Abstract

In the title compound, C16H17NO4, the dihedral angle between benzene rings is 72.7 (2)°. The meth-oxy groups are rotated by 2.4 (2) and -4.9 (2) (benzil-idene moiety) and by 5.6 (3)° (aniline moiety) relative to the adjacent benzene ring. In the crystal, the mol-ecules are linked into chains along [101] through C-H⋯O and O-H⋯N hydrogen bonds.

Highlights

  • In the title compound, C16H17NO4, the dihedral angle between benzene rings is 72.7 (2)

  • The molecules are linked into chains along [101] through C—HÁ Á ÁO and O—HÁ Á ÁN hydrogen bonds

  • Syringaldehyde is a product of the catalytic decomposition of lignin (Crestini et al, 2010)

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Summary

Chemical context

Syringaldehyde is a product of the catalytic decomposition of lignin (Crestini et al, 2010). Syringaldehyde is widely used as a molecular marker to monitor pollution sources and detect the extent of combustion (Robinson et al, 2006). It is known to be an antioxidant (Ibrahim et al, 2012), anticancer, antiinflammatory (Duke, 2003) and antifungal agent (Gurpilhares et al, 2006). Its Schiff bases are known to exhibit a wide range of biological activities (Shi & Zhou, 2011; da Silva et al, 2011)

Structural commentary
Supramolecular features
Synthesis
Refinement

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