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(C
5H
5)(C
26H
23P)]I, which is shown to crystallize in two concomitant polymorphic forms,
viz. a triclinic form, (I), in the space group
P, and a monoclinic form, (II), in the space group
P2
1/
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
CCDC references: 1540743; 1540742
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)]·I | Z = 2 |
Mr = 614.25 | F(000) = 616 |
Triclinic, P1 | Dx = 1.491 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6203 (12) Å | Cell parameters from 9951 reflections |
b = 11.8441 (13) Å | θ = 2.4–30.4° |
c = 12.3126 (13) Å | µ = 1.76 mm−1 |
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 tube | 4193 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
CCD rotation images, thick slices scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −12→12 |
Tmin = 0.626, Tmax = 0.746 | k = −14→14 |
15904 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H-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 parameters | Δρmax = 1.28 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | −0.0433 (4) | 0.3128 (4) | 0.1616 (3) | 0.0283 (8) | |
C2 | −0.1088 (4) | 0.3109 (4) | 0.2528 (4) | 0.0346 (9) | |
H2 | −0.1064 | 0.2646 | 0.3069 | 0.041* | |
C3 | −0.1786 (4) | 0.3928 (4) | 0.2459 (5) | 0.0480 (13) | |
H3 | −0.2316 | 0.4074 | 0.2941 | 0.058* | |
C4 | −0.1549 (5) | 0.4483 (4) | 0.1550 (5) | 0.0509 (14) | |
H4 | −0.1876 | 0.5062 | 0.1331 | 0.061* | |
C5 | −0.0710 (5) | 0.3988 (4) | 0.1026 (4) | 0.0410 (11) | |
H5 | −0.0394 | 0.4194 | 0.04 | 0.049* | |
C6 | 0.1038 (5) | 0.6397 (6) | 0.4064 (6) | 0.0667 (18) | |
H6 | 0.0485 | 0.6648 | 0.4462 | 0.08* | |
C7 | 0.1417 (5) | 0.6789 (5) | 0.3118 (6) | 0.0654 (18) | |
H7 | 0.1156 | 0.7344 | 0.2776 | 0.079* | |
C8 | 0.2263 (5) | 0.6200 (5) | 0.2769 (5) | 0.0531 (13) | |
H8 | 0.2664 | 0.6303 | 0.2163 | 0.064* | |
C9 | 0.2394 (4) | 0.5424 (5) | 0.3504 (4) | 0.0467 (12) | |
H9 | 0.2887 | 0.4919 | 0.3464 | 0.056* | |
C10 | 0.1640 (5) | 0.5556 (6) | 0.4311 (5) | 0.0582 (15) | |
H10 | 0.1556 | 0.5157 | 0.4902 | 0.07* | |
C11 | 0.0416 (4) | 0.2459 (4) | 0.1316 (3) | 0.0267 (8) | |
H11 | 0.0986 | 0.2771 | 0.0852 | 0.032* | |
C12 | 0.0459 (4) | 0.1458 (4) | 0.1633 (3) | 0.0252 (8) | |
H12 | −0.0083 | 0.1139 | 0.2112 | 0.03* | |
C13 | 0.1342 (4) | 0.0808 (4) | 0.1257 (3) | 0.0236 (8) | |
H13A | 0.1517 | 0.0991 | 0.0547 | 0.028* | |
H13B | 0.0813 | −0.0092 | 0.1106 | 0.028* | |
C21 | 0.2747 (4) | 0.0983 (3) | 0.3639 (3) | 0.0246 (8) | |
C22 | 0.3166 (5) | 0.0135 (4) | 0.4089 (3) | 0.0373 (10) | |
H22 | 0.3605 | −0.0279 | 0.37 | 0.045* | |
C23 | 0.2928 (5) | −0.0096 (5) | 0.5128 (4) | 0.0447 (11) | |
H23 | 0.3192 | −0.0673 | 0.5428 | 0.054* | |
C24 | 0.2291 (5) | 0.0549 (4) | 0.5705 (4) | 0.0458 (12) | |
H24 | 0.2145 | 0.0411 | 0.6403 | 0.055* | |
C25 | 0.1874 (5) | 0.1390 (4) | 0.5260 (4) | 0.0393 (10) | |
H25 | 0.1434 | 0.1803 | 0.565 | 0.047* | |
C26 | 0.2105 (4) | 0.1622 (4) | 0.4236 (3) | 0.0330 (9) | |
H26 | 0.1836 | 0.22 | 0.3943 | 0.04* | |
C31 | 0.3876 (4) | 0.0333 (3) | 0.1754 (3) | 0.0209 (7) | |
C32 | 0.5333 (4) | 0.0864 (4) | 0.1918 (4) | 0.0337 (9) | |
H32 | 0.5854 | 0.1712 | 0.2278 | 0.04* | |
C33 | 0.6002 (4) | 0.0134 (4) | 0.1549 (4) | 0.0376 (10) | |
H33 | 0.697 | 0.0494 | 0.1654 | 0.045* | |
C34 | 0.5243 (4) | −0.1120 (4) | 0.1027 (3) | 0.0372 (10) | |
H34 | 0.5699 | −0.1613 | 0.0793 | 0.045* | |
C35 | 0.3801 (5) | −0.1647 (4) | 0.0850 (4) | 0.0388 (10) | |
H35 | 0.3288 | −0.2493 | 0.0484 | 0.047* | |
C36 | 0.3107 (4) | −0.0931 (4) | 0.1211 (3) | 0.0326 (9) | |
H36 | 0.2136 | −0.1294 | 0.109 | 0.039* | |
C41 | 0.4074 (4) | 0.2904 (3) | 0.2498 (3) | 0.0218 (7) | |
C42 | 0.4069 (4) | 0.3421 (4) | 0.1553 (3) | 0.0296 (9) | |
H42 | 0.3521 | 0.2917 | 0.0829 | 0.036* | |
C43 | 0.4875 (4) | 0.4678 (4) | 0.1696 (4) | 0.0343 (9) | |
H43 | 0.487 | 0.5018 | 0.1066 | 0.041* | |
C44 | 0.5697 (4) | 0.5442 (4) | 0.2775 (4) | 0.0325 (9) | |
H44 | 0.6233 | 0.6291 | 0.287 | 0.039* | |
C45 | 0.5707 (4) | 0.4926 (4) | 0.3701 (3) | 0.0302 (9) | |
H45 | 0.6256 | 0.5435 | 0.4423 | 0.036* | |
C46 | 0.4914 (4) | 0.3665 (4) | 0.3578 (3) | 0.0244 (8) | |
H46 | 0.4941 | 0.3328 | 0.4209 | 0.029* | |
P1 | 0.30112 (9) | 0.12593 (9) | 0.22908 (8) | 0.0202 (2) | |
Fe1 | 0.03261 (6) | 0.48883 (5) | 0.26937 (5) | 0.03260 (15) | |
I1 | 0.15066 (3) | 0.20933 (3) | 0.83998 (2) | 0.03103 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0212 (18) | 0.027 (2) | 0.034 (2) | 0.0095 (16) | 0.0056 (16) | 0.0056 (17) |
C2 | 0.024 (2) | 0.031 (2) | 0.048 (3) | 0.0088 (17) | 0.0148 (18) | 0.0076 (19) |
C3 | 0.021 (2) | 0.035 (3) | 0.075 (4) | 0.0096 (19) | 0.010 (2) | −0.010 (2) |
C4 | 0.031 (2) | 0.030 (2) | 0.079 (4) | 0.017 (2) | −0.011 (2) | 0.000 (2) |
C5 | 0.036 (2) | 0.035 (2) | 0.045 (3) | 0.014 (2) | −0.003 (2) | 0.010 (2) |
