1-[(2-Chloro-7,8-dimethyl-quinolin-3-yl)meth-yl]pyridin-2(1H)-one.

In the title compound, C(17)H(15)ClN(2)O, the quinoline ring system is nearly planar, with a maximum deviation from the mean plane of 0.074 (2) Å, and makes a dihedral angle of 81.03 (7)° with the pyridone ring. The crystal packing is stabilized by π-π stacking inter-actions between the pyridone and benzene rings of the quinoline ring system [centroid-centroid distance = 3.6754 (10) Å]. Furthermore, weak inter-molecular C-H⋯O hydrogen bonding links mol-ecules into supra-molecular chains along [001].

Related literature

For 2-pyridone analogues, see: Arman et al. (2009 ▶); Clegg & Nichol (2004 ▶); Nichol & Clegg (2005 ▶). For alkaloid analogues of natural or synthetic anti­cancer agents, see: Roopan & Khan (2009 ▶). For N-alkyl­ation in organic synthesis, see: Roopan et al. (2010 ▶).

Experimental

Crystal data

C17H15ClN2O

M = 298.76

Monoclinic,

a = 7.07034 (17) Å

b = 15.4729 (4) Å

c = 13.1704 (3) Å

β = 96.342 (2)°

V = 1432.01 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.24 × 0.15 × 0.12 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.953, T max = 0.968

15150 measured reflections

2810 independent reflections

2008 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.108

S = 1.06

2810 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011505/xu2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011505/xu2741Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15ClN2O	F(000) = 624
Mr = 298.76	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1523 reflections
a = 7.07034 (17) Å	θ = 2.6–26.0°
b = 15.4729 (4) Å	µ = 0.27 mm−1
c = 13.1704 (3) Å	T = 295 K
β = 96.342 (2)°	Block, colourless
V = 1432.01 (6) Å3	0.24 × 0.15 × 0.12 mm
Z = 4

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2810 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2008 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.953, Tmax = 0.968	k = −19→19
15150 measured reflections	l = −16→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.060P)2] where P = (Fo2 + 2Fc2)/3
2810 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
Cl1	1.38101 (6)	0.30106 (3)	0.46949 (4)	0.0555 (2)
O1	0.8143 (2)	0.15968 (9)	0.50257 (10)	0.0645 (5)
N1	1.14556 (19)	0.39838 (9)	0.35696 (10)	0.0395 (5)
N2	0.8843 (2)	0.24988 (9)	0.63744 (10)	0.0401 (5)
C1	1.1608 (2)	0.35195 (10)	0.43917 (13)	0.0376 (5)
C2	1.0220 (2)	0.33920 (11)	0.50689 (12)	0.0379 (5)
C3	0.8596 (2)	0.38656 (11)	0.48572 (12)	0.0388 (6)
C4	0.6662 (2)	0.48857 (11)	0.37163 (14)	0.0448 (6)
C5	0.6463 (3)	0.53389 (12)	0.28258 (14)	0.0504 (7)
C6	0.7855 (3)	0.53271 (11)	0.21389 (14)	0.0465 (6)
C7	0.9535 (2)	0.48792 (11)	0.23822 (13)	0.0406 (6)
C8	0.9779 (2)	0.44201 (10)	0.33237 (12)	0.0347 (5)
C9	0.8327 (2)	0.44006 (10)	0.39814 (12)	0.0360 (5)
C10	1.0577 (3)	0.27637 (13)	0.59472 (14)	0.0485 (6)
C11	0.8430 (3)	0.28316 (12)	0.72898 (14)	0.0490 (7)
C12	0.6894 (3)	0.25858 (13)	0.77200 (14)	0.0533 (7)
C13	0.5686 (3)	0.19603 (12)	0.72202 (15)	0.0525 (7)
C14	0.6077 (3)	0.16224 (12)	0.63285 (14)	0.0490 (6)
C15	0.7703 (3)	0.18774 (11)	0.58469 (13)	0.0435 (6)
C16	0.7440 (3)	0.57702 (15)	0.11113 (15)	0.0744 (9)
C17	1.1065 (3)	0.48403 (13)	0.16669 (14)	0.0544 (7)
H3	0.76520	0.38360	0.52950	0.0470*
H4	0.57050	0.48960	0.41470	0.0540*
H5	0.53700	0.56680	0.26650	0.0600*
H10A	1.12000	0.22540	0.57130	0.0580*
H10B	1.14370	0.30290	0.64830	0.0580*
H11	0.92440	0.32400	0.76200	0.0590*
H12	0.66280	0.28230	0.83370	0.0640*
H13	0.46110	0.17800	0.75090	0.0630*
H14	0.52600	0.12080	0.60130	0.0590*
H16A	0.84350	0.61760	0.10210	0.1120*
H16B	0.62460	0.60700	0.10850	0.1120*
H16C	0.73740	0.53460	0.05770	0.1120*
H17A	1.06670	0.44600	0.11080	0.0820*
H17B	1.22240	0.46280	0.20300	0.0820*
H17C	1.12740	0.54080	0.14090	0.0820*

	U11	U22	U33	U12	U13	U23
Cl1	0.0391 (3)	0.0611 (4)	0.0671 (4)	0.0103 (2)	0.0101 (2)	0.0147 (2)
O1	0.0904 (11)	0.0639 (9)	0.0404 (7)	−0.0009 (8)	0.0126 (7)	−0.0064 (6)
N1	0.0385 (8)	0.0395 (8)	0.0416 (8)	−0.0019 (7)	0.0091 (6)	0.0031 (7)
N2	0.0456 (9)	0.0409 (8)	0.0341 (8)	−0.0025 (7)	0.0055 (7)	0.0053 (7)
C1	0.0338 (9)	0.0344 (9)	0.0446 (10)	0.0002 (7)	0.0046 (7)	0.0005 (8)
C2	0.0381 (9)	0.0360 (9)	0.0396 (9)	−0.0050 (8)	0.0047 (7)	0.0015 (7)
C3	0.0368 (10)	0.0403 (10)	0.0403 (9)	−0.0030 (8)	0.0090 (7)	−0.0005 (8)
C4	0.0429 (10)	0.0416 (10)	0.0512 (11)	0.0045 (8)	0.0106 (8)	−0.0010 (9)
C5	0.0489 (11)	0.0394 (11)	0.0617 (12)	0.0082 (9)	0.0012 (9)	0.0035 (9)
C6	0.0527 (11)	0.0379 (10)	0.0475 (11)	−0.0025 (9)	−0.0001 (9)	0.0069 (8)
C7	0.0452 (10)	0.0355 (10)	0.0409 (10)	−0.0057 (8)	0.0045 (8)	0.0004 (8)
C8	0.0357 (9)	0.0305 (9)	0.0383 (9)	−0.0026 (7)	0.0053 (7)	0.0007 (7)
C9	0.0357 (9)	0.0310 (9)	0.0413 (9)	−0.0027 (7)	0.0043 (7)	−0.0024 (7)
C10	0.0410 (10)	0.0559 (12)	0.0483 (11)	−0.0010 (9)	0.0041 (8)	0.0133 (9)
C11	0.0636 (13)	0.0443 (11)	0.0388 (10)	−0.0033 (10)	0.0042 (9)	−0.0013 (8)
C12	0.0699 (14)	0.0542 (12)	0.0382 (10)	0.0064 (10)	0.0166 (10)	0.0012 (9)
C13	0.0506 (12)	0.0581 (13)	0.0502 (12)	0.0049 (10)	0.0116 (9)	0.0191 (10)
C14	0.0526 (12)	0.0477 (11)	0.0445 (10)	−0.0078 (9)	−0.0049 (9)	0.0098 (9)
C15	0.0538 (11)	0.0414 (10)	0.0342 (9)	0.0028 (9)	0.0000 (8)	0.0044 (8)
C16	0.0791 (16)	0.0780 (16)	0.0635 (14)	0.0081 (13)	−0.0036 (12)	0.0300 (12)
C17	0.0606 (13)	0.0582 (12)	0.0463 (11)	−0.0009 (10)	0.0139 (10)	0.0102 (9)

Cl1—C1	1.7511 (15)	C11—C12	1.335 (3)
O1—C15	1.237 (2)	C12—C13	1.405 (3)
N1—C1	1.294 (2)	C13—C14	1.342 (3)
N1—C8	1.372 (2)	C14—C15	1.429 (3)
N2—C10	1.463 (3)	C3—H3	0.9300
N2—C11	1.372 (2)	C4—H4	0.9300
N2—C15	1.390 (2)	C5—H5	0.9300
C1—C2	1.411 (2)	C10—H10A	0.9700
C2—C3	1.365 (2)	C10—H10B	0.9700
C2—C10	1.511 (3)	C11—H11	0.9300
C3—C9	1.415 (2)	C12—H12	0.9300
C4—C5	1.360 (3)	C13—H13	0.9300
C4—C9	1.407 (2)	C14—H14	0.9300
C5—C6	1.409 (3)	C16—H16A	0.9600
C6—C7	1.382 (3)	C16—H16B	0.9600
C6—C16	1.517 (3)	C16—H16C	0.9600
C7—C8	1.423 (2)	C17—H17A	0.9600
C7—C17	1.512 (3)	C17—H17B	0.9600
C8—C9	1.415 (2)	C17—H17C	0.9600
Cl1···C3i	3.6175 (15)	C11···H3	3.0500
Cl1···C14i	3.324 (2)	C15···H17Av	2.9400
Cl1···C15i	3.468 (2)	C16···H17A	3.0500
Cl1···H3i	3.0300	C16···H17C	2.7500
Cl1···H10A	2.6700	C17···H16A	2.8500
Cl1···H10B	3.0400	C17···H16C	2.9400
Cl1···H12ii	3.1000	H3···Cl1vi	3.0300
Cl1···H13ii	3.0100	H3···N2	2.6000
O1···C2	3.140 (2)	H3···C11	3.0500
O1···C12iii	3.318 (2)	H3···H4	2.5300
O1···H10A	2.4700	H4···H3	2.5300
O1···H17Civ	2.7000	H4···H4viii	2.5800
O1···H12iii	2.5200	H5···H16B	2.3200
O1···H17Av	2.7100	H10A···Cl1	2.6700
N1···H17B	2.3800	H10A···O1	2.4700
N2···H3	2.6000	H10B···Cl1	3.0400
C2···O1	3.140 (2)	H10B···H11	2.2900
C3···Cl1vi	3.6175 (15)	H10B···C5vii	3.0200
C3···C11	3.595 (2)	H11···H10B	2.2900
C3···C15	3.427 (2)	H11···C6vii	3.0100
C4···C13iii	3.495 (3)	H11···C7vii	3.0400
C6···C14iii	3.394 (3)	H11···H16Avii	2.4600
C7···C14iii	3.543 (3)	H11···H17Cvii	2.5000
C7···C15iii	3.546 (2)	H12···Cl1ix	3.1000
C9···C13iii	3.513 (2)	H12···O1v	2.5200
C9···C12iii	3.586 (3)	H13···Cl1ix	3.0100
C11···C3	3.595 (2)	H16A···C17	2.8500
C12···O1v	3.318 (2)	H16A···H17C	2.3400
C12···C9v	3.586 (3)	H16A···H11vii	2.4600
C13···C9v	3.513 (2)	H16B···H5	2.3200
C13···C4v	3.495 (3)	H16C···C17	2.9400
C14···C6v	3.394 (3)	H17A···C16	3.0500
C14···C7v	3.543 (3)	H17A···O1iii	2.7100
C14···Cl1vi	3.324 (2)	H17A···C15iii	2.9400
C15···C3	3.427 (2)	H17B···N1	2.3800
C15···C7v	3.546 (2)	H17C···C16	2.7500
C15···Cl1vi	3.468 (2)	H17C···H16A	2.3400
C5···H10Bvii	3.0200	H17C···O1x	2.7000
C6···H11vii	3.0100	H17C···H11vii	2.5000
C7···H11vii	3.0400
C1—N1—C8	117.44 (13)	N2—C15—C14	114.82 (15)
C10—N2—C11	120.11 (15)	C2—C3—H3	119.00
C10—N2—C15	117.76 (14)	C9—C3—H3	120.00
C11—N2—C15	122.06 (15)	C5—C4—H4	120.00
Cl1—C1—N1	115.48 (12)	C9—C4—H4	120.00
Cl1—C1—C2	117.13 (12)	C4—C5—H5	119.00
N1—C1—C2	127.38 (14)	C6—C5—H5	119.00
C1—C2—C3	115.09 (15)	N2—C10—H10A	109.00
C1—C2—C10	120.33 (14)	N2—C10—H10B	109.00
C3—C2—C10	124.58 (15)	C2—C10—H10A	109.00
C2—C3—C9	120.99 (14)	C2—C10—H10B	109.00
C5—C4—C9	119.53 (16)	H10A—C10—H10B	108.00
C4—C5—C6	122.27 (18)	N2—C11—H11	119.00
C5—C6—C7	120.08 (17)	C12—C11—H11	119.00
C5—C6—C16	119.16 (18)	C11—C12—H12	121.00
C7—C6—C16	120.68 (17)	C13—C12—H12	121.00
C6—C7—C8	118.09 (15)	C12—C13—H13	120.00
C6—C7—C17	122.09 (16)	C14—C13—H13	120.00
C8—C7—C17	119.79 (14)	C13—C14—H14	119.00
N1—C8—C7	118.03 (13)	C15—C14—H14	119.00
N1—C8—C9	120.77 (14)	C6—C16—H16A	110.00
C7—C8—C9	121.19 (13)	C6—C16—H16B	109.00
C3—C9—C4	123.20 (14)	C6—C16—H16C	110.00
C3—C9—C8	118.04 (13)	H16A—C16—H16B	109.00
C4—C9—C8	118.71 (14)	H16A—C16—H16C	109.00
N2—C10—C2	113.49 (15)	H16B—C16—H16C	109.00
N2—C11—C12	121.90 (18)	C7—C17—H17A	109.00
C11—C12—C13	118.58 (18)	C7—C17—H17B	109.00
C12—C13—C14	120.33 (19)	C7—C17—H17C	109.00
C13—C14—C15	122.32 (18)	H17A—C17—H17B	110.00
O1—C15—N2	119.46 (18)	H17A—C17—H17C	109.00
O1—C15—C14	125.72 (17)	H17B—C17—H17C	109.00
C8—N1—C1—Cl1	−177.63 (11)	C9—C4—C5—C6	1.4 (3)
C8—N1—C1—C2	1.3 (2)	C5—C4—C9—C8	1.9 (2)
C1—N1—C8—C7	−175.25 (15)	C5—C4—C9—C3	−175.64 (16)
C1—N1—C8—C9	3.7 (2)	C4—C5—C6—C7	−3.3 (3)
C10—N2—C11—C12	−177.86 (18)	C4—C5—C6—C16	173.50 (18)
C11—N2—C15—C14	0.5 (2)	C16—C6—C7—C17	2.7 (3)
C10—N2—C15—O1	−2.8 (2)	C5—C6—C7—C8	1.6 (3)
C15—N2—C11—C12	−0.9 (3)	C5—C6—C7—C17	179.44 (17)
C11—N2—C15—O1	−179.78 (17)	C16—C6—C7—C8	−175.12 (16)
C10—N2—C15—C14	177.47 (16)	C6—C7—C8—C9	1.7 (2)
C11—N2—C10—C2	−104.43 (18)	C17—C7—C8—N1	2.8 (2)
C15—N2—C10—C2	78.5 (2)	C6—C7—C8—N1	−179.28 (15)
N1—C1—C2—C3	−5.0 (3)	C17—C7—C8—C9	−176.16 (15)
N1—C1—C2—C10	174.62 (16)	C7—C8—C9—C4	−3.5 (2)
Cl1—C1—C2—C10	−6.5 (2)	C7—C8—C9—C3	174.16 (15)
Cl1—C1—C2—C3	173.96 (12)	N1—C8—C9—C4	177.54 (15)
C1—C2—C3—C9	3.5 (2)	N1—C8—C9—C3	−4.8 (2)
C1—C2—C10—N2	−161.79 (15)	N2—C11—C12—C13	0.7 (3)
C3—C2—C10—N2	17.8 (2)	C11—C12—C13—C14	−0.2 (3)
C10—C2—C3—C9	−176.05 (16)	C12—C13—C14—C15	−0.3 (3)
C2—C3—C9—C4	178.47 (16)	C13—C14—C15—O1	−179.63 (19)
C2—C3—C9—C8	0.9 (2)	C13—C14—C15—N2	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2	0.93	2.60	2.902 (2)	100
C10—H10A···Cl1	0.97	2.67	2.987 (2)	100
C12—H12···O1v	0.93	2.52	3.318 (2)	143
C17—H17B···N1	0.96	2.38	2.821 (2)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.52	3.318 (2)	143

Symmetry code: (i) .