N,N,N′,N′,N′′-Penta­methyl-N′′-[3-(tri­methyl­aza­nium­yl)prop­yl]guanidinium bis­(tetra­phenyl­borate)

Tiritiris, I.

doi:10.1107/S1600536813001992

Volume 69
Part 2
Page o292
February 2013

Received 17 January 2013
Accepted 20 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.108
Data-to-parameter ratio = 20.0
Details

N,N,N',N',N''-Pentamethyl-N''-[3-(trimethylazaniumyl)propyl]guanidinium bis(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 crystal structure of the title salt, C₁₂H₃₀N₄²⁺·2C₂₄H₂₀B^-, the C-N bond lengths in the central CN₃ unit of the guanidinium ion are 1.3388 (17), 1.3390 (16) and 1.3540 (17) Å, indicating partial double-bond character in each. The central C atom is bonded to the three N atoms in a nearly ideal trigonal-planar geometry and the positive charge is delocalized in the CN₃ plane. The bonds between the N atoms and the terminal C-methyl groups of the guanidinium moiety, all have values close to a typical single bond [1.4630 (16)-1.4697 (17) Å]. C-H [pi] interactions are present between the guanidinium H atoms and the phenyl C atoms of one tetraphenylborate ion. The phenyl rings form a kind of aromatic pocket, in which the guanidinium ion is embedded.

Related literature

For the synthesis of N''-[3-(dimethylamino)propyl]- N,N,N',N'-tetramethylguanidine, see: Tiritiris & Kantlehner (2012). For the crystal structures of alkali metal tetraphenylborates, see: Behrens et al. (2012).

Experimental

Crystal data

C₁₂H₃₀N₄⁺·2C₂₄H₂₀B^-
M_r = 868.82
Monoclinic, P 2₁ /c
a = 17.7622 (4) Å
b = 16.1667 (3) Å
c = 17.3787 (4) Å
= 98.045 (1)°
V = 4941.29 (18) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 100 K
0.27 × 0.25 × 0.20 mm

Data collection

Bruker-Nonius KappaCCD diffractometer
22713 measured reflections
12056 independent reflections
8821 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.108
S = 1.02
12056 reflections
603 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg4, Cg5, Cg6, and Cg8 are the centroids of the C13-C18,C31-C36, C37-C42, C43-C48 and C55-C60 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3CCg7	0.98	2.62	3.3783 (16)	134
C7-H7BCg1	0.99	2.80	3.7805 (14)	169
C9-H9BCg6	0.99	2.52	3.4075 (14)	149
C11-H11CCg5ⁱ	0.98	2.62	3.4852 (15)	147
C12-H12ACg4	0.98	2.59	3.4044 (15)	141
C12-H12BCg8ⁱⁱ	0.98	2.69	3.5990 (15)	155
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; 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: ZL2530 ).

Acknowledgements

The author thanks Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for measuring the crystal data.

References

Behrens, U., Hoffmann, F. & Olbrich, F. (2012). Organometallics, 31, 905-913.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Hooft, R. W. W. (2004). COLLECT. Bruker-Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.

organic compounds