Crystal and Molecular Structure of N-[2-(6-Methoxy-2-oxo-2H-Chromen-4-yl-Benzofuran-3-yl]- Benzamide

G. Anuradha, G. Vasuki, Imtiyaz Ahmed Khan, Manohar V. Kulkarni

Department of Chemistry, Karnatak University, Dharwad, India.
Department of Physics, Kunthavai Naachiar Government Arts College (w) (Autonomous), Thanjavur, India.

DOI: 10.4236/csta.2012.13020                

Abstract

The crystal structure of the potential active N-[2-(6-Methoxy-2-oxo-2H-chromen-4-yl)-benzofuran-3-yl]-benzamide (C₂₅H₁₇NO₅) (I) has been determined from single crystal X-ray diffraction data. The title compound crystallizes in the monoclinic space group P 21/n, with a = 12.0551(11), b = 9.7853(8), c = 16.6517(16) , β = 90.092(4)^o, V = 1964.28(3) ³, D_calc = 1.391 Mg/m³, Z = 4. In the structure, intermolecular H-bonds lead to the formation of a centrosymmetric dimer of the molecule. There is an intramolecular C7—H7…N1 hydrogen bond forming a closed seven membered ring. There are also intramolecular π-π interactions presented between the 3,6-Dihydro-2H-pyran ring of the chromen moiety [Cg2…Cg2 distance = 3.5812(13) ]. The packing structure is stabilized by these C—H…N, N—H…O hydrogen bonds, C—H… π and π…π interactions.

Keywords

Benzamide; Benzofuran; 2H-Chromen; Single Crystal Structure; X-Ray Diffraction

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	V. Z. Rodrigues, B. T. Gowda, V. Vrábel and J. Ko?í?ek, “4-Chloro-N-(3,5-Dimethylphenyl)Benzamide,” Acta Crystallographica E, Vol. 68, Part 3, 2012, p. o820. doi:10.1107/S1600536812007180
[2]	V. Maddi, S. N. Mamledesai, D. Satyanarayana and S. Swamy, “Synthesis and Antiinflammatory Activity of Substituted (2-Oxochromen-3-yl)Benzamides,” Indian Journal of Pharamceutical Sciences, Vol. 69, No. 6, 2007, pp. 847-849. doi:10.4103/0250-474X.39452
[3]	L. Muruganandam, S. Rajeswari, D. Tamilvendan, V. Ramkumar and G. V. Prabhu, “N-[Morpholino(phenyl)methyl] benzamide,” Acta Crystallographica E, Vol. 65, Part 3, 2009, p. o578. doi:10.1107/S1600536809005327
[4]	Anuradha Gurumoorthy, Vasuki Gopalsamy, K. Ramamurthi, Poonam Piplani and Ruchi Malik, “N-[4-(2-Morpholinoethoxy)Phenyl] Acetamide Monohydrate,” Acta Crystllographica E, Vol. 67, Part 2, 2011, p. o262. doi:10.1107/S1600536810053675
[5]	A. Saeed, S. Hussain and M. Bolte, “N-(2-MethoxyPhenyl)-2-Nitrobenzamide,” Acta Crystallographica E, Vol. 64, Part 12, 2008, p. o521. doi:10.1107/S1600536808002298
[6]	A. Saeed, R. A. Khera, N. Abbas, J. Simpson and R. G. Stanley, “N-Butyl-4-Chlorobenzamide,” Acta Crystallographica E, Vol. 64, Part 12, 2008, pp. o2322-o2323. doi:10.1107/S1600536808036313
[7]	Bruker, “APEX2 and SAINT-Plus,” Bruker AXS Inc., Madison, 2004.
[8]	G. M. Sheldrick, “SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement,” University of Gottingen, Gottingen, 1997.
[9]	G. M. Sheldrick, “A Short History of SHELX,” Acta Crystallographica A, Vol. 64, Part 1, 2008, pp. 112-122. doi:10.1107/S0108767307043930
[10]	L. J. Farrugia, “ORTEP-3 for Windows—A Version of ORTEP-III with a Graphical User Interface (GUI),” Journal of Applied Crystallography, Vol. 30, No. 1, 1997, p. 565. doi:10.1107/S0021889897003117
[11]	A. L. Spek, “Structure Validation in Chemical Crystallography,” Acta Crystallographica D, Vol. 65, Part 2, 2009, pp. 148-155. doi:10.1107/S090744490804362X
[12]	L. J. Farrugia, “WinGX Suite for Small-Molecule Single-Crystal Crystallography,” Journal of Applied Crystallography, Vol. 32, Part 4, 1999, pp. 837-838. doi:10.1107/S0021889899006020
[13]	Neerja Gupta and Ruby Naaz, International Journal of Pharma and Bio Sciences, Vol. 1, No. 3, 2010, pp. 1-7.
[14]	M. D. Ghate, M. V. Kulkarni, R. Shobha and S. Y. Kattimani, “Synthesis of Vanillin Ethers from 4-(Bromomethyl) Coumarins as Anti-Inflammatory Agents,” European Journal of Medicinal Chemistry, Vol. 38, No. 3, 2003, pp. 297-302. doi:10.1016/S0223-5234(03)00016-3