##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-05-03
_journal_date_accepted     2005-05-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      6
_journal_page_first     o1785
_journal_page_last     o1787
_journal_paper_category     EO
_publ_contact_author_name     'Ufuk Çoruh^*^'
_publ_contact_author_address
;
Department of Computer Education and Instructional Technology
Faculty of Education
Ondokuz Mayıs University
55200-Atakum/Samsun
Turkey
;
_publ_contact_author_email     ucoruh@omu.edu.tr
_publ_contact_author_fax     '90-362-4450300'
_publ_contact_author_phone     '90-362-4450118-389'
_publ_section_title
;
1-(Benzoylmethyl)-4-(3,5-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
    'Sancak, Kemal'
;
Department of Chemistry
Faculty of Arts and Sciences
Karadeniz Teknik University
61080 Trabzon
Turkey
;
    'Çoruh, Ufuk'
;
Department of Computer Education and Instructional Technology
Faculty of Education
Ondokuz Mayıs University
55200 Atakum/Samsun
Turkey
;
    'Ünver, Yasemin'
;
Department of Chemistry
Faculty of Arts and Sciences
Karadeniz Teknik University
61080 Trabzon
Turkey
;
    'Vázquez-López, Ezequiel M.'
;
Departamento de Química Inorgánica
Facultade de Ciencias-Química
Universidade de Vigo
36200-Vigo
Galicia
Spain
;
data_I
_chemical_name_systematic
;
1-(Benzoylmethyl)-4-(3,5-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     'C19 H18 N6 O2 S'
_chemical_formula_sum     'C19 H18 N6 O2 S'
_chemical_formula_iupac     'C19 H18 N6 O2 S'
_chemical_formula_weight     394.45
_chemical_melting_point     ?
_symmetry_cell_setting     'orthorhombic'
_symmetry_space_group_name_H-M     'P c a 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y, z'
    '-x+1/2, y, z+1/2'
_cell_length_a     9.8596(10)
_cell_length_b     23.584(2)
_cell_length_c     8.4499(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1964.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2375
_cell_measurement_theta_min     1.978
_cell_measurement_theta_max     28.01
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.34
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.333
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     0.192
_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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11257
_diffrn_reflns_av_R_equivalents     0.0394
_diffrn_reflns_av_sigmaI/netI     0.0724
_diffrn_reflns_theta_min     1.73
_diffrn_reflns_theta_max     28.01
_diffrn_reflns_theta_full     28.01
_diffrn_measured_fraction_theta_max     1.978
_diffrn_measured_fraction_theta_full     1.978
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     11
_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     4305
_reflns_number_gt     2374
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1332
_refine_ls_R_factor_gt     0.0851
_refine_ls_wR_factor_gt     0.2296
_refine_ls_wR_factor_ref     0.2490
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     4305
_refine_ls_number_parameters     205
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.1325P)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     0.049
_refine_ls_shift/su_mean     0.022
_refine_diff_density_max     0.789
_refine_diff_density_min     -0.482
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1821 Friedel pairs'
_refine_ls_abs_structure_Flack     0.0(3)
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, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
        'PARST (Nardelli, 1995), PLATON (Spek, 1997) and WinGX (Farrugia, 1999)'
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
    C21 -0.2155(7) 0.2896(3) 0.3254(9) 0.0718(18) Uani d . 1 . . C
