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Volume 64 
Part 10 
Pages o1895-o1896  
October 2008  

Received 2 September 2008
Accepted 3 September 2008
Online 6 September 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 24.1
Details
Open access

N,N'-Bis(5-bromo-2-hydroxybenzylidene)-2,2-dimethylpropane-1,3-diamine

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 crystal structure of the title Schiff base compound, C19H20Br2N2O2, contains two crystallographically independent molecules (A and B) in the asymmetric unit, with similar conformations. Intramolecular O-H...N (× 4) and C-H...N (× 5) hydrogen bonds form six- and five-membered rings, producing S(6) and S(5) ring motifs, respectively. One of the N atoms in molecule A acts as a trifurcated acceptor, the rest of the N atoms being bifurcated acceptors. The dihedral angles between the benzene rings in molecules A and B are 47.83 (17) and 61.11 (17)°, respectively. The molecular conformation is stabilized by intramolecular O-H...N and C-H...N hydrogen bonds. The short distances between the centroids of the benzene rings [3.7799 (19)-3.890 (2) Å] indicate the existence of [pi]-[pi] interactions. In addition, the crystal structure is further stabilized by an intermolecular C-H...O hydrogen bond, C-H...[pi] interactions, and short intermolecular Br...Br and Br...O contacts [3.4786 (5) and 3.149 (3) Å, respectively].

Related literature

For 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-S19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For information on Schiff base ligands and complexes and their applications, see, for example: Fun, Kargar & Kia (2008[Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308.]); Fun, Kia & Kargar (2008[Fun, H.-K., Kia, R. & Kargar, H. (2008). Acta Cryst. E64, o1335.]); Fun, Mirkhani et al. (2008a[Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008a). Acta Cryst. E64, o1374-o1375.],b[Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008b). Acta Cryst. E64, o1471.]); Calligaris & Randaccio (1987[Calligaris, M. & Randaccio, L. (1987). Comprehensive Coordination Chemistry, Vol. 2, edited by G. Wilkinson, pp. 715-738. London: Pergamon.]); Casellato & Vigato (1977[Casellato, U. & Vigato, P. A. (1977). Coord. Chem. Rev. 23, 31-50.]); Pal et al. (2005[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.]); Reglinski et al. 2004[Reglinski, J., Taylor, M. K. & Kennedy, A. R. (2004). Acta Cryst. C60, o169-o172.]; Hou et al. (2001[Hou, B., Friedman, N., Ruhman, S., Sheves, M. & Ottolenghi, M. (2001). J. Phys. Chem. B, 105, 7042-7048.]); Ren et al. (2002[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.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20Br2N2O2

  • Mr = 468.19

  • Monoclinic, C 2/c

  • a = 31.7684 (10) Å

  • b = 6.2436 (2) Å

  • c = 38.7287 (11) Å

  • [beta] = 99.870 (2)°

  • V = 7568.1 (4) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 4.30 mm-1

  • T = 100.0 (1) K

  • 0.52 × 0.10 × 0.06 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 = 0.213, Tmax = 0.782

  • 47391 measured reflections

  • 11172 independent reflections

  • 6920 reflections with I > 2[sigma](I)

  • Rint = 0.080

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.110

  • S = 1.01

  • 11172 reflections

  • 463 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.57 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1B-H1OB...N1B 0.85 1.81 2.580 (4) 151
O2A-H2OA...N2A 0.85 (4) 1.79 (4) 2.578 (4) 154 (4)
O1A-H1OA...N1A 0.79 (5) 1.85 (5) 2.572 (4) 153 (4)
O2B-H2OB...N2B 0.73 (5) 1.94 (5) 2.586 (4) 149 (5)
C8A-H8AA...N2A 0.99 2.58 2.960 (4) 103
C8B-H8BA...N2B 0.99 2.60 2.966 (4) 102
C16B-H16B...O2Bi 0.95 2.58 3.290 (5) 131
C19A-H19B...N1A 0.98 2.58 2.918 (4) 100
C19A-H19C...N2A 0.98 2.58 2.933 (5) 101
C19B-H19F...N1B 0.98 2.60 2.926 (5) 100
C7B-H7BA...Cg1ii 0.95 2.96 3.571 (4) 123
C18B-H18D...Cg2iii 0.98 2.77 3.652 (4) 151
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y-1, z; (iii) [x, -y-1, z-{\script{1\over 2}}]. Cg1 and Cg2 are the centroids of the C1A-C6A and C12A-C17A benzene rings, respectively.

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, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2626 ).


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 an award of a post-doctoral 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.  [CrossRef] [ChemPort] [ISI]
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.
Casellato, U. & Vigato, P. A. (1977). Coord. Chem. Rev. 23, 31-50.  [CrossRef] [ChemPort] [ISI]
Fun, H.-K., Kargar, H. & Kia, R. (2008). Acta Cryst. E64, o1308.  [CSD] [CrossRef] [details]
Fun, H.-K., Kia, R. & Kargar, H. (2008). Acta Cryst. E64, o1335.  [CSD] [CrossRef] [details]
Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008a). Acta Cryst. E64, o1374-o1375.  [CrossRef] [details]
Fun, H.-K., Mirkhani, V., Kia, R. & Vartooni, A. R. (2008b). Acta Cryst. E64, o1471.  [CSD] [CrossRef] [details]
Hou, B., Friedman, N., Ruhman, S., Sheves, M. & Ottolenghi, M. (2001). J. Phys. Chem. B, 105, 7042-7048.  [CrossRef] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Reglinski, J., Taylor, M. K. & Kennedy, A. R. (2004). Acta Cryst. C60, o169-o172.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [CrossRef] [details]


Acta Cryst (2008). E64, o1895-o1896   [ doi:10.1107/S160053680802816X ]

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