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

Ni, L.; Zhao, J.-L.; Wei, H.

doi:10.1107/S1600536809030530

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2103

doi:10.1107/S1600536809030530

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

Lei Ni,^a ^* Ji-Li Zhao ^a and Hong Wei ^a

^aCollege of Chemistry and Biology, Beihua University, Jilin 132013, People's Republic of China
^*Correspondence e-mail: nilei_bh@163.com

(Received 9 July 2009; accepted 31 July 2009; online 8 August 2009)

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, P 2₁ /n
a = 5.6670 (11) Å
b = 23.117 (5) Å
c = 7.6880 (15) Å
β = 108.17 (3)°
V = 956.9 (3) Å³
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[F² > 2σ(F²)] = 0.047
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030530/hb5023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030530/hb5023Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.

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

Crystal data top

C₁₀H₁₂N₂O	F(000) = 376
M_r = 176.22	D_x = 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 top

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

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters not refined
S = 1.00	w = 1/[σ²(F_o²) + (0.087P)² + 0.1213P] where P = (F_o² + 2F_c²)/3
1775 reflections	(Δ/σ)_max < 0.001
121 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₀H₁₂N₂O	V = 956.9 (3) Å³
M_r = 176.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.6670 (11) Å	µ = 0.08 mm⁻¹
b = 23.117 (5) Å	T = 295 K
c = 7.6880 (15) Å	0.12 × 0.10 × 0.08 mm
β = 108.17 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1775 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1403 reflections with I > 2σ(I)
T_min = 0.990, T_max = 0.994	R_int = 0.027
7131 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.143	H-atom parameters not refined
S = 1.00	Δρ_max = 0.18 e Å⁻³
1775 reflections	Δρ_min = −0.15 e Å⁻³
121 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
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O
M_r	176.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	5.6670 (11), 23.117 (5), 7.6880 (15)
β (°)	108.17 (3)
V (Å³)	956.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.990, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	7131, 1775, 1403
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.143, 1.00
No. of reflections	1775
No. of parameters	121
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors acknowledge financial support from the Science Foundation of Beihua University.

References

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