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Acta Cryst. (2013). E69, o1053-o1054  [ doi:10.1107/S1600536813014530 ]

rac-4-(4-Chlorophenyl)-2-methylamino-3-nitro-5,6,7,8-tetrahydro-4H-chromen-5-one

P. Narayanan, J. Kamalraja, P. T. Perumal and K. Sethusankar

Abstract: The title compound, C16H15ClN2O4, contains a chiral centre and crystallizes as a racemate. The methylene group [beta]-positioned to the carbonyl group is partially (21%) disordered. It flips to the opposite sides of the corresponding six-membered carbocycle by -0.304 (3) and 0.197 (11) Å, producing alternative envelope conformations. The planes of the pyran and chlorophenyl rings form a dihedral angle of 86.25 (9)°. The molecular structure is characterized by an intramolecular N-H...O interaction, which generates an S(6) ring motif. The corresponding amino N atom deviates from the plane of the pyran ring by 0.1634 (19) Å. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming C(8) chains running parallel to the b-axis direction. The crystal structure also features C-H...[pi] interactions.


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