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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2103.
Published online 2009 August 8. doi:  10.1107/S1600536809030530
PMCID: PMC2969911

(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 [triangle]); Liu et al. (2009 [triangle]); Kida et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2103-scheme1.jpg

Experimental

Crystal data

  • C10H12N2O
  • M r = 176.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2103-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2004 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

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

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

Acknowledgments

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

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 Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

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

Crystal data

C10H12N2OF(000) = 376
Mr = 176.22Dx = 1.223 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1775 reflections
a = 5.6670 (11) Åθ = 1.8–25.5°
b = 23.117 (5) ŵ = 0.08 mm1
c = 7.6880 (15) ÅT = 295 K
β = 108.17 (3)°Block, yellow
V = 956.9 (3) Å30.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer1775 independent reflections
Radiation source: fine-focus sealed tube1403 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −6→6
Tmin = 0.990, Tmax = 0.994k = −27→28
7131 measured reflectionsl = −9→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters not refined
S = 1.00w = 1/[σ2(Fo2) + (0.087P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3
1775 reflections(Δ/σ)max < 0.001
121 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.15 e Å3

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 (Å2)

xyzUiso*/Ueq
C10.3675 (4)0.01987 (8)−0.3188 (3)0.0664 (6)
H1A0.2562−0.0080−0.29450.100*
H1B0.52320.0016−0.30920.100*
H1C0.29640.0351−0.44010.100*
C20.5845 (4)0.11075 (9)−0.1969 (3)0.0674 (6)
H2A0.50720.1481−0.20790.101*
H2B0.63850.1038−0.30170.101*
H2C0.72510.1096−0.08790.101*
C30.2893 (3)0.06861 (7)−0.0630 (2)0.0456 (4)
H30.18430.0377−0.06330.055*
C40.3024 (3)0.11046 (7)0.0648 (2)0.0464 (4)
H40.40060.14300.07030.056*
C50.1648 (3)0.10380 (7)0.1890 (2)0.0445 (4)
C60.1719 (3)0.15207 (6)0.3237 (2)0.0423 (4)
C70.0089 (3)0.15063 (8)0.4258 (2)0.0533 (5)
H7−0.10380.12040.41180.064*
C80.0165 (4)0.19467 (9)0.5484 (2)0.0615 (5)
H8−0.09160.19470.61790.074*
C90.1851 (4)0.23816 (8)0.5661 (2)0.0608 (5)
H90.19510.26820.64840.073*
C100.3406 (4)0.23655 (8)0.4592 (2)0.0584 (5)
H100.45490.26640.47200.070*
N10.4076 (3)0.06659 (6)−0.18682 (18)0.0500 (4)
N20.3368 (3)0.19482 (6)0.33867 (18)0.0505 (4)
O10.0370 (3)0.06092 (5)0.19576 (18)0.0657 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0977 (16)0.0551 (11)0.0587 (11)0.0089 (10)0.0423 (11)−0.0012 (9)
C20.0611 (12)0.0857 (14)0.0628 (12)−0.0074 (10)0.0303 (10)0.0026 (10)
C30.0508 (9)0.0462 (9)0.0432 (9)0.0036 (7)0.0197 (7)0.0052 (7)
C40.0487 (9)0.0464 (9)0.0466 (9)−0.0007 (7)0.0185 (7)−0.0010 (7)
C50.0491 (9)0.0431 (9)0.0427 (9)0.0008 (7)0.0164 (7)0.0007 (7)
C60.0457 (9)0.0423 (9)0.0387 (8)0.0060 (7)0.0128 (7)0.0034 (6)
C70.0541 (10)0.0571 (11)0.0531 (10)0.0016 (8)0.0232 (8)−0.0037 (8)
C80.0649 (12)0.0701 (13)0.0560 (11)0.0110 (10)0.0284 (9)−0.0077 (9)
C90.0763 (13)0.0555 (11)0.0482 (10)0.0122 (9)0.0161 (9)−0.0103 (8)
C100.0730 (12)0.0476 (10)0.0519 (10)−0.0048 (9)0.0158 (9)−0.0051 (8)
N10.0591 (9)0.0520 (8)0.0462 (8)0.0031 (6)0.0271 (7)0.0023 (6)
N20.0581 (9)0.0476 (8)0.0466 (8)−0.0037 (7)0.0178 (7)−0.0031 (6)
O10.0896 (10)0.0554 (8)0.0676 (9)−0.0208 (7)0.0472 (8)−0.0144 (6)

Geometric parameters (Å, °)

C1—N11.451 (2)C5—O11.2384 (18)
C1—H1A0.9600C5—C61.514 (2)
C1—H1B0.9600C6—N21.340 (2)
C1—H1C0.9600C6—C71.386 (2)
C2—N11.450 (2)C7—C81.379 (2)
C2—H2A0.9600C7—H70.9300
C2—H2B0.9600C8—C91.364 (3)
C2—H2C0.9600C8—H80.9300
C3—N11.325 (2)C9—C101.380 (3)
C3—C41.364 (2)C9—H90.9300
C3—H30.9300C10—N21.333 (2)
C4—C51.417 (2)C10—H100.9300
C4—H40.9300
N1—C1—H1A109.5C4—C5—C6118.57 (14)
N1—C1—H1B109.5N2—C6—C7122.61 (15)
H1A—C1—H1B109.5N2—C6—C5118.10 (14)
N1—C1—H1C109.5C7—C6—C5119.29 (15)
H1A—C1—H1C109.5C8—C7—C6119.01 (17)
H1B—C1—H1C109.5C8—C7—H7120.5
N1—C2—H2A109.5C6—C7—H7120.5
N1—C2—H2B109.5C9—C8—C7118.94 (17)
H2A—C2—H2B109.5C9—C8—H8120.5
N1—C2—H2C109.5C7—C8—H8120.5
H2A—C2—H2C109.5C8—C9—C10118.55 (16)
H2B—C2—H2C109.5C8—C9—H9120.7
N1—C3—C4128.04 (15)C10—C9—H9120.7
N1—C3—H3116.0N2—C10—C9123.96 (17)
C4—C3—H3116.0N2—C10—H10118.0
C3—C4—C5119.39 (15)C9—C10—H10118.0
C3—C4—H4120.3C3—N1—C2121.81 (14)
C5—C4—H4120.3C3—N1—C1121.65 (15)
O1—C5—C4124.55 (15)C2—N1—C1116.54 (14)
O1—C5—C6116.87 (14)C10—N2—C6116.93 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5023).

References

  • Bruker (2004). APEX2, SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kida, N., Hikita, M., Kashima, I., Okubo, M., Itoi, M., Enomoto, M., Kato, K., Takata, M. & Kojima, N. (2009). J. Am. Chem. Soc.131, 212–220. [PubMed]
  • Liu, Y., Turner, D. B., Singh, T. N., Angeles-Boza, A. M., Chouai, A., Dunbar, K. R. & Turro, C. (2009). J. Am. Chem. Soc.131, 26–27. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, X., Dou, J., Wei, P., Li, D., Li, B., Shi, C. & Hu, B. (2009). Inorg. Chim. Acta, 362, 3325–3332.

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