Crystal and Molecular Structure of 4-Benzoyl-1,5-diphenyl-1H-pyrazole-3-carbonitrile

Abstract

The crystal structure of potential active 4-benzoyl-1,5-diphenyl-1H*-pyrazole-3-carbonitrile (C23H15N3O) (I) has been determined from single crystal X-ray diffraction data. Also IR, Uv-vis and NMR spectral data were determined. The title compound crystallizes in the monoclinic space group P* 21/c, with a* = 9.3167(2), b* = 20.6677(3), c* = 10.6143(3) ?, β* = 112.665(3)°, V* = 1886.00(8) ?3, Dcalc* = 1.23g cm-3, Z* = 4. In the structure, intermolecular H*-bonds lead to the formation of a centrosymmetric dimmer of the molecule. Furthermore, the compound has a wide transmission window (300 to 1100 nm) with a transparency of nearly 100% and the UV cut-off wavelength occurs at 242 nm.

Share and Cite:

Korkusuz, E. , Şahin, E. and Yildirim, İ. (2012) Crystal and Molecular Structure of 4-Benzoyl-1,5-diphenyl-1H-pyrazole-3-carbonitrile. Crystal Structure Theory and Applications, 1, 1-8. doi: 10.4236/csta.2012.11001.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] A. M. Farghaly, N. S. Habib, M. A. Khalil and O. A. El- Sayed, Alexandria, Journal of Pharmaceutical Sciences, Vol. 3, 1989, p. 9.
[2] R. N. Mahajan, F. H. Havaldar and P. S. Fernandes, Jour- nal of Indian Chemical Society, Vol. 68, 1991, p. 245.
[3] P. G. Baraldi, S. Manfredini, R. Romagnoli, L. Stevanato, A. N. Zaid and R. Manservigi, “Synthesis and Anti-HSV-1 Activity of 6 Substituted Pyrazolo [3,4-d] Pyridazin- 7-one Nucleosides,” Nucleosides and Nucleotides, Vol. 17, No. 12, 1998, pp. 2165-2173. doi:10.1080/07328319808004307
[4] S. L. Janus, A. Z. Magdif, B. P. Erik and N. Claus, Monatshefte für Chemie/Chemical Monthly, Vol. 130, 1999, 1167.
[5] ?. Bildirici, A. ?ener and ?. Tozlu, “Further Derivatives of 4-Benzoyl-1,5-Diphenyl-1H-Pyrazole-3-Carboxylic Acid and Their Antibacterial Activities,” Medicinal Chemistry Research, Vol. 16, No. 7-9, 2007, pp. 418-426. doi:10.1007/s00044-007-9082-z
[6] S. Suzuki and A. Inoue, “Japanese Kokai Tokyo Koho JP 02 172 988 [90172988],” Chemical Abstracts, Vol. 113, 1990, Article ID: 218276.
[7] G. J. Hatheway, C. Hansch, K. H. Kim. S. R. Milstein, C. L. Schimidt, R. N. Smith and F. R. Quin, “Antitumor 1-(X-aryl)-3,3-dialkyltriazenes. 1. Quantitative Structure- Activity Relationships vs L1210 Leukemia in Mice,” Journal of Medical Chemisty, Vol. 21, No. 6, 1978, pp. 563-574. doi:10.1021/jm00204a012
[8] H. Katayama and T. Oshiyama, “Preparation and Bioac- tivity of Pyrazole Derivatives as Potential Cross-Linking Agent,” Canadian Journal of Chemistry, Vol. 75, No. 6, 1997, pp. 913-919. doi:10.1139/v97-109
[9] E. Badawey and I. M. El-Ashmawey, “Nonsteroidal Anti- inflammatory Agents—Part 1: Antiinflammatory, Anal- gesic and Antipyretic Activity of Some New 1-(Pyrimidin- 2yl)-3-Pyrazolin-5-ones and 2-(Pyrimidin-2-yl)-1,2,4,5,6, 7-Hexahydro-3H-indazol-3-ones,”European Journal of Medicinal Chemistry, Vol. 33, No. 5, 1998, pp. 349-361. doi:10.1016/S0223-5234(98)80002-0
[10] O. Bruno, A. Ranise, F. Bondavalli, P. Schenone and M. D’amico, Farmaco 47, 1992, p. 1235.
[11] P. D. Mishra, S. Wahidullah and S. Y. Kamat, Indian Journal of Chemistry, Vol. B 37, 1998, p. 199.
[12] W. T. Thomson, “Agricultural Chemicals-Book II: Herbicides,” 13th Edition, Thomson Publications, Fresno, 1997, pp. 268-278.
[13] M. Londershausen, “Review: Approaches to New Para- siticides,” Pesticide Science, Vol. 48, No. 4, 1996, pp. 269-292. doi:10.1002/(SICI)1096-9063(199612)48:4<269::AID-PS478>3.0.CO;2-B
[14] H. S. Chen and Z. M. Li, Chemical Journal of Chinese Universities, Vol. 19, 1998, p. 572.
[15] M. Kurowaski, A. Dunky and M. Geddawi, European Journal of Clinical Pharmacology, Vol. 307, 1987, p. 31.
[16] F. Lepage, B. Hublot, Eur. Pat. Appl. EP.459, 887; Chemical Abstracts, Vol. 116, 1992, 128917.
[17] D. M. Bailey, P. E. Hansen, A. G. Hlavac, E. R. Baizman, J. Pearl, A. F. Defelice and M. E. Feigenson, “3,4-Di- phenyl-1H-pyrazole-1-propanamine Antidepressants,” Jour- nal of Medical Chemisty, Vol. 28, No. 2, 1985, pp. 256- 260. doi:10.1021/jm00380a020
[18] R. H. Wiley and P. Wiley, “Pyrazolones, Pyrazolidones and Derivatives,” John Wiley and Sons, New York, 1964, p. 102.
[19] E. E. Baroni and K. A. Kovyrzina, Zhurnal Obshchei Khim, Vol. 31, 1961, p. 1641.
[20] S. Ohuchi, S. Okada, CA 130, 120912, JP 10338589, 1998.
[21] Y. Yoshikawa, K. Tomiya, T. Kitajima, H. Katsuta, O. Takahashi, S. Inami, Y. Yanase, N. Tomura, J. Kishi and H. Kawasima, CA 129, 16051, EP 841336 (1998).
[22] E. Ziegler, M. Eder, C. Belegratis, and E. Prewedourakis, “Synthesen von Heterocyclen, 103. Mitt.: über Reaktionen mit Oxalylchlorid (Kurze Mitteilung),” Monatshefte für Chemie/Chemical Monthly, Vol. 98, No. 6, 1967, pp. 2249-2251. doi:10.1007/BF00902421
[23] G. Kollenz, C. O. Kappe and H. A. El Nabey, “On the Reac- tion of 2,2,6,6-Tetramethyl-3,5-heptanedione (‘Dipivaloyl- methane’) with Oxalyl Chloride,” Heterocycles, Vol. 32, No. 4, 1991, pp. 669-673. doi:10.3987/COM-91-5679
[24] ?. ?. ?lhan, E. Sar?p?nar and Y. Ak?amur, Journal of Heterocyclic Chemistry, Vol. 42, 2005, p. 117.
[25] ?. Y?ld?r?m, F. Kandemirli and Y. Ak?amur, “Experimental and Quantum-Chemical Calculations on Some 1H- pyrazole-3-carboxamide and -3-Carboxylate Derivatives Formation,” Journal of Molecular Structure, Vol. 738, No. 1-3, 2005, pp. 275-279. doi:10.1016/j.molstruc.2004.12.026
[26] ?. Y?ld?r?m and F. Kandemirli, “Experimental and Theoretical Studies on the Functionalization Reactions of 4-Benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic Acid and-Acid Chloride with Various Aminophenols,” Structural Chemistry, Vol. 17, No. 2, 2006, pp. 241-247. doi:10.1007/s11224-006-9052-y
[27] Y. Ak?amur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E. M. Peters and H. G. von Schnering, “Reaktionen mit Cyclischen Oxalylverbindungen, XXIV. Zur Reaktion von 4-Benzoyl-5-phenyl-furan-2,3-dion mit Phe- nylhydrazonen bzw. Phenylhydrazin,” Monatshefte Für Chemie/Chemical Monthly, Vol. 117, No. 2, 1986, pp. 231-245. doi:10.1007/BF00809443
[28] Y. Ak?amur, A. ?ener, A. M. Ipekoglu and G. Kollenz, Journal of Heterocyclic Chemistry, Vol. 34, 1997, p. 221.
[29] A. ?ener, R. Kas?mogullar?, M. K. ?ener, I. Bildirici and Y. Ak?amur, Journal of Heterocyclic Chemistry, Vol. 39, 2002, p. 869.
[30] M. A. Cohen, J. Sawden and N. J. Turner, “Selective Hydrolysis of Nitriles under Mild Conditions by an Enzyme,” Tetrahedron Letters, Vol. 31, No. 49, 1990, 7223-7226. doi:10.1016/S0040-4039(00)97285-X
[31] M. E. Fabiani, Drug News & Perspectives, Vol. 12, 1999, pp. 207.
[32] F. F. Fleming, L. Yao, P. C. Ravikumar, L. Funk and B. C. Shook, Journal of Medical Chemisty, Vol. 53, No. 22, 2010, pp. 7902-7917.
[33] Rigaku/MSC, Inc., 9009 new Trails Drive, The Woodlands, TX 77381.
[34] G. M. Sheldrick, “SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement,” University of G?ttingen, 1997.
[35] L. Infants, C. Foces-Foces, R. M. Claramunt, C. Lopez and J. Elguero, “Tautomerism of NH-Pyrazolinones in the Solid State: The Case of 3(5)-Ethoxycarbonyl-5(3)- Hydroxypyrazole,” Journal of Molecular Structure, Vol. 447, No. 1-2, 1998, pp. 71-79. doi:10.1016/S0022-2860(98)00305-6
[36] F. Jimenez-Cruz, S. Hernandez-Ortega and H. Rios-Oli- vares, Journal of Molecular Structure, Vol. 650, 2003, p. 223.
[37] J. Quiroga-Puello, B. I. Obando, C. Foces-Foces, L. In- fantes, R. M. Claramunt, P. Cabildo, J. A. Jiminez and J. Elguero, Tetrahedron, Vol. 53, 1997, p. 10783.
[38] R. Krishna, D. Velmurugan, R. Murugesan, M. S. Sundaram and R. Raghunathan, Acta Crystallographica, Vol. C55, 1999, p. 1676.
[39] M. Burke-Laing and M. Laing, Acta Crystallographica, Vol. B32, 1976, p. 3216.
[40] G. C. Bassler, T. C. Morrill and R. M. Silverstein, “Spectrometric Identification of Organic Compounds,” Wiley, New York, 1991.

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.