Propynylferrocene and (phenyl­ethyn­yl)­ferrocene

The title compounds, propynylferrocene, [Fe(C₅H₅)(C₈H₇)], (I), and (phenyl­ethyn­yl)ferrocene, [Fe(C₅H₅)(C₁₃H₉)], (II), are stabilized by weak C—H...π inter­actions. The C[triple bond]C bond distances in these mol­ecules are in the range 1.182 (3)–1.192 (3) Å. In (II), the ferrocenyl and phenyl groups are perpendicular, making an angle of 89.06 (13)°, which is a rare occurrence.

S1. Comment

Recently, alkyne chemistry has experienced a major renaissance by the involvement of molecules with C≡C bonds in the frontiers of modern organic chemistry, namely biochemistry, materials science and organometallic chemistry (Stang & Diederich, 1995; Diederich et al., 2005). In this regard, ferrocenylalkynes occupy an important position since they can be converted to a structurally diverse set of ferrocenyl (Fc) compounds that are attractive synthetic targets owing to their physical, chemical and biological properties (Togni & Hayashi, 1995). The Fc group is often incorporated into a bioactive compound to obtain enhanced biological activities (Zora et al., 2002, 2003; Jaouen et al., 2004). In addition, the Fc group is ideal for use in drug design owing to its low toxicity, stability and lipophilicity (Biot et al., 2000).

There is considerable interest in the synthesis of new materials with large second-order optical nonlinearities because of their potential use in device applications related to telecommunications, optical computing, optical storage, and optical information processing (Williams, 1984; Chemla & Zyss, 1987). In this regard, ferrocene-based donor–acceptor chromophores are widely investigated for their linear and nonlinear optical properties (Barlow & Marder, 2000; Stankovic et al., 2001). In particular, ethynylferrocene (Wurst et al., 1995; Polin & Schottenberger, 1995 or??? 1996) and its derivatives (Nock & Schottenberger, 1993; Ingham et al., 1994) have attracted substantial interest due to the potential for electronic communication through the unsaturated alkyne linkage to the Fe center. There are also examples of ethynylferrocene linked through the alkyne spacer group to other metal centers (Berry et al., 2004; Laus et al., 2005). In this respect, crystal structures of ethynylferrocene (Wurst et al., 1995; Steiner et al., 1996) and its derivatives (Ingham et al., 1994; Dufkova et al., 2003; Hocek et al., 2004) have gained importance. We report here the crystal structures of propynylferrocene, (I), and (phenylethynyl)ferrocene, (II).

The molecular structure of (I) is shown in Fig. 1. Selected bond distances and angles are given in Table 1. There are two molecules present in the asymmetric unit of (I). The C≡C bond distances in these molecules are 1.182 (3) and 1.184 (3) Å, which are in accord with those in similar complexes such as 1,1,3-triferrocenylprop-2-yn-1-ol [1.180 (13) Å; Lucasser et al., 1995)]and 1-trimethylsilylethynylferrocene [1.188 (7) Å; Schottenberger et al., 1999]. The Fe—Cg_s and Fe—Cg_as distances are in the range 1.6388 (11)–1.6467 (11) Å, and the Cg_s—Fe—Cg_as angles are 178.64 (8) and 178.77 (5)°, where Cg_s and Cg_as are the substituted and unsubstituted Cp ring centroids. The Cp rings in each molecule are almost parallel since the angles between the Cp ring planes are 1.43 (10) and 1.71 (19)°. The Cp rings of Fc groups deviate slightly from the eclipsed conformation as evidenced by the average C—Cg_s—Cg_as—C torsion angles of 7.41 (3) and -4.71 (3)°. The C—C bond distances in Cp rings range from 1.342 (5) to 1.427 (3)°, while the Fe—C bond lengths range between 2.006 (3) and 2.0510 (17)°, all of which are as expected.

As in ethynylferrocene (Wurst et al., 1995; Steiner et al., 1996), there are no direction-specific aromatic π–π interactions between adjacent rings in (I), but there are two C—H···π interactions (Cg1 and Cg2 are the centroids of the C1–C5 and C21–C25 rings, resepctively; Table 2 and Fig. 2).

The molecular structure of (II) is shown in Fig. 3. Selected bond distances and angles are given in Table 3. Compound (II) comprises Fc and Ph rings linked by an acetylene residue. The unusual feature of (II) is that substituted Cp ring and Ph ring are almost perpendicular, with an angle of 89.06 (13)°, which is a rare occurrence. This is clearly an indication of the interrupted conjugation between the Fc and Ph groups. However, in 1,1'-bis(phenylethynyl)ferrocene (Ingham et al., 1994), a closely related compound, there is not a large tilting of the phenyl groups from the planes of the cyclopentadienyl rings since the angles between phenyl rings and the cyclopentadienyl rings are 11.2 (2) and 26.6 (2)°. Moreover, a literature search for crystal structures incorporating the diphenylacetylene group has revealed some derivatives including tolane (Mavridis & Moustakali-Mavridis, 1977), perfluorodiphenylacetylene (Goodhand & Hamor, 1979), octafluoronaphthalene–diphenylacetylene (1/1) (Collings et al., 2001) and N-[4-(phenylethynyl)phenyl]benzamide (Yin et al., 2005). In all, ethynyl-bridged Ph rings are found to be almost coplanar, which is in contrast to the situation in (II).

The C≡C bond length in (II) is 1.192 (3) Å, which is in agreement with those in 1,1'-bis(phenylethynyl)ferrocene (Ingham et al., 1994) and (Z)-1,4-diferrocenylbut-1-en-3-yne [1.199 (4) Å; Wurst et al., 1995]. The Fc group is almost in the eclipsed conformation since the average C11—Cg_s—Cg_as—C6 pseudo-torsion angle is 0.60 (4)°. The centroids of the Cp rings are almost equidistant from Fe atoms as indicated by the Fe—Cg_s and Fe—Cg_as distances of 1.641 (12) and 1.642 (12) Å, respectively. The Cg_s—Fe—Cg_as angle is 179.16 (6)°. The Cp rings are almost parallel since the angle between the Cp ring planes is 1.62 (16)°. The C—C bond distances in the Cp rings range from 1.390 (4) to 1.428?(3) Å. The Fe—C bond lengths are in the range 2.021 (3)–2.039 (2) Å.

