Akademik Veri Yönetim Sistemi
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.370-381, 2020 (ESCI)
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 be plane is formed by a combination of O-H-Hydethy center dot center dot center dot N-Thz hydrogen bonds and weak C-H-Imdz center dot center dot center dot O-Imdz and C-H-Bnz center dot center dot center dot O-Imdz (Hydethy = hydroxyethyl, Thz = thiazole, Imdz = imidazolidine and Bnz = benzene) interactions, together with C-H-Imdz center dot center dot center dot pi(ring) and head-to-tail slipped pi-stacking [centroid-to-centroid distances = 3.6507 (7) and 3.6866 (7) angstrom] 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 center dot center dot center dot H (47.0%), H center dot center dot center dot O/O center dot center dot center dot H (16.9%), H center dot center dot center dot C/C center dot center dot center dot H (8.0%) and H center dot center dot center dot S/S center dot center dot center dot 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 center dot center dot center dot N and C-H center dot center dot center dot O hydrogen-bond energies are 68.5 (for O-H-Hydethy center dot center dot center dot N-Thz), 60.1 (for C-H-bnz center dot center dot center dot O-Imdz) and 41.8 kJ mol(-1) (for C-H-Imdz center dot center dot center dot O-Imdz). Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state.