(Z)-4-Bromo-N-{(Z)-3-[(4-bromo-2,6-diisopropyl-phen-yl)imino]-butan-2-yl-idene}-2,6-diisopropyl-aniline.

The title compound, C(28)H(38)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 1,4-diaza-butadiene mean plane [dihedral angle = 78.23 (3)°]. No hydrogen bonding or aromatic stacking is observed in the crystal structure.

Related literature

For applications of diimine catalysts, see: Cotts et al. (2000 ▶); Ittel et al. (2000 ▶); Johnson et al. (1995 ▶); Zhang & Ye (2012 ▶).

Experimental

Crystal data

C28H38Br2N2

M = 562.42

Monoclinic,

a = 9.099 (3) Å

b = 12.199 (4) Å

c = 13.566 (5) Å

β = 104.905 (5)°

V = 1455.2 (9) Å3

Z = 2

Mo Kα radiation

μ = 2.80 mm−1

T = 296 K

0.25 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.541, T max = 0.618

7266 measured reflections

2685 independent reflections

1460 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.179

S = 0.94

2685 reflections

150 parameters

84 restraints

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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/S160053681205194X/xu5664sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205194X/xu5664Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205194X/xu5664Isup3.cml

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

C28H38Br2N2	F(000) = 580
Mr = 562.42	Dx = 1.284 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1370 reflections
a = 9.099 (3) Å	θ = 2.9–21.4°
b = 12.199 (4) Å	µ = 2.80 mm−1
c = 13.566 (5) Å	T = 296 K
β = 104.905 (5)°	Block, yellow
V = 1455.2 (9) Å3	0.25 × 0.23 × 0.19 mm
Z = 2

Bruker APEXII CCD diffractometer	2685 independent reflections
Radiation source: fine-focus sealed tube	1460 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.541, Tmax = 0.618	k = −12→14
7266 measured reflections	l = −16→14

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.1P)2 + 0.7029P] where P = (Fo2 + 2Fc2)/3
2685 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.46 e Å−3
84 restraints	Δρmin = −0.40 e Å−3

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	0.35688 (8)	0.65673 (6)	0.10127 (7)	0.0922 (4)
C1	0.7029 (6)	0.8851 (4)	0.1392 (4)	0.0489 (12)
C2	0.5759 (6)	0.8270 (4)	0.1476 (4)	0.0533 (14)
H2	0.5247	0.8477	0.1958	0.064*
C3	0.5254 (6)	0.7392 (5)	0.0851 (4)	0.0539 (14)
C4	0.5971 (7)	0.7079 (4)	0.0117 (4)	0.0557 (15)
H4	0.5608	0.6482	−0.0301	0.067*
C5	0.7232 (7)	0.7651 (4)	−0.0001 (5)	0.0585 (14)
C6	0.7756 (6)	0.8543 (4)	0.0646 (4)	0.0452 (13)
C7	0.7611 (8)	0.9814 (5)	0.2083 (5)	0.0662 (14)
H7	0.8701	0.9872	0.2130	0.079*
C8	0.6907 (11)	1.0865 (6)	0.1624 (7)	0.126 (3)
H8A	0.7162	1.0991	0.0990	0.188*
H8B	0.7283	1.1459	0.2084	0.188*
H8C	0.5822	1.0819	0.1505	0.188*
C9	0.7469 (11)	0.9636 (8)	0.3149 (6)	0.120 (3)
H9A	0.8150	1.0122	0.3607	0.180*
H9B	0.7725	0.8891	0.3348	0.180*
H9C	0.6443	0.9783	0.3175	0.180*
C10	0.8059 (9)	0.7265 (6)	−0.0773 (6)	0.0804 (16)
H10	0.8666	0.7876	−0.0923	0.096*
C11	0.9126 (12)	0.6347 (7)	−0.0315 (8)	0.132 (3)
H11A	0.9847	0.6606	0.0287	0.199*
H11B	0.9656	0.6101	−0.0802	0.199*
H11C	0.8555	0.5750	−0.0139	0.199*
C12	0.6986 (12)	0.6892 (8)	−0.1768 (7)	0.126 (3)
H12A	0.6336	0.6323	−0.1632	0.189*
H12B	0.7566	0.6616	−0.2214	0.189*
H12C	0.6378	0.7500	−0.2086	0.189*
C13	0.9228 (6)	0.9765 (4)	−0.0034 (4)	0.0512 (14)
C14	0.7932 (7)	1.0159 (6)	−0.0879 (5)	0.081 (2)
H14A	0.8104	0.9956	−0.1523	0.122*
H14B	0.7856	1.0942	−0.0843	0.122*
H14C	0.7003	0.9831	−0.0812	0.122*
N1	0.9141 (5)	0.9060 (3)	0.0633 (3)	0.0504 (11)

	U11	U22	U33	U12	U13	U23
Br1	0.0812 (6)	0.0846 (6)	0.1286 (8)	−0.0381 (4)	0.0595 (5)	−0.0188 (4)
C1	0.053 (3)	0.045 (3)	0.054 (3)	−0.005 (2)	0.023 (2)	−0.001 (2)
C2	0.053 (3)	0.054 (3)	0.058 (4)	−0.001 (3)	0.023 (3)	−0.001 (3)
C3	0.055 (3)	0.052 (3)	0.060 (4)	−0.011 (3)	0.026 (3)	0.005 (3)
C4	0.070 (4)	0.034 (3)	0.066 (4)	−0.014 (3)	0.024 (3)	−0.004 (3)
C5	0.075 (3)	0.043 (3)	0.070 (3)	−0.012 (3)	0.043 (3)	0.001 (3)
C6	0.046 (3)	0.037 (3)	0.055 (3)	−0.005 (2)	0.017 (3)	0.008 (2)
C7	0.076 (3)	0.062 (3)	0.067 (3)	−0.015 (3)	0.028 (3)	−0.015 (3)
C8	0.145 (7)	0.070 (5)	0.145 (6)	−0.001 (5)	0.005 (6)	−0.036 (5)
C9	0.155 (7)	0.131 (6)	0.083 (5)	−0.052 (5)	0.045 (5)	−0.038 (5)
C10	0.100 (4)	0.066 (3)	0.095 (4)	−0.016 (3)	0.060 (3)	−0.018 (3)
C11	0.131 (7)	0.129 (6)	0.163 (7)	0.022 (5)	0.085 (6)	−0.026 (6)
C12	0.153 (7)	0.147 (6)	0.100 (6)	−0.030 (6)	0.073 (5)	−0.040 (5)
C13	0.053 (3)	0.045 (3)	0.059 (4)	−0.006 (2)	0.019 (3)	0.007 (3)
C14	0.059 (4)	0.083 (5)	0.093 (5)	−0.012 (3)	0.005 (4)	0.039 (4)
N1	0.052 (3)	0.044 (3)	0.059 (3)	−0.006 (2)	0.022 (2)	0.005 (2)

Br1—C3	1.894 (5)	C9—H9A	0.9600
C1—C2	1.384 (7)	C9—H9B	0.9600
C1—C6	1.396 (7)	C9—H9C	0.9600
C1—C7	1.511 (8)	C10—C11	1.507 (11)
C2—C3	1.371 (7)	C10—C12	1.517 (11)
C2—H2	0.9300	C10—H10	0.9800
C3—C4	1.376 (8)	C11—H11A	0.9600
C4—C5	1.387 (7)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.402 (7)	C12—H12A	0.9600
C5—C10	1.513 (8)	C12—H12B	0.9600
C6—N1	1.414 (7)	C12—H12C	0.9600
C7—C8	1.495 (10)	C13—N1	1.265 (6)
C7—C9	1.501 (9)	C13—C14	1.497 (8)
C7—H7	0.9800	C13—C13i	1.498 (10)
C8—H8A	0.9600	C14—H14A	0.9600
C8—H8B	0.9600	C14—H14B	0.9600
C8—H8C	0.9600	C14—H14C	0.9600
C2—C1—C6	118.8 (5)	H9A—C9—H9B	109.5
C2—C1—C7	120.9 (5)	C7—C9—H9C	109.5
C6—C1—C7	120.2 (5)	H9A—C9—H9C	109.5
C3—C2—C1	120.2 (5)	H9B—C9—H9C	109.5
C3—C2—H2	119.9	C11—C10—C5	109.2 (6)
C1—C2—H2	119.9	C11—C10—C12	110.1 (7)
C2—C3—C4	121.2 (5)	C5—C10—C12	112.8 (6)
C2—C3—Br1	119.7 (4)	C11—C10—H10	108.2
C4—C3—Br1	119.0 (4)	C5—C10—H10	108.2
C3—C4—C5	120.3 (5)	C12—C10—H10	108.2
C3—C4—H4	119.8	C10—C11—H11A	109.5
C5—C4—H4	119.8	C10—C11—H11B	109.5
C4—C5—C6	118.4 (5)	H11A—C11—H11B	109.5
C4—C5—C10	119.8 (5)	C10—C11—H11C	109.5
C6—C5—C10	121.7 (5)	H11A—C11—H11C	109.5
C1—C6—C5	121.1 (5)	H11B—C11—H11C	109.5
C1—C6—N1	118.6 (5)	C10—C12—H12A	109.5
C5—C6—N1	119.9 (5)	C10—C12—H12B	109.5
C8—C7—C9	113.0 (7)	H12A—C12—H12B	109.5
C8—C7—C1	111.3 (5)	C10—C12—H12C	109.5
C9—C7—C1	112.5 (5)	H12A—C12—H12C	109.5
C8—C7—H7	106.5	H12B—C12—H12C	109.5
C9—C7—H7	106.5	N1—C13—C14	125.7 (5)
C1—C7—H7	106.5	N1—C13—C13i	116.6 (6)
C7—C8—H8A	109.5	C14—C13—C13i	117.8 (6)
C7—C8—H8B	109.5	C13—C14—H14A	109.5
H8A—C8—H8B	109.5	C13—C14—H14B	109.5
C7—C8—H8C	109.5	H14A—C14—H14B	109.5
H8A—C8—H8C	109.5	C13—C14—H14C	109.5
H8B—C8—H8C	109.5	H14A—C14—H14C	109.5
C7—C9—H9A	109.5	H14B—C14—H14C	109.5
C7—C9—H9B	109.5	C13—N1—C6	122.2 (4)
C6—C1—C2—C3	1.6 (8)	C4—C5—C6—N1	172.3 (5)
C7—C1—C2—C3	−179.3 (5)	C10—C5—C6—N1	−4.1 (9)
C1—C2—C3—C4	−1.3 (9)	C2—C1—C7—C8	−90.6 (8)
C1—C2—C3—Br1	177.3 (4)	C6—C1—C7—C8	88.5 (8)
C2—C3—C4—C5	0.2 (9)	C2—C1—C7—C9	37.4 (8)
Br1—C3—C4—C5	−178.4 (4)	C6—C1—C7—C9	−143.5 (6)
C3—C4—C5—C6	0.4 (9)	C4—C5—C10—C11	−81.6 (8)
C3—C4—C5—C10	176.9 (6)	C6—C5—C10—C11	94.7 (8)
C2—C1—C6—C5	−0.9 (8)	C4—C5—C10—C12	41.1 (9)
C7—C1—C6—C5	180.0 (5)	C6—C5—C10—C12	−142.6 (7)
C2—C1—C6—N1	−173.4 (5)	C14—C13—N1—C6	0.5 (9)
C7—C1—C6—N1	7.5 (8)	C13i—C13—N1—C6	−179.2 (6)
C4—C5—C6—C1	−0.1 (8)	C1—C6—N1—C13	−106.2 (6)
C10—C5—C6—C1	−176.4 (6)	C5—C6—N1—C13	81.2 (7)