Crystal structure of 3-(benzo[<i>d</i>]thiazol-2-yl)-6-methyl-2<i>H</i>-chromen-2-one

Abdallah, Amira E. M.; Elgemeie, Galal H.; Jones, Peter G.

doi:10.1107/s205698902300347x

Acta Cryst E

2023

DOI: 10.1107/s205698902300347x

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Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

Amira E. M. Abdallah

Galal H. Elgemeie

Peter G. Jones

Abstract: The molecule of the title compound, C17H11NO2S, is almost planar, with an interplanar angle of 3.01 (3)° between the benzothiazole and chromene ring systems. A short intramolecular S...O=C contact of 2.727 (2) Å is observed. The crystal packing involves a layer structure parallel to (211), containing dimeric inversion-symmetric units connected by a `weak' C—H...O=C hydrogen bond.

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“…Figure 3. X-ray single crystal structure of the compound 9d.Reproduced with permission of the International Union ofCrystallography under the open-access licence 25. …”

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Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations

2023

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This study revealed the design and preparation of new 3-(benzo[d]thiazol-2-yl)-2H-chromen-2-one derivatives 9a–h. The structures of the synthesized products were elucidated by their spectroscopic data and X-ray crystallography for compounds 9a and 9d. The prepared new compounds were measured for their fluorescence, and a good result indicated that the emission efficiency was decreased by increasing the electron-withdrawing groups from the unsubstituted compound 9a to the highly substituted derivative 9h (2 Br heavy atoms). On the other hand, the B3LYP/6-311G** theoretical level of theory was used to optimize the quantum mechanical calculations of the geometrical characteristics and energy of the novel compounds 9a–h under study. The electronic transition was investigated using the TD-DFT/PCM B3LYP approach, which uses time-dependent density functional calculations. Moreover, the compounds exhibited nonlinear optical properties (NLO) and a small HOMO–LUMO energy gap, which makes them easy to polarize. Furthermore, the acquired infrared spectra were compared with the expected harmonic vibrations of the substances 9a–h. On the other hand, binding energy analyses of compounds 9a–h with human corona virus nucleocapsid protein Nl63 (PDB ID: 5epw) were predicted using molecular docking and virtual screening tools. The results showed a promising binding and how these potent compounds were inhibiting the COVID-19 virus. Compound 9h was the most active anti-COVID-19 agent among all the synthesized benzothiazolyl-coumarin derivatives, as it forms five bonds. The presence of the two bromine atoms in its structure was responsible for the potent activity.

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“…Figure 3. X-ray single crystal structure of the compound 9d.Reproduced with permission of the International Union ofCrystallography under the open-access licence 25. …”

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confidence: 99%

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations

2023

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Crystal structure of 2-{[5-(methylsulfanyl)-4-phenyl-4H-1,2,4-triazol-3-yl]methyl}benzo[d]thiazole

Azzam,

Elgemeie,

Elboshi

et al. 2023

Acta Crystallogr E Cryst Commun

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In the structure of the title compound, C17H14N4O2, the triazole ring exhibits interplanar angles of 63.86 (2) and 76.96 (2)° with the phenyl and benzothiazole planes, respectively. The C—C—C angle at the methylene group is rather wide at 114.28 (4)°. The packing involves three borderline C—H...N contacts, two of which combine to form layers parallel to ac, and a pairing of the triazole rings across an inversion centre [interplanar distance of 3.1852 (2) Å].

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Crystal structure of 3-(benzo[d]thiazol-2-yl)-6-methyl-2H-chromen-2-one

Cited by 2 publications

References 26 publications

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations

Novel Fluorescent Benzothiazolyl-Coumarin Hybrids as Anti-SARS-COVID-2 Agents Supported by Molecular Docking Studies: Design, Synthesis, X-ray Crystal Structures, DFT, and TD-DFT/PCM Calculations

Crystal structure of 2-{[5-(methylsulfanyl)-4-phenyl-4H-1,2,4-triazol-3-yl]methyl}benzo[d]thiazole

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