Ethyl 2-methyl-5-oxo-4-(3,4,5-trimeth-oxy-phen-yl)-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

In the mol-ecular structure of the title compound, C(22)H(27)NO(6), the dihydro-pyridine ring adopts a flattened boat conformation while the cyclo-hexenone ring is in an envelope conformation. In the crystal, mol-ecules stack parallel to the crystallographic a axis linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For general background to the biological activity of quinoline derivatives, see: Baba (1997 ▶); Baba et al. (1997 ▶,1998 ▶); Davies et al. (2005 ▶); Rose & Draeger et al. (1992 ▶); Warrior et al. (2005 ▶).

Experimental

Crystal data

C22H27NO6

M = 401.44

Triclinic,

a = 7.512 (2) Å

b = 10.402 (1) Å

c = 14.568 (3) Å

α = 109.77 (3)°

β = 95.42 (1)°

γ = 104.41 (2)°

V = 1017.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.26 × 0.24 × 0.21 mm

Data collection

Nonius MACH3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.976, T max = 0.980

4471 measured reflections

3574 independent reflections

2653 reflections with I > 2σ(I)

R int = 0.013

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.129

S = 1.03

3574 reflections

268 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030333/jh2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030333/jh2183Isup2.hkl

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

C22H27NO6	Z = 2
Mr = 401.44	F(000) = 428
Triclinic, P1	Dx = 1.310 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.512 (2) Å	Cell parameters from 25 reflections
b = 10.402 (1) Å	θ = 2–25°
c = 14.568 (3) Å	µ = 0.10 mm−1
α = 109.77 (3)°	T = 294 K
β = 95.42 (1)°	Block, colourless
γ = 104.41 (2)°	0.26 × 0.24 × 0.21 mm
V = 1017.4 (4) Å3

Nonius MACH3 diffractometer	2653 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
graphite	θmax = 25.0°, θmin = 2.1°
ω–2θ scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.976, Tmax = 0.980	l = −17→17
4471 measured reflections	3 standard reflections every 60 min
3574 independent reflections	intensity decay: none

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.3979P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3574 reflections	Δρmax = 0.23 e Å−3
268 parameters	Δρmin = −0.18 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: 0.013 (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
C22	0.4600 (4)	0.2952 (4)	0.0056 (2)	0.0841 (9)
H22A	0.4922	0.3586	−0.0293	0.101*
H22B	0.3534	0.2153	−0.0339	0.101*
H22C	0.5642	0.2613	0.0178	0.101*
H1N	−0.286 (4)	−0.135 (3)	0.2897 (18)	0.061 (7)*
O4	0.68460 (19)	0.35699 (15)	0.22606 (11)	0.0519 (4)
O3	0.36747 (19)	0.26111 (15)	0.50993 (10)	0.0523 (4)
N1	−0.1712 (2)	−0.09684 (18)	0.30488 (13)	0.0405 (4)
O1	0.41288 (19)	−0.16053 (16)	0.25103 (12)	0.0588 (4)
C6	0.1238 (2)	−0.11864 (19)	0.27165 (13)	0.0323 (4)
C1	−0.0644 (2)	−0.17812 (19)	0.25700 (13)	0.0347 (4)
C8	0.0925 (2)	0.09809 (19)	0.40306 (13)	0.0346 (4)
C9	−0.0944 (2)	0.0320 (2)	0.38398 (14)	0.0356 (4)
C15	0.4536 (2)	0.20151 (19)	0.27900 (14)	0.0371 (4)
H15	0.5452	0.1991	0.3256	0.044*
O2	0.0990 (2)	0.30115 (19)	0.54511 (14)	0.0765 (6)
C5	0.2404 (3)	−0.2085 (2)	0.23209 (15)	0.0407 (5)
C16	0.5036 (3)	0.28065 (19)	0.22121 (15)	0.0388 (4)
O6	0.4166 (2)	0.36880 (18)	0.09651 (13)	0.0659 (5)
C19	0.1316 (3)	0.1295 (2)	0.19881 (14)	0.0393 (4)
H19	0.0068	0.0788	0.1914	0.047*
C7	0.2165 (2)	0.03861 (18)	0.33288 (13)	0.0330 (4)
H7	0.3332	0.0471	0.3740	0.040*
C14	0.2679 (2)	0.12545 (18)	0.26814 (13)	0.0332 (4)
O5	0.0588 (2)	0.21801 (19)	0.06860 (13)	0.0656 (5)
C3	−0.0564 (3)	−0.3963 (2)	0.12134 (17)	0.0557 (6)
H3A	−0.0602	−0.3578	0.0694	0.067*
H3B	−0.1143	−0.4991	0.0910	0.067*
C18	0.1810 (3)	0.2088 (2)	0.14062 (15)	0.0430 (5)
C17	0.3684 (3)	0.2858 (2)	0.15175 (15)	0.0438 (5)
C11	0.1788 (3)	0.2281 (2)	0.49145 (15)	0.0446 (5)
C2	−0.1646 (3)	−0.3315 (2)	0.19699 (16)	0.0448 (5)
H2A	−0.2869	−0.3398	0.1631	0.054*
H2B	−0.1832	−0.3840	0.2408	0.054*
C10	−0.2342 (3)	0.0813 (2)	0.44419 (16)	0.0479 (5)
H10A	−0.1986	0.0885	0.5112	0.058*
H10B	−0.3565	0.0135	0.4152	0.058*
H10C	−0.2366	0.1733	0.4445	0.058*
C4	0.1457 (3)	−0.3643 (2)	0.16960 (18)	0.0539 (6)
H4A	0.1496	−0.4198	0.2111	0.065*
H4B	0.2156	−0.3952	0.1179	0.065*
C20	−0.1304 (3)	0.1336 (3)	0.04654 (18)	0.0630 (7)
H20A	−0.1993	0.1503	−0.0050	0.076*
H20B	−0.1835	0.1588	0.1051	0.076*
H20C	−0.1369	0.0342	0.0244	0.076*
C21	0.8277 (3)	0.3578 (3)	0.29756 (19)	0.0573 (6)
H21A	0.9466	0.4146	0.2935	0.069*
H21B	0.8305	0.2616	0.2845	0.069*
H21C	0.8025	0.3978	0.3630	0.069*
C13	0.6642 (3)	0.4322 (3)	0.5930 (2)	0.0768 (8)
H13A	0.7287	0.5156	0.6512	0.092*
H13B	0.6768	0.4544	0.5347	0.092*
H13C	0.7174	0.3564	0.5904	0.092*
C12	0.4662 (3)	0.3867 (3)	0.59723 (18)	0.0667 (7)
H12A	0.4530	0.3652	0.6565	0.080*
H12B	0.4124	0.4635	0.6007	0.080*

	U11	U22	U33	U12	U13	U23
C22	0.0715 (18)	0.133 (3)	0.080 (2)	0.0367 (18)	0.0272 (15)	0.072 (2)
O4	0.0339 (8)	0.0517 (9)	0.0690 (10)	0.0004 (6)	0.0116 (7)	0.0298 (8)
O3	0.0343 (8)	0.0524 (9)	0.0480 (8)	0.0054 (6)	0.0031 (6)	−0.0016 (7)
N1	0.0211 (8)	0.0445 (9)	0.0519 (10)	0.0076 (7)	0.0058 (7)	0.0150 (8)
O1	0.0272 (8)	0.0560 (9)	0.0804 (11)	0.0141 (7)	0.0118 (7)	0.0085 (8)
C6	0.0257 (9)	0.0357 (10)	0.0354 (9)	0.0083 (7)	0.0064 (7)	0.0137 (8)
C1	0.0276 (9)	0.0381 (10)	0.0394 (10)	0.0079 (8)	0.0057 (8)	0.0172 (8)
C8	0.0294 (9)	0.0378 (10)	0.0375 (10)	0.0117 (8)	0.0073 (8)	0.0139 (8)
C9	0.0310 (10)	0.0411 (10)	0.0407 (10)	0.0154 (8)	0.0094 (8)	0.0189 (8)
C15	0.0280 (9)	0.0374 (10)	0.0428 (11)	0.0072 (8)	0.0046 (8)	0.0139 (8)
O2	0.0504 (10)	0.0693 (11)	0.0758 (12)	0.0162 (8)	0.0164 (9)	−0.0140 (9)
C5	0.0321 (10)	0.0433 (11)	0.0455 (11)	0.0111 (8)	0.0085 (8)	0.0152 (9)
C16	0.0322 (10)	0.0323 (10)	0.0487 (11)	0.0065 (8)	0.0120 (8)	0.0128 (8)
O6	0.0674 (11)	0.0684 (11)	0.0800 (12)	0.0172 (9)	0.0201 (9)	0.0508 (10)
C19	0.0279 (9)	0.0405 (10)	0.0452 (11)	0.0065 (8)	0.0061 (8)	0.0138 (9)
C7	0.0230 (8)	0.0367 (10)	0.0379 (10)	0.0082 (7)	0.0054 (7)	0.0129 (8)
C14	0.0278 (9)	0.0311 (9)	0.0370 (10)	0.0084 (7)	0.0077 (7)	0.0082 (8)
O5	0.0493 (10)	0.0834 (12)	0.0730 (11)	0.0173 (8)	−0.0018 (8)	0.0458 (10)
C3	0.0474 (13)	0.0447 (12)	0.0554 (13)	0.0020 (10)	0.0087 (10)	0.0035 (10)
C18	0.0408 (11)	0.0454 (11)	0.0438 (11)	0.0160 (9)	0.0042 (9)	0.0167 (9)
C17	0.0456 (12)	0.0406 (11)	0.0496 (12)	0.0129 (9)	0.0128 (9)	0.0215 (9)
C11	0.0380 (11)	0.0462 (11)	0.0463 (11)	0.0114 (9)	0.0111 (9)	0.0133 (9)
C2	0.0322 (10)	0.0419 (11)	0.0521 (12)	0.0030 (8)	0.0034 (9)	0.0145 (9)
C10	0.0340 (11)	0.0593 (13)	0.0570 (13)	0.0217 (9)	0.0163 (9)	0.0223 (10)
C4	0.0470 (12)	0.0435 (12)	0.0636 (14)	0.0163 (10)	0.0146 (11)	0.0080 (10)
C20	0.0466 (13)	0.0887 (18)	0.0515 (13)	0.0309 (13)	0.0002 (10)	0.0186 (13)
C21	0.0307 (11)	0.0586 (14)	0.0789 (16)	0.0055 (10)	0.0112 (11)	0.0268 (12)
C13	0.0482 (14)	0.0747 (17)	0.0697 (17)	0.0042 (12)	−0.0008 (12)	−0.0059 (14)
C12	0.0475 (13)	0.0650 (15)	0.0528 (14)	0.0008 (11)	0.0051 (11)	−0.0078 (12)

