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6-bromoindigo dye.

David J Szalda1, Keith Ramig, Olga Lavinda

  • 1Department of Natural Sciences, Baruch College, New York, NY 10010, USA. dszalda@baruch.cuny.edu

Acta Crystallographica. Section C, Crystal Structure Communications
|April 6, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of 6-Bromoindigo (MBI), revealing significant Br-atom disorder and shorter C-Br bonds compared to 6,6'-dibromoindigo (DBI). These findings impact understanding of indigo derivative packing and interactions.

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Area of Science:

  • Crystallography
  • Materials Science
  • Organic Chemistry

Background:

  • Indigo and its derivatives are important dyes with unique structural properties.
  • Understanding the crystal packing and intermolecular interactions of halogenated indigo compounds is crucial for materials science applications.

Purpose of the Study:

  • To elucidate the crystal structure of 6-Bromoindigo (MBI).
  • To investigate the impact of bromine atom disorder on MBI's structural parameters and intermolecular interactions.
  • To compare the structural features of MBI with those of 6,6 -dibromoindigo (DBI).

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure of MBI.
  • The crystal structure was refined considering Br-atom disorder and merohedral twinning.
  • Quantum mechanical calculations using density functional theory (DFT) and the quantum theory of atoms in molecules (QTAIM) were performed to analyze intermolecular interactions.

Main Results:

  • 6-Bromoindigo (MBI) crystallizes with significant Br-atom disorder (0.682:0.318 occupancy).
  • The disorder leads to shorter C-Br bond lengths in MBI compared to DBI.
  • Stacking interactions and hydrogen bonds in MBI are similar to indigo and DBI, with a notable C-Br...C interaction replacing C-Br...Br interactions found in DBI.
  • The indigo ring atoms exhibit slight displacements due to packing disorder.

Conclusions:

  • The crystal structure of 6-Bromoindigo (MBI) is characterized by significant Br-atom disorder, influencing its C-Br bond lengths.
  • Intermolecular interactions in MBI, including a C-Br...C contact, differ from those in DBI.
  • The study provides insights into the structural variations and packing behavior of halogenated indigo derivatives.