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Quantitative investigation of intermolecular interactions in dimorphs of 3-Chloro-N-(2-fluorophenyl)benzamide and 2-Iodo-N-(4- bromophenyl)benzamide

  • Rahul Shukla
  • Susanta K Nayak
  • Deepak Chopra
  • M Kishore Reddy
  • Tayur N Guru Row
Regular Article

Abstract

In this study, we have analyzed the role of different intermolecular interactions in the polymorphic modifications of 3-chloro-N-(2-fluorophenyl)benzamide (I) and 2-iodo-N-(4- bromophenyl)benzamide (II). The crystals were obtained via slow evaporation method with the alteration of solvents for crystallization. The already reported form [Cryst. Growth Des. (2011) 11:1578] crystallizes in P2\(_{1}\)/c with Z\(^\prime \)=2 [Form IA], while the new form crystallizes in Pna2\(_{1}\) with Z\(^\prime \)=1 [Form IB]. The latter compound crystallizes in P2\(_{1}\)/n with Z\(^\prime \)=1 [Form IIA] and in Pbca with Z\(^\prime \)=1 [Form IIB]. Weak Cl\(\cdot \cdot \cdot \)Cl and C-H\(\cdot \cdot \cdot \)F interactions in the former (IA, IB) and weak I\(\cdot \cdot \cdot \)I and C-H\(\cdot \cdot \cdot \uppi \) interactions in the latter (IIA, IIB) play a vital role in the formation of different polymorphic modifications leading to the observation of conformational and packing polymorphs, respectively. PIXEL calculations show that most of the interactions present in the crystal structures are dispersive in nature. 2D Fingerprint plots revealed that the relative contribution of different intermolecular interactions in different polymorphic forms was different.

Graphical abstract

SYNOPSIS We have analyzed the role of different intermolecular interactions and evaluated their contributions in the polymorphic modifications of 3-chloro-N-(2-fluorophenyl)benzamide (I) and 2-iodo-N-(4- bromophenyl)benzamide (II).

Keywords

Halogen benzamides intermolecular interactions dispersion polymorphs 

Notes

Acknowledgements

We thank DST, India for the XRD facility at IISc, Bangalore. RS thanks DST-INSPIRE for the PhD Fellowship. SKN thanks CSIR & DST for financial assistance. DC thanks IISER Bhopal for research facilities and infrastructure.

Conflict of interest

The authors declare that there is no conflict of interest.

Supplementary material

12039_2018_1444_MOESM1_ESM.pdf (2.3 mb)
Supplementary material 1 (pdf 2382 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Department of ChemistryIndian Institute of Science Education and ResearchBhopalIndia
  2. 2.Department of ChemistryVisvesvaraya National Institute of TechnologyNagpurIndia
  3. 3.Solid State and Structural Chemistry UnitIndian Institute of ScienceBangaloreIndia

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