Received 19 April 2013
In the title compound, C12H17NO3, which was synthesized by Wagner-Meerwein rearrangement of the N-nitroimine, the ring-junction C-C bond length is comparatively long [1.573 (2) Å] due to a steric repulsion between the methyl groups at these atoms, which also leads to an increase in the C-C-C angles along this C4 chain [118.10 (13) and 115.04 (15) °, respectively]. In the crystal, N-HO-C and N-HO=C hydrogen bonds are formed between the amide group and the two O-atom acceptors of the lactone group, forming a chain along .
For applications of nitroimines and their derivatives in organic synthesis, see: Squire et al. (2002); Bulman Page et al. (2000); Lalk et al. (1999), as organocatalysts, see: Parrott, et al. (2008) and in medicinal chemistry, see: Ranise et al. (1990); Bondavalli et al. (1987). For bond angles in related structures, see: Noe et al. (1996); Knollmuller et al. (1998).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2095 ).
Bondavalli, F., Bruno, O., Ranise, A., Schenone, P., Susanna, V., Lisa, M., Maione, S. & Marmo, E. (1987). Il Farmaco, 42, 947-953.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bulman Page, P. C., Murrell, V. L., Limousin, C., Laffan, D. D. P., Bethell, D., Slawin, A. M. Z. & Smith, T. A. D. (2000). J. Org. Chem. 65, 4204-4207.
Knollmuller, M., Gartner, P., Ferencic, M., Noe, C. R. & Mereiter, K. (1998). Eur. J. Org. Chem. pp. 2507-2511.
Lalk, M., Peseke, K. & Reinke, H. (1999). J. Prakt. Chem. 341, 552-556.
Noe, C. R., Knollmuller, M., Gartner, P., Mereiter, K. & Steinbauer, G. (1996). Liebigs Ann. pp. 1015-1021.
Parrott, R. W. & Hitchcock, S. R. II (2008). Tetrahedron Asymmetry, 19, 19-26.
Ranise, A., Bondavalli, F., Bruno, O., Schenone, P., Faillace, G., Coluccino, A., Filippelli, W., Di Sarno, A. & Marmo, E. (1990). Il Farmaco, 45, 187-202.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Squire, M. D., Burwell, A., Ferrence, G. M. & Hitchcock, S. R. (2002). Tetrahedron Asymmetry, 17, 1849-1854.