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Volume 69 
Part 12 
Page o1772  
December 2013  

Received 28 October 2013
Accepted 7 November 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.121
Data-to-parameter ratio = 10.4
Details
Open access

2-N-Benzyl-2,6-dide­oxy-2,6-imino-3,4-O-iso­propyl­idene-D-allono­nitrile

aDepartment of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, England, and bDepartment of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, England
Correspondence e-mail: sarah.jenkinson@chem.ox.ac.uk

X-ray crystallography firmly established the relative stereochemistry of the title compound, C16H20N2O3. The acetonide ring adopts an envelope conformation with one of the O atoms as the flap and the piperidine ring adopts a slightly twisted boat conformation. The absolute configuration was determined by use of D-ribose as the starting material. The compound exists as O-H...O hydrogen-bonded chains of mol­ecules running parallel to the b axis.

Related literature

For the biological activity of polyhy­droxy­lated piperidines, see: Nash et al. (2011[Nash, R. J., Kato, A., Yu, C.-Y. & Fleet, G. W. J. (2011). Future Med. Chem. 3, 1513-1521.]); Watson et al. (2001[Watson, A. A., Fleet, G. W. J., Asano, N., Molyneux, R. J. & Nash, R. J. (2001). Phytochemistry, 56, 265-295.]). For a related [alpha]-imino­nitrile, see: Ayers et al. (2012[Ayers, B. J., Jenkinson, S. F., Fleet, G. W. J. & Thompson, A. L. (2012). Acta Cryst. E68, o1474.]). For the hydrogen-atom treatment, see; Cooper et al. (2010[Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.]). For details of the low temperature equipment used in the experiment, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For the weighting scheme, see: Prince (1982[Prince, E. (1982). In Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag.]); Watkin (1994[Watkin, D. (1994). Acta Cryst. A50, 411-437.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20N2O3

  • Mr = 288.35

  • Orthorhombic, P 21 21 21

  • a = 8.3978 (3) Å

  • b = 11.2689 (4) Å

  • c = 15.9210 (6) Å

  • V = 1506.67 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.4 × 0.4 × 0.2 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; 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.]) Tmin = 0.91, Tmax = 0.98

  • 11529 measured reflections

  • 1970 independent reflections

  • 1422 reflections with I > 2.0[sigma](I)

  • Rint = 0.079

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.121

  • S = 0.95

  • 1970 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H11...O6i 0.86 2.05 2.850 (5) 156 (1)
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]).; cell refinement: DENZO/SCALEPACK (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/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: CRYSTALS.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5665 ).


References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Ayers, B. J., Jenkinson, S. F., Fleet, G. W. J. & Thompson, A. L. (2012). Acta Cryst. E68, o1474.  [CSD] [CrossRef] [IUCr Journals]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [Web of Science] [CrossRef] [IUCr Journals]
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 43, 1100-1107.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Nash, R. J., Kato, A., Yu, C.-Y. & Fleet, G. W. J. (2011). Future Med. Chem. 3, 1513-1521.  [CrossRef] [ChemPort] [PubMed]
Nonius (2001). 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.
Prince, E. (1982). In Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag.
Watkin, D. (1994). Acta Cryst. A50, 411-437.  [CrossRef] [IUCr Journals]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.
Watson, A. A., Fleet, G. W. J., Asano, N., Molyneux, R. J. & Nash, R. J. (2001). Phytochemistry, 56, 265-295.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1772  [ doi:10.1107/S1600536813030584 ]

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