N,N′-Bis(4-bromo­benzyl­idene)butane-1,4-diamine

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

doi:10.1107/S1600536808028122

Volume 64
Part 10
Page o1894
October 2008

Received 30 August 2008
Accepted 3 September 2008
Online 6 September 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.092
Data-to-parameter ratio = 28.3
Details

N,N'-Bis(4-bromobenzylidene)butane-1,4-diamine

Hoong-Kun Fun,^a ^* Hadi Kargar ^b ⁺ and Reza Kia ^a

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
Correspondence e-mail: hkfun@usm.my

The molecule of the title Schiff base compound, C₁₈H₁₈Br₂N₂, lies across a crystallographic inversion centre and adopts an E configuration with respect to the C=N bond. In the crystal structure, molecules are linked into chains along [201] through intermolecular BrBr interactions [3.3747 (3) Å], which are significantly shorter than the sum of the van der Waals radii for Br atoms (3.70 Å). The crystal structure is further stabilized by [pi] - [pi] stacking interactions [centroid-centroid distance 3.6811 (11) Å].

Related literature

For halogen-halogen interactions, see: Ramasubbu et al. (1986); Brammer et al. (2003). For the crystal structures of related compounds, see: Fun et al. (2008); Fun, Kia & Kargar (2008a,b); Fun & Kia (2008a,b). For bond-length data, see: Allen et al. (1987). For hydrogen-bondong motifs, see: Bernstein et al. (1995). For background, see: Casellato & Vigato (1977).

Experimental

Crystal data

C₁₈H₁₈Br₂N₂
M_r = 422.16
Monoclinic, P 2₁ /c
a = 11.2612 (5) Å
b = 9.5213 (4) Å
c = 8.2645 (4) Å
= 100.040 (3)°
V = 872.56 (7) Å³
Z = 2
Mo K radiation
= 4.64 mm^-1
T = 100.0 (1) K
0.52 × 0.23 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.192, T_max = 0.688
15460 measured reflections
3843 independent reflections
2600 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.092
S = 1.02
3843 reflections
136 parameters
All H-atom parameters refined
_max = 0.68 e Å^-3
_min = -0.59 e Å^-3

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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2242 ).

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 postdoctoral research fellowship. HK thanks PNU for financial support.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Brammer, L., Espallargas, M. E. & Adams, H. (2003). CrystEngComm, 5, 343-345.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Casellato, U. & Vigato, P. A. (1977). Coord. Chem. Rev. 23, 31-50.
Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308.
Fun, H.-K. & Kia, R. (2008a). Acta Cryst. E64, m1081-m1082.
Fun, H.-K. & Kia, R. (2008b). Acta Cryst. E64, m1116-m1117.
Fun, H.-K., Kia, R. & Kargar, H. (2008a). Acta Cryst. E64, o1335.
Fun, H.-K., Kia, R. & Kargar, H. (2008b). Acta Cryst. E64, o1855.
Ramasubbu, N., Parthasathy, R. & Murry-Rust, P. (1986). J. Am. Chem. Soc. 108, 4308-4314.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds