Diethyl 4-(2-meth-oxy-phen-yl)-2,6-di-methyl-1,4-di-hydro-pyridine-3,5-di-carboxyl-ate.

In the title compound, C20H25NO5, the di-hydro-pyridine ring adopts a flattened boat conformation. The meth-oxy-phenyl 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 di-hydro-pyridine ring. In the crystal, mol-ecules are connected by N-H⋯O hydrogen bonds into R 4 (4)(24) tetra-meric rings. A region of disordered electron density, located at the center of four adjacent mol-ecules, 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 = 359.41

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.167

S = 1.00

4755 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

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).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009951/pk2475sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009951/pk2475Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009951/pk2475Isup3.cml

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

C20H25NO5	Dx = 1.147 Mg m−3
Mr = 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

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

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(Fo2) + (0.0855P)2 + 0.9222P] where P = (Fo2 + 2Fc2)/3
4755 reflections	(Δ/σ)max = 0.008
241 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.20 e Å−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
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)

	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)

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)

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

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) .