8-(4-Chloro­benzyl­idene)-4-(4-chloro­phen­yl)-2-phenyl-5,6,7,8-tetra­hydro­quinoline

Jian, F.; Zhai, X.

doi:10.1107/S1600536810017769

Volume 66
Part 6
Page o1423
June 2010

Received 17 March 2010
Accepted 14 May 2010
Online 22 May 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.102
Data-to-parameter ratio = 13.6
Details

8-(4-Chlorobenzylidene)-4-(4-chlorophenyl)-2-phenyl-5,6,7,8-tetrahydroquinoline

Fangfang Jian ^a ^* and Xin Zhai ^a

^aNew Materials & Function Coordination Chemistry Laboratory, Qingdao University of Science & Technology, Qingdao 266042, People's Republic of China
Correspondence e-mail: ffj2003@163169.net

In the crystal structure of the title compound, C₂₈H₂₁Cl₂N, [pi] - [pi] interactions link pairs of molecules into centrosymmetric dimers with a distance of 3.756 (3) Å between the centroids of the pyridine rings. Weak intermolecular C-HCl hydrogen bonds further link these dimers into chains propagating along [ $[\overline{1}]$ 01]. The pyridine ring forms dihedral angles of 21.52 (1) and 55.87 (2)°, respectively, with the phenyl ring and the 4-chlorophenyl ring.

Related literature

For applications of pyridyl-containing compounds, see: Yan et al. (2007); Barton & Ollis (1979); Katritzky & Marson (1984); Constable et al. (1994); Eryazici et al. (2006).

Experimental

Crystal data

C₂₈H₂₁Cl₂N
M_r = 442.36
Triclinic, $[P \overline 1]$
a = 10.0583 (10) Å
b = 10.6483 (10) Å
c = 10.8792 (10) Å
= 82.028 (2)°
= 89.345 (1)°
= 71.335 (2)°
V = 1092.53 (18) Å³
Z = 2
Mo K radiation
= 0.31 mm^-1
T = 295 K
0.23 × 0.20 × 0.19 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
5765 measured reflections
3810 independent reflections
3211 reflections with I > 2(I)
R_int = 0.014
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.102
S = 1.06
3810 reflections
280 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C20-H20ACl1ⁱ	0.93	2.80	3.476 (2)	130
Symmetry code: (i) x-1, y, z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2704 ).

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (grant Nos. Y2006B08 & Z2007B01).

References

Barton, D. & Ollis, D. (1979). Comprehensive Organic Chemistry, Vol. 4, pp. 468-469. Oxford, New York: Pergamon Press.
Constable, E. C., Martínez-Mánez, R., Chargill Thompson, A. M. W. & Walker, J. V. (1994). J. Chem. Soc. pp. 1585-1594.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Eryazici, I., Moorefield, C. N., Durmus, S. & Newkome, G. R. (2006). J. Org. Chem. 71, 1009-1014.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.
Katritzky, A. R. & Marson, C. M. (1984). Angew. Chem. Int. Ed. Engl. 23, 420-429.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yan, C. G., Cai, X. M., Wang, Q. F., Wang, T. Y. & Zheng, M. (2007). Nat. Prop. Liais. Coord. Paris, 5, 945-947.

organic compounds