3-Chloro-4-methyl-quinolin-2(1H)-one.

Abstract

The title compound, C(10)H(8)ClNO, is almost planar (r.m.s. deviation for the 13 non-H atoms = 0.023 Å). In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) rings. Weak aromatic π-π stacking inter-actions [centroid-centroid distance = 3.7622 (12) Å] also occur.

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3-Chloro-4-methylquinolin-2(1H)-one
Mohamed G. Kassem,aHazem A. Ghabbour,aHatem A.
Abdel-Aziz,aHoong-Kun Funb*‡ and Chin Wei Ooib
aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud
University, PO Box 2457, Riyadh 11451, Saudi Arabia, andbX-ray Crystallography
Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my
Received 5 March 2012; accepted 6 March 2012
Key indicators: single-crystal X-ray study; T = 296 K; mean ?(C–C) = 0.003 A ˚;
R factor = 0.037; wR factor = 0.105; data-to-parameter ratio = 11.9.
The title compound, C10H8ClNO, is almost planar (r.m.s.
deviation for the 13 non-H atoms = 0.023 A˚). In the crystal,
inversion dimers linked by pairs of N—H???O hydrogen bonds
generate R2
[centroid–centroid distance = 3.7622 (12) A˚] also occur.
2(8) rings. Weak aromatic ?–? stacking interactions
Related literature
For the biological activity of quinoline, see: Michael et al.
(1996). For the synthesis, see: Hodgkinson & Staskun (1969).
For hydrogen-bond motifs, see: Bernstein et al. (1995). For a
related structure, see: Vasuki et al. (2001). For bond-length
data, see: Allen et al. (1987).
Experimental
Crystal data
C10H8ClNO
Mr= 193.62
Monoclinic, P21=c
a = 3.9361 (2) A˚
b = 12.9239 (6) A˚
c = 17.1019 (7) A˚
? = 100.197 (4)?
V = 856.23 (7) A˚3
Z = 4
Cu K? radiation
? = 3.56 mm?1
T = 296 K
0.92 ? 0.10 ? 0.10 mm
Data collection
Bruker APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
Tmin= 0.138, Tmax= 0.720
5522 measured reflections
1434 independent reflections
1178 reflections with I > 2?(I)
Rint= 0.040
Refinement
R[F2> 2?(F2)] = 0.037
wR(F2) = 0.105
S = 1.00
1434 reflections
120 parameters
H-atom parameters constrained
??max= 0.18 e A˚?3
??min= ?0.21 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
N1—H1???O1i
Symmetry code: (i) ?x þ 2;?y þ 1;?z þ 1.
D—HH???AD???AD—H???A
0.931.912.816 (2) 166
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT
(Bruker, 2009); data reduction: SAINT; 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 PLATON (Spek,
2009).
HKFand CWO thank Universiti Sains Malaysia (USM) for
the Research University Grant (1001/PFIZIK/811160). CWO
also thanks the Malaysian Government and USM for the
award of the post of research assistant under the Research
University Grant (1001/PFIZIK/811151). The authors thank
the Deanship of Scientific Research and the Research Center,
College of Pharmacy, King Saud University.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: HB6671).
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,
R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555–1573.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison,
Wisconsin, USA.
Hodgkinson, A. J. & Staskun, B. (1969). J. Org. Chem. 34, 1709–1713.
Michael, J. P., De Koning, C. B. & Stanbury, T. V. (1996). Tetrahedron Lett. 37,
9403–9406.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Vasuki, G., Parthasarathi, V., Ramamurthi, K., Jaisankar, P. & Varghese, B.
(2001). Acta Cryst. E57, o234–o235.
organic compounds
Acta Cryst. (2012). E68, o1043doi:10.1107/S1600536812009889 Kassem et al.
o1043
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
‡ Thomson Reuters ResearcherID: A-3561-2009.

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supplementary materials
Acta Cryst. (2012). E68, o1043 [doi:10.1107/S1600536812009889]
3-Chloro-4-methylquinolin-2(1H)-one
Mohamed G. Kassem, Hazem A. Ghabbour, Hatem A. Abdel-Aziz, Hoong-Kun Fun and Chin
Wei Ooi
Comment
For the previous reports of the chemistry and the biological activity of quinolines, see Michael et al. (1996).
In the title compound (Fig. 1), the quinoline ring (N1/C1–C9) is essentially planar with a maximum deviation of 0.012
(2) Å at atom C1. The bond lengths (Allen et al., 1987) and angles are within normal ranges are comparable to the related
structure (Vasuki et al., 2001).
In the crystal structure (Fig. 2), the adjacent molecules are linked via pair of N1—H1···O1 (Table 1) hydrogen bonds,
forming dimers with an R22 (8) ring motif (Bernstein et al., 1995). The crystal structure is further stabilized by weak π—π
interactions between the benzene ring (Cg1; C4–C9) and quinoline ring (Cg2; N1/C1–C9). [Cg1···Cg2 = 3.7622 (12) Å;
1+x, y, z].
Experimental
This compound was prepared according to the reported method (Hodgkinson & Staskun, 1969). Colorless needles of the
title compound were grown from a mixed solution of EtOH/DMF (V/V = 2/1) by slow evaporation at room temperature.
Refinement
Atom H1 was located from the difference map and was fixed at their found positions with Uiso(H) = 1.2 Ueq(N) [N–H =
0.9256 Å]. The remaining H atoms were positioned geometrically and refined using a riding model with Uiso(H) = 1.2 or
1.5Ueq(C) (C—H = 0.93 and 0.96 Å). A rotating group model was applied to the methyl group.
Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009);
program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL
(Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication:
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

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Figure 1
The molecular structure of the title compound, showing 30% probability displacement ellipsoids.

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Acta Cryst. (2012). E68, o1043
Figure 2
The crystal packing of the title compound, viewed along the b axis. H atoms not involved in the intermolecular
interactions (dashed lines) have been omitted for clarity.
3-Chloro-4-methylquinolin-2(1H)-one
Crystal data
C10H8ClNO
Mr = 193.62
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 3.9361 (2) Å
b = 12.9239 (6) Å
c = 17.1019 (7) Å
β = 100.197 (4)°
V = 856.23 (7) Å3
Z = 4
F(000) = 400
Dx = 1.502 Mg m−3
Cu Kα radiation, λ = 1.54178 Å
Cell parameters from 615 reflections
θ = 4.3–63.6°
µ = 3.56 mm−1
T = 296 K
Needle, colourless
0.92 × 0.10 × 0.10 mm

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Acta Cryst. (2012). E68, o1043
Data collection
Bruker APEXII CCD
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
φ and ω scans
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
Tmin = 0.138, Tmax = 0.720
5522 measured reflections
1434 independent reflections
1178 reflections with I > 2σ(I)
Rint = 0.040
θmax = 64.9°, θmin = 4.3°
h = −4→3
k = −15→14
l = −20→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.037
wR(F2) = 0.105
S = 1.00
1434 reflections
120 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0755P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.18 e Å−3
Δρmin = −0.21 e Å−3
Extinction correction: SHELXTL (Sheldrick,
2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.0031 (9)
Special details
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)
xyzUiso*/Ueq
Cl1
O1
N1
H1
C1
C2
C3
C4
C5
H5A
C6
H6A
C7
H7A
C8
1.04066 (14)
1.0673 (4)
0.7804 (4)
0.7928
0.9152 (5)
0.8689 (5)
0.7149 (4)
0.5836 (5)
0.4234 (5)
0.3935
0.3104 (6)
0.2094
0.3468 (6)
0.2690
0.4965 (5)
0.51266 (4)
0.46152 (12)
0.60196 (13)
0.5780
0.54435 (15)
0.58782 (15)
0.68001 (14)
0.73765 (14)
0.83478 (16)
0.8637
0.88763 (17)
0.9525
0.84441 (18)
0.8804
0.74913 (17)
0.76645 (3)
0.60239 (9)
0.54512 (9)
0.4947
0.60939 (12)
0.68546 (11)
0.69302 (11)
0.62192 (11)
0.62245 (12)
0.6706
0.55307 (14)
0.5546
0.48054 (14)
0.4337
0.47760 (12)
0.0516 (2)
0.0560 (4)
0.0422 (4)
0.051*
0.0414 (4)
0.0386 (4)
0.0371 (4)
0.0368 (4)
0.0446 (5)
0.054*
0.0529 (6)
0.064*
0.0552 (6)
0.066*
0.0477 (5)

