organic compounds
Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]-1,4,5,6-tetrahydropyridine-3-carboxylate
aLatvian Institute of Organic Synthesis, Riga, LV 1006, Latvia
*Correspondence e-mail: gduburs@osi.lv
In the title molecule, C20H18N2O3, an intramolecular N—H⋯O hydrogen bond leads to a cis conformation of the pyridinyl-vinyl fragment. The phenyl and pyridine rings are inclined to one another by 77.3 (1) °. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked by C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional structure.
Related literature
For applications of dihydropyridones, see: Dong et al. (2005); Elias et al. (2008). For a description of the Cambridge Structural Database, see: Allen (2002).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: KappaCCD Server Software (Nonius, 1999); cell DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: maXus (Mackay et al., 1999).
Supporting information
10.1107/S1600536812048532/cv5365sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048532/cv5365Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048532/cv5365Isup3.cml
In a 50 ml RB was placed 0.59 g (0.001 mol) of the DHPOD 6-methyltriphenylphosphonium bromide and dissolved in 25 ml dry THF. Under an Ar atmosphere while stirring magnetically 0.22 g (0.001 mol) of tBuOK was added. The orange solution was stirred for 30 min and 0.11 g (0.001 mol) of 2-pyridinecarboxaldehyde was added. The solution was allowed to stir at RT overnight, 3 ml of aqueous solution containing 0.6 g NH4Cl was added and after stirring 15 min the layers were separated. The THF was removed under reduced pressure and the sticky reaction product was dissolved in min. EtOAc. After addition of hexane the precipitated triphenylphosphine oxide was filtered off and the solvent removed to leave 0.55 g of product. The product was purified using prep. HPLC with 50% EtOAc / DCM as
The solvent was removed providing 0.21 g of product (62% yield) which was recrystallized from EtOH giving 100 mg of light green needles.Atoms H1, H4, H18 and H19 were located on a difference map and isotropically refined. All other H-atoms were positioned geometrically (C—H = 0.93–0.97 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(parent atom).
Data collection: KappaCCD (Nonius, 1999); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: maXus (Mackay et al., 1999).
Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme. Dashed lines denote intramolecular hydrogen bonds. |
C20H18N2O3 | Dx = 1.351 Mg m−3 |
Mr = 334.36 | Melting point: 504 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5746 (2) Å | Cell parameters from 2317 reflections |
b = 16.4083 (6) Å | θ = 0.9–27.5° |
c = 18.0930 (8) Å | µ = 0.09 mm−1 |
β = 96.5018 (14)° | T = 193 K |
V = 1644.32 (11) Å3 | Needle, colourless |
Z = 4 | 0.41 × 0.12 × 0.07 mm |
F(000) = 704 |
Bruker–Nonius KappaCCD diffractometer | 2483 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.053 |
Graphite monochromator | θmax = 28.6°, θmin = 1.6° |
ϕ and ω scan | h = −7→7 |
7024 measured reflections | k = −20→22 |
4206 independent reflections | l = −24→24 |
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)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.7901P] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.019 |
4206 reflections | Δρmax = 0.23 e Å−3 |
242 parameters | Δρmin = −0.22 e Å−3 |
0 restraints |
C20H18N2O3 | V = 1644.32 (11) Å3 |
Mr = 334.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.5746 (2) Å | µ = 0.09 mm−1 |
b = 16.4083 (6) Å | T = 193 K |
c = 18.0930 (8) Å | 0.41 × 0.12 × 0.07 mm |
β = 96.5018 (14)° |
Bruker–Nonius KappaCCD diffractometer | 2483 reflections with I > 2σ(I) |
7024 measured reflections | Rint = 0.053 |
4206 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.23 e Å−3 |
4206 reflections | Δρmin = −0.22 e Å−3 |
242 parameters |
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 | ||
N1 | 0.3841 (3) | 0.31397 (11) | 0.68159 (10) | 0.0317 (4) | |
H1 | 0.249 (4) | 0.3452 (16) | 0.6900 (13) | 0.050 (7)* | |
C2 | 0.4865 (4) | 0.26644 (13) | 0.73871 (12) | 0.0343 (5) | |
C3 | 0.7199 (4) | 0.22630 (13) | 0.72613 (12) | 0.0349 (5) | |
H3A | 0.7385 | 0.1771 | 0.7559 | 0.042* | |
H3B | 0.8519 | 0.2626 | 0.7433 | 0.042* | |
C4 | 0.7383 (3) | 0.20413 (12) | 0.64446 (11) | 0.0281 (5) | |
H4 | 0.910 (4) | 0.1941 (13) | 0.6403 (11) | 0.030 (5)* | |
C5 | 0.6556 (3) | 0.27567 (12) | 0.59458 (11) | 0.0275 (4) | |
C6 | 0.4830 (3) | 0.32727 (12) | 0.61506 (11) | 0.0281 (4) | |
O7 | 0.3935 (3) | 0.26137 (10) | 0.79683 (9) | 0.0471 (4) | |
C8 | 0.6075 (3) | 0.12466 (12) | 0.62263 (11) | 0.0266 (4) | |
C9 | 0.7212 (4) | 0.05100 (13) | 0.64153 (13) | 0.0357 (5) | |
H9 | 0.8757 | 0.0510 | 0.6671 | 0.043* | |
C10 | 0.6078 (4) | −0.02244 (14) | 0.62283 (14) | 0.0429 (6) | |
H10 | 0.6862 | −0.0712 | 0.6360 | 0.052* | |
C11 | 0.3794 (4) | −0.02351 (14) | 0.58485 (13) | 0.0442 (6) | |
H11 | 0.3044 | −0.0728 | 0.5715 | 0.053* | |
C12 | 0.2630 (4) | 0.04892 (15) | 0.56682 (13) | 0.0411 (5) | |
H12 | 0.1078 | 0.0484 | 0.5418 | 0.049* | |
C13 | 0.3754 (4) | 0.12274 (13) | 0.58566 (12) | 0.0327 (5) | |
H13 | 0.2945 | 0.1713 | 0.5734 | 0.039* | |
C14 | 0.7626 (4) | 0.28495 (13) | 0.52436 (12) | 0.0320 (5) | |
O15 | 0.7451 (4) | 0.34235 (11) | 0.48210 (12) | 0.0704 (6) | |
O16 | 0.8913 (3) | 0.21953 (9) | 0.50878 (8) | 0.0371 (4) | |
C17 | 1.0023 (4) | 0.22380 (15) | 0.44055 (13) | 0.0441 (6) | |
H17A | 1.0904 | 0.1745 | 0.4344 | 0.053* | |
H17B | 1.1107 | 0.2694 | 0.4426 | 0.053* | |
H17C | 0.8795 | 0.2304 | 0.3993 | 0.053* | |
C18 | 0.3926 (4) | 0.39772 (13) | 0.57107 (13) | 0.0357 (5) | |
H18 | 0.468 (4) | 0.4026 (15) | 0.5270 (14) | 0.043 (6)* | |
C19 | 0.2314 (4) | 0.45687 (14) | 0.58015 (13) | 0.0378 (5) | |
H19 | 0.219 (4) | 0.4957 (15) | 0.5424 (14) | 0.045 (7)* | |
C20 | 0.0609 (4) | 0.47713 (12) | 0.63325 (12) | 0.0323 (5) | |
N21 | 0.0217 (3) | 0.42656 (10) | 0.68919 (10) | 0.0313 (4) | |
C22 | −0.1441 (4) | 0.44794 (13) | 0.73342 (12) | 0.0348 (5) | |
H22 | −0.1708 | 0.4131 | 0.7722 | 0.042* | |
C23 | −0.2784 (4) | 0.51884 (14) | 0.72480 (13) | 0.0398 (5) | |
H23 | −0.3942 | 0.5307 | 0.7564 | 0.048* | |
C24 | −0.2370 (4) | 0.57122 (14) | 0.66859 (14) | 0.0429 (6) | |
H24 | −0.3229 | 0.6197 | 0.6616 | 0.052* | |
C25 | −0.0651 (4) | 0.55059 (14) | 0.62245 (13) | 0.0400 (5) | |
H25 | −0.0333 | 0.5855 | 0.5843 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0379 (9) | 0.0272 (9) | 0.0312 (10) | 0.0031 (8) | 0.0090 (7) | 0.0037 (8) |
C2 | 0.0473 (12) | 0.0256 (11) | 0.0303 (12) | −0.0044 (9) | 0.0058 (9) | −0.0001 (9) |
C3 | 0.0420 (12) | 0.0286 (11) | 0.0321 (12) | −0.0019 (9) | −0.0040 (9) | 0.0029 (9) |
C4 | 0.0249 (10) | 0.0252 (10) | 0.0338 (12) | 0.0011 (8) | 0.0016 (8) | 0.0029 (9) |
C5 | 0.0270 (9) | 0.0234 (10) | 0.0316 (11) | −0.0020 (8) | 0.0013 (8) | 0.0019 (8) |
C6 | 0.0302 (10) | 0.0258 (10) | 0.0284 (11) | −0.0023 (8) | 0.0031 (8) | 0.0019 (8) |
O7 | 0.0687 (11) | 0.0392 (9) | 0.0355 (9) | 0.0043 (8) | 0.0157 (8) | 0.0077 (7) |
C8 | 0.0288 (10) | 0.0251 (10) | 0.0273 (10) | 0.0023 (8) | 0.0097 (8) | 0.0012 (8) |
C9 | 0.0344 (11) | 0.0308 (11) | 0.0437 (13) | 0.0054 (9) | 0.0116 (9) | 0.0019 (10) |
C10 | 0.0577 (15) | 0.0250 (11) | 0.0505 (15) | 0.0047 (10) | 0.0256 (12) | 0.0005 (10) |
C11 | 0.0577 (15) | 0.0345 (13) | 0.0444 (14) | −0.0161 (11) | 0.0233 (12) | −0.0118 (11) |
C12 | 0.0380 (12) | 0.0459 (14) | 0.0397 (13) | −0.0108 (11) | 0.0061 (9) | −0.0067 (11) |
C13 | 0.0313 (10) | 0.0321 (11) | 0.0348 (12) | −0.0009 (9) | 0.0045 (8) | −0.0003 (9) |
C14 | 0.0327 (10) | 0.0263 (11) | 0.0377 (12) | 0.0021 (9) | 0.0074 (9) | 0.0029 (9) |
O15 | 0.0974 (15) | 0.0479 (11) | 0.0770 (14) | 0.0346 (10) | 0.0584 (12) | 0.0312 (10) |
O16 | 0.0439 (8) | 0.0318 (8) | 0.0377 (9) | 0.0096 (7) | 0.0129 (7) | 0.0041 (7) |
C17 | 0.0530 (14) | 0.0389 (13) | 0.0432 (14) | 0.0117 (11) | 0.0183 (11) | 0.0049 (11) |
C18 | 0.0422 (12) | 0.0329 (12) | 0.0339 (13) | 0.0065 (10) | 0.0132 (10) | 0.0072 (10) |
C19 | 0.0449 (12) | 0.0332 (12) | 0.0375 (13) | 0.0080 (10) | 0.0139 (10) | 0.0106 (11) |
C20 | 0.0379 (11) | 0.0279 (11) | 0.0316 (12) | −0.0015 (9) | 0.0069 (9) | −0.0019 (9) |
N21 | 0.0373 (9) | 0.0262 (9) | 0.0315 (10) | −0.0027 (7) | 0.0081 (7) | −0.0007 (7) |
C22 | 0.0419 (11) | 0.0319 (11) | 0.0319 (12) | −0.0051 (10) | 0.0098 (9) | −0.0028 (9) |
C23 | 0.0431 (12) | 0.0377 (13) | 0.0406 (13) | 0.0009 (10) | 0.0142 (10) | −0.0060 (11) |
C24 | 0.0520 (13) | 0.0318 (12) | 0.0470 (15) | 0.0113 (10) | 0.0141 (11) | 0.0005 (11) |
C25 | 0.0511 (13) | 0.0293 (11) | 0.0418 (13) | 0.0069 (10) | 0.0143 (10) | 0.0056 (10) |
N1—C2 | 1.367 (3) | C12—H12 | 0.9300 |
N1—C6 | 1.397 (3) | C13—H13 | 0.9300 |
N1—H1 | 0.94 (3) | C14—O15 | 1.210 (3) |
C2—O7 | 1.227 (3) | C14—O16 | 1.339 (2) |
C2—C3 | 1.498 (3) | O16—C17 | 1.444 (3) |
C3—C4 | 1.537 (3) | C17—H17A | 0.9600 |
C3—H3A | 0.9700 | C17—H17B | 0.9600 |
C3—H3B | 0.9700 | C17—H17C | 0.9600 |
C4—C5 | 1.520 (3) | C18—C19 | 1.345 (3) |
C4—C8 | 1.524 (3) | C18—H18 | 0.95 (2) |
C4—H4 | 0.98 (2) | C19—C20 | 1.465 (3) |
C5—C6 | 1.364 (3) | C19—H19 | 0.93 (3) |
C5—C14 | 1.471 (3) | C20—N21 | 1.346 (3) |
C6—C18 | 1.460 (3) | C20—C25 | 1.398 (3) |
C8—C13 | 1.388 (3) | N21—C22 | 1.337 (3) |
C8—C9 | 1.389 (3) | C22—C23 | 1.383 (3) |
C9—C10 | 1.385 (3) | C22—H22 | 0.9300 |
C9—H9 | 0.9300 | C23—C24 | 1.371 (3) |
C10—C11 | 1.377 (3) | C23—H23 | 0.9300 |
C10—H10 | 0.9300 | C24—C25 | 1.382 (3) |
C11—C12 | 1.375 (3) | C24—H24 | 0.9300 |
C11—H11 | 0.9300 | C25—H25 | 0.9300 |
C12—C13 | 1.388 (3) | ||
C2—N1—C6 | 124.69 (18) | C11—C12—H12 | 119.7 |
C2—N1—H1 | 117.6 (15) | C13—C12—H12 | 119.7 |
C6—N1—H1 | 117.2 (15) | C8—C13—C12 | 120.6 (2) |
O7—C2—N1 | 120.4 (2) | C8—C13—H13 | 119.7 |
O7—C2—C3 | 124.0 (2) | C12—C13—H13 | 119.7 |
N1—C2—C3 | 115.55 (19) | O15—C14—O16 | 119.9 (2) |
C2—C3—C4 | 113.83 (17) | O15—C14—C5 | 127.9 (2) |
C2—C3—H3A | 108.8 | O16—C14—C5 | 112.22 (17) |
C4—C3—H3A | 108.8 | C14—O16—C17 | 115.65 (17) |
C2—C3—H3B | 108.8 | O16—C17—H17A | 109.5 |
C4—C3—H3B | 108.8 | O16—C17—H17B | 109.5 |
H3A—C3—H3B | 107.7 | H17A—C17—H17B | 109.5 |
C5—C4—C8 | 113.75 (16) | O16—C17—H17C | 109.5 |
C5—C4—C3 | 109.83 (17) | H17A—C17—H17C | 109.5 |
C8—C4—C3 | 111.70 (16) | H17B—C17—H17C | 109.5 |
C5—C4—H4 | 108.5 (12) | C19—C18—C6 | 134.3 (2) |
C8—C4—H4 | 106.1 (12) | C19—C18—H18 | 114.0 (15) |
C3—C4—H4 | 106.6 (12) | C6—C18—H18 | 111.6 (15) |
C6—C5—C14 | 122.53 (18) | C18—C19—C20 | 137.4 (2) |
C6—C5—C4 | 119.60 (18) | C18—C19—H19 | 113.4 (15) |
C14—C5—C4 | 117.85 (17) | C20—C19—H19 | 109.1 (15) |
C5—C6—N1 | 119.77 (18) | N21—C20—C25 | 121.03 (19) |
C5—C6—C18 | 123.61 (19) | N21—C20—C19 | 121.74 (19) |
N1—C6—C18 | 116.62 (18) | C25—C20—C19 | 117.21 (19) |
C13—C8—C9 | 118.24 (19) | C22—N21—C20 | 118.07 (18) |
C13—C8—C4 | 122.47 (17) | N21—C22—C23 | 123.8 (2) |
C9—C8—C4 | 119.28 (17) | N21—C22—H22 | 118.1 |
C10—C9—C8 | 120.9 (2) | C23—C22—H22 | 118.1 |
C10—C9—H9 | 119.5 | C24—C23—C22 | 118.5 (2) |
C8—C9—H9 | 119.5 | C24—C23—H23 | 120.8 |
C11—C10—C9 | 120.3 (2) | C22—C23—H23 | 120.8 |
C11—C10—H10 | 119.9 | C23—C24—C25 | 118.8 (2) |
C9—C10—H10 | 119.9 | C23—C24—H24 | 120.6 |
C12—C11—C10 | 119.5 (2) | C25—C24—H24 | 120.6 |
C12—C11—H11 | 120.3 | C24—C25—C20 | 119.9 (2) |
C10—C11—H11 | 120.3 | C24—C25—H25 | 120.1 |
C11—C12—C13 | 120.5 (2) | C20—C25—H25 | 120.1 |
C6—N1—C2—O7 | 176.29 (19) | C10—C11—C12—C13 | 0.9 (3) |
C6—N1—C2—C3 | −0.7 (3) | C9—C8—C13—C12 | −1.4 (3) |
O7—C2—C3—C4 | 151.0 (2) | C4—C8—C13—C12 | 179.99 (19) |
N1—C2—C3—C4 | −32.2 (3) | C11—C12—C13—C8 | 0.4 (3) |
C2—C3—C4—C5 | 46.1 (2) | C6—C5—C14—O15 | 11.9 (4) |
C2—C3—C4—C8 | −81.1 (2) | C4—C5—C14—O15 | −169.8 (2) |
C8—C4—C5—C6 | 95.1 (2) | C6—C5—C14—O16 | −167.78 (17) |
C3—C4—C5—C6 | −30.9 (2) | C4—C5—C14—O16 | 10.6 (2) |
C8—C4—C5—C14 | −83.3 (2) | O15—C14—O16—C17 | 0.2 (3) |
C3—C4—C5—C14 | 150.69 (18) | C5—C14—O16—C17 | 179.93 (18) |
C14—C5—C6—N1 | 178.39 (18) | C5—C6—C18—C19 | −178.3 (2) |
C4—C5—C6—N1 | 0.1 (3) | N1—C6—C18—C19 | 1.3 (4) |
C14—C5—C6—C18 | −1.9 (3) | C6—C18—C19—C20 | −4.9 (5) |
C4—C5—C6—C18 | 179.75 (18) | C18—C19—C20—N21 | −5.5 (4) |
C2—N1—C6—C5 | 18.1 (3) | C18—C19—C20—C25 | 176.1 (3) |
C2—N1—C6—C18 | −161.56 (19) | C25—C20—N21—C22 | 1.1 (3) |
C5—C4—C8—C13 | −27.0 (3) | C19—C20—N21—C22 | −177.3 (2) |
C3—C4—C8—C13 | 98.1 (2) | C20—N21—C22—C23 | 0.3 (3) |
C5—C4—C8—C9 | 154.43 (19) | N21—C22—C23—C24 | −1.2 (3) |
C3—C4—C8—C9 | −80.6 (2) | C22—C23—C24—C25 | 0.7 (3) |
C13—C8—C9—C10 | 1.1 (3) | C23—C24—C25—C20 | 0.6 (4) |
C4—C8—C9—C10 | 179.8 (2) | N21—C20—C25—C24 | −1.6 (3) |
C8—C9—C10—C11 | 0.1 (3) | C19—C20—C25—C24 | 176.9 (2) |
C9—C10—C11—C12 | −1.2 (3) |
Cg is the centroid of the C8–C13 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···O15i | 0.93 | 2.42 | 3.257 (3) | 150 |
C24—H24···O7ii | 0.93 | 2.49 | 3.318 (3) | 149 |
C13—H13···O16iii | 0.93 | 2.54 | 3.300 (3) | 139 |
C19—H19···O15i | 0.93 (3) | 2.71 (3) | 3.489 (3) | 142 (2) |
C23—H23···Cgii | 0.93 | 2.66 | 3.480 | 147 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H18N2O3 |
Mr | 334.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 5.5746 (2), 16.4083 (6), 18.0930 (8) |
β (°) | 96.5018 (14) |
V (Å3) | 1644.32 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.41 × 0.12 × 0.07 |
Data collection | |
Diffractometer | Bruker–Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7024, 4206, 2483 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.674 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.149, 0.96 |
No. of reflections | 4206 |
No. of parameters | 242 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.22 |
Computer programs: KappaCCD (Nonius, 1999), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), maXus (Mackay et al., 1999).
Cg is the centroid of the C8–C13 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···O15i | 0.93 | 2.42 | 3.257 (3) | 150 |
C24—H24···O7ii | 0.93 | 2.49 | 3.318 (3) | 149 |
C13—H13···O16iii | 0.93 | 2.54 | 3.300 (3) | 139 |
C23—H23···Cgii | 0.93 | 2.66 | 3.480 | 147 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y+1/2, −z+3/2; (iii) x−1, y, z. |
Acknowledgements
This study was supported by the Latvian National Research Programme 2010-2013 Development of prevention, treatment, diagnostic means and practice and biomedicine technologies for improvement of public health.
References
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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.
Dihydropyridones are important intermediates for the synthesis of natural products, particularly alkaloids (Dong et al., 2005; Elias et al., 2008). They have been extensively investigated as valuable building blocks for the construction of piperidines, perhydroquinolines, indolizidines, quinolizidines and other alkaloid systems, with a wide range of biological and pharmacological activities. Herewith we present the title compound (I).
The main feature of (I) (Fig. 1) is cis-conformation of the pyridinylvinyl fragment, see Table 1 for selected torsion angles. A search of the Cambridge Structural Database (CSD, Version 5.33; November, 2012) (Allen, 2002) indicates that there is no entry containing pyridinylvinyl substituent in cis-conformation. Molecular cis-conformation is stabilized by strong intramolecular hydrogen bond of NH···N type (Table 2). By means of this bond the additional seven-membered cycle is formed in the molecular structure. In the molecule there is also an intramolecular hydrogen bond of CH···O type (Table 2). This bond leads to formation of the additional six-membered cycle in the molecule.
In the crystal structure there are shortened C···O contacts. These contacts can be described as weak CH···O type intermolecular hydrogen bonds. Also it should be noted a weak CH···π type H-bond. The geometrical parameters of these H-bonds are given in Table 2.