[Journal logo]

Volume 69 
Part 4 
Pages o495-o496  
April 2013  

Received 14 February 2013
Accepted 27 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.106
Data-to-parameter ratio = 13.2
Details
Open access

{2,7-Diethoxy-8-[(naphthalen-1-yl)carbonyl]naphthalen-1-yl}(naphthalen-1-yl)methanone

aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, Koganei, Tokyo 184-8588, Japan, and bDivision of Liberal Arts, Kogakuin University, Hachioji, Tokyo 192-0015, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp

In the title compound, C36H28O4, the 1-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 76.59 (4)°. The dihedral angles between the central 2,7-diethoxynaphthalene ring system and the terminal naphthalene ring systems are 86.48 (4) and 83.97 (4)°. In the crystal, C-H...[pi] interactions between the central naphthalene ring systems and the naphthoyl groups are observed along the a axis, with the molecules forming a columnar structure. The columns are linked into chains parallel to the b axis by C-H...O interactions.

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.]); Sakamoto et al. (2012[Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.]); Isogai et al. (2013[Isogai, A., Tsumuki, T., Murohashi, S., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o71.]); Tsumuki et al. (2013[Tsumuki, T., Okamoto, A., Oike, H. & Yonezawa, N. (2013). Acta Cryst. E69, o369.]); 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

  • Triclinic, [P \overline 1]

  • a = 8.76532 (16) Å

  • b = 11.4266 (2) Å

  • c = 14.1972 (3) Å

  • [alpha] = 99.080 (1)°

  • [beta] = 99.036 (1)°

  • [gamma] = 104.277 (1)°

  • V = 1331.94 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 193 K

  • 0.60 × 0.40 × 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 = 0.689, Tmax = 0.877

  • 24143 measured reflections

  • 4800 independent reflections

  • 4142 reflections with I > 2[sigma](I)

  • Rint = 0.043

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

  • wR(F2) = 0.106

  • S = 1.07

  • 4800 reflections

  • 364 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg6 are the centroids of the C16-C21 and C27-C32 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3...Cg4i 0.95 2.77 3.5662 (15) 142
C7-H7...Cg6i 0.95 2.76 3.5662 (16) 143
C30-H30...O2ii 0.95 2.53 3.3289 (19) 142
C34-H34A...O1iii 0.98 2.47 3.423 (2) 163
C35-H35B...O2iv 0.99 2.59 3.5476 (17) 163
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+1, -z+1; (iv) -x, -y+2, -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: PK2467 ).


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., 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.
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.
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.  [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]
Tsumuki, T., Okamoto, A., Oike, H. & Yonezawa, N. (2013). Acta Cryst. E69, o369.  [CrossRef] [details]
Yoshiwaka, S., Hijikata, D., Sasagawa, K., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o242.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o495-o496   [ doi:10.1107/S1600536813005710 ]

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.