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Volume 69 
Part 9 
Page o1386  
September 2013  

Received 16 July 2013
Accepted 31 July 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.042
wR = 0.113
Data-to-parameter ratio = 12.6
Details
Open access

4-Cyclopropyl-1-(6'-deoxy-1',2'-O-isopropylidene-[alpha]-D-glucofuranosyl)-1H-1,2,3-triazole

aNew Drug Reseach & Development Center, Zhengzhou Univresity, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: zqr409@163.com

In the title compound, C14H21N3O5, the tetrahydrofuran ring adopts an envelope conformation with the C atom bearing the substituent as the flap. The pentafuranose ring adopts a twisted conformation about the C-C bond fusing the rings. The dihedral angle between these rings (all atoms), which are cis fused, is 72.89 (14)°. The cyclopropane ring is disordered over two orientations in a 0.576 (5):0.424 (5) ratio; the dihedral angles subtended to the triazole ring are 53.3 (11) and 46.6 (9)°, respectively. In the crystal, the molecules are linked by O-H...N and O-H...O hydrogen bonds, generating (001) sheets. A weak C-H...O interaction also occurs.

Related literature

For further synthetic details, see: Pradere et al. (2008[Pradere, U., Roy, V. & McBrayer, R. T. (2008). Tetrahedron, 64, 9044-9051.]). For background to 1,2,3-triazoles, see: Alvarez et al. (1994[Alvarez, R., Velazquez, S., San-Felix, A., Aquaro, S. & De Clercq, E. (1994). J. Med. Chem. 37, 4185-4194.]); Genin et al. (2000[Genin, M. J., Allwine, D. A., Anderson, D. J. & Barbachyn, M. (2000). J. Med. Chem., 43, 953-970.]).

[Scheme 1]

Experimental

Crystal data
  • C14H21N3O5

  • Mr = 311.34

  • Orthorhombic, P 21 21 21

  • a = 8.5905 (3) Å

  • b = 8.7215 (3) Å

  • c = 20.7373 (7) Å

  • V = 1553.68 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.85 mm-1

  • T = 291 K

  • 0.22 × 0.2 × 0.18 mm

Data collection
  • Bruker MWPC diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). FRAMBO, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsion, USA.]) Tmin = 0.835, Tmax = 0.862

  • 5692 measured reflections

  • 2778 independent reflections

  • 2503 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.06

  • 2778 reflections

  • 220 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...N3i 0.83 (2) 1.95 (2) 2.767 (3) 171 (3)
O5-H5...O3ii 0.82 (3) 2.02 (3) 2.821 (3) 164 (3)
C7-H7...O1iii 0.93 2.59 3.496 (3) 165
Symmetry codes: (i) x, y+1, z; (ii) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]; (iii) x+1, y, z.

Data collection: FRAMBO (Bruker, 2004[Bruker (2004). FRAMBO, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsion, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). FRAMBO, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsion, 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7111 ).


Acknowledgements

We gratefully acknowledge the financial support of the National Natural Science Foundation of China (grant No. 81172937).

References

Alvarez, R., Velazquez, S., San-Felix, A., Aquaro, S. & De Clercq, E. (1994). J. Med. Chem. 37, 4185-4194.  [CrossRef] [ChemPort] [PubMed] [ISI]
Bruker (2004). FRAMBO, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsion, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Genin, M. J., Allwine, D. A., Anderson, D. J. & Barbachyn, M. (2000). J. Med. Chem., 43, 953-970.  [ISI] [CrossRef] [PubMed] [ChemPort]
Pradere, U., Roy, V. & McBrayer, R. T. (2008). Tetrahedron, 64, 9044-9051.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1386  [ doi:10.1107/S1600536813021351 ]

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