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Volume 69 
Part 5 
Page o733  
May 2013  

Received 30 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.126
Data-to-parameter ratio = 13.9
Details
Open access

Isopropyl 3-phenylisoxazole-5-carboxylate

aDepartment of Chemistry, School of Preclinical Medicine, Shanxi Medical University, 56 Xinjian South Road, 030001 Tai Yuan, People's Republic of China,bAffiliated Hospital of Xi'an Medical College, 48 Fenggao West Road, 710077 Xi-An, People's Republic of China, and cDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
Correspondence e-mail: syzhang@fmmu.edu.cn

In the title compound, C13H13NO3, the isoxazole ring is approximately coplanar with the phenyl ring, the dihedral angle between their planes being 7.37 (19)°. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of C-H...O hydrogen bonds, generating a ring of graph-set motif R22(10).

Related literature

For the biological activity of isoxazole derivatives, see: Angibaud et al. (2003[Angibaud, P., Bourdrez, X., Devine, A., End, D. W., Freyne, E., Ligny, Y., Muller, P., Mannens, G., Pilatte, I., Poncelet, V., Skrzat, S., Smets, G., Van Dun, J., Van Remoortere, P., Venet, M. & Wouters, W. (2003). Bioorg. Med. Chem. Lett. 13, 1543-1548.]). For the structure of a related compound, see: Yao & Deng (2008[Yao, Z. & Deng, J.-C. (2008). Acta Cryst. E64, o131.]). For the synthesis of 3-phenylisoxazole-5-carboxylic acid, see: Liu et al. (2006[Liu, L.-J., Yong, J.-P., Dai, X.-J., Jia, J., Wang, X.-Z. & Wang, J.-W. (2006). Chem. J. Chin. Univ. 27, 1669-1672.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO3

  • Mr = 231.24

  • Monoclinic, P 21 /n

  • a = 4.6311 (10) Å

  • b = 16.596 (4) Å

  • c = 15.897 (3) Å

  • [beta] = 98.321 (4)°

  • V = 1208.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.36 × 0.28 × 0.17 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.984

  • 6039 measured reflections

  • 2169 independent reflections

  • 1511 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.126

  • S = 1.03

  • 2169 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O2i 0.93 2.37 3.277 (2) 166
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5055 ).


Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (21172262).

References

Angibaud, P., Bourdrez, X., Devine, A., End, D. W., Freyne, E., Ligny, Y., Muller, P., Mannens, G., Pilatte, I., Poncelet, V., Skrzat, S., Smets, G., Van Dun, J., Van Remoortere, P., Venet, M. & Wouters, W. (2003). Bioorg. Med. Chem. Lett. 13, 1543-1548.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Liu, L.-J., Yong, J.-P., Dai, X.-J., Jia, J., Wang, X.-Z. & Wang, J.-W. (2006). Chem. J. Chin. Univ. 27, 1669-1672.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yao, Z. & Deng, J.-C. (2008). Acta Cryst. E64, o131.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o733  [ doi:10.1107/S1600536813009392 ]

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