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In the centrosymmetric title compound, [Ru(CN)2(C9H17N)4], the central Ru atom is octa­hedrally coordinated by four isocyanide and two cyanide ligands in a trans configuration. The corresponding cis isomer, which is also produced in the reaction of Ru3(CO)12 with isooctylisocyanide, is not configurationally stable and slowly isomerizes into the trans isomer in solution.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021532/at2039sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021532/at2039Isup2.hkl
Contains datablock I

CCDC reference: 613567

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.072
  • Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.51 Ratio
Author Response: Some of the methyl groups show high thermal parameters but they were not refinable in terms of disordered tert. butyl substituents.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C2      ..       8.27 su
Author Response: This problem might be due to the fact that no absorption correction was applied. Nevertheless, it does not seem to be too serious considering R- values and standard deviations of bond lengths and angles.
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ru1    -   C2      ..      12.58 su
Author Response: This problem might be due to the fact that no absorption correction was applied. Nevertheless, it does not seem to be too serious considering R- values and standard deviations of bond lengths and angles.

Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.48 Ratio
Author Response: Some of the methyl groups show high thermal parameters but they were not refinable in terms of disordered tert. butyl substituents.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C12     ..       5.02 su
Author Response: This problem might be due to the fact that no absorption correction was applied. Nevertheless, it does not seem to be too serious considering R- values and standard deviations of bond lengths and angles.
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ru1    -   C1      ..       8.01 su
Author Response: This problem might be due to the fact that no absorption correction was applied. Nevertheless, it does not seem to be too serious considering R- values and standard deviations of bond lengths and angles.
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ru1    -   C11     ..       9.83 su
Author Response: This problem might be due to the fact that no absorption correction was applied. Nevertheless, it does not seem to be too serious considering R- values and standard deviations of bond lengths and angles.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
Author Response: This is the quarternary carbon atom of a tert. butyl group with the methyl groups showing high thermal parameters but they were not refinable in terms of disordered tert. butyl substituents.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      33.00 A   3  
Author Response: This is most probably due to the very bulky isooctyl substituents. Nevertheless, no electron density was observed which could be attributed to a solvent molecule.

0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 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 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

trans-Dicyanotetrakis(1,1,3,3-tetramethylbutyl isocyanide)ruthenium(II) top
Crystal data top
[Ru(CN)2(C8H17N)4]F(000) = 764
Mr = 710.06Dx = 1.097 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4878 reflections
a = 10.3752 (2) Åθ = 2.7–27.5°
b = 13.6464 (5) ŵ = 0.39 mm1
c = 15.3603 (5) ÅT = 173 K
β = 98.800 (2)°Block, colourless
V = 2149.17 (11) Å30.12 × 0.10 × 0.07 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
3547 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
φ and ω scansh = 1313
8584 measured reflectionsk = 1716
4878 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0318P)2 + 0.0187P]
where P = (Fo2 + 2Fc2)/3
4878 reflections(Δ/σ)max = 0.001
215 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.46 e Å3
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
Ru10.00000.00000.00000.01594 (7)
C10.14218 (17)0.06158 (15)0.06333 (12)0.0247 (4)
N10.22373 (16)0.09461 (16)0.09605 (12)0.0430 (5)
C20.13965 (17)0.08932 (14)0.05798 (12)0.0207 (4)
N20.22796 (14)0.13528 (12)0.08896 (10)0.0235 (4)
C30.35829 (17)0.17351 (15)0.12154 (13)0.0265 (5)
C40.3437 (2)0.28145 (17)0.14447 (15)0.0411 (6)
H4A0.29350.28690.19340.062*
H4B0.43020.31050.16180.062*
H4C0.29800.31620.09300.062*
C50.4082 (2)0.11477 (19)0.20450 (13)0.0389 (6)
H5A0.34720.12170.24690.058*
H5B0.41530.04550.18910.058*
H5C0.49410.13940.23070.058*
C60.44555 (18)0.15084 (18)0.05124 (13)0.0353 (5)
H6A0.53700.15790.08050.042*
H6B0.43270.08070.03600.042*
C70.43438 (18)0.20726 (19)0.03665 (14)0.0368 (6)
C80.29437 (18)0.2167 (2)0.08365 (14)0.0421 (6)
H8A0.24450.25800.04860.063*
H8B0.29430.24670.14160.063*
H8C0.25430.15160.09090.063*
C90.5099 (2)0.1458 (3)0.09572 (16)0.0669 (9)
H9A0.50890.17910.15230.100*
H9B0.60020.13760.06680.100*
H9C0.46870.08130.10570.100*
C100.4980 (3)0.3081 (2)0.02555 (18)0.0722 (10)
H10A0.44610.35100.00670.108*
H10B0.58630.30180.00740.108*
H10C0.50260.33630.08370.108*
C110.05030 (16)0.09345 (14)0.09957 (12)0.0206 (4)
N30.08281 (14)0.14724 (12)0.15633 (10)0.0252 (4)
C120.12474 (17)0.21359 (15)0.22995 (12)0.0243 (4)
C130.23146 (19)0.16028 (17)0.29176 (14)0.0355 (5)
H13A0.19670.09860.31130.053*
H13B0.26110.20170.34310.053*
H13C0.30500.14630.26060.053*
C140.00758 (18)0.23104 (17)0.27742 (14)0.0334 (5)
H14A0.01590.16960.30410.050*
H14B0.06650.25420.23510.050*
H14C0.03000.28050.32350.050*
C150.18591 (17)0.30676 (15)0.19704 (13)0.0259 (4)
H15A0.21990.34520.25030.031*
H15B0.26290.28480.17140.031*
C160.11275 (19)0.37975 (16)0.13091 (14)0.0331 (5)
C170.0657 (3)0.33358 (18)0.04076 (15)0.0483 (6)
H17A0.00560.28780.04560.072*
H17B0.13800.29820.02070.072*
H17C0.03460.38510.00170.072*
C180.0030 (2)0.42938 (19)0.16432 (18)0.0528 (7)
H18A0.07450.38230.16310.079*
H18B0.03240.48530.12640.079*
H18C0.02400.45230.22480.079*
C190.2124 (3)0.4600 (2)0.1194 (2)0.0587 (8)
H19A0.24250.49100.17650.088*
H19B0.17140.50950.07790.088*
H19C0.28680.43090.09660.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01688 (11)0.01551 (11)0.01478 (11)0.00013 (9)0.00037 (7)0.00130 (11)
C10.0228 (10)0.0276 (12)0.0219 (10)0.0015 (8)0.0023 (8)0.0045 (9)
N10.0268 (9)0.0646 (15)0.0366 (11)0.0073 (9)0.0019 (8)0.0210 (10)
C20.0263 (10)0.0190 (10)0.0171 (10)0.0048 (8)0.0048 (8)0.0033 (8)
N20.0231 (8)0.0253 (10)0.0217 (9)0.0051 (7)0.0021 (6)0.0032 (7)
C30.0194 (9)0.0352 (13)0.0237 (11)0.0061 (8)0.0010 (8)0.0020 (9)
C40.0457 (13)0.0373 (14)0.0404 (14)0.0137 (11)0.0073 (10)0.0133 (12)
C50.0373 (12)0.0555 (16)0.0224 (11)0.0004 (11)0.0007 (9)0.0010 (11)
C60.0202 (10)0.0568 (16)0.0286 (12)0.0039 (10)0.0027 (8)0.0062 (11)
C70.0230 (10)0.0602 (17)0.0273 (12)0.0001 (10)0.0038 (8)0.0078 (11)
C80.0312 (11)0.0645 (18)0.0294 (12)0.0011 (11)0.0005 (9)0.0157 (12)
C90.0532 (16)0.115 (3)0.0376 (15)0.0289 (17)0.0220 (12)0.0178 (17)
C100.0684 (19)0.092 (3)0.0546 (18)0.0408 (17)0.0036 (15)0.0207 (17)
C110.0197 (9)0.0197 (10)0.0222 (10)0.0019 (7)0.0025 (7)0.0022 (9)
N30.0290 (8)0.0225 (10)0.0224 (9)0.0011 (7)0.0010 (7)0.0025 (8)
C120.0274 (10)0.0246 (11)0.0197 (10)0.0032 (8)0.0000 (8)0.0092 (9)
C130.0368 (11)0.0380 (14)0.0288 (12)0.0031 (10)0.0040 (9)0.0025 (10)
C140.0333 (11)0.0375 (14)0.0307 (12)0.0082 (10)0.0091 (9)0.0111 (10)
C150.0250 (10)0.0234 (11)0.0292 (11)0.0032 (8)0.0036 (8)0.0056 (9)
C160.0352 (11)0.0252 (12)0.0398 (13)0.0002 (9)0.0083 (9)0.0006 (10)
C170.0681 (16)0.0405 (16)0.0341 (14)0.0087 (12)0.0007 (12)0.0119 (12)
C180.0585 (16)0.0406 (16)0.0614 (17)0.0217 (12)0.0160 (13)0.0053 (14)
C190.0582 (17)0.0357 (14)0.081 (2)0.0093 (13)0.0086 (15)0.0144 (16)
Geometric parameters (Å, º) top
Ru1—C21.9958 (19)C10—H10A0.9800
Ru1—C2i1.9958 (19)C10—H10B0.9800
Ru1—C11i1.998 (2)C10—H10C0.9800
Ru1—C111.998 (2)C11—N31.150 (2)
Ru1—C12.0658 (19)N3—C121.462 (2)
Ru1—C1i2.0658 (19)C12—C131.528 (3)
C1—N11.141 (2)C12—C141.529 (2)
C2—N21.151 (2)C12—C151.540 (3)
N2—C31.464 (2)C13—H13A0.9800
C3—C51.527 (3)C13—H13B0.9800
C3—C41.527 (3)C13—H13C0.9800
C3—C61.543 (3)C14—H14A0.9800
C4—H4A0.9800C14—H14B0.9800
C4—H4B0.9800C14—H14C0.9800
C4—H4C0.9800C15—C161.538 (3)
C5—H5A0.9800C15—H15A0.9900
C5—H5B0.9800C15—H15B0.9900
C5—H5C0.9800C16—C171.532 (3)
C6—C71.543 (3)C16—C191.535 (3)
C6—H6A0.9900C16—C181.534 (3)
C6—H6B0.9900C17—H17A0.9800
C7—C81.526 (3)C17—H17B0.9800
C7—C101.525 (4)C17—H17C0.9800
C7—C91.536 (3)C18—H18A0.9800
C8—H8A0.9800C18—H18B0.9800
C8—H8B0.9800C18—H18C0.9800
C8—H8C0.9800C19—H19A0.9800
C9—H9A0.9800C19—H19B0.9800
C9—H9B0.9800C19—H19C0.9800
C9—H9C0.9800
C2—Ru1—C2i180.00 (9)H9A—C9—H9C109.5
C2—Ru1—C11i92.21 (7)H9B—C9—H9C109.5
C2i—Ru1—C11i87.79 (7)C7—C10—H10A109.5
C2—Ru1—C1187.79 (7)C7—C10—H10B109.5
C2i—Ru1—C1192.21 (7)H10A—C10—H10B109.5
C11i—Ru1—C11180.0C7—C10—H10C109.5
C2—Ru1—C193.64 (7)H10A—C10—H10C109.5
C2i—Ru1—C186.36 (7)H10B—C10—H10C109.5
C11i—Ru1—C188.80 (7)N3—C11—Ru1178.05 (15)
C11—Ru1—C191.20 (7)C11—N3—C12178.61 (19)
C2—Ru1—C1i86.36 (7)N3—C12—C13106.70 (16)
C2i—Ru1—C1i93.64 (7)N3—C12—C14107.52 (15)
C11i—Ru1—C1i91.20 (7)C13—C12—C14109.35 (17)
C11—Ru1—C1i88.80 (7)N3—C12—C15110.26 (15)
C1—Ru1—C1i180.0C13—C12—C15107.52 (15)
N1—C1—Ru1177.74 (17)C14—C12—C15115.19 (17)
N2—C2—Ru1173.99 (16)C12—C13—H13A109.5
C2—N2—C3165.96 (19)C12—C13—H13B109.5
N2—C3—C5106.00 (16)H13A—C13—H13B109.5
N2—C3—C4107.66 (16)C12—C13—H13C109.5
C5—C3—C4110.28 (18)H13A—C13—H13C109.5
N2—C3—C6107.42 (15)H13B—C13—H13C109.5
C5—C3—C6108.56 (16)C12—C14—H14A109.5
C4—C3—C6116.38 (18)C12—C14—H14B109.5
C3—C4—H4A109.5H14A—C14—H14B109.5
C3—C4—H4B109.5C12—C14—H14C109.5
H4A—C4—H4B109.5H14A—C14—H14C109.5
C3—C4—H4C109.5H14B—C14—H14C109.5
H4A—C4—H4C109.5C16—C15—C12124.40 (16)
H4B—C4—H4C109.5C16—C15—H15A106.2
C3—C5—H5A109.5C12—C15—H15A106.2
C3—C5—H5B109.5C16—C15—H15B106.2
H5A—C5—H5B109.5C12—C15—H15B106.2
C3—C5—H5C109.5H15A—C15—H15B106.4
H5A—C5—H5C109.5C17—C16—C19108.5 (2)
H5B—C5—H5C109.5C17—C16—C18109.06 (19)
C3—C6—C7122.60 (18)C19—C16—C18107.4 (2)
C3—C6—H6A106.7C17—C16—C15112.80 (18)
C7—C6—H6A106.7C19—C16—C15105.39 (18)
C3—C6—H6B106.7C18—C16—C15113.43 (18)
C7—C6—H6B106.7C16—C17—H17A109.5
H6A—C6—H6B106.6C16—C17—H17B109.5
C8—C7—C10109.9 (2)H17A—C17—H17B109.5
C8—C7—C9107.56 (19)C16—C17—H17C109.5
C10—C7—C9107.9 (2)H17A—C17—H17C109.5
C8—C7—C6113.26 (16)H17B—C17—H17C109.5
C10—C7—C6112.29 (19)C16—C18—H18A109.5
C9—C7—C6105.5 (2)C16—C18—H18B109.5
C7—C8—H8A109.5H18A—C18—H18B109.5
C7—C8—H8B109.5C16—C18—H18C109.5
H8A—C8—H8B109.5H18A—C18—H18C109.5
C7—C8—H8C109.5H18B—C18—H18C109.5
H8A—C8—H8C109.5C16—C19—H19A109.5
H8B—C8—H8C109.5C16—C19—H19B109.5
C7—C9—H9A109.5H19A—C19—H19B109.5
C7—C9—H9B109.5C16—C19—H19C109.5
H9A—C9—H9B109.5H19A—C19—H19C109.5
C7—C9—H9C109.5H19B—C19—H19C109.5
Symmetry code: (i) x, y, z.
 

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