##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#                                                                            #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-04-29
_journal_date_accepted     2009-04-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      6
_journal_page_first     o1187
_journal_page_last     o1187
_journal_paper_category     QO
_journal_coeditor_code     HK2679
_publ_contact_author_name     'Songlei Zhu'
_publ_contact_author_address
;
Department of Chemistry,
Xuzhou Medical College,
Xuzhou 221002,
People's Republic of China
;
_publ_contact_author_email     'songleizhu@126.com'
_publ_contact_author_fax     '86 516 83979800'
_publ_contact_author_phone     '86 516 83979800'
_publ_section_title
;
6-(1<i>H</i>-Indol-3-yl)-4-phenyl-2,2'-bipyridine-5-carbonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Weijun Zhu' ?
;
Xuzhou College of Industrial Technology,
Xuzhou 221140,
People's Republic of China
;
    'Yan Xiang' ?
;
Xuzhou Pharmaceutical College,
Xuzhou 221116,
People's Republic of China
;
    'Songlei Zhu' ?
;
Xuzhou Medical College,
Xuzhou 221002,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6-(1<i>H</i>-Indol-3-yl)-4-phenyl-2,2'-bipyridine-5-carbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H16 N4'
_chemical_formula_sum     'C25 H16 N4'
_chemical_formula_iupac     'C25 H16 N4'
_chemical_formula_weight     372.42
_chemical_melting_point     ?
_chemical_melting_point_gt     567
_chemical_melting_point_lt     568
_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     9.7744(16)
_cell_length_b     9.7927(11)
_cell_length_c     11.233(2)
_cell_angle_alpha     73.121(13)
_cell_angle_beta     86.008(16)
_cell_angle_gamma     63.853(10)
_cell_volume     921.5(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3008
_cell_measurement_theta_min     3.1
_cell_measurement_theta_max     25.3
_cell_measurement_temperature     291(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     388
_exptl_absorpt_coefficient_mu     0.082
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Jacobson, 1998)'
_exptl_absorpt_correction_T_min     0.966
_exptl_absorpt_correction_T_max     0.976
_exptl_special_details
;
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku Mercury'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     8987
_diffrn_reflns_av_R_equivalents     0.0266
_diffrn_reflns_av_sigmaI/netI     0.0353
_diffrn_reflns_theta_min     3.10
_diffrn_reflns_theta_max     25.34
_diffrn_reflns_theta_full     25.34
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     3349
_reflns_number_gt     2614
_reflns_threshold_expression     I>2/s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0739
_refine_ls_R_factor_gt     0.0544
_refine_ls_wR_factor_gt     0.1159
_refine_ls_wR_factor_ref     0.1264
_refine_ls_goodness_of_fit_ref     1.122
_refine_ls_restrained_S_all     1.122
_refine_ls_number_reflns     3349
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.1499P] where P=(Fo^2^+2Fc^2^)/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     0.158
_refine_diff_density_min     -0.205
_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'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2001)'
_computing_cell_refinement     'CrystalClear (Rigaku/MSC, 2001)'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                              'ORTEPII (Johnson, 1976)  and PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    N N1 0.94201(16) 0.20772(17) 0.54741(13) 0.0355(4) Uani d . 1 . .
    N N2 1.20413(18) 0.3774(2) 0.44026(14) 0.0455(4) Uani d . 1 . .
    N N3 0.5855(2) 0.1895(2) 0.28547(16) 0.0606(5) Uani d . 1 . .
    N N4 0.64100(17) -0.04598(18) 0.69177(14) 0.0422(4) Uani d . 1 . .
    H H4 0.5936 -0.1043 0.7025 0.051 Uiso calc R 1 . .
    C C1 1.01436(19) 0.2799(2) 0.46717(16) 0.0347(4) Uani d . 1 . .
    C C2 0.98275(19) 0.3310(2) 0.33960(16) 0.0371(4) Uani d . 1 . .
    H H2 1.0382 0.3776 0.2873 0.045 Uiso calc R 1 . .
    C C3 0.86846(19) 0.3126(2) 0.28960(16) 0.0353(4) Uani d . 1 . .
    C C4 0.79281(19) 0.2362(2) 0.37308(16) 0.0348(4) Uani d . 1 . .
