2-[(Dimethyl­amino)­methyl­idene]propane­dinitrile

Kant, R.; Gupta, V.K.; Kapoor, K.; Patil, D.R.; Deshmukh, M.B.

doi:10.1107/S1600536813004960

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 (C-C) = 0.003 Å
R = 0.066
wR = 0.206
Data-to-parameter ratio = 15.7
Details

2-[(Dimethylamino)methylidene]propanedinitrile

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a D. R. Patil ^b and Madhukar B. Deshmukh ^b

^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-HN hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For applications of enamines, see: Omran et al. (1997); Saleh et al. (1999). For related structures, see: Kant et al. (2012); Karlsen et al. (2002).

Experimental

Crystal data

C₆H₇N₃
M_r = 121.15
Monoclinic, P 2₁ /c
a = 4.0368 (3) Å
b = 15.5642 (10) Å
c = 10.8500 (7) Å
= 97.488 (6)°
V = 675.89 (8) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.637, T_max = 1.000
15029 measured reflections
1320 independent reflections
875 reflections with I > 2(I)
R_int = 0.067

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.206
S = 1.05
1320 reflections
84 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2N8ⁱ	0.93	2.51	3.399 (4)	161
C4-H4BN9ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds