[2,7-Dimeth­oxy-8-(2,4,6-trimethyl­benzo­yl)naphthalen-1-yl](2,4,6-trimethyl­phen­yl)methanone

Muto, T.; Sasagawa, K.; Okamoto, A.; Oike, H.; Yonezawa, N.

doi:10.1107/S1600536811051579

Volume 68
Part 1
Page o23
January 2012

Received 17 November 2011
Accepted 30 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 13.9
Details

[2,7-Dimethoxy-8-(2,4,6-trimethylbenzoyl)naphthalen-1-yl](2,4,6-trimethylphenyl)methanone

Toyokazu Muto,^a Kosuke Sasagawa,^a Akiko Okamoto,^a ^* Hideaki Oike ^a and Noriyuki Yonezawa ^a

^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, C₃₂H₃₂O₄, the dihedral angle between the two benzene rings of the 2,4,6-trimethylbenzoyl groups is 71.43 (7)°. The dihedral angles between the two benzene rings and the naphthalene ring system are 81.58 (5) and 84.92 (6)°. An intramolecular C-HO interaction is observed.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For the structures of closely related compounds, see: Muto et al. (2010, 2011a,b).

Experimental

Crystal data

C₃₂H₃₂O₄
M_r = 480.58
Monoclinic, P 2₁ /n
a = 7.71685 (14) Å
b = 29.2344 (5) Å
c = 11.5567 (2) Å
= 102.879 (1)°
V = 2541.57 (8) Å³
Z = 4
Cu K radiation
= 0.65 mm^-1
T = 193 K
0.60 × 0.40 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999) T_min = 0.697, T_max = 0.938
45450 measured reflections
4657 independent reflections
4131 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.121
S = 1.09
4657 reflections
334 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C29-H29CO2	0.98	2.33	3.1669 (19)	143

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2004 (Burla et al., 2005); 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: VM2138 ).

Acknowledgements

The authors express their gratitude to Master Daichi Hijikata, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture and Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice.

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.
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.
Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752.
Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011a). Acta Cryst. E67, o2813.
Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011b). Acta Cryst. E67, o3062.
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.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds