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Synthesis, Crystal Structure and Hydrogen-Bonding Patterns in (RS)-1-Carbamoyl Pyrrolidine-2-Carboxylic Acid

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Abstract

The title compound, N-carbamoyl-dl-proline, C6H10N2O3, crystallizes in the triclinic P-1 space group with unit cell parameters a = 7.610 (4) Å, b = 9.259 (5) Å, c = 11.749 (7) Å, α = 110.294 (11)°, β = 101.304 (13)°, γ = 91.391 (16)°, with two crystallographically independent molecules in the asymmetric unit. The ureido and carboxyl groups are equatorial and axial to the pyrrolidine rings, respectively. The pyrrolidine rings adopt envelope and twisted conformations in the residue A and B, respectively. The molecules are joined by N–H···O and O–H···O hydrogen bonds into cyclic structures with graph set R 22 (8), forming infinite chains parallel to the cb plane with graph set C 22 (14), that are further connected via N–H···O hydrogen bonds into a three-dimensional network.

Graphical Abstract

The molecules of N-carbamoyl-dl-proline are joined by N–H···O and O–H···O hydrogen bonds into cyclic structures with graph set R 22 (8), forming infinite ribbons parallel to the cb plane with graph-set C 22 (14), that are further connected via N–H···O hydrogen bonds into a three-dimensional network.

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References

  1. Huang M, Greaves LM (2003) Cell Mol Life Soc 97:1354

    Google Scholar 

  2. Kuilenburg ABP, van Lenthe H, Lofer M, van Gennip AH (2004) Clin Chem 50:2117

    Article  Google Scholar 

  3. Klucher G, Rabier D, Poggi-Travert F, Meyer-Gast D, Bardet J, Drouin V, Cadoudal M, Saudubray JM (1996) J Inherit Metab Dis 19:220

    Article  Google Scholar 

  4. Theis S, Hartrodt B, Kottra G, Neubert K, Daniel H (2002) Mol Pharmacol 61:214

    Article  CAS  Google Scholar 

  5. Busse WD, Hansen SR, Carpenter FH (1976) J Am Chem Soc 96:5949

    Article  Google Scholar 

  6. Vermouth CG, Bourguignon JJ, Schlewer G, Gies GP, Shoenfelder A, Melikian A, Bouchet MJ, Chantreaux D, Molimard JC, Heaulme M, Chambon JP, Biziere K (1987) J Med Chem 30:239

    Article  Google Scholar 

  7. Suzuki M, Yamazaki T, Ohta H, Shima K, Ohi K, Nishiyama S, Sugai T (2000) Synlett 189:192

    Google Scholar 

  8. Lagrille O, Taillades J, Boiteau L, Commeyras A (2002) Eur J Org Chem 6:1026

    Article  Google Scholar 

  9. Kravchenko AN, Chikunov IE (2006) Russ Chem Rev 75:191

    Article  CAS  Google Scholar 

  10. Altenbuchner J, Siemann-Herzberg M, Syldatk C (2001) Curr Opin Biotechnol 12:559

    Article  CAS  Google Scholar 

  11. Chen H, Ho C, Liu J, Lin K, Wang Y, Lu Ch, Liu H (2003) Biotechnol Prog 19:864

    Article  CAS  Google Scholar 

  12. Burton S, Dorrington RA (2004) Tetrahedron Asymmetr 15:2737

    Article  CAS  Google Scholar 

  13. Desiraju GR (2010) J Chem Sci 122:667

    Article  CAS  Google Scholar 

  14. Vishweshwar P, McMahon JA, Peterson ML, Hickey MB, Shattock TR, Zaworotko MJ (2005) Chem Comm 23: 4601

  15. Mahapatra S, Thakur TS, Joseph S, Varughese S, Desiraju GR (2010) Cryst Growth Des 10:3191

    Article  CAS  Google Scholar 

  16. Kuhn B, Mohr P, Stahl M (2010) J Med Chem 53:2601

    Article  CAS  Google Scholar 

  17. Khan M, Enkelmann V, Brunklaus G (2010) J Am Chem Soc 132:5254

    Article  CAS  Google Scholar 

  18. Seijas LE, Delgado GE, Mora AJ, Bahsas A, Uzcategui J (2006) Av Quím 1:3

    Google Scholar 

  19. Seijas LE, Delgado GE, Mora AJ, Bahsas A, Briceño A (2007) Acta Cryst C63:303

    Google Scholar 

  20. Delgado GE, Mora AJ, Uzcátegui J, Bahsas A, Briceño A (2007) Acta Cryst C63:o448

    CAS  Google Scholar 

  21. Seijas LE, Mora AJ, Delgado GE, Brunelli M, Fitch AN (2010) Powder Diffr 25:342

    Article  CAS  Google Scholar 

  22. Rigaku (2002) CrystalClear. Rigaku Corporation, Tokyo

    Google Scholar 

  23. Rigaku/MSC (2004) Crystal structure. Rigaku/MSC, Texas

    Google Scholar 

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

    CAS  Google Scholar 

  25. Brandenburg K (1998) Diamond. Crystal Impact GbR, Bonn

    Google Scholar 

  26. Myung S, Pink M, Baik MH, Clemmer DE (2005) Acta Cryst C61:o506

    CAS  Google Scholar 

  27. Seijas LE, Delgado GE, Mora AJ, Fitch AN, Brunelli M (2010) Powder Diffr 25:235

    Article  CAS  Google Scholar 

  28. Wallach O (1895) Justus Liebig’s Ann Chem 286:90

    Article  CAS  Google Scholar 

  29. Dalhus B, Görbitz CH (2004) J Mol Struc Theochem 675:47

    Article  CAS  Google Scholar 

  30. Allen FH (2002) Acta Cryst B58:380

    CAS  Google Scholar 

  31. Yennaward HP, Viswamitra M (1988) Acta Cryst C44:718

    Google Scholar 

  32. Zavargulis ES, Hambley TW (1994) Acta Cryst C50:2058

    Google Scholar 

  33. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354

    Article  CAS  Google Scholar 

  34. Griffin JF, Duax W, Weeks M (1984) Atlas of steroid structure. Plenum Publishing Corporation, New York

    Google Scholar 

  35. Spek AL (2003) J Appl Cryst 36:7

    Article  CAS  Google Scholar 

  36. Etter MC (1990) Acc Chem Res 23:120

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by CDCHT-ULA (grant C-1755-11-08-B) and FONACIT (grant LAB-97000821).

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Authors and Affiliations

  1. Laboratorio de Cristalografía, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida, 5101, Venezuela

    Gerzon E. Delgado, Luis E. Seijas, Asiloé J. Mora, Teresa González & Alexander Briceño

  2. Centro de Química, Instituto Venezolano de Investigaciones Científicas (IVIC), Apartado 21827, Caracas, 1020, Venezuela

    Teresa González & Alexander Briceño

Authors
  1. Gerzon E. Delgado
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  2. Luis E. Seijas
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  3. Asiloé J. Mora
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  4. Teresa González
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  5. Alexander Briceño
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Correspondence to Gerzon E. Delgado.

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Delgado, G.E., Seijas, L.E., Mora, A.J. et al. Synthesis, Crystal Structure and Hydrogen-Bonding Patterns in (RS)-1-Carbamoyl Pyrrolidine-2-Carboxylic Acid. J Chem Crystallogr 42, 388–393 (2012). https://doi.org/10.1007/s10870-011-0259-4

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  • DOI: https://doi.org/10.1007/s10870-011-0259-4

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