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

2-(丙-2-炔-1-基氧基)萘-1,4-二酮的两种多晶型物:溶剂依赖性结晶

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Abstract

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-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.

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