##############################################################################
###                                                                        ###
###        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     2006-01-16
_journal_date_accepted     2006-01-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      2
_journal_page_first     o857
_journal_page_last     o858
_journal_paper_category     EO
_journal_coeditor_code     CV6640
_publ_contact_author_name     'Jian-wu Wang'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering,
Shandong University,
Jinan 250100,
People's Republic of China
;
_publ_contact_author_email     yugp2005@yahoo.com.cn
_publ_contact_author_fax     '+86-531-88564464'
_publ_contact_author_phone     '+86-531-88564464'
_publ_section_title
;\
1-(4,6-Dimethoxy-1,3,5-triazin-2-yloxy)-1H-pyridino[2,3-d]\
triazole
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Da-Tong Zhang' .
;
School of Chemistry and Chemical Engineering,
Shandong University,
Jinan 250100,
People's Republic of China
;
    'Fang-Qang Sun' .
;
School of Chemistry and Chemical Engineering,
Shandong University,
Jinan 250100,
People's Republic of China
;
    'Gui-Yun Duan' .
;
School of Chemistry and Chemical Engineering,
Shandong University,
Jinan 250100,
People's Republic of China
;
    'Jian-Wu Wang' .
;
School of Chemistry and Chemical Engineering,
Shandong University,
Jinan 250100,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(4,6-Dimethoxy-1,3,5-triazin-2-yloxy)-1H-pyridino[2,3-d]triazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H9 N7 O3'
_chemical_formula_sum     'C10 H9 N7 O3'
_chemical_formula_iupac     'C10 H9 N7 O3'
_chemical_formula_weight     275.24
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.7412(19)
_cell_length_b     10.530(2)
_cell_length_c     13.881(3)
_cell_angle_alpha     81.964(3)
_cell_angle_beta     89.058(3)
_cell_angle_gamma     76.467(3)
_cell_volume     1229.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1528
_cell_measurement_theta_min     2.42
_cell_measurement_theta_max     22.43
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.487
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     568
_exptl_absorpt_coefficient_mu     0.116
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9552
_exptl_absorpt_correction_T_max     0.9684
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(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     6260
_diffrn_reflns_av_R_equivalents     0.0142
_diffrn_reflns_av_sigmaI/netI     0.0340
_diffrn_reflns_theta_min     1.48
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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 > 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     4273
_reflns_number_gt     3416
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0687
_refine_ls_R_factor_gt     0.0548
_refine_ls_wR_factor_gt     0.1290
_refine_ls_wR_factor_ref     0.1392
_refine_ls_goodness_of_fit_ref     1.090
_refine_ls_restrained_S_all     1.090
_refine_ls_number_reflns     4273
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0643P)²+0.1542P] 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     0.167
_refine_diff_density_min     -0.216
_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, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_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
    O1 0.37799(19) 0.44865(16) 0.84885(13) 0.0587(5) Uani d . 1 . . O
    O2 0.1215(2) 0.85965(16) 0.87452(14) 0.0627(5) Uani d . 1 . . O
    O3 0.6580(2) 0.74972(19) 0.89096(15) 0.0704(5) Uani d . 1 . . O
    O4 0.30287(19) 0.27619(15) 0.56331(12) 0.0539(4) Uani d . 1 . . O
    O5 -0.0171(2) 0.64580(16) 0.63154(15) 0.0685(5) Uani d . 1 . . O
    O6 0.1006(2) 0.28786(17) 0.86618(13) 0.0668(5) Uani d . 1 . . O
    N1 0.5668(3) 0.4539(2) 0.66567(16) 0.0600(6) Uani d . 1 . . N
    N2 0.7100(3) 0.1992(2) 0.85962(16) 0.0665(6) Uani d . 1 . . N
    N3 0.5847(3) 0.2667(2) 0.89786(16) 0.0657(6) Uani d . 1 . . N
    N4 0.5192(2) 0.36691(18) 0.83064(15) 0.0522(5) Uani d . 1 . . N
    N5 0.2498(2) 0.65297(19) 0.86509(15) 0.0522(5) Uani d . 1 . . N
    N6 0.3900(2) 0.81687(19) 0.87963(13) 0.0484(5) Uani d . 1 . . N
    N7 0.5296(2) 0.5956(2) 0.87216(15) 0.0525(5) Uani d . 1 . . N
    N8 0.1776(2) 0.0294(2) 0.57196(16) 0.0589(6) Uani d . 1 . . N
    N9 0.5751(2) -0.0074(2) 0.64232(16) 0.0591(6) Uani d . 1 . . N
    N10 0.5279(2) 0.1203(2) 0.62374(16) 0.0564(6) Uani d . 1 . . N
    N11 0.3771(2) 0.14781(18) 0.59594(14) 0.0457(5) Uani d . 1 . . N
    N12 0.1463(2) 0.46196(18) 0.59808(15) 0.0510(5) Uani d . 1 . . N
    N13 0.0302(2) 0.47130(18) 0.75356(16) 0.0503(5) Uani d . 1 . . N
    N14 0.2062(2) 0.27395(17) 0.71977(14) 0.0467(5) Uani d . 1 . . N
    C1 0.7230(3) 0.2597(2) 0.76616(18) 0.0487(6) Uani d . 1 . . C
    C2 0.8311(3) 0.2323(3) 0.6931(2) 0.0598(7) Uani d . 1 . . C
    H2B 0.9162 0.1595 0.7009 0.072 Uiso calc R 1 . . H
    C3 0.8043(3) 0.3188(3) 0.6094(2) 0.0637(7) Uani d . 1 . . C
    H3B 0.8744 0.3067 0.5585 0.076 Uiso calc R 1 . . H
    C4 0.6740(3) 0.4251(3) 0.5985(2) 0.0685(8) Uani d . 1 . . C
    H4A 0.6610 0.4804 0.5393 0.082 Uiso calc R 1 . . H
    C5 0.5993(3) 0.3682(2) 0.74659(17) 0.0440(5) Uani d . 1 . . C
    C6 0.3898(3) 0.5737(2) 0.86318(17) 0.0472(6) Uani d . 1 . . C
    C7 0.2598(3) 0.7752(2) 0.87333(16) 0.0477(6) Uani d . 1 . . C
    C8 0.5198(3) 0.7221(3) 0.88086(17) 0.0499(6) Uani d . 1 . . C
    C9 0.1225(3) 0.9943(2) 0.8837(2) 0.0758(9) Uani d . 1 . . C
    H9B 0.0162 1.0458 0.8839 0.114 Uiso calc R 1 . . H
    H9C 0.1771 1.0300 0.8299 0.114 Uiso calc R 1 . . H
    H9D 0.1748 0.9965 0.9435 0.114 Uiso calc R 1 . . H
    C10 0.6603(4) 0.8833(3) 0.9030(3) 0.0873(10) Uani d . 1 . . C
    H10B 0.7672 0.8901 0.9089 0.131 Uiso calc R 1 . . H
    H10C 0.6043 0.9061 0.9605 0.131 Uiso calc R 1 . . H
    H10D 0.6108 0.9426 0.8474 0.131 Uiso calc R 1 . . H
    C11 0.4507(3) -0.0615(2) 0.62583(16) 0.0435(5) Uani d . 1 . . C
    C12 0.4345(3) -0.1907(2) 0.63291(17) 0.0552(7) Uani d . 1 . . C
    H12B 0.5175 -0.2625 0.6526 0.066 Uiso calc R 1 . . H
    C13 0.2913(3) -0.2056(3) 0.60960(19) 0.0624(7) Uani d . 1 . . C
    H13B 0.2739 -0.2900 0.6130 0.075 Uiso calc R 1 . . H
    C14 0.1685(3) -0.0958(3) 0.5803(2) 0.0685(8) Uani d . 1 . . C
    H14B 0.0720 -0.1119 0.5654 0.082 Uiso calc R 1 . . H
    C15 0.3213(3) 0.0383(2) 0.59527(15) 0.0414(5) Uani d . 1 . . C
    C16 0.2131(3) 0.3396(2) 0.63354(17) 0.0434(5) Uani d . 1 . . C
    C17 0.0543(3) 0.5229(2) 0.6633(2) 0.0502(6) Uani d . 1 . . C
    C18 0.1115(3) 0.3483(2) 0.77727(18) 0.0476(6) Uani d . 1 . . C
    C19 -0.1174(3) 0.7185(3) 0.6996(3) 0.0889(11) Uani d . 1 . . C
    H19A -0.1636 0.8061 0.6683 0.133 Uiso calc R 1 . . H
    H19B -0.0557 0.7231 0.7550 0.133 Uiso calc R 1 . . H
    H19C -0.1991 0.6743 0.7203 0.133 Uiso calc R 1 . . H
    C20 0.0084(4) 0.3641(3) 0.9347(2) 0.0903(11) Uani d . 1 . . C
    H20A 0.0100 0.3097 0.9964 0.135 Uiso calc R 1 . . H
    H20B -0.0981 0.3957 0.9109 0.135 Uiso calc R 1 . . H
    H20C 0.0522 0.4378 0.9424 0.135 Uiso calc R 1 . . H
_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
    O1 N4 . 1.372(2) yes
    O1 C6 . 1.386(3) ?
    O2 C7 . 1.324(3) ?
    O2 C9 . 1.443(3) ?
    O3 C8 . 1.321(3) ?
    O3 C10 . 1.444(3) ?
    O4 N11 . 1.372(2) yes
    O4 C16 . 1.387(3) ?
    O5 C17 . 1.315(3) ?
    O5 C19 . 1.451(3) ?
    O6 C18 . 1.320(3) ?
    O6 C20 . 1.444(3) ?
    N1 C4 . 1.325(3) yes
    N1 C5 . 1.328(3) ?
    N2 N3 . 1.307(3) yes
    N2 C1 . 1.379(3) ?
    N3 N4 . 1.331(3) yes
    N4 C5 . 1.351(3) ?
    N5 C6 . 1.312(3) ?
    N5 C7 . 1.331(3) ?
    N6 C7 . 1.321(3) ?
    N6 C8 . 1.322(3) ?
    N7 C6 . 1.307(3) ?
    N7 C8 . 1.337(3) ?
    N8 C14 . 1.329(3) ?
    N8 C15 . 1.330(3) ?
    N9 N10 . 1.301(3) yes
    N9 C11 . 1.377(3) ?
    N10 N11 . 1.333(3) yes
    N11 C15 . 1.354(3) ?
    N12 C16 . 1.313(3) ?
    N12 C17 . 1.332(3) ?
    N13 C18 . 1.322(3) ?
    N13 C17 . 1.328(3) ?
    N14 C16 . 1.304(3) ?
    N14 C18 . 1.336(3) ?
    C1 C5 . 1.375(3) ?
    C1 C2 . 1.389(3) ?
    C2 C3 . 1.359(4) ?
    C2 H2B . 0.9300 ?
    C3 C4 . 1.391(4) ?
    C3 H3B . 0.9300 ?
    C4 H4A . 0.9300 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C9 H9D . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C10 H10D . 0.9600 ?
    C11 C15 . 1.378(3) ?
    C11 C12 . 1.390(3) ?
    C12 C13 . 1.347(4) ?
    C12 H12B . 0.9300 ?
    C13 C14 . 1.399(4) ?
    C13 H13B . 0.9300 ?
    C14 H14B . 0.9300 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
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
    N4 O1 C6 . . 113.69(18) yes
    C7 O2 C9 . . 117.1(2) ?
    C8 O3 C10 . . 117.9(2) ?
    N11 O4 C16 . . 113.48(16) yes
    C17 O5 C19 . . 116.9(2) ?
    C18 O6 C20 . . 117.4(2) ?
    C4 N1 C5 . . 111.4(2) ?
    N3 N2 C1 . . 108.1(2) ?
    N2 N3 N4 . . 107.2(2) ?
    N3 N4 C5 . . 112.89(19) ?
    N3 N4 O1 . . 119.56(19) ?
    C5 N4 O1 . . 127.33(19) ?
    C6 N5 C7 . . 111.3(2) ?
    C7 N6 C8 . . 113.5(2) ?
    C6 N7 C8 . . 110.9(2) ?
    C14 N8 C15 . . 110.9(2) ?
    N10 N9 C11 . . 108.31(19) ?
    N9 N10 N11 . . 107.28(19) ?
    N10 N11 C15 . . 112.81(18) ?
    N10 N11 O4 . . 118.89(18) ?
    C15 N11 O4 . . 127.96(19) ?
    C16 N12 C17 . . 111.4(2) ?
    C18 N13 C17 . . 113.5(2) ?
    C16 N14 C18 . . 111.0(2) ?
    C5 C1 N2 . . 109.0(2) ?
    C5 C1 C2 . . 117.7(2) ?
    N2 C1 C2 . . 133.3(2) ?
    C3 C2 C1 . . 115.6(2) ?
    C3 C2 H2B . . 122.2 ?
    C1 C2 H2B . . 122.2 ?
    C2 C3 C4 . . 121.2(3) ?
    C2 C3 H3B . . 119.4 ?
    C4 C3 H3B . . 119.4 ?
    N1 C4 C3 . . 125.2(3) ?
    N1 C4 H4A . . 117.4 ?
    C3 C4 H4A . . 117.4 ?
    N1 C5 N4 . . 128.4(2) ?
    N1 C5 C1 . . 128.9(2) ?
    N4 C5 C1 . . 102.76(19) ?
    N7 C6 N5 . . 130.5(2) ?
    N7 C6 O1 . . 118.7(2) ?
    N5 C6 O1 . . 110.8(2) ?
    N6 C7 O2 . . 119.5(2) ?
    N6 C7 N5 . . 126.7(2) ?
    O2 C7 N5 . . 113.8(2) ?
    O3 C8 N6 . . 119.5(2) ?
    O3 C8 N7 . . 113.5(2) ?
    N6 C8 N7 . . 127.0(2) ?
    O2 C9 H9B . . 109.5 ?
    O2 C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O2 C9 H9D . . 109.5 ?
    H9B C9 H9D . . 109.5 ?
    H9C C9 H9D . . 109.5 ?
    O3 C10 H10B . . 109.5 ?
    O3 C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    O3 C10 H10D . . 109.5 ?
    H10B C10 H10D . . 109.5 ?
    H10C C10 H10D . . 109.5 ?
    N9 C11 C15 . . 109.2(2) ?
    N9 C11 C12 . . 133.0(2) ?
    C15 C11 C12 . . 117.8(2) ?
    C13 C12 C11 . . 116.0(2) ?
    C13 C12 H12B . . 122.0 ?
    C11 C12 H12B . . 122.0 ?
    C12 C13 C14 . . 120.8(2) ?
    C12 C13 H13B . . 119.6 ?
    C14 C13 H13B . . 119.6 ?
    N8 C14 C13 . . 125.7(3) ?
    N8 C14 H14B . . 117.1 ?
    C13 C14 H14B . . 117.1 ?
    N8 C15 N11 . . 128.8(2) ?
    N8 C15 C11 . . 128.8(2) ?
    N11 C15 C11 . . 102.4(2) ?
    N14 C16 N12 . . 130.7(2) ?
    N14 C16 O4 . . 118.8(2) ?
    N12 C16 O4 . . 110.5(2) ?
    O5 C17 N13 . . 119.5(2) ?
    O5 C17 N12 . . 114.1(2) ?
    N13 C17 N12 . . 126.4(2) ?
    O6 C18 N13 . . 119.0(2) ?
    O6 C18 N14 . . 114.0(2) ?
    N13 C18 N14 . . 127.0(2) ?
    O5 C19 H19A . . 109.5 ?
    O5 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O5 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O6 C20 H20A . . 109.5 ?
    O6 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O6 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 N2 N3 N4 . . . . 0.3(3) ?
    N2 N3 N4 C5 . . . . 0.0(3) ?
    N2 N3 N4 O1 . . . . 175.0(2) ?
    C6 O1 N4 N3 . . . . 109.2(2) ?
    C6 O1 N4 C5 . . . . -76.6(3) ?
    C11 N9 N10 N11 . . . . 0.0(3) ?
    N9 N10 N11 C15 . . . . -0.2(3) ?
    N9 N10 N11 O4 . . . . -173.99(18) ?
    C16 O4 N11 N10 . . . . -98.7(2) ?
    C16 O4 N11 C15 . . . . 88.6(3) ?
    N3 N2 C1 C5 . . . . -0.5(3) ?
    N3 N2 C1 C2 . . . . 179.7(3) ?
    C5 C1 C2 C3 . . . . 1.4(3) ?
    N2 C1 C2 C3 . . . . -178.9(3) ?
    C1 C2 C3 C4 . . . . -1.6(4) ?
    C5 N1 C4 C3 . . . . 0.4(4) ?
    C2 C3 C4 N1 . . . . 0.8(5) ?
