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

Chiririwa, H.; Moss, J.R.; Hendricks, D.; Meijboom, R.

doi:10.1107/S1600536812040809

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.045
wR = 0.125
Data-to-parameter ratio = 15.9
Details

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

Haleden Chiririwa,^a ^* John R. Moss,^a Denver Hendricks ^b and Reinout Meijboom ^c

^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); Haga & Koizumi (1985); Chiririwa et al. (2011a,b).

Experimental

Crystal data

C₁₈H₁₆N₂S₂
M_r = 324.45
Triclinic, $[P \overline 1]$
a = 8.8517 (3) Å
b = 10.3937 (5) Å
c = 10.5763 (4) Å
= 63.836 (2)°
= 69.023 (2)°
= 72.394 (2)°
V = 803.22 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.931, T_max = 0.959
34407 measured reflections
3282 independent reflections
2478 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.125
S = 1.06
3282 reflections
206 parameters
9 restraints
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.48 e Å^-3

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005), ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Chiririwa, H., Meijboom, R. & Omondi, B. (2011b). Acta Cryst. E67, o922.
Chiririwa, H., Moss, J. R., Su, H., Hendricks, D. & Meijboom, R. (2011a). Acta Cryst. E67, o921.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Haga, M. & Koizumi, K. (1985). Inorg. Chim. Acta, 104, 47-50.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds