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Volume 69 
Part 6 
Page o897  
June 2013  

Received 3 April 2013
Accepted 26 April 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.111
Data-to-parameter ratio = 12.4
Details
Open access

5-Methyl-3-phenylisoxazole-4-carboxylic acid

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India, and cDepartment of Physics, St Philomena's College, Mysore, India
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

In the title compound, C11H9NO3, the phenyl and isoxazole rings form a dihedral angle of 56.64 (8)°. The carboxy group is almost in the same plane as the isoxazole ring with a C-C-C-O torsion angle of -3.3 (2)°. In the crystal, pairs of O-H...O hydrogen bonds link the molecules into head-to-head dimers. C-H...N hydrogen bonds and [pi]-[pi] stacking interactions between phenyl rings [centroid-centroid distance = 3.9614 (17)Å] link the dimers into a three-dimensional network.

Related literature

For the biological and pharmaceutical importance of isoxazoles, see: Basappa et al., (2003[Basappa, M. P., Sadashiva, K., Mantelingu, S., Nanjunda, S. & Rangappa, K. S. (2003). Bioorg. Med. Chem. Lett. 11, 4539-4544.]); Conti et al. (1998[Conti, P., Dallanoce, C., Amici, M. D., Micheli, C. D. & Klotz, K. N. (1998). Bioorg. Med. Chem. 6, 401-408.]); Kang et al. (2000[Kang, Y. Y., Shin, K. L., Yoo, K. H., Seo, K. J., Hong, C. Y., Lee, C. S., Park, S. Y., Kim, D. J. & Park, S. W. (2000). Bioorg. Med. Chem. Lett. 10, 95-99.]); Lee et al. (2009[Lee, Y., Park, S. M. & Kim, B. H. (2009). Bioorg. Med. Chem. Lett. 19, 1126-1128.]); Shin et al. (2005[Shin, K. D., Lee, M. Y., Shin, D. S., Lee, S., Son, K. H., Koh, S., Paik, Y. K., Kwon, B. M. & Han, D. C. (2005). J. Biol. Chem. 280, 41439-41448.]); Stevens & Albizati (1984[Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.]). For bond-length and angle data in related structures, see: Wolf et al. (1995[Wolf, R., Wong, M. W., Kennard, C. H. L. & Wentrup, C. (1995). J. Am. Chem. Soc. 117, 6789-6790.]); Chandra et al., (2013[Chandra, Raghu, K., Srikantamurthy, N., Umesha, K. B., Palani, K. & Mahendra, M. (2013). Acta Cryst. E69, o388.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9NO3

  • Mr = 203.19

  • Monoclinic, P 21 /n

  • a = 11.953 (4) Å

  • b = 5.981 (2) Å

  • c = 14.142 (5) Å

  • [beta] = 105.548 (6)°

  • V = 974.0 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 273 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 8619 measured reflections

  • 1712 independent reflections

  • 1558 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.05

  • 1712 reflections

  • 138 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O14-H14...O15i 0.82 1.81 2.6252 (18) 172
C11-H11A...N8ii 0.96 2.51 3.427 (2) 159
Symmetry codes: (i) -x+2, -y, -z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2504 ).


Acknowledgements

The authors would like to thank the UGC, New Delhi, Government of India, for awarding a project under the head F·No.41-920/2012(SR) dated: 25-07-2012.

References

Basappa, M. P., Sadashiva, K., Mantelingu, S., Nanjunda, S. & Rangappa, K. S. (2003). Bioorg. Med. Chem. Lett. 11, 4539-4544.  [ChemPort]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chandra, Raghu, K., Srikantamurthy, N., Umesha, K. B., Palani, K. & Mahendra, M. (2013). Acta Cryst. E69, o388.  [CrossRef] [details]
Conti, P., Dallanoce, C., Amici, M. D., Micheli, C. D. & Klotz, K. N. (1998). Bioorg. Med. Chem. 6, 401-408.  [CrossRef] [ChemPort] [PubMed]
Kang, Y. Y., Shin, K. L., Yoo, K. H., Seo, K. J., Hong, C. Y., Lee, C. S., Park, S. Y., Kim, D. J. & Park, S. W. (2000). Bioorg. Med. Chem. Lett. 10, 95-99.  [CrossRef] [PubMed] [ChemPort]
Lee, Y., Park, S. M. & Kim, B. H. (2009). Bioorg. Med. Chem. Lett. 19, 1126-1128.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shin, K. D., Lee, M. Y., Shin, D. S., Lee, S., Son, K. H., Koh, S., Paik, Y. K., Kwon, B. M. & Han, D. C. (2005). J. Biol. Chem. 280, 41439-41448.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Stevens, R. V. & Albizati, K. F. (1984). Tetrahedron Lett. 25, 4587-4591.  [CrossRef] [ChemPort] [ISI]
Wolf, R., Wong, M. W., Kennard, C. H. L. & Wentrup, C. (1995). J. Am. Chem. Soc. 117, 6789-6790.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o897  [ doi:10.1107/S1600536813011410 ]

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