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

Hijikata, D.; Sasagawa, K.; Yoshiwaka, S.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S160053681204408X

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 13.2
Details

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

Daichi Hijikata,^a Kosuke Sasagawa,^a Sayaka Yoshiwaka,^a Akiko Okamoto ^a ^* and Noriyuki Yonezawa ^a

^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-HO 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 et al. (2011, 2012). For the structures of closely related compounds, see: Watanabe et al. (2010); Sakamoto et al. (2012).

Experimental

Crystal data

C₃₆H₂₂F₂O₄
M_r = 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 radiation
= 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) T_min = 0.691, T_max = 0.925
96215 measured reflections
5011 independent reflections
4671 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.091
S = 1.06
5011 reflections
380 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31-C36 ring.

D-HA	D-H	HA	DA	D-HA
C6-H6O3ⁱ	0.95	2.40	3.3477 (15)	172
C13-H13Cgⁱⁱ	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); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); 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.
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.
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.

organic compounds