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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 [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.088
Data-to-parameter ratio = 12.0
Details
Open access

6-Chloroquinolin-2(1H)-one

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-H...O hydrogen bonds link the molecules into [010] C(4) chains. Aromatic [pi]-[pi] stacking interactions [shortest centroid...centroid distance = 3.685 (3) Å] are also observed.

Related literature

For background to quinoline derivatives as pharmaceuticals, see: Luo et al. (2011[Luo, Y.-H., Qian, X.-M., Gao, G., Li, J.-F. & Mao, S.-L. (2011). Acta Cryst. E67, m172.]).

[Scheme 1]

Experimental

Crystal data
  • C9H6ClNO

  • Mr = 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[alpha] radiation

  • [mu] = 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[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.917, Tmax = 0.917

  • 9911 measured reflections

  • 1353 independent reflections

  • 1161 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 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[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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.  [CSD] [CrossRef] [details]
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o188  [ doi:10.1107/S1600536811053359 ]

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