3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study

Tan, Sang Loon * and Ainnul H. S. Azizan, * and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2019) 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 75 (10). pp. 1472-1478. ISSN 2056-9890 (In Press)

Tiekink 3 3 Bis 2 hydroxyethyl Acta Cryst. (2019) E75 1472.pdf - Accepted Version
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Official URL: http://doi.org/10.1107/S2056989019012581


In the title tri-substituted thiourea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the molecule [the S—C—N—C torsion angle is-49.3 (2)⁰]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 A ˚ ) with the hydroxyethyl groups lying to either side of this plane. One hydroxyethyl group is orientated towards the thioamide functionality enabling the formation of an intramolecular N—H...O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)⁰] between the planes through the CN2S atoms and the 4-tolyl ring indicates the molecule is twisted. The experimental molecular structure is close to the gas-phase, geometryoptimized structure calculated by DFT methods. In the molecular packing, hydroxyl-O—H...O(hydroxyl) and hydroxyl-O—H...S(thione) hydrogen bonds lead to the formation of a supramolecular layer in the ab plane; no directional interactions are found between layers. The influence of the specified supramolecular interactions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent interaction plots; the interaction energies point to the important stabilization provided by directional O—H...O hydrogen bonds.

Item Type: Article
Uncontrolled Keywords: crystal structure; thiourea; hydrogen bonding; Hirshfeld surface analysis; computational chemistry.
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 23 Sep 2019 02:10
Last Modified: 12 Oct 2020 07:22
URI: http://eprints.sunway.edu.my/id/eprint/1102

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