title: 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.
abstract: 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, while (II) crystallizes in the space group P21/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.
authors.affiliation: Department of Inorganic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, G. Narutowicza 11/12, 80-233 Gdańsk, Poland.
authors.forename: Andrzej
authors.initials: A
authors.lastname: Okuniewski
authors.affiliation: Department of Inorganic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, G. Narutowicza 11/12, 80-233 Gdańsk, Poland.
authors.forename: Damian
authors.initials: D
authors.lastname: Rosiak
authors.affiliation: Department of Inorganic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, G. Narutowicza 11/12, 80-233 Gdańsk, Poland.
authors.forename: Jarosław
authors.initials: J
authors.lastname: Chojnacki
authors.affiliation: Department of Inorganic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, G. Narutowicza 11/12, 80-233 Gdańsk, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Becker
keywords: benzoylthiourea; crystal structure; hydrogen bonding; quasi-aromaticity; stacking interactions