Abstract
The title compound, C13H8O3, crystallizes in two polymorphs, namely the monoclinic (space group P21/c) and triclinic (space group Pī) forms, obtained from N,N-di-methyl-formamide and isopropyl alcohol solutions, respectively. The mol-ecular structures and conformations in the two forms are essentially the same as each other. The naphtho-quinone ring systems are essentially planar with r.m.s. deviations of 0.015 and 0.029 Å for the monoclinic and triclinic forms, respectively. The O-propargyl groups are coplanar with the naphtho-quinone units with r.m.s deviations ranging from 0.04 to 0.09 Å. In the monoclinic crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds, forming a tape structure running along [120]. The tapes are further linked by a C-H⋯π inter-action into a layer parallel to the ab plane. Adjacent layers are linked by another C-H⋯π inter-action. In the triclinic crystal, mol-ecules are linked via C-H⋯O and π-π inter-actions, forming a layer parallel to the ab plane. Adjacent layers are linked by a C-H⋯π inter-action.
Highlights
The title compound, C13H8O3, crystallizes in two polymorphs, namely the monoclinic and triclinic forms, obtained from N,N-dimethylformamide and isopropyl alcohol solutions, respectively
The present study shows that the title compound has two polymorphs, monoclinic and triclinic, crystallized from N,N-dimethylformamide (DMF) and isopropyl alcohol, respectively
Molecules are linked via pairs of C—HÁ Á ÁO hydrogen bonds (C3—H3Á Á ÁO2i and C13— H13Á Á ÁO1ii; symmetry codes as in Table 1), forming a tape structure running along [120]
Summary
Naphthoquinone derivatives have been studied intensively over the past few decades, mostly because of their numerous biological activities, mainly antimicrobial and antitumor (Fujii et al, 1992; Hussain et al, 2007; Epifano et al, 2014). Among the substances that comprise this class, some synthetic bioactive derivatives have been obtained from lawsone (2-hydroxynaphthalene-1,4dione) (Jordao et al, 2015). Lawsone shows three sites able to be alkylated (Lamoureux et al, 2008), resulting in O-alkyl and C-alkyl derivatives difficult to purify in some cases in some cases (Kongkathip et al, 2003). The title compound was obtained in higher yields since oxygen better accommodates the negative charge generated in the enolate formation, using a weak base, propargyl bromide, aprotic solvent and heat. The present study shows that the title compound has two polymorphs, monoclinic (space group P21/c) and triclinic (space group P"ı), crystallized from N,N-dimethylformamide (DMF) and isopropyl alcohol, respectively
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