Abstract
In the title tri-substituted thio-urea derivative, C13H18N2O3S, the thione-S and carbonyl-O atoms lie, to a first approximation, to the same side of the mol-ecule [the S-C-N-C torsion angle is -49.3 (2)°]. The CN2S plane is almost planar (r.m.s. deviation = 0.018 Å) with the hy-droxy-ethyl groups lying to either side of this plane. One hy-droxy-ethyl group is orientated towards the thio-amide functionality enabling the formation of an intra-molecular N-H⋯O hydrogen bond leading to an S(7) loop. The dihedral angle [72.12 (9)°] between the planes through the CN2S atoms and the 4-tolyl ring indicates the mol-ecule is twisted. The experimental mol-ecular structure is close to the gas-phase, geometry-optimized structure calculated by DFT methods. In the mol-ecular packing, hydroxyl-O-H⋯O(hydrox-yl) and hydroxyl-O-H⋯S(thione) hydrogen bonds lead to the formation of a supra-molecular layer in the ab plane; no directional inter-actions are found between layers. The influence of the specified supra-molecular inter-actions is apparent in the calculated Hirshfeld surfaces and these are shown to be attractive in non-covalent inter-action plots; the inter-action energies point to the important stabilization provided by directional O-H⋯O hydrogen bonds.
Highlights
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 À49.3 (2)]
Hydroxyl-O—HÁ Á ÁO(hydroxyl) and hydroxyl-O—HÁ Á ÁS(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—HÁ Á ÁO hydrogen bonds
Summary
The amine-H atoms in thiourea, H2NC( S)NH2, can be systematically replaced to generate up to tetra-functionalized molecules, i.e. R1(R2)NC( S)N(R3)R4 for R1–4 = alkyl/aryl. The present study concerns a tri-substituted example, i.e. an N,N0-di(alkyl/aryl)-N0-benzoylthiourea derivative, notable for having a carbonyl group connected to the thiourea framework. Thiourea molecules are of interest in themselves and as ligands for metal ions (Saeed et al, 2014). The free molecules, including benzoyl derivatives, are well-known to exhibit various biological properties, for example, anti-bacterial, antifungal and anti-viral activities as well as cytotoxicity (Hallur et al, 2006; Cunha et al, 2007; Saeed et al, 2010; Gunasekaran et al, 2017; Zhang et al, 2018; Gunasekaran, Ng et al, 2012). The structure features a tri-substituted thiourea molecule with one N atom bearing a benzoyl residue and the other, carrying two hydroxyethyl groups. The bond angles subtended at the C1 and C6 atoms follow the expected trends in that those involving the formally doubly bonded atoms are wider, by approximately 10, compared with the other angles, Table 1
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