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Crystal Structure and Electronic Properties of a Piroxicam Derivative: A Combined X-Ray Analysis and Quantum Mechanical Studies

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Abstract

A piroxicam derivative, 4-acetamidobenzenesulfonate-2-methyl-N-(2-pyridal)-2H-1,2-benzothiazine-1,1-dioxide (2), has been synthesized and structurally characterized by X-ray analysis. The electronic structure of (2) was calculated at the DFT level using the hybrid exchange–correlation functional BLYP. The optimized molecular geometry of (2) corresponds closely to that obtained from the X-ray structure analysis. Intermolecular N–H···O and C–H···O hydrogen bonds connect the molecules in (2) forming a two-dimensional supramolecular frameworks in (011) plane, which are further linked via π···π interactions to generate a three dimensional architecture. The relative contribution of different interactions to Hirshfeld surface indicates that the H···H and O···H contacts can account for about 76 % of the total Hirshfeld surface area in (2). The HOMO–LUMO energy gap of 2.77 eV indicates a high kinetic stability of (2).

Graphical Abstract

A piroxicam derivative, 4-acetamidobenzenesulfonate-2-methyl-N-(2-pyridal)-2H-1,2-benzothiazine-1,1-dioxide has been synthesized and structurally characterized by X-ray analysis which generates a three dimensional architecture. Most important figure

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Acknowledgments

The authors are grateful to Prof. Monika Mukherjee, Department of Solid State Physics, IACS, Kolkata-700032, India, for helping in DFT calculations.

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Author notes

  1. Soumen Ghosh

    Present address: Department of Physics, Gour Mahavidyalaya, Mangalbari, Malda, 732142, India

Authors and Affiliations

  1. Department of Physics, Jadavpur University, Kolkata, 700032, India

    Alok K. Mukherjee

  2. Department of Solid State Physics, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, 700032, India

    Dipak K. Hazra & Basab Chattopadhyay

  3. Department of Chemistry, MNR Post-Graduate College, Kukatpally, Hyderabad, India

    Sarbani Pal

  4. Department of Chemistry, University of Manchester, Manchester, M13 9PL, UK

    Madeleine Helliwell

Authors
  1. Soumen Ghosh
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  2. Dipak K. Hazra
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  3. Basab Chattopadhyay
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  4. Sarbani Pal
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  5. Madeleine Helliwell
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  6. Alok K. Mukherjee
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Correspondence to Alok K. Mukherjee.

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Ghosh, S., Hazra, D.K., Chattopadhyay, B. et al. Crystal Structure and Electronic Properties of a Piroxicam Derivative: A Combined X-Ray Analysis and Quantum Mechanical Studies. J Chem Crystallogr 42, 1067–1074 (2012). https://doi.org/10.1007/s10870-012-0360-3

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  • DOI: https://doi.org/10.1007/s10870-012-0360-3

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