N-[Ethyl(2-hydroxyethyl)carbamothioyl]-2-methylbenzamide

The title compound, C13H18N2O2S, adopts a cis conformation between the methylbenzoyl and thiono groups across their thiourea C—N bond. However, the methylbenzoyl group and N2CS thiourea moiety are twisted by 15.03 (3)°. In the molecule there is an N—H⋯O hydrogen bond. In the crystal, molecules are linked by O—H⋯O interactions, generating chains extending along the c-axis direction.

The title compound, C 13 H 18 N 2 O 2 S, adopts a cis conformation between the methylbenzoyl and thiono groups across their thiourea C-N bond. However, the methylbenzoyl group and N 2 CS thiourea moiety are twisted by 15.03 (3) . In the molecule there is an N-HÁ Á ÁO hydrogen bond. In the crystal, molecules are linked by O-HÁ Á ÁO interactions, generating chains extending along the c-axis direction.

Synthesis and crystallization
An acetone (30 ml) solution of 2-(ethylamino)ethanol (0.18 g, 2 mmol) was added to a round-bottomed flask containing 2-methylbenzoyl isothiocyanate (0.31 g,2 mmol). The mixture was refluxed for 3h. After cooling the solution was filtered off and the filtrate was left to evaporate at room temperature. The solid formed was washed with water and cold ethanol.
Crystals suitable for X-ray study were obtained by recrystallization from DMSO.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C-H= 0.93-0.97Å and N-H = 0.86Å with U iso (H)= 1.2U eq [C (methylene and aromatic),N] and 1.5 U eq [C (methyl)]. The hydroxyl hydrogen atom was located from Fourier map and refined isotropically with O-H restraint to 0.81Å with esd of 0.01.

Results and discussion
The carbonoylthiourea derivatives with a secondary amine group at the terminal thiourea moiety are expected to adopt a cis conformation with respect to the position of the carbonoyl against the thiono group. Such a configuration will allow the ligand to chelate with metals in bidentate manner. Thus, 2,4-dichloro-N-[ethyl(hydroxyethyl)carbamothioyl]benzamide (Sapari et al.,2013) and N[ethyl(hydroxyethyl)carbamothioyl]-2-iodo-benzamide (Awang et al., 2013) adopt the said conformation. The title compound is analogous to the two compounds but having a methyl group attached at position-2 of the benzene ring ( Fig.1). However, the title molecule maintains a cis conformation between the carbonyl and thiono groups across the C8-N1 bond and twisted by torsion angle of O1-C8-N1-C9 and S1-C9-N1-C8 of 7.1 (3)and 47.1 (2)° respectively. Both S1/N1/N2/C9 thiourea moiety and (C1-C8) benzyl fragments are planar with maximum deviation of 0.031 (2)Å for C4 atom from the least square plane of the benzyl fragment. The two planes make dihedral angle of 15.03 (3)°. The bond lengths and angles are in normal ranges (Allen et al.,1987) and comparable to those in the two analogs. There is an intramolecular hydrogen bond N1-H1A···O2 between the amido hydrogen and hydroxyl oxygen atom. In the crystal structure, the molecules are linked by O2-H2A···O1 intermolecular hydrogen bond (see Table 1 for symmetry codes) to form one-dimensional chains along the c-axis direction (Fig.2). In addition, there is a C-H.. π bond between H12B and (C1-C6) centroid (-x,1-y,-z) with the H12B···C g distance of 2.84Å and C12-H12B -C g angle, 137°.  The molecular structure of (I), with displacement ellipsods drawn at the 50% probability level. The dashed line indicates the intramolecular hydrogen bond.

Figure 2
Packing of (I) viewed down the a-axis. The dashed lines indicate intermolecular hydrogen bonds.

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 > 2sigma(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.