2,7-Dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene

Abstract

Key indicators: single-crystal X-ray study; T = 193 K; mean (C-C) = 0.002 Å; R factor = 0.036; wR factor = 0.099; data-to-parameter ratio = 13.6.In the title molecule {systematic name: [2,7-dimethoxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methanone}, C 38 H 28 O 6 , the 4-phenoxybenzoyl units adopt a syn orientation with respect to the naphthalene ring system. The internal benzene rings, A and B, make dihedral angles of 86.72 (5) and 79.22 (5) with the naphthalene ring system. The two terminal benzene rings, C and D, of the 4-phenoxybenzoyl groups are twisted with respect to benzene rings A and B, with dihedral angles of A/C = 62.72 (8) and B/D = 87.61 (6) . In the crystal, H atoms in the naphthalene system make two types of intermolecular C-HÁ Á ÁO interactions with the carbonyl O atom and the phenyl etheral O atom of neighbouring molecules. Molecules are further linked by C-HÁ Á Á interactions involving a H atom of terminal benzene ring D and the -system of the internal benzene ring A, forming dimers centered about an inversion center. Related literature

[8-(4-Butoxybenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-butoxyphenyl)methanone

“…The aroyl groups in these compounds are perpendicularly attached to the naphthalene rings and oriented in opposite directions. On the other hand, X-ray structure of 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene (Hijikata et al, 2010) having the aroyl groups oriented in the same directions has been also revealed. As a part of our ongoing studies on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, 1,8-diaroylnaphthalene bearing butoxy groups, is discussed in this article.…”

[2,7-Dimethoxy-8-(2-naphthoyl)naphthalen-1-yl](naphthalen-2-yl)methanone

“…For the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene giving aroylated naphthalene compounds, see: Okamoto & Yonezawa (2009). For the structures of closely related compounds, see: Hijikata et al (2010); Muto et al (2010); Nakaema et al (2008); Nishijima et al (2010).…”

“…In these compounds, two aroyl groups tend to attach in nearly perpendicular manner and orient in opposite direction. Recently, the crystal structure of 2,7-dimethoxy-1,8-bis(4-phenoxybenzoyl)naphthalene has been clarified as syn-conformation, where two phenoxybenzoyl groups are oriented in the same direction (Hijikata et al, 2010). As a part of our continuous studies on the molecular structures of homologous aroylated 2,7-dimethoxynaphthalene molecules, the X-ray crystal structure of the title compound, (I), bis(2-naphthoylated) 2,7-dimethoxynaphthalene, is discussed in this article.…”

Crystal structure of 1-(4-hydroxybenzoyl)-2,7-dimethoxynaphthalene: Contribution of classical and non-classical hydrogen bonding interactions to the molecular packing structure

“…peri-Aroylated naphthalene compounds thus obtained are proved to have non-coplanarly accumulated aromatic-rings-structure in crystal, i.e., the aroyl groups are twistedly situated to the naphthalene ring core in a perpendicular fashion [7][8][9]. Besides, the two aroyl groups are ordinarily oriented in an opposite direction with a few exceptional compounds bearing unidirectionally-aligned aroyl groups [10,11]. The non-coplanarly congested aromatic rings spatial organization makes the authors imagine that formation of strong π…π stacking interactions should be restricted.…”