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Volume 68 
Part 11 
Pages o3075-o3076  
November 2012  

Received 27 September 2012
Accepted 2 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.005 Å
R = 0.087
wR = 0.231
Data-to-parameter ratio = 18.4
Details
Open access

3-Oxo-2,3-dihydro-1H-inden-4-yl acetate

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

In the title compound, C11H10O3, the 1-indanone unit is essentially planar (r.m.s. deviation = 0.036 Å). In the crystal, molecules are linked by non-classical C-H...O hydrogen bonds, forming a C(6) chain along [010].

Related literature

For the preparation of the title compound, see: Rahimizadeh et al. (2010[Rahimizadeh, M., Pordel, M., Bakavoli, M. & Eshghi, H. (2010). Dyes Pigm. 86, 266-270.]). For applications of indanone derivatives, see: 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.]); 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.]); 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. (2010a[Ali, M. A., Ismail, R., Choon, T. S., Rosli, M. M. & Fun, H.-K. (2010a). Acta Cryst. E66, o2878.],b[Ali, M. A., Ismail, R., Tan, S. C., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o2875.],c[Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010c). Acta Cryst. E66, o2753.],d[Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010d). 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 C-H...O hydrogen bonds, see: Li et al. (2011a[Li, C. J., Feng, Y. Q., Liu, X. J. & Zhang, T. Y. (2011a). Chin. Chem. Lett. 22, 539-542.],b[Li, H. Q., Zhang, Z. B. & Li, L. (2011b). Chin. Chem. Lett. 22, 280-283.]); Wang & Chen (2011[Wang, E. J. & Chen, G. Y. (2011). Chin. Chem. Lett. 22, 847-850.]); Xi et al. (2010[Xi, H. T., Yi, T. T. & Sun, X. Q. (2010). Chin. Chem. Lett. 21, 633-636.]). 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
  • C11H10O3

  • Mr = 190.19

  • Orthorhombic, P b c a

  • a = 9.8514 (10) Å

  • b = 8.9757 (7) Å

  • c = 21.917 (3) Å

  • V = 1938.0 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 297 K

  • 0.76 × 0.60 × 0.28 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.761, Tmax = 1.000

  • 8705 measured reflections

  • 2339 independent reflections

  • 1302 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.087

  • wR(F2) = 0.231

  • S = 1.10

  • 2339 reflections

  • 127 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8A...O3i 0.93 2.46 3.223 (5) 139
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: FF2083 ).


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., Choon, T. S., Rosli, M. M. & Fun, H.-K. (2010a). Acta Cryst. E66, o2878.  [CSD] [CrossRef] [details]
Ali, M. A., Ismail, R., Tan, S. C., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o2875.  [CSD] [CrossRef] [details]
Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010c). Acta Cryst. E66, o2753.  [CSD] [CrossRef] [details]
Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010d). 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 (2001). SMART, SAINT and SADABS. 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]
Li, C. J., Feng, Y. Q., Liu, X. J. & Zhang, T. Y. (2011a). Chin. Chem. Lett. 22, 539-542.  [CSD] [CrossRef] [ChemPort]
Li, X., Kim, S.-H. & Son, Y.-A. (2009). Dyes Pigm. 82, 293-298.  [CrossRef] [ChemPort]
Li, H. Q., Zhang, Z. B. & Li, L. (2011b). Chin. Chem. Lett. 22, 280-283.  [CrossRef] [ChemPort]
Rahimizadeh, M., Pordel, M., Bakavoli, M. & Eshghi, H. (2010). Dyes Pigm. 86, 266-270.  [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]
Wang, E. J. & Chen, G. Y. (2011). Chin. Chem. Lett. 22, 847-850.  [CrossRef] [ChemPort]
Xi, H. T., Yi, T. T. & Sun, X. Q. (2010). Chin. Chem. Lett. 21, 633-636.  [CSD] [CrossRef] [ChemPort]
Yu, S. B., Liu, H. M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264-267.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3075-o3076   [ doi:10.1107/S1600536812041293 ]

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