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Volume 69 
Part 4 
Page o554  
April 2013  

Received 8 March 2013
Accepted 14 March 2013
Online 20 March 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 19.7
Details
Open access

2-Benzylsulfanyl-N-(1,3-dimethylimidazolidin-2-ylidene)aniline

aUniversität Paderborn, Fakultät für Naturwissenschaften, Department Chemie, Warburger Strasse 100, 33098 Paderborn, Germany
Correspondence e-mail: ulrich.floerke@upb.de

The molecular structure of the title compound, C18H21N3S, shows a twisted conformation with a dihedral angle of 67.45 (4)° between the aromatic ring planes and an N-C-C-S torsion angle of -5.01 (13)°. The imidazolidine ring and the aniline moiety make a dihedral angle of 56.03 (4)° and the asscociated C-N-C angle is 125.71 (10)°. The guanidine-like C=N double bond is clearly localized, with a bond length of 1.2879 (14) Å. The C-S-C angle is 102.12 (5)° and the S-C(aromatic) and S-C bond lengths are 1.7643 (11) and 1.8159 (12) Å.

Related literature

For a related structure, see: Neuba et al. (2007[Neuba, A., Flörke, U. & Henkel, G. (2007). Acta Cryst. E63, o3476-o3477.]). For the synthesis, see: Herres-Pawlis et al. (2005[Herres-Pawlis, S., Neuba, A., Seewald, O., Seshadri, T., Egold, H., Flörke, U. & Henkel, G. (2005). Eur. J. Org. Chem. pp. 4879-4890.]); Lindoy & Livingstone (1968[Lindoy, L. F. & Livingstone, S. E. (1968). Inorg. Chem. 7, 1149-1154.]).

[Scheme 1]

Experimental

Crystal data
  • C18H21N3S

  • Mr = 311.44

  • Triclinic, [P \overline 1]

  • a = 7.9814 (5) Å

  • b = 8.1158 (5) Å

  • c = 13.9440 (9) Å

  • [alpha] = 97.232 (1)°

  • [beta] = 102.721 (1)°

  • [gamma] = 107.915 (1)°

  • V = 819.89 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 120 K

  • 0.47 × 0.36 × 0.31 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.913, Tmax = 0.941

  • 7869 measured reflections

  • 3959 independent reflections

  • 3652 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.095

  • S = 1.04

  • 3959 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2203 ).


Acknowledgements

We thank the German research council (DFG) and the Federal Ministry of education and research (BMBF) for continued support of our work.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Herres-Pawlis, S., Neuba, A., Seewald, O., Seshadri, T., Egold, H., Flörke, U. & Henkel, G. (2005). Eur. J. Org. Chem. pp. 4879-4890.  [CSD] [CrossRef]
Lindoy, L. F. & Livingstone, S. E. (1968). Inorg. Chem. 7, 1149-1154.  [CrossRef] [ChemPort] [ISI]
Neuba, A., Flörke, U. & Henkel, G. (2007). Acta Cryst. E63, o3476-o3477.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o554  [ doi:10.1107/S1600536813007101 ]

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