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Volume 66 
Part 10 
Page o2497  
October 2010  

Received 6 August 2010
Accepted 18 August 2010
Online 4 September 2010

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.098
Data-to-parameter ratio = 11.7
Details
Open access

(E)-Ethyl 2-cyano-3-[5-nitro-2-(pyrrolidin-1-yl)phenyl]acrylate

aLaboratoire de Cristallographie et Physique Moléculaire, UFR-SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire, and bLaboratoire de Chimie Organique Structurale, UFR-SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire
Correspondence e-mail: marcellin.yapo@univ-cocody.ci

The title compound, C16H17N3O4, was prepared by the reaction of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde and ethyl cyanoacetate. The molecular structure adopts an E conformation with respect to the C=C double bond. The five-membered ring has a half-chair conformation, with puckering parameters Q(2)= 0.399 (2) Å and [varphi] = 93.1 (3)°. In the crystal, inversion dimers , linked by pairs of C-H...O interactions, are further connected through C-H...N hydrogen bonds. Weak slipped [pi]-[pi] interactions occur between symmetry-related benzene rings [centroid-centroid distance = 3.785 (1)Å].

Related literature

For related structures, see: Yapo et al. (2010[Yapo, Y. M., Konan, K. M., Adjou, A., Timotou, A. & Tenon, J. A. (2010). Acta Cryst. E66, o1735.]); Zhang et al. (2009a[Zhang, D., Zhang, X. & Guo, L. (2009a). Acta Cryst. E65, o90.],b[Zhang, S.-J., Zheng, X.-M. & Hu, W.-X. (2009b). Acta Cryst. E65, o2351.]). For reference bond lengths, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17N3O4

  • Mr = 315.33

  • Triclinic, [P \overline 1]

  • a = 8.4137 (3) Å

  • b = 9.9517 (4) Å

  • c = 10.3731 (5) Å

  • [alpha] = 73.065 (1)°

  • [beta] = 71.388 (2)°

  • [gamma] = 72.523 (4)°

  • V = 766.56 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 223 K

  • 0.15 × 0.05 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 12261 measured reflections

  • 3925 independent reflections

  • 2436 reflections with I > 3[sigma](I)

  • Rint = 0.04

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.098

  • S = 1.01

  • 2436 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 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
C15-H152...O2i 0.98 2.50 3.356 (2) 145
C16-H163...N3ii 0.98 2.60 3.574 (3) 172
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: CRYSTALS.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2594 ).


Acknowledgements

The authors wish to thank the Laboratoire de Physique des Interactions Ioniques et Moléculaires of Provence University (France) for the use of the diffractometer.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [CrossRef] [details]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yapo, Y. M., Konan, K. M., Adjou, A., Timotou, A. & Tenon, J. A. (2010). Acta Cryst. E66, o1735.  [CrossRef] [details]
Zhang, D., Zhang, X. & Guo, L. (2009a). Acta Cryst. E65, o90.  [CSD] [CrossRef] [details]
Zhang, S.-J., Zheng, X.-M. & Hu, W.-X. (2009b). Acta Cryst. E65, o2351.  [CSD] [CrossRef] [details]


Acta Cryst (2010). E66, o2497  [ doi:10.1107/S1600536810033374 ]

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