5,6,7-Trichloro-2-meth­oxy-8-hy­droxy­quinoline

Chen, Q.-M.; Yi, G.-B.; An, L.-K.; Feng, X.-L.

doi:10.1107/S1600536811010853

Volume 67
Part 5
Page o1108
May 2011

Received 22 February 2011
Accepted 23 March 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.110
Data-to-parameter ratio = 13.8
Details

5,6,7-Trichloro-2-methoxy-8-hydroxyquinoline

Qiu-Mao Chen,^a,^b Guo-Bin Yi,^a Lin-Kun An ^b and Xiao-Long Feng ^c ^*

^aFaculty of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China,^bSchool of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China, and ^cInstrumental Analysis & Research Center, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China
Correspondence e-mail: pusfxl@mail.sysu.edu.cn

In the title compound, C₁₀H₆Cl₃NO₂, a mean plane fitted through all non-H atoms has an r.m.s. deviation of 0.035 Å. In the crystal, adjacent molecules are connected by O-HO hydrogen bonds and [pi] - [pi] stacking interactions [centroid-centroid distance = 3.650 (1) Å], resulting in an infinite chain which propagates in the b-axis direction.

Related literature

The title compound was obtained as an unexpected product from an attempt to synthesize a Top1 (DNA topoisomerase IB) inhibitor For general background to Top1, see: Pommier (2006). For the synthesis, see: Shen et al. (2008); Cheng et al. (2008).

Experimental

Crystal data

C₁₀H₆Cl₃NO₂
M_r = 278.51
Monoclinic, P 2₁ /c
a = 10.0782 (3) Å
b = 4.9979 (1) Å
c = 21.5827 (6) Å
= 99.287 (2)°
V = 1072.87 (5) Å³
Z = 4
Cu K radiation
= 7.61 mm^-1
T = 150 K
0.40 × 0.21 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Onyx Nova diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.151, T_max = 0.312
4752 measured reflections
2035 independent reflections
1812 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.110
S = 1.04
2035 reflections
147 parameters
H-atom parameters constrained
_max = 0.98 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO2ⁱ	0.84	2.25	2.9844 (16)	146
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2089 ).

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (No. 30801425) and Guangdong Natural Science Fund (No. 10151008901000022).

References

Cheng, Y., An, L. K., Wu, N., Wang, X. D., Bu, X. Z., Huang, Z. S. & Gu, L. Q. (2008). Bioorg. Med. Chem. 16, 4617-4625.
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Pommier, Y. (2006). Nature Rev. 6, 789-802.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shen, D. Q., Cheng, Y., An, L. K., Bu, X. Z., Huang, Z. S. & Gu, L. Q. (2008). Chin. Chem. Lett. 19, 533-536.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds