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Asymmetric base pairing in the complex 5-fluorocytosinium chloride/5-fluorocytosine monohydrate

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The structure of the complex 5-Fluorocytosinium chloride/5-Fluorocytosine monohydrate has been studied by X-ray diffraction methods. It crystallizes in the monoclinic system, space group P 21 /n, a = 7.1257 (15), b = 8.351 (3), c = 21.520 (4) Å, β = 92.89 (8)°, V = 1279.0 (6) Å3, Z = 4. The structure consists of triple hydrogen-bonded 5-Fluorocytosine pairs, water molecules and chloride anions. Asymmetric reversed Watson-Crick base pairing occurs between one protonated (5FcytH+) and one neutral 5-Fluorocytosine (5Fcyt) molecule.

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References

  1. Jeffrey, G.A. An Introduction to Hydrogen Bonding; Oxford University Press, New York, 1997.

    Google Scholar 

  2. Lavery, R.; Zakrewska, K. In Oxford Handbook of Nucleic Acid Structure; Neidle S., Ed.; Oxford University Press, New York, 1999, pp 39–76.

  3. Desiraju, G.R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.

    Article  CAS  Google Scholar 

  4. Nangia, A.; Desiraju, G.R. In Topics in Current Chemistry Springer Berlin Heidelberg, 1998, pp 57–95.

  5. Meléndez, R.E.; Hamilton, A.D. In Topics in Current Chemistry Springer Berlin Heidelberg, 1998, pp 97–129.

  6. Portalone, G.; Bencivenni, L.; Colapietro, M.; Pieretti, A.; Ramondo, F. Acta Chem. Scand. 1999, 1, 57.

    Article  Google Scholar 

  7. Brunetti, B.; Piacente, V.; Portalone, G. J. Chem. Eng. Data 2000, 45, 242.

    Article  CAS  Google Scholar 

  8. Brunetti, B.; Piacente, V.; Portalone, G. J. Chem. Eng. Data 2002, 47, 17.

    Google Scholar 

  9. Portalone, G.; Ballirano, P.; Maras, A. J. Mol. Struct. 2002, 608, 35.

    Google Scholar 

  10. Portalone, G.; Colapietro, M. Acta Cryst. 2004, E60, o1165.

  11. Portalone, G.; Colapietro, M. J. Chem. Crystallogr. 2004, 34, 609.

    Article  CAS  Google Scholar 

  12. Portalone, G.; Colapietro, M. Acta Cryst. 2006, E62, o1059.

  13. Patel, D.J.; Bouaziz, S.; Kettani, A.; Wang, Y. In Oxford Handbook of Nucleic Acid Structure; Neidle S., Ed.; Oxford University Press, New York, 1999; pp 389–453.

  14. Kurozumi, K.; Tamiya, T.; Ono, Y.; Otsuka, S.; Kambara, H.; Adachi, Y.; Ichikawa, T.; Hamada, H.; Ohmoto, T. J. Neuro-Oncol. 2004, 66, 117.

    Article  Google Scholar 

  15. Colapietro, M.; Cappuccio, G.; Marciante, C.; Pifferi, A.; Spagna, R.; Helliwell, J.R. J. Appl. Crystallogr. 1992, 25, 192.

    Article  Google Scholar 

  16. Altomare, A.; Burla, M.C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.

    Article  CAS  Google Scholar 

  17. Sheldrick, G.M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1997.

  18. Farrugia, L.J. J. Appl. Cryst. 1997, 30, 565.

    Article  CAS  Google Scholar 

  19. Hulme, A.T.; Tocher, D.A. Cryst. Growth Des. 2006, 6, 481.

    Article  CAS  Google Scholar 

  20. Prabakaran, P.; Murugesan, S.; Thomas Muthiah; P.; Bocelli; G.; Righi, L. Acta Cryst. 2001, E57, o933.

  21. Smith, G.; Wermuth, U.D.; Healy, P.C. Acta Cryst. 2005, E61, o746 (and references therein).

  22. Etter, M.C.; MacDonald, J.C.; Bernstein, J. Acta Cryst. 1990, B46, 256.

    CAS  Google Scholar 

  23. Bernstein, J.; Davis, R.E.; Shimoni, L.; Chang, N.-L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555.

    Article  CAS  Google Scholar 

  24. Fujinami, F.; Ogawa, K.; Arakawa, Y.; Shirotake, S.; Fuji, S.; Tomita, K.-I. Acta Cryst. 1979, B35, 968.

    CAS  Google Scholar 

  25. Salam, M.A.; Aoki, K. Inorg. Chim. Acta 2000, 311, 15.

    Article  CAS  Google Scholar 

  26. Schimanski, A.; Freisinger, E.; Erxleben, A.; Lippert, B. Inorg. Chim. Acta 1998, 283, 223.

    Article  CAS  Google Scholar 

  27. Műller, J.; Freisinger, E. Acta Cryst. 2005, E61, o320.

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Authors and Affiliations

  1. Department of Chemistry, University of Rome I ‘La Sapienza’, P.le Aldo Moro, 5, I-00185, Rome, Italy

    Gustavo Portalone & Marcello Colapietro

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  1. Gustavo Portalone
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  2. Marcello Colapietro
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Correspondence to Gustavo Portalone.

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Supplementary material

CCDC-609444 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/data request/cif; by e-mailing data request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223–336033.

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Portalone, G., Colapietro, M. Asymmetric base pairing in the complex 5-fluorocytosinium chloride/5-fluorocytosine monohydrate. J Chem Crystallogr 37, 141–145 (2007). https://doi.org/10.1007/s10870-006-9169-2

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