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Crystal structure and halogen-hydrogen bonding of a Delepine reaction inter-mediate.

ABSTRACT: The reaction of 1,5-di-bromo-pentane with urotropine results in crystals of the title mol-ecular salt, 5-bromo-urotropinium bromide [systematic name: 1-(5-bro-mo-pent-yl)-3,5,7-tri-aza-1-azoniatri-cyclo-[3.3.1.1^3,7]decane bromide], C₁₁H₂₂BrN₄ ⁺·Br^- (1), crystallizing in space group P2₁/n. The packing in compound 1 is directed mainly by H?H van der Waals inter-actions and C-H?Br hydrogen bonds, as revealed by Hirshfeld surface analysis. Comparison with literature examples of alkyl-urotropinium halides shows that the inter-actions in 1 are consistent with those in other bromides and simple chloride and iodide species.

SUBMITTER: Mulrooney DZT

PROVIDER: S-EPMC7784050 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Crystal structure and halogen-hydrogen bonding of a Delépine reaction inter-mediate.

Mulrooney David Z T DZT Müller-Bunz Helge H Keene Tony D TD

Acta crystallographica. Section E, Crystallographic communications 20210101 Pt 1

The reaction of 1,5-di-bromo-pentane with urotropine results in crystals of the title mol-ecular salt, 5-bromo-urotropinium bromide [systematic name: 1-(5-bro-mo-pent-yl)-3,5,7-tri-aza-1-azoniatri-cyclo-[3.3.1.13,7]decane bromide], C11H22BrN4 +·Br- (1), crystallizing in space group P21/n. The packing in compound 1 is directed mainly by H⋯H van der Waals inter-actions and C-H⋯Br hydrogen bonds ...[more]

PMID: 33520273

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