Selective synthesis of (3-ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide: crystal structure determination of two polymorphs

Bouchene, R.; Daran, J.C.; Merazig, H.; Manoury, E.; Bouacida, S.

doi:10.1107/S2053229617004867

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Selective synthesis of (3-ferrocenylprop-2-en-1-yl)triphenylphosphonium iodide: crystal structure determination of two polymorphs

R. Bouchene, J. C. Daran, H. Merazig, E. Manoury and S. Bouacida

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.

Keywords: ferrocenyl compounds; phosphonium; allyl compounds; polymorphs; salts; crystal structure; database analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617004867/ku3195sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617004867/ku3195Isup2.hkl Contains datablock I
	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)]·I	Z = 2
M_r = 614.25	F(000) = 616
Triclinic, P1	D_x = 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	R_int = 0.023
CCD rotation images, thick slices scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.626, T_max = 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(F_o²) + (0.P)² + 4.8514P] where P = (F_o² + 2F_c²)/3
4796 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 1.28 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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
M_r = 614.25	D_x = 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	R_int = 0.047
CCD rotation images, thick slices scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
T_min = 0.699, T_max = 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(F_o²) + (0.0151P)² + 2.0496P] where P = (F_o² + 2F_c²)/3
5396 reflections	(Δ/σ)_max = 0.005
352 parameters	Δρ_max = 0.52 e Å⁻³
10 restraints	Δρ_min = −0.50 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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, °) top

Parameter	(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 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_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) 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···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.

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