N,N'-Bis(3-bromo-benzyl-idene)ethane-1,2-diamine.

The mol-ecule of the title Schiff base compound, C(16)H(14)Br(2)N(2), lies across a crystallographic inversion centre. The C=N bond adopts a trans configuration. The imino group is coplanar with the benzene ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the dimethyl-ene bridge. The inter-esting feature of the structure is the weak Br⋯Br inter-action [3.7501 (2) Å] linking the mol-ecules into chains along the c axis. These chains are stacked along the b axis.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶); Fun, Mirkhani et al. (2008 ▶); Calligaris & Randaccio, (1987 ▶). For information on Schiff base complexes and their applications, see, for example: Kia, Mirkhani, Harkema & van Hummel (2007 ▶); Kia, Mirkhani, Kalman & Deak (2007 ▶); Pal et al. (2005 ▶); Hou et al. (2001 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C16H14Br2N2

M = 394.11

Monoclinic,

a = 6.2578 (1) Å

b = 4.6549 (1) Å

c = 25.3272 (5) Å

β = 93.592 (1)°

V = 736.32 (2) Å3

Z = 2

Mo Kα radiation

μ = 5.50 mm−1

T = 100.0 (1) K

0.57 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.125, T max = 0.393

24876 measured reflections

3822 independent reflections

2975 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.066

S = 1.07

3822 reflections

119 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.61 e Å−3

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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021132/at2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021132/at2587Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14Br2N2	F000 = 388
Mr = 394.11	Dx = 1.778 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8650 reflections
a = 6.2578 (1) Å	θ = 3.2–38.3º
b = 4.6549 (1) Å	µ = 5.50 mm−1
c = 25.3272 (5) Å	T = 100.0 (1) K
β = 93.592 (1)º	Block, colourless
V = 736.32 (2) Å3	0.57 × 0.22 × 0.17 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	2975 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 100.0(1) K	θmax = 37.5º
φ and ω scans	θmin = 3.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.125, Tmax = 0.393	k = −7→7
24876 measured reflections	l = −43→43

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0244P)2 + 0.509P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3822 reflections	Δρmax = 0.69 e Å−3
119 parameters	Δρmin = −0.61 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.30202 (2)	0.03394 (3)	0.278341 (6)	0.02085 (4)
N1	0.35517 (18)	0.8207 (3)	0.44274 (5)	0.0165 (2)
C1	0.2106 (2)	0.3996 (3)	0.36391 (5)	0.0158 (2)
C2	0.1288 (2)	0.1862 (3)	0.33044 (5)	0.0165 (2)
C3	−0.0766 (2)	0.0762 (3)	0.33433 (6)	0.0188 (3)
C4	−0.2013 (2)	0.1822 (3)	0.37319 (6)	0.0194 (3)
C5	−0.1226 (2)	0.3970 (3)	0.40730 (6)	0.0181 (2)
C6	0.0838 (2)	0.5062 (3)	0.40303 (5)	0.0158 (2)
C7	0.1634 (2)	0.7313 (3)	0.43991 (6)	0.0162 (2)
C8	0.4077 (2)	1.0477 (3)	0.48093 (6)	0.0171 (2)
H1	0.348 (3)	0.476 (4)	0.3617 (9)	0.021 (5)*
H3	−0.128 (3)	−0.067 (5)	0.3113 (9)	0.026 (6)*
H4	−0.344 (3)	0.115 (5)	0.3752 (8)	0.025 (5)*
H5	−0.207 (4)	0.474 (5)	0.4344 (10)	0.030 (6)*
H7	0.064 (3)	0.805 (5)	0.4623 (8)	0.019 (5)*
H8A	0.448 (3)	1.212 (5)	0.4612 (8)	0.024 (5)*
H8B	0.283 (3)	1.109 (4)	0.5004 (7)	0.014 (4)*

	U11	U22	U33	U12	U13	U23
Br1	0.02520 (7)	0.02173 (8)	0.01584 (6)	0.00015 (5)	0.00296 (4)	−0.00294 (6)
N1	0.0157 (5)	0.0168 (6)	0.0168 (5)	−0.0003 (4)	0.0000 (4)	−0.0027 (4)
C1	0.0152 (5)	0.0160 (6)	0.0160 (5)	0.0002 (4)	−0.0002 (4)	0.0008 (5)
C2	0.0188 (5)	0.0167 (6)	0.0137 (5)	0.0010 (4)	−0.0007 (4)	−0.0002 (4)
C3	0.0206 (6)	0.0168 (7)	0.0183 (6)	−0.0013 (5)	−0.0037 (4)	−0.0018 (5)
C4	0.0153 (5)	0.0196 (7)	0.0232 (7)	−0.0019 (4)	−0.0014 (5)	−0.0012 (5)
C5	0.0154 (5)	0.0184 (7)	0.0205 (6)	−0.0008 (4)	0.0012 (4)	−0.0019 (5)
C6	0.0151 (5)	0.0147 (6)	0.0173 (5)	0.0000 (4)	−0.0003 (4)	−0.0010 (4)
C7	0.0154 (5)	0.0162 (6)	0.0170 (6)	0.0007 (4)	0.0001 (4)	−0.0015 (5)
C8	0.0160 (5)	0.0170 (6)	0.0179 (6)	0.0001 (4)	−0.0018 (4)	−0.0030 (5)

Br1—C2	1.8967 (14)	C4—C5	1.391 (2)
N1—C7	1.2676 (17)	C4—H4	0.95 (2)
N1—C8	1.4564 (19)	C5—C6	1.3985 (19)
C1—C2	1.383 (2)	C5—H5	0.96 (2)
C1—C6	1.399 (2)	C6—C7	1.470 (2)
C1—H1	0.93 (2)	C7—H7	0.93 (2)
C2—C3	1.393 (2)	C8—C8i	1.525 (3)
C3—C4	1.385 (2)	C8—H8A	0.96 (2)
C3—H3	0.93 (2)	C8—H8B	0.991 (19)
C7—N1—C8	116.70 (12)	C4—C5—H5	121.6 (14)
C2—C1—C6	118.96 (12)	C6—C5—H5	118.0 (14)
C2—C1—H1	122.9 (13)	C5—C6—C1	119.58 (13)
C6—C1—H1	118.1 (13)	C5—C6—C7	119.22 (13)
C1—C2—C3	121.90 (13)	C1—C6—C7	121.20 (12)
C1—C2—Br1	119.28 (10)	N1—C7—C6	123.50 (13)
C3—C2—Br1	118.81 (11)	N1—C7—H7	120.7 (12)
C4—C3—C2	118.88 (13)	C6—C7—H7	115.8 (12)
C4—C3—H3	121.0 (14)	N1—C8—C8i	109.87 (15)
C2—C3—H3	120.1 (13)	N1—C8—H8A	106.8 (12)
C3—C4—C5	120.27 (13)	C8i—C8—H8A	110.5 (12)
C3—C4—H4	119.5 (13)	N1—C8—H8B	112.9 (11)
C5—C4—H4	120.1 (13)	C8i—C8—H8B	110.9 (11)
C4—C5—C6	120.41 (14)	H8A—C8—H8B	105.7 (17)
C6—C1—C2—C3	0.5 (2)	C4—C5—C6—C7	−179.45 (14)
C6—C1—C2—Br1	−178.55 (10)	C2—C1—C6—C5	−0.4 (2)
C1—C2—C3—C4	−0.6 (2)	C2—C1—C6—C7	179.52 (13)
Br1—C2—C3—C4	178.42 (11)	C8—N1—C7—C6	179.20 (13)
C2—C3—C4—C5	0.7 (2)	C5—C6—C7—N1	172.14 (14)
C3—C4—C5—C6	−0.6 (2)	C1—C6—C7—N1	−7.8 (2)
C4—C5—C6—C1	0.5 (2)	C7—N1—C8—C8i	123.51 (16)