organic compounds
Diethyl 2,6-dimethyl-4-(4-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylate
aDepartment of Chemistry, Dezhou University, Shandong 253023, People's Republic of China
*Correspondence e-mail: liyumei_dzc@yahoo.com.cn
In the title compound, C18H22N2O4, the dihedral angle between the two rings is 87.90 (6)°. The mean devation of the atoms in the dihydropyridine plane is 0.082 (3) Å. In the crystal, molecules are linked by intermolecular N—H⋯N hydrogen bonds, generating chains.
Related literature
For general background to the biological activity of 1,4-dihydropyridine derivatives, see: Gaudio et al. (1994).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2004); cell 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: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536810016934/om2336sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016934/om2336Isup2.hkl
Diethyl 2,6-dimethyl-4-(4-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylate was purchased from Jinan Henghua Science & Technology Co. Ltd. Diethyl 2,6-dimethyl-4-(4-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylate (1 mmoL 0.39 g) was dissolved in 20 ml ethanol, which was evaporated in an open flask at room temperature. One week later, yellow block crystals suitable for the X-ray experiment were obained. Anal. C18H22N2O4: C, 65.37; H, 6.66; N, 8.48 %. Found: C, 65.32; H, 6.45; N, 8.39 %.
All hydrogen atoms bound to aromatic carbon atoms were refined in calculated positions using a riding model with a C—H distance of 0.93 Å and Uiso = 1.2Ueq(C). For methyl groups C—H distances were 0.96 Å and Uiso = 1.5Ueq(C) . Two of the methyl groups were found to have two sets of methyl hydrogens and were refined with AFIX 127 and major part occupanices that refined to 0.60 (2) and 0.59 (2) for C17 and C18, respectively. The hydrogen atom attached to the hydropyridine nitrogen was freely refined.
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).
The molecular structure of the title compound is shown in Fig 1. The dihedral angle between the two rings is 87.90 (6) °. The mean devation of the dihydropyridine plane is 0.082 (3)Å. The intermolecular hydrogen bonding of N(2)—H(2A)···N(1) leads to a consolidation of the structure (Fig. 2; Table 1).
For general background to the biological activity of 1,4-dihydropyridine derivatives, see: Gaudio et al. (1994).
Data collection: APEX2 (Bruker, 2004); cell
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: SHELXL97 (Sheldrick, 2008).C18H22N2O4 | F(000) = 704 |
Mr = 330.38 | Dx = 1.223 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2361 reflections |
a = 11.5550 (2) Å | θ = 2.3–24.5° |
b = 13.1707 (2) Å | µ = 0.09 mm−1 |
c = 11.8020 (2) Å | T = 296 K |
β = 92.705 (2)° | Block, yellow |
V = 1794.11 (5) Å3 | 0.12 × 0.10 × 0.08 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3152 independent reflections |
Radiation source: fine-focus sealed tube | 2308 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→13 |
Tmin = 0.990, Tmax = 0.993 | k = −15→15 |
9122 measured reflections | l = −14→13 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2873P] where P = (Fo2 + 2Fc2)/3 |
3152 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C18H22N2O4 | V = 1794.11 (5) Å3 |
Mr = 330.38 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.5550 (2) Å | µ = 0.09 mm−1 |
b = 13.1707 (2) Å | T = 296 K |
c = 11.8020 (2) Å | 0.12 × 0.10 × 0.08 mm |
β = 92.705 (2)° |
Bruker APEXII CCD diffractometer | 3152 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2308 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.993 | Rint = 0.032 |
9122 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.15 e Å−3 |
3152 reflections | Δρmin = −0.19 e Å−3 |
227 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.33862 (13) | 0.01201 (15) | 0.15684 (14) | 0.0917 (6) | |
O2 | 0.50534 (12) | −0.07176 (10) | 0.16753 (11) | 0.0597 (4) | |
O3 | 0.80150 (10) | 0.08444 (10) | 0.58574 (10) | 0.0539 (4) | |
O4 | 0.81559 (11) | −0.01782 (11) | 0.43654 (12) | 0.0630 (4) | |
N1 | 0.82662 (14) | 0.18151 (15) | 0.07048 (14) | 0.0616 (5) | |
N2 | 0.47955 (13) | 0.18372 (12) | 0.43985 (13) | 0.0472 (4) | |
H2N | 0.4391 (17) | 0.2279 (15) | 0.4751 (16) | 0.058 (6)* | |
C1 | 0.76016 (19) | 0.23648 (17) | 0.13643 (17) | 0.0626 (6) | |
H1 | 0.7595 | 0.3066 | 0.1272 | 0.075* | |
C2 | 0.69267 (17) | 0.19512 (14) | 0.21726 (16) | 0.0527 (5) | |
H2 | 0.6482 | 0.2374 | 0.2610 | 0.063* | |
C3 | 0.69017 (13) | 0.09216 (12) | 0.23420 (13) | 0.0376 (4) | |
C4 | 0.75744 (16) | 0.03451 (15) | 0.16496 (15) | 0.0525 (5) | |
H4 | 0.7586 | −0.0358 | 0.1717 | 0.063* | |
C5 | 0.82298 (17) | 0.08201 (18) | 0.08560 (17) | 0.0631 (6) | |
H5 | 0.8674 | 0.0415 | 0.0399 | 0.076* | |
C6 | 0.76250 (15) | 0.04661 (14) | 0.48574 (14) | 0.0431 (4) | |
C7 | 0.91311 (16) | 0.04589 (17) | 0.62964 (17) | 0.0601 (5) | |
H7A | 0.9739 | 0.0664 | 0.5806 | 0.072* | |
H7B | 0.9116 | −0.0277 | 0.6328 | 0.072* | |
C8 | 0.9350 (2) | 0.0879 (2) | 0.7438 (2) | 0.0949 (9) | |
H8A | 0.9386 | 0.1606 | 0.7394 | 0.142* | |
H8B | 1.0072 | 0.0622 | 0.7754 | 0.142* | |
H8C | 0.8734 | 0.0684 | 0.7911 | 0.142* | |
C9 | 0.43413 (16) | 0.00167 (16) | 0.20127 (15) | 0.0514 (5) | |
C10 | 0.4620 (2) | −0.13703 (19) | 0.0762 (2) | 0.0795 (7) | |
H10A | 0.4463 | −0.0974 | 0.0079 | 0.095* | |
H10B | 0.3905 | −0.1694 | 0.0967 | 0.095* | |
C11 | 0.5496 (3) | −0.2133 (3) | 0.0566 (3) | 0.1604 (18) | |
H11A | 0.6205 | −0.1805 | 0.0384 | 0.241* | |
H11B | 0.5236 | −0.2562 | −0.0053 | 0.241* | |
H11C | 0.5624 | −0.2536 | 0.1238 | 0.241* | |
C12 | 0.61631 (13) | 0.04467 (13) | 0.32414 (13) | 0.0373 (4) | |
H12 | 0.6308 | −0.0286 | 0.3252 | 0.045* | |
C13 | 0.48786 (14) | 0.06167 (13) | 0.29414 (14) | 0.0405 (4) | |
C14 | 0.42771 (14) | 0.13185 (13) | 0.34979 (14) | 0.0424 (4) | |
C15 | 0.58549 (14) | 0.15725 (13) | 0.49037 (14) | 0.0425 (4) | |
C16 | 0.65116 (13) | 0.08686 (12) | 0.44024 (13) | 0.0381 (4) | |
C17 | 0.61248 (18) | 0.21403 (17) | 0.59884 (16) | 0.0614 (6) | |
H17A | 0.6361 | 0.1669 | 0.6575 | 0.092* | 0.60 (2) |
H17B | 0.5447 | 0.2499 | 0.6205 | 0.092* | 0.60 (2) |
H17C | 0.6739 | 0.2615 | 0.5878 | 0.092* | 0.60 (2) |
H17D | 0.6004 | 0.2854 | 0.5864 | 0.092* | 0.40 (2) |
H17E | 0.6918 | 0.2023 | 0.6233 | 0.092* | 0.40 (2) |
H17F | 0.5625 | 0.1907 | 0.6561 | 0.092* | 0.40 (2) |
C18 | 0.30334 (15) | 0.16157 (17) | 0.32620 (17) | 0.0584 (5) | |
H18A | 0.2596 | 0.1466 | 0.3913 | 0.088* | 0.59 (2) |
H18B | 0.2721 | 0.1242 | 0.2620 | 0.088* | 0.59 (2) |
H18C | 0.2989 | 0.2330 | 0.3102 | 0.088* | 0.59 (2) |
H18D | 0.2941 | 0.1892 | 0.2511 | 0.088* | 0.41 (2) |
H18E | 0.2816 | 0.2116 | 0.3804 | 0.088* | 0.41 (2) |
H18F | 0.2548 | 0.1028 | 0.3321 | 0.088* | 0.41 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0504 (9) | 0.1327 (15) | 0.0895 (11) | 0.0078 (9) | −0.0249 (9) | −0.0411 (11) |
O2 | 0.0560 (8) | 0.0669 (9) | 0.0552 (8) | −0.0058 (7) | −0.0078 (7) | −0.0177 (7) |
O3 | 0.0388 (7) | 0.0738 (9) | 0.0480 (7) | 0.0130 (6) | −0.0106 (6) | −0.0075 (6) |
O4 | 0.0505 (8) | 0.0732 (9) | 0.0643 (9) | 0.0217 (7) | −0.0080 (7) | −0.0164 (7) |
N1 | 0.0482 (10) | 0.0823 (13) | 0.0547 (10) | −0.0138 (9) | 0.0065 (8) | 0.0115 (9) |
N2 | 0.0358 (8) | 0.0622 (10) | 0.0436 (9) | 0.0121 (7) | −0.0003 (7) | −0.0067 (8) |
C1 | 0.0689 (14) | 0.0555 (12) | 0.0637 (13) | −0.0175 (11) | 0.0050 (11) | 0.0075 (10) |
C2 | 0.0552 (12) | 0.0487 (11) | 0.0551 (11) | −0.0048 (9) | 0.0113 (9) | −0.0026 (9) |
C3 | 0.0289 (8) | 0.0479 (10) | 0.0355 (9) | −0.0015 (7) | −0.0038 (7) | −0.0004 (7) |
C4 | 0.0520 (11) | 0.0542 (12) | 0.0522 (11) | 0.0069 (9) | 0.0121 (9) | 0.0029 (9) |
C5 | 0.0491 (12) | 0.0853 (17) | 0.0563 (13) | 0.0091 (11) | 0.0171 (10) | 0.0050 (11) |
C6 | 0.0383 (10) | 0.0507 (10) | 0.0401 (10) | 0.0015 (8) | 0.0004 (8) | 0.0003 (8) |
C7 | 0.0367 (10) | 0.0759 (14) | 0.0662 (13) | 0.0114 (10) | −0.0129 (9) | −0.0020 (11) |
C8 | 0.0617 (15) | 0.144 (2) | 0.0762 (16) | 0.0252 (16) | −0.0278 (13) | −0.0237 (17) |
C9 | 0.0433 (11) | 0.0666 (13) | 0.0441 (11) | −0.0083 (9) | 0.0010 (9) | −0.0025 (9) |
C10 | 0.0852 (17) | 0.0833 (17) | 0.0684 (14) | −0.0116 (14) | −0.0149 (13) | −0.0286 (13) |
C11 | 0.172 (4) | 0.139 (3) | 0.164 (3) | 0.065 (3) | −0.066 (3) | −0.101 (3) |
C12 | 0.0350 (9) | 0.0402 (9) | 0.0366 (9) | −0.0001 (7) | 0.0009 (7) | 0.0014 (7) |
C13 | 0.0342 (9) | 0.0510 (10) | 0.0362 (9) | −0.0058 (8) | 0.0011 (7) | 0.0040 (8) |
C14 | 0.0329 (9) | 0.0555 (11) | 0.0386 (9) | −0.0012 (8) | 0.0011 (7) | 0.0066 (8) |
C15 | 0.0363 (9) | 0.0543 (11) | 0.0366 (9) | 0.0025 (8) | −0.0002 (8) | 0.0015 (8) |
C16 | 0.0324 (9) | 0.0443 (10) | 0.0374 (9) | 0.0013 (7) | −0.0002 (7) | 0.0008 (7) |
C17 | 0.0537 (12) | 0.0806 (14) | 0.0493 (11) | 0.0159 (10) | −0.0048 (9) | −0.0170 (10) |
C18 | 0.0339 (10) | 0.0825 (14) | 0.0586 (12) | 0.0053 (9) | −0.0019 (9) | 0.0038 (11) |
O1—C9 | 1.207 (2) | C9—C13 | 1.465 (2) |
O2—C9 | 1.342 (2) | C10—C11 | 1.452 (4) |
O2—C10 | 1.449 (2) | C10—H10A | 0.9700 |
O3—C6 | 1.339 (2) | C10—H10B | 0.9700 |
O3—C7 | 1.458 (2) | C11—H11A | 0.9600 |
O4—C6 | 1.211 (2) | C11—H11B | 0.9600 |
N1—C5 | 1.324 (3) | C11—H11C | 0.9600 |
N1—C1 | 1.333 (3) | C12—C16 | 1.515 (2) |
N2—C14 | 1.377 (2) | C12—C13 | 1.526 (2) |
N2—C15 | 1.381 (2) | C12—H12 | 0.9800 |
N2—H2N | 0.86 (2) | C13—C14 | 1.346 (2) |
C1—C2 | 1.373 (3) | C14—C18 | 1.503 (2) |
C1—H1 | 0.9300 | C15—C16 | 1.352 (2) |
C2—C3 | 1.371 (2) | C15—C17 | 1.503 (2) |
C2—H2 | 0.9300 | C17—H17A | 0.9600 |
C3—C4 | 1.381 (2) | C17—H17B | 0.9600 |
C3—C12 | 1.527 (2) | C17—H17C | 0.9600 |
C4—C5 | 1.382 (3) | C17—H17D | 0.9600 |
C4—H4 | 0.9300 | C17—H17E | 0.9600 |
C5—H5 | 0.9300 | C17—H17F | 0.9600 |
C6—C16 | 1.470 (2) | C18—H18A | 0.9600 |
C7—C8 | 1.467 (3) | C18—H18B | 0.9600 |
C7—H7A | 0.9700 | C18—H18C | 0.9600 |
C7—H7B | 0.9700 | C18—H18D | 0.9600 |
C8—H8A | 0.9600 | C18—H18E | 0.9600 |
C8—H8B | 0.9600 | C18—H18F | 0.9600 |
C8—H8C | 0.9600 | ||
C9—O2—C10 | 116.92 (16) | H11A—C11—H11B | 109.5 |
C6—O3—C7 | 116.02 (14) | C10—C11—H11C | 109.5 |
C5—N1—C1 | 115.87 (17) | H11A—C11—H11C | 109.5 |
C14—N2—C15 | 123.55 (16) | H11B—C11—H11C | 109.5 |
C14—N2—H2N | 118.7 (13) | C16—C12—C13 | 111.71 (13) |
C15—N2—H2N | 116.8 (13) | C16—C12—C3 | 110.18 (13) |
N1—C1—C2 | 123.51 (19) | C13—C12—C3 | 110.37 (13) |
N1—C1—H1 | 118.2 | C16—C12—H12 | 108.2 |
C2—C1—H1 | 118.2 | C13—C12—H12 | 108.2 |
C3—C2—C1 | 120.68 (18) | C3—C12—H12 | 108.2 |
C3—C2—H2 | 119.7 | C14—C13—C9 | 121.67 (16) |
C1—C2—H2 | 119.7 | C14—C13—C12 | 120.43 (15) |
C2—C3—C4 | 116.16 (16) | C9—C13—C12 | 117.87 (15) |
C2—C3—C12 | 121.52 (15) | C13—C14—N2 | 120.11 (15) |
C4—C3—C12 | 122.32 (15) | C13—C14—C18 | 126.85 (16) |
C3—C4—C5 | 119.59 (18) | N2—C14—C18 | 113.03 (16) |
C3—C4—H4 | 120.2 | C16—C15—N2 | 119.26 (15) |
C5—C4—H4 | 120.2 | C16—C15—C17 | 128.02 (15) |
N1—C5—C4 | 124.17 (19) | N2—C15—C17 | 112.72 (15) |
N1—C5—H5 | 117.9 | C15—C16—C6 | 125.97 (15) |
C4—C5—H5 | 117.9 | C15—C16—C12 | 121.10 (14) |
O4—C6—O3 | 121.74 (15) | C6—C16—C12 | 112.88 (14) |
O4—C6—C16 | 122.14 (16) | C15—C17—H17A | 109.5 |
O3—C6—C16 | 116.11 (15) | C15—C17—H17B | 109.5 |
O3—C7—C8 | 107.81 (17) | H17A—C17—H17B | 109.5 |
O3—C7—H7A | 110.1 | C15—C17—H17C | 109.5 |
C8—C7—H7A | 110.1 | H17A—C17—H17C | 109.5 |
O3—C7—H7B | 110.1 | H17B—C17—H17C | 109.5 |
C8—C7—H7B | 110.1 | C15—C17—H17D | 109.5 |
H7A—C7—H7B | 108.5 | C15—C17—H17E | 109.5 |
C7—C8—H8A | 109.5 | H17D—C17—H17E | 109.5 |
C7—C8—H8B | 109.5 | C15—C17—H17F | 109.5 |
H8A—C8—H8B | 109.5 | H17D—C17—H17F | 109.5 |
C7—C8—H8C | 109.5 | H17E—C17—H17F | 109.5 |
H8A—C8—H8C | 109.5 | C14—C18—H18A | 109.5 |
H8B—C8—H8C | 109.5 | C14—C18—H18B | 109.5 |
O1—C9—O2 | 120.87 (17) | H18A—C18—H18B | 109.5 |
O1—C9—C13 | 127.63 (19) | C14—C18—H18C | 109.5 |
O2—C9—C13 | 111.50 (15) | H18A—C18—H18C | 109.5 |
O2—C10—C11 | 108.0 (2) | H18B—C18—H18C | 109.5 |
O2—C10—H10A | 110.1 | C14—C18—H18D | 109.5 |
C11—C10—H10A | 110.1 | C14—C18—H18E | 109.5 |
O2—C10—H10B | 110.1 | H18D—C18—H18E | 109.5 |
C11—C10—H10B | 110.1 | C14—C18—H18F | 109.5 |
H10A—C10—H10B | 108.4 | H18D—C18—H18F | 109.5 |
C10—C11—H11A | 109.5 | H18E—C18—H18F | 109.5 |
C10—C11—H11B | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1i | 0.86 (2) | 2.13 (2) | 2.984 (2) | 171.8 (18) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H22N2O4 |
Mr | 330.38 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 11.5550 (2), 13.1707 (2), 11.8020 (2) |
β (°) | 92.705 (2) |
V (Å3) | 1794.11 (5) |
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) |
Tmin, Tmax | 0.990, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9122, 3152, 2308 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.128, 1.03 |
No. of reflections | 3152 |
No. of parameters | 227 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.19 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1i | 0.86 (2) | 2.13 (2) | 2.984 (2) | 171.8 (18) |
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. A83, 1110–1115. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).
The molecular structure of the title compound is shown in Fig 1. The dihedral angle between the two rings is 87.90 (6) °. The mean devation of the dihydropyridine plane is 0.082 (3)Å. The intermolecular hydrogen bonding of N(2)—H(2A)···N(1) leads to a consolidation of the structure (Fig. 2; Table 1).