1-Benzoyl-3-methyl-3-pentylthiourea

Abstract

Two independent mol­ecules comprise the asymmetric unit of the title compound, C14H20N2OS. These differ in the relative orientations of the pentyl chains [C—C—C—C torsion angles = −176.7 (3) and 176.4 (3)°]. Significant twists are evident in each mol­ecule, the dihedral angles formed between the thio­urea and amide residues being 53.47 (17) and 55.81 (17)°. In the crystal, each mol­ecule self-associates via a centrosymmetric eight-membered {⋯HNC=S}2 synthon, and these are connected into a supra­molecular chain along [110] via C—H⋯O contacts. Disorder is noted for one of the independent mol­ecules in that two orientations (50:50) were resolved for its benzene ring.

Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: An experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea

“…deviation 0.115 Å) shows that there are no remarkable differences between the two molecules, as can be observed inFigure 5.The carbonyl oxygen in the amide group is slightly out of the mean plane of the benzene ring, the N1-C7-C1-C2 torsion angle being 50.8(2)º, in reasonable agreement with the computed value for the free molecule of 40.9º (seeFigure 3). Similar conformational features were reported for chloro-benzoyl thioureas[59,60]. Bond lengths and angles in the heavy atom skeletons are within normal ranges[61,62] (see Tables S5 and S6in the Supplementary data).…”