(6-Fluoro-2-oxo-2H-chromen-4-yl)methyl diethylcarbamodithioate

Abstract

The title compound, C15H16FNO2S2, crystallizes with two independent molecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the ethyl groups. The chromene rings are planar (r.m.s. deviations = 0.013 Å for both molecules), with the maximum deviation from the ring planes being 0.014 (2) and 0.018 (2) Å for atoms C9A and C9B, respectively. The mean plane of the chromene ring makes dihedral angles of 80.01 (7) and 76.97 (8)° with the carbamodithioate moiety [(N—C(=S)—S] of molecules A and B, respectively. In the crystal, the two molecules are linked by C—H...S hydrogen bonds, forming a ladder-like arrangement propagating along the a-axis direction. Within the ladders there are offset π–π interactions involving the coumarins rings of the B molecules [intercentroid distances vary from 3.705 (2) to 3.860 (1) Å]. Neighbouring ladders are linked via offset π–π interactions involving the coumarins rings of the A molecules [intercentroid distances vary from 3.539 (1) to 3.601 (1) Å]. These latter interactions lead to the formation of layers parallel to the ac plane.

Keywords

• crystal structure
• chromene derivatives
• carbamodithioate
• hydrogen bonding
• offset π–π interactions