Crystal structures of 1-hydroxy-4-propyloxy-9,10-anthraquinone and its acetyl derivative

Acta Crystallographica Section E: Crystallographic Communications

Chitoshi Kitamura¹  Hidemi Nakagawa¹ 

[1] Department of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan;

关键词: crystal structure;    anthraquinone;    hydrogen bonding;    π–π stacking;    C—H ...O interactions;   

DOI  :  10.1107/S2056989017015973

来源: DOAJ

【 摘 要 】

1-Hydroxy-4-propyloxy-9,10-anthraquinone, C17H14O4, (I), and its acetyl derivative, 4-acetyloxy-4-propyloxy-9,10-anthraquinone, C19H16O5, (II), were synthesized from the commercially available dye quinizarin. In both compounds, the anthraquinone frameworks are close to planarity. There is a large difference in the conformation of the propyloxy group; the molecule of (I) adopts a gauche conformation [O—C—C—C = −64.4 (2)°], although the molecule of (II) takes a trans-planar conformation (zigzag) [O—C—C—C = 176.1 (3)°]. In the molecule of (I), there is an intramolecular O—H...O hydrogen bond. In both crystals, the molecules are linked by C—H ...O hydrogen bonds. A difference in the molecular arrangements of (I) and (II) is found along the stacking directions.

【 授权许可】

Unknown