1,8-Dibenzoyl-2,7-dimethoxynaphthalene

Abstract

The mol­ecule of the title compound, C26H20O4, is located on a twofold rotation axis. The two benzoyl groups are situated in an anti orientation. The dihedral angle between the mean planes of the phenyl ring and the naphthalene ring system is 80.25 (6)°. The phenyl and carbonyl groups in each benzoyl group are almost coplanar. The mol­ecular packing is stabilized by weak C—H⋯O hydrogen bonds and a π–π stacking inter­action between the phenyl rings [centroid–centroid and inter­planar distances of 3.6383 (10) and 3.294 Å, respectively].

1,8-Bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene

“…For related structures, see: Muto et al (2010); Nakaema et al (2007Nakaema et al ( , 2008; Watanabe et al (2010a,b). For work-up procedure in the preparation of the title compound, see: Bellamy et al (1984).…”

“…The aromatic rings in this molecule are clarified to be assembled with non-coplanar configuration resulting in partial disruption of π-conjugated ring systems. Recently, we reported the X-ray crystal structures of 1,8-diaroylated 2,7-dimethoxynaphthalenes such as 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al, 2007), 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al, 2008), bis(4-bromophenyl) (2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al, 2010a), (Watanabe et al, 2010b) and 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al, in press). As a part of our continuous study on the molecular structures of this kind of homologous molecules, the X-ray crystal structure of title compound, (I), a peri-aroylnaphthalene bearing amino groups, is discussed in this article.…”

Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its analogous benzoylnaphthalene

“…The molecular structure of 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al, 2008), showing the atom-labelling scheme and with displacement ellipsoids drawn at the 50% probability level [symmetry code: (iv) Àx, y, Àz + CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: Il Milione (Burla et al, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008). (7) 0.0132 (7) 0.0051 (7) O7 0.0421 (8) 0.0287 (7) 0.0347 (8) …”

“…According to X-ray crystal structure studies, the resulting 1,8-diaroylated naphthalene derivatives, such as 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema et al, 2008), have a noncoplanar organization of the aromatic rings. Herein, the X-ray crystal structure of the title compound, 1,8-dibenzoyl-2,7-dihydroxynaphthalene, (I), is reported.…”

“…These dimeric aggregates are connected into layers in the bc plane by intermolecular (naphthalene)C-HÁ Á ÁO C interactions. On the other hand, the analogous compound bearing methoxy groups at the 2-and 7-positions of the naphthalene ring, namely 1,8-dibenzoyl-2,7-dimethoxynaphthalene [Nakaema et al (2008). Acta Cryst.…”