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

In the title compound, C(19)H(15)ClN(2)O, the quinoline ring forms a dihedral angle of 43.24 (1)° with the benzene ring of the dihydroquinolinyl system. In the crystal, mol-ecules are linked through a single weak C-H⋯O hydrogen bond, forming ribbons which extend along (100), giving alternating zigzag mol-ecular layers which stack down the b-axis direction.

Related literature

For applications of similar structures see: Chandrasekhar et al. (2007 ▶); Varma & Saini (1997 ▶); Donnelly & Farrell (1990 ▶); Hemanth Kumar et al. (2004 ▶). For the synthesis of the 2-amino­chalcone, see: Gao et al. (1996 ▶). For related structures, see: Bouraiou et al. (2008 ▶, 2011 ▶); Belfaitah et al. (2006 ▶); Benzerka et al. (2011 ▶).

Experimental

Crystal data

C19H15ClN2O

M = 322.78

Orthorhombic,

a = 13.8912 (8) Å

b = 12.4572 (4) Å

c = 17.8617 (11) Å

V = 3090.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 295 K

0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

6664 measured reflections

3537 independent reflections

1696 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.169

S = 1.00

3537 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.27 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., 2003 ▶); 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, I. DOI: 10.1107/S1600536812020831/zs2200sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020831/zs2200Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020831/zs2200Isup3.cml

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

C19H15ClN2O	F(000) = 1344
Mr = 322.78	Dx = 1.387 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3949 reflections
a = 13.8912 (8) Å	θ = 2.9–27.5°
b = 12.4572 (4) Å	µ = 0.25 mm−1
c = 17.8617 (11) Å	T = 295 K
V = 3090.9 (3) Å3	Needle, colourless
Z = 8	0.15 × 0.06 × 0.05 mm

Nonius KappaCCD diffractometer	1696 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590 diffractometer	Rint = 0.072
Graphite monochromator	θmax = 27.5°, θmin = 2.9°
Detector resolution: 9 pixels mm-1	h = −18→17
CCD rotation images, thick slices scans	k = −16→16
6664 measured reflections	l = −23→23
3537 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.5198P] where P = (Fo2 + 2Fc2)/3
3537 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.27 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
Cl1	1.00123 (7)	0.53833 (7)	0.38618 (6)	0.0598 (3)
O1	1.00620 (19)	0.1322 (2)	0.36882 (17)	0.0724 (9)
N1	0.8795 (2)	0.6237 (2)	0.47797 (17)	0.0467 (7)
N2	0.7597 (2)	0.3073 (2)	0.34987 (16)	0.0461 (7)
C1	0.8911 (2)	0.5416 (2)	0.43385 (19)	0.0430 (8)
C2	0.8250 (2)	0.4560 (2)	0.42234 (18)	0.0408 (7)
C3	0.7405 (2)	0.4630 (2)	0.46099 (18)	0.0430 (8)
H3	0.6944	0.4096	0.4554	0.052*
C4	0.7221 (2)	0.5504 (2)	0.50953 (18)	0.0411 (8)
C5	0.6356 (2)	0.5626 (2)	0.54971 (19)	0.0453 (8)
H5	0.5879	0.5108	0.5447	0.054*
C6	0.6196 (3)	0.6486 (2)	0.59604 (19)	0.0474 (9)
C7	0.6938 (3)	0.7251 (3)	0.60359 (19)	0.0515 (9)
H7	0.6842	0.7834	0.6353	0.062*
C8	0.7791 (3)	0.7169 (2)	0.56608 (19)	0.0508 (9)
H8	0.8269	0.7682	0.5728	0.061*
C9	0.7940 (2)	0.6298 (2)	0.51708 (19)	0.0424 (8)
C10	0.5261 (3)	0.6631 (3)	0.6368 (2)	0.0687 (12)
H10A	0.4871	0.7146	0.6107	0.103*
H10B	0.5385	0.6883	0.6867	0.103*
H10C	0.4927	0.5957	0.6391	0.103*
C11	0.8477 (2)	0.3617 (2)	0.37226 (19)	0.0442 (8)
H11	0.8803	0.3883	0.3273	0.053*
C12	0.9131 (3)	0.2810 (2)	0.41094 (19)	0.0479 (9)
H12A	0.9741	0.3151	0.4226	0.058*
H12B	0.8838	0.2588	0.4577	0.058*
C13	0.9313 (3)	0.1834 (3)	0.3631 (2)	0.0475 (8)
C14	0.8524 (2)	0.1510 (2)	0.31357 (18)	0.0420 (8)
C15	0.7678 (2)	0.2110 (2)	0.31041 (18)	0.0412 (8)
C16	0.6899 (3)	0.1735 (3)	0.2677 (2)	0.0523 (9)
H16	0.633	0.2127	0.266	0.063*
C17	0.6976 (3)	0.0793 (3)	0.2284 (2)	0.0534 (9)
H17	0.6453	0.0546	0.2008	0.064*
C18	0.7825 (3)	0.0204 (3)	0.2292 (2)	0.0559 (9)
H18	0.7878	−0.0423	0.2012	0.067*
C19	0.8584 (3)	0.0556 (2)	0.2717 (2)	0.0505 (9)
H19	0.915	0.0157	0.2728	0.061*
H2	0.717 (3)	0.348 (2)	0.3321 (19)	0.05*

