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Volume 69 
Part 6 
Page o992  
June 2013  

Received 14 May 2013
Accepted 24 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.106
Data-to-parameter ratio = 12.4
Details
Open access

N'-Hydroxypyridine-2-carboximidamide-succinic acid (2/1)

aDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
Correspondence e-mail: shawnlau.zj@hotmail.com

The asymmetric unit of the title co-crystal, C6H7N3O·0.5C4H6O4, comprises one N'-hydroxypyridine-2-carboximidamide molecule and half a succinic acid molecule (the whole molecule is generated by inversion symmetry). In the crystal, molecules are assembled into columns along [110], via strong N-H...O, O-H...O and O-H...N hydrogen bonds.

Related literature

For background to cocrystals and their applications, see: Biradha et al. (2009[Biradha, K., Roy, S. & Mahata, G. (2009). Cryst. Growth Des. 9, 5006-5008.]); Desiraju (1995[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.], 2003[Desiraju, G. R. (2003). J. Mol. Struct. 656, 5-15.]).

[Scheme 1]

Experimental

Crystal data
  • C6H7N3O·0.5C4H6O4

  • Mr = 196.19

  • Monoclinic, P 21 /c

  • a = 8.6707 (8) Å

  • b = 5.2628 (4) Å

  • c = 20.6693 (15) Å

  • [beta] = 93.014 (7)°

  • V = 941.87 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.32 × 0.28 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.966, Tmax = 0.984

  • 4220 measured reflections

  • 1733 independent reflections

  • 1255 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.106

  • S = 1.05

  • 1733 reflections

  • 140 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...N3 0.84 (1) 1.80 (1) 2.6362 (18) 175 (2)
O1-H1...O2 0.83 (1) 1.96 (1) 2.7608 (18) 164 (2)
N2-H2B...O1i 0.86 (1) 2.26 (1) 3.025 (2) 149 (2)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2507 ).


Acknowledgements

This project was supported by the Expert Project of Key Basic Research of the Ministry of Science and Technology of China (grant No. 2003CCA00800), the Science and Technology Department of Zhejiang Province (grant No. 2006 C21105) and the Education Department of Zhejiang Province.

References

Biradha, K., Roy, S. & Mahata, G. (2009). Cryst. Growth Des. 9, 5006-5008.  [CrossRef]
Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.  [CrossRef] [ChemPort] [ISI]
Desiraju, G. R. (2003). J. Mol. Struct. 656, 5-15.  [ISI] [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o992  [ doi:10.1107/S1600536813014359 ]

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