Received 26 May 2013
In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N-C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intramolecular C-HO hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent molecules are linked via N-HO hydrogen bonds, forming chains propagating along . The chains are linked via weak C-HO hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C-H interactions.
For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Tang et al. (2007). For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Colgan et al. (1996).
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 for Windows (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: SU2607 ).
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SK, TS and DV thank the UGC (SAP-CAS) for the departmental facilities. SK also thanks DST PURSE for a Junior Research Fellowship and TS also thanks DST Inspire for a fellowship.
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