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Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline


Soundararajan Krishnan (1) orcid , Thanigaimani Kaliyaperumal (2) orcid , Ramalingam Marimuthu (3,*) orcid , Sethuraman Velusamy (4) orcid

(1) Department of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam - 613 403, Thanjavur, Tamil Nadu, India
(2) Department of Chemistry, Government Arts College, Tiruchirappalli - 620 022, Tamil Nadu, India
(3) Department of Chemistry, Bon Secours College for Women, Thanjavur - 613 006, Tamil Nadu, India
(4) Department of Chemistry, Periyar Maniammai Institute of Science and Technology, Vallam - 613 403, Thanjavur, Tamil Nadu, India
(*) Corresponding Author

Received: 13 Aug 2021 | Revised: 15 Oct 2021 | Accepted: 16 Oct 2021 | Published: 31 Dec 2021 | Issue Date: December 2021

Abstract


The crystal structure investigation of the title compound 4-((pyrrolidin-1-ylsulfonyl) methyl)aniline (PSMA) C11H16N2O2S shows that the molecule is essentially coplanar with a dihedral angle of 26.70(14)°between the pyrrolidine and the benzene rings. A pair of strong N-H···O hydrogen bonds produces continuous two-dimensional sheets with R22(18) ring motifs. The crystal structure also features a weak C-H···π interaction resulting in a three-dimensional network. Density functional theory (DFT) calculations reveal that the experimental and calculated geometric parameters of the molecule are nearly the same. Hirshfeld surface analysis has been carried out to study the various intermolecular interactions responsible for the crystal packing. Theoretical calculations indicate an excellent correlation between the experimental and the simulated UV spectra.


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Keywords


Sulfonamide drugs; Electronic spectrum; Density function theory; Computational chemistry; Hirshfeld surface analysis; Single crystal X-ray diffraction

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DOI: 10.5155/eurjchem.12.4.419-431.2177

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Periyar Maniammai Institute of Science and Technology, Vallam, Thanjavur-613403, Tamilnadu, India.

Citations

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[1]. Zhen Wang, Feng-Lan Zhao, Gui-Ge Hou, Qing-Guo Meng
Crystal structure of methyl ((4-aminobenzyl)sulfonyl)-L-prolinate, C13H18N2O4S
Zeitschrift für Kristallographie - New Crystal Structures  238(4), 725, 2023
DOI: 10.1515/ncrs-2023-0173
/

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How to cite


Krishnan, S.; Kaliyaperumal, T.; Marimuthu, R.; Velusamy, S. Eur. J. Chem. 2021, 12(4), 419-431. doi:10.5155/eurjchem.12.4.419-431.2177
Krishnan, S.; Kaliyaperumal, T.; Marimuthu, R.; Velusamy, S. Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline. Eur. J. Chem. 2021, 12(4), 419-431. doi:10.5155/eurjchem.12.4.419-431.2177
Krishnan, S., Kaliyaperumal, T., Marimuthu, R., & Velusamy, S. (2021). Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline. European Journal of Chemistry, 12(4), 419-431. doi:10.5155/eurjchem.12.4.419-431.2177
Krishnan, Soundararajan, Thanigaimani Kaliyaperumal, Ramalingam Marimuthu, & Sethuraman Velusamy. "Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline." European Journal of Chemistry [Online], 12.4 (2021): 419-431. Web. 10 Dec. 2023
Krishnan, Soundararajan, Kaliyaperumal, Thanigaimani, Marimuthu, Ramalingam, AND Velusamy, Sethuraman. "Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline" European Journal of Chemistry [Online], Volume 12 Number 4 (31 December 2021)

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