Browse > Article
http://dx.doi.org/10.13160/ricns.2013.6.4.197

Crystal and Molecular Structure of 4,6-Dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo [8.8.0.02,7.013,18]octadeca-2(7),13,15,17-tetraene-3,5,11-trione 2-ethoxyphenyl (2E)-but-2-enoate  

Ganapathy, Jagadeesan (Department of Physics, Presidency College)
Damodharan, Kannan (Department of Organic Chemistry, University of Madras, Guindy Campus)
Manickam, Bakthadoss (Department of Organic Chemistry, University of Madras, Guindy Campus)
Sanmargam, Aravindhan (Department of Physics, Presidency College)
Publication Information
Journal of Integrative Natural Science / v.6, no.4, 2013 , pp. 197-204 More about this Journal
Abstract
The crystal structure of the potential active 4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo [8.8.0.02,7.013,18] octadeca-2(7),13,15,17-tetraene-3,5,11-trione 2-ethoxyphenyl (2E)-but-2-enoate ($C_{22}H_{18}N_2O_5$) has been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P_12_1/c_1$ with unit cell dimension a=15.2039(8), b=12.3888(6) and c= 9.8162(5) [alpha & $gamma=90^{\circ}$ beta=98.113(2)]. In the structure fused pyrone and pyran rings each adopt a sofa/envelop conformation. The crystal structure is stabilized by intramolecular C-H... O hydrogen bond interaction.
Keywords
Pyrone; Pyran; Cumarine; Single Crystal Structure; X-ray Diffraction;
Citations & Related Records
연도 인용수 순위
  • Reference
1 V. Maddi, S. N. Mamledesai, D. Satyanarayana, and S. Swamy, "Synthesis and antiinflammatory activity of aubstituted (2-oxochromen-3-yl)benzamides", Indian Journal of Pharamceutical Sciences, Vol. 69, pp. 847-849, 2007.   DOI
2 S. Kawaii, Y. Tomono, K. Ogawa, M. Sugiura, M. Yano, Y. Yoshizawa, C. Ito, and H. Furukawa, "Antiproliferative effect of isopentenylated coumarins on several cancer cell lines", Anticancer Res., Vol. 21, pp. 1905-1911, 2001.
3 C. F. Hossain, E. Okuyama, and M. Yamazaki, "A new series of coumarin derivatives having monoamine oxidase inhibitory activity from Monascus anka", Chem. Pharm. Bull., Vol. 44, pp. 1535-1539, 1996.   DOI   ScienceOn
4 R. K. Goel, R. N. Maiti, M. Manickam, and A. B. Ray, "Antiulcer activity of naturally occurring pyrano- coumarin and isocoumarins and their effect on prostanoid synthesis using human colonic mucosa", Indian J. Exp. Biol., Vol. 35, pp. 1080-1083, 1997.
5 J. R. Casley-Smith, C. T. Wang, J. R. Casley-Smith, and C. Zi-hai, "Treatment of filarial lymphoedema and elephantiasis with 5,6-benzo-${\alpha}$-pyrone (coumarin)", Br. Med. J., Vol. 307, pp. 1037-1041, 1993.   DOI
6 C. R. Su, S. F. Yeh, C. M. Liu, A. G. Damu, T. H. Kuo, P. C. Chiang, K. F. Bastow, K. H. Lee, and T. S. Wu, "Anti-HBV and cytotoxic activities of pyranocoumarin derivatives", Bioorg. Med. Chem., Vol. 17, pp. 6137-6143, 2009.   DOI   ScienceOn
7 Z. Q. Xu, K. Pupek, W. J. Suling, L. Enache, and M. T. Flavin, "Pyranocoumarin, a novel anti-TB pharmacophore: synthesis and biological evaluation against Mycobacterium tuberculosis", Bioorg. Med. Chem., Vol. 14, pp. 4610-4626, 2006.   DOI   ScienceOn
8 F. Pavao, M. S. Castilho, M. T. Pupo, R. L. A. Dias, A. G. Correa, J. B. Fernandes, M. F. G. F. Da Silva, J. Mafezoli, P. C. Vieir, and G. Oliva, "Structure of Trypanosoma cruzi glycosomal glyceraldehyde-3- phosphate dehydrogenase complexed with chalepin, a natural product inhibitor, at 1.95 A resolution", FEBS Lett., Vol. 520, pp. 13-17, 2002.   DOI   ScienceOn
9 Bruker, APEX2 and SAINT-Plus, Bruker AXS Inc., Madison, 2004.
10 G. M. Sheldrick, SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement, University of Gottingen, Gottingen, 1997.
11 G. M. Sheldrick. "A short history of SHELX", Acta Cryst. A, Vol. 64, pp. 112-122, 2008.   DOI   ScienceOn
12 G. Jagadeesan, D. Kannan, M. Bakthadoss, and S. Aravindhan, "14-Ethoxy-4,6,9-trimethyl-8,12-dioxa- 4,6-diazatetracyclo-[8.8.0.02,7.013,18]octadeca-2(7), 13,15,17-tetraene-3,5,11-trione", Acta Cryst. E, Vol. 69, p. o272, 2013.   DOI   ScienceOn
13 L. J. Farrugia. "ORTEP-3 for windows-a version of ORTEP-III with a graphical user interface (GUI)", J. Appl. Crystallog., Vol. 30, p. 565, 1997.
14 A. L. Spek, "Structure validation in chemical crystallography", Acta Cryst. D, Vol. 65, pp. 48-155, 2009.   DOI   ScienceOn
15 L. J. Farrugia, "WinGX suite for small-molecule single-crystal crystallography", J. Appl. Crystallog., Vol. 32, pp. 837-838, 1999.   DOI
16 G. Jagadeesan, D. Kannan, M. Bakthadoss, and S. Aravindhan, "14-Ethoxy-4,6- dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo- [8.8.0.02,7.013,18]octadeca-2(7),13,15,17-tetraene- 3,5,11-trione", Acta Cryst. E, Vol. 69, p. o80, 2013.
17 M. Nardelli, "Ring asymmetry parameters from outof- plane atomic displacements", Acta Cryst. C, Vol. 39, pp. 1141-1142, 1983.   DOI