6-Chloro­quinolin-2(1H)-one

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

doi:10.1107/S1600536811053359

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o188

doi:10.1107/S1600536811053359

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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

(Received 2 December 2011; accepted 12 December 2011; online 21 December 2011)

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 π–π 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 ).

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 Kα radiation
μ = 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 > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(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
Δρ_max = 0.17 e Å⁻³
Δρ_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); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053359/hb6549sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053359/hb6549Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053359/hb6549Isup3.cml

checkCIF report

Related literature top

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

Experimental top

The title compound was purchased from ChemFuture PharmaTech, Ltd (Nanjing, Jiangsu). Pink prisms were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing view down the a axis showing hydrogen bonds as dashed lines.

6-Chloroquinolin-2(1H)-one top

Crystal data top

C₉H₆ClNO	F(000) = 736
M_r = 179.60	D_x = 1.548 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1357 reflections
a = 24.951 (19) Å	θ = 1.6–25.0°
b = 7.733 (6) Å	µ = 0.44 mm⁻¹
c = 7.988 (6) Å	T = 296 K
V = 1541 (2) Å³	Prism, pink
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku SCXmini CCD diffractometer	1353 independent reflections
Radiation source: fine-focus sealed tube	1161 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 1.6°
CCD_Profile_fitting scans	h = −29→29
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
T_min = 0.917, T_max = 0.917	l = −8→9
9911 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0469P)² + 0.4479P] where P = (F_o² + 2F_c²)/3
1353 reflections	(Δ/σ)_max = 0.001
113 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

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

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
1353 reflections	Δρ_min = −0.23 e Å⁻³
113 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.73621 (2)	1.01875 (7)	0.69204 (7)	0.0614 (2)
N1	0.54956 (5)	0.88864 (17)	1.12378 (17)	0.0369 (3)
O1	0.49027 (5)	0.70991 (15)	1.25021 (16)	0.0472 (3)
C1	0.53024 (6)	0.7277 (2)	1.1598 (2)	0.0369 (4)
C5	0.59440 (6)	0.9205 (2)	1.02710 (19)	0.0349 (4)
C2	0.55943 (7)	0.5842 (2)	1.0882 (2)	0.0398 (4)
H2	0.5477	0.4719	1.1079	0.048*
C4	0.62280 (6)	0.7806 (2)	0.95924 (19)	0.0357 (4)
C9	0.66766 (7)	0.8129 (2)	0.8591 (2)	0.0409 (4)
H9	0.6871	0.7214	0.8140	0.049*
C7	0.65567 (7)	1.1184 (2)	0.8970 (2)	0.0487 (5)
H7	0.6671	1.2308	0.8759	0.058*
C8	0.68283 (7)	0.9794 (2)	0.8280 (2)	0.0426 (4)
C3	0.60308 (7)	0.6101 (2)	0.9940 (2)	0.0404 (4)
H3	0.6211	0.5151	0.9500	0.049*
C6	0.61155 (7)	1.0894 (2)	0.9970 (2)	0.0453 (4)
H6	0.5933	1.1821	1.0443	0.054*
H1	0.5337 (8)	0.980 (2)	1.170 (2)	0.044 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0512 (3)	0.0595 (3)	0.0736 (4)	0.0024 (2)	0.0190 (2)	0.0143 (2)
N1	0.0428 (8)	0.0276 (7)	0.0404 (8)	0.0031 (6)	0.0035 (6)	−0.0012 (6)
O1	0.0483 (7)	0.0359 (7)	0.0574 (8)	−0.0015 (5)	0.0130 (7)	0.0020 (6)
C1	0.0406 (9)	0.0330 (9)	0.0371 (9)	−0.0011 (7)	−0.0033 (7)	0.0012 (7)
C5	0.0383 (8)	0.0322 (8)	0.0342 (8)	0.0014 (7)	−0.0020 (7)	−0.0001 (7)
C2	0.0470 (10)	0.0269 (8)	0.0454 (9)	0.0006 (7)	−0.0023 (8)	−0.0004 (7)
C4	0.0394 (8)	0.0317 (9)	0.0359 (9)	0.0045 (6)	−0.0050 (7)	0.0004 (7)
C9	0.0399 (9)	0.0400 (9)	0.0428 (10)	0.0078 (7)	−0.0007 (8)	−0.0004 (8)
C7	0.0499 (10)	0.0343 (9)	0.0618 (11)	−0.0035 (8)	0.0056 (9)	0.0036 (9)
C8	0.0368 (9)	0.0450 (10)	0.0461 (10)	0.0016 (7)	0.0009 (7)	0.0049 (8)
C3	0.0475 (10)	0.0298 (8)	0.0440 (10)	0.0078 (7)	−0.0022 (8)	−0.0025 (7)
C6	0.0506 (10)	0.0294 (9)	0.0558 (11)	0.0031 (7)	0.0071 (9)	−0.0024 (8)

Geometric parameters (Å, º) top

Cl1—C8	1.745 (2)	C4—C9	1.398 (2)
N1—C1	1.365 (2)	C4—C3	1.434 (2)
N1—C5	1.382 (2)	C9—C8	1.365 (3)
N1—H1	0.887 (19)	C9—H9	0.9300
O1—C1	1.239 (2)	C7—C6	1.379 (3)
C1—C2	1.445 (2)	C7—C8	1.385 (3)
C5—C6	1.395 (2)	C7—H7	0.9300
C5—C4	1.402 (2)	C3—H3	0.9300
C2—C3	1.339 (2)	C6—H6	0.9300
C2—H2	0.9300

C1—N1—C5	124.49 (14)	C8—C9—C4	119.66 (15)
C1—N1—H1	118.7 (12)	C8—C9—H9	120.2
C5—N1—H1	116.7 (12)	C4—C9—H9	120.2
O1—C1—N1	120.54 (15)	C6—C7—C8	119.65 (16)
O1—C1—C2	123.46 (15)	C6—C7—H7	120.2
N1—C1—C2	116.00 (15)	C8—C7—H7	120.2
N1—C5—C6	120.77 (14)	C9—C8—C7	121.59 (17)
N1—C5—C4	119.20 (14)	C9—C8—Cl1	119.31 (14)
C6—C5—C4	120.03 (16)	C7—C8—Cl1	119.06 (14)
C3—C2—C1	121.17 (15)	C2—C3—C4	121.70 (15)
C3—C2—H2	119.4	C2—C3—H3	119.2
C1—C2—H2	119.4	C4—C3—H3	119.2
C9—C4—C5	119.21 (15)	C7—C6—C5	119.83 (16)
C9—C4—C3	123.33 (15)	C7—C6—H6	120.1
C5—C4—C3	117.44 (15)	C5—C6—H6	120.1

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₉H₆ClNO
M_r	179.60
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	296
a, b, c (Å)	24.951 (19), 7.733 (6), 7.988 (6)
V (Å³)	1541 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.917, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	9911, 1353, 1161
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.088, 1.06
No. of reflections	1353
No. of parameters	113
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

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+1/2, −z+5/2.

Acknowledgements

We thank Southeast University for support.

References

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