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Volume 69 
Part 4 
Page o500  
April 2013  

Received 30 January 2013
Accepted 24 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.038
wR = 0.112
Data-to-parameter ratio = 12.5
Details
Open access

Diethyl 1,8-bis(4-methylphenyl)-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 and Technology, Kancheepuram 631 502, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cPostgraduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India
Correspondence e-mail: seshadri_pr@yahoo.com

The title compound, C30H30O5, is the Diels-Alder adduct from 1,3-diphenylbenzo[c]furan and diethyl maleate. The molecule comprises 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 the 4-methylphenyl substituents in the 1- and 8-positions is 62.1 (1)°. The ethyl group of one ester group and the ethoxy group of the other ester group are disordered over two sets of sites, with occupancy ratios of 0.43 (2):0.57 (2) and 0.804 (7):0.196 (7), respectively. In the crystal, inversion dimers are formed through pairs of C-H...O interactions.

Related literature

For background to Diels-Alder reactions, see: Akio & Toshiki (2010[Akio, K. & Toshiki, N. (2010). J. Org. Chem. 75, 3133-3136.]). For related structures, see: 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.]); Takahashi et al. (2003[Takahashi, I., Tsuzuki, M., Kitajima, H., Hetanaka, M., Maeda, S., Yamano, A., Ohta, T. & Hosoi, S. (2003). Anal. Sci. 19, 973-974.]); Simpson et al. (2004[Simpson, M., Storey, J. M. D. & Harrison, W. T. A. (2004). Acta Cryst. E60, o1081-o1083.]); Toze et al. (2010[Toze, F. A. A., Ershova, J. D., Obushak, M. D., Zubkov, F. I. & Khrustalev, V. N. (2010). Acta Cryst. E66, o1388-o1389.]). 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
  • C30H30O5

  • Mr = 470.54

  • Triclinic, [P \overline 1]

  • a = 9.8722 (3) Å

  • b = 10.7413 (3) Å

  • c = 13.3081 (3) Å

  • [alpha] = 109.319 (1)°

  • [beta] = 105.045 (1)°

  • [gamma] = 90.374 (1)°

  • V = 1279.45 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 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 = 0.951, Tmax = 0.953

  • 21475 measured reflections

  • 4505 independent reflections

  • 3754 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.112

  • S = 1.03

  • 4505 reflections

  • 360 parameters

  • 84 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, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O4i 0.93 2.66 3.558 (2) 164
C11-H11...O2ii 0.93 2.66 3.433 (2) 141
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. 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: 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: SHELXL97, 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: IM2419 ).


Acknowledgements

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

References

Akio, K. & Toshiki, N. (2010). J. Org. Chem. 75, 3133-3136.  [PubMed]
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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Simpson, M., Storey, J. M. D. & Harrison, W. T. A. (2004). Acta Cryst. E60, o1081-o1083.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Takahashi, I., Tsuzuki, M., Kitajima, H., Hetanaka, M., Maeda, S., Yamano, A., Ohta, T. & Hosoi, S. (2003). Anal. Sci. 19, 973-974.  [CSD] [CrossRef] [PubMed] [ChemPort]
Toze, F. A. A., Ershova, J. D., Obushak, M. D., Zubkov, F. I. & Khrustalev, V. N. (2010). Acta Cryst. E66, o1388-o1389.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o500  [ doi:10.1107/S1600536813005291 ]

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