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Volume 69 
Part 7 
Page o1040  
July 2013  

Received 28 May 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.137
Data-to-parameter ratio = 11.0
Details
Open access

N-[3-(Dimethylamino)propyl]-N,N',N',N'',N''-pentamethylguanidinium 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, C11H27N4+·C24H20B-, the C-N bond lengths in the central CN3 unit of the guanidinium ion are 1.333 (4), 1.334 (4) and 1.351 (4) Å, indicating partial double-bond character. The C atom of this unit is bonded to the three N atoms in a nearly ideal trigonal-planar geometry [N-C-N angles = 118.8 (3), 120.0 (3) and 121.2 (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 have values in the range 1.459 (4)-1.478 (4) Å, close to a typical single bond. In the crystal, there are C-H...[pi] interactions between the guanidinium H atoms and the phenyl rings of the tetraphenylborate ion. These interactions combine to form a ladder of linked chains of ions which runs parallel to the c axis.

Related literature

For the synthesis of N''-[3-(dimethylamino)propyl]-N,N,N',N'-tetramethylguanidine, 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''-tetramethyl-N''-[3-(trimethylazaniumyl)propyl]guanidinium bis(tetraphenylborate) acetone disolvate, see: Tiritiris (2013[Tiritiris, I. (2013). Acta Cryst. E69, o337-o338.]).

[Scheme 1]

Experimental

Crystal data
  • C11H27N4+·C24H20B-

  • Mr = 534.58

  • Orthorhombic, P n a 21

  • a = 20.5074 (7) Å

  • b = 15.4134 (5) Å

  • c = 9.8568 (3) Å

  • V = 3115.62 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.20 × 0.18 × 0.13 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • 7338 measured reflections

  • 4035 independent reflections

  • 3181 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.137

  • S = 1.05

  • 4035 reflections

  • 368 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C30-C35, C18-C23 and C24-C29 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2C...Cg1i 0.98 2.48 3.425 (1) 162
C7-H7A...Cg2ii 0.99 2.84 3.821 (1) 170
C3-H3A...Cg2i 0.98 2.89 3.680 (1) 138
C9-H9A...Cg3iii 0.99 2.82 3.610 (1) 136
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]; (iii) [-x+{\script{1\over 2}}, 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, D-53002 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: GO2091 ).


Acknowledgements

The author thanks Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for collecting 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, D-53002 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] [ChemPort] [IUCr Journals]
Tiritiris, I. (2013). Acta Cryst. E69, o337-o338.  [CrossRef] [ChemPort] [IUCr Journals]
Tiritiris, I. & Kantlehner, W. (2012). Z. Naturforsch. Teil B, 67, 685-698.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1040  [ doi:10.1107/S1600536813014906 ]

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