Crystal structures of two hydrazinecarbothioamide derivatives: (E)-N-ethyl-2-[(4-oxo-4H-chromen-3-yl) methylidene]hydrazinecarbothioamide hemi-hydrate and (E)-2-[(4-chloro-2H-chromen-3-yl)-methylidene]-N-phenylhydrazinecarbothioamide

Abstract

The title compounds, C13H13N3O2S·0.5H2O, (I), and C17H14ClN3OS, (II), are hydrazinecarbothioamide derivatives. Compound (I) crystallizes with two independent molecules (A and B) and a water molecule of crystallization in the asymmetric unit. The chromene moiety is essentially planar in molecules A and B, with maximum deviations of 0.028 (3) and 0.016 (3) Å, respectively, for the carbonyl C atoms. In (II), the pyran ring of the chromene moiety adopts a screw-boat conformation and the phenyl ring is inclined by 61.18 (9)° to its mean plane. In the crystal of (I), bifurcated N - H⋯O and C - H⋯O hydrogen bonds link the two independent molecules forming A-B dimers with two R 12(6) ring motifs, and R 22(10) and R 22(14) ring motifs. In addition to these, the water molecule forms tetrafurcated hydrogen bonds which alternately generate R44(12) and R66(22) graph-set ring motifs. There are also π-π [inter-centroid distances = 3.5648 (14) and 3.6825 (15) Å] interactions present, leading to the formation of columns along the c-axis direction. In the crystal of (II), molecules are linked by pairs of N - H⋯S hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The dimers are linked by C - H⋯π interactions, forming ribbons lying parallel to (210).