(E)-3-Dimethyl­amino-1-(2-pyrid­yl)prop-2-en-1-one

Abstract

The mol­ecule of the title compound, C₁₀H₁₂N₂O, is approximately planar, with an r.m.s. deviation of 0.072 Å from the mean plane for the non-H atoms. It was synthesized from 2-acetyl­pyridine and N,N-dimethyl­formamide dimethyl acetal in a one-step reaction.

Related literature

For background to related heteroaromatic compounds, see: Zhang et al. (2009 ▶); Liu et al. (2009 ▶); Kida et al. (2009 ▶).

Experimental

Crystal data

• C₁₀H₁₂N₂O

• M _r = 176.22

• Monoclinic,

• a = 5.6670 (11) Å

• b = 23.117 (5) Å

• c = 7.6880 (15) Å

• β = 108.17 (3)°

• V = 956.9 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 295 K

• 0.12 × 0.10 × 0.08 mm

Data collection

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.990, T _max = 0.994

• 7131 measured reflections

• 1775 independent reflections

• 1403 reflections with I > 2σ(I)

• R _int = 0.027

Refinement

• R[F ² > 2σ(F ²)] = 0.047

• wR(F ²) = 0.143

• S = 1.00

• 1775 reflections

• 121 parameters

• H-atom parameters not refined

• Δρ_max = 0.18 e Å⁻³

• Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); 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: SHELXTL.

Supplementary Material

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

supplementary crystallographic information

Comment

Derives of heteroaromatic ligands have proven to be extremely popular amongst coordination chemists for a wide range of applications because of their ease of synthesis, ease of functionalization, and the steric protection which they afford to metal centres (Zhang et al.; Liu et al.; Kida et al.). Here, we report the synthesis and structure of the title compound, (I).

As shown in Fig. 1, non-hydrogen atoms including the pyridine ring, N,N-Dimethylamino, and prop-2-en-1-one are coplanar with Rms deviation of fitted atoms being 0.0724 Å. The title compound is synthesized from 2-acetylpyridine and N,N-dimethylformamide-dimethyl acetal by one step.

Experimental

A mixture of 2-acetylpyridine(10 mmol) and N,N-dimethylformamide-dimethyl acetal(40 ml) was refluxed for four hours. After concentration in vacuo, recrystallization of the orange residue from ethanol afforded yellow blocks of (I). Anal. Calc. for C₁₀H₁₂N₂O: C 68.10, H 6.81, N 15.89%; Found: C 68.02, H 6.63, N 15.79%.

Refinement

All H atoms were geometrically positioned (C—H = 0.93–0.97Å) and refined as riding with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Figures

Fig. 1.

The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.

Crystal data

C10H12N2O	F(000) = 376
Mr = 176.22	Dx = 1.223 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1775 reflections
a = 5.6670 (11) Å	θ = 1.8–25.5°
b = 23.117 (5) Å	µ = 0.08 mm−1
c = 7.6880 (15) Å	T = 295 K
β = 108.17 (3)°	Block, yellow
V = 956.9 (3) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	1775 independent reflections
Radiation source: fine-focus sealed tube	1403 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.990, Tmax = 0.994	k = −27→28
7131 measured reflections	l = −9→9

Refinement

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) = 0.143	H-atom parameters not refined
S = 1.00	w = 1/[σ2(Fo2) + (0.087P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3
1775 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3675 (4)	0.01987 (8)	−0.3188 (3)	0.0664 (6)
H1A	0.2562	−0.0080	−0.2945	0.100*
H1B	0.5232	0.0016	−0.3092	0.100*
H1C	0.2964	0.0351	−0.4401	0.100*
C2	0.5845 (4)	0.11075 (9)	−0.1969 (3)	0.0674 (6)
H2A	0.5072	0.1481	−0.2079	0.101*
H2B	0.6385	0.1038	−0.3017	0.101*
H2C	0.7251	0.1096	−0.0879	0.101*
C3	0.2893 (3)	0.06861 (7)	−0.0630 (2)	0.0456 (4)
H3	0.1843	0.0377	−0.0633	0.055*
C4	0.3024 (3)	0.11046 (7)	0.0648 (2)	0.0464 (4)
H4	0.4006	0.1430	0.0703	0.056*
C5	0.1648 (3)	0.10380 (7)	0.1890 (2)	0.0445 (4)
C6	0.1719 (3)	0.15207 (6)	0.3237 (2)	0.0423 (4)
C7	0.0089 (3)	0.15063 (8)	0.4258 (2)	0.0533 (5)
H7	−0.1038	0.1204	0.4118	0.064*
C8	0.0165 (4)	0.19467 (9)	0.5484 (2)	0.0615 (5)
H8	−0.0916	0.1947	0.6179	0.074*
C9	0.1851 (4)	0.23816 (8)	0.5661 (2)	0.0608 (5)
H9	0.1951	0.2682	0.6484	0.073*
C10	0.3406 (4)	0.23655 (8)	0.4592 (2)	0.0584 (5)
H10	0.4549	0.2664	0.4720	0.070*
N1	0.4076 (3)	0.06659 (6)	−0.18682 (18)	0.0500 (4)
N2	0.3368 (3)	0.19482 (6)	0.33867 (18)	0.0505 (4)
O1	0.0370 (3)	0.06092 (5)	0.19576 (18)	0.0657 (4)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0977 (16)	0.0551 (11)	0.0587 (11)	0.0089 (10)	0.0423 (11)	−0.0012 (9)
C2	0.0611 (12)	0.0857 (14)	0.0628 (12)	−0.0074 (10)	0.0303 (10)	0.0026 (10)
C3	0.0508 (9)	0.0462 (9)	0.0432 (9)	0.0036 (7)	0.0197 (7)	0.0052 (7)
C4	0.0487 (9)	0.0464 (9)	0.0466 (9)	−0.0007 (7)	0.0185 (7)	−0.0010 (7)
C5	0.0491 (9)	0.0431 (9)	0.0427 (9)	0.0008 (7)	0.0164 (7)	0.0007 (7)
C6	0.0457 (9)	0.0423 (9)	0.0387 (8)	0.0060 (7)	0.0128 (7)	0.0034 (6)
C7	0.0541 (10)	0.0571 (11)	0.0531 (10)	0.0016 (8)	0.0232 (8)	−0.0037 (8)
C8	0.0649 (12)	0.0701 (13)	0.0560 (11)	0.0110 (10)	0.0284 (9)	−0.0077 (9)
C9	0.0763 (13)	0.0555 (11)	0.0482 (10)	0.0122 (9)	0.0161 (9)	−0.0103 (8)
C10	0.0730 (12)	0.0476 (10)	0.0519 (10)	−0.0048 (9)	0.0158 (9)	−0.0051 (8)
N1	0.0591 (9)	0.0520 (8)	0.0462 (8)	0.0031 (6)	0.0271 (7)	0.0023 (6)
N2	0.0581 (9)	0.0476 (8)	0.0466 (8)	−0.0037 (7)	0.0178 (7)	−0.0031 (6)
O1	0.0896 (10)	0.0554 (8)	0.0676 (9)	−0.0208 (7)	0.0472 (8)	−0.0144 (6)

Geometric parameters (Å, °)

C1—N1	1.451 (2)	C5—O1	1.2384 (18)
C1—H1A	0.9600	C5—C6	1.514 (2)
C1—H1B	0.9600	C6—N2	1.340 (2)
C1—H1C	0.9600	C6—C7	1.386 (2)
C2—N1	1.450 (2)	C7—C8	1.379 (2)
C2—H2A	0.9600	C7—H7	0.9300
C2—H2B	0.9600	C8—C9	1.364 (3)
C2—H2C	0.9600	C8—H8	0.9300
C3—N1	1.325 (2)	C9—C10	1.380 (3)
C3—C4	1.364 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—N2	1.333 (2)
C4—C5	1.417 (2)	C10—H10	0.9300
C4—H4	0.9300
N1—C1—H1A	109.5	C4—C5—C6	118.57 (14)
N1—C1—H1B	109.5	N2—C6—C7	122.61 (15)
H1A—C1—H1B	109.5	N2—C6—C5	118.10 (14)
N1—C1—H1C	109.5	C7—C6—C5	119.29 (15)
H1A—C1—H1C	109.5	C8—C7—C6	119.01 (17)
H1B—C1—H1C	109.5	C8—C7—H7	120.5
N1—C2—H2A	109.5	C6—C7—H7	120.5
N1—C2—H2B	109.5	C9—C8—C7	118.94 (17)
H2A—C2—H2B	109.5	C9—C8—H8	120.5
N1—C2—H2C	109.5	C7—C8—H8	120.5
H2A—C2—H2C	109.5	C8—C9—C10	118.55 (16)
H2B—C2—H2C	109.5	C8—C9—H9	120.7
N1—C3—C4	128.04 (15)	C10—C9—H9	120.7
N1—C3—H3	116.0	N2—C10—C9	123.96 (17)
C4—C3—H3	116.0	N2—C10—H10	118.0
C3—C4—C5	119.39 (15)	C9—C10—H10	118.0
C3—C4—H4	120.3	C3—N1—C2	121.81 (14)
C5—C4—H4	120.3	C3—N1—C1	121.65 (15)
O1—C5—C4	124.55 (15)	C2—N1—C1	116.54 (14)
O1—C5—C6	116.87 (14)	C10—N2—C6	116.93 (15)