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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1847.
Published online 2009 July 11. doi:  10.1107/S1600536809025331
PMCID: PMC2977183

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

Abstract

The mol­ecular skeleton of the title mol­ecule, C9H11NOS, is essentially planar: the thio­phene ring is inclined to the mean plane of the rest non-H atoms by 2.92 (3)°. The crystal packing exhibits no significantly short inter­molecular contacts.

Related literature

For general backgroud, see Amari et al. (1993 [triangle]). For the crystal structures of related compounds, see: Li et al. (2005 [triangle]); Hu et al. (2007 [triangle]); Bi (2009 [triangle]).

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Object name is e-65-o1847-scheme1.jpg

Experimental

Crystal data

  • C9H11NOS
  • M r = 181.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1847-efi1.jpg
  • a = 5.9618 (12) Å
  • b = 8.1241 (16) Å
  • c = 19.449 (4) Å
  • β = 92.910 (3)°
  • V = 940.8 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 291 K
  • 0.45 × 0.30 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.867, T max = 0.964
  • 4740 measured reflections
  • 1636 independent reflections
  • 1137 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.124
  • S = 1.05
  • 1636 reflections
  • 111 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025331/cv2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025331/cv2582Isup2.hkl

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

Acknowledgments

The author is indebted to the National Natural Science Foundation of China for financial support (grant No. 20871039).

supplementary crystallographic information

Comment

Many coordinated complexes derived from 2-[3-(dimethylamino)prop-2-enoyl] pyridine or thiophene have been reported recently in chemical research (Amari et al., 1993; Bi, 2009; Hu & Tian, 2007; Li et al., 2005). In continuation of our ongoing program directed to the development of similar compounds (Bi, 2009), herein we report the molecular structure of the title compound (I) - the newly synthesized ligand derived from 2-acetylthiophene.

In (I) (Fig. 1), the dihedral angle between the thiophene ring and the mean plane of the restnon-hydrogen atoms is 2.92 (3)°. The crystal packing exhibits no significantly short intermolecular contacts.

Experimental

All solvents and chemicals were of analytical grade and were used without further purification. A solution of 2-acetylthiophene (0.2 mmol) and dimethoxy-N,N-dimethylmethanamine(0.2 mmol) in 150 ml DMF was refluxed for 8 h, and then concentrated to give the title compound. Single crystals suitable for X-ray analysis were grown from the methanol solution by slow evaporation at room temperature in air. Anal. Calcd.for C9H11NOS: C, 59.64; H, 6.12; N, 7.73. Found: C, 39.65; H,6.16; N, 7.71.

Refinement

All hydrogen atoms were geometrically positioned (C—H 0.93–0.97 Å) and refined as riding, with Uiso(H)=1.2–1.5 Ueq of the parent atom.

Figures

Fig. 1.
Molecular structure of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids.

Crystal data

C9H11NOSF(000) = 384
Mr = 181.26Dx = 1.280 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 955 reflections
a = 5.9618 (12) Åθ = 2.7–20.2°
b = 8.1241 (16) ŵ = 0.30 mm1
c = 19.449 (4) ÅT = 291 K
β = 92.910 (3)°Block, yellow
V = 940.8 (3) Å30.45 × 0.30 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1636 independent reflections
Radiation source: fine-focus sealed tube1137 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −7→6
Tmin = 0.867, Tmax = 0.964k = −9→8
4740 measured reflectionsl = −23→19

