4-Ethyl-3-(3-pyrid­yl)-1H-1,2,4-triazole-5(4H)-thione 0.095-hydrate

Muhammad Zareef; Muhammad Arfan; Rashid Iqbal; Masood Parvez

doi:10.1107/S1600536808011744

. 2008 Apr 30;64(Pt 5):o945. doi: 10.1107/S1600536808011744

4-Ethyl-3-(3-pyridyl)-1H-1,2,4-triazole-5(4H)-thione 0.095-hydrate

Muhammad Zareef ^a,^*, Muhammad Arfan ^a, Rashid Iqbal ^a, Masood Parvez ^b

PMCID: PMC2961273 PMID: 21202426

Abstract

The title compound, C₉H₁₀N₄S·0.095H₂O, consists of discrete 4-ethyl-3-(3-pyridyl)-1H-1,2,4-triazole-5(4H)-thione molecules and a disordered molecule of water of hydration with partial occupancy, lying on a twofold rotation axis. The dihedral angle between the pyridine and triazole rings is 41.73 (8)°. In the crystal structure, molecules are hydrogen bonded via triazole NH groups and pyridyl N atoms, forming chains parallel to the a axis.

Related literature

For related literature, see: Ahmad et al. (2001 ▶); Chai et al. (2003 ▶); Dege et al. (2004 ▶, 2005 ▶)); Demir et al. (2006 ▶); Dobosz et al. (2003 ▶); Hashimoto et al. (1990 ▶); Kanazawa et al. (1988 ▶); Mazur et al. (2006 ▶).

Experimental

Crystal data

C₉H₁₀N₄S·0.095H₂O
M _r = 207.96
Monoclinic,
a = 14.076 (5) Å
b = 8.877 (5) Å
c = 16.216 (8) Å
β = 93.25 (3)°
V = 2023.0 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 173 (2) K
0.18 × 0.16 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.950, T _max = 0.972
3392 measured reflections
2297 independent reflections
1616 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.107
S = 1.05
2297 reflections
137 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011744/lh2615sup1.cif

e-64-0o945-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011744/lh2615Isup2.hkl

e-64-0o945-Isup2.hkl^{(110.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N4ⁱ	0.88 (2)	1.94 (2)	2.792 (3)	162 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Disubstituted 1,2,4-triazoles and their derivatives are very important five membered heterocyclic compounds for their biological and pharmacological activities, such as antitumoral, inhibition of cholesterol, fungicidal, herbicidal, anticonvulsant (Kanazawa et al., 1988; Chai et al., 2003; Hashimoto et al., 1990). Herein, we report the synthesis and crystal structure of the title compound, (I).

The structure of (I) is composed of independent molecules of 4-ethyl-2,4-dihydro-5-(3-pyridyl)-3H-1,2,4-triazole-3-thione (Fig. 1) and a disordered water of hydration with partial occupancy lying on a two-fold rotation axis. The bond distances and bond angles in (I) agree well with the corresponding bond distances and angles reported in some compounds closely related to (I) (e.g., Dege et al., 2004, 2005; Mazur et al., 2006; Dobosz et al., 2003; Demir, et al., 2006). The mean-planes formed by the pyridyl and triazole rings in (I) lie at 41.73 (8)° with respect to each other while the mean-plane of the ethyl group is inclined with the triazole ring at 80.39 (13)°.

The water of hydration is surrounded by four molecules of (I) with S1···O1 and N1···O1 separation of 3.074 (4) and 3.382 (9) Å, respectively (Fig. 2). The molecules of (I) are hydrogen bonded via N2—H2···N4 forming chains lying parallel to the a axis (details of hydrogen bonding geometry have been given in Table 1). The shortest distance between the centroids of pyridyl and triazole rings from two different molecules lying about inversion centers is 4.350 (3) Å.

Experimental

The title compound was prepared from the corresponding thiosemicarbazide by following the reported procedure (Ahmad et al., 2001). 4-Ethyl-1-(2-pyridoyl)thiosemicarbazide (12 mmol) was dissolved in an aqueous 4 N sodium hydroxide solution (65 ml). The solution was heated to reflux for 11.5 h, cooled and filtered. The filtrate was acidified to pH of 4–5, with 4 N hydrochloric acid. The solid product was filtered off, washed with water and recrystallized from aqueous ethanol (60%). Crystals of (I) were grown by slow evaporation of the ethanol over 15 days at room temperature (yield 72%).