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Volume 68 
Part 11 
Page o3246  
November 2012  

Received 18 October 2012
Accepted 24 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 13.2
Details
Open access

(4-Fluorophenyl)[8-(4-fluorobenzoyl)-2,7-diphenoxynaphthalen-1-yl]methanone

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, C36H22F2O4, the aromatic rings of the benzoyl and phenoxy groups make dihedral angles of 72.07 (5), 73.24 (5), 62.49 (5) and 77.96 (6)° with the naphthalene ring system. In the crystal, C-H...O hydrogen bonds and C-H...[pi] interactions are observed.

Related literature

For information on 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.], 2012[Okamoto, A., Hijikata, D., Sakai, N. & Yonezawa, N. (2012). Polym. J. In the press.]). For the 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.]); Sakamoto et al. (2012[Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.]).

[Scheme 1]

Experimental

Crystal data
  • C36H22F2O4

  • Mr = 556.54

  • Orthorhombic, P b c n

  • a = 22.3058 (4) Å

  • b = 14.6047 (3) Å

  • c = 16.8302 (3) Å

  • V = 5482.76 (18) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.80 mm-1

  • T = 193 K

  • 0.50 × 0.30 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.691, Tmax = 0.925

  • 96215 measured reflections

  • 5011 independent reflections

  • 4671 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.06

  • 5011 reflections

  • 380 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31-C36 ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O3i 0.95 2.40 3.3477 (15) 172
C13-H13...Cgii 0.95 2.87 3.6924 (15) 145
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) [-x, y, -z+{\script{1\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: RZ5018 ).


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. In the press.
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.
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.  [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, o3246  [ doi:10.1107/S160053681204408X ]

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