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Volume 69 
Part 1 
Page o18  
January 2013  

Received 19 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 135 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 16.6
Details
Open access

(E)-3-Dimethylamino-1-(1,3-thiazol-2-yl)prop-2-en-1-one

aDepartment of Pharmaceutical and Bioengineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China, and bState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
Correspondence e-mail: yuluot@scu.edu.cn

In the title compound, C8H10N2OS, the 3-(dimethylamino)prop-2-en-1-one unit is approximately planar [give r.m.s. deviation] and the mean plane through the seven non-H atoms makes a dihedral angle of 8.88 (3)° with the thiazole ring. The carbonyl and ring C=N double bonds adjacent to the carbonyl group are trans [N-C-C-O = 172.31 (15) °], while the conformation of the carbonyl and propene double bonds is cis [O-C-C-C = 2.2 (2)°]. In the crystal, short C-H...N and C-H...O interactions together with C-H...[pi] interactions generate a three-dimensional network.

Related literature

For the biological activity of enaminone derivatives, see: Zeng (2010[Zeng, X. X. (2010). Bioorg. Med. Chem. Lett. 20, 6282-6285.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10N2OS

  • Mr = 182.24

  • Monoclinic, P 21 /n

  • a = 5.6252 (2) Å

  • b = 22.5957 (8) Å

  • c = 7.5777 (3) Å

  • [beta] = 109.498 (4)°

  • V = 907.93 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 135 K

  • 0.35 × 0.30 × 0.30 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.974, Tmax = 1.000

  • 3683 measured reflections

  • 1846 independent reflections

  • 1565 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.090

  • S = 1.06

  • 1846 reflections

  • 111 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/N1/C1-C3 ring.

D-H...A D-H H...A D...A D-H...A
C2-H2...N1i 0.95 2.62 3.560 (2) 169
C6-H6...O1ii 0.95 2.60 3.462 (2) 151
C8-H8A...O1ii 0.98 2.31 3.269 (2) 167
C9-H9C...O1iii 0.98 2.51 3.433 (2) 157
C9-H9A...Cg1iv 0.98 2.93 3.549 (2) 122
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z; (iii) x+1, y, z; (iv) x, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2183 ).


Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray data collection.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zeng, X. X. (2010). Bioorg. Med. Chem. Lett. 20, 6282-6285.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o18  [ doi:10.1107/S1600536812048817 ]

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