(2-Hy­droxy-7-meth­oxy­naphthalen-1-yl)(phen­yl)methanone

Atsushi Nagasawa; Ryosuke Mitsui; Yuichi Kato; Akiko Okamoto; Noriyuki Yonezawa

doi:10.1107/S1600536810038547

. 2010 Sep 30;66(Pt 10):o2677. doi: 10.1107/S1600536810038547

(2-Hydroxy-7-methoxynaphthalen-1-yl)(phenyl)methanone

Atsushi Nagasawa ^a, Ryosuke Mitsui ^a, Yuichi Kato ^a, Akiko Okamoto ^a, Noriyuki Yonezawa ^a,^*

PMCID: PMC2983170 PMID: 21587645

Abstract

In the molecule of the title compound, C₁₈H₁₄O₃, there is an intramolecular O—H⋯O=C hydrogen bond between the carbonyl and hydroxy groups on the naphthalene ring system. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the phenyl ring are 30.58 (6) and 42.82 (7)°, respectively, while the dihedral angle between the naphthalene ring system and the phenyl ring is 58.65 (5)°. In the crystal, molecules are connected by pairs of intermolecular O—H⋯O=C hydrogen bonds, forming centrosymmetric dimers.

Related literature

For closely related structures, see: Hijikata et al. (2010 ▶); Kato et al. (2010 ▶); Mitsui et al. (2009 ▶); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶).

Experimental

Crystal data

C₁₈H₁₄O₃
M _r = 278.29
Monoclinic,
a = 9.81012 (18) Å
b = 6.27891 (11) Å
c = 22.0737 (4) Å
β = 93.167 (1)°
V = 1357.59 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 193 K
0.60 × 0.40 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.586, T _max = 0.754
20565 measured reflections
2496 independent reflections
2244 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.103
S = 1.08
2496 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038547/is2606sup1.cif

e-66-o2677-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038547/is2606Isup2.hkl

e-66-o2677-Isup2.hkl^{(120.1KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.92 (2)	1.77 (2)	2.5792 (14)	145 (2)
O1—H1⋯O3ⁱ	0.92 (2)	2.32 (2)	3.0088 (16)	132.4 (18)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would express their gratitude to Professor Keiichi Noguchi for technical advice. This work was partially supported by a Sasagawa Scientific research grant from the Japan Science Society.

supplementary crystallographic information

Comment

Recently, we reported the crystal structures of several 1-aroylated 2,7-dimethoxynaphthalene homologues exemplified by 1-benzoyl-2,7-dimethoxynaphthalene (Kato et al., 2010) and 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa, 2008). Methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al., 2010). Furthermore, we also reported the crystal structure of 1-monoaroylnaphthalene derivatives having 2-oxy group exemplified by (4-chlorobenzoyl)(2-hydroxy-7-methoxynaphthalene-1-yl)metanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008) and (4-chlorophenyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al., 2009). As a part of our ongoing studies on the synthesis and crystal structure analysis of aroylated naphthalene derivatives, we prepared and analysed the crystal structure of 1-benzoyl-2-hydroxy-7-methoxynaphthalene (I). The title compound was prepared by chemoselective demethylation of 1-benzoyl-2,7-dimethoxynaphthalene with aluminium trichloride.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is shown in Fig. 1. In the molecule of (I), the intramolecular O—H···O═C hydrogen bond that forms a six-membered ring including carbonyl and hydroxy groups on the naphthalene ring is observed [O3···H1 = 1.77 (2) Å]. The conformation of these groups resembles to that of (4-chlorobenzoyl)(2-hydroxy-7-methoxynaphthalen-1-yl)metanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008). The angles of C═O bond vector against the least-squares plane of the naphthalene ring (C1–C10) and benzene ring (C12–C17) are 30.58 (6) and 42.82 (7)°, respectively. The dihedral angle between the naphthalene ring (C1–C10) and benzene ring (C12–C17) is 58.65 (5)°.

In the crystal structure, the molecular packing of (I) is mainly stabilized by intermolecular hydrogen bond and van der Waals interaction. Two adjacent naphthalene rings are exactly parallel and the intermolecular O—H···O═C hydrogen bond between the hydroxy group and the carbonyl oxygen on the naphthalene ring (Fig. 2) along the c axis, is observed [O3···H1 = 2.32 (2) Å]. The oxygen atom in the methoxy group interacts with carbon atom in the methoxy group of the next molecule, i.e. two methoxy groups in the adjacent molecules interact with each other [O2···C18 = 3.060 (2) Å] along the a axis. The naphthalene rings interact with the carbonyl groups [C4···O3 = 3.036 (18) Å] along the b axis. The benzoyl groups interact with the methyl groups (C16···H18A = 2.88 Å) along the a axis.

Experimental

To a solution of 1-benzoyl-2,7-dimethoxynaphthalene (2.92 g, 10 mmol) in CH₂Cl₂ (100 ml) was added AlCl₃ (6.65 g, 50 mmol). The reaction mixture was refluxed for 30 min giving a dark red solution, which was then poured into H₂O (30 ml). The aqueous layer was extracted with CHCl₃(30 ml × 3). The combined organic layers were washed with brine (30 ml × 3), and dried over MgSO₄ overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from hexane to give compound (I) as yellow platelets (m.p. 371.8–372.3 K, yield 1.45 g, 52%).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 11.64 (s, 1H), 7.85 (d, 1H), 7.64–7.60 (m, 3H), 7.55 (tt, 1H), 7.43 (t, 2H) 7.08 (d, 1H), 6.89 (dd, 1H), 6.59 (d, 1H), 3.27 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 200.8, 162.8, 158.2, 140.8, 136.5, 134.1, 132.3, 130.1, 129.14, 128.8, 123.7, 116.5, 115.9, 113.7, 106.5, 54.5; IR (KBr): 3446, 1617, 1572, 1511, 1200; HRMS (m/z): [M + H]⁺ calcd for C₁₈H₁₅O₃, 279.1021; found, 279.0999.