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Volume 69 
Part 4 
Page o544  
April 2013  

Received 7 March 2013
Accepted 11 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.120
Data-to-parameter ratio = 13.6
Details
Open access

1,8-Bis(4-fluorobenzoyl)naphthalen-2,7-diyl dimethanesulfonate

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

The molecule of the title compound, C26H18F2O8S2, lies across a crystallographic twofold rotation axis. The benzene rings of the 4-fluorobenzoyl groups make dihedral angles of 78.93 (12)° with the naphthalene ring system. An intramolecular C-H...[pi] interaction occurs. In the crystal, a number of C-H...O interactions link the molecules, forming a three-dimensional structure.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, 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 crystal structures of closely related compounds, see: Watanabe et al. (2010[Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.]); Tsumuki et al. (2011[Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.]); Hijikata et al. (2010[Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.], 2012[Hijikata, D., Sasagawa, K., Yoshiwaka, S., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o3246.]); Sasagawa et al. (2013[Sasagawa, K., Takeuchi, R., Kusakabe, T., Yonezawa, N. & Okamoto, A. (2013). Acta Cryst. E69, o444-o445.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18F2O8S2

  • Mr = 560.52

  • Monoclinic, C 2/c

  • a = 7.376 (3) Å

  • b = 16.468 (7) Å

  • c = 20.075 (9) Å

  • [beta] = 96.123 (6)°

  • V = 2424.4 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 173 K

  • 0.10 × 0.10 × 0.05 mm

Data collection
  • Rigaku Saturn70 diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.945, Tmax = 0.945

  • 8755 measured reflections

  • 2360 independent reflections

  • 1617 reflections with I > 2[sigma](I)

  • Rint = 0.074

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.120

  • S = 1.03

  • 2360 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
C14-H14A...Cg 0.98 2.87 3.805 (4) 160
C14-H14B...O1i 0.98 2.45 3.399 (4) 163
C14-H14C...O4ii 0.98 2.46 3.304 (4) 144
C12-H12...O4iii 0.95 2.50 3.285 (4) 140
C4-H4...O1iv 0.95 2.54 3.415 (4) 153
Symmetry codes: (i) [-x, y, -z+{\script{1\over 2}}]; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+2, -z+1; (iv) [-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, 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: SU2570 ).


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.
Hijikata, D., Sasagawa, K., Yoshiwaka, S., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o3246.  [CSD] [CrossRef] [details]
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.  [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, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Takeuchi, R., Kusakabe, T., Yonezawa, N. & Okamoto, A. (2013). Acta Cryst. E69, o444-o445.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.  [CSD] [CrossRef] [details]
Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o544  [ doi:10.1107/S1600536813006788 ]

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