2-[Carbamo-thio-yl(2-hy-droxy-eth-yl)amino]-ethyl benzoate: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The title di-substituted thio-urea, C12H16N2O3S, has the hy-droxy-lethyl 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, carbon-yl) 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, supra-molecular layers propagating in the ac plane are formed via a combination of hydroxyl-O-H?S(thione), amine-N-H?O(hydroxyl, carbon-yl) hydrogen-bonds. The layers stack along the b axis with inter-digitation of the benzene rings allowing the formation of ?-? stacking [inter-centroid separation = 3.8722?(7)?Å] and parallel C=O?? inter-actions. 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 inter-actions involving the benzene residue.

SUBMITTER: Tan SL 

PROVIDER: S-EPMC7274010 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature