[Journal logo]

Volume 69 
Part 4 
Page o520  
April 2013  

Received 18 February 2013
Accepted 5 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.098
Data-to-parameter ratio = 14.6
Details
Open access

N-Cyclohexyl-3-methylbenzamidine

aInstitute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China
Correspondence e-mail: sdbai@sxu.edu.cn

The title amidine compound, C14H20N2, prepared by a one-pot reaction, is asymmetric as only one N atom has an alkyl substituent. The terminal cyclohexyl group connected to the amino N atom is located on the other side of the N-C-N skeleton to the 4-methylbenzene ring and has a chair conformation. The dihedral angle between the phenyl ring and the NCN plane is 47.87 (12)°. In the crystal, molecules are linked via N-H...N hydrogen bonds, forming chains propagating along the a-axis direction.

Related literature

For reviews of related metal amidinates and their applications in olefin polymerization, see: Edelmann (1994[Edelmann, F. T. (1994). Coord. Chem. Rev. 137, 403-481.]); Barker & Kilner (1994[Barker, J. & Kilner, M. (1994). Coord. Chem. Rev. 133, 219-300.]); Collins (2011[Collins, S. (2011). Coord. Chem. Rev. 255, 118-138.]); Bai et al. (2010[Bai, S. D., Tong, H. B., Guo, J. P., Zhou, M. S., Liu, D. S. & Yuan, S. F. (2010). Polyhedron, 29, 262-269.]); Yang et al. (2013[Yang, Q. K., Zhou, M. S., Tong, H. B., Guo, D. L. & Liu, D. S. (2013). Inorg. Chem. Commun. 29, 1-3.]). For a review of neutral amidines, see: Coles (2006[Coles, M. P. (2006). Dalton Trans. pp. 985-1001.]). For a related synthetic method for amidines, see: Wang et al. (2008[Wang, J. F., Xu, F., Cai, T. & Shen, Q. (2008). Org. Lett. 10, 445-448.]). For related silyl-linked bis(amidinate) ligands, see: Bai et al. (2006[Bai, S. D., Guo, J. P. & Liu, D. S. (2006). Dalton Trans. pp. 2244-2250.]).

[Scheme 1]

Experimental

Crystal data
  • C14H20N2

  • Mr = 216.32

  • Orthorhombic, P 21 21 21

  • a = 9.064 (2) Å

  • b = 11.417 (3) Å

  • c = 12.311 (3) Å

  • V = 1274.0 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 200 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.980, Tmax = 0.987

  • 7147 measured reflections

  • 2244 independent reflections

  • 1758 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.098

  • S = 1.02

  • 2244 reflections

  • 154 parameters

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.90 (2) 2.08 (2) 2.975 (2) 168.0 (18)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2395 ).


Acknowledgements

This work was supported by grants from the Natural Science Foundation of China (20702029) and the Natural Science Foundation of Shanxi Province (2008011024).

References

Bai, S. D., Guo, J. P. & Liu, D. S. (2006). Dalton Trans. pp. 2244-2250.  [CSD] [CrossRef]
Bai, S. D., Tong, H. B., Guo, J. P., Zhou, M. S., Liu, D. S. & Yuan, S. F. (2010). Polyhedron, 29, 262-269.  [ISI] [CSD] [CrossRef] [ChemPort]
Barker, J. & Kilner, M. (1994). Coord. Chem. Rev. 133, 219-300.  [CrossRef] [ChemPort] [ISI]
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Coles, M. P. (2006). Dalton Trans. pp. 985-1001.  [CrossRef]
Collins, S. (2011). Coord. Chem. Rev. 255, 118-138.  [ISI] [CrossRef] [ChemPort]
Edelmann, F. T. (1994). Coord. Chem. Rev. 137, 403-481.  [CrossRef] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, J. F., Xu, F., Cai, T. & Shen, Q. (2008). Org. Lett. 10, 445-448.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Yang, Q. K., Zhou, M. S., Tong, H. B., Guo, D. L. & Liu, D. S. (2013). Inorg. Chem. Commun. 29, 1-3.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o520  [ doi:10.1107/S1600536813006272 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.