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

Zhang, P.; Zhu, W.

doi:10.1107/S1600536810018155

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1424

https://doi.org/10.1107/S1600536810018155

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

Peng Zhang ^a and Weiqun Zhu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: zhuwq@sdu.edu.cn

(Received 13 May 2010; accepted 17 May 2010; online 22 May 2010)

In the title compound, C₂₀H₂₂N₂O₄, the dihedral angle between the roughly planar dihydropyridine ring (r.m.s. deviation = 0.092 Å) and the benzene ring is 87.09 (6)°. One of the ethoxy side chains is disordered over two orientations in a 0.669 (14):0.331 (14) ratio. In the crystal, molecules are linked by N—H⋯N hydrogen bonds, generating chains.

Related literature

For general background to dihydropyridine derivatives, see: Gaudio et al. (1994 ).

Experimental

Crystal data

C₂₀H₂₂N₂O₄
M_r = 354.40
Monoclinic, P 2₁ /n
a = 10.4596 (13) Å
b = 9.5117 (12) Å
c = 19.160 (2) Å
β = 91.493 (1)°
V = 1905.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.990, T_max = 0.993
10000 measured reflections
3298 independent reflections
2408 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.162
S = 1.02
3298 reflections
249 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1ⁱ	0.86	2.32	3.098 (3)	150
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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 global, I. DOI: https://doi.org/10.1107/S1600536810018155/hb5444sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018155/hb5444Isup2.hkl

checkCIF report

Comment top

The synthesis of 1,4-dihydropyridine derivatives has attracted continuous research interest due to various vasodilator, anti-hypertensive, bronchodilator, heptaprotective, anti-tumor, anti-mutagenic, geroprotective and anti-diabetic agents (Gaudio et al., 1994). Here, we describe the recystallization and structural characterization of the title compound.

The molecular structure is shown in Fig 1. The dihedral angle between the two rings is 87.09 (6) °. The mean devation of the dihydropyridine plane is 0.0824 Å. The intermolecular hydrogen bonding of N2—H2···N1 leads to a consolidation of the structure (Fig. 2; Table 1).

Related literature top

For general background to dihydropyridine derivatives, see: Gaudio et al. (1994).

Experimental top

Diethyl 2,6-dimethyl-4-(4-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (1 mmol 0.39 g) was dissolved in 20 ml ethanol was evaporated in one open flask at room temperature. One week later, yellow blocks of (I) were obained. Anal. C₂₀H₂₂N₂O₄: C, 67.72; H, 5.64; N, 7.90 %. Found: C, 67.56; H, 5.46; N, 7.61 %.

Structure description top

For general background to dihydropyridine derivatives, see: Gaudio et al. (1994).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. The molecular structure of (I) showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), displayed with N—H···N hydrogen bonds as dashed lines.

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

Crystal data top

C₂₀H₂₂N₂O₄	F(000) = 752
M_r = 354.40	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3532 reflections
a = 10.4596 (13) Å	θ = 2.4–25.9°
b = 9.5117 (12) Å	µ = 0.09 mm⁻¹
c = 19.160 (2) Å	T = 296 K
β = 91.493 (1)°	Block, colorless
V = 1905.6 (4) Å³	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3298 independent reflections
Radiation source: fine-focus sealed tube	2408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
T_min = 0.990, T_max = 0.993	k = −9→11
10000 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.0857P)² + 0.6251P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3298 reflections	Δρ_max = 0.31 e Å⁻³
249 parameters	Δρ_min = −0.28 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

