##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_I
_audit_creation_method     SHELXL-2013
_journal_date_recd_electronic     2023-03-28
_journal_date_accepted     2023-04-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      5
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023003237
_journal_coeditor_code     TX2066
_publ_contact_author_name     'Ajaya Bhattarai'
_publ_contact_author_address
;
Department of Chemistry,
M.M.A.M.C (Tribhuvan University) Biratnagar,
Nepal
;
_publ_contact_author_email     'ajaya.bhattarai@mmamc.tu.edu.np'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure and Hirshfeld surface analysis of
1,6-diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Farid N. Naghiyev'
;
Department of Chemistry,
Baku State University, Z. Khalilov str. 23,
Az, 1148 Baku, Azerbaijan
;
    'Victor N. Khrustalev'
;
Peoples' Friendship University of Russia (RUDN University),
Miklukho-Maklay St. 6, Moscow, 117198
Russian Federation
N. D. Zelinsky Institute of Organic Chemistry RAS,
Leninsky Prosp. 47, Moscow, 119991
Russian Federation
;
    'Akkurt, Mehmet'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Ali N. Khalilov'
;
"Composite Materials" Scientific Research Center,
Azerbaijan State Economic University (UNEC),
H. Aliyev str. 135, Az 1063,
Baku, Azerbaijan
Department of Chemistry,
Baku State University, Z. Khalilov str. 23,
Az, 1148 Baku, Azerbaijan
;
    'Ajaya Bhattarai'
;
Department of Chemistry,
M.M.A.M.C (Tribhuvan University) Biratnagar,
Nepal
;
    'Fuad Sh. Kerimli'
;
Department of Chemistry,
Baku State University, Z. Khalilov str. 23,
Az, 1148 Baku, Azerbaijan
;
    'İbrahim G. Mamedov'
;
Department of Chemistry,
Baku State University, Z. Khalilov str. 23,
Az, 1148 Baku, Azerbaijan
;
_publ_section_synopsis
;
In the crystal, molecules are linked by intermolecular N---H...O and N---H...N
hydrogen bonds into ribbons parallel to (022) along the a axis. These
ribbons are connected by N---H...O, N---H...N  hydrogen bonds and van der
Waals interactions.
;
_chemical_name_systematic
;
1,6-Diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H7 N5 O S'
_chemical_formula_sum     'C11 H7 N5 O S'
_chemical_formula_iupac     'C11 H7 N5 O S'
_chemical_formula_weight     257.28
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.94782(10)
_cell_length_b     9.03908(9)
_cell_length_c     14.87299(18)
_cell_angle_alpha     90.9441(9)
_cell_angle_beta     104.1197(10)
_cell_angle_gamma     111.7451(10)
_cell_volume     1075.92(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     26181
_cell_measurement_theta_min     3.06
_cell_measurement_theta_max     78.78
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.588
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     528
_exptl_absorpt_coefficient_mu     2.652
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_absorpt_correction_T_min     0.505
_exptl_absorpt_correction_T_max     0.561
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type     'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     32558
_diffrn_reflns_av_R_equivalents     0.0326
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_theta_min     3.086
_diffrn_reflns_theta_max     79.279
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.974
_diffrn_measured_fraction_theta_full     0.996
_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     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     4547
_reflns_number_gt     4467
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0408
_refine_ls_R_factor_gt     0.0404
_refine_ls_wR_factor_gt     0.1042
_refine_ls_wR_factor_ref     0.1045
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     4547
_refine_ls_number_parameters     362
_refine_ls_number_restraints     11
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'w=1/[σ²(Fo²)+(0.046P)²+1.11P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.454
_refine_diff_density_min     -0.457
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0028(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_cell_refinement
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.42276(5) 0.52922(6) 0.09865(3) 0.02122(13) Uani d 1 . .
    O O1 0.79462(15) 0.40083(16) 0.42272(9) 0.0213(3) Uani d 1 . .
    N N1 0.96105(17) 0.46444(18) 0.32428(10) 0.0155(3) Uani d 1 . .
    N N2 1.07380(19) 0.4068(2) 0.38163(11) 0.0204(3) Uani d 1 . .
    H H2A 1.022(3) 0.306(3) 0.3791(16) 0.024 Uiso d 1 . .
    H H2B 1.100(3) 0.458(3) 0.4416(17) 0.024 Uiso d 1 . .
    N N3 0.44940(19) 0.4937(2) 0.33818(11) 0.0234(3) Uani d 1 . .
    N N4 0.9777(2) 0.6738(2) 0.03594(12) 0.0287(4) Uani d 1 . .
    N N5 1.14206(19) 0.5269(2) 0.23148(11) 0.0209(3) Uani d 1 . .
    H H5A 1.166(3) 0.560(3) 0.1804(18) 0.025 Uiso d 1 . .
    H H5B 1.208(3) 0.495(3) 0.2738(17) 0.025 Uiso d 1 . .
    C C2 0.8182(2) 0.4562(2) 0.34957(12) 0.0167(3) Uani d 1 . .
    C C3 0.7099(2) 0.5149(2) 0.28660(12) 0.0180(3) Uani d 1 . .
    C C4 0.7451(2) 0.5773(2) 0.20585(12) 0.0178(3) Uani d 1 . .
    C C5 0.8932(2) 0.5840(2) 0.18606(12) 0.0170(3) Uani d 1 . .
    C C6 1.0017(2) 0.5258(2) 0.24648(12) 0.0168(3) Uani d 1 . .
    C C7 0.5643(2) 0.5051(2) 0.31343(12) 0.0181(3) Uani d 1 . .
    C C8 0.6340(2) 0.6391(2) 0.14265(12) 0.0175(3) Uani d 1 . .
    C C9 0.6819(2) 0.7868(2) 0.10847(12) 0.0175(3) Uani d 1 . .
    H H9 0.7933 0.8642 0.1235 0.021 Uiso calc 1 . .
    C C10 0.5435(3) 0.8072(2) 0.04835(14) 0.0249(4) Uani d 1 . .
    H H10 0.5523 0.9018 0.0193 0.030 Uiso calc 1 . .
    C C11 0.3974(2) 0.6796(2) 0.03603(13) 0.0239(4) Uani d 1 . .
    H H11 0.2935 0.6741 -0.0026 0.029 Uiso calc 1 . .
    C C12 0.9363(2) 0.6369(2) 0.10243(13) 0.0202(4) Uani d 1 . .
    S S2 0.80863(7) -0.08316(7) 0.72047(4) 0.02529(14) Uani d 0.9 A 1
    S S2' 0.6895(15) -0.0343(17) 0.8718(3) 0.0314(5) Uani d 0.1 A 2
    O O2 0.11544(15) -0.02340(16) 0.64254(9) 0.0214(3) Uani d 1 . .
    N N6 0.31497(17) 0.12527(18) 0.57464(10) 0.0160(3) Uani d 1 . .
    N N7 0.19787(19) 0.1759(2) 0.51471(11) 0.0193(3) Uani d 1 . .
    H H7A 0.129(3) 0.094(3) 0.4695(17) 0.023 Uiso d 1 . .
    H H7B 0.140(3) 0.197(3) 0.5497(16) 0.023 Uiso d 1 . .
    N N8 0.2765(2) -0.1813(2) 0.82807(11) 0.0230(3) Uani d 1 . .
    N N9 0.86800(19) 0.19394(19) 0.57542(11) 0.0213(3) Uani d 1 . .
    N N10 0.4975(2) 0.25717(19) 0.48991(11) 0.0190(3) Uani d 1 . .
    H H10A 0.424(3) 0.292(3) 0.4638(16) 0.023 Uiso d 1 . .
    H H10B 0.591(3) 0.293(3) 0.4796(16) 0.023 Uiso d 1 . .
    C C13 0.2627(2) 0.0251(2) 0.64097(12) 0.0174(3) Uani d 1 . .
    C C14 0.3908(2) -0.0122(2) 0.70405(12) 0.0198(4) Uani d 1 . .
    C C15 0.5502(2) 0.0312(2) 0.69219(12) 0.0194(4) Uani d 1 . .
    C C16 0.5878(2) 0.1196(2) 0.61720(12) 0.0161(3) Uani d 1 . .
    C C17 0.4699(2) 0.1710(2) 0.55950(12) 0.0164(3) Uani d 1 . .
    C C18 0.3323(2) -0.1073(2) 0.77379(12) 0.0181(3) Uani d 1 . .
    C C19 0.6737(2) -0.0168(2) 0.75586(11) 0.0189(3) Uani d 1 . .
    C C20 0.6928(6) -0.0243(7) 0.84874(15) 0.0314(5) Uani d 0.9 A 1
    H H20 0.6287 0.0068 0.8819 0.038 Uiso calc 0.9 A 1
    C C21 0.8164(3) -0.0824(3) 0.89227(16) 0.0287(5) Uani d 0.9 A 1
    H H21 0.8463 -0.0917 0.9571 0.034 Uiso calc 0.9 A 1
    C C22 0.8866(3) -0.1231(3) 0.82943(14) 0.0211(4) Uani d 0.9 A 1
    H H22 0.9689 -0.1681 0.8445 0.025 Uiso calc 0.9 A 1
    C C20' 0.7887(14) -0.0522(15) 0.7247(13) 0.02529(14) Uani d 0.1 A 2
    H H20A 0.7989 -0.0491 0.6626 0.030 Uiso calc 0.1 A 2
    C C21' 0.891(2) -0.0945(14) 0.8000(13) 0.0211(4) Uani d 0.1 A 2
    H H21A 0.9796 -0.1234 0.7924 0.025 Uiso calc 0.1 A 2
    C C22' 0.8558(11) -0.0913(9) 0.8836(15) 0.0287(5) Uani d 0.1 A 2
    H H22A 0.9139 -0.1166 0.9398 0.034 Uiso calc 0.1 A 2
    C C23 0.7447(2) 0.1620(2) 0.59624(12) 0.0170(3) Uani d 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 C11 . 1.713(2) ?
    S1 C8 . 1.7239(18) ?
    O1 C2 . 1.237(2) ?
    N1 C6 . 1.362(2) ?
    N1 C2 . 1.395(2) ?
    N1 N2 . 1.4148(19) ?
    N2 H2A . 0.85(3) ?
    N2 H2B . 0.93(2) ?
    N3 C7 . 1.145(2) ?
    N4 C12 . 1.151(2) ?
    N5 C6 . 1.325(2) ?
    N5 H5A . 0.87(3) ?
    N5 H5B . 0.88(3) ?
    C2 C3 . 1.433(2) ?
    C3 C4 . 1.391(2) ?
    C3 C7 . 1.426(2) ?
    C4 C5 . 1.406(2) ?
    C4 C8 . 1.468(2) ?
    C5 C6 . 1.412(2) ?
    C5 C12 . 1.429(2) ?
    C8 C9 . 1.388(3) ?
    C9 C10 . 1.415(2) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.353(3) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
    S2 C22 . 1.702(2) ?
    S2 C19 . 1.7120(17) ?
    S2' C19 . 1.711(3) ?
    S2' C22' . 1.719(3) ?
    O2 C13 . 1.232(2) ?
    N6 C17 . 1.369(2) ?
    N6 C13 . 1.397(2) ?
    N6 N7 . 1.4192(19) ?
    N7 H7A . 0.91(3) ?
    N7 H7B . 0.88(2) ?
    N8 C18 . 1.147(2) ?
    N9 C23 . 1.153(2) ?
    N10 C17 . 1.322(2) ?
    N10 H10A . 0.85(2) ?
    N10 H10B . 0.84(3) ?
    C13 C14 . 1.442(2) ?
    C14 C15 . 1.389(2) ?
    C14 C18 . 1.432(2) ?
    C15 C16 . 1.417(2) ?
    C15 C19 . 1.471(2) ?
    C16 C17 . 1.414(2) ?
    C16 C23 . 1.427(2) ?
    C19 C20 . 1.356(2) ?
    C19 C20' . 1.360(3) ?
    C20 C21 . 1.418(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.360(2) ?
    C21 H21 . 0.9500 ?
    C22 H22 . 0.9500 ?
    C20' C21' . 1.420(3) ?
    C20' H20A . 0.9500 ?
    C21' C22' . 1.359(3) ?
    C21' H21A . 0.9500 ?
    C22' H22A . 0.9500 ?
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
    C11 S1 C8 . . 91.74(9) ?
    C6 N1 C2 . . 124.17(14) ?
    C6 N1 N2 . . 116.35(13) ?
    C2 N1 N2 . . 119.48(14) ?
    N1 N2 H2A . . 106.5(16) ?
    N1 N2 H2B . . 105.8(14) ?
    H2A N2 H2B . . 111(2) ?
    C6 N5 H5A . . 118.2(16) ?
    C6 N5 H5B . . 119.1(15) ?
    H5A N5 H5B . . 123(2) ?
    O1 C2 N1 . . 118.98(15) ?
    O1 C2 C3 . . 125.41(15) ?
    N1 C2 C3 . . 115.61(14) ?
    C4 C3 C7 . . 122.82(15) ?
    C4 C3 C2 . . 122.37(15) ?
    C7 C3 C2 . . 114.82(15) ?
    C3 C4 C5 . . 118.57(15) ?
    C3 C4 C8 . . 121.73(15) ?
    C5 C4 C8 . . 119.68(15) ?
    C4 C5 C6 . . 120.31(15) ?
    C4 C5 C12 . . 123.03(15) ?
    C6 C5 C12 . . 116.49(15) ?
    N5 C6 N1 . . 117.64(15) ?
    N5 C6 C5 . . 123.40(16) ?
    N1 C6 C5 . . 118.96(15) ?
    N3 C7 C3 . . 176.99(18) ?
    C9 C8 C4 . . 126.08(16) ?
    C9 C8 S1 . . 111.33(13) ?
    C4 C8 S1 . . 122.57(13) ?
    C8 C9 C10 . . 111.33(16) ?
    C8 C9 H9 . . 124.3 ?
    C10 C9 H9 . . 124.3 ?
    C11 C10 C9 . . 113.81(17) ?
    C11 C10 H10 . . 123.1 ?
    C9 C10 H10 . . 123.1 ?
    C10 C11 S1 . . 111.78(14) ?
    C10 C11 H11 . . 124.1 ?
    S1 C11 H11 . . 124.1 ?
    N4 C12 C5 . . 175.40(18) ?
    C22 S2 C19 . . 92.90(9) ?
    C19 S2' C22' . . 91.8(9) ?
    C17 N6 C13 . . 124.25(14) ?
    C17 N6 N7 . . 117.12(14) ?
    C13 N6 N7 . . 118.50(13) ?
    N6 N7 H7A . . 108.6(15) ?
    N6 N7 H7B . . 106.1(15) ?
    H7A N7 H7B . . 110(2) ?
    C17 N10 H10A . . 117.1(16) ?
    C17 N10 H10B . . 121.3(16) ?
    H10A N10 H10B . . 120(2) ?
    O2 C13 N6 . . 119.40(15) ?
    O2 C13 C14 . . 124.96(16) ?
    N6 C13 C14 . . 115.63(15) ?
    C15 C14 C18 . . 124.60(16) ?
    C15 C14 C13 . . 122.10(16) ?
    C18 C14 C13 . . 113.12(15) ?
    C14 C15 C16 . . 118.19(15) ?
    C14 C15 C19 . . 119.86(15) ?
    C16 C15 C19 . . 121.94(15) ?
    C17 C16 C15 . . 121.00(15) ?
    C17 C16 C23 . . 116.69(15) ?
    C15 C16 C23 . . 122.31(15) ?
    N10 C17 N6 . . 117.38(15) ?
    N10 C17 C16 . . 124.41(16) ?
    N6 C17 C16 . . 118.18(15) ?
    N8 C18 C14 . . 175.66(18) ?
    C20 C19 C15 . . 126.3(2) ?
    C20' C19 C15 . . 120.7(8) ?
    C20' C19 S2' . . 113.7(9) ?
