##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2008-08-29
_journal_date_accepted     2008-09-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     12
_journal_page_first     o2425
_journal_page_last     o2425
_journal_paper_category     QO
_journal_coeditor_code     HK2521
_publ_contact_author_name     'Hao Xu'
_publ_contact_author_address
;
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     cnjyc@sohu.com
_publ_contact_author_fax     '86 25 83433454'
_publ_contact_author_phone     '86 25 83433454'
_publ_section_title
;\
1-(4,5-Dinitro-10-azatricyclo[6.3.1.0^2,7^]dodeca-2,4,6-trien-10-yl)-2,2,2-\
trifluoroethanone
;
loop_
    _publ_author_name
    _publ_author_address
    'Hao Xu'
;
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Ji-Cai Quan'
;
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Jian Xu'
;
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Jing Chen'
;
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
    'Jin-Tang Wang'
;
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;\
1-(4,5-Dinitro-10-azatricyclo[6.3.1.0^2,7^]dodeca-2,4,6-trien-10-yl)-2,2,2-\
trifluoroethanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 F3 N3 O5'
_chemical_formula_sum     'C13 H10 F3 N3 O5'
_chemical_formula_iupac     'C13 H10 F3 N3 O5'
_chemical_formula_weight     345.24
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     9.6400(19)
_cell_length_b     7.7430(15)
_cell_length_c     18.687(4)
_cell_angle_alpha     90.00
_cell_angle_beta     96.98(3)
_cell_angle_gamma     90.00
_cell_volume     1384.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     13
_cell_measurement_temperature     294(2)
_exptl_crystal_description     red
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.656
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.154
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9554
_exptl_absorpt_correction_T_max     0.9848
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'ω/2θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2673
_diffrn_reflns_av_R_equivalents     0.0520
_diffrn_reflns_av_sigmaI/netI     0.0382
_diffrn_reflns_theta_min     2.13
_diffrn_reflns_theta_max     25.28
_diffrn_reflns_theta_full     25.28
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0
_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 > σ(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.
;
_reflns_number_total     2513
_reflns_number_gt     1592
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1051
_refine_ls_R_factor_gt     0.0609
_refine_ls_wR_factor_gt     0.1365
_refine_ls_wR_factor_ref     0.1826
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     2513
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'calc w = 1/[σ²(Fo²)+(0.05P)²+4P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.329
_refine_diff_density_min     -0.348
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    F F1 0.3302(4) 0.7803(5) 0.23330(19) 0.1036(13) Uani d . 1 . .
    F F2 0.1596(3) 0.6268(5) 0.25814(17) 0.0907(12) Uani d . 1 . .
    F F3 0.3030(3) 0.5239(4) 0.19179(13) 0.0702(9) Uani d . 1 . .
    O O1 0.4775(4) 0.6527(5) 0.34298(19) 0.0681(10) Uani d . 1 . .
    O O2 0.1222(4) 0.4522(5) 0.6478(2) 0.0812(12) Uani d . 1 . .
    O O3 0.0247(4) 0.2030(5) 0.65267(18) 0.0733(11) Uani d . 1 . .
    O O4 -0.2298(3) 0.1740(6) 0.4660(2) 0.0772(12) Uani d . 1 . .
    O O5 -0.1736(4) 0.3629(5) 0.5498(2) 0.0749(11) Uani d . 1 . .
    N N1 0.3630(3) 0.3999(5) 0.34108(16) 0.0398(8) Uani d . 1 . .
    N N2 0.0824(4) 0.3155(6) 0.6213(2) 0.0512(10) Uani d . 1 . .
    N N3 -0.1427(4) 0.2615(5) 0.5031(2) 0.0532(10) Uani d . 1 . .
    C C1 0.2916(5) 0.6217(7) 0.2505(2) 0.0557(12) Uani d . 1 . .
    C C2 0.3865(4) 0.5564(6) 0.3165(2) 0.0446(10) Uani d . 1 . .
    C C3 0.4621(4) 0.3471(7) 0.4042(2) 0.0486(11) Uani d . 1 . .
    H H3A 0.4714 0.4406 0.4390 0.058 Uiso calc R 1 . .
    H H3B 0.5532 0.3272 0.3887 0.058 Uiso calc R 1 . .
    C C4 0.4159(4) 0.1853(6) 0.4403(2) 0.0442(10) Uani d . 1 . .
    H H4A 0.4872 0.1443 0.4784 0.053 Uiso calc R 1 . .
    C C5 0.3737(5) 0.0456(7) 0.3846(3) 0.0569(12) Uani d . 1 . .
    H H5A 0.3600 -0.0649 0.4072 0.068 Uiso calc R 1 . .
    H H5B 0.4419 0.0331 0.3509 0.068 Uiso calc R 1 . .
    C C6 0.2364(4) 0.1203(6) 0.3485(2) 0.0476(11) Uani d . 1 . .
    H H6A 0.1799 0.0323 0.3208 0.057 Uiso calc R 1 . .
    C C7 0.2679(5) 0.2734(7) 0.3008(2) 0.0524(12) Uani d . 1 . .
    H H7A 0.3105 0.2310 0.2598 0.063 Uiso calc R 1 . .
    H H7B 0.1811 0.3304 0.2827 0.063 Uiso calc R 1 . .
    C C8 0.2766(4) 0.2163(5) 0.4683(2) 0.0393(9) Uani d . 1 . .
    C C9 0.2468(4) 0.2693(5) 0.5352(2) 0.0398(10) Uani d . 1 . .
    H H9A 0.3181 0.2968 0.5715 0.048 Uiso calc R 1 . .
    C C10 0.1095(4) 0.2805(5) 0.5470(2) 0.0391(9) Uani d . 1 . .
    C C11 0.0006(4) 0.2439(5) 0.4922(2) 0.0381(9) Uani d . 1 . .
    C C12 0.0337(4) 0.1944(6) 0.4239(2) 0.0417(10) Uani d . 1 . .
    H H12A -0.0365 0.1737 0.3861 0.050 Uiso calc R 1 . .
    C C13 0.1695(4) 0.1778(5) 0.4143(2) 0.0418(10) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    F1 0.150(3) 0.070(2) 0.083(2) 0.000(2) -0.017(2) 0.0327(19)
    F2 0.0614(19) 0.134(3) 0.076(2) 0.042(2) 0.0060(15) 0.020(2)
    F3 0.0736(19) 0.102(2) 0.0356(14) 0.0003(17) 0.0089(12) -0.0006(15)
    O1 0.072(2) 0.053(2) 0.074(2) -0.0176(19) -0.0145(18) 0.0037(18)
    O2 0.100(3) 0.075(3) 0.068(2) -0.011(2) 0.005(2) -0.030(2)
    O3 0.095(3) 0.076(3) 0.056(2) -0.005(2) 0.0403(19) 0.009(2)
    O4 0.0338(17) 0.108(3) 0.087(3) -0.016(2) -0.0066(17) -0.001(2)
    O5 0.054(2) 0.078(3) 0.098(3) 0.0127(19) 0.029(2) -0.007(2)
    N1 0.0348(17) 0.053(2) 0.0291(16) -0.0060(16) -0.0073(13) -0.0019(15)
    N2 0.050(2) 0.056(3) 0.045(2) 0.007(2) -0.0007(17) -0.003(2)
    N3 0.043(2) 0.055(3) 0.060(2) 0.0015(19) 0.0023(19) 0.018(2)
    C1 0.054(3) 0.067(3) 0.046(3) 0.004(3) 0.008(2) 0.014(2)
    C2 0.045(2) 0.051(3) 0.039(2) 0.002(2) 0.0101(18) 0.007(2)
    C3 0.033(2) 0.069(3) 0.042(2) -0.007(2) -0.0008(17) 0.009(2)
    C4 0.033(2) 0.058(3) 0.042(2) 0.007(2) 0.0055(17) 0.010(2)
    C5 0.061(3) 0.052(3) 0.063(3) 0.004(2) 0.027(2) 0.003(2)
    C6 0.049(2) 0.053(3) 0.041(2) -0.013(2) 0.0063(19) -0.007(2)
    C7 0.053(3) 0.071(3) 0.033(2) -0.016(2) 0.0025(19) -0.009(2)
    C8 0.041(2) 0.038(2) 0.037(2) 0.0014(18) -0.0044(17) 0.0045(18)
    C9 0.036(2) 0.045(2) 0.034(2) -0.0047(19) -0.0095(16) 0.0003(18)
    C10 0.041(2) 0.039(2) 0.035(2) -0.0009(18) -0.0026(17) 0.0051(18)
    C11 0.0318(19) 0.038(2) 0.042(2) 0.0017(17) -0.0023(16) 0.0104(18)
    C12 0.038(2) 0.045(3) 0.039(2) -0.0061(19) -0.0050(17) 0.0008(19)
    C13 0.047(2) 0.039(2) 0.038(2) -0.0066(19) -0.0014(18) 0.0015(19)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s.
planes) are estimated using the full covariance matrix. The cell e.s.d.'s
are taken into account individually in the estimation of e.s.d.'s in
distances, angles and torsion angles; correlations between e.s.d.'s in
cell parameters are only used when they are defined by crystal symmetry.
An approximate (isotropic) treatment of cell e.s.d.'s is used for
estimating e.s.d.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    F1 C1 . 1.334(6) ?
    F2 C1 . 1.298(5) ?
    F3 C1 . 1.348(6) ?
    O1 C2 . 1.210(5) ?
    O2 N2 . 1.211(5) ?
    O3 N2 . 1.221(5) ?
    O4 N3 . 1.227(5) ?
    O5 N3 . 1.236(5) ?
    N1 C2 . 1.325(6) ?
    N1 C3 . 1.482(5) ?
    N1 C7 . 1.483(5) ?
    N2 C10 . 1.470(5) ?
    N3 C11 . 1.427(5) ?
    C1 C2 . 1.530(6) ?
    C3 C4 . 1.516(6) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C8 . 1.519(5) ?
    C4 C5 . 1.521(6) ?
    C4 H4A . 0.9800 ?
    C5 C6 . 1.525(6) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C13 . 1.523(6) ?
    C6 C7 . 1.535(6) ?
    C6 H6A . 0.9800 ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.379(6) ?
    C8 C13 . 1.385(5) ?
    C9 C10 . 1.370(5) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.403(5) ?
    C11 C12 . 1.407(6) ?
    C12 C13 . 1.349(6) ?
    C12 H12A . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 N1 C3 . . 114.0(3) ?
    C2 N1 C7 . . 123.4(3) ?
    C3 N1 C7 . . 121.4(4) ?
    O2 N2 O3 . . 124.6(4) ?
    O2 N2 C10 . . 117.6(4) ?
    O3 N2 C10 . . 117.8(4) ?
    O4 N3 O5 . . 122.9(4) ?
    O4 N3 C11 . . 118.3(4) ?
    O5 N3 C11 . . 118.8(4) ?
    F2 C1 F1 . . 107.7(4) ?
    F2 C1 F3 . . 106.5(4) ?
    F1 C1 F3 . . 105.6(4) ?
    F2 C1 C2 . . 114.8(4) ?
    F1 C1 C2 . . 110.0(4) ?
    F3 C1 C2 . . 111.8(4) ?
    O1 C2 N1 . . 124.6(4) ?
    O1 C2 C1 . . 117.3(4) ?
    N1 C2 C1 . . 118.1(4) ?
    N1 C3 C4 . . 112.7(3) ?
    N1 C3 H3A . . 109.0 ?
    C4 C3 H3A . . 109.0 ?
    N1 C3 H3B . . 109.0 ?
    C4 C3 H3B . . 109.0 ?
    H3A C3 H3B . . 107.8 ?
    C3 C4 C8 . . 110.0(4) ?
    C3 C4 C5 . . 110.6(3) ?
    C8 C4 C5 . . 100.0(3) ?
    C3 C4 H4A . . 111.9 ?
    C8 C4 H4A . . 111.9 ?
    C5 C4 H4A . . 111.9 ?
    C4 C5 C6 . . 100.3(4) ?
    C4 C5 H5A . . 111.7 ?
    C6 C5 H5A . . 111.7 ?
    C4 C5 H5B . . 111.7 ?
    C6 C5 H5B . . 111.7 ?
    H5A C5 H5B . . 109.5 ?
    C13 C6 C5 . . 100.5(3) ?
    C13 C6 C7 . . 112.1(4) ?
    C5 C6 C7 . . 109.1(4) ?
    C13 C6 H6A . . 111.5 ?
    C5 C6 H6A . . 111.5 ?
    C7 C6 H6A . . 111.5 ?
    N1 C7 C6 . . 111.6(3) ?
    N1 C7 H7A . . 109.3 ?
    C6 C7 H7A . . 109.3 ?
    N1 C7 H7B . . 109.3 ?
    C6 C7 H7B . . 109.3 ?
    H7A C7 H7B . . 108.0 ?
    C9 C8 C13 . . 120.4(4) ?
    C9 C8 C4 . . 130.6(4) ?
    C13 C8 C4 . . 109.1(4) ?
    C10 C9 C8 . . 118.4(3) ?
    C10 C9 H9A . . 120.8 ?
    C8 C9 H9A . . 120.8 ?
    C9 C10 C11 . . 121.5(4) ?
    C9 C10 N2 . . 116.7(3) ?
    C11 C10 N2 . . 121.6(4) ?
    C10 C11 C12 . . 119.0(4) ?
    C10 C11 N3 . . 121.9(4) ?
    C12 C11 N3 . . 119.0(4) ?
    C13 C12 C11 . . 118.4(4) ?
    C13 C12 H12A . . 120.8 ?
    C11 C12 H12A . . 120.8 ?
    C12 C13 C8 . . 122.2(4) ?
    C12 C13 C6 . . 130.3(4) ?
    C8 C13 C6 . . 107.5(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N1 C2 O1 . . . . -1.8(6) ?
    C7 N1 C2 O1 . . . . -169.0(4) ?
    C3 N1 C2 C1 . . . . 178.8(4) ?
    C7 N1 C2 C1 . . . . 11.6(6) ?
    F2 C1 C2 O1 . . . . -121.0(5) ?
    F1 C1 C2 O1 . . . . 0.6(6) ?
    F3 C1 C2 O1 . . . . 117.5(5) ?
    F2 C1 C2 N1 . . . . 58.5(6) ?
    F1 C1 C2 N1 . . . . -179.9(4) ?
    F3 C1 C2 N1 . . . . -63.0(5) ?
    C2 N1 C3 C4 . . . . 168.3(4) ?
    C7 N1 C3 C4 . . . . -24.2(5) ?
    N1 C3 C4 C8 . . . . -61.6(5) ?
    N1 C3 C4 C5 . . . . 48.0(5) ?
    C3 C4 C5 C6 . . . . -71.8(4) ?
    C8 C4 C5 C6 . . . . 44.2(4) ?
    C4 C5 C6 C13 . . . . -44.6(4) ?
    C4 C5 C6 C7 . . . . 73.4(4) ?
    C2 N1 C7 C6 . . . . -167.6(4) ?
    C3 N1 C7 C6 . . . . 26.0(5) ?
    C13 C6 C7 N1 . . . . 58.8(5) ?
    C5 C6 C7 N1 . . . . -51.7(5) ?
    C3 C4 C8 C9 . . . . -93.2(5) ?
    C5 C4 C8 C9 . . . . 150.4(5) ?
    C3 C4 C8 C13 . . . . 88.4(4) ?
    C5 C4 C8 C13 . . . . -28.0(4) ?
    C13 C8 C9 C10 . . . . 0.8(6) ?
    C4 C8 C9 C10 . . . . -177.4(4) ?
    C8 C9 C10 C11 . . . . -1.7(6) ?
    C8 C9 C10 N2 . . . . 172.3(4) ?
    O2 N2 C10 C9 . . . . 63.6(5) ?
    O3 N2 C10 C9 . . . . -114.5(5) ?
    O2 N2 C10 C11 . . . . -122.3(5) ?
    O3 N2 C10 C11 . . . . 59.5(6) ?
    C9 C10 C11 C12 . . . . 0.1(6) ?
    N2 C10 C11 C12 . . . . -173.6(4) ?
    C9 C10 C11 N3 . . . . -177.6(4) ?
    N2 C10 C11 N3 . . . . 8.7(6) ?
    O4 N3 C11 C10 . . . . -154.4(4) ?
    O5 N3 C11 C10 . . . . 25.1(6) ?
    O4 N3 C11 C12 . . . . 28.0(6) ?
    O5 N3 C11 C12 . . . . -152.6(4) ?
    C10 C11 C12 C13 . . . . 2.4(6) ?
    N3 C11 C12 C13 . . . . -179.8(4) ?
    C11 C12 C13 C8 . . . . -3.4(6) ?
    C11 C12 C13 C6 . . . . 177.3(4) ?
    C9 C8 C13 C12 . . . . 1.8(7) ?
    C4 C8 C13 C12 . . . . -179.6(4) ?
    C9 C8 C13 C6 . . . . -178.8(4) ?
    C4 C8 C13 C6 . . . . -0.2(5) ?
    C5 C6 C13 C12 . . . . -152.3(5) ?
    C7 C6 C13 C12 . . . . 91.9(5) ?
    C5 C6 C13 C8 . . . . 28.3(5) ?
    C7 C6 C13 C8 . . . . -87.5(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C7 H7B F2 . 0.97 2.34 3.002(6) 124.00
    C9 H9A O1 3_666 0.93 2.41 3.338(5) 173.00
