Received 26 June 2013
The title compound, C10H22N22+·2Br-, was synthesized via reduction of 2,2'-dipyridyl with Ni-Al alloy/KOH, followed by separation of diastereoisomers (meso and rac) by recrystallization from ethanol. Although the two bridging C atoms are optically active, these two chiral centers adopt an (S,R) configuration; thus, the title compound contains an achiral meso form of 2,2'-bipiperidine. Both of the piperidinium rings adopt chair conformations, and the two N atoms are trans to each other; an inversion center is located in the mid-point of the central C-C bond. The conformation of the organic moiety resembles that of 1,1'-bi(cyclohexane). The organic diammonium cations are linked to each other through hydrogen bonding with bromide counter-ions, each of which forms two hydrogen bonds (N-HBr) with two adjacent organic cations, thus linking the latter together in sheets parallel to (100).
For more details about synthetic and characterization methods, see: Denmark et al. (2006); Herrmann et al. (2006). For the chemistry of related complexes, see: Mikhalyova et al. (2012); Lyakin et al. (2012). For a related structure (the racemic isomer of the title compound), see: Laars et al. (2011).
Data collection: APEX2 and Bruker Instrument Service (Bruker, 2013); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2557 ).
This material is based upon work supported by the US Department of Energy, Office of Basic Energy Science, grant No. DE-FG02-06ER15799. X-ray diffraction instrumentation was purchased with the help of funding from the National Science Foundation (MRI CHE-1229426).
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