3a,11b-Dihydr­oxy-2-oxo-2,3,3a,11b-tetra­hydro-1H-imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride

Huang, Y.; Chen, M.-H.; Zhang, Y.-Q.; Xue, S.-F.; Tao, Z.

doi:10.1107/S160053680802093X

Volume 64
Part 8
Page o1489
August 2008

Received 7 June 2008
Accepted 7 July 2008
Online 16 July 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 11.9
Details

3a,11b-Dihydroxy-2-oxo-2,3,3a,11b-tetrahydro-1H-imidazo[4,5-f][1,10]phenanthrolin-7-ium chloride

Ying Huang,^a Ming-Hua Chen,^a Yun-Qian Zhang,^a Sai-Feng Xue ^a and Zhu Tao ^b ^*

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
Correspondence e-mail: sci.yqzhang@gzu.edu.cn

In the crystal structure of the title compound, C₁₃H₁₁N₄O₃⁺·Cl^-, the dihedral angle between the two pyridine rings is 9.72 (9) Å. Ions are linked via N-HCl, O-HCl and O-HO hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background, see: Zhao et al. (2004); Zheng et al. (2005).

Experimental

Crystal data

C₁₃H₁₁N₄O₃⁺·Cl^-
M_r = 306.71
Monoclinic, P 2₁ /c
a = 7.9420 (13) Å
b = 20.352 (3) Å
c = 8.2972 (14) Å
= 106.620 (5)°
V = 1285.1 (4) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 293 (2) K
0.31 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.909, T_max = 0.943
13480 measured reflections
2261 independent reflections
2094 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 1.05
2261 reflections
190 parameters
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1ACl1ⁱ	0.86	2.41	3.1512 (17)	145
N3-H3AO2ⁱⁱ	0.86	2.65	3.146 (2)	118
N4-H4Cl1ⁱⁱⁱ	0.86	2.50	3.2490 (16)	147
O2-H2ACl1	0.82	2.28	3.0712 (15)	163
O3-H3BO1^iv	0.82	1.89	2.6867 (18)	165
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2573 ).

Acknowledgements

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003) and the Foundation of the Governor of Guizhou Province, China.

References

Bruker, (2005). APEX2, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhao, Y. J., Xue, S. F., Zhu, Q. J., Tao, Z., Zhang, J. X., Wei, Z. B., Long, L. S., Hu, M. L., Xiao, H. P. & Day, A. I. (2004). Chin. Sci. Bull. 49, 1111-1116.
Zheng, L. M., Zhu, J. N., Zhang, Y. Q., Tao, Z., Xue, S. F., Zhu, Q. J., Wei, Z. B. & Long, L. S. (2005). Chin. J. Inorg. Chem. 21, 1583-1588.

organic compounds