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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026008972

Synthesis, crystal structure and Hirshfeld surface analysis of (Z)-2-({amino­[6-phenyl-3-(4-methylphen­yl)-1,2,4-triazin-5-yl]methyl­­idene}amino)-6-meth­­oxy­benzo[d]thia­zole-4,7-diyl di­acetate

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Yaroslav K. Shtaitz,a,b Dmitry S. Kopchuk,a,b,c Vasiliy S. Gaviko,a,d Menberu Mengesha Woldemariam,e* Mehmet Akkurt,f Nizami A. Ekberovg and Asmet N. Azizovah,i

aThe Ural Federal University, named after the first president of Russia, B. N. Yeltsin, Mira. 19 st., 620002, Yekaterinburg, Russian Federation, bPostovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Sof'i Kovalevskoy 22 st., 620137, Yekaterinburg, Russian Federation, cSirius University of Science and Technology, Olympic Avenue 1, 354340, Sirius Federal Territory, Russian Federation, dM. N. Mikheev Institute of Metal Physics of the Ural Branch of the Russian Academy of Sciences, Sof'i Kovalevskoy 18 st., 620108, Yekaterinburg, Russian Federation, eDepartment of Physics, Jimma University, Jimma, Ethiopia, fDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, gAzerbaijan State Pedagogical University, 68 Uzeyir Hajibeyov St., AZ 1000, Baku, Azerbaijan, hScientific Research Centre (SRC), Azerbaijan Medical University, A. Kasumzade, St. 14, AZ 1022, Baku, Azerbaijan, and iScientific Research Center, Baku Engineering University, Hasan Aliyev str. 120, AZ0101, Khirdalan, Absheron, Azerbaijan
*Correspondence e-mail: [email protected]

Edited by F. F. Ferreira, Universidade Federal do ABC, Brazil (Received 11 August 2026; accepted 28 August 2026; online 8 September 2026)

The stable conformation of the title mol­ecule, C29H24N6O5S, is caused by two intra­molecular N—H⋯N hydrogen bonds producing fused S(5) and S(6) rings. In the crystal, mol­ecules are connected by inter­molecular N—H⋯O inter­actions along the b-axis direction, forming C(9) chains. Furthermore, there are π–π inter­actions [centroid–to-centroid distance = 3.8200 (12) Å] between the benzene ring of the p-tolyl group and the 1,2,4-triazine ring in the same direction. As a result, the mol­ecules form ribbons along the b-axis direction,. A Hirshfeld surface analysis was performed, showing the predominance of H⋯H, O⋯H/H⋯O, C⋯H/H⋯C and N⋯H/H⋯N contacts.

CCDC reference: 2584107

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1. Chemical context

Metal-mediated or metal-free activation of nitriles (C≡N triple bonds) is a powerful synthetic strategy for the functionalization of organo­nitriles to form new N-heterocycles, ligands, metal complexes, catalysts, etc. (Kopylovich et al., 2011View full citation; Mahmudov et al., 2014View full citation). Recently, we developed a new synthetic method for functionalizing the C≡N nitrile group of 5-cyano-1,2,4-triazines with heterocyclic amines via a nucleophilic ipso-substitution reaction (Krinochkin et al., 2022View full citation; Rammohan et al., 2021View full citation); therefore, as a continuation of this work, we investigated 2-amino­benzo­thia­zole as a nucleophile. It was found, that upon solvent-free inter­action of 6-phenyl-3-(p-tol­yl)-1,2,4-triazine-5-carbo­nitrile (1) with 6-meth­oxy­benzo[d]thia­zol-2-amine (2) at 423 K, the reaction yields the unexpected product (Z)-N′-(6-meth­oxy­benzo[d]thia­zol-2-yl)-6-phenyl-3-(p-tol­yl)-1,2,4-triazine-5-carboximidamide (3). An attempt of oxidative cyclization of a six-membered intra­molecular resonance-assisted hydrogen-bonding synthon (Mahmudov & Pombeiro, 2016View full citation) in (3) with lead tetra­acetate in a benzene–acetic acid mixture (Mishra et al., 2007View full citation) resulted in the di­acyl­ated product (Z)-2-({amino­[6-phenyl-3-(p-tol­yl)-1,2,4-triazin-5-yl]methyl­ene}amino)-6-meth­oxy­benzo[d]thia­zole-4,7-diyl di­acetate (4). The structures of the obtained compounds were confirmed by 1H NMR spectroscopy, mass spectrometry, and elemental analysis, as well as by single-crystal X-ray diffraction for compound (4).

