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Volume 69 
Part 5 
Page o637  
May 2013  

Received 15 March 2013
Accepted 26 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.108
Data-to-parameter ratio = 12.4
Details
Open access

[2,7-Diethoxy-8-(4-fluorobenzoyl)naphthalen-1-yl](4-fluorophenyl)methanone

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology (TUAT), Koganei, Tokyo 184-8588, Japan, and bInternational Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp

In the molecule of the title compound, C28H22F2O4, the benzoyl groups are aligned almost antiparallel and the fluorobenzene rings form a dihedral angle of 14.12 (7)°. The dihedral angles between the 2,7-diethoxynaphthalene ring system and the benzene rings are 70.00 (4) and 67.28 (4)°. In the crystal, molecules are linked by C-H...O and C-H...F hydrogen bonds, forming layers parallel to the ab plane. The layers are further connected by [pi]-[pi] interactions [centroid-centroid distances of 3.6115 (10) Å] into a three-dimensional structure.

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]); Okamoto et al. (2011[Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.]). For the structures of closely related compounds, see: Nakaema et al. (2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]); Watanabe et al. (2010[Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.]), Isogai et al. (2013[Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71.]).

[Scheme 1]

Experimental

Crystal data
  • C28H22F2O4

  • Mr = 460.46

  • Monoclinic, P 21 /n

  • a = 7.8592 (18) Å

  • b = 21.243 (5) Å

  • c = 13.941 (3) Å

  • [beta] = 105.141 (3)°

  • V = 2246.6 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 173 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku Saturn70 diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.980, Tmax = 0.980

  • 14368 measured reflections

  • 3836 independent reflections

  • 3439 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.108

  • S = 1.00

  • 3836 reflections

  • 309 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O1i 0.95 2.30 3.1939 (17) 156
C23-H23...O2ii 0.95 2.37 3.3214 (18) 176
C6-H6...F1iii 0.95 2.44 3.1937 (17) 136
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5052 ).


Acknowledgements

The authors express their gratitude to Associate Professor Hikaru Takaya and Professor Masaharu Nakamura, Institute for Chemical Research, Kyoto University, for their kind advice. This work was partially supported by the Collaborative Research Program of the Institute for Chemical Research, Kyoto University (grant No. 2012-72).

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [ISI] [CrossRef] [ChemPort] [details]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71.  [CSD] [CrossRef] [details]
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.  [CSD] [CrossRef] [details]
Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.  [ISI] [CrossRef] [ChemPort]
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.  [ISI] [CrossRef] [ChemPort]
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o637  [ doi:10.1107/S1600536813008295 ]

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