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

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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.

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ACKNOWLEDGMENTS

The authors thank the Research Fund of Istanbul University for financial support of this work.

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Correspondence to M. Yıldız or A. F. Tuyun.

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Yıldız, M., Bayrak, N., Yıldırım, H. et al. Crystal Structure of 2-(Hexyloxy)benzo[b]phenazine-6,11-dione. Crystallogr. Rep. 63, 925–929 (2018). https://doi.org/10.1134/S1063774518060317

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  • DOI: https://doi.org/10.1134/S1063774518060317

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