Abstract
The title compound (I), 4-(2,4-dihydroxybenzlideneamino)-5-methyl-2H-1,2,4-triazol-3(4H)-one was characterized by single crystal X-ray diffraction. This crystal is monoclinic, space group P21/c with a = 10.1447(7) Å, b = 7.0972(3) Å, c = 14.6726(10) Å, β = 98107(5)°, V = 1045.85(11) Å3, Z = 4, D c = 1.487 g/cm3, F 00 = 488, R = 0.039 and wR = 0.1025, S = 1.003, T = 293 (2) K. The title molecule is planar: the angle between the triazole ring and benzene ring is 179.1(1)°. The crystal structure contains two intramolecular (O–H···N and C–H···O) and three intermolecular interaction (O–H···N, N–H···O, and C–H···O). In addition, there is also π–π interactions.
Graphical Abstract
Crystal structure analysis of 4-(2,4-dihydroxybenzylideneamino)-5-methyl-2H-1,2,4-triazol-3(4H)-one
.
Similar content being viewed by others
References
Tsukuda T, Shiratori Y, Watanabe M, Ontsuka H, Hattori K, Shirai M, Shimma N (1998) Bioorg Med Chem Lett 8:1819–1824
Witkoaski JT, Robins RK, Sidwell RW, Simon LN (1972) J Med Chem 15:1150–1154
Sachse GB, Buerstell H (1979) Ger Offen 2:760–826
Tanaka G (1974) Japan Kokai 973:7495
Griffin DA, Mannion SK (1986) Eur Pat Appl EP 199:474
Jenkins TC, Stratfort IJ (1987) Anticancer Drug Des 4:145–160
Husain MI, Amir M (1986) J Indian Chem Soc 63:317
Chiu SHL, Huskey SEW (1998) Drug Metabol Dispos 26:838–847
Eliott R, Sunley RL, Griffin DA (1986) UK Pat Appl GB 2:175
Ünver Y, Dugdu E, Sancak K, Er M, Karaoglu ŞA (2009) Turk J Chem 33:135–147
Santen JR (2003) Steroids 68:559–567
Clemons M, Colemon RE, Verma S (2004) Cancer Treat Rew 30:325–332
Foroumadi A, Soltani F, Moshafi MF, Ashraf-Askari R (2003) IL Farmaco 58:1023–1028
Foroumadi A, Mansouri S, Kiani Z, Rahmani A (2003) A Eur J Med Chem 38:851–854
Foroumadi A, Mirzai M, Shafiee A (2001) IL Farmaco 56:621–623
Demirayak Ş, Benkli K, Güven K (2000) Eur J Chem 35:1037–1040
Demirbaş A, Johansson CB, Duman N, İkizler AA (1996) Acta Pol Pharm Drug Res 53:117–121
İkizler AA, Uzunali E, Demirbaş A (2000) Indian J Pharm 5:289–292
Holla BS, Poorjary KN, Tao BS, Shivananda MK (2002) Eur J Med Chem 37:511–517
Holla BS, Sarojini BK, Rao BS, Akberali PM, Kumari NS, Shatty V (2001) Il Farmaco 56:565–570
Ünver Y, Dugdu E, Sancak K, Er M, Karaoğlu ŞA (2008) J Chem 32:41–455
Stoe & Cie (2002) X-AREA (version 1.18) and X-RED32 (version 1.04). Stoe & Cie, Darmstadt, Germany
Farrugia LJ (1997) ORTEP III for windows. J Appl Cryst 30:565
Farrugia LJ (1999) WinGX for windows. J Appl Cryst 32:837–838
Seldrick GM (1997) SHELXS-97 and SHELXL-97. Programs for the solution and refinement of crystal structures. University of Göttingen, Germany
Fun HK, Jebas SR, Raob JN, Kalluraya B (2009) Acta Cryst E 65:o48
Fun HK, Kia R, Mirkhanib V, Zargoshi H (2008) Acta Cryst E64:o1790–o1791
Liu T (2009) Acta Cryst E65:o1502
Acknowledgments
The authors thank the Faculty of Art and Science, Ondokuz Mayıs Universty, Turkey, for the use of the STOE IPDS 2 diffractometer.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ustabaş, R., Ünlüer, D. & Kör, G. Crystal Structure 4-(2,4-Dihydroxybenzylideneamino)-5-methyl-2H-1,2,4-triazol-3(4H)-one. J Chem Crystallogr 41, 1237–1240 (2011). https://doi.org/10.1007/s10870-011-0081-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10870-011-0081-z