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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 P1̅, 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.
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- Publication version
- Accepted or Published Version
- DOI:
- Digital Object Identifier (open in new tab) 10.1107/S2053229616019495
- License
- Copyright (2017 International Union of Crystallography)
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
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Acta Crystallographica Section C-Structural Chemistry
no. 73,
pages 52 - 56,
ISSN: 2053-2296 - Language:
- English
- Publication year:
- 2017
- Bibliographic description:
- Okuniewski A., Rosiak D., Chojnacki J., Becker B.: 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// Acta Crystallographica Section C-Structural Chemistry. -Vol. 73, (2017), s.52-56
- DOI:
- Digital Object Identifier (open in new tab) 10.1107/s2053229616019495
- Verified by:
- Gdańsk University of Technology
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