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.

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??(ring) and head-to-tail slipped ?-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.

SUBMITTER: Srhir M 

PROVIDER: S-EPMC7057389 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature