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Two Polymorphs of 1-(2-Methyl-3-oxoisoindolin-5-yl)urea

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Abstract

4-Ureidophthalimide or ureido isoindolin-1-one based ligands were shown by NMR spectroscopy and theoretical studies to bind the CG base pairs in the major groove. To examine this hydrogen-bonded complex, we cocrystallized 5-fluorocytosine, 9-methylguanine and 1-(2-methyl-3-oxoisoindolin-5-yl)urea. Two polymorphs of the latter compound were obtained during the cocrystallization attempts. Both crystallized in monoclinic space groups: form Ia in P21/c with cell parameters of a = 11.382(2), b = 6.042(1), c = 14.102(2) Å and β = 96.51(1)°, and form Ib in P21/n with cell parameters of a = 7.092(1), b = 11.643(2), c = 11.580(2) Å and β = 93.48(1)°. An identical molecular conformation of the two polymorphs is observed. Both polymorphs have an R 22 (8) N–H···O interaction linking the urea fragments of two molecules to a centrosymmetric dimer. Nevertheless, the crystal packing for both forms is completely different. In Ia, two dimers are connected by two R 12 (6) N–H···O bonds simultaneously to a shifted ribbon motif, whereas in Ib the two R 12 (6) interactions link two molecules from two different dimers.

Graphical Abstract

Two polymorphs of 1-(2-methyl-3-oxoisoindolin-5-yl)urea show similar R 22 (8) and R 12 (6) hydrogen-bond patterns but one completely different crystal packing.

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References

  1. Pabo CO, Sauer RT (1984) Annu Rev Biochem 53:293

    Article  CAS  Google Scholar 

  2. Luscombe NM, Austin SE, Berman HM, Thornton JM (2000) Genome Biol 1:1

    Article  Google Scholar 

  3. Jones S, Daley DTA, Luscombe NM, Berman HM, Thornton JM (2001) Nucl Acids Res 29(4):943

    Article  CAS  Google Scholar 

  4. Mankin A (2006) Nat Struct Mol Biol 13(10):858

    Article  CAS  Google Scholar 

  5. Inouye M, Hyodo Y, Nakazumi H (1999) J Org Chem 64:2704

    Article  CAS  Google Scholar 

  6. Gait MJ, Karn J (1993) Trends Biochem Sci 18(7):255

    Article  CAS  Google Scholar 

  7. Gallego J, Varani G (2001) Acc Chem Res 34:836

    Article  CAS  Google Scholar 

  8. Mertz E, Mattei S, Zimmerman SC (2000) Org Lett 2(19):2931

    Article  CAS  Google Scholar 

  9. Xiao Z, Weisz K (2007) J Phys Org Chem 20:771

    Article  CAS  Google Scholar 

  10. Allen FH (2002) Acta Cryst B58:380 (CSD, Version 5.3 of November 2009, plus four updates)

  11. Fujita S, Takenaka A, Sasada Y (1984) Bull Chem Soc Jpn 57:1707

    Article  CAS  Google Scholar 

  12. Fujita S, Takenaka A, Sasada Y (1985) Biochemistry 24:508

    Article  CAS  Google Scholar 

  13. O’Brien EJ (1967) Acta Cryst 23:92

    Article  Google Scholar 

  14. Tanaka H, Shiomi D, Ise T, Sato K, Takui T (2007) Cryst Eng Commun 9:767

    CAS  Google Scholar 

  15. Borsche W, Diacont K, Hanau H (1934) Chem Ber 67:675

    Google Scholar 

  16. Sheldrick GM (2008) Acta Cryst A64:112

    CAS  Google Scholar 

  17. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) J Appl Cryst 41:466 (Mercury Version 2.3)

    Article  CAS  Google Scholar 

  18. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed Engl 34:1555

    Article  CAS  Google Scholar 

  19. Ciajolo MR, Lelj F, Tancredi T, Temussi PA, Tuzi A (1982) Acta Cryst B38:2928

    CAS  Google Scholar 

  20. Nastopoulos V, Weiler J (1988) Acta Cryst C44:500

    CAS  Google Scholar 

  21. Hooft RWW, Kanters JA, Kroon J (1991) J Mol Struct 263:267

    Article  CAS  Google Scholar 

  22. Nastopoulos V, Germain G, Weiler J (1991) Acta Cryst C47:1546

    CAS  Google Scholar 

  23. Bott RC, Smith G, Wermuth UD, Dwyer NC (2000) Aust J Chem 53:767

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Institut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt am Main, Germany

    Maya Tutughamiarso & Mirko Zeiger

  2. Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438, Frankfurt am Main, Germany

    Michael Bolte

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  1. Maya Tutughamiarso
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  2. Mirko Zeiger
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  3. Michael Bolte
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Correspondence to Michael Bolte.

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Tutughamiarso, M., Zeiger, M. & Bolte, M. Two Polymorphs of 1-(2-Methyl-3-oxoisoindolin-5-yl)urea. J Chem Crystallogr 41, 1150–1153 (2011). https://doi.org/10.1007/s10870-011-0061-3

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  • DOI: https://doi.org/10.1007/s10870-011-0061-3

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