##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-04-18
_journal_date_accepted     2007-05-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      6
_journal_page_first     o2888
_journal_page_last     o2888
_journal_paper_category     QO
_journal_coeditor_code     HK2234
_publ_contact_author_name     'Dr. Mingjie Zhang'
_publ_contact_author_address
; Department of Chemistry,Tianjin University
  Tianjin 300072
  People's Republic of China
;
_publ_contact_author_email     mjzhangtju@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86 022 27892351'
_publ_section_title
;
4-Hydroxy-3-methoxybenzaldehyde (pyrazin-2-yl)hydrazone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chang-Ying Liu' .
; Department of Chemistry, Tianjin University
  Tianjin 300072
  People's Republic of China
;
    'Jing Hu' .
; Department of Chemistry, Tianjin University
  Tianjin 300072
  People's Republic of China
;
    'Yan-Qiao Zhang' .
; Department of Chemistry, Tianjin University
  Tianjin 300072
  People's Republic of China
;
    'Zhi-Chen Zhu' .
; Department of Material Science and Engineering
  Tianjin Institute of Urban Construction
  Tianjin 300384
  People's Republic of China
;
    'Ming-Jie Zhang' .
; Department of Chemistry, Tianjin University
  Tianjin 300072
  People's Republic of China
;
data_I
_chemical_name_systematic
;
4-Hydroxy-3-methoxybenzaldehyde (pyrazin-2-yl)hydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H12 N4 O2'
_chemical_formula_sum     'C12 H12 N4 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C12 H12 N4 O2'
_chemical_formula_weight     244.26
_chemical_melting_point     196
_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     43.862(6)
_cell_length_b     7.9026(11)
_cell_length_c     13.4958(19)
_cell_angle_alpha     90.00
_cell_angle_beta     92.783(3)
_cell_angle_gamma     90.00
_cell_volume     4672.4(11)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     2951
_cell_measurement_theta_min     2.79
_cell_measurement_theta_max     23.27
_cell_measurement_temperature     294(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.389
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2048
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9766
_exptl_absorpt_correction_T_max     0.9882
_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     'Bruker CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12989
_diffrn_reflns_av_R_equivalents     0.0382
_diffrn_reflns_av_sigmaI/netI     0.0483
_diffrn_reflns_theta_min     0.93
_diffrn_reflns_theta_max     26.38
_diffrn_reflns_theta_full     26.38
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -45
_diffrn_reflns_limit_h_max     54
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     .
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     .
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_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     4741
_reflns_number_gt     2870
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0849
_refine_ls_R_factor_gt     0.0417
_refine_ls_wR_factor_gt     0.0975
_refine_ls_wR_factor_ref     0.1181
_refine_ls_goodness_of_fit_ref     0.989
_refine_ls_restrained_S_all     0.989
_refine_ls_number_reflns     4741
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.056P)²+1.0712P] 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     0.213
_refine_diff_density_min     -0.201
_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, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
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
    O O1 0.09624(3) -0.0018(2) 0.35987(9) 0.0491(4) Uani d . 1 . .
    H H1 0.1125 -0.0479 0.3489 0.074 Uiso calc R 1 . .
    O O2 0.12414(3) -0.05024(18) 0.19008(9) 0.0412(4) Uani d . 1 . .
    O O3 0.88212(3) 0.37662(18) 0.52439(11) 0.0522(4) Uani d . 1 . .
    H H3 0.8939 0.4482 0.5043 0.078 Uiso calc R 1 . .
    O O4 0.84359(3) 0.17444(17) 0.60218(10) 0.0454(4) Uani d . 1 . .
    N N1 -0.07790(4) 0.4233(2) -0.07185(13) 0.0457(5) Uani d . 1 . .
    N N2 -0.03900(4) 0.3369(2) -0.21998(12) 0.0424(4) Uani d . 1 . .
    N N3 -0.00114(4) 0.2727(3) -0.10462(12) 0.0508(5) Uani d . 1 . .
