Abstract
The title compound, C18H20N2O3, crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydroxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intramolecular N—H⋯O and one intermolecular O—H⋯O. As a result, the carbonyl C=O distance is long, at 1.310 (2) Å, which may suggest the molecule 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)°].
Highlights
The title compound, C18H20N2O3, crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydroxy tautomer
There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intramolecular N— HÁ Á ÁO and one intermolecular O—HÁ Á ÁO
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)]
Summary
Key indicators: single-crystal X-ray study; T = 295 K; mean (C–C) = 0.002 A; R factor = 0.041; wR factor = 0.124; data-to-parameter ratio = 12.4. The title compound, C18H20N2O3, crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydroxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intramolecular N— HÁ Á ÁO and one intermolecular O—HÁ Á ÁO. The carbonyl C O distance is long, at 1.310 (2) A , which may suggest the molecule 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)]
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