Ethyl 4-(4-chloro-phen-yl)-2-methyl-5-oxo-5,6,7,8-tetra-hydro-quinoline-3-carboxyl-ate.

In the title compound, C19H18ClNO3, the non-aromatic part of the fused ring system adopts an envelope conformation with the central methyl-ene C atom as the flap. The dihedral angle between the pyridine and benzene rings is 56.98 (3)°. In the crystal, mol-ecules are linked into double layers parallel to (100) by a network of weak C-H⋯O inter-actions.

Related literature

For the synthetic procedure, see: Fang et al. (2007 ▶); Mirza-Aghayan et al. (2012 ▶). For a related structure, see: Sicheri et al. (1992 ▶).

Experimental

Crystal data

C19H18ClNO3

M = 343.79

Monoclinic,

a = 12.5736 (7) Å

b = 8.3815 (4) Å

c = 17.4945 (8) Å

β = 112.151 (2)°

V = 1707.59 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.49 × 0.42 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.891, T max = 0.932

15658 measured reflections

3860 independent reflections

2725 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 1.00

3860 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016541/fy2095sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016541/fy2095Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016541/fy2095Isup3.cml

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

C19H18ClNO3	F(000) = 720
Mr = 343.79	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10595 reflections
a = 12.5736 (7) Å	θ = 3.1–27.4°
b = 8.3815 (4) Å	µ = 0.24 mm−1
c = 17.4945 (8) Å	T = 296 K
β = 112.151 (2)°	Chunk, yellow
V = 1707.59 (15) Å3	0.49 × 0.42 × 0.30 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3860 independent reflections
Radiation source: rotating anode	2725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.891, Tmax = 0.932	l = −18→22
15658 measured reflections

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.6492P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3860 reflections	Δρmax = 0.28 e Å−3
220 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (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	0.42545 (16)	0.6493 (2)	0.58924 (11)	0.0375 (4)
C2	0.41107 (17)	0.7151 (2)	0.51265 (11)	0.0413 (4)
C3	0.50712 (19)	0.7626 (2)	0.49622 (12)	0.0473 (5)
C4	0.62896 (17)	0.6962 (2)	0.62798 (12)	0.0436 (4)
C5	0.75005 (18)	0.7044 (3)	0.69010 (14)	0.0580 (6)
H5A	0.7673	0.8142	0.7080	0.070*
H5B	0.8018	0.6734	0.6633	0.070*
C6	0.77367 (19)	0.6007 (3)	0.76517 (14)	0.0581 (6)
H6A	0.8455	0.6329	0.8081	0.070*
H6B	0.7811	0.4905	0.7511	0.070*
C7	0.67692 (18)	0.6145 (3)	0.79737 (12)	0.0539 (5)
H7A	0.6935	0.5475	0.8457	0.065*
H7B	0.6707	0.7240	0.8132	0.065*
C8	0.56577 (17)	0.5633 (2)	0.73116 (12)	0.0426 (4)
C9	0.53856 (16)	0.6381 (2)	0.64827 (11)	0.0388 (4)
C10	0.32257 (15)	0.6031 (2)	0.60723 (11)	0.0368 (4)
C11	0.30200 (17)	0.6742 (2)	0.67217 (11)	0.0426 (4)
H11	0.3545	0.7475	0.7056	0.051*
C12	0.20518 (18)	0.6381 (2)	0.68790 (12)	0.0466 (5)
H12	0.1922	0.6862	0.7315	0.056*
C13	0.12768 (16)	0.5288 (2)	0.63758 (12)	0.0434 (4)
C14	0.14541 (17)	0.4562 (2)	0.57310 (12)	0.0461 (5)
H14	0.0925	0.3829	0.5400	0.055*
C15	0.24351 (16)	0.4933 (2)	0.55776 (11)	0.0426 (4)
H15	0.2562	0.4445	0.5142	0.051*
C16	0.29397 (18)	0.7489 (2)	0.44907 (11)	0.0454 (5)
C17	0.1340 (2)	0.9227 (3)	0.41726 (18)	0.0778 (8)
H17A	0.0757	0.8430	0.4117	0.093*
H17B	0.1365	0.9418	0.3633	0.093*
C18	0.1069 (2)	1.0718 (3)	0.4508 (2)	0.0846 (8)
H18A	0.1020	1.0508	0.5033	0.127*
H18B	0.0348	1.1129	0.4134	0.127*
H18C	0.1663	1.1488	0.4576	0.127*
C19	0.4969 (2)	0.8326 (3)	0.41431 (14)	0.0654 (6)
H19A	0.5631	0.8971	0.4216	0.098*
H19B	0.4290	0.8974	0.3930	0.098*
H19C	0.4920	0.7480	0.3761	0.098*
Cl1	0.00542 (5)	0.48132 (7)	0.65772 (4)	0.0647 (2)
N1	0.61354 (15)	0.7536 (2)	0.55298 (11)	0.0497 (4)
O1	0.50420 (13)	0.46307 (17)	0.74340 (9)	0.0545 (4)
O2	0.24504 (13)	0.86760 (17)	0.47419 (9)	0.0560 (4)
O3	0.25193 (14)	0.68423 (19)	0.38335 (9)	0.0642 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0394 (10)	0.0356 (9)	0.0393 (10)	−0.0022 (7)	0.0169 (8)	−0.0045 (7)
C2	0.0432 (11)	0.0426 (10)	0.0390 (10)	−0.0019 (8)	0.0166 (8)	−0.0033 (7)
C3	0.0537 (13)	0.0487 (11)	0.0459 (11)	−0.0031 (9)	0.0262 (10)	−0.0020 (8)
C4	0.0394 (11)	0.0446 (10)	0.0500 (11)	−0.0014 (8)	0.0205 (9)	−0.0058 (8)
C5	0.0382 (12)	0.0722 (14)	0.0639 (14)	−0.0048 (10)	0.0196 (10)	−0.0048 (11)
C6	0.0400 (12)	0.0701 (14)	0.0582 (13)	0.0018 (10)	0.0117 (10)	−0.0068 (10)
C7	0.0464 (12)	0.0677 (13)	0.0432 (11)	−0.0007 (10)	0.0117 (9)	−0.0050 (9)
C8	0.0390 (10)	0.0466 (10)	0.0423 (10)	0.0047 (8)	0.0155 (8)	−0.0018 (8)
C9	0.0383 (10)	0.0395 (9)	0.0397 (10)	−0.0003 (7)	0.0161 (8)	−0.0045 (7)
C10	0.0337 (9)	0.0383 (9)	0.0365 (9)	−0.0006 (7)	0.0111 (7)	0.0014 (7)
C11	0.0406 (11)	0.0461 (10)	0.0408 (10)	−0.0086 (8)	0.0149 (8)	−0.0091 (8)
C12	0.0471 (12)	0.0515 (11)	0.0461 (11)	−0.0019 (8)	0.0231 (9)	−0.0066 (8)
C13	0.0330 (10)	0.0481 (10)	0.0501 (11)	−0.0007 (8)	0.0168 (8)	0.0036 (8)
C14	0.0376 (11)	0.0476 (10)	0.0492 (11)	−0.0089 (8)	0.0117 (9)	−0.0075 (8)
C15	0.0410 (11)	0.0470 (10)	0.0394 (10)	−0.0026 (8)	0.0148 (8)	−0.0067 (7)
C16	0.0505 (12)	0.0481 (10)	0.0382 (10)	−0.0041 (9)	0.0173 (9)	0.0018 (8)
C17	0.0601 (16)	0.0666 (15)	0.0816 (18)	0.0133 (12)	−0.0019 (13)	−0.0026 (13)
C18	0.0680 (18)	0.0735 (17)	0.112 (2)	0.0162 (13)	0.0335 (17)	0.0057 (16)
C19	0.0703 (16)	0.0826 (16)	0.0528 (13)	−0.0089 (12)	0.0341 (12)	0.0065 (11)
Cl1	0.0444 (3)	0.0791 (4)	0.0791 (4)	−0.0094 (3)	0.0330 (3)	−0.0020 (3)
N1	0.0463 (10)	0.0581 (10)	0.0523 (10)	−0.0038 (8)	0.0271 (8)	−0.0016 (8)
O1	0.0472 (9)	0.0600 (9)	0.0539 (9)	−0.0002 (7)	0.0163 (7)	0.0149 (7)
O2	0.0498 (9)	0.0548 (8)	0.0536 (9)	0.0088 (6)	0.0084 (7)	−0.0054 (6)
O3	0.0649 (11)	0.0769 (10)	0.0418 (8)	0.0010 (8)	0.0100 (7)	−0.0117 (7)

