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

Zhu, S.-L.

doi:10.1107/S1600536811000213

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 (C-C) = 0.003 Å
R = 0.024
wR = 0.059
Data-to-parameter ratio = 12.1
Details

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

Song-Lei Zhu ^a ^*

^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-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.

Related literature

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).

Experimental

Crystal data

C₁₇H₁₀BrNO₅
M_r = 388.17
Monoclinic, P 2₁ /c
a = 11.358 (3) Å
b = 13.428 (3) Å
c = 10.360 (2) Å
= 113.307 (3)°
V = 1451.1 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.173, T_max = 0.366
13755 measured reflections
2655 independent reflections
2544 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.059
S = 1.08
2655 reflections
220 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.84	1.98	2.7672 (17)	155
O5-H5O1	0.84	1.81	2.5486 (19)	145
N1-H1AO4ⁱⁱ	0.88	2.16	2.940 (2)	148
C7-H7O2ⁱⁱⁱ	0.95	2.49	3.429 (2)	172
C8-H8O1ⁱⁱⁱ	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); 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 ).

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.
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.
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.
Soine, T. O. (1964). J. Pharm. Sci. 53, 231-264.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhu, S.-L. (2008). Acta Cryst. E64, o1162.

organic compounds