Skip to main content
SpringerLink
Log in

An X-Ray Crystallographic Study of N-Methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

4H-chromenes are among the essential groups of biologically important compounds used as synthetic ligands for drug designing and discovery process. In this study, we have presented the single-crystal structure analysis of racemic 4H-chromene derivative namely N-methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine. The optical rotation measurement data is supporting that the title compound is racemic in nature. The compound was crystallized in monoclinic crystal system in the non-centrosymmetric space group P21 with unit cell parameters a = 5.1041 (3), b = 7.7519 (4), c = 14.7974 (8), α = 90°, β = 97.088 (5)° and γ = 90°. The nitro group of title compound is disordered over two orientations (N3A/O4A/O5A & N3B/O4B/O5B) with the refined site-occupancy ratio of 0.626(6)/0.374(6). The structure was solved by direct methods using the program SHELXS-97 and refined by SHELXL-97 with the full-matrix least square procedure to a final R-value of 0.0429 and Goodness of Fit (GooF) of 0.982. The molecules in the unit cell are stabilized by N–H···O and C–H···O types of hydrogen bonds. The intermolecular hydrogen bonds are forming C (6) motifs, which is observed to contribute the crystal packing stability. Moreover, the intramolecular hydrogen bonds are forming S (6) motif essential to stabilize the molecular structure of title compound.

Graphical Abstract

Graph-set S (6) and C (6) motifs are involved in stability of the structure and packing respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Cai SX (2007) Recent Patents Anticancer Drug Discov 2:79

    Article  CAS  Google Scholar 

  2. Cai SX (2008) Bioorg Med Chem Lett 18:603

    Article  Google Scholar 

  3. Cai SX, Drewe J, Kasibhatla S (2006) Curr Med Chem 13:2627

    Article  CAS  Google Scholar 

  4. Gabor M (1988) The pharmacology of benzopyrone derivatives and related compounds. Akademiai Kiado, Budapest, p 253

    Google Scholar 

  5. Brooks GT (1998) Pestic Sci 22:41

    Article  Google Scholar 

  6. Valenti P, Da Re P, Rampa A, Montanari P, Carrara M, Cima L (1993) Anticancer Drug Des 8:349

    CAS  Google Scholar 

  7. Tang Q-G, Wu W-Y, He W, Sun H-S, Guo C (2007) Acta Cryst E63:o1437

    CAS  Google Scholar 

  8. Kooijman H, Spek AL, Kleijn H, van Maanen HL, Jastrzebski JTBH, van Kozikowski AP (1984) Acc Chem Res 17:410

    Article  Google Scholar 

  9. Ellis GP (1997) Chromenes, chromanones and chromones. Wiley, New York, p 1196

    Google Scholar 

  10. Chenera B, West ML, Finkelstein JA, Dreyer GBJ (1993) J Org Chem 58:5605

    Article  CAS  Google Scholar 

  11. Li H-Q, Xiao Z-P, Han Y, Fang R-Q, Zhu H-L (2007) Acta Cryst E63:o3923

    CAS  Google Scholar 

  12. Atwal KS, Grover GJ, Ferrara FN, Ahmed SZ, Sleph PG, Dzwonczyk S, Normandin DE (1995) J Med Chem 38:1966

    Article  CAS  Google Scholar 

  13. Wang JL, Liu D, Zhang ZJ, Shan S, Han X, Srinivasula SM, Croce CM, Alnemri ES, Huang Z (2000) Proc Natl Acad Sci USA 97:7124

    Article  CAS  Google Scholar 

  14. Sheldrick GM (1993) SHELX93, program for crystal structure refinement. University of Gottingen, Gottingen

    Google Scholar 

  15. Oxford Diffraction (2009) CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton

    Google Scholar 

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

    CAS  Google Scholar 

  17. Farrugia LJ (1997) J Appl Cryst 30:565

    Article  CAS  Google Scholar 

  18. Spek AL (2009) Acta Cryst D 65:148

    Article  Google Scholar 

  19. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J (2006) J Appl Cryst 39:453

    Article  CAS  Google Scholar 

  20. Bhaskaran S, Velmurugan D, Ravikumar K, Geetha K, Rao HSP (2006) Acta Cryst E62:o188

    CAS  Google Scholar 

  21. Gayathri D, Velmurugan D, Ravikumar K, Geetha K, Rao HSP (2006) Acta Cryst E62:o1961

    CAS  Google Scholar 

  22. Butcher RJ, Jasinski JP, Yathirajan HS, Narayana B, Samshad (2007) Acta Cryst E63:o3412

    CAS  Google Scholar 

  23. Nallasivam A, Nethaji M, Vembu N, Ragunathan V, Sulochana N (2009) Acta Cryst E65:o504

    CAS  Google Scholar 

  24. Brito I, Bórquez J, Loyola LA, López-Rodríguez M (2008) Acta Cryst E64:o285

    CAS  Google Scholar 

  25. Hao L, Chen J, Zhang X (2010) Acta Cryst E66:o1564

    CAS  Google Scholar 

  26. Muthukumaran J, Parthiban A, Manivel P, Rao HSP, Krishna R (2011) Acta Cryst E67:o1395

    CAS  Google Scholar 

  27. Muthukumaran J, Parthiban A, Kannan M, Rao HSP, Krishna R (2011) Acta Cryst E67:o898

    CAS  Google Scholar 

  28. Muthukumaran J, Parthiban A, Manivel P, Rao HSP, Krishna R (2011) Acta Cryst E67:o1276

    CAS  Google Scholar 

  29. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) J Chem Soc Perkin Trans 2 12:S1

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

JM thanks the Council for Scientific and Industrial Research (CSIR) for a Senior Research Fellowship (SRF). RK thank the Centre for Bioinformatics (Funded by Department of Biotechnology and Department of Information Technology, New Delhi, India), Pondicherry University for providing the computational facilities to carry out this research work. AP thanks Pondicherry University for fellowship. HSP thanks the UGC (University Grant Commission) for the Special Assistance Programme (SAP) and the Department of Science and Technology (DST) for the Fund for Improvement of Science and Technology Infrastructure in Universities and Higher Educational Institutions (FIST).

Author information

Authors and Affiliations

  1. Centre for Bioinformatics, School of Life Sciences, Pondicherry University, Puducherry, 605014, India

    J. Muthukumaran & R. Krishna

  2. Department of Chemistry, Pondicherry University, Puducherry, 605014, India

    A. Parthiban & H. Surya Prakash Rao

Authors
  1. J. Muthukumaran
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. Parthiban
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. Surya Prakash Rao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. Krishna
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to H. Surya Prakash Rao or R. Krishna.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Muthukumaran, J., Parthiban, A., Rao, H.S.P. et al. An X-Ray Crystallographic Study of N-Methyl-3-nitro-4-(nitromethyl)-4H-chromen-2-amine. J Chem Crystallogr 41, 1927–1934 (2011). https://doi.org/10.1007/s10870-011-0201-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0201-9

Keywords

Search

Navigation