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

Lin, H.-Y.; Chang, C.-W.; Tsai, H.-Y.; Luo, M.-H.; Chen, K.-Y.

doi:10.1107/S1600536812041293

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 (C-C) = 0.005 Å
R = 0.087
wR = 0.231
Data-to-parameter ratio = 18.4
Details

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

Hong-Yi Lin,^a Che-Wei Chang,^a Hsing-Yang Tsai,^a Ming-Hui Luo ^a and Kew-Yu Chen ^a ^*

^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-HO hydrogen bonds, forming a C(6) chain along [010].

Related literature

For the preparation of the title compound, see: Rahimizadeh et al. (2010). For applications of indanone derivatives, see: Borbone et al. (2011); Borge et al. (2010); Cai et al. (2005); Cui et al. (2009); Fu & Wang (2008); Li et al. (2009); Sousa et al. (2011); Tang et al. (2011); Yu et al. (2011). For related structures, see: Ali et al. (2010a,b,c,d); Chen et al. (2011a,b). For C-HO hydrogen bonds, see: Li et al. (2011a,b); Wang & Chen (2011); Xi et al. (2010). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₁H₁₀O₃
M_r = 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 radiation
= 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) T_min = 0.761, T_max = 1.000
8705 measured reflections
2339 independent reflections
1302 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.087
wR(F²) = 0.231
S = 1.10
2339 reflections
127 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8AO3ⁱ	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); 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: 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.
Ali, M. A., Ismail, R., Tan, S. C., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o2875.
Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010c). Acta Cryst. E66, o2753.
Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010d). Acta Cryst. E66, o2864.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290-295.
Borge, J., Cadierno, V., Díez, J., García-Garrido, S. E. & Gimeno, J. (2010). Dyes Pigm. 87, 209-217.
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.
Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.
Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.
Cui, Y., Ren, H., Yu, J., Wang, Z. & Qian, G. (2009). Dyes Pigm. 81, 53-57.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Fu, T. L. & Wang, I. J. (2008). Dyes Pigm. 76, 590-595.
Li, C. J., Feng, Y. Q., Liu, X. J. & Zhang, T. Y. (2011a). Chin. Chem. Lett. 22, 539-542.
Li, X., Kim, S.-H. & Son, Y.-A. (2009). Dyes Pigm. 82, 293-298.
Li, H. Q., Zhang, Z. B. & Li, L. (2011b). Chin. Chem. Lett. 22, 280-283.
Rahimizadeh, M., Pordel, M., Bakavoli, M. & Eshghi, H. (2010). Dyes Pigm. 86, 266-270.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sousa, C. M., Berthet, J., Delbaere, S. & Coelho, P. J. (2011). Dyes Pigm. 92, 537-541.
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.
Wang, E. J. & Chen, G. Y. (2011). Chin. Chem. Lett. 22, 847-850.
Xi, H. T., Yi, T. T. & Sun, X. Q. (2010). Chin. Chem. Lett. 21, 633-636.
Yu, S. B., Liu, H. M., Luo, Y. & Lu, W. (2011). Chin. Chem. Lett. 22, 264-267.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References