O-Propyl N-phenylthiocarbamate

Two independent molecules comprise the asymmetric unit in the title thiocarbamide derivative, C10H13NOS. These differ in the relative orientations of terminal ethyl groups [C—C—C—O torsion angles = −66.95 (13) and 55.92 (13)°, respectively]. The phenyl ring is twisted out of the plane of the central residue [Cq—N—Cph—Cph = −146.20 (12) and −144.15 (12)°, respectively; q = quaternary and ph = phenyl]. The independent molecules are linked into a dimeric aggregate by N—H⋯S hydrogen bonds and an eight-membered thioamide {⋯H—N—C=S}2 synthon.


Experimental
Crystal data H atoms treated by a mixture of independent and constrained refinement Á max = 0.22 e Å À3 Á min = À0.26 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). PS thanks the Development and Promotion of Science and Technology Talents Project (DPST), Thailand, for support to enable study at the University of Malaya. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12). supplementary materials Acta Cryst. (2012). E68, o1774 [doi:10.1107/S160053681202140X]

Comment
The title thiocarbamate, (I), was investigated as a continuation of systematic evaluation of the structural features of this class of compound (Ho et al., 2005;Kuan et al., 2007). In (I), Fig. 1, two independent molecules comprise the asymmetric unit, and these have very similar molecular conformations as seen in the overlay diagram, Fig. 2. The difference arises in the pseudo mirror relationship in the terminal ethyl group as seen in the C1-C2-C3-O1 and C11 -C12-C13-O2 torsion angles of -66.95 (13) and 55.92 (13)°, respectively. A further twist is evident in the molecule as seen in the value of the C4-N1-C5-C6 torsion angle of -146.20 (12)°; the equivalent torsion angle for the second independent molecule [C14-N2-C15-C16] is -144.15 (12)°. The geometric parameters match literature precedents (Ho et al., 2005;Kuan et al., 2007) The independent molecules are linked into a dimeric aggregate by N-H···S hydrogen bonds and an eight-membered thioamide {···H-N-C=S} 2 synthon, Table 1, as found in most thiocarbamate structures (Kuan et al., 2007). Molecules assemble into a three-dimensional architecture with no specific interactions between them.

Experimental
Phenyl isothiocyanate (2 ml) was added drop-wise to a stirred solution of NaOH (1 mol equiv.) in n-propanol (20 ml) and stirred for 3 h. Excess HCl (5M) was then added and the solution was stirred for a further 1 h. The product was then  The molecular structures of the two independent molecules comprising (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. The dashed lines represent N-H hydrogen bonds.

Figure 2
Overlay diagram of the two independent molecules comprising the asymmetric unit of (I). The first independent molecule (with the S1 atom) is shown in red and the second (S2) in blue. The S, O and N atoms in each molecule have been overlapped.

Special details
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.71820 (