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Volume 69 
Part 7 
Page o1168  
July 2013  

Received 19 April 2013
Accepted 21 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.141
Data-to-parameter ratio = 11.3
Details
Open access

2,6-Dimethyl-4-oxo-3-oxatricyclo[5.2.1.02,6]decane-1-carboxamide

aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01033 Kyiv, Ukraine
Correspondence e-mail: 417lab@gmail.com

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-H...O-C and N-H...O=C hydrogen bonds are formed between the amide group and the two O-atom acceptors of the lactone group, forming a chain along [001].

Related literature

For applications of nitroimines and their derivatives in organic synthesis, see: Squire et al. (2002[Squire, M. D., Burwell, A., Ferrence, G. M. & Hitchcock, S. R. (2002). Tetrahedron Asymmetry, 17, 1849-1854.]); Bulman Page et al. (2000[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.]); Lalk et al. (1999[Lalk, M., Peseke, K. & Reinke, H. (1999). J. Prakt. Chem. 341, 552-556.]), as organocatalysts, see: Parrott, et al. (2008[Parrott, R. W. & Hitchcock, S. R. II (2008). Tetrahedron Asymmetry, 19, 19-26.]) and in medicinal chemistry, see: Ranise et al. (1990[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.]); Bondavalli et al. (1987[Bondavalli, F., Bruno, O., Ranise, A., Schenone, P., Susanna, V., Lisa, M., Maione, S. & Marmo, E. (1987). Il Farmaco, 42, 947-953.]). For bond angles in related structures, see: Noe et al. (1996[Noe, C. R., Knollmuller, M., Gartner, P., Mereiter, K. & Steinbauer, G. (1996). Liebigs Ann. pp. 1015-1021.]); Knollmuller et al. (1998[Knollmuller, M., Gartner, P., Ferencic, M., Noe, C. R. & Mereiter, K. (1998). Eur. J. Org. Chem. pp. 2507-2511.]).

[Scheme 1]

Experimental

Crystal data
  • C12H17NO3

  • Mr = 223.27

  • Triclinic, [P \overline 1]

  • a = 7.0659 (3) Å

  • b = 7.8206 (3) Å

  • c = 10.4595 (3) Å

  • [alpha] = 79.667 (2)°

  • [beta] = 80.471 (2)°

  • [gamma] = 81.579 (2)°

  • V = 556.69 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.25 × 0.2 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.986

  • 8729 measured reflections

  • 2405 independent reflections

  • 1754 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.141

  • S = 0.92

  • 2405 reflections

  • 213 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H10...O3i 0.91 (2) 2.17 (2) 3.065 (2) 168.7 (18)
N1-H11...O2ii 0.89 (2) 2.02 (3) 2.912 (2) 177 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2095 ).


References

Bondavalli, F., Bruno, O., Ranise, A., Schenone, P., Susanna, V., Lisa, M., Maione, S. & Marmo, E. (1987). Il Farmaco, 42, 947-953.  [ChemPort]
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.  [PubMed]
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.  [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
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.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Squire, M. D., Burwell, A., Ferrence, G. M. & Hitchcock, S. R. (2002). Tetrahedron Asymmetry, 17, 1849-1854.  [CrossRef]


Acta Cryst (2013). E69, o1168  [ doi:10.1107/S1600536813017248 ]

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