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

In the title tri-substituted thio­urea derivative, C(13)H(18)N(2)O(3)S, 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)°]. The CN(2)S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hy­droxy­ethyl...

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Detalles Bibliográficos
Autores principales: Tan, Sang Loon, Azizan, Ainnul Hamidah Syahadah, Jotani, Mukesh M., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6775753/
https://www.ncbi.nlm.nih.gov/pubmed/31636978
http://dx.doi.org/10.1107/S2056989019012581
Descripción
Sumario:In the title tri-substituted thio­urea derivative, C(13)H(18)N(2)O(3)S, 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)°]. The CN(2)S plane is almost planar (r.m.s. deviation = 0.018 Å) 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)°] between the planes through the CN(2)S atoms and the 4-tolyl ring indicates the mol­ecule is twisted. The experimental mol­ecular structure is close to the gas-phase, geometry-optimized 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.