2-[N-(2,4-Dimeth­oxy­phen­yl)acetamido]-1,3-thia­zol-4-yl acetate

Horishny, V.; Lesyk, R.; Kowiel, M.; Gzella, A.K.

doi:10.1107/S1600536813003474

Volume 69
Part 3
Pages o356-o357
March 2013

Received 1 February 2013
Accepted 4 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 18.0
Details

2-[N-(2,4-Dimethoxyphenyl)acetamido]-1,3-thiazol-4-yl acetate

Volodymyr Horishny,^a Roman Lesyk,^a Marcin Kowiel ^b and Andrzej K. Gzella ^b,^c ^*

^aDepartment of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv, 79010, Ukraine,^bDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznan, Poland, and ^cFaculty of Pharmacy, Ludwik Rydygier Collegium Medicum in Bydgoszcz, Nicolaus Copernicus University in Torun, ul. A. Jurasza 2, 85-089 Bydgoszcz, Poland
Correspondence e-mail: akgzella@ump.edu.pl

The title compound, C₁₅H₁₆N₂O₅S, is a product of the reaction of 2-(2,4-dimethoxyphenylamino)-1,3-thiazol-4(5H)-one with acetic anhydride. The presence of the acetyl and acetoxy groups in the molecule indicates that the starting thiazole exists as a tautomer in the reaction mixture with exocyclic amino and enol moieties. The acetyl group is tilted slightly from the heterocyclic ring plane [dihedral angle = 4.46 (11)°], while the acetoxy group is almost perpendicular to this ring [dihedral angle = 88.14 (12)°]. An intramolecular acetyl-methoxy C-HO interaction is noted. In the crystal, molecules are connected into a three-dimensional architecture by C-HO interactions.

Related literature

For the biological activity of 2-arylaminothiazol-4-one derivatives, see: Chen et al. (2007); Eriksson et al. (2007); Lesyk & Zimenkovsky (2004); Lesyk et al. (2011); Ottana et al. (2005); Subtelna et al. (2010); Vassilev et al. (2006). For prototropic tautomerism studies, see: Subtelna et al. (2010); Lesyk et al. (2003); Vana et al. (2009).

Experimental

Crystal data

C₁₅H₁₆N₂O₅S
M_r = 336.36
Triclinic, $[P \overline 1]$
a = 9.1486 (11) Å
b = 9.3592 (13) Å
c = 10.2823 (8) Å
= 69.212 (10)°
= 82.910 (8)°
= 77.220 (11)°
V = 801.73 (16) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 130 K
0.30 × 0.30 × 0.10 mm

Data collection

Agilent Xcalibur Atlas diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 $[Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.919, T_max = 1.000
10576 measured reflections
3822 independent reflections
3281 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.093
S = 1.06
3822 reflections
212 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9AO16	0.96	2.57	3.1838 (19)	122
C5-H5O18ⁱ	0.93	2.47	3.2465 (18)	141
C15-H15O8ⁱⁱ	0.93	2.52	3.3117 (18)	143
C17-H17CO8ⁱⁱⁱ	0.96	2.35	3.2945 (19)	170
Symmetry codes: (i) x, y-1, z+1; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011 $[Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5194 ).

References

Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Chen, S., Chen, L., Le, N. T., Zhao, C., Sidduri, A., Lou, J. P., Michoud, C., Portland, L., Jackson, N. & Liu, J. J. (2007). Bioorg. Med. Chem. Lett. 17, 2134-2138.
Eriksson, B., Kurz, G., Hedberg, C. & Westman, J. (2007). Patent No. WO2007010273.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Lesyk, R. B. & Zimenkovsky, B. S. (2004). Curr. Org. Chem. 8, 1547-1577.
Lesyk, R. B., Zimenkovsky, B. S., Kaminskyy, D. V., Kryshchyshyn, A. P., Havrylyuk, D. Ya., Atamanyuk, D. V., Subtel'na, I. Yu. & Khyluk, D. V. (2011). Biopolym. Cell. 27, 107-117.
Lesyk, R., Zimenkovsky, B., Subtelna, I., Nektegayev, I. & Kazmirchuk, G. (2003). Acta Pol. Pharm. 60, 457-466.
Ottana, R., Carotti, S., Maccari, R., Landini, I., Chiricosta, G., Caciagli, B., Vigorita, M. G. & Mini, E. (2005). Bioorg. Med. Chem. Lett. 15, 3930-3933.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Subtelna, I., Atamanyuk, D., Szymanska, E., Kiec-Kononowicz, K., Zimenkovsky, B., Vasylenko, O., Gzella, A. & Lesyk, R. (2010). Bioorg. Med. Chem. 18, 5089-5101.
Vana, J., Hanusek, J., Ruzicka, A. & Sedlak, M. (2009). J. Heterocycl. Chem. 46, 635-639.
Vassilev, L. T., Tovar, C., Chen, S., Knezevic, D., Zhao, X., Sun, H., Heimbrook, D. C. & Chen, L. (2006). Proc. Natl Acad. Sci. USA, 103, 10660-10665.

organic compounds