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

Yapo, Y.M.; Abou, B.C.; Adjou, A.; Kakou-Yao, R.; Tenon, J.A.

doi:10.1107/S1600536810033374

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 (C-C) = 0.003 Å
R = 0.045
wR = 0.098
Data-to-parameter ratio = 11.7
Details

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

Yapi Marcellin Yapo,^a ^* Bakary Coulibaly Abou,^a Ané Adjou,^b Rita Kakou-Yao ^a and Jules A. Tenon ^a

^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-HO interactions, are further connected through C-HN 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); Zhang et al. (2009a,b). For reference bond lengths, see: Allen (2002). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₆H₁₇N₃O₄
M_r = 315.33
Triclinic, $[P \overline 1]$
a = 8.4137 (3) Å
b = 9.9517 (4) Å
c = 10.3731 (5) Å
= 73.065 (1)°
= 71.388 (2)°
= 72.523 (4)°
V = 766.56 (6) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.04

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.098
S = 1.01
2436 reflections
208 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H152O2ⁱ	0.98	2.50	3.356 (2)	145
C16-H163N3ⁱⁱ	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); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); 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.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
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.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Yapo, Y. M., Konan, K. M., Adjou, A., Timotou, A. & Tenon, J. A. (2010). Acta Cryst. E66, o1735.
Zhang, D., Zhang, X. & Guo, L. (2009a). Acta Cryst. E65, o90.
Zhang, S.-J., Zheng, X.-M. & Hu, W.-X. (2009b). Acta Cryst. E65, o2351.

organic compounds