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

摘要

1-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, C16H16N2O3S, (I), and 1-benzoyl-3-(2-hydroxypropyl)thiourea, C11H14N2O2S, (II), have been synthesized and characterized. Compound (I) crystallizes in the space group P (1) over bar, while (II) crystallizes in the space group P2(1)/c. In both structures, intramolecular N-H center dot center dot center dot O 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-H center dot center dot center dot O, C-H center dot center dot center dot S and C-H center dot center dot center dot pi interactions are also present. In (I), there is one molecule in the asymmetric unit. Pairs of molecules are connected via two intermolecular N-H center dot center dot center dot S 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-H center dot center dot center dot O and O-H center dot center dot center dot S hydrogen bonds that join molecules into chains extending in the [001] direction.