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Volume 69 
Part 3 
Page o433  
March 2013  

Received 14 February 2013
Accepted 20 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.066
wR = 0.206
Data-to-parameter ratio = 15.7
Details
Open access

2-[(Dimethylamino)methylidene]propanedinitrile

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 moleclue, C6H7N3, the mean plane of the dimethylamino group [maximum deviation = 0.006 (2) Å] forms a dihedral angle of 7.95 (18)° with the mean plane of the propanedinitrile fragment [maximum deviation = 0.008 (2) Å]. In the crystal, weak C-H...N hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For applications of enamines, see: Omran et al. (1997[Omran, F. A., Awadi, N. A., Khair, A. A. E. & Elnagdi, M. H. (1997). Org. Prep. Proced. Int. D29, 285-292.]); Saleh et al. (1999[Saleh, B. A., Abdelkhalik, M. M., Enzy, A. A. & Elnagdi, M. H. (1999). J. Chem. Res. (S), pp. 654-655.]). For related structures, see: Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Salunkhe, D. K. & Deshmukh, M. B. (2012). Acta Cryst. E68, o3121.]); Karlsen et al. (2002[Karlsen, H., Kolsaker, P., Rømming, C. & Uggerud, E. (2002). J. Chem. Soc. Perkin Trans. 2, pp. 404-409.]).

[Scheme 1]

Experimental

Crystal data
  • C6H7N3

  • Mr = 121.15

  • Monoclinic, P 21 /c

  • a = 4.0368 (3) Å

  • b = 15.5642 (10) Å

  • c = 10.8500 (7) Å

  • [beta] = 97.488 (6)°

  • V = 675.89 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 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 = 0.637, Tmax = 1.000

  • 15029 measured reflections

  • 1320 independent reflections

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

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.206

  • S = 1.05

  • 1320 reflections

  • 84 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N8i 0.93 2.51 3.399 (4) 161
C4-H4B...N9ii 0.96 2.62 3.569 (4) 170
Symmetry codes: (i) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

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: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5587 ).


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

Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Salunkhe, D. K. & Deshmukh, M. B. (2012). Acta Cryst. E68, o3121.  [CSD] [CrossRef] [details]
Karlsen, H., Kolsaker, P., Rømming, C. & Uggerud, E. (2002). J. Chem. Soc. Perkin Trans. 2, pp. 404-409.
Omran, F. A., Awadi, N. A., Khair, A. A. E. & Elnagdi, M. H. (1997). Org. Prep. Proced. Int. D29, 285-292.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Saleh, B. A., Abdelkhalik, M. M., Enzy, A. A. & Elnagdi, M. H. (1999). J. Chem. Res. (S), pp. 654-655.
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 (2013). E69, o433  [ doi:10.1107/S1600536813004960 ]

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