    H21A -0.1231 0.2993 0.3493 0.108 Uiso calc R 1 . . H
    H21B -0.2636 0.2821 0.4220 0.108 Uiso calc R 1 . . H
    H21C -0.2579 0.3206 0.2708 0.108 Uiso calc R 1 . . H
    C24 -0.0511(7) 0.1362(3) -0.0252(8) 0.0712(18) Uani d . 1 . . C
    H24A 0.0408 0.1450 0.0030 0.107 Uiso calc R 1 . . H
    H24B -0.0647 0.1436 -0.1357 0.107 Uiso calc R 1 . . H
    H24C -0.0686 0.0969 -0.0038 0.107 Uiso calc R 1 . . H
    S1 0.2367(2) 0.08207(7) 0.2536(3) 0.0847(7) Uani d . 1 . . S
    C12 0.0974(7) 0.1029(2) 0.3504(9) 0.0671(9) Uani d . 1 . . C
    C14 0.0497(6) 0.0113(2) 0.2719(8) 0.0671(9) Uani d . 1 . . C
    H14 0.0030 -0.0226 0.2593 0.081 Uiso calc R 1 . . H
    C13 -0.0089(7) 0.0579(2) 0.3570(9) 0.0671(9) Uani d . 1 . . C
    H13 -0.0936 0.0596 0.4051 0.081 Uiso calc R 1 . . H
    C15 0.1735(6) 0.0183(2) 0.2114(9) 0.0671(9) Uani d . 1 . . C
    H15 0.2190 -0.0091 0.1527 0.081 Uiso calc R 1 . . H
    N1 0.2321(4) 0.23199(16) 0.2994(5) 0.0409(10) Uani d . 1 . . N
    O21 0.0466(4) 0.30132(15) 0.0085(5) 0.0544(10) Uani d . 1 . . O
    N2 0.0302(4) 0.22939(17) 0.1982(5) 0.0408(10) Uani d . 1 . . N
    N3 0.2201(4) 0.27117(16) 0.1792(5) 0.0444(11) Uani d . 1 . . N
    O2 0.2294(4) 0.37618(15) 0.3103(5) 0.0573(10) Uani d . 1 . . O
    N4 -0.1023(4) 0.21345(17) 0.1681(5) 0.0435(10) Uani d . 1 . . N
    C1 0.1148(5) 0.20693(19) 0.3102(6) 0.0390(11) Uani d . 1 . . C
    C11 0.0851(5) 0.1612(2) 0.4232(6) 0.0471(13) Uani d . 1 . . C
    H11A -0.0062 0.1661 0.4637 0.057 Uiso calc R 1 . . H
    H11B 0.1473 0.1640 0.5119 0.057 Uiso calc R 1 . . H
    C2 0.0941(5) 0.2727(2) 0.1140(6) 0.0404(12) Uani d . 1 . . C
    C32 0.3260(5) 0.36382(19) 0.2312(6) 0.0387(11) Uani d . 1 . . C
    N5 -0.2754(5) 0.1702(2) 0.0655(8) 0.0707(15) Uani d . 1 . . N
    C22 -0.2183(5) 0.2388(2) 0.2246(7) 0.0510(14) Uani d . 1 . . C
    C31 0.3325(5) 0.3081(2) 0.1408(7) 0.0447(12) Uani d . 1 . . C
    H31A 0.3318 0.3159 0.0281 0.054 Uiso calc R 1 . . H
    H31B 0.4169 0.2890 0.1657 0.054 Uiso calc R 1 . . H
    C34 0.4666(8) 0.4442(3) 0.3228(10) 0.0786(9) Uani d . 1 . . C
    H34 0.4075 0.4492 0.4075 0.094 Uiso calc R 1 . . H
    N6 -0.3222(4) 0.2135(2) 0.1651(7) 0.0644(14) Uani d . 1 . . N
    C33 0.4447(7) 0.4012(3) 0.2167(10) 0.0786(9) Uani d . 1 . . C
    C23 -0.1441(6) 0.1714(2) 0.0682(8) 0.0570(15) Uani d . 1 . . C
    C38 0.5374(7) 0.3948(3) 0.0956(10) 0.0786(9) Uani d . 1 . . C
    H38 0.5253 0.3658 0.0223 0.094 Uiso calc R 1 . . H
    C36 0.6659(8) 0.4733(3) 0.1849(10) 0.0786(9) Uani d U 1 . . C
    H36 0.7394 0.4977 0.1740 0.094 Uiso calc R 1 . . H
    C35 0.5783(7) 0.4810(3) 0.3038(10) 0.0786(9) Uani d . 1 . . C
    H35 0.5911 0.5107 0.3745 0.094 Uiso calc R 1 . . H
    C37 0.6487(7) 0.4308(3) 0.0809(10) 0.0786(9) Uani d . 1 . . C
    H37 0.7108 0.4254 -0.0005 0.094 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
    C21 C22 . 1.470(8) y
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C24 C23 . 1.467(9) y
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 0.9600 ?
    S1 C15 . 1.666(6) y
    S1 C12 . 1.672(8) y
    C12 C13 . 1.493(8) ?
    C12 C11 . 1.512(8) ?
    C14 C15 . 1.333(9) ?
    C14 C13 . 1.434(10) ?
    C14 H14 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C15 H15 . 0.9300 ?
    N1 C1 . 1.303(6) y
    N1 N3 . 1.379(6) y
    O21 C2 . 1.212(6) y
    N2 C1 . 1.368(6) y
    N2 N4 . 1.383(5) y
    N2 C2 . 1.395(6) y
    N3 C2 . 1.360(6) y
    N3 C31 . 1.447(6) y
    O2 C32 . 1.199(6) y
    N4 C23 . 1.366(7) y
    N4 C22 . 1.377(6) y
    C1 C11 . 1.470(7) y
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C32 C33 . 1.470(8) ?
    C32 C31 . 1.520(7) ?
    N5 C23 . 1.296(7) y
    N5 N6 . 1.403(8) y
    C22 N6 . 1.287(7) y
    C31 H31A . 0.9700 ?
    C31 H31B . 0.9700 ?
    C34 C33 . 1.371(10) ?
    C34 C35 . 1.411(9) ?
    C34 H34 . 0.9300 ?
    C33 C38 . 1.381(10) ?
    C38 C37 . 1.392(9) ?
    C38 H38 . 0.9300 ?
    C36 C35 . 1.337(10) ?
    C36 C37 . 1.345(9) ?
    C36 H36 . 0.9300 ?
    C35 H35 . 0.9300 ?
    C37 H37 . 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
    C22 C21 H21A . . 109.5 ?
    C22 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C22 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C15 S1 C12 . . 93.6(3) ?
    C13 C12 C11 . . 125.1(6) ?
    C13 C12 S1 . . 112.7(5) ?
    C11 C12 S1 . . 122.1(4) ?
    C15 C14 C13 . . 117.8(6) ?
    C15 C14 H14 . . 121.2 ?
    C13 C14 H14 . . 121.1 ?
    C14 C13 C12 . . 104.0(6) ?
    C14 C13 H13 . . 128.0 ?
    C12 C13 H13 . . 128.0 ?
    C14 C15 S1 . . 111.9(6) ?
    C14 C15 H15 . . 124.0 ?
    S1 C15 H15 . . 124.1 ?
    C1 N1 N3 . . 106.2(4) y
    C1 N2 N4 . . 126.7(4) y
    C1 N2 C2 . . 111.2(4) y
    N4 N2 C2 . . 122.1(4) y
    C2 N3 N1 . . 113.3(4) y
    C2 N3 C31 . . 126.4(4) y
    N1 N3 C31 . . 120.2(4) y
    C23 N4 C22 . . 106.2(4) y
    C23 N4 N2 . . 126.6(4) y
    C22 N4 N2 . . 127.1(4) y
    N1 C1 N2 . . 108.5(4) y
    N1 C1 C11 . . 123.7(4) y
    N2 C1 C11 . . 127.8(4) y
    C1 C11 C12 . . 112.8(5) ?
    C1 C11 H11A . . 109.0 ?
    C12 C11 H11A . . 109.0 ?
    C1 C11 H11B . . 109.0 ?
    C12 C11 H11B . . 109.0 ?
    H11A C11 H11B . . 107.8 ?
    O21 C2 N3 . . 131.7(5) y
    O21 C2 N2 . . 127.5(4) y
    N3 C2 N2 . . 100.7(4) y
    O2 C32 C33 . . 122.2(5) ?
    O2 C32 C31 . . 121.6(4) ?
    C33 C32 C31 . . 116.3(5) ?
    C23 N5 N6 . . 107.5(5) y
    N6 C22 N4 . . 108.9(5) y
    N6 C22 C21 . . 128.3(5) y
    N4 C22 C21 . . 122.7(5) y
    N3 C31 C32 . . 112.1(4) y
    N3 C31 H31A . . 109.2 y
    C32 C31 H31A . . 109.2 ?
    N3 C31 H31B . . 109.2 ?
    C32 C31 H31B . . 109.2 ?
    H31A C31 H31B . . 107.9 ?
    C33 C34 C35 . . 120.2(8) ?
    C33 C34 H34 . . 119.9 ?
    C35 C34 H34 . . 119.9 ?
    C22 N6 N5 . . 108.1(5) y
    C34 C33 C38 . . 117.5(6) ?
    C34 C33 C32 . . 121.0(7) ?
    C38 C33 C32 . . 121.5(6) ?
    N5 C23 N4 . . 109.2(5) y
    N5 C23 C24 . . 127.0(6) y
    N4 C23 C24 . . 123.7(5) ?
    C33 C38 C37 . . 121.4(7) ?
    C33 C38 H38 . . 119.3 ?
    C37 C38 H38 . . 119.3 ?
    C35 C36 C37 . . 120.7(7) ?
    C35 C36 H36 . . 119.6 ?
    C37 C36 H36 . . 119.7 ?
    C36 C35 C34 . . 120.5(7) ?
    C36 C35 H35 . . 119.8 ?
    C34 C35 H35 . . 119.7 ?
    C36 C37 C38 . . 119.7(8) ?
    C36 C37 H37 . . 120.1 ?
    C38 C37 H37 . . 120.1 ?
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
    C15 S1 C12 C13 . . . . 1.3(6) ?
    C15 S1 C12 C11 . . . . -179.3(5) ?
    C15 C14 C13 C12 . . . . -0.4(8) ?
    C11 C12 C13 C14 . . . . 179.8(6) ?
    S1 C12 C13 C14 . . . . -0.7(7) ?
    C13 C14 C15 S1 . . . . 1.3(8) ?
    C12 S1 C15 C14 . . . . -1.5(6) ?
    C1 N1 N3 C2 . . . . 1.5(5) ?
    C1 N1 N3 C31 . . . . 177.5(4) ?
    C1 N2 N4 C23 . . . . -87.7(6) ?
    C2 N2 N4 C23 . . . . 93.1(6) ?
    C1 N2 N4 C22 . . . . 96.7(6) ?
    C2 N2 N4 C22 . . . . -82.6(6) ?
    N3 N1 C1 N2 . . . . 0.5(5) ?
    N3 N1 C1 C11 . . . . 178.9(4) ?
    N4 N2 C1 N1 . . . . 178.4(5) ?
    C2 N2 C1 N1 . . . . -2.3(5) ?
    N4 N2 C1 C11 . . . . 0.1(8) ?
    C2 N2 C1 C11 . . . . 179.4(5) ?
    N1 C1 C11 C12 . . . . -97.4(6) y
    N2 C1 C11 C12 . . . . 80.7(6) y
    C13 C12 C11 C1 . . . . -127.8(6) ?
    S1 C12 C11 C1 . . . . 52.8(7) ?
    N1 N3 C2 O21 . . . . 179.7(5) ?
    C31 N3 C2 O21 . . . . 4.0(9) ?
    N1 N3 C2 N2 . . . . -2.8(5) ?
    C31 N3 C2 N2 . . . . -178.4(4) ?
    C1 N2 C2 O21 . . . . -179.3(5) ?
    N4 N2 C2 O21 . . . . 0.1(8) ?
    C1 N2 C2 N3 . . . . 3.0(5) ?
    N4 N2 C2 N3 . . . . -177.6(4) ?
    C23 N4 C22 N6 . . . . 0.8(6) ?
    N2 N4 C22 N6 . . . . 177.2(4) ?
    C23 N4 C22 C21 . . . . -174.4(5) ?
    N2 N4 C22 C21 . . . . 1.9(8) ?
    C2 N3 C31 C32 . . . . 83.7(6) y
    N1 N3 C31 C32 . . . . -91.7(5) y
    O2 C32 C31 N3 . . . . -7.4(7) ?
    C33 C32 C31 N3 . . . . 172.2(5) ?
    N4 C22 N6 N5 . . . . -0.3(6) ?
    C21 C22 N6 N5 . . . . 174.7(6) y
    C23 N5 N6 C22 . . . . -0.5(7) ?
    C35 C34 C33 C38 . . . . 1.7(11) ?
    C35 C34 C33 C32 . . . . -177.7(6) ?
    O2 C32 C33 C34 . . . . 17.1(9) ?
    C31 C32 C33 C34 . . . . -162.5(6) ?
    O2 C32 C33 C38 . . . . -162.3(6) ?
    C31 C32 C33 C38 . . . . 18.2(9) ?
    N6 N5 C23 N4 . . . . 1.0(7) ?
    N6 N5 C23 C24 . . . . -176.0(6) ?
    C22 N4 C23 N5 . . . . -1.1(6) ?
    N2 N4 C23 N5 . . . . -177.5(5) ?
    C22 N4 C23 C24 . . . . 176.0(5) ?
    N2 N4 C23 C24 . . . . -0.4(8) ?
    C34 C33 C38 C37 . . . . -0.3(11) ?
    C32 C33 C38 C37 . . . . 179.1(6) ?
    C37 C36 C35 C34 . . . . 0.4(12) ?
    C33 C34 C35 C36 . . . . -1.8(11) ?
    C35 C36 C37 C38 . . . . 1.0(11) ?
    C33 C38 C37 C36 . . . . -1.1(11) ?
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
    C21 H21A N2 . 0.96 2.59 3.014(6) 107 yes
    C24 H24A N2 . 0.96 2.60 3.012(6) 106 yes
    C24 H24B N6 4_454 0.96 2.60 3.424(6) 143 yes
    C31 H31A O2 4_554 0.97 2.40 3.284(3) 150 yes
    C11 H11A N5 4_455 0.97 2.32 3.286(6) 175 yes
    C21 H21B Cg1 4_455 0.96 2.65 3.439(5) 140 yes
    C21 H21C Cg2 1_455 0.96 3.34 4.262(5) 162 yes
    C24 H24C Cg3 . 0.96 3.19 3.640(5) 110 yes
    C24 H24A Cg3 . 0.96 3.30 3.640(5) 103 yes
