Piperidine-1-carboxamidinium ethyl carbonate

Tiritiris, I.

doi:10.1107/S1600536812045497

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 (C-C) = 0.002 Å
R = 0.042
wR = 0.106
Data-to-parameter ratio = 17.2
Details

Piperidine-1-carboxamidinium ethyl carbonate

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 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-HO 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). For the crystal structure of piperidine-1-carboximidamide, see: Tiritiris (2012), and for the crystal structure of sodium methyl carbonate, see: Kunert et al. (1998).

Experimental

Crystal data

C₆H₁₄N₃⁺·C₃H₅O₃^-
M_r = 217.27
Monoclinic, P 2₁ /n
a = 11.8320 (6) Å
b = 7.2407 (4) Å
c = 13.3755 (9) Å
= 105.292 (3)°
V = 1105.33 (11) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.047

Refinement

R[F² > 2(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
_max = 0.28 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H11O2ⁱ	0.88 (2)	1.99 (2)	2.812 (1)	155 (1)
N1-H12O2ⁱⁱ	0.88 (2)	1.88 (2)	2.747 (1)	173 (1)
N2-H21O1ⁱⁱ	0.84 (2)	2.19 (2)	3.033 (1)	175 (1)
N2-H22O1ⁱⁱⁱ	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); 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: 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.
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. (2012). Acta Cryst. E68, o3253.
Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.

organic compounds

Piperidine-1-carboxamidinium ethyl carbonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References