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Volume 68 
Part 1 
Page o6  
January 2012  

Received 24 November 2011
Accepted 28 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.130
Data-to-parameter ratio = 11.6
Details
Open access

Benzene-1,3,5-tricarboxylic acid-5-(4-pyridyl)pyrimidine (1/1)

aResearch Center of Medical Chemistry & Chemical Biology, Chongqing Technology and Business University, Chongqing 400067, People's Republic of China, and bCollege of Pharmacy, Binzhou Medical University, Yantai 264003, People's Republic of China
Correspondence e-mail: guigehou@163.com

In the pyrimidine molecule of the title compound, C9H7N3·C9H6O6, the pyridine ring is oriented at 33.26 (11)° with respect to the pyrimidine ring. In the benzene-1,3,5-tricarboxylic acid molecule, the three carboxy groups are twisted by 7.92 (9), 8.68 (10) and 17.07 (10)° relative to the benzene ring. Classical O-H...N and O-H...O hydrogen bonds and weak C-H...O and C-H...N hydrogen bonds occur in the crystal structure.

Related literature

For hydrogen bonding in pyrimidine derivatives, see: Hou et al. (2011[Hou, G.-G., Ma, L.-Y. & Dai, X.-P. (2011). Acta Cryst. C67, m321-m323.]); Horikoshi et al. (2004[Horikoshi, R., Nambu, C. & Mochida, T. (2004). New J. Chem. 28, 26-33.]); Georgiev et al. (2004[Georgiev, I., Bosch, E., Barnes, C. L. & Draganjac, M. (2004). Cryst. Growth Des. 4, 235-239.]); Santoni et al. (2008[Santoni, M.-P. C., Yu, S. H., Hanan, G. S., Proust, A. & Hasenknopf, B. (2008). Acta Cryst. E64, o584.]); Huang & Parquette (2000[Huang, B. & Parquette, J. R. (2000). Org. Lett. 2, 239-242.]). For co-crystals of organic acids and pyrimidine, see: Bhogala & Nangia(2003[Bhogala, B. R. & Nangia, A. (2003). Cryst. Growth Des. 3, 547-554.]); Du et al. (2005[Du, M., Zhang, Z.-H. & Zhao, X.-J. (2005). Cryst. Growth Des. 2, 1247-1254.]); Hou et al. (2008[Hou, G.-G., Liu, L.-L., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2008). Acta Cryst. E64, o997.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7N3·C9H6O6

  • Mr = 367.31

  • Monoclinic, P 21 /c

  • a = 8.3532 (19) Å

  • b = 14.865 (3) Å

  • c = 13.066 (3) Å

  • [beta] = 98.325 (4)°

  • V = 1605.4 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 298 K

  • 0.32 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • 8278 measured reflections

  • 2967 independent reflections

  • 2142 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.130

  • S = 1.04

  • 2967 reflections

  • 256 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N3i 0.95 (3) 1.70 (3) 2.652 (2) 173 (3)
O3-H3A...O2ii 0.92 (3) 1.84 (3) 2.720 (2) 161 (3)
O5-H5A...N1 0.95 (3) 1.68 (3) 2.626 (2) 177 (3)
C3-H3...O3ii 0.93 2.48 3.367 (3) 159
C14-H14...N2iii 0.93 2.59 3.335 (3) 137
Symmetry codes: (i) x+1, y, z-1; (ii) -x+2, -y+1, -z; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and SMART. 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: XU5398 ).


Acknowledgements

The authors thank the Scientific Research Project of Chongqing Education Committee, China (KJ100720 and KJTD201020) and Chongqing Technology and Business University, China (2010-56-07) for supporting this work.

References

Bhogala, B. R. & Nangia, A. (2003). Cryst. Growth Des. 3, 547-554.  [CSD] [CrossRef] [ChemPort]
Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Du, M., Zhang, Z.-H. & Zhao, X.-J. (2005). Cryst. Growth Des. 2, 1247-1254.  [CSD] [CrossRef]
Georgiev, I., Bosch, E., Barnes, C. L. & Draganjac, M. (2004). Cryst. Growth Des. 4, 235-239.  [CSD] [CrossRef] [ChemPort]
Horikoshi, R., Nambu, C. & Mochida, T. (2004). New J. Chem. 28, 26-33.  [ISI] [CSD] [CrossRef] [ChemPort]
Hou, G.-G., Liu, L.-L., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2008). Acta Cryst. E64, o997.  [CSD] [CrossRef] [details]
Hou, G.-G., Ma, L.-Y. & Dai, X.-P. (2011). Acta Cryst. C67, m321-m323.  [CSD] [CrossRef] [details]
Huang, B. & Parquette, J. R. (2000). Org. Lett. 2, 239-242.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Santoni, M.-P. C., Yu, S. H., Hanan, G. S., Proust, A. & Hasenknopf, B. (2008). Acta Cryst. E64, o584.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o6  [ doi:10.1107/S1600536811051075 ]

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