3-(1-Benzofuran-2-yl)-1H-1,2,4-triazole-5(4H)-thione monohydrate

Hoong-Kun Fun; Suhana Arshad; Nithinchandra; Balakrishna Kalluraya; Shobhitha Shetty

doi:10.1107/S1600536812025305

. 2012 Jun 13;68(Pt 7):o2067. doi: 10.1107/S1600536812025305

3-(1-Benzofuran-2-yl)-1H-1,2,4-triazole-5(4H)-thione monohydrate

Hoong-Kun Fun ^a,^*,^‡, Suhana Arshad ^a, Nithinchandra ^b, Balakrishna Kalluraya ^b, Shobhitha Shetty ^b

PMCID: PMC3393331 PMID: 22807888

Abstract

In the title hydrate, C₁₀H₇N₃OS·H₂O, the essentially planar benzofuran [maximum deviation = 0.006 (1) Å] and 4,5-dihydro-1H-1,2,4-triazole [maximum deviation = 0.007 (1) Å] rings form a dihedral angle of 11.67 (6)°. In the crystal, O—H⋯N, O—H⋯S, N—H⋯O and N—H⋯S hydrogen bonds link the molecules into sheets lying parallel to the bc plane. Aromatic π–π stacking interactions [centroid–centroid distances = 3.5078 (8)–3.6113 (8) Å] are also observed.

Related literature

For background to 1,2,4-triazoles, see: Shujuan et al. (2004 ▶); Clemons et al. (2004 ▶); Johnston (2002 ▶); Wei et al. (2007 ▶). For related structures, see: Jing et al. (2012 ▶); Fun et al. (2011 ▶); Abdel-Aziz et al. (2011 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₀H₇N₃OS·H₂O
M _r = 235.26
Monoclinic,
a = 7.1446 (1) Å
b = 8.8075 (1) Å
c = 17.3274 (2) Å
β = 111.942 (1)°
V = 1011.36 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.39 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.891, T _max = 0.955
19917 measured reflections
4162 independent reflections
3347 reflections with > I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.108
S = 1.07
4162 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025305/hb6837sup1.cif

e-68-o2067-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025305/hb6837Isup2.hkl

e-68-o2067-Isup2.hkl^{(204KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025305/hb6837Isup3.cml

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
O1W—H1OW⋯N2ⁱ	0.90	2.05	2.9135 (14)	160
O1W—H2OW⋯S1ⁱⁱ	0.82	2.46	3.2674 (11)	167
N1—H1N1⋯O1W ⁱⁱⁱ	0.90 (2)	1.81 (2)	2.7100 (14)	172.6 (19)
N3—H1N3⋯S1^iv	0.846 (18)	2.498 (18)	3.3242 (10)	165.7 (16)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. BK is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

supplementary crystallographic information

Comment

The 1,2,4-triazole nucleus has been incorporated into a wide variety of therapeutically interesting compounds. Several compounds containing 1,2,4-triazole rings are well known as drugs. For example, fluconazole is used as an antimicrobial drug (Shujuan et al., 2004), whereas vorozole, letrozole and anastrozole are non-steroidal drugs used for the treatment of cancer (Clemons et al., 2004) and loreclezole is used as an anticonvulsant (Johnston, 2002). Similarly substituted derivatives of triazole possess comprehensive bioactivities such as antimicrobial, anti-inflammatory, analgesic, antihypertensive, anticonvulsant and antiviral activities (Wei et al., 2007). We now report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), consists of one 5-(1-Benzofuran-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione molecule and one water molecule. The benzofuran ring (O1/C3–C10) and the 4,5-dihydro -1H-1,2,4-triazole ring (N1–N3/C1/C2) are essentially planar with maximum deviations of 0.006 (1) Å at atom O1 and 0.007 (1) Å at atom N3, respectively. The dihedral angle between the benzofuran and 4,5-dihydro- 1H-1,2,4-triazole rings is 11.67 (6)°. Bond lengths and angles are within normal ranges and comparable to the related structures (Jing et al., 2012; Fun et al., 2011; Abdel-Aziz et al., 2011).

The crystal packing is shown in Fig. 2. The molecules are linked via O1W—H1OW···N2, O1W—H2OW···S1, N1—H1N1···O1W and N3—H1N3···S1 hydrogen bonds (Table 1) into two-dimensional networks parallel to bc-plane. π–π interactions of Cg1···Cg1 = 3.6113 (8) Å (symmetry code: 1 - x, -y, 1 - z), Cg1···Cg2 = 3.5078 (8) Å (symmetry code: 2 - x, -y, 1 - z), Cg2···Cg3 = 3.5881 (8) Å (symmetry code: 1 - x, -y, 1 - z) and Cg3···Cg2 = 3.6056 (8) Å (symmetry code: 2 - x, -y, 1 - z) further stabilized the crystal structure [Cg1, Cg2 and Cg3 are the centroids of the O1/C3–C5/C10, N1–N3/C1/C2 and C5–C10 rings, respectively].

Experimental

A mixture of 2-(1-benzofuran-2-ylcarbonyl)hydrazinecarbothioamide (0.01 mol) and 10% KOH (10 ml) was refluxed for 3 h. The mixture was cooled to room temperature and then neutralized by the gradual addition of glacial acetic acid. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Yellow blocks of the title compound were obtained by slow evaporation of the ethanolic solution.