1-{(E)-[4-(4-Meth-oxy-phen-yl)butan-2-yl-idene]amino}-3-methyl-thio-urea

Abstract

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(13)H(19)N(3)OS, which differ in the conformations of the residues linking the thio-urea and the terminal benzene ring, as manifested in the C(m)-C(m)-C(a)-C(a) torsion angles [78.03 (16) and -93.64 (16)°, respectively; m = methyl-ene and a = aromatic]. The dihedral angles [84.40 (4) and 88.28 (5)°] formed between the thio-urea residue and the benzene ring indicate an almost orthogonal relationship. In each thio-urea residue, the N-H hydrogen atoms are anti, and the terminal N-H hydrogen atom forms an intra-molecular N-H⋯N hydrogen bond with the imine-N atom. In each case, the conformation about the imine C=N double bond [1.2812 (17) and 1.2801 (17) Å] is E. In the crystal, the mol-ecules are connected by N-H⋯S hydrogen bonds and these are connected into four mol-ecule aggregates via N-H⋯O hydrogen bonds, which are assembled into a two-dimensional array parallel to (011) via C-H⋯π and π-π inter-actions [ring centroid-centroid distance = 3.8344 (9) Å].

Fig. 1.

The molecular structure of the two independent molecules in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Hydrogen bonds are shown as dashed lines.

Fig. 2.

An overlay diagram of two independent molecules in (I). The S1-containing molecule is illustrated in red and the S2-molecule in blue. Molecules have been aligned so that the N1,S1,N2 and N4,S2,N5 planes are overlapped.

Fig. 3.

A view of the supramolecular layer parallel to (011) in (I) mediated by N—H···S, N—H···O, C—H···π and π–π interactions shown as blue, orange, brown and purple dashed lines, respectively.

Fig. 4.

A view in projection down the a axis of the unit-cell contents for (I). The N—H···S, N—H···O, C—H···π and π–π interactions shown as blue, orange, brown and purple dashed lines, respectively.