Ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-ylsulfan­yl)acetate

Muhammad Zareef; Rashid Iqbal; Muhammad Arfan; Masood Parvez

doi:10.1107/S1600536808007125

. 2008 Mar 20;64(Pt 4):o736. doi: 10.1107/S1600536808007125

Ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-ylsulfanyl)acetate

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

PMCID: PMC2961061 PMID: 21202126

Abstract

The title molecule, C₁₂H₁₂N₂O₃S, is composed of two individually planar units, viz. 5-phenyl-1,3,4-oxadiazol-2-yl-sulfanyl and ethyl acetate, which are oriented at almost right angles [80.07 (8)°] with respect to each other. The structure is stabilized by weak intermolecular C—H⋯O and C—H⋯N hydrogen bonds. The phenyl and oxadiazole rings show π–π stacking interactions [centroid–centroid distance = 3.846 (2) Å] and there is also a short π-interaction between the carbonyl O atom and the oxadiazole ring [the distance from this O atom to the centroid of the oxadiazole ring is 3.156 (2) Å].

Related literature

For related literature, see: Cao et al. (2002 ▶); Iqbal et al. (2007 ▶); Kadi et al. (2007 ▶); Mir & Siddiqui (1970 ▶); Zareef et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C₁₂H₁₂N₂O₃S
M _r = 264.30
Monoclinic,
a = 8.777 (3) Å
b = 11.008 (5) Å
c = 13.177 (6) Å
β = 103.59 (3)°
V = 1237.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 173 (2) K
0.16 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.959, T _max = 0.979
5263 measured reflections
2820 independent reflections
1943 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.117
S = 1.02
2820 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.27 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/S1600536808007125/fb2092sup1.cif

e-64-0o736-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007125/fb2092Isup2.hkl

e-64-0o736-Isup2.hkl^{(135.6KB, 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
C4—H4⋯O2ⁱ	0.95	2.51	3.268 (3)	137
C9—H9B⋯N1ⁱⁱ	0.99	2.38	3.293 (3)	153

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

supplementary crystallographic information

Comment

Substituted-1,3,4-oxadiazole derivatives are of significant interest due to their chemotherapeutic effects (Kadi et al., 2007; Zareef et al., 2006; Zareef et al., 2007; Cao et al., 2002). Based on the known structures of the 2,5-disubstituted-1,3,4-oxadiazoles with diverse biological activities and their derivatives, we have designed and synthesized several new derivatives of 1,3,4-oxadiazole (Zareef et al., 2007). In this paper, we report the structure of one of these compounds.

The structure of the title compound (Fig. 1) is composed of two essentially planar moieties, C1—C8/N1/N2/O1/S1 and C9—C12/O2/O3 the least-square planes of which are inclined at 80.07 (8)°; the maximum deviations from the respective least square planes are: O1 = 0.037 (2) and C11 = 0.048 (2) Å. The structure is stabilized by two intermolecular interactions C4—H4···O2 and C9—H9B···N1 (Table 1). The shortest distance between the centroids of the phenyl and the oxadiazole rings of the adjacent molecules is 3.846 (2) Å which indicates the existence of π-π stacking interactions. In addition, there is a π-interaction between the carbonyl O-atom and the oxadiazole ring. (The distance from this O atom to the centroid of the oxadiazole ring is 3.156 (2) Å). The bond distances and angles in the title compound are in agreement with the corresponding ones reported in the similar structure of Ethyl 2-({5-[2-(benzoylamino)phenyl]-1,3,4-oxadiazol-2-yl}sulfanyl)acetate (Iqbal et al., 2007).

Experimental

The title compound was prepared according to the procedure reported in the literature (Zareef et al., 2006; Mir & Siddiqui, 1970). To a solution of benzoic acid hydrazide (50 mmol) in ethanol (150 ml) was added carbon disulfide (55 mmol), followed by the addition of KOH (50 mmol) dissolved in 25 ml of water. The reaction mixture was stirred and subjected to reflux for 19 h. After reaction completion, excess ethanol was distilled off. The crude solid obtained was dissolved in water (50 ml) and acidified with 4 N HCl to pH 2–3. The product was filtered, washed with water and recrystallized from aqueous ethanol (20–30%). The resulting 5-phenyl-2-mercapto-1,3,4-oxadiazole (20 mmol) was dissolved in saturated aqueous sodium hydrogencarbonate solution while stirring. The required ethylbromoacetate (20 mmol) in absolute ethanol (10 ml) was added and the reaction mixture was stirred for 7 h at 325–335 K. After reaction completion, the resulting solid was filtered off, washed with water and recrystallized from aqueous ethanol (60%) (Yield = 75%; m.p. = 344–345 K). Prismatic crystals suitable for crystallographic study were grown from ethanol solution by slow evaporation at room temperature.