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Volume 69 
Part 4 
Page o504  
April 2013  

Received 29 December 2012
Accepted 28 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.187
Data-to-parameter ratio = 15.4
Details
Open access

Ethyl 2-(4-methylbenzoyl)-2,3-dihydro-1H-indene-2-carboxylate

aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
Correspondence e-mail: qwjgq@163.com

The title compound, C20H20O3, contains two fused rings with a quaternary carbon centre connecting p-toluoyl and ethoxycarbonyl groups. The dihedral angle between the fused benzene ring and the three-C-atom plane (derived from O=C-C-C=O) is 82.5 (4)°, whereas the dihedral angle between the planes of the benzene rings is 53.4 (2)°. In the crystal, molecules are linked via C-H...Oester hydrogen bonds, forming chains propagating along [010].

Related literature

For the preparation and crystal engineering studies of the title compound, see: Singh & Paul (2006[Singh, P. & Paul, K. (2006). J. Heterocycl. Chem. 43, 607-611.]); Wang & Wu (2012[Wang, J. & Wu, A. (2012). Org. Lett. 14, 6060-6063.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20O3

  • Mr = 308.37

  • Monoclinic, P 21 /c

  • a = 8.1957 (14) Å

  • b = 6.1287 (10) Å

  • c = 32.995 (5) Å

  • [beta] = 93.014 (3)°

  • V = 1655.0 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 298 K

  • 0.12 × 0.10 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.990, Tmax = 0.992

  • 11945 measured reflections

  • 3241 independent reflections

  • 2482 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.187

  • S = 1.09

  • 3241 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O1i 0.93 2.60 3.357 (3) 139
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.]); cell refinement: SAINT(Bruker, 2004[Bruker (2004). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2108 ).


Acknowledgements

The authors are grateful to the Central China Normal University for financial support and thank Dr Xiang-Gao Meng for the X-ray data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, P. & Paul, K. (2006). J. Heterocycl. Chem. 43, 607-611.  [CrossRef] [ChemPort]
Wang, J. & Wu, A. (2012). Org. Lett. 14, 6060-6063.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o504  [ doi:10.1107/S1600536813005801 ]

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