Abstract
Two crystallographically independent mol-ecules (A and B) are present in the asymmetric unit of the title compound, C11H9IN2OS, which differ mainly in the dihedral angle between the phenyl and thia-zole rings [38.94 (16) and 32.12 (15)°, respectively]. In the crystal, the mol-ecules form ⋯A⋯B⋯A⋯B⋯ chains along the [001] and [010] directions through moderate N-H⋯O hydrogen bonds and C-H⋯π inter-actions, respectively. The overall three-dimensional network is formed by I⋯I and I⋯S inter-actions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯C/C⋯H (26.2%), H⋯H (20.9%), H⋯I/I⋯H (19.4%) and H⋯O/O⋯H (6.8%) inter-actions.
Highlights
The 1,3-thiazole ring is a structural motif frequently found in the pharmaceutical field in antibacterial (Alam et al, 2014), antifungal (Yu et al, 2007) and antiviral (Liu et al, 2011) agents among others
The principal difference between these molecules is the dihedral angle between the phenyl and thiazole rings
Unlike the related compound 2-acetamido-4-p-tolyl-1,3-thiazole (Lynch et al, 2004) in which the molecule is essentially flat, the presence of the iodine atom at C5 or C16 of the title compound induces rotation of the phenyl group attached to the thiazole ring, as observed in some bromine-substituted phenylthiazole compounds
Summary
The 1,3-thiazole ring is a structural motif frequently found in the pharmaceutical field in antibacterial (Alam et al, 2014), antifungal (Yu et al, 2007) and antiviral (Liu et al, 2011) agents among others. Halo-1,3-thiazole derivatives have proven to be suitable substrates in oxidative addition reactions in the presence of palladium (Wang et al, 2015; Hammerle et al, 2010). The presence of halogens in the core of thiazole derivatives opens the door to using them as suitable substrates for coupling reactions and to expand the therapeutic potential of a compound by improving the pharmaceutical properties. Transition-metal-catalysed reactions constitute one of the most important and attractive research areas in academia, as well as in the pharmaceutical and fine chemical industries (Zhao et al, 2017; Jana et al, 2011). Cross-coupling reactions usually require, in addition to a transition metal, that the electrophilic coupling partner possesses leaving groups such as BrÀ or IÀ among others. The development of suitable halo-1,3thiazole substrates for cross-coupling reactions allows us to report the crystal structure and the Hirshfeld surface analysis of N-(5-iodo-4-phenylthiazol-2-yl)acetamide
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