Synthesis, crystal structure and Hirshfeld surface analysis of 3,3′-[ethane-1,2-diylbis(sulfanedi­yl)]bis­(1H-1,2,4-triazol-5-amine)

Mavlonova, S.; Khayrullaev, G.; Rakhmonova, D.; Berdimuratova, M.; Kadirova, S.; Ashurov, J.; Torambetov, B.

doi:10.1107/S2056989026003464

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Volume 82| Part 5| May 2026| Pages 446-449

https://doi.org/10.1107/S2056989026003464

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Synthesis, crystal structure and Hirshfeld surface analysis of 3,3′-[ethane-1,2-diylbis(sulfanediyl)]bis(1H-1,2,4-triazol-5-amine)

Shakhnoza Mavlonova,^a Giyosiddin Khayrullaev,^a Dilnoza Rakhmonova,^a Mirigul Berdimuratova,^b Shakhnoza Kadirova,^a Jamshid Ashurov ^c and Batirbay Torambetov ^a ^*

^aNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St., Tashkent, 100174, Uzbekistan, ^bKarakalpak State University, 1 Ch. Abdirov St. Nukus, 230112, Uzbekistan, and ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek St., 83, Tashkent, 100125, Uzbekistan
^*Correspondence e-mail: [email protected]

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 23 March 2026; accepted 2 April 2026; online 10 April 2026)

The title compound, C₆H₁₀N₈S₂, crystallizes in the monoclinic crystal system with P2₁/c space group. The molecular geometry features a flexible ethylenedithio spacer inducing a 76.69 (11)° dihedral angle between triazole moieties; this twist precludes π–π stacking. The crystal cohesion is instead driven by a two-dimensional supramolecular framework maintained by strong N—H⋯N hydrogen bonds and auxiliary N⋯S and C⋯S contacts. Quantitative Hirshfeld surface analysis confirms the dominance of hydrogen-involving interactions (98.8%), with N⋯H (40.4%) and H⋯H (27.1%) as the primary contributors to the packing arrangement.

Keywords: molecular structure; crystal structure; 1,2,4-triazole; hydrogen bond; Hirshfeld analysis.

CCDC reference: 2543358

1. Chemical context

The 1,2,4-triazole ring is an important five-membered heterocyclic scaffold containing three nitrogen atoms that impart distinctive electronic characteristics and a relatively high dipole moment (Kaur & Chawla, 2017 ; El–Sebaey, 2020 ; Naeem, et al., 2025 ). It has attracted considerable interest in coordination chemistry, where the differing nucleophilicity enables diverse coordination modes, including monodentate, bidentate, and bridging arrangements (Zhang et al., 2008 ; Deswal et al., 2024 ; Bodurlar et al., 2025 ; Bader et al., 2020 ). Derivatives of 1,2,4-triazole are also well known for their wide range of biological activities, such as anticancer, antioxidant, analgesic, antimalarial, antituberculosis, insecticidal, antimycobacterial, antimicrobial, anticonvulsant, anti-inflammatory, antifungal, and antibacterial properties (El-Sherief et al., 2018 ; Sathyanarayana & Poojary, 2020 ; Wen et al., 2020 ; Gultekin et al., 2018 ). Representative examples of triazole are reported by Nuralieva et al. (2025 ), Pirimova et al. (2022 ), and Torambetov et al. (2025 ). Such compounds function as multitopic ligands bearing both thiol (–SH) and amine (–NH₂) functional groups. The presence of this soft sulfur and hard nitrogen donor atoms allows these molecules to participate in a range of coordination environments, facilitating the formation of complex, high-dimensional crystalline architectures stabilized by extensive hydrogen-bonding networks in metal complexes (Lin et al., 2017 ; Ma et al., 2008 ; Rakova et al., 2003 ). As a continuation of our previous work (Khayrullaev, et al., 2023 ), we report here the synthesis and single-crystal structural characterization of 3,3′-[ethane-1,2-diylbis(sulfanediyl)]bis(1H-1,2,4-triazol-5-amine), a derivative containing two (3-amino-1,2,4-triazol-5-yl)sulfanyl units interconnected through an ethylene spacer.

