5-Hy­droxy­indan-1-one

Chen, K.-Y.; Fang, T.-C.; Chang, M.-J.

doi:10.1107/S1600536811010956

Volume 67
Part 4
Page o992
April 2011

Received 16 March 2011
Accepted 24 March 2011
Online 31 March 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.081
Data-to-parameter ratio = 11.8
Details

5-Hydroxyindan-1-one

Kew-Yu Chen,^a ^* Tzu-Chien Fang ^a and Ming-Jen Chang ^a

^aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
Correspondence e-mail: kyuchen@fcu.edu.tw

In the title compound (5HIN), C₉H₈O₂, is perfectly planar as all atoms, except the H atoms of both CH₂ groups, lie on a crystallographic mirror plane. In the crystal, molecules are linked by strong intermolecular O-HO hydrogen bonds, forming an infinite chain along [100], generating a C(8) motif.

Related literature

For the spectroscopy of the title compound, see: Magnusson et al. (1964). For the synthetic and biological applications on indanones, see: Cai et al. (2005); De Paulis et al. (1981); Howbert & Crowell (1990); Kwiecien et al. (1991). For the preparation, see: Danishefsky et al. (1979). For related structures, see: Chen et al. (2011); Li et al. (2007); Saeed & Bolte (2007). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₉H₈O₂
M_r = 148.15
Orthorhombic, P n m a
a = 13.9126 (7) Å
b = 6.7332 (4) Å
c = 7.5368 (3) Å
V = 706.02 (6) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 297 K
0.39 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.991, T_max = 1.000
2023 measured reflections
920 independent reflections
605 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.081
S = 1.03
920 reflections
78 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1ⁱ	0.98 (2)	1.69 (2)	2.6618 (19)	173 (2)
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2345 ).

Acknowledgements

Financial support from the National Science Council of the Republic of China is gratefully acknowledged.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011). Acta Cryst. E67, o927.
Danishefsky, S., Harayama, T. & Singh, R. K. (1979). J. Am. Chem. Soc. 101, 7008-7012.
De Paulis, T., Betts, C. R., Smith, H. E., Mobley, P. L., Marnier, D. H. & Sulser, F. (1981). J. Med. Chem. 24, 1021-1024.
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Saeed, A. & Bolte, M. (2007). Acta Cryst. E63, o2757.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds