rac-2,2′-Bipiperidine-1,1′-diium dibromide

Laars, M.; Ausmees, K.; Kudrjashova, M.; Kanger, T.; Werner, F.

doi:10.1107/S1600536811016084

Volume 67
Part 6
Page o1324
June 2011

Received 10 April 2011
Accepted 27 April 2011
Online 7 May 2011

Key indicators
Single-crystal X-ray study
T = 300 K
Mean (C-C) = 0.006 Å
R = 0.038
wR = 0.093
Data-to-parameter ratio = 17.5
Details

rac-2,2'-Bipiperidine-1,1'-diium dibromide

Marju Laars,^a Kerti Ausmees,^a Marina Kudrjashova,^a Tõnis Kanger ^a and Franz Werner ^a ^*

^aTallinn University of Technology, Department of Chemistry, Akadeemia tee 15, 12618 Tallinn, Estonia
Correspondence e-mail: fwerner@chemnet.ee

In the title compound, C₁₀H₂₂N₂²⁺·2Br^-, a precursor in the synthesis of organocatalysts, the bipiperidinium ion is located on a twofold rotation axis which passes through the mid-point of the central C-C bond. The piperidinium ring adopts a chair conformation. In the crystal, the cations are linked together by Br^- ions through N-HBr hydrogen bonds, forming layers parallel to the ab plane.

Related literature

For the synthesis, see: Krumholz (1953); Herrmann et al. (2006). For the application of N-substituted enantiopure derivatives of the title compound in organocatalysis, see: Laars et al. (2008). For details of the Cu^II-catalysed Henry reaction, see: Noole et al. (2010). For related structures, see: Sato et al. (1982); Baran et al. (1992a,b); Intini et al. (2008).

Experimental

Crystal data

C₁₀H₂₂N₂²⁺·2Br^-
M_r = 330.12
Monoclinic, C 2/c
a = 11.789 (2) Å
b = 10.6403 (18) Å
c = 11.6632 (17) Å
= 107.687 (5)°
V = 1393.9 (4) Å³
Z = 4
Mo K radiation
= 5.79 mm^-1
T = 300 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART X2S diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.151, T_max = 0.391
4225 measured reflections
1225 independent reflections
1012 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.093
S = 1.08
1224 reflections
70 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.47 e Å^-3
_min = -0.94 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NABr1ⁱ	0.95 (4)	2.36 (4)	3.293 (3)	168 (3)
N1-H1NBBr1ⁱⁱ	0.92 (4)	2.34 (4)	3.228 (3)	162 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: GIS (Bruker, 2010); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2700 ).

Acknowledgements

The authors thank for funding grant agreement No. 229830 IC-UP2 under the 7^th Framework Programme of the European Commission, the EU European Regional Development Fund (3.2.0101.08-0017), the Estonian Science Foundation (grant No. 8289) and the Ministry of Education and Research (grant No. 0142725 s06).

References

Baran, P., Valigura, D., Svoboda, I. & Fuess, H. (1992a). Z. Kristallogr. 202, 137-139.
Baran, P., Valigura, D., Svoboda, I. & Fuess, H. (1992b). Z. Kristallogr. 202, 142-144.
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). GIS. Bruker AXS Inc., Madison, Wisconsin, USA.
Herrmann, W. A., Baskakov, D., Herdtweck, E., Hoffmann, S. D., Bunlaksananusorn, T., Rampf, F. & Rodefeld, L. (2006). Organometallics, 25, 2449-2456.
Intini, F. P., Cini, R., Tamasi, G., Hursthouse, M. B. & Natile, G. (2008). Inorg. Chem. 47, 4909-4917.
Krumholz, P. (1953). J. Am. Chem. Soc. 75, 2163-2166.
Laars, M., Kriis, K., Kailas, T., Müürisepp, A.-M., Pehk, T., Kanger, T. & Lopp, M. (2008). Tetrahedron Asymmetry, 19, 641-645.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Noole, A., Lippur, K., Metsala, A., Lopp, M. & Kanger, T. (2010). J. Org. Chem. 75, 1313-1316.
Sato, M., Sato, Y., Yano, S., Yoshikawa, S., Toriumi, K., Itoh, H. & Itho, T. (1982). Inorg. Chem. 21, 2360-2364.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds