[2,7-Dihy­droxy-8-(4-phen­oxy­benzo­yl)naphthalen-1-yl](4-phen­oxy­phen­yl)methanone

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

doi:10.1107/S1600536812052038

. 2013 Jan 9;69(Pt 2):o208–o209. doi: 10.1107/S1600536812052038

[2,7-Dihydroxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methanone

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

PMCID: PMC3569745 PMID: 23424491

Abstract

In the title compound, C₃₆H₂₄O₆, the benzoyl groups at the 1- and 8-positions of the naphthalene system are in an anti orientation. Both carbonyl groups form intramolecular O—H⋯O hydrogen bonds with hydroxy groups affording six-membered rings. The benzene rings of the benzoyl groups make dihedral angles of 59.26 (13) and 59.09 (13)° with the naphthalene ring system. Zigzag C—H⋯O chains and ladder C—H⋯O chains between the phenoxybenzoyl groups along the ab diagonals form an undulating checkered sheet. The molecules are further connected into a three-dimensional network by C—H⋯π interactions.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶, 2013 ▶). For the structures of (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone and 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene, see: Watanabe et al. (2010 ▶) andr Hijikata et al. (2010 ▶), respectively. graphic file with name e-69-0o208-scheme1.jpg

Experimental

Crystal data

C₃₆H₂₄O₆
M _r = 552.55
Monoclinic,
a = 16.0313 (3) Å
b = 18.4956 (3) Å
c = 12.1238 (2) Å
β = 131.389 (1)°
V = 2696.95 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 193 K
0.60 × 0.55 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.661, T _max = 0.929
22236 measured reflections
4868 independent reflections
4527 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.096
S = 1.08
4868 reflections
382 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 2389 Friedel pairs
Flack parameter: 0.05 (19)

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.^{(37.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812052038/rn2112sup1.cif

e-69-0o208-sup1.cif^{(37.5KB, cif)}

Click here for additional data file.^{(233.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812052038/rn2112Isup2.hkl

e-69-0o208-Isup2.hkl^{(233.6KB, hkl)}

Click here for additional data file.^{(10.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812052038/rn2112Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C25—C30 and C31—C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1	0.84	1.83	2.560 (3)	145
O6—H6A⋯O2	0.84	1.88	2.563 (3)	138
C26—H26⋯O4ⁱ	0.95	2.48	3.377 (4)	157
C27—H27⋯O1ⁱ	0.95	2.51	3.269 (4)	137
C32—H32⋯O3ⁱⁱ	0.95	2.49	3.382 (4)	156
C33—H33⋯O2ⁱⁱ	0.95	2.51	3.270 (4)	137
C14—H14⋯Cg1ⁱⁱⁱ	0.95	2.80	3.740 (2)	171
C21—H21⋯Cg2^iv	0.95	2.80	3.740 (2)	171

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

Acknowledgments

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

supplementary crystallographic information

Comment

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009; Okamoto et al., 2011). As one of the applications of peri-aroylnaphthalene synthetic studies, the authors have integrated the resulting molecular unit to the poly(ether ketone) backbone via nucleophilic aromatic substitution polycondensation (Okamoto et al., 2013). The poly(ether ketone)s composed of 1,8-diaroylenenaphthalene units show unique thermal properties and solubility for organic solvents. These notable properties could arise from the structural features of the 1,8-diaroylene naphthalene units. Under these circumstances, the authors have undertaken the X-ray crystal structural study of several 1,8-diaroylated naphthalene analogues exemplified by (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone (Watanabe et al., 2010) and 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene (Hijikata et al., 2010). These molecules have essentially the same non-coplanar features. The two aroyl groups are twisted so they are almost perpendicular to the naphthalene rings.

The molecular structure of the title compound is displayed in Fig. 1. Two benzoyl groups are on the 1,8-positions of the naphthalene ring and are in an anti orientation relative to one another. The benzene rings of the benzoyl groups make dihedral angles with the naphthalene ring of 59.26 (13) and 59.09 (13)°, respectively. The dihedral angles between the benzene rings of the benzoyl groups and those of the phenoxy groups are 69.05 (13) and 69.02 (13)°. Both carbonyl groups form intramolecular O—H···O hydrogen bonds with hydroxy groups affording six-membered rings. (Fig. 1, Table 1).

In the crystal structure, the molecular packing of the title compound is stabilized mainly by C—H···O and C—H···π interactions. The aromatic hydrogen atoms of the phenoxy groups form two types of intermolecular C—H···O interactions with the ethereal oxygen atom of the phenoxy groups(C26—H26···O4ⁱ= 2.48 Å, C32—H32···O3ⁱⁱ= 2.49 Å; Fig. 2 and Table 1) and the carbonyl oxygen atom (C27—H27···O1ⁱ= 2.51 Å, C33—H33···O2ⁱⁱ= 2.51 Å; Fig. 2 and Table 1). Intermolecular C—H···π interactions between the aromatic hydrogen atom of the benzoyl group and the centroid of the benzene ring of the phenoxy group (C14—H14···Cg1ⁱⁱⁱ= 2.80 Å, C21—H21···Cg2^iv= 2.80 Å; Fig. 3 and Table 1) are observed.

Experimental

To a stirring solution of 1,8-bis(4-phenoxybenzoyl)-2,7-dimethoxynaphthalene (1.0 mmol, 580 mg) in dichloromethane (1.0 ml) at 0°C was added 1.0 M boron tribromide solution in dichloromethane (4.4 ml) slowly, and the reaction mixture was allowed to reach the room temperature. After the reaction mixture had been stirred at room temperature for 48 h, the reaction mixture was cooled to 0 ^oC and very slowly quenched with water and extracted with CHCl₃. The organic layer thus obtained was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give a cake. The crude product was purified by column chromatography (silica gel, CHCl₃) to give the title compound (isolated yield 88%). Single crystals suitable for X-ray diffraction were obtained by crystallization from Et₂O-hexane (v/v = 1:2).

¹H NMR δ (300 MHz, CDCl₃): 6.82–6.84 (4H, m), 7.08–7.26 (10H, m), 7.40 (4H, t, J=7.9 Hz) 7.86 (2H, d, J=8.9 Hz), 11.29 (2H, s) p.p.m.

¹³C NMR δ (75 MHz, CDCl₃): 115.13, 117.03, 117.28, 120.02, 122.02, 124.46, 130.00, 130.68, 133.79, 136.09, 155.58, 161.74, 195.80 p.p.m.

IR (KBr): 3396(O—H), 1620 (C=O), 1608, 1583, 1487 (Ar, naphthalene) cm^-1.

HRMS (m/z): [M + H]⁺ calcd for C₃₆H₂₅O₆, 553.1651 found, 553.1637.

m.p. 464.6–465.9 K.