Received 23 October 2012
In the title compound, C29H28N2O4, the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced by 0.643 (2) Å from the mean plane formed by the remaining ring atoms. The pyrrolidine ring makes a dihedral angle of 86.1 (8)° with the indoline ring system. In the crystal, N-HO hydrogen bonds result in the formation of cyclic centrosymmetric dimers [R22(8)]. C-H interactions also occur, leading to a chain along the b-axis direction. There is a rather weak - electron interaction between the pyrrazole and benzene rings, with a centroid-centroid distance of 3.765 (1) Å.
For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995). For related structures, see: Ganesh et al. (2012); Narayanan et al. (2012). For graph-set notation, see: Bernstein et al. (1995).
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: ORTEP-3 (Farrugia, 2012); 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: PV2600 ).
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SN thanks the University Grant Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship under the SAP programme.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.
Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o3345.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Waldmann, H. (1995). Synlett, pp. 133-141.