[Journal logo]

Volume 69 
Part 10 
Pages o1504-o1505  
October 2013  

Received 15 August 2013
Accepted 23 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.005 Å
R = 0.072
wR = 0.162
Data-to-parameter ratio = 11.7
Details
Open access

(2R*,4R*,7S*,10R*,12R*)-3,11,13,15-Tetraoxapentacyclo[5.5.3.01,7.02,4.010,12]pentadeca-5,8-dien-14-one

aSchool of Chemistry, University of Hyderabad, Hyderabad 500 046, India
Correspondence e-mail: gmsc@uohyd.ernet.in

The title compound, C11H8O5, features a `skipped' diene, an anti-bis(epoxide) and a cyclic carbonate, all embedded in a densely functionalized [4.4.3]propellane scaffold. The crystal packing of this diepoxide is effected primarily by C-H...O hydrogen bonds, which link the molecules into tapes along the b axis. Inter-tape connectivity is brought about by centrosymmetrically disposed pairs of C...O contacts [3.183 (4) Å] between the C[delta]+=O[delta]- dipoles of neighbouring carbonate moieties.

Related literature

For our report on the crystal structure of (1s,6s)-11,13-dioxatricyclo[4.4.3.01,6]trideca-2,4,7,9-tetraen-12-one, the synthetic precursor of the title compound, see: Mehta & Sen (2011[Mehta, G. & Sen, S. (2011). Cryst. Growth Des. 11, 3721-3724.]). For salient references related to the chemistry of molecules, featuring two abutting 1,3-cyclohexadiene (CHD) units embedded in a rigid 11,13-dioxa[4.4.3]propellane framework, see: Ashkenazi et al. (1978[Ashkenazi, P., Kalo, J., Rüttimann, A. & Ginsburg, D. (1978). Tetrahedron, 34, 2161-2165.]); Paquette et al. (1990[Paquette, L. A., Liang, S., Waykole, L., DeLucca, G., Jendralla, H., Rogers, R. D., Kratz, D. & Gleiter, R. (1990). J. Org. Chem. 55, 1598-1611.]). For references representing our own previous studies on the modes of self-assembly in oxygenated CHDs, see: Mehta & Sen (2010[Mehta, G. & Sen, S. (2010). Tetrahedron Lett. 51, 503-507.]) and citations therein. For a reference related to VEGA ZZ 3.0.0 the program used to generate the MEP surface diagram of the title compound, see: Pedretti et al. (2004[Pedretti, A., Villa, L. & Vistoli, G. (2004). J. Comput. Aided Mol. Des. 18, 167-173.]). For a discussion on graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). For a discussion on ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For details of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Bruno et al. (2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8O5

  • Mr = 220.17

  • Monoclinic, P 21 /c

  • a = 7.170 (3) Å

  • b = 7.809 (3) Å

  • c = 16.357 (6) Å

  • [beta] = 93.301 (6)°

  • V = 914.3 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 291 K

  • 0.23 × 0.17 × 0.13 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.971, Tmax = 0.984

  • 6504 measured reflections

  • 1691 independent reflections

  • 1319 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.162

  • S = 1.18

  • 1691 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O4i 0.98 2.53 3.509 (5) 174
C3-H3...O5ii 0.98 2.55 3.313 (4) 134
C10-H10...O5i 0.98 2.49 3.379 (4) 151
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc. Madison. Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc. Madison. Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and CAMERON (Watkin et al., 1993[Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); 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: IS5298 ).


Acknowledgements

GM wishes to thank the Government of India for the award of National Research Professorship. SS and CSA thank the University Grants Commission, India, for the award of Dr D. S. Kothari postdoctoral fellowships. GM acknowledges the research support from Eli Lilly and Jubilant-Bhartia Foundations, and the facilities extended by the University of Hyderabad.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Ashkenazi, P., Kalo, J., Rüttimann, A. & Ginsburg, D. (1978). Tetrahedron, 34, 2161-2165.  [CrossRef] [ChemPort] [Web of Science]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (1998). SMART and SAINT. Bruker AXS Inc. Madison. Wisconsin, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.  [Web of Science] [CrossRef] [IUCr Journals]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Mehta, G. & Sen, S. (2010). Tetrahedron Lett. 51, 503-507.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Mehta, G. & Sen, S. (2011). Cryst. Growth Des. 11, 3721-3724.  [CSD] [CrossRef] [ChemPort]
Paquette, L. A., Liang, S., Waykole, L., DeLucca, G., Jendralla, H., Rogers, R. D., Kratz, D. & Gleiter, R. (1990). J. Org. Chem. 55, 1598-1611.  [CSD] [CrossRef] [ChemPort]
Pedretti, A., Villa, L. & Vistoli, G. (2004). J. Comput. Aided Mol. Des. 18, 167-173.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.


Acta Cryst (2013). E69, o1504-o1505   [ doi:10.1107/S1600536813023817 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.