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The dimerization of 2,6-dimethyl­phenyl isocyanide by a double insertion of 2,6-dimethyl­phenyl isocyanide with MeLi, followed by treatment with Me3SiCl, gave the title compound, C22H30N2Si, which adopts the trans configuration with respect to the position of the 2,6-dimethyl­phenyl­amine groups about the central C—C bond. The mol­ecule is stabilized by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021003/ym2004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021003/ym2004Isup2.hkl
Contains datablock I

CCDC reference: 613870

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.076
  • wR factor = 0.218
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.122 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT480_ALERT_4_C Long H...A H-Bond Reported H4C .. C7 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. C8 .. 2.80 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B .. C9 .. 3.15 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4C .. C11 .. 3.08 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C4 .. C7 .. 96.50 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.

1-Trimethylsilyl-2-methyl-1,2-bis(2,6-dimethylphenyl isonitrile) top
Crystal data top
C22H30N2SiF(000) = 760
Mr = 350.57Dx = 1.106 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4520 reflections
a = 8.159 (5) Åθ = 2.5–27.5°
b = 12.612 (8) ŵ = 0.12 mm1
c = 20.486 (12) ÅT = 150 K
β = 92.692 (8)°Plate, light orange
V = 2106 (2) Å30.18 × 0.16 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEX CCD with an Oxford Cryosystems low-temperature device
diffractometer
4258 independent reflections
Radiation source: normal-focus sealed tube3308 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.122
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.967, Tmax = 0.997k = 1514
11514 measured reflectionsl = 025
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.077H-atom parameters constrained
wR(F2) = 0.218 w = 1/[σ2(Fo2) + (0.0932P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
3308 reflectionsΔρmax = 0.35 e Å3
269 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (3)
Special details top

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.

It was quite difficult to get suitable crystals for the title compound. The data shows a crystal diffracting weakly,so that produces a Rint of 0.12. However, the highest diffraction symmetric compatible with cell metrics is like triclinic, P-1.

RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.122 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ········· 0.12 PLAT340_ALERT_3_C Low Bond Precision on C—C bonds (x 1000) Ang ··· 9

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.86950 (18)0.20827 (11)0.03501 (7)0.0549 (5)
N10.8171 (4)0.2990 (3)0.16380 (17)0.0431 (10)
N20.9935 (4)0.0551 (3)0.13450 (18)0.0457 (10)
C10.8647 (5)0.2214 (4)0.1286 (2)0.0427 (12)
C20.9249 (5)0.1267 (4)0.1681 (2)0.0427 (12)
C30.9025 (6)0.1233 (4)0.2391 (2)0.0517 (13)
H3A0.78850.11270.24680.078*
H3B0.93870.18910.25850.078*
H3C0.96560.06600.25810.078*
C40.7887 (6)0.3272 (4)0.0094 (2)0.0596 (15)
H4A0.79010.31500.05560.089*
H4B0.85610.38740.00200.089*
H4C0.67820.34060.00250.089*
C50.7335 (9)0.0955 (5)0.0113 (3)0.094 (2)
H5A0.62870.10500.02990.142*
H5B0.78200.03060.02730.142*
H5C0.71950.09250.03540.142*
C61.0843 (7)0.1912 (5)0.0098 (3)0.0824 (19)
H6A1.12960.12750.02890.124*
H6B1.14900.25090.02440.124*
H6C1.08490.18630.03700.124*
C70.7570 (5)0.3957 (3)0.1353 (2)0.0400 (11)
C80.8659 (5)0.4791 (4)0.1266 (2)0.0427 (12)
C90.8027 (6)0.5735 (4)0.1013 (2)0.0505 (13)
H90.87370.62970.09440.061*
C100.6380 (6)0.5859 (4)0.0861 (2)0.0533 (13)
H100.59840.64990.06920.064*
C110.5318 (6)0.5030 (4)0.0960 (2)0.0556 (14)
H110.42040.51180.08560.067*
C120.5880 (6)0.4065 (4)0.1211 (2)0.0480 (13)
C131.0464 (5)0.4653 (4)0.1414 (2)0.0596 (14)
H13A1.06360.43120.18310.089*
H13B1.09880.53350.14260.089*
H13C1.09230.42240.10820.089*
C140.4745 (6)0.3159 (4)0.1306 (3)0.0617 (15)
H14A0.49730.26050.10020.093*
H14B0.36320.33940.12320.093*
H14C0.48970.28950.17440.093*
C151.0606 (6)0.0390 (4)0.1621 (2)0.0420 (12)
C161.2322 (5)0.0483 (3)0.1701 (2)0.0444 (12)
C171.2967 (6)0.1438 (4)0.1891 (2)0.0524 (13)
H171.41000.15030.19480.063*
C181.2000 (6)0.2310 (4)0.2001 (2)0.0529 (13)
H181.24710.29570.21220.064*
C191.0299 (6)0.2202 (4)0.1928 (2)0.0521 (13)
H190.96330.27820.20080.062*
C200.9586 (5)0.1249 (4)0.1739 (2)0.0435 (12)
C211.3403 (6)0.0452 (4)0.1586 (2)0.0611 (15)
H21A1.45200.02720.17060.092*
H21B1.30660.10390.18460.092*
H21C1.33160.06430.11320.092*
C220.7744 (5)0.1165 (4)0.1665 (2)0.0575 (14)
H22A0.73370.08100.20390.086*
H22B0.72780.18630.16320.086*
H22C0.74450.07700.12770.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.0580 (10)0.0512 (10)0.0549 (9)0.0092 (8)0.0028 (7)0.0003 (8)
N10.028 (2)0.040 (2)0.061 (2)0.0012 (19)0.0048 (18)0.002 (2)
N20.037 (2)0.039 (3)0.060 (3)0.0039 (19)0.0053 (19)0.005 (2)
C10.023 (3)0.036 (3)0.068 (3)0.001 (2)0.005 (2)0.000 (3)
C20.029 (3)0.036 (3)0.062 (3)0.003 (2)0.005 (2)0.002 (3)
C30.050 (3)0.044 (3)0.060 (3)0.007 (2)0.006 (2)0.004 (3)
C40.060 (4)0.064 (4)0.054 (3)0.015 (3)0.006 (2)0.002 (3)
C50.138 (6)0.071 (4)0.072 (4)0.024 (4)0.020 (4)0.006 (3)
C60.082 (4)0.096 (5)0.071 (4)0.048 (4)0.025 (3)0.022 (3)
C70.033 (3)0.037 (3)0.050 (3)0.006 (2)0.001 (2)0.004 (2)
C80.036 (3)0.040 (3)0.052 (3)0.001 (2)0.004 (2)0.003 (2)
C90.043 (3)0.046 (3)0.062 (3)0.007 (2)0.006 (3)0.003 (3)
C100.052 (4)0.041 (3)0.065 (3)0.009 (3)0.010 (3)0.003 (3)
C110.043 (3)0.051 (3)0.072 (4)0.011 (3)0.006 (3)0.007 (3)
C120.038 (3)0.047 (3)0.058 (3)0.004 (2)0.001 (2)0.001 (3)
C130.035 (3)0.061 (4)0.082 (4)0.001 (3)0.010 (3)0.009 (3)
C140.038 (3)0.056 (4)0.091 (4)0.005 (2)0.003 (3)0.014 (3)
C150.038 (3)0.042 (3)0.046 (3)0.002 (2)0.002 (2)0.000 (2)
C160.034 (3)0.035 (3)0.063 (3)0.002 (2)0.000 (2)0.004 (3)
C170.030 (3)0.053 (3)0.074 (3)0.002 (3)0.002 (2)0.001 (3)
C180.034 (3)0.047 (3)0.077 (4)0.008 (2)0.003 (3)0.001 (3)
C190.043 (3)0.051 (3)0.062 (3)0.007 (3)0.004 (2)0.007 (3)
C200.033 (3)0.044 (3)0.053 (3)0.006 (2)0.005 (2)0.001 (3)
C210.045 (3)0.064 (4)0.074 (4)0.007 (3)0.003 (3)0.004 (3)
C220.040 (3)0.060 (3)0.072 (3)0.004 (3)0.000 (3)0.002 (3)
Geometric parameters (Å, º) top
Si1—C11.926 (5)C10—C111.379 (6)
Si1—C41.859 (5)C10—H100.9300
Si1—C51.854 (6)C11—C121.392 (6)
Si1—C61.863 (5)C11—H110.9300
N1—C11.288 (5)C12—C141.489 (6)
N1—C71.428 (5)C13—H13A0.9600
N2—C21.281 (5)C13—H13B0.9600
N2—C151.414 (5)C13—H13C0.9600
C1—C21.511 (6)C14—H14A0.9600
C2—C31.474 (6)C14—H14B0.9600
C3—H3A0.9600C14—H14C0.9600
C3—H3B0.9600C15—C201.394 (6)
C3—H3C0.9600C15—C161.407 (6)
C4—H4A0.9600C16—C171.364 (6)
C4—H4B0.9600C16—C211.497 (6)
C4—H4C0.9600C17—C181.379 (6)
C5—H5A0.9600C17—H170.9300
C5—H5B0.9600C18—C191.396 (6)
C5—H5C0.9600C18—H180.9300
C6—H6A0.9600C19—C201.384 (6)
C6—H6B0.9600C19—H190.9300
C6—H6C0.9600C20—C221.507 (6)
C7—C81.394 (6)C21—H21A0.9600
C7—C121.402 (6)C21—H21B0.9600
C8—C91.389 (6)C21—H21C0.9600
C8—C131.500 (6)C22—H22A0.9600
C9—C101.374 (6)C22—H22B0.9600
C9—H90.9300C22—H22C0.9600
C5—Si1—C4107.3 (3)C11—C10—H10120.2
C5—Si1—C6113.4 (3)C10—C11—C12121.3 (5)
C4—Si1—C6105.9 (2)C10—C11—H11119.4
C5—Si1—C1106.6 (2)C12—C11—H11119.4
C4—Si1—C1113.2 (2)C11—C12—C7117.8 (5)
C6—Si1—C1110.5 (2)C11—C12—C14121.5 (4)
C1—N1—C7121.8 (4)C7—C12—C14120.7 (4)
C2—N2—C15123.2 (4)C8—C13—H13A109.5
N1—C1—C2113.6 (4)C8—C13—H13B109.5
N1—C1—Si1130.1 (4)H13A—C13—H13B109.5
C2—C1—Si1116.4 (3)C8—C13—H13C109.5
N2—C2—C3126.0 (4)H13A—C13—H13C109.5
N2—C2—C1114.1 (4)H13B—C13—H13C109.5
C3—C2—C1119.9 (4)C12—C14—H14A109.5
C2—C3—H3A109.5C12—C14—H14B109.5
