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Single crystal inspection, Hirshfeld surface investigation and DFT study of a novel derivative of 4-fluoroaniline: 4-((4-fluorophenyl)amino)-4-oxobutanoic acid (BFAOB)

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Abstract

The title compound, C10H10FNO3, also known as [4-((4-fluorophenyl)amino)-4-oxobutanoic acid] (BFAOB), is synthesized efficiently, and its structure is confirmed by the SC-XRD technique, which indicates that two crystallographically different molecules are present in the asymmetric unit. The fluorobenzene ring is oriented at a dihedral angle of 76.09 (9)° and 23.7 (2)° with respect to acetamide moiety in the first and second types of molecule, respectively. A molecular overlay plot is employed to explore the difference between two types of molecules. Strong hydrogen bonding of type N–H…O, O–H…O and comparatively weak hydrogen bonding of type C-H…O stabilize the crystal packing. The titled compound is also characterized by powder XRD. Hirshfeld surface inspection is carried out to explore the non-covalent interactions that are responsible for crystal packing. DFT calculations demonstrate the high stability of BFAOB crystal compound.

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Acknowledgements

M. M. A. and MI express appreciation to the Deanship of Scientific Research at King Khalid University, Saudi Arabia for funding through the research groups program under grant number R.G.P. 2/109/42.

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Authors and Affiliations

  1. Department of Physics, University of Sargodha, Sargodha, 40100, Pakistan

    Muhammad Ashfaq, Muhammad Nawaz Tahir & Budar Munir

  2. Department of Physics, University of Mianwali, Mianwali, 42200, Pakistan

    Muhammad Ashfaq & Gulzar Ahmed

  3. Department of Chemistry, University of Mianwali, Mianwali, 42200, Pakistan

    Khurram Shahzad Munawar

  4. Department of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan

    Khurram Shahzad Munawar

  5. Department of Chemical and Biomolecular Engineering, University of California Irvine, Irvine, CA, 92697, USA

    Georgii Bogdanov

  6. Department of Chemistry, Government College University, Faisalabad, Pakistan

    Akbar Ali

  7. Department of Electrical and Computer Engineering, National University of Singapore, Singapore, 117583, Singapore

    Arulraj Ramalingam

  8. Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia

    Mohammed Mujahid Alam & Muhammad Imran

  9. Research and Development Centre, Bharathiar University, Coimbatore, Tamil Nadu, 641046, India

    Sivakumar Sambandam

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  1. Muhammad Ashfaq
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Ashfaq, M., Munawar, K.S., Bogdanov, G. et al. Single crystal inspection, Hirshfeld surface investigation and DFT study of a novel derivative of 4-fluoroaniline: 4-((4-fluorophenyl)amino)-4-oxobutanoic acid (BFAOB). J IRAN CHEM SOC 19, 1953–1961 (2022). https://doi.org/10.1007/s13738-021-02432-4

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