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Volume 68 
Part 12 
Page o3496  
December 2012  

Received 6 November 2012
Accepted 26 November 2012
Online 30 November 2012

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.143
Data-to-parameter ratio = 13.0
Details
Open access

(3aRS,7aSR)-7a-Methoxy-2-oxo-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4,4-dicarbonitrile

María González,a* Andrea Martínez,a Marcos L. Rivadullaa and Berta Covelob

aDpto. Química Orgánica, Facultade de Química, Universidade de Vigo, E-36310 Vigo, Spain, and bUnidad de Difracción de Raios X de Monocristal, Servicio Determinación Estructural, Proteómica e Xenómica, CACTI-Universidade de Vigo, E-36310 Vigo, Spain
Correspondence e-mail: magonpe@uvigo.es

The racemic title compound, C11H12N2O3, contains a [4.3.0]bicyclic unit in which the shared C-C bond adopts a cis configuration. The five- and six-membered rings are in twisted envelope (with the bridgehead C atom bearing the methoxy substituent as the flap) and distorted chair conformations, respectively. In the crystal, the molecules are linked via weak C-H...O iteractions, forming ladder-like chains along [010].

Related literature

For related syntheses of natural products, see: Jones & Goodbrand (1977[Jones, J. B. & Goodbrand, H. B. (1977). Can. J. Chem. 55, 2685-2691.]). For details of a synthesis using different starting materials, see: Alonso et al. (2005[Alonso, D., Pérez, M., Gómez, G., Covelo, B. & Fall, Y. (2005). Tetrahedron, 61, 2021-2026.]); Pérez et al. (2004[Pérez, M., Canoa, P., Gómez, G., Terán, C. & Fall, Y. (2004). Tetrahedron Lett. 45, 5207-5209.], 2005[Pérez, M., Canoa, P., Gómez, G., Teijeira, M. & Fall, Y. (2005). Synthesis, pp. 411-414.]). For a related structure, see: Grudniewska et al. (2011[Grudniewska, A., Dancewicz, K., Bialonska, A., Ciunik, Z., Gabrýs, B. & Wawrzenczyk, C. (2011). Advances, 1, 498-510.]). For puckering parameters, see, Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C11H12N2O3

  • Mr = 220.23

  • Monoclinic, P 21 /n

  • a = 11.816 (3) Å

  • b = 7.228 (2) Å

  • c = 13.017 (4) Å

  • [beta] = 104.250 (5)°

  • V = 1077.6 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.49 × 0.24 × 0.19 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.697, Tmax = 0.745

  • 5473 measured reflections

  • 1893 independent reflections

  • 1244 reflections with I > 2[sigma](I)

  • Rint = 0.030
Refinement

  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.143

  • S = 1.03

  • 1893 reflections

  • 146 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...O3i 0.97 2.59 3.290 (3) 129
C8-H8C...O2ii 0.96 2.46 3.219 (4) 136
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, 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: PLATON (Spek, 2011)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.] and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2158 ).

Acknowledgements

This work was supported financially by the Spanish Ministry of Foreign Affairs and Cooperation (PCIA/030052/10) and the Xunta de Galicia (INCITE845B-2010/020, INCITE08PXIB314255PR).

References

Alonso, D., Pérez, M., Gómez, G., Covelo, B. & Fall, Y. (2005). Tetrahedron, 61, 2021-2026.  [CrossRef] [ChemPort]
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Grudniewska, A., Dancewicz, K., Bialonska, A., Ciunik, Z., Gabrýs, B. & Wawrzenczyk, C. (2011). Advances, 1, 498-510.  [ChemPort]
Jones, J. B. & Goodbrand, H. B. (1977). Can. J. Chem. 55, 2685-2691.  [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Pérez, M., Canoa, P., Gómez, G., Teijeira, M. & Fall, Y. (2005). Synthesis, pp. 411-414.
Pérez, M., Canoa, P., Gómez, G., Terán, C. & Fall, Y. (2004). Tetrahedron Lett. 45, 5207-5209.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2012). E68, o3496  [ doi:10.1107/S1600536812048519 ]

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