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

Sasagawa, K.; Sakamoto, R.; Hijikata, D.; Yonezawa, N.; Okamoto, A.

doi:10.1107/S1600536813004820

Volume 69
Part 3
Page o440
March 2013

Received 2 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 13.4
Details

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

Kosuke Sasagawa,^a Rei Sakamoto,^a Daichi Hijikata,^a Noriyuki Yonezawa ^a and Akiko Okamoto ^a ^*

^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 title molecule, C₂₅H₂₀O₄, the naphthalene and phenoxy groups are oriented nearly perpendicular with respect to the benzene ring of the benzoyl group, with dihedral angles of 89.61 (5) and 86.13 (6)°, respectively. The crystal structure features C-HO and C-H [pi] interactions.

Related literature

For the formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Hijikata et al. (2010); Nakaema et al. (2008); Sasagawa et al. (2013); Tsumuki et al. (2011, 2012).

Experimental

Crystal data

C₂₅H₂₀O₄
M_r = 384.41
Monoclinic, P 2₁ /n
a = 10.9512 (2) Å
b = 15.8830 (3) Å
c = 11.2184 (2) Å
= 92.460 (1)°
V = 1949.51 (6) Å³
Z = 4
Cu K radiation
= 0.71 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) T_min = 0.674, T_max = 0.871
35423 measured reflections
3551 independent reflections
3228 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.097
S = 1.05
3551 reflections
265 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C20-C25 and C12-C17 benzene rings, respectively.

D-HA	D-H	HA	DA	D-HA
C21-H21O2ⁱ	0.95	2.56	3.3738 (17)	143
C19-H19ACg1ⁱⁱ	0.98	2.74	3.6967 (18)	164
C19-H19CCg2ⁱⁱⁱ	0.98	2.67	3.6249 (18)	165
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2553 ).

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 Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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.
Nakaema, K., Watanabe, S., Okamoto, A., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o807.
Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Sakamoto, R., Hijikata, D., Okamoto, A. & Yonezawa, N. (2013). Acta Cryst. E69, o363.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tsumuki, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2095.
Tsumuki, T., Isogai, A., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2595.

organic compounds