##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2016-12-10
_journal_date_accepted     2016-12-16
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616020010
_journal_coeditor_code     SU4113
_publ_contact_author_name     'Dr. Hewen Wang'
_publ_contact_author_address
; College of Chemical Engineering,
  Huanggang Normal University,
  Huanggang, 438000,
  People's Republic of China
;
_publ_contact_author_email     qqhrchemistry@aliyun.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
3-(4-Amino-3-ethyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-1,\
3-diphenylpropan-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Jianchao Xu'
;
  College of Chemical Engineering,
  Huanggang Normal University,
  Huanggang 438000,
  People's Republic of China
;
    'Hewen Wang'
;
  College of Chemical Engineering,
  Huanggang Normal University,
  Huanggang 438000,
  People's Republic of China
;
_publ_section_synopsis
;
In the title triazole derivative, the 1,2,4-triazole ring forms dihedral angles
of 58.64(9) and 87.68(9)° with the phenyl rings. In the crystal, molecules
are linked by N---H...O, N---H...S and C---H...S hydrogen bonds, forming
chains propagating along the c-axis direction.
;
data_I
_database_code_depnum_ccdc_archive     'CCDC 1523058'
_chemical_name_systematic
;\
3-(4-Amino-3-ethyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-\
1,3-diphenylpropan-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H20 N4 O S'
_chemical_formula_sum     'C19 H20 N4 O S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C19 H20 N4 O S'
_chemical_formula_weight     352.45
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.4024(15)
_cell_length_b     17.797(2)
_cell_length_c     10.2829(14)
_cell_angle_alpha     90.00
_cell_angle_beta     112.908(7)
_cell_angle_gamma     90.00
_cell_volume     1753.5(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6033
_cell_measurement_theta_min     2.1
_cell_measurement_theta_max     28.0
_cell_measurement_temperature     113(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.335
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     744
_exptl_absorpt_coefficient_mu     0.199
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku/MSC, 2005)
;
_exptl_absorpt_correction_T_min     0.9612
_exptl_absorpt_correction_T_max     0.9726
_exptl_special_details     ?
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     multilayer
_diffrn_measurement_device_type     'Rigaku Saturn CCD area detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     14.22
_diffrn_reflns_number     18273
_diffrn_reflns_av_R_equivalents     0.0607
_diffrn_reflns_av_sigmaI/netI     0.0666
_diffrn_reflns_theta_min     2.13
_diffrn_reflns_theta_max     27.93
_diffrn_reflns_theta_full     27.93
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
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     4199
_reflns_number_gt     2965
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0635
_refine_ls_R_factor_gt     0.0447
_refine_ls_wR_factor_gt     0.0903
_refine_ls_wR_factor_ref     0.0990
_refine_ls_goodness_of_fit_ref     0.971
_refine_ls_restrained_S_all     0.971
_refine_ls_number_reflns     4199
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0439P)²+0.0000P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.335
_refine_diff_density_min     -0.326
_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
;
    S S 0.1246 0.1234
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
_computing_data_collection
;
CrystalClear (Rigaku/MSC, 2005)
;
_computing_cell_refinement
;
CrystalClear (Rigaku/MSC, 2005)
;
_computing_data_reduction
;
CrystalClear (Rigaku/MSC, 2005)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
CrystalStructure (Rigaku/MSC, 2005)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.12424(4) 0.20783(2) 0.57027(4) 0.02353(13) Uani d . 1 1 . .
    O O1 0.29173(11) 0.38597(6) 0.39457(12) 0.0258(3) Uani d . 1 1 . .
    N N1 0.09813(13) 0.35970(7) 0.53152(13) 0.0191(3) Uani d . 1 1 . .
    N N2 0.14589(13) 0.42626(7) 0.60247(14) 0.0215(3) Uani d . 1 1 . .
    N N3 0.22893(13) 0.32917(7) 0.74060(13) 0.0178(3) Uani d . 1 1 . .
    N N4 0.31459(14) 0.28805(8) 0.85958(15) 0.0225(3) Uani d . 1 1 . .
    H H4A 0.3163(17) 0.2402(11) 0.8276(19) 0.034 Uiso d . 1 1 . .
    H H4B 0.2634(19) 0.2836(10) 0.914(2) 0.034 Uiso d . 1 1 . .
    C C1 0.39700(16) 0.51862(10) 0.33197(17) 0.0236(4) Uani d . 1 1 . .
    H H1 0.4613 0.4798 0.3783 0.028 Uiso calc R 1 1 . .
    C C2 0.44514(17) 0.58554(10) 0.30018(18) 0.0274(4) Uani d . 1 1 . .
    H H2 0.5426 0.5931 0.3277 0.033 Uiso calc R 1 1 . .
    C C3 0.35281(18) 0.64159(10) 0.22870(19) 0.0300(4) Uani d . 1 1 . .
    H H3 0.3865 0.6873 0.2058 0.036 Uiso calc R 1 1 . .
    C C4 0.21096(18) 0.63089(10) 0.19061(19) 0.0293(4) Uani d . 1 1 . .
    H H4 0.1470 0.6690 0.1404 0.035 Uiso calc R 1 1 . .
    C C5 0.16246(17) 0.56481(9) 0.22558(18) 0.0243(4) Uani d . 1 1 . .
    H H5 0.0652 0.5583 0.2010 0.029 Uiso calc R 1 1 . .
    C C6 0.25453(15) 0.50757(9) 0.29653(16) 0.0203(4) Uani d . 1 1 . .
    C C7 0.20880(16) 0.43628(9) 0.33978(16) 0.0207(4) Uani d . 1 1 . .
    C C8 0.05603(16) 0.42832(9) 0.31349(17) 0.0212(4) Uani d . 1 1 . .
    H H8A 0.0012 0.4275 0.2103 0.025 Uiso calc R 1 1 . .
    H H8B 0.0267 0.4731 0.3522 0.025 Uiso calc R 1 1 . .
    C C9 0.02112(16) 0.35844(9) 0.37787(16) 0.0206(4) Uani d . 1 1 . .
    H H9 0.0539 0.3139 0.3401 0.025 Uiso calc R 1 1 . .
    C C10 -0.13554(16) 0.35072(9) 0.33486(17) 0.0196(4) Uani d . 1 1 . .
    C C11 -0.19972(17) 0.36120(9) 0.42884(18) 0.0248(4) Uani d . 1 1 . .
    H H11 -0.1447 0.3715 0.5253 0.030 Uiso calc R 1 1 . .
    C C12 -0.34399(17) 0.35674(10) 0.3831(2) 0.0289(4) Uani d . 1 1 . .
    H H12 -0.3871 0.3634 0.4485 0.035 Uiso calc R 1 1 . .
    C C13 -0.42453(17) 0.34270(10) 0.2433(2) 0.0290(4) Uani d . 1 1 . .
    H H13 -0.5233 0.3411 0.2116 0.035 Uiso calc R 1 1 . .
    C C14 -0.36106(17) 0.33084(10) 0.14891(19) 0.0275(4) Uani d . 1 1 . .
    H H14 -0.4162 0.3202 0.0527 0.033 Uiso calc R 1 1 . .
    C C15 -0.21747(16) 0.33454(9) 0.19507(18) 0.0247(4) Uani d . 1 1 . .
    H H15 -0.1743 0.3259 0.1302 0.030 Uiso calc R 1 1 . .
    C C16 0.14737(15) 0.29898(9) 0.61269(17) 0.0182(4) Uani d . 1 1 . .
    C C17 0.22746(16) 0.40574(9) 0.72990(16) 0.0188(4) Uani d . 1 1 . .
    C C18 0.31117(17) 0.45732(9) 0.84495(17) 0.0237(4) Uani d . 1 1 . .
    H H18A 0.3114 0.5075 0.8036 0.028 Uiso calc R 1 1 . .
    H H18B 0.4088 0.4391 0.8846 0.028 Uiso calc R 1 1 . .
    C C19 0.26191(17) 0.46595(10) 0.96465(17) 0.0251(4) Uani d . 1 1 . .
    H H19A 0.1654 0.4841 0.9272 0.038 Uiso calc R 1 1 . .
    H H19B 0.3218 0.5021 1.0336 0.038 Uiso calc R 1 1 . .
    H H19C 0.2666 0.4172 1.0107 0.038 Uiso calc R 1 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
    S1 C16 . 1.6727(16) ?
    O1 C7 . 1.2185(18) ?
    N1 C16 . 1.3394(19) ?
    N1 N2 . 1.3784(17) ?
    N1 C9 . 1.4674(19) ?
    N2 C17 . 1.3057(19) ?
    N3 C17 . 1.367(2) ?
    N3 C16 . 1.3674(19) ?
    N3 N4 . 1.4063(18) ?
    N4 H4A . 0.916(19) ?
    N4 H4B . 0.91(2) ?
    C1 C2 . 1.380(2) ?
    C1 C6 . 1.396(2) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.381(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.385(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.381(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.394(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.483(2) ?
    C7 C8 . 1.511(2) ?
    C8 C9 . 1.518(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.520(2) ?
    C9 H9 . 1.0000 ?
    C10 C11 . 1.385(2) ?
    C10 C15 . 1.386(2) ?
    C11 C12 . 1.389(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.376(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.386(2) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.382(2) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C17 C18 . 1.483(2) ?
    C18 C19 . 1.514(2) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
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
    C16 N1 N2 . . 113.07(12) ?
    C16 N1 C9 . . 125.08(13) ?
    N2 N1 C9 . . 121.09(12) ?
    C17 N2 N1 . . 104.50(13) ?
    C17 N3 C16 . . 109.34(13) ?
    C17 N3 N4 . . 124.91(13) ?
    C16 N3 N4 . . 125.31(13) ?
    N3 N4 H4A . . 105.5(11) ?
    N3 N4 H4B . . 104.8(11) ?
    H4A N4 H4B . . 103.7(15) ?
    C2 C1 C6 . . 120.42(15) ?
    C2 C1 H1 . . 119.8 ?
    C6 C1 H1 . . 119.8 ?
    C1 C2 C3 . . 120.54(16) ?
    C1 C2 H2 . . 119.7 ?
    C3 C2 H2 . . 119.7 ?
    C2 C3 C4 . . 119.66(17) ?
    C2 C3 H3 . . 120.2 ?
    C4 C3 H3 . . 120.2 ?
    C5 C4 C3 . . 120.03(16) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 120.82(16) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 118.49(15) ?
    C5 C6 C7 . . 123.16(14) ?
    C1 C6 C7 . . 118.33(14) ?
    O1 C7 C6 . . 121.02(15) ?
    O1 C7 C8 . . 121.32(15) ?
    C6 C7 C8 . . 117.67(13) ?
    C7 C8 C9 . . 114.34(13) ?
    C7 C8 H8A . . 108.7 ?
    C9 C8 H8A . . 108.7 ?
    C7 C8 H8B . . 108.7 ?
    C9 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    N1 C9 C8 . . 109.51(13) ?
    N1 C9 C10 . . 112.89(13) ?
    C8 C9 C10 . . 111.02(12) ?
    N1 C9 H9 . . 107.7 ?
    C8 C9 H9 . . 107.7 ?
    C10 C9 H9 . . 107.7 ?
    C11 C10 C15 . . 118.87(15) ?
    C11 C10 C9 . . 122.59(14) ?
    C15 C10 C9 . . 118.52(14) ?
    C10 C11 C12 . . 120.46(16) ?
    C10 C11 H11 . . 119.8 ?
    C12 C11 H11 . . 119.8 ?
    C13 C12 C11 . . 120.14(17) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 119.80(15) ?
    C12 C13 H13 . . 120.1 ?
    C14 C13 H13 . . 120.1 ?
    C15 C14 C13 . . 119.88(16) ?
    C15 C14 H14 . . 120.1 ?
    C13 C14 H14 . . 120.1 ?
    C14 C15 C10 . . 120.81(16) ?
    C14 C15 H15 . . 119.6 ?
    C10 C15 H15 . . 119.6 ?
    N1 C16 N3 . . 103.06(13) ?
    N1 C16 S1 . . 129.69(12) ?
    N3 C16 S1 . . 127.19(12) ?
    N2 C17 N3 . . 110.01(13) ?
    N2 C17 C18 . . 125.30(15) ?
    N3 C17 C18 . . 124.64(14) ?
    C17 C18 C19 . . 115.59(14) ?
    C17 C18 H18A . . 108.4 ?
