##############################################################################
###                                                                        ###
###        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     2007-06-20
_journal_date_accepted     2007-07-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3443
_journal_page_last     o3443
_journal_paper_category     QO
_journal_coeditor_code     IS2184
_publ_contact_author_name     'Dr. Resat Ustabas '
_publ_contact_author_address
;
Anatolian Trade High School
Teacher of Physics
Merzifon-05300
Amasya
Turkey
;
_publ_contact_author_email     rustabas@omu.edu.tr
_publ_contact_author_fax     ' '
_publ_contact_author_phone     ' '
_publ_section_title
;
1-Acetonyl-4-(2,5-dimethyl-4H-1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-\
1H-1,2,4-triazol-5(4H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    "Ustabaş, Reşat"
;
Anatolian Trade High School
Teacher of Physics
Merzifon 05300
Amasya
Turkey
;
    "Çoruh, Ufuk"
;
Department of Computer Education and Instructional Technology
Educational Faculty
Ondokuz Mayıs University
55200 Atakum-Samsun
Turkey
;
    'Sancak, Kemal'
;
Department of Chemistry
Faculty of Arts and Sciences
Karadeniz Teknik University
61080 Trabzon
Turkey
;
    'Demirkan, Esra'
;
Department of Chemistry
Faculty of Arts and Sciences
Karadeniz Teknik University
61080 Trabzon
Turkey
;
data_I
_chemical_name_systematic
;
1-acetonyl-4-(2,5-dimethyl-4H-\
1,2,4-triazol-4-yl)-3-(2-thienylmethyl)-1H-1,2,4-triazol-5(4H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H16 N6 O2 S'
_chemical_formula_sum     'C14 H16 N6 O2 S'
_chemical_formula_iupac     'C14 H16 N6 O2 S'
_chemical_formula_weight     332.39
_chemical_melting_point     ?
_symmetry_cell_setting     'monoclinic'
_symmetry_space_group_name_H-M     'C 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'
_cell_length_a     21.1928(16)
_cell_length_b     9.6058(6)
_cell_length_c     8.3020(7)
_cell_angle_alpha     90.00
_cell_angle_beta     106.696(6)
_cell_angle_gamma     90.00
_cell_volume     1618.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3185
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     27.12
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.364
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     696
_exptl_absorpt_coefficient_mu     0.219
_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     293(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     9238
_diffrn_reflns_av_R_equivalents     0.0390
_diffrn_reflns_av_sigmaI/netI     0.0288
_diffrn_reflns_theta_min     2.35
_diffrn_reflns_theta_max     27.12
_diffrn_reflns_theta_full     27.12
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -27
_diffrn_reflns_limit_h_max     27
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_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     3357
_reflns_number_gt     3185
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0353
_refine_ls_R_factor_gt     0.0332
_refine_ls_wR_factor_gt     0.0955
_refine_ls_wR_factor_ref     0.0968
_refine_ls_goodness_of_fit_ref     1.063
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     3357
_refine_ls_number_parameters     246
_refine_ls_number_restraints     179
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0678P)²+0.126P] 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     0.149
_refine_diff_density_min     -0.177
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.015(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 1644 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.02(8)
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'
    'S' 'S' 0.1246 0.1234
                         '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     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.03169(6) 0.79946(12) -0.49156(15) 0.0472(3) Uani d . 1 . .
    N N1 0.13400(7) 0.64873(13) -0.25347(17) 0.0422(3) Uani d . 1 B .
    N N6 0.11847(7) 0.99970(13) -0.14966(18) 0.0393(3) Uani d . 1 . .
    N N5 0.07161(7) 0.98340(12) -0.30460(17) 0.0398(3) Uani d . 1 . .
    C C41 0.19981(8) 0.84790(17) 0.0412(2) 0.0438(3) Uani d DU 1 . .
    H H41A 0.1928 0.7556 0.0803 0.053 Uiso calc R 1 A 1
    H H41B 0.1976 0.9139 0.1278 0.053 Uiso calc R 1 A 1
    C C42 0.26718(8) 0.85404(16) 0.0173(2) 0.0445(3) Uani d PDU 0.559(3) B 1
    S S1 0.32023(8) 0.71922(19) 0.0776(3) 0.0634(5) Uani d PDU 0.559(3) B 1
    C C43 0.3784(4) 0.8126(10) 0.0046(16) 0.0627(17) Uani d PDU 0.559(3) B 1
    H H43 0.4199 0.7770 0.0110 0.075 Uiso calc PR 0.559(3) B 1
    C C44 0.3585(4) 0.9386(11) -0.0606(16) 0.0633(15) Uani d PDU 0.559(3) B 1
    H H44 0.3831 1.0013 -0.1033 0.076 Uiso calc PR 0.559(3) B 1
    C C45 0.2952(5) 0.9576(8) -0.0527(14) 0.0614(16) Uani d PDU 0.559(3) B 1
    H H45 0.2720 1.0385 -0.0938 0.074 Uiso calc PR 0.559(3) B 1
    C C42' 0.26718(8) 0.85404(16) 0.0173(2) 0.0445(3) Uani d PDU 0.441(3) B 2
    S S1' 0.29405(13) 0.9970(2) -0.0653(4) 0.0565(5) Uani d PDU 0.441(3) B 2
    C C43' 0.3687(5) 0.9102(13) -0.047(2) 0.0600(18) Uani d PDU 0.441(3) B 2
    H H43' 0.4027 0.9515 -0.0798 0.072 Uiso calc PR 0.441(3) B 2
    C C44' 0.3743(7) 0.7795(13) 0.018(2) 0.068(2) Uani d PDU 0.441(3) B 2
    H H44' 0.4096 0.7185 0.0342 0.082 Uiso calc PR 0.441(3) B 2
    C C45' 0.3165(5) 0.7580(9) 0.0556(15) 0.0654(19) Uani d PDU 0.441(3) B 2
    H H45' 0.3105 0.6757 0.1085 0.078 Uiso calc PR 0.441(3) B 2
    C C3 0.06799(7) 0.85162(14) -0.36608(19) 0.0381(3) Uani d . 1 B .
    C C52 -0.03960(8) 1.0779(2) -0.3428(2) 0.0517(4) Uani d . 1 . .
    O O2 -0.05226(8) 0.97759(18) -0.2716(2) 0.0688(4) Uani d . 1 . .
    N N4 0.11834(6) 0.78629(12) -0.24189(17) 0.0396(3) Uani d . 1 . .
    C C4 0.14634(7) 0.87926(14) -0.11427(19) 0.0372(3) Uani d . 1 B .
    C C1 0.09964(10) 0.53665(16) -0.2186(2) 0.0487(4) Uani d . 1 . .
    N N3 0.17852(10) 0.46323(18) -0.3180(3) 0.0668(5) Uani d . 1 . .
    N N2 0.12657(10) 0.42417(16) -0.2552(2) 0.0648(5) Uani d . 1 B .
    C C51 0.02666(8) 1.09491(16) -0.3740(2) 0.0442(3) Uani d . 1 . .
    H H51A 0.0205 1.0996 -0.4943 0.053 Uiso calc R 1 . .
    H H51B 0.0460 1.1823 -0.3252 0.053 Uiso calc R 1 . .
    C C2 0.18161(9) 0.59797(19) -0.3193(2) 0.0506(4) Uani d . 1 B .
    C C11 0.04103(12) 0.5476(2) -0.1593(3) 0.0646(5) Uani d . 1 B .
    H H11A 0.0328 0.6437 -0.1408 0.097 Uiso calc R 1 . .
    H H11B 0.0482 0.4970 -0.0559 0.097 Uiso calc R 1 . .
    H H11C 0.0038 0.5093 -0.2423 0.097 Uiso calc R 1 . .
    C C53 -0.08696(15) 1.1932(4) -0.4126(5) 0.0988(10) Uani d . 1 . .
    H H53A -0.1278 1.1756 -0.3880 0.148 Uiso calc R 1 . .
    H H53B -0.0946 1.1981 -0.5322 0.148 Uiso calc R 1 . .
    H H53C -0.0688 1.2798 -0.3625 0.148 Uiso calc R 1 . .
    C C22 0.22523(12) 0.6864(3) -0.3854(3) 0.0695(6) Uani d . 1 . .
    H H22A 0.2169 0.7825 -0.3674 0.104 Uiso calc R 1 B .
    H H22B 0.2169 0.6695 -0.5037 0.104 Uiso calc R 1 . .
    H H22C 0.2703 0.6647 -0.3283 0.104 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 C3 . 1.2114(19) ?
    N1 C2 . 1.368(2) ?
    N1 N4 . 1.3726(17) ?
    N1 C1 . 1.376(2) ?
    N6 C4 . 1.2939(19) ?
    N6 N5 . 1.3897(19) ?
    N5 C3 . 1.3587(18) ?
    N5 C51 . 1.4392(19) ?
    C41 C4 . 1.483(2) ?
    C41 C42 . 1.498(2) ?
    C41 H41A . 0.9700 ?
    C41 H41B . 0.9700 ?
    C42 C45 . 1.371(9) ?
    C42 S1 . 1.694(2) ?
    S1 C43 . 1.766(8) ?
    C43 C44 . 1.343(8) ?
    C43 H43 . 0.9300 ?
    C44 C45 . 1.375(13) ?
    C44 H44 . 0.9300 ?
    C45 H45 . 0.9300 ?
    S1' C43' . 1.756(10) ?
    C43' C44' . 1.358(10) ?
    C43' H43' . 0.9300 ?
    C44' C45' . 1.362(16) ?
    C44' H44' . 0.9300 ?
    C45' H45' . 0.9300 ?
    C3 N4 . 1.4011(19) ?
    C52 O2 . 1.201(3) ?
    C52 C53 . 1.495(3) ?
    C52 C51 . 1.508(2) ?
    N4 C4 . 1.3824(19) ?
    C1 N2 . 1.298(3) ?
    C1 C11 . 1.465(3) ?
    N3 C2 . 1.296(3) ?
    N3 N2 . 1.398(3) ?
    C51 H51A . 0.9700 ?
    C51 H51B . 0.9700 ?
    C2 C22 . 1.473(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C53 H53A . 0.9600 ?
    C53 H53B . 0.9600 ?
    C53 H53C . 0.9600 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 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
    C2 N1 N4 . . 126.30(14) ?
    C2 N1 C1 . . 107.52(14) ?
    N4 N1 C1 . . 125.81(14) ?
    C4 N6 N5 . . 105.52(12) ?
    C3 N5 N6 . . 113.63(12) ?
    C3 N5 C51 . . 125.70(14) ?
    N6 N5 C51 . . 120.09(13) ?
    C4 C41 C42 . . 113.30(12) ?
    C4 C41 H41A . . 108.9 ?
    C42 C41 H41A . . 108.9 ?
    C4 C41 H41B . . 108.9 ?
    C42 C41 H41B . . 108.9 ?
    H41A C41 H41B . . 107.7 ?
    C45 C42 C41 . . 129.1(4) ?
    C45 C42 S1 . . 110.4(4) ?
    C41 C42 S1 . . 120.51(14) ?
    C42 S1 C43 . . 88.8(4) ?
    C44 C43 S1 . . 115.3(9) ?
    C44 C43 H43 . . 122.3 ?
    S1 C43 H43 . . 122.3 ?
    C43 C44 C45 . . 107.3(10) ?
    C43 C44 H44 . . 126.4 ?
    C45 C44 H44 . . 126.4 ?
    C42 C45 C44 . . 118.2(8) ?
    C42 C45 H45 . . 120.9 ?
    C44 C45 H45 . . 120.9 ?
    C44' C43' S1' . . 116.6(12) ?
    C44' C43' H43' . . 121.7 ?
    S1' C43' H43' . . 121.7 ?
    C43' C44' C45' . . 104.4(13) ?
    C43' C44' H44' . . 127.8 ?
    C45' C44' H44' . . 127.8 ?
    C44' C45' H45' . . 119.2 ?
    O1 C3 N5 . . 131.43(14) ?
    O1 C3 N4 . . 127.49(13) ?
    N5 C3 N4 . . 101.07(12) ?
    O2 C52 C53 . . 124.4(2) ?
    O2 C52 C51 . . 121.49(16) ?
    C53 C52 C51 . . 114.1(2) ?
    N1 N4 C4 . . 128.05(12) ?
    N1 N4 C3 . . 121.87(12) ?
    C4 N4 C3 . . 110.07(12) ?
    N6 C4 N4 . . 109.64(13) ?
    N6 C4 C41 . . 124.33(14) ?
    N4 C4 C41 . . 126.02(13) ?
    N2 C1 N1 . . 107.86(18) ?
    N2 C1 C11 . . 127.64(18) ?
    N1 C1 C11 . . 124.42(15) ?
    C2 N3 N2 . . 108.53(15) ?
    C1 N2 N3 . . 108.08(16) ?
    N5 C51 C52 . . 113.11(14) ?
    N5 C51 H51A . . 109.0 ?
    C52 C51 H51A . . 109.0 ?
    N5 C51 H51B . . 109.0 ?
    C52 C51 H51B . . 109.0 ?
    H51A C51 H51B . . 107.8 ?
    N3 C2 N1 . . 107.94(18) ?
    N3 C2 C22 . . 128.11(17) ?
    N1 C2 C22 . . 123.88(17) ?
    C1 C11 H11A . . 109.5 ?
    C1 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C1 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C52 C53 H53A . . 109.5 ?
    C52 C53 H53B . . 109.5 ?
    H53A C53 H53B . . 109.5 ?
    C52 C53 H53C . . 109.5 ?
    H53A C53 H53C . . 109.5 ?
    H53B C53 H53C . . 109.5 ?
    C2 C22 H22A . . 109.5 ?
    C2 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C2 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 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 N6 N5 C3 . . . . 1.96(16) ?
    C4 N6 N5 C51 . . . . 173.77(13) ?
    C4 C41 C42 C45 . . . . 50.9(6) ?
    C4 C41 C42 S1 . . . . -128.07(16) ?
    C45 C42 S1 C43 . . . . 0.3(7) ?
    C41 C42 S1 C43 . . . . 179.5(4) ?
    C42 S1 C43 C44 . . . . 0.3(9) ?
    S1 C43 C44 C45 . . . . -0.8(13) ?
    C41 C42 C45 C44 . . . . -180.0(8) ?
    S1 C42 C45 C44 . . . . -0.9(12) ?
    C43 C44 C45 C42 . . . . 1.1(15) ?
    S1' C43' C44' C45' . . . . -1.8(18) ?
    N6 N5 C3 O1 . . . . 176.56(14) ?
    C51 N5 C3 O1 . . . . 5.3(3) ?
    N6 N5 C3 N4 . . . . -2.60(16) ?
    C51 N5 C3 N4 . . . . -173.87(13) ?
    C2 N1 N4 C4 . . . . -87.1(2) ?
    C1 N1 N4 C4 . . . . 100.82(19) ?
    C2 N1 N4 C3 . . . . 93.89(19) ?
    C1 N1 N4 C3 . . . . -78.2(2) ?
    O1 C3 N4 N1 . . . . 2.3(2) ?
    N5 C3 N4 N1 . . . . -178.52(13) ?
    O1 C3 N4 C4 . . . . -176.90(14) ?
    N5 C3 N4 C4 . . . . 2.31(15) ?
    N5 N6 C4 N4 . . . . -0.33(15) ?
    N5 N6 C4 C41 . . . . -179.87(13) ?
    N1 N4 C4 N6 . . . . 179.59(14) ?
    C3 N4 C4 N6 . . . . -1.31(16) ?
    N1 N4 C4 C41 . . . . -0.9(2) ?
    C3 N4 C4 C41 . . . . 178.23(13) ?
    C42 C41 C4 N6 . . . . -97.73(17) ?
    C42 C41 C4 N4 . . . . 82.80(18) ?
    C2 N1 C1 N2 . . . . 2.27(19) ?
    N4 N1 C1 N2 . . . . 175.59(15) ?
    C2 N1 C1 C11 . . . . -174.74(19) ?
    N4 N1 C1 C11 . . . . -1.4(3) ?
    N1 C1 N2 N3 . . . . -1.1(2) ?
    C11 C1 N2 N3 . . . . 175.8(2) ?
    C2 N3 N2 C1 . . . . -0.5(2) ?
    C3 N5 C51 C52 . . . . 72.9(2) ?
    N6 N5 C51 C52 . . . . -97.89(16) ?
    O2 C52 C51 N5 . . . . -2.3(2) ?
    C53 C52 C51 N5 . . . . 179.6(2) ?
    N2 N3 C2 N1 . . . . 1.9(2) ?
    N2 N3 C2 C22 . . . . -175.4(2) ?
    N4 N1 C2 N3 . . . . -175.84(15) ?
    C1 N1 C2 N3 . . . . -2.57(19) ?
    N4 N1 C2 C22 . . . . 1.6(3) ?
    C1 N1 C2 C22 . . . . 174.83(19) ?
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
    C22 H22B N2 2_564 0.96 2.557 3.352(3) 140 yes
    C41 H41A N3 2_565 0.97 2.317 3.287(3) 178 yes
    C43 H43 O1 4_565 0.93 2.487 3.414(10) 174 yes
    C44' H44' O2 4_565 0.93 2.460 3.162(14) 132 yes
    C51 H51A O2 2_574 0.97 2.488 3.318(2) 143 yes
