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Volume 69 
Part 4 
Page o503  
April 2013  

Received 20 February 2013
Accepted 26 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.003 Å
R = 0.074
wR = 0.148
Data-to-parameter ratio = 21.6
Details
Open access

7-Hydroxymethyl-2-pivaloylamino-1,8-naphthyridine

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
Correspondence e-mail: hkfun@usm.my

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-H...N hydrogen bond, which generates an S(5) ring motif. In the crystal, molecules are linked into inversion dimers by pairs of N-H...O hydrogen bonds, generating 18-membered R22(18) ring motifs.

Related literature

For general background to and the medicinal properties of 1,8-naphthyridine derivatives see: Badawneh et al. (2001[Badawneh, M., Ferrarini, P. L., Calderone, V., Manera, C., Martinotti, E., Mori, C., Saccomanni, G. & Testai, L. (2001). Eur. J. Med. Chem. 36, 925-934.]); Litvinov (2004[Litvinov, V. P. (2004). Russ. Chem. Rev. 73, 637-669.]). For standard bond-length data, see: Allen et al. (1987[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.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17N3O2

  • Mr = 259.31

  • Monoclinic, P 21 /c

  • a = 14.7026 (3) Å

  • b = 6.2586 (1) Å

  • c = 14.7035 (3) Å

  • [beta] = 97.447 (2)°

  • V = 1341.57 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 297 K

  • 0.51 × 0.46 × 0.08 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.956, Tmax = 0.993

  • 20410 measured reflections

  • 3949 independent reflections

  • 2551 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.148

  • S = 1.14

  • 3949 reflections

  • 183 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H1N3...O2i 0.83 (2) 2.09 (2) 2.900 (2) 168 (2)
O2-H1O2...N2 0.86 (3) 2.10 (3) 2.648 (2) 121 (2)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5047 ).


Acknowledgements

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.

References

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.
Badawneh, M., Ferrarini, P. L., Calderone, V., Manera, C., Martinotti, E., Mori, C., Saccomanni, G. & Testai, L. (2001). Eur. J. Med. Chem. 36, 925-934.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Litvinov, V. P. (2004). Russ. Chem. Rev. 73, 637-669.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o503  [ doi:10.1107/S1600536813005527 ]

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