3-Carboxy-5-(pyridinium-4-yl)benzoate: a redetermination

Shi-Jie Li,Wen-Dong Song,Dong-Liang Miao,Shao-Wei Tong

doi:10.1107/s1600536811016394

Abstract

The title compound, C13H9NO4, crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl OH group deprotonated. The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14)° between them. A previous report of this stucture claims, we believe incorrectly, that neither of the carboxylate groups is deprotonated [Zhang et al. (2010 ▶). Acta Cryst. E66, o2928–o2928]. In the crystal, intermolecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen-bonding interactions link adjacent molecules into a three-dimensional supramolecular network.

Highlights

The title compound, C13H9NO4, crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl
The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14) between them
For coordination polymers based on pyridinecarboxylate ligands, see: Lu & Luck (2003); Ma et al (2009)

Summary

Data collection

Shao-Wei Tonga a College of Food Science and Technology, Guangdong Ocean University, Zhanjiang. R factor = 0.050; wR factor = 0.142; data-to-parameter ratio = 6.2. The title compound, C13H9NO4, crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl. The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14) between them. A previous report of this stucture claims, we believe incorrectly, that neither of the carboxylate groups is deprotonated [Zhang et al (2010). Intermolecular O—H O, N—H O and weak C—H O hydrogen-bonding interactions link adjacent molecules into a three-dimensional supramolecular network. Symmetry codes: (i) x þ 14; y 14; z 14; (ii) x þ 12; y; z 12; (iii) x þ 1; y; z; (iv). Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL

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Crystal data

Special details