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

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

doi:10.1107/S160053680802816X

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 (C-C) = 0.005 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 24.1
Details

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

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

^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-HN (× 4) and C-HN (× 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-HN and C-HN 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-HO hydrogen bond, C-H [pi] interactions, and short intermolecular BrBr and BrO contacts [3.4786 (5) and 3.149 (3) Å, respectively].

Related literature

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For information on Schiff base ligands and complexes and their applications, see, for example: Fun, Kargar & Kia (2008); Fun, Kia & Kargar (2008); Fun, Mirkhani et al. (2008a,b); Calligaris & Randaccio (1987); Casellato & Vigato (1977); Pal et al. (2005); Reglinski et al. 2004; Hou et al. (2001); Ren et al. (2002).

Experimental

Crystal data

C₁₉H₂₀Br₂N₂O₂
M_r = 468.19
Monoclinic, C 2/c
a = 31.7684 (10) Å
b = 6.2436 (2) Å
c = 38.7287 (11) Å
= 99.870 (2)°
V = 7568.1 (4) Å³
Z = 16
Mo K radiation
= 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) T_min = 0.213, T_max = 0.782
47391 measured reflections
11172 independent reflections
6920 reflections with I > 2(I)
R_int = 0.080

Refinement

R[F² > 2(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
_max = 0.57 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1B-H1OBN1B	0.85	1.81	2.580 (4)	151
O2A-H2OAN2A	0.85 (4)	1.79 (4)	2.578 (4)	154 (4)
O1A-H1OAN1A	0.79 (5)	1.85 (5)	2.572 (4)	153 (4)
O2B-H2OBN2B	0.73 (5)	1.94 (5)	2.586 (4)	149 (5)
C8A-H8AAN2A	0.99	2.58	2.960 (4)	103
C8B-H8BAN2B	0.99	2.60	2.966 (4)	102
C16B-H16BO2Bⁱ	0.95	2.58	3.290 (5)	131
C19A-H19BN1A	0.98	2.58	2.918 (4)	100
C19A-H19CN2A	0.98	2.58	2.933 (5)	101
C19B-H19FN1B	0.98	2.60	2.926 (5)	100
C7B-H7BACg1ⁱⁱ	0.95	2.96	3.571 (4)	123
C18B-H18DCg2ⁱⁱⁱ	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); 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: 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

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organic compounds