1-{[(Z)-Cyclopentylidene]amino}-3-phenylthiourea

The sample of the title compound, C12H15N3S, chosen for study consisted of triclinic crystals twinned by a 180° rotation about the a axis. The five-membered ring adopts a twisted conformation. The dihedral angle between the phenyl ring and the mean plane of the thiourea unit is 78.22 (8)°. In the crystal, molecules are linked via pairs of N—H⋯S hydrogen bonds forming inversion dimers.

The sample of the title compound, C 12 H 15 N 3 S, chosen for study consisted of triclinic crystals twinned by a 180 rotation about the a axis. The five-membered ring adopts a twisted conformation. The dihedral angle between the phenyl ring and the mean plane of the thiourea unit is 78.22 (8) . In the crystal, molecules are linked via pairs of N-HÁ Á ÁS hydrogen bonds forming inversion dimers.
The support of NSF-MRI grant No. 1228232 for the purchase of the diffractometer is gratefully acknowledged.
Supporting information for this paper is available from the IUCr electronic archives (Reference: SJ5395).

Comment
For the past few decades, thiourea derivatives have attracted great attention not only because they are important building blocks in the synthesis of heterocycles and organo-metal complexes (Yin et al., 2008) but also due to their broad spectrum of biological activities such as anti-bacterial, anti-cancer (Saeed et al., 2010), anti-malarial (Solomon et al., 2010, anti-tuberculosis (Karakuş & Rollas 2002) anti-convulsion, analgesic and HDL-elevating properties. In addition, metal complex of thiourea derivatives exhibit anti-inflammatory, anti-cancer and anti-fungal activities (Abdullah & Salh, 2010). Furthermore, the thiourea structure contains a central hydrophilic part and two hydrophobic moieties forming a butterfly-like conformation. This conformation is a part of the structure of an anti-HIV agent (Struga et al., 2009). In the crystal structure, the molecules are connected by weak N-H···S interactions ( Fig. 2 and Table 1).

Experimental
The title compound was prepared according to our previously reported method (Akkurt et al., 2014). Colourless crystals suitable for X-ray diffraction were obtained by crystallization of (I) from ethanol.

Refinement
H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 -0.98 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N-H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 -1.5 times those of the attached atoms. The crystal used proved to be twinned by a 180° rotation about a, CELL_NOW, (Sheldrick, 2008a)   Perspective view of I with 50% probability displacement ellipsoids.

Figure 2
Packing viewed down the a axis and showing N-H···S interactions. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.28 e Å −3 Δρ min = −0.20 e Å −3 Special details Experimental. Analysis of 985 reflections having I/σ(I) > 15 and chosen from the full data set with CELL_NOW (Sheldrick, 2008a) showed the crystal to belong to the triclinic system and to be twinned by a 180° rotation about the a axis. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 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. H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 -0.99 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N-H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.89113 (