Abstract
The title compound, C11H9N3OS, (I), crystallizes in the monoclinic space group P21/n. The mol-ecular conformation is nearly planar and features an intra-molecular chalcogen bond between the thio-phene S and the imine N atoms. Within the crystal, the strongest inter-actions between mol-ecules are the N-H⋯O hydrogen bonds, which organize them into inversion dimers. The dimers are linked through short C-H⋯N contacts and are stacked into layers propagating in the (001) plane. The crystal structure features π-π stacking between the pyridine aromatic ring and the azomethine double bond. The calculated energies of pairwise inter-molecular inter-actions within the stacks are considerably larger than those found for the inter-actions between the layers.
Highlights
The title compound, C11H9N3OS, (I), crystallizes in the monoclinic space group P21/n
Hydrazones are a versatile group of organic structures that have been the subject of numerous studies in chemical (Barluenga & Valdes, 2011), biomedical (Narang et al, 2012), and materials (Serbutoviez et al, 1995) sciences for decades
Two p-electrons of the sulfur atom participate in aromatic bonding, while another lone pair of p-electrons occupies the sp2 orbital, with the maximum of the electron density localized in the thiophene ring plane
Summary
Hydrazones are a versatile group of organic structures that have been the subject of numerous studies in chemical (Barluenga & Valdes, 2011), biomedical (Narang et al, 2012), and materials (Serbutoviez et al, 1995) sciences for decades. Hydrazone-based iron chelators have found applications as analytical reagents (Singh et al, 1982) and have been proposed for the treatment of bacterial, fungal, and protozoan infections (Narang et al, 2012; Rzhepishevska et al, 2014), as well as health disorders involving alterations in iron metabolism, such as hemochromatosis (Jansova & Simunek, 2019), cancer (Lovejoy & Richardson, 2003), and neurodegenerative diseases (Richardson, 2004). Since iron has been identified as a critical co-factor of bacterial phenazine cytotoxicity to mammalian host cells (Mossine et al, 2016), the application of efficient iron chelators to the infection sites could restrict proliferation of the pathogen and protect the infected tissue from injury caused by toxic bacterial metabolites (Mossine et al, 2018). We report on the molecular and crystal structures of (I), with an emphasis on the non-covalent interactions in the structure
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
