(2,7-Dimethoxynaphthalen-1-yl)(phenyl)methanone

Abstract

The asymmetric unit of the title compound, C19H16O3, contains three independent conformers. Each of the three conformers has essentially the same feature of non-coplanar aromatic rings whereby the aroyl group at the 1-position of the naphthalene ring is twisted in a perpendicular manner to the naphthalene ring. The dihedral angles between the benzene ring planes and the naphthalene ring systems are 75.34 (7), 86.47 (7) and 76.55 (6)° in the three conformers. The crystal structure is stabilized by inter­molecular C—H⋯O hydrogen bonds.

Hydrogen bonding between aromatic H and F groups leading to a stripe structure withR- andS-columns: the crystal structure of (2,7-dimethoxynaphthalen-1-yl)(3-fluorophenyl)methanone and comparison with its 1-aroylnaphthalene analogues

“…However, peri-aroylnaphthalene compounds might not be the best models because their internal steric repulsion presumably restricts the formation of intermolecular interactions. To the best of our knowledge, 1-aroylated naphthalene compounds have essentially the same noncoplanar structure as their 1,8-diaroylated naphthalene homologues in the crystalline state (Kato et al, 2010;Watanabe et al, 2011). On the other hand, the dihedral angle between the benzene and naphthalene rings of 1-aroylated naphthalene is smaller than that of the 1,8-diaroylated naphthalene analogue.…”

“…Several years ago, we reported the crystal structures of two 1-aroylated naphthalene analogues, namely (2,7-dimethoxynaphthalen-1-yl)(phenyl)methanone (or 1-benzoyl-2,7-dimethoxynaphthalene) (Kato et al, 2010), (II) (Fig. 5), and (2,7-dimethoxynaphthalen-1-yl)(4-fluorophenyl)methanone [or 1-(4-fluorobenzoyl)-2,7-dimethoxynaphthalene] (Watanabe et al, 2010), (III) (Fig.…”

(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.…”

Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds

“…Solvents were dried and purified using standard procedures [27]. Synthetic methods and spectral data for 1benzoyl-2,7-dimethoxynaphthalene [28] have been reported in literature. 1 H NMR spectra were recorded on a JEOL JNM-AL300 spectrometer (300 MHz).…”