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Volume 69 
Part 4 
Pages o498-o499  
April 2013  

Received 7 February 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 = 0.041
wR = 0.129
Data-to-parameter ratio = 17.0
Details
Open access

Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-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, 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...[pi] interactions. In addition, C-H...O interactions are observed.

Related literature

For background to Diels-Alder reactions, see: Denmark & Thorarensen (1996[Denmark, S. E. & Thorarensen, A. (1996). Chem. Rev. 96, 137-166.]). For related structures, see: 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, 973-974.]); Fun et al. (2011[Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o701-o702.]); Gurbanov et al. (2009[Gurbanov, A. V., Nikitina, E. V., Sorokina, E. A., Zubkov, F. I. & Khrustalev, V. N. (2009). Acta Cryst. E65, o3243-o3244.]); Balakrishnan et al. (2013[Balakrishnan, B., Nandakumar, M., Seshadri, P. R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o323.]). 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
  • C25H20O5S

  • Mr = 432.47

  • Triclinic, [P \overline 1]

  • a = 7.5966 (15) Å

  • b = 10.877 (2) Å

  • c = 13.515 (3) Å

  • [alpha] = 91.339 (5)°

  • [beta] = 93.456 (4)°

  • [gamma] = 100.129 (5)°

  • V = 1096.6 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • 19981 measured reflections

  • 5464 independent reflections

  • 4142 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

  • wR(F2) = 0.129

  • S = 1.03

  • 5464 reflections

  • 321 parameters

  • 52 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
C11-H11...O4i 0.93 2.47 3.378 (1) 165
C17-H17B...Cgii 0.96 3.26 3.99 (2) 136
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison. Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: IM2420 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Balakrishnan, B., Nandakumar, M., Seshadri, P. R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o323.  [CrossRef] [details]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison. Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Denmark, S. E. & Thorarensen, A. (1996). Chem. Rev. 96, 137-166.  [CrossRef] [PubMed] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Suwunwong, T. & Chantrapromma, S. (2011). Acta Cryst. E67, o701-o702.  [CSD] [CrossRef] [details]
Gurbanov, A. V., Nikitina, E. V., Sorokina, E. A., Zubkov, F. I. & Khrustalev, V. N. (2009). Acta Cryst. E65, o3243-o3244.  [CSD] [CrossRef] [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]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o498-o499   [ doi:10.1107/S1600536813005308 ]

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