Crystallographic study of self-organization in the solid state including quasi-aromatic pseudo-ring stacking interactions in 1-benzoyl-3-(3,4-di-methoxyphenyl)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, C_16H_16N_2O_3S, (I), and 1-benzoyl-3-(2-hydroxypropyl)thiourea, C_11H_14N_2O_2S, (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—H ???O hydrogen bonding is present. The resulting six-membered pseudo-rings are quasi-aromatic and, in each case, interact with phenyl rings via stacking-type interactions. C—H ??? O, C—H ??? S and C—H ??? π interactions are also present. In (I), there is one molecule in the asymmetric unit. Pairs of molecules are connected via two intermolecular N—H ??? 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 ??? O and O—H ??? S hydrogen bonds that join molecules into chains extending in the [001] direction.