##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-06-30
_journal_date_accepted     2005-07-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      9
_journal_page_first     o2791
_journal_page_last     o2792
_journal_paper_category     EO
_journal_coeditor_code     OB6548
_publ_contact_author_name     'Prof. Ding, Ming-Wu, Prof. He, Hong-Wu'
_publ_contact_author_address
; Key Laboratory of Pesticide and Chemical Biology
  College of Chemistry
  Central China Normal University
  Wuhan  430079
  People's Republic of China
;
_publ_contact_author_email     dmw711@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
5,6-Dianilino-3-(4-chlorophenyl)-3,6-dihydro-1,2,3-triazolo[4,5-d]\
pyrimidin-7-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Zhao, Jun-Feng' .
;
Key Laboratory of Pesticide and Chemical Biology
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Hu, Yang-Gen' .
;
Key Laboratory of Pesticide and Chemical Biology
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Ding, Ming-Wu' .
;
Key Laboratory of Pesticide and Chemical Biology
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'He, Hong-Wu' .
;
Key Laboratory of Pesticide and Chemical Biology
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
data_2
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5,6-Dianilino-3-(4-chlorophenyl)-3,6-dihydro-1,2,3-triazolo[4,5-d]pyrimidin-
7-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H16 Cl N7 O'
_chemical_formula_sum     'C22 H16 Cl N7 O'
_chemical_formula_iupac     'C22 H16 Cl N7 O'
_chemical_formula_weight     429.87
_chemical_melting_point     512
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/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     14.981(2)
_cell_length_b     7.6973(12)
_cell_length_c     17.468(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.0010(10)
_cell_angle_gamma     90.00
_cell_volume     2014.3(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2384
_cell_measurement_theta_min     2.89
_cell_measurement_theta_max     21.99
_cell_measurement_temperature     292(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.417
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     888
_exptl_absorpt_coefficient_mu     0.221
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     292(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     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12017
_diffrn_reflns_av_R_equivalents     0.0634
_diffrn_reflns_av_sigmaI/netI     0.0674
_diffrn_reflns_theta_min     1.79
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_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     4395
_reflns_number_gt     2595
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0858
_refine_ls_R_factor_gt     0.0497
_refine_ls_wR_factor_gt     0.1112
_refine_ls_wR_factor_ref     0.1250
_refine_ls_goodness_of_fit_ref     0.901
_refine_ls_restrained_S_all     0.901
_refine_ls_number_reflns     4395
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0602P)²] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.425
_refine_diff_density_min     -0.368
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.00050(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT-Plus (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2001)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    C1 0.38608(16) -0.0134(3) 0.40410(13) 0.0660(7) Uani d . 1 . . C
    H1 0.3356 0.0482 0.4191 0.079 Uiso calc R 1 . . H
    C2 0.42405(17) 0.0163(3) 0.33326(14) 0.0700(7) Uani d . 1 . . C
    H2 0.3994 0.0992 0.3008 0.084 Uiso calc R 1 . . H
    C3 0.49758(16) -0.0753(3) 0.31059(12) 0.0553(6) Uani d . 1 . . C
    C4 0.53438(14) -0.1995(3) 0.35809(12) 0.0574(6) Uani d . 1 . . C
    H4 0.5839 -0.2629 0.3423 0.069 Uiso calc R 1 . . H
    C5 0.49713(14) -0.2288(3) 0.42927(12) 0.0529(5) Uani d . 1 . . C
    H5 0.5217 -0.3118 0.4617 0.063 Uiso calc R 1 . . H
    C6 0.42330(13) -0.1347(3) 0.45223(11) 0.0458(5) Uani d . 1 . . C
    C7 0.31902(13) -0.0782(2) 0.56385(11) 0.0428(5) Uani d . 1 . . C
    C8 0.30472(13) -0.1735(2) 0.62912(10) 0.0435(5) Uani d . 1 . . C
    C9 0.23816(13) -0.1207(3) 0.68341(11) 0.0461(5) Uani d . 1 . . C
    C10 0.22188(13) 0.1289(3) 0.59387(11) 0.0431(5) Uani d . 1 . . C
    C11 0.18987(15) 0.4089(2) 0.52738(11) 0.0474(5) Uani d . 1 . . C
    C12 0.12057(17) 0.5253(3) 0.51824(13) 0.0639(6) Uani d . 1 . . C
    H12 0.0709 0.5199 0.5501 0.077 Uiso calc R 1 . . H
    C13 0.12552(19) 0.6501(3) 0.46131(15) 0.0794(8) Uani d . 1 . . C
    H13 0.0791 0.7293 0.4556 0.095 Uiso calc R 1 . . H
    C14 0.1977(2) 0.6588(3) 0.41336(15) 0.0818(8) Uani d . 1 . . C
    H14 0.1994 0.7401 0.3740 0.098 Uiso calc R 1 . . H
    C15 0.2674(2) 0.5456(3) 0.42422(15) 0.0762(8) Uani d . 1 . . C
    H15 0.3176 0.5532 0.3930 0.091 Uiso calc R 1 . . H
    C16 0.26413(16) 0.4206(3) 0.48093(13) 0.0605(6) Uani d . 1 . . C
    H16 0.3118 0.3447 0.4878 0.073 Uiso calc R 1 . . H
    C17 0.03856(13) 0.0183(2) 0.68339(11) 0.0441(5) Uani d . 1 . . C
    C18 -0.02896(15) 0.0324(3) 0.73664(13) 0.0602(6) Uani d . 1 . . C
    H18 -0.0183 0.0867 0.7833 0.072 Uiso calc R 1 . . H
    C19 -0.11271(17) -0.0346(4) 0.72046(17) 0.0778(8) Uani d . 1 . . C
    H19 -0.1582 -0.0257 0.7564 0.093 Uiso calc R 1 . . H
    C20 -0.12868(17) -0.1141(4) 0.65144(17) 0.0796(8) Uani d . 1 . . C
    H20 -0.1846 -0.1612 0.6410 0.095 Uiso calc R 1 . . H
    C21 -0.06210(18) -0.1238(3) 0.59810(15) 0.0725(7) Uani d . 1 . . C
    H21 -0.0735 -0.1751 0.5509 0.087 Uiso calc R 1 . . H
    C22 0.02157(15) -0.0587(3) 0.61338(12) 0.0572(6) Uani d . 1 . . C
    H22 0.0665 -0.0664 0.5768 0.069 Uiso calc R 1 . . H
    Cl1 0.54410(5) -0.03631(9) 0.22126(4) 0.0831(3) Uani d . 1 . . Cl
    N1 0.38419(10) -0.1658(2) 0.52542(9) 0.0449(4) Uani d . 1 . . N
    N2 0.40903(12) -0.3101(2) 0.56786(9) 0.0542(5) Uani d . 1 . . N
    N3 0.36098(11) -0.3130(2) 0.63005(9) 0.0526(5) Uani d . 1 . . N
    N4 0.28118(11) 0.0749(2) 0.54387(9) 0.0450(4) Uani d . 1 . . N
    N5 0.19470(10) 0.0323(2) 0.65726(9) 0.0430(4) Uani d . 1 . . N
    N6 0.18025(11) 0.2832(2) 0.58623(9) 0.0514(4) Uani d . 1 . . N
    H6 0.1428 0.3090 0.6218 0.062 Uiso calc R 1 . . H
    N7 0.12268(11) 0.0947(2) 0.69985(9) 0.0471(4) Uani d . 1 . . N
    H7 0.1289 0.1744 0.7339 0.057 Uiso calc R 1 . . H
    O1 0.21644(9) -0.1877(2) 0.74336(8) 0.0596(4) Uani d . 1 . . O
_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 C6 . 1.374(3) ?
    C1 C2 . 1.381(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.367(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.381(3) ?
    C3 Cl1 . 1.735(2) ?
    C4 C5 . 1.382(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.9300 ?
    C6 N1 . 1.426(2) ?
    C7 N4 . 1.353(2) yes
    C7 N1 . 1.363(2) yes
    C7 C8 . 1.373(3) yes
    C8 N3 . 1.365(2) yes
    C8 C9 . 1.435(3) yes
    C9 O1 . 1.212(2) yes
    C9 N5 . 1.421(2) yes
    C10 N4 . 1.313(2) yes
    C10 N6 . 1.348(2) ?
    C10 N5 . 1.395(2) yes
    C11 C16 . 1.380(3) ?
    C11 C12 . 1.381(3) ?
    C11 N6 . 1.419(2) ?
    C12 C13 . 1.385(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.369(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.374(4) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.382(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.379(3) ?
    C17 C22 . 1.383(3) ?
    C17 N7 . 1.420(2) ?
    C18 C19 . 1.386(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.373(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.367(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.376(3) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    N1 N2 . 1.386(2) yes
    N2 N3 . 1.303(2) yes
    N5 N7 . 1.396(2) ?
    N6 H6 . 0.8600 ?
    N7 H7 . 0.8600 ?
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
    C6 C1 C2 . . 119.6(2) ?
    C6 C1 H1 . . 120.2 ?
    C2 C1 H1 . . 120.2 ?
    C3 C2 C1 . . 120.4(2) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 120.3(2) ?
    C2 C3 Cl1 . . 119.68(19) ?
    C4 C3 Cl1 . . 119.99(18) ?
    C3 C4 C5 . . 119.5(2) ?
    C3 C4 H4 . . 120.2 ?
    C5 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 119.9(2) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C1 C6 C5 . . 120.2(2) ?
    C1 C6 N1 . . 119.71(18) ?
    C5 C6 N1 . . 120.07(18) ?
    N4 C7 N1 . . 127.13(17) ?
    N4 C7 C8 . . 127.89(18) ?
    N1 C7 C8 . . 104.86(17) ?
    N3 C8 C7 . . 109.50(18) ?
    N3 C8 C9 . . 130.11(18) ?
    C7 C8 C9 . . 120.40(18) ?
    O1 C9 N5 . . 120.50(19) ?
    O1 C9 C8 . . 129.57(19) ?
    N5 C9 C8 . . 109.93(17) ?
    N4 C10 N6 . . 121.75(18) ?
    N4 C10 N5 . . 123.80(18) ?
    N6 C10 N5 . . 114.42(18) ?
    C16 C11 C12 . . 119.7(2) ?
    C16 C11 N6 . . 123.53(19) ?
    C12 C11 N6 . . 116.7(2) ?
    C11 C12 C13 . . 119.5(2) ?
    C11 C12 H12 . . 120.2 ?
    C13 C12 H12 . . 120.2 ?
    C14 C13 C12 . . 121.0(2) ?
    C14 C13 H13 . . 119.5 ?
    C12 C13 H13 . . 119.5 ?
    C13 C14 C15 . . 119.0(2) ?
    C13 C14 H14 . . 120.5 ?
    C15 C14 H14 . . 120.5 ?
    C14 C15 C16 . . 120.9(3) ?
    C14 C15 H15 . . 119.6 ?
    C16 C15 H15 . . 119.6 ?
    C11 C16 C15 . . 119.7(2) ?
    C11 C16 H16 . . 120.1 ?
    C15 C16 H16 . . 120.1 ?
    C18 C17 C22 . . 119.7(2) ?
    C18 C17 N7 . . 118.83(18) ?
    C22 C17 N7 . . 121.33(19) ?
    C17 C18 C19 . . 119.8(2) ?
    C17 C18 H18 . . 120.1 ?
    C19 C18 H18 . . 120.1 ?
    C20 C19 C18 . . 120.2(3) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C21 C20 C19 . . 119.7(2) ?
    C21 C20 H20 . . 120.1 ?
    C19 C20 H20 . . 120.1 ?
    C20 C21 C22 . . 120.8(2) ?
    C20 C21 H21 . . 119.6 ?
    C22 C21 H21 . . 119.6 ?
    C21 C22 C17 . . 119.7(2) ?
    C21 C22 H22 . . 120.1 ?
    C17 C22 H22 . . 120.1 ?
    C7 N1 N2 . . 108.98(15) yes
    C7 N1 C6 . . 130.72(16) yes
    N2 N1 C6 . . 120.23(16) yes
    N3 N2 N1 . . 108.11(15) ?
    N2 N3 C8 . . 108.55(16) ?
    C10 N4 C7 . . 112.81(16) ?
    C10 N5 N7 . . 117.73(16) ?
    C10 N5 C9 . . 124.29(17) ?
    N7 N5 C9 . . 117.90(15) ?
    C10 N6 C11 . . 128.70(18) ?
    C10 N6 H6 . . 115.6 ?
    C11 N6 H6 . . 115.6 ?
    N5 N7 C17 . . 115.84(15) ?
    N5 N7 H7 . . 122.1 ?
    C17 N7 H7 . . 122.1 ?
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
    C6 C1 C2 C3 . . . . 0.7(4) ?
    C1 C2 C3 C4 . . . . 0.4(4) ?
    C1 C2 C3 Cl1 . . . . 179.83(19) ?
    C2 C3 C4 C5 . . . . -1.0(3) ?
    Cl1 C3 C4 C5 . . . . 179.63(16) ?
    C3 C4 C5 C6 . . . . 0.3(3) ?
    C2 C1 C6 C5 . . . . -1.3(3) ?
    C2 C1 C6 N1 . . . . -180.0(2) ?
    C4 C5 C6 C1 . . . . 0.8(3) ?
    C4 C5 C6 N1 . . . . 179.42(17) ?
    N4 C7 C8 N3 . . . . -175.33(17) ?
    N1 C7 C8 N3 . . . . 0.9(2) ?
    N4 C7 C8 C9 . . . . 5.0(3) ?
    N1 C7 C8 C9 . . . . -178.79(16) ?
    N3 C8 C9 O1 . . . . 0.3(4) ?
    C7 C8 C9 O1 . . . . 179.94(19) ?
    N3 C8 C9 N5 . . . . -178.88(18) ?
    C7 C8 C9 N5 . . . . 0.7(2) ?
    C16 C11 C12 C13 . . . . 1.5(3) ?
    N6 C11 C12 C13 . . . . -179.4(2) ?
    C11 C12 C13 C14 . . . . 0.7(4) ?
    C12 C13 C14 C15 . . . . -2.5(4) ?
    C13 C14 C15 C16 . . . . 2.2(4) ?
    C12 C11 C16 C15 . . . . -1.8(3) ?
    N6 C11 C16 C15 . . . . 179.10(19) ?
    C14 C15 C16 C11 . . . . 0.0(4) ?
    C22 C17 C18 C19 . . . . 1.6(3) ?
    N7 C17 C18 C19 . . . . 177.3(2) ?
    C17 C18 C19 C20 . . . . -0.3(4) ?
    C18 C19 C20 C21 . . . . -1.3(4) ?
    C19 C20 C21 C22 . . . . 1.6(4) ?
    C20 C21 C22 C17 . . . . -0.3(4) ?
    C18 C17 C22 C21 . . . . -1.3(3) ?
    N7 C17 C22 C21 . . . . -176.85(19) ?
    N4 C7 N1 N2 . . . . 175.54(17) ?
    C8 C7 N1 N2 . . . . -0.7(2) ?
    N4 C7 N1 C6 . . . . -7.5(3) ?
    C8 C7 N1 C6 . . . . 176.20(17) ?
    C1 C6 N1 C7 . . . . -9.8(3) ?
    C5 C6 N1 C7 . . . . 171.53(19) ?
    C1 C6 N1 N2 . . . . 166.80(19) ?
    C5 C6 N1 N2 . . . . -11.8(3) ?
    C7 N1 N2 N3 . . . . 0.3(2) ?
    C6 N1 N2 N3 . . . . -177.00(16) ?
    N1 N2 N3 C8 . . . . 0.3(2) ?
    C7 C8 N3 N2 . . . . -0.7(2) ?
    C9 C8 N3 N2 . . . . 178.91(19) ?
    N6 C10 N4 C7 . . . . 176.47(16) ?
    N5 C10 N4 C7 . . . . -5.4(3) ?
    N1 C7 N4 C10 . . . . -178.09(18) ?
    C8 C7 N4 C10 . . . . -2.7(3) ?
    N4 C10 N5 N7 . . . . -171.47(16) ?
    N6 C10 N5 N7 . . . . 6.8(2) ?
    N4 C10 N5 C9 . . . . 11.7(3) ?
    N6 C10 N5 C9 . . . . -170.05(16) ?
    O1 C9 N5 C10 . . . . 172.35(17) ?
    C8 C9 N5 C10 . . . . -8.4(2) ?
    O1 C9 N5 N7 . . . . -4.5(3) ?
    C8 C9 N5 N7 . . . . 174.82(15) ?
    N4 C10 N6 C11 . . . . 0.7(3) ?
    N5 C10 N6 C11 . . . . -177.63(17) ?
    C16 C11 N6 C10 . . . . -22.1(3) ?
    C12 C11 N6 C10 . . . . 158.80(19) ?
    C10 N5 N7 C17 . . . . 98.39(19) ?
    C9 N5 N7 C17 . . . . -84.6(2) ?
    C18 C17 N7 N5 . . . . 160.60(17) ?
    C22 C17 N7 N5 . . . . -23.9(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
    N6 H6 N7 . 0.86 2.16 2.606(2) 112 yes
    N7 H7 N3 2_556 0.86 2.38 3.065(2) 137 yes
    N7 H7 O1 2_556 0.86 2.58 3.098(2) 120 yes
    C1 H1 N4 . 0.93 2.34 2.982(3) 126 no
    C5 H5 N2 . 0.93 2.51 2.827(3) 100 no
    C16 H16 N4 . 0.93 2.34 2.891(3) 118 no