[Scheme 1]

2. Structural commentary

The title mol­ecule (Fig. 1[link]) has a stable conformation due to two intra­molecular N—H⋯N hydrogen bonds that produce fused S(5) and S(6) rings (Table 1[link]; Bernstein et al., 1995View full citation). In a six-membered resonance-assisted hydrogen-bonding (RAHB) ring, the N3—H3B⋯N1 bond with [N⋯N distance = 2.676 (2) Å] falls in the N⋯N distance range [2.542–2.897 Å] observed for other supra­molecular synthons (Gurbanov et al., 2020View full citation), and indicates a low delocalization within the heterodienic moiety. The N—H⋯N angle of 130.8 (19)° differs significantly from the average O—H⋯O angle (149°; Bertolasi et al., 1993View full citation) of β-diketone enols involved in similar intra­molecular RAHB.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3A⋯O2i 0.87 (2) 2.59 (2) 3.229 (3) 130.5 (18)
N3—H3A⋯N4 0.87 (2) 2.23 (2) 2.613 (2) 106.8 (17)
N3—H3B⋯N1 0.93 (2) 1.97 (2) 2.676 (2) 130.8 (19)
C17—H17⋯O5ii 0.93 2.55 3.390 (5) 150
C26—H26B⋯O2iii 0.96 2.58 3.390 (4) 143
C27—H27A⋯O3iv 0.96 2.53 3.389 (4) 150
C27—H27B⋯O5Av 0.96 2.29 3.194 (8) 156
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation; (v) Mathematical equation.
[Figure 1]
Figure 1
Mol­ecular structure of the title compound showing the atomic labelling. Displacement ellipsoids are drawn at the 30% probability level.

The 1,3-benzo­thia­zole ring system (S1/N1/C1–C7) is essentially planar with a r.m.s. deviation of 0.0255 Å. The least-squares plane of this ring system forms angles of 17.2 (1), 81.2 (1), and 20.4 (1)° with the ring planes of the 1,2,4-triazine ring (N4–N6/C10–C12) and the benzene ring planes (C13–C18 and C20–C25) of its attached phenyl and 4-methyl­phenyl groups, respectively. The rings (C13–C18 and C20–C25) of the phenyl and 4-methyl­phenyl groups form angles of 62.1 (1)° with each other, while they make angles of 64.0 (1) and 5.8 (1)°, respectively, with the 1,2,4-triazine ring plane (N4–N6/C10–C12).

3. Supra­molecular features

In the crystal, the mol­ecules, arranged at angles of approximately 45° to the a-axis direction and at equal inter­vals, are linked by inter­molecular N—H⋯O inter­actions (Table 1[link]) along the b-axis direction, forming C(9) chains. In addition, there are π-π inter­actions [Cg2⋯Cg5a = 3.8200 (12) Å, shift = 1.107 Å and Cg5⋯Cg2b = 3.8200 (12) Å, shift = 0.963 Å; symmetry codes (a) x, −1 + y, z and (b) x, 1 + y, z] between the centroids Cg2 and Cg5 of the 1,2,4-triazine ring and the benzene ring of the p-tolyl group, along the b-axis direction (Fig. 2[link]a,b). Thus, the mol­ecules form ribbons along the b-axis direction. The cohesion of the packing is ensured by C—H⋯O inter­actions between these ribbons.

[Figure 2]
Figure 2
(a) Partial view of N—H⋯O hydrogen bonds and π–π inter­actions (dashed lines) in the unit cell of the title compound. H atoms not involved in hydrogen bonding and the minor component of the disordered O5 atom are omitted. (b) A different view of these inter­actions within a unit cell.

4. Hirshfeld surface analysis

A Hirshfeld surface analysis and the corresponding fingerprint plots were generated using CrystalExplorer software (Spackman et al., 2021View full citation) to further investigate and qu­antify the contributions of the various inter­molecular inter­actions in the crystal. The Hirshfeld surface mapped over dnorm using a fixed colour scale of −0.3005 (red) to 1.3598 (blue) a.u. and corresponding colours representing various inter­actions is shown in Fig. 3[link]. The two-dimensional fingerprint plots for all inter­molecular inter­actions and those delineated into specific contacts are shown in Fig. 4[link]. The largest contribution comes from H⋯H contacts at 40.3% of the total, which is consistent with the significant hydrogen content of the mol­ecule. The next most important contact is O⋯H/H⋯O at 20.1%, which primarily comes from the intra­molecular O—H⋯O and inter­molecular N—H⋯O as well as C—H⋯O inter­actions. The C⋯H/H⋯C inter­actions account for 15.4% while N⋯H/H⋯N contacts contribute 8.2%, followed by N⋯C/C⋯N contacts contributing 4.0%. Further, 3.9, 2.2, 1.2, 1.1, 0.5, 0.2 and 0.1% contributions corresponding to S⋯H/H⋯S, O⋯C/C⋯O, S⋯C/C⋯S, O⋯N/N⋯O, N⋯N, S⋯O/O⋯S and S⋯N/N⋯S contacts, respectively, are also observed.

[Figure 3]
Figure 3
Hirshfeld surface of the title compound mapped over dnorm.
[Figure 4]
Figure 4
Hirshfeld surface mapped over dnorm and the corresponding two-dimensional fingerprint plots for the title compound. (a) All inter­actions (100%) and the relative contributions of (b) H⋯H (40.3%), (c) O⋯H/H⋯O (20.1%), (d) C⋯H/H⋯C (15.4%) and (e) N⋯H/H⋯N (8.2%) inter­actions to the Hirshfeld surface are indicated. The di and de values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 6.00, update of April 2025; Groom et al., 2016View full citation) for the N′-(1,3-benzo­thia­zol-2-yl)-1,2,4-triazine-5-carboximidamide unit generated six closely related compounds: (Z)-N-(4-meth­oxy­benzo[d]thia­zol-2-yl)-3,6-di-p-tolyl-1,2,4-triazine-5-carb­oximidamide (QARLOP: Shtaitz et al., 2026View full citation), N-[(1,3-benzo­thia­zol-2-yl)carbamo­thio­yl]-4-bromo­benzamide (JOM­GOL: Sow et al., 2024View full citation), N′-(1,3-benzo­thia­zol-2-yl)benzene­sulfono­hydrazide (COCFOS: Baddeley et al., 2019View full citation), N-(1,3-benzo­thia­zol-2-yl)acetamide (TIJPAF: Nayak et al., 2013View full citation), 2-[(6-meth­oxy-1,3-benzo­thia­zol-2-yl)carbonoimido­yl]phenol (SUFFEG: Hijji et al., 2015View full citation) and N-(4,6-di­methyl­pyrimidin-2-yl)-1,3-benzo­thia­zol-2-amine (YAJBUI: Mohamed et al., 2011View full citation).

QARLOP crystallizes in the triclinic PMathematical equation space group while JOMGOL and YAJBUI crystallize in the monoclinic P21/n space group. COCFOS has two mol­ecules (A and B) in the asymmetric unit and crystallizes in the ortho­rhom­bic space group Pbca. TIJPAF has two mol­ecules (A and B) in the asymmetric unit and crystallizes in the monoclinic space group P21/c. SUFFEG has two mol­ecules in the asymmetric unit and crystallizes in the ortho­rhom­bic space group Pna21.

In the crystal of QARLOP, inter­molecular C—H⋯O and C—H⋯N hydrogen bonds form layers parallel to the (010) plane. Furthermore, π–π and C—H⋯π [centroid-to-centroid distance = 3.7380 (12) Å] inter­actions connect mol­ecules, forming ribbons along the a-axis direction. In JOMGOL, inter­molecular C—H⋯N, C—H⋯S, and N—H⋯S hydrogen bonds form layers parallel to the ac plane. In YAJBUI, N—H⋯N hydrogen bonds link the mol­ecules, generating a centrosymmetric cyclic hydrogen-bonded dimer with an R22(8) motif. In COCFOS, the A and B mol­ecules in the asymmetric unit are linked into a supra­molecular dimer via pairwise hydrazinyl-N—H⋯N(thia­zol­yl) hydrogen bonds. Hydrazinyl-N—H⋯O(sulfon­yl) hydrogen bonds between A mol­ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol­ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol­ecules along [001]. The result is an undulating supra­molecular layer. Layers stack along the b-axis direction with benzo­thia­zole-C—H⋯O(sulfon­yl) points of contact being evident. In TIJPAF, the A and B mol­ecules in the asymmetric unit are linked by N—H⋯N hydrogen-bond pairs, forming R22(8) dimer motifs along the [100] axis. In SUFFEG, a pair of C—H⋯O bonds connects two mol­ecules in the asymmetric unit with the ring motif R22(20). Weak inter­molecular C—H⋯N inter­actions also link these dimers, forming sheets parallel to the ab plane.

6. Synthesis and crystallization

The starting compound 5-cyano-1,2,4-triazine was prepared according to a literature procedure (Kozhevnikov et al., 2002View full citation), and a known synthetic procedure (Shtaitz et al., 2026View full citation) was used in the synthesis of (4).

Synthesis of compound (3). 0.37 mmol of 6-phenyl-3-(p-tol­yl)-1,2,4-triazine-5-carbo­nitrile (1) and 0.41 mmol of 6-meth­oxy­benzo[d]thia­zol-2-amine (2) were added into a round-bottom flask and the resulting mixture was heated at 423 K for 8 h under an inert atmosphere. The product was isolated by column chromatography (eluent AcOEt:CDCl3 = 1:9; Rf 0.7 0.4). The pure product (Z)-N′-(6-meth­oxy­benzo[d]thia­zol-2-yl)-6-phenyl-3-(p-tol­yl)-1,2,4-triazine-5-carboximid­amide (3) was obtained by recrystallization from ethanol solution. Yield 72 mg (43%). 1H NMR (400 MHz, CDCl3): δ = 2.48 (s, 3H, CH3), 3.84 (s, 3H, OCH3), 6.99–7.02 (dd, 1H, H-5 (benzo­thia­zole), J 8.9 2.6 Hz,), 7.38–7.42 (m, 2H, C6H4CH3), 7.45–7.50 (m, 3H, Ph), 7.56 (br. s, 1H, NH), 7.69–7.72 [m, 1H, H-4 (benzo­thia­zole)], 7.77–7.80 (m, 2H, Ph), 8.49–8.53 (m, C6H4CH3), 10.18 (br. s, 1H, NH). Mass-spectrum, m/z (Irel, %): m/z: 453.15 [M + H]+ (100). Found, %: C 66.34, H 4.44, N 18.58. C25H20N6OS. Calculated, %: C 66.35, H 4.45, N 18.57.

