Crystallographic study of self-organization in the solid state including quasi-aromatic pseudo-ring stacking interactions in 1-benzoyl-3-(3,4-dimethoxyphenyl)thiourea and 1-benzoyl-3-(2-hydroxypropyl)thiourea (original) (raw)

2017, Acta Crystallographica Section C: Structural Chemistry

Benzoylthioureas contain both carbonyl and thiocarbonyl functional groups and are of interest for their biological activity, metal coordination ability and involvement in hydrogen-bond formation. Two novel 1-benzoylthiourea derivatives, namely 1-benzoyl-3-(3,4-dimethoxyphenyl)thiourea, C 16 H 16 N 2 O 3 S, (I), and 1-benzoyl-3-(2-hydroxypropyl)thiourea, C 11 H 14 N 2 O 2 S, (II), have been synthesized and characterized. Compound (I) crystallizes in the space group P1, while (II) crystallizes in the space group P2 1 /c. In both structures, intramolecular N-HÁ Á ÁO hydrogen bonding is present. The resulting six-membered pseudorings are quasi-aromatic and, in each case, interact with phenyl rings via stacking-type interactions. C-HÁ Á ÁO, C-HÁ Á ÁS and C-HÁ Á Á interactions are also present. In (I), there is one molecule in the asymmetric unit. Pairs of molecules are connected via two intermolecular N-HÁ Á ÁS hydrogen bonds, forming centrosymmetric dimers. In (II), there are two symmetry-independent molecules that differ mainly in the relative orientations of the phenyl rings with respect to the thiourea cores. Additional strong hydrogen-bond donor and acceptor-OH groups participate in the formation of intermolecular N-HÁ Á ÁO and O-HÁ Á ÁS hydrogen bonds that join molecules into chains extending in the [001] direction.