Methyl 6-oxo-4-phenyl-2-[(Z)-2-(pyridin-2-yl)ethen-yl]-1,4,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title mol-ecule, C20H18N2O3, an intra-molecular 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, mol-ecules 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 inter-actions, 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 = 334.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.149

S = 0.96

4206 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048532/cv5365sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048532/cv5365Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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)

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

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⋯Cg ii	0.93	2.66	3.480	147

Symmetry codes: (i) ; (ii) ; (iii) .