[2,7-Dihy­droxy-8-(4-phen­oxy­benzo­yl)naphthalen-1-yl](4-phen­oxy­phen­yl)methanone

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

doi:10.1107/S1600536812052038

Volume 69
Part 2
Pages o208-o209
February 2013

Received 8 December 2012
Accepted 29 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.096
Data-to-parameter ratio = 12.7
Details

[2,7-Dihydroxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)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, C₃₆H₂₄O₆, the benzoyl groups at the 1- and 8-positions of the naphthalene system are in an anti orientation. Both carbonyl groups form intramolecular O-HO hydrogen bonds with hydroxy groups affording six-membered rings. The benzene rings of the benzoyl groups make dihedral angles of 59.26 (13) and 59.09 (13)° with the naphthalene ring system. Zigzag C-HO chains and ladder C-HO chains between the phenoxybenzoyl groups along the ab diagonals form an undulating checkered sheet. The molecules are further connected into a three-dimensional network by C-H [pi] interactions.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011, 2013). For the structures of (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone and 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene, see: Watanabe et al. (2010) andr Hijikata et al. (2010), respectively.

Experimental

Crystal data

C₃₆H₂₄O₆
M_r = 552.55
Monoclinic, C c
a = 16.0313 (3) Å
b = 18.4956 (3) Å
c = 12.1238 (2) Å
= 131.389 (1)°
V = 2696.95 (9) Å³
Z = 4
Cu K radiation
= 0.75 mm^-1
T = 193 K
0.60 × 0.55 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999) T_min = 0.661, T_max = 0.929
22236 measured reflections
4868 independent reflections
4527 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.096
S = 1.08
4868 reflections
382 parameters
2 restraints
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.21 e Å^-3
Absolute structure: Flack (1983), 2389 Friedel pairs
Flack parameter: 0.05 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C25-C30 and C31-C36 rings, respectively.

D-HA	D-H	HA	DA	D-HA
O5-H5AO1	0.84	1.83	2.560 (3)	145
O6-H6AO2	0.84	1.88	2.563 (3)	138
C26-H26O4ⁱ	0.95	2.48	3.377 (4)	157
C27-H27O1ⁱ	0.95	2.51	3.269 (4)	137
C32-H32O3ⁱⁱ	0.95	2.49	3.382 (4)	156
C33-H33O2ⁱⁱ	0.95	2.51	3.270 (4)	137
C14-H14Cg1ⁱⁱⁱ	0.95	2.80	3.740 (2)	171
C21-H21Cg2^iv	0.95	2.80	3.740 (2)	171
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x, -y, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: RN2112 ).

Acknowledgements

The authors would like to 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.
Okamoto, A., Hijikata, D., Sakai, N. & Yonezawa, N. (2013). Polym. J. In the press. doi:10.1038/pj.2012.135.
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.
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