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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.095
Data-to-parameter ratio = 17.8
Details
Open access

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

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-H...O interactions.

Related literature

For the biological activity of 2-aryl(heteryl)aminothiazol-4-one derivatives, see: Ates et al. (2000[Ates, O., Altintas, H. & Otukb, G. (2000). Arzneim. Forsch. 6, 569-575.]); Eleftheriou et al. (2012[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 et al. (2007[Eriksson, B., Kurz, G., Hedberg, C. & Westman, J. (2007). Patent No. WO2007010273.]); Lesyk & Zimenkovsky (2004[Lesyk, R. B. & Zimenkovsky, B. S. (2004). Curr. Org. Chem. 8, 1547-1577.]); Lesyk et al. (2003[Lesyk, R., Zimenkovsky, B., Subtelna, I., Nektegayev, I. & Kazmirchuk, G. (2003). Acta Pol. Pharm. 60, 457-466.], 2011[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.]); Rout & Mahapatra (1955[Rout, M. K. & Mahapatra, G. N. (1955). J. Am. Chem. Soc. 5, 2427-2428.]); Subtel'na et al. (2010[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.]). For prototropic tautomerism studies, see: Lesyk et al. (2003[Lesyk, R., Zimenkovsky, B., Subtelna, I., Nektegayev, I. & Kazmirchuk, G. (2003). Acta Pol. Pharm. 60, 457-466.]); Subtel'na et al. (2010[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.]). For bond-length data, see: Allen et al. (1987[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.]). For a related structural study, see: Horishny et al. (2013[Horishny, V., Lesyk, R., Kowiel, M. & Gzella, A. K. (2013). Acta Cryst. E69, o356-o357.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14N2O4S

  • Mr = 306.33

  • Triclinic, [P \overline 1]

  • a = 8.9445 (5) Å

  • b = 9.5736 (8) Å

  • c = 9.9078 (9) Å

  • [alpha] = 115.509 (9)°

  • [beta] = 93.381 (6)°

  • [gamma] = 108.144 (6)°

  • V = 708.95 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.860, Tmax = 1.000

  • 12469 measured reflections

  • 3445 independent reflections

  • 3075 reflections with I > 2[sigma](I)

  • Rint = 0.022

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

  • wR(F2) = 0.095

  • S = 1.06

  • 3445 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O20i 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[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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort] [PubMed]
Eriksson, B., Kurz, G., Hedberg, C. & Westman, J. (2007). Patent No. WO2007010273.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Horishny, V., Lesyk, R., Kowiel, M. & Gzella, A. K. (2013). Acta Cryst. E69, o356-o357.  [CrossRef] [details]
Lesyk, R. B. & Zimenkovsky, B. S. (2004). Curr. Org. Chem. 8, 1547-1577.  [ISI] [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
Lesyk, R., Zimenkovsky, B., Subtelna, I., Nektegayev, I. & Kazmirchuk, G. (2003). Acta Pol. Pharm. 60, 457-466.  [PubMed] [ChemPort]
Rout, M. K. & Mahapatra, G. N. (1955). J. Am. Chem. Soc. 5, 2427-2428.  [CrossRef] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [ChemPort] [PubMed]


Acta Cryst (2013). E69, o391  [ doi:10.1107/S1600536813004236 ]

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