Synthesis, crystal structure, hydrogen bonding interactions analysis of novel acyl thiourea derivative

The N‐(p‐methoxybenzoyl)‐N′‐(2,4‐dinitrophenyl amino)thiourea has been synthesized and characterized by FT‐IR, 1H NMR, and elemental analyses techniques. Also, its molecular structure was determined by single‐crystal X‐ray diffraction. It revealed that the title compound crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell, space group Pna2(1) with a = 18.857(5) Å, b = 8.148(2) Å, c = 22.443(6) Å, β = 90.00°, C15H13N5O6S, Mr = 391.36, V = 3448.2(15) Å3, Z = 8, Dc = 1.508 g·cm−1, F(000) = 1616, μ = 0.233 mm−1, S = 1.06, the final R = 0.0626, and wR (I > 2ϭ(I)) = 0.1392. Intramolecular NH … N, CH … N, and NH … O hydrogen bonds indicate that the molecule conformation was mostly planar. Crystal structure stacking through the NH … O, CH … O, and NH … S hydrogen bonds, and two π … π interactions arrangement revealed their conspicuous role in the stabilization of the molecular structure. The type and nature of intermolecular interactions in the crystal structure were investigated by Hirshfeld surfaces and their associated two‐dimensional fingerprint plots. Furthermore, shape index and curvedness surfaces further confirmed π … π stacking interactions with different features of molecule A and B. More importantly, the reduced density gradient (RDG) function provides a real‐space function for discussing noncovalent interactions (NCI) in title compound, including van der Waals interactions and CH … π contacts in addition to hydrogen bonding interactions within molecule.