1-Hy­droxy-11H-benzo[b]fluoren-11-one

Chen, K.-Y.; Chang, M.-J.; Fang, T.-C.

doi:10.1107/S160053681104760X

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 (C-C) = 0.004 Å
R = 0.047
wR = 0.153
Data-to-parameter ratio = 13.1
Details

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

Kew-Yu Chen,^a ^* Ming-Jen Chang ^a and Tzu-Chien Fang ^a

^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-HO hydrogen bond generates an S(6) ring motif. In the crystal, inversion-related molecules are linked by pairs of weak C-HO 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); Tang et al. (2011). For applications of proton-transfer dyes, see: Chen & Pang (2009, 2010); Chuang et al. (2011); Han et al. (2010); Ito et al. (2011); Jung et al. (2009); Lim et al. (2011). For related structures, see: Chen et al. (2011a,b); Li et al. (2007); Saeed & Bolte (2007). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₇H₁₀O₂
M_r = 246.25
Monoclinic, P 2₁ /c
a = 12.474 (2) Å
b = 6.4401 (12) Å
c = 15.601 (3) Å
= 109.188 (3)°
V = 1183.6 (4) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.087

Refinement

R[F² > 2(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
_max = 0.19 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1	1.11 (4)	1.90 (4)	2.877 (3)	145 (3)
C3-H3AO1ⁱ	0.93	2.52	3.369 (3)	151
Symmetry code: (i) -x+1, -y-1, -z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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 (Farrugia, 1999).

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

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organic compounds