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Volume 69 
Part 6 
Page o853  
June 2013  

Received 22 April 2013
Accepted 3 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.051
wR = 0.152
Data-to-parameter ratio = 13.1
Details
Open access

5-Methyl-N-(1,3-thiazol-2-yl)isoxazole-4-carboxamide

aState Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: dcwang@njut.edu.cn

In the title compound, C8H7N3O2S, the dihedral angle between the thiazol and isoxazole rings is 34.08 (13)°. In the crystal, the molecules are linked by pairs of N-H...N hydrogen bonds, forming inversion dimers, and C-H...O interactions, resulting in chains along the b-axis direction.

Related literature

For background to isoxazole-containing drugs, see: Shaw et al. (2011[Shaw, J. J., Chen, B., Wooley, P., Palfey, B., Lee, A. R., Huang, W. H. & Zeng, D. (2011). Am. J. Biomed. Sci. 3, 218-227.]); Schattenkirchner (2000[Schattenkirchner, M. (2000). Immunopharmacology, 47, 291-298.]); Huang et al. (2003[Huang, W. H., Yang, C. L., Lee, A. R. & Chiu, H. F. (2003). Chem. Pharm. Bull. 51, 313-314.]). For the crystal structure of a related compound, see: Wang et al. (2011[Wang, D.-C., Huang, L.-C., Liu, H.-Q., Peng, Y.-R. & Song, J.-S. (2011). Acta Cryst. E67, o3207.]).

[Scheme 1]

Experimental

Crystal data
  • C8H7N3O2S

  • Mr = 209.23

  • Monoclinic, P 21 /c

  • a = 8.8460 (18) Å

  • b = 10.742 (2) Å

  • c = 10.024 (2) Å

  • [beta] = 107.27 (3)°

  • V = 909.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.907, Tmax = 0.968

  • 3462 measured reflections

  • 1676 independent reflections

  • 1298 reflections with I > 2[sigma](I)

  • Rint = 0.060

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.152

  • S = 1.00

  • 1676 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...N1i 0.86 2.14 2.970 (3) 162
C6-H6A...O1ii 0.93 2.36 3.287 (4) 171
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius,1994)[Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]; cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2631 ).


References

Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Huang, W. H., Yang, C. L., Lee, A. R. & Chiu, H. F. (2003). Chem. Pharm. Bull. 51, 313-314.  [CrossRef] [PubMed] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Schattenkirchner, M. (2000). Immunopharmacology, 47, 291-298.  [ISI] [CrossRef] [PubMed] [ChemPort]
Shaw, J. J., Chen, B., Wooley, P., Palfey, B., Lee, A. R., Huang, W. H. & Zeng, D. (2011). Am. J. Biomed. Sci. 3, 218-227.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, D.-C., Huang, L.-C., Liu, H.-Q., Peng, Y.-R. & Song, J.-S. (2011). Acta Cryst. E67, o3207.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o853  [ doi:10.1107/S1600536813012105 ]

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