    C C5 0.83308(19) 0.1829(2) 0.50305(16) 0.0334(4) Uani d . 1 . .
    C C6 1.13427(19) 0.3032(2) 0.52184(16) 0.0354(4) Uani d . 1 . .
    C C7 1.1727(2) 0.2494(2) 0.64913(18) 0.0449(5) Uani d . 1 . .
    H H7 1.1226 0.1981 0.7039 0.054 Uiso calc R 1 . .
    C C8 1.2862(2) 0.2731(3) 0.6929(2) 0.0519(5) Uani d . 1 . .
    H H8 1.3135 0.2383 0.7779 0.062 Uiso calc R 1 . .
    C C9 1.3586(2) 0.3482(2) 0.6104(2) 0.0494(5) Uani d . 1 . .
    H H9 1.4361 0.3648 0.6378 0.059 Uiso calc R 1 . .
    C C10 1.3136(2) 0.3981(3) 0.4861(2) 0.0521(5) Uani d . 1 . .
    H H10 1.3625 0.4497 0.4302 0.063 Uiso calc R 1 . .
    C C11 0.8284(2) 0.3777(2) 0.15322(16) 0.0379(4) Uani d . 1 . .
    C C12 0.9407(2) 0.3356(2) 0.07066(17) 0.0445(5) Uani d . 1 . .
    H H12 1.0400 0.2617 0.1010 0.053 Uiso calc R 1 . .
    C C13 0.9065(3) 0.4026(3) -0.05660(18) 0.0529(6) Uani d . 1 . .
    H H13 0.9823 0.3725 -0.1114 0.063 Uiso calc R 1 . .
    C C14 0.7602(3) 0.5140(3) -0.10229(19) 0.0555(6) Uani d . 1 . .
    H H14 0.7376 0.5599 -0.1878 0.067 Uiso calc R 1 . .
    C C15 0.6484(3) 0.5570(3) -0.02151(19) 0.0532(6) Uani d . 1 . .
    H H15 0.5498 0.6323 -0.0525 0.064 Uiso calc R 1 . .
    C C16 0.6809(2) 0.4891(2) 0.10587(18) 0.0460(5) Uani d . 1 . .
    H H16 0.6039 0.5181 0.1600 0.055 Uiso calc R 1 . .
    C C17 0.6772(2) 0.2108(2) 0.32443(17) 0.0423(5) Uani d . 1 . .
    C C18 0.7603(2) 0.1025(2) 0.59690(16) 0.0352(4) Uani d . 1 . .
    C C19 0.6856(2) 0.0176(2) 0.58127(17) 0.0385(4) Uani d . 1 . .
    H H19 0.6682 0.0056 0.5054 0.046 Uiso calc R 1 . .
    C C20 0.6833(2) -0.0028(2) 0.78422(17) 0.0380(4) Uani d . 1 . .
    C C21 0.6582(2) -0.0376(2) 0.90989(18) 0.0476(5) Uani d . 1 . .
    H H21 0.6081 -0.1001 0.9444 0.057 Uiso calc R 1 . .
    C C22 0.7105(3) 0.0240(3) 0.98141(19) 0.0568(6) Uani d . 1 . .
    H H22 0.6957 0.0029 1.0663 0.068 Uiso calc R 1 . .
    C C23 0.7851(3) 0.1175(3) 0.92946(19) 0.0601(6) Uani d . 1 . .
    H H23 0.8188 0.1581 0.9803 0.072 Uiso calc R 1 . .
    C C24 0.8104(2) 0.1515(3) 0.80452(18) 0.0507(5) Uani d . 1 . .
    H H24 0.8605 0.2143 0.7711 0.061 Uiso calc R 1 . .
