Crystal structure of 5,11-dihydropyrido-[2,3-b][1,4]benzodiazepin-6-one

Noura M. Riad; Darius P. Zlotos; Ulrike Holzgrabe; W. T A Harrison

doi:10.1107/S2056989015006817

Crystal structure of 5,11-dihydropyrido-[2,3-b][1,4]benzodiazepin-6-one

Noura M. Riad, Darius P. Zlotos^*, Ulrike Holzgrabe, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

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Abstract

The title compound, C₁₂H₉N₃O, is an intermediate in the synthesis of the muscarinic M2 receptor antagonist AFDX-384. The seven-membered ring adopts a boat conformation and the dihedral angle between the planes of the aromatic rings is 41.51 (9)°. In the crystal, molecules are linked into [001] chains of alternating inversion dimers formed by pairs of N - H⋯O hydrogen bonds and pairs of N - H⋯N hydrogen bonds. In both cases, R²₂(8) loops are generated.

Original language	English
Pages (from-to)	o304-o305
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	5
Early online date	11 Apr 2015
DOIs	https://doi.org/10.1107/S2056989015006817
Publication status	Published - 1 May 2015

Keywords

Boat conformation
Crystal structure
Hydrogen bonding
Pyridobenzodiazepine

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10.1107/S2056989015006817Licence: CC BY

Crystal structure of 5,11-dihydropyrido-[2,3-b][1,4]benzodiazepin-6-one
© 2015 Riadet al. Licence: Creative Commons Attribution (CC-BY) https://creativecommons.org/licenses/by/4.0/
Final published version, 289 KBLicence: CC BY

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Riad, N. M., Zlotos, D. P., Holzgrabe, U., & Harrison, W. T. A. (Ed.) (2015). Crystal structure of 5,11-dihydropyrido-[2,3-b][1,4]benzodiazepin-6-one. Acta Crystallographica Section E: Structure Reports Online, 71(5), o304-o305. https://doi.org/10.1107/S2056989015006817

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abstract = "The title compound, C12H9N3O, is an intermediate in the synthesis of the muscarinic M2 receptor antagonist AFDX-384. The seven-membered ring adopts a boat conformation and the dihedral angle between the planes of the aromatic rings is 41.51 (9)°. In the crystal, molecules are linked into [001] chains of alternating inversion dimers formed by pairs of N - H⋯O hydrogen bonds and pairs of N - H⋯N hydrogen bonds. In both cases, R22(8) loops are generated.",

keywords = "Boat conformation, Crystal structure, Hydrogen bonding, Pyridobenzodiazepine",

author = "Riad, {Noura M.} and Zlotos, {Darius P.} and Ulrike Holzgrabe and Harrison, {W. T A}",

note = "Acknowledgements The authors thank Andreas Lorbach and Todd B. Marder (Institute of Inorganic Chemistry, Wuerzburg University) for the data collection and structure solution. We appreciate the financial support provided to NMR by the Deutscher Akademischer Austauschdienst (DAAD). Thanks are also due to the Deutsche Forschungsgemeinschaft for financial support (SFB 630, Recognition, Preparation and Functional Analysis of Agents against Infectious Diseases, project A1).",

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