	U11	U22	U33	U12	U13	U23
Cl1	0.0485 (5)	0.0545 (5)	0.0763 (7)	−0.0051 (4)	0.0144 (5)	0.0027 (5)
O1	0.0539 (18)	0.0643 (16)	0.099 (2)	0.0201 (13)	−0.0134 (16)	−0.0173 (15)
N1	0.0479 (18)	0.0388 (14)	0.0534 (17)	−0.0029 (13)	−0.0024 (14)	−0.0010 (13)
N2	0.0408 (17)	0.0419 (15)	0.0554 (18)	0.0075 (12)	−0.0080 (14)	−0.0077 (13)
C1	0.0382 (19)	0.0412 (17)	0.050 (2)	0.0007 (14)	0.0014 (15)	0.0067 (15)
C2	0.0450 (19)	0.0353 (16)	0.0421 (18)	0.0008 (14)	−0.0046 (16)	0.0041 (14)
C3	0.045 (2)	0.0360 (16)	0.0482 (19)	−0.0027 (14)	−0.0011 (16)	−0.0015 (15)
C4	0.047 (2)	0.0352 (15)	0.0412 (18)	0.0007 (15)	0.0025 (15)	0.0043 (14)
C5	0.047 (2)	0.0378 (16)	0.051 (2)	−0.0021 (14)	−0.0016 (17)	0.0033 (15)
C6	0.057 (2)	0.0407 (17)	0.045 (2)	0.0054 (16)	0.0057 (17)	0.0048 (15)
C7	0.062 (2)	0.0438 (18)	0.049 (2)	0.0108 (17)	−0.0084 (19)	−0.0058 (16)
C8	0.059 (2)	0.0394 (17)	0.053 (2)	−0.0029 (16)	−0.0091 (19)	−0.0063 (16)
C9	0.043 (2)	0.0382 (16)	0.0454 (19)	−0.0004 (14)	−0.0040 (16)	0.0028 (14)
C10	0.075 (3)	0.054 (2)	0.078 (3)	0.007 (2)	0.022 (2)	−0.004 (2)
C11	0.042 (2)	0.0401 (17)	0.050 (2)	0.0005 (14)	−0.0020 (16)	−0.0038 (15)
C12	0.047 (2)	0.0439 (18)	0.053 (2)	0.0052 (15)	−0.0083 (17)	−0.0013 (15)
C13	0.042 (2)	0.0461 (18)	0.054 (2)	0.0036 (16)	0.0013 (17)	0.0044 (16)
C14	0.044 (2)	0.0397 (16)	0.0423 (19)	−0.0002 (14)	0.0043 (15)	0.0014 (14)
C15	0.042 (2)	0.0396 (16)	0.0419 (18)	0.0000 (14)	0.0038 (15)	0.0004 (14)
C16	0.047 (2)	0.055 (2)	0.055 (2)	−0.0028 (16)	−0.0017 (17)	−0.0058 (17)
C17	0.060 (3)	0.053 (2)	0.047 (2)	−0.0127 (17)	−0.0048 (19)	−0.0062 (16)
C18	0.071 (3)	0.0454 (18)	0.051 (2)	−0.0023 (18)	0.005 (2)	−0.0066 (16)
C19	0.061 (2)	0.0423 (17)	0.048 (2)	0.0054 (16)	0.0067 (19)	0.0001 (16)

