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Volume 68 
Part 11 
Page o3062  
November 2012  

Received 17 September 2012
Accepted 25 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.089
Data-to-parameter ratio = 18.0
Details
Open access

3-(3,4-Dichlorobenzylidene)chroman-4-one

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa,bChemistry Department, University of Cape Town, Rondebosch, 7701, South Africa, and cSchool of Chemical Engineering, University of KwaZulu-Natal, Durban 4041, South Africa
Correspondence e-mail: Koorbanally@ukzn.ac.za

The distinctive feature of the structure of the title compound, C16H10Cl2O2, is the formation of a zigzag chain along [100] via Cl...Cl interactions [3.591 (1) and 3.631 (1) Å]. The chromanone moiety is fused with the benzene ring and adopts a half-chair conformation. The dihedral angle between the benzene ring of the chromanone moiety and the dichlorobenzene plane is 56.14 (8)°.

Related literature

For background to homoisoflavonoids, see: Kirkiacharian et al. (1984[Kirkiacharian, B. S., Gomis, M., Tongo, H. G., Mahuteau, J. & Brion, J. D. (1984). Org. Magn. Reson. 22, 106-108.]). For a related structure, see: Gopaul et al. (2012[Gopaul, K., Shaikh, M., Ramjugernath, D., Koorbanally, N. A. & Omondi, B. (2012). Acta Cryst. E68, o1006.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10Cl2O2

  • Mr = 305.14

  • Monoclinic, P 21 /c

  • a = 3.9224 (3) Å

  • b = 11.5175 (10) Å

  • c = 28.957 (3) Å

  • [beta] = 92.270 (2)°

  • V = 1307.12 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.49 mm-1

  • T = 173 K

  • 0.16 × 0.12 × 0.11 mm

Data collection
  • Bruker Kappa Duo APEXII Diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.925, Tmax = 0.948

  • 15291 measured reflections

  • 3258 independent reflections

  • 2611 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.089

  • S = 1.03

  • 3258 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5252 ).


Acknowledgements

We thank the University of KwaZulu-Natal and the South Africa Research Chairs initiative of the Department of Science and Technology for financial support and the National Research Foundation of South Africa for a bursary for KG.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gopaul, K., Shaikh, M., Ramjugernath, D., Koorbanally, N. A. & Omondi, B. (2012). Acta Cryst. E68, o1006.  [CSD] [CrossRef] [details]
Kirkiacharian, B. S., Gomis, M., Tongo, H. G., Mahuteau, J. & Brion, J. D. (1984). Org. Magn. Reson. 22, 106-108.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3062  [ doi:10.1107/S1600536812040561 ]

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