Supramolecular architectures in the co-crystals involving carboxylic acids and 1,2-bis(4-pyridyl)ethane, an extended bipyridyl type ligand

Abstract

In the present study 1,2-bis(4-pyridyl)ethane (BPA) crystallizes with 2-chlorobenzoic acid (2CBA), 4-methylbenzoic acid (4MBA), phthalic acid (PA), succinic acid (SA) and adipic acid (AA) to yield co-crystals BPA.2CBA ( 1), BPA.4MBA ( 2), BPA.PA ( 3), BPA.SA ( 4) and BPA.AA ( 5) respectively. All the five co-crystals are constituted by the utilization of the R 2 2 (7) synthon, created by the combination of hard N-H⋯O and complementary soft C–H⋯O hydrogen bonds. 1 and 2 illustrate the formation of three component aggregate as in both cases BPA interacts with carboxylic acids to form supramolecular ladder-type assembies. Molecular recognition in co-crystals 3–5 results in the formation of extended infinite tapes and differ further as a consequence of the soft C–H⋯O bonds and stacking interactions. Structure 3 shows the formation of zig-zag tapes while 4 and 5 form linear infinite tapes. Structure 4 shows isostructural behaviour with an analogous structure previously reported (Bowes et al. (2003) [77]).The isostructurality is because of the structural resemblance between both the entities in the co-crystals – fumaric acid/succinic acid and 1,2-bis(4-pyridyl)ethane/1,2-bis(4-pyridyl)ethene. Compound 5 shows good degree of resemblance with another reported analogous structure-1,2-bis(4-pyridyl)ethene adipic acid. (Zhang et al. (2003) [72]). Structure 5 and the reported structure form similar supramolecular sheets through intertape interactions differing from each other only in the alignment of neighboring tapes. The linear tapes in both the cases are linked laterally through different C–H⋯O interactions and ventrally through different stacking interactions. This work illustrates the construction of different supramolecular architectures and the role of weak C–H⋯O hydrogen bonds and stacking interactions in the higher level of supramolecular organization.