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Volume 69 
Part 1 
Page o71  
January 2013  

Received 5 December 2012
Accepted 6 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 14.0
Details
Open access

(8-Benzoyl-2,7-diethoxynaphthalen-1-yl)(phenyl)methanone

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp

In the title compound, C28H24O4, the benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, and the benzene rings make a dihedral angle of 20.03 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 68.42 (5) and 71.69 (5)°. In the crystal, adjacent molecules are linked via C-H...O hydrogen bonds, forming chains propagating along [100].

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]); Okamoto et al. (2011[Okamoto, A., Mitsui, R. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.]). For the structures of closely related compounds, see: Nakaema et al. (2008[Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.]); Nishijima et al. (2010[Nishijima, T., Kataoka, K., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2904-o2905.]); Sasagawa et al. (2011[Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.]); Tsumuki et al. (2011[Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.]); Muto et al. (2012[Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2012). Acta Cryst. E68, o1200.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24O4

  • Mr = 424.47

  • Monoclinic, P 21 /n

  • a = 7.92185 (14) Å

  • b = 20.6794 (4) Å

  • c = 14.2130 (3) Å

  • [beta] = 106.043 (1)°

  • V = 2237.68 (7) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 193 K

  • 0.60 × 0.50 × 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 = 0.689, Tmax = 0.936

  • 39782 measured reflections

  • 4076 independent reflections

  • 3736 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.05

  • 4076 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14...O3i 0.95 2.37 3.2404 (16) 153
C21-H21...O4ii 0.95 2.39 3.3326 (16) 171
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

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: SU2538 ).


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 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.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2012). Acta Cryst. E68, o1200.  [CSD] [CrossRef] [details]
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.  [CSD] [CrossRef] [details]
Nishijima, T., Kataoka, K., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2904-o2905.  [CSD] [CrossRef] [details]
Okamoto, A., Mitsui, R. & 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., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o71  [ doi:10.1107/S1600536812049963 ]

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