Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one
The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C=C and carbonyl C=O double bonds in the enone unit. The molecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, molecules...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-05-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019005243 |
| _version_ | 1818492711291846656 |
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| author | Muhamad Fikri Zaini Ibrahim Abdul Razak Wan Mohd Khairul Suhana Arshad |
| author_facet | Muhamad Fikri Zaini Ibrahim Abdul Razak Wan Mohd Khairul Suhana Arshad |
| author_sort | Muhamad Fikri Zaini |
| collection | DOAJ |
| description | The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C=C and carbonyl C=O double bonds in the enone unit. The molecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, molecules are linked into inversion dimers with an R22(10) graph-set motif via pairs of C—H...O hydrogen bonds. The intermolecular interactions were analysed and quantified by Hirshfeld surface analysis. The molecular structure was optimized and a small HOMO–LUMO energy gap of 2.55 eV was obtained using the DFT method at the B3LYP/6–311 G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52 eV obtained from the UV–vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996 (16):0.8004 (16). |
| first_indexed | 2024-12-10T17:46:32Z |
| format | Article |
| id | doaj.art-3eda9e52b3a54d8ab7a690693ad914de |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-10T17:46:32Z |
| publishDate | 2019-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-3eda9e52b3a54d8ab7a690693ad914de2022-12-22T01:39:12ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-05-0175568568910.1107/S2056989019005243is5513Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-oneMuhamad Fikri Zaini0Ibrahim Abdul Razak1Wan Mohd Khairul2Suhana 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, MalaysiaSchool of Fundamental Science, Universiti Malaysia Terengganu, 21030, Kuala Terengganu, Terengganu, MalaysiaX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, MalaysiaThe title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C=C and carbonyl C=O double bonds in the enone unit. The molecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, molecules are linked into inversion dimers with an R22(10) graph-set motif via pairs of C—H...O hydrogen bonds. The intermolecular interactions were analysed and quantified by Hirshfeld surface analysis. The molecular structure was optimized and a small HOMO–LUMO energy gap of 2.55 eV was obtained using the DFT method at the B3LYP/6–311 G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52 eV obtained from the UV–vis analysis. The crystal used was a two-component merohedral twin with a refined ratio of 0.1996 (16):0.8004 (16).http://scripts.iucr.org/cgi-bin/paper?S2056989019005243chalconecrystal structureDFTHirshfeld surfaceUV–VisHOMO–LUMO |
| spellingShingle | Muhamad Fikri Zaini Ibrahim Abdul Razak Wan Mohd Khairul Suhana Arshad Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one Acta Crystallographica Section E: Crystallographic Communications chalcone crystal structure DFT Hirshfeld surface UV–Vis HOMO–LUMO |
| title | Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one |
| title_full | Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one |
| title_fullStr | Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one |
| title_full_unstemmed | Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one |
| title_short | Crystal structure and optical properties of fused-ring chalcone (E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one |
| title_sort | crystal structure and optical properties of fused ring chalcone e 3 anthracen 9 yl 1 4 nitrophenyl prop 2 en 1 one |
| topic | chalcone crystal structure DFT Hirshfeld surface UV–Vis HOMO–LUMO |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019005243 |
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