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Volume 68 
Part 12 
Page o3287  
December 2012  

Received 27 October 2012
Accepted 30 October 2012
Online 3 November 2012

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Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.116
Data-to-parameter ratio = 14.4
Details
Open access

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

Daichi Hijikata,a Kosuke Sasagawa,a Sayaka Yoshiwaka,a Akiko Okamotoa* and Noriyuki Yonezawaa

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology (TUAT), Koganei, Tokyo 184.8588, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp

In the title compound, C32H30F2O4, the benzene rings of the benzoyl groups make dihedral angles of 74.55 (6) and 74.39 (7)° with the naphthalene ring system. In the crystal, intra- and intermolecular C-H...[pi] interactions are observed between the butoxy group and the aromatic rings. There are also C-H...F hydrogen bonds present that link the molecules into chains propagating along [010].

Related literature

For the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, 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.], 2012[Okamoto, A., Hijikata, D., Sakai, N. & Yonezawa, N. (2012). Polym. J. doi: 10.1038/pj.2012.135.]). For the crystal structures of similar compounds, see: Sasagawa et al. (2011[Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.]); Watanabe et al. (2010[Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.]).

[Scheme 1]

Experimental

Crystal data

  • C32H30F2O4

  • Mr = 516.56

  • Monoclinic, P 21 /c

  • a = 8.26012 (15) Å

  • b = 20.2309 (4) Å

  • c = 16.5268 (3) Å

  • [beta] = 99.918 (1)°

  • V = 2720.51 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.75 mm-1

  • T = 193 K

  • 0.60 × 0.50 × 0.50 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.661, Tmax = 0.705

  • 50395 measured reflections

  • 4971 independent reflections

  • 4715 reflections with I > 2[sigma](I)

  • Rint = 0.047
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.116

  • S = 1.03

  • 4971 reflections

  • 346 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C12-C17 and C5-C10 rings, respectively.
D-H...A D-H H...A D...A D-H...A
C27-H27B...Cg1 0.99 2.79 3.7754 (19) 175
C26-H26A...Cg2i 0.99 2.54 3.4239 (16) 145
C3-H3...F2ii 0.95 2.50 3.4408 (17) 169
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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: SU2520 ).

Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

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.
Okamoto, A., Hijikata, D., Sakai, N. & Yonezawa, N. (2012). Polym. J. doi: 10.1038/pj.2012.135.
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 (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.  [CSD] [CrossRef] [details]

Acta Cryst (2012). E68, o3287  [ doi:10.1107/S1600536812044923 ]

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