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1,1'-[m-Phenyl-enebis(nitrilo-methanylyl-idene)]dinaphthalen-2-ol-1,1'-[m-phenyl-enebis(imino-methanylyl-idene)]dinaphthalen-2(1H)-one (0.58/0.42).


ABSTRACT: In the solid state the title Schiff base, 0.58C(28)H(20)N(2)O(2)·0.42C(28)H(20)N(2)O(2), exists both as the keto-imino and as the enol-amino tautomer, which is manifested in the disorder of the H atom in the intra-molecular hydrogen-bonded ring. The naphthalene ring systems show some distortion, which is consistent with the quinoid effect. The ratio of the enol form refined to 58?(5)%. The mol-ecule has crystallographically imposed symmetry: a twofold axis passes through the central benzene ring. Crystals are built up of layers parallel to (010). Stacking interactions between the layers involve only standard van der Waals attraction forces between apolar groups. The alignment of the aromatic rings in neighbouring layers shows a herringbone motif. A weak C-H?O inter-action is observed.

SUBMITTER: Blagus A 

PROVIDER: S-EPMC3247324 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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1,1'-[m-Phenyl-enebis(nitrilo-methanylyl-idene)]dinaphthalen-2-ol-1,1'-[m-phenyl-enebis(imino-methanylyl-idene)]dinaphthalen-2(1H)-one (0.58/0.42).

Blagus Anita A   Kaitner Branko B  

Acta crystallographica. Section E, Structure reports online 20111012 Pt 11


In the solid state the title Schiff base, 0.58C(28)H(20)N(2)O(2)·0.42C(28)H(20)N(2)O(2), exists both as the keto-imino and as the enol-amino tautomer, which is manifested in the disorder of the H atom in the intra-molecular hydrogen-bonded ring. The naphthalene ring systems show some distortion, which is consistent with the quinoid effect. The ratio of the enol form refined to 58 (5)%. The mol-ecule has crystallographically imposed symmetry: a twofold axis passes through the central benzene ring  ...[more]

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