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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

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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.

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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).

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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.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Science Education and Research, Bhopal, Madhya Pradesh, 462 066, India

    Rahul Shukla & Deepak Chopra

  2. Department of Chemistry, Visvesvaraya National Institute of Technology, Nagpur, Maharashtra, 440 010, India

    Susanta K Nayak

  3. Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, Karnataka, 560 012, India

    M Kishore Reddy & Tayur N Guru Row

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  1. Rahul Shukla
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Shukla, R., Nayak, S.K., Chopra, D. et al. Quantitative investigation of intermolecular interactions in dimorphs of 3-Chloro-N-(2-fluorophenyl)benzamide and 2-Iodo-N-(4- bromophenyl)benzamide. J Chem Sci 130, 38 (2018). https://doi.org/10.1007/s12039-018-1444-1

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