C6 | 0.033 (3) | 0.058 (4) | 0.083 (4) | 0.017 (3) | −0.001 (3) | −0.027 (3) |
C7 | 0.042 (3) | 0.024 (3) | 0.107 (5) | 0.010 (2) | −0.013 (3) | 0.002 (3) |
C8 | 0.032 (2) | 0.043 (3) | 0.067 (3) | 0.000 (2) | 0.007 (2) | 0.012 (3) |
C9 | 0.024 (2) | 0.050 (3) | 0.059 (3) | 0.016 (2) | 0.002 (2) | 0.007 (2) |
C10 | 0.034 (3) | 0.072 (4) | 0.046 (3) | 0.008 (3) | 0.001 (2) | 0.001 (3) |
C11 | 0.0236 (19) | 0.031 (2) | 0.0255 (19) | 0.0123 (17) | 0.0078 (15) | 0.0043 (16) |
C12 | 0.0160 (17) | 0.032 (2) | 0.0254 (19) | 0.0097 (16) | 0.0047 (15) | 0.0029 (16) |
C13 | 0.0192 (18) | 0.028 (2) | 0.0217 (18) | 0.0104 (16) | 0.0039 (14) | 0.0005 (15) |
C21 | 0.0234 (18) | 0.0225 (19) | 0.0214 (18) | 0.0039 (15) | 0.0062 (15) | 0.0018 (15) |
C22 | 0.049 (3) | 0.038 (2) | 0.026 (2) | 0.021 (2) | 0.0111 (19) | 0.0050 (18) |
C23 | 0.062 (3) | 0.043 (3) | 0.030 (2) | 0.022 (2) | 0.012 (2) | 0.012 (2) |
C24 | 0.058 (3) | 0.044 (3) | 0.027 (2) | 0.007 (2) | 0.019 (2) | 0.010 (2) |
C25 | 0.038 (2) | 0.048 (3) | 0.029 (2) | 0.015 (2) | 0.0152 (19) | 0.001 (2) |
C26 | 0.029 (2) | 0.036 (2) | 0.030 (2) | 0.0113 (18) | 0.0094 (17) | −0.0016 (18) |
C31 | 0.0229 (18) | 0.0255 (19) | 0.0169 (17) | 0.0121 (15) | 0.0060 (14) | 0.0063 (14) |
C32 | 0.025 (2) | 0.036 (2) | 0.039 (2) | 0.0127 (18) | 0.0074 (17) | 0.0047 (19) |
C33 | 0.025 (2) | 0.051 (3) | 0.041 (2) | 0.020 (2) | 0.0112 (18) | 0.007 (2) |
C34 | 0.040 (2) | 0.050 (3) | 0.031 (2) | 0.033 (2) | 0.0074 (18) | 0.003 (2) |
C35 | 0.041 (2) | 0.033 (2) | 0.041 (2) | 0.020 (2) | 0.005 (2) | −0.0030 (19) |
C36 | 0.026 (2) | 0.034 (2) | 0.035 (2) | 0.0140 (18) | 0.0050 (17) | −0.0004 (18) |
C41 | 0.0171 (17) | 0.0252 (19) | 0.0226 (18) | 0.0087 (15) | 0.0069 (14) | 0.0026 (15) |
C42 | 0.029 (2) | 0.032 (2) | 0.0242 (19) | 0.0097 (17) | 0.0081 (16) | 0.0043 (17) |
C43 | 0.039 (2) | 0.035 (2) | 0.033 (2) | 0.0142 (19) | 0.0167 (18) | 0.0155 (19) |
C44 | 0.025 (2) | 0.026 (2) | 0.043 (2) | 0.0046 (17) | 0.0157 (18) | 0.0044 (18) |
C45 | 0.0231 (19) | 0.033 (2) | 0.030 (2) | 0.0106 (17) | 0.0060 (16) | −0.0018 (17) |
C46 | 0.0184 (17) | 0.029 (2) | 0.0263 (19) | 0.0117 (16) | 0.0060 (15) | 0.0048 (16) |
P1 | 0.0182 (4) | 0.0231 (5) | 0.0192 (4) | 0.0090 (4) | 0.0061 (4) | 0.0029 (4) |
Fe1 | 0.0205 (3) | 0.0273 (3) | 0.0460 (4) | 0.0113 (2) | 0.0032 (2) | 0.0021 (3) |
I1 | 0.03366 (15) | 0.03771 (16) | 0.02755 (14) | 0.01734 (12) | 0.01290 (11) | 0.01189 (11) |
Geometric parameters (Å, º) top
C1—C2 | 1.429 (6) | C21—C22 | 1.388 (6) |
C1—C5 | 1.424 (6) | C21—C26 | 1.404 (5) |
C1—C11 | 1.461 (5) | C21—P1 | 1.797 (4) |
C1—Fe1 | 2.056 (4) | C22—C23 | 1.400 (6) |
C2—C3 | 1.425 (6) | C22—H22 | 0.93 |
C2—Fe1 | 2.039 (4) | C23—C24 | 1.391 (7) |
C2—H2 | 0.93 | C23—H23 | 0.93 |
C3—C4 | 1.403 (8) | C24—C25 | 1.378 (7) |
C3—Fe1 | 2.044 (4) | C24—H24 | 0.93 |
C3—H3 | 0.93 | C25—C26 | 1.379 (6) |
C4—C5 | 1.426 (7) | C25—H25 | 0.93 |
C4—Fe1 | 2.047 (4) | C26—H26 | 0.93 |
C4—H4 | 0.93 | C31—C36 | 1.388 (5) |
C5—Fe1 | 2.033 (4) | C31—C32 | 1.398 (5) |
C5—H5 | 0.93 | C31—P1 | 1.796 (3) |
C6—C7 | 1.396 (9) | C32—C33 | 1.381 (6) |
C6—C10 | 1.408 (8) | C32—H32 | 0.93 |
C6—Fe1 | 2.040 (5) | C33—C34 | 1.372 (6) |
C6—H6 | 0.93 | C33—H33 | 0.93 |
C7—C8 | 1.412 (8) | C34—C35 | 1.382 (6) |
C7—Fe1 | 2.038 (5) | C34—H34 | 0.93 |
C7—H7 | 0.93 | C35—C36 | 1.386 (5) |
C8—C9 | 1.412 (7) | C35—H35 | 0.93 |
C8—Fe1 | 2.045 (5) | C36—H36 | 0.93 |
C8—H8 | 0.93 | C41—C46 | 1.396 (5) |
C9—C10 | 1.414 (7) | C41—C42 | 1.399 (5) |
C9—Fe1 | 2.039 (4) | C41—P1 | 1.802 (4) |
C9—H9 | 0.93 | C42—C43 | 1.379 (6) |
C10—Fe1 | 2.040 (5) | C42—H42 | 0.93 |
C10—H10 | 0.93 | C43—C44 | 1.391 (6) |
C11—C12 | 1.319 (5) | C43—H43 | 0.93 |
C11—H11 | 0.93 | C44—C45 | 1.377 (6) |
C12—C13 | 1.506 (5) | C44—H44 | 0.93 |
C12—H12 | 0.93 | C45—C46 | 1.384 (6) |
C13—P1 | 1.809 (3) | C45—H45 | 0.93 |
C13—H13A | 0.97 | C46—H46 | 0.93 |
C13—H13B | 0.97 | | |
| | | |
C2—C1—C5 | 107.0 (4) | C21—C26—H26 | 120.1 |
C2—C1—C11 | 129.2 (4) | C36—C31—C32 | 119.5 (3) |
C5—C1—C11 | 123.8 (4) | C36—C31—P1 | 120.0 (3) |
C2—C1—Fe1 | 68.9 (2) | C32—C31—P1 | 120.4 (3) |
C5—C1—Fe1 | 68.8 (2) | C33—C32—C31 | 120.2 (4) |
C11—C1—Fe1 | 125.7 (3) | C33—C32—H32 | 119.9 |
C3—C2—C1 | 107.5 (4) | C31—C32—H32 | 119.9 |
C3—C2—Fe1 | 69.8 (2) | C34—C33—C32 | 120.3 (4) |
C1—C2—Fe1 | 70.2 (2) | C34—C33—H33 | 119.9 |
C3—C2—H2 | 126.3 | C32—C33—H33 | 119.9 |
C1—C2—H2 | 126.3 | C33—C34—C35 | 119.8 (4) |
Fe1—C2—H2 | 125.3 | C33—C34—H34 | 120.1 |
C4—C3—C2 | 109.5 (4) | C35—C34—H34 | 120.1 |
C4—C3—Fe1 | 70.1 (3) | C34—C35—C36 | 120.9 (4) |
C2—C3—Fe1 | 69.4 (2) | C34—C35—H35 | 119.5 |
C4—C3—H3 | 125.3 | C36—C35—H35 | 119.5 |
C2—C3—H3 | 125.3 | C35—C36—C31 | 119.3 (4) |
Fe1—C3—H3 | 126.9 | C35—C36—H36 | 120.4 |
C3—C4—C5 | 106.9 (4) | C31—C36—H36 | 120.4 |
C3—C4—Fe1 | 69.8 (3) | C46—C41—C42 | 119.5 (3) |
