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

You, X.-Y.; Shi, Y.-J.; Yu, L.-T.

doi:10.1107/S1600536812048817

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 16.6
Details

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

Xin-Yu You,^a Yao-Jie Shi ^b and Luo-Ting Yu ^b ^*

^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-HN and C-HO interactions together with C-H [pi] interactions generate a three-dimensional network.

Related literature

For the biological activity of enaminone derivatives, see: Zeng (2010).

Experimental

Crystal data

C₈H₁₀N₂OS
M_r = 182.24
Monoclinic, P 2₁ /n
a = 5.6252 (2) Å
b = 22.5957 (8) Å
c = 7.5777 (3) Å
= 109.498 (4)°
V = 907.93 (6) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.974, T_max = 1.000
3683 measured reflections
1846 independent reflections
1565 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.090
S = 1.06
1846 reflections
111 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C2-H2N1ⁱ	0.95	2.62	3.560 (2)	169
C6-H6O1ⁱⁱ	0.95	2.60	3.462 (2)	151
C8-H8AO1ⁱⁱ	0.98	2.31	3.269 (2)	167
C9-H9CO1ⁱⁱⁱ	0.98	2.51	3.433 (2)	157
C9-H9ACg1^iv	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); 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.
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.
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zeng, X. X. (2010). Bioorg. Med. Chem. Lett. 20, 6282-6285.

organic compounds