European Journal of Chemistry

Synthesis, X-ray structure, and DFT analysis of a binary complex of 3,3'-[(3-benzimidazolyl)methylene]bis(4-hydroxy-2H-1-benzopyran-2-one): 5-Methyl-1,3-thiazol-2(3H)-imine

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Published: Dec 31, 2020
DOI: https://doi.org/10.5155/eurjchem.11.4.324-333.2028
Keywords:
DFT, Direct methods, X-ray diffraction, Crystal structure, Benzopyran derivatives, Intermolecular interactions
Section
Research Article
Issue
Vol. 11 No. 4 (2020): December 2020
Dates
Received 2020-08-18
Accepted 2020-10-22
Published 2020-12-31
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Gopal Sharma
X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu Tawi, 180006, India
http://orcid.org/0000-0003-4780-2804
Anshul Uppal
X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu Tawi, 180006, India
http://orcid.org/0000-0001-8203-616X
Sumati Anthal
X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu Tawi, 180006, India
http://orcid.org/0000-0001-7947-7335
Madhukar Baburao Deshmukh
Department of Chemistry, Shivaji University, Kolhapur, 416004, India
http://orcid.org/0000-0001-7097-2356
Priyanka Pandharinath Mohire
Department of Chemistry, Shivaji University, Kolhapur, 416004, India
http://orcid.org/0000-0003-4644-1111
Tanaji Ramchandra Bhosale
Department of Chemistry, Shivaji University, Kolhapur, 416004, India
http://orcid.org/0000-0002-0372-7702
Chellappanpillai Sudarsanakumar
School of Pure and Applied Physics, Mahatma Gandhi University, Kerala, 686560, India
http://orcid.org/0000-0003-2750-7795
Rajni Kant
X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu Tawi, 180006, India
http://orcid.org/0000-0001-8043-2329

Abstract

A combined theoretical and experimental investigation on a pharmaceutically important binary complex 3,3'-[(3-benzimidazolyl)methylene]bis(4-hydroxy-2H-1-benzopyran-2-one): 5-methyl-1,3-thiazol-2(3H)-imine is presented in this manuscript. The compound crystallizes in the monoclinic crystal system with space group Cc with unit cell parameters: a = 19.8151(8) Å, b = 15.2804(6) Å, c = 8.3950(4) Å, β = 94.0990(10)°, V = 2535.36(19) Å3, Z = 4, T = 296(2) K, μ(MoKα) = 0.184 mm-1, Dcalc = 1.490 g/cm3, 35833 reflections measured (5.332° ≤ 2Θ ≤ 56.678°), 6168 unique (Rint = 0.0467, Rsigma = 0.0388) which were used in all calculations. The final R1 was 0.0435 (I > 2σ(I)) and wR2 was 0.1073 (all data). The crystal structure has been determined by the conventional X-ray diffraction method, solved by direct methods and refined by the full matrix least squares procedure. Intramolecular hydrogen bonding of the type C–H⋅⋅⋅O and O–H⋅⋅⋅O is present and the crystal structure stabilizes via N–H…O, C–H…N and O–H…N intermolecular interactions. The optimized structural parameters have been compared and the parameters like ionization potential, electron affinity, global hardness, electron chemical potential, electronegativity, and global electrophilicity based on HOMO and LUMO energy values were calculated at B3LYP/6-311G(d,p) level of theory for a better understanding of the structural properties of the binary complex.


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Sharma, G.; Uppal, A.; Anthal, S.; Deshmukh, M. B.; Mohire, P. P.; Bhosale, T. R.; Sudarsanakumar, C.; Kant, R. Synthesis, X-Ray Structure, and DFT Analysis of a Binary Complex of 3,3’-[(3-benzimidazolyl)methylene]bis(4-Hydroxy-2H-1-Benzopyran-2-one): 5-Methyl-1,3-Thiazol-2(3H)-Imine. Eur. J. Chem. 2020, 11, 324-333.

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Supporting Agencies

Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 Project (Ref. No, RUSA/JU/2/2019-20/111/3588-3636), India.
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