Structure of the co-crystalline solid formed between 1,4-dichloronaphthalene-2,3-diol and dioxane

1,4-Dichloronaphthalene-2,3-diol

“…Data collection: CAD-4 Manual (Schagen et al, 1989); cell refinement: CAD-4 Manual; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al, 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: local programs. 1,4-Dichloronaphthalene-2,3-diol forms a 2:1 inclusion compound with dioxane, the structure of which (in space group P2 1 /c) has been reported earlier (Ahn et al, 1995). However, crystallization from benzene, chloroform, diethyl ether, ethanol or methanol yields solvent-free material.…”

“…For related structures, see: Ahn et al (1995Ahn et al ( , 1996. For the synthesis, see: Zincke & Fries (1904); Ahn et al (1995). For related literature, see: Coppens & Hamilton (1970).…”

2,3-Dichlorobenzene-1,4-diol

“…Crystal structures of related dichloronaphthalenediols have been previously reported by us (Ahn et al, 1995(Ahn et al, , 1996. In the title compound (Fig 1), each molecule participates in four hydrogen bonds, two as donor and two as acceptor, creating a layer structure in the ac plane with O1-H1O1···O2-H1O2···O1-H1O1··· chains parallel to a (Fig 2, Table 1).…”

“…For the structures of related dichloronaphthalenediols, see: Ahn et al (1995Ahn et al ( , 1996. For the preparation of the title compound, see: Beddoes et al (1981).…”

4-Chloro-1-naphthol

“…Halo-substituted hydroxyaromatic compounds (among them the title compound) are a class of starting materials for the preparation of bis(hydroxyaromatic) compounds, which find many uses in chemical applications such as dyes, plastics, pharmaceuticals and agrochemicals, and in forming polymers such as polycarbonates, polyestercarbonates, polyesters, polyethers, polyetherimides and polyether ketones (Patel et al, 2005). A search of the Cambridge Structural Database (CSD, Version 5.30 of November 2008;Allen, 2002) for chloro-substituted hydroxy-derivatives of naphthalene revealed only five reports of four chloro-substituted naphthalenediols, namely 1,5-dichloro-2,6-dihydroxynaphthalene [CSD refcodes JIMFAM (Nakasuji et al, 1991) and JIMFAM01 (Ahn et al, 1995)], 1,5-dichloro-2,6-naphthoquinone 1,5-dichloro-2,6-dihydroxynaphthalene (JIMDUE; Nakasuji et al, 1991), 1,5-dichloronaphthalene-2,6-diol dioxane solvate (RAYPOW; Ahn et al, 1995) and bis(1,4-dichloronaphthalene-2,3-diol) dioxane (ZIPYEC; Ahn et al, 1994), and no prior reports of the structures of chlorosubstituted naphthols. Thus, this paper concerning the results of structural studies of the title compound, (I), would appear to be the first example involving a chloronaphthol.…”