6-Bromoindigo dye

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2012-04, Vol.68 (4), p.o160-o163
• Main Authors: Szalda, David J., Ramig, Keith, Lavinda, Olga, Koren, Zvi C., Massa, Lou
• Format: Article
• Language: English
• Subjects: Asymmetry; Bonding; Coloring Agents - chemistry; Crystal structure; Crystallography; Density functional theory; Disorders; Hydrogen Bonding; Hydrogen bonds; Indigo; Indoles - chemistry; Mathematical models; Models, Molecular; Molecular Structure; Quantum theory; Stacking
• ISSN: 0108-2701; 1600-5759
• DOI: 10.1107/S0108270112006440

6‐Bromoindigo (MBI) [systematic name: 6‐bromo‐2‐(3‐oxo‐2,3‐dihydro‐1H‐indol‐2‐ylidene)‐2,3‐dihydro‐1H‐indol‐3‐one], C16H9BrN2O2, crystallizes with one disordered molecule in the asymmetric unit about a pseudo‐inversion center, as shown by the Br‐atom disorder of 0.682 (3):0.318 (3). The 18 indigo ring atoms occupy two sites which are displaced by 0.34 Å from each other as a result of this packing disorder. This difference in occupancy factors results in each atom in the reported model used to represent the two disordered sites being 0.08 Å from the higher‐occupancy site and 0.26 Å from the lower‐occupancy site. Thus, as a result of the disorder, the C—Br bond lengths in the disordered components are 0.08 and 0.26 Å shorter than those found in 6,6′‐dibromoindigo (DBI) [Süsse & Krampe (1979). Naturwissenschaften, 66, 110], although the distances within the indigo ring are similar to those found in DBI. The crystals are also twinned by merohedry. Stacking interactions and hydrogen bonds are similar to those found in the structures of indigo and DBI. In MBI, an interaction of the type C—Br...C replaces the C—Br...Br interactions found in DBI. The interactions in MBI were calculated quantum mechanically using density functional theory and the quantum theory of atoms in molecules.