Buy article online - an online subscription or single-article purchase is required to access this article.
share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Supporting information
Supporting informationclose
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2007). E63, m2567
https://doi.org/10.1107/S1600536807045825
Download PDF of article
Download PDF of articleclose
Supporting information
Supporting informationclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

μ-[Bis(3,3-dimethyl­but-1-yn­yl)diphenyl­silane]bis­[(cyclo­octa-1,5-diene)­nickel(II)](Ni—Ni)

W. Imhof, T. Klettke and D. Walther
The title compound, [Ni2(C24H28Si)(C8H12)2], was obtained from the reaction of the symmetrical diyne bis­(3,3-dimethyl­but-1-yn­yl)diphenyl­silane with bis­(cyclo­octa-1,5-diene)nickel. In the resulting mol­ecule, two Ni(cod) (cod is cyclo­octa-1,5-diene) units are coordinated by one of the C[triple bond]C triple bonds, resulting in the formation of a dinickelatetra­hedrane. The second triple bond remains uncoordinated even if an excess amount of the diyne is used in the reaction.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045825/cf2141sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045825/cf2141Isup2.hkl
Contains datablock I

CCDC reference: 663622

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.027
  • wR factor = 0.070
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found




Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.63 Ratio
Author Response: The highest Ueq values are observed for methyl groups of tert. butyl groups and some aromatic CH functions. Unfortunately, it was not possible to refine any disorder in these regions of the molecule. On the other hand, the lowest Ueq values are those for quarternary carbon atoms and carbon atoms that are bound to the nickel atoms which therefore show a very low thermal motion. 

Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C9
Author Response: The highest Ueq values are observed for methyl groups of tert. butyl groups and some aromatic CH functions (e.g. C16). Unfortunately, it was not possible to refine any disorder in these regions of the molecule. On the other hand, the lowest Ueq values are those for quarternary carbon atoms (e.g. C9 and C13)and carbon atoms that are bound to the nickel atoms which therefore show a very low thermal motion. 

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.82
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
Author Response: The highest Ueq values are observed for methyl groups of tert. butyl groups and some aromatic CH functions (e.g. C16). Unfortunately, it was not possible to refine any disorder in these regions of the molecule. On the other hand, the lowest Ueq values are those for quarternary carbon atoms (e.g. C9 and C13)and carbon atoms that are bound to the nickel atoms which therefore show a very low thermal motion. 
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
Author Response: The highest Ueq values are observed for methyl groups of tert. butyl groups and some aromatic CH functions (e.g. C16). Unfortunately, it was not possible to refine any disorder in these regions of the molecule. On the other hand, the lowest Ueq values are those for quarternary carbon atoms (e.g. C9 and C13)and carbon atoms that are bound to the nickel atoms which therefore show a very low thermal motion. 
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C1     -   C2     ...       1.35 Ang.


Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.822
            Tmax scaled      0.745 Tmin scaled      0.676
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.45
           From the CIF: _reflns_number_total               4246
           Count of symmetry unique reflns         4280
           Completeness (_total/calc)             99.21%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1


   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

In the course of a study on the reactivity of alkynols and alkynylsilanes toward Ni(0) compounds such as [Ni(cdt)] (cdt = 1,5,9-cyclododecatriene) or [Ni(cod)2] (cod = cycloocta-1,5-diene) it was shown that the reactions with alkynes produce organometallic compounds of the general formulae [Ni(alkyne)2] or [Ni3(alkyne)4] which crystallize as hydrogen-bonded supramolecular structures if alkynols are used as the starting material (Braga et al., 1997; Klettke et al., 1996; Walther et al., 1994, 1995, 1997; Walther, Klettke, Imhof & Görls, 1996; Walther, Klettke, Schmidt et al., 1996). The reaction of tert-butyltriphenylsilylacetylene with [Ni(cod)2] leads to a mononuclear complex in which one Ni(cod) unit is coordinated by the carbon-carbon triple bond (Walther et al., 1997). In contrast, the reaction of the symmetrical diyne bis(3,3-dimethylbut-1-ynyl)diphenylsilane does not lead to a dinuclear nickel complex with one Ni(cod) fragment per carbon-carbon triple bond but to the title compound 1.

Corresponding to the IR spectrum, which is indicative of one coordinated and one non-coordinated carbon-carbon triple bond, the structural analysis of the title compound shows that two Ni(cod) units are bound to one of the alkynyl subunits, thereby establishing a nickel–nickel bond and forming a dinickelatetrahedrane derivative. By coordination to the transition metal centers the C1—C2 bond is elongated by 0.152 Å compared to the uncoordinated C3—C4 bond. In addition, the bond angles Si1—C2—C1 and C2—C1—C5 are observed to be 153.8 (3) and 141.3 (3)°, respectively, whereas the corresponding bond angles Si1—C3—C4 and C3—C4—C9 are close to linearity [175.5 (3) and 178.8 (4)°].

Related literature top

The closely related complex [(tert-butyltriphenylsilylacetlyene)nickel(cycloocta-1,5-diene)] was reported by Walther et al. (1997). For other related literature, see: Braga et al. (1997); Klettke et al. (1996); Walther et al. (1994, 1995); Walther, Klettke, Imhof & Görls (1996); Walther, Klettke, Schmidt et al. (1996).

Experimental top

1.04 mmol (285 mg) [Ni(cod)2] and 0.52 mmol (179 mg) bis-3,3-dimethylbut-1-ynyl)diphenylsilane were combined in 10 ml n-pentane and stirred at room temperature until all the starting material had dissolved. During the reaction the solution developed an intense red color. After the reaction had finished the solution was kept at 273 K. Two days later deep red crystals suitable for X-ray structural analysis could be collected (0.24 mmol, 163 mg, yield 46.4%). IR (nujol mull, 295 K): 1521 cm-1, 2147 cm-1; MS (EI): 676 (M+, 1), 568 (M+ - cod, 1), 510 (M+– Ni(cod), 3), 460 (M+ - Ni(cod) - C3H8, 5, 67 (C5H7, 100); elemental analysis for C40H52SiNi2 (calcd.): C 70.72 (70.83), H 7.98 (7.73), Ni 17.42 (17.30)%.

Refinement top

Hydrogen atoms were positioned geometrically and refined using a riding model with with C—H = 0.95–0.99 Å and with Uiso(H) = 1.5Ueq(C).

Structure description top

In the course of a study on the reactivity of alkynols and alkynylsilanes toward Ni(0) compounds such as [Ni(cdt)] (cdt = 1,5,9-cyclododecatriene) or [Ni(cod)2] (cod = cycloocta-1,5-diene) it was shown that the reactions with alkynes produce organometallic compounds of the general formulae [Ni(alkyne)2] or [Ni3(alkyne)4] which crystallize as hydrogen-bonded supramolecular structures if alkynols are used as the starting material (Braga et al., 1997; Klettke et al., 1996; Walther et al., 1994, 1995, 1997; Walther, Klettke, Imhof & Görls, 1996; Walther, Klettke, Schmidt et al., 1996). The reaction of tert-butyltriphenylsilylacetylene with [Ni(cod)2] leads to a mononuclear complex in which one Ni(cod) unit is coordinated by the carbon-carbon triple bond (Walther et al., 1997). In contrast, the reaction of the symmetrical diyne bis(3,3-dimethylbut-1-ynyl)diphenylsilane does not lead to a dinuclear nickel complex with one Ni(cod) fragment per carbon-carbon triple bond but to the title compound 1.

Corresponding to the IR spectrum, which is indicative of one coordinated and one non-coordinated carbon-carbon triple bond, the structural analysis of the title compound shows that two Ni(cod) units are bound to one of the alkynyl subunits, thereby establishing a nickel–nickel bond and forming a dinickelatetrahedrane derivative. By coordination to the transition metal centers the C1—C2 bond is elongated by 0.152 Å compared to the uncoordinated C3—C4 bond. In addition, the bond angles Si1—C2—C1 and C2—C1—C5 are observed to be 153.8 (3) and 141.3 (3)°, respectively, whereas the corresponding bond angles Si1—C3—C4 and C3—C4—C9 are close to linearity [175.5 (3) and 178.8 (4)°].

The closely related complex [(tert-butyltriphenylsilylacetlyene)nickel(cycloocta-1,5-diene)] was reported by Walther et al. (1997). For other related literature, see: Braga et al. (1997); Klettke et al. (1996); Walther et al. (1994, 1995); Walther, Klettke, Imhof & Görls (1996); Walther, Klettke, Schmidt et al. (1996).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the labeling scheme and 40% probability displacement ellipsoids for non-H atoms.
µ-[Bis(3,3-dimethylbut-1-ynyl)diphenylsilane]bis[(cycloocta-1,5- diene)nickel(II)](Ni—Ni) top
Crystal data top
[Ni2(C24H28Si)(C8H12)2]F(000) = 724
Mr = 678.31Dx = 1.276 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 10.167 (2) Åθ = 13.4–25.1°
b = 9.617 (2) ŵ = 1.13 mm−1
c = 18.110 (4) ÅT = 183 K
β = 94.68 (3)°Block, red
V = 1764.8 (6) Å30.32 × 0.28 × 0.26 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer		3931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
ω/2θ scansh = −1→13
Absorption correction: ψ scan
(North et al., 1968)		k = −12→0
Tmin = 0.823, Tmax = 0.906l = −23→23
4489 measured reflections3 standard reflections every 120 min
4246 independent reflections intensity decay: 0.1%
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)] = 0.027H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0315P)2 + 0.65P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
4246 reflectionsΔρmax = 0.38 e Å−3
394 parametersΔρmin = −0.32 e Å−3
1 restraintAbsolute structure: Flack (1983), with 4 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.006 (13)
Crystal data top
[Ni2(C24H28Si)(C8H12)2]V = 1764.8 (6) Å3
Mr = 678.31Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.167 (2) ŵ = 1.13 mm−1
b = 9.617 (2) ÅT = 183 K
c = 18.110 (4) Å0.32 × 0.28 × 0.26 mm
β = 94.68 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		3931 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.019
Tmin = 0.823, Tmax = 0.9063 standard reflections every 120 min
4489 measured reflections intensity decay: 0.1%
4246 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.070Δρmax = 0.38 e Å−3
S = 1.15Δρmin = −0.32 e Å−3
4246 reflectionsAbsolute structure: Flack (1983), with 4 Friedel pairs
394 parametersAbsolute structure parameter: 0.006 (13)
1 restraint
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.47667 (4)0.78591 (4)0.21857 (2)0.02036 (9)
Ni20.24266 (3)0.83291 (4)0.14742 (2)0.01928 (9)
Si10.22104 (8)0.62681 (9)0.29347 (4)0.01964 (17)
C10.3630 (3)0.6769 (3)0.15160 (16)0.0188 (6)
C20.3092 (3)0.6903 (3)0.21689 (16)0.0191 (6)
C30.1678 (3)0.7751 (4)0.34747 (16)0.0271 (6)
C40.1411 (3)0.8711 (4)0.38577 (18)0.0279 (7)
