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3-[(Z)-(4-Diethyl-amino-6-oxocyclo-hexa-2,4-dien-1-yl-idene)methyl-amino]benzoic acid.

ABSTRACT: The title compound, C(18)H(20)N(2)O(3), crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydr-oxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intra-molecular N-H?O and one inter-molecular O-H?O. As a result, the carbonyl C=O distance is long, at 1.310?(2)?Å, which may suggest the mol-ecule has a significant zwitterionic character. The dihedral angle between the benzene ring planes is 15.05?(7)°. As a result of the intramolecular hydrogen bond, the bridging C-C=N-C group is almost coplanar with the benzene ring that has the diethylamino substituent [dihedral angle 2.35?(15)°].

SUBMITTER: Swamy MT

PROVIDER: S-EPMC2915231 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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3-[(Z)-(4-Diethyl-amino-6-oxocyclo-hexa-2,4-dien-1-yl-idene)methyl-amino]benzoic acid.

Swamy M T MT Narayana B B Yathirajan H S HS Sarojini B K BK Kubicki Maciej M

Acta crystallographica. Section E, Structure reports online 20071206 Pt 1

The title compound, C(18)H(20)N(2)O(3), crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydr-oxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intra-molecular N-H⋯O and one inter-molecular O-H⋯O. As a result, the carbonyl C=O distance is long, at 1.310 (2) Å, which may suggest the mol-ecule has a significant zwitterionic character. The dihedral angle ...[more]

PMID: 21200729

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