Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis

Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis

In the solid state, the title compound, C12H16BrNO5 [systematic name: 4-bromo-2-((1E)-{[1,3-dihy­droxy-2-(hy­droxy­meth­yl)propan-2-yl]iminium­yl}meth­yl)-6-meth­oxy­benzen-1-olate], C12H16BrNO5, is found in the keto-amine tautomeric form, with an intra­molecular iminium-N-H...O(phenolate) hydrogen...

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Bibliographic Details
Main Authors: Lee, See Mun *, Lo, Kong Mun *, Tan, Sang Loon *, Tiekink, Edward R. T. *
Format: Article
Language:English
Published: International Union of Crystallography 2016
Subjects:
QD Chemistry
Online Access:http://eprints.sunway.edu.my/646/
http://eprints.sunway.edu.my/646/1/Acta%20E_RC%202016%201223.pdf
Description
Summary:In the solid state, the title compound, C12H16BrNO5 [systematic name: 4-bromo-2-((1E)-{[1,3-dihy­droxy-2-(hy­droxy­meth­yl)propan-2-yl]iminium­yl}meth­yl)-6-meth­oxy­benzen-1-olate], C12H16BrNO5, is found in the keto-amine tautomeric form, with an intra­molecular iminium-N-H...O(phenolate) hydrogen bond and an E conformation about the C=N bond. Both gauche (two) and anti relationships are found for the methyl­hydroxy groups. In the crystal, a supra­molecular layer in the bc plane is formed via hy­droxy-O-H...O(hy­droxy) and charge-assisted hy­droxy-O-H...O(phenolate) hydrogen-bonding inter­actions; various C-H...O inter­actions provide additional cohesion to the layers, which stack along the a axis with no directional inter­actions between them. A Hirshfeld surface analysis confirms the lack of specific inter­actions in the inter-layer region.

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