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Volume 68 
Part 6 
Page o1625  
June 2012  

Received 19 April 2012
Accepted 28 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.101
Data-to-parameter ratio = 14.8
Details
Open access

Oxalic acid-pyridine-4-carbonitrile (1/2)

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: chenxinyuanseu@yahoo.com.cn

In the title compound, 2C6H4N2·C2H2O4, the oxalic acid molecule lies about an inversion center. The pyridine ring of the pyridine-4-carbonitrile molecule is almost planar, the largest deviation from the least-squares plane being 0.006 (1) Å; the nitrile N atom deviates from this plane by 0.114 (1) Å. In the crystal, the oxalic acid molecules and the pyridine-4-carbonitrile molecules form stacks. Neighboring molecules within the stacks are related by translation in the a direction, with interplanar distances of 3.183 (1) and 3.331 (2) Å, respectively. Each oxalic acid molecule forms strong O-H...N hydrogen bonds with two molecules of pyridine-4-carbonitrile. Besides this, there are also weak C-H...O interactions.

Related literature

For the structures and ferroelectric properties of related compounds, see: Fu et al. (2011a[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011a). J. Am. Chem. Soc. 133, 12780-12786.],b[Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011b). Angew. Chem. Int. Ed. 50, 11947-11951.],c[Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011c). Adv. Mater. 23, 5658-5662.]); Dai & Chen (2011[Dai, J. & Chen, X.-Y. (2011). Acta Cryst. E67, o287.]); Xu et al. (2011[Xu, R.-J., Fu, D.-W., Dai, J., Zhang, Y., Ge, J.-Z. & Ye, H.-Y. (2011). Inorg. Chem. Commun. 14, 1093-1096.]); Zheng (2011[Zheng, W.-N. (2011). Acta Cryst. E67, m344.]). For standard bond lengths, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C6H4N2·0.5C2H2O4

  • Mr = 149.13

  • Triclinic, [P \overline 1]

  • a = 3.6842 (6) Å

  • b = 7.5816 (5) Å

  • c = 12.4511 (1) Å

  • [alpha] = 78.258 (1)°

  • [beta] = 85.301 (1)°

  • [gamma] = 82.547 (1)°

  • V = 337.08 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.10 × 0.03 × 0.03 mm

Data collection
  • Rigaku SCXmini Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.910, Tmax = 1.000

  • 3634 measured reflections

  • 1528 independent reflections

  • 1268 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

  • wR(F2) = 0.101

  • S = 1.04

  • 1528 reflections

  • 103 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.82 (1) 1.80 (1) 2.6173 (12) 176 (2)
C4-H4A...O1i 0.93 2.48 3.3640 (13) 160
Symmetry code: (i) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2054 ).


Acknowledgements

This work was supported by a start-up grant from Southeast University, China.

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.
Dai, J. & Chen, X.-Y. (2011). Acta Cryst. E67, o287.  [CSD] [CrossRef] [details]
Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011c). Adv. Mater. 23, 5658-5662.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G. & Huang, S. P. D. (2011a). J. Am. Chem. Soc. 133, 12780-12786.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Fu, D.-W., Zhang, W., Cai, H.-L., Zhang, Y., Ge, J.-Z., Xiong, R.-G., Huang, S. P. D. & Nakamura, T. (2011b). Angew. Chem. Int. Ed. 50, 11947-11951.  [ISI] [CSD] [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xu, R.-J., Fu, D.-W., Dai, J., Zhang, Y., Ge, J.-Z. & Ye, H.-Y. (2011). Inorg. Chem. Commun. 14, 1093-1096.  [ISI] [CSD] [CrossRef] [ChemPort]
Zheng, W.-N. (2011). Acta Cryst. E67, m344.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o1625  [ doi:10.1107/S1600536812019137 ]

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