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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 [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.096
Data-to-parameter ratio = 12.7
Details
Open access

[2,7-Dihydroxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)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, 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-H...O 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-H...O chains and ladder C-H...O 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, 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.], 2013[Okamoto, A., Hijikata, D., Sakai, N. & Yonezawa, N. (2013). Polym. J. In the press. doi:10.1038/pj.2012.135.]). 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[Watanabe, S., Nagasawa, A., Okamoto, A., Noguchi, K. & Yonezawa, N. (2010). Acta Cryst. E66, o329.]) andr Hijikata et al. (2010[Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C36H24O6

  • Mr = 552.55

  • Monoclinic, C c

  • a = 16.0313 (3) Å

  • b = 18.4956 (3) Å

  • c = 12.1238 (2) Å

  • [beta] = 131.389 (1)°

  • V = 2696.95 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.661, Tmax = 0.929

  • 22236 measured reflections

  • 4868 independent reflections

  • 4527 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.08

  • 4868 reflections

  • 382 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 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-H...A D-H H...A D...A D-H...A
O5-H5A...O1 0.84 1.83 2.560 (3) 145
O6-H6A...O2 0.84 1.88 2.563 (3) 138
C26-H26...O4i 0.95 2.48 3.377 (4) 157
C27-H27...O1i 0.95 2.51 3.269 (4) 137
C32-H32...O3ii 0.95 2.49 3.382 (4) 156
C33-H33...O2ii 0.95 2.51 3.270 (4) 137
C14-H14...Cg1iii 0.95 2.80 3.740 (2) 171
C21-H21...Cg2iv 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[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: 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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [details]
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort]
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.  [ISI] [CrossRef] [ChemPort]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
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 (2013). E69, o208-o209   [ doi:10.1107/S1600536812052038 ]

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