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Volume 69 
Part 2 
Pages o153-o154  
February 2013  

Received 29 November 2012
Accepted 18 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.012 Å
R = 0.051
wR = 0.164
Data-to-parameter ratio = 11.6
Details
Open access

N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)acetamide-pyrrolidine-2,5-dione (1/1)

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

In the title co-crystal, C12H11Br2N3O·C4H5NO2, the naphthyridine derivative and the pyrrolidine-2,5-dione molecules have crystallographic mirror-plane symmetry with all non-H atoms, except the Br atom, located on the mirror plane. In the crystal, N-H...N, N-H...O and C-H...O hydrogen bonds link the molecules into heterodimers. These dimers are further linked into a one-dimensional structure along [010] by weak C-Br...O interactions [Br...O = 3.028 (5) Å and C-Br...O = 158.52 (4)°].

Related literature

For coordination properties of 1,8-naphthyridine ligands, see: 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.]); Chang et al. (2011[Chang, Y. H., Liu, Z. Y., Liu, Y. H., Peng, S. M., Chen, J. T. & Liu, S. T. (2011). Dalton Trans. 40, 489-494.]); Das et al. (2012[Das, R. K., Sarkar, M., Wahidur Rahaman, S. M., Doucet, H. & Bera, J. K. (2012). Eur. J. Inorg. Chem. pp. 1680-1687.]); 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.]). For similar structures, see: 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.]). For applications of similar compounds, see: Samadi et al. (2011[Samadi, A., Valderas, C., Ríos, C. D. I., Bastida, A., Chioua, M., González-Lafuente, L., Colmena, I., Gandía, L., Romero, A., Barrio, L. D., Martín-de-Saavedra, M. D., López, M. G., Villarroya, M. & Marco-Contelles, J. (2011). Bioorg. Med. Chem. 19, 122-133.]); Li et al. (2012[Li, Z. X., Zhao, W. Y., Li, X. Y., Zhu, Y. Y., Liu, C. M., Wang, L. N., Yu, M. M., Wei, L. H., Tang, M. S. & Zhang, H. Y. (2012). Inorg. Chem. 51, 12444-12449.]); Tanaka et al. (2012[Tanaka, K., Murakami, M., Jeon, J. H. & Chujo, Y. (2012). Org. Biomol. Chem. 10, 90-95.]). For information on their synthesis, see: Henry & Hammond (1977[Henry, R. A. & Hammond, P. R. (1977). J. Heterocycl. Chem. pp. 1109-1114.]); Wang et al. (2008[Wang, D.-H., Yu, Y.-M., Chen, J.-H. & Fu, W.-F. (2008). Acta Cryst. E64, o112.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11Br2N3O·C4H5NO2

  • Mr = 472.15

  • Monoclinic, P 21 /m

  • a = 11.537 (2) Å

  • b = 7.0093 (14) Å

  • c = 11.632 (2) Å

  • [beta] = 106.57 (3)°

  • V = 901.6 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 4.52 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.450, Tmax = 0.497

  • 7056 measured reflections

  • 1723 independent reflections

  • 1220 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.164

  • S = 1.12

  • 1723 reflections

  • 148 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.92 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6A...O1 0.93 2.25 2.838 (10) 121
C9-H9A...O3i 0.98 2.55 3.507 (11) 166
N4-H4A...N1ii 0.86 2.56 3.317 (9) 147
N4-H4A...N2ii 0.86 2.24 3.045 (8) 157
N3-H3A...O2i 0.86 2.18 3.038 (9) 177
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear. 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: GK2541 ).


Acknowledgements

Support is acknowledged 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

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chang, Y. H., Liu, Z. Y., Liu, Y. H., Peng, S. M., Chen, J. T. & Liu, S. T. (2011). Dalton Trans. 40, 489-494.  [CSD] [CrossRef] [ChemPort] [PubMed]
Das, R. K., Sarkar, M., Wahidur Rahaman, S. M., Doucet, H. & Bera, J. K. (2012). Eur. J. Inorg. Chem. pp. 1680-1687.  [ISI] [CSD] [CrossRef]
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.
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]
Li, Z. X., Zhao, W. Y., Li, X. Y., Zhu, Y. Y., Liu, C. M., Wang, L. N., Yu, M. M., Wei, L. H., Tang, M. S. & Zhang, H. Y. (2012). Inorg. Chem. 51, 12444-12449.  [ISI] [CrossRef] [ChemPort]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Samadi, A., Valderas, C., Ríos, C. D. I., Bastida, A., Chioua, M., González-Lafuente, L., Colmena, I., Gandía, L., Romero, A., Barrio, L. D., Martín-de-Saavedra, M. D., López, M. G., Villarroya, M. & Marco-Contelles, J. (2011). Bioorg. Med. Chem. 19, 122-133.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tanaka, K., Murakami, M., Jeon, J. H. & Chujo, Y. (2012). Org. Biomol. Chem. 10, 90-95.  [CrossRef] [ChemPort] [PubMed]
Wang, D.-H., Yu, Y.-M., Chen, J.-H. & Fu, W.-F. (2008). Acta Cryst. E64, o112.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o153-o154   [ doi:10.1107/S1600536812051112 ]

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