Abstract
The title compound, C17H17N3O, crystallizes with two independent mol-ecules in the asymmetric unit. The semicarbazone moieties of these independent mol-ecules (I and II) are essentially planar [maximum deviation of 0.042 (1) Å in mol-ecule I and 0.041 (1) Å in mol-ecule II], with the terminal phenyl rings twisted away from the mean plane of the semicarbazone moiety, making dihedral angles of 60.26 (8) and 28.76 (9)° in mol-ecule I and 31.07 (9) and 35.45 (8)° in mol-ecule II. The mol-ecules both exhibit an E configuration with respect to the C=C and azomethine C=N bonds. In the crystal, two classical N-H⋯O hydrogen-bonding inter-actions are present between the two mol-ecules, forming a centrosymmetric dimer, while a weak C-H⋯O non-classical hydrogen-bonding inter-action, with a donor-acceptor distance of 3.476 (2) Å, inter-connects two neighbouring centrosymmetric dimers to form a cage-like structure. These cage structures are inter-connected by weak C-H⋯π inter-actions with an H⋯π distance of 2.790 Å, forming supra-molecular chains along the c-axis direction.
Highlights
N5—H50Á Á ÁO1 N2—H20Á Á ÁO2 N3—H30Á Á ÁN1 N6—H60Á Á ÁN4 C13—H13Á Á ÁO2i C32—H32Á Á ÁCg1ii
Semicarbazones are oxygen and nitrogen contributor ligands whose significance lies in their versatility of molecular sequence, which allows diverse geometries to be obtained
The title compound crystallizes in the triclinic space group P1 symmetry with two independent molecules, I and II, in the asymmetric unit (Fig. 1)
Summary
Semicarbazones are oxygen and nitrogen contributor ligands whose significance lies in their versatility of molecular sequence, which allows diverse geometries to be obtained. Semicarbazones exhibit amido–iminol tautomerism in solution due to the interaction of solvent molecules, but generally exist in the amido form in the solid state. Semicarbazones can function as brilliant ligands in a variety of metal ions (Kala et al, 2007) and co-ordinate to metal ions either in neutral (Siji et al, 2011) or in anionic forms (Reena et al, 2008). Structural studies of many semicarbazones and N4-phenylsemicarbazones have been reported and some of them adopt an E configuration with respect to the azomethine double bond along with both inter- and intramolecular hydrogen-bonding interactions (Reena et al, 2010; Layana et al, 2014, 2018). Symmetry codes: (i) Àx þ 1; Ày; Àz þ 1; (ii) Àx þ 1; Ày; Àz þ 2
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