[Journal logo]

Volume 68 
Part 11 
Page o3097  
November 2012  

Received 2 October 2012
Accepted 5 October 2012
Online 10 October 2012

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 17.2
Details
Open access

4-Hydroxyindan-1-one

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

The molecule of the title compound, C9H8O2, is essentially planar except for the methylene H atoms [maximum deviation = 0.028 (1) Å]. In the crystal, the molecules are linked by classical O-H...O hydrogen bonds and weak C-H...O interactions into chains along [110] and [1-10].

Related literature

For the preparation of the title compound, see: Gerasov et al. (2011[Gerasov, A. O., Zyabrev, K. V., Shandura, M. P. & Kovtun, Y. P. (2011). Dyes Pigm. 89, 76-85.]). For applications of indanone derivatives, see: Tang et al. (2011[Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Am. Chem. Soc. 133, 17738-17745.]); Borbone et al. (2011[Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290-295.]); Borge et al. (2010[Borge, J., Cadierno, V., Díez, J., García-Garrido, S. E. & Gimeno, J. (2010). Dyes Pigm. 87, 209-217.]); Cai et al. (2005[Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluor. Chem. 126, 479-482.]); Cui et al. (2009[Cui, Y., Ren, H., Yu, J., Wang, Z. & Qian, G. (2009). Dyes Pigm. 81, 53-57.]); Fu & Wang (2008[Fu, T.-L. & Wang, I.-J. (2008). Dyes Pigm. 76, 590-595.]); Li et al. (2009[Li, X., Kim, S. H. & Son, Y. A. (2009). Dyes Pigm. 82, 293-298.]); Sousa et al. (2011[Sousa, C. M., Berthet, J., Delbaere, S. & Coelho, P. J. (2011). Dyes Pigm. 92, 537-541.]); Yu et al. (2011[Yu, S.-B., Liu, H.-M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264-267.]). For related structures, see: Ali et al. (2010[Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o2864.]); Chen et al. (2011a[Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.],b[Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8O2

  • Mr = 148.15

  • Monoclinic, C 2/c

  • a = 13.5890 (6) Å

  • b = 8.6160 (3) Å

  • c = 13.9435 (6) Å

  • [beta] = 116.738 (6)°

  • V = 1457.98 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 297 K

  • 0.63 × 0.60 × 0.38 mm

Data collection
  • Bruker SMART CCD detector diffractometer

  • 6305 measured reflections

  • 1794 independent reflections

  • 1289 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.06

  • 1794 reflections

  • 104 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2i 0.94 (2) 1.75 (2) 2.6918 (18) 175 (2)
C2-H2A...O2i 0.93 2.59 3.255 (2) 129
Symmetry code: (i) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5628 ).


Acknowledgements

This work was supported by the National Science Council (grant No. NSC 101-2113-M-035-001-MY2) and Feng Chia University in Taiwan. The authors appreciate the Precision Instrument Support Center of Feng Chia University in providing fabrication and measurement facilities.

References

Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o2864.  [CSD] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290-295.  [CSD] [CrossRef] [ChemPort]
Borge, J., Cadierno, V., Díez, J., García-Garrido, S. E. & Gimeno, J. (2010). Dyes Pigm. 87, 209-217.  [CSD] [CrossRef] [ChemPort]
Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluor. Chem. 126, 479-482.  [ISI] [CrossRef] [ChemPort]
Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.  [CSD] [CrossRef] [details]
Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.  [CSD] [CrossRef] [details]
Cui, Y., Ren, H., Yu, J., Wang, Z. & Qian, G. (2009). Dyes Pigm. 81, 53-57.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fu, T.-L. & Wang, I.-J. (2008). Dyes Pigm. 76, 590-595.  [CrossRef] [ChemPort]
Gerasov, A. O., Zyabrev, K. V., Shandura, M. P. & Kovtun, Y. P. (2011). Dyes Pigm. 89, 76-85.  [CrossRef] [ChemPort]
Li, X., Kim, S. H. & Son, Y. A. (2009). Dyes Pigm. 82, 293-298.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sousa, C. M., Berthet, J., Delbaere, S. & Coelho, P. J. (2011). Dyes Pigm. 92, 537-541.  [CrossRef]
Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Am. Chem. Soc. 133, 17738-17745.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Yu, S.-B., Liu, H.-M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264-267.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3097  [ doi:10.1107/S1600536812041669 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.