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This work is part of a project studying the reactivity of a new ferrocenyl allyl­ammonium salt, [3-(tri­methyl­azaniumyl)prop-1-en-1-yl]ferrocene iodide, (1+)·I, with different nucleophiles. With nitro­gen-based nucleophiles, different ferrocenyl allyl­amine isomers have been synthesized successfully in good yield. Optimization of the basicity of the reaction medium has allowed selection of the best operating conditions to obtain the targeted isomer. In a similar way and in order to introduce phospho­rus-containing functional groups, the reaction of ammonium salt (1+)·I with a phospho­rus nucleophile, namely tri­phenyl­phosphane, was attempted. It was then possible to isolate single crystals of (3-ferrocenylprop-2-en-1-yl)tri­phenyl­phospho­nium iodide, [Fe(C5H5)(C26H23P)]I, which is shown to crystallize in two concomitant polymorphic forms, viz. a triclinic form, (I), in the space group P\overline{1}, and a monoclinic form, (II), in the space group P21/c. In the inter-ion packing of polymorph (I), the cations form bilayer ribbons via C—H...π and π–π stacking inter­actions. In polymorph (II), where π–π inter­actions do not occur, adjacent mol­ecules are joined by C—H...π inter­actions into a one-dimensional helical arrangement along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617004867/ku3195sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617004867/ku3195Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617004867/ku3195IIsup3.hkl
Contains datablock II

CCDC references: 1540743; 1540742

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011); data reduction: APEX2 (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997), DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

(I) (3-Ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide top
Crystal data top
[Fe(C5H5)(C26H23P)]·IZ = 2
Mr = 614.25F(000) = 616
Triclinic, P1Dx = 1.491 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.6203 (12) ÅCell parameters from 9951 reflections
b = 11.8441 (13) Åθ = 2.4–30.4°
c = 12.3126 (13) ŵ = 1.76 mm1
α = 99.255 (6)°T = 150 K
β = 100.973 (5)°Prism, yellow
γ = 111.584 (5)°0.15 × 0.13 × 0.12 mm
V = 1367.9 (3) Å3
Data collection top
Bruker APEXII
diffractometer
4796 independent reflections
Radiation source: fine-focus sealed tube4193 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
CCD rotation images, thick slices scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1212
Tmin = 0.626, Tmax = 0.746k = 1414
15904 measured reflectionsl = 1414
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.P)2 + 4.8514P]
where P = (Fo2 + 2Fc2)/3
4796 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 1.28 e Å3
0 restraintsΔρmin = 0.56 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C10.0433 (4)0.3128 (4)0.1616 (3)0.0283 (8)
C20.1088 (4)0.3109 (4)0.2528 (4)0.0346 (9)
H20.10640.26460.30690.041*
C30.1786 (4)0.3928 (4)0.2459 (5)0.0480 (13)
H30.23160.40740.29410.058*
C40.1549 (5)0.4483 (4)0.1550 (5)0.0509 (14)
H40.18760.50620.13310.061*
C50.0710 (5)0.3988 (4)0.1026 (4)0.0410 (11)
H50.03940.41940.040.049*
C60.1038 (5)0.6397 (6)0.4064 (6)0.0667 (18)
H60.04850.66480.44620.08*
C70.1417 (5)0.6789 (5)0.3118 (6)0.0654 (18)
H70.11560.73440.27760.079*
C80.2263 (5)0.6200 (5)0.2769 (5)0.0531 (13)
H80.26640.63030.21630.064*
C90.2394 (4)0.5424 (5)0.3504 (4)0.0467 (12)
H90.28870.49190.34640.056*
C100.1640 (5)0.5556 (6)0.4311 (5)0.0582 (15)
H100.15560.51570.49020.07*
C110.0416 (4)0.2459 (4)0.1316 (3)0.0267 (8)
H110.09860.27710.08520.032*
C120.0459 (4)0.1458 (4)0.1633 (3)0.0252 (8)
H120.00830.11390.21120.03*
C130.1342 (4)0.0808 (4)0.1257 (3)0.0236 (8)
H13A0.15170.09910.05470.028*
H13B0.08130.00920.11060.028*
C210.2747 (4)0.0983 (3)0.3639 (3)0.0246 (8)
C220.3166 (5)0.0135 (4)0.4089 (3)0.0373 (10)
H220.36050.02790.370.045*
C230.2928 (5)0.0096 (5)0.5128 (4)0.0447 (11)
H230.31920.06730.54280.054*
C240.2291 (5)0.0549 (4)0.5705 (4)0.0458 (12)
H240.21450.04110.64030.055*
