syn and anti conformations in 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid and two related salts.

doi:10.1107/S2053229614007827

Paper

syn and anti conformations in 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid and two related salts.

Published May 15, 2014 · A. Yatsenko, K. Paseshnichenko

Acta crystallographica. Section C, Structural chemistry

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Abstract

The crystal structures of 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid, C13H9N3O5, (I), ammonium 2-hydroxy-5-[(E)-phenyldiazenyl]benzoate, NH4(+)·C13H9N2O3(-), (II), and sodium 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoate trihydrate, Na(+)·C13H8N3O5(-)·3H2O, (III), have been determined using single-crystal X-ray diffraction. In (I) and (III), the phenyldiazenyl and carboxylic acid/carboxylate groups are in an anti orientation with respect to each other, which is in accord with the results of density functional theory (DFT) calculations, whereas in (II), the anion adopts a syn conformation. In (I), molecules form slanted stacks along the [100] direction. In (II), anions form bilayers parallel to (010), the inner part of the bilayers being formed by the benzene rings, with the -OH and -COO(-) substituents on the bilayer surface. The NH4(+) cations in (II) are located between the bilayers and are engaged in numerous N-H···O hydrogen bonds. In (III), anions form layers parallel to (001). Both Na(+) cations have a distorted octahedral environment, with four octahedra edge-shared by bridging water O atoms, forming [Na4(H2O)12](4+) units.

Study Snapshot

The crystal structures of 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid and related salts reveal anti-oriented phenyldiazenyl and carboxylic acid/carboxylate groups in both acid and salt forms, with

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

syn and anti conformations in 2-hydroxy-5-[(E)-(4-nitrophenyl)diazenyl]benzoic acid and two related salts.

References

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This compound exhibits asymmetric unit structure with two independent 3,5-dimethylpyrazole and two independent 2-hydroxy-5-(phenyldiazenyl)benzoic acid molecules linked by intermolecular hydrogen bonds and weak C-H interactions.

Experimental and density functional theory (DFT) studies on (E)-2-Acetyl-4-(4-nitrophenyldiazenyl) phenol

The crystal structure of (E)-2-Acetyl-4-(4-nitrophenyldiazenyl) phenol is adopted to its E configuration and linked by C HO hydrogen bonds, with optimized molecular structure and geometry using B3LYP density functional theory.

publCIF: software for editing, validating and formatting crystallographic information files

PublCIF is a free software tool for creating, editing, validating, and formatting crystallographic information files for journal publication, providing access to resources and tools for structure report preparation.

Citations

Carboxylate-phenolate tautomerism in 5-[(nitrophenyl)diazenyl]salicylate anions.

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