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Stabilization of the DMSO Solvate of 2-Chloro-5-nitrobenzoic acid (Mesalazine Impurity M) by Bifurcated Hydrogen Bonds: Crystallographic, Spectroscopic, Thermal and Computational Studies

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Abstract

The strategy for choosing the optimal solvent DMSO to produce the solvate of Mesalazine impurity M is demonstrated and the possibility of selective crystallization as a means to remove the impurity from the drug substance is proposed. The single crystal XRD was undertaken to identify molecular interactions that take place to compensate for the unsatisfied arrangement of hydrogen bonds in the supramolecular architecture. Interestingly, formation of O–H⋯S, O–H⋯O, and C–H⋯O connections leads to loop/ring motifs stabilizing the crystal entity. In the present study, purification of the drug molecule remains a chief objective for future investigations, since crystallization of Mesalazine impurity M alone cannot conclusively guarantee separation of impurity.

Graphical Abstract

The present work emphasized hydrogen bonding interactions that play an important role in the supramolecular assembly of DMSO solvate of the Mesalazine impurity M.

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Abbreviations

CIF:

Crystallographic information file

CSD:

Cambridge structural database

CNBA:

2-Chloro-5-nitrobenzoic acid

DMSO:

Dimethyl sulfoxide

Mp:

Melting point

MEP:

Molecular electrostatic potential

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Acknowledgements

UL thanks DST-PURSE Lab, Mangalore University and Nitte University Centre for Science Education and Research, Mangaluru for structural analysis and microphotographs. BN acknowledges UGC for financial support through the BSR one-time Grant (SR/S/Z/-23/2010/32) for the purchase of chemicals. MKS acknowledges IOE and DST-PURSE, Vijnana Bhavan, University of Mysore, Mysuru. UL also thank Anupam G. Lobo for helping in Hirshfeld surfaces analysis.

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Authors and Affiliations

  1. Department of Industrial Chemistry, Mangalore University, Mangalagangothri, Mangalore, 574199, India

    U. Likhitha, B. Narayana & B. K. Sarojini

  2. Department of Studies in Chemistry, Mangalore University, Mangalagangothri, Mangalore, 574199, India

    B. Narayana & P. J. Srijana

  3. IOE, Vijnana Bhavan, University of Mysore, Mysore, 570006, India

    S. Madan Kumar

  4. Department of Pharmaceutics, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal, 576104, India

    Naha Anup

  5. Department of Studies in Chemistry, University of Mysore, Mangalagangothri, Mysore, 570006, India

    H. S. Yathirajan

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Correspondence to B. Narayana.

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Likhitha, U., Narayana, B., Sarojini, B.K. et al. Stabilization of the DMSO Solvate of 2-Chloro-5-nitrobenzoic acid (Mesalazine Impurity M) by Bifurcated Hydrogen Bonds: Crystallographic, Spectroscopic, Thermal and Computational Studies. J Chem Crystallogr 52, 276–286 (2022). https://doi.org/10.1007/s10870-021-00913-1

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