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Volume 69 
Part 8 
Page o1223  
August 2013  

Received 8 June 2013
Accepted 2 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.145
Data-to-parameter ratio = 11.2
Details
Open access

(Z)-Ethyl 2-cyano-3-(1H-imidazol-2-yl)acrylate

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad 580 001, Karnatak, India,bDepartment of Biotechnology, Dr. M.G.R Educational and Research Institute University, Periyar E.V.R. High Road, Maduravoyal, Chennai 600 095, India, and cDepartment of Image Science and Engineering, Pukyong National University, Busan 608 739, Republic of Korea
Correspondence e-mail: ytjeong@pknu.ac.kr

The crystal structure of the title compound, C9H9N3O2, features N-H...N and C-H...O interactions. The N-H...N interaction generates a chain running along the a axis and the C-H...O interaction generates a chain along the c axis. An intramolecular C-H...O interaction is also observed.

Related literature

For background references and the biological importance of related compounds, see: Bigi et al. (1999[Bigi, F., Chesini, L., Maggi, R. & Sartori, G. (1999). J. Org. Chem. 64, 1033-1035.]); Yu et al. (2000[Yu, N., Aramini, J. M. M., Germann, W. & Huang, Z. (2000). Tetrahedron Lett. 41, 6993-6996.]). For the synthesis, see: Knoevenagel (1898[Knoevenagel, E. (1898). Berichte, 31, 2585-2596.]); Yadav et al. (2004[Yadav, J. S., Subba Reddy, B. V., Basak, A. K., Visali, B., Narsaiah, A. V. & Nagaiah, K. (2004). Eur. J. Org. Chem. pp. 546-551.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9N3O2

  • Mr = 191.19

  • Orthorhombic, P c a 21

  • a = 10.0768 (7) Å

  • b = 12.0387 (8) Å

  • c = 7.7047 (6) Å

  • V = 934.67 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.4 × 0.23 × 0.2 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.984

  • 7118 measured reflections

  • 1436 independent reflections

  • 1189 reflections with ( > 2[sigma](I)

  • Rint = 0.033

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

  • wR(F2) = 0.145

  • S = 0.83

  • 1436 reflections

  • 128 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O1 0.93 2.38 2.771 (3) 105
N1-H1A...N2i 0.86 2.11 2.951 (3) 167
C1-H1...O1ii 0.93 2.45 3.328 (4) 158
Symmetry codes: (i) [x-{\script{1\over 2}}, -y, z]; (ii) [-x, -y, z-{\script{1\over 2}}].

Data collection: SMART (Bruker 2001[Bruker (2001). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SADABS, SMART 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2635 ).


Acknowledgements

The authors thank the Director, USIC Karnatak University Dharwad, India, for the X-ray data collection.

References

Bigi, F., Chesini, L., Maggi, R. & Sartori, G. (1999). J. Org. Chem. 64, 1033-1035.  [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Knoevenagel, E. (1898). Berichte, 31, 2585-2596.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yadav, J. S., Subba Reddy, B. V., Basak, A. K., Visali, B., Narsaiah, A. V. & Nagaiah, K. (2004). Eur. J. Org. Chem. pp. 546-551.  [CrossRef]
Yu, N., Aramini, J. M. M., Germann, W. & Huang, Z. (2000). Tetrahedron Lett. 41, 6993-6996.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1223  [ doi:10.1107/S1600536813018278 ]

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