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Volume 68 
Part 11 
Page o3063  
November 2012  

Received 26 September 2012
Accepted 27 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.116
Data-to-parameter ratio = 15.1
Details
Open access

7-Methoxyindan-1-one

aDepartment of Chemistry, Tung Hai University, 407 Taichung, Taiwan, and bDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
Correspondence e-mail: kyuchen@fcu.edu.tw

In the title compound, C10H10O2, the 1-indanone unit is essentially planar (r.m.s. deviation = 0.028 Å). In the crystal, molecules are linked via C-H...O hydrogen bonds, forming layers lying parallel to the ab plane. This two-dimensional structure is stabilized by a weak C-H...[pi] interaction. A second weak C-H...[pi] interaction links the layers, forming a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Li et al. (2011[Li, Z., Lin, Y., Xia, J.-L., Zhang, H., Fan, F., Zeng, Q., Feng, D., Yin, J. & Liu, S. H. (2011). Dyes Pigm. 90, 245-252.]). For applications of indanone derivatives, see: 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.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10O2

  • Mr = 162.18

  • Orthorhombic, P b c a

  • a = 8.5386 (7) Å

  • b = 10.4949 (9) Å

  • c = 18.8536 (16) Å

  • V = 1689.5 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 297 K

  • 0.64 × 0.55 × 0.32 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 = 0.683, Tmax = 1.000

  • 8807 measured reflections

  • 1663 independent reflections

  • 1278 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.116

  • S = 1.02

  • 1663 reflections

  • 110 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C5-C9 ring.

D-H...A D-H H...A D...A D-H...A
C3-H3B...O2i 0.97 2.60 3.5183 (18) 159
C7-H7A...O1ii 0.93 2.57 3.4802 (18) 167
C10-H10B...O1iii 0.96 2.59 3.486 (2) 156
C4-H4A...Cg1iv 0.97 2.80 3.6430 (16) 146
C10-H10A...Cg1v 0.96 2.82 3.6260 (16) 143
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iv) -x, -y+1, -z; (v) [-x, y+{\script{1\over 2}}, -z+{\script{1\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: ZL2507 ).


Acknowledgements

This work was supported by the National Science Council, Tung Hai University and Feng Chia University in Taiwan.

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]
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, Z., Lin, Y., Xia, J.-L., Zhang, H., Fan, F., Zeng, Q., Feng, D., Yin, J. & Liu, S. H. (2011). Dyes Pigm. 90, 245-252.  [CSD] [CrossRef] [ChemPort]
Li, H. Q., Zhang, Z. B. & Li, L. (2011b). Chin. Chem. Lett. 22, 280-283.  [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]


Acta Cryst (2012). E68, o3063  [ doi:10.1107/S1600536812040743 ]

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