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

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• 作者：Andrzej Okuniewski ; Damian Rosiak ; Jarosław Chojnacki and Barbara Becker
• 关键词：benzoylthiourea ; crystal structure ; hydrogen bonding ; quasi-aromaticity ; stacking interactions
• 刊名：Acta Crystallographica Section C
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：73
• 期：1
• 页码：52-56
• 全文大小：692K
• ISSN：1600-5759

文摘

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 m>Pm>, while (II) crystallizes in the space group m>Pm>2₁/m>cm>. 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 m>viam> 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 m>viam> 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.