Received 20 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, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
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In the title compound, C14H17N3O2, the mean plane of the 1,8-naphthyridine ring system (r.m.s deviation = 0.020 Å) forms a dihedral angle of 23.4 (1)° with the acetamide moiety (r.m.s deviation = 0.001 Å). The molecular structure is stabilized by an intramolecular O-HN hydrogen bond, which generates an S(5) ring motif. In the crystal, molecules are linked into inversion dimers by pairs of N-HO hydrogen bonds, generating 18-membered R22(18) ring motifs.
For general background to and the medicinal properties of 1,8-naphthyridine derivatives see: Badawneh et al. (2001); Litvinov (2004). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).
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: RZ5047 ).
The authors thank Universiti Sains Malaysia (USM) for the RUC grant (Structure Determination of 50 kDa Outer Membrane Proteins From S.typhi By X-ray Protein Crystallography, No. 1001/PSKBP/8630013) and APEX DE2012 grant (No.1002/PFIZIK/910323). The authors also thank the CSIR and DST, Government of India, for financial support.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.