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The title compound, [VCl(C7H7N){Fe(C8H13NSi)2}] or [FeV(C7H7N)(C8H13NSi)2Cl], crystallizes with the aromatic ring in the p-tolyl­imido unit parallel to the two cyclo­penta­dienyl rings of the ferrocene moiety; the vanadium-bound chloride ion also lies in the plane occupied by the imido ligand. A mirror plane bisects the molecule through the V atom, the imido ligand and the Fe atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032648/wm2041sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032648/wm2041IIsup2.hkl
Contains datablock II

CCDC reference: 621519

Key indicators

  • Single-crystal X-ray study
  • T = 147 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.027
  • wR factor = 0.034
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.72 Deg.
Author Response: Due to the detector configuration employed, data beyond 0.85 \%A was not collected.

Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5884 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.72 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.08 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Si1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 1998); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.

Chloro(p-tolylimido-κN)[N,N'-(trimethylsilyl)ferrocene-1,1'- diaminato-κ2N,N']vanadium(V) top
Crystal data top
[FeV(C7H7N)(C8H13NSi)2Cl]F(000) = 1144.00
Mr = 549.95Dx = 1.388 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ac 2nCell parameters from 3806 reflections
a = 14.981 (1) Åθ = 3.3–24.6°
b = 15.423 (1) ŵ = 1.11 mm1
c = 11.3884 (8) ÅT = 147 K
V = 2631.4 (3) Å3Prism, red
Z = 40.27 × 0.21 × 0.17 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
1752 reflections with I > 3σ(I)
ω scansRint = 0.024
Absorption correction: multi-scan
(Blessing, 1995)
θmax = 24.7°
Tmin = 0.728, Tmax = 0.828h = 017
11979 measured reflectionsk = 018
2332 independent reflectionsl = 013
Refinement top
Refinement on FH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027 w = 1/[σ2(Fo) + 0.00022|Fo|2]
wR(F2) = 0.035(Δ/σ)max = 0.0004
S = 1.55Δρmax = 0.39 e Å3
1752 reflectionsΔρmin = 0.34 e Å3
157 parameters
Special details top

Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 3.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.58299 (3)0.25000.04443 (5)0.0243 (2)
V10.79806 (4)0.25000.02787 (5)0.0205 (2)
Cl10.82425 (6)0.25000.22308 (8)0.0312 (3)
Si10.80551 (5)0.04670 (5)0.05816 (7)0.0288 (2)
N10.7514 (1)0.1429 (1)0.0155 (2)0.0229 (6)
N20.9020 (2)0.25000.0222 (2)0.0239 (8)
C10.6597 (2)0.1427 (2)0.0163 (2)0.0229 (7)
C20.5861 (2)0.1443 (2)0.0634 (2)0.0271 (7)
C30.5068 (2)0.1439 (2)0.0044 (3)0.0343 (8)
C40.5294 (2)0.1422 (2)0.1236 (3)0.0357 (8)
C50.6238 (2)0.1411 (2)0.1326 (2)0.0274 (7)
C60.7184 (2)0.0363 (2)0.0836 (3)0.052 (1)
C70.8799 (2)0.0118 (2)0.0627 (3)0.068 (1)
C80.8704 (2)0.0670 (2)0.1930 (3)0.054 (1)
C90.9946 (2)0.25000.0348 (3)0.0220 (10)
C101.0348 (2)0.25000.1446 (3)0.026 (1)
C111.1278 (2)0.25000.1522 (3)0.028 (1)
C121.1812 (2)0.25000.0535 (3)0.026 (1)
C131.1396 (2)0.25000.0554 (3)0.030 (1)
C141.0472 (2)0.25000.0653 (3)0.0250 (10)
C151.2809 (3)0.25000.0640 (4)0.038 (1)
H10.58970.14540.14660.0325*
H20.44780.14460.02610.0412*
H30.48860.14180.18750.0429*
H40.65730.13960.20340.0329*
H51.17510.25000.12450.0354*
H61.02010.25000.14070.0300*
H70.99940.25000.21380.0308*
H81.15510.25000.22750.0332*
H91.29620.25000.14550.0455*
H101.30410.19970.02800.0455*
H110.68560.04520.01320.0618*
H120.67930.01710.14380.0618*
H130.74580.08920.10670.0618*
H140.84540.00170.13140.0812*
H150.90970.04010.04090.0812*
H160.92260.05590.07790.0812*
H170.89910.01500.21680.0649*
H180.83150.08630.25340.0649*
H190.91410.11030.17800.0649*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0168 (3)0.0220 (3)0.0342 (3)0.00000.0028 (2)0.0000
V10.0159 (3)0.0202 (3)0.0254 (3)0.00000.0013 (3)0.0000
Cl10.0244 (5)0.0432 (6)0.0260 (5)0.00000.0015 (4)0.0000
Si10.0271 (4)0.0223 (4)0.0371 (5)0.0033 (3)0.0044 (3)0.0023 (3)
N10.019 (1)0.020 (1)0.029 (1)0.0007 (9)0.0024 (9)0.0002 (9)
N20.019 (2)0.025 (2)0.027 (2)0.00000.001 (1)0.0000
C10.021 (1)0.016 (1)0.032 (2)0.000 (1)0.001 (1)0.000 (1)
C20.025 (1)0.024 (1)0.033 (2)0.004 (1)0.003 (1)0.002 (1)
C30.019 (1)0.029 (2)0.055 (2)0.005 (1)0.003 (1)0.001 (1)
C40.028 (2)0.028 (2)0.051 (2)0.004 (1)0.016 (1)0.003 (1)
C50.029 (1)0.024 (1)0.029 (2)0.000 (1)0.000 (1)0.005 (1)
C60.050 (2)0.026 (2)0.079 (2)0.003 (1)0.014 (2)0.012 (2)
C70.069 (2)0.055 (2)0.079 (3)0.034 (2)0.021 (2)0.005 (2)
C80.066 (2)0.037 (2)0.059 (2)0.007 (2)0.028 (2)0.015 (2)
C90.016 (2)0.019 (2)0.031 (2)0.00000.004 (2)0.0000
C100.021 (2)0.031 (2)0.025 (2)0.00000.004 (2)0.0000
C110.024 (2)0.030 (2)0.029 (2)0.00000.009 (2)0.0000
C120.018 (2)0.023 (2)0.036 (2)0.00000.000 (2)0.0000
C130.025 (2)0.034 (2)0.030 (2)0.00000.006 (2)0.0000
C140.021 (2)0.031 (2)0.023 (2)0.00000.003 (2)0.0000
C150.025 (2)0.042 (3)0.048 (3)0.00000.002 (2)0.0000
Geometric parameters (Å, º) top
Fe1—C12.040 (2)C9—C141.386 (5)
Fe1—C1i2.040 (2)C10—C111.396 (5)
Fe1—C22.042 (3)C11—C121.379 (5)
Fe1—C2i2.042 (3)C12—C131.388 (5)
Fe1—C32.047 (3)C12—C151.499 (5)
Fe1—C3i2.047 (3)C13—C141.389 (5)
Fe1—C42.055 (3)C2—H10.950
Fe1—C4i2.055 (3)C3—H20.950
Fe1—C52.050 (3)C4—H30.950
Fe1—C5i2.050 (3)C5—H40.950
V1—Cl12.257 (1)C6—H110.950
V1—N11.861 (2)C6—H120.950
V1—N1i1.861 (2)C6—H130.950
V1—N21.658 (3)C7—H140.950
Si1—N11.759 (2)C7—H150.950
Si1—C61.850 (3)C7—H160.950
Si1—C71.851 (3)C8—H170.950
Si1—C81.844 (3)C8—H180.950
N1—C11.420 (3)C8—H190.950
N2—C91.395 (4)C10—H70.950
C1—C21.427 (3)C11—H80.950
C1—C51.430 (3)C13—H50.950
C2—C31.418 (4)C14—H60.950
C3—C41.399 (4)C15—H90.956
C4—C51.418 (4)C15—H100.943
C9—C101.388 (5)C15—H10i0.943
C1—Fe1—C1i108.4 (1)Fe1—C5—C470.0 (2)
C1—Fe1—C240.94 (10)C1—C5—C4107.9 (2)
C1—Fe1—C2i122.72 (10)N2—C9—C10121.6 (3)
C1—Fe1—C368.3 (1)N2—C9—C14118.8 (3)
C1—Fe1—C3i158.1 (1)C10—C9—C14119.6 (3)
C1—Fe1—C468.44 (10)C9—C10—C11119.2 (3)
C1—Fe1—C4i161.0 (1)C10—C11—C12121.9 (3)
C1—Fe1—C540.93 (10)C11—C12—C13117.9 (3)
C1—Fe1—C5i125.02 (10)C11—C12—C15120.9 (3)
C2—Fe1—C2i106.0 (1)C13—C12—C15121.2 (3)
C2—Fe1—C340.6 (1)C12—C13—C14121.3 (3)
C2—Fe1—C3i121.2 (1)C9—C14—C13120.0 (3)
C2—Fe1—C468.1 (1)Fe1—C2—H1125.910
C2—Fe1—C4i156.8 (1)C1—C2—H1126.231
C2—Fe1—C568.5 (1)C3—C2—H1126.232
C2—Fe1—C5i160.4 (1)Fe1—C3—H2126.228
C3—Fe1—C3i106.2 (1)C2—C3—H2125.510
C3—Fe1—C439.9 (1)C4—C3—H2125.513
C3—Fe1—C4i121.8 (1)Fe1—C4—H3126.310
C3—Fe1—C567.7 (1)C3—C4—H3125.917
C3—Fe1—C5i158.5 (1)C5—C4—H3125.915
C4—Fe1—C4i108.0 (1)Fe1—C5—H4126.364
C4—Fe1—C540.4 (1)C1—C5—H4126.024
C4—Fe1—C5i124.4 (1)C4—C5—H4126.027
C5—Fe1—C5i110.0 (1)Si1—C6—H11109.470
CL1—V1—N1109.09 (6)Si1—C6—H12109.469
CL1—V1—N1i109.09 (6)Si1—C6—H13109.472
CL1—V1—N2100.1 (1)H11—C6—H12109.469
N1—V1—N1i125.2 (1)H11—C6—H13109.475
N1—V1—N2105.16 (7)H12—C6—H13109.472
N1—V1i—N2105.16 (7)Si1—C7—H14109.463
N1—Si1—C6107.5 (1)Si1—C7—H15109.463
N1—Si1—C7108.5 (1)Si1—C7—H16109.465
N1—Si1—C8109.2 (1)H14—C7—H15109.476
C6—Si1—C7109.8 (2)H14—C7—H16109.481
C6—Si1—C8111.1 (2)H15—C7—H16109.480
C7—Si1—C8110.6 (2)Si1—C8—H17109.460
V1—N1—Si1130.4 (1)Si1—C8—H18109.466
V1—N1—C1107.3 (2)Si1—C8—H19109.464
Si1—N1—C1120.9 (2)H17—C8—H18109.478
V1—N2—C9165.7 (3)H17—C8—H19109.476
Fe1—C1—N1125.6 (2)H18—C8—H19109.484
Fe1—C1—C269.6 (1)C9—C10—H7120.384
Fe1—C1—C569.9 (1)C11—C10—H7120.384
N1—C1—C2125.8 (2)C10—C11—H8119.048
N1—C1—C5126.9 (2)C12—C11—H8119.037
C2—C1—C5107.4 (2)C12—C13—H5119.332
Fe1—C2—C169.5 (1)C14—C13—H5119.336
Fe1—C2—C369.9 (1)C9—C14—H6120.001
C1—C2—C3107.5 (2)C13—C14—H6119.996
Fe1—C3—C269.5 (1)C12—C15—H9108.351
Fe1—C3—C470.4 (2)C12—C15—H10109.377
C2—C3—C4109.0 (2)C12—C15—H10i109.377
Fe1—C4—C369.8 (2)H9—C15—H10109.512
Fe1—C4—C569.6 (1)H9—C15—H10i109.512
C3—C4—C5108.2 (2)H10—C15—H10i110.673
Fe1—C5—C169.2 (1)
Fe1—C1—N1—V121.1 (2)C1—Fe1—C5—C4119.3 (2)
Fe1—C1—N1—Si1170.6 (1)C1—Fe1—C5i—C4i163.3 (2)
Fe1—C1—C2—C359.8 (2)C1—N1—Si1—C612.5 (2)
Fe1—C1—C5—C459.5 (2)C1—N1—Si1—C7106.3 (2)
Fe1—C1i—N1i—V121.1 (2)C1—N1—Si1—C8133.1 (2)
Fe1—C1i—N1i—Si1i170.6 (1)C1—C2—Fe1—C2i121.8 (1)
Fe1—C1i—C2i—C3i59.8 (2)C1—C2—Fe1—C3118.6 (2)
Fe1—C1i—C5i—C4i59.5 (2)C1—C2—Fe1—C3i163.2 (1)
Fe1—C2—C1—N1119.9 (2)C1—C2—Fe1—C481.9 (2)
Fe1—C2—C1—C559.9 (2)C1—C2—Fe1—C4i166.6 (2)
Fe1—C2—C3—C459.5 (2)C1—C2—Fe1—C538.3 (1)
Fe1—C2i—C1i—N1i119.9 (2)C1—C2—Fe1—C5i51.2 (4)
Fe1—C2i—C1i—C5i59.9 (2)C1—C2—C3—C40.1 (3)
Fe1—C2i—C3i—C4i59.5 (2)C1—C5—Fe1—C238.3 (1)
Fe1—C3—C2—C159.6 (2)C1—C5—Fe1—C2i38.8 (4)
Fe1—C3—C4—C559.2 (2)C1—C5—Fe1—C382.2 (2)
Fe1—C3i—C2i—C1i59.6 (2)C1—C5—Fe1—C3i159.4 (3)
Fe1—C3i—C4i—C5i59.2 (2)C1—C5—Fe1—C4119.3 (2)
Fe1—C4—C3—C258.9 (2)C1—C5—Fe1—C4i163.7 (1)
Fe1—C4—C5—C159.0 (2)C1—C5—Fe1—C5i120.8 (1)
Fe1—C4i—C3i—C2i58.9 (2)C1—C5—C4—C30.3 (3)
Fe1—C4i—C5i—C1i59.0 (2)C2—Fe1—C1—C5118.4 (2)
Fe1—C5—C1—N1120.1 (3)C2—Fe1—C1i—C5i165.5 (1)
Fe1—C5—C1—C259.7 (2)C2—Fe1—C2i—C3i119.5 (1)
Fe1—C5—C4—C359.3 (2)C2—Fe1—C3—C4120.1 (2)
Fe1—C5i—C1i—N1i120.1 (3)C2—Fe1—C3i—C4i162.0 (1)
Fe1—C5i—C1i—C2i59.7 (2)C2—Fe1—C4—C337.3 (2)
Fe1—C5i—C4i—C3i59.3 (2)C2—Fe1—C4—C582.1 (2)
V1—N1—Si1—C6177.8 (2)C2—Fe1—C4i—C3i42.0 (3)
V1—N1—Si1—C759.0 (2)C2—Fe1—C4i—C5i161.5 (2)
V1—N1—Si1—C861.6 (2)C2—Fe1—C5—C481.0 (2)
V1—N1—C1—C2110.4 (2)C2—Fe1—C5i—C4i158.1 (3)
V1—N1—C1—C569.4 (3)C2—C1—Fe1—C337.9 (2)
V1—N1i—C1i—C2i110.4 (2)C2—C1—Fe1—C3i41.4 (3)
V1—N1i—C1i—C5i69.4 (3)C2—C1—Fe1—C481.0 (2)
V1—N2—C9—C10180.0C2—C1—Fe1—C4i163.8 (3)
V1—N2—C9—C140.0C2—C1—Fe1—C5118.4 (2)
CL1—V1—N1—Si188.4 (1)C2—C1—Fe1—C5i161.4 (1)
CL1—V1—N1—C178.5 (2)C2—C1—C5—C40.3 (3)
CL1—V1—N1i—Si1i88.4 (1)C2—C3—Fe1—C3i119.3 (1)
CL1—V1—N1i—C1i78.5 (2)C2—C3—Fe1—C4120.1 (2)
CL1—V1—N2—C90.0C2—C3—Fe1—C4i159.8 (2)
Si1—N1—V1—N1i139.78 (10)C2—C3—Fe1—C582.5 (2)
Si1—N1—V1—N218.3 (2)C2—C3—Fe1—C5i170.7 (3)
Si1—N1—C1—C281.3 (3)C2—C3—C4—C50.3 (3)
Si1—N1—C1—C598.9 (3)C3—Fe1—C1—C580.5 (2)
N1—V1—N1i—C1i53.4 (2)C3—Fe1—C1i—C5i159.8 (2)
N1—V1—N2—C9113.11 (7)C3—Fe1—C3i—C4i120.5 (1)
N1—C1—Fe1—C1i1.0 (3)C3—Fe1—C4—C5119.5 (2)
N1—C1—Fe1—C2120.0 (3)C3—Fe1—C4i—C5i163.8 (2)
N1—C1—Fe1—C2i43.9 (2)C3—Fe1—C5—C437.1 (2)
N1—C1—Fe1—C3157.9 (2)C3—Fe1—C5i—C4i40.2 (3)
N1—C1—Fe1—C3i78.6 (3)C3—C2—Fe1—C436.7 (2)
N1—C1—Fe1—C4159.0 (2)C3—C2—Fe1—C4i48.0 (3)
N1—C1—Fe1—C4i76.2 (4)C3—C2—Fe1—C580.4 (2)
N1—C1—Fe1—C5121.6 (3)C3—C2—Fe1—C5i169.8 (3)
N1—C1—Fe1—C5i41.4 (3)C3—C2—C1—C50.1 (3)
N1—C1—C2—C3179.7 (2)C3—C4—Fe1—C4i118.3 (2)
N1—C1—C5—C4179.5 (2)C3—C4—Fe1—C5119.5 (2)
N2—V1—N1—C1174.9 (2)C3—C4—Fe1—C5i159.9 (2)
N2—V1—N1i—C1i174.9 (2)C4—Fe1—C1—C537.4 (2)
N2—C9—C10—C11180.0C4—Fe1—C1i—C5i45.4 (4)
N2—C9—C14—C13180.0C4—Fe1—C4i—C5i122.2 (1)
C1—Fe1—C1i—C2i119.0 (1)C4—C3—Fe1—C537.6 (2)
C1—Fe1—C1i—C5i122.6 (1)C4—C3—Fe1—C5i50.6 (3)
C1—Fe1—C2—C3118.6 (2)C4—C5—Fe1—C5i119.9 (2)
C1—Fe1—C2i—C3i161.0 (1)C9—C10—C11—C120.0
C1—Fe1—C3—C238.2 (1)C9—C14—C13—C120.0
C1—Fe1—C3—C481.9 (2)C10—C9—C14—C130.0
C1—Fe1—C3i—C2i47.4 (3)C10—C11—C12—C130.0
C1—Fe1—C3i—C4i167.5 (2)C10—C11—C12—C15180.0
C1—Fe1—C4—C381.6 (2)C11—C10—C9—C140.0
C1—Fe1—C4—C537.9 (2)C11—C12—C13—C140.0
C1—Fe1—C4i—C3i165.7 (3)C14—C13—C12—C15180.0
C1—Fe1—C4i—C5i46.2 (4)
Symmetry code: (i) x, y+1/2, z.
 

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