Hierarchy of supramolecular synthons: persistent hydroxyl...pyridine hydrogen bonds in cocrystals that contain a cyano acceptor.
An analysis of the Cambridge Structural Database reveals >99% occurrence of the hydroxyl...pyridine supramolecular heterosynthon in crystal structures that contain hydroxyl and pyridine moieties in the absence of other hydrogen-bonding moieties. The occurrence of the hydroxyl...cyano supramolecular heterosynthon in crystal structures that contain hydroxyl and cyano moieties is ca. 77%. Such high frequencies indicate that these heterosynthons are strongly favored over the competing hydroxyl...hydroxyl supramolecular homosynthon. However, the CSD does not contain enough information to evaluate which supramolecular heterosynthon prevails when only OH, pyridine, and CN moieties are present in a crystal structure. We have addressed the competition between the hydroxyl...pyridine and the hydroxyl...cyano supramolecular heterosynthons by characterizing a series of 17 cocrystals that are composed of cocrystal formers which contain a permutation of OH, pyridine, and CN functional groups. Structural analysis reveals that all cocrystals are sustained by the hydroxyl...pyridine heterosynthon.
Bis
Joanna A
JA
Department of Chemistry, University of South Florida, CHE205, 4202 East Fowler Avenue, Tampa, Florida 33620, USA.
Vishweshwar
Peddy
P
Weyna
David
D
Zaworotko
Michael J
MJ
D002626:Chemistry, Pharmaceutical; D003460:Crystallization; D018360:Crystallography, X-Ray; D003486:Cyanides / Q000737:chemistry; D006860:Hydrogen Bonding; D006878:Hydroxides / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry
D003486:Cyanides; D006878:Hydroxides; D004364:Pharmaceutical Preparations; D011725:Pyridines; C031356:hydroxide ion