    C C25 0.7595(2) 0.0901(2) 0.72879(16) 0.0366(4) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0353(8) 0.0367(9) 0.0374(8) -0.0191(7) 0.0027(7) -0.0097(7)
    N2 0.0430(9) 0.0583(11) 0.0475(9) -0.0321(8) 0.0058(8) -0.0173(8)
    N3 0.0675(12) 0.0748(13) 0.0507(10) -0.0502(11) -0.0130(9) 0.0006(9)
    N4 0.0439(9) 0.0449(9) 0.0476(9) -0.0298(8) 0.0052(7) -0.0109(7)
    C1 0.0320(9) 0.0349(10) 0.0378(10) -0.0153(8) 0.0024(8) -0.0102(8)
    C2 0.0336(9) 0.0415(11) 0.0369(10) -0.0206(8) 0.0024(8) -0.0058(8)
    C3 0.0354(10) 0.0346(10) 0.0355(10) -0.0159(8) 0.0005(8) -0.0081(8)
    C4 0.0346(9) 0.0346(10) 0.0362(10) -0.0172(8) 0.0001(8) -0.0082(8)
    C5 0.0329(9) 0.0314(9) 0.0385(10) -0.0157(8) 0.0034(8) -0.0114(8)
    C6 0.0319(9) 0.0355(10) 0.0407(10) -0.0152(8) 0.0036(8) -0.0134(8)
    C7 0.0452(11) 0.0490(12) 0.0415(11) -0.0237(10) -0.0025(9) -0.0083(9)
    C8 0.0514(12) 0.0575(13) 0.0492(12) -0.0256(11) -0.0101(10) -0.0131(10)
    C9 0.0334(10) 0.0567(13) 0.0663(14) -0.0199(10) -0.0016(10) -0.0281(11)
    C10 0.0458(12) 0.0661(14) 0.0611(13) -0.0364(11) 0.0121(10) -0.0249(11)
    C11 0.0418(10) 0.0419(11) 0.0360(10) -0.0255(9) 0.0003(8) -0.0080(8)
    C12 0.0459(11) 0.0509(12) 0.0399(11) -0.0266(10) 0.0016(9) -0.0089(9)
    C13 0.0668(14) 0.0664(15) 0.0398(11) -0.0420(13) 0.0114(10) -0.0171(10)
    C14 0.0770(16) 0.0650(15) 0.0357(11) -0.0472(13) -0.0048(11) -0.0026(10)
    C15 0.0566(13) 0.0545(13) 0.0463(12) -0.0306(11) -0.0118(11) 0.0018(10)
    C16 0.0448(11) 0.0539(12) 0.0410(10) -0.0260(10) -0.0005(9) -0.0085(9)
    C17 0.0457(11) 0.0469(12) 0.0382(10) -0.0283(10) 0.0001(9) -0.0042(9)
    C18 0.0334(9) 0.0345(10) 0.0388(10) -0.0164(8) 0.0030(8) -0.0098(8)
    C19 0.0408(10) 0.0398(11) 0.0387(10) -0.0215(9) 0.0030(8) -0.0109(8)
    C20 0.0339(10) 0.0373(10) 0.0436(11) -0.0174(8) 0.0041(8) -0.0105(8)
    C21 0.0476(12) 0.0545(13) 0.0449(11) -0.0305(10) 0.0111(9) -0.0091(10)
    C22 0.0709(15) 0.0729(15) 0.0377(11) -0.0436(13) 0.0129(10) -0.0146(11)
    C23 0.0815(16) 0.0805(16) 0.0432(12) -0.0570(14) 0.0122(11) -0.0205(11)
    C24 0.0656(14) 0.0626(13) 0.0424(11) -0.0457(12) 0.0096(10) -0.0145(10)
    C25 0.0356(10) 0.0374(10) 0.0394(10) -0.0199(8) 0.0033(8) -0.0091(8)
_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
    N1 C1 . 1.339(2) ?
    N1 C5 . 1.347(2) ?
    N2 C10 . 1.334(2) ?
    N2 C6 . 1.341(2) ?
    N3 C17 . 1.144(2) ?
    N4 C19 . 1.354(2) ?
    N4 C20 . 1.377(2) ?
    N4 H4 . 0.8600 ?
    C1 C2 . 1.381(2) ?
    C1 C6 . 1.490(2) ?
    C2 C3 . 1.385(2) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.404(2) ?
    C3 C11 . 1.484(2) ?
    C4 C5 . 1.420(2) ?
    C4 C17 . 1.432(2) ?
    C5 C18 . 1.465(2) ?
    C6 C7 . 1.388(2) ?
    C7 C8 . 1.377(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.368(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.371(3) ?
    C9 H9 . 0.9300 ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.385(3) ?
    C11 C16 . 1.391(3) ?
    C12 C13 . 1.384(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.378(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.369(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.384(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C18 C19 . 1.375(2) ?
    C18 C25 . 1.451(2) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.384(3) ?
    C20 C25 . 1.405(2) ?
    C21 C22 . 1.372(3) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.389(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.376(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.398(3) ?
    C24 H24 . 0.9300 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 N1 C5 . . 119.18(15) ?
    C10 N2 C6 . . 117.30(17) ?
    C19 N4 C20 . . 109.41(15) ?
    C19 N4 H4 . . 125.3 ?
    C20 N4 H4 . . 125.3 ?
    N1 C1 C2 . . 123.09(15) ?
    N1 C1 C6 . . 116.67(15) ?
    C2 C1 C6 . . 120.24(16) ?
    C1 C2 C3 . . 119.94(16) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C2 C3 C4 . . 117.25(16) ?
    C2 C3 C11 . . 119.47(16) ?
    C4 C3 C11 . . 123.25(15) ?
    C3 C4 C5 . . 120.12(15) ?
    C3 C4 C17 . . 118.82(15) ?
    C5 C4 C17 . . 121.05(16) ?
    N1 C5 C4 . . 120.37(15) ?
    N1 C5 C18 . . 115.71(15) ?
    C4 C5 C18 . . 123.91(15) ?
    N2 C6 C7 . . 122.15(16) ?
    N2 C6 C1 . . 115.83(15) ?
    C7 C6 C1 . . 122.01(16) ?
    C8 C7 C6 . . 118.82(18) ?
    C8 C7 H7 . . 120.6 ?
    C6 C7 H7 . . 120.6 ?
    C9 C8 C7 . . 119.50(19) ?
    C9 C8 H8 . . 120.2 ?
    C7 C8 H8 . . 120.2 ?
    C8 C9 C10 . . 118.03(18) ?
    C8 C9 H9 . . 121.0 ?
    C10 C9 H9 . . 121.0 ?
    N2 C10 C9 . . 124.20(19) ?
    N2 C10 H10 . . 117.9 ?
    C9 C10 H10 . . 117.9 ?
    C12 C11 C16 . . 118.78(17) ?
    C12 C11 C3 . . 119.99(16) ?
    C16 C11 C3 . . 121.11(17) ?
    C13 C12 C11 . . 120.51(19) ?
    C13 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    C14 C13 C12 . . 120.1(2) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C15 C14 C13 . . 119.85(19) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C14 C15 C16 . . 120.5(2) ?
    C14 C15 H15 . . 119.8 ?
    C16 C15 H15 . . 119.8 ?
    C15 C16 C11 . . 120.2(2) ?
    C15 C16 H16 . . 119.9 ?
    C11 C16 H16 . . 119.9 ?
    N3 C17 C4 . . 179.5(2) ?
    C19 C18 C25 . . 105.64(15) ?
    C19 C18 C5 . . 128.12(16) ?
    C25 C18 C5 . . 126.18(15) ?
    N4 C19 C18 . . 110.50(16) ?
    N4 C19 H19 . . 124.7 ?
    C18 C19 H19 . . 124.7 ?
    N4 C20 C21 . . 129.29(17) ?
    N4 C20 C25 . . 107.56(15) ?
    C21 C20 C25 . . 123.15(17) ?
    C22 C21 C20 . . 117.15(18) ?
    C22 C21 H21 . . 121.4 ?
    C20 C21 H21 . . 121.4 ?
    C21 C22 C23 . . 121.23(19) ?
    C21 C22 H22 . . 119.4 ?
    C23 C22 H22 . . 119.4 ?
    C24 C23 C22 . . 121.5(2) ?
    C24 C23 H23 . . 119.2 ?
    C22 C23 H23 . . 119.2 ?
    C23 C24 C25 . . 118.88(18) ?
    C23 C24 H24 . . 120.6 ?
    C25 C24 H24 . . 120.6 ?
    C24 C25 C20 . . 118.06(17) ?
    C24 C25 C18 . . 135.01(17) ?
    C20 C25 C18 . . 106.88(15) ?
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
    C5 N1 C1 C2 . . . . 0.0(3) ?
    C5 N1 C1 C6 . . . . -179.68(15) ?
    N1 C1 C2 C3 . . . . 2.0(3) ?
    C6 C1 C2 C3 . . . . -178.34(16) ?
    C1 C2 C3 C4 . . . . -2.2(3) ?
    C1 C2 C3 C11 . . . . 175.87(17) ?
    C2 C3 C4 C5 . . . . 0.7(3) ?
    C11 C3 C4 C5 . . . . -177.30(16) ?
    C2 C3 C4 C17 . . . . -178.14(16) ?
    C11 C3 C4 C17 . . . . 3.8(3) ?
    C1 N1 C5 C4 . . . . -1.6(2) ?
    C1 N1 C5 C18 . . . . 179.67(15) ?
    C3 C4 C5 N1 . . . . 1.2(3) ?
    C17 C4 C5 N1 . . . . -179.95(17) ?
    C3 C4 C5 C18 . . . . 179.84(16) ?
    C17 C4 C5 C18 . . . . -1.3(3) ?
    C10 N2 C6 C7 . . . . 0.0(3) ?
    C10 N2 C6 C1 . . . . -179.08(16) ?
    N1 C1 C6 N2 . . . . -179.21(15) ?
    C2 C1 C6 N2 . . . . 1.1(3) ?
    N1 C1 C6 C7 . . . . 1.7(3) ?
    C2 C1 C6 C7 . . . . -178.01(17) ?
    N2 C6 C7 C8 . . . . 0.0(3) ?
    C1 C6 C7 C8 . . . . 179.07(17) ?
    C6 C7 C8 C9 . . . . -0.3(3) ?
    C7 C8 C9 C10 . . . . 0.4(3) ?
    C6 N2 C10 C9 . . . . 0.2(3) ?
    C8 C9 C10 N2 . . . . -0.4(3) ?
    C2 C3 C11 C12 . . . . 54.4(2) ?
    C4 C3 C11 C12 . . . . -127.63(19) ?
    C2 C3 C11 C16 . . . . -121.39(19) ?
    C4 C3 C11 C16 . . . . 56.6(3) ?
    C16 C11 C12 C13 . . . . -0.3(3) ?
    C3 C11 C12 C13 . . . . -176.21(17) ?
    C11 C12 C13 C14 . . . . 1.0(3) ?
    C12 C13 C14 C15 . . . . -0.7(3) ?
    C13 C14 C15 C16 . . . . -0.1(3) ?
    C14 C15 C16 C11 . . . . 0.8(3) ?
    C12 C11 C16 C15 . . . . -0.5(3) ?
    C3 C11 C16 C15 . . . . 175.28(17) ?
    N1 C5 C18 C19 . . . . -157.15(17) ?
    C4 C5 C18 C19 . . . . 24.1(3) ?
    N1 C5 C18 C25 . . . . 19.5(3) ?
    C4 C5 C18 C25 . . . . -159.21(17) ?
    C20 N4 C19 C18 . . . . 0.8(2) ?
    C25 C18 C19 N4 . . . . -0.5(2) ?
    C5 C18 C19 N4 . . . . 176.68(17) ?
    C19 N4 C20 C21 . . . . 178.41(19) ?
    C19 N4 C20 C25 . . . . -0.8(2) ?
    N4 C20 C21 C22 . . . . -178.64(19) ?
    C25 C20 C21 C22 . . . . 0.5(3) ?
    C20 C21 C22 C23 . . . . 0.1(3) ?
    C21 C22 C23 C24 . . . . -0.3(4) ?
    C22 C23 C24 C25 . . . . 0.0(4) ?
    C23 C24 C25 C20 . . . . 0.6(3) ?
    C23 C24 C25 C18 . . . . 177.8(2) ?
    N4 C20 C25 C24 . . . . 178.46(16) ?
    C21 C20 C25 C24 . . . . -0.8(3) ?
    N4 C20 C25 C18 . . . . 0.5(2) ?
    C21 C20 C25 C18 . . . . -178.79(17) ?
    C19 C18 C25 C24 . . . . -177.5(2) ?
    C5 C18 C25 C24 . . . . 5.3(3) ?
    C19 C18 C25 C20 . . . . 0.0(2) ?
    C5 C18 C25 C20 . . . . -177.27(16) ?
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
    N4 H4 N3 2_656 0.86 2.23 3.066(2) 164
    C12 H12 Cg5 2_576 0.93 2.84 3.649(3) 146
    C23 H23 Cg4 1_554 0.93 2.91 3.711(3) 145