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Volume 69 
Part 4 
Page o489  
April 2013  

Received 19 February 2013
Accepted 23 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.160
Data-to-parameter ratio = 15.1
Details
Open access

N-(7-Methyl-1,8-naphthyridin-2-yl)acetamide-acetic acid (1/1)

aCollege of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, People's Republic of China,bSchool of Computer Science and Technology, Harbin Institute of Technology, Harbin 150001, People's Republic of China, and cSchool of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia
Correspondence e-mail: chishaoming@gmail.com

In the title adduct, C11H11N3O·C2H4O2, all non-H atoms of the acetamide molecule are roughly coplanar, with an r.m.s. deviation of 0.0720 Å. The dihedral angle between the ring plane and the acetamide group is 8.5 (2)°. In the crystal, O-H...N and N-H...O hydrogen bonds link the acetamide and acetic acid molecules.

Related literature

For the synthesis of 7-amino-2-methyl-1,8-naphthyridine, see: Brown (1965[Brown, E. V. (1965). J. Org. Chem. 30, 1607-1610.]); Henry & Hammond (1977[Henry, R. A. & Hammond, P. R. (1977). J. Heterocycl. Chem. pp. 1109-1114.]). For the coordination modes of 1,8-naphthyridine ligands, see: Zong et al. (2004[Zong, R. F., Naud, F., Segal, C., Burke, J., Wu, F. Y. & Thummel, R. (2004). Inorg. Chem. 43, 6195-6202.]); Zúñiga et al. (2011[Zúñiga, C., Moya, S. A., Fuentealba, M., Aranda, B. & Aguirre, P. (2011). Inorg. Chem. Commun. 14, 964-967.]); Li et al. (2011[Li, Z. X., Li, C., Mu, W. H., Xiong, S. X. & Fu, W. F. (2011). Inorg. Chim. Acta, 379, 7-15.]); Gan et al. (2011[Gan, X., Chi, S. M., Mu, W. H., Yao, J. C., Quan, L., Li, C., Bian, Z. Y., Chen, Y. & Fu, W. F. (2011). Dalton Trans. 40, 7365-7374.]). For their biological activity, see: Sivakumar et al. (2011[Sivakumar, P., Iyer, G. & Doble, M. (2011). Med. Chem. Res. pp. 1-8.]); Roma et al. (2000[Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1026.]); 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.]); Nagasawa et al. (2011[Nagasawa, J. Y., Song, J., Chen, H., Kim, H. W., Blazel, J., Ouk, S., Groschel, B., Borges, V., Ong, V., Yeh, L. T., Girardet, J. L., Vernier, J. M., Raney, A. K. & Pinkerton, A. B. (2011). Bioorg. Med. Chem. Lett. 21, 760-763.]); Capozzi et al. (2012[Capozzi, A., Mantuano, E., Matarrese, P., Saccomanni, G., Manera, C., Mattei, V., Gambardella, L., Malorni, W., Sorice, M. & Misasi, R. (2012). Anticancer Agents Med. Chem. 12, 653-662.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11N3O·C2H4O2

  • Mr = 261.28

  • Triclinic, [P \overline 1]

  • a = 8.3628 (17) Å

  • b = 9.0904 (18) Å

  • c = 9.5093 (19) Å

  • [alpha] = 71.30 (3)°

  • [beta] = 76.43 (3)°

  • [gamma] = 78.64 (3)°

  • V = 659.8 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.15 × 0.10 × 0.07 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.986, Tmax = 0.993

  • 5757 measured reflections

  • 2591 independent reflections

  • 1014 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.160

  • S = 0.91

  • 2591 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...N2i 0.82 1.96 2.774 (3) 173
N1-H1A...O2ii 0.86 2.07 2.931 (3) 178
Symmetry codes: (i) x+1, y-1, z; (ii) x-1, y+1, z.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2092 ).


Acknowledgements

The authors acknowledge support from the `Spring Sunshine' Plan of the Ministry of Education of China (grant No. Z2011125) and the National Natural Science Foundation of China (grant No. 21262049)

References

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]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brown, E. V. (1965). J. Org. Chem. 30, 1607-1610.  [CrossRef] [ChemPort]
Capozzi, A., Mantuano, E., Matarrese, P., Saccomanni, G., Manera, C., Mattei, V., Gambardella, L., Malorni, W., Sorice, M. & Misasi, R. (2012). Anticancer Agents Med. Chem. 12, 653-662.  [CrossRef] [ChemPort] [PubMed]
Gan, X., Chi, S. M., Mu, W. H., Yao, J. C., Quan, L., Li, C., Bian, Z. Y., Chen, Y. & Fu, W. F. (2011). Dalton Trans. 40, 7365-7374.  [CSD] [CrossRef] [ChemPort] [PubMed]
Henry, R. A. & Hammond, P. R. (1977). J. Heterocycl. Chem. pp. 1109-1114.  [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Li, Z. X., Li, C., Mu, W. H., Xiong, S. X. & Fu, W. F. (2011). Inorg. Chim. Acta, 379, 7-15.  [ISI] [CSD] [CrossRef] [ChemPort]
Nagasawa, J. Y., Song, J., Chen, H., Kim, H. W., Blazel, J., Ouk, S., Groschel, B., Borges, V., Ong, V., Yeh, L. T., Girardet, J. L., Vernier, J. M., Raney, A. K. & Pinkerton, A. B. (2011). Bioorg. Med. Chem. Lett. 21, 760-763.  [CrossRef] [ChemPort] [PubMed]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1026.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sivakumar, P., Iyer, G. & Doble, M. (2011). Med. Chem. Res. pp. 1-8.
Zong, R. F., Naud, F., Segal, C., Burke, J., Wu, F. Y. & Thummel, R. (2004). Inorg. Chem. 43, 6195-6202.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zúñiga, C., Moya, S. A., Fuentealba, M., Aranda, B. & Aguirre, P. (2011). Inorg. Chem. Commun. 14, 964-967.


Acta Cryst (2013). E69, o489  [ doi:10.1107/S1600536813005242 ]

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