##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-11-28
_journal_date_accepted     2007-12-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o69
_journal_page_last     o72
_journal_paper_category     FO
_journal_coeditor_code     AV3132
_publ_contact_author_name     'Cao, Li-Ping'
_publ_contact_author_address
;
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
_publ_contact_author_email     'chlpcao@mails.ccnu.edu.cn'
_publ_contact_author_fax     '86 27 67867955'
_publ_contact_author_phone     '86 27 67867129'
_publ_section_title
;
Two-dimensional hydrogen-bonded networks in two novel glycoluril derivatives
;
loop_
    _publ_author_name
    _publ_author_address
    'Li-Ping Cao'
;
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Xiang-Gao Meng'
;
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Meng Gao'
;
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Neng-Fang She'
;
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'An-Xin Wu'
;
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6-ethyl-1,4-dioxo-2,2a,3,4,6,7-hexahydro-1H,5H-2,3,4a,6,7a-
pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H21 N5 O6'
_chemical_formula_sum     'C14 H21 N5 O6'
_chemical_formula_iupac     'C14 H21 N5 O6'
_chemical_formula_weight     355.36
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     23.898(2)
_cell_length_b     10.4791(9)
_cell_length_c     15.9302(13)
_cell_angle_alpha     90.00
_cell_angle_beta     119.4120(10)
_cell_angle_gamma     90.00
_cell_volume     3475.2(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2051
_cell_measurement_theta_min     2.18
_cell_measurement_theta_max     22.26
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1504
_exptl_absorpt_coefficient_mu     0.108
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9788
_exptl_absorpt_correction_T_max     0.9893
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine focus sealed Siemens Mo tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     '0.3° wide ω exposures'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10973
_diffrn_reflns_av_R_equivalents     0.0458
_diffrn_reflns_av_sigmaI/netI     0.0474
_diffrn_reflns_theta_min     2.18
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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.
;
_reflns_number_total     3061
_reflns_number_gt     2206
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1003
_refine_ls_R_factor_gt     0.0689
_refine_ls_wR_factor_gt     0.1579
_refine_ls_wR_factor_ref     0.1723
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_restrained_S_all     1.069
_refine_ls_number_reflns     3061
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0728P)²+4.4873P] 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     0.220
_refine_diff_density_min     -0.405
_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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'PLATON (Spek, 2003)'
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
    C C1 0.17081(14) 0.3335(3) 0.2399(2) 0.0357(7) Uani d . 1 . .
    C C2 0.16144(14) -0.0151(3) 0.2027(2) 0.0417(8) Uani d . 1 . .
    C C3 0.17397(14) 0.1757(3) 0.1383(2) 0.0369(7) Uani d . 1 . .
    C C4 0.17494(15) 0.2013(3) 0.0443(2) 0.0450(8) Uani d . 1 A .
    C C5 0.1455(3) 0.3511(6) -0.0811(4) 0.1038(18) Uani d . 1 A 1
    H H5A 0.1715 0.4275 -0.0673 0.125 Uiso calc R 1 A 1
    H H5B 0.1643 0.2854 -0.1022 0.125 Uiso calc R 1 A 1
    C C6 0.0812(4) 0.3775(7) -0.1567(5) 0.157(3) Uani d . 1 A 1
    H H6A 0.0558 0.3013 -0.1716 0.235 Uiso calc R 1 A 1
    H H6B 0.0823 0.4061 -0.2131 0.235 Uiso calc R 1 A 1
    H H6C 0.0626 0.4427 -0.1358 0.235 Uiso calc R 1 A 1
    C C7 0.10693(13) 0.1752(2) 0.1334(2) 0.0352(7) Uani d . 1 . .
    C C8 0.05016(15) 0.1789(3) 0.0301(2) 0.0432(8) Uani d . 1 . .
    C C9 -0.04711(19) 0.2766(4) -0.0793(3) 0.0722(12) Uani d . 1 . .
    H H9A -0.0754 0.2055 -0.0879 0.087 Uiso calc R 1 . .
    H H9B -0.0341 0.2708 -0.1281 0.087 Uiso calc R 1 . .
    C C10 -0.0806(3) 0.3966(5) -0.0894(4) 0.1050(17) Uani d . 1 . .
    H H10A -0.0877 0.4077 -0.0355 0.158 Uiso calc R 1 . .
    H H10B -0.1212 0.3954 -0.1480 0.158 Uiso calc R 1 . .
    H H10C -0.0551 0.4660 -0.0915 0.158 Uiso calc R 1 . .
    C C11 0.07313(14) 0.2671(3) 0.2454(2) 0.0414(8) Uani d . 1 . .
    H H11A 0.0853 0.3351 0.2925 0.050 Uiso calc R 1 . .
    H H11B 0.0278 0.2771 0.1994 0.050 Uiso calc R 1 . .
    C C12 0.06719(16) 0.0436(3) 0.2241(3) 0.0485(8) Uani d . 1 . .
    H H12A 0.0219 0.0485 0.1766 0.058 Uiso calc R 1 . .
    H H12B 0.0748 -0.0383 0.2564 0.058 Uiso calc R 1 . .
    C C13 0.14668(17) 0.1292(4) 0.3792(3) 0.0594(10) Uani d . 1 . .
    H H13A 0.1791 0.1533 0.3623 0.071 Uiso calc R 1 . .
    H H13B 0.1531 0.0399 0.3976 0.071 Uiso calc R 1 . .
    C C14 0.1555(3) 0.2066(6) 0.4628(3) 0.1041(17) Uani d . 1 . .
    H H14A 0.1538 0.2956 0.4474 0.156 Uiso calc R 1 . .
    H H14B 0.1964 0.1873 0.5176 0.156 Uiso calc R 1 . .
    H H14C 0.1219 0.1871 0.4774 0.156 Uiso calc R 1 . .
    N N1 0.20655(13) 0.2775(2) 0.2060(2) 0.0437(7) Uani d . 1 . .
    H H1 0.2470(17) 0.302(3) 0.222(2) 0.052 Uiso d . 1 . .
    N N2 0.19845(13) 0.0500(2) 0.1748(2) 0.0454(7) Uani d . 1 . .
    H H2 0.2345(17) 0.017(3) 0.175(2) 0.054 Uiso d . 1 . .
    N N3 0.11016(11) 0.2801(2) 0.19456(17) 0.0345(6) Uani d . 1 . .
    N N4 0.10575(11) 0.0516(2) 0.17482(19) 0.0398(6) Uani d . 1 . .
    N N5 0.08274(12) 0.1450(2) 0.2943(2) 0.0446(7) Uani d . 1 . .
    O O1 0.18833(10) 0.41850(19) 0.30059(16) 0.0477(6) Uani d . 1 . .
    O O2 0.17362(10) -0.1192(2) 0.24359(18) 0.0548(6) Uani d . 1 . .
    O O3 0.20115(14) 0.1339(3) 0.0142(2) 0.0730(8) Uani d . 1 . .
    O O4 0.14544(13) 0.3091(2) 0.00594(18) 0.0666(7) Uani d . 1 . .
    O O5 0.04553(12) 0.1026(2) -0.02871(18) 0.0681(8) Uani d . 1 . .
    O O6 0.00918(10) 0.2715(2) 0.01628(16) 0.0523(6) Uani d . 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.226(3) ?
    C1 N1 . 1.349(4) yes
    C1 N3 . 1.381(4) yes
    C2 O2 . 1.230(3) ?
    C2 N2 . 1.353(4) yes
    C2 N4 . 1.370(4) yes
    C3 N2 . 1.443(4) yes
    C3 N1 . 1.443(4) yes
    C3 C4 . 1.532(5) ?
    C3 C7 . 1.565(4) ?
    C4 O3 . 1.190(4) ?
    C4 O4 . 1.313(4) ?
    C5 C6 . 1.439(8) ?
    C5 O4 . 1.455(5) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C7 N3 . 1.446(3) yes
    C7 N4 . 1.460(3) yes
    C7 C8 . 1.536(4) ?
    C8 O5 . 1.194(4) ?
    C8 O6 . 1.318(4) ?
    C9 O6 . 1.456(4) ?
    C9 C10 . 1.457(6) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 N5 . 1.456(4) yes
    C11 N3 . 1.470(4) yes
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 N5 . 1.452(4) yes
    C12 N4 . 1.478(4) yes
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 N5 . 1.470(4) yes
    C13 C14 . 1.483(6) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    N1 H1 . 0.91(3) ?
    N2 H2 . 0.93(3) ?
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
    O1 C1 N1 . . 126.4(3) ?
    O1 C1 N3 . . 124.8(3) ?
    N1 C1 N3 . . 108.8(2) ?
    O2 C2 N2 . . 126.7(3) ?
    O2 C2 N4 . . 124.3(3) ?
    N2 C2 N4 . . 108.9(3) ?
    N2 C3 N1 . . 114.2(3) ?
    N2 C3 C4 . . 110.9(2) ?
    N1 C3 C4 . . 109.9(2) ?
    N2 C3 C7 . . 102.7(2) ?
    N1 C3 C7 . . 101.7(2) ?
    C4 C3 C7 . . 117.3(2) ?
    O3 C4 O4 . . 126.2(3) ?
    O3 C4 C3 . . 123.6(3) ?
    O4 C4 C3 . . 110.1(3) ?
    C6 C5 O4 . . 110.8(4) ?
    C6 C5 H5A . . 109.5 ?
    O4 C5 H5A . . 109.5 ?
    C6 C5 H5B . . 109.5 ?
    O4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 108.1 ?
    N3 C7 N4 . . 112.1(2) ?
    N3 C7 C8 . . 115.5(2) ?
    N4 C7 C8 . . 107.7(2) ?
    N3 C7 C3 . . 104.5(2) ?
    N4 C7 C3 . . 103.1(2) ?
    C8 C7 C3 . . 113.4(2) ?
    O5 C8 O6 . . 125.9(3) ?
    O5 C8 C7 . . 121.1(3) ?
    O6 C8 C7 . . 113.0(3) ?
    O6 C9 C10 . . 108.8(4) ?
    O6 C9 H9A . . 109.9 ?
    C10 C9 H9A . . 109.9 ?
    O6 C9 H9B . . 109.9 ?
    C10 C9 H9B . . 109.9 ?
    H9A C9 H9B . . 108.3 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N5 C11 N3 . . 113.4(2) ?
    N5 C11 H11A . . 108.9 ?
    N3 C11 H11A . . 108.9 ?
    N5 C11 H11B . . 108.9 ?
    N3 C11 H11B . . 108.9 ?
    H11A C11 H11B . . 107.7 ?
    N5 C12 N4 . . 112.1(2) ?
    N5 C12 H12A . . 109.2 ?
    N4 C12 H12A . . 109.2 ?
    N5 C12 H12B . . 109.2 ?
    N4 C12 H12B . . 109.2 ?
    H12A C12 H12B . . 107.9 ?
    N5 C13 C14 . . 112.9(3) ?
    N5 C13 H13A . . 109.0 ?
    C14 C13 H13A . . 109.0 ?
    N5 C13 H13B . . 109.0 ?
    C14 C13 H13B . . 109.0 ?
    H13A C13 H13B . . 107.8 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C1 N1 C3 . . 114.0(2) ?
    C1 N1 H1 . . 124(2) ?
    C3 N1 H1 . . 122(2) ?
    C2 N2 C3 . . 113.0(2) ?
    C2 N2 H2 . . 125(2) ?
    C3 N2 H2 . . 122(2) ?
    C1 N3 C7 . . 110.8(2) ?
    C1 N3 C11 . . 120.7(2) ?
    C7 N3 C11 . . 117.0(2) ?
    C2 N4 C7 . . 111.6(2) ?
    C2 N4 C12 . . 123.9(3) ?
    C7 N4 C12 . . 116.5(2) ?
    C12 N5 C11 . . 108.5(2) ?
    C12 N5 C13 . . 112.5(3) ?
    C11 N5 C13 . . 114.2(2) ?
    C4 O4 C5 . . 116.9(3) ?
    C8 O6 C9 . . 115.5(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    N2 C3 C4 O3 . . . . -10.3(4) ?
    N1 C3 C4 O3 . . . . 116.9(3) ?
    C7 C3 C4 O3 . . . . -127.7(3) ?
    N2 C3 C4 O4 . . . . 172.3(3) ?
    N1 C3 C4 O4 . . . . -60.5(3) ?
    C7 C3 C4 O4 . . . . 54.9(3) ?
    N2 C3 C7 N3 . . . . 121.3(2) ?
    N1 C3 C7 N3 . . . . 2.9(3) yes
    C4 C3 C7 N3 . . . . -116.9(3) ?
    N2 C3 C7 N4 . . . . 4.0(3) ?
    N1 C3 C7 N4 . . . . -114.4(2) ?
    C4 C3 C7 N4 . . . . 125.8(3) ?
    N2 C3 C7 C8 . . . . -112.2(3) ?
    N1 C3 C7 C8 . . . . 129.4(2) ?
    C4 C3 C7 C8 . . . . 9.6(3) yes
    N3 C7 C8 O5 . . . . 174.2(3) ?
    N4 C7 C8 O5 . . . . -59.8(4) ?
    C3 C7 C8 O5 . . . . 53.7(4) ?
    N3 C7 C8 O6 . . . . -6.6(4) ?
    N4 C7 C8 O6 . . . . 119.5(3) ?
    C3 C7 C8 O6 . . . . -127.1(3) ?
    O1 C1 N1 C3 . . . . 177.1(3) ?
    N3 C1 N1 C3 . . . . -3.3(3) ?
    N2 C3 N1 C1 . . . . -109.7(3) ?
    C4 C3 N1 C1 . . . . 125.0(3) ?
    C7 C3 N1 C1 . . . . 0.1(3) ?
    O2 C2 N2 C3 . . . . -173.6(3) ?
    N4 C2 N2 C3 . . . . 8.7(4) ?
    N1 C3 N2 C2 . . . . 101.4(3) ?
    C4 C3 N2 C2 . . . . -133.9(3) ?
    C7 C3 N2 C2 . . . . -7.8(3) ?
    O1 C1 N3 C7 . . . . -175.1(3) ?
    N1 C1 N3 C7 . . . . 5.3(3) ?
    O1 C1 N3 C11 . . . . -32.9(4) ?
    N1 C1 N3 C11 . . . . 147.5(3) ?
    N4 C7 N3 C1 . . . . 105.9(3) ?
    C8 C7 N3 C1 . . . . -130.3(3) ?
    C3 C7 N3 C1 . . . . -5.0(3) ?
    N4 C7 N3 C11 . . . . -37.8(3) ?
    C8 C7 N3 C11 . . . . 86.0(3) ?
    C3 C7 N3 C11 . . . . -148.8(2) ?
    N5 C11 N3 C1 . . . . -91.8(3) ?
    N5 C11 N3 C7 . . . . 48.2(3) ?
    O2 C2 N4 C7 . . . . 176.6(3) ?
    N2 C2 N4 C7 . . . . -5.7(4) ?
    O2 C2 N4 C12 . . . . 28.9(5) ?
    N2 C2 N4 C12 . . . . -153.3(3) ?
    N3 C7 N4 C2 . . . . -111.0(3) ?
    C8 C7 N4 C2 . . . . 120.9(3) ?
    C3 C7 N4 C2 . . . . 0.8(3) ?
    N3 C7 N4 C12 . . . . 39.2(3) ?
    C8 C7 N4 C12 . . . . -88.8(3) ?
    C3 C7 N4 C12 . . . . 151.0(3) ?
    N5 C12 N4 C2 . . . . 95.4(3) ?
    N5 C12 N4 C7 . . . . -50.8(4) ?
    N4 C12 N5 C11 . . . . 57.0(3) ?
    N4 C12 N5 C13 . . . . -70.4(3) ?
    N3 C11 N5 C12 . . . . -56.0(3) ?
    N3 C11 N5 C13 . . . . 70.4(3) ?
    C14 C13 N5 C12 . . . . -162.6(3) ?
    C14 C13 N5 C11 . . . . 73.0(4) ?
    O3 C4 O4 C5 . . . . -0.8(6) ?
    C3 C4 O4 C5 . . . . 176.5(4) ?
    C6 C5 O4 C4 . . . . 127.1(5) ?
    O5 C8 O6 C9 . . . . 1.6(5) ?
    C7 C8 O6 C9 . . . . -177.6(3) ?
    C10 C9 O6 C8 . . . . -168.8(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
    _geom_hbond_publ_flag
    N2 H2 O1 4_545 0.93(3) 1.98(4) 2.886(3) 166(3) yes
    N1 H1 O2 4 0.91(3) 1.89(4) 2.786(3) 170(3) yes
    C13 H13B O3 6_556 0.97 2.45 3.342(4) 153 yes
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
6-ethyl-2a,7b-diphenyl-2,2a,3,4,6,7-hexahydro-1H,5H-2,3,4a,6,7a-
pentaazacyclopenta[cd]azulene-1,4-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H21 N5 O2'
_chemical_formula_sum     'C20 H21 N5 O2'
_chemical_formula_iupac     'C20 H21 N5 O2'
_chemical_formula_weight     363.42
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     P21/n
_symmetry_space_group_name_Hall     '-P 2yn'
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     8.0724(5)
_cell_length_b     11.6462(7)
_cell_length_c     19.2338(12)
_cell_angle_alpha     90.00
_cell_angle_beta     100.4620(10)
_cell_angle_gamma     90.00
_cell_volume     1778.16(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2090
_cell_measurement_theta_min     2.60
_cell_measurement_theta_max     21.42
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.358
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     768
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9820
_exptl_absorpt_correction_T_max     0.9909
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine focus sealed Siemens Mo tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     '0.3° wide ω exposures'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16184
_diffrn_reflns_av_R_equivalents     0.0577
_diffrn_reflns_av_sigmaI/netI     0.0569
_diffrn_reflns_theta_min     2.05
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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.
;
_reflns_number_total     3860
_reflns_number_gt     2581
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1032
_refine_ls_R_factor_gt     0.0632
_refine_ls_wR_factor_gt     0.1435
_refine_ls_wR_factor_ref     0.1587
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.035
_refine_ls_number_reflns     3860
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0709P)²+0.4735P] 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     0.283
_refine_diff_density_min     -0.207
_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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART (Bruker, 2001)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'PLATON (Spek, 2003)'
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
    C C1 0.6718(3) 0.68744(19) 0.17062(11) 0.0291(5) Uani d . 1 . .
    C C2 0.7753(3) 0.7129(2) 0.11401(12) 0.0364(6) Uani d . 1 . .
    C C3 0.8332(3) 0.8224(3) 0.10483(15) 0.0554(8) Uani d . 1 . .
    H H3 0.8148 0.8808 0.1355 0.066 Uiso calc R 1 . .
    C C4 0.9187(4) 0.8459(4) 0.0501(2) 0.0841(12) Uani d . 1 . .
    H H4 0.9598 0.9194 0.0450 0.101 Uiso calc R 1 . .
    C C5 0.9428(4) 0.7610(5) 0.0035(2) 0.0976(16) Uani d . 1 . .
    H H5 0.9982 0.7772 -0.0337 0.117 Uiso calc R 1 . .
    C C6 0.8854(4) 0.6531(4) 0.01190(17) 0.0835(12) Uani d . 1 . .
    H H6 0.9018 0.5957 -0.0198 0.100 Uiso calc R 1 . .
    C C7 0.8028(3) 0.6279(3) 0.06721(13) 0.0560(8) Uani d . 1 . .
    H H7 0.7657 0.5535 0.0729 0.067 Uiso calc R 1 . .
    C C8 0.4729(3) 0.69466(18) 0.14481(10) 0.0263(5) Uani d . 1 . .
    C C9 0.4133(3) 0.73594(19) 0.06922(10) 0.0279(5) Uani d . 1 . .
    C C10 0.3957(3) 0.8517(2) 0.05468(12) 0.0427(6) Uani d . 1 . .
    H H10 0.4153 0.9046 0.0915 0.051 Uiso calc R 1 . .
    C C11 0.3490(3) 0.8901(3) -0.01449(15) 0.0565(8) Uani d . 1 . .
    H H11 0.3381 0.9684 -0.0237 0.068 Uiso calc R 1 . .
    C C12 0.3189(3) 0.8137(3) -0.06903(14) 0.0591(8) Uani d . 1 . .
    H H12 0.2868 0.8395 -0.1153 0.071 Uiso calc R 1 . .
    C C13 0.3364(4) 0.6988(3) -0.05513(13) 0.0594(8) Uani d . 1 . .
    H H13 0.3166 0.6464 -0.0922 0.071 Uiso calc R 1 . .
    C C14 0.3832(3) 0.6596(2) 0.01343(11) 0.0425(6) Uani d . 1 . .
    H H14 0.3945 0.5812 0.0221 0.051 Uiso calc R 1 . .
    C C15 0.5532(3) 0.8141(2) 0.24338(11) 0.0341(5) Uani d . 1 . .
    C C16 0.5426(3) 0.5117(2) 0.19058(10) 0.0311(5) Uani d . 1 . .
    C C17 0.2468(3) 0.7614(2) 0.20744(12) 0.0369(6) Uani d . 1 . .
    H H17A 0.2318 0.8093 0.2471 0.044 Uiso calc R 1 . .
    H H17B 0.1707 0.7891 0.1659 0.044 Uiso calc R 1 . .
    C C18 0.2402(3) 0.5693(2) 0.16625(11) 0.0344(5) Uani d . 1 . .
    H H18A 0.1651 0.5878 0.1223 0.041 Uiso calc R 1 . .
    H H18B 0.2186 0.4905 0.1782 0.041 Uiso calc R 1 . .
    C C19 0.2732(4) 0.6034(3) 0.29320(12) 0.0527(7) Uani d . 1 . .
    H H19A 0.2798 0.5202 0.2931 0.063 Uiso calc R 1 . .
    H H19B 0.3865 0.6332 0.3073 0.063 Uiso calc R 1 . .
    C C20 0.1691(5) 0.6403(4) 0.34440(16) 0.0899(12) Uani d . 1 . .
    H H20A 0.1698 0.7226 0.3473 0.135 Uiso calc R 1 . .
    H H20B 0.2140 0.6086 0.3900 0.135 Uiso calc R 1 . .
    H H20C 0.0557 0.6138 0.3293 0.135 Uiso calc R 1 . .
    N N1 0.6980(3) 0.76980(19) 0.22757(10) 0.0407(5) Uani d . 1 . .
    H H1 0.797(3) 0.809(2) 0.2453(13) 0.049 Uiso d . 1 . .
    N N2 0.6905(2) 0.56991(18) 0.19555(10) 0.0367(5) Uani d . 1 . .
    H H2 0.787(3) 0.531(2) 0.2024(12) 0.044 Uiso d . 1 . .
    N N3 0.4207(2) 0.77285(16) 0.19596(9) 0.0295(4) Uani d . 1 . .
    N N4 0.4148(2) 0.57886(15) 0.15536(9) 0.0286(4) Uani d . 1 . .
    N N5 0.2025(2) 0.64405(18) 0.22146(9) 0.0369(5) Uani d . 1 . .
    O O1 0.5438(2) 0.88198(15) 0.29134(8) 0.0477(5) Uani d . 1 . .
    O O2 0.5242(2) 0.41385(15) 0.21175(9) 0.0454(5) Uani d . 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N1 . 1.442(3) yes
    C1 N2 . 1.449(3) yes
    C1 C2 . 1.517(3) ?
    C1 C8 . 1.594(3) ?
    C2 C3 . 1.381(4) ?
    C2 C7 . 1.383(4) ?
    C3 C4 . 1.386(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.372(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.358(6) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.386(4) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 N4 . 1.454(3) yes
    C8 N3 . 1.458(3) yes
    C8 C9 . 1.524(3) ?
    C9 C10 . 1.379(3) ?
    C9 C14 . 1.380(3) ?
    C10 C11 . 1.389(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.363(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.367(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.382(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 O1 . 1.227(3) ?
    C15 N3 . 1.361(3) yes
    C15 N1 . 1.361(3) yes
    C16 O2 . 1.229(3) ?
    C16 N2 . 1.361(3) yes
    C16 N4 . 1.371(3) yes
    C17 N5 . 1.451(3) yes
    C17 N3 . 1.467(3) yes
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 N5 . 1.447(3) yes
    C18 N4 . 1.466(3) yes
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 C20 . 1.470(4) ?
    C19 N5 . 1.472(3) yes
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    N1 H1 . 0.93(3) ?
    N2 H2 . 0.89(3) ?
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
    N1 C1 N2 . . 112.64(18) ?
    N1 C1 C2 . . 113.02(19) ?
    N2 C1 C2 . . 112.63(18) ?
    N1 C1 C8 . . 101.63(16) ?
    N2 C1 C8 . . 101.02(17) ?
    C2 C1 C8 . . 114.87(16) ?
    C3 C2 C7 . . 118.7(2) ?
    C3 C2 C1 . . 121.1(2) ?
    C7 C2 C1 . . 120.1(2) ?
    C2 C3 C4 . . 120.4(3) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 120.2(4) ?
    C5 C4 H4 . . 119.9 ?
    C3 C4 H4 . . 119.9 ?
    C6 C5 C4 . . 119.8(3) ?
    C6 C5 H5 . . 120.1 ?
    C4 C5 H5 . . 120.1 ?
    C5 C6 C7 . . 120.6(4) ?
    C5 C6 H6 . . 119.7 ?
    C7 C6 H6 . . 119.7 ?
    C2 C7 C6 . . 120.3(3) ?
    C2 C7 H7 . . 119.8 ?
    C6 C7 H7 . . 119.8 ?
    N4 C8 N3 . . 110.19(16) ?
    N4 C8 C9 . . 111.82(16) ?
    N3 C8 C9 . . 111.53(17) ?
    N4 C8 C1 . . 103.87(16) ?
    N3 C8 C1 . . 102.77(15) ?
    C9 C8 C1 . . 116.06(16) ?
    C10 C9 C14 . . 118.3(2) ?
    C10 C9 C8 . . 120.33(19) ?
    C14 C9 C8 . . 121.3(2) ?
    C9 C10 C11 . . 120.6(2) ?
    C9 C10 H10 . . 119.7 ?
    C11 C10 H10 . . 119.7 ?
    C12 C11 C10 . . 120.4(3) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C11 C12 C13 . . 119.4(2) ?
    C11 C12 H12 . . 120.3 ?
    C13 C12 H12 . . 120.3 ?
    C12 C13 C14 . . 120.7(3) ?
    C12 C13 H13 . . 119.6 ?
    C14 C13 H13 . . 119.6 ?
    C9 C14 C13 . . 120.6(3) ?
    C9 C14 H14 . . 119.7 ?
    C13 C14 H14 . . 119.7 ?
    O1 C15 N3 . . 125.6(2) ?
    O1 C15 N1 . . 125.8(2) ?
    N3 C15 N1 . . 108.55(19) ?
    O2 C16 N2 . . 126.6(2) ?
    O2 C16 N4 . . 124.6(2) ?
    N2 C16 N4 . . 108.81(19) ?
    N5 C17 N3 . . 112.84(19) ?
    N5 C17 H17A . . 109.0 ?
    N3 C17 H17A . . 109.0 ?
    N5 C17 H17B . . 109.0 ?
    N3 C17 H17B . . 109.0 ?
    H17A C17 H17B . . 107.8 ?
    N5 C18 N4 . . 113.27(18) ?
    N5 C18 H18A . . 108.9 ?
    N4 C18 H18A . . 108.9 ?
    N5 C18 H18B . . 108.9 ?
    N4 C18 H18B . . 108.9 ?
    H18A C18 H18B . . 107.7 ?
    C20 C19 N5 . . 111.2(2) ?
    C20 C19 H19A . . 109.4 ?
    N5 C19 H19A . . 109.4 ?
    C20 C19 H19B . . 109.4 ?
    N5 C19 H19B . . 109.4 ?
    H19A C19 H19B . . 108.0 ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C15 N1 C1 . . 114.12(19) ?
    C15 N1 H1 . . 116.8(16) ?
    C1 N1 H1 . . 126.8(15) ?
    C16 N2 C1 . . 114.20(18) ?
    C16 N2 H2 . . 119.4(17) ?
    C1 N2 H2 . . 124.4(16) ?
    C15 N3 C8 . . 112.62(18) ?
    C15 N3 C17 . . 126.04(18) ?
    C8 N3 C17 . . 116.55(17) ?
    C16 N4 C8 . . 111.40(17) ?
    C16 N4 C18 . . 122.86(18) ?
    C8 N4 C18 . . 115.65(17) ?
    C18 N5 C17 . . 109.79(17) ?
    C18 N5 C19 . . 113.4(2) ?
    C17 N5 C19 . . 114.3(2) ?
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
    N1 C1 C2 C3 . . . . -23.1(3) ?
    N2 C1 C2 C3 . . . . -152.1(2) ?
    C8 C1 C2 C3 . . . . 92.9(3) ?
    N1 C1 C2 C7 . . . . 161.6(2) ?
    N2 C1 C2 C7 . . . . 32.5(3) ?
    C8 C1 C2 C7 . . . . -82.4(3) ?
    C7 C2 C3 C4 . . . . -0.6(4) ?
    C1 C2 C3 C4 . . . . -176.0(2) ?
    C2 C3 C4 C5 . . . . 1.6(4) ?
    C3 C4 C5 C6 . . . . -1.2(5) ?
    C4 C5 C6 C7 . . . . -0.1(5) ?
    C3 C2 C7 C6 . . . . -0.7(4) ?
    C1 C2 C7 C6 . . . . 174.7(2) ?
    C5 C6 C7 C2 . . . . 1.0(5) ?
    N1 C1 C8 N4 . . . . -119.56(17) ?
    N2 C1 C8 N4 . . . . -3.42(19) ?
    C2 C1 C8 N4 . . . . 118.06(19) ?
    N1 C1 C8 N3 . . . . -4.7(2) yes
    N2 C1 C8 N3 . . . . 111.44(17) ?
    C2 C1 C8 N3 . . . . -127.07(19) ?
    N1 C1 C8 C9 . . . . 117.3(2) ?
    N2 C1 C8 C9 . . . . -126.58(19) ?
    C2 C1 C8 C9 . . . . -5.1(3) yes
    N4 C8 C9 C10 . . . . 154.5(2) ?
    N3 C8 C9 C10 . . . . 30.6(3) ?
    C1 C8 C9 C10 . . . . -86.6(3) ?
    N4 C8 C9 C14 . . . . -28.5(3) ?
    N3 C8 C9 C14 . . . . -152.4(2) ?
    C1 C8 C9 C14 . . . . 90.4(3) ?
    C14 C9 C10 C11 . . . . -0.1(4) ?
    C8 C9 C10 C11 . . . . 177.0(2) ?
    C9 C10 C11 C12 . . . . 0.3(4) ?
    C10 C11 C12 C13 . . . . -0.5(4) ?
    C11 C12 C13 C14 . . . . 0.3(4) ?
    C10 C9 C14 C13 . . . . -0.1(4) ?
    C8 C9 C14 C13 . . . . -177.1(2) ?
    C12 C13 C14 C9 . . . . 0.0(4) ?
    O1 C15 N1 C1 . . . . 177.0(2) ?
    N3 C15 N1 C1 . . . . -4.5(3) ?
    N2 C1 N1 C15 . . . . -101.6(2) ?
    C2 C1 N1 C15 . . . . 129.4(2) ?
    C8 C1 N1 C15 . . . . 5.7(2) ?
    O2 C16 N2 C1 . . . . -175.6(2) ?
    N4 C16 N2 C1 . . . . 6.5(2) ?
    N1 C1 N2 C16 . . . . 106.0(2) ?
    C2 C1 N2 C16 . . . . -124.7(2) ?
    C8 C1 N2 C16 . . . . -1.7(2) ?
    O1 C15 N3 C8 . . . . 179.3(2) ?
    N1 C15 N3 C8 . . . . 0.8(3) ?
    O1 C15 N3 C17 . . . . -26.3(4) ?
    N1 C15 N3 C17 . . . . 155.3(2) ?
    N4 C8 N3 C15 . . . . 112.8(2) ?
    C9 C8 N3 C15 . . . . -122.4(2) ?
    C1 C8 N3 C15 . . . . 2.6(2) ?
    N4 C8 N3 C17 . . . . -44.3(2) ?
    C9 C8 N3 C17 . . . . 80.5(2) ?
    C1 C8 N3 C17 . . . . -154.46(17) ?
    N5 C17 N3 C15 . . . . -103.2(2) ?
    N5 C17 N3 C8 . . . . 50.4(2) ?
    O2 C16 N4 C8 . . . . 173.2(2) ?
    N2 C16 N4 C8 . . . . -8.9(2) ?
    O2 C16 N4 C18 . . . . 29.4(3) ?
    N2 C16 N4 C18 . . . . -152.67(19) ?
    N3 C8 N4 C16 . . . . -101.92(19) ?
    C9 C8 N4 C16 . . . . 133.45(18) ?
    C1 C8 N4 C16 . . . . 7.6(2) ?
    N3 C8 N4 C18 . . . . 44.7(2) ?
    C9 C8 N4 C18 . . . . -80.0(2) ?
    C1 C8 N4 C18 . . . . 154.14(16) ?
    N5 C18 N4 C16 . . . . 90.4(2) ?
    N5 C18 N4 C8 . . . . -52.0(2) ?
    N4 C18 N5 C17 . . . . 54.1(2) ?
    N4 C18 N5 C19 . . . . -75.1(2) ?
    N3 C17 N5 C18 . . . . -53.0(2) ?
    N3 C17 N5 C19 . . . . 75.7(2) ?
    C20 C19 N5 C18 . . . . -150.6(3) ?
    C20 C19 N5 C17 . . . . 82.5(3) ?
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
    _geom_hbond_publ_flag
    N2 H2 O1 2_645 0.89(3) 2.20(3) 3.043(3) 158(2) yes
    N1 H1 O2 2_655 0.93(3) 1.96(3) 2.873(3) 168(2) yes
    C18 H18B O1 2_545 0.97 2.62 3.370(3) 134.0(10)
                                                yes
    C17 H17A O2 2_555 0.97 2.64 3.404(3) 135.0(10)
                                                yes
