Crystal and mol­ecular structure of 2-methyl-1,4-phenyl­ene bis­(3,5-di­bromo­benzoate)

Abstract

Mol­ecules of the aryl diester, 2-methyl-1,4-phenyl­ene bis­(3,5-di­bromo­benzoate), crystallized out from the melt (m.p. = 502 K/DSC). The crystal structure consists of a C—H⋯Br hydrogen-bonded network and weaker, offset π–π inter­actions.

The aryl diester compound, 2-methyl-1,4-phenyl­ene bis­(3,5-di­bromo­benzoate), C₂₁H₁₂Br₄O₄, was synthesized by esterification of methyl hydro­quinone with 3,5-di­bromo­benzoic acid. A crystalline sample was obtained by cooling a sample of the melt (m.p. = 502 K/DSC) to room temperature. The mol­ecular structure consists of a central benzene ring with anti-3,5-di­bromo­benzoate groups symmetrically attached at the 1 and 4 positions and a methyl group attached at the 2 position of the central ring. In the crystal structure (space group P

), mol­ecules of the title aryl diester are located on inversion centers imposing disorder of the methyl group and H atom across the central benzene ring. The crystal structure is consolidated by a network of C—H⋯Br hydrogen bonds in addition to weaker and offset π–π inter­actions involving the central benzene rings as well as the rings of the attached 3,5-di­bromo­benzoate groups.