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Volume 69 
Part 3 
Page o323  
March 2013  

Received 10 December 2012
Accepted 28 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.041
wR = 0.110
Data-to-parameter ratio = 12.8
Details
Open access

Diethyl 1,8-diphenyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6-triene-9,10-dicarboxylate

aDepartment of Physics, P. T. Lee Chengalvaraya Naicker College of Engineering & Technology, Kancheepuram 631 502, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cPostGraduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India
Correspondence e-mail: seshadri_pr@yahoo.com

The title compound, C28H26O5, is the Diels-Alder adduct from 1,3-diphenylbenzo[c]furan and diethyl maleate. The molecule comprises of a fused tricyclic system containing two five-membered rings, which are in envelope conformations with the O atom at the flap, and a six-membered ring adopting a boat conformation. The dihedral angle between phenyl substituents in the 1,8-positions is 55.1 (1)°. The ethyl groups are disordered over two sets of sites, with occupancy ratios of 0.648 (9):0.352 (9) and 0.816 (1):0.184 (1). In the crystal, pairs of C-H...[pi] interactions link the molecules into inversion dimers.

Related literature

For background to Diels-Alder reactions, see: Stevens & Richards (1997[Stevens, A. M. & Richards, C. J. (1997). Tetrahedron Lett. 38, 7805-7808.]). For related structures, see: Doboszewski et al. (2010[Doboszewski, B., Silva, P. R. da, Nazarenko, A. Y. & Nemykin, V. N. (2010). Acta Cryst. E66, o3217-o3218.]); Toze et al. (2011[Toze, F. A. A., Airiyan, I. K., Nikitina, E. V., Sorokina, E. A. & Khrustalev, V. N. (2011). Acta Cryst. E67, o2852-o2853.]); Bailey et al. (1995[Bailey, J. H., Coulter, C. V., Pratt, A. J. & Robinson, W. T. (1995). J. Chem. Soc. Perkin Trans. 1, pp. 589-592.]); Ohwada et al. (2001[Ohwada, T., Miura, M., Tanaka, H., Sakamoto, S., Yamaguchi, K., Ikeda, H. & Inagaki, S. (2001). J. Am. Chem. Soc. 123, 10164-10172.]); Takahashi et al. (2003[Takahashi, I., Tsuzuki, M., Kitajima, H., Hetanaka, M., Maeda, S., Yamano, A., Ohta, T. & Hosoi, S. (2003). Anal. Sci. 19, 973-.]). For puckering and asymmetry parameters, see: Cremer & Pople(1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C28H26O5

  • Mr = 442.49

  • Triclinic, [P \overline 1]

  • a = 9.7126 (3) Å

  • b = 11.5930 (3) Å

  • c = 12.5989 (5) Å

  • [alpha] = 115.013 (2)°

  • [beta] = 107.126 (2)°

  • [gamma] = 97.431 (1)°

  • V = 1174.60 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.991

  • 20057 measured reflections

  • 4124 independent reflections

  • 3271 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.110

  • S = 1.06

  • 4124 reflections

  • 323 parameters

  • 40 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7and C9-C14 rings respectively.

D-H...A D-H H...A D...A D-H...A
C28-H28B...Cg1i 0.98 3.00 3.601 (7) 121
C5-H5...Cg2ii 0.93 2.89 3.693 (3) 145
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2416 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bailey, J. H., Coulter, C. V., Pratt, A. J. & Robinson, W. T. (1995). J. Chem. Soc. Perkin Trans. 1, pp. 589-592.  [CrossRef]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Doboszewski, B., Silva, P. R. da, Nazarenko, A. Y. & Nemykin, V. N. (2010). Acta Cryst. E66, o3217-o3218.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Ohwada, T., Miura, M., Tanaka, H., Sakamoto, S., Yamaguchi, K., Ikeda, H. & Inagaki, S. (2001). J. Am. Chem. Soc. 123, 10164-10172.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stevens, A. M. & Richards, C. J. (1997). Tetrahedron Lett. 38, 7805-7808.  [CrossRef] [ChemPort] [ISI]
Takahashi, I., Tsuzuki, M., Kitajima, H., Hetanaka, M., Maeda, S., Yamano, A., Ohta, T. & Hosoi, S. (2003). Anal. Sci. 19, 973-.  [CSD] [CrossRef] [PubMed] [ChemPort]
Toze, F. A. A., Airiyan, I. K., Nikitina, E. V., Sorokina, E. A. & Khrustalev, V. N. (2011). Acta Cryst. E67, o2852-o2853.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o323  [ doi:10.1107/S1600536813002791 ]

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