Received 17 November 2010
In the molecule of the title compound, C16H13N3O4, the atoms of the spiro pyran ring are nearly planar with a maximum deviation of 0.095 (2) Å. The indole and pyran rings are oriented at a dihedral angle of 87.3 (9)°. In the crystal, molecules are linked by intermolecular N-HN and N-HO hydrogen bonds.
For the indole nucleus, see: Da-Silva et al. (2001). Compounds carrying the indole moiety exhibit antibacterial and fungicidal activity, see: Joshi & Chand (1982). Spirooxindole ring systems are found in a number of alkaloids like horsifiline, spirotryprostatin and elacomine, see: Abdel-Rahman et al. (2004). For our work on the preparation of heterocyclic compounds involving indole derivatives, see: Zhu et al. (2007).
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2334 ).
This work was partially supported by the Natural Science Foundation of Higher Education Institutions of Jiangsu Province (grant No. 09KJB150012) and the Special Presidential Foundation of Xuzhou Medical College (grant Nos. 09KJZ19 and 2010KJZ20) and the Open Foundation of the Key Laboratory of Cancer Biotherapy of Xuzhou Medical College (grant No. C0901).
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