C22—O6	1.402 (3)	C19—H19	0.9300
C22—H22A	0.9600	C7—C14	1.525 (2)
C22—H22B	0.9600	C7—H7	0.9800
C22—H22C	0.9600	O5—C18	1.372 (2)
O4—C16	1.375 (2)	O5—C20	1.413 (3)
O4—C21	1.421 (3)	C3—C2	1.506 (3)
O3—C11	1.350 (2)	C3—C4	1.516 (3)
O3—C12	1.446 (3)	C3—H3A	0.9700
N1—C1	1.374 (2)	C3—H3B	0.9700
N1—C9	1.379 (3)	C18—C17	1.399 (3)
N1—H1N	0.83 (3)	C2—H2A	0.9700
O1—C5	1.234 (2)	C2—H2B	0.9700
C6—C1	1.358 (2)	C10—H10A	0.9600
C6—C5	1.453 (3)	C10—H10B	0.9600
C6—C7	1.512 (3)	C10—H10C	0.9600
C1—C2	1.486 (3)	C4—H4A	0.9700
C8—C9	1.355 (2)	C4—H4B	0.9700
C8—C11	1.461 (3)	C20—H20A	0.9600
C8—C7	1.528 (2)	C20—H20B	0.9600
C9—C10	1.508 (3)	C20—H20C	0.9600
C15—C16	1.379 (3)	C21—H21A	0.9600
C15—C14	1.386 (2)	C21—H21B	0.9600
C15—H15	0.9300	C21—H21C	0.9600
O2—C11	1.209 (2)	C13—C12	1.458 (3)
C5—C4	1.505 (3)	C13—H13A	0.9600
C16—C17	1.389 (3)	C13—H13B	0.9600
O6—C17	1.376 (2)	C13—H13C	0.9600
C19—C18	1.384 (3)	C12—H12A	0.9700
C19—C14	1.387 (3)	C12—H12B	0.9700
O6—C22—H22A	109.5	O5—C18—C19	125.06 (18)
O6—C22—H22B	109.5	O5—C18—C17	114.73 (18)
H22A—C22—H22B	109.5	C19—C18—C17	120.20 (18)
O6—C22—H22C	109.5	O6—C17—C16	120.62 (18)
H22A—C22—H22C	109.5	O6—C17—C18	120.21 (18)
H22B—C22—H22C	109.5	C16—C17—C18	119.13 (18)
C16—O4—C21	117.61 (16)	O2—C11—O3	121.13 (19)
C11—O3—C12	116.21 (17)	O2—C11—C8	126.93 (19)
C1—N1—C9	122.70 (16)	O3—C11—C8	111.93 (16)
C1—N1—H1N	116.1 (17)	C1—C2—C3	111.44 (16)
C9—N1—H1N	120.6 (17)	C1—C2—H2A	109.3
C1—C6—C5	119.71 (16)	C3—C2—H2A	109.3
C1—C6—C7	121.31 (16)	C1—C2—H2B	109.3
C5—C6—C7	118.90 (15)	C3—C2—H2B	109.3
C6—C1—N1	119.52 (17)	H2A—C2—H2B	108.0
C6—C1—C2	124.04 (17)	C9—C10—H10A	109.5
N1—C1—C2	116.30 (16)	C9—C10—H10B	109.5
C9—C8—C11	120.34 (17)	H10A—C10—H10B	109.5
C9—C8—C7	120.86 (17)	C9—C10—H10C	109.5
C11—C8—C7	118.80 (16)	H10A—C10—H10C	109.5
C8—C9—N1	119.58 (17)	H10B—C10—H10C	109.5
C8—C9—C10	126.59 (18)	C5—C4—C3	113.84 (18)
N1—C9—C10	113.77 (16)	C5—C4—H4A	108.8
C16—C15—C14	120.44 (18)	C3—C4—H4A	108.8
C16—C15—H15	119.8	C5—C4—H4B	108.8
C14—C15—H15	119.8	C3—C4—H4B	108.8
O1—C5—C6	121.43 (18)	H4A—C4—H4B	107.7
O1—C5—C4	120.26 (18)	O5—C20—H20A	109.5
C6—C5—C4	118.29 (16)	O5—C20—H20B	109.5
O4—C16—C15	124.14 (18)	H20A—C20—H20B	109.5
O4—C16—C17	115.44 (17)	O5—C20—H20C	109.5
C15—C16—C17	120.42 (17)	H20A—C20—H20C	109.5
C17—O6—C22	113.52 (19)	H20B—C20—H20C	109.5
C18—C19—C14	120.14 (17)	O4—C21—H21A	109.5
C18—C19—H19	119.9	O4—C21—H21B	109.5
C14—C19—H19	119.9	H21A—C21—H21B	109.5
C6—C7—C14	112.18 (15)	O4—C21—H21C	109.5
C6—C7—C8	110.40 (14)	H21A—C21—H21C	109.5
C14—C7—C8	111.39 (14)	H21B—C21—H21C	109.5
C6—C7—H7	107.6	C12—C13—H13A	109.5
C14—C7—H7	107.6	C12—C13—H13B	109.5
C8—C7—H7	107.6	H13A—C13—H13B	109.5
C15—C14—C19	119.66 (17)	C12—C13—H13C	109.5
C15—C14—C7	119.36 (16)	H13A—C13—H13C	109.5
C19—C14—C7	120.98 (16)	H13B—C13—H13C	109.5
C18—O5—C20	118.35 (18)	O3—C12—C13	110.0 (2)
C2—C3—C4	110.79 (18)	O3—C12—H12A	109.7
C2—C3—H3A	109.5	C13—C12—H12A	109.7
C4—C3—H3A	109.5	O3—C12—H12B	109.7
C2—C3—H3B	109.5	C13—C12—H12B	109.7
C4—C3—H3B	109.5	H12A—C12—H12B	108.2
H3A—C3—H3B	108.1
C5—C6—C1—N1	171.81 (16)	C6—C7—C14—C15	−120.58 (18)
C7—C6—C1—N1	−5.1 (3)	C8—C7—C14—C15	115.10 (18)
C5—C6—C1—C2	−3.6 (3)	C6—C7—C14—C19	59.5 (2)
C7—C6—C1—C2	179.45 (17)	C8—C7—C14—C19	−64.8 (2)
C9—N1—C1—C6	−14.9 (3)	C20—O5—C18—C19	−4.4 (3)
C9—N1—C1—C2	160.86 (18)	C20—O5—C18—C17	174.56 (19)
C11—C8—C9—N1	−174.65 (17)	C14—C19—C18—O5	178.62 (19)
C7—C8—C9—N1	5.4 (3)	C14—C19—C18—C17	−0.3 (3)
C11—C8—C9—C10	2.4 (3)	C22—O6—C17—C16	91.5 (3)
C7—C8—C9—C10	−177.55 (17)	C22—O6—C17—C18	−90.4 (3)
C1—N1—C9—C8	14.7 (3)	O4—C16—C17—O6	−3.2 (3)
C1—N1—C9—C10	−162.71 (17)	C15—C16—C17—O6	177.59 (18)
C1—C6—C5—O1	−173.80 (19)	O4—C16—C17—C18	178.77 (17)
C7—C6—C5—O1	3.2 (3)	C15—C16—C17—C18	−0.5 (3)
C1—C6—C5—C4	4.2 (3)	O5—C18—C17—O6	3.4 (3)
C7—C6—C5—C4	−178.84 (18)	C19—C18—C17—O6	−177.62 (18)
C21—O4—C16—C15	−2.2 (3)	O5—C18—C17—C16	−178.56 (18)
C21—O4—C16—C17	178.60 (18)	C19—C18—C17—C16	0.5 (3)
C14—C15—C16—O4	−178.84 (17)	C12—O3—C11—O2	0.6 (3)
C14—C15—C16—C17	0.3 (3)	C12—O3—C11—C8	−178.82 (19)
C1—C6—C7—C14	−103.04 (19)	C9—C8—C11—O2	−12.8 (3)
C5—C6—C7—C14	80.0 (2)	C7—C8—C11—O2	167.2 (2)
C1—C6—C7—C8	21.8 (2)	C9—C8—C11—O3	166.62 (17)
C5—C6—C7—C8	−155.10 (16)	C7—C8—C11—O3	−13.4 (2)
C9—C8—C7—C6	−22.0 (2)	C6—C1—C2—C3	−24.4 (3)
C11—C8—C7—C6	158.08 (16)	N1—C1—C2—C3	160.04 (18)
C9—C8—C7—C14	103.36 (19)	C4—C3—C2—C1	49.9 (3)
C11—C8—C7—C14	−76.6 (2)	O1—C5—C4—C3	−158.6 (2)
C16—C15—C14—C19	−0.2 (3)	C6—C5—C4—C3	23.5 (3)
C16—C15—C14—C7	179.89 (16)	C2—C3—C4—C5	−50.4 (3)
C18—C19—C14—C15	0.1 (3)	C11—O3—C12—C13	−164.3 (2)
C18—C19—C14—C7	−179.92 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.98	2.36	2.720 (2)	101
N1—H1N···O1i	0.83 (3)	2.21 (3)	2.995 (2)	160 (3)
C2—H2B···O4ii	0.97	2.55	3.340 (3)	138
C10—H10B···O1i	0.96	2.59	3.429 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (3)	2.21 (3)	2.995 (2)	160 (3)
C2—H2B⋯O4ii	0.97	2.55	3.340 (3)	138
C10—H10B⋯O1i	0.96	2.59	3.429 (3)	146

Symmetry codes: (i) ; (ii) .