N-(3-Chloropropionyl)-N′-phenylthiourea

The title compound, C10H11ClN2OS, adopts a cis-trans configuration with respect to the position of the phenyl and 3-chloropropionyl groups relative to the thiono group across the C—N bonds. The benzene ring is perpendicular to the propionyl thiourea fragment with a dihedral angle of 82.62 (10)°. An intramolecular N—H⋯O interaction occurs. The crystal structure is stabilized by intermolecular N—H⋯S hydrogen bonds, which link pairs of molecules, building up R 2 2(8) ring motifs, and C—H.. π interactions.

The title compound, C 10 H 11 ClN 2 OS, adopts a cis-trans configuration with respect to the position of the phenyl and 3-chloropropionyl groups relative to the thiono group across the C-N bonds. The benzene ring is perpendicular to the propionyl thiourea fragment with a dihedral angle of 82.62 (10) . An intramolecular N-HÁ Á ÁO interaction occurs. The crystal structure is stabilized by intermolecular N-HÁ Á ÁS hydrogen bonds, which link pairs of molecules, building up R 2 2 (8) ring motifs, and C-H.. interactions.

Comment
The presence of both alpha and ipso chlorine atoms in 2-chloropropionyl chloride could lead to a complicated reaction when reacted with a nucleophile such as thiocyanate depending on the solvent used. For example, the reaction of 2-chloropropionyl chloride with ammonium thiocyanate and succeedingly with aniline in acetone was found to give 4,5,6-trimethyl-1phenyl-3,4-dihydropyrimidine-2(1H)-thione (Ismail et al., 2007) instead of the expected N-phenyl-N'-(2-chloropropionyl) thiourea. However, in the present study, the same reaction but with 3-chloropropionyl chloride, the expected N-phenyl-N'- The whole molecule is not planar (Fig.1). The benzene (C5-C10) ring and propionylthiourea fragment, S1/N1/N2/ (C1-C4) are each planar with maximum deviation of 0.062 (2)Å for C3 atom from the least square plane. The benzene ring is roughly perpendicular to the propionylthiourea fragment with dihedral angle between the two planes of 82.62 (10)°. A smaller dihedral angle of 12.68 (7)° was observed in an analogous compound of N-(3-chloropropionyl)-N'(4-fluorophenyl) thiourea (II) (Ismail & Yamin, 2009).The trans-cis configuration of the propionyl and phenyl groups relative to the thiono group respectively, across their C-N bonds, is maintained. The bond lengths and angles are in normal range (Allen et al.,1987) and comparable to those in (II).

Refinement
After locating the hydrogen atoms from a different-Fourier map, they were positioned geonmetrically with C-H=0.93-0.97Å and N-H=0.86Å respectively, and constrained to all their parent atoms with U iso (H)=1.2U eq (parent atom). There is a highest peak and deepest hole of 0.97 and 0.81 Å respectively from S1 atom.  Fig. 1. The molecular structure of (I),with displacement ellipsods drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 Rfactors(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.