(E,E)-1,2-Bis[1-(2-bromo-phen-yl)ethyl-idene]hydrazine.

In the title compound, C(16)H(14)Br(2)N(2), the complete molecule is generated by a crystallographic twofold axis. The dihedral angle between the two benzene rings is 35.28 (8)° and that between the best planes of two ethyl-idinehydrazine N-N=C-Me units is 87.67 (11)°. Each of these N/N/C/C planes makes a dihedral angle of 63.81 (10)° with the adjacent benzene ring. In the crystal, the mol-ecules are arranged into a layer parallel to the ac plane through C-H⋯π inter-actions. C⋯Br short contacts [3.4032 (18)-3.5969 (19) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Zhao et al. (2006 ▶). For background to and the biological activity of hydro­zones, see: Avaji et al. (2009 ▶); El-Tabl et al. (2008 ▶); Rollas & Küçükgüzel (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H14Br2N2

M = 394.11

Orthorhombic,

a = 17.2162 (3) Å

b = 11.8414 (3) Å

c = 7.6953 (2) Å

V = 1568.79 (6) Å3

Z = 4

Mo Kα radiation

μ = 5.16 mm−1

T = 100 K

0.41 × 0.27 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.227, T max = 0.462

18529 measured reflections

3458 independent reflections

2397 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.02

3458 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.40 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029867/is2578sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029867/is2578Isup2.hkl

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

C16H14Br2N2	Dx = 1.669 Mg m−3
Mr = 394.11	Melting point = 387–389 K
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 3458 reflections
a = 17.2162 (3) Å	θ = 3.4–35.0°
b = 11.8414 (3) Å	µ = 5.16 mm−1
c = 7.6953 (2) Å	T = 100 K
V = 1568.79 (6) Å3	Block, colorless
Z = 4	0.41 × 0.27 × 0.18 mm
F(000) = 776

Bruker APEXII CCD area-detector diffractometer	3458 independent reflections
Radiation source: sealed tube	2397 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 35.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
Tmin = 0.227, Tmax = 0.462	k = −19→17
18529 measured reflections	l = −12→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.033P)2 + 0.5992P] where P = (Fo2 + 2Fc2)/3
3458 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	0.634618 (11)	0.935005 (14)	0.01020 (2)	0.03110 (7)
N1	0.53208 (8)	0.65309 (11)	0.19436 (17)	0.0228 (3)
C1	0.64389 (9)	0.79361 (14)	−0.1054 (2)	0.0234 (3)
C2	0.70442 (10)	0.77985 (16)	−0.2228 (2)	0.0294 (3)
H2A	0.7383	0.8391	−0.2459	0.035*
C3	0.71362 (10)	0.67629 (16)	−0.3054 (2)	0.0328 (4)
H3A	0.7538	0.6662	−0.3847	0.039*
C4	0.66330 (11)	0.58836 (16)	−0.2698 (2)	0.0312 (4)
H4A	0.6695	0.5193	−0.3256	0.037*
C5	0.60342 (10)	0.60310 (15)	−0.1509 (2)	0.0253 (3)
H5A	0.5700	0.5433	−0.1274	0.030*
C6	0.59263 (9)	0.70617 (13)	−0.06618 (19)	0.0209 (3)
C7	0.52783 (9)	0.71762 (13)	0.06106 (19)	0.0205 (3)
C8	0.46160 (10)	0.79632 (16)	0.0247 (2)	0.0289 (3)
H8A	0.4138	0.7545	0.0230	0.043*
H8B	0.4693	0.8319	−0.0860	0.043*
H8C	0.4592	0.8529	0.1138	0.043*

	U11	U22	U33	U12	U13	U23
Br1	0.03424 (10)	0.01869 (9)	0.04038 (11)	−0.00163 (6)	−0.00389 (8)	0.00074 (7)
N1	0.0244 (6)	0.0181 (6)	0.0259 (6)	0.0005 (5)	0.0057 (5)	0.0004 (5)
C1	0.0236 (7)	0.0204 (7)	0.0261 (7)	0.0020 (6)	−0.0017 (6)	0.0031 (6)
C2	0.0238 (8)	0.0320 (9)	0.0324 (8)	0.0002 (7)	0.0023 (6)	0.0113 (7)
C3	0.0296 (9)	0.0395 (11)	0.0293 (8)	0.0076 (8)	0.0100 (7)	0.0063 (7)
C4	0.0337 (9)	0.0305 (9)	0.0295 (8)	0.0078 (7)	0.0072 (7)	−0.0017 (7)
C5	0.0264 (8)	0.0220 (7)	0.0275 (7)	0.0016 (6)	0.0042 (6)	−0.0004 (6)
C6	0.0216 (7)	0.0203 (7)	0.0208 (6)	0.0029 (6)	0.0005 (5)	0.0016 (5)
C7	0.0204 (7)	0.0188 (7)	0.0222 (6)	0.0006 (5)	0.0004 (5)	−0.0031 (5)
C8	0.0255 (8)	0.0368 (9)	0.0244 (7)	0.0091 (7)	−0.0007 (6)	0.0003 (6)

Br1—C1	1.9027 (16)	C4—C5	1.389 (2)
N1—C7	1.2812 (19)	C4—H4A	0.9300
N1—N1i	1.398 (2)	C5—C6	1.396 (2)
C1—C2	1.389 (2)	C5—H5A	0.9300
C1—C6	1.393 (2)	C6—C7	1.491 (2)
C2—C3	1.390 (3)	C7—C8	1.499 (2)
C2—H2A	0.9300	C8—H8A	0.9600
C3—C4	1.382 (3)	C8—H8B	0.9600
C3—H3A	0.9300	C8—H8C	0.9600
C7—N1—N1i	116.45 (14)	C4—C5—H5A	119.5
C2—C1—C6	121.93 (16)	C6—C5—H5A	119.5
C2—C1—Br1	118.05 (13)	C1—C6—C5	117.65 (14)
C6—C1—Br1	119.97 (12)	C1—C6—C7	123.27 (14)
C1—C2—C3	119.09 (16)	C5—C6—C7	119.08 (14)
C1—C2—H2A	120.5	N1—C7—C6	115.40 (14)
C3—C2—H2A	120.5	N1—C7—C8	124.31 (14)
C4—C3—C2	120.19 (16)	C6—C7—C8	120.22 (13)
C4—C3—H3A	119.9	C7—C8—H8A	109.5
C2—C3—H3A	119.9	C7—C8—H8B	109.5
C3—C4—C5	120.05 (17)	H8A—C8—H8B	109.5
C3—C4—H4A	120.0	C7—C8—H8C	109.5
C5—C4—H4A	120.0	H8A—C8—H8C	109.5
C4—C5—C6	121.08 (16)	H8B—C8—H8C	109.5
C6—C1—C2—C3	0.8 (2)	C4—C5—C6—C1	0.1 (2)
Br1—C1—C2—C3	178.28 (13)	C4—C5—C6—C7	−179.65 (16)
C1—C2—C3—C4	−0.3 (3)	N1i—N1—C7—C6	−173.12 (13)
C2—C3—C4—C5	−0.2 (3)	N1i—N1—C7—C8	3.8 (2)
C3—C4—C5—C6	0.3 (3)	C1—C6—C7—N1	−117.18 (17)
C2—C1—C6—C5	−0.7 (2)	C5—C6—C7—N1	62.6 (2)
Br1—C1—C6—C5	−178.13 (12)	C1—C6—C7—C8	65.7 (2)
C2—C1—C6—C7	179.07 (15)	C5—C6—C7—C8	−114.47 (18)
Br1—C1—C6—C7	1.7 (2)

Cg1 is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1ii	0.93	2.83	3.7246 (17)	161
C8—H8A···Cg1iii	0.96	2.93	3.4989 (18)	119

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1i	0.93	2.83	3.7246 (17)	161
C8—H8A⋯Cg1ii	0.96	2.93	3.4989 (18)	119

Symmetry codes: (i) ; (ii) .