3-[3-(3-Fluoro­phen­yl)-1,2,4-oxadiazol-5-yl]propionic acid

Suseanne K M Santos; Ricardo A W Neves Filho; Adailton J Bortoluzzi; Rajendra M Srivastava

doi:10.1107/S1600536808042001

. 2008 Dec 17;65(Pt 1):o146. doi: 10.1107/S1600536808042001

3-[3-(3-Fluorophenyl)-1,2,4-oxadiazol-5-yl]propionic acid

Suseanne K M Santos ^a, Ricardo A W Neves Filho ^a, Adailton J Bortoluzzi ^b, Rajendra M Srivastava ^a,^*

PMCID: PMC2968061 PMID: 21581604

Abstract

In the title compound, C₁₁H₉FN₂O₃, the benzene ring is almost coplanar with the heterocyclic ring, making a dihedral angle of 14.0 (1)°. The plane of the carboxyl group is rotated by 14.7 (3)° with respect to the 1,2,4-oxadiazole ring plane. The aliphatic chain exhibits a standard zigzag arrangement. Two intermolecular O—H⋯O hydrogen bonds between the carboxyl groups related by an inversion centre promote a dimeric structure formation. The dimers are stacked along the crystallographic a axis.

Related literature

For general background, see: Gallardo et al. (2008 ▶); Jakopin & Dolenc (2008 ▶). For related structures, see: Wang et al. (2006 ▶, 2007 ▶); Yan, Xing et al. (2006 ▶); Yan et al. (2006a ▶,b ▶). For the method of preparation, see: Sindkhedkar et al. (2008 ▶); Srivastava & Seabra (1997 ▶).

Experimental

Crystal data

C₁₁H₉FN₂O₃
M _r = 236.20
Triclinic,
a = 5.055 (1) Å
b = 5.905 (1) Å
c = 17.967 (1) Å
α = 85.769 (5)°
β = 87.965 (7)°
γ = 81.252 (7)°
V = 528.47 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 (2) K
0.50 × 0.33 × 0.07 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2136 measured reflections
2066 independent reflections
1557 reflections with I > 2σ(I)
R _int = 0.010
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.112
S = 1.06
2066 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042001/is2367sup1.cif

e-65-0o146-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042001/is2367Isup2.hkl

e-65-0o146-Isup2.hkl^{(99.5KB, 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
O10—H10⋯O9ⁱ	0.97 (3)	1.68 (3)	2.650 (2)	179 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial assistance. SKMS thanks the Programa Institucional de Bolsas de Iniciação Científica (PIBIC/CNPq) for an Undergraduate fellowship.

supplementary crystallographic information

Comment

1,2,4-Oxadiazoles are well known compounds, which exhibit a large number of biological activities (Jakopin & Dolenc, 2008). Recently, the use of this heterocycle as core for luminescent liquid crystals has also been described (Gallardo et al., 2008).

In the title compound (Fig. 1), the bond lengths and angles are in agreement with the values previously reported for 1,2,4-oxadiazole-containing molecules (Wang et al., 2006, 2007; Yan, Xing et al., 2006; Yan et al., 2006a,b). The torsion angle N2—C3—C11—C16 between the benzene ring attached to C-3 of the 1,2,4-oxadiazole system is -13.6 (2)°, thus, both rings are almost coplanar. The C-5 side-chain containing a carboxylic acid group shows a zigzag arrangement, having the torsion angle C5—C6—C7—C8 of -179.4 (1)°. In addition, the plane of the carboxylic group is also rotated by 14.7 (3)° with respect to the mean plane of the 1,2,4-oxadiazole five-membered ring, but in opposite direction of deviation of the fluoro-phenyl ring. This makes the molecular structure to be slightly twisted. Carboxylic groups are involved in centrosymmetric intermolecular hydrogen-bonding forming a dimeric structure (Fig. 2). The dimmers are perfectly stacked along the crystallographic a axis (Fig. 3).

Experimental

The title compound was synthesized following the procedure reported earlier for the analogous compounds (Srivastava & Seabra, 1997; Sindkhedkar et al., 2008). A mixture of 3-fluorbenzamidoxime (2.0 mmol) and succinic anhydride (2.2 mmol) was heated in a domestic microwave oven for 10 min. The crude material was purified by column chromatography. Crystallization of pure material from chloroform, from which a suitable crystal was chosen for the X-ray crystallographic experiment.