RESUMO
The title compound, C18H12Cl2N2OS, consists of a di-hydro-benzo-thia-zine unit linked by a -CH group to a 2,4-di-chloro-phenyl substituent, and to a propane-nitrile unit is folded along the Sâ¯N axis and adopts a flattened-boat conformation. The propane-nitrile moiety is nearly perpendicular to the mean plane of the di-hydro-benzo-thia-zine unit. In the crystal, C-HBnzâ¯NPrpnit and C-HPrpnitâ¯OThz (Bnz = benzene, Prpnit = propane-nitrile and Thz = thia-zine) hydrogen bonds link the mol-ecules into inversion dimers, enclosing R 2 2(16) and R 2 2(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=Oâ¯Cl inter-actions. π-π contacts between the benzene and phenyl rings, [centroid-centroid distance = 3.974â (1)â Å] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Hâ¯H (23.4%), Hâ¯Cl/Clâ¯H (19.5%), Hâ¯C/Câ¯H (13.5%), Hâ¯N/Nâ¯H (13.3%), Câ¯C (10.4%) and Hâ¯O/Oâ¯H (5.1%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry calculations indicate that the two independent C-HBnzâ¯NPrpnit and C-HPrpnitâ¯OThz hydrogen bonds in the crystal impart about the same energy (ca 43â kJâ mol-1). Density functional theory (DFT) optimized structures at the B3LYP/6-311â G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.