3-Acetyl-1-(3-chlorophenyl)thiourea

In the title compound, C9H9ClN2OS, the 3-chlorophenyl and acetylthiourea fragments are oriented at a dihedral angle of 62.68 (5)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. Molecules are linked into dimers via a cyclic R 2 2(8) motif of N—H⋯S hydrogen bonds. These dimers are further connected through C—H⋯S interactions, completing an R 2 2(12) motif, into chains along [010].


Raza Comment
The title compound ( Fig. 1) has been synthesized as a continuation of our work to find new enzyme inhibitors.
The mixture was refluxed for 5-10 min, then poured on ice cooled water, which resulted in crude precipitate.
Recrystallization of the precipitate from ethyl acetate yielded colorless rods (m.p. 374 K).

Refinement
The H atoms were positioned geometrically (C-H = 0.93-0.96 Å, N-H = 0.86 Å) and refined as riding with U iso (H) = xU eq (C, N), where x = 1.5 for methyl groups and x = 1.2 for other H atoms.

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009   The partial packing (PLATON; Spek, 2009) showing molecules connected via N-H···O and C-H···S interactions. Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) 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.