4,6-Di-bromo-N-{3-[(4,6-di-bromo-2,3-di-methyl-phenyl)imino]butan-2-yl-idene}-2,3-di-methyl-aniline.

The title compound, C20H20Br4N2, is a product of the condensation reaction of 4,6-di-bromo-2,3-di-methyl-aniline and butane-2,3-dione. The mol-ecule has a center of symmetry at the mid-point of the central C-C bond. The dihedral angle between the benzene ring and the 1,4-di-aza-butadiene plane is 78.3 (2)°. Niether hydrogen bonding nor aromatic stacking is observed in the crystal structure.

Related literature

For applications of di­imine–metal catalysts, see: Johnson et al. (1995 ▶). For related structures, see: Gao et al. (2012 ▶); Sun et al. (2012 ▶); Popeney et al. (2012 ▶); Shi et al. (2012 ▶); Zhang & Ye (2012 ▶); Killian et al. (1996 ▶); Yuan et al. (2005 ▶, 2011 ▶).

Experimental

Crystal data

C20H20Br4N2

M = 607.98

Monoclinic,

a = 5.5582 (6) Å

b = 12.8881 (15) Å

c = 14.8377 (11) Å

β = 98.782 (8)°

V = 1050.43 (19) Å3

Z = 2

Cu Kα radiation

μ = 9.40 mm−1

T = 150 K

0.29 × 0.17 × 0.16 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.688, T max = 1.000

4675 measured reflections

1921 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.135

S = 1.11

1921 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −1.04 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">RED (Agilent, 2013 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: OLEX2; software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813023921/rk2409sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023921/rk2409Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023921/rk2409Isup3.cml

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

C20H20Br4N2	F(000) = 588
Mr = 607.98	Dx = 1.922 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 5.5582 (6) Å	Cell parameters from 2210 reflections
b = 12.8881 (15) Å	θ = 3.4–70.4°
c = 14.8377 (11) Å	µ = 9.40 mm−1
β = 98.782 (8)°	T = 150 K
V = 1050.43 (19) Å3	Block, clear light yellow
Z = 2	0.29 × 0.17 × 0.16 mm

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	1921 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1777 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 16.0733 pixels mm-1	θmax = 68.2°, θmin = 4.6°
ω–scans	h = −6→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −15→15
Tmin = 0.688, Tmax = 1.000	l = −17→17
4675 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0802P)2 + 2.2115P] where P = (Fo2 + 2Fc2)/3
1921 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −1.04 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Br2	0.84461 (11)	0.31214 (5)	0.68427 (4)	0.0431 (2)
N1	0.5517 (8)	0.5134 (4)	0.6182 (3)	0.0327 (9)
C2	0.2754 (9)	0.4881 (4)	0.8311 (3)	0.0269 (9)
C3	0.6169 (9)	0.3862 (4)	0.7425 (3)	0.0277 (10)
C4	0.4939 (9)	0.4723 (4)	0.7012 (3)	0.0275 (10)
C5	0.3261 (10)	0.5238 (4)	0.7464 (3)	0.0296 (10)
C6	0.4633 (10)	0.4739 (4)	0.5417 (3)	0.0341 (11)
C7	0.5762 (9)	0.3504 (4)	0.8271 (3)	0.0293 (10)
H7	0.6616	0.2939	0.8548	0.035*
C1	0.1862 (10)	0.6189 (4)	0.7022 (3)	0.0341 (11)
H1A	0.0200	0.5999	0.6813	0.051*
H1B	0.2604	0.6422	0.6515	0.051*
H1C	0.1912	0.6736	0.7463	0.051*
C8	0.2980 (12)	0.3814 (5)	0.5268 (3)	0.0438 (14)
H8A	0.1479	0.4010	0.4898	0.066*
H8B	0.2654	0.3560	0.5845	0.066*
H8C	0.3751	0.3278	0.4964	0.066*
C9	0.0867 (10)	0.5414 (4)	0.8773 (4)	0.0378 (12)
H9A	0.1616	0.5968	0.9148	0.057*
H9B	0.0170	0.4924	0.9146	0.057*
H9C	−0.0388	0.5691	0.8321	0.057*
C10	0.4039 (9)	0.4017 (4)	0.8689 (3)	0.0277 (10)
Br1	0.34078 (11)	0.34478 (4)	0.98167 (3)	0.0379 (2)

	U11	U22	U33	U12	U13	U23
Br2	0.0473 (4)	0.0546 (4)	0.0317 (3)	−0.0012 (3)	0.0199 (3)	−0.0110 (2)
N1	0.043 (2)	0.043 (2)	0.0129 (18)	−0.0155 (19)	0.0064 (16)	0.0029 (17)
C2	0.035 (2)	0.030 (2)	0.017 (2)	−0.0044 (19)	0.0075 (17)	−0.0020 (17)
C3	0.038 (2)	0.032 (2)	0.015 (2)	−0.005 (2)	0.0109 (17)	−0.0075 (18)
C4	0.042 (3)	0.032 (2)	0.0096 (19)	−0.012 (2)	0.0066 (17)	−0.0023 (17)
C5	0.047 (3)	0.026 (2)	0.015 (2)	−0.006 (2)	0.0046 (19)	0.0011 (18)
C6	0.047 (3)	0.044 (3)	0.013 (2)	−0.016 (2)	0.0102 (19)	0.001 (2)
C7	0.042 (3)	0.025 (2)	0.022 (2)	−0.003 (2)	0.007 (2)	−0.0012 (17)
C1	0.053 (3)	0.029 (2)	0.019 (2)	−0.004 (2)	0.001 (2)	0.0107 (19)
C8	0.061 (4)	0.058 (3)	0.013 (2)	−0.031 (3)	0.007 (2)	0.000 (2)
C9	0.045 (3)	0.042 (3)	0.029 (3)	0.005 (2)	0.015 (2)	−0.003 (2)
C10	0.044 (3)	0.030 (2)	0.0102 (18)	−0.004 (2)	0.0077 (17)	0.0000 (17)
Br1	0.0605 (4)	0.0407 (4)	0.0159 (3)	0.0013 (2)	0.0171 (2)	0.00654 (19)

Br2—C3	1.895 (5)	C7—H7	0.9300
N1—C4	1.422 (6)	C7—C10	1.385 (7)
N1—C6	1.273 (6)	C1—H1A	0.9600
C2—C5	1.406 (6)	C1—H1B	0.9600
C2—C9	1.504 (7)	C1—H1C	0.9600
C2—C10	1.395 (7)	C8—H8A	0.9600
C3—C4	1.395 (7)	C8—H8B	0.9600
C3—C7	1.388 (6)	C8—H8C	0.9600
C4—C5	1.397 (7)	C9—H9A	0.9600
C5—C1	1.543 (7)	C9—H9B	0.9600
C6—C6i	1.518 (9)	C9—H9C	0.9600
C6—C8	1.501 (7)	C10—Br1	1.908 (4)
C6—N1—C4	121.1 (4)	C5—C1—H1B	109.5
C5—C2—C9	120.5 (5)	C5—C1—H1C	109.5
C10—C2—C5	117.4 (4)	H1A—C1—H1B	109.5
C10—C2—C9	122.1 (4)	H1A—C1—H1C	109.5
C4—C3—Br2	121.1 (3)	H1B—C1—H1C	109.5
C7—C3—Br2	117.2 (4)	C6—C8—H8A	109.5
C7—C3—C4	121.6 (4)	C6—C8—H8B	109.5
C3—C4—N1	121.1 (4)	C6—C8—H8C	109.5
C3—C4—C5	119.1 (4)	H8A—C8—H8B	109.5
C5—C4—N1	119.6 (4)	H8A—C8—H8C	109.5
C2—C5—C1	118.9 (5)	H8B—C8—H8C	109.5
C4—C5—C2	120.9 (4)	C2—C9—H9A	109.5
C4—C5—C1	120.2 (4)	C2—C9—H9B	109.5
N1—C6—C6i	115.8 (6)	C2—C9—H9C	109.5
N1—C6—C8	126.4 (4)	H9A—C9—H9B	109.5
C8—C6—C6i	117.8 (5)	H9A—C9—H9C	109.5
C3—C7—H7	121.1	H9B—C9—H9C	109.5
C10—C7—C3	117.8 (5)	C2—C10—Br1	120.6 (4)
C10—C7—H7	121.1	C7—C10—C2	123.2 (4)
C5—C1—H1A	109.5	C7—C10—Br1	116.2 (4)
Br2—C3—C4—N1	−6.1 (6)	C5—C2—C10—C7	−0.1 (7)
Br2—C3—C4—C5	179.4 (3)	C5—C2—C10—Br1	−178.0 (4)
Br2—C3—C7—C10	−177.8 (4)	C6—N1—C4—C3	82.4 (7)
N1—C4—C5—C2	−176.5 (4)	C6—N1—C4—C5	−103.1 (6)
N1—C4—C5—C1	5.7 (7)	C7—C3—C4—N1	174.7 (4)
C3—C4—C5—C2	−1.9 (7)	C7—C3—C4—C5	0.2 (7)
C3—C4—C5—C1	−179.7 (4)	C9—C2—C5—C4	−177.4 (5)
C3—C7—C10—C2	−1.5 (7)	C9—C2—C5—C1	0.4 (7)
C3—C7—C10—Br1	176.5 (4)	C9—C2—C10—C7	179.1 (5)
C4—N1—C6—C6i	179.2 (6)	C9—C2—C10—Br1	1.2 (7)
C4—N1—C6—C8	−1.5 (10)	C10—C2—C5—C4	1.8 (7)
C4—C3—C7—C10	1.5 (7)	C10—C2—C5—C1	179.6 (4)