Two thiosemicarbazones derived from salicylaldehyde: very specific hydrogen-bonding interactions of the N-H...S=C type.
The molecular structures of two salicylaldehyde thiosemicarbazone derivatives, namely salicylaldehyde 4-phenylthiosemicarbazone, C(14)H(13)N(3)OS, (I), and 4-methoxysalicylaldehyde 4-phenylthiosemicarbazone, C(15)H(15)N(3)O(2)S, (II), both of potential pharmacological interest, are found in the keto (thione) tautomeric form. The first compound represents a second triclinic polymorph of composition beta-C(14)H(13)N(3)OS. Although both polymorphs crystallize in the same space group (P1), the alpha-polymorph [Seena, Kurup & Suresh (2008). J. Chem. Crystallogr. 38, 93-96] differs from the beta form in its unit-cell volume at 293 K. The molecules in the crystal structures of (I) and (II) are linked into centrosymmetric R(2)(2)(8) dimers by hydrogen bonds of the N-H...S=C type. These dimers are connected through pi-pi stacking and T-shaped C-H...pi interactions into three-dimensional networks.
Laboratory of General and Inorganic Chemistry, Department of Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia.
Mirta
M
Rubcić
Ivica
I
Dilović
Marina
M
Cindrić
Dubravka
D
Matković-Calogović
D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D003460:Crystallization; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry; D006860:Hydrogen Bonding; D009584:Nitrogen / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry*
C533318:4-methoxysalicylaldehyde 4-phenylthiosemicarbazone; D000447:Aldehydes; D013882:Thiosemicarbazones; C062542:salicylaldehyde thiosemicarbazone; D002244:Carbon; D006859:Hydrogen; D009584:Nitrogen