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Selective crystallization of indigo B by a modified sublimation method and its redetermined structure.

ABSTRACT: Good-quality single crystals of the title compound, indigo B [systematic name: 2-(3-oxoindolin-2-yl-idene)indolin-3-one], C(16)H(10)N(2)O(2), have been prepared with high selectivity by a sublimation process. The previous structure of indigo B [Süsse & Wolf (1980 ?). Naturwissenschaften, 67, 453], which showed that the complete mol-ecule is generated by crystallographic inversion symmetry has been confirmed, but the present study reports more realistic geometrical parameters and modern standards of precision (e.g. ? for C-C bonds = 0.002-0.003?Å). Each mol-ecule features two intra-molecular N-H?O hydrogen bonds. In the crystal, mol-ecules are linked by strong face-to-face ?-? stacking inter-actions involving both the six- and five-membered rings [centroid-centroid separations = 3.6290?(14) and 3.6506?(14)?Å] and inter-molecular N-H?O hydrogen bonds.

SUBMITTER: Kettner F

PROVIDER: S-EPMC3247602 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Selective crystallization of indigo B by a modified sublimation method and its redetermined structure.

Kettner Florian F Hüter Lucie L Schäfer Johanna J Röder Konstantin K Purgahn Uta U Krautscheid Harald H

Acta crystallographica. Section E, Structure reports online 20111008 Pt 11

Good-quality single crystals of the title compound, indigo B [systematic name: 2-(3-oxoindolin-2-yl-idene)indolin-3-one], C(16)H(10)N(2)O(2), have been prepared with high selectivity by a sublimation process. The previous structure of indigo B [Süsse & Wolf (1980 ▶). Naturwissenschaften, 67, 453], which showed that the complete mol-ecule is generated by crystallographic inversion symmetry has been confirmed, but the present study reports more realistic geometrical parameters and modern standards ...[more]

PMID: 22219907

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