Abstract
The cage of 2,5-di-aza-bicyclo-[2.2.1]heptane is frequently employed in synthetic chemistry as a rigid bicyclic counterpart of the piperazine ring. The 2,5-di-azabicyclo-[2.2.1]heptane scaffold is incorporated into a variety of compounds having pharmacological and catalytic applications. The unsubstituted parent ring of the system, 2,5-di-aza-bicyclo-[2.2.1]heptane itself, has not been structurally characterized. We herein report on the mol-ecular structure of the parent ring in (1S,4S)-2,5-diazo-niabi-cyclo-[2.2.1]heptane dibromide, C5H12N22+·2Br-. The asymmetric unit contains two crystallographically independent cages of 2,5-di-aza-bicyclo-[2.2.1]heptane. Each cage is protonated at the two nitro-gen sites. The overall charge balance is maintained by four crystallographically independent bromide ions. In the crystal, the components of the structure are linked via a complex three-dimensional network of N-H⋯Br hydrogen bonds.
Highlights
The cage of 2,5-diazabicyclo[2.2.1]heptane is frequently employed in synthetic chemistry as a rigid bicyclic counterpart of the piperazine ring
The 2,5-diazabicyclo[2.2.1]heptane scaffold is incorporated into a variety of compounds having pharmacological and catalytic applications
In spite of bridge-imparted rigidity, the hexagonal ring of 2,5-diazabicyclo[2.2.1]heptane can be affected by some geometric distortions
Summary
Derivatives of the bicyclic nucleus of 2,5-diazabicyclo[2.2.1]heptane comprise a wide family of biochemically active compounds (Murineddu et al, 2012), including antibiotics (McGuirk et al, 1992; Remuzon et al, 1993), vasodilating (López-Ortiz et al, 2014) and antitumor agents (Hamblett et al, 2007; Shchekotikhin et al, 2014; Gerstenberger et al, 2016; Laskar et al, 2017). Numerous synthetic routes for the preparation of 2,5-diazabicyclo[2.2.1]heptane derivatives have been introduced (see: Portoghese & Mikhail, 1966; Jordis et al., 1990; Yakovlev et al, 2000; Fiorelli et al, 2005; Beinat et al., 2013; Cui et al, 2015; Choi et al, 2016 and the references cited therein). The parent ring of unsubstituted 2,5-diazabicyclo[2.2.1]heptane has not been structurally characterized. Symmetry codes: (i) x þ 1; y 12; z þ 32; (ii) x þ 1; y þ 12; z þ 32
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