Two polymorphs of 2-(prop-2-yn-1-yl­oxy)naphthalene-1,4-dione: solvent-dependent crystallization

The title compound, C(13)H(8)O(3), crystallizes in two polymorphs, namely the monoclinic (space group P2(1)/c) and triclinic (space group Pī) forms, obtained from N,N-di­methyl­formamide and isopropyl alcohol solutions, respectively. The mol­ecular structures and conformations in the two forms are essentially the same as each other. The naphtho­quinone 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 naphtho­quinone units with r.m.s deviations ranging from 0.04 to 0.09 Å. In the monoclinic crystal, mol­ecules 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 inter­action into a layer parallel to the ab plane. Adjacent layers are linked by another C—H⋯π inter­action. In the triclinic crystal, mol­ecules are linked via C—H⋯O and π–π inter­actions, forming a layer parallel to the ab plane. Adjacent layers are linked by a C—H⋯π inter­action.