N,N,N′,N′-Tetra­methyl­guanidinium tetra­phenyl­borate

Tiritiris, I.

doi:10.1107/S160053681204860X

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 (C-C) = 0.001 Å
R = 0.041
wR = 0.112
Data-to-parameter ratio = 24.4
Details

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

Ioannis Tiritiris ^a ^*

^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); Berg et al. (2010); Tiritiris et al. (2011); Criado et al. (2000); Kanters et al. (1992); Bujak et al. (1999); Wong et al. (2004); Pajzderska et al. (2002).

Experimental

Crystal data

C₅H₁₄N₃⁺·C₂₄H₂₀B^-
M_r = 435.40
Monoclinic, P 2₁ /n
a = 10.9512 (5) Å
b = 18.1315 (9) Å
c = 12.5453 (7) Å
= 96.594 (2)°
V = 2474.5 (2) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.021

Refinement

R[F² > 2(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
_max = 0.40 e Å^-3
_min = -0.31 e Å^-3

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); 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.
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.
Criado, A., Diánez, M. J., Pérez-Garrido, S., Fernandes, I. M. L., Belsley, M. & de Matos Gomes, E. (2000). Acta Cryst. C56, 888-889.
Fischer, A. K. & Jones, P. G. (2002). Acta Cryst. E58, o218-o219.
Kanters, J. A., ter Horst, E. H. & Grech, E. (1992). Acta Cryst. C48, 1345-1347.
Pajzderska, A., Maluszynska, H. & Wasicki, J. (2002). Z. Naturforsch. Teil A, 57, 847-853.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.
Wong, A., Whitehead, R. D., Gan, Z. & Wu, G. (2004). J. Phys. Chem. A, 108, 10551-10559.

organic compounds