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Volume 68 
Part 11 
Page o3137  
November 2012  

Received 18 September 2012
Accepted 27 September 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.045
wR = 0.125
Data-to-parameter ratio = 15.9
Details
Open access

1-(Thiophen-2-yl)-N-(4-{(E)-[(thiophen-2-yl)methyl]iminomethyl}benzylidene)methanamine

aDepartment of Chemistry, University of Cape Town, Private Bag, Rondebosch, 7707, South Africa,bDivision of Medical Biochemistry, Faculty of Health Sciences, Private Bag X3, Observatory 7935, South Africa, and cResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, PO Box 524 Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: harrychiririwa@yahoo.com

The title compound C18H16N2S2, crystallizes with two independent half-molecules in the asymmetric unit, in one of which the thiophene rings are disordered in a 0.67:0.33 ratio. Each independent molecule lies across a crystallographic centre of symmetry. The dihedral angle between central (half) benzene ring and the thiophene ring is 11.82°.

Related literature

For similar thiophenyldimine-based bridging ligands, see: Chakraborty et al. (1999[Chakraborty, S., Munshi, P. & Lahiri, G. K. (1999). Polyhedron, 18, 1437-1444.]); Haga & Koizumi (1985[Haga, M. & Koizumi, K. (1985). Inorg. Chim. Acta, 104, 47-50.]); Chiririwa et al. (2011a[Chiririwa, H., Moss, J. R., Su, H., Hendricks, D. & Meijboom, R. (2011a). Acta Cryst. E67, o921.],b[Chiririwa, H., Meijboom, R. & Omondi, B. (2011b). Acta Cryst. E67, o922.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16N2S2

  • Mr = 324.45

  • Triclinic, [P \overline 1]

  • a = 8.8517 (3) Å

  • b = 10.3937 (5) Å

  • c = 10.5763 (4) Å

  • [alpha] = 63.836 (2)°

  • [beta] = 69.023 (2)°

  • [gamma] = 72.394 (2)°

  • V = 803.22 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 173 K

  • 0.22 × 0.20 × 0.13 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.959

  • 34407 measured reflections

  • 3282 independent reflections

  • 2478 reflections with I > 2[sigma](I)

  • Rint = 0.052

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

  • wR(F2) = 0.125

  • S = 1.06

  • 3282 reflections

  • 206 parameters

  • 9 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]), ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2071 ).


Acknowledgements

Mintek and Project AuTEK are acknowledged for funding this project.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakraborty, S., Munshi, P. & Lahiri, G. K. (1999). Polyhedron, 18, 1437-1444.  [ISI] [CrossRef] [ChemPort]
Chiririwa, H., Meijboom, R. & Omondi, B. (2011b). Acta Cryst. E67, o922.  [CSD] [CrossRef] [details]
Chiririwa, H., Moss, J. R., Su, H., Hendricks, D. & Meijboom, R. (2011a). Acta Cryst. E67, o921.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Haga, M. & Koizumi, K. (1985). Inorg. Chim. Acta, 104, 47-50.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3137  [ doi:10.1107/S1600536812040809 ]

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