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Crystal structures of 1-hy-droxy-4-prop-yloxy-9,10-anthra-quinone and its acetyl derivative.

ABSTRACT: 1-Hy-droxy-4-prop-yloxy-9,10-anthra-quinone, C₁₇H₁₄O₄, (I), and its acetyl derivative, 4-acet-yloxy-4-prop-yloxy-9,10-anthra-quinone, C₁₉H₁₆O₅, (II), were synthesized from the commercially available dye quinizarin. In both compounds, the anthra-quinone frameworks are close to planarity. There is a large difference in the conformation of the prop-yloxy group; the mol-ecule of (I) adopts a gauche conformation [O-C-C-C = -64.4?(2)°], although the mol-ecule of (II) takes a trans-planar conformation (zigzag) [O-C-C-C = 176.1?(3)°]. In the mol-ecule of (I), there is an intra-molecular O-H?O hydrogen bond. In both crystals, the mol-ecules are linked by C-H ?O hydrogen bonds. A difference in the mol-ecular arrangements of (I) and (II) is found along the stacking directions.

SUBMITTER: Nakagawa H

PROVIDER: S-EPMC5730237 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Crystal structures of 1-hy-droxy-4-prop-yloxy-9,10-anthra-quinone and its acetyl derivative.

Nakagawa Hidemi H Kitamura Chitoshi C

Acta crystallographica. Section E, Crystallographic communications 20171110 Pt 12

1-Hy-droxy-4-prop-yloxy-9,10-anthra-quinone, C17H14O4, (I), and its acetyl derivative, 4-acet-yloxy-4-prop-yloxy-9,10-anthra-quinone, C19H16O5, (II), were synthesized from the commercially available dye quinizarin. In both compounds, the anthra-quinone frameworks are close to planarity. There is a large difference in the conformation of the prop-yloxy group; the mol-ecule of (I) adopts a gauche conformation [O-C-C-C = -64.4 ...[more]

PMID: 29250400

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