3-Chloro-4-methyl­quinolin-2(1H)-one

Kassem, M.G.; Ghabbour, H.A.; Abdel-Aziz, H.A.; Fun, H.-K.; Ooi, C.W.

doi:10.1107/S1600536812009889

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1043

doi:10.1107/S1600536812009889

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3-Chloro-4-methylquinolin-2(1H)-one

Mohamed G. Kassem,^a Hazem A. Ghabbour,^a Hatem A. Abdel-Aziz,^a Hoong-Kun Fun ^b ^*‡ and Chin Wei Ooi ^b

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-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; online 14 March 2012)

The title compound, C₁₀H₈ClNO, 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 R₂²(8) rings. Weak aromatic π–π stacking interactions [centroid–centroid distance = 3.7622 (12) Å] also occur.

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
M_r = 193.62
Monoclinic, P 2₁ /c
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
Cu Kα radiation
μ = 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 ) T_min = 0.138, T_max = 0.720
5522 measured reflections
1434 independent reflections
1178 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.00
1434 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.93	1.91	2.816 (2)	166
Symmetry code: (i) -x+2, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009889/hb6671sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009889/hb6671Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009889/hb6671Isup3.cml

checkCIF report

Comment top

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].

Related literature top

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 top

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.

Structure description top

For the previous reports of the chemistry and the biological activity of quinolines, see Michael et al. (1996).

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).

Computing details top

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).

Figures top

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

Crystal data top

C₁₀H₈ClNO	F(000) = 400
M_r = 193.62	D_x = 1.502 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 615 reflections
a = 3.9361 (2) Å	θ = 4.3–63.6°
b = 12.9239 (6) Å	µ = 3.56 mm⁻¹
c = 17.1019 (7) Å	T = 296 K
β = 100.197 (4)°	Needle, colourless
V = 856.23 (7) Å³	0.92 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1434 independent reflections
Radiation source: fine-focus sealed tube	1178 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 64.9°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→3
T_min = 0.138, T_max = 0.720	k = −15→14
5522 measured reflections	l = −20→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0755P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
1434 reflections	Δρ_max = 0.18 e Å⁻³
120 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (9)

Crystal data top

C₁₀H₈ClNO	V = 856.23 (7) Å³
M_r = 193.62	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 3.9361 (2) Å	µ = 3.56 mm⁻¹
b = 12.9239 (6) Å	T = 296 K
c = 17.1019 (7) Å	0.92 × 0.10 × 0.10 mm
β = 100.197 (4)°

Data collection top

Bruker APEXII CCD diffractometer	1434 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1178 reflections with I > 2σ(I)
T_min = 0.138, T_max = 0.720	R_int = 0.040
5522 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
1434 reflections	Δρ_min = −0.21 e Å⁻³
120 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	1.04066 (14)	0.51266 (4)	0.76645 (3)	0.0516 (2)
O1	1.0673 (4)	0.46152 (12)	0.60239 (9)	0.0560 (4)
N1	0.7804 (4)	0.60196 (13)	0.54512 (9)	0.0422 (4)
H1	0.7928	0.5780	0.4947	0.051*
C1	0.9152 (5)	0.54435 (15)	0.60939 (12)	0.0414 (4)
C2	0.8689 (5)	0.58782 (15)	0.68546 (11)	0.0386 (4)
C3	0.7149 (4)	0.68001 (14)	0.69302 (11)	0.0371 (4)
C4	0.5836 (5)	0.73765 (14)	0.62192 (11)	0.0368 (4)
C5	0.4234 (5)	0.83478 (16)	0.62245 (12)	0.0446 (5)
H5A	0.3935	0.8637	0.6706	0.054*
C6	0.3104 (6)	0.88763 (17)	0.55307 (14)	0.0529 (6)
H6A	0.2094	0.9525	0.5546	0.064*
C7	0.3468 (6)	0.84441 (18)	0.48054 (14)	0.0552 (6)
H7A	0.2690	0.8804	0.4337	0.066*
C8	0.4965 (5)	0.74913 (17)	0.47760 (12)	0.0477 (5)
H8A	0.5166	0.7198	0.4290	0.057*
C9	0.6184 (5)	0.69643 (15)	0.54803 (11)	0.0385 (4)
C10	0.6782 (6)	0.72335 (16)	0.77284 (11)	0.0468 (5)
H10A	0.7537	0.6728	0.8133	0.070*
H10B	0.4407	0.7403	0.7728	0.070*
H10C	0.8168	0.7846	0.7833	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0660 (4)	0.0475 (3)	0.0416 (3)	0.0056 (2)	0.0105 (2)	0.0074 (2)
O1	0.0806 (11)	0.0439 (9)	0.0462 (9)	0.0171 (8)	0.0183 (7)	−0.0027 (7)
N1	0.0548 (10)	0.0398 (9)	0.0339 (9)	0.0011 (7)	0.0134 (7)	−0.0035 (7)
C1	0.0486 (11)	0.0363 (10)	0.0412 (10)	−0.0011 (8)	0.0129 (8)	−0.0036 (8)
C2	0.0443 (10)	0.0376 (10)	0.0351 (10)	−0.0038 (7)	0.0104 (7)	0.0000 (8)
C3	0.0386 (10)	0.0392 (10)	0.0349 (10)	−0.0065 (7)	0.0105 (7)	−0.0042 (8)
C4	0.0369 (10)	0.0363 (10)	0.0382 (10)	−0.0046 (7)	0.0090 (7)	−0.0041 (8)
C5	0.0451 (11)	0.0415 (11)	0.0474 (12)	−0.0002 (8)	0.0086 (8)	−0.0062 (9)
C6	0.0528 (12)	0.0430 (11)	0.0610 (14)	0.0065 (9)	0.0046 (10)	0.0014 (10)
C7	0.0574 (13)	0.0547 (14)	0.0506 (13)	0.0009 (10)	0.0014 (10)	0.0121 (10)
C8	0.0559 (12)	0.0498 (12)	0.0374 (11)	−0.0005 (9)	0.0084 (8)	0.0017 (9)
C9	0.0395 (10)	0.0389 (10)	0.0380 (10)	−0.0045 (7)	0.0096 (7)	−0.0026 (8)
C10	0.0551 (12)	0.0491 (12)	0.0380 (10)	0.0024 (9)	0.0128 (8)	−0.0080 (9)

Geometric parameters (Å, º) top

Cl1—C2	1.728 (2)	C5—C6	1.373 (3)
O1—C1	1.243 (3)	C5—H5A	0.9300
N1—C1	1.355 (3)	C6—C7	1.391 (3)
N1—C9	1.382 (3)	C6—H6A	0.9300
N1—H1	0.9256	C7—C8	1.370 (3)
C1—C2	1.458 (3)	C7—H7A	0.9300
C2—C3	1.353 (3)	C8—C9	1.393 (3)
C3—C4	1.442 (3)	C8—H8A	0.9300
C3—C10	1.506 (2)	C10—H10A	0.9600
C4—C9	1.400 (3)	C10—H10B	0.9600
C4—C5	1.406 (3)	C10—H10C	0.9600

C1—N1—C9	124.95 (17)	C5—C6—C7	120.2 (2)
C1—N1—H1	119.6	C5—C6—H6A	119.9
C9—N1—H1	115.4	C7—C6—H6A	119.9
O1—C1—N1	121.42 (18)	C8—C7—C6	120.4 (2)
O1—C1—C2	123.80 (19)	C8—C7—H7A	119.8
N1—C1—C2	114.78 (17)	C6—C7—H7A	119.8
C3—C2—C1	123.60 (18)	C7—C8—C9	119.5 (2)
C3—C2—Cl1	122.45 (15)	C7—C8—H8A	120.3
C1—C2—Cl1	113.93 (15)	C9—C8—H8A	120.3
C2—C3—C4	118.30 (17)	N1—C9—C8	119.43 (18)
C2—C3—C10	122.04 (18)	N1—C9—C4	119.21 (18)
C4—C3—C10	119.65 (17)	C8—C9—C4	121.37 (19)
C9—C4—C5	117.48 (18)	C3—C10—H10A	109.5
C9—C4—C3	119.13 (18)	C3—C10—H10B	109.5
C5—C4—C3	123.38 (18)	H10A—C10—H10B	109.5
C6—C5—C4	121.0 (2)	C3—C10—H10C	109.5
C6—C5—H5A	119.5	H10A—C10—H10C	109.5
C4—C5—H5A	119.5	H10B—C10—H10C	109.5

C9—N1—C1—O1	−177.64 (19)	C9—C4—C5—C6	−0.9 (3)
C9—N1—C1—C2	1.9 (3)	C3—C4—C5—C6	178.36 (19)
O1—C1—C2—C3	177.3 (2)	C4—C5—C6—C7	1.4 (3)
N1—C1—C2—C3	−2.2 (3)	C5—C6—C7—C8	−0.3 (3)
O1—C1—C2—Cl1	−0.8 (3)	C6—C7—C8—C9	−1.2 (3)
N1—C1—C2—Cl1	179.65 (14)	C1—N1—C9—C8	178.74 (18)
C1—C2—C3—C4	1.2 (3)	C1—N1—C9—C4	−0.6 (3)
Cl1—C2—C3—C4	179.19 (13)	C7—C8—C9—N1	−177.72 (19)
C1—C2—C3—C10	−178.76 (18)	C7—C8—C9—C4	1.6 (3)
Cl1—C2—C3—C10	−0.7 (3)	C5—C4—C9—N1	178.79 (17)
C2—C3—C4—C9	0.2 (3)	C3—C4—C9—N1	−0.5 (3)
C10—C3—C4—C9	−179.84 (16)	C5—C4—C9—C8	−0.5 (3)
C2—C3—C4—C5	−179.06 (18)	C3—C4—C9—C8	−179.88 (17)
C10—C3—C4—C5	0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.93	1.91	2.816 (2)	166

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₈ClNO
M_r	193.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	3.9361 (2), 12.9239 (6), 17.1019 (7)
β (°)	100.197 (4)
V (Å³)	856.23 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.56
Crystal size (mm)	0.92 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.138, 0.720
No. of measured, independent and observed [I > 2σ(I)] reflections	5522, 1434, 1178
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.587

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.00
No. of reflections	1434
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.93	1.91	2.816 (2)	166

Symmetry code: (i) −x+2, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and 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.

References

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