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Volume 69 
Part 3 
Page o388  
March 2013  

Received 6 February 2013
Accepted 9 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.125
Data-to-parameter ratio = 18.0
Details
Open access

3-(4-Methoxyphenyl)-5-methylisoxazole-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 cSER-CAT, APS, Argonne National Laboratory, Argonne, IL 60439, USA
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

In the title compound, C12H11NO4, the dihedral angle between the benzene and isoxazole rings is 42.52 (8)°. The carboxylic acid group is close to being coplanar with the isoxazole ring [dihedral angle = 5.3 (2)°]. In the crystal, inversion dimers linked by pairs of O-H...O hydrogen bonds generate R22(8) loops.

Related literature

For the biological and pharmaceutical properties of isoxazoles, see: Changtam et al. (2010[Changtam, C., Hongmanee, P. & Suksamrarn, A. (2010). Eur. J. Med. Chem. 45, 4446-4457.]); Eddington et al. (2002[Eddington, N. D., Cox, D. S., Roberts, R. R., Butcher, R. J., Edafiogho, I. O., Stables, J. P., Cooke, N., Goodwin, A. M., Smith, C. A. & Scott, K. R. (2002). Eur. J. Med. Chem. 37, 635-648.]); Kozikowski et al. (2008[Kozikowski, A. P., Tapadar, S., Luchini, D. N., Kim, K. H. & Billadeau, D. D. (2008). J. Med. Chem. 51, 4370-4373.]); Lee et al. (2009[Lee, Y., Park, S. M. & Kim, B. H. (2009). Bioorg. Med. Chem. Lett. 19, 1126-1128.]); Panda et al. (2009[Panda, S. S., Chowdary, P. V. R. & Jayashree, B. S. (2009). Indian J. Pharm. Sci. 71, 684-687.]); 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.]). For the agrochemical importance of isoxazoles, see: Pinho e Melo (2005[Pinho e Melo, T. M. V. D. (2005). Curr. Org. Chem. 9, 925-958.]7). For a related structure, see: Wolf et al. (1995[Wolf, R., Wong, M. W., Kennard, C. H. L. & Wentrup, C. (1995). J. Am. Chem. Soc. 117, 6789-6790.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11NO4

  • Mr = 233.22

  • Monoclinic, P 21 /c

  • a = 6.4147 (2) Å

  • b = 14.6321 (6) Å

  • c = 11.9911 (5) Å

  • [beta] = 97.220 (2)°

  • V = 1116.57 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.989

  • 11200 measured reflections

  • 2811 independent reflections

  • 2083 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.125

  • S = 1.04

  • 2811 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O17-H17...O16i 0.82 1.79 2.6034 (16) 173
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: HB7037 ).


Acknowledgements

C thanks the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009-2010/10.07.2012.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Changtam, C., Hongmanee, P. & Suksamrarn, A. (2010). Eur. J. Med. Chem. 45, 4446-4457.  [ISI] [CrossRef] [ChemPort] [PubMed]
Eddington, N. D., Cox, D. S., Roberts, R. R., Butcher, R. J., Edafiogho, I. O., Stables, J. P., Cooke, N., Goodwin, A. M., Smith, C. A. & Scott, K. R. (2002). Eur. J. Med. Chem. 37, 635-648.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Kozikowski, A. P., Tapadar, S., Luchini, D. N., Kim, K. H. & Billadeau, D. D. (2008). J. Med. Chem. 51, 4370-4373.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, Y., Park, S. M. & Kim, B. H. (2009). Bioorg. Med. Chem. Lett. 19, 1126-1128.  [CrossRef] [PubMed] [ChemPort]
Panda, S. S., Chowdary, P. V. R. & Jayashree, B. S. (2009). Indian J. Pharm. Sci. 71, 684-687.  [CrossRef] [ChemPort] [PubMed]
Pinho e Melo, T. M. V. D. (2005). Curr. Org. Chem. 9, 925-958.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [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] [details]
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, o388  [ doi:10.1107/S1600536813004029 ]

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