Bis(2,9-dimethyl-1,10-phenanthrolin-1-ium) 2,5-dicarboxybenzene-1,4- dicarboxylate-2,9-dimethyl-1,10-phenanthroline-benzene-1,2,4,5-tetracarboxylic acid (1/2/1)

Abstract

The asymmetric unit of the title co-crystal, 2C14H 13N2+·C10H4O 82-·2C14H12N 2·C10H6O8, comprises a 2,9-dimethyl-1,10-phenanthrolin-1-ium cation (Me2PhenH+) and a 2,9-dimethyl-1,10-phenanthroline molecule (Me2Phen), each in a general position, and half each of a 2,5-dicarboxybenzene-1,4-dicarboxylate dianion (LH22-) and a benzene-1,2,4,5-tetracarboxylic acid molecule (LH4), each being disposed about a centre of inversion. Small twists are evident in the dianion [the C - C - C - O torsion angles are 168.41 (18) and 16.2 (3)°], whereas a major twist is found for one carboxylic acid group in the neutral molecule [C - C - C - O = 66.3 (2) and 18.2 (3)°]. The most prominent feature of the crystal packing is the formation of linear supramolecular chains along [001] mediated by charge-assisted O - H⋯O- hydrogen bonding between alternating LH4 and LH22-. These are connected to the Me 2PhenH+ and Me2Phen species by N - H⋯O and O - H⋯N hydrogen bonds, respectively. A three-dimensional architecture is formed by C - H⋯O and π-π interactions [inter-centroid distance = 3.5337 (17) Å]. © 2013 Arman et al.