C250.1874 (5)0.1390 (4)0.5260 (4)0.0393 (10)
H250.14340.18030.5650.047*
C260.2105 (4)0.1622 (4)0.4236 (3)0.0330 (9)
H260.18360.220.39430.04*
C310.3876 (4)0.0333 (3)0.1754 (3)0.0209 (7)
C320.5333 (4)0.0864 (4)0.1918 (4)0.0337 (9)
H320.58540.17120.22780.04*
C330.6002 (4)0.0134 (4)0.1549 (4)0.0376 (10)
H330.6970.04940.16540.045*
C340.5243 (4)0.1120 (4)0.1027 (3)0.0372 (10)
H340.56990.16130.07930.045*
C350.3801 (5)0.1647 (4)0.0850 (4)0.0388 (10)
H350.32880.24930.04840.047*
C360.3107 (4)0.0931 (4)0.1211 (3)0.0326 (9)
H360.21360.12940.1090.039*
C410.4074 (4)0.2904 (3)0.2498 (3)0.0218 (7)
C420.4069 (4)0.3421 (4)0.1553 (3)0.0296 (9)
H420.35210.29170.08290.036*
C430.4875 (4)0.4678 (4)0.1696 (4)0.0343 (9)
H430.4870.50180.10660.041*
C440.5697 (4)0.5442 (4)0.2775 (4)0.0325 (9)
H440.62330.62910.2870.039*
C450.5707 (4)0.4926 (4)0.3701 (3)0.0302 (9)
H450.62560.54350.44230.036*
C460.4914 (4)0.3665 (4)0.3578 (3)0.0244 (8)
H460.49410.33280.42090.029*
P10.30112 (9)0.12593 (9)0.22908 (8)0.0202 (2)
Fe10.03261 (6)0.48883 (5)0.26937 (5)0.03260 (15)
I10.15066 (3)0.20933 (3)0.83998 (2)0.03103 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0212 (18)0.027 (2)0.034 (2)0.0095 (16)0.0056 (16)0.0056 (17)
C20.024 (2)0.031 (2)0.048 (3)0.0088 (17)0.0148 (18)0.0076 (19)
C30.021 (2)0.035 (3)0.075 (4)0.0096 (19)0.010 (2)0.010 (2)
C40.031 (2)0.030 (2)0.079 (4)0.017 (2)0.011 (2)0.000 (2)
C50.036 (2)0.035 (2)0.045 (3)0.014 (2)0.003 (2)0.010 (2)
C60.033 (3)0.058 (4)0.083 (4)0.017 (3)0.001 (3)0.027 (3)
C70.042 (3)0.024 (3)0.107 (5)0.010 (2)0.013 (3)0.002 (3)
C80.032 (2)0.043 (3)0.067 (3)0.000 (2)0.007 (2)0.012 (3)
C90.024 (2)0.050 (3)0.059 (3)0.016 (2)0.002 (2)0.007 (2)
C100.034 (3)0.072 (4)0.046 (3)0.008 (3)0.001 (2)0.001 (3)
C110.0236 (19)0.031 (2)0.0255 (19)0.0123 (17)0.0078 (15)0.0043 (16)
C120.0160 (17)0.032 (2)0.0254 (19)0.0097 (16)0.0047 (15)0.0029 (16)
C130.0192 (18)0.028 (2)0.0217 (18)0.0104 (16)0.0039 (14)0.0005 (15)
C210.0234 (18)0.0225 (19)0.0214 (18)0.0039 (15)0.0062 (15)0.0018 (15)
C220.049 (3)0.038 (2)0.026 (2)0.021 (2)0.0111 (19)0.0050 (18)
C230.062 (3)0.043 (3)0.030 (2)0.022 (2)0.012 (2)0.012 (2)
C240.058 (3)0.044 (3)0.027 (2)0.007 (2)0.019 (2)0.010 (2)
C250.038 (2)0.048 (3)0.029 (2)0.015 (2)0.0152 (19)0.001 (2)
C260.029 (2)0.036 (2)0.030 (2)0.0113 (18)0.0094 (17)0.0016 (18)
C310.0229 (18)0.0255 (19)0.0169 (17)0.0121 (15)0.0060 (14)0.0063 (14)
C320.025 (2)0.036 (2)0.039 (2)0.0127 (18)0.0074 (17)0.0047 (19)
C330.025 (2)0.051 (3)0.041 (2)0.020 (2)0.0112 (18)0.007 (2)
C340.040 (2)0.050 (3)0.031 (2)0.033 (2)0.0074 (18)0.003 (2)
C350.041 (2)0.033 (2)0.041 (2)0.020 (2)0.005 (2)0.0030 (19)
C360.026 (2)0.034 (2)0.035 (2)0.0140 (18)0.0050 (17)0.0004 (18)
C410.0171 (17)0.0252 (19)0.0226 (18)0.0087 (15)0.0069 (14)0.0026 (15)
C420.029 (2)0.032 (2)0.0242 (19)0.0097 (17)0.0081 (16)0.0043 (17)
C430.039 (2)0.035 (2)0.033 (2)0.0142 (19)0.0167 (18)0.0155 (19)
C440.025 (2)0.026 (2)0.043 (2)0.0046 (17)0.0157 (18)0.0044 (18)
C450.0231 (19)0.033 (2)0.030 (2)0.0106 (17)0.0060 (16)0.0018 (17)
C460.0184 (17)0.029 (2)0.0263 (19)0.0117 (16)0.0060 (15)0.0048 (16)
P10.0182 (4)0.0231 (5)0.0192 (4)0.0090 (4)0.0061 (4)0.0029 (4)
Fe10.0205 (3)0.0273 (3)0.0460 (4)0.0113 (2)0.0032 (2)0.0021 (3)
I10.03366 (15)0.03771 (16)0.02755 (14)0.01734 (12)0.01290 (11)0.01189 (11)
Geometric parameters (Å, º) top
C1—C21.429 (6)C21—C221.388 (6)
C1—C51.424 (6)C21—C261.404 (5)
C1—C111.461 (5)C21—P11.797 (4)
C1—Fe12.056 (4)C22—C231.400 (6)
C2—C31.425 (6)C22—H220.93
C2—Fe12.039 (4)C23—C241.391 (7)
C2—H20.93C23—H230.93
C3—C41.403 (8)C24—C251.378 (7)
C3—Fe12.044 (4)C24—H240.93
C3—H30.93C25—C261.379 (6)
C4—C51.426 (7)C25—H250.93
C4—Fe12.047 (4)C26—H260.93
C4—H40.93C31—C361.388 (5)
C5—Fe12.033 (4)C31—C321.398 (5)
C5—H50.93C31—P11.796 (3)
C6—C71.396 (9)C32—C331.381 (6)
C6—C101.408 (8)C32—H320.93
C6—Fe12.040 (5)C33—C341.372 (6)
C6—H60.93C33—H330.93
C7—C81.412 (8)C34—C351.382 (6)
C7—Fe12.038 (5)C34—H340.93
C7—H70.93C35—C361.386 (5)
C8—C91.412 (7)C35—H350.93
C8—Fe12.045 (5)C36—H360.93
C8—H80.93C41—C461.396 (5)
C9—C101.414 (7)C41—C421.399 (5)
C9—Fe12.039 (4)C41—P11.802 (4)
C9—H90.93C42—C431.379 (6)
C10—Fe12.040 (5)C42—H420.93
C10—H100.93C43—C441.391 (6)
C11—C121.319 (5)C43—H430.93
C11—H110.93C44—C451.377 (6)
C12—C131.506 (5)C44—H440.93
C12—H120.93C45—C461.384 (6)
C13—P11.809 (3)C45—H450.93
C13—H13A0.97C46—H460.93
C13—H13B0.97
C2—C1—C5107.0 (4)C21—C26—H26120.1
C2—C1—C11129.2 (4)C36—C31—C32119.5 (3)
C5—C1—C11123.8 (4)C36—C31—P1120.0 (3)
C2—C1—Fe168.9 (2)C32—C31—P1120.4 (3)
C5—C1—Fe168.8 (2)C33—C32—C31120.2 (4)
C11—C1—Fe1125.7 (3)C33—C32—H32119.9
C3—C2—C1107.5 (4)C31—C32—H32119.9
C3—C2—Fe169.8 (2)C34—C33—C32120.3 (4)
C1—C2—Fe170.2 (2)C34—C33—H33119.9
C3—C2—H2126.3C32—C33—H33119.9
C1—C2—H2126.3C33—C34—C35119.8 (4)
Fe1—C2—H2125.3C33—C34—H34120.1
C4—C3—C2109.5 (4)C35—C34—H34120.1
C4—C3—Fe170.1 (3)C34—C35—C36120.9 (4)
C2—C3—Fe169.4 (2)C34—C35—H35119.5
C4—C3—H3125.3C36—C35—H35119.5
C2—C3—H3125.3C35—C36—C31119.3 (4)
Fe1—C3—H3126.9C35—C36—H36120.4
C3—C4—C5106.9 (4)C31—C36—H36120.4
C3—C4—Fe169.8 (3)C46—C41—C42119.5 (3)
C5—C4—Fe169.0 (2)C46—C41—P1121.3 (3)
C3—C4—H4126.5C42—C41—P1119.2 (3)
C5—C4—H4126.5C43—C42—C41120.0 (4)
Fe1—C4—H4126.2C43—C42—H42120
C4—C5—C1109.1 (4)C41—C42—H42120
C4—C5—Fe170.0 (3)C42—C43—C44120.6 (4)
C1—C5—Fe170.5 (2)C42—C43—H43119.7
C4—C5—H5125.5C44—C43—H43119.7
C1—C5—H5125.5C45—C44—C43119.3 (4)
Fe1—C5—H5125.6C45—C44—H44120.4
C7—C6—C10108.1 (5)C43—C44—H44120.4
C7—C6—Fe169.9 (3)C44—C45—C46121.2 (4)
C10—C6—Fe169.8 (3)C44—C45—H45119.4
C7—C6—H6125.9C46—C45—H45119.4
C10—C6—H6125.9C45—C46—C41119.5 (4)
Fe1—C6—H6125.9C45—C46—H46120.3
C6—C7—C8108.4 (5)C41—C46—H46120.3
C6—C7—Fe170.0 (3)C21—P1—C31109.29 (17)
C8—C7—Fe170.0 (3)C21—P1—C41108.83 (17)
C6—C7—H7125.8C31—P1—C41110.27 (16)
C8—C7—H7125.8C21—P1—C13110.54 (17)
Fe1—C7—H7125.7C31—P1—C13108.26 (16)
C9—C8—C7107.9 (5)C41—P1—C13109.64 (17)
C9—C8—Fe169.5 (3)C5—Fe1—C268.55 (19)
C7—C8—Fe169.5 (3)C5—Fe1—C6151.7 (2)
C9—C8—H8126.1C2—Fe1—C6127.5 (2)
C7—C8—H8126.1C5—Fe1—C7118.6 (2)
Fe1—C8—H8126.5C2—Fe1—C7164.5 (2)
C8—C9—C10107.5 (5)C6—Fe1—C740.0 (3)
C8—C9—Fe170.0 (3)C5—Fe1—C10166.5 (2)
C10—C9—Fe169.7 (3)C2—Fe1—C10108.6 (2)
C8—C9—H9126.2C6—Fe1—C1040.4 (2)
C10—C9—H9126.2C7—Fe1—C1067.7 (3)
Fe1—C9—H9125.6C5—Fe1—C9128.4 (2)
C6—C10—C9108.1 (5)C2—Fe1—C9119.65 (19)
C6—C10—Fe169.8 (3)C6—Fe1—C968.1 (2)
C9—C10—Fe169.7 (3)C7—Fe1—C968.1 (2)
C6—C10—H10125.9C10—Fe1—C940.6 (2)
C9—C10—H10125.9C5—Fe1—C367.8 (2)
Fe1—C10—H10126.1C2—Fe1—C340.85 (17)
C12—C11—C1126.9 (4)C6—Fe1—C3107.8 (2)
C12—C11—H11116.5C7—Fe1—C3126.5 (2)
C1—C11—H11116.5C10—Fe1—C3119.3 (2)
C11—C12—C13123.4 (4)C9—Fe1—C3153.6 (2)
C11—C12—H12118.3C5—Fe1—C8108.5 (2)
C13—C12—H12118.3C2—Fe1—C8153.77 (19)
C12—C13—P1114.0 (2)C6—Fe1—C867.7 (2)
C12—C13—H13A108.8C7—Fe1—C840.4 (2)
P1—C13—H13A108.8C10—Fe1—C867.8 (2)
C12—C13—H13B108.8C9—Fe1—C840.5 (2)
P1—C13—H13B108.8C3—Fe1—C8164.2 (2)
H13A—C13—H13B107.7C5—Fe1—C440.91 (19)
C22—C21—C26120.0 (4)C2—Fe1—C468.82 (19)
C22—C21—P1120.3 (3)C6—Fe1—C4117.4 (2)
C26—C21—P1119.7 (3)C7—Fe1—C4106.9 (2)
C21—C22—C23119.9 (4)C10—Fe1—C4151.6 (2)
C21—C22—H22120C9—Fe1—C4165.6 (2)
C23—C22—H22120C3—Fe1—C440.1 (2)
C24—C23—C22119.2 (4)C8—Fe1—C4127.1 (2)
C24—C23—H23120.4C5—Fe1—C140.76 (16)
C22—C23—H23120.4C2—Fe1—C140.85 (16)
C25—C24—C23120.9 (4)C6—Fe1—C1165.9 (3)
C25—C24—H24119.5C7—Fe1—C1153.1 (2)
C23—C24—H24119.5C10—Fe1—C1128.6 (2)
C24—C25—C26120.2 (4)C9—Fe1—C1109.03 (18)
C24—C25—H25119.9C3—Fe1—C168.29 (16)
C26—C25—H25119.9C8—Fe1—C1119.72 (19)
C25—C26—C21119.8 (4)C4—Fe1—C168.94 (17)
C25—C26—H26120.1
C5—C1—C2—C31.6 (4)C10—C6—Fe1—C881.5 (4)
C11—C1—C2—C3179.6 (4)C7—C6—Fe1—C483.8 (4)
Fe1—C1—C2—C360.1 (3)C10—C6—Fe1—C4157.0 (3)
C5—C1—C2—Fe158.4 (3)C7—C6—Fe1—C1162.5 (6)
C11—C1—C2—Fe1119.5 (4)C10—C6—Fe1—C143.3 (9)
C1—C2—C3—C41.7 (5)C6—C7—Fe1—C5155.5 (3)
Fe1—C2—C3—C458.7 (3)C8—C7—Fe1—C585.3 (4)
C1—C2—C3—Fe160.4 (3)C6—C7—Fe1—C241.3 (9)
C2—C3—C4—C51.0 (5)C8—C7—Fe1—C2160.5 (7)
Fe1—C3—C4—C559.3 (3)C8—C7—Fe1—C6119.2 (5)
C2—C3—C4—Fe158.3 (3)C6—C7—Fe1—C1037.7 (3)
C3—C4—C5—C10.0 (5)C8—C7—Fe1—C1081.5 (4)
Fe1—C4—C5—C159.8 (3)C6—C7—Fe1—C981.6 (3)
C3—C4—C5—Fe159.8 (3)C8—C7—Fe1—C937.6 (3)
C2—C1—C5—C41.1 (5)C6—C7—Fe1—C373.1 (4)
C11—C1—C5—C4179.1 (4)C8—C7—Fe1—C3167.7 (3)
Fe1—C1—C5—C459.6 (3)C6—C7—Fe1—C8119.2 (5)
C2—C1—C5—Fe158.5 (3)C6—C7—Fe1—C4112.7 (3)
C11—C1—C5—Fe1119.5 (4)C8—C7—Fe1—C4128.1 (4)
C10—C6—C7—C80.2 (6)C6—C7—Fe1—C1170.7 (4)
Fe1—C6—C7—C859.8 (3)C8—C7—Fe1—C151.5 (6)
C10—C6—C7—Fe159.6 (4)C6—C10—Fe1—C5158.1 (9)
C6—C7—C8—C90.6 (6)C9—C10—Fe1—C538.8 (11)
Fe1—C7—C8—C959.2 (3)C6—C10—Fe1—C2126.5 (4)
C6—C7—C8—Fe159.8 (4)C9—C10—Fe1—C2114.2 (3)
C7—C8—C9—C100.8 (5)C9—C10—Fe1—C6119.3 (5)
Fe1—C8—C9—C1059.9 (3)C6—C10—Fe1—C737.4 (3)
C7—C8—C9—Fe159.1 (3)C9—C10—Fe1—C781.9 (4)
C7—C6—C10—C90.2 (6)C6—C10—Fe1—C9119.3 (5)
Fe1—C6—C10—C959.4 (3)C6—C10—Fe1—C383.1 (4)
C7—C6—C10—Fe159.6 (4)C9—C10—Fe1—C3157.6 (3)
C8—C9—C10—C60.6 (5)C6—C10—Fe1—C881.2 (4)
Fe1—C9—C10—C659.5 (3)C9—C10—Fe1—C838.1 (3)
C8—C9—C10—Fe160.1 (3)C6—C10—Fe1—C446.9 (6)
C2—C1—C11—C1219.1 (7)C9—C10—Fe1—C4166.2 (4)
C5—C1—C11—C12163.3 (4)C6—C10—Fe1—C1167.7 (3)
Fe1—C1—C11—C12109.9 (4)C9—C10—Fe1—C173.0 (4)
C1—C11—C12—C13178.4 (3)C8—C9—Fe1—C572.3 (4)
C11—C12—C13—P197.6 (4)C10—C9—Fe1—C5169.3 (3)
C26—C21—C22—C231.0 (6)C8—C9—Fe1—C2157.4 (3)
P1—C21—C22—C23178.6 (3)C10—C9—Fe1—C284.2 (4)
C21—C22—C23—C241.1 (7)C8—C9—Fe1—C680.9 (4)
C22—C23—C24—C251.1 (7)C10—C9—Fe1—C637.5 (4)
C23—C24—C25—C261.1 (7)C8—C9—Fe1—C737.6 (4)
C24—C25—C26—C211.0 (6)C10—C9—Fe1—C780.8 (4)
C22—C21—C26—C251.0 (6)C8—C9—Fe1—C10118.4 (5)
P1—C21—C26—C25178.6 (3)C8—C9—Fe1—C3166.9 (4)
C36—C31—C32—C330.4 (6)C10—C9—Fe1—C348.5 (6)
P1—C31—C32—C33177.1 (3)C10—C9—Fe1—C8118.4 (5)
C31—C32—C33—C340.6 (7)C8—C9—Fe1—C434.5 (9)
C32—C33—C34—C351.3 (7)C10—C9—Fe1—C4152.9 (7)
C33—C34—C35—C361.1 (7)C8—C9—Fe1—C1113.8 (3)
C34—C35—C36—C310.2 (7)C10—C9—Fe1—C1127.8 (3)
C32—C31—C36—C350.6 (6)C4—C3—Fe1—C538.5 (3)
P1—C31—C36—C35176.9 (3)C2—C3—Fe1—C582.5 (3)
C46—C41—C42—C430.8 (5)C4—C3—Fe1—C2121.0 (4)
P1—C41—C42—C43179.9 (3)C4—C3—Fe1—C6111.7 (3)
C41—C42—C43—C440.1 (6)C2—C3—Fe1—C6127.3 (3)
C42—C43—C44—C450.6 (6)C4—C3—Fe1—C771.4 (4)
C43—C44—C45—C460.1 (6)C2—C3—Fe1—C7167.6 (3)
C44—C45—C46—C410.9 (5)C4—C3—Fe1—C10154.2 (3)
C42—C41—C46—C451.3 (5)C2—C3—Fe1—C1084.8 (3)
P1—C41—C46—C45179.5 (3)C4—C3—Fe1—C9171.9 (4)
C22—C21—P1—C311.4 (4)C2—C3—Fe1—C950.9 (5)
C26—C21—P1—C31179.0 (3)C4—C3—Fe1—C840.9 (9)
C22—C21—P1—C41121.9 (3)C2—C3—Fe1—C8161.9 (7)
C26—C21—P1—C4158.5 (3)C2—C3—Fe1—C4121.0 (4)
C22—C21—P1—C13117.7 (3)C4—C3—Fe1—C182.7 (3)
C26—C21—P1—C1361.9 (3)C2—C3—Fe1—C138.3 (3)
C36—C31—P1—C2180.0 (3)C9—C8—Fe1—C5128.0 (3)
C32—C31—P1—C2197.6 (3)C7—C8—Fe1—C5112.7 (4)
C36—C31—P1—C41160.4 (3)C9—C8—Fe1—C249.1 (6)
C32—C31—P1—C4122.0 (4)C7—C8—Fe1—C2168.4 (5)
C36—C31—P1—C1340.5 (4)C9—C8—Fe1—C681.9 (4)
C32—C31—P1—C13142.0 (3)C7—C8—Fe1—C637.3 (4)
C46—C41—P1—C2120.4 (3)C9—C8—Fe1—C7119.3 (5)
C42—C41—P1—C21160.4 (3)C9—C8—Fe1—C1038.1 (3)
C46—C41—P1—C3199.5 (3)C7—C8—Fe1—C1081.1 (4)
C42—C41—P1—C3179.7 (3)C7—C8—Fe1—C9119.3 (5)
C46—C41—P1—C13141.4 (3)C9—C8—Fe1—C3158.2 (7)
C42—C41—P1—C1339.4 (3)C7—C8—Fe1—C339.0 (10)
C12—C13—P1—C2156.8 (3)C9—C8—Fe1—C4169.8 (3)
C12—C13—P1—C31176.4 (3)C7—C8—Fe1—C470.9 (4)
C12—C13—P1—C4163.2 (3)C9—C8—Fe1—C184.8 (3)
C4—C5—Fe1—C282.0 (3)C7—C8—Fe1—C1155.9 (3)
C1—C5—Fe1—C237.9 (2)C3—C4—Fe1—C5118.2 (4)
C4—C5—Fe1—C648.5 (6)C3—C4—Fe1—C237.0 (3)
C1—C5—Fe1—C6168.4 (4)C5—C4—Fe1—C281.3 (3)
C4—C5—Fe1—C782.8 (4)C3—C4—Fe1—C685.3 (4)
C1—C5—Fe1—C7157.3 (3)C5—C4—Fe1—C6156.4 (3)
C4—C5—Fe1—C10162.2 (9)C3—C4—Fe1—C7127.2 (3)
C1—C5—Fe1—C1042.3 (10)C5—C4—Fe1—C7114.5 (3)
C4—C5—Fe1—C9166.5 (3)C3—C4—Fe1—C1053.1 (6)
C1—C5—Fe1—C973.6 (3)C5—C4—Fe1—C10171.4 (4)
C4—C5—Fe1—C337.8 (3)C3—C4—Fe1—C9165.5 (7)
C1—C5—Fe1—C382.1 (3)C5—C4—Fe1—C947.2 (9)
C4—C5—Fe1—C8125.8 (3)C5—C4—Fe1—C3118.2 (4)
C1—C5—Fe1—C8114.3 (3)C3—C4—Fe1—C8167.1 (3)
C1—C5—Fe1—C4119.9 (4)C5—C4—Fe1—C874.7 (4)
C4—C5—Fe1—C1119.9 (4)C3—C4—Fe1—C180.9 (3)
C3—C2—Fe1—C580.4 (3)C5—C4—Fe1—C137.3 (3)
C1—C2—Fe1—C537.8 (2)C2—C1—Fe1—C5119.1 (3)
C3—C2—Fe1—C672.6 (4)C11—C1—Fe1—C5117.1 (5)
C1—C2—Fe1—C6169.2 (3)C5—C1—Fe1—C2119.1 (3)
C3—C2—Fe1—C740.3 (9)C11—C1—Fe1—C2123.9 (5)
C1—C2—Fe1—C7158.5 (8)C2—C1—Fe1—C637.8 (8)
C3—C2—Fe1—C10113.6 (3)C5—C1—Fe1—C6156.9 (7)
C1—C2—Fe1—C10128.2 (3)C11—C1—Fe1—C686.0 (8)
C3—C2—Fe1—C9156.7 (3)C2—C1—Fe1—C7167.5 (4)
C1—C2—Fe1—C985.1 (3)C5—C1—Fe1—C748.4 (5)
C1—C2—Fe1—C3118.2 (4)C11—C1—Fe1—C768.7 (6)
C3—C2—Fe1—C8169.0 (5)C2—C1—Fe1—C1072.5 (3)
C1—C2—Fe1—C850.8 (6)C5—C1—Fe1—C10168.4 (3)
C3—C2—Fe1—C436.3 (3)C11—C1—Fe1—C1051.4 (4)
C1—C2—Fe1—C481.9 (3)C2—C1—Fe1—C9113.7 (3)
C3—C2—Fe1—C1118.2 (4)C5—C1—Fe1—C9127.3 (3)
C7—C6—Fe1—C550.2 (6)C11—C1—Fe1—C910.2 (4)
C10—C6—Fe1—C5169.4 (4)C2—C1—Fe1—C338.3 (3)
C7—C6—Fe1—C2167.1 (3)C5—C1—Fe1—C380.7 (3)
C10—C6—Fe1—C273.7 (4)C11—C1—Fe1—C3162.2 (4)
C10—C6—Fe1—C7119.2 (5)C2—C1—Fe1—C8156.8 (3)
C7—C6—Fe1—C10119.2 (5)C5—C1—Fe1—C884.2 (3)
C7—C6—Fe1—C981.5 (3)C11—C1—Fe1—C832.9 (4)
C10—C6—Fe1—C937.7 (3)C2—C1—Fe1—C481.6 (3)
C7—C6—Fe1—C3126.2 (3)C5—C1—Fe1—C437.5 (3)
C10—C6—Fe1—C3114.6 (4)C11—C1—Fe1—C4154.6 (4)
C7—C6—Fe1—C837.7 (3)
(II) (3-Ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide top
Crystal data top
[Fe(C5H5)(C26H23P)]·IF(000) = 1232
Mr = 614.25Dx = 1.549 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9962 reflections
a = 10.1090 (16) Åθ = 2.5–26.1°
b = 10.6299 (15) ŵ = 1.82 mm1
c = 25.148 (4) ÅT = 150 K
β = 102.868 (7)°Prism, red
V = 2634.4 (7) Å30.13 × 0.11 × 0.06 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
5396 independent reflections
Radiation source: fine-focus sealed tube4161 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
CCD rotation images, thick slices scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1212
Tmin = 0.699, Tmax = 0.745k = 1313
50617 measured reflectionsl = 2931
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0151P)2 + 2.0496P]
where P = (Fo2 + 2Fc2)/3
5396 reflections(Δ/σ)max = 0.005
352 parametersΔρmax = 0.52 e Å3
10 restraintsΔρmin = 0.50 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
Fe10.07591 (3)0.92217 (3)0.811703 (13)0.02405 (9)
P10.58954 (6)0.65946 (5)0.90227 (2)0.01960 (13)
C10.1316 (2)0.8232 (2)0.88333 (9)0.0225 (5)
C20.1548 (2)0.9550 (2)0.89213 (9)0.0268 (6)
H20.23810.99270.90650.032*
C30.0298 (3)1.0182 (3)0.87538 (10)0.0352 (6)
H30.01661.10460.8770.042*
C40.0717 (3)0.9284 (3)0.85583 (10)0.0351 (7)
H40.16340.94510.84250.042*
C50.0097 (2)0.8082 (3)0.86010 (9)0.0302 (6)
H50.05360.73230.84950.036*
C60.1139 (15)0.8288 (13)0.7456 (6)0.033 (4)0.54
H60.12020.7420.74230.04*0.54
C70.2216 (11)0.9082 (19)0.7675 (5)0.053 (7)0.54
H70.31170.88510.78080.064*0.54
C80.167 (2)1.0301 (14)0.7656 (9)0.060 (7)0.54
H80.21571.10260.77820.073*0.54
C90.028 (2)1.0249 (19)0.7418 (14)0.050 (6)0.54
H90.03121.09290.73530.061*0.54
C100.0052 (15)0.899 (2)0.7294 (10)0.043 (4)0.54
H100.09070.86750.71330.052*0.54
C6B0.176 (2)0.8507 (12)0.7575 (7)0.039 (7)0.46
H6B0.22280.77480.76190.047*0.46
C7B0.2330 (16)0.9668 (18)0.7739 (8)0.040 (4)0.46
H7B0.32310.98260.79070.048*0.46
C8B0.128 (2)1.0562 (14)0.7605 (11)0.031 (3)0.46
H8B0.13651.14220.76730.037*0.46
C9B0.0090 (17)0.993 (2)0.7349 (15)0.039 (6)0.46
H9B0.07511.02970.72140.046*0.46
C10B0.038 (2)0.8642 (18)0.7334 (8)0.046 (7)0.46
H10B0.02230.80030.71910.056*0.46
C110.2326 (2)0.7227 (2)0.89490 (9)0.0228 (5)
H110.2110.64620.87710.027*
C120.3528 (2)0.7329 (2)0.92901 (9)0.0213 (5)
H120.3730.80850.94770.026*
C130.4586 (2)0.6316 (2)0.93959 (9)0.0226 (5)
H13A0.4160.5510.92890.027*
H13B0.49930.62820.97830.027*
C210.6595 (2)0.8117 (2)0.92184 (9)0.0216 (5)
C220.7822 (2)0.8208 (2)0.95968 (9)0.0264 (6)
H220.8340.74920.97050.032*
C230.8270 (3)0.9366 (3)0.98116 (10)0.0354 (6)
H230.90880.94271.00680.043*
C240.7518 (3)1.0427 (3)0.96501 (10)0.0384 (7)
H240.7831.12020.97980.046*
C250.6303 (3)1.0358 (2)0.92712 (11)0.0356 (6)
H250.581.10830.91630.043*
C260.5834 (3)0.9196 (2)0.90515 (10)0.0289 (6)
H260.50170.91410.87950.035*
C310.5195 (2)0.6558 (2)0.83027 (9)0.0217 (5)
C320.5704 (3)0.7327 (2)0.79466 (9)0.0300 (6)
H320.63870.79050.80830.036*
C330.5192 (3)0.7231 (3)0.73892 (10)0.0362 (7)
H330.55340.77390.7150.043*
C340.4178 (3)0.6383 (3)0.71917 (10)0.0371 (7)
H340.38250.63270.68180.044*
C350.3678 (3)0.5613 (2)0.75413 (10)0.0351 (6)
H350.29950.50380.74020.042*
C360.4184 (2)0.5688 (2)0.80975 (9)0.0272 (6)
H360.38520.51610.83330.033*
C410.7169 (2)0.5392 (2)0.91854 (9)0.0216 (5)
C420.7599 (2)0.4958 (2)0.97192 (9)0.0238 (5)
H420.72140.52780.99940.029*
C430.8602 (2)0.4047 (2)0.98383 (9)0.0274 (6)
H430.88860.37531.01940.033*
C440.9177 (3)0.3577 (2)0.94337 (10)0.0329 (6)
H440.98520.29680.95160.04*
C450.8760 (3)0.4004 (3)0.89086 (11)0.0470 (8)
H450.91550.36840.86370.056*
C460.7762 (3)0.4902 (3)0.87810 (10)0.0370 (7)
H460.74820.51840.84230.044*
I10.316992 (19)0.295651 (16)0.900690 (7)0.03630 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02670 (19)0.03007 (19)0.01633 (18)0.00157 (16)0.00680 (14)0.00163 (14)
P10.0236 (3)0.0207 (3)0.0142 (3)0.0007 (3)0.0037 (2)0.0004 (2)
C10.0231 (13)0.0310 (14)0.0144 (11)0.0031 (10)0.0062 (10)0.0001 (10)
C20.0279 (14)0.0336 (14)0.0179 (12)0.0009 (11)0.0031 (10)0.0040 (10)
C30.0438 (17)0.0411 (16)0.0230 (14)0.0153 (14)0.0121 (12)0.0001 (12)
C40.0234 (14)0.0635 (19)0.0192 (13)0.0085 (14)0.0064 (11)0.0053 (13)
C50.0253 (13)0.0459 (16)0.0203 (13)0.0059 (13)0.0070 (10)0.0034 (12)
C60.050 (13)0.033 (4)0.020 (7)0.008 (7)0.013 (9)0.002 (4)
C70.026 (6)0.12 (2)0.021 (5)0.007 (11)0.015 (5)0.000 (13)
C80.082 (15)0.058 (12)0.055 (13)0.043 (11)0.046 (13)0.013 (11)
C90.086 (15)0.039 (6)0.034 (11)0.030 (8)0.030 (11)0.022 (7)
C100.042 (6)0.065 (10)0.022 (5)0.003 (7)0.006 (5)0.002 (7)
C6B0.046 (17)0.042 (12)0.036 (14)0.024 (10)0.025 (13)0.018 (10)
C7B0.029 (6)0.061 (12)0.030 (7)0.006 (7)0.008 (5)0.016 (8)
C8B0.044 (8)0.026 (4)0.026 (5)0.009 (5)0.014 (6)0.006 (4)
C9B0.025 (5)0.064 (15)0.027 (8)0.007 (7)0.006 (4)0.019 (12)
C10B0.070 (18)0.059 (13)0.012 (7)0.025 (11)0.011 (12)0.002 (9)
C110.0291 (13)0.0246 (13)0.0169 (12)0.0062 (11)0.0099 (10)0.0002 (10)
C120.0259 (13)0.0239 (13)0.0159 (12)0.0039 (10)0.0082 (10)0.0014 (9)
C130.0275 (13)0.0243 (13)0.0166 (12)0.0033 (10)0.0062 (10)0.0016 (10)
C210.0250 (12)0.0248 (13)0.0160 (12)0.0040 (10)0.0069 (10)0.0002 (10)
C220.0277 (13)0.0336 (15)0.0188 (12)0.0057 (11)0.0072 (11)0.0016 (10)
C230.0402 (16)0.0422 (17)0.0240 (14)0.0180 (14)0.0073 (12)0.0057 (12)
C240.060 (2)0.0317 (15)0.0289 (15)0.0197 (14)0.0225 (15)0.0090 (12)
C250.0541 (19)0.0241 (14)0.0349 (15)0.0013 (13)0.0236 (14)0.0020 (11)
C260.0338 (14)0.0287 (14)0.0245 (13)0.0003 (12)0.0070 (11)0.0023 (11)
C310.0271 (13)0.0226 (12)0.0158 (12)0.0034 (10)0.0053 (10)0.0004 (9)
C320.0369 (15)0.0305 (14)0.0223 (13)0.0036 (12)0.0061 (11)0.0010 (10)
C330.0500 (17)0.0403 (16)0.0208 (14)0.0058 (14)0.0134 (12)0.0064 (12)
C340.0495 (17)0.0470 (17)0.0129 (13)0.0125 (15)0.0030 (12)0.0050 (12)
C350.0372 (15)0.0405 (16)0.0250 (14)0.0017 (13)0.0016 (12)0.0119 (12)
C360.0331 (14)0.0268 (13)0.0218 (13)0.0027 (11)0.0063 (11)0.0031 (10)
C410.0253 (13)0.0204 (12)0.0193 (12)0.0024 (10)0.0053 (10)0.0012 (10)
C420.0284 (13)0.0284 (13)0.0168 (12)0.0008 (11)0.0096 (10)0.0006 (10)
C430.0302 (14)0.0311 (14)0.0204 (13)0.0025 (12)0.0046 (11)0.0081 (11)
C440.0378 (15)0.0293 (14)0.0312 (15)0.0124 (12)0.0067 (12)0.0031 (11)
C450.063 (2)0.0550 (19)0.0265 (15)0.0299 (16)0.0181 (14)0.0000 (13)
C460.0523 (18)0.0435 (16)0.0160 (13)0.0182 (14)0.0098 (12)0.0045 (11)
I10.05332 (12)0.02727 (9)0.03013 (10)0.00953 (9)0.01316 (8)0.00407 (8)
Geometric parameters (Å, º) top
Fe1—C81.996 (18)C9B—H9B0.93
Fe1—C10B2.018 (19)C10B—H10B0.93
Fe1—C6B2.018 (13)C11—C121.327 (3)
Fe1—C22.032 (2)C11—H110.93
Fe1—C92.04 (3)C12—C131.499 (3)
Fe1—C72.038 (13)C12—H120.93
Fe1—C9B2.04 (3)C13—H13A0.97
Fe1—C32.039 (2)C13—H13B0.97
Fe1—C52.041 (2)C21—C221.389 (3)
Fe1—C62.044 (14)C21—C261.393 (3)
P1—C211.790 (2)C22—C231.380 (3)
P1—C311.792 (2)C22—H220.93
P1—C411.795 (2)C23—C241.370 (4)
P1—C131.810 (2)C23—H230.93
C1—C51.427 (3)C24—C251.378 (4)
C1—C21.430 (3)C24—H240.93
C1—C111.461 (3)C25—C261.393 (3)
C2—C31.410 (3)C25—H250.93
C2—H20.93C26—H260.93
C3—C41.407 (4)C31—C361.390 (3)
C3—H30.93C31—C321.393 (3)
C4—C51.417 (4)C32—C331.386 (3)
C4—H40.9301C32—H320.93
C5—H50.93C33—C341.373 (4)
C6—C71.391 (12)C33—H330.93
C6—C101.398 (13)C34—C351.377 (4)
C6—H60.93C34—H340.93
C7—C81.404 (13)C35—C361.381 (3)
C7—H70.93C35—H350.93
C8—C91.402 (12)C36—H360.93
C8—H80.93C41—C461.392 (3)
C9—C101.400 (13)C41—C421.394 (3)
C9—H90.93C42—C431.385 (3)
C10—H100.93C42—H420.93
C6B—C7B1.385 (15)C43—C441.374 (3)
C6B—C10B1.399 (13)C43—H430.93
C6B—H6B0.93C44—C451.371 (4)
C7B—C8B1.406 (15)C44—H440.93
C7B—H7B0.93C45—C461.374 (4)
C8B—C9B1.407 (14)C45—H450.93
C8B—H8B0.93C46—H460.93
C9B—C10B1.399 (13)
C8—Fe1—C10B67.7 (7)Fe1—C9—H9126.2
C8—Fe1—C6B57.2 (5)C6—C10—C9107.2 (13)
C10B—Fe1—C6B40.6 (4)C6—C10—Fe169.3 (10)
C8—Fe1—C2110.4 (5)C9—C10—Fe168.9 (15)
C10B—Fe1—C2166.2 (7)C6—C10—H10126.4
C6B—Fe1—C2126.3 (6)C9—C10—H10126.4
C8—Fe1—C940.7 (5)Fe1—C10—H10126.8
C10B—Fe1—C950.4 (9)C7B—C6B—C10B110.3 (11)
C6B—Fe1—C971.1 (8)C7B—C6B—Fe172.6 (10)
C2—Fe1—C9137.1 (7)C10B—C6B—Fe169.7 (9)
C8—Fe1—C740.7 (4)C7B—C6B—H6B124.9
C10B—Fe1—C756.5 (5)C10B—C6B—H6B124.9
C6B—Fe1—C721.9 (3)Fe1—C6B—H6B124.4
C2—Fe1—C7112.6 (4)C6B—C7B—C8B106.9 (12)
C9—Fe1—C768.2 (7)C6B—C7B—Fe167.9 (10)
C8—Fe1—C9B48.6 (9)C8B—C7B—Fe169.8 (14)
C10B—Fe1—C9B40.3 (5)C6B—C7B—H7B126.6
C6B—Fe1—C9B67.0 (7)C8B—C7B—H7B126.6
C2—Fe1—C9B148.5 (7)Fe1—C7B—H7B127.3
C9—Fe1—C9B11.6 (9)C7B—C8B—C9B107.9 (12)
C7—Fe1—C9B68.8 (8)C7B—C8B—Fe170.6 (13)
C8—Fe1—C3112.6 (5)C9B—C8B—Fe168.9 (17)
C10B—Fe1—C3153.3 (7)C7B—C8B—H8B126
C6B—Fe1—C3162.9 (6)C9B—C8B—H8B126
C2—Fe1—C340.52 (10)Fe1—C8B—H8B126.2
C9—Fe1—C3111.0 (7)C10B—C9B—C8B108.5 (10)
C7—Fe1—C3141.6 (5)C10B—C9B—Fe169.0 (14)
C9B—Fe1—C3118.3 (7)C8B—C9B—Fe171.0 (16)
C8—Fe1—C5177.6 (7)C10B—C9B—H9B125.7
C10B—Fe1—C5112.8 (5)C8B—C9B—H9B125.7
C6B—Fe1—C5121.5 (4)Fe1—C9B—H9B125.6
C2—Fe1—C568.48 (10)C9B—C10B—C6B106.4 (9)
C9—Fe1—C5141.6 (7)C9B—C10B—Fe170.7 (16)
C7—Fe1—C5137.3 (6)C6B—C10B—Fe169.7 (8)
C9B—Fe1—C5133.4 (7)C9B—C10B—H10B126.8
C3—Fe1—C568.13 (11)C6B—C10B—H10B126.8
C8—Fe1—C667.2 (6)Fe1—C10B—H10B124.5
C10B—Fe1—C624.1 (5)C12—C11—C1124.6 (2)
C6B—Fe1—C619.1 (4)C12—C11—H11117.7
C2—Fe1—C6142.1 (4)C1—C11—H11117.7
C9—Fe1—C667.0 (8)C11—C12—C13124.8 (2)
C7—Fe1—C639.8 (4)C11—C12—H12117.6
C9B—Fe1—C659.5 (8)C13—C12—H12117.6
C3—Fe1—C6177.3 (4)C12—C13—P1111.45 (15)
C5—Fe1—C6112.2 (4)C12—C13—H13A109.3
C21—P1—C31109.90 (10)P1—C13—H13A109.3
C21—P1—C41111.19 (11)C12—C13—H13B109.3
C31—P1—C41108.48 (10)P1—C13—H13B109.3
C21—P1—C13107.15 (10)H13A—C13—H13B108
C31—P1—C13110.51 (11)C22—C21—C26119.9 (2)
C41—P1—C13109.61 (10)C22—C21—P1119.30 (18)
C5—C1—C2106.7 (2)C26—C21—P1120.25 (18)
C5—C1—C11126.2 (2)C23—C22—C21119.7 (2)
C2—C1—C11127.1 (2)C23—C22—H22120.1
C5—C1—Fe169.16 (13)C21—C22—H22120.1
C2—C1—Fe168.74 (13)C24—C23—C22120.4 (2)
C11—C1—Fe1126.32 (15)C24—C23—H23119.8
C3—C2—C1108.4 (2)C22—C23—H23119.8
C3—C2—Fe169.99 (14)C23—C24—C25120.8 (2)
C1—C2—Fe170.30 (13)C23—C24—H24119.6
C3—C2—H2125.8C25—C24—H24119.6
C1—C2—H2125.8C24—C25—C26119.6 (3)
Fe1—C2—H2125.5C24—C25—H25120.2
C4—C3—C2108.4 (2)C26—C25—H25120.2
C4—C3—Fe170.26 (14)C21—C26—C25119.6 (2)
C2—C3—Fe169.49 (13)C21—C26—H26120.2
C4—C3—H3125.8C25—C26—H26120.2
C2—C3—H3125.8C36—C31—C32119.9 (2)
Fe1—C3—H3126C36—C31—P1118.82 (17)
C3—C4—C5108.0 (2)C32—C31—P1121.15 (18)
C3—C4—Fe169.48 (14)C33—C32—C31119.9 (2)
C5—C4—Fe169.44 (13)C33—C32—H32120
C3—C4—H4126C31—C32—H32120
C5—C4—H4126C34—C33—C32119.7 (2)
Fe1—C4—H4126.7C34—C33—H33120.2
C4—C5—C1108.4 (2)C32—C33—H33120.2
C4—C5—Fe170.02 (14)C33—C34—C35120.7 (2)
C1—C5—Fe170.05 (13)C33—C34—H34119.7
C4—C5—H5125.8C35—C34—H34119.7
C1—C5—H5125.8C34—C35—C36120.4 (2)
Fe1—C5—H5125.7C34—C35—H35119.8
C7—C6—C10109.9 (13)C36—C35—H35119.8
C7—C6—Fe169.8 (8)C35—C36—C31119.4 (2)
C10—C6—Fe170.9 (12)C35—C36—H36120.3
C7—C6—H6125.1C31—C36—H36120.3
C10—C6—H6125.1C46—C41—C42119.1 (2)
Fe1—C6—H6125.8C46—C41—P1120.24 (17)
C6—C7—C8106.3 (10)C42—C41—P1120.61 (17)
C6—C7—Fe170.3 (8)C43—C42—C41119.7 (2)
C8—C7—Fe168.0 (9)C43—C42—H42120.1
C6—C7—H7126.9C41—C42—H42120.1
C8—C7—H7126.9C44—C43—C42120.3 (2)
Fe1—C7—H7126.3C44—C43—H43119.9
