N,N'-Bis(4-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 and adopts an E configuration with respect to the azomethine C=N bond. The imino group is coplanar with the aromatic ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the dimethyl-ene bridge. The crystal structure is stabilized by inter-molecular C-H⋯π inter-actions and Br⋯Br [3.6307 (4) Å] short contacts.

Related literature

For the values of bond lengths, see Allen et al. (1987 ▶). For related structures see, for example: Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶); Habibi et al. (2007 ▶); 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 ▶); Amirnasr et al. (2002 ▶); Pal et al. (2005 ▶); Hou et al. (2001 ▶); Ren et al. (2002 ▶).

Experimental

Crystal data

C16H14Br2N2

M = 394.11

Monoclinic,

a = 13.8417 (5) Å

b = 7.4796 (3) Å

c = 7.1531 (3) Å

β = 95.692 (1)°

V = 736.91 (5) Å3

Z = 2

Mo Kα radiation

μ = 5.49 mm−1

T = 100.0 (1) K

0.45 × 0.24 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2005 ▶) T min = 0.189, T max = 0.853

10096 measured reflections

2148 independent reflections

1773 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.069

S = 1.06

2148 reflections

99 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.45 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/S1600536808019594/at2584sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019594/at2584Isup2.hkl

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

C16H14Br2N2	F000 = 388
Mr = 394.11	Dx = 1.776 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3320 reflections
a = 13.8417 (5) Å	θ = 3.1–31.6º
b = 7.4796 (3) Å	µ = 5.49 mm−1
c = 7.1531 (3) Å	T = 100.0 (1) K
β = 95.6920 (10)º	Block, colourless
V = 736.91 (5) Å3	0.45 × 0.24 × 0.03 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	2148 independent reflections
Radiation source: fine-focus sealed tube	1773 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
T = 100.0(1) K	θmax = 30.0º
φ and ω scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker 2005)	h = −19→19
Tmin = 0.189, Tmax = 0.853	k = −10→9
10096 measured reflections	l = −10→10

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) = 0.069	w = 1/[σ2(Fo2) + (0.0291P)2 + 0.1298P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2148 reflections	Δρmax = 0.73 e Å−3
99 parameters	Δρmin = −0.45 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	0.901280 (16)	0.57354 (3)	−0.36941 (3)	0.02279 (8)
N1	0.57142 (14)	0.4729 (2)	0.2936 (2)	0.0199 (4)
C1	0.67242 (16)	0.5432 (3)	−0.0377 (3)	0.0185 (4)
H1A	0.6068	0.5727	−0.0490	0.022*
C2	0.72773 (16)	0.5762 (2)	−0.1849 (3)	0.0187 (4)
H2A	0.7001	0.6316	−0.2937	0.022*
C3	0.82508 (15)	0.5259 (3)	−0.1685 (3)	0.0172 (4)
C4	0.86807 (16)	0.4432 (2)	−0.0085 (3)	0.0183 (4)
H4A	0.9327	0.4073	−0.0005	0.022*
C5	0.81247 (16)	0.4149 (2)	0.1402 (3)	0.0179 (4)
H5A	0.8408	0.3615	0.2496	0.021*
C6	0.71515 (16)	0.4652 (2)	0.1284 (3)	0.0169 (4)
C7	0.65967 (17)	0.4292 (2)	0.2901 (3)	0.0185 (4)
H7A	0.6909	0.3717	0.3944	0.022*
C8	0.52516 (17)	0.4197 (3)	0.4604 (3)	0.0202 (4)
H8A	0.4726 (17)	0.323 (3)	0.418 (3)	0.025 (6)*
H8B	0.5700 (17)	0.359 (3)	0.553 (3)	0.014 (5)*

	U11	U22	U33	U12	U13	U23
Br1	0.02663 (14)	0.02485 (12)	0.01759 (12)	−0.00239 (9)	0.00569 (9)	0.00236 (8)
N1	0.0245 (9)	0.0218 (8)	0.0134 (8)	0.0011 (7)	0.0025 (7)	0.0012 (6)
C1	0.0196 (10)	0.0176 (10)	0.0178 (10)	0.0016 (7)	−0.0005 (8)	−0.0006 (7)
C2	0.0250 (11)	0.0172 (9)	0.0131 (9)	0.0030 (8)	−0.0015 (8)	0.0005 (7)
C3	0.0231 (11)	0.0143 (8)	0.0143 (9)	−0.0018 (8)	0.0024 (8)	−0.0009 (7)
C4	0.0193 (10)	0.0164 (9)	0.0188 (9)	−0.0014 (7)	0.0006 (8)	−0.0018 (7)
C5	0.0239 (11)	0.0148 (9)	0.0144 (9)	−0.0008 (8)	−0.0008 (8)	0.0002 (7)
C6	0.0249 (11)	0.0122 (8)	0.0135 (9)	−0.0011 (7)	0.0013 (8)	−0.0026 (6)
C7	0.0265 (11)	0.0155 (9)	0.0132 (9)	−0.0012 (8)	0.0002 (8)	−0.0010 (7)
C8	0.0231 (11)	0.0215 (10)	0.0167 (10)	0.0002 (8)	0.0050 (8)	0.0021 (8)

Br1—C3	1.8987 (19)	C4—C5	1.389 (3)
N1—C7	1.267 (3)	C4—H4A	0.9300
N1—C8	1.464 (3)	C5—C6	1.393 (3)
C1—C2	1.384 (3)	C5—H5A	0.9300
C1—C6	1.400 (3)	C6—C7	1.475 (3)
C1—H1A	0.9300	C7—H7A	0.9300
C2—C3	1.393 (3)	C8—C8i	1.526 (4)
C2—H2A	0.9300	C8—H8A	1.05 (2)
C3—C4	1.383 (3)	C8—H8B	0.97 (2)
C7—N1—C8	116.51 (18)	C4—C5—H5A	119.4
C2—C1—C6	120.0 (2)	C6—C5—H5A	119.4
C2—C1—H1A	120.0	C5—C6—C1	119.23 (18)
C6—C1—H1A	120.0	C5—C6—C7	118.59 (18)
C1—C2—C3	119.43 (19)	C1—C6—C7	122.15 (19)
C1—C2—H2A	120.3	N1—C7—C6	123.10 (19)
C3—C2—H2A	120.3	N1—C7—H7A	118.5
C4—C3—C2	121.58 (18)	C6—C7—H7A	118.5
C4—C3—Br1	119.00 (15)	N1—C8—C8i	109.9 (2)
C2—C3—Br1	119.42 (15)	N1—C8—H8A	107.5 (13)
C3—C4—C5	118.43 (19)	C8i—C8—H8A	108.8 (13)
C3—C4—H4A	120.8	N1—C8—H8B	112.2 (12)
C5—C4—H4A	120.8	C8i—C8—H8B	113.6 (13)
C4—C5—C6	121.22 (19)	H8A—C8—H8B	104.4 (18)
C6—C1—C2—C3	2.1 (3)	C4—C5—C6—C7	179.13 (17)
C1—C2—C3—C4	0.1 (3)	C2—C1—C6—C5	−2.6 (3)
C1—C2—C3—Br1	−179.35 (14)	C2—C1—C6—C7	179.26 (17)
C2—C3—C4—C5	−1.7 (3)	C8—N1—C7—C6	176.96 (18)
Br1—C3—C4—C5	177.70 (14)	C5—C6—C7—N1	178.68 (18)
C3—C4—C5—C6	1.2 (3)	C1—C6—C7—N1	−3.2 (3)
C4—C5—C6—C1	1.0 (3)	C7—N1—C8—C8i	129.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1	0.93	2.99	3.7143 (19)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cg1	0.93	2.99	3.7143 (19)	136

Cg1 is the centroid of the C1–C6 benzene ring.