Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy
The functionalization of N-(benzo[d]thiazol-2-yl)benzamide with a nitro (NO2) substituent influences the solid-state arrangement, absorption and fluorescence properties of these compounds. Each of these compounds crystallised in a different crystal system or space group, namely a monoclinic crystal...
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| Format: | Article |
| Language: | English |
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MDPI
2020
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| Online Access: | http://psasir.upm.edu.my/id/eprint/78018/ http://psasir.upm.edu.my/id/eprint/78018/1/78018.pdf |
| _version_ | 1848858390194814976 |
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| author | Abdul Latiff, Aqilah Chong, Yan Yi Lee, Mark Wun Fui Kassim, Mohammad |
| author_facet | Abdul Latiff, Aqilah Chong, Yan Yi Lee, Mark Wun Fui Kassim, Mohammad |
| author_sort | Abdul Latiff, Aqilah |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | The functionalization of N-(benzo[d]thiazol-2-yl)benzamide with a nitro (NO2) substituent influences the solid-state arrangement, absorption and fluorescence properties of these compounds. Each of these compounds crystallised in a different crystal system or space group, namely a monoclinic crystal system with P21/n and C2/c space groups for o-NO2 and m-NO2 derivatives, respectively, and an orthorhombic crystal system (Pbcn space group) for p-NO2 derivative. The o-NO2 substituent with intrinsic steric hindrance engendered a distorted geometry. Conversely, the m-NO2 derivate displayed the most planar geometry among the analogues. The solid-state architectures of these compounds were dominated by the N−H···N and C−H···O intermolecular hydrogen bonds and were further stabilised by other weak interactions. The dimer synthons of the compounds were established via a pair of N−H···N hydrogen bonds. These findings were corroborated by a Hirshfeld surface analysis and two-dimensional (2D) fingerprint plot. The interaction energies within the crystal packing were calculated (CE-B3LYP/6-31G(d,p)) and the energy frameworks were modelled by CrystalExplorer17.5. The highly distorted o-NO2 congener synthon relied mainly on the dispersion forces, which included π–π interactions compared to the electrostatic attractions found in m-NO2. Besides, the latter possesses an elevated asphericity character, portraying a marked directionality in the crystal array. The electrostatic and dispersion forces were regarded as the dominant factors in stabilising the crystal packing. |
| first_indexed | 2025-11-15T12:12:41Z |
| format | Article |
| id | upm-78018 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T12:12:41Z |
| publishDate | 2020 |
| publisher | MDPI |
| recordtype | eprints |
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| spelling | upm-780182020-06-02T03:06:22Z http://psasir.upm.edu.my/id/eprint/78018/ Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy Abdul Latiff, Aqilah Chong, Yan Yi Lee, Mark Wun Fui Kassim, Mohammad The functionalization of N-(benzo[d]thiazol-2-yl)benzamide with a nitro (NO2) substituent influences the solid-state arrangement, absorption and fluorescence properties of these compounds. Each of these compounds crystallised in a different crystal system or space group, namely a monoclinic crystal system with P21/n and C2/c space groups for o-NO2 and m-NO2 derivatives, respectively, and an orthorhombic crystal system (Pbcn space group) for p-NO2 derivative. The o-NO2 substituent with intrinsic steric hindrance engendered a distorted geometry. Conversely, the m-NO2 derivate displayed the most planar geometry among the analogues. The solid-state architectures of these compounds were dominated by the N−H···N and C−H···O intermolecular hydrogen bonds and were further stabilised by other weak interactions. The dimer synthons of the compounds were established via a pair of N−H···N hydrogen bonds. These findings were corroborated by a Hirshfeld surface analysis and two-dimensional (2D) fingerprint plot. The interaction energies within the crystal packing were calculated (CE-B3LYP/6-31G(d,p)) and the energy frameworks were modelled by CrystalExplorer17.5. The highly distorted o-NO2 congener synthon relied mainly on the dispersion forces, which included π–π interactions compared to the electrostatic attractions found in m-NO2. Besides, the latter possesses an elevated asphericity character, portraying a marked directionality in the crystal array. The electrostatic and dispersion forces were regarded as the dominant factors in stabilising the crystal packing. MDPI 2020 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/78018/1/78018.pdf Abdul Latiff, Aqilah and Chong, Yan Yi and Lee, Mark Wun Fui and Kassim, Mohammad (2020) Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy. Crystals, 10 (5). art. no. 348. pp. 1-14. ISSN 2073-4352 https://www.mdpi.com/2073-4352/10/5/348 10.3390/cryst10050348 |
| spellingShingle | Abdul Latiff, Aqilah Chong, Yan Yi Lee, Mark Wun Fui Kassim, Mohammad Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy |
| title | Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy |
| title_full | Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy |
| title_fullStr | Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy |
| title_full_unstemmed | Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy |
| title_short | Insight into positional isomerism of N-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, Hirshfeld surface analysis and interaction energy |
| title_sort | insight into positional isomerism of n-(benzo[d]thiazol-2-yl)-o/m/p-nitrobenzamide: crystal structure, hirshfeld surface analysis and interaction energy |
| url | http://psasir.upm.edu.my/id/eprint/78018/ http://psasir.upm.edu.my/id/eprint/78018/ http://psasir.upm.edu.my/id/eprint/78018/ http://psasir.upm.edu.my/id/eprint/78018/1/78018.pdf |