Received 28 November 2012
The title indole derivative, C17H15NO3S, crystallizes with two independent molecules in the asymmetric unit. The benzene ring of the tosyl group is almost perpedicular to the indole ring in both molecules, with interplanar angles of 82.60 (5)° and 81.82 (6)°. The two molecules are, as a consequence, able to form an almost centrosymmetric non-bonded dimer, in which the molecules are linked by pairs of C-H interactions. The crystal structure displays a three-dimensional network of C-HO interactions. A - interaction occurs between inversion-related indole rings with a centroid-centroid distance of 3.6774 (16) Å and an interplanar angle of 1.53 (15)°. This interaction leads to a stacking of molecules along the a axis.
For studies of reactions involving indoles, see: Pathak et al. (2006); Pelly et al. (2005); Sharma et al. (2010). It is interesting to note that the reaction used to synthesize this product has been reported to be ineffective when carried out in acetone, see: Kothandaraman et al. (2011).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and SCHAKAL-99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2083 ).
This work was supported by the University of the Witwatersrand and National Research Foundation, Pretoria.
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