(8-Benzoyl-2,7-dimeth­oxy­naphthalen-1-yl)(4-phen­oxy­phen­yl)methanone

Sasagawa, K.; Sakamoto, R.; Takeuchi, R.; Yonezawa, N.; Okamoto, A.

doi:10.1107/S1600536813004303

Volume 69
Part 3
Pages o395-o396
March 2013

Received 9 February 2013
Accepted 13 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R = 0.032
wR = 0.085
Data-to-parameter ratio = 7.7
Details

(8-Benzoyl-2,7-dimethoxynaphthalen-1-yl)(4-phenoxyphenyl)methanone

Kosuke Sasagawa,^a Rei Sakamoto,^a Ryo Takeuchi,^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 molecule of the title compound, C₃₂H₂₄O₅, the benzoyl group and the 4-phenoxy substituted benzoyl group at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel. The two benzene rings make a dihedral angle of 21.18 (10)°, and are inclined to the naphthalene ring system by 86.53 (9) and 82.95 (8)°, respectively. In the crystal, C-HO interactions are observed involving aromatic and methoxy H atoms with ketonic carbonyl O atoms, as well as C-H [pi] interactions between aromatic H atoms and the [pi] -systems of naphthalene and benzene rings. These interactions form a three-dimensional architecture and afford a waved alignment of the naphthalene ring systems along the c axis.

Related literature

For the synthesis 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: Nakaema et al. (2008); Hijikata et al. (2010); Sasagawa et al. (2011, 2013); Muto et al. (2012).

Experimental

Crystal data

C₃₂H₂₄O₅
M_r = 488.51
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.19645 (10) Å
b = 11.5051 (2) Å
c = 26.4916 (4) Å
V = 2498.18 (7) Å³
Z = 4
Cu K radiation
= 0.71 mm^-1
T = 193 K
0.60 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) T_min = 0.802, T_max = 0.868
46867 measured reflections
2605 independent reflections
2543 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.085
S = 1.04
2605 reflections
337 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C27-C32, C12-C17 and C5-C10 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C30-H30O5ⁱ	0.95	2.52	3.423 (3)	158
C7-H7O5ⁱⁱ	0.95	2.37	3.304 (3)	168
C25-H25BO5ⁱⁱ	0.98	2.34	3.122 (3)	136
C3-H3O1ⁱⁱⁱ	0.95	2.40	3.310 (2)	160
C20-H20Cg1^iv	0.95	2.84	3.652 (3)	144
C23-H23Cg2^v	0.95	2.76	3.628 (2)	151
C29-H29Cg3ⁱ	0.95	2.85	3.652 (3)	142
Symmetry codes: (i) x+1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007); 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: VM2188 ).

Acknowledgements

Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, is thanked for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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organic compounds