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

Abstract

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.

Exploring 5-fluoronicotinic acid as a versatile building block for the generation of topologically diverse metal–organic and supramolecular Ni, Co, and Cd networks

“…4c). 17, 21 The topological analysis of an underlying network of 2 disclosed an interesting example of parallel 2D + 2D interpenetration, 22 wherein each H-bonded layer is composed of 4-connected Co nodes and 2-connected 5-Fnic À and H 2 biim linkers (Fig. S1 and S2 †).…”

“…19, 21,22 For example, an enhanced thermal stability of derivative 2 over 4 can be explained by the observed 2D + 2D interpenetration of the sql nets in 2. 17,19,21,22 Although a vast number of topological types has been theoretically predicted or experimentally determined, the identication of novel topologies is a constantly growing research direction.…”

Using crystallography, topology and graph set analysis for the description of the hydrogen bond network of triamterene: a rational approach to solid form selection

“…A further paper by Zolotarev et al [23] shows how a study of topology can be incorporated into the prediction of possible crystal forms.…”

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

“…For example, substitution of the methyl group to the chloro-, azide-or iodo-groups gives isostructural pairs in nearly 30% of cases. Recently possibility of prediction of H-bonded motifs using a topological approach was demonstrated for some families of organic molecules with a large number of X-rayed representatives [315,316]. This method schematically represented in Figure 15 utilizes the idea that (i) only a limited number of architectures can be formed from a particular building block with a given connectivity, (ii) overall topology of a network depends on connectivity of building blocks, and (iii) propensities of various networks appearance are not equal.…”

“…This method schematically represented in Figure 15 utilizes the idea that (i) only a limited number of architectures can be formed from a particular building block with a given connectivity, (ii) overall topology of a network depends on connectivity of building blocks, and (iii) propensities of various networks appearance are not equal. While relations between connectivity of an organic molecule and resulting network and corresponding propensities of their appearance have already been published [315,317], this approach does not allow evaluating the most abundant molecular connectivity of insufficiently studied families of organic compounds. Recently, maps of electrostatic potential, the Full Interaction Maps, and the H-bonding Propensities were compared as the tools to overcome this problem for heterocycle-1-carbohydrazoneamides [194].…”