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)]
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Acta Crystallographica Section E Structure Reports Online
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
