Crystal structure and Hirshfeld surface analysis of 2-amino-5-bromo-1,3,4-triazol-3-ium chloride monohydrate

Torambetov, B.; Akkurt, M.; Hasanov, K.I.; Manahelohe, G.M.; Ashurov, J.; Kadirova, S.

doi:10.1107/S2056989026004378

research communications

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ISSN: 2056-9890

Volume 82| Part 5| May 2026| Pages 525-529

https://doi.org/10.1107/S2056989026004378

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Crystal structure and Hirshfeld surface analysis of 2-amino-5-bromo-1,3,4-triazol-3-ium chloride monohydrate

Batirbay Torambetov,^a Mehmet Akkurt,^b Khudayar I. Hasanov,^c Gizachew Mulugeta Manahelohe,^d ^* Jamshid Ashurov ^e and Shakhnoza Kadirova ^a

^aNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St., Tashkent, 100174, Uzbekistan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^cAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14, AZ 1022, Baku, Azerbaijan, ^dDepartment of Chemistry, University of Gondar, PO Box 196, Gondar, Ethiopia, and ^eInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek, St, 83, Tashkent, 100125, Uzbekistan
^*Correspondence e-mail: [email protected]

Edited by Y. Ozawa, University of Hyogo, Japan (Received 5 March 2026; accepted 25 April 2026; online 29 April 2026)

In the title salt, C₂H₃BrN₃S⁺·Cl⁻·H₂O, the cation C₂H₃BrN₃S⁺ cation, the Cl⁻ anion and the water molecule are linked by N—H⋯Cl, N—H⋯O and O—H⋯Cl hydrogen bonds, forming molecular layers parallel to the (002) plane. The crystal packing is further reinforced by van der Waals interactions between these layers but C—H⋯π and π–π interactions are not observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to study the intermolecular interactions.

Keywords: crystal structure; hydrogen bonds; van der Waals interactions; Hirshfeld surface analysis.

CCDC reference: 2549381

1. Chemical context

Thiadiazole is a five-membered ring system containing a chalcogen-bond-donor sulfur atom (Gurbanov et al., 2023 ), a hydrogen-bonding domain, and a two-electron donor nitrogen system that exhibits a strong coordination ability (Khojabaeva et al., 2025 ; Mahmudov et al., 2021 ). The 1,3,4-thiadiazole moiety is present as a core structural component in an array of drug categories such as anti-inflammatory, antimicrobial, analgesic, anticancer, anti-epileptic, antineoplastic, antiviral, and antitubercular agents (Jain et al., 2013 ; Torambetov et al., 2026 ). Transition-metal complexes of thiadiazole ligands have also attracted much attention due to their high synthetic potential for synthesis, crystal engineering and catalysis (Mamedov et al., 2006 ; Nuralieva et al., 2025 , 2026 ). Functionalization of the thiadiazol moiety with a non-covalent bond-donor or acceptor sites can be used a synthetic tool to improve their functional properties (Huseynov et al., 2021 ; Naghiyev et al., 2023 ).

In a continuation of our work in this area, we functionalized a thiadiazol, 5-bromo-1,3,4-thiadiazol-2-amine, which exhibits various sorts of intermolecular non-covalent interactions.

2. Structural commentary

In the (C₂H₃BrN₃S)⁺ cation of the title salt, (Fig. 1), the five-membered ring is quite planar (r.m.s. deviation = 0.004 Å). The N1—N2—C2—Br1 and C1—S1—C2—Br1 torsion angles are −179.2 (3) and 178.6 (3)°, respectively. The Br—C [Br1—C2 = 1.855 (5) Å], S—C [S1—C1 = 1.733 (5) and S1—C2 = 1.740 (5) Å], N=C [N1—C1 = 1.323 (6) and N2—C2 =1.277 (7) Å] and N—N [N1—N2 = 1.364 (6) Å] bond lengths, and the C—S—C [C1—S1—C2) 86.9 (2)°] and C=N—N [C1=N1—N2 = 117.5 (4) and C2=N2—N1 = 108.9 (4)°] angles are within normal values and are also compatible with those of the structures in the database survey section.

Figure 1
View of the asymmetric unit the title salt, showing the atom labeling and the 50% probability ellipsoids for non-hydrogen atoms.

3. Supramolecular features and Hirshfeld surface analysis

In the title salt, the (C₂H₃BrN₃S)⁺ cation, the Cl⁻ anion, and the water molecule are linked by N—H⋯Cl, N—H⋯O, and O—H⋯Cl hydrogen bonds, forming molecular layers parallel to the (002) plane (Table 1, Figs. 2, 3 and 4). van der Waals interactions between these layers consolidate the crystal packing. C—H⋯π and π–π interactions were not observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1ⁱ	0.85	2.32	3.144 (4)	163
O1—H1B⋯Cl1ⁱⁱ	0.85	2.37	3.196 (4)	163
N3—H3A⋯Cl1ⁱ	0.86	2.38	3.221 (5)	168
N3—H3B⋯Cl1	0.86	2.29	3.127 (5)	163
N1—H1⋯O1	0.83 (3)	1.86 (3)	2.685 (6)	176 (7)
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A partial packing diagram showing the O—H⋯Cl, N—H⋯Cl and N—H⋯O hydrogen bonds (dashed lines). Symmetry codes: (i) 2 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (ii) −1 + x, y, z; (iii) 2 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (iv) 1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z.

Figure 3
Crystal packing of the title salt viewed along the a-axis direction. Intermolecular hydrogen bonds are shown as dashed lines.

Figure 4
Crystal packing of the title salt viewed along the b-axis direction.

Hirshfeld surface analysis was performed to visualize and quantify the intermolecular interactions in the cation of the title salt using CrystalExplorer (Spackman et al., 2021 ). The Hirshfeld surfaces were mapped over d_norm in the range −0.7220 (red) to +0,9614 (blue) a.u. (Fig. 5). The red regions are attributed to the N1—H1⋯O1 and N3—H3B⋯Cl1 interactions (Tables 1 and 2). The two-dimensional fingerprint plots indicate that the major contributions to the crystal packing are from Br⋯H/H⋯Br (21.4%), H⋯H (9.6%) and Cl⋯H/H⋯Cl (7.5%) interactions as shown in Fig. 6. Other, less notable contacts are from N⋯C/C⋯N (5.5%), N⋯N (5.3%), O⋯H/H⋯O (5.2%), N⋯H/H⋯N (5.1%), S⋯N/N⋯S (4.6%), Br⋯S/S⋯Br (4.3%), Br⋯O/O⋯Br (4.1%), C⋯H/H⋯C (4.1%), Cl⋯S/S⋯Cl (3.1%), Br⋯Cl/Cl⋯Br (2.2%), Cl⋯C/C⋯Cl (2.0%), Br⋯N/N⋯Br (1.8%), Cl⋯N/N⋯Cl (1.2%), S⋯O/O⋯S (0.8%), S⋯C/C⋯S (0.7%), Br⋯·C/C⋯Br (0.3%), C⋯C (0.1%) and O⋯C/C⋯O (0.1%) interactions.

Table 2
Summary of short interatomic contacts (Å)

Contact	Distance	Symmetry operation
Br1⋯H1B	3.09	x, −1 + y, z
Br1⋯O1	3.50	− $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, 1 − z
Br1⋯O1	3.56	$[{1\over 2}]$ + x, $[{1\over 2}]$ − y, 1 − z
H1⋯O1	1.85	x, y, z
H3B⋯Cl1	2.29	x, y, z
H3A⋯Cl1	2.38	2 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
C1⋯Cl1	3.51	−1 + x, y, z
Cl1⋯H1B	2.37	1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
Cl1⋯H1A	2.32	2 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z

Figure 5
The Hirshfeld surface of the (C₂H₃BrN₃S)⁺ cation of the title salt mapped over d_norm (color code. Br: green, C: gray; Cl: violet, H: white; O: red; N: blue; S: yellow).

Figure 6
The two-dimensional fingerprint plots, showing (a) all interactions, and those delineated into (b) Br⋯H/H⋯Br, (c) S⋯H/H⋯S, (d) H⋯H, (e) Cl⋯H/H⋯Cl, (f) N⋯C/C⋯N, (g) N⋯N, (h) O⋯H/H⋯O, (i) N⋯H/H⋯N and (j) S⋯N/N⋯S interactions; d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 6.00, last update April 2025; Groom et al., 2016 ) for the cation without the Br atom gave one hit and this is a copper complex. When the unprotonated molecule is searched for by removing Br, 240 results are obtained, and most of these are metal complexes. The three most similar compounds to the title salt containing the 2-amino-5-bromo-1,3,4-triazol-3-ium unit are CSD refcodes AYOVAM (Zhang et al., 2011 ), VIKSOZ (Smith & Lynch, 2013 ) and BOMROM (Smith & Lynch, 2014 ).

In AYOVAM, the strongest N—H⋯N intermolecular hydrogen bond, between the amine group and one thiadiazole N atom, forms centrosymmetric dimers. The other amine H atom extends the supramolecular network, forming an N—H⋯N contact with the other thiadiazole N atom. In VIKSOZ, the amine-heteroatom N—H⋯N hydrogen bond between the heterodimers results in a one-dimensional chain structure stretching along the c-axis direction. In BOMROM, the heterodimers are extended into a chain along the b-axis direction through an amine N—H⋯N thiadiazole hydrogen bond. In the title compound, the crystal packing is achieved through intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds.

5. Synthesis and crystallization

To a solution of 2-amino-1,3,4-thiadiazole (5 g, 48.45 mmol) in methanol (70 mL), sodium bicarbonate (8.14 g, 96.90 mmol) and bromine (2.5 mL, 48.45 mmol) were added. The reaction mixture was stirred at room temperature until the disappearance of the starting material (30–40 minutes). The methanol was removed under vacuum and the crude product was diluted with water (15 mL), filtered, dry in vacuo to give a brown solid, 5-bromo-1,3,4-thiadiazol-2-amine (94%). Colorless crystals suitable for X-ray analysis were obtained by slow evaporation of a mixture of 1 M HCl (pH = 0) and methanol (v/v, 1:2) solution. Analysis calculated for C₂H₅BrClN₃OS (M = 234.50): C 10.24, H 2.15, N 17.95; found: C 10.20, H 2.10, N 17.92%. ¹H NMR (300 MHz, DMSO-d⁶): δ 7.84 (3H). ¹³C NMR (75 MHz, DMSO-d₆) δ 154.8 and 159.1.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The water H-atom positions were determined from the difference-Fourier map, with their thermal characteristics restricted to 1.5 times those of the oxygen atom. The hydrogen atom of the NH group was identified in the difference-Fourier map, refined freely with 1.2U_eq(N), while the hydrogen atoms of the NH₂ groups were positioned geometrically and assigned thermal parameter values at 1.2 times that of the connected nitrogen atom.

Table 3
Experimental details

Crystal data
Chemical formula	C₂H₃BrN₃S⁺·Cl⁻·H₂O
M_r	234.51
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.3575 (1), 9.5328 (1), 15.0588 (2)
V (Å³)	769.08 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	12.49
Crystal size (mm)	0.18 × 0.14 × 0.08

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 )
T_min, T_max	0.341, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6293, 1495, 1485
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.09
No. of reflections	1495
No. of parameters	90
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.48
Absolute structure	Flack x determined using 579 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 ).
Absolute structure parameter	0.03 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2020), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2549381

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026004378/ox2022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026004378/ox2022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004378/ox2022Isup3.cml

checkCIF report

Computing details top

2-Amino-5-bromo-1,3,4-triazol-3-ium chloride monohydrate top

Crystal data top

C₂H₃BrN₃S⁺·Cl⁻·H₂O	D_x = 2.025 Mg m⁻³
M_r = 234.51	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 6428 reflections
a = 5.3575 (1) Å	θ = 2.9–71.3°
b = 9.5328 (1) Å	µ = 12.49 mm⁻¹
c = 15.0588 (2) Å	T = 293 K
V = 769.08 (2) Å³	Block, colourles
Z = 4	0.18 × 0.14 × 0.08 mm
F(000) = 456

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	1495 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1485 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.056
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.4°, θ_min = 5.5°
ω scans	h = −5→6
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −11→11
T_min = 0.341, T_max = 1.000	l = −18→18
6293 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0666P)² + 0.3887P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.035	(Δ/σ)_max < 0.001
wR(F²) = 0.097	Δρ_max = 0.63 e Å⁻³
S = 1.09	Δρ_min = −0.48 e Å⁻³
1495 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
90 parameters	Extinction coefficient: 0.0048 (8)
5 restraints	Absolute structure: Flack x determined using 579 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
Primary atom site location: dual	Absolute structure parameter: 0.03 (3)
Hydrogen site location: mixed

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
Br1	0.29817 (13)	−0.05893 (6)	0.45541 (4)	0.0458 (3)
Cl1	1.2003 (2)	0.21834 (13)	0.18983 (8)	0.0381 (4)
S1	0.7039 (2)	0.11486 (12)	0.35421 (8)	0.0319 (3)
O1	0.3054 (8)	0.5998 (4)	0.3940 (3)	0.0435 (9)
H1A	0.431399	0.647416	0.377691	0.065*
H1B	0.180495	0.648222	0.377514	0.065*
N1	0.4579 (7)	0.3315 (4)	0.3915 (3)	0.0269 (8)
N2	0.3207 (8)	0.2273 (4)	0.4298 (3)	0.0288 (8)
N3	0.8144 (10)	0.3806 (5)	0.3069 (3)	0.0420 (11)
H3A	0.785060	0.469288	0.306957	0.050*
H3B	0.943662	0.348223	0.279993	0.050*
C1	0.6621 (8)	0.2948 (5)	0.3479 (3)	0.0254 (9)
C2	0.4283 (9)	0.1099 (5)	0.4153 (3)	0.0280 (10)
H1	0.406 (12)	0.414 (3)	0.394 (4)	0.036 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0516 (4)	0.0277 (4)	0.0581 (4)	−0.0044 (3)	0.0093 (3)	0.0041 (2)
Cl1	0.0264 (5)	0.0377 (7)	0.0501 (7)	0.0046 (5)	−0.0006 (5)	−0.0154 (5)
S1	0.0258 (5)	0.0263 (6)	0.0435 (6)	0.0058 (5)	0.0041 (5)	−0.0054 (5)
O1	0.0295 (17)	0.0276 (19)	0.073 (3)	0.0051 (16)	0.006 (2)	0.0073 (17)
N1	0.0231 (17)	0.022 (2)	0.036 (2)	0.0028 (16)	0.0047 (16)	−0.0036 (15)
N2	0.0259 (19)	0.026 (2)	0.0342 (19)	−0.0007 (17)	0.0043 (16)	−0.0015 (16)
N3	0.036 (2)	0.030 (2)	0.060 (3)	0.001 (2)	0.022 (2)	−0.006 (2)
C1	0.019 (2)	0.024 (2)	0.033 (2)	−0.0016 (17)	0.0011 (17)	−0.0043 (18)
C2	0.026 (2)	0.027 (2)	0.031 (2)	0.001 (2)	−0.0031 (18)	−0.0049 (18)

Geometric parameters (Å, º) top

Br1—C2	1.855 (5)	N1—C1	1.323 (6)
S1—C1	1.733 (5)	N1—H1	0.83 (3)
S1—C2	1.740 (5)	N2—C2	1.277 (7)
O1—H1A	0.8500	N3—H3A	0.8600
O1—H1B	0.8501	N3—H3B	0.8600
N1—N2	1.364 (6)	N3—C1	1.309 (7)

C1—S1—C2	86.9 (2)	C1—N3—H3B	120.0
H1A—O1—H1B	104.5	N1—C1—S1	110.0 (4)
N2—N1—H1	119 (5)	N3—C1—S1	124.3 (4)
C1—N1—N2	117.5 (4)	N3—C1—N1	125.7 (5)
C1—N1—H1	123 (5)	S1—C2—Br1	121.0 (3)
C2—N2—N1	108.9 (4)	N2—C2—Br1	122.4 (4)
H3A—N3—H3B	120.0	N2—C2—S1	116.7 (4)
C1—N3—H3A	120.0

N1—N2—C2—Br1	−179.2 (3)	C1—S1—C2—N2	−0.6 (4)
N1—N2—C2—S1	−0.1 (5)	C1—N1—N2—C2	1.0 (6)
N2—N1—C1—S1	−1.4 (5)	C2—S1—C1—N1	1.1 (4)
N2—N1—C1—N3	179.6 (5)	C2—S1—C1—N3	−180.0 (5)
C1—S1—C2—Br1	178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1ⁱ	0.85	2.32	3.144 (4)	163
O1—H1B···Cl1ⁱⁱ	0.85	2.37	3.196 (4)	163
N3—H3A···Cl1ⁱ	0.86	2.38	3.221 (5)	168
N3—H3B···Cl1	0.86	2.29	3.127 (5)	163
N1—H1···O1	0.83 (3)	1.86 (3)	2.685 (6)	176 (7)

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

Summary of short interatomic contacts (Å) top

Contact	Distance	Symmetry operation
Br1···H1B	3.09	x, -1 + y, z
Br1···O1	3.50	-1/2 + x, 1/2 - y, 1 - z
Br1···O1	3.56	1/2 + x, 1/2 - y, 1 - z
H1···O1	1.85	x, y, z
H3B···Cl1	2.29	x, y, z
H3A···Cl1	2.38	2 - x, 1/2 + y, 1/2 - z
C1···Cl1	3.51	-1 + x, y, z
Cl1···H1B	2.37	1 - x, -1/2 + y, 1/2 - z
Cl1···H1A	2.32	2 - x, -1/2 + y, 1/2 - z

Acknowledgements

The authors' contributions are as follows; conceptualization BT, MA and GMM; synthesis, KIH and BT; X-ray analysis JA and SK; founding KIH and BT; writing (review and editing of the manuscript) BT, and MA; supervision SK, MA and GMM.

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ISSN: 2056-9890

Volume 82| Part 5| May 2026| Pages 525-529

https://doi.org/10.1107/S2056989026004378

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure and Hirshfeld surface analysis of 2-amino-5-bromo-1,3,4-triazol-3-ium chloride monohydrate

1. Chemical context

2. Structural commentary

3. Supra­molecular features and Hirshfeld surface analysis

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

3. Supramolecular features and Hirshfeld surface analysis