Cl1—C1	1.751 (3)	C8—H8	0.93
O1—C13	1.224 (4)	C10—H10A	0.96
N1—C1	1.301 (4)	C10—H10B	0.96
N1—C9	1.380 (4)	C10—H10C	0.96
N2—C15	1.395 (4)	C11—C12	1.522 (4)
N2—C11	1.454 (4)	C11—H11	0.98
N2—H2	0.85 (3)	C12—C13	1.507 (4)
C1—C2	1.423 (4)	C12—H12A	0.97
C2—C3	1.364 (5)	C12—H12B	0.97
C2—C11	1.509 (4)	C13—C14	1.466 (5)
C3—C4	1.415 (4)	C14—C15	1.395 (4)
C3—H3	0.93	C14—C19	1.406 (4)
C4—C5	1.407 (5)	C15—C16	1.404 (4)
C4—C9	1.412 (4)	C16—C17	1.372 (4)
C5—C6	1.372 (4)	C16—H16	0.93
C5—H5	0.93	C17—C18	1.389 (5)
C6—C7	1.410 (5)	C17—H17	0.93
C6—C10	1.500 (5)	C18—C19	1.372 (5)
C7—C8	1.365 (5)	C18—H18	0.93
C7—H7	0.93	C19—H19	0.93
C8—C9	1.409 (4)
C1—N1—C9	117.2 (3)	H10A—C10—H10C	109.5
C15—N2—C11	118.2 (3)	H10B—C10—H10C	109.5
C15—N2—H2	112 (2)	N2—C11—C2	110.5 (3)
C11—N2—H2	115 (2)	N2—C11—C12	108.6 (3)
N1—C1—C2	126.6 (3)	C2—C11—C12	111.7 (3)
N1—C1—Cl1	114.9 (2)	N2—C11—H11	108.7
C2—C1—Cl1	118.4 (2)	C2—C11—H11	108.7
C3—C2—C1	115.7 (3)	C12—C11—H11	108.7
C3—C2—C11	122.0 (3)	C13—C12—C11	112.1 (3)
C1—C2—C11	122.3 (3)	C13—C12—H12A	109.2
C2—C3—C4	121.1 (3)	C11—C12—H12A	109.2
C2—C3—H3	119.5	C13—C12—H12B	109.2
C4—C3—H3	119.5	C11—C12—H12B	109.2
C5—C4—C9	118.7 (3)	H12A—C12—H12B	107.9
C5—C4—C3	123.4 (3)	O1—C13—C14	122.8 (3)
C9—C4—C3	118.0 (3)	O1—C13—C12	121.0 (3)
C6—C5—C4	122.0 (3)	C14—C13—C12	116.1 (3)
C6—C5—H5	119	C15—C14—C19	118.8 (3)
C4—C5—H5	119	C15—C14—C13	120.5 (3)
C5—C6—C7	117.9 (3)	C19—C14—C13	120.6 (3)
C5—C6—C10	121.8 (3)	C14—C15—N2	120.5 (3)
C7—C6—C10	120.3 (3)	C14—C15—C16	119.5 (3)
C8—C7—C6	122.4 (3)	N2—C15—C16	119.9 (3)
C8—C7—H7	118.8	C17—C16—C15	120.2 (3)
C6—C7—H7	118.8	C17—C16—H16	119.9
C7—C8—C9	119.4 (3)	C15—C16—H16	119.9
C7—C8—H8	120.3	C16—C17—C18	120.9 (3)
C9—C8—H8	120.3	C16—C17—H17	119.6
N1—C9—C8	118.9 (3)	C18—C17—H17	119.6
N1—C9—C4	121.5 (3)	C19—C18—C17	119.3 (3)
C8—C9—C4	119.6 (3)	C19—C18—H18	120.4
C6—C10—H10A	109.5	C17—C18—H18	120.4
C6—C10—H10B	109.5	C18—C19—C14	121.3 (3)
H10A—C10—H10B	109.5	C18—C19—H19	119.4
C6—C10—H10C	109.5	C14—C19—H19	119.4
C9—N1—C1—C2	−1.0 (5)	C15—N2—C11—C12	−50.0 (4)
C9—N1—C1—Cl1	−179.8 (2)	C3—C2—C11—N2	21.5 (4)
N1—C1—C2—C3	1.2 (5)	C1—C2—C11—N2	−160.2 (3)
Cl1—C1—C2—C3	180.0 (2)	C3—C2—C11—C12	−99.5 (4)
N1—C1—C2—C11	−177.2 (3)	C1—C2—C11—C12	78.8 (4)
Cl1—C1—C2—C11	1.6 (4)	N2—C11—C12—C13	54.4 (4)
C1—C2—C3—C4	−0.5 (5)	C2—C11—C12—C13	176.5 (3)
C11—C2—C3—C4	177.9 (3)	C11—C12—C13—O1	151.2 (3)
C2—C3—C4—C5	178.9 (3)	C11—C12—C13—C14	−32.2 (4)
C2—C3—C4—C9	−0.4 (5)	O1—C13—C14—C15	178.7 (3)
C9—C4—C5—C6	−0.4 (5)	C12—C13—C14—C15	2.1 (5)
C3—C4—C5—C6	−179.6 (3)	O1—C13—C14—C19	2.3 (5)
C4—C5—C6—C7	−1.0 (5)	C12—C13—C14—C19	−174.2 (3)
C4—C5—C6—C10	177.9 (3)	C19—C14—C15—N2	−178.6 (3)
C5—C6—C7—C8	0.8 (5)	C13—C14—C15—N2	5.0 (5)
C10—C6—C7—C8	−178.2 (3)	C19—C14—C15—C16	2.0 (5)
C6—C7—C8—C9	0.9 (5)	C13—C14—C15—C16	−174.4 (3)
C1—N1—C9—C8	179.3 (3)	C11—N2—C15—C14	20.8 (4)
C1—N1—C9—C4	0.0 (5)	C11—N2—C15—C16	−159.8 (3)
C7—C8—C9—N1	178.4 (3)	C14—C15—C16—C17	−1.0 (5)
C7—C8—C9—C4	−2.3 (5)	N2—C15—C16—C17	179.6 (3)
C5—C4—C9—N1	−178.6 (3)	C15—C16—C17—C18	−1.0 (5)
C3—C4—C9—N1	0.7 (5)	C16—C17—C18—C19	1.9 (6)
C5—C4—C9—C8	2.0 (5)	C17—C18—C19—C14	−0.9 (5)
C3—C4—C9—C8	−178.7 (3)	C15—C14—C19—C18	−1.0 (5)
C15—N2—C11—C2	−172.8 (3)	C13—C14—C19—C18	175.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2	0.93	2.45	2.788 (4)	102
C11—H11···Cl1	0.98	2.72	3.074 (3)	102
C17—H17···O1i	0.93	2.49	3.243 (5)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.93	2.49	3.243 (5)	138

Symmetry code: (i) .