6-Chloro­quinolin-2(1H)-one

Zhang, C.-G.; Luo, Y.-H.

doi:10.1107/S1600536811053359

Volume 68
Part 1
Page o188
January 2012

Received 2 December 2011
Accepted 12 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.030
wR = 0.088
Data-to-parameter ratio = 12.0
Details

6-Chloroquinolin-2(1H)-one

Chen-Guang Zhang ^a ^* and Yang-Hui Luo ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: chmsunbw@seu.edu.cn

In the title compound, C₉H₆ClNO, the Cl atom deviates by 0.142 (1) Å from the quinoline ring mean plane (r.m.s. deviation = 0.013 Å). In the crystal, N-HO hydrogen bonds link the molecules into [010] C(4) chains. Aromatic [pi] - [pi] stacking interactions [shortest centroidcentroid distance = 3.685 (3) Å] are also observed.

Related literature

For background to quinoline derivatives as pharmaceuticals, see: Luo et al. (2011).

Experimental

Crystal data

C₉H₆ClNO
M_r = 179.60
Orthorhombic, P c c n
a = 24.951 (19) Å
b = 7.733 (6) Å
c = 7.988 (6) Å
V = 1541 (2) Å³
Z = 8
Mo K radiation
= 0.44 mm^-1
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.917, T_max = 0.917
9911 measured reflections
1353 independent reflections
1161 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.088
S = 1.06
1353 reflections
113 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.887 (19)	1.98 (2)	2.859 (2)	168.7 (17)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6549 ).

Acknowledgements

We thank Southeast University for support.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Luo, Y.-H., Qian, X.-M., Gao, G., Li, J.-F. & Mao, S.-L. (2011). Acta Cryst. E67, m172.
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds