TY - JOUR
T1 - Hierarchy of supramolecular synthons
T2 - Persistent hydroxyl⋯pyridine hydrogen bonds in cocrystals that contain a cyano acceptor
AU - Bis, Joanna A.
AU - Vishweshwar, Peddy
AU - Weyna, David
AU - Zaworotko, Michael J.
PY - 2007/5
Y1 - 2007/5
N2 - 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.
AB - 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.
KW - Cambridge Structural Database
KW - Cocrystal
KW - Pharmaceutical cocrystal
KW - Polymorphism in cocrystals
KW - Supramolecular heterosynthon
UR - http://www.scopus.com/inward/record.url?scp=34250891895&partnerID=8YFLogxK
U2 - 10.1021/mp070012s
DO - 10.1021/mp070012s
M3 - Article
C2 - 17500564
AN - SCOPUS:34250891895
SN - 1543-8384
VL - 4
SP - 401
EP - 416
JO - Molecular Pharmaceutics
JF - Molecular Pharmaceutics
IS - 3
ER -