N-(4-Amino-1,2,5-oxa­diazol-3-yl)formamide

Guseinov, F.I.; Hökelek, T.; Shuvalova, E.V.; Samigullina, A.I.; Ekberov, N.A.; Hasanov, K.I.; Al-Douh, M.H.

doi:10.1107/S2414314625007205

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 8| August 2025| x250720

https://doi.org/10.1107/S2414314625007205

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N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide

Firudin I. Guseinov,^a,^b Tuncer Hökelek,^c Elena V. Shuvalova,^b Aida I. Samigullina,^b Nizami A. Ekberov,^d Khudayar I. Hasanov ^e and Mohammed Hadi Al-Douh ^f ^*

^aKosygin State University of Russia, 117997 Moscow, Russian Federation, ^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation, ^cHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^dAzerbaijan State Pedagogical University, 68 Uzeyir Hajibeyov St., AZ 1000, Baku, Azerbaijan, ^eAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14, AZ1022 Baku, Azerbaijan, and ^fChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 June 2025; accepted 13 August 2025; online 15 August 2025)

The asymmetric unit of the title compound, C₃H₄N₄O₂, contains two coplanar molecules (A and B) completely located on mirror planes. In the crystal, N—H⋯O, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds link the molecules into sheets parallel to (010). There are neither significant π–π nor C—H⋯π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packings of molecules A and B are from H⋯O/O⋯H (32.4% for A, 30.1% for B), H⋯N/N⋯H (28.2%, 31.5%) and H⋯H (12.3%, 8.0%) interactions.

Keywords: crystal structure; non-covalent interactions; 2,2-dihalo-3-oxoaldehydes; pyrazol.

CCDC reference: 2480423

Structure description

Oxadiazole is a five-membered heterocyclic compound with one oxygen and two nitrogen atoms. The oxadiazole scaffold is a commonly utilized pharmacophore and has been subjected to extensive studies in recent years because of its metabolic profile and ability to engage in hydrogen-bonding with receptor sites (Khan et al., 2017 ; Khalilov, 2021 ). Oxadiazole derivatives have also attracted significant attention because of their reactivity (Guseinov et al., 2024 ), diverse functional (Aliyeva et al., 2024 ) and pharmacological properties, including anti-inflammatory, antibacterial, antihypertension, muscle relaxing and anticancer activities (Boström et al., 2012 ). Moreover, derivatization of the oxadiazole synthon with non-covalent donor or acceptor sites for hydrogen-bonding interactions can be applied as a synthetic strategy in the improvement of functional properties of its metal complexes (Mahmudov et al., 2022 ). Herein, we report synthesis, molecular and crystal structures together with Hirshfeld surface analysis of a new aldehyde and NH-functionalized oxadiazole derivative, C₃H₄N₄O₂.

