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

Jiang, Y.-K.; Hou, G.-G.

doi:10.1107/S1600536811051075

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 (C-C) = 0.003 Å
R = 0.055
wR = 0.130
Data-to-parameter ratio = 11.6
Details

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

Yan-Ke Jiang ^a and Gui-Ge Hou ^b ^*

^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-HN and O-HO hydrogen bonds and weak C-HO and C-HN hydrogen bonds occur in the crystal structure.

Related literature

For hydrogen bonding in pyrimidine derivatives, see: Hou et al. (2011); Horikoshi et al. (2004); Georgiev et al. (2004); Santoni et al. (2008); Huang & Parquette (2000). For co-crystals of organic acids and pyrimidine, see: Bhogala & Nangia(2003); Du et al. (2005); Hou et al. (2008).

Experimental

Crystal data

C₉H₇N₃·C₉H₆O₆
M_r = 367.31
Monoclinic, P 2₁ /c
a = 8.3532 (19) Å
b = 14.865 (3) Å
c = 13.066 (3) Å
= 98.325 (4)°
V = 1605.4 (6) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.042

Refinement

R[F² > 2(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
_max = 0.22 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N3ⁱ	0.95 (3)	1.70 (3)	2.652 (2)	173 (3)
O3-H3AO2ⁱⁱ	0.92 (3)	1.84 (3)	2.720 (2)	161 (3)
O5-H5AN1	0.95 (3)	1.68 (3)	2.626 (2)	177 (3)
C3-H3O3ⁱⁱ	0.93	2.48	3.367 (3)	159
C14-H14N2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
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.
Georgiev, I., Bosch, E., Barnes, C. L. & Draganjac, M. (2004). Cryst. Growth Des. 4, 235-239.
Horikoshi, R., Nambu, C. & Mochida, T. (2004). New J. Chem. 28, 26-33.
Hou, G.-G., Liu, L.-L., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2008). Acta Cryst. E64, o997.
Hou, G.-G., Ma, L.-Y. & Dai, X.-P. (2011). Acta Cryst. C67, m321-m323.
Huang, B. & Parquette, J. R. (2000). Org. Lett. 2, 239-242.
Santoni, M.-P. C., Yu, S. H., Hanan, G. S., Proust, A. & Hasenknopf, B. (2008). Acta Cryst. E64, o584.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds