(3,6-Dimethoxy-2-naphthyl)(4-fluorobenzoyl)methanone

Abstract

In the title compound, C19H15FO3, the dihedral angle between the naphthalene ring system and the benzene ring is 62.93 (5)°. The bridging carbonyl C—C(=O)—C plane makes dihedral angles of 45.55 (6) and 28.62 (7)°, respectively, with the naphthalene ring system and the benzene ring. Weak inter­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions stabilize the crystal packing.

(3,6-Dimethoxynaphthalen-2-yl)(phenyl)methanone

“…For electrophilic aromatic substitution of naphthalene derivatives affording peri-aroylated compounds regioselectively, see: Okamoto & Yonezawa (2009). For the structures of closely related compounds, see: ; ; Muto et al (2010); ; Nakaema, Watanabe et al (2008); Nishijima et al (2010); Watanabe et al (2010).…”

“…Such 1-aroylnaphthalene homologues as (2,7-dimethoxynaphthalen-1-yl)(3-nitrophenyl)methanone are also revealed to have essentially the same non-coplanar structure as observed for 1,8diaroylated naphthalenes. Furthermore, we reported the crystal structure analysis of the corresponding β-isomers of 3aroyl-2,7-dimethoxynaphthalenes such as 2-(4-chlorobenzoyl)-3,6-dimethoxynaphthalene and (4-fluorophenyl) (3,6-dimethoxy-2-naphthyl)methanone (Watanabe et al, 2010). In the 3-aroylated naphthalenes, which are generally regarded to be thermodynamically more stable than the corresponding 1-positioned isomeric molecules, the aroyl groups are connected to the naphthalene rings in a moderately twisted fashion.…”

(2,7-Dimethoxynaphthalen-1-yl)(2,4,6-trimethylphenyl)methanone

“…For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al (2011). For the structures of closely related compounds, see: Muto et al (2010); Watanabe et al (2010Watanabe et al ( , 2011.…”

“…The arylcarbonyl groups at the 1,8-positions of the naphthalene rings in these compounds are connected in an almost perpendicular fashion. Besides, the crystal structures of arylcarbonylated naphthalene homologues, 1-monoarylcarbonylated naphthalene compounds and the β-isomers of 3-monoarylcarbonylated naphthalene compounds, have been also clarified such as (2,7-dimethoxynaphthalen-1-yl)(4-fluorophenyl)methanone (Watanabe et al, 2011) and (3,6-dimethoxy-2-naphthyl)(4-fluorobenzoyl)methanone (Watanabe, Muto, Nagasawa et al, 2010).…”