[Journal logo]

Volume 67 
Part 5 
Page o1060  
May 2011  

Received 29 March 2011
Accepted 31 March 2011
Online 7 April 2011

[bt5503sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.056
wR = 0.155
Data-to-parameter ratio = 17.2
Details
Open access

Butane-1,4-diammonium bis(perchlorate)

Charmaine Ardernea* and Gert J. Krugera

aDepartment of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: carderne@uj.ac.za

The butane-1,4-diammonium cation of the title compound, C4H14N22+·2ClO4-, lies on a special position of site symmetry 2/m, whereas the perchlorate anion is located on a crystallographic mirror plane. An intricate three-dimensional hydrogen-bonding network exists in the crystal structure with each H atom of the ammonium group exhibiting bifurcated interactions to the perchlorate anion. Complex hydrogen-bonded ring and chain motifs are also evident, in particular a 50-membered ring with graph-set notation R1010(50) is identified.

Related literature

For related structural studies of butane-1,4-diammonium salts, see: van Blerk & Kruger (2007[Blerk, C. van & Kruger, G. J. (2007). Acta Cryst. E63, o342-o344.]); Lemmerer & Billing (2006[Lemmerer, A. & Billing, D. G. (2006). Acta Cryst. E62, o1954-o1956.]); Gabro et al. (2009[Gabro, M., Lalancette, R. A. & Bernal, I. (2009). Acta Cryst. E65, o1352.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C4H14N22+·2ClO4-

  • Mr = 289.07

  • Monoclinic, C 2/m

  • a = 19.4755 (10) Å

  • b = 5.6210 (3) Å

  • c = 5.3470 (2) Å

  • [beta] = 97.222 (3)°

  • V = 580.70 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 296 K

  • 0.50 × 0.34 × 0.16 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (AX-Scale; Bruker, 2008[Bruker (2008). AXScale, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.757, Tmax = 0.912

  • 3067 measured reflections

  • 793 independent reflections

  • 694 reflections with I > 2s(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.155

  • S = 1.17

  • 793 reflections

  • 46 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.89 2.35 3.035 (3) 134
N1-H1N...O1ii 0.89 2.35 3.035 (3) 134
N1-H2N...O1 0.89 2.68 3.435 (4) 143
N1-H2N...O3 0.89 2.21 3.0308 (14) 153
Symmetry codes: (i) x, y, z+1; (ii) x, -y, z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). AXScale, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). AXScale, APEX2 and 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]) and Mercury (Macrae et al., 2006[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.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5503 ).

Acknowledgements

The authors acknowledge the National Research Foundation Thuthuka programme (GUN 66314) and the University of Johannesburg for funding and facilities for this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Blerk, C. van & Kruger, G. J. (2007). Acta Cryst. E63, o342-o344.  [CSD] [CrossRef] [details]
Bruker (2008). AXScale, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gabro, M., Lalancette, R. A. & Bernal, I. (2009). Acta Cryst. E65, o1352.  [CSD] [CrossRef] [details]
Lemmerer, A. & Billing, D. G. (2006). Acta Cryst. E62, o1954-o1956.  [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2011). E67, o1060  [ doi:10.1107/S1600536811012025 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.