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Volume 68 
Part 5 
Page o1537  
May 2012  

Received 7 April 2012
Accepted 20 April 2012
Online 25 April 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.097
Data-to-parameter ratio = 14.3
Details
Open access

Methyl 5-hydroxy-3-phenyl-1,2-oxazolidine-5-carboxylate

aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: yejia407169849@163.com

In the title compound, C11H13NO4, the isoxazolidine ring has an envelope conformation with the O atom as the flap. In the crystal, molecules are liked via N-H...O and bifurcated O-H...(O,N) hydrogen bonds forming chains propagating along [010]. There are also C-H...O interactions present.

Related literature

For the use of isoxazolidine-containing compounds as building blocks in synthesis, see: Carrillo et al. (2006[Carrillo, N., Davalos, E. A., Russak, J. A. & Bode, J. W. (2006). J. Am. Chem. Soc. 128, 1452-1453.]); Lv et al. (2010[Lv, J., Li, X., Zhong, L., Luo, S. & Cheng, J. P. (2010). Org. Lett. 12, 1096-1099.]); Ibrahem et al. (2007[Ibrahem, I., Rios, R., Vesely, J., Zhao, G. L. & Cordova, A. (2007). Chem. Commun. 8, 849-851.]); Sharma et al. (1999[Sharma, G. V. M., Reddy, I. S., Reddy, V. G. & Rao, A. V. R. (1999). Tetrahedron Asymmetry, 10, 229-235.]). For information on conjugation additions to [alpha],[beta]-unsaturated ketones, see: Wu et al. (2006[Wu, Y. C., Liu, L., Li, H. J., Wang, D. & Chen, Y. J. (2006). J. Org. Chem. 71, 6592-6595.]). For standard bond-lengths see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13NO4

  • Mr = 223.22

  • Monoclinic, P 21 /n

  • a = 11.8322 (3) Å

  • b = 6.0853 (1) Å

  • c = 15.8570 (3) Å

  • [beta] = 101.864 (2)°

  • V = 1117.35 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.85 mm-1

  • T = 291 K

  • 0.40 × 0.36 × 0.30 mm

Data collection
  • Oxford Gemini S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.726, Tmax = 0.784

  • 10901 measured reflections

  • 2165 independent reflections

  • 1921 reflections with I > 2[sigma](I)

  • Rint = 0.034

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

  • wR(F2) = 0.097

  • S = 1.05

  • 2165 reflections

  • 151 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H4...O1i 0.907 (18) 2.315 (18) 3.1158 (15) 147.0 (13)
O2-H9...O1i 0.82 2.51 3.0673 (13) 127
O2-H9...N1i 0.82 1.99 2.7826 (16) 162
C11-H11A...O3ii 0.96 2.54 3.480 (2) 166
C11-H11C...O2iii 0.96 2.53 3.419 (2) 154
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x, y+1, z; (iii) -x+2, -y, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2406 ).


Acknowledgements

The authors thank the Testing Centre of Sichuan University for the diffraction measurements and China West Normal University for suport.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Carrillo, N., Davalos, E. A., Russak, J. A. & Bode, J. W. (2006). J. Am. Chem. Soc. 128, 1452-1453.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Ibrahem, I., Rios, R., Vesely, J., Zhao, G. L. & Cordova, A. (2007). Chem. Commun. 8, 849-851.  [CrossRef]
Lv, J., Li, X., Zhong, L., Luo, S. & Cheng, J. P. (2010). Org. Lett. 12, 1096-1099.  [ISI] [CrossRef] [ChemPort] [PubMed]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sharma, G. V. M., Reddy, I. S., Reddy, V. G. & Rao, A. V. R. (1999). Tetrahedron Asymmetry, 10, 229-235.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wu, Y. C., Liu, L., Li, H. J., Wang, D. & Chen, Y. J. (2006). J. Org. Chem. 71, 6592-6595.  [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o1537  [ doi:10.1107/S1600536812017576 ]

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