Abstract
The title compound, C23H23FN3O2 has been synthesized and the structure was investigated by X-ray diffraction studies. The compound crystallizes in the triclinic crystal class in the space group \(P\overline{1}\) with cell parameters a = 9.345(2) Å, b = 10.940(3) Å, c = 11.986(4) Å, α = 72.349(6)°, β = 68.106(18)°, γ = 66.867(5)°, Z = 2 and V = 1027.8(5) Å3. 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. One of the oxygen atoms attached to the hydantoin ring simultaneously accepts two hydrogen bonds to form a three centered hydrogen bonding pattern.
Graphical Abstract
Hydantoins have been reported for their effect on proliferation of human ovarian tumor cells and murine osteosarcoma cells, which have metastatic potential to lung and liver, which prompted us to synthesize the title compound and we are reporting its crystal and molecular structure here.
Similar content being viewed by others
References
Ananda Kumar CS, Benaka Prasad SB, Vinaya K, Chandrappa S, Thimmegowda NR, Ranganatha SS, Rangappa KS (2009) Invest New Drugs 27:131
Kavitha CV, Nambiar M, Ananda Kumar CS, Choudhary B, Muniyappa K, Rangappa KS, Raghavan SC (2009) Biochem Pharmacol 77:348
Thenmozhiyal JC, Wong PTH, Chui WK (2004) J Comb Chem 4:175
Nefzi A, Giulianotti L, Truong L, Rattan S, Ostresh JM, Joughten RA (2002) J Comb Chem 4:175
Somsak L, Nagy V, Hadady Z, Felfoldi N, Docsa T, Gergely P (2005) Frontiers in medicinal chemistry. Bentham Science Publishers, Bussum, The Netherlands, p 253.
Basappa, Ananda Kumar CS, Nanjunda Swamy S, Sugahara K, Rangappa KS (2009) Bioorg Med Chem 17(14):4928
Otwinowski Z, Minor W, Carter CW Jr, Sweet RM (1997) Macromol Crystallogr 276:307
Mackay S, Gillmore CJ, Edwards C, Shankland K (1999) maXus Computer programme for the solution and refinement of crystal strucutures. Bruker Nonius/Mac-Science/The University of Glasgow, The Netherlands/Japan/UK
Sheldrick GM (2008) Acta Crystallogr A 64:112
Spek AL (1998) Acta Crystallogr A 46:C34
Todorov PT, Petrova RN, Naydenova EM, Shivachev BL (2008) Cent Eur J Chem 7:14
Galvez E, Martinez M, Gonzalez J, Trigo GG, Smith-Verdier P, Florencio R, Garcia-Blanco S (1983) J Pharm Sci 72:881
Yu FL, Schwalbea CH, Watkin DJ (2004) Acta Crystallogr C 60:714
Cremer D, Pople JA (1975) J Am Chem Soc B 12:1354
Smith-Verdier P, Florencio F, Garcia-Blanco S (1977) Acta Crystallogr B 33:3381
Rangappa KS, Mallesh H, Anilkumar NV, Yathirajan HS, Sridhar MA, Lokanath NK, Shashidhara Prasad J (2000) J Chem Crystallogr 30:255
Mullica DF, Trawick ML, Wu PWN, Sappenfield EL (1998) J Chem Crystallogr 28:761
Gauthier TJ, Yokum TS, Guillermo AM, Mclaughlin ML, Liu YH, Frank RR (1997) Acta Crystallogr C 53:1659
Acknowledgments
The authors are grateful to DST and Government of India and University of Mysore for financial assistance under the projects SP/I2/FOO/93. One of the authors (H. R. Manjunath) thanks UGC-BRS and University of Mysore for the award of fellowship.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Manjunath, H.R., Naveen, S., Ananda Kumar, C.S. et al. Crystal and Molecular Structure Studies of 1′-Benzyl-8-(4-fluorobenzyl)-8-azaspiro[bicyclo-[3.2.1]octane-3,4′-imidazolodine]-2′,5′-dione. J Chem Crystallogr 42, 504–507 (2012). https://doi.org/10.1007/s10870-011-9995-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10870-011-9995-8