Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 7 (July 2013)

organic compounds

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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