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Volume 69 
Part 5 
Page o748  
May 2013  

Received 2 December 2012
Accepted 8 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.055
wR = 0.192
Data-to-parameter ratio = 12.6
Details
Open access

Ethyl (E)-2-cyano-3-(4-methylphenyl)acrylate: a second monoclinic polymorph

aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
Correspondence e-mail: kong_lin2009@126.com

The title compound, C13H13NO2, was previously described in space group P21/c by He et al. [Acta Cryst. (1993), C49, 2000-2002]. The ethyl group is disordered over two sets of sites in a 0.615 (10):0.385 (10) ratio. The C-O-C-C torsion angles containing the ethyl group are -111.6 (10) and 177.9 (7)°, while in the previously reported polymorph, the torsion angle is -167.3 (2)°. The molecules pack to form a three-dimensional structure in the ABAB style along the c-axis direction in the title compound, but parallel to the a-axis direction in the reported polymorph.

Related literature

For the first polymorph, see: He et al. (1993[He, Y., Shi, J. & Su, G. (1993). Acta Cryst. C49, 2000-2002.]). For background to intramolecular charge-transfer molecules and their use in the construction of one- to three-dimesional organic nanostructures, see: Zhang et al. (2007[Zhang, X. J., Zhang, X. H., Zou, K., Lee, C. S. & Lee, S. T. (2007). J. Am. Chem. Soc. 129, 3527-3532.]); Zhang et al. (2008[Zhang, X. J., Zhang, X. H., Wang, B., Zhang, C. Y., Chang, J. C., Lee, C. S. & Lee, S. T. (2008). J. Phys. Chem. C, pp. 16264-16268.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO2

  • Mr = 215.24

  • Monoclinic, P 21 /c

  • a = 4.7616 (4) Å

  • b = 17.7989 (15) Å

  • c = 14.2841 (12) Å

  • [beta] = 93.8021 (10)°

  • V = 1207.93 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 298 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan phi and omega scans Tmin = 0.984, Tmax = 0.984

  • 8359 measured reflections

  • 2117 independent reflections

  • 1617 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.192

  • S = 1.11

  • 2117 reflections

  • 168 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Data collection: APEX2 (Bruker, 2002[Bruker (2002). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). 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: AA2081 ).


Acknowledgements

We gratefully acknowledge the NSFC(21101001), and the 211 Project of Anhui University for supporting this study.

References

Bruker (2002). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
He, Y., Shi, J. & Su, G. (1993). Acta Cryst. C49, 2000-2002.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Zhang, X. J., Zhang, X. H., Wang, B., Zhang, C. Y., Chang, J. C., Lee, C. S. & Lee, S. T. (2008). J. Phys. Chem. C, pp. 16264-16268.
Zhang, X. J., Zhang, X. H., Zou, K., Lee, C. S. & Lee, S. T. (2007). J. Am. Chem. Soc. 129, 3527-3532.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o748  [ doi:10.1107/S1600536813009550 ]

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