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

Gou, G.-Z.; Kou, J.-F.; Zhou, Q.-D.; Chi, S.-M.

doi:10.1107/S1600536812051112

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 (C-C) = 0.012 Å
R = 0.051
wR = 0.164
Data-to-parameter ratio = 11.6
Details

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

Gao-Zhang Gou,^a Jun-Feng Kou,^a Qing-Di Zhou ^b and Shao-Ming Chi ^a ^*

^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-HN, N-HO and C-HO hydrogen bonds link the molecules into heterodimers. These dimers are further linked into a one-dimensional structure along [010] by weak C-BrO interactions [BrO = 3.028 (5) Å and C-BrO = 158.52 (4)°].

Related literature

For coordination properties of 1,8-naphthyridine ligands, see: Gan et al. (2011); Chang et al. (2011); Das et al. (2012); Li et al. (2011). For similar structures, see: Li et al. (2011). For applications of similar compounds, see: Samadi et al. (2011); Li et al. (2012); Tanaka et al. (2012). For information on their synthesis, see: Henry & Hammond (1977); Wang et al. (2008).

Experimental

Crystal data

C₁₂H₁₁Br₂N₃O·C₄H₅NO₂
M_r = 472.15
Monoclinic, P 2₁ /m
a = 11.537 (2) Å
b = 7.0093 (14) Å
c = 11.632 (2) Å
= 106.57 (3)°
V = 901.6 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.450, T_max = 0.497
7056 measured reflections
1723 independent reflections
1220 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.164
S = 1.12
1723 reflections
148 parameters
H-atom parameters constrained
_max = 0.72 e Å^-3
_min = -0.92 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6AO1	0.93	2.25	2.838 (10)	121
C9-H9AO3ⁱ	0.98	2.55	3.507 (11)	166
N4-H4AN1ⁱⁱ	0.86	2.56	3.317 (9)	147
N4-H4AN2ⁱⁱ	0.86	2.24	3.045 (8)	157
N3-H3AO2ⁱ	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); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg,1999); 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.
Das, R. K., Sarkar, M., Wahidur Rahaman, S. M., Doucet, H. & Bera, J. K. (2012). Eur. J. Inorg. Chem. pp. 1680-1687.
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.
Henry, R. A. & Hammond, P. R. (1977). J. Heterocycl. Chem. pp. 1109-1114.
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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.
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Wang, D.-H., Yu, Y.-M., Chen, J.-H. & Fu, W.-F. (2008). Acta Cryst. E64, o112.

organic compounds