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Updated: Sep 1, 2025
Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Crystal structure, Hirshfeld surface analysis and DFT calculations of
Imane Faraj1, Ali Oubella2,3, Karim Chkirate1
1Laboratory of Heterocyclic Organic Chemistry, Medicines Science Research Center, Pharmacochemistry Competence Center, Mohammed V University in Rabat, Faculté des Sciences, Av. Ibn Battouta, BP 1014, Rabat, Morocco.
Abstract:
The asymmetric unit of the title compound, C14H13NO4, contains three independent mol-ecules, which differ slightly in conformation. Each contains an intra-molecular N-H⋯O hydrogen bond. In the crystal, O-H⋯O hydrogen bonds form chains of mol-ecules, which are linked into corrugated sheets parallel to (03) plane by C-H⋯O hydrogen bonds together with π inter-actions between the carbonyl groups and the 2-hy-droxy-phenyl rings. The layers are linked by further C-H⋯O hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (49.0%), H⋯O/O⋯H (28.3%) and H⋯C/C⋯H (10.9%) inter-actions. van der Waals inter-actions are the dominant inter-actions in the crystal packing. Moreover, density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behavior was elucidated to determine the energy gap of 4.53 eV.
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