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Volume 69 
Part 1 
Page o146  
January 2013  

Received 5 December 2012
Accepted 13 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.035
wR = 0.107
Data-to-parameter ratio = 13.0
Details
Open access

[2,7-Dimethoxy-8-(4-methoxybenzoyl)naphthalen-1-yl](4-methoxyphenyl)methanone chloroform monosolvate

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 compound, C28H24O6·CHCl3, the two 4-methoxybenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel, the benzene rings making a dihedral angle of 25.76 (7)°. The naphthalene ring system makes dihedral angles of 72.51 (7) and 73.33 (7)° with the benzene rings. In the crystal, the naphthalene molecules are linked by C-H...O interactions, forming a helical chain along the b-axis direction. A C-H...Cl interaction is also observed between the aroylated naphthalene and chloroform molecules. The chloroform molecule is disordered over two positions with site occupancies of 0.478 (5) and 0.522 (5).

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto et al. (2011[Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283-1284.]); Okamoto & Yonezawa (2009[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]). For structures of closely related compounds, see: Hijikata et al. (2010[Hijikata, D., Takada, T., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2902-o2903.]); Sasagawa et al. (2011[Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24O6·CHCl3

  • Mr = 575.84

  • Monoclinic, P 21 /c

  • a = 8.2781 (2) Å

  • b = 21.4763 (5) Å

  • c = 15.5370 (4) Å

  • [beta] = 98.448 (2)°

  • V = 2732.25 (12) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 3.39 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 = 0.282, Tmax = 0.728

  • 50703 measured reflections

  • 4994 independent reflections

  • 4305 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.107

  • S = 1.10

  • 4994 reflections

  • 385 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O5i 0.95 2.37 3.1460 (19) 139
C13-H13...Cl3ii 0.95 2.75 3.647 (2) 159
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

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: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 Ridgeational 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: IS5230 ).


Acknowledgements

The authors express their gratitude to Master Atsushi Nagasawa and 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 a Sasagawa Scientific Research Grant from the Japan Science Society, Tokyo, Japan.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridgeational 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]
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.
Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o146  [ doi:10.1107/S1600536812050799 ]

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