3-(4-Meth­oxy­phen­yl)-5-methylisoxazole-4-carb­oxy­lic acid

Chandra; Raghu, K.; Srikantamurthy, N.; Umesha, K.B.; Palani, K.; Mahendra, M.

doi:10.1107/S1600536813004029

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.125
Data-to-parameter ratio = 18.0
Details

3-(4-Methoxyphenyl)-5-methylisoxazole-4-carboxylic acid

Chandra,^a K. Raghu,^b N. Srikantamurthy,^b K. B. Umesha,^b K. Palani ^c and M. Mahendra ^a ^*

^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-HO hydrogen bonds generate R₂²(8) loops.

Related literature

For the biological and pharmaceutical properties of isoxazoles, see: Changtam et al. (2010); Eddington et al. (2002); Kozikowski et al. (2008); Lee et al. (2009); Panda et al. (2009); Shin et al. (2005). For the agrochemical importance of isoxazoles, see: Pinho e Melo (20057). For a related structure, see: Wolf et al. (1995).

Experimental

Crystal data

C₁₂H₁₁NO₄
M_r = 233.22
Monoclinic, P 2₁ /c
a = 6.4147 (2) Å
b = 14.6321 (6) Å
c = 11.9911 (5) Å
= 97.220 (2)°
V = 1116.57 (7) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.979, T_max = 0.989
11200 measured reflections
2811 independent reflections
2083 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.125
S = 1.04
2811 reflections
156 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O17-H17O16ⁱ	0.82	1.79	2.6034 (16)	173
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
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, A. P., Tapadar, S., Luchini, D. N., Kim, K. H. & Billadeau, D. D. (2008). J. Med. Chem. 51, 4370-4373.
Lee, Y., Park, S. M. & Kim, B. H. (2009). Bioorg. Med. Chem. Lett. 19, 1126-1128.
Panda, S. S., Chowdary, P. V. R. & Jayashree, B. S. (2009). Indian J. Pharm. Sci. 71, 684-687.
Pinho e Melo, T. M. V. D. (2005). Curr. Org. Chem. 9, 925-958.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wolf, R., Wong, M. W., Kennard, C. H. L. & Wentrup, C. (1995). J. Am. Chem. Soc. 117, 6789-6790.

organic compounds