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Volume 69 
Part 2 
Page o242  
February 2013  

Received 5 December 2012
Accepted 10 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 14.0
Details
Open access

[8-(4-Phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl)methanone

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp

The entire title molecule, C42H36O6, is completed by the application of a twofold axis. The 4-phenoxybenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel. The dihedral angle between the best planes of the benzene rings of the benzoyl moieties and the naphthalene ring system is 70.52 (5)° and that between the best planes of the benzene rings of the phenoxy groups and the naphthalene ring system is 27.80 (6)°. In the crystal, molecules are linked into a three-dimensional architecture by C-H...O and 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.]). For the structures of closely related compounds, see: Hijikata et al. (2010[Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.]); Sasagawa et al. (2012[Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2596.]); Muto et al. (2010[Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752.]); Nakaema et al. (2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]).

[Scheme 1]

Experimental

Crystal data
  • C42H36O6

  • Mr = 636.71

  • Monoclinic, C 2/c

  • a = 22.7084 (4) Å

  • b = 10.3582 (2) Å

  • c = 14.7152 (3) Å

  • [beta] = 100.106 (1)°

  • V = 3407.58 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.66 mm-1

  • T = 193 K

  • 0.60 × 0.60 × 0.50 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.693, Tmax = 0.734

  • 28911 measured reflections

  • 3101 independent reflections

  • 2749 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.04

  • 3101 reflections

  • 221 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12...O1i 0.95 2.44 3.3398 (15) 158
C16-H16...Cgii 0.95 2.97 3.8383 (19) 152
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+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: PK2459 ).


Acknowledgements

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Shorai Foundation for Science and Technology.

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.
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.  [CSD] [CrossRef] [details]
Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752.  [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 (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2596.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o242  [ doi:10.1107/S1600536813000913 ]

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