Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one
The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent molecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related molecules are linked into dimers via intermolecular hydrogen bonds...
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doaj-d3b4f8bd6460472bb2c6153b3fd53d272020-11-24T21:18:44ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-01-01751586310.1107/S2056989018017371rz5249Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-oneMuhamad Fikri Zaini0Ibrahim Abdul Razak1Mohamad Zahid Anis2Suhana Arshad3X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, MalaysiaX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, MalaysiaX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, MalaysiaX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, MalaysiaThe asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent molecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related molecules are linked into dimers via intermolecular hydrogen bonds, forming rings with R12(6), R22(10) and R22(14) graph-set motifs. The dimers are further connected by C—H...O interactions into chains parallel to [001]. A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by H...H contacts (26.3%). Calculations performed on the optimized structure obtained using density functional theory (DFT) at B3LYP with the 6–311 G++(d,p) basis set reveal that the HOMO–LUMO energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications. The nucleophilic and electrophilic binding site regions are elucidated using the molecular electrostatic potential (MEP).http://scripts.iucr.org/cgi-bin/paper?S2056989018017371halogen chalconecrystal structureDFTHirshfeld surfaceUV–visHOMO–LUMOmolecular electrostatic potential |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Muhamad Fikri Zaini Ibrahim Abdul Razak Mohamad Zahid Anis Suhana Arshad |
spellingShingle |
Muhamad Fikri Zaini Ibrahim Abdul Razak Mohamad Zahid Anis Suhana Arshad Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one Acta Crystallographica Section E: Crystallographic Communications halogen chalcone crystal structure DFT Hirshfeld surface UV–vis HOMO–LUMO molecular electrostatic potential |
author_facet |
Muhamad Fikri Zaini Ibrahim Abdul Razak Mohamad Zahid Anis Suhana Arshad |
author_sort |
Muhamad Fikri Zaini |
title |
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one |
title_short |
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one |
title_full |
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one |
title_fullStr |
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one |
title_full_unstemmed |
Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one |
title_sort |
crystal structure, hirshfeld surface analysis and dft studies of (e)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2019-01-01 |
description |
The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent molecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related molecules are linked into dimers via intermolecular hydrogen bonds, forming rings with R12(6), R22(10) and R22(14) graph-set motifs. The dimers are further connected by C—H...O interactions into chains parallel to [001]. A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by H...H contacts (26.3%). Calculations performed on the optimized structure obtained using density functional theory (DFT) at B3LYP with the 6–311 G++(d,p) basis set reveal that the HOMO–LUMO energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications. The nucleophilic and electrophilic binding site regions are elucidated using the molecular electrostatic potential (MEP). |
topic |
halogen chalcone crystal structure DFT Hirshfeld surface UV–vis HOMO–LUMO molecular electrostatic potential |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989018017371 |
work_keys_str_mv |
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