Received 14 January 2010
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
Correspondence e-mail: firstname.lastname@example.org
The asymmetric unit of the title compound, C14H6Cl6N2, contains two crystallographically independent molecules, each of which is slightly twisted from planarity. The dihedral angles between the central ring and the two outer rings are 3.81 (7) and 4.30 (7)° in one molecule, and 4.13 (8) and 4.10 (7)° in the other. In the crystal structure, molecules are interlinked by C-ClCl interactions into sheets parallel to the ac plane. These sheets are stacked along the b axis in such a way that the molecules are antiparallel; they are further connected into a supramolecular network. There are no classical hydrogen bonds. CCl [3.637 (2) Å], ClCl [3.5639 (5)-3.6807 (8) Å] and ClN [3.3802 (15)-3.4093 (15) Å] short contacts and - interactions, with centroid-centroid distances in the range 3.5868 (9)-3.7844 (9) Å, are observed.
For reference bond-length data, see: Allen et al. (1987). For background to and applications of 1,10-phenanthroline derivatives, see: Armaroli et al. 1992); Beer et al. (1993); Emmerling et al. (2007); Goswami et al. (2007); Wesselinova et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2373 ).
SG and ACM thank the Indian Government for financial support. SC thanks the Prince of Songkla University for financial support through the Crystal Materials Research Unit. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Armaroli, N., Cola, L. D., Balzani, V., Sauvage, J.-P., Dietrich-Buchecker, C. D. & Kern, J. M. (1992). J. Chem. Soc. Faraday Trans. 88, 553-556.
Beer, R. H., Jimenez, J. & Drago, R. S. (1993). J. Org. Chem. 58, 1746-1747.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Emmerling, F., Orgzall, I., Dietzel, B., Schulz, B. W., Reck, G. & Schulz, B. (2007). J. Mol. Struct. 832, 124-131.
Goswami, S. P., Maity, A. C. & Fun, H.-K. (2007). Chem. Lett. 36, 552-553.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wesselinova, D., Neykov, M., Kaloyanov, N., Toshkova, R. & Dimitrov, G. (2009). Eur. J. Med. Chem. 44, 2720-2723.