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Volume 69 
Part 9 
Page o1416  
September 2013  

Received 19 July 2013
Accepted 8 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.010 Å
R = 0.076
wR = 0.212
Data-to-parameter ratio = 15.5
Details
Open access

6,8-Dichloro-4-oxochromene-3-carbaldehyde

aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

The asymmetric unit of the title compound, C10H4Cl2O3, contain two essentially planar independent molecules (mean atomic deviations from the corresponding least-square planes are 0.041 and 0.045 Å for molecules 1 and 2, respectively). In the crystal, molecules are linked through a pair of halogen bonds [Cl...O separations are 3.044 (5) and 3.033 (6) Å, C-Cl...O angles are 160.4 (3) and 162.8 (3)°, and C=O...Cl angles are 138.7 (4) and 139.6 (4)°, respectively, in molecules 1 and 2] and C-H...O hydrogen bonds into slightly folded bands [the dihedral angle between the planes of neighboring molecules is 8.6 (2)°] along the c-axis direction.

Related literature

For the biological activity of the title and related compounds, see: Shim et al. (2003[Shim, Y. S., Kim, K. C., Chi, D. Y., Lee, K. H. & Cho, H. (2003). Bioorg. Med. Chem. Lett. 13, 2561-2563.]); Kawase et al. (2007[Kawase, M., Tanaka, T., Kan, H., Tani, S., Nakashima, H. & Sakagami, H. (2007). In Vivo, 21, 829-834.]); Dückert et al. (2012[Dückert, H., Pries, V., Khedkar, V., Menninger, S., Bruss, H., Bird, A. W., Maliga, Z., Brockmeyer, A., Janning, P., Hyman, A., Grimme, S., Schürmann, M., Preut, H., Hübel, K., Ziegler, S., Kumar, K. & Waldmann, H. (2012). Nat. Chem. Biol. 8, 179-184.]). For related structures, see: Ishikawa et al. (2013a[Ishikawa, Y. & Motohashi, Y. (2013a). Acta Cryst. E69, o1225.],b[Ishikawa, Y. & Motohashi, Y. (2013b). Acta Cryst. E69, o1226.]). For halogen bonding, see: Auffinger et al. (2004[Auffinger, P., Hays, F. A., Westhof, E. & Ho, P. S. (2004). Proc. Natl Acad. Sci. USA, 101, 16789-16794.]); Metrangolo et al. (2005[Metrangolo, P., Neukirch, H., Pilati, T. & Resnati, G. (2005). Acc. Chem. Res. 38, 386-395.]); Wilcken et al. (2013[Wilcken, R., Zimmermann, M. O., Lange, A., Joerger, A. C. & Boeckler, F. M. (2013). J. Med. Chem. 56, 1363-1388.]).

[Scheme 1]

Experimental

Crystal data
  • C10H4Cl2O3

  • Mr = 243.05

  • Triclinic, [P \overline 1]

  • a = 8.288 (8) Å

  • b = 8.325 (7) Å

  • c = 13.706 (7) Å

  • [alpha] = 96.55 (6)°

  • [beta] = 92.23 (7)°

  • [gamma] = 101.98 (7)°

  • V = 917.2 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.68 mm-1

  • T = 100 K

  • 0.42 × 0.22 × 0.08 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.841, Tmax = 0.947

  • 5130 measured reflections

  • 4203 independent reflections

  • 2596 reflections with F2 > 2[sigma](F2)

  • Rint = 0.057

  • 3 standard reflections every 150 reflections intensity decay: 4.9%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.212

  • S = 1.10

  • 4203 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.79 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4bi-H2bi...O2a 0.95 2.35 3.246 (8) 157
C4a-H2a...O2bi 0.95 2.35 3.259 (8) 160
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: WinAFC (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC; data reduction: WinAFC; 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: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2111 ).


Acknowledgements

We acknowledge the University of Shizuoka for instrumental support.

References

Auffinger, P., Hays, F. A., Westhof, E. & Ho, P. S. (2004). Proc. Natl Acad. Sci. USA, 101, 16789-16794.  [CrossRef] [PubMed] [ChemPort]
Dückert, H., Pries, V., Khedkar, V., Menninger, S., Bruss, H., Bird, A. W., Maliga, Z., Brockmeyer, A., Janning, P., Hyman, A., Grimme, S., Schürmann, M., Preut, H., Hübel, K., Ziegler, S., Kumar, K. & Waldmann, H. (2012). Nat. Chem. Biol. 8, 179-184.
Ishikawa, Y. & Motohashi, Y. (2013a). Acta Cryst. E69, o1225.  [CrossRef] [details]
Ishikawa, Y. & Motohashi, Y. (2013b). Acta Cryst. E69, o1226.  [CrossRef] [details]
Kawase, M., Tanaka, T., Kan, H., Tani, S., Nakashima, H. & Sakagami, H. (2007). In Vivo, 21, 829-834.  [PubMed] [ChemPort]
Metrangolo, P., Neukirch, H., Pilati, T. & Resnati, G. (2005). Acc. Chem. Res. 38, 386-395.  [ISI] [CrossRef] [PubMed] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shim, Y. S., Kim, K. C., Chi, D. Y., Lee, K. H. & Cho, H. (2003). Bioorg. Med. Chem. Lett. 13, 2561-2563.  [CrossRef] [PubMed] [ChemPort]
Wilcken, R., Zimmermann, M. O., Lange, A., Joerger, A. C. & Boeckler, F. M. (2013). J. Med. Chem. 56, 1363-1388.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1416  [ doi:10.1107/S1600536813022228 ]

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