Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylate

B Balakrishnan,Arasambattu K Mohanakrishnan,Meganathan Nandakumar,Pandamangalam R Seshadri

doi:10.1107/s1600536813005308

B Balakrishnan, Arasambattu K Mohanakrishnan + Show 2 more

Open Access

https://doi.org/10.1107/s1600536813005308

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Abstract

The title compound, C25H20O5S, is the product of a Diels–Alder reaction. The molecule consists of a fused tricyclic system containing two five-membered rings and one six-membered ring. The five-membered rings both show an envelope conformation with the O atom at the flap, whereas the six-membered ring adopts a boat conformation. The thiophene ring is disordered over two sets of sites with an occupancy ratio of 0.53 (1):0.47 (1). The dihedral angles between the 4-methylphenyl ring and the major and minor components of the thiophene ring are 66.3 (1) and 67.9 (1)°, respectively, while the dihedral angle between the disordered thiophenyl components is 3.1 (1)°. The mean plane of the tricyclic ring system makes dihedral angles of 35.8 (1), 30.8 (1) and 32.8 (1)°, respectively, with the 4-methylphenyl ring and the major and minor components of the thiophenyl ring. In the crystal, inversion dimers are formed through pairs of C—H⋯π interactions. In addition, C—H⋯O interactions are observed.

Highlights

The molecule consists of a fused tricyclic system containing two five-membered rings and one sixmembered ring
The thiophene ring is disordered over two sets of sites with an occupancy ratio of 0.53 (1):0.47 (1)
The dihedral angles between the 4-methylphenyl ring and the major and minor components of the thiophene ring are 66.3 (1) and 67.9 (1), respectively, while the dihedral angle between the disordered thiophenyl components is 3.1 (1)

Summary

Crystal data a b

Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.002 Å; disorder in main residue; R factor = 0.041; wR factor = 0.129; data-to-parameter ratio = 17.0. The thiophene ring is disordered over two sets of sites with an occupancy ratio of 0.53 (1):0.47 (1). The dihedral angles between the 4-methylphenyl ring and the major and minor components of the thiophene ring are 66.3 (1) and 67.9 (1) , respectively, while the dihedral angle between the disordered thiophenyl components is 3.1 (1). The mean plane of the tricyclic ring system makes dihedral angles of 35.8 (1), 30.8 (1). 32.8 (1) , respectively, with the 4-methylphenyl ring and the major and minor components of the thiophenyl ring.

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