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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 [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 13.9
Details
Open access

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

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-H...O interaction is observed.

Related literature

For 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: Muto et al. (2010[Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752.], 2011a[Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011a). Acta Cryst. E67, o2813.],b[Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011b). Acta Cryst. E67, o3062.]).

[Scheme 1]

Experimental

Crystal data
  • C32H32O4

  • Mr = 480.58

  • Monoclinic, P 21 /n

  • a = 7.71685 (14) Å

  • b = 29.2344 (5) Å

  • c = 11.5567 (2) Å

  • [beta] = 102.879 (1)°

  • V = 2541.57 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.697, Tmax = 0.938

  • 45450 measured reflections

  • 4657 independent reflections

  • 4131 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.121

  • S = 1.09

  • 4657 reflections

  • 334 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C29-H29C...O2 0.98 2.33 3.1669 (19) 143

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[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.]); 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: 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.  [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.
Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752.  [CSD] [CrossRef] [details]
Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011a). Acta Cryst. E67, o2813.  [CSD] [CrossRef] [details]
Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011b). Acta Cryst. E67, o3062.  [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/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o23  [ doi:10.1107/S1600536811051579 ]

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