Received 4 December 2010
In the molecule of the title compound, C17H10BrNO5, the indoline system and the attached coumarin ring are each essentially planar with maximum deviations of 0.074 (2) and 0.062 (2) Å, respectively. The dihedral angle between them is 85.09 (3)°. In the crystal, all heteroatoms (except for the coumarin oxo O atoms) are involved in intra- and intermolecular hydrogen bonds. An intramolecular O-HO hydrogen bond occurs. In the crystal, molecules are linked through O-HO, N-HO and C-HO contacts, forming a complex three-dimensional structure.
For general background to indoles and their biological activity, see: Da-Silva et al. (2001); Joshi & Chand (1982). Coumarin and its derivatives are important in the perfume, cosmetic and pharmaceutical industries, see: Soine (1964). For the synthesis of indole and coumarin derivatives in water, see: Zhu (2008).
Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2009); 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: BH2329 ).
This work was partially supported by the Natural Science Foundation of Higher Education Institutions of Jiangsu Province (grant No. 09KJB150012), 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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