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Acta Cryst. (2012). E68, o1043
H8A
C9
C10
H10A
H10B
H10C
0.5166
0.6184 (5)
0.6782 (6)
0.7537
0.4407
0.8168
0.7198
0.69643 (15)
0.72335 (16)
0.6728
0.7403
0.7846
0.4290
0.54803 (11)
0.77284 (11)
0.8133
0.7728
0.7833
0.057*
0.0385 (4)
0.0468 (5)
0.070*
0.070*
0.070*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
Cl1
O1
N1
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
0.0660 (4)
0.0806 (11)
0.0548 (10)
0.0486 (11)
0.0443 (10)
0.0386 (10)
0.0369 (10)
0.0451 (11)
0.0528 (12)
0.0574 (13)
0.0559 (12)
0.0395 (10)
0.0551 (12)
0.0475 (3)
0.0439 (9)
0.0398 (9)
0.0363 (10)
0.0376 (10)
0.0392 (10)
0.0363 (10)
0.0415 (11)
0.0430 (11)
0.0547 (14)
0.0498 (12)
0.0389 (10)
0.0491 (12)
0.0416 (3)
0.0462 (9)
0.0339 (9)
0.0412 (10)
0.0351 (10)
0.0349 (10)
0.0382 (10)
0.0474 (12)
0.0610 (14)
0.0506 (13)
0.0374 (11)
0.0380 (10)
0.0380 (10)
0.0056 (2)
0.0171 (8)
0.0011 (7)
−0.0011 (8)
−0.0038 (7)
−0.0065 (7)
−0.0046 (7)
−0.0002 (8)
0.0065 (9)
0.0009 (10)
−0.0005 (9)
−0.0045 (7)
0.0024 (9)
0.0105 (2)
0.0183 (7)
0.0134 (7)
0.0129 (8)
0.0104 (7)
0.0105 (7)
0.0090 (7)
0.0086 (8)
0.0046 (10)
0.0014 (10)
0.0084 (8)
0.0096 (7)
0.0128 (8)
0.0074 (2)
−0.0027 (7)
−0.0035 (7)
−0.0036 (8)
0.0000 (8)
−0.0042 (8)
−0.0041 (8)
−0.0062 (9)
0.0014 (10)
0.0121 (10)
0.0017 (9)
−0.0026 (8)
−0.0080 (9)
Geometric parameters (Å, º)
Cl1—C2
O1—C1
N1—C1
N1—C9
N1—H1
C1—C2
C2—C3
C3—C4
C3—C10
C4—C9
C4—C5
1.728 (2)
1.243 (3)
1.355 (3)
1.382 (3)
0.9256
1.458 (3)
1.353 (3)
1.442 (3)
1.506 (2)
1.400 (3)
1.406 (3)
C5—C6
C5—H5A
C6—C7
C6—H6A
C7—C8
C7—H7A
C8—C9
C8—H8A
C10—H10A
C10—H10B
C10—H10C
1.373 (3)
0.9300
1.391 (3)
0.9300
1.370 (3)
0.9300
1.393 (3)
0.9300
0.9600
0.9600
0.9600
C1—N1—C9
C1—N1—H1
C9—N1—H1
O1—C1—N1
O1—C1—C2
N1—C1—C2
C3—C2—C1
C3—C2—Cl1
C1—C2—Cl1
C2—C3—C4
C2—C3—C10
C4—C3—C10
124.95 (17)
119.6
115.4
121.42 (18)
123.80 (19)
114.78 (17)
123.60 (18)
122.45 (15)
113.93 (15)
118.30 (17)
122.04 (18)
119.65 (17)
C5—C6—C7
C5—C6—H6A
C7—C6—H6A
C8—C7—C6
C8—C7—H7A
C6—C7—H7A
C7—C8—C9
C7—C8—H8A
C9—C8—H8A
N1—C9—C8
N1—C9—C4
C8—C9—C4
120.2 (2)
119.9
119.9
120.4 (2)
119.8
119.8
119.5 (2)
120.3
120.3
119.43 (18)
119.21 (18)
121.37 (19)

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C9—C4—C5
C9—C4—C3
C5—C4—C3
C6—C5—C4
C6—C5—H5A
C4—C5—H5A
117.48 (18)
119.13 (18)
123.38 (18)
121.0 (2)
119.5
119.5
C3—C10—H10A
C3—C10—H10B
H10A—C10—H10B
C3—C10—H10C
H10A—C10—H10C
H10B—C10—H10C
109.5
109.5
109.5
109.5
109.5
109.5
C9—N1—C1—O1
C9—N1—C1—C2
O1—C1—C2—C3
N1—C1—C2—C3
O1—C1—C2—Cl1
N1—C1—C2—Cl1
C1—C2—C3—C4
Cl1—C2—C3—C4
C1—C2—C3—C10
Cl1—C2—C3—C10
C2—C3—C4—C9
C10—C3—C4—C9
C2—C3—C4—C5
C10—C3—C4—C5
−177.64 (19)
1.9 (3)
177.3 (2)
−2.2 (3)
−0.8 (3)
179.65 (14)
1.2 (3)
179.19 (13)
−178.76 (18)
−0.7 (3)
0.2 (3)
−179.84 (16)
−179.06 (18)
0.9 (3)
C9—C4—C5—C6
C3—C4—C5—C6
C4—C5—C6—C7
C5—C6—C7—C8
C6—C7—C8—C9
C1—N1—C9—C8
C1—N1—C9—C4
C7—C8—C9—N1
C7—C8—C9—C4
C5—C4—C9—N1
C3—C4—C9—N1
C5—C4—C9—C8
C3—C4—C9—C8
−0.9 (3)
178.36 (19)
1.4 (3)
−0.3 (3)
−1.2 (3)
178.74 (18)
−0.6 (3)
−177.72 (19)
1.6 (3)
178.79 (17)
−0.5 (3)
−0.5 (3)
−179.88 (17)
Hydrogen-bond geometry (Å, º)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i
0.93 1.91 2.816 (2) 166
Symmetry code: (i) −x+2, −y+1, −z+1.