Dimethyl 2,2-bis­(2-cyano­ethyl)malonate

Wang, G.-W.; Zhuang, L.-H.; Wu, W.-Y.; Wang, J.-T.

doi:10.1107/S1600536808005850

Volume 64
Part 5
Page o856
May 2008

Received 25 February 2008
Accepted 3 March 2008
Online 16 April 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.065
wR = 0.155
Data-to-parameter ratio = 14.0
Details

Dimethyl 2,2-bis(2-cyanoethyl)malonate

Guo-Wei Wang,^a Ling-Hua Zhuang,^a Wen-Yuan Wu ^a and Jin-Tang Wang ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: wjt@njut.edu.cn

The asymmetric unit of the title compound, C₁₁H₁₄N₂O₄, contains one half-molecule; a twofold rotation axis passes through the central C atom. Intermolecular C-HN hydrogen bonds link the molecules into a one-dimensional supramolecular structure.

Related literature

For general background, see: Kim et al. (2001); Chetia et al. (2004); Zhang et al. (2004); Ranu & Banerjee (2005). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₄N₂O₄
M_r = 238.24
Monoclinic, C 2/c
a = 13.071 (3) Å
b = 8.5060 (17) Å
c = 10.914 (2) Å
= 90.55 (3)°
V = 1213.4 (4) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.961, T_max = 0.975
1140 measured reflections
1091 independent reflections
860 reflections with I > 2(I)
R_int = 0.048
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.155
S = 0.99
1091 reflections
78 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6BN1ⁱ	0.96	2.57	3.494 (5)	161
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2080 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Chetia, A., Saikia, C. J., Lekhok, K. C. & Boruah, R. C. (2004). Tetrahedron Lett. 45, 2649-2651.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Kim, D. Y., Huh, S. C. & Kim, S. M. (2001). Tetrahedron Lett. 42, 6299-6301.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Ranu, B. C. & Banerjee, S. (2005). Org. Lett. 7, 3049-3052.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, Z., Dong, Y.-W., Wang, G.-W. & Komatsu, K. (2004). Synlett, 1, 61-64.

organic compounds