Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 12 (December 2013)

organic compounds

Acta Cryst. (2013). C69, 1563-1566    [ doi:10.1107/S010827011303196X ]

Inter­molecular C-H...O, Cl...Cl and [pi]-[pi] inter­actions in the 2-di­chloro­methyl derivative of vitamin K3

R. Soave and P. Colombo

Abstract: The title 1,4-naphtho­quinone, 2-di­chloro­methyl-3-methyl-1,4-di­hydro­naphthalene-1,4-dione, C12H8Cl2O2, is a chlorinated derivative of vitamin K3, which is a synthetic compound also known as menadione. Mol­ecules of (I) are planar and lie on a crystallographic mirror plane (Z' = 0.5) in the space group Pnma. They are connected to each other by C-H...O hydrogen bonds, forming two-dimensional layers parallel to the ac plane. In addition, Cl...Cl and [pi]-[pi] inter­actions link adjacent mol­ecules in different layers, thus forming zigzag ribbons along the b axis, such that a three-dimensional architecture is generated.

CCDC reference: 973339

Formula: C12H8Cl2O2

Keywords: crystal structure; 1,4-naphtho­quinones; halogen bond; anti­cancer activity; C-H...O hydrogen bonding; vitamin K3 derivative.

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[ doi:10.1107/S010827011303196X/ky3044Isup3.cml ]
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