Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethen­yl]-1,4,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Smits, R.; Belyakov, S.; Vigante, B.; Duburs, G.

doi:10.1107/S1600536812048532

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3489

doi:10.1107/S1600536812048532

Open

access

Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]-1,4,5,6-tetrahydropyridine-3-carboxylate

Rufus Smits,^a Sergey Belyakov,^a Brigita Vigante ^a and Gunars Duburs ^a ^*

^aLatvian Institute of Organic Synthesis, Riga, LV 1006, Latvia
^*Correspondence e-mail: gduburs@osi.lv

(Received 15 November 2012; accepted 26 November 2012; online 30 November 2012)

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

C₂₀H₁₈N₂O₃
M_r = 334.36
Monoclinic, P 2₁ /c
a = 5.5746 (2) Å
b = 16.4083 (6) Å
c = 18.0930 (8) Å
β = 96.5018 (14)°
V = 1644.32 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.41 × 0.12 × 0.07 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
7024 measured reflections
4206 independent reflections
2483 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.149
S = 0.96
4206 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-1, y, z.

Data collection: KappaCCD Server Software (Nonius, 1999 ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812048532/cv5365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048532/cv5365Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048532/cv5365Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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 eluent. The solvent was removed providing 0.21 g of product (62% yield) which was recrystallized from EtOH giving 100 mg of light green needles.

Computing details top

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).

Figures top

Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom numbering scheme. Dashed lines denote intramolecular hydrogen bonds.

Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]- 1,4,5,6-tetrahydropyridine-3-carboxylate top

Crystal data top

C₂₀H₁₈N₂O₃	D_x = 1.351 Mg m⁻³
M_r = 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

Data collection top

Bruker–Nonius KappaCCD diffractometer	2483 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 28.6°, θ_min = 1.6°
ϕ and ω scan	h = −7→7
7024 measured reflections	k = −20→22
4206 independent reflections	l = −24→24

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0562P)² + 0.7901P] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.019
4206 reflections	Δρ_max = 0.23 e Å⁻³
242 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints

Crystal data top

C₂₀H₁₈N₂O₃	V = 1644.32 (11) Å³
M_r = 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)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	2483 reflections with I > 2σ(I)
7024 measured reflections	R_int = 0.053
4206 independent reflections

Refinement top

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	Δρ_max = 0.23 e Å⁻³
4206 reflections	Δρ_min = −0.22 e Å⁻³
242 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dong, D., Bi, X., Liu, Q. & Cong, F. (2005). Chem. Commun. pp. 3580–3582. Web of Science CrossRef Google Scholar
Elias, R. S., Saeed, B. A., Saour, K. Y. & Al-Masoudi, N. A. (2008). Tetrahedron Lett. 49, 3049–3051. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (1999). maXus. Bruker–Nonius, The Netherlands, MacScience, Japan, and The University of Glasgow, Scotland. Google Scholar
Nonius (1999). KappaCCD Server Software. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3489

doi:10.1107/S1600536812048532

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethen­yl]-1,4,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethenyl]-1,4,5,6-tetrahydropyridine-3-carboxylate