[Journal logo]

Volume 69 
Part 4 
Page o557  
April 2013  

Received 21 February 2013
Accepted 15 March 2013
Online 20 March 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 12.3
Details
Open access

Bis(1-benzoyl-7-methoxynaphthalen-2-yl) terephthalate

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Naka-machi, 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 title molecule, C44H30O8, lies about a crystallographic inversion centre located at the centre of the central benzene ring. The benzene rings in the benzoyl and the terephthalate units make dihedral angles of 67.05 (7)° and 57.57 (7)°, respectively, with the naphthalene ring system. There is an intramolecular C-H...O interaction between the ketonic carbonyl O atom and an H atom on the naphthalene ring system. In the crystal, C-H...O interaction of the benzene ring in the benzoyl group and weak C=O...[pi] interaction [O...centroid = 3.375 (2) Å] of the naphthalene ring with the O atom in the ketonic carbonyl group are observed. These interactions form layers parallel to the bc plane.

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 structures of closely related compounds, see: Kato et al. (2010[Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659.]); Nakaema et al. (2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]); Sakamoto et al. (2012[Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.], 2013[Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o210.]).

[Scheme 1]

Experimental

Crystal data
  • C44H30O8

  • Mr = 686.72

  • Monoclinic, P 21 /c

  • a = 9.977 (5) Å

  • b = 14.922 (7) Å

  • c = 11.709 (6) Å

  • [beta] = 106.610 (5)°

  • V = 1670.5 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.16 × 0.13 × 0.03 mm

Data collection
  • Rigaku Saturn70 diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.985, Tmax = 0.997

  • 10969 measured reflections

  • 2909 independent reflections

  • 2354 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.122

  • S = 1.04

  • 2909 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O1 0.95 2.41 2.965 (3) 117
C16-H16...O1i 0.95 2.55 3.258 (3) 132
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2006[Rigaku (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2113 ).


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 Institute for Chemical Research, Kyoto University (grant No. 2012-72).

References

Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659.  [CSD] [CrossRef] [details]
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.  [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 (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.  [CSD] [CrossRef] [details]
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o210.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o557  [ doi:10.1107/S1600536813007186 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.