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Crystal structures of 3,5-bis-[(E)-3-hy-droxy-benzyl-idene]-1-methyl-piperidin-4-one and 3,5-bis-[(E)-2-chloro-benzyl-idene]-1-methyl-piperidin-4-one.

ABSTRACT: The title compounds, C20H19NO3, (1), and C20H17Cl2NO, (2), are the 3-hy-droxy-benzyl-idene and 2-chloro-benzyl-idene derivatives, respectively, of curcumin [systematic name: (1E,6E)-1,7-bis-(4-hy-droxy-3-meth-oxy-phen-yl)-1,6-hepta-diene-3,5-dione]. The dihedral angles between the benzene rings in each compound are 21.07?(6)° for (1) and 13.4?(3)° for (2). In both compounds, the piperidinone rings adopt a sofa confirmation and the methyl group attached to the N atom is in an equatorial position. In the crystal of (1), two pairs of O-H?N and O-H?O hydrogen bonds link the mol-ecules, forming chains along [10-1]. The chains are linked via C-H?O hydrogen bonds, forming undulating sheets parallel to the ac plane. In the crystal of (2), mol-ecules are linked by weak C-H?Cl hydrogen bonds, forming chains along the [204] direction. The chains are linked along the a-axis direction by ?-? inter-actions [inter-centroid distance = 3.779?(4)?Å]. For compound (2), the crystal studied was a non-merohedral twin with the refined ratio of the twin components being 0.116?(6):0.886?(6).

SUBMITTER: Eryanti Y

PROVIDER: S-EPMC4719820 | biostudies-other | 2015 Dec

REPOSITORIES: biostudies-other

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