(8-Bromo-2-hydroxy-7-methoxy-1-naphthyl)(4-chlorobenzoyl)methanone

Abstract

In the title compound, C18H12BrClO3, the naphthalene ring system and the benzene ring make a dihedral angle of 82.18 (9)°. The conformation around the central C=O group is such that the C=O bond vector forms a larger angle to the plane of the naphthalene ring system than to the plane of the benzene ring, viz. 60.91 (16)° versus 13.94 (16)°. In the crystal structure, two π–π inter­actions formed between the naphthalene ring systems [centroid–centroid distances of 3.8014 (13) and 3.9823 (13) Å] and inter­molecular O—H⋯O and C—H⋯O hydrogen bonds are present.

Crystal structure and Hirshfeld surface analysis of 2-hydroxy-7-methoxy-1,8-bis(2,4,6-trichlorobenzoyl)naphthalene

“…Among these, three had bromo group(s) at the 8-position, 3,8-positions, and 3,6-positions of the naphthalene ring core, viz. PUKGIM (Mitsui, Nakaema, Nagasawa et al, 2010), YUNWOP and YUPWEM . Four compounds had an 8-benzoyl group, i.e., 1,8-diaroylated naphthalene compounds, viz.…”

(4-Chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone

“…Recently, we reported the crystal structures of 1-aroylated 2,7-dimethoxynaphthalenes, 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa, 2008), (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone , (4-chlorophenyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al, 2009), 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene (Mitsui, Nakaema, Nagasawa et al, 2010) and (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone (Mitsui, Nagasawa, Watanabe et al, 2010). As a part of our ongoing studies on the synthesis and crystal structure analysis of aroylated naphthalene derivatives, we prepared and analysed the structure of crystal of 2,5-dibromo-4-(4-chlorobenzoyl)-3-hydroxy-6-methoxynaphthalene, (I).…”

“…For related structures, see: Mitsui et al (2009); Mitsui, Nakaema, Nagasawa et al (2010); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008); ; Mitsui, Nagasawa, Watanabe et al (2010). For information on halogenÁ Á Áhalogen contacts, see: Moorthy et al (2002); Pedireddi et al (1994); Saruma & Desiraju (1986).…”

(4-Chlorophenyl)(3,6-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone

“…For the structures of closely related compounds, see: Mitsui et al (2008aMitsui et al ( ,b, 2009Mitsui et al ( , 2010a. For a review of halogen bonding, see: Politzer et al (2007).…”

“…oxynaphthalene (Mitsui et al, 2008a), (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al, 2008b), (4-chlorophenyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al, 2009), 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene (Mitsui et al, 2010a), (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone (Mitsui et al, 2010b) and (4-chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone (Mitsui et al, 2010c). As a part of our ongoing studies on the synthesis and crystal structure analysis of aroylated naphthalene derivatives, we prepared and analysed the structure of a single crystal of 2,7-dibromo-4-(4-chlorobenzoyl)-3hydroxy-6-methoxynaphthalene, (I).…”