N-H···O and C-H···O interaction mimicry in the 1:1 molecular complexes of 5,5-diethylbarbituric acid with urea and acetamide

Current Science

Volumn 98, Issue 6, 2010, Pages 793-802

  Thakur, Tejender S ^a   Azim, Yasser ^b   Srinu, Tothadi ^a   Desiraju, Gautam R ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b ALIGARH MUSLIM UNIVERSITY   (India)

Author keywords

Barbital; Co crystal; Hydrogen bond; Isostruc turality; X ray crystallography

Indexed keywords

EID: 77953353071     PISSN: 00113891     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Anthony, A., Jaskólski, M., Nangia, A. and Desiraju, G.R., Isostructurality in crystalline oxa-androgens. A case of C-O-H···O and C-H···O interaction mimicry and solid solution formation. Chem. Commun., 1998, 2537-2538.
2. Desiraju, G.R., C-H···O and other weak hydrogen bonds. From crystal engineering to virtual screening. Chem. Commun., 2005, 2995-3001.
3. Desiraju, G.R. and Steiner, T., The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1998.
4. For a description of a very recent recommendation to IUPAC on a modern definition of the term 'hydrogen bond', see http://ipc.iisc.ernet.in/~arunan/iupac/.
5. Childs, S.L. and Zaworotko, M.J., The reemergence of cocrys-tals: the crystal clear writing is on the wall. Introduction to virtual special issue on pharmaceutical cocrystals. Cryst. Growth Des., 2009, 9, 4208-4211.
6. Gartland, G.L. and Craven, B.M., Hydrogen bonding N-H···O=C of barbiturates: the (1: 1) crystal complex of urea and 5,5-diethylbarbituric acid (barbital). Acta Crystallogr. Sect. B, 1974, 30, 980-987.
7. Hsu, I.N. and Craven, B.M., The crystal structure of 1: 1 complex of acetamide with 5,5-diethylbarbituric acid (barbital). Acta Crystallogr. Sect. B, 1974, 30, 974-979.
8. Donohue, J., In Structural Chemistry and Molecular Biology (eds Rich, A. and Davidson, N.), Freeman, San Francisco, 1968, pp. 443-465.
9. Berkovitch-Yellin, Z. and Leiserowitz, L., The role played by C-H···O and C-H···N interactions in determining molecular packing and conformation. Acta Crystallogr., Sect. B, 1984, 40, 159-165.
10. Desiraju, G.R., Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989.
11. Gatti, C., May, E., Destro, R. and Cargnoni, F., Fundamental properties and nature of C-H···O interactions in crystals on the basis of experimental and theoretical charge densities. The case of 3,4-bis(dimethylamino)-3-cyclobutene-1,2-dione (DMACB) crystal. J. Phys. Chem. A, 2002, 106, 2707-2720.
12. Castellano, R.K., Progress towards understanding the nature and function of C-H···O interactions. Curr. Org. Chem., 2004, 8, 845-865.
13. Demartin, F., Fillippini, G., Gavezzotti, A. and Rizzato, S., X-ray diffraction and packing analysis on vintage crystals: Wilhelm Koerner's nitrobenzene derivatives from the school of agriculture sciences in Milano. Acta Crystallogr. Sect. B, 2004, 60, 609-620.
14. Dunitz, J.D. and Gavezzotti, A., Towards a quantitative description of crystal packing in terms of molecular pairs: application to the hexamorphic crystal system, 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile. Cryst. Growth Des., 2005, 5, 2180-2189.
15. 60: temperature dependence of weak C-H···O interactions. Helv. Chim. Acta, 1996, 79, 1047-1058.
16. Trask, A.V. and Jones, W., Crystal engineering of organic cocrystals by the solid state grinding approach. Top. Curr. Chem., 2005, 254, 41-70.
17. SMART, Version 5.05; Bruker AXS, Inc.: Madison, WI, 1998.
18. SAINT, Version 6.2; Bruker AXS, Inc.: Madison, WI, 2001.
19. Sheldrick, G.M., SHELXTL V5.1; Madison, WI, 1998.
20. CrystalClear 2.0, Rigaku Corporation, Tokyo, Japan.
21. Farrugia, L.J., Wingx suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr., 1999, 32, 837-838.
22. Desiraju, G.R., Supramolecular synthons in crystal engineering-a new organic synthesis. Angew. Chem. Int. Ed. Engl., 1995, 34, 2311-2327.