Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-(1,3-benzothiazol-2-yl)-3-(2-hydroxyethyl)imidazolidin-2-one

In the title molecule, C₁₂H₁₃N₃O₂S, the benzothiazine 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 = hydroxyethyl, Thz = thiazole, Imdz = imidazolidine and Bnz = benzene) interactions, together with C-HImdz p(ring) and head-to-tail slipped p-stacking [centroid-to-centroid distances = 3.6507 14;(7) and 3.6866 14;(7) 14;Å] interactions between thiazole 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%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions 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 14;kJ 14;mol^-1 (for C-HImdz OImdz). Density functional theory (DFT) optimized structures at the B3LYP/6-311 14;G(d,p) level are compared with the experimentally determined molecular structure in the solid state.