CRYSTAL AND MOLECULAR STRUCTURE STUDIES OF 1′-BENZYL-8-(4-FLUOROBENZYL)-8-AZASPIRO[BICYCLO-[3.2.1]OCTANE-3,4′-IMIDAZOLIDINE]-2′,5′-DIONE
H.R. Manjunath1, S. Naveen2, C.S. Ananda Kumar3, S.B. Benaka Prasad4, M.V. Deepa Naveen5, M.A. Sridhar1, J. Shashidhara Prasad1, K.S. Rangappa3
1 Department of Studies in Physics, University of Mysore
2 Department of Physics, Sri Bhagawan Mahaveer Jain College of Engineering, Jain University
3 Department of Studies in Chemistry, University of Mysore
4 Department of Chemistry, Sri Bhagawan Mahaveer Jain College of Engineering, Jain University
5 Department of Physics, RNS Insitute of Technology
mas@physics.uni-mysore.ac.in
Keywords: hydantoins, crystal structure, spiro centered, chair conformation, hydrogen bonding
Pages: 986-990
Abstract
The title compound 1′-Benzyl-8-(4-fluorobenzyl)-8-azaspiro[bicyclo[3.2.1] octane-3,4′-imidazolidine]-2′,5′-dione, C23H23FN3O2 is synthesized and the structure is investigated by X-ray diffraction studies. The compound crystallizes in the triclinic crystal class in the P1 space group. The hydantoin ring adopts a planar conformation and is affected by the π conjugation. The pyrrolidine and piperidine rings in the bicyclo octane moiety adopt envelope and chair conformations respectively. The structure exhibits both inter- and intramolecular hydrogen bonds of the type N-H…O, C-H…O, and C-H…N. The oxygen atom in the hydantoin ring simultaneously accepts two hydrogen bonds to form a three-centered hydrogen bonding pattern.
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