Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis

Abstract

The structure of 1-(2-oxo-2H-chromene-3-carbonyl)-3-(2-methoxy-phenyl)thiourea (1) has been determined by single-crystal X-ray crystallography. This compound crystallizes in the monoclinic space group P21/c with a = 7.455 (2) Å, b = 12.744 (3) Å, c = 16.892 (4) Å, β = 90.203 (6)° and Z = 4. Both, the coumarin and the phenyl rings are nearly coplanar with the central 1-acylthiourea group, with the CO and CS bonds adopting an opposite orientation. Intramolecular N–H···O, C–H···O, and C–H···S hydrogen bonds are favored by the planar conformation. The molecules are packed through C–H···O, C–H···S and C–H···C hydrogen bonds, and two π···π interactions with offset arrangement. Inter-centroid distance of 3.490 (2) Å, slip angles of 18.5 and 20.9°, and vertical displacements of 1.10 and 1.24 Å are the stacking parameters corresponding to the stronger π···π interaction. Hirshfeld surface analysis was performed for visualizing, exploring and quantifying intermolecular interactions in the crystal lattice of compound 1, and compared with two closely related species. Shape index and Curvedness surfaces indicated π-stacking with different features in opposed sides of the molecule. Fingerprint plot showed C···C contacts with similar contributions to the crystal packing in comparison with those associated to hydrogen bonds. Enrichment ratios for H···H, O···H, S···H and C···C contacts revealed a high propensity to form in the crystal.