C5—C4—Fe1 | 69.0 (2) | C46—C41—P1 | 121.3 (3) |
C3—C4—H4 | 126.5 | C42—C41—P1 | 119.2 (3) |
C5—C4—H4 | 126.5 | C43—C42—C41 | 120.0 (4) |
Fe1—C4—H4 | 126.2 | C43—C42—H42 | 120 |
C4—C5—C1 | 109.1 (4) | C41—C42—H42 | 120 |
C4—C5—Fe1 | 70.0 (3) | C42—C43—C44 | 120.6 (4) |
C1—C5—Fe1 | 70.5 (2) | C42—C43—H43 | 119.7 |
C4—C5—H5 | 125.5 | C44—C43—H43 | 119.7 |
C1—C5—H5 | 125.5 | C45—C44—C43 | 119.3 (4) |
Fe1—C5—H5 | 125.6 | C45—C44—H44 | 120.4 |
C7—C6—C10 | 108.1 (5) | C43—C44—H44 | 120.4 |
C7—C6—Fe1 | 69.9 (3) | C44—C45—C46 | 121.2 (4) |
C10—C6—Fe1 | 69.8 (3) | C44—C45—H45 | 119.4 |
C7—C6—H6 | 125.9 | C46—C45—H45 | 119.4 |
C10—C6—H6 | 125.9 | C45—C46—C41 | 119.5 (4) |
Fe1—C6—H6 | 125.9 | C45—C46—H46 | 120.3 |
C6—C7—C8 | 108.4 (5) | C41—C46—H46 | 120.3 |
C6—C7—Fe1 | 70.0 (3) | C21—P1—C31 | 109.29 (17) |
C8—C7—Fe1 | 70.0 (3) | C21—P1—C41 | 108.83 (17) |
C6—C7—H7 | 125.8 | C31—P1—C41 | 110.27 (16) |
C8—C7—H7 | 125.8 | C21—P1—C13 | 110.54 (17) |
Fe1—C7—H7 | 125.7 | C31—P1—C13 | 108.26 (16) |
C9—C8—C7 | 107.9 (5) | C41—P1—C13 | 109.64 (17) |
C9—C8—Fe1 | 69.5 (3) | C5—Fe1—C2 | 68.55 (19) |
C7—C8—Fe1 | 69.5 (3) | C5—Fe1—C6 | 151.7 (2) |
C9—C8—H8 | 126.1 | C2—Fe1—C6 | 127.5 (2) |
C7—C8—H8 | 126.1 | C5—Fe1—C7 | 118.6 (2) |
Fe1—C8—H8 | 126.5 | C2—Fe1—C7 | 164.5 (2) |
C8—C9—C10 | 107.5 (5) | C6—Fe1—C7 | 40.0 (3) |
C8—C9—Fe1 | 70.0 (3) | C5—Fe1—C10 | 166.5 (2) |
C10—C9—Fe1 | 69.7 (3) | C2—Fe1—C10 | 108.6 (2) |
C8—C9—H9 | 126.2 | C6—Fe1—C10 | 40.4 (2) |
C10—C9—H9 | 126.2 | C7—Fe1—C10 | 67.7 (3) |
Fe1—C9—H9 | 125.6 | C5—Fe1—C9 | 128.4 (2) |
C6—C10—C9 | 108.1 (5) | C2—Fe1—C9 | 119.65 (19) |
C6—C10—Fe1 | 69.8 (3) | C6—Fe1—C9 | 68.1 (2) |
C9—C10—Fe1 | 69.7 (3) | C7—Fe1—C9 | 68.1 (2) |
C6—C10—H10 | 125.9 | C10—Fe1—C9 | 40.6 (2) |
C9—C10—H10 | 125.9 | C5—Fe1—C3 | 67.8 (2) |
Fe1—C10—H10 | 126.1 | C2—Fe1—C3 | 40.85 (17) |
C12—C11—C1 | 126.9 (4) | C6—Fe1—C3 | 107.8 (2) |
C12—C11—H11 | 116.5 | C7—Fe1—C3 | 126.5 (2) |
C1—C11—H11 | 116.5 | C10—Fe1—C3 | 119.3 (2) |
C11—C12—C13 | 123.4 (4) | C9—Fe1—C3 | 153.6 (2) |
C11—C12—H12 | 118.3 | C5—Fe1—C8 | 108.5 (2) |
C13—C12—H12 | 118.3 | C2—Fe1—C8 | 153.77 (19) |
C12—C13—P1 | 114.0 (2) | C6—Fe1—C8 | 67.7 (2) |
C12—C13—H13A | 108.8 | C7—Fe1—C8 | 40.4 (2) |
P1—C13—H13A | 108.8 | C10—Fe1—C8 | 67.8 (2) |
C12—C13—H13B | 108.8 | C9—Fe1—C8 | 40.5 (2) |
P1—C13—H13B | 108.8 | C3—Fe1—C8 | 164.2 (2) |
H13A—C13—H13B | 107.7 | C5—Fe1—C4 | 40.91 (19) |
C22—C21—C26 | 120.0 (4) | C2—Fe1—C4 | 68.82 (19) |
C22—C21—P1 | 120.3 (3) | C6—Fe1—C4 | 117.4 (2) |
C26—C21—P1 | 119.7 (3) | C7—Fe1—C4 | 106.9 (2) |
C21—C22—C23 | 119.9 (4) | C10—Fe1—C4 | 151.6 (2) |
C21—C22—H22 | 120 | C9—Fe1—C4 | 165.6 (2) |
C23—C22—H22 | 120 | C3—Fe1—C4 | 40.1 (2) |
C24—C23—C22 | 119.2 (4) | C8—Fe1—C4 | 127.1 (2) |
C24—C23—H23 | 120.4 | C5—Fe1—C1 | 40.76 (16) |
C22—C23—H23 | 120.4 | C2—Fe1—C1 | 40.85 (16) |
C25—C24—C23 | 120.9 (4) | C6—Fe1—C1 | 165.9 (3) |
C25—C24—H24 | 119.5 | C7—Fe1—C1 | 153.1 (2) |
C23—C24—H24 | 119.5 | C10—Fe1—C1 | 128.6 (2) |
C24—C25—C26 | 120.2 (4) | C9—Fe1—C1 | 109.03 (18) |
C24—C25—H25 | 119.9 | C3—Fe1—C1 | 68.29 (16) |
C26—C25—H25 | 119.9 | C8—Fe1—C1 | 119.72 (19) |
C25—C26—C21 | 119.8 (4) | C4—Fe1—C1 | 68.94 (17) |
C25—C26—H26 | 120.1 | | |
| | | |
C5—C1—C2—C3 | 1.6 (4) | C10—C6—Fe1—C8 | −81.5 (4) |
C11—C1—C2—C3 | 179.6 (4) | C7—C6—Fe1—C4 | −83.8 (4) |
Fe1—C1—C2—C3 | 60.1 (3) | C10—C6—Fe1—C4 | 157.0 (3) |
C5—C1—C2—Fe1 | −58.4 (3) | C7—C6—Fe1—C1 | 162.5 (6) |
C11—C1—C2—Fe1 | 119.5 (4) | C10—C6—Fe1—C1 | 43.3 (9) |
C1—C2—C3—C4 | −1.7 (5) | C6—C7—Fe1—C5 | 155.5 (3) |
Fe1—C2—C3—C4 | 58.7 (3) | C8—C7—Fe1—C5 | −85.3 (4) |
C1—C2—C3—Fe1 | −60.4 (3) | C6—C7—Fe1—C2 | 41.3 (9) |
C2—C3—C4—C5 | 1.0 (5) | C8—C7—Fe1—C2 | 160.5 (7) |
Fe1—C3—C4—C5 | 59.3 (3) | C8—C7—Fe1—C6 | 119.2 (5) |
C2—C3—C4—Fe1 | −58.3 (3) | C6—C7—Fe1—C10 | −37.7 (3) |
C3—C4—C5—C1 | 0.0 (5) | C8—C7—Fe1—C10 | 81.5 (4) |
Fe1—C4—C5—C1 | 59.8 (3) | C6—C7—Fe1—C9 | −81.6 (3) |
C3—C4—C5—Fe1 | −59.8 (3) | C8—C7—Fe1—C9 | 37.6 (3) |
C2—C1—C5—C4 | −1.1 (5) | C6—C7—Fe1—C3 | 73.1 (4) |
C11—C1—C5—C4 | −179.1 (4) | C8—C7—Fe1—C3 | −167.7 (3) |
Fe1—C1—C5—C4 | −59.6 (3) | C6—C7—Fe1—C8 | −119.2 (5) |
C2—C1—C5—Fe1 | 58.5 (3) | C6—C7—Fe1—C4 | 112.7 (3) |
C11—C1—C5—Fe1 | −119.5 (4) | C8—C7—Fe1—C4 | −128.1 (4) |
C10—C6—C7—C8 | −0.2 (6) | C6—C7—Fe1—C1 | −170.7 (4) |
Fe1—C6—C7—C8 | −59.8 (3) | C8—C7—Fe1—C1 | −51.5 (6) |
C10—C6—C7—Fe1 | 59.6 (4) | C6—C10—Fe1—C5 | 158.1 (9) |
C6—C7—C8—C9 | 0.6 (6) | C9—C10—Fe1—C5 | 38.8 (11) |
Fe1—C7—C8—C9 | −59.2 (3) | C6—C10—Fe1—C2 | −126.5 (4) |
C6—C7—C8—Fe1 | 59.8 (4) | C9—C10—Fe1—C2 | 114.2 (3) |
C7—C8—C9—C10 | −0.8 (5) | C9—C10—Fe1—C6 | −119.3 (5) |
Fe1—C8—C9—C10 | −59.9 (3) | C6—C10—Fe1—C7 | 37.4 (3) |
C7—C8—C9—Fe1 | 59.1 (3) | C9—C10—Fe1—C7 | −81.9 (4) |
C7—C6—C10—C9 | −0.2 (6) | C6—C10—Fe1—C9 | 119.3 (5) |
Fe1—C6—C10—C9 | 59.4 (3) | C6—C10—Fe1—C3 | −83.1 (4) |
C7—C6—C10—Fe1 | −59.6 (4) | C9—C10—Fe1—C3 | 157.6 (3) |
C8—C9—C10—C6 | 0.6 (5) | C6—C10—Fe1—C8 | 81.2 (4) |
Fe1—C9—C10—C6 | −59.5 (3) | C9—C10—Fe1—C8 | −38.1 (3) |
C8—C9—C10—Fe1 | 60.1 (3) | C6—C10—Fe1—C4 | −46.9 (6) |
C2—C1—C11—C12 | 19.1 (7) | C9—C10—Fe1—C4 | −166.2 (4) |
C5—C1—C11—C12 | −163.3 (4) | C6—C10—Fe1—C1 | −167.7 (3) |
Fe1—C1—C11—C12 | 109.9 (4) | C9—C10—Fe1—C1 | 73.0 (4) |
C1—C11—C12—C13 | 178.4 (3) | C8—C9—Fe1—C5 | 72.3 (4) |
C11—C12—C13—P1 | 97.6 (4) | C10—C9—Fe1—C5 | −169.3 (3) |
C26—C21—C22—C23 | 1.0 (6) | C8—C9—Fe1—C2 | 157.4 (3) |
P1—C21—C22—C23 | −178.6 (3) | C10—C9—Fe1—C2 | −84.2 (4) |
C21—C22—C23—C24 | −1.1 (7) | C8—C9—Fe1—C6 | −80.9 (4) |
C22—C23—C24—C25 | 1.1 (7) | C10—C9—Fe1—C6 | 37.5 (4) |
C23—C24—C25—C26 | −1.1 (7) | C8—C9—Fe1—C7 | −37.6 (4) |
C24—C25—C26—C21 | 1.0 (6) | C10—C9—Fe1—C7 | 80.8 (4) |
C22—C21—C26—C25 | −1.0 (6) | C8—C9—Fe1—C10 | −118.4 (5) |
P1—C21—C26—C25 | 178.6 (3) | C8—C9—Fe1—C3 | −166.9 (4) |
C36—C31—C32—C33 | −0.4 (6) | C10—C9—Fe1—C3 | −48.5 (6) |
P1—C31—C32—C33 | 177.1 (3) | C10—C9—Fe1—C8 | 118.4 (5) |
C31—C32—C33—C34 | −0.6 (7) | C8—C9—Fe1—C4 | 34.5 (9) |
C32—C33—C34—C35 | 1.3 (7) | C10—C9—Fe1—C4 | 152.9 (7) |
C33—C34—C35—C36 | −1.1 (7) | C8—C9—Fe1—C1 | 113.8 (3) |
C34—C35—C36—C31 | 0.2 (7) | C10—C9—Fe1—C1 | −127.8 (3) |
C32—C31—C36—C35 | 0.6 (6) | C4—C3—Fe1—C5 | −38.5 (3) |
P1—C31—C36—C35 | −176.9 (3) | C2—C3—Fe1—C5 | 82.5 (3) |
C46—C41—C42—C43 | −0.8 (5) | C4—C3—Fe1—C2 | −121.0 (4) |
P1—C41—C42—C43 | 179.9 (3) | C4—C3—Fe1—C6 | 111.7 (3) |
C41—C42—C43—C44 | −0.1 (6) | C2—C3—Fe1—C6 | −127.3 (3) |
C42—C43—C44—C45 | 0.6 (6) | C4—C3—Fe1—C7 | 71.4 (4) |
C43—C44—C45—C46 | −0.1 (6) | C2—C3—Fe1—C7 | −167.6 (3) |
C44—C45—C46—C41 | −0.9 (5) | C4—C3—Fe1—C10 | 154.2 (3) |
C42—C41—C46—C45 | 1.3 (5) | C2—C3—Fe1—C10 | −84.8 (3) |
P1—C41—C46—C45 | −179.5 (3) | C4—C3—Fe1—C9 | −171.9 (4) |
C22—C21—P1—C31 | −1.4 (4) | C2—C3—Fe1—C9 | −50.9 (5) |
C26—C21—P1—C31 | 179.0 (3) | C4—C3—Fe1—C8 | 40.9 (9) |
C22—C21—P1—C41 | −121.9 (3) | C2—C3—Fe1—C8 | 161.9 (7) |
C26—C21—P1—C41 | 58.5 (3) | C2—C3—Fe1—C4 | 121.0 (4) |
C22—C21—P1—C13 | 117.7 (3) | C4—C3—Fe1—C1 | −82.7 (3) |
C26—C21—P1—C13 | −61.9 (3) | C2—C3—Fe1—C1 | 38.3 (3) |
C36—C31—P1—C21 | 80.0 (3) | C9—C8—Fe1—C5 | −128.0 (3) |
C32—C31—P1—C21 | −97.6 (3) | C7—C8—Fe1—C5 | 112.7 (4) |
C36—C31—P1—C41 | −160.4 (3) | C9—C8—Fe1—C2 | −49.1 (6) |
C32—C31—P1—C41 | 22.0 (4) | C7—C8—Fe1—C2 | −168.4 (5) |
C36—C31—P1—C13 | −40.5 (4) | C9—C8—Fe1—C6 | 81.9 (4) |
C32—C31—P1—C13 | 142.0 (3) | C7—C8—Fe1—C6 | −37.3 (4) |
C46—C41—P1—C21 | 20.4 (3) | C9—C8—Fe1—C7 | 119.3 (5) |
C42—C41—P1—C21 | −160.4 (3) | C9—C8—Fe1—C10 | 38.1 (3) |
C46—C41—P1—C31 | −99.5 (3) | C7—C8—Fe1—C10 | −81.1 (4) |
C42—C41—P1—C31 | 79.7 (3) | C7—C8—Fe1—C9 | −119.3 (5) |
C46—C41—P1—C13 | 141.4 (3) | C9—C8—Fe1—C3 | 158.2 (7) |
C42—C41—P1—C13 | −39.4 (3) | C7—C8—Fe1—C3 | 39.0 (10) |
C12—C13—P1—C21 | 56.8 (3) | C9—C8—Fe1—C4 | −169.8 (3) |
C12—C13—P1—C31 | 176.4 (3) | C7—C8—Fe1—C4 | 70.9 (4) |
C12—C13—P1—C41 | −63.2 (3) | C9—C8—Fe1—C1 | −84.8 (3) |
C4—C5—Fe1—C2 | 82.0 (3) | C7—C8—Fe1—C1 | 155.9 (3) |
C1—C5—Fe1—C2 | −37.9 (2) | C3—C4—Fe1—C5 | 118.2 (4) |
C4—C5—Fe1—C6 | −48.5 (6) | C3—C4—Fe1—C2 | 37.0 (3) |
C1—C5—Fe1—C6 | −168.4 (4) | C5—C4—Fe1—C2 | −81.3 (3) |
C4—C5—Fe1—C7 | −82.8 (4) | C3—C4—Fe1—C6 | −85.3 (4) |
C1—C5—Fe1—C7 | 157.3 (3) | C5—C4—Fe1—C6 | 156.4 (3) |
C4—C5—Fe1—C10 | 162.2 (9) | C3—C4—Fe1—C7 | −127.2 (3) |
C1—C5—Fe1—C10 | 42.3 (10) | C5—C4—Fe1—C7 | 114.5 (3) |
C4—C5—Fe1—C9 | −166.5 (3) | C3—C4—Fe1—C10 | −53.1 (6) |
C1—C5—Fe1—C9 | 73.6 (3) | C5—C4—Fe1—C10 | −171.4 (4) |
C4—C5—Fe1—C3 | 37.8 (3) | C3—C4—Fe1—C9 | 165.5 (7) |
C1—C5—Fe1—C3 | −82.1 (3) | C5—C4—Fe1—C9 | 47.2 (9) |
C4—C5—Fe1—C8 | −125.8 (3) | C5—C4—Fe1—C3 | −118.2 (4) |
C1—C5—Fe1—C8 | 114.3 (3) | C3—C4—Fe1—C8 | −167.1 (3) |
C1—C5—Fe1—C4 | −119.9 (4) | C5—C4—Fe1—C8 | 74.7 (4) |
C4—C5—Fe1—C1 | 119.9 (4) | C3—C4—Fe1—C1 | 80.9 (3) |
C3—C2—Fe1—C5 | −80.4 (3) | C5—C4—Fe1—C1 | −37.3 (3) |
C1—C2—Fe1—C5 | 37.8 (2) | C2—C1—Fe1—C5 | −119.1 (3) |
C3—C2—Fe1—C6 | 72.6 (4) | C11—C1—Fe1—C5 | 117.1 (5) |
C1—C2—Fe1—C6 | −169.2 (3) | C5—C1—Fe1—C2 | 119.1 (3) |
C3—C2—Fe1—C7 | 40.3 (9) | C11—C1—Fe1—C2 | −123.9 (5) |
C1—C2—Fe1—C7 | 158.5 (8) | C2—C1—Fe1—C6 | 37.8 (8) |
C3—C2—Fe1—C10 | 113.6 (3) | C5—C1—Fe1—C6 | 156.9 (7) |
C1—C2—Fe1—C10 | −128.2 (3) | C11—C1—Fe1—C6 | −86.0 (8) |
C3—C2—Fe1—C9 | 156.7 (3) | C2—C1—Fe1—C7 | −167.5 (4) |
C1—C2—Fe1—C9 | −85.1 (3) | C5—C1—Fe1—C7 | −48.4 (5) |
C1—C2—Fe1—C3 | 118.2 (4) | C11—C1—Fe1—C7 | 68.7 (6) |
C3—C2—Fe1—C8 | −169.0 (5) | C2—C1—Fe1—C10 | 72.5 (3) |
C1—C2—Fe1—C8 | −50.8 (6) | C5—C1—Fe1—C10 | −168.4 (3) |
C3—C2—Fe1—C4 | −36.3 (3) | C11—C1—Fe1—C10 | −51.4 (4) |
C1—C2—Fe1—C4 | 81.9 (3) | C2—C1—Fe1—C9 | 113.7 (3) |
C3—C2—Fe1—C1 | −118.2 (4) | C5—C1—Fe1—C9 | −127.3 (3) |
C7—C6—Fe1—C5 | −50.2 (6) | C11—C1—Fe1—C9 | −10.2 (4) |
C10—C6—Fe1—C5 | −169.4 (4) | C2—C1—Fe1—C3 | −38.3 (3) |
C7—C6—Fe1—C2 | −167.1 (3) | C5—C1—Fe1—C3 | 80.7 (3) |
C10—C6—Fe1—C2 | 73.7 (4) | C11—C1—Fe1—C3 | −162.2 (4) |
C10—C6—Fe1—C7 | −119.2 (5) | C2—C1—Fe1—C8 | 156.8 (3) |
C7—C6—Fe1—C10 | 119.2 (5) | C5—C1—Fe1—C8 | −84.2 (3) |
C7—C6—Fe1—C9 | 81.5 (3) | C11—C1—Fe1—C8 | 32.9 (4) |
C10—C6—Fe1—C9 | −37.7 (3) | C2—C1—Fe1—C4 | −81.6 (3) |
C7—C6—Fe1—C3 | −126.2 (3) | C5—C1—Fe1—C4 | 37.5 (3) |
C10—C6—Fe1—C3 | 114.6 (4) | C11—C1—Fe1—C4 | 154.6 (4) |
C7—C6—Fe1—C8 | 37.7 (3) | | |
(II) (3-Ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide
top
Crystal data top
[Fe(C5H5)(C26H23P)]·I | F(000) = 1232 |
Mr = 614.25 | Dx = 1.549 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9962 reflections |
a = 10.1090 (16) Å | θ = 2.5–26.1° |
b = 10.6299 (15) Å | µ = 1.82 mm−1 |
c = 25.148 (4) Å | T = 150 K |
β = 102.868 (7)° | Prism, red |
V = 2634.4 (7) Å3 | 0.13 × 0.11 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker APEXII diffractometer | 5396 independent reflections |
Radiation source: fine-focus sealed tube | 4161 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
CCD rotation images, thick slices scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −12→12 |
Tmin = 0.699, Tmax = 0.745 | k = −13→13 |
50617 measured reflections | l = −29→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.049 | H-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 parameters | Δρmax = 0.52 e Å−3 |
10 restraints | Δρmin = −0.50 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 0.07591 (3) | 0.92217 (3) | 0.811703 (13) | 0.02405 (9) | |
P1 | 0.58954 (6) | 0.65946 (5) | 0.90227 (2) | 0.01960 (13) | |
C1 | 0.1316 (2) | 0.8232 (2) | 0.88333 (9) | 0.0225 (5) | |
C2 | 0.1548 (2) | 0.9550 (2) | 0.89213 (9) | 0.0268 (6) | |
H2 | 0.2381 | 0.9927 | 0.9065 | 0.032* | |
C3 | 0.0298 (3) | 1.0182 (3) | 0.87538 (10) | 0.0352 (6) | |
H3 | 0.0166 | 1.1046 | 0.877 | 0.042* | |
C4 | −0.0717 (3) | 0.9284 (3) | 0.85583 (10) | 0.0351 (7) | |
H4 | −0.1634 | 0.9451 | 0.8425 | 0.042* | |
C5 | −0.0097 (2) | 0.8082 (3) | 0.86010 (9) | 0.0302 (6) | |
H5 | −0.0536 | 0.7323 | 0.8495 | 0.036* | |
C6 | 0.1139 (15) | 0.8288 (13) | 0.7456 (6) | 0.033 (4) | 0.54 |
H6 | 0.1202 | 0.742 | 0.7423 | 0.04* | 0.54 |
C7 | 0.2216 (11) | 0.9082 (19) | 0.7675 (5) | 0.053 (7) | 0.54 |
H7 | 0.3117 | 0.8851 | 0.7808 | 0.064* | 0.54 |
C8 | 0.167 (2) | 1.0301 (14) | 0.7656 (9) | 0.060 (7) | 0.54 |
H8 | 0.2157 | 1.1026 | 0.7782 | 0.073* | 0.54 |
C9 | 0.028 (2) | 1.0249 (19) | 0.7418 (14) | 0.050 (6) | 0.54 |
H9 | −0.0312 | 1.0929 | 0.7353 | 0.061* | 0.54 |
C10 | −0.0052 (15) | 0.899 (2) | 0.7294 (10) | 0.043 (4) | 0.54 |
H10 | −0.0907 | 0.8675 | 0.7133 | 0.052* | 0.54 |
C6B | 0.176 (2) | 0.8507 (12) | 0.7575 (7) | 0.039 (7) | 0.46 |
H6B | 0.2228 | 0.7748 | 0.7619 | 0.047* | 0.46 |
C7B | 0.2330 (16) | 0.9668 (18) | 0.7739 (8) | 0.040 (4) | 0.46 |
H7B | 0.3231 | 0.9826 | 0.7907 | 0.048* | 0.46 |
C8B | 0.128 (2) | 1.0562 (14) | 0.7605 (11) | 0.031 (3) | 0.46 |
H8B | 0.1365 | 1.1422 | 0.7673 | 0.037* | 0.46 |
C9B | 0.0090 (17) | 0.993 (2) | 0.7349 (15) | 0.039 (6) | 0.46 |
H9B | −0.0751 | 1.0297 | 0.7214 | 0.046* | 0.46 |
C10B | 0.038 (2) | 0.8642 (18) | 0.7334 (8) | 0.046 (7) | 0.46 |
H10B | −0.0223 | 0.8003 | 0.7191 | 0.056* | 0.46 |
C11 | 0.2326 (2) | 0.7227 (2) | 0.89490 (9) | 0.0228 (5) | |
H11 | 0.211 | 0.6462 | 0.8771 | 0.027* | |
C12 | 0.3528 (2) | 0.7329 (2) | 0.92901 (9) | 0.0213 (5) | |
H12 | 0.373 | 0.8085 | 0.9477 | 0.026* | |
C13 | 0.4586 (2) | 0.6316 (2) | 0.93959 (9) | 0.0226 (5) | |
H13A | 0.416 | 0.551 | 0.9289 | 0.027* | |
H13B | 0.4993 | 0.6282 | 0.9783 | 0.027* | |
C21 | 0.6595 (2) | 0.8117 (2) | 0.92184 (9) | 0.0216 (5) | |
C22 | 0.7822 (2) | 0.8208 (2) | 0.95968 (9) | 0.0264 (6) | |
H22 | 0.834 | 0.7492 | 0.9705 | 0.032* | |
C23 | 0.8270 (3) | 0.9366 (3) | 0.98116 (10) | 0.0354 (6) | |
H23 | 0.9088 | 0.9427 | 1.0068 | 0.043* | |
C24 | 0.7518 (3) | 1.0427 (3) | 0.96501 (10) | 0.0384 (7) | |
H24 | 0.783 | 1.1202 | 0.9798 | 0.046* | |
C25 | 0.6303 (3) | 1.0358 (2) | 0.92712 (11) | 0.0356 (6) | |
H25 | 0.58 | 1.1083 | 0.9163 | 0.043* | |
C26 | 0.5834 (3) | 0.9196 (2) | 0.90515 (10) | 0.0289 (6) | |
H26 | 0.5017 | 0.9141 | 0.8795 | 0.035* | |
C31 | 0.5195 (2) | 0.6558 (2) | 0.83027 (9) | 0.0217 (5) | |
C32 | 0.5704 (3) | 0.7327 (2) | 0.79466 (9) | 0.0300 (6) | |
H32 | 0.6387 | 0.7905 | 0.8083 | 0.036* | |
C33 | 0.5192 (3) | 0.7231 (3) | 0.73892 (10) | 0.0362 (7) | |
H33 | 0.5534 | 0.7739 | 0.715 | 0.043* | |
C34 | 0.4178 (3) | 0.6383 (3) | 0.71917 (10) | 0.0371 (7) | |
H34 | 0.3825 | 0.6327 | 0.6818 | 0.044* | |
C35 | 0.3678 (3) | 0.5613 (2) | 0.75413 (10) | 0.0351 (6) | |
H35 | 0.2995 | 0.5038 | 0.7402 | 0.042* | |
C36 | 0.4184 (2) | 0.5688 (2) | 0.80975 (9) | 0.0272 (6) | |
H36 | 0.3852 | 0.5161 | 0.8333 | 0.033* | |
C41 | 0.7169 (2) | 0.5392 (2) | 0.91854 (9) | 0.0216 (5) | |
C42 | 0.7599 (2) | 0.4958 (2) | 0.97192 (9) | 0.0238 (5) | |
H42 | 0.7214 | 0.5278 | 0.9994 | 0.029* | |
C43 | 0.8602 (2) | 0.4047 (2) | 0.98383 (9) | 0.0274 (6) | |
H43 | 0.8886 | 0.3753 | 1.0194 | 0.033* | |
C44 | 0.9177 (3) | 0.3577 (2) | 0.94337 (10) | 0.0329 (6) | |
H44 | 0.9852 | 0.2968 | 0.9516 | 0.04* | |
C45 | 0.8760 (3) | 0.4004 (3) | 0.89086 (11) | 0.0470 (8) | |
H45 | 0.9155 | 0.3684 | 0.8637 | 0.056* | |
C46 | 0.7762 (3) | 0.4902 (3) | 0.87810 (10) | 0.0370 (7) | |
H46 | 0.7482 | 0.5184 | 0.8423 | 0.044* | |
I1 | 0.316992 (19) | 0.295651 (16) | 0.900690 (7) | 0.03630 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.02670 (19) | 0.03007 (19) | 0.01633 (18) | 0.00157 (16) | 0.00680 (14) | 0.00163 (14) |
P1 | 0.0236 (3) | 0.0207 (3) | 0.0142 (3) | −0.0007 (3) | 0.0037 (2) | 0.0004 (2) |
C1 | 0.0231 (13) | 0.0310 (14) | 0.0144 (11) | −0.0031 (10) | 0.0062 (10) | 0.0001 (10) |
C2 | 0.0279 (14) | 0.0336 (14) | 0.0179 (12) | 0.0009 (11) | 0.0031 (10) | −0.0040 (10) |
C3 | 0.0438 (17) | 0.0411 (16) | 0.0230 (14) | 0.0153 (14) | 0.0121 (12) | 0.0001 (12) |
C4 | 0.0234 (14) | 0.0635 (19) | 0.0192 (13) | 0.0085 (14) | 0.0064 (11) | 0.0053 (13) |
C5 | 0.0253 (13) | 0.0459 (16) | 0.0203 (13) | −0.0059 (13) | 0.0070 (10) | 0.0034 (12) |
C6 | 0.050 (13) | 0.033 (4) | 0.020 (7) | 0.008 (7) | 0.013 (9) | 0.002 (4) |
C7 | 0.026 (6) | 0.12 (2) | 0.021 (5) | −0.007 (11) | 0.015 (5) | 0.000 (13) |
C8 | 0.082 (15) | 0.058 (12) | 0.055 (13) | −0.043 (11) | 0.046 (13) | −0.013 (11) |
C9 | 0.086 (15) | 0.039 (6) | 0.034 (11) | 0.030 (8) | 0.030 (11) | 0.022 (7) |
C10 | 0.042 (6) | 0.065 (10) | 0.022 (5) | −0.003 (7) | 0.006 (5) | −0.002 (7) |
C6B | 0.046 (17) | 0.042 (12) | 0.036 (14) | 0.024 (10) | 0.025 (13) | 0.018 (10) |
C7B | 0.029 (6) | 0.061 (12) | 0.030 (7) | 0.006 (7) | 0.008 (5) | 0.016 (8) |
C8B | 0.044 (8) | 0.026 (4) | 0.026 (5) | 0.009 (5) | 0.014 (6) | 0.006 (4) |
C9B | 0.025 (5) | 0.064 (15) | 0.027 (8) | 0.007 (7) | 0.006 (4) | 0.019 (12) |
C10B | 0.070 (18) | 0.059 (13) | 0.012 (7) | −0.025 (11) | 0.011 (12) | −0.002 (9) |
C11 | 0.0291 (13) | 0.0246 (13) | 0.0169 (12) | −0.0062 (11) | 0.0099 (10) | −0.0002 (10) |
C12 | 0.0259 (13) | 0.0239 (13) | 0.0159 (12) | −0.0039 (10) | 0.0082 (10) | −0.0014 (9) |
C13 | 0.0275 (13) | 0.0243 (13) | 0.0166 (12) | −0.0033 (10) | 0.0062 (10) | 0.0016 (10) |
C21 | 0.0250 (12) | 0.0248 (13) | 0.0160 (12) | −0.0040 (10) | 0.0069 (10) | 0.0002 (10) |
C22 | 0.0277 (13) | 0.0336 (15) | 0.0188 (12) | −0.0057 (11) | 0.0072 (11) | 0.0016 (10) |
C23 | 0.0402 (16) | 0.0422 (17) | 0.0240 (14) | −0.0180 (14) | 0.0073 (12) | −0.0057 (12) |
C24 | 0.060 (2) | 0.0317 (15) | 0.0289 (15) | −0.0197 (14) | 0.0225 (15) | −0.0090 (12) |
C25 | 0.0541 (19) | 0.0241 (14) | 0.0349 (15) | 0.0013 (13) | 0.0236 (14) | 0.0020 (11) |
C26 | 0.0338 (14) | 0.0287 (14) | 0.0245 (13) | 0.0003 (12) | 0.0070 (11) | 0.0023 (11) |
C31 | 0.0271 (13) | 0.0226 (12) | 0.0158 (12) | 0.0034 (10) | 0.0053 (10) | −0.0004 (9) |
C32 | 0.0369 (15) | 0.0305 (14) | 0.0223 (13) | −0.0036 (12) | 0.0061 (11) | 0.0010 (10) |
C33 | 0.0500 (17) | 0.0403 (16) | 0.0208 (14) | 0.0058 (14) | 0.0134 (12) | 0.0064 (12) |
C34 | 0.0495 (17) | 0.0470 (17) | 0.0129 (13) | 0.0125 (15) | 0.0030 (12) | −0.0050 (12) |
C35 | 0.0372 (15) | 0.0405 (16) | 0.0250 (14) | −0.0017 (13) | 0.0016 (12) | −0.0119 (12) |
C36 | 0.0331 (14) | 0.0268 (13) | 0.0218 (13) | −0.0027 (11) | 0.0063 (11) | −0.0031 (10) |
C41 | 0.0253 (13) | 0.0204 (12) | 0.0193 (12) | −0.0024 (10) | 0.0053 (10) | −0.0012 (10) |
C42 | 0.0284 (13) | 0.0284 (13) | 0.0168 (12) | −0.0008 (11) | 0.0096 (10) | −0.0006 (10) |
C43 | 0.0302 (14) | 0.0311 (14) | 0.0204 (13) | 0.0025 (12) | 0.0046 (11) | 0.0081 (11) |
C44 | 0.0378 (15) | 0.0293 (14) | 0.0312 (15) | 0.0124 (12) | 0.0067 (12) | 0.0031 (11) |
C45 | 0.063 (2) | 0.0550 (19) | 0.0265 (15) | 0.0299 (16) | 0.0181 (14) | 0.0000 (13) |
C46 | 0.0523 (18) | 0.0435 (16) | 0.0160 (13) | 0.0182 (14) | 0.0098 (12) | 0.0045 (11) |
I1 | 0.05332 (12) | 0.02727 (9) | 0.03013 (10) | −0.00953 (9) | 0.01316 (8) | −0.00407 (8) |
Geometric parameters (Å, º) top
Fe1—C8 | 1.996 (18) | C9B—H9B | 0.93 |
Fe1—C10B | 2.018 (19) | C10B—H10B | 0.93 |
Fe1—C6B | 2.018 (13) | C11—C12 | 1.327 (3) |
Fe1—C2 | 2.032 (2) | C11—H11 | 0.93 |
Fe1—C9 | 2.04 (3) | C12—C13 | 1.499 (3) |
Fe1—C7 | 2.038 (13) | C12—H12 | 0.93 |
Fe1—C9B | 2.04 (3) | C13—H13A | 0.97 |
Fe1—C3 | 2.039 (2) | C13—H13B | 0.97 |
Fe1—C5 | 2.041 (2) | C21—C22 | 1.389 (3) |
Fe1—C6 | 2.044 (14) | C21—C26 | 1.393 (3) |
P1—C21 | 1.790 (2) | C22—C23 | 1.380 (3) |
P1—C31 | 1.792 (2) | C22—H22 | 0.93 |
P1—C41 | 1.795 (2) | C23—C24 | 1.370 (4) |
P1—C13 | 1.810 (2) | C23—H23 | 0.93 |
C1—C5 | 1.427 (3) | C24—C25 | 1.378 (4) |
C1—C2 | 1.430 (3) | C24—H24 | 0.93 |
C1—C11 | 1.461 (3) | C25—C26 | 1.393 (3) |
C2—C3 | 1.410 (3) | C25—H25 | 0.93 |
C2—H2 | 0.93 | C26—H26 | 0.93 |
C3—C4 | 1.407 (4) | C31—C36 | 1.390 (3) |
C3—H3 | 0.93 | C31—C32 | 1.393 (3) |
C4—C5 | 1.417 (4) | C32—C33 | 1.386 (3) |
C4—H4 | 0.9301 | C32—H32 | 0.93 |
C5—H5 | 0.93 | C33—C34 | 1.373 (4) |
C6—C7 | 1.391 (12) | C33—H33 | 0.93 |
C6—C10 | 1.398 (13) | C34—C35 | 1.377 (4) |
C6—H6 | 0.93 | C34—H34 | 0.93 |
C7—C8 | 1.404 (13) | C35—C36 | 1.381 (3) |
C7—H7 | 0.93 | C35—H35 | 0.93 |
C8—C9 | 1.402 (12) | C36—H36 | 0.93 |
C8—H8 | 0.93 | C41—C46 | 1.392 (3) |
C9—C10 | 1.400 (13) | C41—C42 | 1.394 (3) |
C9—H9 | 0.93 | C42—C43 | 1.385 (3) |
C10—H10 | 0.93 | C42—H42 | 0.93 |
C6B—C7B | 1.385 (15) | C43—C44 | 1.374 (3) |
C6B—C10B | 1.399 (13) | C43—H43 | 0.93 |
C6B—H6B | 0.93 | C44—C45 | 1.371 (4) |
C7B—C8B | 1.406 (15) | C44—H44 | 0.93 |
C7B—H7B | 0.93 | C45—C46 | 1.374 (4) |
C8B—C9B | 1.407 (14) | C45—H45 | 0.93 |
C8B—H8B | 0.93 | C46—H46 | 0.93 |
C9B—C10B | 1.399 (13) | | |
| | | |
C8—Fe1—C10B | 67.7 (7) | Fe1—C9—H9 | 126.2 |
C8—Fe1—C6B | 57.2 (5) | C6—C10—C9 | 107.2 (13) |
C10B—Fe1—C6B | 40.6 (4) | C6—C10—Fe1 | 69.3 (10) |
C8—Fe1—C2 | 110.4 (5) | C9—C10—Fe1 | 68.9 (15) |
C10B—Fe1—C2 | 166.2 (7) | C6—C10—H10 | 126.4 |
C6B—Fe1—C2 | 126.3 (6) | C9—C10—H10 | 126.4 |
C8—Fe1—C9 | 40.7 (5) | Fe1—C10—H10 | 126.8 |
C10B—Fe1—C9 | 50.4 (9) | C7B—C6B—C10B | 110.3 (11) |
C6B—Fe1—C9 | 71.1 (8) | C7B—C6B—Fe1 | 72.6 (10) |
C2—Fe1—C9 | 137.1 (7) | C10B—C6B—Fe1 | 69.7 (9) |
C8—Fe1—C7 | 40.7 (4) | C7B—C6B—H6B | 124.9 |
C10B—Fe1—C7 | 56.5 (5) | C10B—C6B—H6B | 124.9 |
C6B—Fe1—C7 | 21.9 (3) | Fe1—C6B—H6B | 124.4 |
C2—Fe1—C7 | 112.6 (4) | C6B—C7B—C8B | 106.9 (12) |
C9—Fe1—C7 | 68.2 (7) | C6B—C7B—Fe1 | 67.9 (10) |
C8—Fe1—C9B | 48.6 (9) | C8B—C7B—Fe1 | 69.8 (14) |
C10B—Fe1—C9B | 40.3 (5) | C6B—C7B—H7B | 126.6 |
C6B—Fe1—C9B | 67.0 (7) | C8B—C7B—H7B | 126.6 |
C2—Fe1—C9B | 148.5 (7) | Fe1—C7B—H7B | 127.3 |
C9—Fe1—C9B | 11.6 (9) | C7B—C8B—C9B | 107.9 (12) |
C7—Fe1—C9B | 68.8 (8) | C7B—C8B—Fe1 | 70.6 (13) |
C8—Fe1—C3 | 112.6 (5) | C9B—C8B—Fe1 | 68.9 (17) |
C10B—Fe1—C3 | 153.3 (7) | C7B—C8B—H8B | 126 |
C6B—Fe1—C3 | 162.9 (6) | C9B—C8B—H8B | 126 |
C2—Fe1—C3 | 40.52 (10) | Fe1—C8B—H8B | 126.2 |
C9—Fe1—C3 | 111.0 (7) | C10B—C9B—C8B | 108.5 (10) |
C7—Fe1—C3 | 141.6 (5) | C10B—C9B—Fe1 | 69.0 (14) |
C9B—Fe1—C3 | 118.3 (7) | C8B—C9B—Fe1 | 71.0 (16) |
C8—Fe1—C5 | 177.6 (7) | C10B—C9B—H9B | 125.7 |
C10B—Fe1—C5 | 112.8 (5) | C8B—C9B—H9B | 125.7 |
C6B—Fe1—C5 | 121.5 (4) | Fe1—C9B—H9B | 125.6 |
C2—Fe1—C5 | 68.48 (10) | C9B—C10B—C6B | 106.4 (9) |
C9—Fe1—C5 | 141.6 (7) | C9B—C10B—Fe1 | 70.7 (16) |
C7—Fe1—C5 | 137.3 (6) | C6B—C10B—Fe1 | 69.7 (8) |
C9B—Fe1—C5 | 133.4 (7) | C9B—C10B—H10B | 126.8 |
C3—Fe1—C5 | 68.13 (11) | C6B—C10B—H10B | 126.8 |
C8—Fe1—C6 | 67.2 (6) | Fe1—C10B—H10B | 124.5 |
C10B—Fe1—C6 | 24.1 (5) | C12—C11—C1 | 124.6 (2) |
C6B—Fe1—C6 | 19.1 (4) | C12—C11—H11 | 117.7 |
C2—Fe1—C6 | 142.1 (4) | C1—C11—H11 | 117.7 |
C9—Fe1—C6 | 67.0 (8) | C11—C12—C13 | 124.8 (2) |
C7—Fe1—C6 | 39.8 (4) | C11—C12—H12 | 117.6 |
C9B—Fe1—C6 | 59.5 (8) | C13—C12—H12 | 117.6 |
C3—Fe1—C6 | 177.3 (4) | C12—C13—P1 | 111.45 (15) |
C5—Fe1—C6 | 112.2 (4) | C12—C13—H13A | 109.3 |
C21—P1—C31 | 109.90 (10) | P1—C13—H13A | 109.3 |
C21—P1—C41 | 111.19 (11) | C12—C13—H13B | 109.3 |
C31—P1—C41 | 108.48 (10) | P1—C13—H13B | 109.3 |
C21—P1—C13 | 107.15 (10) | H13A—C13—H13B | 108 |
C31—P1—C13 | 110.51 (11) | C22—C21—C26 | 119.9 (2) |
C41—P1—C13 | 109.61 (10) | C22—C21—P1 | 119.30 (18) |
C5—C1—C2 | 106.7 (2) | C26—C21—P1 | 120.25 (18) |
C5—C1—C11 | 126.2 (2) | C23—C22—C21 | 119.7 (2) |
C2—C1—C11 | 127.1 (2) | C23—C22—H22 | 120.1 |
C5—C1—Fe1 | 69.16 (13) | C21—C22—H22 | 120.1 |
C2—C1—Fe1 | 68.74 (13) | C24—C23—C22 | 120.4 (2) |
C11—C1—Fe1 | 126.32 (15) | C24—C23—H23 | 119.8 |
C3—C2—C1 | 108.4 (2) | C22—C23—H23 | 119.8 |
C3—C2—Fe1 | 69.99 (14) | C23—C24—C25 | 120.8 (2) |
C1—C2—Fe1 | 70.30 (13) | C23—C24—H24 | 119.6 |
C3—C2—H2 | 125.8 | C25—C24—H24 | 119.6 |
C1—C2—H2 | 125.8 | C24—C25—C26 | 119.6 (3) |
Fe1—C2—H2 | 125.5 | C24—C25—H25 | 120.2 |
C4—C3—C2 | 108.4 (2) | C26—C25—H25 | 120.2 |
C4—C3—Fe1 | 70.26 (14) | C21—C26—C25 | 119.6 (2) |
C2—C3—Fe1 | 69.49 (13) | C21—C26—H26 | 120.2 |
C4—C3—H3 | 125.8 | C25—C26—H26 | 120.2 |
C2—C3—H3 | 125.8 | C36—C31—C32 | 119.9 (2) |
Fe1—C3—H3 | 126 | C36—C31—P1 | 118.82 (17) |
C3—C4—C5 | 108.0 (2) | C32—C31—P1 | 121.15 (18) |
C3—C4—Fe1 | 69.48 (14) | C33—C32—C31 | 119.9 (2) |
C5—C4—Fe1 | 69.44 (13) | C33—C32—H32 | 120 |
C3—C4—H4 | 126 | C31—C32—H32 | 120 |
C5—C4—H4 | 126 | C34—C33—C32 | 119.7 (2) |
Fe1—C4—H4 | 126.7 | C34—C33—H33 | 120.2 |
C4—C5—C1 | 108.4 (2) | C32—C33—H33 | 120.2 |
C4—C5—Fe1 | 70.02 (14) | C33—C34—C35 | 120.7 (2) |
C1—C5—Fe1 | 70.05 (13) | C33—C34—H34 | 119.7 |
C4—C5—H5 | 125.8 | C35—C34—H34 | 119.7 |
C1—C5—H5 | 125.8 | C34—C35—C36 | 120.4 (2) |
Fe1—C5—H5 | 125.7 | C34—C35—H35 | 119.8 |
C7—C6—C10 | 109.9 (13) | C36—C35—H35 | 119.8 |
C7—C6—Fe1 | 69.8 (8) | C35—C36—C31 | 119.4 (2) |
C10—C6—Fe1 | 70.9 (12) | C35—C36—H36 | 120.3 |
C7—C6—H6 | 125.1 | C31—C36—H36 | 120.3 |
C10—C6—H6 | 125.1 | C46—C41—C42 | 119.1 (2) |
Fe1—C6—H6 | 125.8 | C46—C41—P1 | 120.24 (17) |
C6—C7—C8 | 106.3 (10) | C42—C41—P1 | 120.61 (17) |
C6—C7—Fe1 | 70.3 (8) | C43—C42—C41 | 119.7 (2) |
C8—C7—Fe1 | 68.0 (9) | C43—C42—H42 | 120.1 |
C6—C7—H7 | 126.9 | C41—C42—H42 | 120.1 |
C8—C7—H7 | 126.9 | C44—C43—C42 | 120.3 (2) |
Fe1—C7—H7 | 126.3 | C44—C43—H43 | 119.9 |
C9—C8—C7 | 109.0 (9) | C42—C43—H43 | 119.9 |
C9—C8—Fe1 | 71.2 (14) | C45—C44—C43 | 120.2 (2) |
C7—C8—Fe1 | 71.2 (8) | C45—C44—H44 | 119.9 |
C9—C8—H8 | 125.5 | C43—C44—H44 | 119.9 |
C7—C8—H8 | 125.5 | C44—C45—C46 | 120.5 (2) |
Fe1—C8—H8 | 123.6 | C44—C45—H45 | 119.8 |
C10—C9—C8 | 107.6 (11) | C46—C45—H45 | 119.8 |
C10—C9—Fe1 | 71.2 (15) | C45—C46—C41 | 120.2 (2) |
C8—C9—Fe1 | 68.2 (12) | C45—C46—H46 | 119.9 |
C10—C9—H9 | 126.2 | C41—C46—H46 | 119.9 |
C8—C9—H9 | 126.2 | | |
| | | |
C1—C2—C3—C4 | −0.4 (3) | C21—P1—C13—C12 | 56.87 (18) |
Fe1—C2—C3—C4 | 59.68 (17) | C31—P1—C13—C12 | −62.85 (19) |
C1—C2—C3—Fe1 | −60.05 (16) | C41—P1—C13—C12 | 177.64 (15) |
C3—C4—C5—C1 | 0.8 (3) | C31—P1—C21—C22 | −139.03 (18) |
Fe1—C4—C5—C1 | 59.78 (15) | C41—P1—C21—C22 | −18.9 (2) |
C3—C4—C5—Fe1 | −58.93 (17) | C13—P1—C21—C22 | 100.87 (19) |
C2—C1—C5—C4 | −1.1 (2) | C31—P1—C21—C26 | 49.7 (2) |
C11—C1—C5—C4 | 179.8 (2) | C41—P1—C21—C26 | 169.78 (18) |
Fe1—C1—C5—C4 | −59.76 (16) | C13—P1—C21—C26 | −70.5 (2) |
C2—C1—C5—Fe1 | 58.71 (15) | C26—C21—C22—C23 | 1.0 (3) |
C11—C1—C5—Fe1 | −120.4 (2) | P1—C21—C22—C23 | −170.31 (18) |
C10—C6—C7—C8 | 1 (2) | C21—C22—C23—C24 | −0.6 (4) |
Fe1—C6—C7—C8 | −58.8 (12) | C22—C23—C24—C25 | 0.0 (4) |
C10—C6—C7—Fe1 | 59.8 (15) | C23—C24—C25—C26 | 0.2 (4) |
C6—C7—C8—C9 | −1 (2) | C22—C21—C26—C25 | −0.8 (3) |
Fe1—C7—C8—C9 | −61.4 (18) | P1—C21—C26—C25 | 170.43 (18) |
C6—C7—C8—Fe1 | 60.3 (11) | C24—C25—C26—C21 | 0.2 (4) |
C7—C8—C9—C10 | 1 (3) | C21—P1—C31—C36 | −155.96 (18) |
Fe1—C8—C9—C10 | −61 (2) | C41—P1—C31—C36 | 82.3 (2) |
C7—C8—C9—Fe1 | 61.5 (14) | C13—P1—C31—C36 | −37.9 (2) |
C7—C6—C10—C9 | 0 (3) | C21—P1—C31—C32 | 28.1 (2) |
Fe1—C6—C10—C9 | 59 (2) | C41—P1—C31—C32 | −93.6 (2) |
C7—C6—C10—Fe1 | −59.1 (13) | C13—P1—C31—C32 | 146.19 (19) |
C8—C9—C10—C6 | 0 (3) | C36—C31—C32—C33 | 0.7 (4) |
Fe1—C9—C10—C6 | −59.0 (18) | P1—C31—C32—C33 | 176.51 (19) |
C8—C9—C10—Fe1 | 59 (2) | C31—C32—C33—C34 | 0.5 (4) |
C10B—C6B—C7B—C8B | 1 (3) | C32—C33—C34—C35 | −1.0 (4) |
Fe1—C6B—C7B—C8B | −59.1 (18) | C33—C34—C35—C36 | 0.4 (4) |
C10B—C6B—C7B—Fe1 | 59.8 (13) | C34—C35—C36—C31 | 0.7 (4) |
C6B—C7B—C8B—C9B | −1 (3) | C32—C31—C36—C35 | −1.2 (3) |
Fe1—C7B—C8B—C9B | −59 (2) | P1—C31—C36—C35 | −177.17 (18) |
C6B—C7B—C8B—Fe1 | 58.0 (15) | C21—P1—C41—C46 | −100.7 (2) |
C7B—C8B—C9B—C10B | 1 (4) | C31—P1—C41—C46 | 20.3 (2) |
Fe1—C8B—C9B—C10B | −59 (2) | C13—P1—C41—C46 | 141.0 (2) |
C7B—C8B—C9B—Fe1 | 60 (2) | C21—P1—C41—C42 | 77.9 (2) |
Fe1—C9B—C10B—C6B | −60.9 (14) | C31—P1—C41—C42 | −161.17 (19) |
C8B—C9B—C10B—Fe1 | 60 (2) | C13—P1—C41—C42 | −40.4 (2) |
C7B—C6B—C10B—C9B | 0 (3) | C46—C41—C42—C43 | −0.2 (4) |
Fe1—C6B—C10B—C9B | 62 (2) | P1—C41—C42—C43 | −178.75 (18) |
C7B—C6B—C10B—Fe1 | −61.5 (14) | C41—C42—C43—C44 | 0.4 (4) |
C5—C1—C11—C12 | −161.0 (2) | C42—C43—C44—C45 | −0.2 (4) |
C2—C1—C11—C12 | 20.0 (4) | C43—C44—C45—C46 | −0.1 (5) |
Fe1—C1—C11—C12 | 109.5 (2) | C44—C45—C46—C41 | 0.3 (5) |
C1—C11—C12—C13 | −177.8 (2) | C42—C41—C46—C45 | −0.1 (4) |
C11—C12—C13—P1 | 100.6 (2) | P1—C41—C46—C45 | 178.4 (2) |
Selected geometric parameters in polymorphs (I) and (II) (Å, °) topParameter | (I) | (II) |
C12—C11—C1 | 126.9 (4) | 124.6 (2) |
C11—C12—C13 | 123.4 (4) | 124.8 (2) |
C2—C1—C11—C12 | 19.1 (7) | 20.0 (4) |
C1—C11—C12—C13 | 178.4 (3) | -177.8 (2) |
C11—C12—C13—P1 | 97.6 (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 topCg1 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 topDihedral_angle | Cg3/Cg4 | Cg4/Cg5 | Cg3/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) topCg3 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···A | D—H | H···A | D···A | D—H···A |
Polymorph (I) | | | | |
C13—H13B···I1i | 0.9700 | 2.9700 | 3.802?(3) | 145.00 |
C3—H3···Cg3ii | 0.9300 | 2.9700 | 3.690?(5) | 135.00 |
C9—H9···Cg3 | 0.9300 | 2.8700 | 3.713?(5) | 151.00 |
Polymorph (II) | | | | |
C13—H13A···I1 | 0.9700 | 2.9200 | 3.891?(2) | 174.00 |
C36—H36···I1 | 0.9300 | 3.0600 | 3.969?(3) | 166.00 |
C45—H45···Cg2iii | 0.9400 | 2.9200 | 3.623?(3) | 132.00 |
C6B—H6B···Cg5 | 0.93 | 2.79 | 3.617?(4) | 149.00 |
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y, z; (iii) -x+1, y+1/2, -z+1/2. |