    C15 C19 S2' . . 125.6(3) ?
    C20 C19 S2 . . 109.75(18) ?
    C15 C19 S2 . . 123.87(12) ?
    C19 C20 C21 . . 114.3(3) ?
    C19 C20 H20 . . 122.8 ?
    C21 C20 H20 . . 122.8 ?
    C22 C21 C20 . . 111.4(2) ?
    C22 C21 H21 . . 124.3 ?
    C20 C21 H21 . . 124.3 ?
    C21 C22 S2 . . 111.52(17) ?
    C21 C22 H22 . . 124.2 ?
    S2 C22 H22 . . 124.2 ?
    C19 C20' C21' . . 109.0(15) ?
    C19 C20' H20A . . 125.5 ?
    C21' C20' H20A . . 125.5 ?
    C22' C21' C20' . . 116(2) ?
    C22' C21' H21A . . 121.9 ?
    C20' C21' H21A . . 121.9 ?
    C21' C22' S2' . . 109.3(16) ?
    C21' C22' H22A . . 125.3 ?
    S2' C22' H22A . . 125.3 ?
    N9 C23 C16 . . 177.12(19) ?
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
    C6 N1 C2 O1 . . . . -178.66(16) ?
    N2 N1 C2 O1 . . . . 1.2(2) ?
    C6 N1 C2 C3 . . . . 1.1(3) ?
    N2 N1 C2 C3 . . . . -179.01(15) ?
    O1 C2 C3 C4 . . . . 179.29(18) ?
    N1 C2 C3 C4 . . . . -0.5(3) ?
    O1 C2 C3 C7 . . . . -0.4(3) ?
    N1 C2 C3 C7 . . . . 179.81(16) ?
    C7 C3 C4 C5 . . . . 179.12(17) ?
    C2 C3 C4 C5 . . . . -0.6(3) ?
    C7 C3 C4 C8 . . . . 0.6(3) ?
    C2 C3 C4 C8 . . . . -179.13(17) ?
    C3 C4 C5 C6 . . . . 1.1(3) ?
    C8 C4 C5 C6 . . . . 179.65(16) ?
    C3 C4 C5 C12 . . . . 176.19(17) ?
    C8 C4 C5 C12 . . . . -5.2(3) ?
    C2 N1 C6 N5 . . . . 179.57(16) ?
    N2 N1 C6 N5 . . . . -0.3(2) ?
    C2 N1 C6 C5 . . . . -0.7(3) ?
    N2 N1 C6 C5 . . . . 179.46(16) ?
    C4 C5 C6 N5 . . . . 179.26(18) ?
    C12 C5 C6 N5 . . . . 3.8(3) ?
    C4 C5 C6 N1 . . . . -0.5(3) ?
    C12 C5 C6 N1 . . . . -175.92(16) ?
    C3 C4 C8 C9 . . . . 129.8(2) ?
    C5 C4 C8 C9 . . . . -48.7(3) ?
    C3 C4 C8 S1 . . . . -52.1(2) ?
    C5 C4 C8 S1 . . . . 129.31(16) ?
    C11 S1 C8 C9 . . . . -0.62(14) ?
    C11 S1 C8 C4 . . . . -178.91(15) ?
    C4 C8 C9 C10 . . . . 179.27(16) ?
    S1 C8 C9 C10 . . . . 1.05(19) ?
    C8 C9 C10 C11 . . . . -1.1(2) ?
    C9 C10 C11 S1 . . . . 0.6(2) ?
    C8 S1 C11 C10 . . . . 0.01(15) ?
    C17 N6 C13 O2 . . . . -172.12(17) ?
    N7 N6 C13 O2 . . . . 3.8(2) ?
    C17 N6 C13 C14 . . . . 8.5(2) ?
    N7 N6 C13 C14 . . . . -175.61(15) ?
    O2 C13 C14 C15 . . . . 172.61(18) ?
    N6 C13 C14 C15 . . . . -8.0(3) ?
    O2 C13 C14 C18 . . . . -2.9(3) ?
    N6 C13 C14 C18 . . . . 176.52(15) ?
    C18 C14 C15 C16 . . . . 177.10(17) ?
    C13 C14 C15 C16 . . . . 2.2(3) ?
    C18 C14 C15 C19 . . . . -2.0(3) ?
    C13 C14 C15 C19 . . . . -176.95(17) ?
    C14 C15 C16 C17 . . . . 3.9(3) ?
    C19 C15 C16 C17 . . . . -177.03(16) ?
    C14 C15 C16 C23 . . . . -176.47(17) ?
    C19 C15 C16 C23 . . . . 2.6(3) ?
    C13 N6 C17 N10 . . . . 175.40(16) ?
    N7 N6 C17 N10 . . . . -0.6(2) ?
    C13 N6 C17 C16 . . . . -2.9(3) ?
    N7 N6 C17 C16 . . . . -178.87(15) ?
    C15 C16 C17 N10 . . . . 178.19(17) ?
    C23 C16 C17 N10 . . . . -1.5(3) ?
    C15 C16 C17 N6 . . . . -3.6(3) ?
    C23 C16 C17 N6 . . . . 176.68(15) ?
    C14 C15 C19 C20 . . . . -36.9(4) ?
    C16 C15 C19 C20 . . . . 144.0(4) ?
    C14 C15 C19 C20' . . . . 146.3(6) ?
    C16 C15 C19 C20' . . . . -32.8(6) ?
    C14 C15 C19 S2' . . . . -33.7(6) ?
    C16 C15 C19 S2' . . . . 147.2(6) ?
    C14 C15 C19 S2 . . . . 139.30(16) ?
    C16 C15 C19 S2 . . . . -39.8(2) ?
    C22' S2' C19 C20 . . . . -73(10) ?
    C22' S2' C19 C20' . . . . 0.00(9) ?
    C22' S2' C19 C15 . . . . 179.99(5) ?
    C22' S2' C19 S2 . . . . 6.2(6) ?
    C22 S2 C19 C20 . . . . 0.9(3) ?
    C22 S2 C19 C20' . . . . 120(7) ?
    C22 S2 C19 C15 . . . . -175.83(17) ?
    C22 S2 C19 S2' . . . . -1.9(5) ?
    C20' C19 C20 C21 . . . . -6.0(10) ?
    C15 C19 C20 C21 . . . . 177.0(2) ?
    S2' C19 C20 C21 . . . . 102(10) ?
    S2 C19 C20 C21 . . . . 0.3(5) ?
    C19 C20 C21 C22 . . . . -1.8(5) ?
    C20 C21 C22 S2 . . . . 2.4(3) ?
    C19 S2 C22 C21 . . . . -1.95(19) ?
    C20 C19 C20' C21' . . . . 2.8(8) ?
    C15 C19 C20' C21' . . . . -179.99(8) ?
    S2' C19 C20' C21' . . . . 0.01(13) ?
    S2 C19 C20' C21' . . . . -60(7) ?
    C19 C20' C21' C22' . . . . -0.01(19) ?
    C20' C21' C22' S2' . . . . 0.01(18) ?
    C19 S2' C22' C21' . . . . -0.01(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
    N2 H2A O2 2_656 0.85(3) 2.37(3) 3.212(2) 174(2)
    N2 H2B O1 2_766 0.93(2) 2.16(3) 3.086(2) 169(2)
    N5 H5B N3 1_655 0.88(3) 2.14(3) 2.944(2) 151(2)
    N7 H7A O2 2_556 0.91(3) 2.26(2) 3.010(2) 139(2)
    N7 H7B N9 1_455 0.88(2) 2.55(2) 3.348(2) 152(2)
    N10 H10A N3 . 0.85(2) 2.62(2) 3.196(2) 126(2)
    N10 H10B O1 . 0.84(3) 2.11(3) 2.921(2) 165(2)
    N5 H5B N2 . 0.88(3) 2.22(3) 2.606(2) 106(2)
    N10 H10A N7 . 0.85(3) 2.23(3) 2.626(3) 109(2)
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.557
_shelx_estimated_absorpt_T_max     0.619
_shelxl_version_number         .2013
