N,N′-Bis(4-chloro-3-fluoro­benzyl­idene)ethane-1,2-diamine

Kia, R.; Fun, H.-K.

doi:10.1107/S1600536808033916

Volume 64
Part 11
Page o2169
November 2008

Received 13 October 2008
Accepted 17 October 2008
Online 22 October 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.113
Data-to-parameter ratio = 21.4
Details

N,N'-Bis(4-chloro-3-fluorobenzylidene)ethane-1,2-diamine

Reza Kia ^a and Hoong-Kun Fun ^a ^*

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title Schiff base compound, C₁₆H₁₂Cl₂F₂N₂, contains one half of the centrosymmetric molecule. Molecules related by translation along the a axis form stacks with short intermolecular CC distances of 3.429 (3) Å. The crystal packing also exhibits short intermolecular ClF contacts of 3.087 (1) Å.

Related literature

For a related structure, see Fun & Kia (2008). For general background, see: Pal et al. (2005); Calligaris & Randaccio (1987); Hou et al. (2001); Ren et al. (2002); Allen et al. (1987).

Experimental

Crystal data

C₁₆H₁₂Cl₂F₂N₂
M_r = 341.18
Monoclinic, P 2₁ /n
a = 4.6542 (1) Å
b = 23.1343 (6) Å
c = 6.9961 (2) Å
= 107.063 (2)°
V = 720.12 (3) Å³
Z = 2
Mo K radiation
= 0.47 mm^-1
T = 100.0 (1) K
0.51 × 0.05 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.795, T_max = 0.983
17372 measured reflections
2139 independent reflections
1705 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.113
S = 1.07
2139 reflections
100 parameters
H-atom parameters constrained
_max = 0.99 e Å^-3
_min = -0.34 e Å^-3

Table 1
Selected interatomic distances (Å)

Cl1F1ⁱ	3.087 (1)
C3C6ⁱⁱ	3.429 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2465 ).

Acknowledgements

HKF and RK thank the Malaysian government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for the award of a post-doctoral research fellowship. We acknowledge Professor A. L. Spek for providing us with a symmetry operation code.

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-S19.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715-738. London: Pergamon.
Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, o1722-o1723.
Hou, B., Friedman, N., Ruhman, S., Sheves, M. & Ottolenghi, M. (2001). J. Phys. Chem. B, 105, 7042-7048.
Pal, S., Barik, A. K., Gupta, S., Hazra, A., Kar, S. K., Peng, S.-M., Lee, G.-H., Butcher, R. J., El Fallah, M. S. & Ribas, J. (2005). Inorg. Chem. 44, 3880-3889.
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410-419.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds