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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2104.
Published online 2009 August 8. doi:  10.1107/S1600536809030542
PMCID: PMC2969928

(E)-3-Dimethyl­amino-1-(4-pyrid­yl)prop-2-en-1-one

Abstract

The title compound, C10H12N2O, is approximately planar, the r.m.s. deviation of the non-H atoms from the mean plane being 0.099 Å.

Related literature

For an isomer of the title compound with the same space group and similar unit-cell parameters, see: Ni et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2104-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-o2104-efi1.jpg
  • a = 5.6300 (11) Å
  • b = 22.850 (5) Å
  • c = 7.8400 (16) Å
  • β = 107.57 (3)°
  • V = 961.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 294 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
  • 5177 measured reflections
  • 1784 independent reflections
  • 1503 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.137
  • S = 1.00
  • 1784 reflections
  • 121 parameters
  • H-atom parameters not refined
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.13 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/S1600536809030542/hb5024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030542/hb5024Isup2.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

As part of our ongoing studies of heteroaromatic compounds (Ni et al., 2009), we now 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 the r.m.s deviation of the fitted atoms being 0.099 Å.

Experimental

A mixture of 4-acetylpyridine(10 mmol) and N,N-dimethylformamide-dimethyl acetal(40 ml) was refluxed for four hours. After concentration invacuo, 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 68.05, H 6.69, N 15.81%.

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 = 1.217 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1784 reflections
a = 5.6300 (11) Åθ = 1.8–25.5°
b = 22.850 (5) ŵ = 0.08 mm1
c = 7.8400 (16) ÅT = 294 K
β = 107.57 (3)°Block, yellow
V = 961.5 (3) Å30.12 × 0.10 × 0.08 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer1784 independent reflections
Radiation source: fine-focus sealed tube1503 reflections with I > 2σ(I)
graphiteRint = 0.022
[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→26
5177 measured reflectionsl = −7→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters not refined
wR(F2) = 0.137w = 1/[σ2(Fo2) + (0.092P)2 + 0.1151P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
1784 reflectionsΔρmax = 0.20 e Å3
121 parametersΔρmin = −0.12 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (6)

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
C10.8254 (2)0.15312 (5)0.68372 (16)0.0403 (3)
C20.6652 (3)0.20055 (6)0.65592 (17)0.0451 (4)
H20.54900.20360.71830.054*
C30.6795 (3)0.24329 (7)0.5346 (2)0.0541 (4)
H30.56980.27470.51800.065*
C40.9907 (3)0.19670 (8)0.4672 (2)0.0634 (5)
H41.10400.19470.40220.076*
C50.9919 (3)0.15168 (7)0.5851 (2)0.0533 (4)
H51.10340.12080.59800.064*
C60.8303 (2)0.10391 (6)0.81421 (18)0.0441 (4)
C70.6972 (2)0.11110 (6)0.94016 (18)0.0452 (4)
H70.60120.14440.93770.054*
C80.7118 (3)0.06832 (6)1.06560 (18)0.0453 (4)
H80.81470.03671.06320.054*
C90.4227 (3)0.11224 (8)1.2011 (2)0.0668 (5)
H9A0.50850.14901.22710.100*
H9B0.35190.10281.29480.100*
H9C0.29240.11501.08940.100*
C100.6374 (3)0.01980 (7)1.3199 (2)0.0641 (5)
H10A0.7505−0.00831.29660.096*
H10B0.48150.00111.31120.096*
H10C0.70690.03551.43800.096*
N10.8397 (3)0.24245 (6)0.44017 (18)0.0617 (4)
N20.5966 (2)0.06690 (5)1.18924 (16)0.0494 (4)
O10.9520 (2)0.05981 (5)0.80351 (16)0.0677 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0414 (7)0.0407 (7)0.0388 (7)−0.0052 (5)0.0120 (5)−0.0024 (5)
C20.0477 (7)0.0453 (8)0.0433 (7)−0.0010 (6)0.0153 (6)−0.0018 (6)
C30.0581 (9)0.0476 (8)0.0541 (9)0.0035 (6)0.0131 (7)0.0068 (6)
C40.0583 (9)0.0715 (11)0.0699 (10)0.0001 (8)0.0337 (8)0.0178 (8)
C50.0500 (8)0.0541 (9)0.0623 (9)0.0035 (6)0.0268 (7)0.0092 (7)
C60.0480 (7)0.0410 (7)0.0460 (7)0.0005 (5)0.0184 (6)0.0004 (6)
C70.0498 (7)0.0429 (7)0.0467 (7)0.0020 (6)0.0202 (6)0.0009 (5)
C80.0499 (8)0.0442 (8)0.0460 (8)−0.0016 (6)0.0210 (6)−0.0037 (6)
C90.0651 (10)0.0810 (12)0.0631 (10)0.0146 (8)0.0326 (8)0.0008 (8)
C100.0914 (12)0.0553 (9)0.0583 (9)−0.0050 (8)0.0415 (9)0.0036 (7)
N10.0633 (8)0.0598 (8)0.0646 (8)−0.0018 (6)0.0232 (7)0.0176 (6)
N20.0576 (7)0.0507 (7)0.0476 (7)0.0002 (5)0.0274 (6)0.0012 (5)
O10.0928 (9)0.0519 (7)0.0772 (8)0.0237 (6)0.0538 (7)0.0171 (5)

Geometric parameters (Å, °)

C1—C21.3846 (18)C7—C81.3713 (19)
C1—C51.3842 (19)C7—H70.9300
C1—C61.5148 (18)C8—N21.3193 (17)
C2—C31.382 (2)C8—H80.9300
C2—H20.9300C9—N21.4476 (19)
C3—N11.329 (2)C9—H9A0.9600
C3—H30.9300C9—H9B0.9600
C4—N11.323 (2)C9—H9C0.9600
C4—C51.382 (2)C10—N21.4555 (19)
C4—H40.9300C10—H10A0.9600
C5—H50.9300C10—H10B0.9600
C6—O11.2357 (16)C10—H10C0.9600
C6—C71.4180 (18)
C2—C1—C5116.72 (12)C6—C7—H7120.4
C2—C1—C6124.44 (12)N2—C8—C7127.45 (13)
C5—C1—C6118.84 (12)N2—C8—H8116.3
C1—C2—C3119.39 (13)C7—C8—H8116.3
C1—C2—H2120.3N2—C9—H9A109.5
C3—C2—H2120.3N2—C9—H9B109.5
N1—C3—C2124.31 (14)H9A—C9—H9B109.5
N1—C3—H3117.8N2—C9—H9C109.5
C2—C3—H3117.8H9A—C9—H9C109.5
N1—C4—C5124.67 (14)H9B—C9—H9C109.5
N1—C4—H4117.7N2—C10—H10A109.5
C5—C4—H4117.7N2—C10—H10B109.5
C4—C5—C1119.24 (14)H10A—C10—H10B109.5
C4—C5—H5120.4N2—C10—H10C109.5
C1—C5—H5120.4H10A—C10—H10C109.5
O1—C6—C7124.21 (12)H10B—C10—H10C109.5
O1—C6—C1117.19 (12)C4—N1—C3115.67 (13)
C7—C6—C1118.60 (11)C8—N2—C9121.45 (12)
C8—C7—C6119.15 (12)C8—N2—C10121.81 (13)
C8—C7—H7120.4C9—N2—C10116.74 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5024).

References

  • Bruker (2004). APEX2, SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ni, L., Zhao, J.-L. & Wei, H. (2009). Acta Cryst. E65, o2103. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography