Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 2 (February 2013)


organic compounds



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


cmldisplay filedownload file

Chemical Markup Language (CML) file (4.6 kbytes)
[ doi:10.1107/S0108270112050822/ln3154Isup4.cml ]
Supplementary material


cmldisplay filedownload file

Chemical Markup Language (CML) file (4.6 kbytes)
[ doi:10.1107/S0108270112050822/ln3154IIsup5.cml ]
Supplementary material


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