Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(4-fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

Acta Crystallographica Section E: Crystallographic Communications

卷:75

Joel T. Mague¹  Tuncer Hökelek²  Younes Ouzidan³  Brahim Hni⁴  Nada Kheira Sebbar⁴  El Mokhtar Essassi⁴  Ahmed Moussaif⁵ 

[1] Department of Chemistry, Tulane University, New Orleans, LA 70118, USA;

[2] Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;

[3] Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'immouzzer, BP 2202, Fez, Morocco;

[4] Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco;

[5] National Center of Energy Sciences and Nuclear Techniques, Rabat, Morocco;

关键词: crystal structure;    dihydrobenzothiazine;    hydrogen bond;    DFT;    Hirshfeld surface;   

DOI  :  10.1107/S2056989019002354

来源: DOAJ

【 摘 要 】

The title compound, C18H12FNOS, is built up from a 4-fluorobenzylidene moiety and a dihydrobenzothiazine unit with a propynyl substituent, with the heterocyclic portion of the dihydrobenzothiazine unit adopting a shallow boat conformation with the propynyl substituent nearly perpendicular to it. The two benzene rings are oriented at a dihedral angle of 43.02 (6)°. In the crystal, C—HFlurphen...FFlurphen (Flurphen = fluorophenyl) hydrogen bonds link the molecules into inversion dimers, enclosing R22(8) ring motifs, with the dimers forming oblique stacks along the a-axis direction. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (33.9%), H...C/C...H (26.7%), H...F/F...H (10.9%) and C...C (10.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

【 授权许可】

Unknown