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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 [sigma](C-C) = 0.001 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 17.6
Details
Open access

2'-Acetonaphthone

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 Car-Car-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-H...O interactions along the ac diagonal.

Related literature

For synthesis details, see: Bassilios & Salem (1952[Bassilios, H. F. & Salem, A. Y. (1952). Bull. Soc. Chim. Fr. pp. 586-592.]). For related structures, see: Kemperman et al. (2000[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.]); Mattheus et al. (2001[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 et al. (1998[Miyake, Y., Hirose, J., Hasegawa, Y., Sada, K. & Miyata, M. (1998). Chem. Commun. pp. 111-112.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10O

  • Mr = 170.20

  • Monoclinic, P 21 /n

  • a = 5.9875 (5) Å

  • b = 7.4025 (7) Å

  • c = 20.2778 (18) Å

  • [beta] = 93.747 (1)°

  • V = 896.84 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]) Tmin = 0.701, Tmax = 0.746

  • 12546 measured reflections

  • 2089 independent reflections

  • 1840 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.118

  • S = 1.08

  • 2089 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O1i 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[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [ISI] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Mattheus, C. C., Dros, A. B., Baas, J., Meetsma, A., Boer, J. L. de & Palstra, T. T. M. (2001). Acta Cryst. C57, 939-941.  [CSD] [CrossRef] [ChemPort] [details]
Miyake, Y., Hirose, J., Hasegawa, Y., Sada, K. & Miyata, M. (1998). Chem. Commun. pp. 111-112.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3112  [ doi:10.1107/S1600536812039554 ]

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