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Choice of hydrogen bonds or halogen bonds by 2-halogenated 5-morpholinomethylphenyl triazolo[1,5-a]pyridine

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Abstract

The crystal structures of halogenated 1,2,4-triazolo[1,5-a]pyridine derivatives disclose intriguing structural chemistry features dictated by the formation of either hydrogen bonds (HBs) or halogen bonds (XBs). 2-Chloride and bromide derivatives (1 and 2) favor HBs, promoting the formation of bent-shaped conformers. The 2-iodide compound (3) favors XBs, leading to different shaped conformers split into polymorphic forms. The XB-mediated crystals (3I and 3II) are more thermodynamically stable than the HB-mediated crystals of 1 and 2.

Graphical abstract: Choice of hydrogen bonds or halogen bonds by 2-halogenated 5-morpholinomethylphenyl triazolo[1,5-a]pyridine

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Publication details

The article was received on 20 Mar 2018, accepted on 02 May 2018 and first published on 18 May 2018


Article type: Communication
DOI: 10.1039/C8CE00423D
Citation: CrystEngComm, 2018, Advance Article
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    Choice of hydrogen bonds or halogen bonds by 2-halogenated 5-morpholinomethylphenyl triazolo[1,5-a]pyridine

    C. Li, Y. Chai, X. Zhou, Z. Shen, B. Ma, B. Chen, R. Huang, H. Chen, W. Li and Y. He, CrystEngComm, 2018, Advance Article , DOI: 10.1039/C8CE00423D

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