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Volume 69 
Part 3 
Page o369  
March 2013  

Received 1 February 2013
Accepted 5 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.097
Data-to-parameter ratio = 13.5
Details
Open access

{2,7-Diethoxy-8-[(naphthalen-2-yl)carbonyl]naphthalen-1-yl}(naphthalen-2-yl)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, C36H28O4, the two 2-naphthoyl groups at the 1- and 8-positions of the central 2,7-diethoxynaphthalene ring system are aligned almost antiparallel and make a dihedral angle of 48.35 (5)°. The dihedral angles between the central 2,7-diethoxynaphthalene ring system and the terminal naphthalene ring systems are 77.64 (4) and 73.73 (4)°. In the crystal, molecules are linked into chains along the a-axis direction by dual C-H...O interactions between naphthoyl groups.

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.]); Tsumuki et al. (2011[Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.]); Sasagawa et al. (2012[Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o3348.]); Isogai et al. (2013[Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71.]); Yoshiwaka et al. (2013[Yoshiwaka, S., Hijikata, D., Sasagawa, K., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o242.]).

[Scheme 1]

Experimental

Crystal data
  • C36H28O4

  • Mr = 524.58

  • Monoclinic, P 21 /c

  • a = 7.86946 (14) Å

  • b = 27.1458 (5) Å

  • c = 12.8490 (2) Å

  • [beta] = 102.267 (1)°

  • V = 2682.16 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 193 K

  • 0.50 × 0.25 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.732, Tmax = 0.878

  • 41696 measured reflections

  • 4914 independent reflections

  • 3996 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.097

  • S = 1.09

  • 4914 reflections

  • 364 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21-H21...O3i 0.95 2.45 3.3958 (18) 173
C25-H25...O4ii 0.95 2.45 3.3996 (18) 176
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: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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: RZ5043 ).


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 an Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [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.
Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71.  [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. & 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.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Hijikata, D., Sakamoto, R., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o3348.  [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]
Yoshiwaka, S., Hijikata, D., Sasagawa, K., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o242.  [CrossRef] [details]


Acta Cryst (2013). E69, o369  [ doi:10.1107/S1600536813003577 ]

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