2-(9-Anthrylmethylideneamino)-4-methylphenol

Andrés Villalpando,Frank R Fronczek,Ralph Isovitsch

doi:10.1107/s1600536810016715

Andrés Villalpando, Frank R Fronczek + Show 1 more

Open Access

https://doi.org/10.1107/s1600536810016715

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Abstract

The title compound, C22H17NO, is a novel Schiff base synthesized via a condensation reaction between 9-anthracenecarboxaldehyde and 2-amino-p-cresol. The asymmetric unit contains two independent molecules that are joined by an O—H⋯OH hydrogen bond. An intramolecular O—H⋯N hydrogen bond occurs in each molecule. π-stacking about inversion centers was observed between adjacent phenol rings [centroid–centroid distance = 3.850 (2) Å] and adjacent anthracene rings [centroid–centroid distance = 3.834 (2) Å]. The C—N=C—C torsion angles between the phenol and anthracene rings are close to 180° with values of 174.06 (15) and 179.85 (14)°.

Highlights

The title compound, C22H17NO, is a novel Schiff base synthesized via a condensation reaction between 9-anthracenecarboxaldehyde and 2-amino-p-cresol
The asymmetric unit contains two independent molecules that are joined by an O— HÁ Á ÁOH hydrogen bond
An intramolecular O—HÁ Á ÁN hydrogen bond occurs in each molecule. -stacking about inversion centers was observed between adjacent phenol rings [centroid–centroid distance = 3.850 (2) A ] and adjacent anthracene rings [centroid–centroid distance = 3.834 (2) A ]

Summary

Structure Reports Online

The title compound, C22H17NO, is a novel Schiff base synthesized via a condensation reaction between 9-anthracenecarboxaldehyde and 2-amino-p-cresol. The asymmetric unit contains two independent molecules that are joined by an O— HÁ Á ÁOH hydrogen bond. An intramolecular O—HÁ Á ÁN hydrogen bond occurs in each molecule. -stacking about inversion centers was observed between adjacent phenol rings [centroid–centroid distance = 3.850 (2) A ] and adjacent anthracene rings [centroid–centroid distance = 3.834 (2) A ]. The C—N C—C torsion angles between the phenol and anthracene rings are close to 180 with values of 174.06 (15) and 179.85 (14). For bond-length data, see: Allen et al (1987). For background to the use of luminescent metal complexes formed by Schiff bases in light emitting diode construction and solar energy collection, see: Liao et al (2009); Mak et al (2009)

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