(E)-4-Bromo-N-{(E)-3-[(4-bromo-2-methyl-phen-yl)imino]-butan-2-yl-idene}-2-methyl-aniline.

The title compound, C(18)H(18)Br(2)N(2), is centrosymmetric with the mid-point of the central C-C bond of the butyl group located on an inversion center. The terminal benzene ring is approximately perpendicular to the central butyl plane [dihedral angle = 71.9 (8)°]. No hydrogen bonding or aromatic stacking is observed in the crystal.

Related literature

For applications of diimine-n class="Chemical">metal catalysts, see: Johnson et al. (1995 ▶); Killian et al. (1996 ▶); Popeney & Guan (2010 ▶); Popeney et al. (2011 ▶); Yuan et al. (2005 ▶). For a related structure, see: Zhang et al. (2013 ▶).

Experimental

Crystal data

C18H18Br2N2

M = 422.16

Orthorhombic,

a = 13.625 (13) Å

b = 7.495 (7) Å

c = 17.029 (17) Å

V = 1739 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.66 mm−1

T = 293 K

0.21 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.441, T max = 0.542

6368 measured reflections

1541 independent reflections

847 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.113

S = 1.05

1541 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.85 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812052087/xu5666sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812052087/xu5666Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812052087/xu5666Isup3.cml

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

C18H18Br2N2	F(000) = 840
Mr = 422.16	Dx = 1.612 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 951 reflections
a = 13.625 (13) Å	θ = 2.8–20.3°
b = 7.495 (7) Å	µ = 4.66 mm−1
c = 17.029 (17) Å	T = 293 K
V = 1739 (3) Å3	Block, yellow
Z = 4	0.21 × 0.20 × 0.15 mm

Bruker APEXII CCD diffractometer	1541 independent reflections
Radiation source: fine-focus sealed tube	847 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
φ and ω scans	θmax = 25.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.441, Tmax = 0.542	k = −9→5
6368 measured reflections	l = −20→18

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0106P)2 + 5.9013P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1541 reflections	Δρmax = 0.70 e Å−3
103 parameters	Δρmin = −0.85 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (5)

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	0.30195 (6)	0.23158 (11)	0.40014 (4)	0.0631 (4)
C1	0.4677 (5)	0.4420 (8)	0.2188 (4)	0.0398 (17)
H1	0.5330	0.4728	0.2107	0.048*
C2	0.4386 (5)	0.3772 (9)	0.2914 (4)	0.0444 (19)
H2	0.4836	0.3653	0.3321	0.053*
C3	0.3421 (5)	0.3308 (8)	0.3021 (4)	0.0374 (17)
C4	0.2742 (5)	0.3508 (7)	0.2429 (4)	0.0341 (16)
H4	0.2092	0.3188	0.2518	0.041*
C5	0.3017 (5)	0.4189 (7)	0.1692 (3)	0.0277 (14)
C6	0.3998 (4)	0.4617 (7)	0.1574 (4)	0.0299 (15)
C7	0.4845 (4)	0.4520 (8)	0.0370 (4)	0.0307 (15)
C8	0.5198 (5)	0.2627 (8)	0.0474 (4)	0.0451 (17)
H8A	0.4765	0.2006	0.0825	0.068*
H8B	0.5850	0.2636	0.0689	0.068*
H8C	0.5205	0.2035	−0.0026	0.068*
C9	0.2258 (4)	0.4423 (8)	0.1053 (4)	0.0452 (18)
H9A	0.2541	0.5074	0.0623	0.068*
H9B	0.1706	0.5071	0.1257	0.068*
H9C	0.2045	0.3273	0.0872	0.068*
N1	0.4299 (4)	0.5380 (6)	0.0839 (3)	0.0331 (13)

	U11	U22	U33	U12	U13	U23
Br1	0.0619 (6)	0.0768 (6)	0.0505 (5)	0.0068 (5)	0.0143 (4)	0.0208 (5)
C1	0.017 (4)	0.044 (4)	0.058 (5)	−0.003 (3)	0.004 (3)	0.006 (4)
C2	0.040 (5)	0.048 (5)	0.045 (4)	−0.005 (4)	−0.007 (3)	0.004 (4)
C3	0.033 (4)	0.031 (4)	0.048 (4)	0.001 (3)	0.003 (4)	0.000 (3)
C4	0.021 (4)	0.030 (3)	0.051 (4)	−0.001 (3)	0.009 (3)	−0.002 (3)
C5	0.024 (4)	0.019 (3)	0.041 (4)	−0.001 (3)	0.002 (3)	−0.001 (3)
C6	0.027 (4)	0.021 (3)	0.042 (4)	0.001 (3)	0.012 (3)	0.000 (3)
C7	0.012 (3)	0.028 (4)	0.052 (4)	−0.005 (3)	0.004 (3)	0.008 (3)
C8	0.043 (4)	0.033 (4)	0.060 (4)	0.012 (4)	0.015 (4)	0.012 (3)
C9	0.033 (5)	0.043 (4)	0.059 (5)	−0.002 (3)	0.003 (4)	0.003 (4)
N1	0.021 (3)	0.030 (3)	0.048 (4)	0.000 (3)	0.006 (3)	0.006 (3)

Br1—C3	1.908 (7)	C6—N1	1.436 (7)
C1—C2	1.386 (9)	C7—N1	1.268 (7)
C1—C6	1.403 (8)	C7—C8	1.509 (8)
C1—H1	0.9300	C7—C7i	1.510 (11)
C2—C3	1.372 (9)	C8—H8A	0.9600
C2—H2	0.9300	C8—H8B	0.9600
C3—C4	1.375 (9)	C8—H8C	0.9600
C4—C5	1.406 (8)	C9—H9A	0.9600
C4—H4	0.9300	C9—H9B	0.9600
C5—C6	1.390 (8)	C9—H9C	0.9600
C5—C9	1.512 (8)
C2—C1—C6	120.8 (6)	C1—C6—N1	120.2 (5)
C2—C1—H1	119.6	N1—C7—C8	126.2 (5)
C6—C1—H1	119.6	N1—C7—C7i	116.6 (7)
C3—C2—C1	118.8 (6)	C8—C7—C7i	117.2 (7)
C3—C2—H2	120.6	C7—C8—H8A	109.5
C1—C2—H2	120.6	C7—C8—H8B	109.5
C2—C3—C4	121.3 (6)	H8A—C8—H8B	109.5
C2—C3—Br1	119.3 (5)	C7—C8—H8C	109.5
C4—C3—Br1	119.4 (5)	H8A—C8—H8C	109.5
C3—C4—C5	120.9 (6)	H8B—C8—H8C	109.5
C3—C4—H4	119.5	C5—C9—H9A	109.5
C5—C4—H4	119.5	C5—C9—H9B	109.5
C6—C5—C4	118.0 (6)	H9A—C9—H9B	109.5
C6—C5—C9	121.8 (6)	C5—C9—H9C	109.5
C4—C5—C9	120.2 (6)	H9A—C9—H9C	109.5
C5—C6—C1	120.1 (6)	H9B—C9—H9C	109.5
C5—C6—N1	119.5 (6)	C7—N1—C6	120.9 (5)
C6—C1—C2—C3	0.6 (10)	C4—C5—C6—N1	−177.6 (5)
C1—C2—C3—C4	−1.3 (10)	C9—C5—C6—N1	2.9 (8)
C1—C2—C3—Br1	177.3 (5)	C2—C1—C6—C5	1.1 (9)
C2—C3—C4—C5	0.3 (9)	C2—C1—C6—N1	176.6 (5)
Br1—C3—C4—C5	−178.3 (4)	C8—C7—N1—C6	3.9 (10)
C3—C4—C5—C6	1.4 (8)	C7i—C7—N1—C6	−177.3 (6)
C3—C4—C5—C9	−179.2 (6)	C5—C6—N1—C7	−112.5 (7)
C4—C5—C6—C1	−2.0 (8)	C1—C6—N1—C7	71.9 (8)
C9—C5—C6—C1	178.5 (5)