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Volume 67 
Part 1 
Page o8  
January 2011  

Received 19 November 2010
Accepted 26 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 13.0
Details
Open access

(E)-N-Benzyl-2-cyano-3-phenylacrylamide

aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: kangtairan@yahoo.com.cn

In the title compound, C17H14N2O, the N-benzylformamide and phenyl groups are located on the opposite sides of the C=C bond, showing an E configuration; the terminal phenyl rings are twisted to each other at a dihedral angle of 63.61 (7)°. Intermolecular classical N-H...N and weak C-H...O hydrogen bonds occur in the crystal structure.

Related literature

For the use of malononitrile-containing compounds as building blocks in syntheses, see: Lee et al. (2002[Lee, S. U., Shin, C. G., Lee, C. K. & Lee, Y. S. (2002). J. Org. Chem. 67, 7019-7028.]); Rajan et al. (2001[Rajan, P., Vedernikova, I., Cos, P., Berghe, D. V., Augustyns, K. & Haemers, A. (2001). Bioorg. Med. Chem. Lett. 11, 215-217.]); Yingyongnarongkul et al. (2006[Yingyongnarongkul, B., Apriatikul, N., Aroonrerk, N. & Suksamrarn, A. (2006). Bioorg. Med. Chem. Lett. 16, 5870-5873.]). For a related structure, see: Kang & Chen (2009[Kang, T.-R. & Chen, L.-M. (2009). Acta Cryst. E65, o3164.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14N2O

  • Mr = 262.30

  • Triclinic, [P \overline 1]

  • a = 5.8956 (3) Å

  • b = 9.9224 (5) Å

  • c = 12.1400 (7) Å

  • [alpha] = 94.508 (5)°

  • [beta] = 99.544 (4)°

  • [gamma] = 98.895 (4)°

  • V = 687.95 (6) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.64 mm-1

  • T = 291 K

  • 0.36 × 0.35 × 0.30 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.803, Tmax = 0.832

  • 5416 measured reflections

  • 2407 independent reflections

  • 2202 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.05

  • 2407 reflections

  • 185 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H4...N1i 0.88 (1) 2.24 (1) 3.0687 (14) 157 (1)
C3-H3...O1ii 0.93 2.36 3.2672 (16) 164
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5098 ).


Acknowledgements

The authors thank the Testing Centre of the Sichuan University for the diffraction measurements and are grateful for financial support from China West Normal University (No. 412374).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kang, T.-R. & Chen, L.-M. (2009). Acta Cryst. E65, o3164.  [CSD] [CrossRef] [details]
Lee, S. U., Shin, C. G., Lee, C. K. & Lee, Y. S. (2002). J. Org. Chem. 67, 7019-7028.  [PubMed]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rajan, P., Vedernikova, I., Cos, P., Berghe, D. V., Augustyns, K. & Haemers, A. (2001). Bioorg. Med. Chem. Lett. 11, 215-217.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yingyongnarongkul, B., Apriatikul, N., Aroonrerk, N. & Suksamrarn, A. (2006). Bioorg. Med. Chem. Lett. 16, 5870-5873.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2011). E67, o8  [ doi:10.1107/S1600536810049548 ]

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