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

• Main Authors: Tan, Sang Loon *, Tiekink, Edward R. T. *
• Format: Article
• Language: English
• Published: International Union of Crystallography 2020
• Subjects: QD Chemistry
• Online Access: http://eprints.sunway.edu.my/1298/1/Tiekink%20Acta%20Cryst%202020%20E76%20933.pdf; http://eprints.sunway.edu.my/1298/; http://doi.org/10.1107/S2056989020006829
• Institution: Sunway University

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.