Morpholine-4-carboxamidinium ethyl carbonate

Tiritiris, I.

doi:10.1107/S1600536812046922

Volume 68
Part 12
Page o3431
December 2012

Received 12 November 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.112
Data-to-parameter ratio = 17.0
Details

Morpholine-4-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

The asymmetric unit of the title salt, C₅H₁₂N₃O⁺·C₃H₅O₃^-, contains two carboxamidinium and two ethyl carbonate ions. In the crystal, the C-N bond lengths in the central CN₃ units of the cations range between 1.324 (2) and 1.352 (2) Å, indicating partial double-bond character. The central C atoms are bonded to the three N atoms in a nearly ideal trigonal-planar geometry and the positive charges are delocalized in the CN₃ planes. The morpholine rings are in chair conformations. The C-O bond lengths in both ethyl carbonate ions are characteristic for delocalized double bonds [1.243 (2)-1.251 (2) Å] and typical single bonds [1.368 (2) and 1.375 (2) Å]. In the crystal, N-HO hydrogen bonds between cations and anions generate a two-dimensional network in the ac plane.

Related literature

For the synthesis and crystal structures of guanidinium hydrogen carbonates, see: Tiritiris et al. (2011). For the crystal structure of 4-morpholinecarboxamidine, see: Tiritiris (2012a). For the crystal structure of piperidine-1-carboxamidinium ethyl carbonate, see: Tiritiris (2012b).

Experimental

Crystal data

C₅H₁₂N₃O⁺·C₃H₅O₃^-
M_r = 219.25
Monoclinic, P 2₁ /n
a = 10.2163 (5) Å
b = 20.8874 (9) Å
c = 10.4616 (5) Å
= 109.505 (2)°
V = 2104.31 (17) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.30 × 0.25 × 0.15 mm

Data collection

Bruker-Nonius KappaCCD diffractometer
9902 measured reflections
5199 independent reflections
2981 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.112
S = 1.00
5199 reflections
305 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H11O4ⁱ	0.84 (2)	2.12 (2)	2.944 (1)	168 (1)
N1-H12O3ⁱⁱ	0.89 (2)	1.91 (2)	2.795 (1)	174 (1)
N2-H21O6	0.85 (2)	1.97 (2)	2.807 (1)	168 (1)
N2-H22O4ⁱⁱ	0.92 (2)	1.95 (2)	2.851 (1)	164 (1)
N4-H41O6ⁱⁱ	0.86 (2)	1.97 (2)	2.817 (1)	167 (1)
N4-H42O7ⁱ	0.93 (2)	2.00 (2)	2.889 (1)	159 (1)
N5-H51O7ⁱⁱ	0.90 (2)	1.99 (2)	2.879 (1)	172 (1)
N5-H52O3ⁱⁱⁱ	0.90 (2)	1.94 (2)	2.776 (1)	154 (1)
Symmetry codes: (i) x, y, z-1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z.

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: KP2441 ).

Acknowledgements

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

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.
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. (2012a). Acta Cryst. E68, o3118.
Tiritiris, I. (2012b). Acta Cryst. E68, o3310.
Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407-418.

organic compounds

Morpholine-4-carboxamidinium ethyl carbonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References