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Volume 68 
Part 12 
Page o3500  
December 2012  

Received 21 November 2012
Accepted 26 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.041
wR = 0.112
Data-to-parameter ratio = 24.4
Details
Open access

N,N,N',N'-Tetramethylguanidinium tetraphenylborate

aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
Correspondence e-mail: Ioannis.Tiritiris@htw-aalen.de

In the title salt, C5H14N3+·C24H20B-, the C-N bond lengths in the central CN3 unit are 1.3322 (11), 1.3385 (12) and 1.3422 (12) Å, indicating partial double-bond character. The central C atom is bonded to the three N atoms in a nearly ideal trigonal-planar geometry [N-C-N angles = 119.51 (8), 119.81 (9) and 120.69 (8)°] and the positive charge is delocalized in the CN3 plane. The bond lengths between the N atoms and the terminal methyl groups all have values close to a typical single bond [1.4597 (12)-1.4695 (13) Å]. The crystal packing is caused by electrostatic interactions between cations and anions.

Related literature

For related structures, see: Fischer & Jones (2002[Fischer, A. K. & Jones, P. G. (2002). Acta Cryst. E58, o218-o219.]); Berg et al. (2010[Berg, R. W., Riisager, A., Van Buu, O. N., Kristensen, S. B., Fehrmann, R., Harris, P. & Brunetti, A. C. (2010). J. Phys. Chem. A, 114, 13175-13181.]); Tiritiris et al. (2011[Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.]); Criado et al. (2000[Criado, A., Diánez, M. J., Pérez-Garrido, S., Fernandes, I. M. L., Belsley, M. & de Matos Gomes, E. (2000). Acta Cryst. C56, 888-889.]); Kanters et al. (1992[Kanters, J. A., ter Horst, E. H. & Grech, E. (1992). Acta Cryst. C48, 1345-1347.]); Bujak et al. (1999[Bujak, M., Osadczuk, P. & Zaleski, J. (1999). Acta Cryst. C55, 1443-1447.]); Wong et al. (2004[Wong, A., Whitehead, R. D., Gan, Z. & Wu, G. (2004). J. Phys. Chem. A, 108, 10551-10559.]); Pajzderska et al. (2002[Pajzderska, A., Maluszynska, H. & Wasicki, J. (2002). Z. Naturforsch. Teil A, 57, 847-853.]).

[Scheme 1]

Experimental

Crystal data
  • C5H14N3+·C24H20B-

  • Mr = 435.40

  • Monoclinic, P 21 /n

  • a = 10.9512 (5) Å

  • b = 18.1315 (9) Å

  • c = 12.5453 (7) Å

  • [beta] = 96.594 (2)°

  • V = 2474.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.23 × 0.16 × 0.12 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • 52874 measured reflections

  • 7573 independent reflections

  • 6738 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.112

  • S = 1.04

  • 7573 reflections

  • 310 parameters

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2091 ).


Acknowledgements

The author thanks Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for the data collection.

References

Berg, R. W., Riisager, A., Van Buu, O. N., Kristensen, S. B., Fehrmann, R., Harris, P. & Brunetti, A. C. (2010). J. Phys. Chem. A, 114, 13175-13181.  [CrossRef] [ChemPort] [PubMed]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bujak, M., Osadczuk, P. & Zaleski, J. (1999). Acta Cryst. C55, 1443-1447.  [CSD] [CrossRef] [details]
Criado, A., Diánez, M. J., Pérez-Garrido, S., Fernandes, I. M. L., Belsley, M. & de Matos Gomes, E. (2000). Acta Cryst. C56, 888-889.  [CrossRef] [details]
Fischer, A. K. & Jones, P. G. (2002). Acta Cryst. E58, o218-o219.  [CrossRef] [details]
Kanters, J. A., ter Horst, E. H. & Grech, E. (1992). Acta Cryst. C48, 1345-1347.  [CrossRef] [details]
Pajzderska, A., Maluszynska, H. & Wasicki, J. (2002). Z. Naturforsch. Teil A, 57, 847-853.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.  [CrossRef] [ChemPort]
Wong, A., Whitehead, R. D., Gan, Z. & Wu, G. (2004). J. Phys. Chem. A, 108, 10551-10559.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3500  [ doi:10.1107/S160053681204860X ]

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