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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_mo_2013417_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F3 N3 O2'
_chemical_formula_weight         409.36

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           ?
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   17.511(14)
_cell_length_b                   8.066(6)
_cell_length_c                   26.88(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3796(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1684
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35922
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.52
_reflns_number_total             8610
_reflns_number_gt                4398
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0473P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(11)
_refine_ls_number_reflns         8610
_refine_ls_number_parameters     543
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.006

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
F3' F 0.12825(19) 0.8474(6) 0.66413(13) 0.1218(14) Uani 1 1 d . . .
F2' F 0.2296(2) 0.9893(5) 0.66856(13) 0.1088(12) Uani 1 1 d . . .
F1' F 0.2350(2) 0.7284(4) 0.67029(18) 0.0934(13) Uani 1 1 d . . .
F2 F 0.37888(18) 0.6744(6) 0.53958(14) 0.1285(14) Uani 1 1 d . . .
F1 F 0.4869(2) 0.7813(4) 0.53496(17) 0.0925(12) Uani 1 1 d . . .
F3 F 0.4759(3) 0.5229(4) 0.53681(13) 0.1245(15) Uani 1 1 d . . .
O1' O 0.30612(16) 0.9416(4) 1.03286(12) 0.0527(8) Uani 1 1 d . . .
O2' O 0.36602(18) 0.7445(4) 0.89409(18) 0.0514(12) Uani 1 1 d . . .
O1 O 0.56342(15) 0.5481(4) 0.17315(11) 0.0480(7) Uani 1 1 d . . .
O2 O 0.62609(17) 0.7535(3) 0.31362(18) 0.0489(11) Uani 1 1 d . . .
C9' C 0.3061(3) 1.2412(7) 1.0397(3) 0.063(2) Uani 1 1 d . . .
H9' H 0.3049 1.2320 1.0742 0.076 Uiso 1 1 calc R . .
N3' N 0.30695(15) 0.9621(4) 0.93033(12) 0.0330(8) Uani 1 1 d . . .
N1' N 0.21321(18) 0.8195(4) 0.98122(14) 0.0379(8) Uani 1 1 d . . .
N3 N 0.56440(16) 0.5383(4) 0.27625(12) 0.0337(8) Uani 1 1 d . . .
N2 N 0.3899(2) 0.7891(4) 0.27916(18) 0.0404(11) Uani 1 1 d . . .
N1 N 0.47181(16) 0.6823(4) 0.22404(13) 0.0339(8) Uani 1 1 d . . .
C10' C 0.3089(3) 1.3934(8) 1.0183(3) 0.070(2) Uani 1 1 d . . .
H1 H 0.3085 1.4881 1.0380 0.084 Uiso 1 1 calc R . .
C8' C 0.3051(3) 1.1008(7) 1.0109(2) 0.0435(14) Uani 1 1 d . . .
C13' C 0.3092(2) 1.1142(6) 0.96002(19) 0.0313(12) Uani 1 1 d . . .
C1' C 0.2386(2) 0.8708(5) 0.93474(16) 0.0355(10) Uani 1 1 d . . .
C2' C 0.1864(2) 0.8115(6) 0.90076(16) 0.0349(10) Uani 1 1 d . . .
C14' C 0.1856(2) 0.8313(5) 0.84670(16) 0.0361(10) Uani 1 1 d . . .
C19' C 0.2332(2) 0.9464(6) 0.82253(18) 0.0448(11) Uani 1 1 d . . .
H13 H 0.2644 1.0155 0.8413 0.054 Uiso 1 1 calc R . .
C18' C 0.2343(2) 0.9581(5) 0.77118(18) 0.0467(11) Uani 1 1 d . . .
H14 H 0.2661 1.0350 0.7558 0.056 Uiso 1 1 calc R . .
C17' C 0.1882(2) 0.8554(6) 0.74263(15) 0.0424(11) Uani 1 1 d . . .
C20' C 0.1937(3) 0.8573(8) 0.6874(2) 0.0668(16) Uani 1 1 d . . .
C7' C 0.2408(2) 0.8493(5) 1.02852(18) 0.0463(11) Uani 1 1 d . . .
C3' C 0.1469(2) 0.7241(5) 0.9724(3) 0.0435(14) Uani 1 1 d . . .
C4' C 0.1110(3) 0.6523(6) 1.0143(2) 0.0575(13) Uani 1 1 d . . .
H2 H 0.0673 0.5884 1.0102 0.069 Uiso 1 1 calc R . .
C5' C 0.1403(3) 0.6765(7) 1.0608(2) 0.0692(15) Uani 1 1 d . . .
H3 H 0.1168 0.6264 1.0879 0.083 Uiso 1 1 calc R . .
C6' C 0.2061(3) 0.7766(6) 1.0687(3) 0.0572(16) Uani 1 1 d . . .
H4 H 0.2253 0.7924 1.1006 0.069 Uiso 1 1 calc R . .
N2' N 0.1307(2) 0.7185(4) 0.92407(19) 0.0434(11) Uani 1 1 d . . .
C11' C 0.3123(3) 1.4074(6) 0.9675(2) 0.0516(16) Uani 1 1 d . . .
H7 H 0.3143 1.5121 0.9531 0.062 Uiso 1 1 calc R . .
C12' C 0.3129(2) 1.2683(5) 0.9373(2) 0.0437(15) Uani 1 1 d . . .
H6 H 0.3156 1.2779 0.9029 0.052 Uiso 1 1 calc R . .
C21' C 0.3714(2) 0.8830(6) 0.91079(16) 0.0376(10) Uani 1 1 d . . .
C22' C 0.4438(2) 0.9822(5) 0.9109(2) 0.0541(12) Uani 1 1 d . . .
H9 H 0.4860 0.9112 0.9028 0.081 Uiso 1 1 calc R . .
H8 H 0.4516 1.0293 0.9433 0.081 Uiso 1 1 calc R . .
H10 H 0.4402 1.0694 0.8867 0.081 Uiso 1 1 calc R . .
C15' C 0.1360(2) 0.7348(5) 0.8170(3) 0.0436(15) Uani 1 1 d . . .
H12 H 0.1022 0.6617 0.8322 0.052 Uiso 1 1 calc R . .
C16' C 0.1370(3) 0.7472(5) 0.7668(3) 0.0485(18) Uani 1 1 d . . .
H11 H 0.1035 0.6835 0.7480 0.058 Uiso 1 1 calc R . .
C10 C 0.5607(3) 0.0985(7) 0.1932(3) 0.0604(18) Uani 1 1 d . . .
H15 H 0.5587 0.0015 0.1745 0.072 Uiso 1 1 calc R . .
C11 C 0.5665(3) 0.0862(7) 0.2452(2) 0.0567(17) Uani 1 1 d . . .
H21 H 0.5695 -0.0161 0.2611 0.068 Uiso 1 1 calc R . .
C12 C 0.5676(3) 0.2321(6) 0.2717(2) 0.0420(15) Uani 1 1 d . . .
H22 H 0.5693 0.2266 0.3063 0.050 Uiso 1 1 calc R . .
C13 C 0.5664(2) 0.3843(7) 0.24975(19) 0.0392(13) Uani 1 1 d . . .
C1 C 0.4963(2) 0.6307(5) 0.27136(15) 0.0309(9) Uani 1 1 d . . .
C2 C 0.4439(2) 0.6957(5) 0.30410(17) 0.0322(10) Uani 1 1 d . . .
C14 C 0.4427(2) 0.6771(5) 0.35886(15) 0.0317(10) Uani 1 1 d . . .
C19 C 0.4888(2) 0.5642(5) 0.38368(16) 0.0414(11) Uani 1 1 d . . .
H28 H 0.5205 0.4945 0.3654 0.050 Uiso 1 1 calc R . .
C18 C 0.4885(2) 0.5535(5) 0.43503(17) 0.0431(11) Uani 1 1 d . . .
H29 H 0.5201 0.4778 0.4511 0.052 Uiso 1 1 calc R . .
C17 C 0.4407(2) 0.6566(5) 0.46261(16) 0.0386(10) Uani 1 1 d . . .
C20 C 0.4454(3) 0.6561(7) 0.51774(18) 0.0551(14) Uani 1 1 d . . .
C3 C 0.4065(3) 0.7767(5) 0.2313(2) 0.0374(13) Uani 1 1 d . . .
C7 C 0.4994(2) 0.6466(5) 0.17675(17) 0.0407(10) Uani 1 1 d . . .
C8 C 0.5621(2) 0.3925(6) 0.1975(2) 0.0412(13) Uani 1 1 d . . .
C22 C 0.7014(2) 0.5156(5) 0.2957(2) 0.0564(13) Uani 1 1 d . . .
H22A H 0.7444 0.5893 0.2946 0.085 Uiso 1 1 calc R . .
H22B H 0.7023 0.4446 0.2670 0.085 Uiso 1 1 calc R . .
H22C H 0.7040 0.4493 0.3253 0.085 Uiso 1 1 calc R . .
C9 C 0.5580(3) 0.2493(6) 0.1685(3) 0.0583(19) Uani 1 1 d . . .
H20 H 0.5536 0.2548 0.1341 0.070 Uiso 1 1 calc R . .
C6 C 0.4649(3) 0.7136(7) 0.1376(2) 0.0558(15) Uani 1 1 d . . .
H25 H 0.4833 0.6910 0.1059 0.067 Uiso 1 1 calc R . .
C5 C 0.4009(3) 0.8187(7) 0.1433(2) 0.0576(14) Uani 1 1 d . . .
H24 H 0.3790 0.8677 0.1154 0.069 Uiso 1 1 calc R . .
C4 C 0.3709(2) 0.8490(5) 0.18919(19) 0.0520(12) Uani 1 1 d . . .
H23 H 0.3279 0.9157 0.1928 0.062 Uiso 1 1 calc R . .
C15 C 0.3942(3) 0.7753(5) 0.3866(2) 0.0391(14) Uani 1 1 d . . .
H27 H 0.3613 0.8484 0.3706 0.047 Uiso 1 1 calc R . .
C16 C 0.3939(3) 0.7660(6) 0.4392(2) 0.0457(16) Uani 1 1 d . . .
H26 H 0.3619 0.8344 0.4576 0.055 Uiso 1 1 calc R . .
C21 C 0.6293(2) 0.6141(5) 0.29584(16) 0.0371(10) 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
F3' C20' 1.307(6) . ?
F2' C20' 1.336(6) . ?
F1' C20' 1.348(6) . ?
F2 C20 1.312(5) . ?
F1 C20 1.328(6) . ?
F3 C20 1.305(6) . ?
O1' C7' 1.369(5) . ?
O1' C8' 1.413(6) . ?
O2' C21' 1.208(5) . ?
O1 C7 1.377(5) . ?
O1 C8 1.415(6) . ?
O2 C21 1.223(5) . ?
C9' C10' 1.358(8) . ?
C9' C8' 1.372(7) . ?
C9' H9' 0.9300 . ?
N3' C21' 1.399(5) . ?
N3' C1' 1.410(4) . ?
N3' C13' 1.464(6) . ?
N1' C7' 1.381(6) . ?
N1' C1' 1.389(5) . ?
N1' C3' 1.412(6) . ?
N3 C21 1.394(5) . ?
N3 C1 1.412(4) . ?
N3 C13 1.432(6) . ?
N2 C3 1.323(7) . ?
N2 C2 1.382(5) . ?
N1 C3 1.387(5) . ?
N1 C7 1.390(5) . ?
N1 C1 1.405(5) . ?
C10' C11' 1.369(8) . ?
C10' H1 0.9300 . ?
C8' C13' 1.374(7) . ?
C13' C12' 1.387(6) . ?
C1' C2' 1.378(5) . ?
C2' N2' 1.381(6) . ?
C2' C14' 1.462(6) . ?
C14' C19' 1.407(6) . ?
C14' C15' 1.412(6) . ?
C19' C18' 1.383(6) . ?
C19' H13 0.9300 . ?
C18' C17' 1.389(6) . ?
C18' H14 0.9300 . ?
C17' C16' 1.409(7) . ?
C17' C20' 1.489(7) . ?
C7' C6' 1.372(7) . ?
C3' N2' 1.331(8) . ?
C3' C4' 1.414(8) . ?
C4' C5' 1.363(7) . ?
C4' H2 0.9300 . ?
C5' C6' 1.423(7) . ?
C5' H3 0.9300 . ?
C6' H4 0.9300 . ?
C11' C12' 1.386(7) . ?
C11' H7 0.9300 . ?
C12' H6 0.9300 . ?
C21' C22' 1.499(5) . ?
C22' H9 0.9600 . ?
C22' H8 0.9600 . ?
C22' H10 0.9600 . ?
C15' C16' 1.353(10) . ?
C15' H12 0.9300 . ?
C16' H11 0.9300 . ?
C10 C9 1.385(7) . ?
C10 C11 1.407(8) . ?
C10 H15 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H21 0.9300 . ?
C12 C13 1.362(6) . ?
C12 H22 0.9300 . ?
C13 C8 1.409(7) . ?
C1 C2 1.375(5) . ?
C2 C14 1.480(6) . ?
C14 C15 1.381(6) . ?
C14 C19 1.387(6) . ?
C19 C18 1.383(5) . ?
C19 H28 0.9300 . ?
C18 C17 1.394(6) . ?
C18 H29 0.9300 . ?
C17 C16 1.358(6) . ?
C17 C20 1.484(6) . ?
C3 C4 1.418(7) . ?
C7 C6 1.328(7) . ?
C8 C9 1.394(7) . ?
C22 C21 1.492(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C9 H20 0.9300 . ?
C6 C5 1.415(7) . ?
C6 H25 0.9300 . ?
C5 C4 1.362(6) . ?
C5 H24 0.9300 . ?
C4 H23 0.9300 . ?
C15 C16 1.415(9) . ?
C15 H27 0.9300 . ?
C16 H26 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
C7' O1' C8' 116.6(3) . . ?
C7 O1 C8 117.7(3) . . ?
C10' C9' C8' 120.5(8) . . ?
C10' C9' H9' 119.8 . . ?
C8' C9' H9' 119.8 . . ?
C21' N3' C1' 118.6(3) . . ?
C21' N3' C13' 124.4(3) . . ?
C1' N3' C13' 114.5(3) . . ?
C7' N1' C1' 131.6(3) . . ?
C7' N1' C3' 122.5(4) . . ?
C1' N1' C3' 105.9(4) . . ?
C21 N3 C1 119.5(3) . . ?
C21 N3 C13 123.2(3) . . ?
C1 N3 C13 115.6(3) . . ?
C3 N2 C2 106.3(4) . . ?
C3 N1 C7 121.9(4) . . ?
C3 N1 C1 106.7(4) . . ?
C7 N1 C1 131.3(3) . . ?
C9' C10' C11' 120.0(7) . . ?
C9' C10' H1 120.0 . . ?
C11' C10' H1 120.0 . . ?
C9' C8' C13' 119.8(6) . . ?
C9' C8' O1' 121.0(6) . . ?
C13' C8' O1' 119.1(5) . . ?
C8' C13' C12' 120.8(5) . . ?
C8' C13' N3' 118.4(5) . . ?
C12' C13' N3' 120.8(5) . . ?
C2' C1' N1' 106.3(3) . . ?
C2' C1' N3' 133.5(4) . . ?
N1' C1' N3' 120.2(4) . . ?
C1' C2' N2' 110.9(4) . . ?
C1' C2' C14' 128.9(4) . . ?
N2' C2' C14' 120.2(4) . . ?
C19' C14' C15' 117.8(5) . . ?
C19' C14' C2' 121.7(4) . . ?
C15' C14' C2' 120.5(4) . . ?
C18' C19' C14' 120.9(4) . . ?
C18' C19' H13 119.5 . . ?
C14' C19' H13 119.5 . . ?
C19' C18' C17' 120.1(4) . . ?
C19' C18' H14 119.9 . . ?
C17' C18' H14 119.9 . . ?
C18' C17' C16' 119.0(5) . . ?
C18' C17' C20' 120.5(5) . . ?
C16' C17' C20' 120.5(5) . . ?
F3' C20' F2' 106.3(5) . . ?
F3' C20' F1' 105.2(5) . . ?
F2' C20' F1' 103.5(5) . . ?
F3' C20' C17' 114.8(5) . . ?
F2' C20' C17' 114.6(5) . . ?
F1' C20' C17' 111.5(5) . . ?
C6' C7' O1' 122.4(5) . . ?
C6' C7' N1' 119.7(4) . . ?
O1' C7' N1' 117.7(4) . . ?
N2' C3' N1' 111.0(5) . . ?
N2' C3' C4' 132.0(5) . . ?
N1' C3' C4' 117.0(6) . . ?
C5' C4' C3' 120.2(5) . . ?
C5' C4' H2 119.9 . . ?
C3' C4' H2 119.9 . . ?
C4' C5' C6' 121.6(5) . . ?
C4' C5' H3 119.2 . . ?
C6' C5' H3 119.2 . . ?
C7' C6' C5' 118.9(6) . . ?
C7' C6' H4 120.6 . . ?
C5' C6' H4 120.6 . . ?
C3' N2' C2' 105.9(4) . . ?
C10' C11' C12' 121.2(6) . . ?
C10' C11' H7 119.4 . . ?
C12' C11' H7 119.4 . . ?
C13' C12' C11' 117.8(6) . . ?
C13' C12' H6 121.1 . . ?
C11' C12' H6 121.1 . . ?
O2' C21' N3' 119.9(4) . . ?
O2' C21' C22' 124.1(4) . . ?
N3' C21' C22' 116.0(4) . . ?
C21' C22' H9 109.5 . . ?
C21' C22' H8 109.5 . . ?
H9 C22' H8 109.5 . . ?
C21' C22' H10 109.5 . . ?
H9 C22' H10 109.5 . . ?
H8 C22' H10 109.5 . . ?
C16' C15' C14' 121.0(5) . . ?
C16' C15' H12 119.5 . . ?
C14' C15' H12 119.5 . . ?
C15' C16' C17' 120.9(5) . . ?
C15' C16' H11 119.5 . . ?
C17' C16' H11 119.5 . . ?
C9 C10 C11 122.7(7) . . ?
C9 C10 H15 118.7 . . ?
C11 C10 H15 118.7 . . ?
C12 C11 C10 117.1(6) . . ?
C12 C11 H21 121.5 . . ?
C10 C11 H21 121.4 . . ?
C13 C12 C11 123.1(7) . . ?
C13 C12 H22 118.4 . . ?
C11 C12 H22 118.4 . . ?
C12 C13 C8 118.4(6) . . ?
C12 C13 N3 124.5(5) . . ?
C8 C13 N3 117.0(5) . . ?
C2 C1 N1 105.2(3) . . ?
C2 C1 N3 134.8(4) . . ?
N1 C1 N3 119.9(3) . . ?
C1 C2 N2 110.7(4) . . ?
C1 C2 C14 127.4(4) . . ?
N2 C2 C14 121.9(4) . . ?
C15 C14 C19 118.3(4) . . ?
C15 C14 C2 119.2(4) . . ?
C19 C14 C2 122.4(4) . . ?
C18 C19 C14 121.2(4) . . ?
C18 C19 H28 119.4 . . ?
C14 C19 H28 119.4 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H29 120.1 . . ?
C17 C18 H29 120.1 . . ?
C16 C17 C18 120.2(4) . . ?
C16 C17 C20 119.9(5) . . ?
C18 C17 C20 119.7(4) . . ?
F3 C20 F2 106.3(5) . . ?
F3 C20 F1 105.3(5) . . ?
F2 C20 F1 104.1(5) . . ?
F3 C20 C17 114.7(5) . . ?
F2 C20 C17 113.4(4) . . ?
F1 C20 C17 112.1(4) . . ?
N2 C3 N1 111.0(4) . . ?
N2 C3 C4 130.4(4) . . ?
N1 C3 C4 118.5(5) . . ?
C6 C7 O1 123.3(5) . . ?
C6 C7 N1 118.8(4) . . ?
O1 C7 N1 117.8(4) . . ?
C9 C8 C13 121.4(6) . . ?
C9 C8 O1 118.5(5) . . ?
C13 C8 O1 120.1(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C9 C8 117.3(7) . . ?
C10 C9 H20 121.3 . . ?
C8 C9 H20 121.3 . . ?
C7 C6 C5 121.2(6) . . ?
C7 C6 H25 119.4 . . ?
C5 C6 H25 119.4 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H24 119.6 . . ?
C6 C5 H24 119.6 . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 H23 120.7 . . ?
C3 C4 H23 120.7 . . ?
C14 C15 C16 120.7(5) . . ?
C14 C15 H27 119.6 . . ?
C16 C15 H27 119.6 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H26 120.2 . . ?
C15 C16 H26 120.1 . . ?
O2 C21 N3 120.9(4) . . ?
O2 C21 C22 122.0(4) . . ?
N3 C21 C22 117.1(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
C8' C9' C10' C11' -1.3(9) . . . . ?
C10' C9' C8' C13' 1.8(9) . . . . ?
C10' C9' C8' O1' 176.7(4) . . . . ?
C7' O1' C8' C9' 111.2(5) . . . . ?
C7' O1' C8' C13' -73.9(5) . . . . ?
C9' C8' C13' C12' -1.2(8) . . . . ?
O1' C8' C13' C12' -176.2(4) . . . . ?
C9' C8' C13' N3' -179.2(4) . . . . ?
O1' C8' C13' N3' 5.8(6) . . . . ?
C21' N3' C13' C8' -98.8(5) . . . . ?
C1' N3' C13' C8' 62.8(5) . . . . ?
C21' N3' C13' C12' 83.2(5) . . . . ?
C1' N3' C13' C12' -115.2(4) . . . . ?
C7' N1' C1' C2' -176.7(4) . . . . ?
C3' N1' C1' C2' 2.3(4) . . . . ?
C7' N1' C1' N3' 4.6(6) . . . . ?
C3' N1' C1' N3' -176.5(3) . . . . ?
C21' N3' C1' C2' -71.6(6) . . . . ?
C13' N3' C1' C2' 125.7(5) . . . . ?
C21' N3' C1' N1' 106.8(4) . . . . ?
C13' N3' C1' N1' -56.0(5) . . . . ?
N1' C1' C2' N2' -2.5(5) . . . . ?
N3' C1' C2' N2' 176.0(4) . . . . ?
N1' C1' C2' C14' 179.5(4) . . . . ?
N3' C1' C2' C14' -2.0(8) . . . . ?
C1' C2' C14' C19' -12.9(7) . . . . ?
N2' C2' C14' C19' 169.2(4) . . . . ?
C1' C2' C14' C15' 167.5(4) . . . . ?
N2' C2' C14' C15' -10.4(6) . . . . ?
C15' C14' C19' C18' -3.4(6) . . . . ?
C2' C14' C19' C18' 177.0(4) . . . . ?
C14' C19' C18' C17' -0.1(7) . . . . ?
C19' C18' C17' C16' 4.0(6) . . . . ?
C19' C18' C17' C20' -174.9(4) . . . . ?
C18' C17' C20' F3' -139.8(5) . . . . ?
C16' C17' C20' F3' 41.4(7) . . . . ?
C18' C17' C20' F2' -16.3(7) . . . . ?
C16' C17' C20' F2' 164.8(4) . . . . ?
C18' C17' C20' F1' 100.7(6) . . . . ?
C16' C17' C20' F1' -78.1(6) . . . . ?
C8' O1' C7' C6' -128.7(5) . . . . ?
C8' O1' C7' N1' 56.3(5) . . . . ?
C1' N1' C7' C6' -177.2(4) . . . . ?
C3' N1' C7' C6' 4.0(6) . . . . ?
C1' N1' C7' O1' -2.1(6) . . . . ?
C3' N1' C7' O1' 179.1(4) . . . . ?
C7' N1' C3' N2' 177.7(4) . . . . ?
C1' N1' C3' N2' -1.3(5) . . . . ?
C7' N1' C3' C4' -2.8(6) . . . . ?
C1' N1' C3' C4' 178.1(4) . . . . ?
N2' C3' C4' C5' 179.3(5) . . . . ?
N1' C3' C4' C5' 0.1(7) . . . . ?
C3' C4' C5' C6' 1.5(8) . . . . ?
O1' C7' C6' C5' -177.2(4) . . . . ?
N1' C7' C6' C5' -2.3(7) . . . . ?
C4' C5' C6' C7' -0.4(8) . . . . ?
N1' C3' N2' C2' -0.2(5) . . . . ?
C4' C3' N2' C2' -179.5(5) . . . . ?
C1' C2' N2' C3' 1.7(5) . . . . ?
C14' C2' N2' C3' 179.9(4) . . . . ?
C9' C10' C11' C12' 0.1(9) . . . . ?
C8' C13' C12' C11' 0.0(7) . . . . ?
N3' C13' C12' C11' 178.0(4) . . . . ?
C10' C11' C12' C13' 0.6(8) . . . . ?
C1' N3' C21' O2' 6.5(6) . . . . ?
C13' N3' C21' O2' 167.4(5) . . . . ?
C1' N3' C21' C22' -175.2(4) . . . . ?
C13' N3' C21' C22' -14.3(6) . . . . ?
C19' C14' C15' C16' 3.1(7) . . . . ?
C2' C14' C15' C16' -177.2(4) . . . . ?
C14' C15' C16' C17' 0.7(7) . . . . ?
C18' C17' C16' C15' -4.3(7) . . . . ?
C20' C17' C16' C15' 174.6(5) . . . . ?
C9 C10 C11 C12 1.5(8) . . . . ?
C10 C11 C12 C13 -2.7(8) . . . . ?
C11 C12 C13 C8 1.5(8) . . . . ?
C11 C12 C13 N3 177.3(4) . . . . ?
C21 N3 C13 C12 82.4(6) . . . . ?
C1 N3 C13 C12 -112.5(5) . . . . ?
C21 N3 C13 C8 -101.7(5) . . . . ?
C1 N3 C13 C8 63.4(5) . . . . ?
C3 N1 C1 C2 0.6(4) . . . . ?
C7 N1 C1 C2 -175.7(4) . . . . ?
C3 N1 C1 N3 -176.8(3) . . . . ?
C7 N1 C1 N3 6.9(6) . . . . ?
C21 N3 C1 C2 -69.9(6) . . . . ?
C13 N3 C1 C2 124.4(5) . . . . ?
C21 N3 C1 N1 106.6(4) . . . . ?
C13 N3 C1 N1 -59.2(5) . . . . ?
N1 C1 C2 N2 -1.9(4) . . . . ?
N3 C1 C2 N2 174.9(4) . . . . ?
N1 C1 C2 C14 179.4(4) . . . . ?
N3 C1 C2 C14 -3.8(7) . . . . ?
C3 N2 C2 C1 2.6(5) . . . . ?
C3 N2 C2 C14 -178.7(4) . . . . ?
C1 C2 C14 C15 168.3(4) . . . . ?
N2 C2 C14 C15 -10.3(6) . . . . ?
C1 C2 C14 C19 -11.7(7) . . . . ?
N2 C2 C14 C19 169.8(4) . . . . ?
C15 C14 C19 C18 -2.3(6) . . . . ?
C2 C14 C19 C18 177.7(4) . . . . ?
C14 C19 C18 C17 0.6(7) . . . . ?
C19 C18 C17 C16 0.7(6) . . . . ?
C19 C18 C17 C20 -174.5(4) . . . . ?
C16 C17 C20 F3 163.6(4) . . . . ?
C18 C17 C20 F3 -21.2(7) . . . . ?
C16 C17 C20 F2 41.2(7) . . . . ?
C18 C17 C20 F2 -143.6(5) . . . . ?
C16 C17 C20 F1 -76.4(6) . . . . ?
C18 C17 C20 F1 98.8(6) . . . . ?
C2 N2 C3 N1 -2.2(5) . . . . ?
C2 N2 C3 C4 -178.9(5) . . . . ?
C7 N1 C3 N2 177.8(4) . . . . ?
C1 N1 C3 N2 1.0(5) . . . . ?
C7 N1 C3 C4 -5.1(6) . . . . ?
C1 N1 C3 C4 178.2(4) . . . . ?
C8 O1 C7 C6 -128.8(5) . . . . ?
C8 O1 C7 N1 53.8(5) . . . . ?
C3 N1 C7 C6 4.3(6) . . . . ?
C1 N1 C7 C6 -179.8(4) . . . . ?
C3 N1 C7 O1 -178.2(3) . . . . ?
C1 N1 C7 O1 -2.4(6) . . . . ?
C12 C13 C8 C9 0.9(7) . . . . ?
N3 C13 C8 C9 -175.3(4) . . . . ?
C12 C13 C8 O1 -177.8(4) . . . . ?
N3 C13 C8 O1 6.1(6) . . . . ?
C7 O1 C8 C9 109.0(5) . . . . ?
C7 O1 C8 C13 -72.3(5) . . . . ?
C11 C10 C9 C8 0.7(9) . . . . ?
C13 C8 C9 C10 -1.9(8) . . . . ?
O1 C8 C9 C10 176.8(4) . . . . ?
O1 C7 C6 C5 -177.8(4) . . . . ?
N1 C7 C6 C5 -0.5(7) . . . . ?
C7 C6 C5 C4 -2.6(8) . . . . ?
C6 C5 C4 C3 1.8(8) . . . . ?
N2 C3 C4 C5 178.5(5) . . . . ?
N1 C3 C4 C5 1.9(7) . . . . ?
C19 C14 C15 C16 2.7(6) . . . . ?
C2 C14 C15 C16 -177.2(4) . . . . ?
C18 C17 C16 C15 -0.3(7) . . . . ?
C20 C17 C16 C15 174.9(4) . . . . ?
C14 C15 C16 C17 -1.5(7) . . . . ?
C1 N3 C21 O2 7.7(6) . . . . ?
C13 N3 C21 O2 172.3(5) . . . . ?
C1 N3 C21 C22 -174.4(4) . . . . ?
C13 N3 C21 C22 -9.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 1007733'
#######################################################################
#
#                 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_mo_2013421_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N3 O2'
_chemical_formula_weight         341.36

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   8.4445(6)
_cell_length_b                   19.2694(14)
_cell_length_c                   20.5785(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3348.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21740
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2933
_reflns_number_gt                2391
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0516P)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         2933
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.570
_refine_ls_restrained_S_all      1.570
_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
O1 O 0.08738(15) 0.09371(6) 0.97500(6) 0.0614(4) Uani 1 1 d . . .
O2 O 0.07908(12) 0.23079(6) 0.83056(6) 0.0522(3) Uani 1 1 d . . .
N1 N 0.23541(14) 0.11899(7) 0.88737(6) 0.0396(3) Uani 1 1 d . . .
N2 N 0.22748(13) 0.14812(7) 0.77283(6) 0.0402(3) Uani 1 1 d . . .
N3 N 0.38539(15) 0.06747(8) 0.72833(7) 0.0476(4) Uani 1 1 d . . .
C1 C 0.3096(2) 0.32231(10) 0.95362(11) 0.0653(5) Uani 1 1 d . . .
H1 H 0.3265 0.3675 0.9679 0.078 Uiso 1 1 calc R . .
C2 C 0.3813(2) 0.26797(10) 0.98521(9) 0.0594(5) Uani 1 1 d . . .
H15 H 0.4462 0.2766 1.0208 0.071 Uiso 1 1 calc R . .
C3 C 0.3578(2) 0.20066(9) 0.96449(8) 0.0487(4) Uani 1 1 d . . .
H3 H 0.4067 0.1640 0.9860 0.058 Uiso 1 1 calc R . .
C4 C 0.26122(17) 0.18788(8) 0.91153(8) 0.0402(4) Uani 1 1 d . . .
C5 C 0.28338(17) 0.10670(8) 0.82304(7) 0.0381(4) Uani 1 1 d . . .
C9 C 0.38304(17) 0.05902(8) 0.79448(8) 0.0411(4) Uani 1 1 d . . .
C16 C 0.48255(17) 0.00563(8) 0.82528(9) 0.0441(4) Uani 1 1 d . . .
C21 C 0.5340(2) -0.05097(9) 0.78922(10) 0.0566(5) Uani 1 1 d . . .
H10 H 0.4997 -0.0565 0.7466 0.068 Uiso 1 1 calc R . .
C20 C 0.6360(2) -0.09922(10) 0.81636(13) 0.0707(6) Uani 1 1 d . . .
H9 H 0.6690 -0.1372 0.7920 0.085 Uiso 1 1 calc R . .
C19 C 0.6887(2) -0.09128(11) 0.87902(13) 0.0728(6) Uani 1 1 d . . .
H2 H 0.7587 -0.1234 0.8968 0.087 Uiso 1 1 calc R . .
C14 C 0.13730(16) 0.07453(8) 0.92287(8) 0.0397(4) Uani 1 1 d . . .
C15 C 0.1020(2) 0.00526(8) 0.89475(8) 0.0500(5) Uani 1 1 d . . .
H4 H 0.0391 -0.0210 0.9248 0.075 Uiso 1 1 calc R . .
H5 H 0.1994 -0.0189 0.8865 0.075 Uiso 1 1 calc R . .
H6 H 0.0448 0.0109 0.8548 0.075 Uiso 1 1 calc R . .
C10 C 0.29272(19) 0.12123(9) 0.71570(8) 0.0447(4) Uani 1 1 d . . .
C18 C 0.6383(2) -0.03627(12) 0.91516(11) 0.0693(6) Uani 1 1 d . . .
H7 H 0.6727 -0.0312 0.9578 0.083 Uiso 1 1 calc R . .
C17 C 0.5357(2) 0.01220(10) 0.88854(9) 0.0561(5) Uani 1 1 d . . .
H8 H 0.5022 0.0496 0.9136 0.067 Uiso 1 1 calc R . .
C11 C 0.2546(2) 0.15421(11) 0.65651(9) 0.0577(5) Uani 1 1 d . . .
H11 H 0.2951 0.1374 0.6175 0.069 Uiso 1 1 calc R . .
C12 C 0.1590(2) 0.21037(11) 0.65684(10) 0.0645(6) Uani 1 1 d . . .
H12 H 0.1314 0.2313 0.6177 0.077 Uiso 1 1 calc R . .
C13 C 0.1004(2) 0.23782(10) 0.71561(10) 0.0572(5) Uani 1 1 d . . .
H14 H 0.0372 0.2773 0.7151 0.069 Uiso 1 1 calc R . .
C6 C 0.13574(17) 0.20696(9) 0.77255(9) 0.0452(4) Uani 1 1 d . . .
C7 C 0.18862(18) 0.24321(8) 0.88060(8) 0.0429(4) Uani 1 1 d . . .
C8 C 0.2127(2) 0.31029(9) 0.90093(10) 0.0577(5) Uani 1 1 d . . .
H13 H 0.1642 0.3471 0.8794 0.069 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
O1 C14 1.2105(19) . ?
O2 C6 1.366(2) . ?
O2 C7 1.4048(19) . ?
N1 C14 1.3980(19) . ?
N1 C5 1.404(2) . ?
N1 C4 1.434(2) . ?
N2 C6 1.373(2) . ?
N2 C5 1.3883(19) . ?
N2 C10 1.398(2) . ?
N3 C10 1.324(2) . ?
N3 C9 1.371(2) . ?
C1 C2 1.373(3) . ?
C1 C8 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H15 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C7 1.385(2) . ?
C5 C9 1.378(2) . ?
C9 C16 1.472(2) . ?
C16 C17 1.383(2) . ?
C16 C21 1.389(2) . ?
C21 C20 1.385(3) . ?
C21 H10 0.9300 . ?
C20 C19 1.373(3) . ?
C20 H9 0.9300 . ?
C19 C18 1.363(3) . ?
C19 H2 0.9300 . ?
C14 C15 1.485(2) . ?
C15 H4 0.9600 . ?
C15 H5 0.9600 . ?
C15 H6 0.9600 . ?
C10 C11 1.411(2) . ?
C18 C17 1.386(3) . ?
C18 H7 0.9300 . ?
C17 H8 0.9300 . ?
C11 C12 1.350(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.410(3) . ?
C12 H12 0.9300 . ?
C13 C6 1.347(2) . ?
C13 H14 0.9300 . ?
C7 C8 1.374(2) . ?
C8 H13 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
C6 O2 C7 117.86(12) . . ?
C14 N1 C5 124.07(13) . . ?
C14 N1 C4 118.43(13) . . ?
C5 N1 C4 116.04(12) . . ?
C6 N2 C5 132.04(14) . . ?
C6 N2 C10 121.65(13) . . ?
C5 N2 C10 106.19(13) . . ?
C10 N3 C9 106.22(13) . . ?
C2 C1 C8 120.41(18) . . ?
C2 C1 H1 119.8 . . ?
C8 C1 H1 119.8 . . ?
C1 C2 C3 120.46(17) . . ?
C1 C2 H15 119.8 . . ?
C3 C2 H15 119.8 . . ?
C2 C3 C4 119.71(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C4 C3 119.09(15) . . ?
C7 C4 N1 119.08(14) . . ?
C3 C4 N1 121.83(14) . . ?
C9 C5 N2 105.88(13) . . ?
C9 C5 N1 133.69(14) . . ?
N2 C5 N1 120.42(14) . . ?
N3 C9 C5 110.68(14) . . ?
N3 C9 C16 120.15(14) . . ?
C5 C9 C16 129.14(15) . . ?
C17 C16 C21 118.25(16) . . ?
C17 C16 C9 121.78(15) . . ?
C21 C16 C9 119.83(17) . . ?
C20 C21 C16 120.4(2) . . ?
C20 C21 H10 119.8 . . ?
C16 C21 H10 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H9 119.8 . . ?
C21 C20 H9 119.8 . . ?
C18 C19 C20 119.86(19) . . ?
C18 C19 H2 120.1 . . ?
C20 C19 H2 120.1 . . ?
O1 C14 N1 118.84(15) . . ?
O1 C14 C15 123.37(15) . . ?
N1 C14 C15 117.78(14) . . ?
C14 C15 H4 109.5 . . ?
C14 C15 H5 109.5 . . ?
H4 C15 H5 109.5 . . ?
C14 C15 H6 109.5 . . ?
H4 C15 H6 109.5 . . ?
H5 C15 H6 109.5 . . ?
N3 C10 N2 110.96(14) . . ?
N3 C10 C11 131.05(17) . . ?
N2 C10 C11 117.98(17) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H7 119.9 . . ?
C17 C18 H7 119.9 . . ?
C18 C17 C16 120.86(18) . . ?
C18 C17 H8 119.6 . . ?
C16 C17 H8 119.6 . . ?
C12 C11 C10 119.54(18) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.00(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C6 C13 C12 120.17(19) . . ?
C6 C13 H14 119.9 . . ?
C12 C13 H14 119.9 . . ?
C13 C6 O2 122.28(17) . . ?
C13 C6 N2 119.55(17) . . ?
O2 C6 N2 118.14(14) . . ?
C8 C7 C4 121.26(16) . . ?
C8 C7 O2 118.74(14) . . ?
C4 C7 O2 119.83(14) . . ?
C7 C8 C1 119.06(17) . . ?
C7 C8 H13 120.5 . . ?
C1 C8 H13 120.5 . . ?

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
C8 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C7 -0.6(2) . . . . ?
C2 C3 C4 N1 178.81(16) . . . . ?
C14 N1 C4 C7 -106.49(16) . . . . ?
C5 N1 C4 C7 60.30(19) . . . . ?
C14 N1 C4 C3 74.13(19) . . . . ?
C5 N1 C4 C3 -119.07(16) . . . . ?
C6 N2 C5 C9 -173.87(14) . . . . ?
C10 N2 C5 C9 2.15(15) . . . . ?
C6 N2 C5 N1 5.8(2) . . . . ?
C10 N2 C5 N1 -178.16(12) . . . . ?
C14 N1 C5 C9 -69.4(2) . . . . ?
C4 N1 C5 C9 124.63(17) . . . . ?
C14 N1 C5 N2 111.01(16) . . . . ?
C4 N1 C5 N2 -54.96(19) . . . . ?
C10 N3 C9 C5 2.05(17) . . . . ?
C10 N3 C9 C16 -176.33(13) . . . . ?
N2 C5 C9 N3 -2.65(16) . . . . ?
N1 C5 C9 N3 177.72(15) . . . . ?
N2 C5 C9 C16 175.55(14) . . . . ?
N1 C5 C9 C16 -4.1(3) . . . . ?
N3 C9 C16 C17 152.93(16) . . . . ?
C5 C9 C16 C17 -25.1(2) . . . . ?
N3 C9 C16 C21 -22.8(2) . . . . ?
C5 C9 C16 C21 159.15(16) . . . . ?
C17 C16 C21 C20 -0.1(2) . . . . ?
C9 C16 C21 C20 175.81(15) . . . . ?
C16 C21 C20 C19 -0.7(3) . . . . ?
C21 C20 C19 C18 1.2(3) . . . . ?
C5 N1 C14 O1 -171.19(14) . . . . ?
C4 N1 C14 O1 -5.5(2) . . . . ?
C5 N1 C14 C15 9.8(2) . . . . ?
C4 N1 C14 C15 175.50(13) . . . . ?
C9 N3 C10 N2 -0.62(16) . . . . ?
C9 N3 C10 C11 178.15(16) . . . . ?
C6 N2 C10 N3 175.55(12) . . . . ?
C5 N2 C10 N3 -0.98(16) . . . . ?
C6 N2 C10 C11 -3.4(2) . . . . ?
C5 N2 C10 C11 -179.93(13) . . . . ?
C20 C19 C18 C17 -0.9(3) . . . . ?
C19 C18 C17 C16 0.2(3) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C9 C16 C17 C18 -175.49(15) . . . . ?
N3 C10 C11 C12 -178.03(16) . . . . ?
N2 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C6 -1.9(3) . . . . ?
C12 C13 C6 O2 -178.63(14) . . . . ?
C12 C13 C6 N2 -0.8(2) . . . . ?
C7 O2 C6 C13 -127.84(16) . . . . ?
C7 O2 C6 N2 54.34(18) . . . . ?
C5 N2 C6 C13 179.00(14) . . . . ?
C10 N2 C6 C13 3.5(2) . . . . ?
C5 N2 C6 O2 -3.1(2) . . . . ?
C10 N2 C6 O2 -178.63(12) . . . . ?
C3 C4 C7 C8 1.0(2) . . . . ?
N1 C4 C7 C8 -178.42(15) . . . . ?
C3 C4 C7 O2 -174.26(14) . . . . ?
N1 C4 C7 O2 6.4(2) . . . . ?
C6 O2 C7 C8 113.26(18) . . . . ?
C6 O2 C7 C4 -71.39(19) . . . . ?
C4 C7 C8 C1 -0.8(3) . . . . ?
O2 C7 C8 C1 174.51(17) . . . . ?
C2 C1 C8 C7 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1007734'
