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

In the title compound, C12H15N3O5S, a tris­ubstituted thio­urea derivative, the central CN2S chromophore is almost planar (r.m.s. deviation = 0.018 Å) and the pendant hy­droxy­ethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the mol­ecule, the S—C—N—C torsion angle of −47.8 (2)° indicates a considerable twist. As one of the hy­droxy­ethyl groups is orientated towards the thio­amide residue, an intra­molecular N—H⋯O hydrogen bond is formed which leads to an S(7) loop. A further twist in the mol­ecule is indicated by the dihedral angle of 65.87 (7)° between the planes through the CN2S chromophore and the 4-nitro­benzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) mol­ecular structures. In the crystal, O—H⋯O and O—H⋯S hydrogen bonds give rise to supra­molecular layers propagating in the ab plane. The connections between layers to consolidate the three-dimensional architecture are of the type C—H⋯O, C—H⋯S and nitro-O⋯π. The nature of the supra­molecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent inter­action plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.