Received 22 March 2010
In the title compound, 2C24H21N3S·C6H6, the two independent Schiff base molecules (A and B) in the asymmetric unit differ in the orientation of the tetrahydrobenzothiophene ring system with respect to the carbazole ring system by 180° rotation about the C-C bond in the C-C=N-C linkage. The two molecules also differ in the orientation of the ethyl groups [C-N-C-C torsion angle of 90.7 (3)° in molecule A, and -79.4 (3)° in molecule B]. In molecule B, two methylene C atoms of the cyclohexene ring are disordered over two sites with occupancies of 0.58 (1) and 0.42 (1). The cyclohexene rings in both molecules adopt half-chair conformations. The dihedral angle between the thiophene ring and the carbazole ring system is 8.07 (9)° in molecule A [3.10 (9)° in molecule B]. In the crystal structure, the independent molecules are linked into dimers by intermolecular C-HN hydrogen bonds. In addition, C-H interactions are observed.
For biological and other applications of Schiff base compounds, see: Abu-Hussen (2006); Elerman et al. (2002); Panneerselvam et al. (2005); Walsh et al. (1996). For ring puckering parameters, see: Cremer & Pople (1975). For a related structure, see: Elerman & Elmali (1998).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5065 ).
HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. The authors thank the Department of Chemistry, King Abdulaziz University, for providing research facilities.
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