Crystal structure and halogen-hydrogen bonding of a Delepine reaction intermediate

The reaction of 1,5-dibromopentane with urotropine results in crystals of the title molecular salt, 5-bromourotropinium bromide [systematic name: 1-(5-bromopentyl)-3,5,7-triaza- 1-azoniatricyclo[3.3.1.1(3,7)] decane bromide], C11H22BrN4+center dot Br- (1), crystallizing in space group P2(1)/n. The packing in compound 1 is directed mainly by H center dot center dot center dot H van der Waals interactions and C-H center dot center dot center dot Br hydrogen bonds, as revealed by Hirshfeld surface analysis. Comparison with literature examples of alkylurotropinium halides shows that the interactions in 1 are consistent with those in other bromides and simple chloride and iodide species.

Automated summary

The study analyzed the crystal structure of the molecular salt formed by the reaction of 1,5-dibromopentane with urotropine, revealing that the interactions in the compound are mainly van der Waals and hydrogen bonds.