Diversifying molecular and topological space via a supramolecular solid-state synthesis: a purely organic mok net sustained by hydrogen bonds

• Main Authors: Shalisa M. Oburn, Michael A. Sinnwell, Devin P. Ericson, Eric W. Reinheimer, Davide M. Proserpio, Ryan H. Groeneman, Leonard MacGillivray
• Format: Article
• Language: English
• Published: International Union of Crystallography 2019-11-01
• Series: IUCrJ
• Subjects: supramolecular chemistry; [2+2] photocycloaddition; three-dimensional hydrogen-bonded organic networks; crystal engineering; intermolecular interactions; co-crystals; organic solid-state reactions
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2052252519011382

A three-dimensional hydrogen-bonded network based on a rare mok topology has been constructed using an organic molecule synthesized in the solid state. The molecule is obtained using a supramolecular protecting-group strategy that is applied to a solid-state [2+2] photodimerization. The photodimerization affords a novel head-to-head cyclobutane product. The cyclobutane possesses tetrahedrally disposed cis-hydrogen-bond donor (phenolic) and cis-hydrogen-bond acceptor (pyridyl) groups. The product self-assembles in the solid state to form a mok network that exhibits twofold interpenetration. The cyclobutane adopts different conformations to provide combinations of hydrogen-bond donor and acceptor sites to conform to the structural requirements of the mok net.