Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid

Abstract

The title cyclobutyl compound, C18H18N2O3S, was synthesized by the interaction of 4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine and maleic anhydride, and crystallizes in the orthorhombic space group P212121 with Z′ = 1. The molecular geometry is partially stabilized by an intramolecular N—H...O hydrogen bond forming an S 1 1(7) ring motif. The molecule is non-planar with a dihedral angle of 88.29 (11)° between the thiazole and benzene rings. In the crystal, the molecules are linked by O—H...N hydrogen bonds, forming supramolecular ribbons with C 1 1(9) chain motifs. To further analyze the intermolecular interactions, a Hirshfeld surface analysis was performed. The results indicate that the most important contributions to the overall surface are from H...H (43%), C...H (18%), O...H (17%) and N...H (6%), interactions.

Synthesis, crystal structure, DFT calculation and Hirshfeld surface analysis of N-(4-methyl phenyl)-2-(3-nitro-benzamido) benzamide

“…However, the bond lengths for the carbonyl groups, C7=O3 and C14=O4 were determined as 1.236 (4) and 1.236 (4) respectively. These C=O bond lengths are comparable to the values of 1.230 (4) and 1.2257 (17) Å previously reported by Simsek et al [19] and Mague [20]. In a work by Yu and Fu [21], N3=O8 [1.201 ( 7) Å] and N3=O9 [1.215 (6) Å] bond lengths are quite close to N3=O3 [1.219 ( 5) Å] and N3=O4 [1.218 (4) Å] bond distances in the title compound.…”