1-(5-Bromo-2-oxoindolin-3-yl-idene)-4-phenyl-thio-semicarbazide

Abstract

In the title compound, C15H11BrN4OS, the least-squares plane through the 5-bromo-isatin fragment forms a dihedral angle of 13.63 (14)° with the phenyl ring. The mol-ecular conformation features intra-molecular N-H⋯N and N-H⋯O hydrogen bonds. In the crystal, mol-ecules are connected via pairs of N-H⋯O inter-actions into centrosymmetric dimers. Additionally, π-π stacking inter-actions link mol-ecules into chains parallel to the a axis with short C⋯C distances being observed between the phenyl and thio-carbonyl [3.236 (8) Å] groups and between the thio-carbonyl and carbonyl [3.351 (4) Å] groups of stacked mol-ecules.

Fig. 1.

The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 40% probability level.

Fig. 2.

Molecules of the title compound connected through inversion centers via pairs of N—H···O interactions. Intramolecular N—H···N and N—H···O hydrogen bonds are also shown. H-interactions are indicated as dashed lines and the Figure is simplified for clarity. Symmetry code: (i)-x,-y + 1,-z + 3.

Fig. 3.

Crystal structure of the title compound in a view along the crystallographic c-axis. The π–π-interactions are drawn as dashed lines, highlighting C···C distances ranging from 3.236 (8) to 3.471 (7) Å. The molecular arrangment in layers, stacked into the direction of the crystallographic a-axis, is simplified for clarity.