C1—C2	1.396 (3)	C10—C11	1.391 (3)
C1—C9	1.411 (3)	C11—C12	1.379 (3)
C1—C10	1.493 (3)	C11—H11	0.9300
C2—C3	1.400 (3)	C12—C13	1.385 (3)
C2—C16	1.500 (3)	C12—H12	0.9300
C3—N1	1.334 (3)	C13—C14	1.372 (3)
C3—C19	1.509 (3)	C13—Cl1	1.748 (2)
C4—N1	1.341 (3)	C14—C15	1.393 (3)
C4—C9	1.400 (3)	C14—H14	0.9300
C4—C5	1.502 (3)	C15—H15	0.9300
C5—C6	1.508 (3)	C16—O3	1.199 (2)
C5—H5A	0.9700	C16—O2	1.329 (2)
C5—H5B	0.9700	C17—O2	1.451 (3)
C6—C7	1.525 (3)	C17—C18	1.474 (4)
C6—H6A	0.9700	C17—H17A	0.9700
C6—H6B	0.9700	C17—H17B	0.9700
C7—C8	1.503 (3)	C18—H18A	0.9600
C7—H7A	0.9700	C18—H18B	0.9600
C7—H7B	0.9700	C18—H18C	0.9600
C8—O1	1.215 (2)	C19—H19A	0.9600
C8—C9	1.496 (3)	C19—H19B	0.9600
C10—C15	1.391 (2)	C19—H19C	0.9600
C2—C1—C9	117.32 (17)	C12—C11—C10	121.26 (17)
C2—C1—C10	119.73 (16)	C12—C11—H11	119.4
C9—C1—C10	122.86 (16)	C10—C11—H11	119.4
C1—C2—C3	119.96 (18)	C11—C12—C13	118.74 (18)
C1—C2—C16	121.46 (17)	C11—C12—H12	120.6
C3—C2—C16	118.39 (17)	C13—C12—H12	120.6
N1—C3—C2	122.12 (18)	C14—C13—C12	121.52 (18)
N1—C3—C19	115.56 (19)	C14—C13—Cl1	119.53 (15)
C2—C3—C19	122.3 (2)	C12—C13—Cl1	118.95 (15)
N1—C4—C9	122.76 (18)	C13—C14—C15	119.31 (17)
N1—C4—C5	115.12 (18)	C13—C14—H14	120.3
C9—C4—C5	122.07 (18)	C15—C14—H14	120.3
C4—C5—C6	114.62 (18)	C10—C15—C14	120.33 (17)
C4—C5—H5A	108.6	C10—C15—H15	119.8
C6—C5—H5A	108.6	C14—C15—H15	119.8
C4—C5—H5B	108.6	O3—C16—O2	124.34 (19)
C6—C5—H5B	108.6	O3—C16—C2	125.48 (19)
H5A—C5—H5B	107.6	O2—C16—C2	110.09 (16)
C5—C6—C7	110.81 (18)	O2—C17—C18	107.7 (2)
C5—C6—H6A	109.5	O2—C17—H17A	110.2
C7—C6—H6A	109.5	C18—C17—H17A	110.2
C5—C6—H6B	109.5	O2—C17—H17B	110.2
C7—C6—H6B	109.5	C18—C17—H17B	110.2
H6A—C6—H6B	108.1	H17A—C17—H17B	108.5
C8—C7—C6	109.46 (17)	C17—C18—H18A	109.5
C8—C7—H7A	109.8	C17—C18—H18B	109.5
C6—C7—H7A	109.8	H18A—C18—H18B	109.5
C8—C7—H7B	109.8	C17—C18—H18C	109.5
C6—C7—H7B	109.8	H18A—C18—H18C	109.5
H7A—C7—H7B	108.2	H18B—C18—H18C	109.5
O1—C8—C9	122.17 (17)	C3—C19—H19A	109.5
O1—C8—C7	122.06 (18)	C3—C19—H19B	109.5
C9—C8—C7	115.71 (17)	H19A—C19—H19B	109.5
C4—C9—C1	118.81 (17)	C3—C19—H19C	109.5
C4—C9—C8	118.73 (17)	H19A—C19—H19C	109.5
C1—C9—C8	122.44 (17)	H19B—C19—H19C	109.5
C15—C10—C11	118.84 (17)	C3—N1—C4	118.87 (17)
C15—C10—C1	120.88 (16)	C16—O2—C17	117.20 (17)
C11—C10—C1	120.24 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O3i	0.97	2.67	3.454 (3)	139
C11—H11···O1ii	0.93	2.45	3.357 (2)	164
C12—H12···O3iii	0.93	2.70	3.569 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O3i	0.97	2.67	3.454 (3)	139
C11—H11⋯O1ii	0.93	2.45	3.357 (2)	164
C12—H12⋯O3iii	0.93	2.70	3.569 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) .