Intermolecular Interactions in Crystalline 1-(Adamantane-1-carbonyl)-3-subsituted Thioureas with Hirshfeld Surface Analysis

SAEED, AAMER; BOLTE, MICHAEL; ERBEN, MAURICIO FEDERICO; PÉREZ, HIRAM

CRYSTENGCOMM

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2015 vol. 17 p. 7551 - 7563

1466-8033

The conformational congested species 1-(adamantane-1-carbonyl)-3-(2,4,6-trimethylphenyl)thiourea has been prepared, fully characterized by elemental analyses, FTIR, 1H, 13C NMR and mass spectroscopy, and the crystal structure determined by using single crystal X-ray diffraction study. The dihedral angle between the plane of 2,4,6-tri-methylphenyl group and the plane of thiourea fragment was optimized by theoretical calculations applying the B3LYP/6-31++G(d,p) level, for the purpose to investigate conformational effects on the stabilization of crystal packing. A detailed analysis of the intermolecular interactions in a series of six closely related phenylthiourea species bearing the 1-(adamantane-1-carbonyl) group have been performed based on the Hirshfeld surfaces and their associated two-dimensional fingerprint plots. The relative contributions of the main intercontacts, as well as the enrichment ratios derived from the Hirshfeld surface analysis establishes the 1-acyl thiourea synton to be a widespread contributor.