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-yl­idene)indolin-3-one], C16H10N2O2, 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 mol­ecule 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 mol­ecule features two intra­molecular N—H⋯O hydrogen bonds. In the crystal, mol­ecules are linked by strong face-to-face π–π stacking inter­actions involving both the six- and five-membered rings [centroid–centroid separations = 3.6290 (14) and 3.6506 (14) Å] and inter­molecular N—H⋯O hydrogen bonds

The development of indigo reduction methods and pre-reduced indigo products

The continuing importance of blue denim maintains indigo as an important vat dye industrially. In this review, we examine the various methods that have been used in the past and are currently used to reduce and dissolve indigo for dyeing. We discuss recent insights into the bacterial fermentation technology, the advantages and disadvantages of the direct chemical methods that have predominated for the last century and potentially cleaner technologies of catalytic hydrogenation and electrochemistry, which are becoming increasingly important. With considerations of environmental impact high on the dyeing industry's agenda, we also discuss the developments that have led to the production of pre-reduced indigo