Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 8 (August 2013)

organic compounds

zp2006 scheme

Acta Cryst. (2013). E69, o1226    [ doi:10.1107/S1600536813018084 ]


Y. Ishikawa and Y. Motohashi

Abstract: In the title compound, C21H15Cl2NO2, the H atom of the -OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is formation of a six-membered ring via an intramolecular O...H-N, rather than O-H...N, hydrogen bond in the molecule. The dihedral angle between the naphthalene ring system and the benzene ring of the 2H-chromen system is 87.41 (4)°. In the crystal, the molecules are packed through N-H...O, [pi]-[pi] [centroid-centroid distances = 3.744 (3) and 3.780 (3) Å], C-Cl...[pi] [Cl...centroid = 3.261 (3) Å], C-H...[pi] and C-H...O interactions.

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