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Crystal Structure of 2-(Hexyloxy)benzo[ b ]phenazine-6,11-dione

Crystal Structure of 2-(Hexyloxy)benzo[ b ]phenazine-6,11-dione Abstract Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in N,N-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[b]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[b]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C22H20N2O3, crystallizes in the sp. gr. P\(\bar {1}\), Z = 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Crystallography Reports Springer Journals

Crystal Structure of 2-(Hexyloxy)benzo[ b ]phenazine-6,11-dione

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References (29)

Publisher
Springer Journals
Copyright
2018 Pleiades Publishing, Inc.
ISSN
1063-7745
eISSN
1562-689X
DOI
10.1134/s1063774518060317
Publisher site
See Article on Publisher Site

Abstract

Abstract Cyclization of 2-chloro-3-((4-(hexyloxy)phenyl)amino)naphthalene-1,4-dione obtained from the reaction of 2,3-dichloro-1,4-naphthoquinone with 4-(hexyloxy)aniline by sodium azide in N,N-dimethylformamide (DMF) at 90–95°C gives 2-(hexyloxy)benzo[b]phenazine-6,11-dione. This is a remarkable example of a general procedure to prepare functionalized benzo[b]phenazine-6,11-dione derivatives. The structure of the title compound was confirmed by single crystal X-ray diffraction analysis. The compound, C22H20N2O3, crystallizes in the sp. gr. P\(\bar {1}\), Z = 2. Both O atoms and one of N atoms are involved in hydrogen bonds forming a network. Besides, there is offset stacking interaction between the planes of polycyclic systems with interplanar distance of 3.383 Å.

Journal

Crystallography ReportsSpringer Journals

Published: Nov 1, 2018

Keywords: Crystallography and Scattering Methods

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