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Volume 69 
Part 6 
Page o940  
June 2013  

Received 22 March 2013
Accepted 15 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.033
wR = 0.094
Data-to-parameter ratio = 14.9
Details
Open access

Pyridine-4-carbaldehyde-fumaric acid (2/1)

aDepartment of Chemistry & Biology, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA, and bInstitute of Applied Physics Academy of Sciences of Moldova, Academy str. 5, MD-2028 Chisinau, Republic of Moldova
Correspondence e-mail: fonari.xray@gmail.com

In the title co-crystal, 2C6H5NO·C4H4O4, two crystallographically different hydrogen-bonded trimers are formed, one in which the components occupy general positions, and one generated by an inversion centre. This results in the uncommon situation of Z = 3 for a triclinic crystal. In the formula units, molecules are linked by O-H...N hydrogen bonds.

Related literature

For background to the synthetic procedure, see: Aakeroy et al. (2006[Aakeroy, C. B., Hussain, I. & Desper, J. (2006). Cryst. Growth Des. 6, 474-480.]); Desiraju (2003[Desiraju, G. R. (2003). CrystEngComm, 5, 466-467.]). For the use of pyridine-4-carboxaldehyde in cytokine suppressive drugs, see: Boehm et al. (1996[Boehm, J. C., Smietana, J. M., Sorenson, M. E., Garigipati, R. S., Gallagher, T. F., Sheldrake, P. L., Bradbeer, J., Badger, A. M., Laydon, J. T., Lee, J. C., Hillegass, L. M., Griswold, D. E., Breton, J. J., Chabot-Fletcher, M. C. & Adams, J. L. (1996). J. Med. Chem. 39, 3929-3937.]). For adducts of neutral pyridine derivatives and neutral fumaric acid, see: Bowes et al. (2003[Bowes, K. F., Ferguson, G., Lough, A. J. & Glidewell, C. (2003). Acta Cryst. B59, 100-117.]); Aakeroy et al. (2002[Aakeroy, C. B., Beatty, A. M. & Helfrich, B. A. (2002). J. Am. Chem. Soc. 124, 14425-14432.], 2006[Aakeroy, C. B., Hussain, I. & Desper, J. (2006). Cryst. Growth Des. 6, 474-480.], 2007[Aakeroy, C. B., Hussain, I., Forbes, S. & Desper, J. (2007). CrystEngComm, 9, 46-54.]); Batchelor et al. (2000[Batchelor, E., Klinowski, J. & Jones, W. (2000). J. Mater. Chem. 10, 839-848.]). For a related structure, see: Liu et al. (2003[Liu, Y., Xu, D.-J. & Hung, C.-H. (2003). Acta Cryst. E59, m297-m299.]).

[Scheme 1]

Experimental

Crystal data
  • 2C6H5NO·C4H4O4

  • Mr = 330.29

  • Triclinic, [P \overline 1]

  • a = 6.9388 (12) Å

  • b = 10.1962 (18) Å

  • c = 17.002 (3) Å

  • [alpha] = 82.450 (3)°

  • [beta] = 78.615 (3)°

  • [gamma] = 80.064 (3)°

  • V = 1155.6 (4) Å3

  • Z = 3

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.04 × 0.03 × 0.02 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.996, Tmax = 0.998

  • 11918 measured reflections

  • 5022 independent reflections

  • 4351 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.094

  • S = 1.06

  • 5022 reflections

  • 337 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O9-H9A...N3 1.030 (19) 1.576 (19) 2.6047 (12) 176.1 (17)
O5-H5...N1 1.03 (2) 1.57 (2) 2.5952 (12) 172.0 (18)
O7-H7...N2 1.050 (19) 1.54 (2) 2.5826 (12) 172.9 (18)

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2133 ).


Acknowledgements

The authors are grateful for NSF support via DMR grant 0934212 (PREM) and CHE 0832622.)

References

Aakeroy, C. B., Beatty, A. M. & Helfrich, B. A. (2002). J. Am. Chem. Soc. 124, 14425-14432.  [ISI] [CSD] [CrossRef] [PubMed]
Aakeroy, C. B., Hussain, I. & Desper, J. (2006). Cryst. Growth Des. 6, 474-480.  [CSD] [CrossRef]
Aakeroy, C. B., Hussain, I., Forbes, S. & Desper, J. (2007). CrystEngComm, 9, 46-54.  [ChemPort]
Batchelor, E., Klinowski, J. & Jones, W. (2000). J. Mater. Chem. 10, 839-848.  [ISI] [CSD] [CrossRef] [ChemPort]
Boehm, J. C., Smietana, J. M., Sorenson, M. E., Garigipati, R. S., Gallagher, T. F., Sheldrake, P. L., Bradbeer, J., Badger, A. M., Laydon, J. T., Lee, J. C., Hillegass, L. M., Griswold, D. E., Breton, J. J., Chabot-Fletcher, M. C. & Adams, J. L. (1996). J. Med. Chem. 39, 3929-3937.  [CrossRef] [ChemPort] [PubMed] [ISI]
Bowes, K. F., Ferguson, G., Lough, A. J. & Glidewell, C. (2003). Acta Cryst. B59, 100-117.  [CSD] [CrossRef] [details]
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (2003). CrystEngComm, 5, 466-467.  [ISI] [CrossRef] [ChemPort]
Liu, Y., Xu, D.-J. & Hung, C.-H. (2003). Acta Cryst. E59, m297-m299.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o940  [ doi:10.1107/S1600536813013445 ]

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