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Volume 69 
Part 5 
Page o678  
May 2013  

Received 15 March 2013
Accepted 1 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.117
Data-to-parameter ratio = 17.0
Details
Open access

4-(4-Fluorobenzoyl)-3-phenyl-3,4-dihydronaphthalen-1(2H)-one

aSchool of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, People's Republic of China
Correspondence e-mail: yiminhu@yahoo.cn

In the title compound, C23H17FO2, the cyclohexenone ring has an envelope conformation, the flap atom being the C atom to which the phenyl ring is attached. The 4-fluorobenzoyl ring and the phenyl ring are inclined to one another by 28.77 (7)°, and by 52.00 (7) and 44.77 (7) °, respectively, to the aromatic ring fused to the cyclohexenone ring. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

Related literature

For the domino reaction as an important tool in the construction of structurally complicated molecules, see: Zhao et al. (2012[Zhao, Q.-S., Hu, Q., Wen, L., Wu, M. & Hu, Y.-M. (2012). Adv. Synth. Catal. 354, 2113-2116.]). For Pd-catalysed cascade reactions, see: Wang & Hu (2011[Wang, H. & Hu, Y. (2011). Acta Cryst. E67, o919.]); Yu & Hu (2012[Yu, T. & Hu, Y. (2012). Acta Cryst. E68, o1184.]). For the use of condensed polycyclic compounds as synthetic building blocks, pharmacophores and electroluminescent materials, see: Rixson et al. (2012[Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. pp. 544-558.]). For cross-coupling reactions of aryl halides with olefins and diynes, see: Hu et al. (2010[Hu, Y.-M., Lin, X.-G., Zhu, T., Wan, J., Sun, Y.-J., Zhao, Q. S. & Yu, T. (2010). Synthesis, 42, 3467-3473.], 2009[Hu, Y.-M., Yu, C.-L., Ren, D., Hu, Q., Zhang, L.-D. & Cheng, D. (2009). Angew. Chem. Int. Ed. 48, 5448-5451.]).

[Scheme 1]

Experimental

Crystal data
  • C23H17FO2

  • Mr = 344.37

  • Monoclinic, P 21 /c

  • a = 8.0063 (6) Å

  • b = 10.6688 (8) Å

  • c = 20.3796 (15) Å

  • [beta] = 97.458 (1)°

  • V = 1726.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.35 × 0.32 × 0.29 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.974

  • 14632 measured reflections

  • 3987 independent reflections

  • 3176 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.117

  • S = 1.03

  • 3987 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14...O1i 0.93 2.53 3.425 (2) 161
C10-H10...O2ii 0.98 2.51 3.1427 (15) 123
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2398 ).


Acknowledgements

We thank the National Science Foundation of China (project Nos. 21272005 and 21072003) for financial support of this work.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hu, Y.-M., Lin, X.-G., Zhu, T., Wan, J., Sun, Y.-J., Zhao, Q. S. & Yu, T. (2010). Synthesis, 42, 3467-3473.  [ISI] [CrossRef]
Hu, Y.-M., Yu, C.-L., Ren, D., Hu, Q., Zhang, L.-D. & Cheng, D. (2009). Angew. Chem. Int. Ed. 48, 5448-5451.  [ISI] [CSD] [CrossRef] [ChemPort]
Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. pp. 544-558.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, H. & Hu, Y. (2011). Acta Cryst. E67, o919.  [CSD] [CrossRef] [details]
Yu, T. & Hu, Y. (2012). Acta Cryst. E68, o1184.  [CSD] [CrossRef] [details]
Zhao, Q.-S., Hu, Q., Wen, L., Wu, M. & Hu, Y.-M. (2012). Adv. Synth. Catal. 354, 2113-2116.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o678  [ doi:10.1107/S1600536813008829 ]

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