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2-[(Naphthalen-1-yl-methyl-idene)amino]-5-methyl-phenol.

ABSTRACT: The title compound, C(18)H(15)NO, is a Schiff base prepared from an acid-catalyzed condensation reaction between 1-naphthaldehyde and 6-amino-m-cresol. Intra-molecular hydrogen bonding occurs via an O-H?N inter-action, generating an S(5) ring motif. Neighboring phenol groups participate in inter-molecular hydrogen bonding through an O-H?O inter-action, forming chains. The O atom of the phenol group also participates in an intermolecular C-H?O interaction with an H atom of one of the naphthalene rings. The C-N=C-C torsion angle between the phenol and naphthalene rings is -179.8?(2)°. Crystal packing involves stacks with the mol-ecules inter-acting through the ?-systems of the C=N with both the phenol system and one of the naphthalene rings.

SUBMITTER: Orona G 

PROVIDER: S-EPMC3200862 | biostudies-other | 2011 Sep

REPOSITORIES: biostudies-other

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2-[(Naphthalen-1-yl-methyl-idene)amino]-5-methyl-phenol.

Orona Gabriella G   Molinar Vanessa V   Fronczek Frank R FR   Isovitsch Ralph R  

Acta crystallographica. Section E, Structure reports online 20110827 Pt 9

The title compound, C(18)H(15)NO, is a Schiff base prepared from an acid-catalyzed condensation reaction between 1-naphthaldehyde and 6-amino-m-cresol. Intra-molecular hydrogen bonding occurs via an O-H⋯N inter-action, generating an S(5) ring motif. Neighboring phenol groups participate in inter-molecular hydrogen bonding through an O-H⋯O inter-action, forming chains. The O atom of the phenol group also participates in an intermolecular C-H⋯O interaction with an H atom of one of the naphthalene  ...[more]