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

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

doi:10.1107/S2056989020001723

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

Acta Crystallogr E Crystallogr Commun. 2020 Feb 14;76(Pt 3):370-376. doi: 10.1107/S2056989020001723. eCollection 2020 Mar 1.

Authors

Mohamed Srhir¹, Nada Kheira Sebbar^{2

1}, Tuncer Hökelek³, Ahmed Moussaif¹, Joel T Mague⁴, Noureddine Hamou Ahabchane¹, El Mokhtar Essassi¹

Affiliations

¹ Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco.
² Faculté des Sciences Appliquées Ait Melloul, Université Ibn Zohr, Agadir, Morocco.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

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-H_Hydethy⋯N_Thz hydrogen bonds and weak C-H_Imdz⋯O_Imdz and C-H_Bnz⋯O_Imdz (Hydethy = hy-droxy-ethyl, Thz = thia-zole, Imdz = imidazolidine and Bnz = benzene) inter-actions, together with C-H_Imdz⋯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-H_Hydethy⋯N_Thz), 60.1 (for C-H_Bnz⋯O_Imdz) and 41.8 kJ mol^-1 (for C-H_Imdz⋯O_Imdz). 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.

Keywords: Hirshfeld surface; benzothiazine; crystal structure; hydrogen bond; triazole; π-stacking.

Grants and funding

This work was funded by National Science Foundation grant 1228232. Tulane University grant . Hacettepe University Scientific Research Project Unit grant 013 D04 602 004 to T. Hökelek.