{2,7-Dimethoxy-8-[4-(propan-2-yloxy)benzoyl]naphthalen-1-yl}[4-(propan-2-yloxy)phenyl]methanone

Abstract

The title compound, C32H32O6, crystallized with two independent molecules in the asymmetric unit. Each molecule has essentially the same feature of non-coplanar aromatic rings whereby the two 4-isopropoxybenzoyl groups are twisted in a perpendicular manner to the naphthalene ring and oriented in the same direction (syn-orientation). The benzene rings of the aroyl groups make dihedral angles of 16.13 (7) and 25.31 (7)° in the two molecules. These benzene rings make dihedral angles of 88.38 (8) and 75.32 (7)° with the naphthalene ring system in one molecule, and 89.71 (7) and 82.11 (7)° in the other. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming a three-dimensional network. In one independent molecule, the 2-propyl groups of both isoprop­oxy groups are disordered over two positions with site occupancies of 0.512 (3) and 0.488 (3).

(4-Ethoxybenzoyl)[8-(4-ethoxybenzoyl)-2,7-dimethoxynaphthalen-1-yl]methanone

“…For formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009); Okamoto et al (2011). For the structures of closely related compounds, see: Hijikata et al (2010); Sasagawa et al (2011Sasagawa et al ( , 2012; Sasagawa, Sakamoto et al (2013); Sasagawa, Takeuchi et al (2013).…”

“…According to the authors′ knowledge, most 1,8-diaroylnaphthalene derivatives have anti-oriented structures. Recently, we have also clarified another structure of the 1,8-diaroylnaphthalene derivatives, where the two aroyl groups are situated in same direction (syn-orientation), 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene (Hijikata et al, 2010) and 1,8-bis(4-isopropoxybenzoyl)-2,7-dimethoxynaphthalene [{2,7-dimethoxy-8-[4-(propan-2-yloxy)-benzoyl]naphthalen-1-yl}[4-(propan-2-yloxy)phenyl]methanone] (Sasagawa, Takeuchi et al, 2013). As a part of our ongoing studies on the molecular structures of these kinds of homologous molecules, the X-ray crystal structure of the title compound, 1,8-diaroylated naphthalene bearing ethoxy groups on the aroyl moieties, is discussed herein.…”

1,8-Bis(4-fluorobenzoyl)naphthalen-2,7-diyl dimethanesulfonate

“…For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009); Okamoto et al (2011). For the crystal structures of closely related compounds, see: Watanabe et al (2010); Tsumuki et al (2011); Hijikata et al (2010Hijikata et al ( , 2012; Sasagawa et al (2013).…”

Crystal Structure of 1,8-Bis(4-Fluorobenzoyl)naphthalene-2,7-Diyl Dibenzoate: Role of (Sp2)c–h…f Hydrogen Bonding as Distinctly Strong Interaction Among Non-Classical Hydrogen Bonds Contributing Stability of the Crystal

“…17,18 Molecular structures of 1,8-diaroylated 2,7-dialkoxynaphthalene compounds in crystals have common features that two aroyl groups are noncoplanarly located to the 2,7-dialkoxynaphthalene core and oriented in an opposite direction 19 with a few exceptional compounds bearing unidirectional-alignment of aroyl groups. [20][21][22] The molecular packing of 1,8-diaroylated 2,7-dialkoxynaphthalene compounds are mainly stabilized by weak hydrogen bonds. Four kinds of noncovalent-bonding interactions, (sp 2 )C-H···O=C hydrogen bond, (sp of frequency.…”