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Open AccessArticle

Insight into Positional Isomerism of N-(Benzo[d]thiazol-2-yl)-o/m/p-Nitrobenzamide: Crystal Structure, Hirshfeld Surface Analysis and Interaction Energy

1
Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Selangor 43600, Malaysia
2
Department of Basic Science and Engineering, Faculty of Agriculture and Food Sciences, Universiti Putra Malaysia, Bintulu, Sarawak 97008, Malaysia
*
Authors to whom correspondence should be addressed.
Crystals 2020, 10(5), 348; https://doi.org/10.3390/cryst10050348
Received: 15 March 2020 / Revised: 14 April 2020 / Accepted: 15 April 2020 / Published: 28 April 2020
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. View Full-Text
Keywords: nitro; N-(benzo[d]thiazol-2-yl)benzamide; hydrogen bondings; non-covalent interactions; Hirshfeld surface; interaction energies nitro; N-(benzo[d]thiazol-2-yl)benzamide; hydrogen bondings; non-covalent interactions; Hirshfeld surface; interaction energies
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Binti Abdul Latiff, A.; Chong, Y.Y.; Mark-Lee, W.F.; Kassim, M.B. Insight into Positional Isomerism of N-(Benzo[d]thiazol-2-yl)-o/m/p-Nitrobenzamide: Crystal Structure, Hirshfeld Surface Analysis and Interaction Energy. Crystals 2020, 10, 348.

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