2′-Acetonaphthone

Shotonwa, I.O.; Boeré, R.T.

doi:10.1107/S1600536812039554

Volume 68
Part 11
Page o3112
November 2012

Received 15 September 2012
Accepted 17 September 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.001 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 17.6
Details

2'-Acetonaphthone

Ibukun O. Shotonwa ^a and René T. Boeré ^a ^*

^aDepartment of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, AB, Canada T1K3M4
Correspondence e-mail: boere@uleth.ca

In the structure of the title compound [systematic name: 1-(naphthalen-2-yl)ethanone], C₁₂H₁₀O, the acetyl group is approximately coplanar with the naphthalene ring with a C_ar-C_ar-C=O torsion angle of 5.8 (2)°. In the crystal, the molecules are packed in a classic herringbone arrangement typical for aromatic polycycles such as pentacene. They are also linked by weak end-to-end C-HO interactions along the ac diagonal.

Related literature

For synthesis details, see: Bassilios & Salem (1952). For related structures, see: Kemperman et al. (2000); Mattheus et al. (2001); Miyake et al. (1998). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₁₂H₁₀O
M_r = 170.20
Monoclinic, P 2₁ /n
a = 5.9875 (5) Å
b = 7.4025 (7) Å
c = 20.2778 (18) Å
= 93.747 (1)°
V = 896.84 (14) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 173 K
0.3 × 0.25 × 0.2 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.701, T_max = 0.746
12546 measured reflections
2089 independent reflections
1840 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.118
S = 1.08
2089 reflections
119 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8O1ⁱ	0.95	2.65	3.324 (1)	129
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5250 ).

Acknowledgements

The Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged for a Discovery Grant. The diffractometer was purchased with the help of NSERC and the University of Lethbridge.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bassilios, H. F. & Salem, A. Y. (1952). Bull. Soc. Chim. Fr. pp. 586-592.
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.
Kemperman, G. J., de Gelder, R., Dommerholt, F. J., Raemakers-Franken, P. C., Klunder, A. J. H. & Zwanenburg, B. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 1425-1429.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Mattheus, C. C., Dros, A. B., Baas, J., Meetsma, A., Boer, J. L. de & Palstra, T. T. M. (2001). Acta Cryst. C57, 939-941.
Miyake, Y., Hirose, J., Hasegawa, Y., Sada, K. & Miyata, M. (1998). Chem. Commun. pp. 111-112.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds