[8-(4-Phen­oxy­benzo­yl)-2,7-bis­(propan-2-yl­oxy)naphthalen-1-yl](4-phen­oxy­phen­yl)methanone

Sayaka Yoshiwaka; Daichi Hijikata; Kosuke Sasagawa; Akiko Okamoto; Noriyuki Yonezawa

doi:10.1107/S1600536813000913

. 2013 Jan 16;69(Pt 2):o242. doi: 10.1107/S1600536813000913

[8-(4-Phenoxybenzoyl)-2,7-bis(propan-2-yloxy)naphthalen-1-yl](4-phenoxyphenyl)methanone

Sayaka Yoshiwaka ^a, Daichi Hijikata ^a, Kosuke Sasagawa ^a, Akiko Okamoto ^a,^*, Noriyuki Yonezawa ^a

PMCID: PMC3569775 PMID: 23424521

Abstract

The entire title molecule, C₄₂H₃₆O₆, is completed by the application of a twofold axis. The 4-phenoxybenzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost antiparallel. The dihedral angle between the best planes of the benzene rings of the benzoyl moieties and the naphthalene ring system is 70.52 (5)° and that between the best planes of the benzene rings of the phenoxy groups and the naphthalene ring system is 27.80 (6)°. In the crystal, molecules are linked into a three-dimensional architecture by C—H⋯O and C—H⋯π interactions.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see; Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Sasagawa et al. (2012 ▶); Muto et al. (2010 ▶); Nakaema et al. (2008 ▶).

Experimental

Crystal data

C₄₂H₃₆O₆
M _r = 636.71
Monoclinic,
a = 22.7084 (4) Å
b = 10.3582 (2) Å
c = 14.7152 (3) Å
β = 100.106 (1)°
V = 3407.58 (11) Å³
Z = 4
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 193 K
0.60 × 0.60 × 0.50 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.693, T _max = 0.734
28911 measured reflections
3101 independent reflections
2749 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.096
S = 1.04
3101 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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 Material

Click here for additional data file.^{(20.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000913/pk2459sup1.cif

e-69-0o242-sup1.cif^{(20.5KB, cif)}

Click here for additional data file.^{(152.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000913/pk2459Isup2.hkl

e-69-0o242-Isup2.hkl^{(152.3KB, hkl)}

Click here for additional data file.^{(12.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000913/pk2459Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.44	3.3398 (15)	158
C16—H16⋯Cg ⁱⁱ	0.95	2.97	3.8383 (19)	152

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Shorai Foundation for Science and Technology.

supplementary crystallographic information

Comment

In the course of our study on electrophilic aromatic aroylation of the naphthalene ring core, 1,8-diaroylnaphthalene compounds have proved to be formed regioselectively by the choice of suitable acidic mediators (Okamoto & Yonezawa, 2009 Okamoto et al., 2011). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene analogues exemplified by 1,8-dibenzoyl-2,7-dimethoxynaphtalene (Nakaema et al., 2008), [2,7-dimethoxy-8-(4-propylbenzoyl)naphthalene-1-yl]-(4-propylphenyl)methanone (Sasagawa et al., 2012) and [2,7-dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone (Muto et al. 2010). In the crystals of these compounds, two aroyl groups tend to attach to the naphthalene ring in nearly perpendicular manners and oriented in the opposite direction (anti-orientation). Recently, the crystal structure of 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene has been clarified to take syn-orientation, where two phenoxybenzoyl groups are positioned on the same side against the naphthalene ring plane (Hijikata et al. 2010). As a part of our continuing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound peri-aroylnaphthalene bearing isopropoxy groups at the 2,7-positions is discussed in this article.

The molecular structure of the title compounds is displayed in Fig 1. Two 4-phenoxybenzoyl groups are situated in anti-orientation and are twisted away from the attached naphthalene ring. This molecule lies on a crystallographic 2-fold axis so that the asymmetric unit consists of one-half of the molecule. The dihedral angle between the best plane of the inner benzene ring of the 4-phenoxybenzoyl groups and the naphthalene system is 70.52 (5)°.

Centrosymmetrically related molecules are linked into dimeric unit by pairs of C—H···π interactions between the hydrogen atom (H16) on the terminal phenoxy group and the π-system of the benzene ring in the benzoyl moiety (C8–C13) (C16—H16···Cgⁱⁱⁱ, Fig. 2). The molecules of the title compound are aligned in an antiparallel fashion with the adjacent molecule. The terminal benzene ring of the phenoxybenzoyl group interacts with the inner benzene ring of the phenoxybenzoyl group of the adjacent molecule. Both of the pairs of the facing benzene rings in the couple of the phenoxybenzoyl groups are situated almost perpendicularly to the benzene ring in the benzoyl moiety (C8–C13). Then two identical interactions are formed to give cyclic structure between the two phenoxybenzoyl groups.

Furthermore, an oxygen atom of the carbonyl group forms intermolecular C—H···O interaction with the m-hydrogen of the benzoyl benzene ring of the other adjacent molecule (C12—H12···O1 = 2.44 Å, Fig. 3).

Experimental

1,8-(4-phenoxybenzoyl)-2,7-dihydroxynaphtalene (0.3 mmol, 157 mg), tetrabutylammonium iodide (0.03 mmol, 113 mg), potassium carbonate (0.9 mmol, 127 mg) and DMF (0.75 ml) were placed into a 10 ml flask, followed by stirring at room temperature under nitrogen for 1 h. 2-Bromopropane (1.8 mmol, 224 mg) was to the solution and heated at 70 °C for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-cold water (20 ml). The aqueous layer was extracted with ethyl acetate (20 ml × 2). The combined extracts were washed with 2 M aqueous NaOH followed by washing the brine. The extracts thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake (yield 22%). Colourless single crystals suitable for X-ray diffraction were obtained by repeated crystallization from methanol.

¹H NMR δ (300 MHz, CDCl₃): 1.04 (12H, d, J = 6.0 Hz), 4.51 (2H, sep, J = 6.0 Hz), 6.89 (4H, d, J = 8.1 Hz), 7.09 (4H, d, J = 8.1 Hz), 7.13 (2H, d, J = 9.0 Hz), 7.17 (2H, d, J = 8.1 Hz), 7.37 (4H, t, J = 8.1 Hz), 7.70 (4H, d, J = 8.1 Hz), 7.86 (2H, d, J = 9.0 Hz),

¹³C NMR δ (125 MHz, CDCl₃): 21.6, 71.5, 113.1, 116.7, 120.0, 122.6, 124.1, 125.2, 129.8, 130.4, 131.3, 131.6, 134.3, 154.6, 155.8, 161.1, 196.0 p.p.m.

IR (KBr): 1656 (C=O), 1601, 1505, 1452 (Ar), 1267 (C—O—C) cm^-1

HRMS (m/z): [M+H]⁺ called. for C₄₂H₃₇O₆, 637.2581, found, 637.2590.

m.p. = 450.2–451.4 K