    H H3B 0.0109 0.2598 -0.1525 0.061 Uiso calc R 1 . .
    N N4 0.00922(4) 0.2394(2) -0.00933(12) 0.0429(4) Uani d . 1 . .
    N N5 0.77115(4) 0.2428(2) 1.12707(13) 0.0466(5) Uani d . 1 . .
    N N6 0.74870(4) 0.5668(2) 1.08398(13) 0.0432(4) Uani d . 1 . .
    N N7 0.78167(4) 0.5929(2) 0.95882(13) 0.0448(5) Uani d . 1 . .
    H H7A 0.7774 0.6990 0.9548 0.054 Uiso calc R 1 . .
    N N8 0.80002(4) 0.5187(2) 0.89084(12) 0.0381(4) Uani d . 1 . .
    C C1 -0.06743(5) 0.3908(3) -0.24004(16) 0.0482(6) Uani d . 1 . .
    H H1A -0.0744 0.3999 -0.3061 0.058 Uiso calc R 1 . .
    C C2 -0.08688(5) 0.4334(3) -0.16788(17) 0.0487(6) Uani d . 1 . .
    H H2 -0.1065 0.4697 -0.1857 0.058 Uiso calc R 1 . .
    C C3 -0.04997(4) 0.3702(3) -0.04990(15) 0.0415(5) Uani d . 1 . .
    H H3A -0.0432 0.3618 0.0163 0.050 Uiso calc R 1 . .
    C C4 -0.03019(4) 0.3260(3) -0.12424(14) 0.0366(5) Uani d . 1 . .
    C C5 0.03653(5) 0.1859(3) 0.00035(14) 0.0407(5) Uani d . 1 . .
    H H5 0.0476 0.1749 -0.0563 0.049 Uiso calc R 1 . .
    C C6 0.05136(4) 0.1408(3) 0.09534(14) 0.0369(5) Uani d . 1 . .
    C C7 0.03815(5) 0.1649(3) 0.18529(15) 0.0467(6) Uani d . 1 . .
    H H7 0.0189 0.2137 0.1868 0.056 Uiso calc R 1 . .
    C C8 0.05330(5) 0.1172(3) 0.27277(15) 0.0461(6) Uani d . 1 . .
    H H8 0.0442 0.1343 0.3328 0.055 Uiso calc R 1 . .
    C C9 0.08172(5) 0.0447(3) 0.27178(14) 0.0367(5) Uani d . 1 . .
    C C10 0.09553(4) 0.0212(2) 0.18214(13) 0.0326(4) Uani d . 1 . .
    C C11 0.08029(4) 0.0694(2) 0.09510(14) 0.0362(5) Uani d . 1 . .
    H H11 0.0895 0.0540 0.0352 0.043 Uiso calc R 1 . .
    C C12 0.13893(5) -0.0775(3) 0.10010(16) 0.0587(7) Uani d . 1 . .
    H H12A 0.1268 -0.1518 0.0581 0.088 Uiso calc R 1 . .
    H H12B 0.1586 -0.1279 0.1144 0.088 Uiso calc R 1 . .
    H H12C 0.1415 0.0287 0.0670 0.088 Uiso calc R 1 . .
    C C13 0.73840(5) 0.4715(3) 1.15752(16) 0.0477(6) Uani d . 1 . .
    H H13 0.7233 0.5156 1.1959 0.057 Uiso calc R 1 . .
    C C14 0.74906(5) 0.3134(3) 1.17852(17) 0.0481(6) Uani d . 1 . .
    H H14 0.7408 0.2527 1.2299 0.058 Uiso calc R 1 . .
    C C15 0.78173(5) 0.3346(3) 1.05504(15) 0.0402(5) Uani d . 1 . .
    H H15 0.7972 0.2904 1.0182 0.048 Uiso calc R 1 . .
    C C16 0.77044(4) 0.4973(2) 1.03167(14) 0.0345(5) Uani d . 1 . .
