(E)-N,N'-Bis(2,6-dimethyl-phen-yl)-N,N'-bis-(trichloro-silyl)ethyl-ene-1,2-diamine.

The asymmetric unit of the title compound, C(18)H(20)Cl(6)N(2)Si(2), contains one half of the centrosymmetric mol-ecule. The two benzene rings are perpendicular to the plane of Si-N-C=C-N-Si fragment, making a dihedral angle of 89.9 (1)°. The crystal packing exhibits short inter-molecular Cl⋯Cl contacts of 3.3119 (17) Å.

Related literature

For the geometric parameters of related compounds, see: Haaf et al. (1998 ▶, 2000 ▶); Baker et al. (2008 ▶); Jones et al. (2002 ▶).

Experimental

Crystal data

C18H20Cl6N2Si2

M = 533.24

Triclinic,

a = 8.1858 (3) Å

b = 8.4249 (3) Å

c = 10.6074 (4) Å

α = 74.583 (3)°

β = 79.999 (2)°

γ = 62.243 (2)°

V = 623.00 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.79 mm−1

T = 273 K

0.14 × 0.12 × 0.08 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.897, T max = 0.939

6168 measured reflections

2168 independent reflections

1729 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.202

S = 1.11

2168 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006011/cv2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006011/cv2522Isup2.hkl

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

C18H20Cl6N2Si2	Z = 1
Mr = 533.24	F(000) = 272
Triclinic, P1	Dx = 1.421 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1858 (3) Å	Cell parameters from 2127 reflections
b = 8.4249 (3) Å	θ = 2.8–25.6°
c = 10.6074 (4) Å	µ = 0.79 mm−1
α = 74.583 (3)°	T = 273 K
β = 79.999 (2)°	Block, yellow
γ = 62.243 (2)°	0.14 × 0.12 × 0.08 mm
V = 623.00 (4) Å3

Bruker APEX2 CCD area-detector diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	1729 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.897, Tmax = 0.939	k = −10→9
6168 measured reflections	l = −12→12

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.133P)2 + 0.1233P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.202	(Δ/σ)max = 0.088
S = 1.11	Δρmax = 0.57 e Å−3
2168 reflections	Δρmin = −0.50 e Å−3
129 parameters

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
Si1	0.34542 (14)	0.80312 (14)	0.19720 (9)	0.0424 (4)
Cl1	0.40381 (19)	1.01460 (17)	0.18495 (14)	0.0736 (5)
Cl2	0.54249 (18)	0.64298 (19)	0.08286 (14)	0.0791 (5)
Cl3	0.36689 (17)	0.65899 (17)	0.38326 (10)	0.0675 (4)
N1	0.1308 (4)	0.8729 (4)	0.1525 (3)	0.0394 (7)
C1	0.0820 (5)	0.9686 (5)	0.0214 (3)	0.0424 (9)
H1	0.1729	0.9875	−0.0375	0.051*
C2	−0.0078 (5)	0.8409 (5)	0.2452 (3)	0.0391 (8)
C3	−0.0237 (6)	0.6787 (5)	0.2607 (4)	0.0510 (10)
C4	−0.1436 (6)	0.6423 (6)	0.3580 (5)	0.0630 (12)
H4	−0.1535	0.5335	0.3706	0.076*
C5	−0.2502 (7)	0.7654 (8)	0.4378 (5)	0.0669 (13)
H5	−0.3294	0.7380	0.5042	0.080*
C6	−0.2389 (6)	0.9273 (7)	0.4189 (4)	0.0623 (12)
H6	−0.3130	1.0103	0.4716	0.075*
C7	−0.1181 (6)	0.9699 (6)	0.3218 (4)	0.0484 (9)
C8	0.0925 (9)	0.5424 (7)	0.1755 (7)	0.0816 (16)
H8A	0.2172	0.4774	0.2026	0.122*
H8B	0.0917	0.6064	0.0858	0.122*
H8C	0.0426	0.4569	0.1838	0.122*
C9	−0.1071 (8)	1.1485 (6)	0.3024 (6)	0.0736 (14)
H9A	−0.0312	1.1381	0.3666	0.110*
H9B	−0.2290	1.2451	0.3122	0.110*
H9C	−0.0541	1.1761	0.2162	0.110*

	U11	U22	U33	U12	U13	U23
Si1	0.0486 (7)	0.0433 (6)	0.0322 (6)	−0.0209 (5)	−0.0094 (4)	0.0021 (4)
Cl1	0.0869 (10)	0.0678 (8)	0.0823 (9)	−0.0503 (7)	−0.0180 (7)	−0.0021 (6)
Cl2	0.0655 (8)	0.0787 (9)	0.0780 (9)	−0.0180 (7)	0.0111 (6)	−0.0291 (7)
Cl3	0.0699 (8)	0.0822 (8)	0.0431 (6)	−0.0385 (7)	−0.0239 (5)	0.0208 (6)
N1	0.0483 (18)	0.0413 (16)	0.0266 (14)	−0.0197 (14)	−0.0087 (12)	−0.0002 (12)
C1	0.054 (2)	0.0413 (19)	0.0289 (18)	−0.0214 (18)	−0.0087 (15)	0.0009 (15)
C2	0.047 (2)	0.0440 (19)	0.0252 (16)	−0.0215 (17)	−0.0092 (14)	0.0006 (15)
C3	0.059 (3)	0.046 (2)	0.050 (2)	−0.025 (2)	−0.0104 (19)	−0.0050 (18)
C4	0.064 (3)	0.061 (3)	0.068 (3)	−0.038 (2)	−0.009 (2)	0.002 (2)
C5	0.061 (3)	0.094 (4)	0.047 (2)	−0.045 (3)	−0.001 (2)	0.001 (2)
C6	0.054 (3)	0.082 (3)	0.045 (2)	−0.024 (2)	0.0039 (19)	−0.021 (2)
C7	0.052 (2)	0.050 (2)	0.040 (2)	−0.0185 (19)	−0.0105 (17)	−0.0067 (17)
C8	0.096 (4)	0.059 (3)	0.100 (4)	−0.039 (3)	0.013 (3)	−0.035 (3)
C9	0.085 (4)	0.059 (3)	0.081 (3)	−0.029 (3)	0.004 (3)	−0.033 (3)

Si1—N1	1.684 (3)	C4—H4	0.9300
Si1—Cl3	2.0119 (13)	C5—C6	1.369 (7)
Si1—Cl2	2.0142 (17)	C5—H5	0.9300
Si1—Cl1	2.0170 (14)	C6—C7	1.396 (6)
N1—C1	1.428 (4)	C6—H6	0.9300
N1—C2	1.444 (4)	C7—C9	1.507 (6)
C1—C1i	1.307 (8)	C8—H8A	0.9600
C1—H1	0.9300	C8—H8B	0.9600
C2—C7	1.399 (6)	C8—H8C	0.9600
C2—C3	1.397 (5)	C9—H9A	0.9600
C3—C4	1.372 (6)	C9—H9B	0.9600
C3—C8	1.509 (7)	C9—H9C	0.9600
C4—C5	1.386 (7)
Cl3···Cl3ii	3.3119 (17)
N1—Si1—Cl3	108.46 (11)	C6—C5—C4	120.1 (4)
N1—Si1—Cl2	112.31 (12)	C6—C5—H5	120.0
Cl3—Si1—Cl2	108.64 (7)	C4—C5—H5	120.0
N1—Si1—Cl1	112.55 (11)	C5—C6—C7	121.1 (4)
Cl3—Si1—Cl1	109.04 (7)	C5—C6—H6	119.4
Cl2—Si1—Cl1	105.73 (7)	C7—C6—H6	119.4
C1—N1—C2	118.7 (3)	C2—C7—C6	117.8 (4)
C1—N1—Si1	120.1 (2)	C2—C7—C9	121.8 (4)
C2—N1—Si1	121.2 (2)	C6—C7—C9	120.4 (4)
C1i—C1—N1	124.4 (4)	C3—C8—H8A	109.5
C1i—C1—H1	117.8	C3—C8—H8B	109.5
N1—C1—H1	117.8	H8A—C8—H8B	109.5
C7—C2—C3	121.4 (3)	C3—C8—H8C	109.5
C7—C2—N1	119.1 (3)	H8A—C8—H8C	109.5
C3—C2—N1	119.5 (3)	H8B—C8—H8C	109.5
C4—C3—C2	118.7 (4)	C7—C9—H9A	109.5
C4—C3—C8	120.2 (4)	C7—C9—H9B	109.5
C2—C3—C8	121.0 (4)	H9A—C9—H9B	109.5
C3—C4—C5	120.9 (4)	C7—C9—H9C	109.5
C3—C4—H4	119.6	H9A—C9—H9C	109.5
C5—C4—H4	119.5	H9B—C9—H9C	109.5
Cl3—Si1—N1—C1	−176.0 (2)	N1—C2—C3—C4	173.7 (4)
Cl2—Si1—N1—C1	−55.9 (3)	C7—C2—C3—C8	178.5 (4)
Cl1—Si1—N1—C1	63.3 (3)	N1—C2—C3—C8	−4.4 (6)
Cl3—Si1—N1—C2	5.2 (3)	C2—C3—C4—C5	1.4 (7)
Cl2—Si1—N1—C2	125.3 (3)	C8—C3—C4—C5	179.5 (5)
Cl1—Si1—N1—C2	−115.5 (3)	C3—C4—C5—C6	1.0 (7)
C2—N1—C1—C1i	0.4 (7)	C4—C5—C6—C7	−1.5 (7)
Si1—N1—C1—C1i	−178.4 (4)	C3—C2—C7—C6	2.9 (6)
C1—N1—C2—C7	−91.3 (4)	N1—C2—C7—C6	−174.2 (3)
Si1—N1—C2—C7	87.6 (4)	C3—C2—C7—C9	−177.7 (4)
C1—N1—C2—C3	91.6 (4)	N1—C2—C7—C9	5.2 (6)
Si1—N1—C2—C3	−89.6 (4)	C5—C6—C7—C2	−0.5 (6)
C7—C2—C3—C4	−3.4 (6)	C5—C6—C7—C9	−179.9 (5)