Two thiosemicarbazones derived from salicylaldehyde: very specific hydrogen‐bonding interactions of the N—H...S=C type |
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Authors: | Mirta Rubč ić ,Ivica ?ilović ,Marina Cindrić ,Dubravka Matković ‐Č alogović |
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Abstract: | The molecular structures of two salicylaldehyde thiosemicarbazone derivatives, namely salicylaldehyde 4‐phenylthiosemicarbazone, C14H13N3OS, (I), and 4‐methoxysalicylaldehyde 4‐phenylthiosemicarbazone, C15H15N3O2S, (II), both of potential pharmacological interest, are found in the keto (thione) tautomeric form. The first compound represents a second triclinic polymorph of composition β‐C14H13N3OS. Although both polymorphs crystallize in the same space group (P), the α‐polymorph [Seena, Kurup & Suresh (2008). J. Chem. Crystallogr. 38 , 93–96] differs from the β form in its unit‐cell volume at 293 K. The molecules in the crystal structures of (I) and (II) are linked into centrosymmetric R22(8) dimers by hydrogen bonds of the N—H...S=C type. These dimers are connected through π–π stacking and T‐shaped C—H...π interactions into three‐dimensional networks. |
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