Received 20 June 2013
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 OH-N, rather than O-HN, 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-HO, - [centroid-centroid distances = 3.744 (3) and 3.780 (3) Å], C-Cl [Clcentroid = 3.261 (3) Å], C-H and C-HO interactions.
Data collection: WinAFC (Rigaku, 1999); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2006 ).
We acknowledge the University of Shizuoka for supporting this study.
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