2-(2-Chloro-6,7-dimethyl-quinolin-3-yl)-2,3-dihydro-quinolin-4(1H)-one.

In the title mol-ecule, C(20)H(17)ClN(2)O, the dihedral angle between the mean plane of the quinoline ring system and the benzene ring of the dihydro-quinolinone moiety is 57.84 (8)°. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of inter-molecular N-H⋯N hydrogen bonds. These dimers are further stabilized by weak π-π stacking inter-actions between pyridine rings with a centroid-centroid distance of 3.9414 (12) Å.

Related literature

For quinoline compounds and their applications, see: Prakash et al. (1994 ▶); Singh & Kapil (1993 ▶); Kalinin et al. (1992 ▶); Xia et al. (1992 ▶); Donnelly & Farrell (1990a ▶,b ▶); Kumar et al. (2004 ▶); Varma & Saini (1997 ▶); Tokes & Litkei (1993 ▶); Tokes & Szilagyi (1987 ▶); Tokes et al. (1992 ▶). For our previous work on quinoline derivatives, see: Belfaitah et al. (2006 ▶); Bouraiou et al. (2008 ▶, 2010 ▶, 2011 ▶); Benzerka et al. (2010 ▶); Ladraa et al. (2010 ▶).

Experimental

Crystal data

C20H17ClN2O

M = 336.81

Triclinic,

a = 7.7345 (4) Å

b = 10.6196 (6) Å

c = 11.3463 (4) Å

α = 96.425 (2)°

β = 100.068 (3)°

γ = 109.576 (1)°

V = 849.84 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

7058 measured reflections

3863 independent reflections

2507 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.133

S = 1.00

3863 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811028170/lh5284sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811028170/lh5284globalsup2.cml

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

C20H17ClN2O	Z = 2
Mr = 336.81	F(000) = 352
Triclinic, P1	Dx = 1.316 Mg m−3
a = 7.7345 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6196 (6) Å	Cell parameters from 3734 reflections
c = 11.3463 (4) Å	θ = 2.9–27.5°
α = 96.425 (2)°	µ = 0.23 mm−1
β = 100.068 (3)°	T = 295 K
γ = 109.576 (1)°	Needle, white
V = 849.84 (7) Å3	0.15 × 0.06 × 0.05 mm