C50.3926 (3)0.5685 (4)0.09442 (16)0.0234 (6)
C60.2651 (4)0.5011 (4)0.06099 (19)0.0314 (8)
H6A0.28590.43440.02270.047*
H6B0.20610.57310.03890.047*
H6C0.22180.45260.09990.047*
C70.4639 (3)0.6365 (4)0.03206 (18)0.0317 (8)
H7A0.47170.5691−0.00790.048*
H7B0.55210.66650.05150.048*
H7C0.41330.71730.01280.048*
C80.4802 (4)0.4529 (4)0.1306 (2)0.0349 (8)
H8A0.50830.39030.09220.052*
H8B0.43020.40020.16520.052*
H8C0.55810.49440.15750.052*
C90.1072 (4)0.9914 (4)0.4316 (2)0.0356 (8)
C10−0.0308 (5)1.0402 (7)0.4058 (4)0.085 (2)
H10A−0.05371.12090.43520.127*
H10B−0.09390.96500.41220.127*
H10C−0.03391.06630.35340.127*
C110.2042 (6)1.1091 (6)0.4213 (3)0.0704 (16)
H11A0.17971.19040.44980.106*
H11B0.20181.13360.36870.106*
H11C0.29351.07910.43870.106*
C120.1168 (7)0.9489 (7)0.5128 (3)0.087 (2)
H12A0.08581.02530.54260.130*
H12B0.20890.92750.52920.130*
H12C0.06210.86640.51880.130*
C130.3236 (3)0.5201 (4)0.36372 (17)0.0266 (7)
C140.3126 (4)0.5377 (5)0.4386 (2)0.0442 (10)
H140.25040.60270.45450.066*
C150.3905 (5)0.4625 (6)0.4915 (2)0.0506 (11)
H150.38050.47650.54270.076*
C160.4795 (5)0.3707 (5)0.4706 (2)0.0491 (11)
H160.53170.31880.50680.074*
C170.4948 (6)0.3521 (7)0.3972 (2)0.082 (2)
H170.55830.28770.38220.123*
C180.4180 (6)0.4269 (6)0.3444 (2)0.0665 (17)
H180.43080.41370.29350.100*
C190.0709 (3)0.5251 (3)0.25825 (17)0.0226 (6)
C200.0106 (3)0.5454 (4)0.18705 (19)0.0318 (8)
H200.04840.60980.15510.048*
C21−0.1031 (4)0.4744 (5)0.1614 (2)0.0403 (9)
H21−0.14230.48990.11270.061*
C22−0.1582 (4)0.3807 (5)0.2079 (3)0.0550 (12)
H22−0.23630.33190.19140.082*
C23−0.1006 (4)0.3587 (6)0.2772 (3)0.0642 (15)
H23−0.13880.29400.30890.096*
C240.0122 (4)0.4286 (5)0.3022 (2)0.0442 (10)
H240.05100.41050.35080.066*
C250.6186 (3)0.8906 (4)0.1628 (2)0.0326 (8)
H250.56920.87520.11670.049*
C260.6765 (3)0.7778 (5)0.19708 (18)0.0321 (7)
H260.66230.69030.17350.048*
C270.7616 (3)0.7799 (6)0.2694 (2)0.0427 (9)
H27A0.80410.87220.27590.064*
H27B0.83220.70940.26760.064*
C280.6818 (4)0.7499 (5)0.3366 (2)0.0438 (10)
H28A0.67260.64810.34210.066*
H28B0.73130.78570.38200.066*
C290.5460 (3)0.8150 (5)0.32953 (17)0.0361 (9)
H290.47660.76080.34660.054*
C300.5120 (4)0.9419 (5)0.3016 (2)0.0361 (9)
H300.42110.96580.29870.054*
C310.6064 (4)1.0495 (5)0.2746 (2)0.0478 (10)
H31A0.69321.03930.30300.072*
H31B0.57251.14350.28450.072*
C320.6256 (5)1.0369 (5)0.1912 (3)0.0471 (10)
H32A0.55691.09290.16300.071*
H32B0.71251.07670.18190.071*
C330.1711 (3)0.8718 (4)0.03922 (18)0.0334 (8)
H330.20320.78500.02320.050*
C340.2636 (4)0.9702 (4)0.0607 (2)0.0334 (8)
H340.35370.94370.06150.050*
C350.2341 (5)1.1186 (5)0.0832 (3)0.0488 (11)
H35A0.15111.14940.05570.073*
H35B0.30581.18000.06880.073*
C360.2208 (6)1.1350 (5)0.1664 (3)0.0556 (12)
H36A0.30861.15680.19140.083*
H36B0.16211.21500.17410.083*
C370.1669 (4)1.0092 (4)0.2022 (2)0.0367 (8)
H370.21100.98160.24810.055*
C380.0622 (3)0.9299 (5)0.1766 (2)0.0353 (8)
H380.04180.85040.20460.053*
C39−0.0238 (4)0.9600 (7)0.1062 (2)0.0571 (14)
H39A−0.02541.06160.09740.086*
H39B−0.11510.92980.11280.086*
C400.0242 (4)0.8871 (7)0.0385 (2)0.0540 (13)
H40A−0.01620.79340.03450.081*
H40B−0.00780.9399−0.00640.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01796 (17)0.02247 (19)0.02058 (18)−0.00277 (16)0.00111 (13)−0.00417 (16)
Ni20.01797 (17)0.01904 (18)0.02100 (18)0.00099 (15)0.00264 (13)0.00367 (15)
Si10.0218 (4)0.0197 (4)0.0176 (4)−0.0009 (3)0.0027 (3)0.0016 (3)
C10.0178 (13)0.0168 (14)0.0211 (13)−0.0009 (12)−0.0017 (10)−0.0001 (12)
C20.0183 (13)0.0197 (15)0.0193 (13)−0.0005 (12)0.0010 (11)0.0036 (12)
C30.0313 (15)0.0281 (16)0.0224 (13)−0.0017 (15)0.0056 (12)0.0016 (14)
C40.0317 (17)0.0283 (18)0.0243 (15)0.0001 (14)0.0058 (13)−0.0008 (13)
C50.0274 (15)0.0217 (16)0.0208 (14)0.0022 (13)0.0000 (12)−0.0042 (12)
C60.0336 (18)0.0288 (19)0.0313 (18)−0.0054 (15)−0.0009 (14)−0.0086 (15)
C70.0330 (17)0.034 (2)0.0287 (16)0.0009 (16)0.0095 (14)−0.0079 (15)
C80.0389 (19)0.0273 (19)0.0375 (18)0.0113 (16)−0.0037 (15)−0.0073 (16)
C90.041 (2)0.0310 (19)0.0358 (18)0.0017 (17)0.0059 (15)−0.0112 (16)
C100.053 (3)0.067 (4)0.133 (5)0.019 (3)−0.005 (3)−0.047 (4)
C110.085 (4)0.037 (3)0.092 (4)−0.016 (3)0.029 (3)−0.026 (3)
C120.165 (7)0.062 (4)0.035 (2)0.019 (4)0.019 (3)−0.012 (2)
C130.0324 (17)0.0248 (17)0.0220 (14)−0.0032 (14)−0.0020 (12)0.0042 (13)
C140.053 (2)0.051 (3)0.0297 (18)0.014 (2)0.0068 (17)0.0096 (18)
C150.071 (3)0.057 (3)0.0232 (17)0.010 (2)−0.0018 (18)0.0112 (19)
C160.063 (3)0.049 (3)0.0328 (19)0.011 (2)−0.0110 (18)0.0103 (18)
C170.112 (4)0.094 (5)0.038 (2)0.075 (4)−0.004 (3)0.000 (3)
C180.095 (4)0.080 (4)0.0233 (18)0.052 (3)−0.007 (2)−0.005 (2)
C190.0216 (14)0.0198 (15)0.0270 (15)−0.0011 (12)0.0051 (12)−0.0010 (12)
C200.0294 (17)0.036 (2)0.0299 (17)−0.0027 (16)0.0044 (14)−0.0026 (15)
C210.0326 (18)0.042 (2)0.045 (2)0.0022 (18)−0.0055 (16)−0.0128 (18)
C220.032 (2)0.035 (2)0.094 (4)−0.0092 (18)−0.015 (2)0.002 (2)
C230.039 (2)0.055 (3)0.097 (4)−0.017 (2)−0.006 (2)0.038 (3)
C240.0343 (19)0.046 (2)0.051 (2)−0.0139 (18)−0.0038 (17)0.021 (2)
C250.0291 (17)0.0346 (19)0.0350 (18)−0.0114 (15)0.0082 (14)−0.0045 (16)
C260.0199 (14)0.0391 (19)0.0378 (17)−0.0057 (16)0.0061 (12)−0.0104 (18)
C270.0255 (16)0.055 (2)0.047 (2)0.0020 (19)−0.0045 (14)−0.011 (2)
C280.0377 (19)0.057 (3)0.0341 (18)−0.003 (2)−0.0123 (15)−0.0043 (19)
