
C4 N1 C1 110.07(15) . . ?
C4 N1 H1C 109.6 . . ?
C1 N1 H1C 109.6 . . ?
C4 N1 H1D 109.6 . . ?
C1 N1 H1D 109.6 . . ?
H1C N1 H1D 108.2 . . ?
C5 N2 C3 116.34(15) . . ?
C5 N2 C2 115.45(15) . . ?
C3 N2 C2 110.65(15) . . ?
C19 N3 H3C 120.0 . . ?
C19 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?
C17 O2 H2 109.5 . . ?
C24 O4 H4 109.5 . . ?
H8A O8 H8B 121.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 56.6(2) . . . . ?
N2 C3 C4 N1 -58.6(2) . . . . ?
C10 C5 C6 F1 175.72(18) . . . . ?
N2 C5 C6 F1 -1.6(3) . . . . ?
C10 C5 C6 C7 -2.5(3) . . . . ?
N2 C5 C6 C7 -179.87(19) . . . . ?
F1 C6 C7 C8 -177.05(18) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C6 C7 C8 C14 -179.27(19) . . . . ?
C7 C8 C9 N4 178.62(18) . . . . ?
C14 C8 C9 N4 -1.0(3) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
C14 C8 C9 C10 178.40(19) . . . . ?
N2 C5 C10 C9 178.87(19) . . . . ?
C6 C5 C10 C9 1.6(3) . . . . ?
N4 C9 C10 C5 179.99(19) . . . . ?
C8 C9 C10 C5 0.6(3) . . . . ?
C8 C9 N4 C12 1.2(3) . . . . ?
C10 C9 N4 C12 -178.1(2) . . . . ?
C8 C9 N4 C15 178.4(2) . . . . ?
C10 C9 N4 C15 -1.0(3) . . . . ?
C9 N4 C12 C13 -1.1(3) . . . . ?
C15 N4 C12 C13 -178.3(2) . . . . ?
N4 C12 C13 C14 0.6(4) . . . . ?
N4 C12 C13 C17 -178.5(2) . . . . ?
C12 C13 C14 O1 178.9(2) . . . . ?
C17 C13 C14 O1 -2.0(4) . . . . ?
C12 C13 C14 C8 -0.3(3) . . . . ?
C17 C13 C14 C8 178.78(19) . . . . ?
C9 C8 C14 O1 -178.7(2) . . . . ?
C7 C8 C14 O1 1.7(3) . . . . ?
C9 C8 C14 C13 0.5(3) . . . . ?
C7 C8 C14 C13 -179.07(19) . . . . ?
C12 N4 C15 C16 96.7(3) . . . . ?
C9 N4 C15 C16 -80.5(3) . . . . ?
C12 C13 C17 O3 -2.4(4) . . . . ?
C14 C13 C17 O3 178.4(2) . . . . ?
C12 C13 C17 O2 177.8(2) . . . . ?
C14 C13 C17 O2 -1.3(3) . . . . ?
C23 C18 C19 N3 -179.92(19) . . . . ?
C24 C18 C19 N3 2.8(3) . . . . ?
C23 C18 C19 C20 1.9(3) . . . . ?
C24 C18 C19 C20 -175.36(15) . . . . ?
N3 C19 C20 C21 178.60(19) . . . . ?
C18 C19 C20 C21 -3.2(3) . . . . ?
N3 C19 C20 C25 -2.8(3) . . . . ?
C18 C19 C20 C25 175.40(16) . . . . ?
C19 C20 C21 C22 1.6(3) . . . . ?
C25 C20 C21 C22 -177.12(19) . . . . ?
C20 C21 C22 C23 1.5(3) . . . . ?
C21 C22 C23 C18 -2.9(3) . . . . ?
C19 C18 C23 C22 1.2(3) . . . . ?
C24 C18 C23 C22 178.49(19) . . . . ?
C23 C18 C24 O5 173.22(19) . . . . ?
C19 C18 C24 O5 -9.5(3) . . . . ?
C23 C18 C24 O4 -7.6(2) . . . . ?
C19 C18 C24 O4 169.70(17) . . . . ?
C21 C20 C25 O6 -169.91(17) . . . . ?
C19 C20 C25 O6 11.4(3) . . . . ?
C21 C20 C25 O7 9.6(3) . . . . ?
C19 C20 C25 O7 -169.06(16) . . . . ?
C3 C4 N1 C1 58.4(2) . . . . ?
C2 C1 N1 C4 -56.9(2) . . . . ?
C10 C5 N2 C3 -8.7(3) . . . . ?
C6 C5 N2 C3 168.45(18) . . . . ?
C10 C5 N2 C2 123.5(2) . . . . ?
C6 C5 N2 C2 -59.4(3) . . . . ?
C4 C3 N2 C5 -168.24(17) . . . . ?
C4 C3 N2 C2 57.4(2) . . . . ?
C1 C2 N2 C5 167.82(18) . . . . ?
C1 C2 N2 C3 -57.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1C O6 0.90 1.78 2.679(2) 175 2_655 yes
N1 H1D O7 0.90 2.18 2.859(2) 132 1_455 yes
N1 H1D O5 0.90 2.36 2.971(2) 126 2_555 yes
O2 H2 O1 0.82 1.79 2.538(3) 150 . yes
N3 H3C O5 0.86 2.04 2.693(2) 132 . yes
N3 H3D O6 0.86 1.99 2.650(2) 133 . yes
O4 H4 O7 0.82 1.84 2.589(2) 152 1_455 yes
O8 H8A O3 0.82 2.36 2.978(4) 133 1_445 yes
O8 H8B O2 0.82 2.41 3.047(5) 135 3_675 yes
C1 H1A O5 0.97 2.55 3.048(3) 112 2_555 yes
C2 H2A F1 0.97 2.26 2.919(3) 124 . yes
C4 H4A O8 0.97 2.31 3.242(4) 160 . yes
C4 H4B O4 0.97 2.37 3.248(3) 150 . yes
C15 H15A O3 0.97 2.49 3.369(4) 150 3_775 yes

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.064






#==============END




data_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H19 F N3 O3), 2(C8 H6 N O4), 7(H2 O)'
_chemical_formula_sum            'C48 H64 F2 N8 O21'
_chemical_formula_weight         1127.07

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)/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                   9.964(3)
_cell_length_b                   14.760(4)
_cell_length_c                   18.275(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.283(5)
_cell_angle_gamma                90.00
_cell_volume                     2687.6(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8005
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1188
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9820
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14525
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4888
_reflns_number_gt                3848
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1565P)²+1.4048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4888
_refine_ls_number_parameters     373
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2475
_refine_ls_wR_factor_gt          0.2345
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3861(3) 0.4562(2) 0.27944(17) 0.0525(7) Uani 1 1 d . . .
H1A H 0.3795 0.4566 0.3324 0.063 Uiso 1 1 calc R . .
H1B H 0.3858 0.3936 0.2631 0.063 Uiso 1 1 calc R . .
C2 C 0.2692(3) 0.5054(2) 0.24678(14) 0.0463(7) Uani 1 1 d . . .
H2A H 0.1865 0.4754 0.2607 0.056 Uiso 1 1 calc R . .
H2B H 0.2667 0.5668 0.2655 0.056 Uiso 1 1 calc R . .
C3 C 0.4034(3) 0.5492(2) 0.14354(15) 0.0440(6) Uani 1 1 d . . .
H3A H 0.4046 0.6122 0.1585 0.053 Uiso 1 1 calc R . .
H3B H 0.4089 0.5471 0.0906 0.053 Uiso 1 1 calc R . .
C4 C 0.5221(3) 0.5009(2) 0.17631(15) 0.0468(7) Uani 1 1 d . . .
H4A H 0.5253 0.4392 0.1583 0.056 Uiso 1 1 calc R . .
H4B H 0.6042 0.5312 0.1620 0.056 Uiso 1 1 calc R . .
C5 C 0.1635(2) 0.53456(17) 0.13004(12) 0.0335(5) Uani 1 1 d . . .
C6 C 0.0432(3) 0.48671(18) 0.13962(13) 0.0377(6) Uani 1 1 d . . .
C7 C -0.0711(2) 0.50904(18) 0.10571(13) 0.0383(6) Uani 1 1 d . . .
H7 H -0.1491 0.4766 0.1152 0.046 Uiso 1 1 calc R . .
C8 C -0.0741(2) 0.58085(17) 0.05611(13) 0.0351(6) Uani 1 1 d . . .
C9 C 0.0443(2) 0.62791(17) 0.04338(13) 0.0345(5) Uani 1 1 d . . .
C10 C 0.1605(2) 0.60533(17) 0.08167(13) 0.0360(6) Uani 1 1 d . . .
H10 H 0.2380 0.6391 0.0742 0.043 Uiso 1 1 calc R . .
C11 C -0.1960(3) 0.60396(19) 0.01869(14) 0.0415(6) Uani 1 1 d . . .
C12 C -0.1863(3) 0.6748(2) -0.03283(15) 0.0447(7) Uani 1 1 d . . .
C13 C -0.0682(3) 0.7185(2) -0.04213(16) 0.0476(7) Uani 1 1 d . . .
H13 H -0.0653 0.7655 -0.0760 0.057 Uiso 1 1 calc R . .
N4 N 0.0430(2) 0.69871(16) -0.00611(13) 0.0424(5) Uani 1 1 d . . .
C15 C 0.1643(3) 0.7521(2) -0.02119(19) 0.0566(8) Uani 1 1 d . . .
H15A H 0.2108 0.7645 0.0245 0.068 Uiso 1 1 calc R . .
H15B H 0.1386 0.8097 -0.0427 0.068 Uiso 1 1 calc R . .
C16 C 0.2571(4) 0.7040(3) -0.0718(2) 0.0739(11) Uani 1 1 d . . .
H16A H 0.2872 0.6488 -0.0494 0.111 Uiso 1 1 calc R . .
H16B H 0.3330 0.7420 -0.0820 0.111 Uiso 1 1 calc R . .
H16C H 0.2108 0.6903 -0.1166 0.111 Uiso 1 1 calc R . .
C17 C -0.3029(3) 0.7040(3) -0.0761(2) 0.0589(8) Uani 1 1 d . . .
C18 C -0.2496(3) 0.3468(2) 0.29773(17) 0.0491(7) Uani 1 1 d . . .
C19 C -0.1128(3) 0.30681(18) 0.30118(15) 0.0416(6) Uani 1 1 d . . .
C20 C -0.0814(3) 0.23415(19) 0.25793(16) 0.0445(7) Uani 1 1 d . . .
H20 H -0.1456 0.2096 0.2266 0.053 Uiso 1 1 calc R . .
C21 C 0.0468(3) 0.19738(19) 0.26112(15) 0.0452(7) Uani 1 1 d . . .
C22 C 0.1408(3) 0.2323(2) 0.30850(16) 0.0468(7) Uani 1 1 d . . .
H22 H 0.2258 0.2066 0.3110 0.056 Uiso 1 1 calc R . .
C23 C 0.1101(3) 0.3054(2) 0.35255(16) 0.0473(7) Uani 1 1 d . . .
C24 C -0.0170(3) 0.34242(19) 0.34786(15) 0.0443(6) Uani 1 1 d . . .
H24 H -0.0384 0.3923 0.3767 0.053 Uiso 1 1 calc R . .
C47 C 0.0760(3) 0.1194(2) 0.21413(16) 0.0484(7) Uani 1 1 d . . .
F1 F 0.04400(18) 0.41385(12) 0.18336(10) 0.0567(5) Uani 1 1 d . . .
N1 N 0.5112(2) 0.50051(16) 0.25683(12) 0.0438(6) Uani 1 1 d . . .
H1C H 0.5818 0.4709 0.2763 0.053 Uiso 1 1 calc R . .
H1D H 0.5127 0.5578 0.2736 0.053 Uiso 1 1 calc R . .
N2 N 0.2795(2) 0.50739(15) 0.16703(12) 0.0379(5) Uani 1 1 d . . .
N3 N 0.2044(3) 0.3415(2) 0.39942(16) 0.0652(8) Uani 1 1 d . . .
H3C H 0.1844 0.3876 0.4261 0.078 Uiso 1 1 calc R . .
H3D H 0.2833 0.3181 0.4020 0.078 Uiso 1 1 calc R . .
O1 O -0.30395(19) 0.56273(17) 0.03097(12) 0.0574(6) Uani 1 1 d . . .
O2 O -0.4149(2) 0.6633(2) -0.06129(14) 0.0692(7) Uani 1 1 d . . .
H2 H -0.4048 0.6314 -0.0249 0.104 Uiso 1 1 calc R . .
O3 O -0.2970(3) 0.7621(2) -0.12221(19) 0.0927(10) Uani 1 1 d . . .
O4 O -0.3430(3) 0.3036(2) 0.2715(2) 0.0912(10) Uani 1 1 d . . .
O5 O -0.2663(2) 0.42484(14) 0.32384(14) 0.0576(6) Uani 1 1 d . . .
O6 O 0.0075(2) 0.09837(17) 0.16224(14) 0.0665(7) Uani 1 1 d . . .
O7 O 0.1824(2) 0.07451(15) 0.23406(13) 0.0599(6) Uani 1 1 d . . .
H7A H 0.1947 0.0324 0.2056 0.090 Uiso 1 1 calc R . .
O8 O 0.4995(4) 0.2748(3) 0.4094(2) 0.1299(15) Uani 1 1 d . . .
H8A H 0.4935 0.3260 0.4266 0.195 Uiso 1 1 d RD . .
H8B H 0.5625 0.2414 0.4200 0.195 Uiso 1 1 d R . .
O9 O 0.5080(3) 0.1770(2) 0.1991(2) 0.1071(13) Uani 1 1 d . . .
H9A H 0.5798 0.2039 0.2028 0.161 Uiso 1 1 d R . .
H9B H 0.4475 0.1851 0.2287 0.161 Uiso 1 1 d R . .
O10 O 0.4778(13) 0.8958(8) 0.9550(3) 0.178(4) Uani 0.50 1 d PU . .
H10A H 0.4122 0.9214 0.9724 0.267 Uiso 0.50 1 d PR . .
H10B H 0.5334 0.8706 0.9812 0.267 Uiso 0.50 1 d PR . .
O11 O 0.3172(14) 0.9663(10) 0.0300(7) 0.184(4) Uani 0.50 1 d PU . .
H11A H 0.3729 0.9992 0.0498 0.277 Uiso 0.50 1 d PR . .
H11B H 0.2405 0.9839 0.0212 0.277 Uiso 0.50 1 d PR . .
O12 O 0.0886(13) 0.0344(10) 0.0209(7) 0.192(5) Uani 0.50 1 d PU . .
H12A H 0.0788 0.0076 -0.0181 0.288 Uiso 0.50 1 d PR . .
H12B H 0.1635 0.0438 0.0381 0.288 Uiso 0.50 1 d PR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.469(4) . ?
C1 C2 1.494(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.462(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.447(3) . ?
C3 C4 1.502(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.476(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.369(4) . ?
C5 N2 1.395(3) . ?
C5 C6 1.403(4) . ?
C6 C7 1.335(4) . ?
C6 F1 1.340(3) . ?
C7 C8 1.395(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(3) . ?
C8 C11 1.433(4) . ?
C9 N4 1.382(3) . ?
C9 C10 1.390(4) . ?
C10 H10 0.9300 . ?
C11 O1 1.257(3) . ?
C11 C12 1.410(4) . ?
C12 C13 1.354(4) . ?
C12 C17 1.467(4) . ?
C13 N4 1.319(4) . ?
C13 H13 0.9300 . ?
N4 C15 1.470(4) . ?
C15 C16 1.490(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.204(5) . ?
C17 O2 1.297(4) . ?
C18 O4 1.224(4) . ?
C18 O5 1.258(4) . ?
C18 C19 1.486(4) . ?
C19 C20 1.369(4) . ?
C19 C24 1.381(4) . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(4) . ?
C21 C47 1.466(4) . ?
C22 C23 1.381(4) . ?
C22 H22 0.9300 . ?
C23 N3 1.376(4) . ?
C23 C24 1.381(4) . ?
C24 H24 0.9300 . ?
C47 O6 1.206(4) . ?
C47 O7 1.301(4) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
N3 H3C 0.8600 . ?
N3 H3D 0.8600 . ?
O2 H2 0.8200 . ?
O7 H7A 0.8200 . ?
O8 H8A 0.8202 . ?
O8 H8B 0.8200 . ?
O9 H9A 0.8201 . ?
O9 H9B 0.8204 . ?
O10 H10A 0.8197 . ?
O10 H10B 0.8202 . ?
O11 H11A 0.8200 . ?
O11 H11B 0.8228 . ?
O12 H12A 0.8202 . ?
O12 H12B 0.8206 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.4(2) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 110.5(2) . . ?
N2 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C4 110.6(2) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 109.7(2) . . ?
N1 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 N2 123.2(2) . . ?
C10 C5 C6 116.7(2) . . ?
N2 C5 C6 120.1(2) . . ?
C7 C6 F1 118.5(2) . . ?
C7 C6 C5 123.0(2) . . ?
F1 C6 C5 118.4(2) . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 C11 121.3(2) . . ?
C7 C8 C11 120.4(2) . . ?
N4 C9 C8 118.9(2) . . ?
N4 C9 C10 121.0(2) . . ?
C8 C9 C10 120.1(2) . . ?
C5 C10 C9 121.6(2) . . ?
C5 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
O1 C11 C12 122.7(2) . . ?
O1 C11 C8 121.6(3) . . ?
C12 C11 C8 115.7(2) . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 C17 118.6(3) . . ?
C11 C12 C17 121.4(3) . . ?
N4 C13 C12 124.1(3) . . ?
N4 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C13 N4 C9 119.9(2) . . ?
C13 N4 C15 118.5(2) . . ?
C9 N4 C15 121.6(2) . . ?
N4 C15 C16 111.9(3) . . ?
N4 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N4 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 121.4(3) . . ?
O3 C17 C12 123.0(3) . . ?
O2 C17 C12 115.5(3) . . ?
O4 C18 O5 121.6(3) . . ?
O4 C18 C19 120.3(3) . . ?
O5 C18 C19 118.1(3) . . ?
C20 C19 C24 119.7(3) . . ?
C20 C19 C18 119.9(3) . . ?
C24 C19 C18 120.4(3) . . ?
C19 C20 C21 119.6(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 C47 121.9(3) . . ?
C20 C21 C47 117.9(3) . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
N3 C23 C24 120.6(3) . . ?
N3 C23 C22 120.9(3) . . ?
C24 C23 C22 118.6(3) . . ?
C23 C24 C19 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
O6 C47 O7 123.1(3) . . ?
O6 C47 C21 123.3(3) . . ?
O7 C47 C21 113.6(3) . . ?
C1 N1 C4 110.4(2) . . ?
C1 N1 H1C 109.6 . . ?
C4 N1 H1C 109.6 . . ?
C1 N1 H1D 109.6 . . ?
C4 N1 H1D 109.6 . . ?
H1C N1 H1D 108.1 . . ?
C5 N2 C3 116.1(2) . . ?
C5 N2 C2 115.3(2) . . ?
C3 N2 C2 111.6(2) . . ?
C23 N3 H3C 120.0 . . ?
C23 N3 H3D 120.0 . . ?
H3C N3 H3D 120.0 . . ?
C17 O2 H2 109.5 . . ?
C47 O7 H7A 109.5 . . ?
H8A O8 H8B 121.3 . . ?
H9A O9 H9B 121.3 . . ?
H10A O10 H10B 121.4 . . ?
H11A O11 H11B 121.7 . . ?
H12A O12 H12B 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 57.9(3) . . . . ?
N2 C3 C4 N1 -56.8(3) . . . . ?
C10 C5 C6 C7 -1.9(4) . . . . ?
N2 C5 C6 C7 -179.8(2) . . . . ?
C10 C5 C6 F1 176.3(2) . . . . ?
N2 C5 C6 F1 -1.6(3) . . . . ?
F1 C6 C7 C8 -175.9(2) . . . . ?
C5 C6 C7 C8 2.3(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C6 C7 C8 C11 178.9(2) . . . . ?
C7 C8 C9 N4 179.4(2) . . . . ?
C11 C8 C9 N4 0.4(4) . . . . ?
C7 C8 C9 C10 -2.4(3) . . . . ?
C11 C8 C9 C10 178.6(2) . . . . ?
N2 C5 C10 C9 177.1(2) . . . . ?
C6 C5 C10 C9 -0.7(4) . . . . ?
