Received 6 September 2013
In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C-C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thiophene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N-HO hydrogen bonds link the molecules, forming inversion dimers with an R22(8) ring motif. The dimers are linked by further N-HO hydrogen bonds, forming a two-dimensional network lying parallel to (100).
For background to indole derivatives and their biological activity, see: Srivastava et al. (2011). For puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995). For a related structure, see: Inglebert et al. (2013).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2642 ).
The authors are gratefully to Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.
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