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Volume 69 
Part 6 
Page o878  
June 2013  

Received 22 March 2013
Accepted 5 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.077
Data-to-parameter ratio = 14.4
Details
Open access

Ethyl 2,5-di-tert-butyl-5-ethoxy-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate

aDepartment of Pharmaceutical Sciences, School of Pharmacy, University of Maryland, Baltimore, MD 21201, USA,bCenter for Biomedical Engineering and Technology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA,cDepartment of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA, and dDepartment of Physiology, School of Medicine, University of Maryland, Baltimore, MD 21201, USA
Correspondence e-mail: jkao@umaryland.edu

The title compound, C17H29NO4, contains a chiral center and crystallizes as a racemate. The asymmetric unit consists of two non-equivalent molecules, in which the carbethoxy groups have markedly different orientations [C(=O)CC(OEt)=O torsion angles = 59.3 (2) and 156.0 (2)°]. In the crystal, molecules form chains along [101] through N-H...O hydrogen bonds.

Related literature

The title compound resulted from an attempt to devise a more efficient synthesis of diethyl 2,5,-di(tert-butyl)-1-hydroxypyrrole-3,4-dicarboxylate, a precursor to an aromatic nitroxide (Ramasseul & Rassat, 1970[Ramasseul, R. & Rassat, A. (1970). Bull. Soc. Chim. Fr. 72, 4330-4340.]). For related synthetic procedures, see also: Riplinger et al. (2009[Riplinger, C., Kao, J. P. Y., Rosen, G. M., Kathirvelu, V., Eaton, G. R., Eaton, S. S., Kutateladze, A. & Neese, F. (2009). J. Am. Chem. Soc. 131, 10092-10106.]); Travis et al. (2003[Travis, B. R., Sivakumar, M., Hollist, G. O. & Borhan, B. (2003). Org. Lett. 5, 3089-3092.]).

[Scheme 1]

Experimental

Crystal data
  • C17H29NO4

  • Mr = 311.41

  • Monoclinic, P 21 /n

  • a = 9.9187 (7) Å

  • b = 16.3916 (11) Å

  • c = 22.2115 (15) Å

  • [beta] = 92.5822 (11)°

  • V = 3607.6 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 150 K

  • 0.42 × 0.40 × 0.33 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.887, Tmax = 0.974

  • 40948 measured reflections

  • 6356 independent reflections

  • 5812 reflections with I > 2[sigma](I)

  • Rint = 0.018

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

  • wR(F2) = 0.077

  • S = 1.00

  • 6356 reflections

  • 441 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4A-H4A...O1Bi 0.832 (16) 2.175 (16) 3.0009 (15) 171.8 (14)
N4B-H4B...O1A 0.862 (16) 2.156 (17) 3.0089 (15) 170.4 (15)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XSHELL (Bruker, 2010[Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2098 ).


Acknowledgements

This work was supported in part by grants GM056481 (JPYK) and EB2034 (GMR) from the US National Institutes of Health.

References

Bruker (2010). APEX2, SAINT and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Ramasseul, R. & Rassat, A. (1970). Bull. Soc. Chim. Fr. 72, 4330-4340.
Riplinger, C., Kao, J. P. Y., Rosen, G. M., Kathirvelu, V., Eaton, G. R., Eaton, S. S., Kutateladze, A. & Neese, F. (2009). J. Am. Chem. Soc. 131, 10092-10106.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Travis, B. R., Sivakumar, M., Hollist, G. O. & Borhan, B. (2003). Org. Lett. 5, 3089-3092.  [ISI] [CrossRef] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o878  [ doi:10.1107/S1600536813012282 ]

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