Crystal structure and Hirshfeld surface analysis of ethyl (E)-4-[(4-hydroxy-3-methoxy-5-nitrobenzylidene)amino]benzoate

Abstract

The title Schiff base compound, C17H16N2O6, has an E configuration with respect to the C=N bond, with a dihedral angle between the two benzene rings of 31.90 (12)°. There is an intramolecular O—H...Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers enclosing an R22(4) ring motif. The dimers are linked about an inversion centre by pairs of C—H...O hydrogen bonds, which enclose R22(22) loops, forming chains propagating along the [10\overline{3}] direction. Hirshfeld surface analysis and fingerprint plots show enrichment ratios for the H...H, O...H and C...H contacts, indicating a high propensity of such interactions in the crystal. Both the nitro group and the CH3–CH2–O– group are positionally disordered.

Keywords

• crystal structure
• Schiff base
• Hirshfeld surface analysis
• hydrogen bonding