(Z)-3-Chloro-N-[(Z)-3-(3-chloro-2-methyl-phenyl-imino)-butan-2-yl-idene]-2-methyl-aniline.

In the title compound, C(18)H(18)Cl(2)N(2), the complete molecule is generated by the application of C(2) symmetry. The C=N bond has an E configuration. The dihedral angle between the benzene ring and the 1,4-diaza-butadiene plane is 66.81 (9)°.

Related literature

For background to the applications of the olefin polymerization Ni(II)-α-diimine catalysts, see: Johnson et al. (1995 ▶); Killian et al. (1996 ▶). For the effect of the ligand structure on the activity of the catalyst and properties of the products, see: Popeney & Guan (2010 ▶); Popeney et al. (2011 ▶); Yuan et al. (2005 ▶). For related structures, see: Kose & McKee (2011 ▶); Wei et al. (2011 ▶).

Experimental

Crystal data

C18H18Cl2N2

M = 333.24

Monoclinic,

a = 8.032 (6) Å

b = 7.372 (5) Å

c = 14.475 (10) Å

β = 93.533 (7)°

V = 855.5 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.918, T max = 0.932

5279 measured reflections

1588 independent reflections

1199 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.06

1588 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052044/bq2319sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052044/bq2319Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052044/bq2319Isup3.cml

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

C18H18Cl2N2	F(000) = 348
Mr = 333.24	Dx = 1.294 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2237 reflections
a = 8.032 (6) Å	θ = 2.8–28.0°
b = 7.372 (5) Å	µ = 0.38 mm−1
c = 14.475 (10) Å	T = 296 K
β = 93.533 (7)°	Block, colorless
V = 855.5 (11) Å3	0.23 × 0.21 × 0.19 mm
Z = 2

Bruker APEXII CCD diffractometer	1588 independent reflections
Radiation source: fine-focus sealed tube	1199 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.918, Tmax = 0.932	k = −8→8
5279 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.4563P] where P = (Fo2 + 2Fc2)/3
1588 reflections	(Δ/σ)max = 0.001
102 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.28 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
C1	0.4602 (2)	0.2982 (3)	0.17826 (13)	0.0373 (5)
C2	0.5314 (2)	0.3432 (3)	0.26633 (13)	0.0382 (5)
C3	0.5281 (3)	0.2084 (3)	0.33347 (14)	0.0451 (5)
C4	0.4584 (3)	0.0403 (3)	0.31793 (16)	0.0532 (6)
H4	0.4589	−0.0453	0.3651	0.064*
C5	0.3875 (3)	0.0005 (3)	0.23100 (16)	0.0532 (6)
H5	0.3391	−0.1124	0.2192	0.064*
C6	0.3887 (3)	0.1286 (3)	0.16168 (15)	0.0469 (5)
H6	0.3411	0.1013	0.1031	0.056*
C7	0.6047 (3)	0.5274 (3)	0.28511 (17)	0.0603 (7)
H7A	0.5640	0.5748	0.3412	0.090*
H7B	0.5730	0.6070	0.2346	0.090*
H7C	0.7241	0.5182	0.2916	0.090*
C8	0.5174 (2)	0.4244 (3)	0.03386 (13)	0.0383 (5)
C9	0.6332 (4)	0.2775 (3)	0.00740 (18)	0.0672 (8)
H9A	0.6605	0.2017	0.0601	0.101*
H9B	0.7334	0.3304	−0.0136	0.101*
H9C	0.5803	0.2058	−0.0414	0.101*
Cl1	0.61699 (10)	0.25335 (11)	0.44457 (4)	0.0788 (3)
N1	0.4462 (2)	0.4357 (2)	0.10980 (11)	0.0421 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0400 (11)	0.0413 (12)	0.0309 (10)	0.0048 (9)	0.0052 (8)	0.0042 (8)
C2	0.0360 (10)	0.0453 (12)	0.0334 (11)	0.0021 (9)	0.0046 (8)	0.0013 (9)
C3	0.0424 (12)	0.0634 (15)	0.0295 (11)	0.0035 (10)	0.0009 (8)	0.0075 (10)
C4	0.0594 (14)	0.0556 (15)	0.0455 (13)	−0.0024 (12)	0.0089 (11)	0.0188 (11)
C5	0.0584 (14)	0.0491 (14)	0.0527 (14)	−0.0101 (11)	0.0075 (11)	0.0077 (11)
C6	0.0527 (13)	0.0505 (14)	0.0370 (12)	−0.0034 (10)	0.0001 (9)	−0.0003 (10)
C7	0.0726 (17)	0.0586 (16)	0.0487 (14)	−0.0108 (13)	−0.0031 (12)	−0.0026 (12)
C8	0.0443 (11)	0.0404 (11)	0.0299 (10)	0.0026 (9)	−0.0003 (8)	0.0024 (9)
C9	0.0875 (19)	0.0616 (16)	0.0553 (15)	0.0312 (14)	0.0260 (14)	0.0189 (13)
Cl1	0.0917 (6)	0.1055 (6)	0.0367 (4)	−0.0069 (4)	−0.0154 (3)	0.0111 (3)
N1	0.0523 (11)	0.0433 (10)	0.0308 (9)	0.0050 (8)	0.0021 (7)	0.0058 (8)

C1—C6	1.391 (3)	C6—H6	0.9300
C1—C2	1.404 (3)	C7—H7A	0.9600
C1—N1	1.417 (3)	C7—H7B	0.9600
C2—C3	1.392 (3)	C7—H7C	0.9600
C2—C7	1.498 (3)	C8—N1	1.273 (3)
C3—C4	1.373 (3)	C8—C9	1.493 (3)
C3—Cl1	1.751 (2)	C8—C8i	1.500 (4)
C4—C5	1.380 (3)	C9—H9A	0.9600
C4—H4	0.9300	C9—H9B	0.9600
C5—C6	1.378 (3)	C9—H9C	0.9600
C5—H5	0.9300
C6—C1—C2	120.64 (19)	C1—C6—H6	119.6
C6—C1—N1	120.53 (18)	C2—C7—H7A	109.5
C2—C1—N1	118.46 (19)	C2—C7—H7B	109.5
C3—C2—C1	116.2 (2)	H7A—C7—H7B	109.5
C3—C2—C7	123.0 (2)	C2—C7—H7C	109.5
C1—C2—C7	120.82 (19)	H7A—C7—H7C	109.5
C4—C3—C2	123.8 (2)	H7B—C7—H7C	109.5
C4—C3—Cl1	117.42 (17)	N1—C8—C9	126.12 (19)
C2—C3—Cl1	118.82 (18)	N1—C8—C8i	116.1 (2)
C3—C4—C5	118.8 (2)	C9—C8—C8i	117.8 (2)
C3—C4—H4	120.6	C8—C9—H9A	109.5
C5—C4—H4	120.6	C8—C9—H9B	109.5
C6—C5—C4	119.8 (2)	H9A—C9—H9B	109.5
C6—C5—H5	120.1	C8—C9—H9C	109.5
C4—C5—H5	120.1	H9A—C9—H9C	109.5
C5—C6—C1	120.8 (2)	H9B—C9—H9C	109.5
C5—C6—H6	119.6	C8—N1—C1	122.45 (18)
C6—C1—C2—C3	1.1 (3)	Cl1—C3—C4—C5	−179.88 (18)
N1—C1—C2—C3	174.16 (17)	C3—C4—C5—C6	0.4 (3)
C6—C1—C2—C7	−178.5 (2)	C4—C5—C6—C1	−0.2 (3)
N1—C1—C2—C7	−5.4 (3)	C2—C1—C6—C5	−0.6 (3)
C1—C2—C3—C4	−0.9 (3)	N1—C1—C6—C5	−173.5 (2)
C7—C2—C3—C4	178.6 (2)	C9—C8—N1—C1	−4.5 (3)
C1—C2—C3—Cl1	179.13 (14)	C8i—C8—N1—C1	176.6 (2)
C7—C2—C3—Cl1	−1.3 (3)	C6—C1—N1—C8	−67.6 (3)
C2—C3—C4—C5	0.2 (4)	C2—C1—N1—C8	119.4 (2)