Diethyl 4-[4-(dimethyl­amino)phen­yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

Ji, X.-L.; Sun, W.-B.; Zhang, Q.; Cao, Y.-P.; Bai, M.-S.

doi:10.1107/S1600536810003508

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o519

doi:10.1107/S1600536810003508

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Diethyl 4-[4-(dimethylamino)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Xiao-Ling Ji,^a Wang-Bin Sun,^a Qian Zhang,^a Yan-Ping Cao ^b and Ming-Sheng Bai ^c ^*

^aCollege of Life Science, Yulin University, Yulin, Shaanxi 719000, People's Republic of China, ^bCollege of Chemistry and Chemical Engineering, Yulin University, Yulin, Shaanxi 719000, People's Republic of China, and ^cCollege of Life Science, Ningxia University, Yinchuan 750021, People's Republic of China
^*Correspondence e-mail: baiming.s@163.com

(Received 3 January 2010; accepted 28 January 2010; online 6 February 2010)

In the title compound, C₂₁H₂₈N₂O₄, the dihydropyridine ring adopts a flattened boat conformation. The mean plane of the dihydropyridine ring and the attached benzene ring form a dihedral angle of 85.1 (1) Å. One of two ethyl fragments is disordered between two conformations in a 0.67 (4):0.33 (4) ratio. In the crystal structure, molecules related by translation along the a axis are linked into chains via intermolecular N—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of compounds containing substituted 1,4-dihydropyridine ring systems, see: Triggle et al.(1980 ); Henry (2004 ). For a related structure, see Sun et al. (2006 ).

Experimental

Crystal data

C₂₁H₂₈N₂O₄
M_r = 372.45
Monoclinic, P 2₁ /n
a = 7.5023 (7) Å
b = 14.9797 (14) Å
c = 18.0691 (19) Å
β = 91.021 (1)°
V = 2030.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.47 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.961
10007 measured reflections
3572 independent reflections
1680 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.202
S = 1.02
3572 reflections
270 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.86	2.18	3.036 (4)	173
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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: 10.1107/S1600536810003508/cv2687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003508/cv2687Isup2.hkl

checkCIF report

Comment top

Substituted 1,4-dihydropyridine ring system exhibit diverse pharmacological activities (Triggle et al., 1980). In addition, several of these compounds were discovered to be highly selective ligands for adenosine receptors, which were recently recognized as potential targets for the development of new drugs for the treatment of Parkinson's disease, hypoxia/ischemia, asthma, kidney disease, epilepsy, and cancer (Henry et al., 2004). In continuation of our ongoing program directed to the development of pyridine chemistry, we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths an angles are normal and are comparable to the values observed in similar compound ethyl 5-carboxy-2,6-dimethyl-4-(4-nitrophenyl) -1,4-dihydropyridine-3-carboxylate (Sun et al., 2006). The carboxylate and methyl groups lie to the each side of the dihydropyridine ring. The dihedral angle between the planes C2/C3/C4 and C1/N1/C5 is 36.9 (3) Å. The dihydropyridine ring adopts a flattened boat conformation and the plane of the base of the boat (C1/C2/C4/C5) forms a dihedral angle of 83.73 (13) Å with the benzene ring.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [100].

Related literature top

For the pharmacological activity of compounds containing substituted 1,4-dihydropyridine ring systems, see: Triggle et al.(1980); Henry et al. (2004). For a related structure, see Sun et al. (2006).

Experimental top

4-(N, N-dimethyl)benzaldehyde (10.0 mmol), 20 ml methanol, ethyl acetoacetate (20 mmol) and NH₄HCO₃ (6 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from methanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₂₁H₂₈N₂O₄: C 67.72, H 7.58, N 7.52%; found: C 67.82, H 7.73, N 7.43%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 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. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids. Only major parts of disordered atoms are shown. H atoms omitted for clarity.

Diethyl 4-[4-(dimethylamino)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₂₁H₂₈N₂O₄	F(000) = 800
M_r = 372.45	D_x = 1.218 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.5023 (7) Å	Cell parameters from 1665 reflections
b = 14.9797 (14) Å	θ = 2.6–20.9°
c = 18.0691 (19) Å	µ = 0.08 mm⁻¹
β = 91.021 (1)°	T = 298 K
V = 2030.3 (3) Å³	Needle, red
Z = 4	0.49 × 0.48 × 0.47 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3572 independent reflections
Radiation source: fine-focus sealed tube	1680 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.960, T_max = 0.961	k = −11→17
10007 measured reflections	l = −21→21

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0653P)² + 1.4769P] where P = (F_o² + 2F_c²)/3
3572 reflections	(Δ/σ)_max = 0.001
270 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₂₈N₂O₄	V = 2030.3 (3) Å³
M_r = 372.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5023 (7) Å	µ = 0.08 mm⁻¹
b = 14.9797 (14) Å	T = 298 K
c = 18.0691 (19) Å	0.49 × 0.48 × 0.47 mm
β = 91.021 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3572 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1680 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.961	R_int = 0.067
10007 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.202	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
3572 reflections	Δρ_min = −0.18 e Å⁻³
270 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
N1	1.0562 (4)	0.1513 (2)	1.06111 (16)	0.0535 (9)
H1	1.1638	0.1618	1.0758	0.064*
N2	0.6296 (5)	0.5330 (2)	0.8972 (2)	0.0785 (11)
O1	0.6518 (4)	0.0907 (2)	0.86907 (16)	0.0810 (10)
O2	0.9341 (5)	0.0681 (3)	0.84207 (18)	0.1139 (14)
O3	0.6311 (3)	0.1834 (2)	1.20424 (14)	0.0693 (9)
O4	0.4439 (3)	0.1727 (2)	1.10883 (14)	0.0679 (9)
C1	1.0290 (5)	0.1244 (2)	0.9891 (2)	0.0495 (10)
C2	0.8620 (5)	0.1274 (2)	0.96009 (18)	0.0464 (9)
C3	0.7131 (5)	0.1728 (2)	1.00311 (17)	0.0436 (9)
H3	0.6020	0.1402	0.9931	0.052*
C4	0.7524 (4)	0.1684 (2)	1.08551 (17)	0.0414 (9)
C5	0.9222 (5)	0.1625 (3)	1.11124 (18)	0.0474 (9)
C6	1.1942 (5)	0.0920 (3)	0.9527 (2)	0.0677 (12)
H6A	1.1736	0.0334	0.9327	0.102*
H6B	1.2902	0.0896	0.9885	0.102*
H6C	1.2250	0.1321	0.9135	0.102*
C7	0.8257 (7)	0.0925 (3)	0.8863 (2)	0.0648 (12)
C8	0.624 (3)	0.0697 (13)	0.7887 (8)	0.077 (4)	0.67 (4)
H8A	0.6810	0.1141	0.7582	0.092*	0.67 (4)
H8B	0.6723	0.0115	0.7771	0.092*	0.67 (4)
C9	0.428 (2)	0.0708 (15)	0.7756 (8)	0.095 (5)	0.67 (4)
H9A	0.3732	0.0268	0.8065	0.142*	0.67 (4)
H9B	0.4022	0.0574	0.7246	0.142*	0.67 (4)
H9C	0.3820	0.1288	0.7873	0.142*	0.67 (4)
C8'	0.557 (5)	0.036 (2)	0.814 (2)	0.079 (9)	0.33 (4)
H8'1	0.4525	0.0074	0.8345	0.094*	0.33 (4)
H8'2	0.6338	−0.0093	0.7929	0.094*	0.33 (4)
C9'	0.508 (6)	0.107 (3)	0.7585 (16)	0.098 (10)	0.33 (4)
H9'1	0.4027	0.1381	0.7745	0.146*	0.33 (4)
H9'2	0.4844	0.0805	0.7111	0.146*	0.33 (4)
H9'3	0.6041	0.1491	0.7547	0.146*	0.33 (4)
C10	0.6878 (4)	0.2688 (2)	0.97650 (17)	0.0420 (9)
C11	0.7898 (5)	0.3382 (3)	1.0039 (2)	0.0577 (11)
H11	0.8738	0.3263	1.0411	0.069*
C12	0.7721 (5)	0.4242 (3)	0.9787 (2)	0.0619 (11)
