1,1-Diethyl-3-(4-methylbenzoyl)thiourea

Abstract

The title compound, C 13 H 18 N 2 OS, crystallizes as NH tautomer. The C5-C8(O)-N system tends to be coplanar with the phenyl ring [C4-C5-C8-O = 8.7 (4)°] because of some π-conjugation along the O-C8-C(Ph) system [C5-C8 = 1.448 (4) Å] and the O···H4 = 2.49Å attractive interaction. The molecules in the crystal are held together by van der Waals forces and an intermolecular N-H···O hydrogen bond.

Polymorphism in bipodalO,O′-dimethylN,N′-(m-phenylenedicarbonyl)bis(thiocarbamate)

“…The approximate anti orientation of the S and O atoms within the C(S)NHC(O) moieties of (I), and of atoms O3 and S2 in (II), is frequently observed in the closely related bipodal N H ,N H ,N HHH ,N HHH -tetraalkyl-N,N HH -aroylbis(thioureas) Ugur et al, 2003). This anti orientation of the S and O atoms is also frequently observed in the monopodal N-aroyl-N H -alkyl-and N-aroyl-N H ,N H -dialkylthioureas (Koch, Sacht, Grimmbacher & Bourne, 1995;Morales et al, 1997Morales et al, , 2000aShanmuga Sundara Raj et al, 1999). The comparable uncommon syn orientation of the thiocarbonyl and carbonyl moieties (S1 and O2) observed in (II) was also observed in the structurally related et al, 2004).…”