2,6-Di-bromo-3,4,5-tri-meth-oxy-benzoic acid

Florian Meurer; Tanya Dimova; Michael Bodensteiner; Iliyan Kolev

doi:10.1107/S2056989023007831

2,6-Di-bromo-3,4,5-tri-meth-oxy-benzoic acid

Acta Crystallogr E Crystallogr Commun. 2023 Sep 14;79(Pt 10):916-919. doi: 10.1107/S2056989023007831. eCollection 2023 Oct 1.

Authors

Florian Meurer¹, Tanya Dimova², Michael Bodensteiner¹, Iliyan Kolev²

Affiliations

¹ Faculty of Chemistry and Pharmacy, University of Regensburg, Universitaetsstr. 31, 93053 Regensburg, Germany.
² Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Medical University "Prof. Dr. Paraskev Stoyanov" Varna, 84 "Tzar Osvoboditel" Blvd., 9000 Varna, Bulgaria.

Abstract

The title compound, 2,6-di-bromo-3,4,5-tri-meth-oxy-benzoic acid (DBrTMBA), C₁₀H₁₀Br₂O₅, was obtained by bromination and transhalogenation of 2-iodo-3,4,5-tri-meth-oxy-benzoic acid with KBrO₃. Like the previously reported 2,6-di-iodo-3,4,5-tri-meth-oxy-benzoic acid (DITMBA), the structure of the title compound features a catemeric arrangement of DBrTMBA mol-ecules along an endless chain of carb-oxy-lic H-carbonyl inter-actions. A short carbon-yl-phenyl contact hints at a possible lone pair(O)-π-hole inter-action further stabilizing the chain-like structure over a dimeric arrangement of the carb-oxy-lic acid.

Keywords: Hirshfeld atom refinement (HAR); NoSpherA2; crystal structure; substituted trimethoxybenzoic acid.

Grants and funding

Funding for this research was provided by the Institutional grant program of Medical University "Prof. Dr. Paraskev Stoyanov", Varna, "Nauka" (Project 20023).