Crystal data top

C₂₀H₂₂N₂O₄	V = 1905.6 (4) Å³
M_r = 354.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4596 (13) Å	µ = 0.09 mm⁻¹
b = 9.5117 (12) Å	T = 296 K
c = 19.160 (2) Å	0.12 × 0.10 × 0.08 mm
β = 91.493 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3298 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2408 reflections with I > 2σ(I)
T_min = 0.990, T_max = 0.993	R_int = 0.020
10000 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	2 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
3298 reflections	Δρ_min = −0.28 e Å⁻³
249 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 > 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	Occ. (<1)
C1	0.5366 (2)	0.1062 (3)	0.32734 (12)	0.0574 (6)
C2	0.4507 (2)	0.0690 (2)	0.27004 (10)	0.0483 (5)
C3	0.3890 (2)	−0.0596 (3)	0.26959 (12)	0.0607 (6)
H3	0.4024	−0.1222	0.3063	0.073*
C4	0.3078 (2)	−0.0948 (2)	0.21466 (12)	0.0573 (6)
H4	0.2670	−0.1817	0.2145	0.069*
C5	0.28599 (19)	−0.0030 (2)	0.15987 (10)	0.0419 (5)
C6	0.3497 (2)	0.1239 (2)	0.16056 (12)	0.0535 (6)
H6	0.3378	0.1854	0.1233	0.064*
C7	0.4306 (2)	0.1614 (2)	0.21529 (12)	0.0552 (6)
H7	0.4713	0.2483	0.2154	0.066*
C8	0.19219 (19)	−0.0393 (2)	0.09975 (11)	0.0444 (5)
H8	0.1533	−0.1305	0.1098	0.053*
C9	0.2616 (2)	−0.0512 (2)	0.03111 (12)	0.0507 (6)
C10	0.2559 (2)	0.0529 (3)	−0.01647 (11)	0.0528 (6)
C11	0.08375 (19)	0.1693 (2)	0.04492 (10)	0.0445 (5)
C12	0.08624 (18)	0.0706 (2)	0.09551 (10)	0.0425 (5)
C13	−0.0033 (2)	0.0607 (2)	0.15302 (12)	0.0490 (5)
C14	−0.1644 (3)	0.1750 (3)	0.21848 (15)	0.0738 (8)
H14A	−0.1152	0.1750	0.2621	0.089*
H14B	−0.2190	0.0925	0.2175	0.089*
C15	−0.2415 (3)	0.3012 (3)	0.2130 (2)	0.0980 (11)
H15A	−0.1871	0.3823	0.2168	0.147*
H15B	−0.3019	0.3025	0.2498	0.147*
H15C	−0.2864	0.3024	0.1687	0.147*
C16	−0.0089 (2)	0.2888 (3)	0.03443 (13)	0.0586 (6)
H16A	−0.0883	0.2659	0.0557	0.088*
H16B	−0.0235	0.3045	−0.0146	0.088*
H16C	0.0261	0.3724	0.0555	0.088*
C17	0.3287 (3)	0.0650 (4)	−0.08253 (13)	0.0756 (8)
H17A	0.4001	0.1272	−0.0752	0.113*
H17B	0.2735	0.1017	−0.1190	0.113*
H17C	0.3592	−0.0261	−0.0958	0.113*
C18	0.3377 (2)	−0.1776 (3)	0.01887 (15)	0.0676 (7)
C19	0.3950 (6)	−0.3990 (5)	0.0605 (3)	0.158 (2)
H19A	0.3515	−0.4556	0.0251	0.190*	0.669 (14)
H19B	0.4793	−0.3765	0.0437	0.190*	0.669 (14)
H19C	0.4473	−0.3909	0.0196	0.190*	0.331 (14)
H19D	0.4514	−0.4147	0.1007	0.190*	0.331 (14)
C20A	0.4079 (13)	−0.4759 (9)	0.1207 (5)	0.185 (6)	0.669 (14)
H20A	0.4549	−0.5603	0.1116	0.278*	0.669 (14)
H20B	0.3248	−0.4999	0.1371	0.278*	0.669 (14)
H20C	0.4530	−0.4213	0.1556	0.278*	0.669 (14)
C20B	0.3114 (12)	−0.5133 (12)	0.0522 (12)	0.141 (9)	0.331 (14)
H20D	0.3600	−0.5980	0.0467	0.212*	0.331 (14)
H20E	0.2573	−0.4988	0.0116	0.212*	0.331 (14)
H20F	0.2598	−0.5213	0.0927	0.212*	0.331 (14)
N1	0.6066 (2)	0.1329 (3)	0.37179 (12)	0.0765 (7)
N2	0.17490 (18)	0.1647 (2)	−0.00618 (9)	0.0534 (5)
H2	0.1813	0.2363	−0.0333	0.064*
O1	0.4059 (2)	−0.2026 (3)	−0.02939 (13)	0.1062 (8)
O2	0.3246 (2)	−0.2705 (2)	0.06982 (13)	0.0967 (7)
O3	−0.07949 (16)	0.17231 (17)	0.16008 (9)	0.0641 (5)
O4	−0.00600 (19)	−0.0369 (2)	0.19268 (11)	0.0824 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0631 (14)	0.0625 (15)	0.0467 (13)	0.0055 (12)	−0.0004 (11)	−0.0063 (11)
C2	0.0482 (12)	0.0555 (13)	0.0413 (11)	0.0057 (10)	−0.0013 (9)	−0.0061 (9)
C3	0.0722 (15)	0.0591 (15)	0.0503 (13)	−0.0007 (12)	−0.0094 (12)	0.0147 (11)
C4	0.0642 (14)	0.0456 (13)	0.0617 (14)	−0.0084 (11)	−0.0080 (11)	0.0095 (10)
C5	0.0410 (10)	0.0396 (11)	0.0452 (11)	0.0051 (9)	0.0025 (8)	−0.0017 (8)
C6	0.0648 (14)	0.0462 (13)	0.0489 (12)	−0.0052 (11)	−0.0103 (11)	0.0075 (10)
C7	0.0603 (13)	0.0466 (12)	0.0582 (13)	−0.0064 (11)	−0.0068 (11)	−0.0006 (10)
C8	0.0446 (11)	0.0371 (11)	0.0513 (12)	−0.0006 (9)	−0.0025 (9)	−0.0032 (9)
C9	0.0453 (12)	0.0539 (13)	0.0525 (12)	0.0024 (10)	−0.0052 (10)	−0.0144 (10)
C10	0.0461 (12)	0.0658 (15)	0.0464 (12)	−0.0015 (11)	−0.0022 (9)	−0.0127 (11)
C11	0.0433 (11)	0.0461 (12)	0.0436 (11)	0.0011 (9)	−0.0056 (9)	−0.0029 (9)
C12	0.0398 (11)	0.0418 (11)	0.0456 (11)	−0.0011 (9)	−0.0029 (9)	−0.0042 (9)
C13	0.0465 (12)	0.0448 (12)	0.0557 (12)	−0.0004 (10)	0.0026 (10)	0.0015 (10)
C14	0.0735 (17)	0.0753 (18)	0.0740 (17)	0.0031 (14)	0.0293 (14)	−0.0027 (14)
C15	0.088 (2)	0.074 (2)	0.135 (3)	0.0022 (16)	0.058 (2)	−0.0069 (19)
C16	0.0624 (14)	0.0569 (14)	0.0562 (13)	0.0106 (11)	−0.0044 (11)	0.0070 (11)
C17	0.0687 (16)	0.106 (2)	0.0526 (14)	0.0028 (15)	0.0107 (12)	−0.0091 (14)
C18	0.0628 (15)	0.0681 (17)	0.0715 (17)	0.0159 (13)	−0.0080 (13)	−0.0218 (14)
C19	0.203 (5)	0.090 (3)	0.183 (5)	0.084 (4)	0.027 (4)	−0.008 (3)
C20A	0.279 (14)	0.093 (5)	0.186 (9)	0.083 (7)	0.039 (9)	0.046 (6)
C20B	0.128 (12)	0.070 (9)	0.23 (2)	0.017 (7)	0.035 (12)	0.030 (10)
N1	0.0915 (16)	0.0847 (16)	0.0522 (12)	−0.0014 (13)	−0.0187 (12)	−0.0122 (11)
N2	0.0585 (11)	0.0569 (11)	0.0450 (10)	0.0036 (9)	0.0028 (8)	0.0062 (8)
O1	0.1042 (16)	0.1076 (18)	0.1084 (17)	0.0390 (14)	0.0303 (14)	−0.0284 (14)
O2	0.1248 (18)	0.0670 (13)	0.0989 (16)	0.0474 (13)	0.0125 (13)	−0.0023 (12)
O3	0.0684 (10)	0.0557 (10)	0.0694 (11)	0.0101 (8)	0.0264 (9)	0.0053 (8)
O4	0.0811 (13)	0.0715 (12)	0.0963 (14)	0.0160 (10)	0.0341 (11)	0.0318 (11)

