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Volume 67 
Part 2 
Page o307  
February 2011  

Received 4 December 2010
Accepted 4 January 2011
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.059
Data-to-parameter ratio = 12.1
Details
Open access

4-Bromo-3-hydroxy-3-(4-hydroxy-2-oxo-2H-chromen-3-yl)indolin-2-one

aDepartment of Chemistry, Xuzhou Medical College, Xuzhou 221004, People's Republic of China
Correspondence e-mail: songleizhu@126.com

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-H...O hydrogen bond occurs. In the crystal, molecules are linked through O-H...O, N-H...O and C-H...O contacts, forming a complex three-dimensional structure.

Related literature

For general background to indoles and their biological activity, see: Da-Silva et al. (2001[Da-Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.]); Joshi & Chand (1982[Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1-12.]). Coumarin and its derivatives are important in the perfume, cosmetic and pharmaceutical industries, see: Soine (1964[Soine, T. O. (1964). J. Pharm. Sci. 53, 231-264.]). For the synthesis of indole and coumarin derivatives in water, see: Zhu (2008[Zhu, S.-L. (2008). Acta Cryst. E64, o1162.]).

[Scheme 1]

Experimental

Crystal data
  • C17H10BrNO5

  • Mr = 388.17

  • Monoclinic, P 21 /c

  • a = 11.358 (3) Å

  • b = 13.428 (3) Å

  • c = 10.360 (2) Å

  • [beta] = 113.307 (3)°

  • V = 1451.1 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.86 mm-1

  • T = 153 K

  • 0.78 × 0.36 × 0.35 mm

Data collection
  • Rigaku Mercury diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.173, Tmax = 0.366

  • 13755 measured reflections

  • 2655 independent reflections

  • 2544 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.059

  • S = 1.08

  • 2655 reflections

  • 220 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.84 1.98 2.7672 (17) 155
O5-H5...O1 0.84 1.81 2.5486 (19) 145
N1-H1A...O4ii 0.88 2.16 2.940 (2) 148
C7-H7...O2iii 0.95 2.49 3.429 (2) 172
C8-H8...O1iii 0.95 2.61 3.217 (2) 122
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+2, -y+1, -z+1; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2001[Rigaku/MSC (2001). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2329 ).


Acknowledgements

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).

References

Da-Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.  [ChemPort]
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA.
Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1-12.  [ChemPort] [PubMed]
Rigaku/MSC (2001). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soine, T. O. (1964). J. Pharm. Sci. 53, 231-264.  [CrossRef] [PubMed] [ChemPort] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zhu, S.-L. (2008). Acta Cryst. E64, o1162.  [CSD] [CrossRef] [details]


Acta Cryst (2011). E67, o307  [ doi:10.1107/S1600536811000213 ]

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