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

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

doi:10.1107/S1600536813004236

Volume 69
Part 3
Page o391
March 2013

Received 7 February 2013
Accepted 12 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 17.8
Details

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

Volodymyr Horishny,^a Roman Lesyk ^a 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 structural analysis of the title compound, C₁₄H₁₄N₂O₄S, particularly the presence of an acetyl group at the exocyclic N atom and the C(H)-C(O₂CMe)-N acetoxy group in the thiazole ring, may indicate that one of the starting materials, i.e. 2-(4-methoxyanilino)-1,3-thiazol-4(5H)-one, exists in the reaction mixture, at least partially, as a tautomer with an exocyclic amine N atom and an enol group. The acetoxy and acetyl groups deviate from the thiazole plane by 69.17 (6) and 7.25 (19)°, respectively. The thiazole and benzene rings form a dihedral angle of 73.50 (4)°. In the crystal, centrosymmetrically related molecules are connected into dimeric aggregates via C-HO interactions.

Related literature

For the biological activity of 2-aryl(heteryl)aminothiazol-4-one derivatives, see: Ates et al. (2000); Eleftheriou et al. (2012); Eriksson et al. (2007); Lesyk & Zimenkovsky (2004); Lesyk et al. (2003, 2011); Rout & Mahapatra (1955); Subtel'na et al. (2010). For prototropic tautomerism studies, see: Lesyk et al. (2003); Subtel'na et al. (2010). For bond-length data, see: Allen et al. (1987). For a related structural study, see: Horishny et al. (2013).

Experimental

Crystal data

C₁₄H₁₄N₂O₄S
M_r = 306.33
Triclinic, $[P \overline 1]$
a = 8.9445 (5) Å
b = 9.5736 (8) Å
c = 9.9078 (9) Å
= 115.509 (9)°
= 93.381 (6)°
= 108.144 (6)°
V = 708.95 (10) Å³
Z = 2
Mo K radiation
= 0.25 mm^-1
T = 130 K
0.50 × 0.50 × 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 = 0.860, T_max = 1.000
12469 measured reflections
3445 independent reflections
3075 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.095
S = 1.06
3445 reflections
193 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O20ⁱ	0.93	2.53	3.200 (2)	129
Symmetry code: (i) -x, -y+1, -z+1.

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: TK5195 ).

References

Agilent (2011). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ates, O., Altintas, H. & Otukb, G. (2000). Arzneim. Forsch. 6, 569-575.
Eleftheriou, P., Geronikaki, A., Hadjipavlou-Litina, D., Vicini, P., Filz, O., Filimonov, D., Poroikov, V., Shailendra, S., Chaudhaery, S. S., Roy, K. K. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 111-124.
Eriksson, B., Kurz, G., Hedberg, C. & Westman, J. (2007). Patent No. WO2007010273.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Horishny, V., Lesyk, R., Kowiel, M. & Gzella, A. K. (2013). Acta Cryst. E69, o356-o357.
Lesyk, R. B. & Zimenkovsky, B. S. (2004). Curr. Org. Chem. 8, 1547-1577.
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Lesyk, R., Zimenkovsky, B., Subtelna, I., Nektegayev, I. & Kazmirchuk, G. (2003). Acta Pol. Pharm. 60, 457-466.
Rout, M. K. & Mahapatra, G. N. (1955). J. Am. Chem. Soc. 5, 2427-2428.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Subtel'na, I., Atamanyuk, D., Szymanska, E., Kiec-Kononowicz, K., Zimenkovsky, B., Vasylenko, O., Gzella, A. & Lesyk, R. (2010). Bioorg. Med. Chem. 18, 5090-5102.

organic compounds