Cocrystals of 1,4-diethynylbenzene with 1,3-diacetylbenzene and benzene-1,4-dicarbaldehyde exhibiting strong nonconventional alkyne-carbonyl C—H…O hydrogen bonds between the components

详细信息    查看全文

• 作者：Eric Bosch
• 关键词：alkyne C&mdash ; H&hellip ; O hydrogen bonds ; nonconventional hydrogen bonds ; cocrystals ; crystal structure ; 1 ; 4-diethynylbenzene ; 1 ; 3-diacetylbenzene ; benzene-1 ; 4-dicarbaldehyde
• 刊名：Acta Crystallographica Section C
• 出版年：2016
• 出版时间：October 2016
• 年：2016
• 卷：72
• 期：10
• 页码：748-752
• 全文大小：808K
• ISSN：1600-5759

文摘

Weak interactions between organic molecules are important in solid-state structures where the sum of the weaker interactions support the overall three-dimensional crystal structure. The sp-C—H…N hydrogen-bonding interaction is strong enough to promote the deliberate cocrystallization of a series of diynes with a series of dipyridines. It is also possible that a similar series of cocrystals could be formed between molecules containing a terminal alkyne and molecules which contain carbonyl O atoms as the potential hydrogen-bond acceptor. I now report the crystal structure of two cocrystals that support this hypothesis. The 1:1 cocrystal of 1,4-diethynylbenzene with 1,3-diacetylbenzene, C₁₀H₆·C₁₀H₁₀O₂, (1), and the 1:1 cocrystal of 1,4-diethynylbenzene with benzene-1,4-dicarbaldehyde, C₁₀H₆·C₈H₆O₂, (2), are presented. In both cocrystals, a strong nonconventional ethynyl–carbonyl sp-C—H…O hydrogen bond is observed between the components. In cocrystal (1), the C—H…O hydrogen-bond angle is 171.8 (16)° and the H…O and C…O hydrogen-bond distances are 2.200 (19) and 3.139 (2) Å, respectively. In cocrystal (2), the C—H…O hydrogen-bond angle is 172.5 (16)° and the H…O and C…O hydrogen-bond distances are 2.25 (2) and 3.203 (2) Å, respectively.