3-Acetyl-2-methyl-4-(pyridin-3-yl)-1,4-di-hydro-indeno-[1,2-b]pyridin-5-one.

In the title compound, C20H16N2O2, the condensed tricyclic fragment is near to planar, with an r.m.s. deviation of 0.0531 Å. The 1,4-di-hydro-pyridine (1,4-DHP) ring adopts a slightly puckered boat-like conformation. The N and opposite C atoms deviate from the least-squares plane of the four other ring atoms by 0.039 (3) and 0.141 (3) Å, respectively. The C=O group located at the tricyclic fragment is fixed in an s-trans orientation, while the second C=O group adopts an s-cis orientation with respect to the double bonds of the 1,4-DHP ring. The pyridine ring has a pseudo-axial orientation with respect to the 1,4-DHP ring. The dihedral angle between the tricyclic system and the pyridine ring is 77.3 (3)°. In the crystal, the pyridine N atom accepts a hydrogen bond from the N-H group of the 1,4-DHP ring. The hydrogen bonds link the mol-ecules into infinite C(8) chains along the b-axis direction.

Related literature

For general information on the relationship between 1,4-di­hydro­pyridine ring substituents and pharmaceutical effects, see: Christopher et al. (2010 ▶); Bisenieks et al. (1987 ▶, 1995 ▶); Ivanov et al. (1989 ▶). For the synthesis of 1,4-DHP-containing tricyclic derivatives, see: Bisenieks et al. (1982 ▶).

Experimental

Crystal data

C20H16N2O2

M = 316.35

Triclinic,

a = 8.4361 (3) Å

b = 8.8812 (3) Å

c = 11.2582 (4) Å

α = 87.692 (2)°

β = 71.022 (2)°

γ = 89.210 (2)°

V = 797.00 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 190 K

0.30 × 0.28 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

5442 measured reflections

3615 independent reflections

2753 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.04

3615 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009719/fy2091sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009719/fy2091Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009719/fy2091Isup3.cml

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

C20H16N2O2	Z = 2
Mr = 316.35	F(000) = 332
Triclinic, P1	Dx = 1.318 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4361 (3) Å	Cell parameters from 8654 reflections
b = 8.8812 (3) Å	θ = 1.0–27.5°
c = 11.2582 (4) Å	µ = 0.09 mm−1
α = 87.692 (2)°	T = 190 K
β = 71.022 (2)°	Plate, red
γ = 89.210 (2)°	0.30 × 0.28 × 0.13 mm
V = 797.00 (5) Å3

Nonius KappaCCD diffractometer	2753 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
CCD scans	h = −10→10
5442 measured reflections	k = −11→10
3615 independent reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1857P] where P = (Fo2 + 2Fc2)/3
3615 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.95378 (15)	0.05051 (14)	0.30285 (11)	0.0282 (3)
H1A	0.9247	0.1425	0.2948	0.034*
O14	0.77556 (15)	−0.36855 (13)	0.58601 (11)	0.0409 (3)
C5	0.90043 (17)	−0.18330 (16)	0.41963 (13)	0.0245 (3)
C6	0.86632 (17)	−0.03576 (16)	0.40434 (13)	0.0243 (3)
C23	0.9277 (2)	−0.53299 (17)	0.30646 (16)	0.0355 (4)
H3	0.9676	−0.5603	0.3722	0.043*
N22	0.85901 (19)	−0.64053 (15)	0.25866 (14)	0.0424 (4)
C18	0.94286 (16)	−0.38372 (16)	0.26401 (13)	0.0237 (3)
C3	1.13273 (17)	−0.15786 (17)	0.21807 (13)	0.0258 (3)
C19	0.87866 (18)	−0.34450 (17)	0.16849 (14)	0.0287 (3)
H3A	0.8850	−0.2454	0.1373	0.034*
C15	1.27713 (18)	−0.22251 (19)	0.11903 (15)	0.0336 (4)
C4	1.02827 (17)	−0.26829 (16)	0.32047 (13)	0.0245 (3)
H7	1.1027	−0.3218	0.3589	0.029*
C2	1.09093 (18)	−0.01006 (17)	0.21154 (13)	0.0279 (3)
C13	0.78546 (18)	−0.24006 (18)	0.53979 (13)	0.0287 (3)
O16	1.33862 (17)	−0.16140 (15)	0.01533 (11)	0.0523 (4)
C24	1.1816 (2)	0.1054 (2)	0.11276 (16)	0.0412 (4)
H11A	1.2993	0.0830	0.0844	0.062*
H11B	1.1638	0.2036	0.1475	0.062*
H11C	1.1397	0.1034	0.0431	0.062*
C20	0.80500 (19)	−0.45370 (19)	0.11972 (15)	0.0346 (4)
H12	0.7604	−0.4287	0.0560	0.042*
C7	0.72519 (17)	0.01618 (17)	0.51290 (13)	0.0274 (3)
C21	0.7984 (2)	−0.59916 (19)	0.16626 (16)	0.0372 (4)
H14	0.7498	−0.6722	0.1322	0.045*
C12	0.67731 (18)	−0.10812 (18)	0.59719 (14)	0.0294 (3)
C8	0.64311 (19)	0.15161 (19)	0.53788 (15)	0.0340 (4)
H16	0.6747	0.2341	0.4818	0.041*
C10	0.4653 (2)	0.0398 (2)	0.73495 (16)	0.0434 (4)
H17	0.3782	0.0497	0.8102	0.052*
C9	0.5097 (2)	0.1612 (2)	0.65120 (16)	0.0411 (4)
H18	0.4505	0.2511	0.6699	0.049*
C17	1.3462 (2)	−0.3722 (2)	0.14648 (18)	0.0454 (5)
H19A	1.2708	−0.4510	0.1440	0.068*
H19B	1.3582	−0.3725	0.2284	0.068*
H19C	1.4536	−0.3885	0.0846	0.068*
C11	0.54884 (19)	−0.0980 (2)	0.70877 (15)	0.0376 (4)
H20	0.5183	−0.1803	0.7652	0.045*

	U11	U22	U33	U12	U13	U23
N1	0.0341 (6)	0.0202 (6)	0.0261 (6)	−0.0024 (5)	−0.0044 (5)	0.0028 (5)
O14	0.0472 (7)	0.0363 (7)	0.0346 (6)	−0.0057 (5)	−0.0084 (5)	0.0139 (5)
C5	0.0275 (7)	0.0254 (8)	0.0205 (7)	−0.0041 (6)	−0.0078 (6)	0.0001 (6)
C6	0.0267 (7)	0.0260 (8)	0.0204 (7)	−0.0037 (5)	−0.0077 (6)	−0.0022 (6)
C23	0.0484 (9)	0.0247 (8)	0.0374 (9)	−0.0005 (7)	−0.0197 (7)	0.0021 (7)
N22	0.0566 (9)	0.0241 (7)	0.0477 (9)	−0.0066 (6)	−0.0184 (7)	0.0002 (6)
C18	0.0234 (6)	0.0221 (7)	0.0243 (7)	0.0018 (5)	−0.0058 (5)	−0.0023 (6)
C3	0.0262 (7)	0.0304 (8)	0.0199 (7)	−0.0047 (6)	−0.0057 (6)	−0.0028 (6)
C19	0.0318 (7)	0.0245 (8)	0.0305 (8)	0.0000 (6)	−0.0112 (6)	0.0005 (6)
C15	0.0292 (7)	0.0397 (9)	0.0290 (8)	−0.0078 (6)	−0.0040 (6)	−0.0111 (7)
C4	0.0268 (7)	0.0247 (7)	0.0233 (7)	−0.0004 (5)	−0.0097 (6)	−0.0004 (6)
C2	0.0315 (7)	0.0306 (8)	0.0202 (7)	−0.0073 (6)	−0.0062 (6)	0.0006 (6)
C13	0.0300 (7)	0.0339 (9)	0.0231 (7)	−0.0066 (6)	−0.0101 (6)	0.0031 (6)
O16	0.0564 (8)	0.0545 (8)	0.0305 (7)	−0.0109 (6)	0.0084 (6)	−0.0084 (6)
C24	0.0468 (9)	0.0371 (10)	0.0320 (9)	−0.0098 (8)	−0.0027 (7)	0.0075 (7)
C20	0.0344 (8)	0.0404 (9)	0.0322 (8)	−0.0029 (7)	−0.0149 (7)	−0.0036 (7)
C7	0.0270 (7)	0.0321 (8)	0.0238 (7)	−0.0031 (6)	−0.0088 (6)	−0.0049 (6)
C21	0.0370 (8)	0.0359 (9)	0.0372 (9)	−0.0104 (7)	−0.0088 (7)	−0.0084 (7)
C12	0.0277 (7)	0.0388 (9)	0.0220 (7)	−0.0045 (6)	−0.0080 (6)	−0.0031 (6)
C8	0.0350 (8)	0.0355 (9)	0.0322 (8)	0.0010 (6)	−0.0111 (7)	−0.0091 (7)
C10	0.0294 (8)	0.0696 (13)	0.0284 (9)	0.0008 (8)	−0.0041 (7)	−0.0165 (9)
C9	0.0338 (8)	0.0522 (11)	0.0389 (9)	0.0079 (7)	−0.0119 (7)	−0.0198 (8)
C17	0.0326 (8)	0.0541 (12)	0.0476 (10)	0.0104 (7)	−0.0086 (8)	−0.0216 (9)
C11	0.0313 (8)	0.0558 (11)	0.0234 (8)	−0.0073 (7)	−0.0057 (6)	−0.0018 (7)

N1—C6	1.3541 (18)	C2—C24	1.500 (2)
N1—C2	1.3923 (19)	C13—C12	1.507 (2)
N1—H1A	0.8600	C24—H11A	0.9600
O14—C13	1.2274 (19)	C24—H11B	0.9600
C5—C6	1.354 (2)	C24—H11C	0.9600
C5—C13	1.459 (2)	C20—C21	1.369 (2)
C5—C4	1.497 (2)	C20—H12	0.9300
C6—C7	1.486 (2)	C7—C8	1.372 (2)
C23—N22	1.340 (2)	C7—C12	1.400 (2)
C23—C18	1.384 (2)	C21—H14	0.9300
C23—H3	0.9300	C12—C11	1.372 (2)
N22—C21	1.338 (2)	C8—C9	1.405 (2)
C18—C19	1.3837 (19)	C8—H16	0.9300
C18—C4	1.5312 (18)	C10—C9	1.375 (3)
C3—C2	1.360 (2)	C10—C11	1.398 (3)
C3—C15	1.485 (2)	C10—H17	0.9300
C3—C4	1.529 (2)	C9—H18	0.9300
C19—C20	1.382 (2)	C17—H19A	0.9600
C19—H3A	0.9300	C17—H19B	0.9600
C15—O16	1.220 (2)	C17—H19C	0.9600
C15—C17	1.505 (2)	C11—H20	0.9300
C4—H7	0.9800
C6—N1—C2	119.88 (13)	C2—C24—H11A	109.5
C6—N1—H1A	120.1	C2—C24—H11B	109.5
C2—N1—H1A	120.1	H11A—C24—H11B	109.5
C6—C5—C13	108.51 (13)	C2—C24—H11C	109.5
C6—C5—C4	122.68 (13)	H11A—C24—H11C	109.5
C13—C5—C4	128.66 (13)	H11B—C24—H11C	109.5
C5—C6—N1	123.00 (13)	C21—C20—C19	119.23 (14)
C5—C6—C7	111.18 (13)	C21—C20—H12	120.4
N1—C6—C7	125.81 (13)	C19—C20—H12	120.4
N22—C23—C18	124.02 (15)	C8—C7—C12	121.17 (14)
N22—C23—H3	118.0	C8—C7—C6	132.56 (15)
C18—C23—H3	118.0	C12—C7—C6	106.25 (13)
C21—N22—C23	117.45 (14)	N22—C21—C20	122.67 (14)
C19—C18—C23	117.09 (13)	N22—C21—H14	118.7
C19—C18—C4	121.92 (13)	C20—C21—H14	118.7
C23—C18—C4	120.99 (13)	C11—C12—C7	121.20 (15)
C2—C3—C15	120.83 (13)	C11—C12—C13	130.70 (15)
C2—C3—C4	122.57 (13)	C7—C12—C13	108.08 (13)
C15—C3—C4	116.45 (13)	C7—C8—C9	117.61 (16)
C20—C19—C18	119.51 (14)	C7—C8—H16	121.2
C20—C19—H3A	120.2	C9—C8—H16	121.2
C18—C19—H3A	120.2	C9—C10—C11	121.08 (15)
O16—C15—C3	122.70 (16)	C9—C10—H17	119.5
O16—C15—C17	118.81 (15)	C11—C10—H17	119.5
C3—C15—C17	118.46 (14)	C10—C9—C8	121.05 (16)
C5—C4—C3	109.63 (12)	C10—C9—H18	119.5
C5—C4—C18	110.49 (11)	C8—C9—H18	119.5
C3—C4—C18	110.48 (11)	C15—C17—H19A	109.5
C5—C4—H7	108.7	C15—C17—H19B	109.5
C3—C4—H7	108.7	H19A—C17—H19B	109.5
C18—C4—H7	108.7	C15—C17—H19C	109.5
C3—C2—N1	121.09 (13)	H19A—C17—H19C	109.5
C3—C2—C24	126.54 (14)	H19B—C17—H19C	109.5
N1—C2—C24	112.36 (13)	C12—C11—C10	117.86 (16)
O14—C13—C5	127.98 (14)	C12—C11—H20	121.1
O14—C13—C12	126.06 (14)	C10—C11—H20	121.1
C5—C13—C12	105.96 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N22i	0.86	2.06	2.916 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N22i	0.86	2.06	2.916 (2)	175

Symmetry code: (i) .