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

Rahul Shukla, Susanta K. Nayak, Deepak Chopra, M. Kishore Reddy, T. N. Guru Row

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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 C–H⋯O[dbnd]C interactions. In addition to that, C–H⋯F–C and C–H⋯π interactions also played an important role in the stabilization. However, 2D Fingerprint analysis revealed that the contribution of C–H⋯F–C interaction in a given structure was also dependent on the contribution of other hydrogens bonds involving halogens.

Original languageEnglish
Pages (from-to)280-288
Number of pages9
JournalJournal of Molecular Structure
StatePublished - 15 Jul 2018
Externally publishedYes


  • 3D isostructurality
  • Halogens
  • Interaction energies

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry


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