N4 C9 C10 C5 -179.0(2) . . . . ?
C8 C9 C10 C5 2.9(4) . . . . ?
C9 C8 C11 O1 -178.7(2) . . . . ?
C7 C8 C11 O1 2.4(4) . . . . ?
C9 C8 C11 C12 1.9(4) . . . . ?
C7 C8 C11 C12 -177.0(2) . . . . ?
O1 C11 C12 C13 178.0(3) . . . . ?
C8 C11 C12 C13 -2.6(4) . . . . ?
O1 C11 C12 C17 -0.6(4) . . . . ?
C8 C11 C12 C17 178.8(2) . . . . ?
C11 C12 C13 N4 0.9(5) . . . . ?
C17 C12 C13 N4 179.6(3) . . . . ?
C12 C13 N4 C9 1.7(4) . . . . ?
C12 C13 N4 C15 -179.6(3) . . . . ?
C8 C9 N4 C13 -2.3(4) . . . . ?
C10 C9 N4 C13 179.6(2) . . . . ?
C8 C9 N4 C15 179.0(3) . . . . ?
C10 C9 N4 C15 0.9(4) . . . . ?
C13 N4 C15 C16 -99.9(3) . . . . ?
C9 N4 C15 C16 78.8(3) . . . . ?
C13 C12 C17 O3 4.0(5) . . . . ?
C11 C12 C17 O3 -177.4(3) . . . . ?
C13 C12 C17 O2 -175.8(3) . . . . ?
C11 C12 C17 O2 2.8(4) . . . . ?
O4 C18 C19 C20 18.3(4) . . . . ?
O5 C18 C19 C20 -163.2(3) . . . . ?
O4 C18 C19 C24 -161.7(3) . . . . ?
O5 C18 C19 C24 16.8(4) . . . . ?
C24 C19 C20 C21 -0.4(4) . . . . ?
C18 C19 C20 C21 179.6(2) . . . . ?
C19 C20 C21 C22 1.4(4) . . . . ?
C19 C20 C21 C47 179.8(2) . . . . ?
C20 C21 C22 C23 -1.2(4) . . . . ?
C47 C21 C22 C23 -179.5(2) . . . . ?
C21 C22 C23 N3 -179.1(3) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
N3 C23 C24 C19 -179.9(3) . . . . ?
C22 C23 C24 C19 1.0(4) . . . . ?
C20 C19 C24 C23 -0.8(4) . . . . ?
C18 C19 C24 C23 179.1(2) . . . . ?
C22 C21 C47 O6 -164.6(3) . . . . ?
C20 C21 C47 O6 17.1(4) . . . . ?
C22 C21 C47 O7 16.0(4) . . . . ?
C20 C21 C47 O7 -162.3(2) . . . . ?
C2 C1 N1 C4 -59.0(3) . . . . ?
C3 C4 N1 C1 58.4(3) . . . . ?
C10 C5 N2 C3 -9.2(4) . . . . ?
C6 C5 N2 C3 168.6(2) . . . . ?
C10 C5 N2 C2 124.1(3) . . . . ?
C6 C5 N2 C2 -58.2(3) . . . . ?
C4 C3 N2 C5 -168.4(2) . . . . ?
C4 C3 N2 C2 56.7(3) . . . . ?
C1 C2 N2 C5 167.2(2) . . . . ?
C1 C2 N2 C3 -57.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1C O5 0.90 1.87 2.763(3) 172 1_655 yes
N1 H1D O9 0.90 1.84 2.734(4) 172 2_655 yes
O2 H2 O1 0.82 1.75 2.500(4) 151 . yes
N3 H3C O12 0.86 2.29 3.105(14) 157 4_566 yes
N3 H3D O8 0.86 2.25 3.105(5) 173 . yes
O7 H7A O5 0.82 1.82 2.590(3) 155 2_545 yes
O8 H8A O10 0.82 2.41 3.062(9) 137 2_646 yes
O9 H9A O4 0.82 2.08 2.725(5) 135 1_655 yes
O10 H10A O11 0.82 1.57 2.355(17) 160 1_556 yes
C2 H2A F1 0.97 2.20 2.860(4) 125 . yes
C4 H4A O2 0.97 2.57 3.378(4) 141 3_565 yes

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.065




