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

Gopaul, K.; Koorbanally, N.A.; Shaikh, M.M.; Su, H.; Ramjugernath, D.

doi:10.1107/S1600536812040561

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 (C-C) = 0.002 Å
R = 0.034
wR = 0.089
Data-to-parameter ratio = 18.0
Details

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

Kaalin Gopaul,^a Neil Anthony Koorbanally,^a ^* Mahidansha M. Shaikh,^a Hong Su ^b and Deresh Ramjugernath ^c

^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 ClCl 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). For a related structure, see: Gopaul et al. (2012).

Experimental

Crystal data

C₁₆H₁₀Cl₂O₂
M_r = 305.14
Monoclinic, P 2₁ /c
a = 3.9224 (3) Å
b = 11.5175 (10) Å
c = 28.957 (3) Å
= 92.270 (2)°
V = 1307.12 (19) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.925, T_max = 0.948
15291 measured reflections
3258 independent reflections
2611 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.089
S = 1.03
3258 reflections
181 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.21 e Å^-3

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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.
Gopaul, K., Shaikh, M., Ramjugernath, D., Koorbanally, N. A. & Omondi, B. (2012). Acta Cryst. E68, o1006.
Kirkiacharian, B. S., Gomis, M., Tongo, H. G., Mahuteau, J. & Brion, J. D. (1984). Org. Magn. Reson. 22, 106-108.
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds