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

Balakrishnan, B.; Nandakumar, M.; Seshadri, P.R.; Mohanakrishnan, A.K.

doi:10.1107/S1600536813002791

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.041
wR = 0.110
Data-to-parameter ratio = 12.8
Details

Diethyl 1,8-diphenyl-11-oxatricyclo[6.2.1.0^2,7]undeca-2,4,6-triene-9,10-dicarboxylate

B. Balakrishnan,^a Meganathan Nandakumar,^b P. R. Seshadri ^c ^* and Arasambattu K. Mohanakrishnan ^b

^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). For related structures, see: Doboszewski et al. (2010); Toze et al. (2011); Bailey et al. (1995); Ohwada et al. (2001); Takahashi et al. (2003). For puckering and asymmetry parameters, see: Cremer & Pople(1975); Nardelli (1983).

Experimental

Crystal data

C₂₈H₂₆O₅
M_r = 442.49
Triclinic, $[P \overline 1]$
a = 9.7126 (3) Å
b = 11.5930 (3) Å
c = 12.5989 (5) Å
= 115.013 (2)°
= 107.126 (2)°
= 97.431 (1)°
V = 1174.60 (7) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.952, T_max = 0.991
20057 measured reflections
4124 independent reflections
3271 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.110
S = 1.06
4124 reflections
323 parameters
40 restraints
H-atom parameters constrained
_max = 0.23 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C28-H28BCg1ⁱ	0.98	3.00	3.601 (7)	121
C5-H5Cg2ⁱⁱ	0.93	2.89	3.693 (3)	145
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON and publCIF (Westrip, 2010).

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

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