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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o146.
Published online 2008 December 17. doi:  10.1107/S1600536808042001
PMCID: PMC2968061

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

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0o146-scheme1.jpg

Experimental

Crystal data

  • C11H9FN2O3
  • M r = 236.20
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o146-efi1.jpg
  • 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
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.21 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Refinement

H atoms attached to C atoms were added at their calculated positions and included in the structure factors calculations, with C—H = 0.93 (aromatic) and 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C). The H atom of carboxylic acid was located in a difference Fourier map and treated as a free atom.

Figures

Fig. 1.
The molecular structure of (I) with labeling scheme. Displacement ellipsoids are shown at the 40% probability level.
Fig. 2.
Dimeric strucuture formed by hydrogen bonding.
Fig. 3.
Molecules of (I) stacked along the a axis.

Crystal data

C11H9FN2O3Z = 2
Mr = 236.20F(000) = 244
Triclinic, P1Dx = 1.484 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 5.055 (1) ÅCell parameters from 25 reflections
b = 5.905 (1) Åθ = 5.0–18.8°
c = 17.967 (1) ŵ = 0.12 mm1
α = 85.769 (5)°T = 293 K
β = 87.965 (7)°Irregular plate, colorless
γ = 81.252 (7)°0.50 × 0.33 × 0.07 mm
V = 528.47 (14) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.010
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.1°
graphiteh = −6→6
ω–2θ scansk = −7→7
2136 measured reflectionsl = −22→0
2066 independent reflections3 standard reflections every 200 reflections
1557 reflections with I > 2σ(I) intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0583P)2 + 0.0868P] where P = (Fo2 + 2Fc2)/3
2066 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.21 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C30.1073 (3)−0.0359 (3)0.24108 (9)0.0403 (4)
C5−0.1973 (3)0.0022 (3)0.32245 (9)0.0412 (4)
C6−0.4105 (3)0.0731 (3)0.37879 (10)0.0463 (4)
H6A−0.34290.02780.42840.056*
H6B−0.5616−0.00640.37220.056*
C7−0.5043 (3)0.3291 (3)0.37270 (10)0.0476 (4)
H7A−0.35290.40860.37880.057*
H7B−0.57380.37410.32330.057*
C8−0.7169 (3)0.4009 (3)0.42998 (9)0.0422 (4)
C110.3022 (3)0.0236 (3)0.18257 (9)0.0415 (4)
C120.2778 (4)0.2461 (3)0.15009 (10)0.0522 (4)
H120.14260.35840.16600.063*
C130.4575 (4)0.2996 (4)0.09349 (11)0.0618 (5)
H130.44130.44850.07150.074*
C140.6588 (4)0.1352 (4)0.06958 (11)0.0594 (5)
H140.77850.17080.03160.071*
C150.6783 (3)−0.0823 (3)0.10322 (10)0.0534 (5)
C160.5063 (3)−0.1432 (3)0.15924 (10)0.0483 (4)
H160.5256−0.29230.18110.058*
N20.0849 (3)−0.2473 (3)0.26222 (9)0.0552 (4)
N4−0.0667 (3)0.1270 (2)0.27700 (8)0.0437 (3)
O1−0.1230 (2)−0.2237 (2)0.31750 (7)0.0555 (4)
O9−0.8599 (2)0.2685 (2)0.45969 (7)0.0547 (3)
O10−0.7395 (3)0.6168 (2)0.44456 (8)0.0551 (3)
F170.8776 (2)−0.2448 (2)0.07982 (7)0.0822 (4)
H10−0.885 (6)0.660 (5)0.4800 (16)0.102 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C30.0353 (8)0.0424 (8)0.0424 (8)−0.0037 (6)0.0030 (7)−0.0040 (7)
C50.0372 (8)0.0418 (8)0.0440 (9)−0.0059 (6)0.0037 (7)−0.0008 (7)
C60.0424 (9)0.0479 (9)0.0476 (9)−0.0091 (7)0.0116 (7)0.0011 (7)
C70.0432 (9)0.0465 (9)0.0510 (10)−0.0062 (7)0.0137 (7)0.0019 (7)
C80.0359 (8)0.0454 (9)0.0442 (9)−0.0060 (7)0.0050 (7)0.0014 (7)
C110.0373 (8)0.0482 (9)0.0402 (8)−0.0093 (7)0.0040 (6)−0.0076 (7)
C120.0533 (10)0.0504 (10)0.0511 (10)−0.0047 (8)0.0130 (8)−0.0059 (8)
C130.0734 (13)0.0582 (12)0.0543 (11)−0.0167 (10)0.0160 (9)−0.0023 (9)
C140.0573 (11)0.0746 (14)0.0489 (10)−0.0210 (10)0.0186 (9)−0.0092 (9)
C150.0414 (9)0.0669 (12)0.0518 (10)−0.0044 (8)0.0114 (8)−0.0165 (9)
C160.0445 (9)0.0497 (10)0.0503 (10)−0.0057 (7)0.0045 (8)−0.0070 (7)
N20.0529 (9)0.0452 (8)0.0633 (10)−0.0008 (6)0.0206 (7)0.0004 (7)
N40.0412 (7)0.0429 (7)0.0468 (8)−0.0076 (6)0.0108 (6)−0.0045 (6)
O10.0560 (7)0.0418 (7)0.0646 (8)−0.0033 (5)0.0208 (6)0.0038 (5)
O90.0488 (7)0.0519 (7)0.0636 (8)−0.0129 (5)0.0229 (6)−0.0052 (6)
O100.0517 (7)0.0471 (7)0.0665 (8)−0.0103 (5)0.0198 (6)−0.0077 (6)
F170.0635 (7)0.0919 (10)0.0841 (9)0.0081 (6)0.0308 (6)−0.0145 (7)

Geometric parameters (Å, °)

C3—N21.298 (2)C11—C121.387 (2)
C3—N41.382 (2)C11—C161.389 (2)
C3—C111.475 (2)C12—C131.390 (3)
C5—N41.291 (2)C12—H120.9300
C5—O11.338 (2)C13—C141.376 (3)
C5—C61.486 (2)C13—H130.9300
C6—C71.511 (2)C14—C151.370 (3)
C6—H6A0.9700C14—H140.9300
C6—H6B0.9700C15—F171.359 (2)
C7—C81.497 (2)C15—C161.370 (2)
C7—H7A0.9700C16—H160.9300
C7—H7B0.9700N2—O11.4183 (19)
C8—O91.2252 (19)O10—H100.97 (3)
C8—O101.308 (2)
N2—C3—N4114.80 (14)C12—C11—C3119.61 (15)
N2—C3—C11122.14 (14)C16—C11—C3120.18 (15)
N4—C3—C11123.06 (14)C11—C12—C13119.36 (17)
N4—C5—O1113.59 (14)C11—C12—H12120.3
N4—C5—C6129.61 (15)C13—C12—H12120.3
O1—C5—C6116.79 (13)C14—C13—C12120.87 (18)
C5—C6—C7112.30 (13)C14—C13—H13119.6
C5—C6—H6A109.1C12—C13—H13119.6
C7—C6—H6A109.1C15—C14—C13118.25 (17)
C5—C6—H6B109.1C15—C14—H14120.9
C7—C6—H6B109.1C13—C14—H14120.9
H6A—C6—H6B107.9F17—C15—C14118.33 (16)
C8—C7—C6112.31 (14)F17—C15—C16118.68 (18)
C8—C7—H7A109.1C14—C15—C16122.99 (17)
C6—C7—H7A109.1C15—C16—C11118.33 (17)
C8—C7—H7B109.1C15—C16—H16120.8
C6—C7—H7B109.1C11—C16—H16120.8
H7A—C7—H7B107.9C3—N2—O1102.97 (13)
O9—C8—O10123.07 (15)C5—N4—C3102.40 (13)
O9—C8—C7122.54 (15)C5—O1—N2106.23 (12)
O10—C8—C7114.38 (14)C8—O10—H10112.6 (16)
C12—C11—C16120.20 (15)
N4—C5—C6—C78.6 (3)C13—C14—C15—C160.2 (3)
O1—C5—C6—C7−172.42 (15)F17—C15—C16—C11−179.68 (16)
C5—C6—C7—C8−179.36 (14)C14—C15—C16—C110.3 (3)
C6—C7—C8—O9−23.4 (2)C12—C11—C16—C15−0.8 (3)
C6—C7—C8—O10157.66 (15)C3—C11—C16—C15178.08 (15)
N2—C3—C11—C12165.28 (17)N4—C3—N2—O1−0.10 (19)
N4—C3—C11—C12−14.0 (2)C11—C3—N2—O1−179.48 (14)
N2—C3—C11—C16−13.6 (2)O1—C5—N4—C3−0.79 (18)
N4—C3—C11—C16167.08 (15)C6—C5—N4—C3178.25 (16)
C16—C11—C12—C130.7 (3)N2—C3—N4—C50.54 (19)
C3—C11—C12—C13−178.15 (17)C11—C3—N4—C5179.91 (15)
C11—C12—C13—C14−0.2 (3)N4—C5—O1—N20.77 (19)
C12—C13—C14—C15−0.3 (3)C6—C5—O1—N2−178.40 (14)
C13—C14—C15—F17−179.80 (17)C3—N2—O1—C5−0.37 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O10—H10···O9i0.97 (3)1.68 (3)2.650 (2)179 (3)

Symmetry codes: (i) −x−2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2367).

References

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