1-Meth­oxy-11H-benzo[b]fluoren-11-one

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

doi:10.1107/S1600536812050076

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 (C-C) = 0.005 Å
R = 0.083
wR = 0.250
Data-to-parameter ratio = 14.0
Details

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

Sin-Kai Fang,^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, 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-HO 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). For applications of indanone derivatives, see: Borbone et al. (2011); Borge et al. (2010); Cai & Dolbier (2005); Cui et al. (2009); Fu & Wang (2008); Li et al. (2009); Rahman et al. (2011); Sousa et al. (2011); Yu et al. (2011). For related structures, see: Chang & Chen (2012); Chen et al. (2011a,b).

Experimental

Crystal data

C₁₈H₁₂O₂
M_r = 260.28
Monoclinic, P 2₁ /c
a = 7.7202 (3) Å
b = 9.2462 (4) Å
c = 18.0294 (8) Å
= 99.935 (2)°
V = 1267.68 (9) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.957, T_max = 0.983
11580 measured reflections
2559 independent reflections
1881 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.083
wR(F²) = 0.250
S = 1.11
2559 reflections
183 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O1ⁱ	0.93	2.57	3.299 (5)	135
C11-H11O1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2005); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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

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organic compounds