A Possible Route toward Expert Systems in Supramolecular Chemistry: 2‑Periodic H‑Bond Patterns in Molecular Crystals

A novel
approach to prediction of supramolecular motifs was applied
to more than 6000 monomolecular structures containing 2-periodic H-bond
patterns. It is shown that a number of topological descriptors allow
one to rationalize supramolecular motifs, find the regularities in
their structure, and store the information in a knowledge database.
The knowledge database can then be used in an expert system to mimic
the work of a human expert and to forecast the method of assembling
molecules into supramolecular ensembles and into extended (periodic)
architectures. The crystals of N-[(4-methylbenzene)­sulfonyl]­serine
were synthesized, and the principles of the expert system were used
to successfully predict the 2-periodic square-lattice H-bond pattern
in this compound.