Methyl 4-(4-meth­oxy­phen­yl)-2-methyl-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

Xiao-Hui Yang; Yong-Hong Zhou; Meng Zhang; Xing Song

doi:10.1107/S1600536810039760

. 2010 Oct 9;66(Pt 11):o2767. doi: 10.1107/S1600536810039760

Methyl 4-(4-methoxyphenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Xiao-Hui Yang ^a, Yong-Hong Zhou ^a,^*, Meng Zhang ^a, Xing Song ^a

PMCID: PMC3009142 PMID: 21588969

Abstract

In the title compound, C₁₉H₂₁NO₄, the dihydropyridine ring adopts a distorted screw-boat conformation. The fused cyclohexenone 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 intramolecular C—H⋯O interaction occurs. In the crystal, molecules are linked by intermolecular 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 _r = 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
Δρ_max = 0.16 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-66-o2767-sup1.cif^{(20.3KB, cif)}

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

e-66-o2767-Isup2.hkl^{(149.2KB, hkl)}

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

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

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the President of the Chinese Academy of Forestry Foundation (CAFYBB2008009).

supplementary crystallographic information

Comment

The development of new methods for the synthesis of 1,4-dihydropyridine derivatives is a motive for the current study. 1,4-dihydropyridine derivatives attract interest because of their presence in numerous natural products. In addition, they exhibit calcium modulatory properties (Rose & Draeger, 1992), antibacterial (Davies et al., 2005) and fungicidal activity (Warrior et al., 2005).

In the title compound the heterocyclic ring adopts a distorted screw-boat conformation (Fig. 1). Atoms C7 and N deviate from the mean plane of C1/C6/C8/C9 by 0.177 (3)Å and 0.067 (7)Å, respectively. The fused cyclohexene ring displays a slightly distorted envelope conformation, with atom C3 out of the plane of the atoms by -0.314 (5)°. The dihedral angle between the mean planes of the benzene and heterocyclic rings is 86.1 (7)°. The methoxy group is nearly coplanar with the attached benzene ring with a C19/O4/C16/C17 torsion angle of -4.1 (6)°. Crystal packing is stabilized by an intermolecular N—H···O hydrogen bond forming an infinite chain of molecules along the c axis (Table 1, Fig. 2).

Experimental

A mixture of 4-methoxybenzaldehyde (2 mmol), methyl 3-oxobutanoate (4 mmol), cyclohexane-1,3-dione (2 mmol) and NH₄CO₃ (2 mmol) was stirred in water (2 ml) at 353 K. After completion of the reaction (TLC monitoring),the mixture was diluted with cold water (20 ml) and filtered to obtain the precipitated product which was further purified by recrystallization. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.