2-[4-Benzyl-5-(2-fur­yl)-4H-1,2,4-triazol-3-ylsulfan­yl]acetamide

Muhammad Zareef; Rashid Iqbal; Muhammad Arfan; Masood Parvez

doi:10.1107/S1600536808017170

. 2008 Jun 13;64(Pt 7):o1259. doi: 10.1107/S1600536808017170

2-[4-Benzyl-5-(2-furyl)-4H-1,2,4-triazol-3-ylsulfanyl]acetamide

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

PMCID: PMC2961744 PMID: 21202893

Abstract

In the title compound, C₁₅H₁₄N₄O₂S, the phenyl ring is inclined at 70.25 (6)° with respect to the approximately planar furyl–triazolsulfanyl–acetamide unit. In the crystal structure, molecules related by inversion centers form dimers via intermolecular N—H⋯O hydrogen bonds between acetamide groups, resulting in eight-membered rings with an R ₂ ²(8) motif. In addition, the other H atom of the acetamide group is involved in an intermolecular hydrogen bond with an N atom of the triazole ring, resulting in chains extended along the c axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a axis.

Related literature

For related literature, see: Ahmad et al. (2001 ▶); Altman & Solomost (1993 ▶); Bernstein et al. (1994 ▶); Chai et al. (2003 ▶); Dege et al. (2004 ▶); Hashimoto et al. (1990 ▶); Kanazawa et al. (1988 ▶); Yildirim et al. (2004 ▶); Zareef, Iqbal & Parvez (2008 ▶); Zareef, Iqbal, Mirza et al. (2008 ▶); Öztürk et al. (2004 ▶).

Experimental

Crystal data

C₁₅H₁₄N₄O₂S
M _r = 314.36
Monoclinic,
a = 15.995 (9) Å
b = 7.261 (3) Å
c = 13.598 (8) Å
β = 105.46 (2)°
V = 1522.1 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.24 × 0.08 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.948, T _max = 0.995
5255 measured reflections
3435 independent reflections
2449 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.105
S = 1.04
3435 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 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: SAPI91 (Fan, 1991 ▶); 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/S1600536808017170/lh2638sup1.cif

e-64-o1259-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017170/lh2638Isup2.hkl

e-64-o1259-Isup2.hkl^{(165KB, 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
N4—H4A⋯O2ⁱ	0.88 (2)	2.01 (2)	2.880 (2)	172 (2)
N4—H4B⋯N2ⁱⁱ	0.89 (2)	2.01 (2)	2.881 (3)	167 (2)
C9—H9B⋯O1	0.99	2.36	3.007 (3)	122

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

supplementary crystallographic information

Comment

Derivatives of 1,2,4-triazole have significant importance for their broad-spectrum biological and pharmacological activities, such as fungicidal, herbicidal, anticonvulsant, antitumoral, inhibition of cholesterol (Chai et al., 2003; Kanazawa et al., 1988; Hashimoto et al., 1990). In addition, they have many applications in the agriculture domain (Altman & Solomost, 1993). In this paper, we report the synthesis and crystal structure of the title compound, (I).

The structure of the title compound (Fig. 1) is composed of a phenyl ring that is inclined at 70.25 (6)° with respect to a somewhat planar furyl-triazol-thio-acetamide moiety. The mean-planes of the furyl and triazole rings lie at 8.34 (13)° with respect to each other while the atoms in the thioacetamide group (S1/C7/C8/O2/N4) also form a plane which is inclined at 9.48 (10) and 3.45 (12)°, respectively, with furyl and triazole rings. Bond distances and bond angles in (I) agree well with the corresponding bond distances and bond angles reported in compounds closely related to (I) (Zareef, Iqbal & Parvez, 2008; Öztürk et al., 2004; Yildirim et al., 2004; Dege et al., 2004); in all these compounds, the mean-planes of the phenyl rings and the furyl-triazole moieties lie close to right angles. The molecules of (I) lying about inversion centers form dimers as a result of intermolecular N—H···O type hydrogen bonding between acetamide groups; the resulting eight membered rings exhibit an R₂²(8)-type motif (Bernstein et al., 1994). The second H-atom of the acetamide group is involved in an intermolecular hydrogen bond with N2 of the triazole ring thus resulting in a chain structure along the c-axis. The overall effect is the formation of a hydrogen-bonded two-dimensional framework perpendicular to the a-axis (Fig. 2). The structure is further stabilized by non-classical intramolecular interactions of the type C—H···O (Table 1).

Experimental

4-Benzyl-1-(2-furoyl)thiosemicarbazide (10 mmol) was dissolved in aqueous 4 N NaOH solution (50 ml). The solution was heated to reflux for 7 h, cooled and filtered. The filtrate was acidified to pH of 4–5, with 4 N HCl. The solid crude product, 4-benzyl-3-(2-furyl)-1H-1,2,4-triazole-5(4H)-thione, was filtered off, washed with water and recrystallized from aqueous ethanol (60%) (Ahmad et al., 2001). Ethyl S-ester of the triazole was prepared following the procedure reported earlier Zareef, Iqbal, Mirza & et al., 2008). Ethyl-[4-benzyl-5-(2-furyl)-(1,2,4-triazol-3-ylthio)]acetate (10 mmol) was dissolved in dry ethanol (60 ml). Dry ammonia gas was bubbled through the ester solution, with continuous stirring, for 5 hr. The progress of the reaction was monitored by TLC (silica; methanol: chloroform; 1:2). The excess solvent was distilled off under reduced pressure. The crude product was washed with cold water and recrystallized from aqueous ethanol (30%). Crystals of the title compound (I) were grown by slow evaporation of an ethanol solution over 9 days at room temperature (yield 77%).