Crystal structure, Hirshfeld surface and crystal void analysis, intermolecular interaction energies, DFT calculations and energy frameworks of 2H-benzo[b][1,4]thiazin-3(4H)-one 1,1-dioxide

In the title molecule, C8H7NO3S, the nitrogen atom has a planar environment, and the thiazine ring exhibits a screw-boat conformation. In the crystal, corrugated layers of molecules parallel to the ab plane are formed by N — H...O and C — H...O hydrogen bonds together with C — H... π (ring) and S=O... π (ring) interactions. The layers are connected by additional C — H...O hydrogen bonds and π -stacking interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...O/O...H (49.4%), H...H (23.0%) and H...C/C...H (14.1%) interactions. The volume of the crystal voids and the percentage of free space were calculated as 75.4   Å 3 and 9.3%. Density functional theory (DFT) computations revealed N — H...O and C — H...O hydrogen-bonding energies of 43.3, 34.7 and 34.4   kJ   mol − 1, respectively. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated via the electrostatic energy contribution. Moreover, the DFT-optimized structure at the B3LYP/ 6 – 311   G(d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO – LUMO behaviour was elucidated to determine the energy gap.
Source: Acta Crystallographica Section E - Category: Chemistry Authors: Tags: Crystal structure hydrogen bond — H... π (ring) interaction -stacking sulfone research communications Source Type: research