The asymmetric unit contains two molecules (A and B, Fig. 1) completely located on mirror planes, making the molecules exactly planar. Small variations are observed in the C8A—N7A—C3A [125.88 (14)°] and C8B—N7B—C3B [125.04 (14)°], N2A—C3A—N7A [125.07 (14)°] and N2B—C3B—N7B [125.41 (14)°], N7A—C3A—C4A [124.71 (14)°] and N7B—C3B—C4B [124.10 (14)°], N5A—C4A—N6A [124.68 (15)°] and N5B—C4B—N6B [125.28 (15)°], N6A—C4A—C3A [127.25 (15)°] and N6B—C4B—C3B [126.16 (15)°], O9A—C8A—N7A [125.23 (15)°] and O9B—C8B—N7B [123.42 (15)°] bond angles due to the strengths of the N—H⋯O and N—H⋯N hydrogen-bonding interactions (Fig. 2,Table 1). Next to these classical hydrogen-bonding interactions, weaker C—H⋯O and C—H⋯N interactions are also present (Table 1), linking the molecules into sheets extending parallel to (010). There are neither significant π–π nor C—H⋯π(ring) interactions present between molecules.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6A—H6A⋯O9Aⁱ	0.88 (3)	2.05 (3)	2.9207 (19)	172 (2)
N6A—H6B⋯O9Bⁱⁱ	0.83 (3)	2.26 (3)	3.074 (2)	164 (2)
N7A—H7A⋯O9Bⁱⁱⁱ	0.87 (3)	1.93 (3)	2.8033 (18)	177 (2)
N7A—H7A⋯O9Bⁱⁱ	0.87 (3)	1.93 (3)	2.8033 (18)	177 (2)
N6B—H6C⋯N5A^iv	0.88 (2)	2.31 (2)	3.189 (2)	175 (2)
N6B—H6D⋯O9A^v	0.85 (3)	2.31 (3)	2.8121 (19)	118 (2)
N6B—H6D⋯N2A^v	0.85 (3)	2.20 (3)	3.0387 (19)	166 (3)
N7B—H7B⋯O1A^iv	0.91 (3)	2.24 (3)	3.0354 (17)	145 (2)
N7B—H7B⋯N5A^iv	0.91 (3)	2.32 (3)	3.2302 (19)	179 (2)
C8A—H8A⋯O1B^vi	0.95	2.32	3.266 (2)	175
C8B—H8B⋯N5B^vii	0.95	2.55	3.489 (2)	170
Symmetry codes: (i) ; (ii) ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) ; (v) ; (vi) ; (vii) $[x+1, -y+{\script{1\over 2}}, z]$ .

Figure 1
The asymmetric unit of the title compound with the atom-numbering scheme and 50% probability ellipsoids.

Figure 2
Partial packing diagram of the title compound, highlighting the layered arrangement. Intermolecular N—H⋯N, N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds are shown as dashed lines.

A Hirshfeld surface (HS) analysis was carried out using CrystalExplorer (Spackman et al., 2021 ) to visualize and quantify the intermolecular interactions. In the HSs plotted over d_norm (Fig. 3a,b), the contact distances equal, shorter and longer with respect to the sum of van der Waals radii are shown by white, red and blue colours, respectively. According to the two-dimensional fingerprint plots, H⋯O/O⋯H, H⋯N/N⋯H and H⋯H contacts make the most important contributions to the HSs (Table 2, Figs. 4 and 5), and they have significant differences due to the different numbers and values of the close contacts.

Table 2
Comparison of the percentage contributions to the crystal packing for molecules A and B

Contacts	A	B
H⋯O/O⋯H	32.4	30.1
H⋯N/N⋯H	28.2	31.5
H⋯H	12.3	8.0
H⋯C/C⋯H	7.2	6.9
N⋯O/O⋯N	5.3	4.3
O⋯O	4.6	1.5
C⋯O/O⋯C	3.9	7.2
C⋯N/N⋯C	3.3	5.6
N⋯N	2.9	5.0

Figure 3
Views of the three-dimensional Hirshfeld surfaces for (a) molecule A and (b) molecule B plotted over d_norm.

Figure 4
The full two-dimensional fingerprint plots for molecule A, showing (a) all interactions, and delineated into (b) H⋯O/O⋯H, (c) H⋯N/N⋯H, (d) H⋯H, (e) H⋯C/C⋯H, (f) N⋯O/O⋯N, (g) O⋯O, (h) C⋯O/O⋯C, (i) C⋯N/N⋯C and (j) N⋯N interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface contacts.

Figure 5
The full two-dimensional fingerprint plots for molecule B; subdivisions are the same as in Fig. 4

Synthesis and crystallization

A mixture of diaminofurazan (20 mg, 0.2 mmol) and 2,2-dichloro-3-oxo-3-phenylpropanal (42.4 mg, 0.2 mmol) in 15 ml of CCl₄ (dry) was boiled for 30 min. The reaction mixture was then cooled to room temperature, the precipitate filtered and recrystallized from chloroform solution. Yield 15.4 mg (62%), ¹H NMR (300 MHz, DMSO-d₆): 10.40 (1H, NH), 8.75 (1H, CHO), 6.11 (2H, NH₂). ¹³C NMR (200 MHz, DMSO-d₆): 143.89, 147.78, 165.90.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3.

