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Volume 67 
Part 8 
Page o2135  
August 2011  

Received 12 July 2011
Accepted 17 July 2011
Online 23 July 2011

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.113
Data-to-parameter ratio = 14.9
Details
Open access

(E)-Ethyl 2-cyano-3-(1H-pyrrol-2-yl)acrylate

Haldorai Yuvaraj,a* D. Gayathri,b Rajesh G. Kalkhambkar,c Vivek K. Guptad and Rajnikantd

aSchool of Chemical Engineering, Yeungnam University, Gyeongsan, Gyeongbuk 712-749, Republic of Korea,bDepartment of Physics, Dr. M.G.R Educational and Research Institute University, Periyar E.V.R High Road, Maduravoyal, Chennai 600 095, India,cDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad 580 001, Karnataka, India, and dPost Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: yuvraj_pd@yahoo.co.in

All the non-H atoms of the title compound, C10H10N2O2, are nearly in the same plane with a maximum deviation of 0.093 (1) Å. In the crystal, adjacent molecules are linked by pairs of intermolecular N-H...O hydrogen bonds, generating inversion dimers with R22(14) ring motifs.

Related literature

For background to and applications of pyrrole derivatives, see: Fischer & Orth (1934[Fischer, H. & Orth, H. (1934). Die Chemie des Pyrrols, Vol. 1, pp. 333. Leipzig: Akademische Verlagsgesellschaft.]). For the Knoevenagel condensation reaction and its applications, see: Knoevenagel (1898[Knoevenagel, E. (1898). Berichte, 31, 2585-2595.]); Bigi et al. (1999[Bigi, F., Chesini, L., Maggi, R. & Sartori, G. (1999). J. Org. Chem. 64, 1033-1035.]). For the synthesis of related compounds, see: Knizhnikov et al. (2007[Knizhnikov, V. A., Borisova, N. E., Yurashevich, N. Y., Popova, L. A., Cherny, A. Yu., Zubreichuk, Z. P. & Reshetova, M. D. (2007). Russ. J. Org. Chem. 43, 855-860.]); Sarda et al. (2009[Sarda, S. R., Jadhav, W. N., Tekale, S. U., Jadhav, G. V., Patil, B. R., Suryawanshi, G. S. & Pawar, R. P. (2009). Lett. Org. Chem. 6, 481-484.]). For related structures, see: Ye et al. (2009[Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.]); Wang & Jian (2008[Wang, J.-G. & Jian, F.-F. (2008). Acta Cryst. E64, o2145.]); Zhang et al. (2009[Zhang, S.-J., Zheng, X.-M. & Hu, W.-X. (2009). Acta Cryst. E65, o2351.]).

[Scheme 1]

Experimental

Crystal data

  • C10H10N2O2

  • Mr = 190.20

  • Monoclinic, P 21 /n

  • a = 6.2811 (2) Å

  • b = 9.4698 (3) Å

  • c = 16.3936 (5) Å

  • [beta] = 92.645 (3)°

  • V = 974.06 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.15 mm
Data collection

  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.971, Tmax = 0.986

  • 18157 measured reflections

  • 1908 independent reflections

  • 1574 reflections with I > 2[sigma](I)

  • Rint = 0.032
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.113

  • S = 1.06

  • 1908 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.09 2.874 (2) 151
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: IS2752 ).

Acknowledgements

The authors thank the Director of the University Sophisticated Instrumentation Facility, University of Jammu, Jammu Tawi, India, for the X-ray data collection. HY gratefully acknowledges Yeungnam University for providing the opportunity to work as an International Research Professor.

References

Bigi, F., Chesini, L., Maggi, R. & Sartori, G. (1999). J. Org. Chem. 64, 1033-1035.  [CrossRef] [PubMed] [ChemPort]
Fischer, H. & Orth, H. (1934). Die Chemie des Pyrrols, Vol. 1, pp. 333. Leipzig: Akademische Verlagsgesellschaft.
Knizhnikov, V. A., Borisova, N. E., Yurashevich, N. Y., Popova, L. A., Cherny, A. Yu., Zubreichuk, Z. P. & Reshetova, M. D. (2007). Russ. J. Org. Chem. 43, 855-860.  [CrossRef] [ChemPort]
Knoevenagel, E. (1898). Berichte, 31, 2585-2595.  [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sarda, S. R., Jadhav, W. N., Tekale, S. U., Jadhav, G. V., Patil, B. R., Suryawanshi, G. S. & Pawar, R. P. (2009). Lett. Org. Chem. 6, 481-484.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, J.-G. & Jian, F.-F. (2008). Acta Cryst. E64, o2145.  [CSD] [CrossRef] [details]
Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.  [CSD] [CrossRef] [details]
Zhang, S.-J., Zheng, X.-M. & Hu, W.-X. (2009). Acta Cryst. E65, o2351.  [CSD] [CrossRef] [details]

Acta Cryst (2011). E67, o2135  [ doi:10.1107/S1600536811028790 ]

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