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

In the title compound, C(19)H(21)NO(4), the dihydro-pyridine ring adopts a distorted screw-boat conformation. The fused cyclo-hexenone ring forms a slightly distorted envelope conformation. The dihedral angle between the mean planes of the benzene and heterocyclic rings is 86.1 (7)°. An intra-molecular C-H⋯O inter-action occurs. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming an infinite chain along the c axis.

Related literature

For the physiological activity of 1,4-dihydro­pyridine derivatives, see: Davies et al. (2005 ▶); Rose & Draeger (1992 ▶); Warrior et al. (2005 ▶).

Experimental

Crystal data

C19H21NO4

M = 327.37

Monoclinic,

a = 13.628 (3) Å

b = 8.6300 (17) Å

c = 14.577 (3) Å

β = 98.39 (3)°

V = 1696.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.982, T max = 0.996

3232 measured reflections

3040 independent reflections

1300 reflections with I > 2σ(I)

R int = 0.078

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.128

S = 1.00

3040 reflections

217 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039760/jj2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039760/jj2057Isup2.hkl

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

C19H21NO4	F(000) = 696
Mr = 327.37	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.628 (3) Å	θ = 9–12°
b = 8.6300 (17) Å	µ = 0.09 mm−1
c = 14.577 (3) Å	T = 293 K
β = 98.39 (3)°	Block, colourless
V = 1696.0 (6) Å3	0.20 × 0.20 × 0.05 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1300 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
graphite	θmax = 25.3°, θmin = 1.5°
ω/2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.982, Tmax = 0.996	l = −17→17
3232 measured reflections	3 standard reflections every 200 reflections
3040 independent reflections	intensity decay: 1%

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3
3040 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Experimental. Absorption correction: semi-empirical absorption based on psi-scan (North et al., 1968)

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
N	0.7089 (2)	−0.1346 (4)	1.10531 (19)	0.0561 (9)
H0A	0.7239	−0.1617	1.1624	0.067*
O1	0.7167 (2)	−0.2573 (3)	0.79342 (17)	0.0675 (8)
C1	0.7348 (2)	−0.2312 (4)	1.0380 (2)	0.0437 (9)
O3	0.5828 (3)	0.3072 (4)	1.0342 (2)	0.1228 (14)
O2	0.5564 (2)	0.2194 (3)	0.8893 (2)	0.0691 (8)
C2	0.7719 (3)	−0.3882 (4)	1.0694 (2)	0.0579 (11)
H2A	0.7161	−0.4545	1.0764	0.069*
H2B	0.8130	−0.3795	1.1294	0.069*
C3	0.8315 (3)	−0.4604 (5)	1.0013 (3)	0.0783 (14)
H3A	0.8450	−0.5680	1.0178	0.094*
H3B	0.8944	−0.4069	1.0040	0.094*
O4	1.0127 (2)	0.2744 (3)	0.7949 (2)	0.0800 (9)
C4	0.7756 (3)	−0.4514 (5)	0.9038 (3)	0.0713 (13)
H4A	0.8194	−0.4841	0.8606	0.086*
H4B	0.7204	−0.5234	0.8983	0.086*
C5	0.7367 (3)	−0.2935 (5)	0.8765 (3)	0.0571 (11)
C6	0.7201 (3)	−0.1864 (4)	0.9470 (2)	0.0444 (9)
C7	0.6864 (3)	−0.0254 (4)	0.9202 (2)	0.0488 (10)
H7A	0.6318	−0.0343	0.8686	0.059*
C8	0.6458 (3)	0.0595 (4)	0.9990 (3)	0.0477 (9)
C9	0.6599 (3)	0.0044 (4)	1.0854 (3)	0.0486 (10)
C10	0.6220 (3)	0.0715 (4)	1.1683 (2)	0.0673 (12)
H10A	0.5884	0.1673	1.1514	0.101*
H10B	0.6767	0.0903	1.2165	0.101*
H10C	0.5767	0.0000	1.1902	0.101*
C11	0.5931 (3)	0.2038 (5)	0.9799 (3)	0.0648 (12)
C12	0.5003 (4)	0.3605 (5)	0.8655 (3)	0.1003 (17)
H12A	0.4785	0.3631	0.7998	0.151*
H12B	0.5416	0.4487	0.8832	0.151*
H12C	0.4437	0.3628	0.8977	0.151*
C13	0.7696 (3)	0.0644 (4)	0.8845 (2)	0.0432 (9)
C14	0.8566 (3)	0.0938 (4)	0.9442 (2)	0.0570 (11)
H14A	0.8619	0.0646	1.0061	0.068*
C15	0.9360 (3)	0.1667 (5)	0.9120 (3)	0.0635 (12)
H15A	0.9937	0.1868	0.9527	0.076*
C16	0.9296 (3)	0.2093 (5)	0.8199 (3)	0.0577 (11)
C17	0.8445 (3)	0.1823 (4)	0.7607 (2)	0.0519 (10)
H17A	0.8393	0.2115	0.6988	0.062*
C18	0.7645 (3)	0.1101 (4)	0.7942 (2)	0.0500 (10)
H18A	0.7063	0.0927	0.7537	0.060*
C19	1.0128 (3)	0.3077 (6)	0.6991 (3)	0.0961 (17)
H19A	1.0752	0.3531	0.6908	0.144*
H19B	0.9602	0.3788	0.6781	0.144*
H19C	1.0032	0.2135	0.6638	0.144*

	U11	U22	U33	U12	U13	U23
N	0.080 (2)	0.055 (2)	0.0358 (17)	0.0012 (18)	0.0164 (16)	−0.0055 (16)
O1	0.096 (2)	0.071 (2)	0.0380 (14)	−0.0014 (16)	0.0202 (15)	−0.0075 (15)
C1	0.047 (2)	0.039 (2)	0.046 (2)	−0.0057 (18)	0.0089 (17)	−0.0011 (18)
O3	0.212 (4)	0.069 (2)	0.091 (3)	0.048 (3)	0.033 (3)	−0.015 (2)
O2	0.076 (2)	0.0566 (19)	0.074 (2)	0.0125 (16)	0.0078 (16)	0.0084 (16)
C2	0.072 (3)	0.047 (3)	0.055 (2)	−0.002 (2)	0.008 (2)	0.002 (2)
C3	0.113 (4)	0.055 (3)	0.066 (3)	0.012 (3)	0.012 (3)	−0.005 (2)
O4	0.072 (2)	0.092 (2)	0.079 (2)	−0.0276 (18)	0.0220 (16)	0.0123 (18)
C4	0.096 (4)	0.060 (3)	0.061 (3)	0.001 (3)	0.022 (3)	−0.008 (2)
C5	0.071 (3)	0.043 (2)	0.060 (3)	−0.010 (2)	0.018 (2)	−0.013 (2)
C6	0.052 (2)	0.044 (2)	0.038 (2)	−0.0081 (19)	0.0100 (17)	−0.0026 (18)
C7	0.056 (2)	0.040 (2)	0.053 (2)	−0.0059 (19)	0.016 (2)	−0.0072 (18)
C8	0.049 (2)	0.040 (2)	0.058 (2)	−0.0060 (19)	0.0200 (19)	−0.007 (2)
C9	0.066 (3)	0.037 (2)	0.048 (2)	0.0044 (19)	0.025 (2)	0.0020 (19)
C10	0.100 (3)	0.051 (3)	0.057 (2)	0.002 (2)	0.034 (2)	−0.009 (2)
C11	0.085 (3)	0.044 (3)	0.069 (3)	−0.007 (3)	0.022 (3)	−0.003 (2)
C12	0.108 (4)	0.072 (3)	0.126 (4)	0.006 (3)	0.032 (3)	0.026 (3)
C13	0.047 (2)	0.037 (2)	0.044 (2)	0.0087 (18)	0.0037 (18)	−0.0025 (17)
C14	0.073 (3)	0.054 (3)	0.042 (2)	−0.009 (2)	0.002 (2)	0.0095 (19)
C15	0.071 (3)	0.063 (3)	0.056 (3)	−0.001 (2)	0.005 (2)	−0.002 (2)
C16	0.061 (3)	0.054 (3)	0.062 (3)	−0.010 (2)	0.021 (2)	−0.008 (2)
C17	0.068 (3)	0.047 (2)	0.042 (2)	−0.013 (2)	0.014 (2)	0.0054 (18)
C18	0.052 (2)	0.053 (3)	0.046 (2)	−0.002 (2)	0.0082 (18)	0.004 (2)
C19	0.086 (4)	0.116 (4)	0.093 (4)	−0.036 (3)	0.035 (3)	0.007 (3)

N—C1	1.372 (4)	C7—H7A	0.9800
N—C9	1.383 (4)	C8—C9	1.334 (4)
N—H0A	0.8600	C8—C11	1.444 (5)
O1—C5	1.242 (4)	C9—C10	1.498 (4)
C1—C6	1.367 (4)	C10—H10A	0.9600
C1—C2	1.495 (4)	C10—H10B	0.9600
O3—C11	1.214 (4)	C10—H10C	0.9600
O2—C11	1.349 (4)	C12—H12A	0.9600
O2—C12	1.453 (4)	C12—H12B	0.9600
C2—C3	1.506 (5)	C12—H12C	0.9600
C2—H2A	0.9700	C13—C18	1.366 (4)
C2—H2B	0.9700	C13—C14	1.388 (4)
C3—C4	1.514 (5)	C14—C15	1.390 (5)
C3—H3A	0.9700	C14—H14A	0.9300
C3—H3B	0.9700	C15—C16	1.383 (5)
O4—C16	1.361 (4)	C15—H15A	0.9300
O4—C19	1.426 (4)	C16—C17	1.361 (5)
C4—C5	1.495 (5)	C17—C18	1.403 (4)
C4—H4A	0.9700	C17—H17A	0.9300
C4—H4B	0.9700	C18—H18A	0.9300
C5—C6	1.425 (4)	C19—H19A	0.9600
C6—C7	1.497 (4)	C19—H19B	0.9600
C7—C13	1.527 (4)	C19—H19C	0.9600
C7—C8	1.532 (4)
C1—N—C9	122.9 (3)	C8—C9—C10	127.2 (4)
C1—N—H0A	118.5	N—C9—C10	112.3 (3)
C9—N—H0A	118.5	C9—C10—H10A	109.5
C6—C1—N	120.4 (3)	C9—C10—H10B	109.5
C6—C1—C2	123.3 (3)	H10A—C10—H10B	109.5
N—C1—C2	116.2 (3)	C9—C10—H10C	109.5
C11—O2—C12	115.1 (3)	H10A—C10—H10C	109.5
C1—C2—C3	111.3 (3)	H10B—C10—H10C	109.5
C1—C2—H2A	109.4	O3—C11—O2	120.2 (4)
C3—C2—H2A	109.4	O3—C11—C8	127.5 (4)
C1—C2—H2B	109.4	O2—C11—C8	112.2 (4)
C3—C2—H2B	109.4	O2—C12—H12A	109.5
H2A—C2—H2B	108.0	O2—C12—H12B	109.5
C2—C3—C4	110.6 (4)	H12A—C12—H12B	109.5
C2—C3—H3A	109.5	O2—C12—H12C	109.5
C4—C3—H3A	109.5	H12A—C12—H12C	109.5
C2—C3—H3B	109.5	H12B—C12—H12C	109.5
C4—C3—H3B	109.5	C18—C13—C14	118.0 (3)
H3A—C3—H3B	108.1	C18—C13—C7	122.6 (3)
C16—O4—C19	117.7 (3)	C14—C13—C7	119.3 (3)
C5—C4—C3	114.0 (3)	C13—C14—C15	120.4 (3)
C5—C4—H4A	108.7	C13—C14—H14A	119.8
C3—C4—H4A	108.7	C15—C14—H14A	119.8
C5—C4—H4B	108.7	C16—C15—C14	120.4 (4)
C3—C4—H4B	108.7	C16—C15—H15A	119.8
H4A—C4—H4B	107.6	C14—C15—H15A	119.8
O1—C5—C6	120.4 (4)	C17—C16—O4	124.5 (4)
O1—C5—C4	120.5 (4)	C17—C16—C15	119.8 (4)
C6—C5—C4	119.1 (3)	O4—C16—C15	115.6 (4)
C1—C6—C5	120.0 (4)	C16—C17—C18	119.2 (3)
C1—C6—C7	120.7 (3)	C16—C17—H17A	120.4
C5—C6—C7	119.2 (3)	C18—C17—H17A	120.4
C6—C7—C13	110.2 (3)	C13—C18—C17	122.1 (3)
C6—C7—C8	112.3 (3)	C13—C18—H18A	119.0
C13—C7—C8	112.3 (3)	C17—C18—H18A	119.0
C6—C7—H7A	107.2	O4—C19—H19A	109.5
C13—C7—H7A	107.2	O4—C19—H19B	109.5
C8—C7—H7A	107.2	H19A—C19—H19B	109.5
C9—C8—C11	119.3 (4)	O4—C19—H19C	109.5
C9—C8—C7	121.3 (4)	H19A—C19—H19C	109.5
C11—C8—C7	119.4 (3)	H19B—C19—H19C	109.5
C8—C9—N	120.4 (3)
C9—N—C1—C6	5.7 (5)	C11—C8—C9—C10	3.5 (6)
C9—N—C1—C2	−170.1 (3)	C7—C8—C9—C10	−177.9 (3)
C6—C1—C2—C3	25.1 (5)	C1—N—C9—C8	−8.0 (5)
N—C1—C2—C3	−159.3 (3)	C1—N—C9—C10	168.2 (3)
C1—C2—C3—C4	−49.6 (5)	C12—O2—C11—O3	−3.8 (6)
C2—C3—C4—C5	49.9 (5)	C12—O2—C11—C8	178.5 (3)
C3—C4—C5—O1	158.2 (4)	C9—C8—C11—O3	22.9 (7)
C3—C4—C5—C6	−23.5 (6)	C7—C8—C11—O3	−155.7 (4)
N—C1—C6—C5	−173.0 (3)	C9—C8—C11—O2	−159.6 (4)
C2—C1—C6—C5	2.4 (5)	C7—C8—C11—O2	21.8 (5)
N—C1—C6—C7	6.9 (5)	C6—C7—C13—C18	112.6 (4)
C2—C1—C6—C7	−177.6 (3)	C8—C7—C13—C18	−121.4 (4)
O1—C5—C6—C1	174.9 (4)	C6—C7—C13—C14	−63.6 (4)
C4—C5—C6—C1	−3.4 (5)	C8—C7—C13—C14	62.4 (4)
O1—C5—C6—C7	−5.1 (5)	C18—C13—C14—C15	−0.4 (5)
C4—C5—C6—C7	176.7 (3)	C7—C13—C14—C15	175.9 (3)
C1—C6—C7—C13	110.8 (4)	C13—C14—C15—C16	−0.7 (6)
C5—C6—C7—C13	−69.3 (4)	C19—O4—C16—C17	−4.1 (6)
C1—C6—C7—C8	−15.3 (5)	C19—O4—C16—C15	174.6 (4)
C5—C6—C7—C8	164.7 (3)	C14—C15—C16—C17	1.2 (6)
C6—C7—C8—C9	13.1 (5)	C14—C15—C16—O4	−177.5 (3)
C13—C7—C8—C9	−111.8 (4)	O4—C16—C17—C18	178.0 (4)
C6—C7—C8—C11	−168.3 (3)	C15—C16—C17—C18	−0.6 (6)
C13—C7—C8—C11	66.8 (4)	C14—C13—C18—C17	1.1 (5)
C11—C8—C9—N	179.2 (3)	C7—C13—C18—C17	−175.1 (3)
C7—C8—C9—N	−2.2 (6)	C16—C17—C18—C13	−0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O1i	0.86	2.05	2.884 (4)	163
C10—H10A···O3	0.96	2.08	2.818 (5)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O1i	0.86	2.05	2.884 (4)	163
C10—H10A⋯O3	0.96	2.08	2.818 (5)	132

Symmetry code: (i) .