2. Structural commentary

The title compound crystallizes in the monoclinic system in the P2₁/c (No. 14) space group with one molecule in the asymmetric unit (Fig. 1). The molecule consists of two (3-amino-1,2,4-triazol-5-yl)sulfanyl units bridged by an ethylene spacer. The molecular geometry is characterized by a pronounced non-coplanar orientation, with the two triazole moieties separated by a dihedral angle of 76.69 (11)° between their mean planes. This significant twist in the molecular backbone is attributed to the conformational flexibility of the ethylenedithio spacer. Consequently, this nearly orthogonal orientation prevents the triazole rings from achieving the facial alignment necessary for π–π stacking, shifting the burden of crystal consolidation onto the extensive hydrogen-bonding network.

Figure 1
The title compound with displacement ellipsoids at the 50% probability level. For visual clarity, hydrogen atoms are represented as spheres of arbitrary size.

3. Supramolecular features

The crystal packing is governed by a sophisticated network of non-covalent interactions rather than traditional stacking motifs. A view of the packing diagram along the b-axis reveals that adjacent 1D molecular chains are linked via N—H⋯N [N8–H8A⋯N1 = 2.62 (3) Å; Table 1] hydrogen bonds, which facilitate the assembly of molecular units along the a-axis direction (Fig. 2). Beyond the primary hydrogen-bonding interactions, the structural architecture is further reinforced by auxiliary N⋯S [3.361 (2) Å] and C⋯S [3.525 (2) Å] intermolecular contacts. Although these interactions are weaker than N—H⋯N interactions, the heteroatom contacts collectively bridge the molecular layers, consolidating the 2D supramolecular framework. The 76.69 (11)° dihedral twist previously mentioned precludes any π–π stacking, thereby increasing reliance on these specific hydrogen bonds and sulfur-mediated contacts for overall crystal cohesion.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯N7ⁱ	0.86	1.99	2.838 (2)	167
N2—H2⋯N5ⁱⁱ	0.86	2.05	2.877 (2)	160
N8—H8A⋯N1ⁱⁱⁱ	0.76 (3)	2.62 (3)	3.232 (3)	140 (2)
N4—H4A⋯N1ⁱⁱ	0.83 (3)	2.56 (3)	3.346 (3)	159 (2)
N8—H8B⋯S2ⁱ	0.85 (3)	2.80 (3)	3.615 (2)	162 (3)
N4—H4B⋯N3^iv	0.90 (3)	2.13 (3)	3.010 (3)	168 (3)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) ; (iv) .

Figure 2
Packing arrangement viewed along the b axis, illustrating the network of intermolecular N—H⋯N, N⋯S, and C⋯S interactions.

4. Hirshfeld surface and fingerprint analysis

Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009 ) and two-dimensional fingerprint plots (Spackman & McKinnon, 2002 ) were performed using CrystalExplorer (Spackman et al., 2021 ). Quantitative Hirshfeld surface analysis demonstrates that the crystal packing is primarily consolidated by hydrogen-involving interactions, which account for a substantial 98.8% of the total surface area. The intermolecular contact distribution is dominated by N⋯H (40.4%), followed by H⋯H (27.1%), S⋯H (17.9%), C⋯H (5.1%), and minor contributions from C⋯S (4.1%) and N⋯S (4.1%). The Hirshfeld surface displays prominent dark-red spots, signifying close contacts that are significantly shorter than the sum of the van der Waals radii (Fig. 3). These spots are primarily attributed to strong N—H⋯N hydrogen bonding between adjacent molecular units. This is further corroborated by the 2D fingerprint plots, which reveal characteristic spikes for N⋯H interactions at approximately d_i + d_e = 1.8 Å and H⋯H contacts at d_i + d_e = 2.6 Å.

Figure 3
Hirshfeld surface and two-dimensional fingerprint plot.

