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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 [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.091
Data-to-parameter ratio = 17.3
Details
Open access

4-Morpholinecarboxamidine

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-H...N and N-H...O 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[Dräger, G., Solodenko, W., Messinger, J., Schön, U. & Kirschning, A. (2002). Tetrahedron Lett. 43, 1401-1403.]). For the crystal structure of 4,4'-carbonyl-dimorpholine, see: Zhou et al. (2003[Zhou, W. Q., Zhu, L. M., Cao, Zh. B., Zhang, Y., Lu, W. D. & Lu, L. D. (2003). J. Mol. Struct. 565, 405-411.]).

[Scheme 1]

Experimental

Crystal data
  • C5H11N3O

  • Mr = 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[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H21...N1i 0.90 (2) 2.03 (2) 2.930 (1) 174 (1)
N2-H22...O1ii 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[Hooft, R. W. W. (2004). COLLECT. 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, 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: 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.  [CrossRef] [details]
Zhou, W. Q., Zhu, L. M., Cao, Zh. B., Zhang, Y., Lu, W. D. & Lu, L. D. (2003). J. Mol. Struct. 565, 405-411.  [ISI] [CrossRef]


Acta Cryst (2012). E68, o3118  [ doi:10.1107/S1600536812042201 ]

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