3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study
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...
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International Union of Crystallography
2019
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| Online Access: | http://eprints.sunway.edu.my/1102/ http://eprints.sunway.edu.my/1102/1/Tiekink%203%203%20Bis%202%20hydroxyethyl%20Acta%20Cryst.%20%282019%29%20E75%201472.pdf |
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| author | Tan, Sang Loon * Ainnul H. S. Azizan, * Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_facet | Tan, Sang Loon * Ainnul H. S. Azizan, * Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_sort | Tan, Sang Loon * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T21:15:59Z |
| format | Article |
| id | sunway-1102 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:15:59Z |
| publishDate | 2019 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-11022020-10-12T07:22:57Z http://eprints.sunway.edu.my/1102/ 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study Tan, Sang Loon * Ainnul H. S. Azizan, * Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry 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. International Union of Crystallography 2019-09-09 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1102/1/Tiekink%203%203%20Bis%202%20hydroxyethyl%20Acta%20Cryst.%20%282019%29%20E75%201472.pdf 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) http://doi.org/10.1107/S2056989019012581 doi:10.1107/S2056989019012581 |
| spellingShingle | QD Chemistry Tan, Sang Loon * Ainnul H. S. Azizan, * Jotani, Mukesh M. Tiekink, Edward R. T. * 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title | 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_full | 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr | 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed | 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_short | 3,3-Bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort | 3,3-bis(2-hydroxyethyl)-1-[(4-methylphenyl)carbonyl]thiourea: crystal structure, hirshfeld surface analysis and computational study |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1102/ http://eprints.sunway.edu.my/1102/ http://eprints.sunway.edu.my/1102/ http://eprints.sunway.edu.my/1102/1/Tiekink%203%203%20Bis%202%20hydroxyethyl%20Acta%20Cryst.%20%282019%29%20E75%201472.pdf |