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. 2011 Jan 12;67(Pt 2):o318.
doi: 10.1107/S1600536811000249.

6,9-Dimeth-oxy-3,4-dihydro-1H-1,4-oxazino[4,3-a]indol-1-one

Cristian O Salas  1 , Ricardo A Tapia, Yolanda Prieto
Affiliations

6,9-Dimeth-oxy-3,4-dihydro-1H-1,4-oxazino[4,3-a]indol-1-one

Cristian O Salas et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The title compound, C(13)H(13)NO(4), is one cyclization product of the reaction of ethyl 1-(2-bromo-eth-yl)-4,7-dimeth-oxy-1H-indole-2-carboxyl-ate with sodium azide in refluxing dioxane and was synthesized with the aim of finding new compounds with biological properties. Bond lengths and angles are within the expected values and confirm the bond orders giving in the scheme. The shortest contacts between mol-ecules are set along the a axis, where stacked mol-ecules related by an inversion center form an ABAB array through π-π stacking inter-actions with centroid-centroid distances ranging from 3.922 (2) to 4.396 (2) Å. Weak C-H⋯O hydrogen bonds further stabilize the structure.

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Figures

Fig. 1.
Fig. 1.
The structure of the title compound, with displacement ellipsoids drawn at the 50% probability level and H atoms with arbitrary radius.
Fig. 2.
Fig. 2.
Intermolecular interactions in the crystal structure of the title compound, A) hydrogen-bonds, B) weak π-π interactions.
Fig. 3.
Fig. 3.
Reaction scheme for the preparation of molecule 2.
See this image and copyright information in PMC

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