C9—C8—C7109.0 (9)C42—C43—H43119.9
C9—C8—Fe171.2 (14)C45—C44—C43120.2 (2)
C7—C8—Fe171.2 (8)C45—C44—H44119.9
C9—C8—H8125.5C43—C44—H44119.9
C7—C8—H8125.5C44—C45—C46120.5 (2)
Fe1—C8—H8123.6C44—C45—H45119.8
C10—C9—C8107.6 (11)C46—C45—H45119.8
C10—C9—Fe171.2 (15)C45—C46—C41120.2 (2)
C8—C9—Fe168.2 (12)C45—C46—H46119.9
C10—C9—H9126.2C41—C46—H46119.9
C8—C9—H9126.2
C1—C2—C3—C40.4 (3)C21—P1—C13—C1256.87 (18)
Fe1—C2—C3—C459.68 (17)C31—P1—C13—C1262.85 (19)
C1—C2—C3—Fe160.05 (16)C41—P1—C13—C12177.64 (15)
C3—C4—C5—C10.8 (3)C31—P1—C21—C22139.03 (18)
Fe1—C4—C5—C159.78 (15)C41—P1—C21—C2218.9 (2)
C3—C4—C5—Fe158.93 (17)C13—P1—C21—C22100.87 (19)
C2—C1—C5—C41.1 (2)C31—P1—C21—C2649.7 (2)
C11—C1—C5—C4179.8 (2)C41—P1—C21—C26169.78 (18)
Fe1—C1—C5—C459.76 (16)C13—P1—C21—C2670.5 (2)
C2—C1—C5—Fe158.71 (15)C26—C21—C22—C231.0 (3)
C11—C1—C5—Fe1120.4 (2)P1—C21—C22—C23170.31 (18)
C10—C6—C7—C81 (2)C21—C22—C23—C240.6 (4)
Fe1—C6—C7—C858.8 (12)C22—C23—C24—C250.0 (4)
C10—C6—C7—Fe159.8 (15)C23—C24—C25—C260.2 (4)
C6—C7—C8—C91 (2)C22—C21—C26—C250.8 (3)
Fe1—C7—C8—C961.4 (18)P1—C21—C26—C25170.43 (18)
C6—C7—C8—Fe160.3 (11)C24—C25—C26—C210.2 (4)
C7—C8—C9—C101 (3)C21—P1—C31—C36155.96 (18)
Fe1—C8—C9—C1061 (2)C41—P1—C31—C3682.3 (2)
C7—C8—C9—Fe161.5 (14)C13—P1—C31—C3637.9 (2)
C7—C6—C10—C90 (3)C21—P1—C31—C3228.1 (2)
Fe1—C6—C10—C959 (2)C41—P1—C31—C3293.6 (2)
C7—C6—C10—Fe159.1 (13)C13—P1—C31—C32146.19 (19)
C8—C9—C10—C60 (3)C36—C31—C32—C330.7 (4)
Fe1—C9—C10—C659.0 (18)P1—C31—C32—C33176.51 (19)
C8—C9—C10—Fe159 (2)C31—C32—C33—C340.5 (4)
C10B—C6B—C7B—C8B1 (3)C32—C33—C34—C351.0 (4)
Fe1—C6B—C7B—C8B59.1 (18)C33—C34—C35—C360.4 (4)
C10B—C6B—C7B—Fe159.8 (13)C34—C35—C36—C310.7 (4)
C6B—C7B—C8B—C9B1 (3)C32—C31—C36—C351.2 (3)
Fe1—C7B—C8B—C9B59 (2)P1—C31—C36—C35177.17 (18)
C6B—C7B—C8B—Fe158.0 (15)C21—P1—C41—C46100.7 (2)
C7B—C8B—C9B—C10B1 (4)C31—P1—C41—C4620.3 (2)
Fe1—C8B—C9B—C10B59 (2)C13—P1—C41—C46141.0 (2)
C7B—C8B—C9B—Fe160 (2)C21—P1—C41—C4277.9 (2)
Fe1—C9B—C10B—C6B60.9 (14)C31—P1—C41—C42161.17 (19)
C8B—C9B—C10B—Fe160 (2)C13—P1—C41—C4240.4 (2)
C7B—C6B—C10B—C9B0 (3)C46—C41—C42—C430.2 (4)
Fe1—C6B—C10B—C9B62 (2)P1—C41—C42—C43178.75 (18)
C7B—C6B—C10B—Fe161.5 (14)C41—C42—C43—C440.4 (4)
C5—C1—C11—C12161.0 (2)C42—C43—C44—C450.2 (4)
C2—C1—C11—C1220.0 (4)C43—C44—C45—C460.1 (5)
Fe1—C1—C11—C12109.5 (2)C44—C45—C46—C410.3 (5)
C1—C11—C12—C13177.8 (2)C42—C41—C46—C450.1 (4)
C11—C12—C13—P1100.6 (2)P1—C41—C46—C45178.4 (2)
Selected geometric parameters in polymorphs (I) and (II) (Å, °) top
Parameter(I)(II)
C12—C11—C1126.9 (4)124.6 (2)
C11—C12—C13123.4 (4)124.8 (2)
C2—C1—C11—C1219.1 (7)20.0 (4)
C1—C11—C12—C13178.4 (3)-177.8 (2)
C11—C12—C13—P197.6 (4)100.6 (2)
Comparison of some geometric parameters within the ferrocene group in (I) and (II) with related mean values extracted from the CSD top
Cg1 is the centroid of the C1–C5 ring and Cg2 that of the C6–C10 ring (C6B–C10B).
(I)(II)CSD
Fe···Cg1 (Å)1.648 (2)1.649 (1)1.64 (1)
Fe···Cg2 (Å)1.652 (3)1.652 (10) [1.663 (11)]1.65 (1)
Cg1···Fe···Cg2 (°)178.72 (13)179.8 (3) [174.8 (3)]178.01(1.17)
Cg1/Cg2 (°)1.10 (2)2.2 (10) [3.7 (10)]2.4(1.5)
Dihedral angles (°) between phenyl rings in the phenyl group top
Dihedral_angleCg3/Cg4Cg4/Cg5Cg3/Cg5
(I)79.87 (13)89.91 (13)66.70 (12)
(II)64.29 (10)89.03 (07)66.20 (09)
Cg3 is the centroid of the phenyl ring C21–C26, Cg4 that of the phenyl ring C31–C36 and Cg5 that of the phenyl ring C41–C46.
Hydrogen-bond geometry (Å, °) for (I) and (II) top
Cg3 is the centroid of the phenyl ring C41–C46, Cg2 that of the phenyl ring C5–C10 and Cg5 that of the phenyl ring C31–C36.
D—H···AD—HH···AD···AD—H···A
Polymorph (I)
C13—H13B···I1i0.97002.97003.802?(3)145.00
C3—H3···Cg3ii0.93002.97003.690?(5)135.00
C9—H9···Cg30.93002.87003.713?(5)151.00
Polymorph (II)
C13—H13A···I10.97002.92003.891?(2)174.00
C36—H36···I10.93003.06003.969?(3)166.00
C45—H45···Cg2iii0.94002.92003.623?(3)132.00
C6B—H6B···Cg50.932.793.617?(4)149.00
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, y+1/2, -z+1/2.
 

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