(Z)-2-(2-Chlorobenzylidene)-4-(prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one

Sebbar, Nada Kheira; Ellouz, Mohamed; Ouzidan, Y.; Kaur, Manpreet; Essassi, El Mokhtar; Jasinski, Jerry P.

doi:10.1107/s2414314617008896

IUCr Data

2017

DOI: 10.1107/s2414314617008896

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(Z)-2-(2-Chlorobenzylidene)-4-(prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one

Nada Kheira Sebbar¹,

Mohamed Ellouz²,

Y. Ouzidan

et al.

Abstract: In the title compound, C18H12ClNOS, the thiazine-3-one ring of the 1,4-thiazin-3-one moiety adopts a slightly distorted twist-boat conformation. The dihedral angle between the benzene rings is 86.2 (1)°. In the crystal, the crystal packing features a single weak C—H...O interaction and weak π–π stacking interactions.

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2019

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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

Hni¹,

Sebbar²,

Hökelek

et al. 2019

Acta Cryst E

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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 R 2 2(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.

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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

Hni¹,

Sebbar²,

Hökelek

et al. 2019

Acta Cryst E

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(Z)-2-(2-Chlorobenzylidene)-4-(prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one

Cited by 1 publication

References 11 publications

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

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

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