Four-Fold Inclined Interpenetrated and Three-Fold Parallel Interpenetrated Hydrogen Bond Networks in 1,3,5-Cyclohexanetricarboxylic Acid Hydrate and Its Molecular Complex with 4,4′-Bipyridine

Abstract

Crystallization of 1,3,5-cyclohexanetricarboxylic acid (CTA) from EtOH affords the 1:1 hydrate, CTA·H2O, with 4-fold inclined interpenetrated (6,3) hydrogen-bonded networks. Crystallization of CTA with 4,4′-bipyridine (bipy) furnishes the complex, CTA·bipy·H2O (2:3:1), that has 3-fold interweaving (6,3) networks with parallel interpenetration. The striking similarity of these hydrogen bond networks to those found in the crystal structure of trimesic acid and its complex with bipy suggests that such interpenetrated networks may be engineered using retrosynthetic strategies.