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5-Hy-droxy-2-{(E)-[(3-nitro-phen-yl)iminio]meth-yl}phenolate.

ABSTRACT: The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C-O(-) bond [1.296?(2)?Å] is shorter than a normal Csp(2)-O(H) bond, and the azomethine C=N bond [1.314?(2)?Å] is longer than a normal C=N double bond. The mol-ecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83?(7) and 8.45?(9)° with the other benzene ring and with the nitro group, respectively. The mol-ecular conformation is stabilized by an intra-molecular N-H?O hydrogen bond. In the crystal, strong O-H?O hydrogen bonds link the mol-ecules into double-stranded chains along the b-axis direction. Within the chains there are ?-? interactions involving the benzene rings of adjacent molecules [centroid-centroid distance = 3.669?(1)?Å]. The chains are linked via C-H?O hydrogen bonds, forming R(2) (1)(6), R(2) (1)(7) and R(2) (2)(10) ring motifs.

SUBMITTER: Shaheen MA

PROVIDER: S-EPMC3435650 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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5-Hy-droxy-2-{(E)-[(3-nitro-phen-yl)iminio]meth-yl}phenolate.

Shaheen Muhammad Ashraf MA Tahir M Nawaz MN Irfan Rana Muhammad RM Iqbal Shahid S Ahmad Saeed S

Acta crystallographica. Section E, Structure reports online 20120801 Pt 9

The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C-O(-) bond [1.296 (2) Å] is shorter than a normal Csp(2)-O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The mol-ecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83 (7) and 8.45 (9)° with the other benzene ring and with the nitro group, respectively. The mol-ecular conformation is stab ...[more]

PMID: 22969523

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