4-Morpholine­carboxamidine

Tiritiris, I.

doi:10.1107/S1600536812042201

Volume 68
Part 11
Page o3118
November 2012

Received 5 October 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.091
Data-to-parameter ratio = 17.3
Details

4-Morpholinecarboxamidine

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 crystal structure of the title compound, C₅H₁₁N₃O, the C=N and C-N bond lengths in the CN₃ unit are 1.2971 (14), 1.3595 (14) (NH₂) and 1.3902 (13) Å, indicating double- and single-bond character, respectively. The N-C-N angles are 115.49 (9)°, 119.68 (10)° and 124.83 (10)°, showing a deviation of the CN₃ plane from an ideal trigonal-planar geometry. The morpholine ring is in a chair conformation. In the crystal, the molecules are linked by N-HN and N-HO hydrogen bonds, generating a three-dimensional network.

Related literature

For the synthesis of carboxamides by amidination of secondary amines with 4-benzyl-3,5-dimethyl-1H-pyrazole-1-carboxamidine hydrochloride, see: Dräger et al. (2002). For the crystal structure of 4,4'-carbonyl-dimorpholine, see: Zhou et al. (2003).

Experimental

Crystal data

C₅H₁₁N₃O
M_r = 129.17
Tetragonal, I 4₁ /a
a = 16.5910 (6) Å
c = 9.7939 (3) Å
V = 2695.9 (2) Å³
Z = 16
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.17 × 0.15 × 0.13 mm

Data collection

Bruker-Nonius KappaCCD diffractometer
2889 measured reflections
1628 independent reflections
1341 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.091
S = 1.06
1628 reflections
94 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H21N1ⁱ	0.90 (2)	2.03 (2)	2.930 (1)	174 (1)
N2-H22O1ⁱⁱ	0.88 (2)	2.13 (2)	3.007 (1)	174 (1)
Symmetry codes: (i) $[y-{\script{1\over 4}}, -x-{\script{1\over 4}}, z-{\script{1\over 4}}]$ ; (ii) $[-y+{\script{1\over 4}}, x-{\script{1\over 4}}, z-{\script{1\over 4}}]$ .

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: ZL2510 ).

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, Bonn, Germany.
Dräger, G., Solodenko, W., Messinger, J., Schön, U. & Kirschning, A. (2002). Tetrahedron Lett. 43, 1401-1403.
Hooft, R. W. W. (2004). COLLECT. 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.
Zhou, W. Q., Zhu, L. M., Cao, Zh. B., Zhang, Y., Lu, W. D. & Lu, L. D. (2003). J. Mol. Struct. 565, 405-411.

organic compounds