2-[Carbamothioyl(2-hydroxyethyl)amino]ethyl benzoate: crystal structure, Hirshfeld surface analysis and computational study

Abstract

The title di-substituted thiourea, C12H16N2O3S, has the hydroxylethyl and ethyl benzoate substituents bound to the same amine-N atom, and is twisted, having a (+)syn-clinal conformation with the Namine—C—C—O(hydroxyl, carbonyl) torsion angles of 49.39 (13) and 59.09 (12)°, respectively; the dihedral angle between the almost planar CN2S core and the pendent benzene ring is 69.26 (4)°. In the crystal, supramolecular layers propagating in the ac plane are formed via a combination of hydroxyl-O—H...S(thione), amine-N—H...O(hydroxyl, carbonyl) hydrogen-bonds. The layers stack along the b axis with inter-digitation of the benzene rings allowing the formation of π–π stacking [inter-centroid separation = 3.8722 (7) Å] and parallel C=O...π interactions. A computational chemistry study shows the conventional hydrogen bonding in the crystal leads to significant electrostatic stabilization but dispersion terms are also apparent, notably through the interactions involving the benzene residue.

Keywords

• crystal structure
• thiourea
• hydrogen bonding
• hirshfeld surface analysis
• computational chemistry