Crystal analysis by Clifford George, Jacqueline Ruiz Ferrer, Paul M. Lahti.
Magnetic Analysis by Fernando Palacio, Patricia Oliete, and Michel Julier.

This molecule was synthesized first by Jacqueline Ruiz, and reported in Jacqueline R. Ferrer, Paul M. Lahti, Clifford George, Patricia Oliete, Michel Julier, Fernando Palacio, Chem. Mater., 13(7), 2447-2454 (2001). It is structurally similar to 2-(N-tert-butylaminoxylphenyl)-benzimidazole (see  Jacqueline R. Ferrer, Paul M. Lahti, Clifford George, Guillermo Antorrena, Fernando Palacio, Chem. Mater., 11, 2205-2210 (1999)), also made by Jacqui.  The crystal packing of the two molecules is very different, however.  Whereas 2-(N-tert-butylaminoxylphenyl)-benzimidazole packs in a bilayer motif with NH - - -N hydrogen bonding, this molecule forms hydrogen bonded dimers via NO - - - HN interactions.

This molecule exhibits antiferromagnetic exchange coupling to give net spin pairing with J/k = -22 K.  Spin parity analysis shows that the main pathway of exchange must be direct spin pairing across the proximate NO sites, whereas any close-contact exchange through the NO - - - HN hydrogen bonds must have a negligible effect on the overall magnetic behavior.  In this case, the hydrogen bonds are solely scaffolding, not electronic pathways for exchange.

Tested on a Windows-based Pentium PC using Netscape version 4.7 with the Chime 2.6 (service pack 3) plugin installed.

Tested on a Windows-based Pentium PC using Internet Explorer version 6 with the Chime 2.6 (service pack 3) plugin installed.