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Volume 66 
Part 2 
Page o377  
February 2010  

Received 19 December 2009
Accepted 4 January 2010
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.007 Å
R = 0.022
wR = 0.052
Data-to-parameter ratio = 16.2
Details
Open access

1-Bromomethyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide

aUniversity of Illinois, School of Chemical Sciences, Box 77-5, 600 South Mathews Avenue, Urbana, Illinois 61801, USA,bUniversity of Illinois, School of Chemical Sciences, Box 59-1, 505 South Mathews Avenue, Urbana, Illinois 61801, USA, and cUniversity of Illinois, School of Chemical Sciences, Box 55-5, 600 South Mathews Avenue, Urbana, Illinois 61801, USA
Correspondence e-mail: jsmoore@illinois.edu

The title compound, C7H14BrN2+·Br-, was prepared by nucleophilic substitution of DABCO (systematic name: 1,4-diazabicyclo[2.2.2]octane) with dibromomethane in acetone. The structure features Br...H close contacts (2.79 and 2.90 Å) as well as a weak bromine-bromide interaction [3.6625 (6) Å].

Related literature

For use of DABCO as an organocatalyst, see Basaviah et al. (2003[Basaviah, D., Rao, A. J. & Satyanarayana, T. (2003). Chem. Rev. 103, 811-891.]). For related haloalkylations of DABCO, see: Almarzoqi et al. (1986[Almarzoqi, B., George, A. V. & Isaacs, N. S. (1986). Tetrahedron Lett. 42, 601-607.]); Fronczek et al. (1990[Fronczek, F. R., Ivie, M. L. & Maverick, A. W. (1990). Acta Cryst. C46, 2057-2062.]); Gustafsson et al. (2005[Gustafsson, B., Håkansson, M. & Jagner, S. (2005). Inorg. Chim. Acta, 358, 1309-1312.]); Banks et al. (1993[Banks, R. E., Sharif, I. & Pritchard, R. G. (1993). Acta Cryst. C49, 492-495.]); Batsanov et al. (2005[Batsanov, A. S., Trmcic, J. & Sandford, G. (2005). Acta Cryst. E61, o681-o682.]); Fletcher Claville et al. (2007[Fletcher Claville, M. O., Payne, R. J., Parker, B. C. & Fronczek, F. R. (2007). Acta Cryst. E63, o2601.]). For inversion twinning, see: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]).

[Scheme 1]

Experimental

Crystal data
  • C7H14BrN2+·Br-

  • Mr = 286.02

  • Orthorhombic, C m c 21

  • a = 7.1100 (3) Å

  • b = 11.8085 (5) Å

  • c = 11.7702 (5) Å

  • V = 988.21 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 8.15 mm-1

  • T = 193 K

  • 0.36 × 0.35 × 0.06 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: integration [SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and XPREP (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.])] Tmin = 0.151, Tmax = 0.744

  • 7347 measured reflections

  • 991 independent reflections

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

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.052

  • S = 1.10

  • 991 reflections

  • 61 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 468 Friedel pairs

  • Flack parameter: -0.004 (17)

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and CrystalMaker (CrystalMaker, 1994[CrystalMaker (1994). CrystalMaker. CrystalMaker Software Ltd, Oxford, England. www.CrystalMaker.com.]); software used to prepare material for publication: XCIF (Bruker, 2005[Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2223 ).


Acknowledgements

This work was supported by the National Science Foundation under NSF Award Nos. CBET-0730667 and CHE-0642413. The Materials Chemistry Laboratory at the University of Illinois was supported in part by grants NSF CHE 95-03145 and NSF CHE 03-43032 from the National Science Foundation.

References

Almarzoqi, B., George, A. V. & Isaacs, N. S. (1986). Tetrahedron Lett. 42, 601-607.  [ChemPort]
Banks, R. E., Sharif, I. & Pritchard, R. G. (1993). Acta Cryst. C49, 492-495.  [CrossRef] [details]
Basaviah, D., Rao, A. J. & Satyanarayana, T. (2003). Chem. Rev. 103, 811-891.  [ISI] [PubMed]
Batsanov, A. S., Trmcic, J. & Sandford, G. (2005). Acta Cryst. E61, o681-o682.  [CSD] [CrossRef] [details]
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SAINT, XCIF and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
CrystalMaker (1994). CrystalMaker. CrystalMaker Software Ltd, Oxford, England. www.CrystalMaker.com.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.  [ISI] [CrossRef] [ChemPort] [details]
Fletcher Claville, M. O., Payne, R. J., Parker, B. C. & Fronczek, F. R. (2007). Acta Cryst. E63, o2601.  [CSD] [CrossRef] [details]
Fronczek, F. R., Ivie, M. L. & Maverick, A. W. (1990). Acta Cryst. C46, 2057-2062.  [CrossRef] [details]
Gustafsson, B., Håkansson, M. & Jagner, S. (2005). Inorg. Chim. Acta, 358, 1309-1312.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o377  [ doi:10.1107/S1600536810000292 ]

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