##############################################################################
#                                                                            #
# 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    # 
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data_I
_audit_creation_method     SHELXL-2013
_journal_date_recd_electronic     2018-01-06
_journal_date_accepted     2018-01-14
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618000871
_journal_coeditor_code     HB4203
_publ_contact_author_name     'Gamal A. El-Hiti'
_publ_contact_author_address
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
P.O. Box 10219
Riyadh 11433
Saudi Arabia
;
_publ_contact_author_email     'gelhiti@ksu.edu.sa'
_publ_contact_author_fax     '00966114693536'
_publ_contact_author_phone     '00966114693778'
_publ_section_title
;\
2-({6-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]imidazo\
[2,1-b]thiazol-5-yl}methylidene)hydrazinecarbothioamide
dimethylformamide 0.25-solvate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'El-Hiti, Gamal A.' .
;
Cornea Research Chair
Department of Optometry
College of Applied Medical Sciences
King Saud University
PO Box 10219
Riyadh 11433
Saudi Arabia
;
    'Abdel-Wahab, Bakr F.' .
;
Department of Chemistry
College of Science and Humanities
Shaqra University
Duwadimi
Saudi Arabia
Applied Organic Chemistry Department, National Research Centre,
Dokki, Giza, Egypt
;
    'Alotaibi, Mohammad Hayal' .
;
National Center for Petrochemicals Technology
King Abdulaziz City for Science and Technology
PO Box 6086
Riyadh 11442
Saudi Arabia
;
    'Hegazy, Amany S.' .
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
UK
;
    'Kariuki, Benson M.'
;
Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.
;
;
School of Chemistry
Cardiff University
Main Building
Park Place
Cardiff CF10 3AT
UK
;
_publ_section_synopsis
;
The asymmetric unit of the title solvate comprises two C₁₇H₁₆N₈S₂
molecules and a dimethylformamide molecule disordered about a crystallographic
inversion centre. Both triazole molecules feature an intramolecular C---H...N
interaction, which generates an S(6) ring in each case.
;
_chemical_name_systematic
;\
2-({6-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]imidazo\
[2,1-b]thiazol-5-yl}methylidene)hydrazinecarbothioamide
dimethylformamide 0.25-solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     '4(C17 H16 N8 S2), C3 H7 N O'
_chemical_formula_sum     'C71 H71 N33 O S8'
_chemical_formula_iupac     '4C17 H16 N8 S2, C3 H7 N O'
_chemical_formula_weight     1659.08
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     18.3427(14)
_cell_length_b     13.5855(10)
_cell_length_c     16.9385(12)
_cell_angle_alpha     90
_cell_angle_beta     110.393(9)
_cell_angle_gamma     90
_cell_volume     3956.4(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4302
_cell_measurement_theta_min     3.8290
_cell_measurement_theta_max     25.9420
_cell_measurement_temperature     296(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.375
_exptl_crystal_size_mid     0.209
_exptl_crystal_size_min     0.186
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1728
_exptl_absorpt_coefficient_mu     0.293
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2014)
;
_shelx_estimated_absorpt_T_min     0.898
_shelx_estimated_absorpt_T_max     0.948
_exptl_absorpt_correction_T_min     0.996
_exptl_absorpt_correction_T_max     0.998
_exptl_special_details
;
Numerical absorption correction based on gaussian integration
over a
 multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Agilent SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     22546
_diffrn_reflns_av_R_equivalents     0.0488
_diffrn_reflns_theta_min     2.422
_diffrn_reflns_theta_max     29.946
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.841
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
All hydrogen atoms were placed in calculated positions and refined using a
riding model. Methyl C---H bonds were fixed at 0.96 Å, with displacement
parameters 1.5 times Ueq(C), and were allowed to spin about the
C---C/C---N bonds. N---H bonds were fixed at 0.86 Å and sp² C---H
distances were set to 0.93 Å and their U(iso) set to 1.2 times the
Ueq for the atoms to which they are bonded. The DMF solvent molecule
is diordered about a crystallographic inversion centre.
;
_reflns_number_total     9646
_reflns_number_gt     5318
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1240
_refine_ls_R_factor_gt     0.0639
_refine_ls_wR_factor_gt     0.1459
_refine_ls_wR_factor_ref     0.1810
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.687
_refine_ls_number_reflns     9646
_refine_ls_number_parameters     533
_refine_ls_number_restraints     61
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0600P)²+2.4742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.452
_refine_diff_density_min     -0.288
_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
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SHELXS2013 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft,
2001)
;
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
    C C1 -0.17220(19) 0.2265(2) 0.22798(18) 0.0442(7) Uani d 1 . .
    C C2 -0.03664(18) 0.1621(2) 0.42338(19) 0.0448(7) Uani d 1 . .
    H H2 -0.0605 0.1912 0.4578 0.054 Uiso calc 1 . .
    C C3 0.03317(17) 0.1064(2) 0.45952(18) 0.0416(7) Uani d 1 . .
    C C4 0.0536(2) 0.0284(3) 0.3275(2) 0.0526(9) Uani d 1 . .
    H H4 0.0134 0.0543 0.2821 0.063 Uiso calc 1 . .
    C C5 0.1076(2) -0.0338(3) 0.3208(2) 0.0578(9) Uani d 1 . .
    H H5 0.1087 -0.0562 0.2693 0.069 Uiso calc 1 . .
    C C6 0.12846(19) 0.0026(2) 0.46744(19) 0.0452(7) Uani d 1 . .
    C C7 0.08037(17) 0.0885(2) 0.54231(18) 0.0425(7) Uani d 1 . .
    C C8 0.07685(17) 0.1309(3) 0.61939(19) 0.0465(8) Uani d 1 . .
    C C9 0.12373(18) 0.1110(3) 0.70155(19) 0.0481(8) Uani d 1 . .
    C C10 0.1875(2) 0.0397(3) 0.7394(2) 0.0657(10) Uani d 1 . .
    H H10A 0.1948 0.0001 0.6958 0.099 Uiso calc 1 . .
    H H10B 0.1744 -0.0020 0.7783 0.099 Uiso calc 1 . .
    H H10C 0.2347 0.0747 0.7687 0.099 Uiso calc 1 . .
    C C11 0.1323(2) 0.1929(3) 0.8362(2) 0.0583(10) Uani d 1 . .
    C C12 0.1221(3) 0.1250(5) 0.8906(3) 0.118(2) Uani d 1 . .
    H H12 0.0917 0.0695 0.8706 0.142 Uiso calc 1 . .
    C C13 0.1585(3) 0.1405(5) 0.9772(3) 0.113(2) Uani d 1 . .
    H H13 0.1510 0.0947 1.0144 0.136 Uiso calc 1 . .
    C C14 0.2041(2) 0.2197(3) 1.0089(2) 0.0658(11) Uani d 1 . .
    C C15 0.2145(3) 0.2844(3) 0.9527(2) 0.0710(11) Uani d 1 . .
    H H15 0.2467 0.3385 0.9727 0.085 Uiso calc 1 . .
    C C16 0.1788(2) 0.2725(3) 0.8668(2) 0.0651(10) Uani d 1 . .
    H H16 0.1864 0.3187 0.8299 0.078 Uiso calc 1 . .
    C C17 0.2440(3) 0.2316(4) 1.1029(2) 0.0878(15) Uani d 1 . .
    H H17A 0.2992 0.2261 1.1168 0.132 Uiso calc 1 . .
    H H17B 0.2263 0.1812 1.1316 0.132 Uiso calc 1 . .
    H H17C 0.2317 0.2951 1.1198 0.132 Uiso calc 1 . .
    C C18 0.69548(19) 0.2204(3) 0.92434(19) 0.0472(8) Uani d 1 . .
    C C19 0.55451(17) 0.3166(2) 0.99815(18) 0.0427(7) Uani d 1 . .
    H H19 0.5798 0.3042 1.0552 0.051 Uiso calc 1 . .
    C C20 0.48128(17) 0.3667(2) 0.97028(17) 0.0403(7) Uani d 1 . .
    C C21 0.4551(2) 0.3982(3) 0.81034(18) 0.0494(8) Uani d 1 . .
    H H21 0.4974 0.3692 0.8012 0.059 Uiso calc 1 . .
    C C22 0.3979(2) 0.4438(3) 0.7517(2) 0.0603(10) Uani d 1 . .
    H H22 0.3956 0.4497 0.6962 0.072 Uiso calc 1 . .
    C C23 0.37887(19) 0.4471(3) 0.88651(18) 0.0457(8) Uani d 1 . .
    C C24 0.43284(17) 0.3984(2) 1.01217(17) 0.0406(7) Uani d 1 . .
    C C25 0.44181(17) 0.3852(3) 1.10053(18) 0.0430(7) Uani d 1 . .
    C C26 0.40246(17) 0.4329(2) 1.14538(17) 0.0409(7) Uani d 1 . .
    C C27 0.3392(2) 0.5065(3) 1.1218(2) 0.0523(9) Uani d 1 . .
    H H27A 0.3301 0.5290 1.0655 0.078 Uiso calc 1 . .
    H H27B 0.3538 0.5612 1.1600 0.078 Uiso calc 1 . .
    H H27C 0.2926 0.4770 1.1247 0.078 Uiso calc 1 . .
    C C28 0.41642(19) 0.4155(3) 1.29788(18) 0.0481(8) Uani d 1 . .
    C C29 0.4243(3) 0.5090(3) 1.3295(2) 0.0717(12) Uani d 1 . .
    H H29 0.4406 0.5597 1.3026 0.086 Uiso calc 1 . .
    C C30 0.4079(3) 0.5276(4) 1.4015(3) 0.0833(14) Uani d 1 . .
    H H30 0.4132 0.5914 1.4227 0.100 Uiso calc 1 . .
    C C31 0.3838(2) 0.4544(3) 1.4426(2) 0.0651(11) Uani d 1 . .
    C C32 0.3755(2) 0.3616(3) 1.4096(2) 0.0644(11) Uani d 1 . .
    H H32 0.3596 0.3110 1.4368 0.077 Uiso calc 1 . .
    C C33 0.3905(2) 0.3413(3) 1.3360(2) 0.0592(10) Uani d 1 . .
    H H33 0.3830 0.2783 1.3131 0.071 Uiso calc 1 . .
    C C34 0.3650(3) 0.4757(4) 1.5213(3) 0.1001(17) Uani d 1 . .
    H H34A 0.3132 0.5016 1.5056 0.150 Uiso calc 1 . .
    H H34B 0.4013 0.5230 1.5553 0.150 Uiso calc 1 . .
    H H34C 0.3687 0.4160 1.5527 0.150 Uiso calc 1 . .
    N N1 -0.13188(16) 0.2004(2) 0.18044(16) 0.0546(8) Uani d 1 . .
    H H1A -0.0849 0.1796 0.2033 0.066 Uiso calc 1 . .
    H H1B -0.1525 0.2043 0.1265 0.066 Uiso calc 1 . .
    N N2 -0.13701(15) 0.2189(2) 0.31172(15) 0.0484(7) Uani d 1 . .
    H H2A -0.1583 0.2432 0.3453 0.058 Uiso calc 1 . .
    N N3 -0.06606(15) 0.1716(2) 0.34324(16) 0.0466(6) Uani d 1 . .
    N N4 0.06536(14) 0.0494(2) 0.41195(15) 0.0426(6) Uani d 1 . .
    N N5 0.13947(15) 0.0238(2) 0.54691(15) 0.0478(7) Uani d 1 . .
    N N6 0.02709(18) 0.2052(3) 0.61998(18) 0.0678(9) Uani d 1 . .
    N N7 0.04052(19) 0.2341(3) 0.69742(19) 0.0737(10) Uani d 1 . .
    N N8 0.09920(16) 0.1767(3) 0.74714(16) 0.0575(8) Uani d 1 . .
    N N9 0.65336(16) 0.2177(2) 0.84265(16) 0.0593(8) Uani d 1 . .
    H H9A 0.6050 0.2340 0.8256 0.071 Uiso calc 1 . .
    H H9B 0.6744 0.1998 0.8069 0.071 Uiso calc 1 . .
    N N10 0.65883(14) 0.2492(2) 0.97685(15) 0.0485(7) Uani d 1 . .
    H H10 0.6813 0.2429 1.0304 0.058 Uiso calc 1 . .
    N N11 0.58528(14) 0.2886(2) 0.94434(15) 0.0439(6) Uani d 1 . .
    N N12 0.44408(14) 0.39909(19) 0.88760(14) 0.0413(6) Uani d 1 . .
    N N13 0.36887(15) 0.4480(2) 0.95978(15) 0.0501(7) Uani d 1 . .
    N N14 0.49389(16) 0.3208(2) 1.15125(17) 0.0565(8) Uani d 1 . .
    N N15 0.48920(16) 0.3257(2) 1.22687(16) 0.0579(8) Uani d 1 . .
    N N16 0.43392(14) 0.3939(2) 1.22340(15) 0.0466(7) Uani d 1 . .
    S S1 -0.26434(5) 0.26826(9) 0.18941(5) 0.0621(3) Uani d 1 . .
    S S2 0.17525(6) -0.06895(8) 0.41659(6) 0.0609(3) Uani d 1 . .
    S S3 0.78985(5) 0.18878(9) 0.96231(5) 0.0624(3) Uani d 1 . .
    S S4 0.32750(6) 0.49162(9) 0.78729(6) 0.0676(3) Uani d 1 . .
    C C35 0.0467(9) -0.0002(12) 1.0935(5) 0.134(4) Uani d 0.5 . .
    H H35 0.0527 0.0519 1.1309 0.161 Uiso calc 0.5 . .
    C C36 -0.0348(7) 0.0759(10) 0.9677(9) 0.108(3) Uani d 0.5 . .
    H H36A -0.0369 0.0804 0.9104 0.163 Uiso calc 0.5 . .
    H H36B -0.0078 0.1321 0.9987 0.163 Uiso calc 0.5 . .
    H H36C -0.0867 0.0741 0.9690 0.163 Uiso calc 0.5 . .
    C C37 0.0126(7) -0.0813(7) 0.9478(8) 0.115(4) Uani d 0.5 . .
    H H37A 0.0088 -0.0562 0.8935 0.173 Uiso calc 0.5 . .
    H H37B -0.0262 -0.1311 0.9410 0.173 Uiso calc 0.5 . .
    H H37C 0.0633 -0.1091 0.9749 0.173 Uiso calc 0.5 . .
    N N17 0.0000 0.0000 1.0000 0.0897(16) Uani d 1 . .
    O O1 0.0702(6) -0.0692(9) 1.1073(6) 0.149(3) Uani d 0.5 . .
_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
    C1 N1 . 1.317(4) ?
    C1 N2 . 1.342(4) ?
    C1 S1 . 1.684(3) ?
    C2 N3 . 1.281(4) ?
    C2 C3 . 1.429(4) ?
    C3 C7 . 1.389(4) ?
    C3 N4 . 1.389(4) ?
    C4 C5 . 1.338(5) ?
    C4 N4 . 1.399(4) ?
    C5 S2 . 1.731(4) ?
    C6 N5 . 1.321(4) ?
    C6 N4 . 1.367(4) ?
    C6 S2 . 1.715(3) ?
    C7 N5 . 1.376(4) ?
    C7 C8 . 1.449(4) ?
    C8 N6 . 1.363(4) ?
    C8 C9 . 1.384(4) ?
    C9 N8 . 1.355(4) ?
    C9 C10 . 1.483(5) ?
    C11 C12 . 1.361(6) ?
    C11 C16 . 1.363(5) ?
    C11 N8 . 1.434(4) ?
    C12 C13 . 1.400(6) ?
    C13 C14 . 1.353(7) ?
    C14 C15 . 1.356(6) ?
    C14 C17 . 1.512(5) ?
    C15 C16 . 1.382(5) ?
    C18 N9 . 1.330(4) ?
    C18 N10 . 1.346(4) ?
    C18 S3 . 1.679(3) ?
    C19 N11 . 1.285(4) ?
    C19 C20 . 1.431(4) ?
    C20 C24 . 1.385(4) ?
    C20 N12 . 1.398(4) ?
    C21 C22 . 1.321(5) ?
    C21 N12 . 1.392(4) ?
    C22 S4 . 1.730(4) ?
    C23 N13 . 1.316(4) ?
    C23 N12 . 1.357(4) ?
    C23 S4 . 1.724(3) ?
    C24 N13 . 1.375(4) ?
    C24 C25 . 1.459(4) ?
    C25 N14 . 1.358(4) ?
    C25 C26 . 1.379(4) ?
    C26 N16 . 1.352(4) ?
    C26 C27 . 1.477(4) ?
    C28 C29 . 1.366(5) ?
    C28 C33 . 1.368(5) ?
    C28 N16 . 1.436(4) ?
    C29 C30 . 1.377(5) ?
    C30 C31 . 1.373(6) ?
    C31 C32 . 1.365(6) ?
    C31 C34 . 1.516(5) ?
    C32 C33 . 1.395(5) ?
    N2 N3 . 1.381(3) ?
    N6 N7 . 1.308(4) ?
    N7 N8 . 1.358(4) ?
    N10 N11 . 1.376(3) ?
    N14 N15 . 1.315(3) ?
    N15 N16 . 1.360(4) ?
    C35 O1 . 1.025(16) ?
    C35 N17 . 1.516(8) ?
    C36 N17 . 1.235(12) ?
    C37 N17 . 1.482(6) ?
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
    N1 C1 N2 . . 117.4(3) ?
    N1 C1 S1 . . 123.7(2) ?
    N2 C1 S1 . . 118.9(2) ?
    N3 C2 C3 . . 119.4(3) ?
    C7 C3 N4 . . 104.3(3) ?
    C7 C3 C2 . . 132.5(3) ?
    N4 C3 C2 . . 123.1(3) ?
    C5 C4 N4 . . 111.1(3) ?
    C4 C5 S2 . . 113.9(3) ?
    N5 C6 N4 . . 113.1(3) ?
    N5 C6 S2 . . 135.2(3) ?
    N4 C6 S2 . . 111.7(2) ?
    N5 C7 C3 . . 111.8(3) ?
    N5 C7 C8 . . 119.0(3) ?
    C3 C7 C8 . . 129.2(3) ?
    N6 C8 C9 . . 108.7(3) ?
    N6 C8 C7 . . 122.8(3) ?
    C9 C8 C7 . . 128.4(3) ?
    N8 C9 C8 . . 103.4(3) ?
    N8 C9 C10 . . 123.5(3) ?
    C8 C9 C10 . . 133.1(3) ?
    C12 C11 C16 . . 119.7(3) ?
    C12 C11 N8 . . 120.1(4) ?
    C16 C11 N8 . . 120.0(3) ?
    C11 C12 C13 . . 118.7(5) ?
    C14 C13 C12 . . 122.5(5) ?
    C13 C14 C15 . . 117.1(4) ?
    C13 C14 C17 . . 120.5(4) ?
    C15 C14 C17 . . 122.3(4) ?
    C14 C15 C16 . . 122.1(4) ?
    C11 C16 C15 . . 119.8(4) ?
    N9 C18 N10 . . 116.9(3) ?
    N9 C18 S3 . . 122.7(2) ?
    N10 C18 S3 . . 120.4(2) ?
    N11 C19 C20 . . 120.0(3) ?
    C24 C20 N12 . . 103.8(3) ?
    C24 C20 C19 . . 132.5(3) ?
    N12 C20 C19 . . 123.7(2) ?
    C22 C21 N12 . . 111.4(3) ?
    C21 C22 S4 . . 114.0(2) ?
    N13 C23 N12 . . 113.8(3) ?
    N13 C23 S4 . . 135.0(3) ?
    N12 C23 S4 . . 111.2(2) ?
    N13 C24 C20 . . 112.2(2) ?
    N13 C24 C25 . . 119.2(2) ?
    C20 C24 C25 . . 128.6(3) ?
    N14 C25 C26 . . 110.0(3) ?
    N14 C25 C24 . . 122.1(3) ?
    C26 C25 C24 . . 127.9(3) ?
    N16 C26 C25 . . 103.1(3) ?
    N16 C26 C27 . . 123.8(3) ?
    C25 C26 C27 . . 133.0(3) ?
    C29 C28 C33 . . 120.5(3) ?
    C29 C28 N16 . . 120.6(3) ?
    C33 C28 N16 . . 118.9(3) ?
    C28 C29 C30 . . 119.5(4) ?
    C31 C30 C29 . . 121.6(4) ?
    C32 C31 C30 . . 118.1(3) ?
    C32 C31 C34 . . 120.6(4) ?
    C30 C31 C34 . . 121.3(4) ?
    C31 C32 C33 . . 121.3(4) ?
    C28 C33 C32 . . 119.0(4) ?
    C1 N2 N3 . . 119.0(2) ?
    C2 N3 N2 . . 116.7(3) ?
    C6 N4 C3 . . 106.8(2) ?
    C6 N4 C4 . . 113.6(3) ?
    C3 N4 C4 . . 139.5(3) ?
    C6 N5 C7 . . 104.1(3) ?
    N7 N6 C8 . . 109.7(3) ?
    N6 N7 N8 . . 106.3(3) ?
    C9 N8 N7 . . 111.9(3) ?
    C9 N8 C11 . . 126.7(3) ?
    N7 N8 C11 . . 121.2(3) ?
    C18 N10 N11 . . 119.6(2) ?
    C19 N11 N10 . . 116.3(2) ?
    C23 N12 C21 . . 114.0(3) ?
    C23 N12 C20 . . 106.6(2) ?
    C21 N12 C20 . . 139.4(3) ?
    C23 N13 C24 . . 103.7(2) ?
    N15 N14 C25 . . 108.3(3) ?
    N14 N15 N16 . . 107.1(2) ?
    C26 N16 N15 . . 111.5(2) ?
    C26 N16 C28 . . 129.0(3) ?
    N15 N16 C28 . . 119.5(2) ?
    C6 S2 C5 . . 89.64(17) ?
    C23 S4 C22 . . 89.28(16) ?
    O1 C35 N17 . . 106.2(12) ?
    C36 N17 C37 . . 121.4(7) ?
    C36 N17 C35 . . 118.7(8) ?
    C37 N17 C35 . . 118.3(7) ?
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
    C10 H10A N5 . 0.96 2.39 3.074(4) 128
    C27 H27A N13 . 0.96 2.41 3.082(4) 127
    N1 H1A N7 4_565 0.86 2.62 3.200(4) 126
    N1 H1B S3 1_454 0.86 2.62 3.470(3) 172
    N2 H2A S3 4_465 0.86 2.65 3.502(3) 174
    N9 H9A N15 4_565 0.86 2.34 3.024(4) 136
    N9 H9B S1 4_666 0.86 2.64 3.433(3) 154
    N10 H10 S1 1_656 0.86 2.55 3.388(3) 166
    C5 H5 O1 1_554 0.93 2.59 3.472(10) 158
    C36 H36C S3 1_455 0.96 2.72 3.536(14) 143
    C37 H37B N6 2_546 0.96 2.45 3.111(11) 126
    C37 H37C S3 3_657 0.96 2.75 3.706(13) 175
_shelxl_version_number         .2013
