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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 [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.111
Data-to-parameter ratio = 12.6
Details
Open access

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

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-H...O hydrogen bond between the phenyl ring and the carbonyl O atom. In the crystal, weak C-H...O 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[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.]); Conti et al. (1998[Conti, P., Dallanoce, C., Amici, M. D., Micheli, C. D. & Klotz, K. N. (1998). Bioorg. Med. Chem. 6, 401-408.]); Changtam et al. (2010[Changtam, C., Hongmanee, P. & Suksamrarn, A. (2010). Eur. J. Med. Chem. 45, 4446-4457.]); Kwon et al., (1995[Kwon, T., Heimann, A. S., Oriaku, E. T., Yoon, K. & Lee, H. J. (1995). J. Med. Chem. 38, 1048-1051.]); Abbiati et al. (2003[Abbiati, G., Beccalli, E. M., Broggini, G. & Zoni, C. (2003). Tetrahedron, 59, 9887-9893.]). For bond-length and angle data in 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
  • C11H9NO2

  • Mr = 187.19

  • Monoclinic, P 21 /n

  • a = 12.144 (4) Å

  • b = 6.734 (2) Å

  • c = 12.333 (4) Å

  • [beta] = 114.589 (5)°

  • V = 917.1 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.111

  • S = 1.07

  • 1610 reflections

  • 128 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
C10-H10...O1 0.93 2.21 3.042 (2) 149
C7-H7C...O6i 0.96 2.61 3.297 (2) 129
C8-H8...O1i 0.93 2.72 3.574 (2) 154
C14-H14...O1i 0.93 2.68 3.526 (2) 151
Symmetry code: (i) x, y+1, z.

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: 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.  [ISI] [CrossRef] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]
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]
Kwon, T., Heimann, A. S., Oriaku, E. T., Yoon, K. & Lee, H. J. (1995). J. Med. Chem. 38, 1048-1051.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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 (2012). E68, o3091  [ doi:10.1107/S1600536812041311 ]

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