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Volume 69 
Part 9 
Page o1391  
September 2013  

Received 3 July 2013
Accepted 15 July 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 133 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.088
Data-to-parameter ratio = 13.6
Details
Open access

2-Isopropyl-2-(6-methoxy-1,3-benzothiazol-2-yl)-5,5-dimethyl-1,3-thiazolidin-4-one

aInstitut für Organische Chemie und Makromolekulare Chemie, Universität Jena, Humboldtstrasse 10, 07743 Jena, Germany, and bInstitut für Anorganische und Analytische Chemie, Friedrich-Schiller-Universität Jena, Humboldtstrasse 8, 07743 Jena, Germany
Correspondence e-mail: c6bera@rz.uni-jena.de

The title compound, C16H20N2O2S2, crystallizes with two enantiomers (A and B) in the asymmetric unit. The most noticeable difference between these two molecules is the relative orientation of the benzothiazole rings, with S-C-C-S torsion angles of -19.4 (2) (molecule A) and 100.6 (1)° (molecule B). The amide structure of the thiazolidinone rings leads to intermolecular hydrogen-bonded dimers of the R and S enantiomers.

Related literature

For chemi- and bioluminescence of firefly luciferin and related compounds, see: Jung et al. (1975[Jung, J., Chin, C.-A. & Song, P.-S. (1975). J. Am. Chem. Soc. 97, 3949-3954.]); Naumov et al. (2009[Naumov, P., Ozawa, Y., Ohkubo, K. & Fukuzumi, S. (2009). J. Am. Chem. Soc. 131, 11590-11605.]); White et al. (1979[White, E. H., Steinmetz, M. G., Miano, J. D., Wildes, P. D. & Morland, R. (1979). J. Am. Chem. Soc. 101, 3199-3208.]); Branchini et al. (2002[Branchini, B. R., Murtiashaw, M. H., Magyar, R. A., Portier, N. C., Ruggiero, M. C. & Stroh, J. G. (2002). J. Am. Chem. Soc. 124, 2112-2113.]). For structure modifications of firefly luciferin, see: Meroni et al. (2009[Meroni, G., Rajabi, M. & Santaniello, E. (2009). ARKIVOC, i, 265-288.]); McCutcheon et al. (2012[McCutcheon, D. C., Paley, M. A., Steinhardt, R. C. & Prescher, J. A. (2012). J. Am. Chem. Soc. 134, 7604-7607.]); Branchini et al. (2012[Branchini, B. R., Woodroofe, C. C., Meisenheimer, P. L., Klaubert, D. H., Kovic, Y., Rosenberg, J. C., Behney, C. E. & Southworth, T. L. (2012). Biochemistry, 51, 9807-9813.]); Würfel (2012[Würfel, H. (2012). PhD thesis. Friedrich-Schiller-University Jena, Germany.]). Luciferin and related structures are widely used in clinical and biochemical applications, see: Schäffer (1987[Schäffer, J. M. (1987). US Patent 4665022.]); Kricka (1988[Kricka, L. J. (1988). Anal. Biochem. 175, 14-21.]); Josel et al. (1994[Josel, H.-P., Herrmann, R., Klein, C. & Heindl, D. (1994). German Patent DE 4210759.]); Shinde et al. (2006[Shinde, R., Perkins, J. & Contag, C. H. (2006). Biochemistry, 45, 11103-11112.]). All solvents were purified and dried according to Armarego & Chai (2009[Armarego, W. L. & Chai, C. L. (2009). Purification of Laboratory Chemicals, 6th ed. Amsterdam: Elsevier.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20N2O2S2

  • Mr = 336.46

  • Triclinic, [P \overline 1]

  • a = 11.3755 (3) Å

  • b = 11.9028 (3) Å

  • c = 12.5261 (3) Å

  • [alpha] = 86.122 (1)°

  • [beta] = 85.949 (1)°

  • [gamma] = 89.206 (1)°

  • V = 1687.86 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 133 K

  • 0.06 × 0.05 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 10948 measured reflections

  • 7580 independent reflections

  • 6827 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.088

  • S = 1.08

  • 7580 reflections

  • 557 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2A-H1NA...O2B 0.81 (3) 2.15 (3) 2.9429 (19) 168 (2)
N2B-H1NB...O2A 0.77 (2) 2.04 (2) 2.802 (2) 173 (2)

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO; 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: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2073 ).


Acknowledgements

The authors thank Roche Diagnostics GmbH, Penzberg, for financial support.

References

Armarego, W. L. & Chai, C. L. (2009). Purification of Laboratory Chemicals, 6th ed. Amsterdam: Elsevier.
Branchini, B. R., Murtiashaw, M. H., Magyar, R. A., Portier, N. C., Ruggiero, M. C. & Stroh, J. G. (2002). J. Am. Chem. Soc. 124, 2112-2113.  [ISI] [CrossRef] [PubMed] [ChemPort]
Branchini, B. R., Woodroofe, C. C., Meisenheimer, P. L., Klaubert, D. H., Kovic, Y., Rosenberg, J. C., Behney, C. E. & Southworth, T. L. (2012). Biochemistry, 51, 9807-9813.  [ISI] [PubMed]
Josel, H.-P., Herrmann, R., Klein, C. & Heindl, D. (1994). German Patent DE 4210759.
Jung, J., Chin, C.-A. & Song, P.-S. (1975). J. Am. Chem. Soc. 97, 3949-3954.  [CrossRef] [ISI]
Kricka, L. J. (1988). Anal. Biochem. 175, 14-21.  [CrossRef] [ChemPort] [PubMed] [ISI]
McCutcheon, D. C., Paley, M. A., Steinhardt, R. C. & Prescher, J. A. (2012). J. Am. Chem. Soc. 134, 7604-7607.  [ISI] [CrossRef] [ChemPort] [PubMed]
Meroni, G., Rajabi, M. & Santaniello, E. (2009). ARKIVOC, i, 265-288.  [CrossRef]
Naumov, P., Ozawa, Y., Ohkubo, K. & Fukuzumi, S. (2009). J. Am. Chem. Soc. 131, 11590-11605.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Schäffer, J. M. (1987). US Patent 4665022.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shinde, R., Perkins, J. & Contag, C. H. (2006). Biochemistry, 45, 11103-11112.  [ISI] [CrossRef] [PubMed] [ChemPort]
White, E. H., Steinmetz, M. G., Miano, J. D., Wildes, P. D. & Morland, R. (1979). J. Am. Chem. Soc. 101, 3199-3208.
Würfel, H. (2012). PhD thesis. Friedrich-Schiller-University Jena, Germany.


Acta Cryst (2013). E69, o1391  [ doi:10.1107/S1600536813019521 ]

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