3-Hydr­oxy-7,8-dimethoxy­quinolin-2(1H)-one

Song, J.; Lin, Y.; Chan, W.L.

doi:10.1107/S1600536808011549

Volume 64
Part 5
Page o934
May 2008

Received 21 April 2008
Accepted 22 April 2008
Online 30 April 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R = 0.054
wR = 0.175
Data-to-parameter ratio = 14.9
Details

3-Hydroxy-7,8-dimethoxyquinolin-2(1H)-one

Jian Song,^a Yongcheng Lin ^b ^* and Wing Lai Chan ^c

^aSchool of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, People's Republic of China,^bSchool of Chemistry and Chemical Engineering, Sun Yat-sun University, Guangzhou 510275, People's Republic of China, and ^cDepartment of Applied Biology and Chemistry Technology, Polytechnic University of Hong Kong, Hong Kong, People's Republic of China
Correspondence e-mail: zsusj@yahoo.com.cn

In the crystal structure of the title compound, C₁₁H₁₁NO₄, intramolecular O-HO hydrogen bonding results in the formation of a planar five-membered ring, which is nearly coplanar with the quinoline group. Intermolecular N-HO hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Beak (1977); Nimlos et al. (1987); Rajnikant et al. (2002); Johnson (1996). For related literature, see: Lin et al. (2000); Song et al. (2006).

Experimental

Crystal data

C₁₁H₁₁NO₄
M_r = 221.21
Monoclinic, P 2₁ /n
a = 4.9655 (16) Å
b = 14.084 (5) Å
c = 14.888 (5) Å
= 96.208 (6)°
V = 1035.1 (6) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 294 (2) K
0.60 × 0.37 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.937, T_max = 0.967
6788 measured reflections
2228 independent reflections
1761 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.174
S = 1.08
2228 reflections
150 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.50 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.90 (3)	2.07 (3)	2.938 (2)	161 (2)
O2-H2O1	0.82	2.33	2.756 (2)	113
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2455 ).

Acknowledgements

Financial support from the National Science Foundation of China (grant No. 20072058), the 863 Foundation of China (grant No. 2003 A A624010) and Guangdong Pharmaceutical University is gratefully acknowledged.

References

Beak, P. (1977). Acc. Chem. Res. 10, 186-192.
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, C. D. (1996). Comprehesive Heterocyclic Chemistry II, Vol. 5, edited by A. R. Katritzky, C. W Rees & E. F. V. Scriven, pp. 15-18. New York: Pergamon.
Lin, Y. C., Shao, Z., Jiang, G., Zhou, S., Cai, J., Vrijmoedand, L. L. P. & Jones, E. B. G. (2000). Tetrahedron, 56, 9607-9609.
Nimlos, M. R., Kelley, D. F. & Bernstein, E. R. (1987). J. Phys. Chem. 91, 6610-6614.
Rajnikant, G. V. K., Deshmukh, M. B. & Varghese, B. (2002). Dinesh Crystallogr. Rep. 47, 449-496.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, J., Lin, Y. C. & Chan, W. L. (2006). Heterocycles, 68, 1185-1190.

organic compounds