Observation of 3D isostructurality in halogen substituted N-benzoyl-N-phenylbenzamides

• Published in: Journal of molecular structure 2018-07, Vol.1164, p.280-288
• Main Authors: Shukla, Rahul, Nayak, Susanta K., Chopra, Deepak, Reddy, M. Kishore, Guru Row, T.N.
• Format: Article
• Language: English
• Subjects: 3D isostructurality; Halogens; Interaction energies
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2018.03.029

The occurrence of 3D isostructurality in six halogen substituted N-benzoyl-N-phenylbenzamides has been reported and this feature has been quantitatively analyzed in this study. 4-fluoro-N-(4-fluorobenzoyl)N-(fluorphenyl)benzamide (1) was observed to be isostructural with 2-fluoro-N-(2-fluorobenzoyl)N-(4-fluorophenyl)benzamide (7), N-(4-bromophenyl)-2-fluoro-N-(2-fluorobenzoyl)benzamide (8) and 2-fluoro-N-(2-fluorobenzoyl)N-(4-iodophenyl)benzamide (9). Similarly, N-(4-chlorophenyl)-4-fluoro-N-(4-fluorobenzoyl)benzamide (2) and N-(4-bromophenyl)-4-fluoro-N-(4-fluorobenzoyl)benzamide (3) was observed to be isostructural with each other. It was clearly evident from the analysis of structural similarity that 3D supramolecular construct present in 2/3 [Set 2] were more identical as compared to those observed in 1/7/8/9 [Set 1]. The molecular packing in both sets of isostructural molecules was observed to be governed by the presence of several CH⋯OC interactions. In addition to that, CH⋯FC and CH⋯π interactions also played an important role in the stabilization. However, 2D Fingerprint analysis revealed that the contribution of CH⋯FC interaction in a given structure was also dependent on the contribution of other hydrogens bonds involving halogens. [Display omitted] •Crystal structures of six halogen substituted N-benzoyl-N-phenylbenzamides has been analyzed.•Observation of 3D isostructurality has been discussed.•Role of different intermolecular interactions has been discussed quantitatively.•2D Fingerprint plots have been analyzed.