H12	0.8445	0.4686	0.9990	0.074*
C13	0.6486 (5)	0.4466 (3)	0.9232 (2)	0.0553 (10)
C14	0.5446 (5)	0.3772 (3)	0.8956 (2)	0.0629 (11)
H14	0.4592	0.3888	0.8589	0.076*
C15	0.5659 (5)	0.2911 (3)	0.9218 (2)	0.0584 (11)
H15	0.4947	0.2462	0.9015	0.070*
C16	0.7323 (7)	0.6039 (3)	0.9282 (3)	0.0911 (16)
H16A	0.7142	0.6064	0.9806	0.137*
H16B	0.6959	0.6593	0.9060	0.137*
H16C	0.8563	0.5937	0.9189	0.137*
C17	0.4833 (7)	0.5557 (3)	0.8486 (3)	0.0834 (15)
H17A	0.4969	0.5257	0.8021	0.125*
H17B	0.4815	0.6190	0.8407	0.125*
H17C	0.3735	0.5374	0.8705	0.125*
C18	0.5961 (5)	0.1746 (2)	1.1321 (2)	0.0467 (9)
C19	0.4839 (5)	0.1922 (3)	1.2541 (2)	0.0735 (14)
H19A	0.3974	0.1452	1.2448	0.088*
H19B	0.4253	0.2493	1.2466	0.088*
C20	0.5528 (7)	0.1859 (4)	1.3293 (3)	0.113 (2)
H20A	0.6072	0.1285	1.3367	0.170*
H20B	0.4570	0.1932	1.3632	0.170*
H20C	0.6400	0.2319	1.3377	0.170*
C21	0.9918 (5)	0.1636 (3)	1.1893 (2)	0.0708 (13)
H21A	0.9342	0.2103	1.2162	0.106*
H21B	1.1181	0.1739	1.1895	0.106*
H21C	0.9677	0.1071	1.2123	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0339 (17)	0.075 (2)	0.0513 (19)	−0.0034 (15)	0.0033 (15)	−0.0005 (16)
N2	0.089 (3)	0.055 (2)	0.091 (3)	−0.002 (2)	−0.019 (2)	0.017 (2)
O1	0.085 (2)	0.086 (2)	0.071 (2)	0.0062 (18)	−0.0216 (17)	−0.0345 (17)
O2	0.108 (3)	0.169 (4)	0.065 (2)	0.033 (3)	0.006 (2)	−0.044 (2)
O3	0.0432 (16)	0.118 (3)	0.0468 (17)	0.0008 (15)	0.0103 (13)	−0.0104 (15)
O4	0.0372 (16)	0.109 (2)	0.0575 (17)	0.0035 (15)	0.0019 (13)	0.0050 (15)
C1	0.043 (2)	0.056 (2)	0.050 (2)	−0.0050 (19)	0.0102 (18)	0.0038 (19)
C2	0.051 (2)	0.048 (2)	0.041 (2)	−0.0027 (18)	0.0047 (18)	−0.0003 (17)
C3	0.039 (2)	0.053 (2)	0.0386 (19)	−0.0056 (17)	0.0000 (16)	0.0004 (17)
C4	0.037 (2)	0.050 (2)	0.0371 (19)	0.0003 (17)	0.0017 (16)	0.0013 (16)
C5	0.040 (2)	0.060 (3)	0.043 (2)	0.0017 (18)	0.0032 (18)	0.0021 (18)
C6	0.056 (3)	0.084 (3)	0.064 (3)	0.004 (2)	0.020 (2)	−0.003 (2)
C7	0.070 (3)	0.070 (3)	0.054 (3)	0.007 (2)	−0.007 (2)	−0.009 (2)
C8	0.081 (10)	0.092 (9)	0.058 (7)	−0.008 (6)	−0.009 (6)	−0.029 (6)
C9	0.079 (10)	0.134 (13)	0.071 (7)	−0.020 (7)	−0.011 (6)	−0.032 (7)
C8'	0.085 (18)	0.079 (17)	0.071 (16)	−0.012 (11)	−0.005 (13)	−0.023 (13)
C9'	0.10 (3)	0.12 (2)	0.075 (14)	−0.004 (16)	−0.022 (15)	0.003 (14)
C10	0.041 (2)	0.051 (2)	0.0346 (19)	−0.0020 (18)	0.0004 (16)	0.0033 (16)
C11	0.054 (2)	0.059 (3)	0.059 (2)	−0.006 (2)	−0.0139 (19)	0.009 (2)
C12	0.063 (3)	0.055 (3)	0.066 (3)	−0.012 (2)	−0.016 (2)	0.006 (2)
C13	0.058 (3)	0.054 (3)	0.053 (2)	0.003 (2)	0.002 (2)	0.010 (2)
C14	0.061 (3)	0.066 (3)	0.061 (3)	0.000 (2)	−0.018 (2)	0.010 (2)
C15	0.062 (3)	0.056 (3)	0.056 (2)	−0.005 (2)	−0.018 (2)	0.002 (2)
C16	0.106 (4)	0.065 (3)	0.102 (4)	−0.010 (3)	−0.005 (3)	0.013 (3)
C17	0.100 (4)	0.069 (3)	0.081 (3)	0.014 (3)	−0.007 (3)	0.019 (3)
C18	0.041 (2)	0.057 (3)	0.041 (2)	0.0039 (18)	0.0010 (18)	0.0046 (18)
C19	0.048 (3)	0.113 (4)	0.059 (3)	0.006 (2)	0.018 (2)	−0.006 (2)
C20	0.095 (4)	0.186 (7)	0.059 (3)	0.004 (4)	0.022 (3)	−0.018 (3)
C21	0.048 (2)	0.112 (4)	0.052 (2)	0.013 (2)	−0.005 (2)	−0.001 (2)