    C C17 0.81365(4) 0.6185(3) 0.83397(15) 0.0381(5) Uani d . 1 . .
    H H17 0.8122 0.7344 0.8445 0.046 Uiso calc R 1 . .
    C C18 0.83143(4) 0.5577(2) 0.75289(14) 0.0326(5) Uani d . 1 . .
    C C19 0.85151(4) 0.6639(2) 0.70776(15) 0.0371(5) Uani d . 1 . .
    H H19 0.8536 0.7752 0.7294 0.045 Uiso calc R 1 . .
    C C20 0.86862(4) 0.6076(2) 0.63082(15) 0.0374(5) Uani d . 1 . .
    H H20 0.8821 0.6811 0.6018 0.045 Uiso calc R 1 . .
    C C21 0.86583(4) 0.4434(2) 0.59665(14) 0.0348(5) Uani d . 1 . .
    C C22 0.84495(4) 0.3358(2) 0.64100(14) 0.0336(5) Uani d . 1 . .
    C C23 0.82815(4) 0.3918(2) 0.71763(14) 0.0332(5) Uani d . 1 . .
    H H23 0.8145 0.3190 0.7464 0.040 Uiso calc R 1 . .
    C C24 0.81790(5) 0.0741(3) 0.62537(17) 0.0499(6) Uani d . 1 . .
    H H24A 0.8191 0.0467 0.6947 0.075 Uiso calc R 1 . .
    H H24B 0.8178 -0.0283 0.5871 0.075 Uiso calc R 1 . .
    H H24C 0.7995 0.1363 0.6099 0.075 Uiso calc R 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
    O1 C9 . 1.371(2) ?
    O1 H1 . 0.8200 yes
    O2 C10 . 1.375(2) ?
    O2 C12 . 1.421(2) ?
    O3 C21 . 1.344(2) ?
    O3 H3 . 0.8200 ?
    O4 C22 . 1.379(2) ?
    O4 C24 . 1.425(2) ?
    N1 C3 . 1.315(2) ?
    N1 C2 . 1.338(3) ?
    N2 C1 . 1.333(2) ?
    N2 C4 . 1.333(2) ?
    N3 C4 . 1.355(2) ?
    N3 N4 . 1.368(2) yes
    N3 H3B . 0.8600 ?
    N4 C5 . 1.271(2) yes
    N5 C15 . 1.315(3) ?
    N5 C14 . 1.341(3) ?
    N6 C16 . 1.332(2) ?
    N6 C13 . 1.342(3) ?
    N7 C16 . 1.351(2) ?
    N7 N8 . 1.380(2) yes
    N7 H7A . 0.8600 ?
    N8 C17 . 1.270(2) yes
    C1 C2 . 1.367(3) ?
    C1 H1A . 0.9300 ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.402(3) ?
    C3 H3A . 0.9300 ?
    C5 C6 . 1.453(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.384(3) ?
    C6 C11 . 1.389(3) ?
    C7 C8 . 1.379(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.373(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.391(3) ?
    C10 C11 . 1.377(3) ?
    C11 H11 . 0.9300 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 C14 . 1.358(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.408(3) ?
    C15 H15 . 0.9300 ?
    C17 C18 . 1.456(3) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.379(3) ?
    C18 C23 . 1.400(3) ?
    C19 C20 . 1.384(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.381(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.405(3) ?
    C22 C23 . 1.372(3) ?
    C23 H23 . 0.9300 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 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
    C9 O1 H1 . . 109.5 ?
    C10 O2 C12 . . 116.66(15) yes
    C21 O3 H3 . . 109.5 ?
    C22 O4 C24 . . 116.84(15) yes
    C3 N1 C2 . . 117.65(17) ?
    C1 N2 C4 . . 116.21(17) ?
    C4 N3 N4 . . 120.62(16) yes
    C4 N3 H3B . . 119.7 ?
    N4 N3 H3B . . 119.7 ?
    C5 N4 N3 . . 115.40(16) yes
    C15 N5 C14 . . 116.28(19) ?
    C16 N6 C13 . . 115.85(18) ?
    C16 N7 N8 . . 119.42(16) yes
    C16 N7 H7A . . 120.3 ?
    N8 N7 H7A . . 120.3 ?
    C17 N8 N7 . . 116.43(17) yes
    N2 C1 C2 . . 122.9(2) ?
    N2 C1 H1A . . 118.5 ?
    C2 C1 H1A . . 118.5 ?
    N1 C2 C1 . . 120.71(19) ?
    N1 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    N1 C3 C4 . . 121.36(19) ?
    N1 C3 H3A . . 119.3 ?
    C4 C3 H3A . . 119.3 ?
    N2 C4 N3 . . 115.78(17) ?
    N2 C4 C3 . . 121.12(18) ?
    N3 C4 C3 . . 123.09(18) ?
    N4 C5 C6 . . 123.47(18) yes
    N4 C5 H5 . . 118.3 ?
    C6 C5 H5 . . 118.3 ?
    C7 C6 C11 . . 118.67(18) ?
    C7 C6 C5 . . 123.47(18) ?
    C11 C6 C5 . . 117.86(17) ?
    C8 C7 C6 . . 120.58(19) ?
    C8 C7 H7 . . 119.7 ?
    C6 C7 H7 . . 119.7 ?
    C9 C8 C7 . . 120.39(18) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    O1 C9 C8 . . 119.17(17) yes
    O1 C9 C10 . . 120.96(18) yes
    C8 C9 C10 . . 119.87(18) ?
    O2 C10 C11 . . 125.68(16) yes
    O2 C10 C9 . . 114.90(16) yes
    C11 C10 C9 . . 119.42(18) ?
    C10 C11 C6 . . 121.07(17) ?
    C10 C11 H11 . . 119.5 ?
    C6 C11 H11 . . 119.5 ?
    O2 C12 H12A . . 109.5 ?
    O2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    O2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    N6 C13 C14 . . 123.07(19) ?
    N6 C13 H13 . . 118.5 ?
    C14 C13 H13 . . 118.5 ?
    N5 C14 C13 . . 121.6(2) ?
    N5 C14 H14 . . 119.2 ?
    C13 C14 H14 . . 119.2 ?
    N5 C15 C16 . . 122.44(19) ?
    N5 C15 H15 . . 118.8 ?
    C16 C15 H15 . . 118.8 ?
    N6 C16 N7 . . 116.79(18) ?
    N6 C16 C15 . . 120.69(18) ?
    N7 C16 C15 . . 122.47(17) ?
    N8 C17 C18 . . 122.33(18) yes
    N8 C17 H17 . . 118.8 ?
    C18 C17 H17 . . 118.8 ?
    C19 C18 C23 . . 118.48(17) ?
    C19 C18 C17 . . 120.55(18) ?
    C23 C18 C17 . . 120.96(17) ?
    C18 C19 C20 . . 121.13(18) ?
    C18 C19 H19 . . 119.4 ?
    C20 C19 H19 . . 119.4 ?
    C21 C20 C19 . . 120.69(18) ?
    C21 C20 H20 . . 119.7 ?
    C19 C20 H20 . . 119.7 ?
    O3 C21 C20 . . 124.72(17) yes
    O3 C21 C22 . . 116.88(17) yes
    C20 C21 C22 . . 118.39(17) ?
    C23 C22 O4 . . 124.72(17) yes
    C23 C22 C21 . . 120.75(18) ?
    O4 C22 C21 . . 114.52(16) yes
    C22 C23 C18 . . 120.54(17) ?
    C22 C23 H23 . . 119.7 ?
    C18 C23 H23 . . 119.7 ?
    O4 C24 H24A . . 109.5 ?
    O4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    O4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 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
    C4 N3 N4 C5 . . . . 178.2(2) ?
