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Volume 68 
Part 11 
Page o3253  
November 2012  

Received 25 October 2012
Accepted 26 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.112
Data-to-parameter ratio = 15.0
Details
Open access

Piperidine-1-carboximidamide

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

In the title compound, C6H13N3, the C=N and C-N bond lengths in the CN3 unit are 1.3090 (17), and 1.3640 (17) (C-NH2) and 1.3773 (16) Å, indicating double- and single-bond character, respectively. The N-C-N angles are 116.82 (12), 119.08 (11) and 124.09 (11)°, showing a deviation of the CN3 plane from an ideal trigonal-planar geometry. The piperidine ring is in a chair conformation. In the crystal, molecules are linked by N-H...N hydrogen bonds, forming a two-dimensional network along the ac plane.

Related literature

For the crystal structure of 4-morpholinecarboxamidine, see: Tiritiris (2012[Tiritiris, I. (2012). Acta Cryst. E68, o3118.]). For the crystal structure of bis(piperidin-1-yl)methanone, see: Betz et al. (2011[Betz, R., Gerber, T. & Schalekamp, H. (2011). Acta Cryst. E67, o397.]).

[Scheme 1]

Experimental

Crystal data
  • C6H13N3

  • Mr = 127.19

  • Monoclinic, P 21 /c

  • a = 12.2193 (9) Å

  • b = 5.5784 (5) Å

  • c = 10.4885 (7) Å

  • [beta] = 91.887 (4)°

  • V = 714.55 (10) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.60 mm-1

  • T = 100 K

  • 0.45 × 0.26 × 0.06 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.830, Tmax = 0.965

  • 4190 measured reflections

  • 1413 independent reflections

  • 1116 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.112

  • S = 1.03

  • 1413 reflections

  • 94 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H21...N1i 0.94 (2) 2.15 (2) 3.071 (1) 168 (1)
N2-H22...N1ii 0.94 (2) 2.15 (2) 3.090 (1) 177 (1)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: GO2073 ).


Acknowledgements

The author thanks Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for measuring the crystal data.

References

Betz, R., Gerber, T. & Schalekamp, H. (2011). Acta Cryst. E67, o397.  [CrossRef] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tiritiris, I. (2012). Acta Cryst. E68, o3118.  [CrossRef] [details]


Acta Cryst (2012). E68, o3253  [ doi:10.1107/S1600536812044467 ]

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