Synthesis of compound (4): To a solution of 203 mg (0.45 mmol) of compound (3) in 15 mL of benzene and 5 mL of glacial acetic acid, 399 mg (0.90 mmol) of lead tetra­acetate were added. The resulting mixture was stirred at 353 K for 24 h. The solvents were removed under reduced pressure (Fig. 5[link]). The product was isolated by column chromatography (eluent AcOEt:CDCl3 = 0.5:9.5; Rf 0.6). A single crystal of compound (4) was obtained by slow evaporation of a chloro­form solution. (4): Yield 77 mg (30%). 1H NMR (300 MHz, DMSO-d6): δ = 2.34 (s, 3H, OAc), 2.43 (s, 3H, OAc), 2.48 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 6.87 (s, 1H, H-5 (benzo­thia­zole), 7.38–7.41 (m, 2H, C6H4CH3), 7.45–7.52 (m, 3H, Ph), 7.69–7.77 (m, 3H, Ph+NH), 8.48–8.52 (m, C6H4CH3), 9.99 (br. s, 1H, NH). Mass-spectrum, m/z (Irel, %): m/z: 569.15 [M+H]+ (100). Found, %: C 61.28, H 4.24, N 14.77. C29H24N6O5S. Calculated, %: C 61.26, H 4.25, N 14.78.

[Figure 5]
Figure 5
Reaction scheme for the title compound.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The H atoms of the NH2 groups were found in difference-Fourier maps and were refined with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). The oxygen atom (O5) of the carbonyl group exhibits disorder at two positions with a final occupancy ratio of 0.617 (4):0.383 (4). The disordered atom was modelled using SADI and EADP constraints.

Table 2
Experimental details

Crystal data
Chemical formula C29H24N6O5S
Mr 568.60
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 19.7610 (5), 5.8264 (2), 24.3643 (5)
β (°) 94.711 (2)
V (Å3) 2795.72 (13)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.17
Crystal size (mm) 0.41 × 0.25 × 0.16
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, HyPix
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2021View full citation)
Tmin, Tmax 0.951, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections 94505, 7321, 3876
Rint 0.094
(sin θ/λ)max (Å−1) 0.695
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.150, 1.04
No. of reflections 7321
No. of parameters 384
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.21, −0.20
Computer programs: CrysAlis PRO (Rigaku OD, 2021View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation), ORTEP-3 for Windows (Farrugia, 2012View full citation) and PLATON (Spek, 2020View full citation).

Supporting information

CCDC reference: 2584107

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008972/ee2032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026008972/ee2032Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026008972/ee2032Isup3.cml

checkCIF report


Computing details top

(Z)-2-({Amino[6-phenyl-3-(4-methylphenyl)-1,2,4-triazin-5-yl]methylidene}amino)-6-methoxybenzo[d]thiazole-4,7-diyl diacetate top
Crystal data top
C29H24N6O5SF(000) = 1184
Mr = 568.60Dx = 1.351 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 19.7610 (5) ÅCell parameters from 14058 reflections
b = 5.8264 (2) Åθ = 1.7–22.1°
c = 24.3643 (5) ŵ = 0.17 mm−1
β = 94.711 (2)°T = 293 K
V = 2795.72 (13) Å3Prism, red
Z = 40.41 × 0.25 × 0.16 mm
Data collection top
XtaLAB Synergy, Dualflex, HyPix
diffractometer		7321 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source3876 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.094
Detector resolution: 10.0000 pixels mm-1θmax = 29.6°, θmin = 1.7°
ω scansh = −26→27
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)		k = −8→8
Tmin = 0.951, Tmax = 0.974l = −33→32
94505 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0629P)2 + 0.2039P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
7321 reflectionsΔρmax = 0.21 e Å−3
384 parametersΔρmin = −0.19 e Å−3
1 restraint
Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.21371 (10)−0.0169 (3)0.37633 (8)0.0501 (5)
C20.17864 (10)−0.2051 (3)0.44712 (8)0.0513 (5)
C30.14532 (10)−0.3400 (3)0.40576 (8)0.0506 (5)
C40.10892 (10)−0.5327 (3)0.41903 (8)0.0549 (5)
C50.10454 (11)−0.5896 (4)0.47403 (9)0.0634 (6)
C60.13858 (12)−0.4578 (4)0.51514 (9)0.0684 (6)
H60.136281−0.4970310.5519380.082*
C70.17540 (11)−0.2705 (4)0.50151 (8)0.0599 (5)
C80.27976 (17)−0.1373 (5)0.54359 (10)0.0828 (8)
C90.27880 (10)0.3049 (3)0.36523 (8)0.0482 (5)
C100.31600 (10)0.4545 (3)0.32773 (7)0.0486 (5)
C110.39337 (10)0.7418 (4)0.32262 (8)0.0526 (5)
C120.31716 (10)0.4223 (4)0.27052 (8)0.0536 (5)
C130.27288 (12)0.2688 (4)0.23534 (8)0.0579 (5)
C140.30056 (15)0.0875 (4)0.20888 (10)0.0819 (7)
H140.3472860.0643480.2120720.098*
C150.2585 (2)−0.0606 (5)0.17743 (12)0.1074 (11)
H150.277110−0.1871090.1609100.129*
C160.1911 (2)−0.0243 (6)0.17039 (11)0.1051 (10)
H160.163484−0.1247430.1490100.126*
C170.16345 (16)0.1595 (6)0.19459 (11)0.0970 (9)
H170.1170270.1869580.1890620.116*
C180.20404 (13)0.3049 (5)0.22724 (10)0.0787 (7)
H180.1846950.4292120.2440690.094*
C190.30912 (18)0.0520 (6)0.57940 (12)0.1174 (11)
H19A0.3061570.1938560.5592940.176*
H19B0.3558420.0188220.5904440.176*
H19C0.2842110.0650470.6114650.176*
C200.43176 (10)0.9356 (4)0.34862 (8)0.0545 (5)
C210.42356 (11)0.9989 (4)0.40250 (9)0.0660 (6)
H210.3932520.9187150.4226000.079*
C220.45978 (13)1.1791 (4)0.42650 (10)0.0745 (7)
H220.4538211.2178240.4628200.089*
C230.50483 (11)1.3039 (4)0.39798 (10)0.0690 (6)
C240.51209 (12)1.2416 (4)0.34442 (10)0.0771 (7)
H240.5418011.3237560.3241560.093*
C250.47656 (12)1.0611 (4)0.32009 (9)0.0716 (6)
H250.4827701.0227930.2837930.086*
C260.54425 (14)1.5043 (5)0.42390 (12)0.0943 (8)
H26A0.5716661.5714260.3973800.141*
H26B0.5729461.4514800.4550520.141*
H26C0.5131551.6170940.4357180.141*
C270.06120 (16)−0.8397 (5)0.54036 (11)0.0985 (9)
H27A0.036967−0.9819710.5420780.148*
H27B0.036742−0.7208090.5575400.148*
H27C0.105512−0.8557840.5592730.148*
C280.02414 (14)−0.6465 (6)0.35039 (12)0.0957 (9)
C290.00301 (16)−0.8326 (5)0.31195 (13)0.1107 (11)
H29A0.036148−0.8506000.2855790.166*
H29B−0.040186−0.7955030.2931160.166*
H29C−0.000710−0.9730750.3320580.166*
N10.21598 (8)−0.0226 (3)0.42984 (6)0.0517 (4)
N20.24549 (8)0.1299 (3)0.34327 (6)0.0532 (4)
N30.28487 (9)0.3671 (3)0.41783 (7)0.0552 (4)
H3A0.3075 (11)0.491 (4)0.4276 (9)0.066*
H3B0.2614 (11)0.277 (4)0.4415 (9)0.066*
N40.35295 (8)0.6197 (3)0.35291 (6)0.0510 (4)
N50.40296 (10)0.6934 (3)0.27026 (7)0.0698 (5)
N60.36328 (10)0.5355 (3)0.24410 (7)0.0698 (5)
O10.20970 (9)−0.1371 (3)0.54256 (6)0.0756 (5)
O20.31015 (11)−0.2704 (4)0.51763 (9)0.1052 (7)
O30.06773 (9)−0.7806 (3)0.48390 (7)0.0806 (5)
O40.08296 (7)−0.6852 (3)0.37831 (6)0.0671 (4)
O50.0017 (2)−0.4394 (7)0.34761 (19)0.1130 (14)0.617 (4)
O5A−0.0205 (3)−0.5585 (12)0.3785 (3)0.1130 (14)0.383 (4)
S10.16294 (3)−0.23292 (9)0.34217 (2)0.05618 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0507 (11)0.0490 (11)0.0500 (11)0.0021 (9)0.0011 (9)−0.0068 (9)
C20.0538 (12)0.0486 (11)0.0514 (11)−0.0045 (9)0.0048 (9)−0.0061 (9)
C30.0480 (11)0.0484 (11)0.0546 (11)0.0008 (9)−0.0008 (9)−0.0062 (9)
C40.0505 (11)0.0480 (12)0.0650 (13)−0.0035 (9)−0.0036 (9)−0.0115 (10)
C50.0621 (13)0.0540 (13)0.0746 (15)−0.0123 (11)0.0078 (11)−0.0011 (11)
C60.0837 (16)0.0635 (15)0.0586 (13)−0.0206 (12)0.0094 (11)−0.0043 (11)
C70.0716 (14)0.0574 (13)0.0507 (12)−0.0142 (11)0.0054 (10)−0.0086 (10)
C80.106 (2)0.084 (2)0.0546 (14)−0.0285 (17)−0.0156 (14)0.0050 (13)
C90.0467 (11)0.0510 (12)0.0470 (11)0.0048 (9)0.0034 (8)−0.0007 (9)
C100.0474 (11)0.0502 (11)0.0482 (11)0.0054 (9)0.0049 (9)−0.0010 (9)
C110.0492 (11)0.0595 (13)0.0497 (11)−0.0002 (10)0.0078 (9)0.0014 (9)
C120.0573 (12)0.0552 (12)0.0484 (11)0.0045 (10)0.0060 (9)−0.0005 (9)
C130.0744 (15)0.0578 (13)0.0412 (10)−0.0001 (11)0.0042 (10)−0.0011 (9)
C140.109 (2)0.0693 (17)0.0663 (14)0.0119 (15)0.0009 (14)−0.0127 (13)
C150.166 (3)0.074 (2)0.0796 (19)0.007 (2)−0.005 (2)−0.0281 (15)
C160.153 (3)0.090 (2)0.0660 (17)−0.030 (2)−0.0258 (19)−0.0088 (16)
C170.091 (2)0.119 (3)0.0759 (17)−0.0212 (18)−0.0224 (15)−0.0093 (18)
C180.0767 (17)0.0887 (19)0.0687 (15)−0.0005 (14)−0.0063 (13)−0.0146 (13)
C190.152 (3)0.104 (2)0.0905 (19)−0.059 (2)−0.0240 (18)−0.0082 (17)
C200.0479 (11)0.0624 (13)0.0533 (12)−0.0021 (10)0.0048 (9)0.0010 (10)
C210.0655 (14)0.0714 (16)0.0623 (13)−0.0108 (12)0.0122 (11)−0.0041 (11)
C220.0804 (16)0.0771 (17)0.0664 (14)−0.0115 (14)0.0088 (12)−0.0146 (12)
C230.0580 (13)0.0686 (15)0.0793 (16)−0.0048 (11)−0.0018 (12)−0.0066 (12)
C240.0677 (15)0.0888 (19)0.0762 (16)−0.0219 (14)0.0147 (12)−0.0011 (14)
C250.0703 (15)0.0850 (17)0.0605 (13)−0.0202 (13)0.0115 (11)−0.0060 (12)
C260.0827 (18)0.086 (2)0.112 (2)−0.0183 (15)−0.0043 (15)−0.0200 (16)
C270.114 (2)0.087 (2)0.096 (2)−0.0385 (18)0.0131 (17)0.0159 (16)
C280.0722 (17)0.100 (2)0.109 (2)0.0191 (16)−0.0275 (15)−0.0398 (18)
C290.099 (2)0.100 (2)0.126 (2)−0.0037 (18)−0.0388 (18)−0.0402 (19)
N10.0569 (10)0.0491 (10)0.0489 (9)−0.0057 (8)0.0031 (7)−0.0051 (7)
N20.0586 (10)0.0508 (10)0.0500 (9)−0.0047 (8)0.0038 (8)−0.0033 (8)
N30.0621 (11)0.0569 (11)0.0469 (10)−0.0117 (9)0.0064 (8)−0.0034 (8)
N40.0518 (9)0.0542 (10)0.0474 (9)−0.0014 (8)0.0066 (7)−0.0017 (8)
N50.0754 (13)0.0807 (14)0.0555 (11)−0.0163 (11)0.0188 (10)−0.0080 (10)
N60.0803 (13)0.0765 (13)0.0540 (10)−0.0130 (11)0.0133 (10)−0.0072 (9)
O10.1031 (13)0.0737 (11)0.0502 (8)−0.0307 (10)0.0067 (8)−0.0101 (7)
O20.0929 (14)0.1154 (17)0.1015 (15)−0.0004 (12)−0.0275 (12)−0.0177 (13)
O30.0867 (12)0.0673 (11)0.0879 (12)−0.0310 (9)0.0085 (9)0.0015 (9)
O40.0606 (9)0.0546 (9)0.0831 (10)−0.0025 (7)−0.0129 (8)−0.0165 (7)
O50.092 (2)0.085 (3)0.152 (4)0.026 (2)−0.051 (2)−0.031 (2)
O5A0.092 (2)0.085 (3)0.152 (4)0.026 (2)−0.051 (2)−0.031 (2)
S10.0613 (3)0.0532 (3)0.0525 (3)−0.0023 (2)−0.0044 (2)−0.0077 (2)
Geometric parameters (Å, º) top
C1—N11.301 (2)C16—H160.9300
C1—N21.363 (2)C17—C181.374 (4)
C1—S11.774 (2)C17—H170.9300
C2—N11.380 (2)C18—H180.9300
C2—C71.385 (3)C19—H19A0.9600
C2—C31.399 (3)C19—H19B0.9600
C3—C41.386 (3)C19—H19C0.9600
C3—S11.732 (2)C20—C251.379 (3)
C4—C51.390 (3)C20—C211.386 (3)
C4—O41.398 (2)C21—C221.374 (3)
C5—O31.362 (2)C21—H210.9300
C5—C61.391 (3)C22—C231.381 (3)
C6—C71.368 (3)C22—H220.9300
C6—H60.9300C23—C241.373 (3)
C7—O11.397 (2)C23—C261.512 (3)
C8—O21.193 (3)C24—C251.372 (3)
C8—O11.383 (3)C24—H240.9300
C8—C191.494 (4)C25—H250.9300
C9—N21.305 (2)C26—H26A0.9600
C9—N31.328 (2)C26—H26B0.9600
C9—C101.498 (3)C26—H26C0.9600
C10—N41.328 (2)C27—O31.434 (3)
C10—C121.408 (3)C27—H27A0.9600
C11—N51.335 (2)C27—H27B0.9600
C11—N41.336 (2)C27—H27C0.9600
C11—C201.474 (3)C28—O5A1.269 (7)
C12—N61.333 (3)C28—O51.285 (4)
C12—C131.475 (3)C28—O41.317 (3)
C13—C141.374 (3)C28—C291.471 (4)
C13—C181.375 (3)C29—H29A0.9600
C14—C151.385 (4)C29—H29B0.9600
C14—H140.9300C29—H29C0.9600
C15—C161.346 (4)N3—H3A0.87 (2)
C15—H150.9300N3—H3B0.93 (2)
C16—C171.358 (4)N5—N61.336 (3)
N1—C1—N2128.96 (18)C8—C19—H19C109.5
N1—C1—S1115.04 (15)H19A—C19—H19C109.5
N2—C1—S1115.99 (14)H19B—C19—H19C109.5
N1—C2—C7124.86 (17)C25—C20—C21117.8 (2)
N1—C2—C3116.42 (17)C25—C20—C11121.24 (18)
C7—C2—C3118.60 (18)C21—C20—C11120.99 (18)
C4—C3—C2120.64 (18)C22—C21—C20120.6 (2)
C4—C3—S1130.31 (16)C22—C21—H21119.7
C2—C3—S1108.94 (15)C20—C21—H21119.7
C3—C4—C5119.52 (18)C21—C22—C23121.6 (2)
C3—C4—O4121.12 (18)C21—C22—H22119.2
C5—C4—O4118.96 (18)C23—C22—H22119.2
O3—C5—C4116.21 (19)C24—C23—C22117.4 (2)
O3—C5—C6123.9 (2)C24—C23—C26120.7 (2)
C4—C5—C6119.85 (19)C22—C23—C26121.9 (2)
C7—C6—C5120.1 (2)C25—C24—C23121.6 (2)
C7—C6—H6120.0C25—C24—H24119.2
C5—C6—H6120.0C23—C24—H24119.2
C6—C7—C2121.26 (19)C24—C25—C20121.0 (2)
C6—C7—O1120.43 (18)C24—C25—H25119.5
C2—C7—O1118.29 (18)C20—C25—H25119.5
O2—C8—O1122.5 (2)C23—C26—H26A109.5
O2—C8—C19127.0 (3)C23—C26—H26B109.5
O1—C8—C19110.5 (3)H26A—C26—H26B109.5
N2—C9—N3127.71 (18)C23—C26—H26C109.5
N2—C9—C10117.43 (16)H26A—C26—H26C109.5
N3—C9—C10114.85 (18)H26B—C26—H26C109.5
N4—C10—C12120.05 (17)O3—C27—H27A109.5
N4—C10—C9114.74 (16)O3—C27—H27B109.5
C12—C10—C9125.09 (18)H27A—C27—H27B109.5
N5—C11—N4123.62 (19)O3—C27—H27C109.5
N5—C11—C20117.64 (17)H27A—C27—H27C109.5
N4—C11—C20118.70 (17)H27B—C27—H27C109.5
N6—C12—C10118.65 (19)O5A—C28—O4114.4 (4)
N6—C12—C13114.57 (17)O5—C28—O4118.3 (3)
C10—C12—C13126.76 (18)O5A—C28—C29117.9 (4)
C14—C13—C18118.5 (2)O5—C28—C29125.5 (3)
C14—C13—C12119.9 (2)O4—C28—C29113.3 (2)
C18—C13—C12121.6 (2)C28—C29—H29A109.5
C13—C14—C15119.6 (3)C28—C29—H29B109.5
C13—C14—H14120.2H29A—C29—H29B109.5
C15—C14—H14120.2C28—C29—H29C109.5
C16—C15—C14121.0 (3)H29A—C29—H29C109.5
C16—C15—H15119.5H29B—C29—H29C109.5
C14—C15—H15119.5C1—N1—C2110.51 (16)
C15—C16—C17119.9 (3)C9—N2—C1119.31 (16)
C15—C16—H16120.1C9—N3—H3A119.6 (14)
C17—C16—H16120.1C9—N3—H3B115.7 (13)
C16—C17—C18120.0 (3)H3A—N3—H3B124.6 (19)
C16—C17—H17120.0C10—N4—C11117.49 (16)
C18—C17—H17120.0C11—N5—N6118.52 (17)
C17—C18—C13120.8 (3)C12—N6—N5120.54 (17)
C17—C18—H18119.6C8—O1—C7116.00 (18)
C13—C18—H18119.6C5—O3—C27117.19 (18)
C8—C19—H19A109.5C28—O4—C4120.97 (18)
C8—C19—H19B109.5C3—S1—C189.06 (9)
H19A—C19—H19B109.5
N1—C2—C3—C4177.28 (18)N4—C11—C20—C21−3.5 (3)
C7—C2—C3—C41.1 (3)C25—C20—C21—C22−0.9 (3)
N1—C2—C3—S10.8 (2)C11—C20—C21—C22179.7 (2)
C7—C2—C3—S1−175.45 (16)C20—C21—C22—C230.6 (4)
C2—C3—C4—C51.2 (3)C21—C22—C23—C240.1 (4)
S1—C3—C4—C5176.86 (17)C21—C22—C23—C26179.2 (2)
C2—C3—C4—O4−171.53 (18)C22—C23—C24—C25−0.6 (4)
S1—C3—C4—O44.2 (3)C26—C23—C24—C25−179.7 (2)
C3—C4—C5—O3179.76 (19)C23—C24—C25—C200.3 (4)
O4—C4—C5—O3−7.4 (3)C21—C20—C25—C240.4 (4)
C3—C4—C5—C6−2.2 (3)C11—C20—C25—C24179.9 (2)
O4—C4—C5—C6170.6 (2)N2—C1—N1—C2−177.39 (19)
O3—C5—C6—C7178.9 (2)S1—C1—N1—C21.7 (2)
C4—C5—C6—C71.0 (4)C7—C2—N1—C1174.3 (2)
C5—C6—C7—C21.3 (4)C3—C2—N1—C1−1.6 (2)
C5—C6—C7—O1180.0 (2)N3—C9—N2—C1−2.1 (3)
N1—C2—C7—C6−178.2 (2)C10—C9—N2—C1176.82 (17)
C3—C2—C7—C6−2.3 (3)N1—C1—N2—C9−6.8 (3)
N1—C2—C7—O13.1 (3)S1—C1—N2—C9174.04 (14)
C3—C2—C7—O1178.99 (18)C12—C10—N4—C11−3.8 (3)
N2—C9—C10—N4−175.32 (17)C9—C10—N4—C11172.47 (16)
N3—C9—C10—N43.8 (2)N5—C11—N4—C10−6.2 (3)
N2—C9—C10—C120.8 (3)C20—C11—N4—C10176.25 (17)
N3—C9—C10—C12179.85 (18)N4—C11—N5—N69.7 (3)
N4—C10—C12—N610.2 (3)C20—C11—N5—N6−172.69 (19)
C9—C10—C12—N6−165.74 (19)C10—C12—N6—N5−6.7 (3)
N4—C10—C12—C13−171.40 (19)C13—C12—N6—N5174.70 (19)
C9—C10—C12—C1312.7 (3)C11—N5—N6—C12−2.8 (3)
N6—C12—C13—C1462.2 (3)O2—C8—O1—C7−12.1 (4)
C10—C12—C13—C14−116.3 (2)C19—C8—O1—C7166.2 (2)
N6—C12—C13—C18−116.5 (2)C6—C7—O1—C8114.8 (2)
C10—C12—C13—C1865.1 (3)C2—C7—O1—C8−66.5 (3)
C18—C13—C14—C15−3.5 (4)C4—C5—O3—C27−178.6 (2)
C12—C13—C14—C15177.8 (2)C6—C5—O3—C273.5 (4)
C13—C14—C15—C162.9 (5)O5A—C28—O4—C4−37.2 (6)
C14—C15—C16—C17−0.3 (5)O5—C28—O4—C422.3 (5)
C15—C16—C17—C18−1.5 (5)C29—C28—O4—C4−176.2 (2)
C16—C17—C18—C130.8 (4)C3—C4—O4—C28−84.3 (3)
C14—C13—C18—C171.7 (4)C5—C4—O4—C28102.9 (3)
C12—C13—C18—C17−179.6 (2)C4—C3—S1—C1−175.9 (2)
N5—C11—C20—C25−0.7 (3)C2—C3—S1—C10.18 (15)
N4—C11—C20—C25177.1 (2)N1—C1—S1—C3−1.14 (16)
N5—C11—C20—C21178.8 (2)N2—C1—S1—C3178.10 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.87 (2)2.59 (2)3.229 (3)130.5 (18)
N3—H3A···N40.87 (2)2.23 (2)2.613 (2)106.8 (17)
N3—H3B···N10.93 (2)1.97 (2)2.676 (2)130.8 (19)
C17—H17···O5ii0.932.553.390 (5)150
C21—H21···N40.932.522.830 (3)100
C25—H25···N50.932.492.809 (3)100
C26—H26B···O2iii0.962.583.390 (4)143
C27—H27A···O3iv0.962.533.389 (4)150
C27—H27B···O5Av0.962.293.194 (8)156
Symmetry codes: (i) x, y+1, z; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y−2, −z+1; (v) −x, −y−1, −z+1.
 

Acknowledgements

The study was carried out with the financial support of the Ministry of Science and Higher Education of the Russian Federation within the framework of the state assignment (subject No. state. reg. 124020200072–0). This work was also supported by the Azerbaijan State Pedagogical University, Azerbaijan Medical University. The authors' contributions are as follows. Conceptualization, MA and MMW; synthesis,YKS, DSK and VSG; X-ray analysis, YKS, DSK and VSG; writing (review and editing of the manuscript) NAE, MA, MMW and KIH; funding acquisition, YKS, DSK, VSG, NAE and KIH; supervision, MA and MMW.

References

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Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026008972