1-[(2-Chloro-7-methyl-3-quinol-yl)meth-yl]pyridin-2(1H)-one.

In the title compound, C(16)H(13)ClN(2)O, the quinoline ring system is essentially planar, with a maximum deviation of 0.021 (2) Å. The pyridone ring is oriented at a dihedral angle of 85.93 (6)° with respect to the quinoline ring system. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules along the b axis. Weak π-π stacking inter-actions [centroid-centroid distances = 3.7218 (9) and 3.6083 (9) Å] are also observed.

Related literature

For related structures, see: Arman et al. (2009 ▶); Clegg & Nichol (2004 ▶); Nichol & Clegg (2005 ▶). For the synthesis of 2-pyridone derivatives, see: Conreaux et al. (2005 ▶); Roopan & Khan (2009 ▶); Roopan et al. (2010 ▶).

Experimental

Crystal data

C16H13ClN2O

M = 284.73

Monoclinic,

a = 11.8934 (3) Å

b = 11.1092 (3) Å

c = 21.2858 (6) Å

β = 102.413 (3)°

V = 2746.67 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.26 × 0.21 × 0.18 mm

Data collection

Oxford Xcalibur diffractometer with an Eos (Nova) CCD detector

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.932, T max = 0.952

13638 measured reflections

2556 independent reflections

1893 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.10

2556 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.22 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 (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/S1600536810011177/is2533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011177/is2533Isup2.hkl

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

C16H13ClN2O	F(000) = 1184
Mr = 284.73	Dx = 1.377 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 985 reflections
a = 11.8934 (3) Å	θ = 3.4–25.5°
b = 11.1092 (3) Å	µ = 0.27 mm−1
c = 21.2858 (6) Å	T = 295 K
β = 102.413 (3)°	Block, colourless
V = 2746.67 (13) Å3	0.26 × 0.21 × 0.18 mm
Z = 8

Oxford Xcalibur diffractometer with an Eos (Nova) CCD detector	2556 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1893 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 25.5°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.932, Tmax = 0.952	k = −13→13
13638 measured reflections	l = −25→25

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.1075P] where P = (Fo2 + 2Fc2)/3
2556 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.22 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	1.09208 (3)	0.30078 (4)	0.05639 (2)	0.0632 (2)
O1	0.85807 (10)	0.41006 (11)	0.21457 (5)	0.0685 (5)
N1	0.89822 (11)	0.31396 (11)	−0.02677 (6)	0.0489 (5)
N2	0.92375 (10)	0.56671 (11)	0.16368 (5)	0.0467 (4)
C1	0.95261 (12)	0.35624 (13)	0.02798 (7)	0.0459 (5)
C2	0.91154 (12)	0.44280 (13)	0.06637 (7)	0.0434 (5)
C3	0.80426 (12)	0.48690 (13)	0.04162 (7)	0.0460 (5)
C4	0.62855 (14)	0.49071 (14)	−0.04533 (8)	0.0542 (6)
C5	0.56786 (14)	0.44843 (16)	−0.10296 (8)	0.0602 (6)
C6	0.61864 (16)	0.35797 (17)	−0.13404 (8)	0.0648 (7)
C7	0.72499 (15)	0.31365 (15)	−0.10943 (7)	0.0580 (6)
C8	0.78938 (13)	0.35771 (14)	−0.05035 (7)	0.0475 (5)
C9	0.73932 (12)	0.44607 (13)	−0.01767 (7)	0.0447 (5)
C10	0.98427 (13)	0.48243 (15)	0.13024 (7)	0.0513 (5)
C11	0.92446 (14)	0.68655 (15)	0.14990 (8)	0.0595 (6)
C12	0.86613 (16)	0.76605 (17)	0.17753 (9)	0.0705 (7)
C13	0.80463 (15)	0.72478 (18)	0.22262 (8)	0.0688 (7)
C14	0.80364 (13)	0.60698 (17)	0.23677 (8)	0.0593 (6)
C15	0.86079 (13)	0.51932 (16)	0.20637 (7)	0.0503 (6)
C16	0.44951 (15)	0.49594 (19)	−0.13245 (9)	0.0845 (8)
H3	0.77340	0.54520	0.06440	0.0550*
H4	0.59630	0.55000	−0.02390	0.0650*
H6	0.57750	0.32750	−0.17290	0.0780*
H7	0.75570	0.25410	−0.13150	0.0700*
H10A	1.00650	0.41230	0.15720	0.0620*
H10B	1.05400	0.52020	0.12310	0.0620*
H11	0.96660	0.71350	0.12060	0.0710*
H12	0.86630	0.84730	0.16710	0.0850*
H13	0.76440	0.77910	0.24280	0.0820*
H14	0.76400	0.58190	0.26770	0.0710*
H16A	0.43010	0.55940	−0.10600	0.1270*
H16B	0.39420	0.43210	−0.13540	0.1270*
H16C	0.44880	0.52660	−0.17470	0.1270*

	U11	U22	U33	U12	U13	U23
Cl1	0.0530 (3)	0.0666 (3)	0.0737 (3)	0.0066 (2)	0.0219 (2)	0.0046 (2)
O1	0.0847 (9)	0.0633 (8)	0.0632 (8)	−0.0139 (7)	0.0289 (6)	0.0034 (6)
N1	0.0569 (8)	0.0505 (8)	0.0446 (8)	−0.0072 (6)	0.0228 (6)	−0.0011 (6)
N2	0.0474 (7)	0.0559 (8)	0.0375 (7)	−0.0067 (6)	0.0108 (6)	−0.0030 (6)
C1	0.0485 (9)	0.0466 (9)	0.0475 (9)	−0.0040 (7)	0.0214 (7)	0.0056 (7)
C2	0.0482 (9)	0.0476 (9)	0.0372 (8)	−0.0069 (7)	0.0154 (7)	0.0024 (6)
C3	0.0492 (9)	0.0486 (9)	0.0422 (9)	−0.0028 (7)	0.0143 (7)	−0.0033 (7)
C4	0.0544 (10)	0.0542 (10)	0.0527 (10)	−0.0062 (8)	0.0085 (8)	0.0039 (8)
C5	0.0572 (10)	0.0661 (11)	0.0532 (11)	−0.0165 (9)	0.0030 (8)	0.0139 (9)
C6	0.0747 (12)	0.0765 (12)	0.0406 (10)	−0.0307 (10)	0.0064 (9)	0.0007 (9)
C7	0.0726 (12)	0.0615 (11)	0.0436 (10)	−0.0180 (9)	0.0205 (9)	−0.0052 (8)
C8	0.0578 (10)	0.0490 (9)	0.0392 (9)	−0.0138 (8)	0.0183 (7)	0.0023 (7)
C9	0.0495 (9)	0.0466 (9)	0.0394 (9)	−0.0080 (7)	0.0125 (7)	0.0033 (7)
C10	0.0462 (9)	0.0643 (10)	0.0449 (9)	−0.0019 (8)	0.0131 (7)	−0.0028 (8)
C11	0.0643 (11)	0.0594 (11)	0.0558 (11)	−0.0124 (9)	0.0150 (8)	0.0015 (8)
C12	0.0798 (13)	0.0590 (11)	0.0725 (13)	−0.0027 (10)	0.0158 (11)	−0.0053 (9)
C13	0.0641 (11)	0.0784 (14)	0.0624 (12)	0.0046 (10)	0.0105 (9)	−0.0214 (10)
C14	0.0525 (10)	0.0839 (13)	0.0437 (9)	−0.0086 (9)	0.0153 (8)	−0.0137 (9)
C15	0.0482 (9)	0.0649 (11)	0.0367 (9)	−0.0122 (8)	0.0069 (7)	−0.0054 (8)
C16	0.0655 (13)	0.0976 (16)	0.0791 (14)	−0.0176 (11)	−0.0096 (11)	0.0184 (12)

Cl1—C1	1.7509 (15)	C11—C12	1.335 (3)
O1—C15	1.228 (2)	C12—C13	1.403 (3)
N1—C1	1.2935 (19)	C13—C14	1.344 (3)
N1—C8	1.373 (2)	C14—C15	1.421 (2)
N2—C10	1.457 (2)	C3—H3	0.9300
N2—C11	1.364 (2)	C4—H4	0.9300
N2—C15	1.3986 (19)	C6—H6	0.9300
C1—C2	1.415 (2)	C7—H7	0.9300
C2—C3	1.363 (2)	C10—H10A	0.9700
C2—C10	1.512 (2)	C10—H10B	0.9700
C3—C9	1.406 (2)	C11—H11	0.9300
C4—C5	1.366 (2)	C12—H12	0.9300
C4—C9	1.412 (2)	C13—H13	0.9300
C5—C6	1.409 (3)	C14—H14	0.9300
C5—C16	1.508 (3)	C16—H16A	0.9600
C6—C7	1.354 (3)	C16—H16B	0.9600
C7—C8	1.412 (2)	C16—H16C	0.9600
C8—C9	1.407 (2)
Cl1···C9i	3.6496 (15)	C15···C10iv	3.592 (2)
Cl1···C5ii	3.6161 (18)	C15···C15iv	3.431 (2)
Cl1···C3i	3.5414 (15)	C16···C14vi	3.526 (3)
Cl1···H10A	2.8500	C5···H12vii	2.8400
Cl1···H10B	2.9100	C6···H14viii	3.0600
Cl1···H16Bii	3.0700	C7···H14viii	2.9900
O1···C2	3.3690 (18)	C8···H10Bi	2.9900
O1···C7ii	3.348 (2)	C11···H3	2.7600
O1···C13iii	3.299 (2)	C14···H16Bvi	2.8600
O1···H10A	2.3500	C15···H3	2.9900
O1···H13iii	2.3700	C16···H12vii	3.0100
O1···H10Aiv	2.8600	H3···N2	2.4700
O1···H7ii	2.6900	H3···C11	2.7600
N2···C15iv	3.3835 (19)	H3···C15	2.9900
N1···H11i	2.8400	H3···H4	2.5000
N1···H10Bi	2.9000	H4···H3	2.5000
N2···H3	2.4700	H4···H16A	2.3400
C1···C6ii	3.507 (2)	H7···O1ii	2.6900
C1···C7ii	3.550 (2)	H10A···Cl1	2.8500
C2···O1	3.3690 (18)	H10A···O1	2.3500
C2···C7ii	3.498 (2)	H10A···O1iv	2.8600
C3···C11	3.295 (2)	H10B···Cl1	2.9100
C3···C15	3.445 (2)	H10B···H11	2.3800
C3···Cl1i	3.5414 (15)	H10B···N1i	2.9000
C5···Cl1ii	3.6161 (18)	H10B···C8i	2.9900
C6···C1ii	3.507 (2)	H11···H10B	2.3800
C7···C2ii	3.498 (2)	H11···N1i	2.8400
C7···O1ii	3.348 (2)	H12···C5vii	2.8400
C7···C1ii	3.550 (2)	H12···C16vii	3.0100
C8···C8ii	3.473 (2)	H12···H16Cvii	2.5800
C9···Cl1i	3.6496 (15)	H13···O1v	2.3700
C10···C15iv	3.592 (2)	H14···C6ix	3.0600
C11···C3	3.295 (2)	H14···C7ix	2.9900
C13···O1v	3.299 (2)	H16A···H4	2.3400
C14···C16vi	3.526 (3)	H16B···C14vi	2.8600
C15···N2iv	3.3835 (19)	H16B···Cl1ii	3.0700
C15···C3	3.445 (2)	H16C···H12vii	2.5800
C1—N1—C8	116.78 (13)	O1—C15—C14	125.67 (15)
C10—N2—C11	119.73 (12)	N2—C15—C14	114.41 (15)
C10—N2—C15	117.73 (13)	C2—C3—H3	119.00
C11—N2—C15	122.42 (13)	C9—C3—H3	119.00
Cl1—C1—N1	115.89 (11)	C5—C4—H4	119.00
Cl1—C1—C2	117.30 (11)	C9—C4—H4	119.00
N1—C1—C2	126.81 (14)	C5—C6—H6	119.00
C1—C2—C3	115.58 (13)	C7—C6—H6	119.00
C1—C2—C10	121.03 (13)	C6—C7—H7	120.00
C3—C2—C10	123.39 (13)	C8—C7—H7	120.00
C2—C3—C9	121.28 (14)	N2—C10—H10A	109.00
C5—C4—C9	121.27 (15)	N2—C10—H10B	109.00
C4—C5—C6	118.03 (16)	C2—C10—H10A	109.00
C4—C5—C16	121.28 (16)	C2—C10—H10B	109.00
C6—C5—C16	120.68 (16)	H10A—C10—H10B	108.00
C5—C6—C7	122.49 (16)	N2—C11—H11	119.00
C6—C7—C8	120.10 (15)	C12—C11—H11	119.00
N1—C8—C7	119.42 (14)	C11—C12—H12	121.00
N1—C8—C9	122.15 (13)	C13—C12—H12	121.00
C7—C8—C9	118.43 (14)	C12—C13—H13	120.00
C3—C9—C4	122.97 (14)	C14—C13—H13	120.00
C3—C9—C8	117.37 (13)	C13—C14—H14	119.00
C4—C9—C8	119.65 (14)	C15—C14—H14	119.00
N2—C10—C2	112.30 (12)	C5—C16—H16A	109.00
N2—C11—C12	121.55 (16)	C5—C16—H16B	109.00
C11—C12—C13	118.81 (17)	C5—C16—H16C	109.00
C12—C13—C14	120.18 (17)	H16A—C16—H16B	109.00
C13—C14—C15	122.51 (16)	H16A—C16—H16C	109.00
O1—C15—N2	119.91 (14)	H16B—C16—H16C	109.00
C8—N1—C1—Cl1	−179.03 (11)	C2—C3—C9—C4	−179.11 (15)
C8—N1—C1—C2	0.2 (2)	C2—C3—C9—C8	0.1 (2)
C1—N1—C8—C7	−179.03 (14)	C9—C4—C5—C6	0.5 (2)
C1—N1—C8—C9	1.3 (2)	C9—C4—C5—C16	179.90 (16)
C11—N2—C10—C2	−85.11 (17)	C5—C4—C9—C3	−179.74 (15)
C15—N2—C10—C2	91.08 (15)	C5—C4—C9—C8	1.0 (2)
C10—N2—C11—C12	177.19 (16)	C4—C5—C6—C7	−1.1 (3)
C15—N2—C11—C12	1.2 (2)	C16—C5—C6—C7	179.45 (17)
C10—N2—C15—O1	0.1 (2)	C5—C6—C7—C8	0.2 (3)
C10—N2—C15—C14	−179.61 (13)	C6—C7—C8—N1	−178.43 (15)
C11—N2—C15—O1	176.14 (14)	C6—C7—C8—C9	1.3 (2)
C11—N2—C15—C14	−3.5 (2)	N1—C8—C9—C3	−1.5 (2)
Cl1—C1—C2—C3	177.80 (11)	N1—C8—C9—C4	177.83 (14)
Cl1—C1—C2—C10	−1.85 (19)	C7—C8—C9—C3	178.85 (14)
N1—C1—C2—C3	−1.4 (2)	C7—C8—C9—C4	−1.9 (2)
N1—C1—C2—C10	178.91 (14)	N2—C11—C12—C13	1.2 (3)
C1—C2—C3—C9	1.2 (2)	C11—C12—C13—C14	−0.9 (3)
C10—C2—C3—C9	−179.19 (14)	C12—C13—C14—C15	−1.7 (3)
C1—C2—C10—N2	−176.75 (13)	C13—C14—C15—O1	−175.85 (16)
C3—C2—C10—N2	3.6 (2)	C13—C14—C15—N2	3.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1v	0.93	2.37	3.299 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.93	2.37	3.299 (2)	173

Symmetry code: (i) .