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Volume 69 
Part 6 
Page o849  
June 2013  

Received 25 February 2013
Accepted 16 April 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.027
wR = 0.070
Data-to-parameter ratio = 15.6
Details
Open access

(E)-9-(But-2-en-1-yl)-6-chloro-9H-purine

aCentre for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1126, 0315 Oslo, Norway, and bDepartment of Chemistry, University of Oslo, PO Box 1033, 0315 Oslo, Norway
Correspondence e-mail: fredrik.lundvall@smn.uio.no, jindrich.kania@kjemi.uio.no

The asymmetric unit of the title compound, C9H9ClN4, contains two molecules. In the crystal, the molecules are ordered in a chain-like fashion along the a axis, and form layers offset relative to the C plane by approximately 30°. This ordering does not, however, appear to be directed by classical hydrogen bonding.The allylic side chains of both independent molecules are disordered, with occupancies of 0.870 (4) and 0.934 (3) for the major components. The disorder components represent two possible spatial orientations of the atoms around the C=C double bond.

Related literature

For synthetic background and applications, see Kania & Gundersen (2013[Kania, J. & Gundersen, L.-L. (2013). Eur. J. Org. Chem. pp. 2008-2019.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9ClN4

  • Mr = 208.65

  • Triclinic, [P \overline 1]

  • a = 8.1818 (11) Å

  • b = 9.7103 (13) Å

  • c = 13.9435 (19) Å

  • [alpha] = 69.642 (1)°

  • [beta] = 75.448 (1)°

  • [gamma] = 67.032 (1)°

  • V = 947.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 100 K

  • 1.13 × 0.35 × 0.22 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.683, Tmax = 0.924

  • 10801 measured reflections

  • 4428 independent reflections

  • 4103 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.070

  • S = 1.04

  • 4428 reflections

  • 283 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2004[Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and ChemBioDraw Ultra (CambridgeSoft, 2009)[CambridgeSoft (2009). ChemBioDraw Ultra. CambridgeSoft Corporation, Cambridge, Massachusetts, USA.]; 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: LR2100 ).


Acknowledgements

We acknowledge the support from the Norwegian Research Council (KOSK II, project 184929 and RENERGI, project 190980) and from the Department of Chemistry, UiO. We also acknowledge Dr David S. Wragg for invaluable assistance with the refinement.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Brandenburg, K. (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
CambridgeSoft (2009). ChemBioDraw Ultra. CambridgeSoft Corporation, Cambridge, Massachusetts, USA.
Kania, J. & Gundersen, L.-L. (2013). Eur. J. Org. Chem. pp. 2008-2019.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o849  [ doi:10.1107/S1600536813010416 ]

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