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Volume 68 
Part 11 
Page o3121  
November 2012  

Received 5 October 2012
Accepted 9 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.134
Data-to-parameter ratio = 15.5
Details
Open access

Methyl (2E)-2-cyano-3-(dimethylamino)prop-2-enoate

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bDepartment of Chemistry, Shivaji University, Kolhapur, 416 004, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title compound, C7H10N2O2, the dimethylamino group is twisted slightly relative to the acrylate fragment, forming a dihedral angle of 11.6 (1)°. In the crystal, molecules are linked via pairs of bifurcated C-H/H...O hydrogen bonds, forming inversion dimers, which are further connected by C-H...N hydrogen bonds into chains along the a-axis direction.

Related literature

For applications of enamines, see: Huang et al. (2007[Huang, J., Liang, Y., Pan, W., Yang, Y. & Dong, D. (2007). Org. Lett. 9, 5345-5348.]); Michael et al. (1999[Michael, J. P., De Konig, C. B., Gravestock, D., Hosken, G. D., Howard, A. S., Jungmann, C. M., Krause, R. W. M., Parsons, A. S., Pelly, S. C. & Stanbury, T. V. (1999). Pure Appl. Chem. 71, 979-988.]). For a related structure, see: Gupta et al. (2007[Gupta, V. P., Sharma, A., Dinesh & Rajnikant (2007). Spectrochim. Acta Part A, 68, 237-244.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10N2O2

  • Mr = 154.17

  • Triclinic, [P \overline 1]

  • a = 7.1102 (5) Å

  • b = 7.8170 (5) Å

  • c = 8.2454 (6) Å

  • [alpha] = 97.270 (6)°

  • [beta] = 93.431 (6)°

  • [gamma] = 115.680 (7)°

  • V = 406.31 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 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 = 0.830, Tmax = 1.000

  • 6682 measured reflections

  • 1593 independent reflections

  • 1126 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.134

  • S = 1.03

  • 1593 reflections

  • 103 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1i 0.93 2.56 3.370 (2) 146
C4-H4A...O1i 0.96 2.58 3.415 (3) 145
C7-H7C...N2ii 0.96 2.58 3.535 (3) 172
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-1, y, z.

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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2525 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gupta, V. P., Sharma, A., Dinesh & Rajnikant (2007). Spectrochim. Acta Part A, 68, 237-244.
Huang, J., Liang, Y., Pan, W., Yang, Y. & Dong, D. (2007). Org. Lett. 9, 5345-5348.  [ISI] [CrossRef] [PubMed] [ChemPort]
Michael, J. P., De Konig, C. B., Gravestock, D., Hosken, G. D., Howard, A. S., Jungmann, C. M., Krause, R. W. M., Parsons, A. S., Pelly, S. C. & Stanbury, T. V. (1999). Pure Appl. Chem. 71, 979-988.  [ISI] [CrossRef] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3121  [ doi:10.1107/S1600536812042304 ]

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