Abstract
In the title hydrated hybrid compound C14H14N2OS2·H2O, the planar imidazo[1,2-a]pyridine ring system is linked to the 1,3-di-thiol-ane moiety by an enone bridge. The atoms of the C-C bond in the 1,3-di-thiol-ane ring are disordered over two positions with occupancies of 0.579 (14) and 0.421 (14) and both disordered rings adopt a half-chair conformation. The oxygen atom of the enone bridge is involved in a weak intra-molecular C-H⋯O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, the hybrid mol-ecules are associated in R 2 2(14) dimeric units by weak C-H⋯O inter-actions. O-H⋯O hydrogen bonds link the water mol-ecules, forming infinite self-assembled chains along the b-axis direction to which the dimers are connected via O-H⋯N hydrogen bonding. Analysis of inter-molecular contacts using Hirshfeld surface analysis and contact enrichment ratio descriptors indicate that hydrogen bonds induced by water mol-ecules are the main driving force in the crystal packing formation.
Highlights
In the title hydrated hybrid compound C14H14N2OS2ÁH2O, the planar imidazo[1,2-a]pyridine ring system is linked to the 1,3-dithiolane moiety by an enone bridge
The oxygen atom of the enone bridge is involved in a weak intramolecular C—HÁ Á ÁO hydrogen bond, which generates an S(6) graph-set motif
Analysis of intermolecular contacts using Hirshfeld surface analysis and contact enrichment ratio descriptors indicate that hydrogen bonds induced by water molecules are the main driving force in the crystal packing formation
Summary
The imidazo[1,2-a]pyridine ring system was described for the first time in 1925 (Chichibabin, 1925). Compounds with the imidazo[1,2-a]pyridine scaffold exhibit a plethora of biological activities, including acting as receptor ligands, anti-infectious agents, enzyme inhibitors etc. We report the synthesis, crystal and molecular structure of the title compound, an hybrid compound containing both imidazo[1,2-a]pyridine and 1,3-dithiolane scaffolds. Since this compound crystallizes as a hydrate, the presence of water molecules in the crystal structure is likely to alter its thermodynamic activity, which would impact its pharmacodynamic properties such as bioavailability and product performance (Khankari & Grant, 1995). To gain a better insight into the cohesive forces between host molecules and intrusive water molecules, and to highlight favored contacts likely to be the crystal driving force, an analysis of intermolecular interactions was carried out using contact enrichment ratios (Jelsch et al, 2014), a descriptor obtained from Hirshfeld surface analysis (Spackman & McKinnon, 2002), which allows an in-depth analysis of the atom–atom contacts in molecular crystals, providing key information on their distribution and is a powerful tool for understanding the most important forces in intermolecular interactions (Jelsch & Bibila Mayaya Bisseyou, 2017)
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