Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 12 (December 2013)


organic compounds



Acta Cryst. (2013). C69, 1537-1540    [ doi:10.1107/S0108270113030801 ]

Two-dimensional hydrogen-bonded supra­molecular networks in the compounds of benzene-1,2,4,5-tetra­carb­oxy­lic acid (pyromellitic acid) with 2,2'-bi­imidazole and 4,4'-di­methyl-2,2'-bi­pyridine

K.-L. Zhong

Abstract: Two products from the proton-transfer reactions of benzene-1,2,4,5-tetra­carb­oxy­lic acid (pyromellitic acid, PMA) with 2,2'-bi­imidazole and 4,4'-dimethyl-2,2'-bipyridine, namely 2,2'-bi­imidazole-3,3'-diium 2,5-di­carb­oxy­benzene-1,4-di­carboxyl­ate, C6H8N42+,C10H4O82-, (I), and 4-methyl-2-(4-methyl­pyridin-2-yl)pyridinium 2,4,5-tri­carb­oxy­benzoate mono­hydrate, C12H13N2+·C10H5O8-·H2O, (II), have been prepared and their structures determined. Both compounds crystallize in the space group P\overline{1}. The asymmetric unit of (I) is composed of two independent ion pairs. Both the 2,2'-bi­imidazole-3,3'-diium dication and the PMA2- anion are located on special positions (inversion centres). The protonated 2,2'-bi­imidazole-3,3'-diium ring H atoms are involved in hydrogen bonding with carboxyl­ate O atoms to form one-dimensional hydrogen-bonded chain structures. Adjacent chains are further linked via carbox­yl-carboxyl O-H...O hydrogen bonding, resulting in a two-dimensional supra­molecular sheet with the R65(34) motif extending in the (1\overline{2}1) plane. In (II), classical O-H...O hydrogen-bond-linked anion-anion units are extended into a one-dimensional chain running parallel to the [100] direction, giving an R22(8)R44(30) motif. The chains are connected by water-carboxyl O-H...O hydrogen bonds to form a two-dimensional network parallel to the (01\overline{1}) plane. The 4-methyl-2-(4-methyl­pyridin-2-yl)pyridinium cations lie between the two-dimensional supra­molecular layers linked via N-H...O hydrogen-bonding inter­actions.

CCDC references: 787056 and 971187

Formula: C6H8N42+·C10H4O82- and C12H13N2+·C10H5O8-·H2O

Keywords: crystal structure; hydrogen bonding; pyromellitic acid; 2,2'-bi­imidazole; 4,4'-dimethyl-2,2'-bi­pyridine.


hkldisplay filedownload file

Structure factor file (CIF format) (176.2 kbytes)
[ doi:10.1107/S0108270113030801/sf3209Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (172.4 kbytes)
[ doi:10.1107/S0108270113030801/sf3209IIsup3.hkl ]
Contains datablock II


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