Engineering Crystalline Architecture with Supramolecular Tapes: Studies on Secondary Donor−Acceptor Interactions in Cocrystals of the Cyclic Dipeptide of Glycine

Abstract

In this study, we examine the noncovalent interactions that occur between the cyclic dipeptide of glycine (GLYDKP) and a carboxylic acid guest. This study complements our earlier studies on the cyclic dipeptide of aspartic acid by exploring further the possibility of using hydrogen-bonded tapes comprised of molecules of GLYDKP, as a scaffold with which to control the location of guest molecules in a crystalline lattice. On the basis of the 11 cocrystals of GLYDKP reported herein, we conclude that guest molecules will be positioned between tapes of GLYDKP if the guest molecules meet the following criteria. First, the width of the guest molecule should be between 4.5 and 8.5 A. Second, interactions between adjacent guest molecules should be stronger than a van der Waals contact. Third, a hydrogen-bond donor (hydroxyl group) and a hydrogen-bond acceptor (carbonyl group) should be present in the structure of the guest with their separation no greater than two bonds between the carbon atom of the carbonyl grou...