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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 18.0
Details
Open access

2-[N-(2,4-Dimethoxyphenyl)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 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-H...O interaction is noted. In the crystal, molecules are connected into a three-dimensional architecture by C-H...O interactions.

Related literature

For the biological activity of 2-arylaminothiazol-4-one derivatives, see: Chen et al. (2007[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 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. (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.]); Ottana et al. (2005[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.]); Subtelna et al. (2010[Subtelna, I., Atamanyuk, D., Szymanska, E., Kiec-Kononowicz, K., Zimenkovsky, B., Vasylenko, O., Gzella, A. & Lesyk, R. (2010). Bioorg. Med. Chem. 18, 5089-5101.]); Vassilev et al. (2006[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.]). For prototropic tautomerism studies, see: Subtelna et al. (2010[Subtelna, I., Atamanyuk, D., Szymanska, E., Kiec-Kononowicz, K., Zimenkovsky, B., Vasylenko, O., Gzella, A. & Lesyk, R. (2010). Bioorg. Med. Chem. 18, 5089-5101.]); Lesyk et al. (2003[Lesyk, R., Zimenkovsky, B., Subtelna, I., Nektegayev, I. & Kazmirchuk, G. (2003). Acta Pol. Pharm. 60, 457-466.]); Vana et al. (2009[Vana, J., Hanusek, J., Ruzicka, A. & Sedlak, M. (2009). J. Heterocycl. Chem. 46, 635-639.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16N2O5S

  • Mr = 336.36

  • Triclinic, [P \overline 1]

  • a = 9.1486 (11) Å

  • b = 9.3592 (13) Å

  • c = 10.2823 (8) Å

  • [alpha] = 69.212 (10)°

  • [beta] = 82.910 (8)°

  • [gamma] = 77.220 (11)°

  • V = 801.73 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.919, Tmax = 1.000

  • 10576 measured reflections

  • 3822 independent reflections

  • 3281 reflections with I > 2[sigma](I)

  • Rint = 0.023

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

  • wR(F2) = 0.093

  • S = 1.06

  • 3822 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9A...O16 0.96 2.57 3.1838 (19) 122
C5-H5...O18i 0.93 2.47 3.2465 (18) 141
C15-H15...O8ii 0.93 2.52 3.3117 (18) 143
C17-H17C...O8iii 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[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: 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.  [CrossRef] [PubMed] [ChemPort]
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]
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]
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.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o356-o357   [ doi:10.1107/S1600536813003474 ]

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