    C4 N1 C5 N4 . . . . 178.7(2) ?
    C4 N1 C5 C1 . . . . -0.6(4) ?
    N3 N4 C5 N1 . . . . -179.7(2) ?
    O1 N4 C5 N1 . . . . 5.7(4) ?
    N3 N4 C5 C1 . . . . -0.3(3) ?
    O1 N4 C5 C1 . . . . -174.8(2) ?
    N2 C1 C5 N1 . . . . 179.9(2) ?
    C2 C1 C5 N1 . . . . -0.3(4) ?
    N2 C1 C5 N4 . . . . 0.5(3) ?
    C2 C1 C5 N4 . . . . -179.7(2) ?
    C8 N7 C6 N5 . . . . -2.7(4) ?
    C8 N7 C6 O1 . . . . 177.1(2) ?
    C7 N5 C6 N7 . . . . 3.3(4) ?
    C7 N5 C6 O1 . . . . -176.49(19) ?
    N4 O1 C6 N7 . . . . -9.7(3) ?
    N4 O1 C6 N5 . . . . 170.17(18) ?
    C8 N6 C7 O2 . . . . 177.9(2) ?
    C8 N6 C7 N5 . . . . -2.5(3) ?
    C9 O2 C7 N6 . . . . -0.6(3) ?
    C9 O2 C7 N5 . . . . 179.7(2) ?
    C6 N5 C7 N6 . . . . -0.4(3) ?
    C6 N5 C7 O2 . . . . 179.3(2) ?
    C10 O3 C8 N6 . . . . 1.7(4) ?
    C10 O3 C8 N7 . . . . -178.8(2) ?
    C7 N6 C8 O3 . . . . -177.3(2) ?
    C7 N6 C8 N7 . . . . 3.2(3) ?
    C6 N7 C8 O3 . . . . 179.5(2) ?
    C6 N7 C8 N6 . . . . -0.9(3) ?
    N10 N9 C11 C15 . . . . 0.3(3) ?
    N10 N9 C11 C12 . . . . 179.3(2) ?
    N9 C11 C12 C13 . . . . -179.5(3) ?
    C15 C11 C12 C13 . . . . -0.5(3) ?
    C11 C12 C13 C14 . . . . 0.0(4) ?
    C15 N8 C14 C13 . . . . 0.1(4) ?
    C12 C13 C14 N8 . . . . 0.3(5) ?
    C14 N8 C15 N11 . . . . 180.0(2) ?
    C14 N8 C15 C11 . . . . -0.8(4) ?
    N10 N11 C15 N8 . . . . 179.7(2) ?
    O4 N11 C15 N8 . . . . -7.2(4) ?
    N10 N11 C15 C11 . . . . 0.3(2) ?
    O4 N11 C15 C11 . . . . 173.44(19) ?
    N9 C11 C15 N8 . . . . -179.7(2) ?
    C12 C11 C15 N8 . . . . 1.0(4) ?
    N9 C11 C15 N11 . . . . -0.3(2) ?
    C12 C11 C15 N11 . . . . -179.6(2) ?
    C18 N14 C16 N12 . . . . 1.4(4) ?
    C18 N14 C16 O4 . . . . -178.2(2) ?
    C17 N12 C16 N14 . . . . -2.2(4) ?
    C17 N12 C16 O4 . . . . 177.40(19) ?
    N11 O4 C16 N14 . . . . -0.8(3) ?
    N11 O4 C16 N12 . . . . 179.54(18) ?
    C19 O5 C17 N13 . . . . 1.0(3) ?
    C19 O5 C17 N12 . . . . -179.1(2) ?
    C18 N13 C17 O5 . . . . -178.5(2) ?
    C18 N13 C17 N12 . . . . 1.6(4) ?
    C16 N12 C17 O5 . . . . -179.4(2) ?
    C16 N12 C17 N13 . . . . 0.5(4) ?
    C20 O6 C18 N13 . . . . -4.5(4) ?
    C20 O6 C18 N14 . . . . 176.1(2) ?
    C17 N13 C18 O6 . . . . 178.1(2) ?
    C17 N13 C18 N14 . . . . -2.6(3) ?
    C16 N14 C18 O6 . . . . -179.4(2) ?
    C16 N14 C18 N13 . . . . 1.3(3) ?
