[Journal logo]

Volume 69 
Part 5 
Page o663  
May 2013  

Received 18 March 2013
Accepted 1 April 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.105
Data-to-parameter ratio = 13.5
Details
Open access

(2,7-Dimethoxynaphthalen-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

The asymmetric unit of the title compound, C23H18O3, contains two independent molecules (A and B). Each molecule has essentially the same conformation (r.m.s. deviation of fitted molecules = 0.173 Å) with the aromatic rings twisted in a near perpendicular manner. The dihedral angles between the two naphthalene ring systems are 79.07 (4) and 88.19 (4)° in the two independent molecules. In the crystal, the A molecules are connected by C-H...O interactions, forming chains along the b-axis direction. Further C-H...O interactions between the H atoms of the methoxy group and the O atoms of the carbonyl units link the A and B molecules, forming a three-dimensional network.

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.]); Kato et al. (2010[Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659.]); Tsumuki et al. (2012[Tsumuki, T., Isogai, A., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2595.], 2013[Tsumuki, T., Takeuchi, R., Kawano, H., Yonezawa, N. & Okamoto, A. (2013). Acta Cryst. E69, o495-o496.]); Sasagawa et al. (2013[Sasagawa, K., Sakamoto, R., Hijikata, D., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o363.]).

[Scheme 1]

Experimental

Crystal data
  • C23H18O3

  • Mr = 342.37

  • Monoclinic, P 21 /n

  • a = 16.1451 (3) Å

  • b = 7.51303 (14) Å

  • c = 29.0107 (5) Å

  • [beta] = 98.547 (1)°

  • V = 3479.88 (11) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.69 mm-1

  • T = 193 K

  • 0.50 × 0.20 × 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 = 0.725, Tmax = 0.934

  • 62016 measured reflections

  • 6349 independent reflections

  • 5490 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.105

  • S = 1.07

  • 6349 reflections

  • 470 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12B...O6 0.98 2.51 3.2862 (18) 136
C19-H19...O3i 0.95 2.40 3.2418 (17) 148
C15-H15...O3 0.95 2.19 2.8397 (16) 125
C38-H38...O6 0.95 2.25 2.8548 (17) 121
Symmetry code: (i) x, y+1, 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: VM2191 ).


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.
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. & 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., Sakamoto, R., Hijikata, D., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o363.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tsumuki, T., Isogai, A., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2595.  [CSD] [CrossRef] [details]
Tsumuki, T., Takeuchi, R., Kawano, H., Yonezawa, N. & Okamoto, A. (2013). Acta Cryst. E69, o495-o496.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o663  [ doi:10.1107/S1600536813008854 ]

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.