C290.0315 (16)0.052 (3)0.0238 (14)−0.0107 (18)−0.0033 (12)−0.0116 (16)
C300.0316 (18)0.042 (2)0.0341 (18)−0.0038 (17)0.0011 (15)−0.0203 (17)
C310.047 (2)0.037 (2)0.059 (3)−0.008 (2)0.002 (2)−0.019 (2)
C320.049 (2)0.031 (2)0.063 (3)−0.0119 (19)0.010 (2)−0.005 (2)
C330.0330 (17)0.040 (2)0.0266 (16)0.0051 (16)−0.0020 (13)0.0090 (15)
C340.0343 (18)0.033 (2)0.0346 (18)0.0073 (16)0.0111 (15)0.0150 (15)
C350.063 (3)0.030 (2)0.056 (3)0.005 (2)0.024 (2)0.015 (2)
C360.083 (3)0.024 (2)0.065 (3)0.004 (2)0.031 (3)0.004 (2)
C370.045 (2)0.0276 (19)0.0398 (19)0.0096 (17)0.0172 (16)0.0038 (16)
C380.0290 (17)0.045 (2)0.0334 (18)0.0102 (17)0.0110 (14)0.0100 (17)
C390.0280 (19)0.095 (4)0.048 (2)0.021 (2)0.0048 (17)0.013 (3)
C400.032 (2)0.088 (4)0.040 (2)0.010 (2)−0.0097 (17)0.003 (2)
Geometric parameters (Å, º) top
Ni1—C11.917 (3)C17—H170.950
Ni1—C21.933 (3)C18—H180.950
Ni1—C252.086 (3)C19—C241.389 (5)
Ni1—C292.093 (3)C19—C201.396 (5)
Ni1—C262.101 (3)C20—C211.389 (5)
Ni1—C302.134 (4)C20—H200.950
Ni1—Ni22.6505 (9)C21—C221.382 (7)
Ni2—C11.933 (3)C21—H210.950
Ni2—C21.945 (3)C22—C231.358 (7)
Ni2—C332.068 (3)C22—H220.950
Ni2—C342.077 (3)C23—C241.374 (6)
Ni2—C372.139 (4)C23—H230.950
Ni2—C382.161 (4)C24—H240.950
Si1—C21.817 (3)C25—C261.360 (6)
Si1—C31.836 (4)C25—C321.498 (6)
Si1—C191.880 (3)C25—H250.950
Si1—C131.882 (3)C26—C271.510 (5)
C1—C21.349 (4)C26—H260.950
C1—C51.517 (4)C27—C281.542 (5)
C3—C41.199 (5)C27—H27A0.990
C4—C91.480 (5)C27—H27B0.990
C5—C61.529 (4)C28—C291.512 (5)
C5—C81.538 (5)C28—H28A0.990
C5—C71.537 (5)C28—H28B0.990
C6—H6A0.980C29—C301.355 (6)
C6—H6B0.980C29—H290.950
C6—H6C0.980C30—C311.519 (6)
C7—H7A0.980C30—H300.950
C7—H7B0.980C31—C321.543 (6)
C7—H7C0.980C31—H31A0.990
C8—H8A0.980C31—H31B0.990
C8—H8B0.980C32—H32A0.990
C8—H8C0.980C32—H32B0.990
C9—C101.516 (6)C33—C341.368 (5)
C9—C111.523 (6)C33—C401.500 (5)
C9—C121.522 (6)C33—H330.950
C10—H10A0.980C34—C351.520 (6)
C10—H10B0.980C34—H340.950
C10—H10C0.980C35—C361.532 (6)
C11—H11A0.980C35—H35A0.990
C11—H11B0.980C35—H35B0.990
C11—H11C0.980C36—C371.497 (6)
C12—H12A0.980C36—H36A0.990
C12—H12B0.980C36—H36B0.990
C12—H12C0.980C37—C381.360 (6)
C13—C181.379 (6)C37—H370.950
C13—C141.380 (5)C38—C391.513 (5)
C14—C151.395 (6)C38—H380.950
C14—H140.950C39—C401.527 (7)
C15—C161.341 (7)C39—H39A0.990
C15—H150.950C39—H39B0.990
C16—C171.363 (6)C40—H40A0.990
C16—H160.950C40—H40B0.990
C17—C181.385 (6)
C1—Ni1—C241.02 (12)C17—C16—H16120.2
C1—Ni1—C25111.24 (13)C16—C17—C18120.1 (4)
C2—Ni1—C25149.87 (13)C16—C17—H17119.9
C1—Ni1—C29144.97 (15)C18—C17—H17119.9
C2—Ni1—C29107.81 (13)C13—C18—C17121.9 (4)
C25—Ni1—C29102.01 (15)C13—C18—H18119.1
C1—Ni1—C26113.86 (13)C17—C18—H18119.1
C2—Ni1—C26147.49 (15)C24—C19—C20116.5 (3)
C25—Ni1—C2637.89 (16)C24—C19—Si1121.9 (3)
C29—Ni1—C2685.86 (14)C20—C19—Si1121.6 (3)
C1—Ni1—C30152.67 (14)C21—C20—C19122.1 (4)
C2—Ni1—C30116.29 (14)C21—C20—H20119.0
C25—Ni1—C3085.32 (15)C19—C20—H20119.0
C29—Ni1—C3037.37 (17)C22—C21—C20118.9 (4)
C26—Ni1—C3092.68 (14)C22—C21—H21120.5
C1—Ni1—Ni246.76 (9)C20—C21—H21120.5
C2—Ni1—Ni247.07 (9)C23—C22—C21120.0 (4)
C25—Ni1—Ni2108.13 (11)C23—C22—H22120.0
C29—Ni1—Ni2131.49 (10)C21—C22—H22120.0
C26—Ni1—Ni2139.42 (10)C22—C23—C24120.9 (4)
C30—Ni1—Ni2108.40 (11)C22—C23—H23119.5
C1—Ni2—C240.71 (12)C24—C23—H23119.5
C1—Ni2—C33110.49 (14)C23—C24—C19121.6 (4)
C2—Ni2—C33144.84 (15)C23—C24—H24119.2
C1—Ni2—C34114.79 (14)C19—C24—H24119.2
C2—Ni2—C34152.39 (13)C26—C25—C32125.9 (4)
C33—Ni2—C3438.54 (15)C26—C25—Ni171.7 (2)
C1—Ni2—C37147.93 (14)C32—C25—Ni1107.6 (3)
C2—Ni2—C37112.22 (14)C26—C25—H25117.1
C33—Ni2—C37100.60 (16)C32—C25—H25117.1
C34—Ni2—C3784.82 (15)Ni1—C25—H2590.8
C1—Ni2—C38150.73 (14)C25—C26—C27125.6 (4)
C2—Ni2—C38113.81 (14)C25—C26—Ni170.46 (19)
C33—Ni2—C3885.03 (14)C27—C26—Ni1109.4 (2)
C34—Ni2—C3892.97 (14)C25—C26—H26117.2
C37—Ni2—C3836.87 (16)C27—C26—H26117.2
C1—Ni2—Ni146.25 (8)Ni1—C26—H2690.1
C2—Ni2—Ni146.69 (9)C26—C27—C28112.4 (3)
C33—Ni2—Ni1136.38 (10)C26—C27—H27A109.1
C34—Ni2—Ni1109.45 (11)C28—C27—H27A109.1
C37—Ni2—Ni1104.63 (12)C26—C27—H27B109.1
C38—Ni2—Ni1134.50 (10)C28—C27—H27B109.1
C2—Si1—C3109.30 (15)H27A—C27—H27B107.9
C2—Si1—C19110.69 (14)C29—C28—C27113.0 (3)
C3—Si1—C19108.57 (14)C29—C28—H28A109.0
C2—Si1—C13114.74 (14)C27—C28—H28A109.0
C3—Si1—C13103.58 (15)C29—C28—H28B109.0
C19—Si1—C13109.59 (15)C27—C28—H28B109.0
C2—C1—C5141.4 (3)H28A—C28—H28B107.8
C2—C1—Ni170.11 (18)C30—C29—C28127.4 (4)
C5—C1—Ni1131.7 (2)C30—C29—Ni172.9 (2)
C2—C1—Ni270.10 (18)C28—C29—Ni1105.0 (2)
C5—C1—Ni2131.8 (2)C30—C29—H29116.3
Ni1—C1—Ni287.00 (13)C28—C29—H29116.3
C1—C2—Si1153.8 (3)Ni1—C29—H2992.2
C1—C2—Ni168.86 (17)C29—C30—C31125.8 (4)
Si1—C2—Ni1129.53 (16)C29—C30—Ni169.7 (2)
C1—C2—Ni269.19 (18)C31—C30—Ni1109.0 (2)
Si1—C2—Ni2124.29 (16)C29—C30—H30117.1
Ni1—C2—Ni286.24 (13)C31—C30—H30117.1
C4—C3—Si1175.5 (3)Ni1—C30—H3091.3
C3—C4—C9178.8 (4)C30—C31—C32113.3 (3)
C1—C5—C6110.7 (3)C30—C31—H31A108.9
C1—C5—C8110.3 (2)C32—C31—H31A108.9
C6—C5—C8107.8 (3)C30—C31—H31B108.9
C1—C5—C7109.9 (3)C32—C31—H31B108.9
C6—C5—C7108.9 (3)H31A—C31—H31B107.7
C8—C5—C7109.2 (3)C25—C32—C31113.8 (4)
C5—C6—H6A109.5C25—C32—H32A108.8
C5—C6—H6B109.5C31—C32—H32A108.8
H6A—C6—H6B109.5C25—C32—H32B108.8
C5—C6—H6C109.5C31—C32—H32B108.8
H6A—C6—H6C109.5H32A—C32—H32B107.7
H6B—C6—H6C109.5C34—C33—C40126.5 (4)
C5—C7—H7A109.5C34—C33—Ni271.1 (2)
C5—C7—H7B109.5C40—C33—Ni2107.4 (2)
H7A—C7—H7B109.5C34—C33—H33116.7
C5—C7—H7C109.5C40—C33—H33116.7
H7A—C7—H7C109.5Ni2—C33—H3391.6
H7B—C7—H7C109.5C33—C34—C35125.4 (4)
C5—C8—H8A109.5C33—C34—Ni270.4 (2)
C5—C8—H8B109.5C35—C34—Ni2111.0 (3)
H8A—C8—H8B109.5C33—C34—H34117.3
C5—C8—H8C109.5C35—C34—H34117.3
H8A—C8—H8C109.5Ni2—C34—H3488.5
H8B—C8—H8C109.5C34—C35—C36113.3 (3)
C4—C9—C10108.7 (3)C34—C35—H35A108.9
C4—C9—C11109.2 (3)C36—C35—H35A108.9
C10—C9—C11108.9 (5)C34—C35—H35B108.9
C4—C9—C12109.4 (4)C36—C35—H35B108.9
C10—C9—C12111.5 (5)H35A—C35—H35B107.7
C11—C9—C12109.1 (4)C37—C36—C35114.0 (4)
C9—C10—H10A109.5C37—C36—H36A108.7
C9—C10—H10B109.5C35—C36—H36A108.7
H10A—C10—H10B109.5C37—C36—H36B108.7
C9—C10—H10C109.5C35—C36—H36B108.7
H10A—C10—H10C109.5H36A—C36—H36B107.6
H10B—C10—H10C109.5C38—C37—C36127.5 (4)
C9—C11—H11A109.5C38—C37—Ni272.4 (2)
C9—C11—H11B109.5C36—C37—Ni2106.4 (2)
H11A—C11—H11B109.5C38—C37—H37116.2
C9—C11—H11C109.5C36—C37—H37116.2
H11A—C11—H11C109.5Ni2—C37—H3791.3
H11B—C11—H11C109.5C37—C38—C39124.2 (4)
C9—C12—H12A109.5C37—C38—Ni270.7 (2)
C9—C12—H12B109.5C39—C38—Ni2108.7 (3)
H12A—C12—H12B109.5C37—C38—H38117.9
C9—C12—H12C109.5C39—C38—H38117.9
H12A—C12—H12C109.5Ni2—C38—H3890.6
H12B—C12—H12C109.5C38—C39—C40112.8 (4)
C18—C13—C14116.3 (3)C38—C39—H39A109.0
C18—C13—Si1122.8 (3)C40—C39—H39A109.0
C14—C13—Si1120.8 (3)C38—C39—H39B109.0
C13—C14—C15121.6 (4)C40—C39—H39B109.0
C13—C14—H14119.2H39A—C39—H39B107.8
C15—C14—H14119.2C33—C40—C39114.9 (3)
C16—C15—C14120.4 (4)C33—C40—H40A108.5
C16—C15—H15119.8C39—C40—H40A108.5
C14—C15—H15119.8C33—C40—H40B108.5
C15—C16—C17119.7 (4)C39—C40—H40B108.5
C15—C16—H16120.2H40A—C40—H40B107.5

Experimental details

Crystal data
Chemical formula[Ni2(C24H28Si)(C8H12)2]
Mr678.31
Crystal system, space groupMonoclinic, P21
Temperature (K)183
a, b, c (Å)10.167 (2), 9.617 (2), 18.110 (4)
β (°) 94.68 (3)
V (Å3)1764.8 (6)
Z2
Radiation typeMo Kα
µ (mm−1)1.13
Crystal size (mm)0.32 × 0.28 × 0.26
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.823, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections		4489, 4246, 3931
Rint0.019
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.070, 1.15
No. of reflections4246
No. of parameters394
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.38, −0.32
Absolute structureFlack (1983), with 4 Friedel pairs
Absolute structure parameter0.006 (13)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), SET4 (de Boer & Duisenberg, 1984), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990).

 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS