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Volume 68 
Part 1 
Page o16  
January 2012  

Received 25 October 2011
Accepted 10 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.153
Data-to-parameter ratio = 13.1
Details
Open access

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

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

The title compound, C17H10O2, is nearly planar, the maximum atomic deviation being 0.053 (2) Å. In the molecule, an intramolecular O-H...O hydrogen bond generates an S(6) ring motif. In the crystal, inversion-related molecules are linked by pairs of weak C-H...O hydrogen bonds, forming dimers. [pi]-[pi] stacking is observed in the crystal structure, the closest centroid-centroid distance being 3.7846 (16) Å.

Related literature

For the spectroscopy and preparation of the title compound, see: Aquino et al. (2005[Aquino, A. J. A., Lischka, H. & Hättig, C. (2005). J. Phys. Chem. A, 109, 3201-3208.]); 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 proton-transfer dyes, see: Chen & Pang (2009[Chen, W.-H. & Pang, Y. (2009). Tetrahedron Lett. 50, 6680-6683.], 2010[Chen, W.-H. & Pang, Y. (2010). Tetrahedron Lett. 51, 1914-1918.]); Chuang et al. (2011[Chuang, W.-T., Hsieh, C.-C., Lai, C.-H., Lai, C.-H., Shih, C.-W., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Org. Chem. 76, 8189-8202.]); Han et al. (2010[Han, D. Y., Kim, J. M., Kim, J., Jung, H. S., Lee, Y. H., Zhang, J. F. & Kim, J. S. (2010). Tetrahedron Lett. 51, 1947-1951.]); Ito et al. (2011[Ito, Y., Amimoto, K. & Kawato, T. (2011). Dyes Pigments, 89, 319-323.]); Jung et al. (2009[Jung, H. Y., Kim, H. J., Vicens, J. & Kim, J. S. (2009). Tetrahedron Lett. 50, 983-987.]); Lim et al. (2011[Lim, C.-K., Seo, J., Kim, S., Kwon, I. C., Ahn, C.-H. & Park, S. Y. (2011). Dyes Pigments, 90, 284-289.]). For related structures, see: 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.]); Li et al. (2007[Li, Z., Xu, J.-H., Rosli, M. M. & Fun, H.-K. (2007). Acta Cryst. E63, o3435.]); Saeed & Bolte (2007[Saeed, A. & Bolte, M. (2007). Acta Cryst. E63, o2757.]). 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
  • C17H10O2

  • Mr = 246.25

  • Monoclinic, P 21 /c

  • a = 12.474 (2) Å

  • b = 6.4401 (12) Å

  • c = 15.601 (3) Å

  • [beta] = 109.188 (3)°

  • V = 1183.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 297 K

  • 0.42 × 0.22 × 0.12 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • 6331 measured reflections

  • 2310 independent reflections

  • 1322 reflections with I > 2[sigma](I)

  • Rint = 0.087

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.153

  • S = 1.03

  • 2310 reflections

  • 176 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O1 1.11 (4) 1.90 (4) 2.877 (3) 145 (3)
C3-H3A...O1i 0.93 2.52 3.369 (3) 151
Symmetry code: (i) -x+1, -y-1, -z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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 (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: XU5365 ).


Acknowledgements

This work was supported by the National Science Council (NSC 99-2113-M-035-001-MY2) and Feng Chia University in Taiwan.

References

Aquino, A. J. A., Lischka, H. & Hättig, C. (2005). J. Phys. Chem. A, 109, 3201-3208.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.  [CSD] [CrossRef] [details]
Chen, W.-H. & Pang, Y. (2009). Tetrahedron Lett. 50, 6680-6683.  [ISI] [CrossRef] [ChemPort]
Chen, W.-H. & Pang, Y. (2010). Tetrahedron Lett. 51, 1914-1918.  [ISI] [CrossRef] [ChemPort]
Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.  [CSD] [CrossRef] [details]
Chuang, W.-T., Hsieh, C.-C., Lai, C.-H., Lai, C.-H., Shih, C.-W., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Org. Chem. 76, 8189-8202.  [CSD] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Han, D. Y., Kim, J. M., Kim, J., Jung, H. S., Lee, Y. H., Zhang, J. F. & Kim, J. S. (2010). Tetrahedron Lett. 51, 1947-1951.  [ISI] [CSD] [CrossRef] [ChemPort]
Ito, Y., Amimoto, K. & Kawato, T. (2011). Dyes Pigments, 89, 319-323.  [CrossRef] [ChemPort]
Jung, H. Y., Kim, H. J., Vicens, J. & Kim, J. S. (2009). Tetrahedron Lett. 50, 983-987.  [ISI] [CrossRef] [ChemPort]
Li, Z., Xu, J.-H., Rosli, M. M. & Fun, H.-K. (2007). Acta Cryst. E63, o3435.  [CSD] [CrossRef] [details]
Lim, C.-K., Seo, J., Kim, S., Kwon, I. C., Ahn, C.-H. & Park, S. Y. (2011). Dyes Pigments, 90, 284-289.  [CrossRef] [ChemPort]
Saeed, A. & Bolte, M. (2007). Acta Cryst. E63, o2757.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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]


Acta Cryst (2012). E68, o16  [ doi:10.1107/S160053681104760X ]

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