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) = 0.124H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2232P] where P = (Fo2 + 2Fc2)/3
1636 reflections(Δ/σ)max < 0.001
111 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.
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
C10.0234 (4)0.4667 (3)0.16370 (13)0.0425 (6)
C20.2349 (4)0.5260 (3)0.18109 (14)0.0462 (7)
H20.35860.51080.15450.055*
C30.2416 (5)0.6127 (3)0.24415 (16)0.0581 (8)
H30.37070.66200.26350.070*
C40.0404 (5)0.6165 (4)0.27337 (15)0.0594 (8)
H40.01550.66850.31490.071*
C5−0.0592 (4)0.3689 (3)0.10366 (14)0.0479 (7)
C60.0996 (4)0.3228 (3)0.05454 (14)0.0481 (7)
H60.25010.35100.06180.058*
C70.0307 (4)0.2381 (3)−0.00247 (14)0.0499 (7)
H7−0.12200.2142−0.00660.060*
C80.3912 (5)0.2183 (5)−0.05347 (19)0.0906 (12)
H8A0.41460.3350−0.05660.136*
H8B0.45320.1650−0.09220.136*
H8C0.46380.1775−0.01170.136*
C90.0524 (6)0.0980 (4)−0.11220 (15)0.0691 (9)
H9A−0.10520.0830−0.10640.104*
H9B0.1233−0.0074−0.11620.104*
H9C0.07320.1611−0.15310.104*
N10.1517 (4)0.1844 (3)−0.05331 (12)0.0566 (6)
O1−0.2623 (3)0.3317 (3)0.09894 (10)0.0688 (6)
S1−0.15994 (12)0.51590 (10)0.22552 (4)0.0598 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0437 (14)0.0414 (15)0.0427 (15)0.0011 (11)0.0066 (12)0.0028 (12)
C20.0414 (14)0.0467 (16)0.0509 (17)−0.0023 (11)0.0057 (12)−0.0032 (13)
C30.0515 (16)0.0588 (19)0.0636 (19)−0.0033 (14)−0.0019 (14)−0.0104 (16)
C40.0681 (19)0.0601 (19)0.0499 (18)0.0025 (15)0.0019 (15)−0.0097 (15)
C50.0451 (15)0.0498 (17)0.0489 (17)−0.0032 (12)0.0040 (13)0.0067 (14)
C60.0435 (14)0.0520 (17)0.0492 (17)−0.0036 (12)0.0065 (13)0.0014 (14)
C70.0480 (16)0.0532 (17)0.0492 (17)0.0003 (12)0.0093 (14)0.0046 (14)
C80.062 (2)0.128 (3)0.084 (3)−0.002 (2)0.0275 (19)−0.016 (2)
C90.091 (2)0.064 (2)0.0531 (19)−0.0050 (18)0.0129 (17)−0.0053 (17)
N10.0547 (14)0.0666 (16)0.0494 (14)−0.0018 (12)0.0109 (11)−0.0068 (13)
O10.0444 (11)0.0969 (16)0.0658 (14)−0.0154 (10)0.0100 (10)−0.0200 (12)
S10.0495 (5)0.0741 (6)0.0571 (5)−0.0014 (4)0.0145 (4)−0.0052 (4)

Geometric parameters (Å, °)

C1—C21.376 (3)C6—H60.9300
C1—C51.476 (4)C7—N11.327 (3)
C1—S11.713 (2)C7—H70.9300
C2—C31.413 (4)C8—N11.455 (4)
C2—H20.9300C8—H8A0.9600
C3—C41.353 (4)C8—H8B0.9600
C3—H30.9300C8—H8C0.9600
C4—S11.688 (3)C9—N11.444 (4)
C4—H40.9300C9—H9A0.9600
C5—O11.247 (3)C9—H9B0.9600
C5—C61.429 (3)C9—H9C0.9600
C6—C71.351 (4)
C2—C1—C5130.4 (2)N1—C7—H7115.7
C2—C1—S1110.8 (2)C6—C7—H7115.7
C5—C1—S1118.81 (18)N1—C8—H8A109.5
C1—C2—C3111.9 (2)N1—C8—H8B109.5
C1—C2—H2124.0H8A—C8—H8B109.5
C3—C2—H2124.0N1—C8—H8C109.5
C4—C3—C2112.9 (3)H8A—C8—H8C109.5
C4—C3—H3123.5H8B—C8—H8C109.5
C2—C3—H3123.5N1—C9—H9A109.5
C3—C4—S1112.0 (2)N1—C9—H9B109.5
C3—C4—H4124.0H9A—C9—H9B109.5
S1—C4—H4124.0N1—C9—H9C109.5
O1—C5—C6124.1 (3)H9A—C9—H9C109.5
O1—C5—C1118.2 (2)H9B—C9—H9C109.5
C6—C5—C1117.7 (2)C7—N1—C9122.3 (2)
C7—C6—C5119.9 (2)C7—N1—C8120.7 (3)
C7—C6—H6120.1C9—N1—C8116.9 (2)
C5—C6—H6120.1C4—S1—C192.36 (13)
N1—C7—C6128.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2582).

References

  • Amari, C., Ianelli, S., Pelizzi, C., Pelizzi, G. & Predieri, G. (1993). Inorg. Chim. Acta, 211, 89–94.
  • Bi, J.-H. (2009). Acta Cryst. E65, m633. [PMC free article] [PubMed]
  • Bruker (2000). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hu, T.-L. & Tian, J.-L. (2007). Acta Cryst. E63, m1092–m1093.
  • Li, G.-X., Li, J.-Q. & Kang, X.-Z. (2005). Acta Cryst. E61, m410–m411.
  • 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