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Volume 66 
Part 2 
Page o424  
February 2010  

Received 14 January 2010
Accepted 15 January 2010
Online 23 January 2010

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.105
Data-to-parameter ratio = 34.1
Details
Open access

2,9-Bis(trichloromethyl)-1,10-phenanthroline1

Hoong-Kun Fun,a*+ Suchada Chantrapromma,b++ Annada C. Maityc and Shyamaprosad Goswamic

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: hkfun@usm.my

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-Cl...Cl 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. C...Cl [3.637 (2) Å], Cl...Cl [3.5639 (5)-3.6807 (8) Å] and Cl...N [3.3802 (15)-3.4093 (15) Å] short contacts and [pi]-[pi] interactions, with centroid-centroid distances in the range 3.5868 (9)-3.7844 (9) Å, are observed.

Related literature

For reference bond-length data, see: Allen et al. (1987[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.]). For background to and applications of 1,10-phenanthroline derivatives, see: Armaroli et al. 1992[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 et al. (1993[Beer, R. H., Jimenez, J. & Drago, R. S. (1993). J. Org. Chem. 58, 1746-1747.]); Emmerling et al. (2007[Emmerling, F., Orgzall, I., Dietzel, B., Schulz, B. W., Reck, G. & Schulz, B. (2007). J. Mol. Struct. 832, 124-131.]); Goswami et al. (2007[Goswami, S. P., Maity, A. C. & Fun, H.-K. (2007). Chem. Lett. 36, 552-553.]); Wesselinova et al. (2009[Wesselinova, D., Neykov, M., Kaloyanov, N., Toshkova, R. & Dimitrov, G. (2009). Eur. J. Med. Chem. 44, 2720-2723.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C14H6Cl6N2

  • Mr = 414.91

  • Monoclinic, P 21 /c

  • a = 24.3001 (6) Å

  • b = 6.8825 (2) Å

  • c = 20.3461 (5) Å

  • [beta] = 114.689 (1)°

  • V = 3091.74 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 1.11 mm-1

  • T = 100 K

  • 0.59 × 0.36 × 0.10 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.561, Tmax = 0.898

  • 63570 measured reflections

  • 13520 independent reflections

  • 9474 reflections with I > 2[sigma](I)

  • Rint = 0.054
Refinement

  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.105

  • S = 1.06

  • 13520 reflections

  • 397 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.54 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2373 ).

Acknowledgements

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.

References

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.  [CrossRef] [ChemPort]
Beer, R. H., Jimenez, J. & Drago, R. S. (1993). J. Org. Chem. 58, 1746-1747.  [CrossRef] [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Emmerling, F., Orgzall, I., Dietzel, B., Schulz, B. W., Reck, G. & Schulz, B. (2007). J. Mol. Struct. 832, 124-131.  [ISI] [CSD] [CrossRef] [ChemPort]
Goswami, S. P., Maity, A. C. & Fun, H.-K. (2007). Chem. Lett. 36, 552-553.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wesselinova, D., Neykov, M., Kaloyanov, N., Toshkova, R. & Dimitrov, G. (2009). Eur. J. Med. Chem. 44, 2720-2723.  [ISI] [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2010). E66, o424  [ doi:10.1107/S1600536810002035 ]

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