C2—C3—H3B109.5H14A—C14—H14B109.5
H3A—C3—H3B109.5C12—C14—H14C109.5
C2—C3—H3C109.5H14A—C14—H14C109.5
H3A—C3—H3C109.5H14B—C14—H14C109.5
H3B—C3—H3C109.5C20—C15—C16121.0 (4)
Si1—C4—H4A109.5C20—C15—N2119.9 (4)
Si1—C4—H4B109.5C16—C15—N2118.7 (4)
H4A—C4—H4B109.5C17—C16—C15118.3 (4)
Si1—C4—H4C109.5C17—C16—C21121.2 (4)
H4A—C4—H4C109.5C15—C16—C21120.5 (4)
H4B—C4—H4C109.5C16—C17—C18122.4 (4)
Si1—C5—H5A109.5C16—C17—H17118.8
Si1—C5—H5B109.5C18—C17—H17118.8
H5A—C5—H5B109.5C17—C18—C19118.6 (5)
Si1—C5—H5C109.5C17—C18—H18120.7
H5A—C5—H5C109.5C19—C18—H18120.7
H5B—C5—H5C109.5C20—C19—C18121.2 (4)
Si1—C6—H6A109.5C20—C19—H19119.4
Si1—C6—H6B109.5C18—C19—H19119.4
H6A—C6—H6B109.5C19—C20—C15118.5 (4)
Si1—C6—H6C109.5C19—C20—C22119.5 (4)
H6A—C6—H6C109.5C15—C20—C22122.0 (4)
H6B—C6—H6C109.5C16—C21—H21A109.5
C8—C7—C12121.8 (4)C16—C21—H21B109.5
C8—C7—N1119.2 (4)H21A—C21—H21B109.5
C12—C7—N1118.9 (4)C16—C21—H21C109.5
C9—C8—C7117.9 (4)H21A—C21—H21C109.5
C9—C8—C13121.2 (4)H21B—C21—H21C109.5
C7—C8—C13120.8 (4)C20—C22—H22A109.5
C10—C9—C8121.6 (4)C20—C22—H22B109.5
C10—C9—H9119.2H22A—C22—H22B109.5
C8—C9—H9119.2C20—C22—H22C109.5
C9—C10—C11119.7 (5)H22A—C22—H22C109.5
C9—C10—H10120.2H22B—C22—H22C109.5
C7—N1—C1—C2179.6 (3)C9—C10—C11—C120.0 (7)
C7—N1—C1—Si10.6 (6)C10—C11—C12—C70.8 (7)
C5—Si1—C1—N1118.8 (5)C10—C11—C12—C14178.7 (5)
C4—Si1—C1—N11.1 (5)C8—C7—C12—C111.9 (7)
C6—Si1—C1—N1117.5 (4)N1—C7—C12—C11177.3 (4)
C5—Si1—C1—C260.9 (4)C8—C7—C12—C14179.7 (4)
C4—Si1—C1—C2178.6 (3)N1—C7—C12—C144.8 (6)
C6—Si1—C1—C262.8 (4)C2—N2—C15—C2082.2 (6)
C15—N2—C2—C30.8 (7)C2—N2—C15—C16105.0 (5)
C15—N2—C2—C1179.0 (4)C20—C15—C16—C170.7 (7)
N1—C1—C2—N2170.8 (4)N2—C15—C16—C17172.0 (4)
Si1—C1—C2—N29.4 (5)C20—C15—C16—C21178.7 (4)
N1—C1—C2—C39.0 (6)N2—C15—C16—C218.6 (6)
Si1—C1—C2—C3170.8 (3)C15—C16—C17—C180.5 (7)
C1—N1—C7—C892.7 (5)C21—C16—C17—C18179.9 (4)
C1—N1—C7—C1291.7 (5)C16—C17—C18—C191.4 (7)
C12—C7—C8—C92.0 (7)C17—C18—C19—C201.0 (7)
N1—C7—C8—C9177.5 (4)C18—C19—C20—C150.1 (7)
C12—C7—C8—C13179.3 (4)C18—C19—C20—C22179.9 (4)
N1—C7—C8—C135.2 (6)C16—C15—C20—C191.0 (7)
C7—C8—C9—C101.1 (7)N2—C15—C20—C19171.6 (4)
C13—C8—C9—C10178.4 (4)C16—C15—C20—C22179.2 (4)
C8—C9—C10—C110.1 (7)N2—C15—C20—C228.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4C···C70.962.853.110 (7)97
C4—H4B···C80.962.803.415 (7)123
C4—H4B···C90.963.153.844 (7)131
C4—H4C···C110.963.083.794 (7)132
C4—H4C···C120.962.703.353 (7)126
 

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