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

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. σ 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 π-π 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.