[Journal logo]

Volume 69 
Part 3 
Pages o337-o338  
March 2013  

Received 29 January 2013
Accepted 29 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.113
Data-to-parameter ratio = 20.6
Details
Open access

N,N,N',N'-Tetramethyl-N''-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate) acetone disolvate

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

In the title solvated salt, C11H28N42+·2C24H20B-·2C3H6O, the C-N bond lengths in the central CN3 unit of the guanidinium ion are 1.3331 (16), 1.3407 (16) and 1.3454 (16) 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 [N-C-N angles = 118.96 (11), 120.51 (12) and 120.53 (11)°] 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 [1.4601 (16)-1.4649 (16) Å]. In the crystal, the guanidinium ion is connected by N-H...O and C-H...O hydrogen bonds with the acetone molecules. C-H...[pi] interactions are present between the guanidinium H atoms and the phenyl rings of both tetraphenylborate ions. The phenyl rings form aromatic pockets, in which the guanidinium ions are embedded.

Related literature

For the crystal structure of ammonium tetraphenylborate, see: Steiner & Mason (2000[Steiner, T. & Mason, S. A. (2000). Acta Cryst. B56, 254-260.]). For the crystal structures of choline tetraphenylborate, triethanolammonium tetraphenylborate dihydrate and 6-ammonio-n-hexanoic acid tetraphenylborate monohydrate, see: Steiner et al. (2001[Steiner, T., Schreurs, A. M. M., Lutz, M. & Kroon, J. (2001). New J. Chem. 25, 174-178.]). For the synthesis of N''-[3-(dimethylamino)propyl]-N,N,N',N'-tetramethylguanidinium chloride, see: Tiritiris & Kantlehner (2012[Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.]). For the crystal structures of alkali metal tetraphenylborates, see: Behrens et al. (2012[Behrens, U., Hoffmann, F. & Olbrich, F. (2012). Organometallics, 31, 905-913.]). For the crystal structure of N,N,N',N',N''-pentamethyl-N''-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate), see: Tiritiris (2013[Tiritiris, I. (2013). Acta Cryst. E69, o292.]).

[Scheme 1]

Experimental

Crystal data
  • C11H28N42+·2C24H20B-·2C3H6O

  • Mr = 970.95

  • Monoclinic, P 21 /c

  • a = 19.8630 (5) Å

  • b = 18.3212 (4) Å

  • c = 16.5349 (3) Å

  • [beta] = 110.763 (1)°

  • V = 5626.5 (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-Nonius KappaCCD diffractometer

  • 25784 measured reflections

  • 13908 independent reflections

  • 10017 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.113

  • S = 1.02

  • 13908 reflections

  • 674 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C42-C47, C48-C53, C18-C23, C36-C41 and C54-C59 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N3-H3...O1i 0.87 (2) 2.18 (2) 2.914 (2) 142 (2)
C11-H11A...O2ii 0.98 2.48 3.368 (2) 151
C10-H10C...Cg1 0.98 2.82 3.693 (1) 150
C8-H8B...Cg2 0.99 2.82 3.510 (2) 127
C3-H3A...Cg3iii 0.98 2.79 3.359 (1) 118
C2-H2C...Cg4iv 0.98 2.61 3.453 (1) 144
C2-H2A...Cg5iv 0.98 2.59 3.393 (1) 140
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+1, -z+1; (iv) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 2004[Hooft, R. W. W. (2004). COLLECT. Bruker-Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: SCALEPACK; 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: ZL2531 ).


Acknowledgements

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

References

Behrens, U., Hoffmann, F. & Olbrich, F. (2012). Organometallics, 31, 905-913.  [CSD] [CrossRef] [ChemPort]
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.  [CrossRef] [details]
Steiner, T. & Mason, S. A. (2000). Acta Cryst. B56, 254-260.  [ISI] [CSD] [CrossRef] [details]
Steiner, T., Schreurs, A. M. M., Lutz, M. & Kroon, J. (2001). New J. Chem. 25, 174-178.  [ISI] [CSD] [CrossRef] [ChemPort]
Tiritiris, I. (2013). Acta Cryst. E69, o292.  [CrossRef] [details]
Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o337-o338   [ doi:10.1107/S1600536813003024 ]

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.