2,7-Dimethoxy-1-(4-nitrobenzoyl)-naphthalene

Abstract

In the title compound, C19H15NO5, the dihedral angle between the naphthalene ring system and the benzene ring is 61.97 (5)°. The dihedral between the naphthalene ring system and the bridging carbonyl C—C(=O)—C plane is 54.68 (6)°, far larger than that [12.54 (7)°] between the phenyl group and the bridging carbonyl group. The nitro group and the phenyl ring are almost coplanar [O—N—C—C torsion angle = 2.94 (19)°]. In the crystal, mol­ecules are linked by C—H⋯π inter­actions and the phenyl rings are involved in a centrosymmetric π–π inter­action with a perpendicular distance of 3.523 Å and a lateral offset of 1.497 Å. In addition, weak inter­molecular C—H⋯O hydrogen bonds are formed between an H atom of one meth­oxy group and a nearby carbonyl O atom.

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

“…Recently, we reported the structures of 1,8-diaroyl-2,7-dimethoxynaphthalenes, i. e., 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al, 2007), bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al, 2010a). In addition, the crystal structural analysis of 1-aroyl-2,7-dimethoxynaphthalenes, i. e., methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al, 2010) and 1-(4-nitorobenzoyl)-2,7-dimethoxynaphthalene (Watanabe et al 2010b), also has revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes.…”

(2,7-Dimethoxynaphthalen-1-yl)(4-fluorophenyl)methanone

“…Recently, we reported the structures of 1,8-diaroyl-2,7-dimethoxynaphthalenes, i. e., (2,7-dimethoxynaphthalene-1,8-diyl)bis(4-fluorophenyl)dimethanone (Watanabe, Nagasawa et al, 2010), bis(4-bromophenyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe, Nakaema, Muto et al, 2010), and [2,7-dimethoxy-8-(4-methylbenzoyl)-1-naphthyl](4-methylphenyl)methanone (Muto et al, 2010). Furthermore, the crystal structures of 1-aroyl-2,7dimethoxynaphthalenes, i. e., 2,7-dimethoxy-1-(4-nitrobenzoyl)naphthalene (Watanabe, Nakaema, Nishijima et al, 2010) and (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (Kato et al, 2010), also exhibit essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. As a part of our ongoing studies on the formation and the structure of the aroylated naphthalene derivatives, the synthesis and crystal structure of (I), a 1-monoaroylnaphthalene bearing fluoro group, is discussed in this report.…”

2-(2,7-Dimethoxy-1-naphthoyl)benzoic acid

“…For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009). For related structures, see: Mitsui, Nakaema et al (2008); Mitsui, Noguchi et al (2009); Watanabe, Nakaema, Muto et al (2010); Watanabe, Nakaema, Nishijima et al (2010); Hijikata et al (2010).…”

“…The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are twisted almost perpendicularly but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings. Moreover, the X-ray crystal structural analysis of 1-(4-substituted benzoylated)naphthalenes, i.e., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al, 2008), (4-chlorobenzoyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al, 2009), 1-(4-nitrobenzoyl)-2,7-dimethoxynaphthalene (Watanabe, Nakaema, Nishijima et al, 2010) and methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al, 2010), has also revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes.…”