Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 1-(1,3-benzo-thia-zol-2-yl)-3-(2-hy-droxy-eth-yl)imidazolidin-2-one.

El Mokhtar Essassi,Joel T Mague,Tuncer Hökelek,Nada Kheira Sebbar,Ahmed Moussaif,Noureddine Hamou Ahabchane,Mohamed Srhir

doi:10.1107/s2056989020001723

Abstract

In the title mol-ecule, C12H13N3O2S, the benzo-thia-zine moiety is slightly non-planar, with the imidazolidine portion twisted only a few degrees out of the mean plane of the former. In the crystal, a layer structure parallel to the bc plane is formed by a combination of O-HHydethy⋯NThz hydrogen bonds and weak C-HImdz⋯OImdz and C-HBnz⋯OImdz (Hydethy = hy-droxy-ethyl, Thz = thia-zole, Imdz = imidazolidine and Bnz = benzene) inter-actions, together with C-HImdz⋯π(ring) and head-to-tail slipped π-stacking [centroid-to-centroid distances = 3.6507 (7) and 3.6866 (7) Å] inter-actions between thia-zole rings. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (47.0%), H⋯O/O⋯H (16.9%), H⋯C/C⋯H (8.0%) and H⋯S/S⋯H (7.6%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, C-H⋯N and C-H⋯O hydrogen-bond energies are 68.5 (for O-HHydethy⋯NThz), 60.1 (for C-HBnz⋯OImdz) and 41.8 kJ mol-1 (for C-HImdz⋯OImdz). Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state.

Highlights

Mohamed Srhir,a* Nada Kheira Sebbar,b,a Tuncer Hokelek,c Ahmed Moussaif,a Joel T
A layer structure parallel to the bc plane is formed by a combination of O—HHydethyÁ Á ÁNThz hydrogen bonds and weak C—HImdzÁ Á ÁOImdz and C—HBnzÁ Á ÁOImdz (Hydethy = hydroxyethyl, Thz = thiazole, Imdz = imidazolidine and Bnz = benzene) interactions, together with C—HImdzÁ Á Á(ring) and head-to-tail slipped -stacking [centroid-to-centroid distances = 3.6507 (7) and 3.6866 (7) A ] interactions between thiazole rings
The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from HÁ Á ÁH (47.0%), HÁ Á ÁO/ OÁ Á ÁH (16.9%), HÁ Á ÁC/CÁ Á ÁH (8.0%) and HÁ Á ÁS/SÁ Á ÁH (7.6%) interactions

Summary

Chemical context

Compounds containing the benzothiazole backbone have been studied extensively in both academic and industrial laboratories (Mekhzoum et al, 2016, 2019; Chakib et al, 2010a,b, 2019). These molecules exhibit a wide range of biological applications including as anti-tumor agents (Beneteau et al, 1999; Caleta et al, 2004), antimicrobial agents (Shastry et al, 2003; Latrofa et al, 2005, Singh et al, 2013), analgesics (Kaur et al, 2010), anti-inflammatory agents (Oketani et al, 2001), anti-HIV agents (Nagarajan et al, 2003; Pitta et al, 2013), anti-leishmanial agents (Delmas et al, 2004), anti-cancer agents (Yang et al, 2003; Huang et al, 2006; Kok et al, 2008), anti-hypertensive agents (Saggu et al, 2002), antioxidants, (Ayhan-Kilcigil et al, 2004) and anti-viral agents (Tewari et al, 2006). The results of the calculations by density functional theory (DFT), carried out at the B3LYP/6-311G (d,p) level, are compared with the experimentally determined molecular structure in the solid state

Supramolecular features

Structural commentary

Hirshfeld surface analysis

Interaction energy calculations

Findings

Database survey