Knowledge-Based Approaches to H‑Bonding Patterns in Heterocycle-1-Carbohydrazoneamides

• Published in: Crystal growth & design 2016-11, Vol.16 (11), p.6354-6362
• Main Authors: Vologzhanina, Anna V, Sokolov, Andrey V, Purygin, Petr P, Zolotarev, Pavel N, Blatov, Vladislav A
• Format: Article
• Language: English
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/acs.cgd.6b00990

We applied the knowledge-based approaches from the CSD-Materials to three novel heterocycle-1-carbohydrazonamides, for which molecular geometry was obtained by means of ab initio calculations, to predict the topological properties of their supramolecular motifs in the crystalline phase. Our survey suggested competition between nitrogen atoms of the heterocycle and carbohydrazonamide moieties to act as acceptors of H-bonding with the donor -NH2 group that can result in polymorphism based on various H-bonded motifs. The possibility of H-bonded polymorphism was proven for imidazole- and triazole-1-carbohydrazones with the ToposPro knowledge databases, which contain information on relations between local connectivity of molecules and topology of the whole H-bonded system. Experimental structures obtained with single crystal X-ray diffraction belong to the most abundant H-bonded motifs with proposed probabilities in the range 6–44%, thus giving evidence that the CSD-Materials and ToposPro knowledge databases can be combined to successfully predict H-bonded networks even for molecular families with a small number of representatives.