Table 3
Experimental details

Crystal data
Chemical formula	C₃H₄N₄O₂
M_r	128.10
Crystal system, space group	Monoclinic, P12₁/m1
Temperature (K)	100
a, b, c (Å)	7.98085 (8), 6.17409 (7), 10.19204 (9)
β (°)	95.2595 (9)
V (Å³)	500.09 (1)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.26
Crystal size (mm)	0.28 × 0.22 × 0.04

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2023 )
T_min, T_max	0.503, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13311, 1182, 1153
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.06
No. of reflections	1182
No. of parameters	128
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.26
Computer programs: CrysAlis PRO (Rigaku OD, 2023), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2480423

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625007205/wm4232sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625007205/wm4232Isup2.hkl

checkCIF report

Computing details top

N-(4-Amino-1,2,5-oxadiazol-3-yl)formamide top

Crystal data top

C₃H₄N₄O₂	F(000) = 264
M_r = 128.10	D_x = 1.701 Mg m⁻³
Monoclinic, P12₁/m1	Cu Kα radiation, λ = 1.54184 Å
a = 7.98085 (8) Å	Cell parameters from 9316 reflections
b = 6.17409 (7) Å	θ = 4.4–78.3°
c = 10.19204 (9) Å	µ = 1.26 mm⁻¹
β = 95.2595 (9)°	T = 100 K
V = 500.09 (1) Å³	Prism, colorless
Z = 4	0.28 × 0.22 × 0.04 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	1182 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1153 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.0000 pixels mm^-1	θ_max = 79.7°, θ_min = 4.4°
ω scans	h = −10→10
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023)	k = −7→7
T_min = 0.503, T_max = 1.000	l = −12→12
13311 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0568P)² + 0.2125P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1182 reflections	Δρ_max = 0.45 e Å⁻³
128 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (10)

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.

Refinement. The NH hydrogen atomss were located in difference-Fourier maps and were refined isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.21691 (14)	0.750000	−0.13259 (11)	0.0213 (3)
O9A	−0.19240 (15)	0.750000	0.09542 (12)	0.0223 (3)
N2A	0.08834 (16)	0.750000	−0.04954 (13)	0.0183 (3)
N5A	0.37506 (17)	0.750000	−0.05892 (14)	0.0212 (3)
N6A	0.46198 (18)	0.750000	0.16804 (16)	0.0309 (4)
H6A	0.569 (4)	0.750000	0.154 (3)	0.034 (6)*
H6B	0.433 (3)	0.750000	0.245 (3)	0.029 (6)*
N7A	0.08165 (16)	0.750000	0.18320 (13)	0.0181 (3)
H7A	0.141 (3)	0.750000	0.259 (3)	0.027 (6)*
C3A	0.16276 (19)	0.750000	0.06877 (15)	0.0163 (3)
C4A	0.34342 (19)	0.750000	0.06452 (16)	0.0191 (3)
C8A	−0.0871 (2)	0.750000	0.18991 (16)	0.0205 (4)
H8A	−0.126486	0.750000	0.275080	0.025*
O1B	0.19712 (15)	0.250000	0.50920 (12)	0.0247 (3)
O9B	0.71609 (15)	0.250000	0.57695 (12)	0.0226 (3)
N2B	0.37256 (17)	0.250000	0.52444 (14)	0.0230 (3)
N5B	0.13570 (18)	0.250000	0.37538 (14)	0.0213 (3)
N6B	0.26997 (19)	0.250000	0.17935 (14)	0.0259 (4)
H6C	0.365 (3)	0.250000	0.141 (2)	0.023 (5)*
H6D	0.177 (4)	0.250000	0.130 (3)	0.039 (7)*
N7B	0.58111 (16)	0.250000	0.37086 (13)	0.0187 (3)
H7B	0.595 (3)	0.250000	0.283 (3)	0.028 (6)*
C3B	0.4166 (2)	0.250000	0.40507 (15)	0.0176 (3)
C4B	0.26997 (19)	0.250000	0.31096 (16)	0.0170 (3)
C8B	0.7209 (2)	0.250000	0.45783 (16)	0.0201 (4)
H8B	0.827870	0.250000	0.423922	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0133 (5)	0.0377 (7)	0.0134 (5)	0.000	0.0029 (4)	0.000
O9A	0.0136 (5)	0.0363 (7)	0.0165 (6)	0.000	0.0000 (4)	0.000
N2A	0.0123 (6)	0.0303 (7)	0.0130 (6)	0.000	0.0045 (5)	0.000
N5A	0.0117 (6)	0.0342 (8)	0.0178 (7)	0.000	0.0018 (5)	0.000
N6A	0.0101 (7)	0.0663 (12)	0.0164 (7)	0.000	0.0013 (5)	0.000
N7A	0.0109 (6)	0.0326 (8)	0.0106 (6)	0.000	0.0005 (5)	0.000
C3A	0.0107 (7)	0.0246 (8)	0.0136 (7)	0.000	0.0017 (5)	0.000
C4A	0.0117 (7)	0.0286 (8)	0.0170 (8)	0.000	0.0019 (6)	0.000
C8A	0.0159 (7)	0.0315 (9)	0.0145 (7)	0.000	0.0025 (6)	0.000
O1B	0.0137 (6)	0.0467 (8)	0.0141 (6)	0.000	0.0026 (4)	0.000
O9B	0.0177 (6)	0.0349 (7)	0.0143 (6)	0.000	−0.0027 (4)	0.000
N2B	0.0126 (6)	0.0404 (9)	0.0159 (7)	0.000	0.0017 (5)	0.000
N5B	0.0150 (6)	0.0361 (8)	0.0127 (6)	0.000	0.0006 (5)	0.000
N6B	0.0116 (7)	0.0540 (10)	0.0117 (6)	0.000	−0.0012 (5)	0.000
N7B	0.0113 (6)	0.0338 (8)	0.0109 (7)	0.000	0.0005 (5)	0.000
C3B	0.0136 (7)	0.0257 (8)	0.0133 (7)	0.000	0.0008 (6)	0.000
C4B	0.0128 (7)	0.0238 (8)	0.0142 (7)	0.000	0.0004 (5)	0.000
C8B	0.0137 (7)	0.0294 (9)	0.0169 (8)	0.000	−0.0010 (6)	0.000

Geometric parameters (Å, º) top

O1A—N2A	1.3888 (16)	O1B—N2B	1.3945 (17)
O1A—N5A	1.4082 (17)	O1B—N5B	1.4064 (17)
O9A—C8A	1.219 (2)	O9B—C8B	1.218 (2)
N2A—C3A	1.294 (2)	N2B—C3B	1.297 (2)
N5A—C4A	1.306 (2)	N5B—C4B	1.307 (2)
N6A—H6A	0.88 (3)	N6B—H6C	0.88 (2)
N6A—H6B	0.83 (3)	N6B—H6D	0.85 (3)
N6A—C4A	1.351 (2)	N6B—C4B	1.341 (2)
N7A—H7A	0.87 (3)	N7B—H7B	0.91 (3)
N7A—C3A	1.385 (2)	N7B—C3B	1.389 (2)
N7A—C8A	1.355 (2)	N7B—C8B	1.360 (2)
C3A—C4A	1.446 (2)	C3B—C4B	1.444 (2)
C8A—H8A	0.9500	C8B—H8B	0.9500

O1A···N7Bⁱ	3.0352 (18)	H6B···O9Bⁱⁱ	2.26 (3)
O1B···C8Bⁱⁱ	3.1671 (5)	N2A···N6B^x	3.039 (2)
O9A···N6Bⁱⁱⁱ	2.812 (2)	N2B···C8B^v	3.1849 (5)
O9A···N2A	2.7947 (18)	N6A···N7A	3.054 (2)
N6A···O9A^iv	2.9206 (19)	N6B···N7B	3.014 (2)
O9B···N7A^v	2.8032 (18)	N2A···H6Dⁱⁱⁱ	2.20 (3)
O9B···N6A^vi	3.074 (2)	H6B···N2Bⁱⁱ	2.69 (3)
O9B···N2B	2.7448 (19)	N5A···H7B^vii	2.32 (3)
O1A···H7B^vii	2.24 (3)	N5A···H6C^vii	2.31 (2)
O1B···H8A^viii	2.3189	H8B···N5B^xi	2.55
H6D···O9A^ix	2.31 (3)	N6B···H7B	2.72 (3)
O9A···H6Cⁱⁱⁱ	2.66 (2)	C8A···H6A^xii	2.74 (3)
H6A···O9A^iv	2.06 (3)	H6B···H7A	2.35 (3)
H6D···O9Aⁱⁱⁱ	2.31 (3)	H6C···H7B	2.24 (4)
O9B···H7A^vi	1.94 (3)

N2A—O1A—N5A	110.56 (11)	N2B—O1B—N5B	111.41 (11)
C3A—N2A—O1A	105.44 (12)	C3B—N2B—O1B	104.56 (13)
C4A—N5A—O1A	105.71 (12)	C4B—N5B—O1B	104.97 (13)
H6A—N6A—H6B	120 (2)	H6C—N6B—H6D	118 (2)
C4A—N6A—H6A	119.8 (17)	C4B—N6B—H6C	121.3 (15)
C4A—N6A—H6B	119.8 (17)	C4B—N6B—H6D	120.5 (18)
C3A—N7A—H7A	119.6 (16)	C3B—N7B—H7B	116.9 (15)
C8A—N7A—H7A	114.5 (16)	C8B—N7B—H7B	118.0 (15)
C8A—N7A—C3A	125.88 (14)	C8B—N7B—C3B	125.04 (14)
N2A—C3A—N7A	125.07 (14)	N2B—C3B—N7B	125.41 (14)
N2A—C3A—C4A	110.23 (13)	N2B—C3B—C4B	110.49 (14)
N7A—C3A—C4A	124.71 (14)	N7B—C3B—C4B	124.10 (14)
N5A—C4A—N6A	124.68 (15)	N5B—C4B—N6B	125.28 (15)
N5A—C4A—C3A	108.07 (14)	N5B—C4B—C3B	108.56 (14)
N6A—C4A—C3A	127.25 (15)	N6B—C4B—C3B	126.16 (15)
O9A—C8A—N7A	125.23 (15)	O9B—C8B—N7B	123.42 (15)
O9A—C8A—H8A	117.4	O9B—C8B—H8B	118.3
N7A—C8A—H8A	117.4	N7B—C8B—H8B	118.3

O1A—N2A—C3A—N7A	180.000 (1)	O1B—N2B—C3B—N7B	180.000 (1)
O1A—N2A—C3A—C4A	0.0	O1B—N2B—C3B—C4B	0.000 (1)
O1A—N5A—C4A—N6A	180.000 (1)	O1B—N5B—C4B—N6B	180.000 (1)
O1A—N5A—C4A—C3A	0.0	O1B—N5B—C4B—C3B	0.000 (1)
N2A—O1A—N5A—C4A	0.000 (1)	N2B—O1B—N5B—C4B	0.000 (1)
N2A—C3A—C4A—N5A	0.0	N2B—C3B—C4B—N5B	0.000 (1)
N2A—C3A—C4A—N6A	180.000 (1)	N2B—C3B—C4B—N6B	180.000 (1)
N5A—O1A—N2A—C3A	0.000 (1)	N5B—O1B—N2B—C3B	0.000 (1)
N7A—C3A—C4A—N5A	180.0	N7B—C3B—C4B—N5B	180.000 (1)
N7A—C3A—C4A—N6A	0.000 (1)	N7B—C3B—C4B—N6B	0.000 (1)
C3A—N7A—C8A—O9A	0.000 (1)	C3B—N7B—C8B—O9B	0.000 (1)
C8A—N7A—C3A—N2A	0.000 (1)	C8B—N7B—C3B—N2B	0.000 (1)
C8A—N7A—C3A—C4A	180.000 (1)	C8B—N7B—C3B—C4B	180.000 (1)

Symmetry codes: (i) −x+1, y+1/2, −z; (ii) −x+1, y+1/2, −z+1; (iii) −x, −y+1, −z; (iv) x+1, y, z; (v) −x+1, y−1/2, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+1, −z; (viii) −x, −y+1, −z+1; (ix) −x, y−1/2, −z; (x) −x, y+1/2, −z; (xi) x+1, −y+1/2, z; (xii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6A—H6A···O9A^iv	0.88 (3)	2.05 (3)	2.9207 (19)	172 (2)
N6A—H6B···O9B^vi	0.83 (3)	2.26 (3)	3.074 (2)	164 (2)
N7A—H7A···O9Bⁱⁱ	0.87 (3)	1.93 (3)	2.8033 (18)	177 (2)
N7A—H7A···O9B^vi	0.87 (3)	1.93 (3)	2.8033 (18)	177 (2)
N6B—H6C···N5A^vii	0.88 (2)	2.31 (2)	3.189 (2)	175 (2)
N6B—H6D···O9Aⁱⁱⁱ	0.85 (3)	2.31 (3)	2.8121 (19)	118 (2)
N6B—H6D···N2Aⁱⁱⁱ	0.85 (3)	2.20 (3)	3.0387 (19)	166 (3)
N7B—H7B···O1A^vii	0.91 (3)	2.24 (3)	3.0354 (17)	145 (2)
N7B—H7B···N5A^vii	0.91 (3)	2.32 (3)	3.2302 (19)	179 (2)
C8A—H8A···O1B^viii	0.95	2.32	3.266 (2)	175
C8B—H8B···N5B^xi	0.95	2.55	3.489 (2)	170

Symmetry codes: (ii) −x+1, y+1/2, −z+1; (iii) −x, −y+1, −z; (iv) x+1, y, z; (vi) −x+1, −y+1, −z+1; (vii) −x+1, −y+1, −z; (viii) −x, −y+1, −z+1; (xi) x+1, −y+1/2, z.

Comparison of the percentage contributions to the crystal packing for molecules A and B top

Contacts	A	B
H···O/O···H	32.4	30.1
H···N/N···H	28.2	31.5
H···H	12.3	8.0
H···C/C···H	7.2	6.9
N···O/O···N	5.3	4.3
O···O	4.6	1.5
C···O/O···C	3.9	7.2
C···N/N···C	3.3	5.6
N···N	2.9	5.0

Acknowledgements

The crystal-structure determination was performed in the Department of Structural Studies of the Zelinsky Institute of Organic Chemistry, Moscow. This work has been supported by the Azerbaijan State Pedagological University and Azerbaijan Medical University. The author's contributions are as follows. Conceptualization, FIG and ANB; synthesis, EVS; X-ray analysis, AIS and TH; Hirshfeld surface analysis, TH; writing (review and editing of the manuscript), TH, NAE and KIH; funding acquisition, NAE and KIH; supervision, FIG, TH and ANB.

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