[Journal logo]

Volume 66 
Part 11 
Page o2928  
November 2010  

Received 29 September 2010
Accepted 3 October 2010
Online 23 October 2010

[xu5043sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.039
wR = 0.107
Data-to-parameter ratio = 6.1
Details
Open access

5-(Pyridin-4-yl)isophthalic acid

Yong-Fang Zhang,a Qing-Fu Zhang,a* Juan Jin,a De-Zhi Suna and Da-Qi Wanga

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: zhangqingfu@foxmail.com

In the title compound, C13H9NO4, the two carboxylic groups and the benzene ring are approximately co-planar with a maximum atomic deviation 0.175 (4) Å, while the pyridine ring is oriented at a dihedral angle of 31.07 (18)° with respect to the benzene ring. In the crystal, molecules are linked by O-H...O, O-H...N and weak C-H...O hydrogen bonds, forming a three-dimensional supramolecular framework.

Related literature

For background to carboxylic acids as supramolecular synthons, see: Desiraju (1995[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl. 34, 2311-2327.]); Thalladi et al. (1996[Thalladi, V. R., Goud, B. S., Hoy, V. J., Allen, F. H., Howard, J. A. K. & Desiraju, G. R. (1996). Chem. Commun. pp. 401-402.]).

[Scheme 1]

Experimental

Crystal data

  • C13H9NO4

  • Mr = 243.21

  • Orthorhombic, F d d 2

  • a = 15.5362 (16) Å

  • b = 37.371 (3) Å

  • c = 7.1716 (9) Å

  • V = 4163.9 (8) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.10 mm
Data collection

  • Siemens SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.988

  • 4224 measured reflections

  • 1004 independent reflections

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

  • Rint = 0.045
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.107

  • S = 1.04

  • 1004 reflections

  • 164 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 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
O2-H2A...N1i 0.82 1.78 2.558 (3) 157
O3-H3A...O2ii 0.82 1.91 2.620 (3) 144
C10-H10...O1iii 0.93 2.57 3.491 (4) 172
Symmetry codes: (i) [-x+{\script{7\over 4}}, y+{\script{1\over 4}}, z-{\script{1\over 4}}]; (ii) [x-{\script{1\over 2}}, y, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z+{\script{1\over 4}}].

Data collection: SMART (Siemens, 1996[Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Systems, 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: XU5043 ).

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 21001061), Liaocheng University Funds for Young Scientists (31805) and the Students Science and Technology Innovation Fund of Liaocheng University, China (SRT10058HX2).

References

Desiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl. 34, 2311-2327.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Systems, Inc., Madison, Wisconsin, USA.
Thalladi, V. R., Goud, B. S., Hoy, V. J., Allen, F. H., Howard, J. A. K. & Desiraju, G. R. (1996). Chem. Commun. pp. 401-402.  [CrossRef]

Acta Cryst (2010). E66, o2928  [ doi:10.1107/S1600536810039474 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.