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Crystal structure and conformational analysis of 2-hy-droxy-3-(2-methyl-prop-1-en-1-yl)naphthalene-1,4-dione.

ABSTRACT: In the structure of the title compound, C14H12O3, the substituent side chain, in which the H atoms of both methyl groups are disordered over six equivalent sites, lies outside of the plane of the naphthalene-dione ring. The ring-to-chain C-C-C-C torsion angles are 50.7 (3), -176.6 (2) and 4.9 (4)°. An intra-molecular meth-yl-hy-droxy C-H⋯O hydrogen bond is present. In the crystal, mol-ecules are primarily connected by inter-molecular O-H⋯O hydrogen bonds, forming a centrosymmetric cyclic dimer motif [graph set R 2 (2)(10)]. Also present is a weak inter-molecular C-H⋯O hydrogen bond linking the dimers and a weak π-π ring inter-action [ring centroid separation = 3.7862 (13) Å], giving layers parallel to (10-3).

SUBMITTER: Alcantara Emiliano S

PROVIDER: S-EPMC4770963 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of 2-hy-droxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione.

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1-(2-Hy-droxy-4-meth-oxy-phen-yl)-3-(4-methyl-phen-yl)prop-2-en-1-one.

Project description:The mol-ecule of the title compound, C(17)H(16)O(3), exists in the E conformation with respect to the central C=C bond, is almost planar(r.m.s. deviation = 0.003?Å) and has an intra-molecular O-H?O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are linked by C-H?O inter-actions.

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