Crystal structure of 8-ethoxy-3-(4-nitrophenyl)-2H-chromen-2-one

Abstract

In the title compound, C17H13NO5, the coumarin ring system is essentially planar (r.m.s. deviation = 0.008 Å). The nitrophenyl ring makes a dihedral angle of 25.27 (9)° with the coumarin ring plane. The nitro group is almost coplanar with the phenyl ring to which it is attached, making a dihedral angle of 4.3 (3)°. The ethoxy group is inclined to the coumarin ring plane by 4.1 (2)°. Electron delocalization was found at the short bridging C—C bond with a bond length of 1.354 (2) Å. In the crystal, molecules are linked via C—H...O hydrogen bonds, forming sheets in the bc plane. The sheets are linked via π–π stacking [centroid–centroid distances = 3.5688 (13) and 3.7514 (13) Å], forming a three-dimensional structure.

Keywords

• crystal structure
• coumarin
• chromen
• C—H...O hydrogen bonds
• π–π stacking