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Volume 69 
Part 7 
Page o1104  
July 2013  

Received 7 May 2013
Accepted 7 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 140 K
Mean [sigma](C-C) = 0.001 Å
R = 0.030
wR = 0.076
Data-to-parameter ratio = 16.9
Details
Open access

(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile

aSchool of Chemistry, University of East Anglia, Norwich NR4 7TJ, England
Correspondence e-mail: a.haines@uea.ac.uk, d.l.hughes@uea.ac.uk

The title compound, C7H8N2O2, formed by dehydration of the corresponding dicarboxamide, crystallizes as rectangular prisms. The molecules have a C2 axis of symmetry through the C atom bearing the methyl groups and the mid-point of the ring C-C bond, and the 1,3-dioxolane ring adopts the extreme twist conformation of the two possible with this symmetry. This brings the two nitrile groups nearest to a linear arrangement when the molecule is viewed along the ring C-C bond. The correct absolute configuration of the molecule was defined by that of the original starting material, (2R,3R)-tartaric acid. The packing is largely controlled by a number of C-H...N interactions.

Related literature

For the first syntheses of the title compound, see: Briggs et al. (1985[Briggs, M. A., Haines, A. H. & Jones, H. F. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 795-798.]). For determination of the absolute configuration of (+)-tartaric acid, see: Bijvoet et al. (1951[Bijvoet, J. M., Peerdeman, A. F. & van Bommel, A. J. (1951). Nature, 168, 271.]). For related structures, see: (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide, Shainyan et al. (2002[Shainyan, B. A., Ustinov, M. V., Bel'skii, B. K. & Nindakova, L. O. (2002). Russ. J. Org. Chem. 38, 104-110.]); (2R,3S)-2,3-dihydroxy-2,3-dicyanoethane and (2R,3S)-2,3-dibenzoyloxy-2,3-dicyanoethane, Rychlewska et al. (2008[Rychlewska, U., Wascinska, N., Warzajtis, B. & Gawronski, J. (2008). Acta Cryst. B64, 497-503.]); and (2S,3S)-2,3-dibenzoyloxy-2,3-dicyanoethane, Gawronski et al. (2007[Gawronski, J., Gawronska, K., Wascinska, N., Plutecka, A. & Rychlewska, U. (2007). Pol. J. Chem. 81, 1917-1925.]). For the Flack x parameter, see: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8N2O2

  • Mr = 152.15

  • Tetragonal, P 41 21 2

  • a = 8.7740 (2) Å

  • c = 10.0282 (3) Å

  • V = 772.00 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 140 K

  • 0.08 × 0.07 × 0.07 mm

Data collection
  • Oxford Diffraction Xcalibur 3/Sapphire3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO RED RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.886, Tmax = 1.000

  • 14922 measured reflections

  • 1133 independent reflections

  • 1073 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.076

  • S = 1.09

  • 1133 reflections

  • 67 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N21i 0.946 (13) 2.450 (13) 3.2530 (14) 142.6 (10)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+{\script{3\over 4}}].

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis PRO RED; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5320 ).


References

Bijvoet, J. M., Peerdeman, A. F. & van Bommel, A. J. (1951). Nature, 168, 271.  [CrossRef] [Web of Science]
Briggs, M. A., Haines, A. H. & Jones, H. F. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 795-798.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Gawronski, J., Gawronska, K., Wascinska, N., Plutecka, A. & Rychlewska, U. (2007). Pol. J. Chem. 81, 1917-1925.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rychlewska, U., Wascinska, N., Warzajtis, B. & Gawronski, J. (2008). Acta Cryst. B64, 497-503.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Shainyan, B. A., Ustinov, M. V., Bel'skii, B. K. & Nindakova, L. O. (2002). Russ. J. Org. Chem. 38, 104-110.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1104  [ doi:10.1107/S1600536813015973 ]

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