Co-operative halogen bonds and nonconventional sp -C—H...O hydrogen bonds in 1:1 cocrystals formed between diethynylpyridines and N -halosuccinimides
Co-operative halogen bonds and nonconventional sp -C—H...O hydrogen bonds in 1:1 cocrystals formed between diethynylpyridines and N -halosuccinimides
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二乙炔基吡啶和 N -卤代琥珀酰亚胺之间形成的 1:1 共晶中的卤素合作键和非常规 sp -C–H...O 氢键
DOI：
10.1107/s2053229622006635
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Bowling, Nathan P.
中科院分区：
文献类型：
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作者：
Bosch, Eric;Bowling, Nathan P.
二乙炔基吡啶和 N-卤代琥珀酰亚胺的 1:1 溶液一起反应形成卤代炔，快速蒸发导致未反应的两种组分的 1:1 共晶体的分离。 2,6-二乙炔吡啶和N-碘代琥珀酰亚胺（C4H4INO2·C9H5N）形成的1:1共晶含有一个N-碘代琥珀酰亚胺-吡啶I⋯N卤键和两个末端炔-琥珀酰亚胺羰基C—H⋯O氢键。三维延伸结构的特点是通过卤素键相互交织的双链超分子聚合物。 3,5-二乙炔吡啶和N-碘代琥珀酰亚胺（C4H4INO2·C9H5N）形成的共晶还具有一个I⋯N卤键和两个C—H⋯O氢键。然而，这些组分形成基本上平面的双链一维之字形超分子聚合物。 3,5-二乙炔吡啶和N-溴代琥珀酰亚胺之间形成的共晶（C4H4BrNO2·C9H5N）与3,5-二乙炔吡啶和N-碘代琥珀酰亚胺之间形成的共晶是同晶的，具有Br…N卤键而不是I…N卤键。
The rapid evaporation of 1:1 solutions of diethynylpyridines and N-halosuccinimides, that react together to form haloalkynes, led to the isolation of unreacted 1:1 cocrystals of the two components. The 1:1 cocrystal formed between 2,6-diethynylpyridine and N-iodosuccinimide (C4H4INO2·C9H5N) contains an N-iodosuccinimide–pyridine I⋯N halogen bond and two terminal alkyne–succinimide carbonyl C—H⋯O hydrogen bonds. The three-dimensional extended structure features interwoven double-stranded supramolecular polymers that are interconnected through halogen bonds. The cocrystal formed between 3,5-diethynylpyridine and N-iodosuccinimide (C4H4INO2·C9H5N) also features an I⋯N halogen bond and two C—H⋯O hydrogen bonds. However, the components form essentially planar double-stranded one-dimensional zigzag supramolecular polymers. The cocrystal formed between 3,5-diethynylpyridine and N-bromosuccinimide (C4H4BrNO2·C9H5N) is isomorphous to the cocrystal formed between 3,5-diethynylpyridine and N-iodosuccinimide, with a Br⋯N halogen bond instead of an I⋯N halogen bond.