Received 12 October 2011
In the title compound, C23H19N3O4, the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3 (1) and 60.4 (1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, molecules are connected by two unique N-HO and O-HO hydrogen-bonding interactions, which form centrosymmetric patterns described by graph-set motifs R22(18) and R22(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C-HO interactions and by aromatic - stacking interactions between the pyran and benzene rings of neighbouring molecules [centroid-centroid distance = 3.755 (1) Å and slippage = 1.371 (2) Å].
For general background to the biological use of pyrrolidine derivatives, see: Pettersson et al. (2011); Bello et al. (2010). For ring puckering parameters, see: Cremer & Pople (1975) and for asymmetry parameters, see: Nardelli (1983). For the structure of another pyrrolidine derivatie, see: Selvanayagam et al. (2011).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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, 1997); 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: NK2121 ).
The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.
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