(Z)-4-Benzyl­idene-3-methyl­isoxazol-5(4H)-one

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

doi:10.1107/S1600536812041311

Volume 68
Part 11
Page o3091
November 2012

Received 30 September 2012
Accepted 2 October 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 12.6
Details

(Z)-4-Benzylidene-3-methylisoxazol-5(4H)-one

Chandra,^a N. Srikantamurthy,^b S. Jeyaseelan,^c K. B. Umesha,^b K. Palani ^d 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,^cDepartment of Physics, St Philomena's College, Mysore, India, and ^dSER-CAT, APS, Argonne National Laboratory, Argonne, IL-60439, USA
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

In the title compound C₁₁H₉NO₂, the phenyl and isoxazole rings are almost coplanar, making a dihedral angle of 1.14 (9)°. This planarity is also assisted by an intramolecular C-HO hydrogen bond between the phenyl ring and the carbonyl O atom. In the crystal, weak C-HO interactions generate a layered structure parallel to the ac plane.

Related literature

For the biological and therapeutic importance of isoxazoles, see: Kang et al. (2000); Conti et al. (1998); Changtam et al. (2010); Kwon et al., (1995); Abbiati et al. (2003). For bond-length and angle data in a related structure, see: Wolf et al. (1995).

Experimental

Crystal data

C₁₁H₉NO₂
M_r = 187.19
Monoclinic, P 2₁ /n
a = 12.144 (4) Å
b = 6.734 (2) Å
c = 12.333 (4) Å
= 114.589 (5)°
V = 917.1 (5) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
6722 measured reflections
1610 independent reflections
1352 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.111
S = 1.07
1610 reflections
128 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10O1	0.93	2.21	3.042 (2)	149
C7-H7CO6ⁱ	0.96	2.61	3.297 (2)	129
C8-H8O1ⁱ	0.93	2.72	3.574 (2)	154
C14-H14O1ⁱ	0.93	2.68	3.526 (2)	151
Symmetry code: (i) x, 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: SJ5268 ).

Acknowledgements

MM would like to thank the University of Mysore for the award of project DV3/136/2007-2008/24.09.09.

References

Abbiati, G., Beccalli, E. M., Broggini, G. & Zoni, C. (2003). Tetrahedron, 59, 9887-9893.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Changtam, C., Hongmanee, P. & Suksamrarn, A. (2010). Eur. J. Med. Chem. 45, 4446-4457.
Conti, P., Dallanoce, C., Amici, M. D., Micheli, C. D. & Klotz, K. N. (1998). Bioorg. Med. Chem. 6, 401-408.
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.
Kwon, T., Heimann, A. S., Oriaku, E. T., Yoon, K. & Lee, H. J. (1995). J. Med. Chem. 38, 1048-1051.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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