    C16 N7 N8 C17 . . . . -169.45(19) ?
    C4 N2 C1 C2 . . . . 0.0(3) ?
    C3 N1 C2 C1 . . . . -0.5(3) ?
    N2 C1 C2 N1 . . . . 0.4(4) ?
    C2 N1 C3 C4 . . . . 0.1(3) ?
    C1 N2 C4 N3 . . . . -179.34(19) ?
    C1 N2 C4 C3 . . . . -0.4(3) ?
    N4 N3 C4 N2 . . . . -172.90(19) ?
    N4 N3 C4 C3 . . . . 8.1(3) ?
    N1 C3 C4 N2 . . . . 0.3(3) ?
    N1 C3 C4 N3 . . . . 179.2(2) ?
    N3 N4 C5 C6 . . . . -178.85(19) ?
    N4 C5 C6 C7 . . . . -5.5(3) ?
    N4 C5 C6 C11 . . . . 174.3(2) ?
    C11 C6 C7 C8 . . . . -0.7(3) ?
    C5 C6 C7 C8 . . . . 179.1(2) ?
    C6 C7 C8 C9 . . . . -0.2(3) ?
    C7 C8 C9 O1 . . . . -179.9(2) ?
    C7 C8 C9 C10 . . . . 0.9(3) ?
    C12 O2 C10 C11 . . . . -0.7(3) ?
    C12 O2 C10 C9 . . . . 179.54(19) ?
    O1 C9 C10 O2 . . . . -0.1(3) ?
    C8 C9 C10 O2 . . . . 179.09(18) ?
    O1 C9 C10 C11 . . . . -179.95(18) ?
    C8 C9 C10 C11 . . . . -0.7(3) ?
    O2 C10 C11 C6 . . . . -179.95(18) ?
    C9 C10 C11 C6 . . . . -0.1(3) ?
    C7 C6 C11 C10 . . . . 0.9(3) ?
    C5 C6 C11 C10 . . . . -178.98(18) ?
    C16 N6 C13 C14 . . . . -0.2(3) ?
    C15 N5 C14 C13 . . . . -0.4(3) ?
    N6 C13 C14 N5 . . . . 0.9(4) ?
    C14 N5 C15 C16 . . . . -0.7(3) ?
    C13 N6 C16 N7 . . . . -178.42(19) ?
    C13 N6 C16 C15 . . . . -0.9(3) ?
    N8 N7 C16 N6 . . . . -168.35(17) ?
    N8 N7 C16 C15 . . . . 14.2(3) ?
    N5 C15 C16 N6 . . . . 1.4(3) ?
    N5 C15 C16 N7 . . . . 178.8(2) ?
    N7 N8 C17 C18 . . . . -174.17(17) ?
    N8 C17 C18 C19 . . . . -164.76(19) ?
    N8 C17 C18 C23 . . . . 16.5(3) ?
    C23 C18 C19 C20 . . . . -1.4(3) ?
    C17 C18 C19 C20 . . . . 179.80(18) ?
    C18 C19 C20 C21 . . . . 0.5(3) ?
    C19 C20 C21 O3 . . . . -178.01(19) ?
    C19 C20 C21 C22 . . . . 0.8(3) ?
    C24 O4 C22 C23 . . . . 16.6(3) ?
    C24 O4 C22 C21 . . . . -164.40(18) ?
    O3 C21 C22 C23 . . . . 177.75(18) ?
    C20 C21 C22 C23 . . . . -1.2(3) ?
    O3 C21 C22 O4 . . . . -1.3(3) ?
    C20 C21 C22 O4 . . . . 179.83(17) ?
    O4 C22 C23 C18 . . . . 179.11(18) ?
    C21 C22 C23 C18 . . . . 0.2(3) ?
    C19 C18 C23 C22 . . . . 1.1(3) ?
    C17 C18 C23 C22 . . . . 179.84(18) ?
