[Journal logo]

Volume 69 
Part 1 
Page o79  
January 2013  

Received 5 October 2012
Accepted 7 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 299 K
Mean [sigma](C-C) = 0.005 Å
R = 0.083
wR = 0.250
Data-to-parameter ratio = 14.0
Details
Open access

1-Methoxy-11H-benzo[b]fluoren-11-one

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

In the title compound, C18H12O2, the non-H atoms are nearly coplanar, the maximum atomic deviation being 0.113 (2) Å. [pi]-[pi] stacking is observed in the crystal structure, the shortest centroid-centroid distance being 3.5983 (19) Å. The molecular packing is further stabilized by weak C-H...O hydrogen bonds, forming an infinite chain along [100] and generating a C(6) motif.

Related literature

For the preparation of the title compound, 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.]). 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 & Dolbier (2005[Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluorine 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.]); Rahman et al. (2011[Rahman, A., Zahrani, S. M. A. & Ajjou, A. A. N. (2011). Chin. Chem. Lett. 22, 691-693.]); 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: Chang & Chen (2012[Chang, Y. J. & Chen, K.-Y. (2012). Acta Cryst. E68, o3063.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H12O2

  • Mr = 260.28

  • Monoclinic, P 21 /c

  • a = 7.7202 (3) Å

  • b = 9.2462 (4) Å

  • c = 18.0294 (8) Å

  • [beta] = 99.935 (2)°

  • V = 1267.68 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 299 K

  • 0.50 × 0.47 × 0.20 mm

Data collection
  • Bruker SMART CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.983

  • 11580 measured reflections

  • 2559 independent reflections

  • 1881 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.083

  • wR(F2) = 0.250

  • S = 1.11

  • 2559 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O1i 0.93 2.57 3.299 (5) 135
C11-H11...O1ii 0.93 2.55 3.298 (4) 138
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5629 ).


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.

References

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). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluorine Chem. 126, 479-482.  [ISI] [CrossRef] [ChemPort]
Chang, Y. J. & Chen, K.-Y. (2012). Acta Cryst. E68, o3063.  [CSD] [CrossRef] [details]
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. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fu, T.-L. & Wang, I.-J. (2008). Dyes Pigm. 76, 590-595.  [CrossRef] [ChemPort]
Li, X., Kim, S. H. & Son, Y. A. (2009). Dyes Pigm. 82, 293-298.  [CrossRef] [ChemPort]
Rahman, A., Zahrani, S. M. A. & Ajjou, A. A. N. (2011). Chin. Chem. Lett. 22, 691-693.  [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 (2013). E69, o79  [ doi:10.1107/S1600536812050076 ]

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.