1-(2-Hydroxyethyl)-3-phenylthiourea

The title compound, C9H12N2OS, was obtained unexpectedly in a multicomponent reaction of an equimolar ratio of phenyl isothiocyanate, malononitrile and aminoethanol. The –C(H2)–N(H)–(C=S)–N(H)– methylthiourea–methane group is almost normal to the phenyl ring, with a dihedral angle of 71.13 (9)°. The N—C—C—O torsion angle is 72.8 (2)°. In the crystal, molecules are connected by N—H⋯O, O—H⋯S and N—H⋯O hydrogen bonds, forming a three-dimensional network.

The title compound, C 9 H 12 N 2 OS, was obtained unexpectedly in a multicomponent reaction of an equimolar ratio of phenyl isothiocyanate, malononitrile and aminoethanol. The -C(H 2 )-N(H)-(C S)-N(H)-methylthiourea-methane group is almost normal to the phenyl ring, with a dihedral angle of 71.13 (9) . The N-C-C-O torsion angle is 72.8 (2) . In the crystal, molecules are connected by N-HÁ Á ÁO, O-HÁ Á ÁS and N-HÁ Á ÁO hydrogen bonds, forming a three-dimensional network.
The Higher Education Authority in Egypt is acknowledged for their financial support of this research project. We also thank Manchester Metropolitan University for supporting this study.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2342).

Experimental
The 1-(2-hydroxyethyl)-3-phenylthiourea has been formed as an unexpected product from a multicomponent reaction of an equimolar ratio of phenylisothiocyanate, malononitrile and amino ethanol. The reaction mixture was heated at 374 K in dioxane (30 ml) for 3 h, then cooled at room temperature to afford a solid precipitate. The product was filtered off, washed with cold ethanol and recrystallized from ethanol. Colourless needles in a spiky shape have been isolated on slow evaporation of a diluted ethanol of the product (yield 39%, m.p. 393 K).

Refinement
All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93Å for aromatic, C-H = 0.97Å for methylene, O-H = 0.82Å for hydroxyl and N-H = 0.86Å for amine H atoms, and with U iso (H) = 1.2(1.5)U eq (C,N,O).

Computing details
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009     where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.31 e Å −3 Δρ min = −0.24 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All s.u.'s are estimated from the variances of the (full) variance-covariance matrix. The cell s.u.'s are taken into account in the estimation of distances, angles and torsion angles. Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > σ(F 2 ) is used only for calculating R-factor etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.