Crystal structure of 2-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-N-phenylhydrazinecarboxamide

Abstract

The title compound, C17H17N3O, crystallizes with two independent molecules in the asymmetric unit. The semicarbazone moieties of these independent molecules (I and II) are essentially planar [maximum deviation of 0.042 (1) Å in molecule I and 0.041 (1) Å in molecule 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 molecule I and 31.07 (9) and 35.45 (8)° in molecule II. The molecules 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 interactions are present between the two molecules, forming a centrosymmetric dimer, while a weak C—H...O non-classical hydrogen-bonding interaction, with a donor–acceptor distance of 3.476 (2) Å, interconnects two neighbouring centrosymmetric dimers to form a cage-like structure. These cage structures are interconnected by weak C—H...π interactions with an H...π distance of 2.790 Å, forming supramolecular chains along the c-axis direction.

Keywords

• crystal structure
• semicarbazone
• phenylhydrazinecarboxamide