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Issue 0, 1969
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Crystal and molecular structure of salicylaldehyde azine


The crystal and molecular structure of salicylaldehyde azine has been determined by Patterson and Fourier methods from three-dimensional X-ray data, and refined by anisotropic least-squares methods to a final R value of 0·087. The crystals are monoclinic, space group P21/c, with two molecules in the unit cell of dimensions a= 8·467, b= 6·318, c= 12·432 Å, β= 112°22′.

The molecules are centrosymmetric and nearly planar; the small deviations from planarity are indicative of intramolecular overcrowding between the two ortho-substituents in the benzene ring. The distribution of bond distances within the benzene ring is consistent with a significant contribution to the structure from a resonance quinonoid form. A strong internal hydrogen bond of 2·645 Å binds the phenolic hydroxy-group to the nearest nitrogen atom in the azine chain.

The molecules are packed in plane-to-plane stacks within the crystal, with a perpendicular spacing between adjacent molecules of about 3·4 Å, which in part accounts for its thermochromic properties.

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Article type: Paper
DOI: 10.1039/J29690000733
Citation: J. Chem. Soc. B, 1969,0, 733-741
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    Crystal and molecular structure of salicylaldehyde azine

    G. Arcovito, M. Bonamico, A. Domenicano and A. Vaciago, J. Chem. Soc. B, 1969, 0, 733
    DOI: 10.1039/J29690000733

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