Received 4 March 2013
aDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India,cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and eDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
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The molecule of the title compound, C12H14N4O, is roughly planar, with a dihedral angle of 8.0 (8)° between the benzene and pyrazole rings, and an intramolecular N-HO hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked into an inversion dimer by a pair of N-HO hydrogen bonds, which form an R22(8) ring motif.
For the biological activity of pyrazolones, see: Amir & Kumar (2005); Rao et al. (2008); Samshuddin et al. (2011). For the radical scavenging capacity of pyrazol-5-ols, see: Sarojini et al. (2010). For related structures, see: Butcher et al. (2011); Samshuddin et al. (2011). For reference bond-length data, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO ; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5254 ).
BKS gratefully acknowledges the Department of Atomic Energy (DAE)/BRNS, Government of India, for providing financial assistance in the BRNS Project (No. 2011/34/20-BRNS/0846). RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Amir, M. & Kumar, S. (2005). Indian. J. Chem. Sect. B, 44, 2532-2537.
Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1019.
Rao, B. S., Akberali, P. M., Holla, B. S. & Sarojini, B. K. (2008). J. Pharmacol. Toxicol. 3, 102-103.
Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Darshan Raj, C. G. & Raghavendra, R. (2011). Med. Chem. Res. 21, 2012-2022.
Sarojini, B. K., Vidyagayatri, M., Darshan Raj, C. G., Barath, B. R. & Manjunatha, H. (2010). Lett. Drug Des. Discov. 7, 214-224.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.