Nonius KappaCCD diffractometer	2507 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.029
graphite	θmax = 27.5°, θmin = 3.0°
Detector resolution: 9 pixels mm-1	h = −10→10
CCD rotation images, thick slices scans	k = −13→13
7058 measured reflections	l = −14→14
3863 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.0886P] where P = (Fo2 + 2Fc2)/3
3863 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2476 (3)	−0.00341 (19)	0.99805 (16)	0.0463 (4)
C2	0.2561 (2)	0.13287 (18)	1.01932 (15)	0.0442 (4)
C3	0.2601 (3)	0.18540 (19)	1.13579 (16)	0.0474 (4)
H3	0.2659	0.2744	1.1546	0.057*
C4	0.2556 (3)	0.10607 (19)	1.22794 (16)	0.0475 (4)
C5	0.2595 (3)	0.1535 (2)	1.35012 (17)	0.0549 (5)
H5	0.2666	0.2423	1.3728	0.066*
C6	0.2531 (3)	0.0720 (2)	1.43636 (17)	0.0578 (5)
C7	0.2407 (3)	−0.0639 (2)	1.40197 (18)	0.0579 (5)
C8	0.2379 (3)	−0.1118 (2)	1.28402 (18)	0.0558 (5)
H8	0.2314	−0.2007	1.2624	0.067*
C9	0.2446 (2)	−0.02881 (19)	1.19481 (16)	0.0476 (4)
C10	0.2307 (4)	−0.1569 (3)	1.4943 (2)	0.0806 (7)
H10A	0.2206	−0.2449	1.4553	0.121*
H10B	0.1225	−0.1653	1.5278	0.121*
H10C	0.3427	−0.1194	1.5584	0.121*
C11	0.2620 (4)	0.1278 (3)	1.56687 (18)	0.0767 (7)
H11A	0.3749	0.1284	1.6184	0.115*
H11B	0.1542	0.0716	1.5921	0.115*
H11C	0.2625	0.2188	1.5729	0.115*
C12	0.2648 (2)	0.21733 (18)	0.91943 (16)	0.0448 (4)
H12	0.1964	0.1569	0.8412	0.054*
C13	0.4673 (3)	0.2922 (2)	0.91241 (18)	0.0535 (5)
H13A	0.5382	0.3471	0.9914	0.064*
H13B	0.5245	0.2265	0.8924	0.064*
C14	0.4785 (3)	0.3822 (2)	0.81848 (18)	0.0566 (5)
C15	0.3261 (3)	0.43479 (19)	0.79376 (17)	0.0524 (5)
C16	0.3250 (4)	0.5217 (2)	0.7094 (2)	0.0738 (7)
H16	0.4184	0.5419	0.6653	0.089*
C17	0.1893 (4)	0.5769 (3)	0.6911 (3)	0.0911 (9)
H17	0.1905	0.6342	0.6348	0.109*
C18	0.0495 (4)	0.5478 (3)	0.7563 (3)	0.0833 (8)
H18	−0.0425	0.5862	0.7438	0.1*
C19	0.0459 (3)	0.4632 (2)	0.8389 (2)	0.0609 (5)
H19	−0.0483	0.4446	0.8824	0.073*
C20	0.1829 (3)	0.40416 (18)	0.85847 (16)	0.0480 (4)
N1	0.2392 (2)	−0.08277 (15)	1.07803 (14)	0.0498 (4)
N2	0.1772 (2)	0.31720 (17)	0.94168 (14)	0.0488 (4)
H2N	0.066 (3)	0.284 (2)	0.9549 (18)	0.059*
O1	0.6107 (2)	0.4116 (2)	0.76829 (17)	0.0858 (5)
Cl1	0.24838 (8)	−0.07686 (5)	0.85241 (5)	0.06466 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0434 (10)	0.0469 (10)	0.0467 (9)	0.0148 (8)	0.0099 (7)	0.0071 (7)
C2	0.0408 (9)	0.0471 (10)	0.0440 (9)	0.0149 (8)	0.0086 (7)	0.0108 (7)
C3	0.0513 (11)	0.0436 (10)	0.0484 (9)	0.0177 (8)	0.0121 (8)	0.0101 (8)
C4	0.0465 (10)	0.0507 (11)	0.0448 (9)	0.0160 (8)	0.0106 (8)	0.0115 (8)
C5	0.0545 (12)	0.0603 (12)	0.0492 (10)	0.0194 (10)	0.0121 (9)	0.0114 (9)
C6	0.0499 (11)	0.0743 (14)	0.0460 (10)	0.0165 (10)	0.0108 (8)	0.0172 (9)
C7	0.0469 (11)	0.0706 (14)	0.0560 (11)	0.0163 (10)	0.0106 (9)	0.0281 (10)
C8	0.0523 (11)	0.0522 (12)	0.0602 (12)	0.0141 (9)	0.0088 (9)	0.0210 (9)
C9	0.0416 (10)	0.0491 (11)	0.0497 (10)	0.0124 (8)	0.0087 (8)	0.0150 (8)
C10	0.0827 (17)	0.0918 (19)	0.0721 (14)	0.0277 (14)	0.0192 (12)	0.0446 (13)
C11	0.0823 (17)	0.0991 (19)	0.0475 (11)	0.0304 (15)	0.0157 (11)	0.0156 (12)
C12	0.0453 (10)	0.0455 (10)	0.0436 (9)	0.0153 (8)	0.0107 (7)	0.0113 (7)
C13	0.0458 (10)	0.0588 (12)	0.0592 (11)	0.0198 (9)	0.0144 (9)	0.0170 (9)
C14	0.0492 (11)	0.0569 (12)	0.0599 (11)	0.0110 (9)	0.0169 (9)	0.0144 (9)
C15	0.0515 (11)	0.0424 (10)	0.0562 (11)	0.0070 (9)	0.0107 (9)	0.0144 (8)
C16	0.0760 (16)	0.0627 (14)	0.0876 (16)	0.0178 (12)	0.0308 (13)	0.0370 (12)
C17	0.102 (2)	0.0756 (18)	0.114 (2)	0.0372 (16)	0.0319 (17)	0.0595 (16)
C18	0.0805 (17)	0.0698 (16)	0.115 (2)	0.0385 (14)	0.0229 (15)	0.0436 (15)
C19	0.0586 (12)	0.0517 (12)	0.0761 (13)	0.0229 (10)	0.0156 (10)	0.0171 (10)
C20	0.0470 (10)	0.0381 (9)	0.0519 (10)	0.0095 (8)	0.0060 (8)	0.0073 (8)
N1	0.0514 (9)	0.0441 (9)	0.0530 (8)	0.0159 (7)	0.0107 (7)	0.0121 (7)
N2	0.0466 (9)	0.0510 (9)	0.0541 (9)	0.0193 (7)	0.0164 (7)	0.0177 (7)
O1	0.0641 (10)	0.1091 (14)	0.0992 (12)	0.0288 (10)	0.0431 (9)	0.0487 (11)
Cl1	0.0817 (4)	0.0589 (3)	0.0535 (3)	0.0264 (3)	0.0186 (2)	0.0028 (2)

C1—N1	1.301 (2)	C11—H11B	0.96
C1—C2	1.418 (3)	C11—H11C	0.96
C1—Cl1	1.7485 (19)	C12—N2	1.459 (2)
C2—C3	1.367 (2)	C12—C13	1.521 (3)
C2—C12	1.519 (2)	C12—H12	0.98
C3—C4	1.412 (2)	C13—C14	1.504 (3)
C3—H3	0.93	C13—H13A	0.97
C4—C9	1.410 (3)	C13—H13B	0.97
C4—C5	1.413 (3)	C14—O1	1.223 (2)
C5—C6	1.373 (3)	C14—C15	1.463 (3)
C5—H5	0.93	C15—C20	1.403 (3)
C6—C7	1.420 (3)	C15—C16	1.403 (3)
C6—C11	1.513 (3)	C16—C17	1.360 (4)
C7—C8	1.371 (3)	C16—H16	0.93
C7—C10	1.512 (3)	C17—C18	1.385 (4)
C8—C9	1.411 (2)	C17—H17	0.93
C8—H8	0.93	C18—C19	1.367 (3)
C9—N1	1.371 (2)	C18—H18	0.93
C10—H10A	0.96	C19—C20	1.400 (3)
C10—H10B	0.96	C19—H19	0.93
C10—H10C	0.96	C20—N2	1.389 (2)
C11—H11A	0.96	N2—H2N	0.86 (2)
N1—C1—C2	126.09 (17)	H11B—C11—H11C	109.5
N1—C1—Cl1	114.81 (14)	N2—C12—C2	110.34 (14)
C2—C1—Cl1	119.11 (13)	N2—C12—C13	108.54 (15)
C3—C2—C1	116.21 (16)	C2—C12—C13	111.35 (15)
C3—C2—C12	121.63 (17)	N2—C12—H12	108.9
C1—C2—C12	122.15 (16)	C2—C12—H12	108.9
C2—C3—C4	120.78 (17)	C13—C12—H12	108.9
C2—C3—H3	119.6	C14—C13—C12	111.87 (16)
C4—C3—H3	119.6	C14—C13—H13A	109.2
C9—C4—C3	117.57 (16)	C12—C13—H13A	109.2
C9—C4—C5	118.52 (16)	C14—C13—H13B	109.2
C3—C4—C5	123.91 (18)	C12—C13—H13B	109.2
C6—C5—C4	121.8 (2)	H13A—C13—H13B	107.9
C6—C5—H5	119.1	O1—C14—C15	122.46 (19)
C4—C5—H5	119.1	O1—C14—C13	121.3 (2)
C5—C6—C7	119.29 (18)	C15—C14—C13	116.24 (17)
C5—C6—C11	120.1 (2)	C20—C15—C16	118.8 (2)
C7—C6—C11	120.59 (19)	C20—C15—C14	120.37 (17)
C8—C7—C6	119.87 (17)	C16—C15—C14	120.79 (19)
C8—C7—C10	119.5 (2)	C17—C16—C15	121.0 (2)
C6—C7—C10	120.6 (2)	C17—C16—H16	119.5
C7—C8—C9	121.2 (2)	C15—C16—H16	119.5
C7—C8—H8	119.4	C16—C17—C18	120.1 (2)
C9—C8—H8	119.4	C16—C17—H17	119.9
N1—C9—C4	122.10 (15)	C18—C17—H17	119.9
N1—C9—C8	118.61 (18)	C19—C18—C17	120.4 (2)
C4—C9—C8	119.29 (17)	C19—C18—H18	119.8
C7—C10—H10A	109.5	C17—C18—H18	119.8
C7—C10—H10B	109.5	C18—C19—C20	120.5 (2)
H10A—C10—H10B	109.5	C18—C19—H19	119.7
C7—C10—H10C	109.5	C20—C19—H19	119.7
H10A—C10—H10C	109.5	N2—C20—C19	120.17 (18)
H10B—C10—H10C	109.5	N2—C20—C15	120.66 (18)
C6—C11—H11A	109.5	C19—C20—C15	119.16 (18)
C6—C11—H11B	109.5	C1—N1—C9	117.23 (16)
H11A—C11—H11B	109.5	C20—N2—C12	115.66 (15)
C6—C11—H11C	109.5	C20—N2—H2N	111.0 (14)
H11A—C11—H11C	109.5	C12—N2—H2N	114.5 (15)
N1—C1—C2—C3	1.6 (3)	N2—C12—C13—C14	−55.2 (2)
Cl1—C1—C2—C3	−178.31 (14)	C2—C12—C13—C14	−176.88 (16)
N1—C1—C2—C12	−179.75 (18)	C12—C13—C14—O1	−153.6 (2)
Cl1—C1—C2—C12	0.3 (2)	C12—C13—C14—C15	28.1 (2)
C1—C2—C3—C4	−0.1 (3)	O1—C14—C15—C20	−176.5 (2)
C12—C2—C3—C4	−178.73 (16)	C13—C14—C15—C20	1.8 (3)
C2—C3—C4—C9	−0.7 (3)	O1—C14—C15—C16	0.5 (3)
C2—C3—C4—C5	179.93 (18)	C13—C14—C15—C16	178.8 (2)
C9—C4—C5—C6	0.1 (3)	C20—C15—C16—C17	0.7 (4)
C3—C4—C5—C6	179.40 (19)	C14—C15—C16—C17	−176.3 (2)
C4—C5—C6—C7	−0.5 (3)	C15—C16—C17—C18	0.1 (4)
C4—C5—C6—C11	178.64 (19)	C16—C17—C18—C19	−0.3 (5)
C5—C6—C7—C8	0.9 (3)	C17—C18—C19—C20	−0.3 (4)
C11—C6—C7—C8	−178.26 (19)	C18—C19—C20—N2	−179.4 (2)
C5—C6—C7—C10	−179.1 (2)	C18—C19—C20—C15	1.1 (3)
C11—C6—C7—C10	1.7 (3)	C16—C15—C20—N2	179.17 (19)
C6—C7—C8—C9	−0.8 (3)	C14—C15—C20—N2	−3.8 (3)
C10—C7—C8—C9	179.2 (2)	C16—C15—C20—C19	−1.3 (3)
C3—C4—C9—N1	0.3 (3)	C14—C15—C20—C19	175.74 (18)
C5—C4—C9—N1	179.64 (17)	C2—C1—N1—C9	−2.1 (3)
C3—C4—C9—C8	−179.37 (17)	Cl1—C1—N1—C9	177.84 (13)
C5—C4—C9—C8	0.0 (3)	C4—C9—N1—C1	1.1 (3)
C7—C8—C9—N1	−179.27 (18)	C8—C9—N1—C1	−179.28 (17)
C7—C8—C9—C4	0.4 (3)	C19—C20—N2—C12	153.97 (18)
C3—C2—C12—N2	−30.9 (2)	C15—C20—N2—C12	−26.5 (2)
C1—C2—C12—N2	150.56 (17)	C2—C12—N2—C20	177.70 (15)
C3—C2—C12—C13	89.7 (2)	C13—C12—N2—C20	55.4 (2)
C1—C2—C12—C13	−88.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1i	0.86 (2)	2.53 (2)	3.297 (2)	148.6 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N1i	0.86 (2)	2.53 (2)	3.297 (2)	148.6 (18)

Symmetry code: (i) .