Received 2 February 2013
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and cDepartment of Chemistry, Mangalore University, Karnataka, India
Correspondence e-mail: email@example.com
The asymmetric unit of the title compound, C9H11N3O2, contains two molecules (A and B), which exist in Z conformations with respect to their C=N double bond. The dihedral angles between the benzene ring and the pendant hydroxycarbamimidoyl and acetamide groups are 28.58 (7) and 1.30 (5)°, respectively, in molecule A and 25.04 (7) and 27.85 (9)°, respectively, in molecule B. An intramolecular N-HN hydrogen bond generates an S(6) ring in both molecules. Molecule A also features an intramolecular C-HO interaction, which closes an S(6) ring. In the crystal, the molecules are linked by N-HO, N-HN, O-HO, O-HN, C-HO and C-HN hydrogen bonds and C-H interactions, generating a three-dimensional network.
For background and applications of amidoximes, see: Clapp (1976, 1984); Jochims (1996); Fylaktakidou et al. (2008); Mansuy & Boucher (2004); Kontogiorgis & Hadjipavlou-Litina (2002); Wang et al. (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7034 ).
HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/CIPPM813040). CWO also thanks the Malaysian Goverment and USM for the award of the post of Research Officer under Research University Grant No. 1001/PFIZIK/811160.
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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clapp, L. B. (1976). In Advances in Heterocyclic Chemistry, Vol. 20, edited by A. R. Katritzky & A. J. Boulton, pp. 65-116. New York: Academic Press.
Clapp, L. B. (1984). In Comprehensive Heterocyclic Chemistry, Vol. 6, edited by K. T. Potts, pp. 365-392. Oxford: Pergamon Press.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E., Varella, E. & Nicolaides, D. N. (2008). Curr. Pharm. Des. 14, 1001-1047.
Jochims, J. C. (1996). In Comprehensive Heterocyclic Chemistry II, Vol. 52, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven, pp. 179-228. Oxford: Pergamon Press.
Kontogiorgis, C. A. & Hadjipavlou-Litina, D. J. (2002). Arzneim. Forsch. Drug. Res. 52, 205-210.
Mansuy, D. & Boucher, J. L. (2004). Free Radic. Biol. Med. 37, 1105-1121.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, P. G., Xian, M., Tang, X., Wu, X., Wen, Z., Cai, T. & Janczuk, A. J. (2002). Chem. Rev. 102, 1091-1134.