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Volume 69 
Part 3 
Page o363  
March 2013  

Received 30 January 2013
Accepted 31 January 2013
Online 9 February 2013

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Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 13.4
Details
Open access

(2,7-Dimethoxynaphthalen-1-yl)(4-methoxyphenyl)methanone

Kosuke Sasagawa,a Rei Sakamoto,a Daichi Hijikata,a Akiko Okamotoa* and Noriyuki Yonezawaa

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

In the molecule of the title compound, C20H18O4, the dihedral angle between the naphthalene ring system and the benzene ring is 81.74 (5)°. An intermolecular C-H...O interaction is formed between an H atom at the 6-position of the naphthalene ring and the O atom of the methoxy group at the 7-position.

Related literature

For formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution 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., Oike, H. & 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.]); Hijikata et al. (2010[Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.]); Kato et al. (2010[Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659.]); Tsumuki et al. (2011[Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.], 2012[Tsumuki, T., Isogai, A., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2595.]).

[Scheme 1]

Experimental

Crystal data

  • C20H18O4

  • Mr = 322.34

  • Monoclinic, P 21 /c

  • a = 14.9638 (2) Å

  • b = 7.9191 (1) Å

  • c = 13.6394 (2) Å

  • [beta] = 92.56°

  • V = 1614.64 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.75 mm-1

  • T = 193 K

  • 0.60 × 0.40 × 0.30 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 1999[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.662, Tmax = 0.806

  • 27665 measured reflections

  • 2957 independent reflections

  • 2701 reflections with I > 2[sigma](I)

  • Rint = 0.051
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.05

  • 2957 reflections

  • 221 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O3i 0.95 2.51 3.4592 (16) 178
Symmetry code: (i) -x, -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: 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: PK2464 ).

Acknowledgements

The authors express their gratitude to Master Toyokazu Muto, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture & Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice. This work was partially supported by the Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant, 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.
Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.  [CSD] [CrossRef] [details]
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., 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.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
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., Isogai, A., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2595.  [CSD] [CrossRef] [details]

Acta Cryst (2013). E69, o363  [ doi:10.1107/S1600536813003218 ]

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