Geometric parameters (Å, º) top

C1—N1	1.137 (3)	C14—H14A	0.9700
C1—C2	1.444 (3)	C14—H14B	0.9700
C2—C7	1.380 (3)	C15—H15A	0.9600
C2—C3	1.383 (3)	C15—H15B	0.9600
C3—C4	1.377 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.380 (3)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.378 (3)	C17—H17A	0.9600
C5—C8	1.533 (3)	C17—H17B	0.9600
C6—C7	1.377 (3)	C17—H17C	0.9600
C6—H6	0.9300	C18—O1	1.206 (3)
C7—H7	0.9300	C18—O2	1.326 (4)
C8—C9	1.523 (3)	C19—C20A	1.370 (8)
C8—C12	1.524 (3)	C19—C20B	1.401 (9)
C8—H8	0.9800	C19—O2	1.440 (4)
C9—C10	1.346 (3)	C19—H19A	0.9700
C9—C18	1.464 (3)	C19—H19B	0.9700
C10—N2	1.377 (3)	C19—H19C	0.9700
C10—C17	1.499 (3)	C19—H19D	0.9700
C11—C12	1.349 (3)	C20A—H20A	0.9600
C11—N2	1.385 (3)	C20A—H20B	0.9600
C11—C16	1.504 (3)	C20A—H20C	0.9600
C12—C13	1.467 (3)	C20B—H20D	0.9600
C13—O4	1.201 (3)	C20B—H20E	0.9600
C13—O3	1.336 (3)	C20B—H20F	0.9600
C14—O3	1.447 (3)	N2—H2	0.8600
C14—C15	1.448 (4)

N1—C1—C2	178.1 (3)	H15B—C15—H15C	109.5
C7—C2—C3	119.8 (2)	C11—C16—H16A	109.5
C7—C2—C1	120.1 (2)	C11—C16—H16B	109.5
C3—C2—C1	120.1 (2)	H16A—C16—H16B	109.5
C4—C3—C2	119.9 (2)	C11—C16—H16C	109.5
C4—C3—H3	120.0	H16A—C16—H16C	109.5
C2—C3—H3	120.0	H16B—C16—H16C	109.5
C3—C4—C5	120.9 (2)	C10—C17—H17A	109.5
C3—C4—H4	119.5	C10—C17—H17B	109.5
C5—C4—H4	119.5	H17A—C17—H17B	109.5
C6—C5—C4	118.5 (2)	C10—C17—H17C	109.5
C6—C5—C8	120.27 (18)	H17A—C17—H17C	109.5
C4—C5—C8	121.25 (19)	H17B—C17—H17C	109.5
C7—C6—C5	121.4 (2)	O1—C18—O2	120.5 (3)
C7—C6—H6	119.3	O1—C18—C9	128.2 (3)
C5—C6—H6	119.3	O2—C18—C9	111.2 (2)
C6—C7—C2	119.5 (2)	C20A—C19—C20B	74.2 (9)
C6—C7—H7	120.3	C20A—C19—O2	112.8 (5)
C2—C7—H7	120.3	C20B—C19—O2	110.7 (7)
C9—C8—C12	111.57 (17)	C20A—C19—H19A	109.0
C9—C8—C5	110.82 (16)	O2—C19—H19A	109.0
C12—C8—C5	109.63 (16)	C20A—C19—H19B	109.0
C9—C8—H8	108.2	C20B—C19—H19B	134.7
C12—C8—H8	108.2	O2—C19—H19B	109.0
C5—C8—H8	108.2	H19A—C19—H19B	107.8
C10—C9—C18	120.7 (2)	C20A—C19—H19C	132.7
C10—C9—C8	121.06 (19)	C20B—C19—H19C	109.5
C18—C9—C8	118.2 (2)	O2—C19—H19C	109.5
C9—C10—N2	119.2 (2)	H19A—C19—H19C	75.2
C9—C10—C17	127.9 (2)	C20B—C19—H19D	109.5
N2—C10—C17	112.9 (2)	O2—C19—H19D	109.5
C12—C11—N2	119.03 (18)	H19A—C19—H19D	137.2
C12—C11—C16	128.49 (19)	H19B—C19—H19D	76.0
N2—C11—C16	112.47 (18)	H19C—C19—H19D	108.1
C11—C12—C13	125.70 (19)	C19—C20A—H20A	109.5
C11—C12—C8	121.06 (18)	C19—C20A—H20B	109.5
C13—C12—C8	113.16 (18)	H20A—C20A—H20B	109.5
O4—C13—O3	121.7 (2)	C19—C20A—H20C	109.5
O4—C13—C12	123.4 (2)	H20A—C20A—H20C	109.5
O3—C13—C12	114.78 (19)	H20B—C20A—H20C	109.5
O3—C14—C15	108.1 (2)	C19—C20B—H20D	109.5
O3—C14—H14A	110.1	C19—C20B—H20E	109.5
C15—C14—H14A	110.1	H20D—C20B—H20E	109.5
O3—C14—H14B	110.1	C19—C20B—H20F	109.5
C15—C14—H14B	110.1	H20D—C20B—H20F	109.5
H14A—C14—H14B	108.4	H20E—C20B—H20F	109.5
C14—C15—H15A	109.5	C10—N2—C11	124.26 (19)
C14—C15—H15B	109.5	C10—N2—H2	117.9
H15A—C15—H15B	109.5	C11—N2—H2	117.9
C14—C15—H15C	109.5	C18—O2—C19	114.2 (3)
H15A—C15—H15C	109.5	C13—O3—C14	118.16 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ⁱ	0.86	2.32	3.098 (3)	150

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O₄
M_r	354.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.4596 (13), 9.5117 (12), 19.160 (2)
β (°)	91.493 (1)
V (Å³)	1905.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.990, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	10000, 3298, 2408
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.162, 1.02
No. of reflections	3298
No. of parameters	249
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), 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
N2—H2···N1ⁱ	0.86	2.32	3.098 (3)	150

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gaudio, A. C., Korolkovas, A. & Takahata, Y. (1994). J. Pharm. Sci. A, 83, 1110–1115. 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

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

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

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