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Note | Special issue | Vol 47, No. 2, 1998, pp.1033-1042
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)94
Iron Chelators of the Class of Pyridoxal Acylhydrazone. Part 5. Crystal Structure and Patterns of Hydrogen Bonding in Pyridoxal Isonicotinoyl Hydrazone (PIH)

Shalom Sarel,* Shmuel Cohen, and Shelly Avramovici-Grisaru

*Department of Pharmaceutical Chemistry, Hebrew University School of Pharmacy, P. O. Box 12065, Jerusalem 91120, Israel


The water-free Pyridoxal Isonicotinoyl Hydrazone {PIH} C14H14N4O3 (mp 268°C) was synthesized, and its crystal structure determined from three-dimensional X-Ray data. The chelator crystallizes in the space group P21/n with Z = 4 and cell dimensions : a =13.072(6) Å, b =13.06(5) Å, c = 8.186(2) Å, b =90.2I°(2). The data produced here confirms that PIH crystallizes in the non-dipolar form, assembled as, 3-D tetramer, composed of a planar 16-membered ring dimer, involving intermolecular H-bondings between the acoholic hydroxyl-oxygen(O2) and the azinic (N3-H) hydrogen. The dimeric macrocycle is attached to two PIH molecules in a perpendicular fashion, and in opposite orientations, to form a 3-D tetramer, by involving intermolecular H-contacts between the alcoholic hydroxyl-H and the pyridinic ring-nitrogen (N4). The azinic-nitrogen (N2) is intramolecularly H-bonded with the phenolic H {O1-H }, to form a stable six-membered ring system.