Diethyl 4-(2-meth­oxy­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

Wang, K.; Wang, Y.; Yao, M.; Xu, D.

doi:10.1107/S1600536813009951

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o785

https://doi.org/10.1107/S1600536813009951

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Diethyl 4-(2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Ke Wang,^a Yifeng Wang,^a Minjie Yao ^a and Danqian Xu ^a ^*

^aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: chrc@zjut.edu.cn

(Received 21 March 2013; accepted 11 April 2013; online 24 April 2013)

In the title compound, C₂₀H₂₅NO₅, the dihydropyridine ring adopts a flattened boat conformation. The methoxyphenyl ring is almost perpendicular to the mean plane of the pyridine ring [dihedral angle = 88.42 (3)°]. The two carbonyl units adopt a synperiplanar conformation with respect to the double bonds in the dihydropyridine ring. In the crystal, molecules are connected by N—H⋯O hydrogen bonds into R₄⁴(24) tetrameric rings. A region of disordered electron density, located at the center of four adjacent molecules, was treated with the SQUEEZE routine in PLATON [Spek (2009 ). Acta Cryst. D65, 148–155]. It is probably the result of traces of the solvent of crystallization and was not taken into account during the structure refinement.

Related literature

For general background to 1,4-dihydropyridine compounds, see: Franke et al. (2008 ); Takemoto et al. (2010 ). For related structures, see: Fun et al. (2012 ); Kapoor et al. (2011 ).

Experimental

Crystal data

C₂₀H₂₅NO₅
M_r = 359.41
Tetragonal, $[P \overline 42_1 c ]$
a = 22.4689 (7) Å
c = 8.2443 (3) Å
V = 4162.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.47 × 0.31 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.952, T_max = 0.982
60800 measured reflections
4755 independent reflections
3128 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.167
S = 1.00
4755 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.86	2.07	2.924 (3)	170
Symmetry code: (i) y, -x+1, -z.

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, 2102).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009951/pk2475sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009951/pk2475Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009951/pk2475Isup3.cml

checkCIF report

Comment top

1,4-Dihydropyridine compounds are important drugs by virtue of their pharmacological activities, and they are used in the treatment of a number of diseases, such as cardiovascular diseases and Alzheimer's disease. In this article, the crystal structure of the dihydropyridine compoud diethyl 4-(2-methoxyphenyl)-2,6- dimethyl-1,4-dihydropyridine-3,5-dicarboxylate is described (Fig. 1). The dihydropyridine ring adopts a flattened boat conformation. The methoxyphenyl ring is almost perpendicular to the mean plane of the pyridine ring [dihedral angle = 88.42 (3)°]. The two carbonyl units adopt a synperiplanar conformation with respect to the double bonds in the dihydropyridine ring. In the crystal, the molecules are connected by intermolecular N—H···O hydrogen bonds into R₄⁴(24) tetrameric rings. A region of disordered electron density, located at the center of four adjacent molecules, was treated using the SQUEEZE routine in PLATON (Spek, 2009), which indicated a solvent-accessible void of of 178 Å³. It is probably due to traces of the solvent of crystallization and was not taken into account during structure refinement.

Related literature top

For general background to 1,4-dihydropyridine compounds, see: Franke et al. (2008); Takemoto et al. (2010). For related structures, see: Fun et al. (2012); Kapoor et al. (2011).

Experimental top

The mixture of 2-methoxybenzaldehyde (1 mmol), ethylacetoacetate (2 mmol) and ammonium acetate(1 mmol) was stirred at at 343 K for 3 h (monitored by TLC). Then the mixture was purified by flash column chromatography (silica gel, Hex/AcOEt, v/v, 3:1) giving the title compound. Single crystals were obtained by slow evaporation of a CH₂Cl₂ and n-Hexane solution.

Structure description top

For general background to 1,4-dihydropyridine compounds, see: Franke et al. (2008); Takemoto et al. (2010). For related structures, see: Fun et al. (2012); Kapoor et al. (2011).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); 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, 2102).

Figures top

	Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. The molecular packing of the title compound showing the R₄⁴(24) tetrameric rings, with N1—H1···O5 hydrogen bonds shown as dashed lines.

Diethyl 4-(2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₀H₂₅NO₅	D_x = 1.147 Mg m⁻³
M_r = 359.41	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42₁c	Cell parameters from 36625 reflections
Hall symbol: P -4 2n	θ = 3.1–27.4°
a = 22.4689 (7) Å	µ = 0.08 mm⁻¹
c = 8.2443 (3) Å	T = 296 K
V = 4162.1 (2) Å³	Block, colorless
Z = 8	0.47 × 0.31 × 0.22 mm
F(000) = 1536

Data collection top

Rigaku R-AXIS RAPID/ZJUG diffractometer	4755 independent reflections
Radiation source: rotating anode	3128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −20→20
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = 0→29
T_min = 0.952, T_max = 0.982	l = 0→10
60800 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0855P)² + 0.9222P] where P = (F_o² + 2F_c²)/3
4755 reflections	(Δ/σ)_max = 0.008
241 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₂₅NO₅	Z = 8
M_r = 359.41	Mo Kα radiation
Tetragonal, P42₁c	µ = 0.08 mm⁻¹
a = 22.4689 (7) Å	T = 296 K
c = 8.2443 (3) Å	0.47 × 0.31 × 0.22 mm
V = 4162.1 (2) Å³

Data collection top

Rigaku R-AXIS RAPID/ZJUG diffractometer	4755 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3128 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.982	R_int = 0.078
60800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
4755 reflections	Δρ_min = −0.20 e Å⁻³
241 parameters

Special details top

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
C1	0.48258 (11)	0.26476 (11)	0.3185 (3)	0.0488 (6)
H1	0.5183	0.2658	0.3866	0.059*
C2	0.43244 (11)	0.29128 (12)	0.4187 (3)	0.0487 (6)
C3	0.39385 (13)	0.33091 (13)	0.3545 (4)	0.0559 (7)
C4	0.45445 (13)	0.34162 (12)	0.1122 (3)	0.0524 (7)
C5	0.49582 (12)	0.30287 (11)	0.1698 (3)	0.0482 (6)
C6	0.47208 (12)	0.19936 (12)	0.2738 (3)	0.0485 (6)
C7	0.51178 (14)	0.15615 (13)	0.3240 (4)	0.0623 (8)
H7	0.5442	0.1673	0.3872	0.075*
C8	0.50466 (18)	0.09635 (15)	0.2830 (5)	0.0797 (10)
H8	0.5316	0.0681	0.3207	0.096*
C9	0.45815 (16)	0.07942 (15)	0.1875 (5)	0.0802 (10)
H9	0.4540	0.0397	0.1575	0.096*
C10	0.41693 (16)	0.12109 (14)	0.1349 (4)	0.0705 (8)
H10	0.3851	0.1095	0.0700	0.085*
C11	0.42368 (13)	0.18025 (12)	0.1801 (4)	0.0546 (7)
C12	0.33177 (15)	0.20776 (18)	0.0506 (5)	0.0826 (11)
H12A	0.3415	0.1878	−0.0490	0.124*
H12B	0.3088	0.2428	0.0273	0.124*
H12C	0.3090	0.1815	0.1184	0.124*
C13	0.42649 (12)	0.27102 (13)	0.5869 (3)	0.0515 (6)
C14	0.47214 (15)	0.21103 (14)	0.7908 (3)	0.0628 (8)
H14A	0.4387	0.1840	0.8019	0.075*
H14B	0.4685	0.2420	0.8722	0.075*
C15	0.52918 (17)	0.17829 (16)	0.8121 (5)	0.0817 (10)
H15A	0.5305	0.1453	0.7383	0.123*
H15B	0.5319	0.1639	0.9215	0.123*
H15C	0.5619	0.2046	0.7904	0.123*
C16	0.34108 (15)	0.35877 (18)	0.4346 (5)	0.0817 (10)
H16A	0.3139	0.3282	0.4683	0.123*
H16B	0.3215	0.3849	0.3594	0.123*
H16C	0.3539	0.3811	0.5275	0.123*
C17	0.45761 (16)	0.37777 (15)	−0.0409 (4)	0.0698 (9)
H17A	0.4739	0.4163	−0.0171	0.105*
H17B	0.4184	0.3823	−0.0853	0.105*
H17C	0.4826	0.3579	−0.1182	0.105*
C18	0.55359 (12)	0.29701 (12)	0.0932 (4)	0.0525 (7)
C19	0.65098 (15)	0.2576 (2)	0.1250 (5)	0.0846 (11)
H19A	0.6722	0.2949	0.1383	0.102*
H19B	0.6512	0.2471	0.0108	0.102*
C20	0.6793 (2)	0.2111 (3)	0.2197 (7)	0.140 (2)
H20A	0.6677	0.2149	0.3313	0.210*
H20B	0.7218	0.2148	0.2110	0.210*
H20C	0.6672	0.1729	0.1794	0.210*
N1	0.40319 (10)	0.35131 (11)	0.1988 (3)	0.0599 (6)
H1A	0.3752	0.3713	0.1532	0.072*
O1	0.38505 (9)	0.22427 (9)	0.1319 (3)	0.0636 (6)
O2	0.47297 (9)	0.23683 (10)	0.6302 (2)	0.0633 (6)
O3	0.38594 (9)	0.28131 (11)	0.6811 (3)	0.0712 (6)
O4	0.59075 (8)	0.26366 (10)	0.1817 (3)	0.0654 (6)
O5	0.56955 (10)	0.31897 (11)	−0.0357 (3)	0.0738 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0473 (14)	0.0528 (14)	0.0462 (13)	0.0037 (11)	0.0026 (12)	0.0049 (12)
C2	0.0461 (14)	0.0570 (15)	0.0429 (13)	−0.0004 (11)	0.0039 (11)	−0.0004 (12)
C3	0.0520 (15)	0.0602 (17)	0.0554 (16)	0.0044 (13)	0.0034 (13)	0.0039 (13)
C4	0.0585 (16)	0.0496 (14)	0.0490 (15)	−0.0008 (12)	−0.0007 (13)	0.0047 (12)
C5	0.0511 (14)	0.0492 (14)	0.0442 (14)	−0.0067 (12)	0.0027 (12)	0.0024 (11)
C6	0.0525 (14)	0.0499 (14)	0.0432 (13)	0.0026 (11)	0.0073 (12)	0.0077 (11)
C7	0.0605 (17)	0.0605 (17)	0.0659 (18)	0.0080 (14)	0.0056 (15)	0.0099 (15)
C8	0.086 (2)	0.0608 (19)	0.092 (3)	0.0170 (17)	0.011 (2)	0.0100 (18)
C9	0.089 (2)	0.0545 (18)	0.097 (3)	0.0006 (17)	0.012 (2)	0.0019 (19)
C10	0.081 (2)	0.0586 (18)	0.072 (2)	−0.0094 (16)	0.0081 (17)	−0.0001 (16)
C11	0.0564 (15)	0.0543 (15)	0.0530 (15)	−0.0003 (13)	0.0088 (13)	0.0092 (13)
C12	0.063 (2)	0.088 (2)	0.096 (3)	−0.0112 (18)	−0.0207 (18)	0.013 (2)
C13	0.0530 (15)	0.0578 (15)	0.0439 (14)	−0.0028 (13)	0.0014 (12)	−0.0015 (12)
C14	0.0764 (19)	0.0706 (18)	0.0415 (14)	−0.0027 (15)	0.0005 (14)	0.0091 (14)
C15	0.102 (3)	0.080 (2)	0.063 (2)	0.017 (2)	−0.004 (2)	0.0156 (18)
C16	0.0598 (19)	0.102 (3)	0.084 (2)	0.0253 (19)	0.0137 (18)	0.006 (2)
C17	0.083 (2)	0.0630 (18)	0.0630 (19)	0.0057 (17)	0.0066 (17)	0.0187 (16)
C18	0.0548 (15)	0.0510 (14)	0.0516 (15)	−0.0058 (12)	0.0025 (13)	0.0010 (13)
C19	0.0505 (17)	0.123 (3)	0.080 (2)	0.0072 (19)	0.0162 (17)	−0.003 (2)
C20	0.088 (3)	0.194 (6)	0.139 (4)	0.073 (3)	0.026 (3)	0.045 (4)
N1	0.0559 (14)	0.0657 (15)	0.0580 (15)	0.0110 (11)	0.0007 (12)	0.0094 (12)
O1	0.0616 (12)	0.0581 (12)	0.0711 (13)	−0.0028 (9)	−0.0114 (10)	0.0088 (10)
O2	0.0647 (12)	0.0804 (14)	0.0447 (10)	0.0107 (11)	0.0054 (9)	0.0094 (10)
O3	0.0668 (13)	0.0950 (16)	0.0517 (12)	0.0103 (12)	0.0162 (11)	0.0039 (11)
O4	0.0472 (10)	0.0853 (14)	0.0637 (13)	0.0086 (10)	0.0097 (10)	0.0092 (11)
O5	0.0707 (14)	0.0829 (15)	0.0678 (14)	−0.0057 (12)	0.0180 (11)	0.0189 (12)

Geometric parameters (Å, º) top

C1—C2	1.519 (4)	C12—H12C	0.9600
C1—C5	1.525 (4)	C13—O3	1.220 (3)
C1—C6	1.533 (4)	C13—O2	1.345 (3)
C1—H1	0.9800	C14—O2	1.446 (3)
C2—C3	1.351 (4)	C14—C15	1.488 (5)
C2—C13	1.466 (4)	C14—H14A	0.9700
C3—N1	1.379 (4)	C14—H14B	0.9700
C3—C16	1.494 (4)	C15—H15A	0.9600
C4—C5	1.359 (4)	C15—H15B	0.9600
C4—N1	1.373 (4)	C15—H15C	0.9600
C4—C17	1.503 (4)	C16—H16A	0.9600
C5—C18	1.449 (4)	C16—H16B	0.9600
C6—C7	1.382 (4)	C16—H16C	0.9600
C6—C11	1.401 (4)	C17—H17A	0.9600
C7—C8	1.395 (5)	C17—H17B	0.9600
C7—H7	0.9300	C17—H17C	0.9600
C8—C9	1.363 (5)	C18—O5	1.225 (3)
C8—H8	0.9300	C18—O4	1.338 (3)
C9—C10	1.387 (5)	C19—O4	1.438 (4)
C9—H9	0.9300	C19—C20	1.451 (6)
C10—C11	1.389 (4)	C19—H19A	0.9700
C10—H10	0.9300	C19—H19B	0.9700
C11—O1	1.374 (3)	C20—H20A	0.9600
C12—O1	1.422 (4)	C20—H20B	0.9600
C12—H12A	0.9600	C20—H20C	0.9600
C12—H12B	0.9600	N1—H1A	0.8600

C2—C1—C5	111.2 (2)	O2—C14—C15	107.2 (3)
C2—C1—C6	113.1 (2)	O2—C14—H14A	110.3
C5—C1—C6	112.0 (2)	C15—C14—H14A	110.3
C2—C1—H1	106.7	O2—C14—H14B	110.3
C5—C1—H1	106.7	C15—C14—H14B	110.3
C6—C1—H1	106.7	H14A—C14—H14B	108.5
C3—C2—C13	121.1 (2)	C14—C15—H15A	109.5
C3—C2—C1	121.5 (2)	C14—C15—H15B	109.5
C13—C2—C1	117.4 (2)	H15A—C15—H15B	109.5
C2—C3—N1	119.1 (3)	C14—C15—H15C	109.5
C2—C3—C16	127.8 (3)	H15A—C15—H15C	109.5
N1—C3—C16	113.1 (3)	H15B—C15—H15C	109.5
C5—C4—N1	119.6 (2)	C3—C16—H16A	109.5
C5—C4—C17	127.4 (3)	C3—C16—H16B	109.5
N1—C4—C17	113.0 (2)	H16A—C16—H16B	109.5
C4—C5—C18	121.2 (2)	C3—C16—H16C	109.5
C4—C5—C1	120.5 (2)	H16A—C16—H16C	109.5
C18—C5—C1	118.3 (2)	H16B—C16—H16C	109.5
C7—C6—C11	116.8 (3)	C4—C17—H17A	109.5
C7—C6—C1	120.1 (3)	C4—C17—H17B	109.5
C11—C6—C1	123.1 (2)	H17A—C17—H17B	109.5
C6—C7—C8	122.0 (3)	C4—C17—H17C	109.5
C6—C7—H7	119.0	H17A—C17—H17C	109.5
C8—C7—H7	119.0	H17B—C17—H17C	109.5
C9—C8—C7	119.8 (3)	O5—C18—O4	121.1 (3)
C9—C8—H8	120.1	O5—C18—C5	127.1 (3)
C7—C8—H8	120.1	O4—C18—C5	111.8 (2)
C8—C9—C10	120.3 (3)	O4—C19—C20	107.8 (3)
C8—C9—H9	119.9	O4—C19—H19A	110.1
C10—C9—H9	119.9	C20—C19—H19A	110.1
C9—C10—C11	119.3 (3)	O4—C19—H19B	110.1
C9—C10—H10	120.3	C20—C19—H19B	110.1
C11—C10—H10	120.3	H19A—C19—H19B	108.5
O1—C11—C10	122.9 (3)	C19—C20—H20A	109.5
O1—C11—C6	115.4 (2)	C19—C20—H20B	109.5
C10—C11—C6	121.7 (3)	H20A—C20—H20B	109.5
O1—C12—H12A	109.5	C19—C20—H20C	109.5
O1—C12—H12B	109.5	H20A—C20—H20C	109.5
H12A—C12—H12B	109.5	H20B—C20—H20C	109.5
O1—C12—H12C	109.5	C4—N1—C3	124.0 (2)
H12A—C12—H12C	109.5	C4—N1—H1A	118.0
H12B—C12—H12C	109.5	C3—N1—H1A	118.0
O3—C13—O2	121.3 (3)	C11—O1—C12	118.7 (3)
O3—C13—C2	127.7 (3)	C13—O2—C14	117.5 (2)
O2—C13—C2	111.0 (2)	C18—O4—C19	117.5 (3)

C5—C1—C2—C3	19.7 (4)	C9—C10—C11—C6	1.9 (5)
C6—C1—C2—C3	−107.3 (3)	C7—C6—C11—O1	−180.0 (2)
C5—C1—C2—C13	−161.9 (2)	C1—C6—C11—O1	−0.9 (4)
C6—C1—C2—C13	71.1 (3)	C7—C6—C11—C10	−2.2 (4)
C13—C2—C3—N1	176.3 (3)	C1—C6—C11—C10	176.8 (3)
C1—C2—C3—N1	−5.4 (4)	C3—C2—C13—O3	7.5 (5)
C13—C2—C3—C16	−1.2 (5)	C1—C2—C13—O3	−171.0 (3)
C1—C2—C3—C16	177.1 (3)	C3—C2—C13—O2	−173.4 (3)
N1—C4—C5—C18	−172.1 (2)	C1—C2—C13—O2	8.2 (3)
C17—C4—C5—C18	7.1 (4)	C4—C5—C18—O5	−9.0 (4)
N1—C4—C5—C1	7.3 (4)	C1—C5—C18—O5	171.6 (3)
C17—C4—C5—C1	−173.4 (3)	C4—C5—C18—O4	170.5 (3)
C2—C1—C5—C4	−20.6 (3)	C1—C5—C18—O4	−8.9 (3)
C6—C1—C5—C4	107.0 (3)	C5—C4—N1—C3	9.9 (4)
C2—C1—C5—C18	158.8 (2)	C17—C4—N1—C3	−169.4 (3)
C6—C1—C5—C18	−73.5 (3)	C2—C3—N1—C4	−11.0 (4)
C2—C1—C6—C7	−119.7 (3)	C16—C3—N1—C4	166.8 (3)
C5—C1—C6—C7	113.7 (3)	C10—C11—O1—C12	8.5 (4)
C2—C1—C6—C11	61.3 (3)	C6—C11—O1—C12	−173.8 (3)
C5—C1—C6—C11	−65.3 (3)	O3—C13—O2—C14	2.1 (4)
C11—C6—C7—C8	0.5 (4)	C2—C13—O2—C14	−177.1 (2)
C1—C6—C7—C8	−178.5 (3)	C15—C14—O2—C13	−177.1 (3)
C6—C7—C8—C9	1.5 (5)	O5—C18—O4—C19	3.7 (4)
C7—C8—C9—C10	−1.9 (6)	C5—C18—O4—C19	−175.9 (3)
C8—C9—C10—C11	0.2 (5)	C20—C19—O4—C18	−169.0 (4)
C9—C10—C11—O1	179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.86	2.07	2.924 (3)	170

Symmetry code: (i) y, −x+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅NO₅
M_r	359.41
Crystal system, space group	Tetragonal, P42₁c
Temperature (K)	296
a, c (Å)	22.4689 (7), 8.2443 (3)
V (Å³)	4162.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.31 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID/ZJUG
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.952, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	60800, 4755, 3128
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.167, 1.00
No. of reflections	4755
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2102).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.86	2.07	2.924 (3)	170

Symmetry code: (i) y, −x+1, −z.

Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (No. Y4110373). We are also grateful for the help of Professor Jian-Ming Gu of Zhejiang University.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Franke, P. T., Johansen, R. L., Bertelsen, S. & Jorgensen, K. A. (2008). Chem. Asian J. 3, 216–224. Web of Science CrossRef PubMed CAS Google Scholar
Fun, H.-K., Hemamalini, M., Reddy, B. P., Vijayakumar, V. & Sarveswari, S. (2012). Acta Cryst. E68, o287–o288. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kapoor, K., Gupta, V. K., Kant, R., Pawar, M. P. & Joshi, H. S. (2011). Acta Cryst. E67, o2979. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takemoto, Y., Yoshida, K., Inokuma, T. & Takasu, K. (2010). Synlett, pp. 1865–1869. Web of Science CrossRef Google Scholar

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

Di­ethyl 4-(2-meth­­oxy­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

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Acknowledgements

References

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Diethyl 4-(2-methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate