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

Sasagawa, K.; Sakamoto, R.; Kusakabe, T.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536812050799

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 (C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.035
wR = 0.107
Data-to-parameter ratio = 13.0
Details

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

Kosuke Sasagawa,^a Rei Sakamoto,^a Taro Kusakabe,^a Akiko Okamoto ^a ^* and Noriyuki Yonezawa ^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 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-HO interactions, forming a helical chain along the b-axis direction. A C-HCl 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 & Yonezawa (2009). For structures of closely related compounds, see: Hijikata et al. (2010); Sasagawa et al. (2011).

Experimental

Crystal data

C₂₈H₂₄O₆·CHCl₃
M_r = 575.84
Monoclinic, P 2₁ /c
a = 8.2781 (2) Å
b = 21.4763 (5) Å
c = 15.5370 (4) Å
= 98.448 (2)°
V = 2732.25 (12) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.282, T_max = 0.728
50703 measured reflections
4994 independent reflections
4305 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.107
S = 1.10
4994 reflections
385 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O5ⁱ	0.95	2.37	3.1460 (19)	139
C13-H13Cl3ⁱⁱ	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); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010); 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: 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.
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 (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sasagawa, K., Muto, T., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o3354.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds