Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 2 (February 2013)


organic compounds



ln3154 scheme

Acta Cryst. (2013). C69, 150-155    [ doi:10.1107/S0108270112050822 ]

Contrasting the supramolecular structures in the isomeric pair 5-bromo-3-nitrosalicylaldehyde phenylhydrazone and 3-bromo-5-nitrosalicylaldehyde phenylhydrazone

L. R. Gomes, J. N. Low and J. L. Wardell

Abstract: Isomeric 5-bromo-3-nitrosalicylaldehyde phenylhydrazone and 3-bromo-5-nitrosalicylaldehyde phenylhydrazone, C13H10BrN3O3, both crystallize with two molecules in the asymmetric unit. In both isomers, an intramolecular O-H...N hydrogen bond links the hydroxy group and the imine N atom. In the 5-bromo-3-nitro isomer, there are two independent N-H...O hydrogen-bonded chains, each molecule in the asymmetric unit forming its own chain. These chains are then linked to form a three-dimensional framework by a combination of weak C-H...O, C-H...Br, C-H...[pi] and [pi]-[pi] stacking interactions. In the 3-bromo-5-nitro isomer, N-H...O hydrogen bonds link the independent molecules alternately into a zigzag chain, which is reinforced by a weak C-H...O interaction. Individual chains are linked by a C-H...Br interaction and a three-dimensional framework is generated by [pi]-[pi] stacking interactions.

Formula: Two isomers of C13H10BrN3O3


hkldisplay filedownload file

Structure factor file (CIF format) (295.5 kbytes)
[ doi:10.1107/S0108270112050822/ln3154Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (287.1 kbytes)
[ doi:10.1107/S0108270112050822/ln3154IIsup3.hkl ]
Contains datablock II


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