    C19 C18 H18A . . 108.4 ?
    C17 C18 H18B . . 108.4 ?
    C19 C18 H18B . . 108.4 ?
    H18A C18 H18B . . 107.4 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 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
    C16 N1 N2 C17 . . . . 0.60(18) ?
    C9 N1 N2 C17 . . . . -169.86(13) ?
    C6 C1 C2 C3 . . . . -2.2(3) ?
    C1 C2 C3 C4 . . . . 1.0(3) ?
    C2 C3 C4 C5 . . . . 0.8(3) ?
    C3 C4 C5 C6 . . . . -1.4(3) ?
    C4 C5 C6 C1 . . . . 0.2(2) ?
    C4 C5 C6 C7 . . . . 178.47(16) ?
    C2 C1 C6 C5 . . . . 1.5(2) ?
    C2 C1 C6 C7 . . . . -176.78(15) ?
    C5 C6 C7 O1 . . . . 175.84(15) ?
    C1 C6 C7 O1 . . . . -5.9(2) ?
    C5 C6 C7 C8 . . . . -4.1(2) ?
    C1 C6 C7 C8 . . . . 174.09(14) ?
    O1 C7 C8 C9 . . . . 7.7(2) ?
    C6 C7 C8 C9 . . . . -172.31(14) ?
    C16 N1 C9 C8 . . . . -146.40(15) ?
    N2 N1 C9 C8 . . . . 22.87(19) ?
    C16 N1 C9 C10 . . . . 89.36(18) ?
    N2 N1 C9 C10 . . . . -101.38(16) ?
    C7 C8 C9 N1 . . . . 60.17(17) ?
    C7 C8 C9 C10 . . . . -174.50(13) ?
    N1 C9 C10 C11 . . . . 13.9(2) ?
    C8 C9 C10 C11 . . . . -109.55(17) ?
    N1 C9 C10 C15 . . . . -167.92(14) ?
    C8 C9 C10 C15 . . . . 68.66(19) ?
    C15 C10 C11 C12 . . . . -1.0(2) ?
    C9 C10 C11 C12 . . . . 177.20(16) ?
    C10 C11 C12 C13 . . . . -0.8(3) ?
    C11 C12 C13 C14 . . . . 1.9(3) ?
    C12 C13 C14 C15 . . . . -1.2(3) ?
    C13 C14 C15 C10 . . . . -0.6(3) ?
    C11 C10 C15 C14 . . . . 1.7(2) ?
    C9 C10 C15 C14 . . . . -176.58(15) ?
    N2 N1 C16 N3 . . . . 0.44(17) ?
    C9 N1 C16 N3 . . . . 170.45(13) ?
    N2 N1 C16 S1 . . . . -176.68(12) ?
    C9 N1 C16 S1 . . . . -6.7(2) ?
    C17 N3 C16 N1 . . . . -1.28(17) ?
    N4 N3 C16 N1 . . . . -173.98(14) ?
    C17 N3 C16 S1 . . . . 175.93(12) ?
    N4 N3 C16 S1 . . . . 3.2(2) ?
    N1 N2 C17 N3 . . . . -1.40(17) ?
    N1 N2 C17 C18 . . . . 176.23(15) ?
    C16 N3 C17 N2 . . . . 1.76(18) ?
    N4 N3 C17 N2 . . . . 174.50(14) ?
    C16 N3 C17 C18 . . . . -175.88(15) ?
    N4 N3 C17 C18 . . . . -3.1(2) ?
    N2 C17 C18 C19 . . . . 109.40(19) ?
    N3 C17 C18 C19 . . . . -73.3(2) ?
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 H4A O1 4_566 0.92(2) 2.39(2) 3.138(2) 139(2)
    N4 H4B S1 4_566 0.91(2) 2.55(2) 3.458(2) 172(2)
    C19 H19C S1 4_566 0.98 2.87 3.743(2) 149
    C12 H12 Cg2 3_566 0.95 2.97 3.711(2) 136
    C18 H18A Cg3 3_566 0.99 2.75 3.7275(18) 170
    C19 H19B Cg2 1_556 0.98 2.75 3.5032(19) 134
    C2 H2 Cg1 3_666 0.95 2.99 3.924(2) 168
