Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 7 (July 2013)

organic compounds

ov3030 scheme

Acta Cryst. (2013). C69, 790-793    [ doi:10.1107/S0108270113015229 ]

Br...O contacts and [pi]-[pi] stacking dominate the packing in methyl 4-bromo-3,5-dimethoxybenzoate

A. Saeed, M. Qasim and J. Simpson

Abstract: The title compound, C10H11BrO4, a useful precursor to pharmaceutically active isocoumarin and isochroman derivatives, crystallizes with two unique molecules in the asymmetric unit. A [pi]-[pi] stacking interaction links the planar molecules in the asymmetric unit. Additional [pi]-[pi] contacts stack pairs of molecules along the c axis. A feature of the crystal packing is the presence of a number of short Br...O contacts. A particularly unusual arrangement involves the formation of dimers, with pairs of Br...O contacts imposing a close Br...Br interaction and generating five-membered rings within an eight-membered ring formed by two Br...O contacts. Only two comparable arrangements have been reported previously. The Br...O contacts combine with weak C-H...O hydrogen bonds to form corrugated sheets of molecules approximately parallel to (001). These sheets are stacked along the c axis by [pi]-[pi] interactions to generate a three-dimensional network.

Formula: C10H11BrO4

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[ doi:10.1107/S0108270113015229/ov3030Isup3.cml ]
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