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Volume 69 
Part 6 
Page o899  
June 2013  

Received 8 May 2013
Accepted 9 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.110
Data-to-parameter ratio = 9.9
Details
Open access

N-[3-(Benzyldimethylazaniumyl)propyl]-N',N',N'',N''-tetramethylguanidinium bis(tetraphenylborate)

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, C17H32N42+·2C24H20B-, the C-N bond lengths in the CN3 unit of the guanidinium ion are 1.323 (4), 1.336 (5) and 1.337 (5) Å, indicating partial double-bond character in each. The C atom of this unit is bonded to the three N atoms in a nearly ideal trigonal-planar geometry [N-C-N angles = 117.7 (4), 120.9 (3) and 121.4 (3)°] 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 [1.452 (5)-1.484 (6) Å]. In the crystal, C-H...[pi] interactions are present between guanidinium H atoms and the phenyl rings of both tetraphenylborate ions. This leads to the formation of a two-dimensional supramolecular pattern along the ab plane.

Related literature

For biosorption of tetradecyl benzyl dimethyl ammonium chloride onto activated sludge, see: Ren et al. (2011[Ren, R., Li, K., Zhang, C., Liu, D. & Sun, J. (2011). Bioresour. Technol. 102, 3799-3804.]). 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 structures of alkali metal tetraphenylborates, see: Behrens et al. (2012[Behrens, U., Hoffmann, F. & Olbrich, F. (2012). Organometallics, 31, 905-913.]). For the structures of N,N,N',N',N''-pentamethyl-N''-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate) and N,N,N',N',N''-tetramethyl-N''-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate) acetone disolvate, see: Tiritiris (2013a[Tiritiris, I. (2013a). Acta Cryst. E69, o292.],b[Tiritiris, I. (2013b). Acta Cryst. E69, o337-o338.]).

[Scheme 1]

Experimental

Crystal data
  • C17H32N42+·2C24H20B-

  • Mr = 930.89

  • Monoclinic, C c

  • a = 17.1981 (3) Å

  • b = 17.3466 (3) Å

  • c = 17.8082 (4) Å

  • [beta] = 94.182 (1)°

  • V = 5298.55 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.19 × 0.17 × 0.13 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • 6442 measured reflections

  • 6442 independent reflections

  • 5242 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.110

  • S = 1.05

  • 6442 reflections

  • 650 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1-Cg5 are the centroids of the C36-C41, C30-C35, C24-C29, C42-C47 and C60-C65 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C11-H11B...Cg1 0.97 2.73 3.699 (2) 174
C11-H11A...Cg2 0.97 2.66 3.509 (2) 145
C14-H14...Cg3i 0.93 2.92 3.531 (2) 124
C9-H9A...Cg4ii 0.97 2.91 3.569 (2) 126
C7-H7A...Cg5iii 0.96 2.82 3.696 (2) 133
Symmetry codes: (i) [x, -y, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

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: ZL2550 ).


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.  [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.
Ren, R., Li, K., Zhang, C., Liu, D. & Sun, J. (2011). Bioresour. Technol. 102, 3799-3804.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tiritiris, I. (2013a). Acta Cryst. E69, o292.  [CSD] [CrossRef] [details]
Tiritiris, I. (2013b). Acta Cryst. E69, o337-o338.  [CrossRef] [ChemPort] [details]
Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o899  [ doi:10.1107/S1600536813012786 ]

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