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Volume 69 
Part 11 
Page o1711  
November 2013  

Received 26 June 2013
Accepted 20 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.018
wR = 0.045
Data-to-parameter ratio = 30.8
Details
Open access

(2R,2'S)-2,2'-Bi­piperidine-1,1'-diium dibromide

aDepartment of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA 02155, USA, and bBruker AXS Inc., 5465 E. Cheryl Parkway, Madison, WI 53711, USA
Correspondence e-mail: elena.rybak-akimova@tufts.edu

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-H...Br) with two adjacent organic cations, thus linking the latter together in sheets parallel to (100).

Related literature

For more details about synthetic and characterization methods, see: Denmark et al. (2006[Denmark, S. E., Fu, J. P. & Lawler, M. J. (2006). J. Org. Chem. 71, 1523-1536.]); Herrmann et al. (2006[Herrmann, W. A., Baskakov, D., Herdtweck, E. D., Hoffmann, S. D., Bunlaksananusorn, T., Rampf, F. & Rodefeld, L. (2006). Organometallics, 25, 2449-2456.]). For the chemistry of related complexes, see: Mikhalyova et al. (2012[Mikhalyova, E. A., Makhlynets, O. V., Palluccio, T. D., Filatov, A. S. & Rybak- Akimova, E. V. (2012). Chem. Commun. 48, 687-689.]); Lyakin et al. (2012[Lyakin, O. Y., Ottenbacher, R. V., Bryliakov, K. P. & Talsi, E. P. (2012). ACS Catal. 2, 1196-1202.]). For a related structure (the racemic isomer of the title compound), see: Laars et al. (2011[Laars, M., Ausmees, K., Kudrjashova, M., Kanger, T. & Werner, F. (2011). Acta Cryst. E67, o1324.]).

[Scheme 1]

Experimental

Crystal data
  • C10H22N22+·2Br-

  • Mr = 330.11

  • Monoclinic, C 2/c

  • a = 17.9719 (9) Å

  • b = 9.7654 (5) Å

  • c = 7.3637 (3) Å

  • [beta] = 92.134 (1)°

  • V = 1291.45 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.25 mm-1

  • T = 100 K

  • 0.55 × 0.23 × 0.10 mm

Data collection
  • Bruker D8 QUEST CMOS diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2012[Sheldrick, G. M. (2012). SADABS. University of Göttingen, Germany.]) Tmin = 0.13, Tmax = 0.57

  • 12426 measured reflections

  • 2155 independent reflections

  • 1955 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.018

  • wR(F2) = 0.045

  • S = 1.11

  • 2155 reflections

  • 70 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.88 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...Br1i 0.913 (16) 2.408 (16) 3.2670 (10) 156.7 (13)
N1-H1B...Br1 0.880 (18) 2.359 (18) 3.2311 (10) 170.9 (14)
Symmetry code: (i) [x, -y+2, z-{\script{1\over 2}}].

Data collection: APEX2 and Bruker Instrument Service (Bruker, 2013[Bruker (2013). APEX2 and Bruker Instrument Service. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2557 ).


Acknowledgements

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).

References

Bruker (2011). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2013). APEX2 and Bruker Instrument Service. Bruker AXS Inc., Madison, Wisconsin, USA.
Denmark, S. E., Fu, J. P. & Lawler, M. J. (2006). J. Org. Chem. 71, 1523-1536.  [CSD] [CrossRef] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Herrmann, W. A., Baskakov, D., Herdtweck, E. D., Hoffmann, S. D., Bunlaksananusorn, T., Rampf, F. & Rodefeld, L. (2006). Organometallics, 25, 2449-2456.  [CrossRef] [ChemPort]
Laars, M., Ausmees, K., Kudrjashova, M., Kanger, T. & Werner, F. (2011). Acta Cryst. E67, o1324.  [CSD] [CrossRef] [IUCr Journals]
Lyakin, O. Y., Ottenbacher, R. V., Bryliakov, K. P. & Talsi, E. P. (2012). ACS Catal. 2, 1196-1202.  [CrossRef] [ChemPort]
Mikhalyova, E. A., Makhlynets, O. V., Palluccio, T. D., Filatov, A. S. & Rybak- Akimova, E. V. (2012). Chem. Commun. 48, 687-689.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2012). SADABS. University of Göttingen, Germany.


Acta Cryst (2013). E69, o1711  [ doi:10.1107/S1600536813028754 ]

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