Geometric parameters (Å, º) top

N1—C1	1.374 (4)	C8'—C9'	1.51 (7)
N1—C5	1.375 (4)	C8'—H8'1	0.9700
N1—H1	0.8600	C8'—H8'2	0.9700
N2—C13	1.384 (5)	C9'—H9'1	0.9600
N2—C16	1.421 (5)	C9'—H9'2	0.9600
N2—C17	1.434 (5)	C9'—H9'3	0.9600
O1—C7	1.336 (5)	C10—C15	1.376 (5)
O1—C8'	1.47 (2)	C10—C11	1.377 (5)
O1—C8	1.497 (11)	C11—C12	1.372 (5)
O2—C7	1.208 (5)	C11—H11	0.9300
O3—C18	1.332 (4)	C12—C13	1.393 (5)
O3—C19	1.444 (4)	C12—H12	0.9300
O4—C18	1.210 (4)	C13—C14	1.388 (5)
C1—C2	1.350 (5)	C14—C15	1.381 (5)
C1—C6	1.495 (5)	C14—H14	0.9300
C2—C7	1.453 (5)	C15—H15	0.9300
C2—C3	1.531 (5)	C16—H16A	0.9600
C3—C4	1.514 (4)	C16—H16B	0.9600
C3—C10	1.528 (5)	C16—H16C	0.9600
C3—H3	0.9800	C17—H17A	0.9600
C4—C5	1.352 (5)	C17—H17B	0.9600
C4—C18	1.459 (5)	C17—H17C	0.9600
C5—C21	1.495 (5)	C19—C20	1.447 (6)
C6—H6A	0.9600	C19—H19A	0.9700
C6—H6B	0.9600	C19—H19B	0.9700
C6—H6C	0.9600	C20—H20A	0.9600
C8—C9	1.48 (3)	C20—H20B	0.9600
C8—H8A	0.9700	C20—H20C	0.9600
C8—H8B	0.9700	C21—H21A	0.9600
C9—H9A	0.9600	C21—H21B	0.9600
C9—H9B	0.9600	C21—H21C	0.9600
C9—H9C	0.9600

C1—N1—C5	124.2 (3)	H9'1—C9'—H9'3	109.5
C1—N1—H1	117.9	H9'2—C9'—H9'3	109.5
C5—N1—H1	117.9	C15—C10—C11	115.7 (3)
C13—N2—C16	120.9 (4)	C15—C10—C3	122.1 (3)
C13—N2—C17	120.2 (4)	C11—C10—C3	122.2 (3)
C16—N2—C17	117.9 (4)	C12—C11—C10	122.6 (4)
C7—O1—C8'	129.0 (13)	C12—C11—H11	118.7
C7—O1—C8	110.6 (8)	C10—C11—H11	118.7
C8'—O1—C8	33.4 (12)	C11—C12—C13	121.7 (4)
C18—O3—C19	118.7 (3)	C11—C12—H12	119.2
C2—C1—N1	118.6 (3)	C13—C12—H12	119.2
C2—C1—C6	127.7 (4)	N2—C13—C14	121.7 (4)
N1—C1—C6	113.7 (3)	N2—C13—C12	122.2 (4)
C1—C2—C7	120.1 (4)	C14—C13—C12	116.1 (4)
C1—C2—C3	119.9 (3)	C15—C14—C13	121.0 (4)
C7—C2—C3	120.0 (3)	C15—C14—H14	119.5
C4—C3—C10	111.8 (3)	C13—C14—H14	119.5
C4—C3—C2	110.4 (3)	C10—C15—C14	122.9 (4)
C10—C3—C2	110.2 (3)	C10—C15—H15	118.5
C4—C3—H3	108.1	C14—C15—H15	118.5
C10—C3—H3	108.1	N2—C16—H16A	109.5
C2—C3—H3	108.1	N2—C16—H16B	109.5
C5—C4—C18	124.6 (3)	H16A—C16—H16B	109.5
C5—C4—C3	120.5 (3)	N2—C16—H16C	109.5
C18—C4—C3	114.9 (3)	H16A—C16—H16C	109.5
C4—C5—N1	118.5 (3)	H16B—C16—H16C	109.5
C4—C5—C21	129.4 (3)	N2—C17—H17A	109.5
N1—C5—C21	112.1 (3)	N2—C17—H17B	109.5
C1—C6—H6A	109.5	H17A—C17—H17B	109.5
C1—C6—H6B	109.5	N2—C17—H17C	109.5
H6A—C6—H6B	109.5	H17A—C17—H17C	109.5
C1—C6—H6C	109.5	H17B—C17—H17C	109.5
H6A—C6—H6C	109.5	O4—C18—O3	120.7 (3)
H6B—C6—H6C	109.5	O4—C18—C4	124.1 (3)
O2—C7—O1	120.4 (4)	O3—C18—C4	115.1 (3)
O2—C7—C2	126.8 (4)	O3—C19—C20	108.4 (4)
O1—C7—C2	112.8 (4)	O3—C19—H19A	110.0
C9—C8—O1	106.0 (14)	C20—C19—H19A	110.0
C9—C8—H8A	110.5	O3—C19—H19B	110.0
O1—C8—H8A	110.5	C20—C19—H19B	110.0
C9—C8—H8B	110.5	H19A—C19—H19B	108.4
O1—C8—H8B	110.5	C19—C20—H20A	109.5
H8A—C8—H8B	108.7	C19—C20—H20B	109.5
O1—C8'—C9'	99 (3)	H20A—C20—H20B	109.5
O1—C8'—H8'1	111.9	C19—C20—H20C	109.5
C9'—C8'—H8'1	111.9	H20A—C20—H20C	109.5
O1—C8'—H8'2	111.9	H20B—C20—H20C	109.5
C9'—C8'—H8'2	111.9	C5—C21—H21A	109.5
H8'1—C8'—H8'2	109.6	C5—C21—H21B	109.5
C8'—C9'—H9'1	109.5	H21A—C21—H21B	109.5
C8'—C9'—H9'2	109.5	C5—C21—H21C	109.5
H9'1—C9'—H9'2	109.5	H21A—C21—H21C	109.5
C8'—C9'—H9'3	109.5	H21B—C21—H21C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.18	3.036 (4)	173

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₈N₂O₄
M_r	372.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.5023 (7), 14.9797 (14), 18.0691 (19)
β (°)	91.021 (1)
V (Å³)	2030.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.49 × 0.48 × 0.47

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	10007, 3572, 1680
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.202, 1.02
No. of reflections	3572
No. of parameters	270
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 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
N1—H1···O4ⁱ	0.86	2.18	3.036 (4)	173.3

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of the College of Life Science, Ningxia University (grant No. 081040).

References

Henry, G. D. (2004). Tetrahedron, 60, 6043-6061. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sun, F.-X., Zhao, H. & Du, H.-X. (2006). Acta Cryst. E62, o5448–o5449. Web of Science CSD CrossRef IUCr Journals Google Scholar
Triggle, A. M., Shefter, E. J. & Triggle, D. (1980). J. Med. Chem. 23, 1442–1445. CrossRef CAS PubMed Web of Science Google Scholar

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Volume 66| Part 3| March 2010| Page o519

doi:10.1107/S1600536810003508

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

Di­ethyl 4-[4-(di­methyl­amino)phen­yl]-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

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