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Volume 68 
Part 12 
Page o3310  
December 2012  

Received 31 October 2012
Accepted 3 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.106
Data-to-parameter ratio = 17.2
Details
Open access

Piperidine-1-carboxamidinium ethyl carbonate

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

In the title salt, C6H14N3+·C3H5O3-, the C-N bond lengths in the central CN3 unit of the carboxamidinium cation are 1.3262 (18), 1.3359 (18) and 1.3498 (18) Å, indicating partial double-bond character. 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 piperidine ring is in a chair conformation. The C-O bond lengths in the ethyl carbonate anion are characteristic for a delocalized double bond and a typical single bond. In the crystal, N-H...O hydrogen bonds between cations and anions generate a two-dimensional network in the direction of the ab plane, whereas adjacent ion pairs form chains running along the b axis.

Related literature

For the synthesis and crystal structures of guanidinium hydrogencarbonates, see: Tiritiris et al. (2011[Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.]). For the crystal structure of piperidine-1-carboximidamide, see: Tiritiris (2012[Tiritiris, I. (2012). Acta Cryst. E68, o3253.]), and for the crystal structure of sodium methyl carbonate, see: Kunert et al. (1998[Kunert, M., Wiegeleben, P., Görls, H. & Dinjus, E. (1998). Inorg. Chem. Commun. 1, 131-133.]).

[Scheme 1]

Experimental

Crystal data
  • C6H14N3+·C3H5O3-

  • Mr = 217.27

  • Monoclinic, P 21 /n

  • a = 11.8320 (6) Å

  • b = 7.2407 (4) Å

  • c = 13.3755 (9) Å

  • [beta] = 105.292 (3)°

  • V = 1105.33 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.25 × 0.20 × 0.05 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • 4452 measured reflections

  • 2638 independent reflections

  • 1982 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.106

  • S = 1.02

  • 2638 reflections

  • 153 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H11...O2i 0.88 (2) 1.99 (2) 2.812 (1) 155 (1)
N1-H12...O2ii 0.88 (2) 1.88 (2) 2.747 (1) 173 (1)
N2-H21...O1ii 0.84 (2) 2.19 (2) 3.033 (1) 175 (1)
N2-H22...O1iii 0.87 (2) 2.06 (2) 2.923 (1) 170 (1)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x, -y+1, -z+1.

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: KP2439 ).


Acknowledgements

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

References

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.
Kunert, M., Wiegeleben, P., Görls, H. & Dinjus, E. (1998). Inorg. Chem. Commun. 1, 131-133.  [ISI] [CrossRef] [ChemPort]
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]
Tiritiris, I. (2012). Acta Cryst. E68, o3253.  [CSD] [CrossRef] [details]
Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3310  [ doi:10.1107/S1600536812045497 ]

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