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

Yang, X.-H.; Zhou, Y.-H.; Zhang, M.; Song, X.

doi:10.1107/S1600536810039760

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2767

https://doi.org/10.1107/S1600536810039760

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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 and Xing Song ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
^*Correspondence e-mail: hmilydear@163.com

(Received 4 September 2010; accepted 5 October 2010; online 9 October 2010)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.070
wR(F²) = 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

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) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039760/jj2057Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing of the title compound, viewed along the a axis. Dashed lines indicate N—H···O hydrogen bonds.

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

Crystal data top

C₁₉H₂₁NO₄	F(000) = 696
M_r = 327.37	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3
3040 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₂₁NO₄	V = 1696.0 (6) Å³
M_r = 327.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.628 (3) Å	µ = 0.09 mm⁻¹
b = 8.6300 (17) Å	T = 293 K
c = 14.577 (3) Å	0.20 × 0.20 × 0.05 mm
β = 98.39 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1300 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.078
T_min = 0.982, T_max = 0.996	3 standard reflections every 200 reflections
3232 measured reflections	intensity decay: 1%
3040 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	1 restraint
wR(F²) = 0.128	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
3040 reflections	Δρ_min = −0.19 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁NO₄
M_r	327.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.628 (3), 8.6300 (17), 14.577 (3)
β (°)	98.39 (3)
V (Å³)	1696.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.982, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	3232, 3040, 1300
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.128, 1.00
No. of reflections	3040
No. of parameters	217
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z+1/2.

Acknowledgements

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

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Davies, D. T., Markwell, R. E., Pearson, N. D. & Takle, A. K. (2005). US Patent 6 911 442. Google Scholar
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rose, U. & Draeger, M. (1992). J. Med. Chem. A, 35, 2238–2243. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Warrior, P., Heiman, D. F., Fugiel, J. A. & Petracek, P. D. (2005). WO Patent 2005060748. Google Scholar

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Volume 66| Part 11| November 2010| Page o2767

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Acknowledgements

References

organic compounds

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