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

Add time:08/29/2019    Source:sciencedirect.com

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.

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