5. Database survey

A search of the Cambridge Structural Database (CSD) using the ConQuest program (Version 6.01, November 2025; Groom et al., 2016 ) identified only 44 crystal structures containing the 3-amino-5-mercapto-1,2,4-triazole moiety. Of these, 25 are organic compounds and 19 are metal-based systems incorporating Fe, Co, Ni, Cu, Ag, Cd, Sn, Pr, Ho, Er, and Re. Among these structures, only two compounds contain two triazole moieties within the same molecule, in which the triazole units are linked by a disulfide bridge (DILZIL, Khayrullaev et al., 2023; SEDMEV, Yang et al., 2012 ). Notably, to date, no crystal structure has been reported featuring two (3-amino-1,2,4-triazol-5-yl)sulfanyl moieties linked by an ethylene spacer, underscoring the novelty of the present study.

6. Synthesis and crystallization

3-Amino-5-mercapto-1,2,4-triazole (1.16 g, 0.01 mol) and KOH (0.56 g, 0.01 mol) were dissolved in methanol (25 mL). The reaction mixture was cooled to 273 K, and 1,2-dichloroethane (0.005 mol) was added dropwise with stirring. The mixture was then refluxed at 338 K for 8 h. The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the solvent was removed under reduced pressure. The residue was dissolved in water (30 mL) and extracted with ethyl acetate (3 × 30 mL). The combined organic layers were dried over anhydrous Na₂SO₄, filtered, and concentrated under vacuum. The resulting solid was dried at room temperature for 4 days to afford colourless crystals (85% yield). The crude crystals was recrystallized from methanol solution.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All hydrogen atoms were located from difference-Fourier maps and refined isotropically.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₀N₈S₂
M_r	258.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.7401 (2), 9.8361 (1), 9.2113 (2)
β (°)	109.069 (2)
V (Å³)	1090.95 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.35
Crystal size (mm)	0.18 × 0.12 × 0.1

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 )
T_min, T_max	0.615, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10263, 2107, 1927
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.09
No. of reflections	2107
No. of parameters	161
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.24
Computer programs: CrysAlis PRO (Rigaku OD, 2021), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2543358

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026003464/tx2108sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026003464/tx2108Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026003464/tx2108Isup3.cml

checkCIF report

Computing details top

3,3'-[Ethane-1,2-diylbis(sulfanediyl)]bis(1H-1,2,4-triazol-5-amine) top

Crystal data top

C₆H₁₀N₈S₂	F(000) = 536
M_r = 258.34	D_x = 1.573 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.7401 (2) Å	Cell parameters from 6441 reflections
b = 9.8361 (1) Å	θ = 3.7–70.8°
c = 9.2113 (2) Å	µ = 4.35 mm⁻¹
β = 109.069 (2)°	T = 293 K
V = 1090.95 (3) Å³	Block, colourless
Z = 4	0.18 × 0.12 × 0.1 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2107 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1927 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.3°, θ_min = 3.7°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	k = −12→11
T_min = 0.615, T_max = 1.000	l = −11→11
10263 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
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) = 0.100	w = 1/[σ²(F_o²) + (0.0551P)² + 0.2828P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2107 reflections	Δρ_max = 0.40 e Å⁻³
161 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
S2	0.31895 (4)	0.55253 (5)	0.90594 (6)	0.04855 (17)
S1	0.08980 (5)	0.65665 (5)	0.44295 (6)	0.05777 (19)
N7	0.47164 (12)	0.50710 (14)	0.75544 (17)	0.0401 (3)
N6	0.47018 (13)	0.28482 (15)	0.75254 (19)	0.0452 (4)
H6	0.485616	0.202665	0.734751	0.054*
N3	0.08227 (13)	0.50853 (16)	0.19660 (18)	0.0458 (4)
N5	0.39835 (13)	0.32119 (15)	0.82907 (19)	0.0459 (4)
N2	0.21243 (14)	0.35730 (16)	0.2911 (2)	0.0493 (4)
H2	0.255533	0.289118	0.295113	0.059*
N1	0.21245 (14)	0.43632 (17)	0.41680 (19)	0.0490 (4)
N8	0.58527 (17)	0.3923 (2)	0.6323 (3)	0.0594 (5)
N4	0.11720 (17)	0.3516 (2)	0.0219 (2)	0.0551 (4)
C5	0.40203 (14)	0.45463 (17)	0.8264 (2)	0.0390 (4)
C6	0.51240 (14)	0.39592 (17)	0.7099 (2)	0.0391 (4)
C1	0.13561 (15)	0.40294 (18)	0.1635 (2)	0.0435 (4)
C2	0.13288 (15)	0.52359 (19)	0.3502 (2)	0.0434 (4)
C4	0.19338 (17)	0.5601 (2)	0.7390 (2)	0.0521 (5)
H4C	0.178660	0.471254	0.691014	0.063*
H4D	0.130775	0.584750	0.771580	0.063*
C3	0.20554 (18)	0.6624 (2)	0.6248 (3)	0.0548 (5)
H3A	0.274469	0.645397	0.604546	0.066*
H3B	0.209829	0.752709	0.668612	0.066*
H8A	0.606 (2)	0.459 (3)	0.610 (3)	0.056 (7)*
H4A	0.147 (2)	0.276 (3)	0.022 (3)	0.061 (7)*
H8B	0.597 (2)	0.315 (3)	0.601 (3)	0.079 (9)*
H4B	0.058 (3)	0.384 (3)	−0.053 (3)	0.078 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0470 (3)	0.0517 (3)	0.0468 (3)	0.00188 (19)	0.0152 (2)	−0.00829 (19)
S1	0.0635 (3)	0.0539 (3)	0.0529 (3)	0.0241 (2)	0.0149 (2)	0.0000 (2)
N7	0.0423 (8)	0.0276 (7)	0.0507 (9)	−0.0013 (6)	0.0155 (7)	0.0015 (6)
N6	0.0512 (9)	0.0270 (7)	0.0612 (10)	0.0001 (6)	0.0238 (8)	−0.0008 (6)
N3	0.0443 (8)	0.0444 (8)	0.0483 (9)	0.0058 (7)	0.0145 (7)	0.0008 (7)
N5	0.0483 (8)	0.0344 (8)	0.0583 (10)	−0.0048 (6)	0.0220 (7)	−0.0004 (7)
N2	0.0513 (9)	0.0413 (8)	0.0576 (10)	0.0106 (7)	0.0209 (8)	0.0000 (7)
N1	0.0502 (9)	0.0451 (9)	0.0506 (9)	0.0114 (7)	0.0151 (7)	0.0003 (7)
N8	0.0710 (12)	0.0387 (10)	0.0846 (14)	0.0037 (9)	0.0474 (11)	0.0068 (9)
N4	0.0613 (11)	0.0509 (11)	0.0556 (11)	0.0043 (9)	0.0224 (9)	−0.0057 (8)
C5	0.0393 (9)	0.0329 (8)	0.0424 (9)	−0.0023 (7)	0.0101 (7)	−0.0020 (7)
C6	0.0405 (9)	0.0305 (8)	0.0453 (9)	−0.0007 (6)	0.0126 (7)	0.0018 (7)
C1	0.0421 (9)	0.0388 (9)	0.0532 (10)	−0.0026 (7)	0.0204 (8)	0.0012 (8)
C2	0.0414 (9)	0.0409 (9)	0.0492 (10)	0.0042 (7)	0.0164 (8)	0.0025 (8)
C4	0.0458 (10)	0.0536 (11)	0.0582 (12)	0.0014 (9)	0.0188 (9)	−0.0047 (9)
C3	0.0612 (12)	0.0431 (10)	0.0623 (13)	0.0015 (9)	0.0230 (10)	−0.0051 (9)

Geometric parameters (Å, º) top

S2—C5	1.7580 (18)	N2—C1	1.338 (3)
S2—C4	1.822 (2)	N1—C2	1.317 (2)
S1—C2	1.7463 (19)	N8—C6	1.345 (3)
S1—C3	1.836 (2)	N8—H8A	0.76 (3)
N7—C5	1.363 (2)	N8—H8B	0.85 (3)
N7—C6	1.335 (2)	N4—C1	1.346 (3)
N6—H6	0.8600	N4—H4A	0.83 (3)
N6—N5	1.372 (2)	N4—H4B	0.90 (3)
N6—C6	1.332 (2)	C4—H4C	0.9700
N3—C1	1.330 (2)	C4—H4D	0.9700
N3—C2	1.358 (2)	C4—C3	1.500 (3)
N5—C5	1.314 (2)	C3—H3A	0.9700
N2—H2	0.8600	C3—H3B	0.9700
N2—N1	1.394 (2)

C5—S2—C4	98.81 (9)	N7—C6—N8	126.52 (17)
C2—S1—C3	100.49 (9)	N6—C6—N7	110.08 (16)
C6—N7—C5	102.77 (14)	N6—C6—N8	123.40 (17)
N5—N6—H6	125.1	N3—C1—N2	110.01 (17)
C6—N6—H6	125.1	N3—C1—N4	125.09 (19)
C6—N6—N5	109.79 (14)	N2—C1—N4	124.88 (19)
C1—N3—C2	102.71 (15)	N3—C2—S1	118.24 (13)
C5—N5—N6	102.53 (14)	N1—C2—S1	125.31 (15)
N1—N2—H2	124.9	N1—C2—N3	116.44 (17)
C1—N2—H2	124.9	S2—C4—H4C	109.5
C1—N2—N1	110.14 (15)	S2—C4—H4D	109.5
C2—N1—N2	100.69 (16)	H4C—C4—H4D	108.1
C6—N8—H8A	119.0 (19)	C3—C4—S2	110.85 (15)
C6—N8—H8B	116 (2)	C3—C4—H4C	109.5
H8A—N8—H8B	124 (3)	C3—C4—H4D	109.5
C1—N4—H4A	113.2 (17)	S1—C3—H3A	109.1
C1—N4—H4B	116.8 (18)	S1—C3—H3B	109.1
H4A—N4—H4B	126 (2)	C4—C3—S1	112.54 (15)
N7—C5—S2	124.53 (13)	C4—C3—H3A	109.1
N5—C5—S2	120.63 (14)	C4—C3—H3B	109.1
N5—C5—N7	114.82 (16)	H3A—C3—H3B	107.8

S2—C4—C3—S1	171.73 (10)	C6—N7—C5—N5	0.7 (2)
N6—N5—C5—S2	177.82 (12)	C6—N6—N5—C5	0.3 (2)
N6—N5—C5—N7	−0.7 (2)	C1—N3—C2—S1	178.47 (14)
N5—N6—C6—N7	0.1 (2)	C1—N3—C2—N1	−0.6 (2)
N5—N6—C6—N8	−179.81 (18)	C1—N2—N1—C2	0.4 (2)
N2—N1—C2—S1	−178.83 (14)	C2—S1—C3—C4	−83.15 (16)
N2—N1—C2—N3	0.2 (2)	C2—N3—C1—N2	0.8 (2)
N1—N2—C1—N3	−0.7 (2)	C2—N3—C1—N4	−177.61 (18)
N1—N2—C1—N4	177.64 (18)	C4—S2—C5—N7	91.57 (16)
C5—S2—C4—C3	−77.89 (16)	C4—S2—C5—N5	−86.75 (16)
C5—N7—C6—N6	−0.48 (19)	C3—S1—C2—N3	−164.45 (15)
C5—N7—C6—N8	179.4 (2)	C3—S1—C2—N1	14.5 (2)
C6—N7—C5—S2	−177.68 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N7ⁱ	0.86	1.99	2.838 (2)	167
N2—H2···N5ⁱⁱ	0.86	2.05	2.877 (2)	160
N8—H8A···N1ⁱⁱⁱ	0.76 (3)	2.62 (3)	3.232 (3)	140 (2)
N4—H4A···N1ⁱⁱ	0.83 (3)	2.56 (3)	3.346 (3)	159 (2)
N8—H8B···S2ⁱ	0.85 (3)	2.80 (3)	3.615 (2)	162 (3)
N4—H4B···N3^iv	0.90 (3)	2.13 (3)	3.010 (3)	168 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z.

Acknowledgements

BT is grateful to the FAIRE programme provided by the Cambridge Crystallographic Data Centre (CCDC) for the opportunity to use the Cambridge Structural Database (CSD) and associated software.

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