As in compound (I) and ethynylferrocene (Wurst et al., 1995; Steiner et al., 1996), compound (II) is also stabilized by four C—H···π interactions, two of them, C14—H14···π and C15—H15···π, being in chelate ring form (Table 4 and Fig. 4) (Cg1, Cg2 and Cg3 are the centroids of the C1–C5, C6–C10 and C13–C18 rings).

S2. Experimental

Compound (I) was prepared from ethynylferrocene by Vilsmeier–Haack formylation (Doisneau et al., 1992). Suitable crystals of (I) were obtained by slow evaporation of a 19:1 hexane–ethyl acetate solution at room temperature. Compound (II) was synthesized by a modified literature procedure (Okuro et al., 1993). Iodobenzene (0.3 ml, 2.38 mmol) and ethynylferrocene (500 mg, 2.38 mmol) were added to a mixture of CuI (23 mg, 0.12 mmol), PPh₃ (62 mg, 0.24 mmol), K₂CO₃ (493 mg, 3.57 mmol) and dimethylformamide (4.8 ml) under argon. The resulting mixture was refluxed at 393 K for 16 h. The solution was then extracted with ether, washed with water and dried over MgSO₄. Final purification was achieved by flash column chromatography on silica gel using hexane as the eluant. The product was obtained in 47% yield. The spectroscopic data for (II) were in agreement with those reported previously for this compounds (Stepnicka et al., 1999). Single crystals of (II) were obtained by slow evaporation of a 19:1 hexane–ethyl acetate solution at room temperature.

S3. Refinement

All H atoms were refined using the riding-model approximation, with C—H = 0.93 Å for aromatic atoms [U_iso(H) = 1.2U_eq(parent atom)] and C—H = 0.96 Å for methyl groups [U_iso(H) = 1.5U_eq(parent atom)].

Computing details

For both compounds, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. A packing diagram of (I), showing the C—H···π interactions as dashed lines. H atoms not involved in C—H···π interactions have been omitted for clarity.
	Fig. 3. A view of (II), with the atom-numbering scheme and 50% probability displacement ellipsoids.
	Fig. 4. A packing diagram of (II), showing the C—H···π interactions as dashed lines. H atoms not involved in C—H···π interactions have been omitted for clarity·[Symmetry code: (i) -x + 1, -y + 1, -z + 1.]

(I) Propynylferrocene

Crystal data

[Fe(C5H5)(C8H7)]	Z = 4
Mr = 224.08	F(000) = 464
Triclinic, P1	Dx = 1.437 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8232 (7) Å	Cell parameters from 24535 reflections
b = 10.3192 (7) Å	θ = 2.2–28.0°
c = 11.1465 (8) Å	µ = 1.41 mm^−1
α = 76.431 (5)°	T = 296 K
β = 86.740 (6)°	Prism, red
γ = 70.527 (5)°	0.60 × 0.49 × 0.40 mm
V = 1035.25 (13) Å^3

Data collection

Stoe IPDS 2 diffractometer	4072 independent reflections
Radiation source: fine-focus sealed tube	3613 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.2°
rotation w scan	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.558, Tmax = 0.670	l = −13→13
15013 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 0.2017P] where P = (Fo^2 + 2Fc^2)/3
4072 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2566 (2)	0.93568 (18)	0.45313 (16)	0.0476 (4)
C2	0.1379 (2)	0.93999 (18)	0.38245 (16)	0.0503 (4)
H2	0.0418	0.9937	0.3885	0.060*
C3	0.1923 (3)	0.8481 (2)	0.30142 (17)	0.0611 (5)
H3	0.1380	0.8314	0.2447	0.073*
C4	0.3425 (3)	0.7867 (2)	0.32163 (19)	0.0658 (6)
H4	0.4045	0.7224	0.2803	0.079*
C5	0.3832 (2)	0.8390 (2)	0.41532 (19)	0.0590 (5)
H5	0.4764	0.8147	0.4467	0.071*
C6	0.2237 (3)	0.6602 (2)	0.66397 (18)	0.0639 (5)
H6	0.2322	0.7027	0.7268	0.077*
C7	0.0953 (3)	0.6810 (2)	0.6018 (2)	0.0740 (7)
H7	0.0037	0.7395	0.6159	0.089*
C8	0.1309 (3)	0.5963 (3)	0.5134 (2)	0.0733 (7)
H8	0.0667	0.5891	0.4592	0.088*
C9	0.2794 (3)	0.5260 (2)	0.5227 (2)	0.0658 (6)
H9	0.3318	0.4638	0.4752	0.079*
C10	0.3360 (2)	0.5650 (2)	0.61544 (19)	0.0609 (5)
H10	0.4326	0.5327	0.6406	0.073*
C11	0.2501 (2)	1.01640 (19)	0.54273 (17)	0.0498 (4)
C12	0.2432 (2)	1.0898 (2)	0.61160 (18)	0.0556 (4)
C13	0.2336 (3)	1.1830 (3)	0.6949 (2)	0.0769 (7)
H13A	0.2280	1.2752	0.6474	0.115*
H13B	0.3177	1.1453	0.7483	0.115*
H13C	0.1488	1.1895	0.7436	0.115*
C21	0.7106 (2)	0.4911 (2)	0.85223 (16)	0.0502 (4)
C22	0.5681 (2)	0.5899 (2)	0.83404 (18)	0.0588 (5)
H22	0.4865	0.5785	0.8756	0.071*
C23	0.5726 (3)	0.7085 (2)	0.74149 (19)	0.0651 (5)
H23	0.4941	0.7886	0.7114	0.078*
C24	0.7158 (3)	0.6847 (2)	0.70271 (18)	0.0642 (5)
H24	0.7481	0.7461	0.6423	0.077*
C25	0.8024 (2)	0.5514 (2)	0.77125 (17)	0.0562 (4)
H25	0.9015	0.5103	0.7647	0.067*
C26	0.7595 (5)	0.6483 (3)	1.0655 (2)	0.0932 (10)
H26	0.7814	0.5630	1.1238	0.112*
C27	0.6225 (4)	0.7494 (6)	1.0382 (4)	0.1195 (15)
H27	0.5362	0.7445	1.0746	0.143*
C28	0.6410 (5)	0.8591 (4)	0.9454 (4)	0.1181 (14)
H28	0.5681	0.9412	0.9086	0.142*
C29	0.7816 (5)	0.8263 (3)	0.9181 (3)	0.1031 (11)
H29	0.8219	0.8820	0.8591	0.124*
C30	0.8558 (3)	0.6978 (3)	0.9909 (3)	0.0853 (8)
H30	0.9548	0.6517	0.9899	0.102*
C31	0.7531 (2)	0.3561 (2)	0.93613 (17)	0.0545 (4)
C32	0.7847 (3)	0.2429 (2)	1.00351 (19)	0.0612 (5)
C33	0.8221 (4)	0.1022 (3)	1.0853 (3)	0.0920 (9)
H33A	0.7515	0.1016	1.1484	0.138*
H33B	0.9156	0.0779	1.1228	0.138*
H33C	0.8239	0.0346	1.0385	0.138*
Fe1	0.23771 (3)	0.73888 (2)	0.48018 (2)	0.04332 (9)
Fe2	0.70385 (3)	0.67878 (3)	0.88701 (2)	0.04716 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0563 (10)	0.0372 (8)	0.0466 (9)	−0.0176 (7)	0.0040 (7)	−0.0019 (7)
C2	0.0611 (11)	0.0397 (9)	0.0442 (9)	−0.0124 (8)	−0.0031 (8)	−0.0035 (7)
C3	0.0912 (15)	0.0480 (10)	0.0406 (9)	−0.0209 (10)	−0.0023 (9)	−0.0058 (8)
C4	0.0839 (15)	0.0520 (11)	0.0554 (11)	−0.0177 (10)	0.0240 (10)	−0.0129 (9)
C5	0.0542 (11)	0.0560 (11)	0.0632 (11)	−0.0208 (9)	0.0125 (9)	−0.0057 (9)
C6	0.0964 (17)	0.0519 (11)	0.0453 (10)	−0.0308 (11)	0.0096 (10)	−0.0071 (8)
C7	0.0593 (13)	0.0536 (12)	0.0943 (16)	−0.0171 (10)	0.0227 (12)	0.0037 (11)
C8	0.0866 (16)	0.0634 (13)	0.0790 (15)	−0.0468 (13)	−0.0174 (12)	0.0035 (11)
C9	0.0915 (16)	0.0369 (10)	0.0680 (12)	−0.0209 (10)	0.0040 (11)	−0.0113 (9)
C10	0.0644 (12)	0.0469 (10)	0.0612 (11)	−0.0146 (9)	−0.0094 (9)	0.0041 (9)
C11	0.0581 (10)	0.0405 (9)	0.0499 (9)	−0.0205 (8)	−0.0036 (8)	−0.0010 (8)
C12	0.0699 (12)	0.0463 (10)	0.0526 (10)	−0.0260 (9)	−0.0047 (9)	−0.0038 (8)
C13	0.117 (2)	0.0633 (14)	0.0656 (13)	−0.0473 (14)	0.0018 (13)	−0.0185 (11)
C21	0.0632 (11)	0.0523 (10)	0.0426 (8)	−0.0264 (9)	−0.0019 (8)	−0.0140 (7)
C22	0.0574 (11)	0.0700 (13)	0.0551 (10)	−0.0290 (10)	−0.0080 (8)	−0.0121 (9)
C23	0.0715 (13)	0.0651 (13)	0.0535 (10)	−0.0185 (10)	−0.0208 (10)	−0.0043 (9)
C24	0.0882 (15)	0.0653 (13)	0.0417 (9)	−0.0333 (12)	−0.0005 (9)	−0.0054 (9)
C25	0.0661 (12)	0.0607 (11)	0.0456 (9)	−0.0242 (10)	0.0074 (8)	−0.0159 (8)
C26	0.175 (3)	0.0758 (17)	0.0476 (12)	−0.066 (2)	−0.0266 (16)	−0.0074 (11)
C27	0.108 (2)	0.206 (5)	0.103 (2)	−0.082 (3)	0.043 (2)	−0.111 (3)
C28	0.147 (3)	0.074 (2)	0.118 (3)	0.012 (2)	−0.040 (3)	−0.055 (2)
C29	0.183 (4)	0.0781 (19)	0.0777 (17)	−0.081 (2)	−0.010 (2)	−0.0140 (15)
C30	0.0820 (17)	0.097 (2)	0.0942 (18)	−0.0349 (15)	−0.0184 (14)	−0.0419 (16)
C31	0.0688 (12)	0.0529 (11)	0.0506 (10)	−0.0280 (9)	0.0002 (8)	−0.0168 (9)
C32	0.0806 (14)	0.0530 (12)	0.0559 (11)	−0.0279 (10)	0.0031 (10)	−0.0150 (9)
C33	0.138 (3)	0.0545 (14)	0.0784 (16)	−0.0329 (15)	0.0030 (16)	−0.0032 (12)
Fe1	0.04950 (15)	0.03504 (13)	0.04301 (14)	−0.01267 (11)	0.00112 (10)	−0.00623 (10)
Fe2	0.05592 (16)	0.04383 (15)	0.04323 (14)	−0.01826 (12)	−0.00377 (11)	−0.00899 (11)

Geometric parameters (Å, º)

C1—C5	1.425 (3)	C21—C22	1.423 (3)
C1—C2	1.427 (3)	C21—C25	1.425 (3)
C1—C11	1.429 (3)	C21—C31	1.427 (3)
C1—Fe1	2.0510 (17)	C21—Fe2	2.0414 (18)
C2—C3	1.417 (3)	C22—C23	1.415 (3)
C2—Fe1	2.0393 (17)	C22—Fe2	2.0318 (19)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.406 (3)	C23—C24	1.406 (3)
C3—Fe1	2.0377 (19)	C23—Fe2	2.0320 (19)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.414 (3)	C24—C25	1.414 (3)
C4—Fe1	2.037 (2)	C24—Fe2	2.039 (2)
C4—H4	0.9300	C24—H24	0.9300
C5—Fe1	2.037 (2)	C25—Fe2	2.0337 (19)
C5—H5	0.9300	C25—H25	0.9300
C6—C10	1.391 (3)	C26—C30	1.371 (4)
C6—C7	1.402 (3)	C26—C27	1.398 (5)
C6—Fe1	2.0340 (19)	C26—Fe2	2.018 (2)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.421 (4)	C27—C28	1.397 (6)
C7—Fe1	2.028 (2)	C27—Fe2	2.011 (3)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.393 (3)	C28—C29	1.342 (5)
C8—Fe1	2.032 (2)	C28—Fe2	2.006 (3)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.396 (3)	C29—C30	1.366 (4)
C9—Fe1	2.037 (2)	C29—Fe2	2.018 (3)
C9—H9	0.9300	C29—H29	0.9300
C10—Fe1	2.0411 (19)	C30—Fe2	2.026 (2)
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.184 (3)	C31—C32	1.182 (3)
C12—C13	1.464 (3)	C32—C33	1.461 (3)
C13—H13A	0.9600	C33—H33A	0.9600
C13—H13B	0.9600	C33—H33B	0.9600
C13—H13C	0.9600	C33—H33C	0.9600
C5—C1—C2	107.29 (17)	C29—C28—H28	125.7
C5—C1—C11	126.39 (18)	C27—C28—H28	125.7
C2—C1—C11	126.30 (17)	Fe2—C28—H28	125.1
C5—C1—Fe1	69.09 (11)	C28—C29—C30	109.0 (3)
C2—C1—Fe1	69.15 (10)	C28—C29—Fe2	70.04 (19)
C11—C1—Fe1	128.26 (12)	C30—C29—Fe2	70.58 (15)
C3—C2—C1	108.01 (18)	C28—C29—H29	125.5
C3—C2—Fe1	69.60 (10)	C30—C29—H29	125.5
C1—C2—Fe1	70.03 (10)	Fe2—C29—H29	125.5
C3—C2—H2	126.0	C29—C30—C26	108.4 (3)
C1—C2—H2	126.0	C29—C30—Fe2	69.94 (16)
Fe1—C2—H2	126.0	C26—C30—Fe2	69.88 (14)
C4—C3—C2	108.17 (19)	C29—C30—H30	125.8
C4—C3—Fe1	69.77 (11)	C26—C30—H30	125.8
C2—C3—Fe1	69.72 (10)	Fe2—C30—H30	126.0
C4—C3—H3	125.9	C32—C31—C21	177.5 (2)
C2—C3—H3	125.9	C31—C32—C33	178.9 (2)
Fe1—C3—H3	126.2	C32—C33—H33A	109.5
C3—C4—C5	108.49 (18)	C32—C33—H33B	109.5
C3—C4—Fe1	69.85 (12)	H33A—C33—H33B	109.5
C5—C4—Fe1	69.72 (11)	C32—C33—H33C	109.5
C3—C4—H4	125.8	H33A—C33—H33C	109.5
C5—C4—H4	125.8	H33B—C33—H33C	109.5
Fe1—C4—H4	126.3	C7—Fe1—C8	40.96 (10)
C4—C5—C1	108.03 (19)	C7—Fe1—C6	40.37 (10)
C4—C5—Fe1	69.66 (12)	C8—Fe1—C6	68.01 (10)
C1—C5—Fe1	70.12 (10)	C7—Fe1—C4	162.56 (11)
C4—C5—H5	126.0	C8—Fe1—C4	124.72 (11)
C1—C5—H5	126.0	C6—Fe1—C4	155.08 (10)
Fe1—C5—H5	125.8	C7—Fe1—C5	155.69 (10)
C10—C6—C7	108.2 (2)	C8—Fe1—C5	161.98 (11)
C10—C6—Fe1	70.32 (11)	C6—Fe1—C5	121.18 (10)
C7—C6—Fe1	69.59 (12)	C4—Fe1—C5	40.62 (9)
C10—C6—H6	125.9	C7—Fe1—C9	67.95 (10)
C7—C6—H6	125.9	C8—Fe1—C9	40.04 (10)
Fe1—C6—H6	125.8	C6—Fe1—C9	67.52 (9)
C6—C7—C8	107.4 (2)	C4—Fe1—C9	107.28 (9)
C6—C7—Fe1	70.04 (12)	C5—Fe1—C9	125.72 (9)
C8—C7—Fe1	69.68 (13)	C7—Fe1—C3	125.93 (10)
C6—C7—H7	126.3	C8—Fe1—C3	106.97 (10)
C8—C7—H7	126.3	C6—Fe1—C3	163.88 (10)
Fe1—C7—H7	125.6	C4—Fe1—C3	40.37 (9)
C9—C8—C7	107.7 (2)	C5—Fe1—C3	68.33 (9)
C9—C8—Fe1	70.18 (12)	C9—Fe1—C3	119.24 (9)
C7—C8—Fe1	69.36 (12)	C7—Fe1—C2	108.22 (9)
C9—C8—H8	126.2	C8—Fe1—C2	120.00 (9)
C7—C8—H8	126.2	C6—Fe1—C2	127.27 (8)
Fe1—C8—H8	125.9	C4—Fe1—C2	68.25 (8)
C8—C9—C10	108.2 (2)	C5—Fe1—C2	68.57 (8)
C8—C9—Fe1	69.78 (12)	C9—Fe1—C2	154.00 (9)
C10—C9—Fe1	70.12 (11)	C3—Fe1—C2	40.69 (8)
C8—C9—H9	125.9	C7—Fe1—C10	67.53 (9)
C10—C9—H9	125.9	C8—Fe1—C10	67.40 (9)
Fe1—C9—H9	125.8	C6—Fe1—C10	39.91 (9)
C6—C10—C9	108.5 (2)	C4—Fe1—C10	120.39 (9)
C6—C10—Fe1	69.77 (11)	C5—Fe1—C10	108.72 (9)
C9—C10—Fe1	69.84 (11)	C9—Fe1—C10	40.04 (9)
C6—C10—H10	125.7	C3—Fe1—C10	154.00 (9)
C9—C10—H10	125.7	C2—Fe1—C10	164.43 (8)
Fe1—C10—H10	126.2	C7—Fe1—C1	120.92 (9)
C12—C11—C1	176.28 (19)	C8—Fe1—C1	155.47 (10)
C11—C12—C13	178.9 (2)	C6—Fe1—C1	109.29 (8)
C12—C13—H13A	109.5	C4—Fe1—C1	68.38 (8)
C12—C13—H13B	109.5	C5—Fe1—C1	40.79 (8)
H13A—C13—H13B	109.5	C9—Fe1—C1	163.52 (9)
C12—C13—H13C	109.5	C3—Fe1—C1	68.49 (8)
H13A—C13—H13C	109.5	C2—Fe1—C1	40.82 (7)
H13B—C13—H13C	109.5	C10—Fe1—C1	127.22 (8)
C22—C21—C25	107.61 (18)	C28—Fe2—C27	40.71 (17)
C22—C21—C31	125.93 (18)	C28—Fe2—C29	38.97 (16)
C25—C21—C31	126.5 (2)	C27—Fe2—C29	67.06 (15)
C22—C21—Fe2	69.19 (11)	C28—Fe2—C26	67.53 (14)
C25—C21—Fe2	69.24 (11)	C27—Fe2—C26	40.58 (15)
C31—C21—Fe2	127.16 (13)	C29—Fe2—C26	66.74 (12)
C23—C22—C21	107.79 (19)	C28—Fe2—C30	66.31 (14)
C23—C22—Fe2	69.63 (12)	C27—Fe2—C30	67.21 (13)
C21—C22—Fe2	69.92 (11)	C29—Fe2—C30	39.48 (13)
C23—C22—H22	126.1	C26—Fe2—C30	39.64 (13)
C21—C22—H22	126.1	C28—Fe2—C22	124.92 (16)
Fe2—C22—H22	125.9	C27—Fe2—C22	107.69 (12)
C24—C23—C22	108.45 (19)	C29—Fe2—C22	160.57 (14)
C24—C23—Fe2	70.04 (12)	C26—Fe2—C22	122.40 (11)
C22—C23—Fe2	69.61 (11)	C30—Fe2—C22	157.83 (11)
C24—C23—H23	125.8	C28—Fe2—C23	107.19 (12)
C22—C23—H23	125.8	C27—Fe2—C23	120.61 (14)
Fe2—C23—H23	126.1	C29—Fe2—C23	124.23 (12)
C23—C24—C25	108.30 (19)	C26—Fe2—C23	156.88 (14)
C23—C24—Fe2	69.53 (12)	C30—Fe2—C23	160.82 (12)
C25—C24—Fe2	69.49 (11)	C22—Fe2—C23	40.75 (9)
C23—C24—H24	125.9	C28—Fe2—C25	154.95 (18)
C25—C24—H24	125.9	C27—Fe2—C25	162.91 (18)
Fe2—C24—H24	126.7	C29—Fe2—C25	121.73 (14)
C24—C25—C21	107.84 (19)	C26—Fe2—C25	126.05 (12)
C24—C25—Fe2	69.86 (12)	C30—Fe2—C25	109.29 (10)
C21—C25—Fe2	69.82 (11)	C22—Fe2—C25	68.85 (9)
C24—C25—H25	126.1	C23—Fe2—C25	68.44 (9)
C21—C25—H25	126.1	C28—Fe2—C24	120.03 (15)
Fe2—C25—H25	125.8	C27—Fe2—C24	155.21 (17)
C30—C26—C27	107.6 (3)	C29—Fe2—C24	107.97 (11)
C30—C26—Fe2	70.48 (14)	C26—Fe2—C24	162.06 (14)
C27—C26—Fe2	69.45 (15)	C30—Fe2—C24	125.48 (12)
C30—C26—H26	126.2	C22—Fe2—C24	68.44 (9)
C27—C26—H26	126.2	C23—Fe2—C24	40.43 (9)
Fe2—C26—H26	125.5	C25—Fe2—C24	40.64 (8)
C28—C27—C26	106.3 (3)	C28—Fe2—C21	162.50 (18)
C28—C27—Fe2	69.44 (17)	C27—Fe2—C21	125.65 (15)
C26—C27—Fe2	69.97 (16)	C29—Fe2—C21	157.34 (15)
C28—C27—H27	126.8	C26—Fe2—C21	109.37 (9)
C26—C27—H27	126.8	C30—Fe2—C21	123.14 (10)
Fe2—C27—H27	125.3	C22—Fe2—C21	40.88 (8)
C29—C28—C27	108.6 (3)	C23—Fe2—C21	68.50 (8)
C29—C28—Fe2	70.99 (17)	C25—Fe2—C21	40.94 (8)
C27—C28—Fe2	69.86 (18)	C24—Fe2—C21	68.45 (8)
C5—C1—C2—C3	−0.70 (19)	C6—C10—Fe1—C5	116.55 (14)
C11—C1—C2—C3	177.69 (17)	C9—C10—Fe1—C5	−123.71 (14)
Fe1—C1—C2—C3	−59.46 (12)	C6—C10—Fe1—C9	−119.7 (2)
C5—C1—C2—Fe1	58.76 (12)	C6—C10—Fe1—C3	−164.7 (2)
C11—C1—C2—Fe1	−122.85 (17)	C9—C10—Fe1—C3	−44.9 (3)
C1—C2—C3—C4	0.3 (2)	C6—C10—Fe1—C2	39.3 (4)
Fe1—C2—C3—C4	−59.39 (14)	C9—C10—Fe1—C2	159.1 (3)
C1—C2—C3—Fe1	59.73 (12)	C6—C10—Fe1—C1	74.84 (16)
C2—C3—C4—C5	0.1 (2)	C9—C10—Fe1—C1	−165.42 (13)
Fe1—C3—C4—C5	−59.20 (14)	C5—C1—Fe1—C7	158.73 (13)
C2—C3—C4—Fe1	59.35 (13)	C2—C1—Fe1—C7	−82.19 (14)
C3—C4—C5—C1	−0.6 (2)	C11—C1—Fe1—C7	38.2 (2)
Fe1—C4—C5—C1	−59.87 (13)	C5—C1—Fe1—C8	−165.1 (2)
C3—C4—C5—Fe1	59.29 (14)	C2—C1—Fe1—C8	−46.1 (2)
C2—C1—C5—C4	0.8 (2)	C11—C1—Fe1—C8	74.4 (3)
C11—C1—C5—C4	−177.60 (17)	C5—C1—Fe1—C6	115.72 (14)
Fe1—C1—C5—C4	59.58 (14)	C2—C1—Fe1—C6	−125.19 (12)
C2—C1—C5—Fe1	−58.79 (12)	C11—C1—Fe1—C6	−4.8 (2)
C11—C1—C5—Fe1	122.81 (17)	C5—C1—Fe1—C4	−37.76 (13)
C10—C6—C7—C8	0.0 (2)	C2—C1—Fe1—C4	81.32 (13)
Fe1—C6—C7—C8	59.95 (14)	C11—C1—Fe1—C4	−158.3 (2)
C10—C6—C7—Fe1	−59.97 (14)	C2—C1—Fe1—C5	119.09 (16)
C6—C7—C8—C9	−0.2 (2)	C11—C1—Fe1—C5	−120.5 (2)
Fe1—C7—C8—C9	59.98 (15)	C5—C1—Fe1—C9	39.9 (3)
C6—C7—C8—Fe1	−60.17 (14)	C2—C1—Fe1—C9	159.0 (3)
C7—C8—C9—C10	0.3 (2)	C11—C1—Fe1—C9	−80.6 (3)
Fe1—C8—C9—C10	59.81 (15)	C5—C1—Fe1—C3	−81.32 (13)
C7—C8—C9—Fe1	−59.46 (14)	C2—C1—Fe1—C3	37.76 (12)
C7—C6—C10—C9	0.2 (2)	C11—C1—Fe1—C3	158.2 (2)
Fe1—C6—C10—C9	−59.28 (14)	C5—C1—Fe1—C2	−119.09 (16)
C7—C6—C10—Fe1	59.52 (14)	C11—C1—Fe1—C2	120.4 (2)
C8—C9—C10—C6	−0.4 (2)	C5—C1—Fe1—C10	74.72 (15)
Fe1—C9—C10—C6	59.23 (14)	C2—C1—Fe1—C10	−166.20 (12)
C8—C9—C10—Fe1	−59.60 (15)	C11—C1—Fe1—C10	−45.8 (2)
C25—C21—C22—C23	0.8 (2)	C29—C28—Fe2—C27	119.1 (3)
C31—C21—C22—C23	−178.92 (18)	C27—C28—Fe2—C29	−119.1 (3)
Fe2—C21—C22—C23	59.57 (14)	C29—C28—Fe2—C26	80.3 (2)
C25—C21—C22—Fe2	−58.77 (13)	C27—C28—Fe2—C26	−38.8 (2)
C31—C21—C22—Fe2	121.51 (18)	C29—C28—Fe2—C30	37.1 (2)
C21—C22—C23—C24	−0.3 (2)	C27—C28—Fe2—C30	−82.0 (2)
Fe2—C22—C23—C24	59.48 (15)	C29—C28—Fe2—C22	−164.95 (17)
C21—C22—C23—Fe2	−59.75 (13)	C27—C28—Fe2—C22	75.9 (2)
C22—C23—C24—C25	−0.4 (2)	C29—C28—Fe2—C23	−123.6 (2)
Fe2—C23—C24—C25	58.85 (14)	C27—C28—Fe2—C23	117.2 (2)
C22—C23—C24—Fe2	−59.21 (14)	C29—C28—Fe2—C25	−47.9 (4)
C23—C24—C25—C21	0.9 (2)	C27—C28—Fe2—C25	−167.0 (2)
Fe2—C24—C25—C21	59.74 (13)	C29—C28—Fe2—C24	−81.5 (2)
C23—C24—C25—Fe2	−58.88 (15)	C27—C28—Fe2—C24	159.4 (2)
C22—C21—C25—C24	−1.0 (2)	C29—C28—Fe2—C21	163.5 (3)
C31—C21—C25—C24	178.69 (17)	C27—C28—Fe2—C21	44.4 (5)
Fe2—C21—C25—C24	−59.76 (14)	C26—C27—Fe2—C28	−117.1 (3)
C22—C21—C25—Fe2	58.74 (13)	C28—C27—Fe2—C29	36.6 (2)
C31—C21—C25—Fe2	−121.54 (18)	C26—C27—Fe2—C29	−80.5 (2)
C30—C26—C27—C28	0.2 (3)	C28—C27—Fe2—C26	117.1 (3)
Fe2—C26—C27—C28	−60.26 (19)	C28—C27—Fe2—C30	79.6 (2)
C30—C26—C27—Fe2	60.43 (18)	C26—C27—Fe2—C30	−37.49 (18)
C26—C27—C28—C29	−0.1 (3)	C28—C27—Fe2—C22	−123.4 (2)
Fe2—C27—C28—C29	−60.7 (2)	C26—C27—Fe2—C22	119.48 (19)
C26—C27—C28—Fe2	60.60 (19)	C28—C27—Fe2—C23	−80.7 (3)
C27—C28—C29—C30	−0.1 (3)	C26—C27—Fe2—C23	162.16 (17)
Fe2—C28—C29—C30	−60.0 (2)	C28—C27—Fe2—C25	161.2 (4)
C27—C28—C29—Fe2	60.0 (2)	C26—C27—Fe2—C25	44.0 (5)
C28—C29—C30—C26	0.2 (3)	C28—C27—Fe2—C24	−46.6 (4)
Fe2—C29—C30—C26	−59.50 (18)	C26—C27—Fe2—C24	−163.8 (2)
C28—C29—C30—Fe2	59.7 (2)	C28—C27—Fe2—C21	−165.0 (2)
C27—C26—C30—C29	−0.2 (3)	C26—C27—Fe2—C21	77.9 (2)
Fe2—C26—C30—C29	59.54 (18)	C30—C29—Fe2—C28	119.7 (3)
C27—C26—C30—Fe2	−59.78 (18)	C28—C29—Fe2—C27	−38.2 (2)
C6—C7—Fe1—C8	118.25 (19)	C30—C29—Fe2—C27	81.5 (2)
C8—C7—Fe1—C6	−118.25 (19)	C28—C29—Fe2—C26	−82.5 (2)
C6—C7—Fe1—C4	158.0 (3)	C30—C29—Fe2—C26	37.2 (2)
C8—C7—Fe1—C4	39.8 (4)	C28—C29—Fe2—C30	−119.7 (3)
C6—C7—Fe1—C5	−48.5 (3)	C28—C29—Fe2—C22	39.8 (4)
C8—C7—Fe1—C5	−166.78 (19)	C30—C29—Fe2—C22	159.5 (3)
C6—C7—Fe1—C9	80.77 (14)	C28—C29—Fe2—C23	74.2 (3)
C8—C7—Fe1—C9	−37.49 (14)	C30—C29—Fe2—C23	−166.11 (18)
C6—C7—Fe1—C3	−168.31 (12)	C28—C29—Fe2—C25	158.3 (2)
C8—C7—Fe1—C3	73.44 (16)	C30—C29—Fe2—C25	−82.0 (2)
C6—C7—Fe1—C2	−126.67 (13)	C28—C29—Fe2—C24	115.8 (2)
C8—C7—Fe1—C2	115.08 (14)	C30—C29—Fe2—C24	−124.5 (2)
C6—C7—Fe1—C10	37.34 (13)	C28—C29—Fe2—C21	−167.2 (3)
C8—C7—Fe1—C10	−80.91 (15)	C30—C29—Fe2—C21	−47.5 (4)
C6—C7—Fe1—C1	−83.68 (14)	C30—C26—Fe2—C28	−79.5 (2)
C8—C7—Fe1—C1	158.07 (13)	C27—C26—Fe2—C28	38.9 (2)
C9—C8—Fe1—C7	−118.7 (2)	C30—C26—Fe2—C27	−118.4 (3)
C9—C8—Fe1—C6	−80.76 (15)	C30—C26—Fe2—C29	−37.1 (2)
C7—C8—Fe1—C6	37.97 (14)	C27—C26—Fe2—C29	81.4 (3)
C9—C8—Fe1—C4	74.76 (17)	C27—C26—Fe2—C30	118.4 (3)
C7—C8—Fe1—C4	−166.51 (14)	C30—C26—Fe2—C22	162.39 (16)
C9—C8—Fe1—C5	43.6 (3)	C27—C26—Fe2—C22	−79.2 (2)
C7—C8—Fe1—C5	162.3 (3)	C30—C26—Fe2—C23	−160.6 (2)
C7—C8—Fe1—C9	118.7 (2)	C27—C26—Fe2—C23	−42.2 (4)
C9—C8—Fe1—C3	115.50 (14)	C30—C26—Fe2—C25	76.2 (2)
C7—C8—Fe1—C3	−125.76 (14)	C27—C26—Fe2—C25	−165.4 (2)
C9—C8—Fe1—C2	157.84 (13)	C30—C26—Fe2—C24	39.2 (4)
C7—C8—Fe1—C2	−83.43 (15)	C27—C26—Fe2—C24	157.6 (3)
C9—C8—Fe1—C10	−37.47 (14)	C30—C26—Fe2—C21	118.95 (18)
C7—C8—Fe1—C10	81.26 (15)	C27—C26—Fe2—C21	−122.6 (2)
C9—C8—Fe1—C1	−169.24 (17)	C29—C30—Fe2—C28	−36.6 (2)
C7—C8—Fe1—C1	−50.5 (3)	C26—C30—Fe2—C28	82.8 (2)
C10—C6—Fe1—C7	119.12 (19)	C29—C30—Fe2—C27	−81.1 (3)
C10—C6—Fe1—C8	80.61 (15)	C26—C30—Fe2—C27	38.4 (2)
C7—C6—Fe1—C8	−38.51 (14)	C26—C30—Fe2—C29	119.5 (3)
C10—C6—Fe1—C4	−45.5 (3)	C29—C30—Fe2—C26	−119.5 (3)
C7—C6—Fe1—C4	−164.6 (2)	C29—C30—Fe2—C22	−162.0 (3)
C10—C6—Fe1—C5	−82.02 (15)	C26—C30—Fe2—C22	−42.6 (4)
C7—C6—Fe1—C5	158.86 (13)	C29—C30—Fe2—C23	37.2 (4)
C10—C6—Fe1—C9	37.20 (14)	C26—C30—Fe2—C23	156.6 (3)
C7—C6—Fe1—C9	−81.92 (15)	C29—C30—Fe2—C25	116.8 (2)
C10—C6—Fe1—C3	155.3 (3)	C26—C30—Fe2—C25	−123.70 (19)
C7—C6—Fe1—C3	36.2 (4)	C29—C30—Fe2—C24	74.4 (2)
C10—C6—Fe1—C2	−167.65 (12)	C26—C30—Fe2—C24	−166.16 (18)
C7—C6—Fe1—C2	73.23 (16)	C29—C30—Fe2—C21	160.2 (2)
C7—C6—Fe1—C10	−119.12 (19)	C26—C30—Fe2—C21	−80.4 (2)
C10—C6—Fe1—C1	−125.48 (13)	C23—C22—Fe2—C28	75.0 (2)
C7—C6—Fe1—C1	115.40 (14)	C21—C22—Fe2—C28	−166.09 (19)
C3—C4—Fe1—C7	43.9 (3)	C23—C22—Fe2—C27	116.7 (2)
C5—C4—Fe1—C7	163.6 (3)	C21—C22—Fe2—C27	−124.5 (2)
C3—C4—Fe1—C8	74.53 (15)	C23—C22—Fe2—C29	45.6 (4)
C5—C4—Fe1—C8	−165.75 (13)	C21—C22—Fe2—C29	164.5 (3)
C3—C4—Fe1—C6	−171.24 (18)	C23—C22—Fe2—C26	158.78 (17)
C5—C4—Fe1—C6	−51.5 (3)	C21—C22—Fe2—C26	−82.36 (18)
C3—C4—Fe1—C5	−119.72 (18)	C23—C22—Fe2—C30	−170.5 (3)
C3—C4—Fe1—C9	115.07 (14)	C21—C22—Fe2—C30	−51.6 (3)
C5—C4—Fe1—C9	−125.21 (13)	C21—C22—Fe2—C23	118.86 (18)
C5—C4—Fe1—C3	119.72 (18)	C23—C22—Fe2—C25	−81.10 (14)
C3—C4—Fe1—C2	−37.71 (12)	C21—C22—Fe2—C25	37.76 (11)
C5—C4—Fe1—C2	82.01 (13)	C23—C22—Fe2—C24	−37.31 (14)
C3—C4—Fe1—C10	156.74 (12)	C21—C22—Fe2—C24	81.55 (13)
C5—C4—Fe1—C10	−83.54 (14)	C23—C22—Fe2—C21	−118.86 (18)
C3—C4—Fe1—C1	−81.80 (13)	C24—C23—Fe2—C28	116.4 (2)
C5—C4—Fe1—C1	37.92 (12)	C22—C23—Fe2—C28	−124.0 (2)
C4—C5—Fe1—C7	−168.1 (2)	C24—C23—Fe2—C27	158.8 (2)
C1—C5—Fe1—C7	−49.1 (3)	C22—C23—Fe2—C27	−81.6 (2)
C4—C5—Fe1—C8	40.9 (3)	C24—C23—Fe2—C29	77.1 (2)
C1—C5—Fe1—C8	159.9 (3)	C22—C23—Fe2—C29	−163.28 (19)
C4—C5—Fe1—C6	157.32 (13)	C24—C23—Fe2—C26	−170.7 (2)
C1—C5—Fe1—C6	−83.67 (14)	C22—C23—Fe2—C26	−51.1 (3)
C1—C5—Fe1—C4	119.01 (17)	C24—C23—Fe2—C30	49.4 (4)
C4—C5—Fe1—C9	73.94 (16)	C22—C23—Fe2—C30	169.0 (3)
C1—C5—Fe1—C9	−167.04 (11)	C24—C23—Fe2—C22	−119.6 (2)
C4—C5—Fe1—C3	−37.25 (13)	C24—C23—Fe2—C25	−37.42 (13)
C1—C5—Fe1—C3	81.76 (12)	C22—C23—Fe2—C25	82.19 (14)
C4—C5—Fe1—C2	−81.15 (13)	C22—C23—Fe2—C24	119.6 (2)
C1—C5—Fe1—C2	37.86 (11)	C24—C23—Fe2—C21	−81.58 (14)
C4—C5—Fe1—C10	115.18 (14)	C22—C23—Fe2—C21	38.03 (13)
C1—C5—Fe1—C10	−125.81 (12)	C24—C25—Fe2—C28	−47.3 (3)
C4—C5—Fe1—C1	−119.01 (17)	C21—C25—Fe2—C28	−166.2 (3)
C8—C9—Fe1—C7	38.33 (15)	C24—C25—Fe2—C27	162.5 (4)
C10—C9—Fe1—C7	−80.86 (15)	C21—C25—Fe2—C27	43.7 (4)
C10—C9—Fe1—C8	−119.2 (2)	C24—C25—Fe2—C29	−80.60 (18)
C8—C9—Fe1—C6	82.11 (16)	C21—C25—Fe2—C29	160.55 (15)
C10—C9—Fe1—C6	−37.08 (14)	C24—C25—Fe2—C26	−163.47 (16)
C8—C9—Fe1—C4	−123.85 (16)	C21—C25—Fe2—C26	77.69 (17)
C10—C9—Fe1—C4	116.96 (15)	C24—C25—Fe2—C30	−122.44 (16)
C8—C9—Fe1—C5	−164.78 (14)	C21—C25—Fe2—C30	118.72 (15)
C10—C9—Fe1—C5	76.03 (16)	C24—C25—Fe2—C22	81.13 (14)
C8—C9—Fe1—C3	−81.59 (17)	C21—C25—Fe2—C22	−37.71 (12)
C10—C9—Fe1—C3	159.21 (14)	C24—C25—Fe2—C23	37.22 (13)
C8—C9—Fe1—C2	−48.2 (3)	C21—C25—Fe2—C23	−81.62 (13)
C10—C9—Fe1—C2	−167.36 (17)	C21—C25—Fe2—C24	−118.84 (18)
C8—C9—Fe1—C10	119.2 (2)	C24—C25—Fe2—C21	118.84 (18)
C8—C9—Fe1—C1	164.1 (3)	C23—C24—Fe2—C28	−81.2 (2)
C10—C9—Fe1—C1	44.9 (3)	C25—C24—Fe2—C28	158.9 (2)
C4—C3—Fe1—C7	−165.14 (14)	C23—C24—Fe2—C27	−48.0 (3)
C2—C3—Fe1—C7	75.48 (16)	C25—C24—Fe2—C27	−167.9 (3)
C4—C3—Fe1—C8	−124.08 (14)	C23—C24—Fe2—C29	−122.09 (19)
C2—C3—Fe1—C8	116.55 (14)	C25—C24—Fe2—C29	118.09 (18)
C4—C3—Fe1—C6	166.6 (3)	C23—C24—Fe2—C26	168.2 (3)
C2—C3—Fe1—C6	47.3 (4)	C25—C24—Fe2—C26	48.3 (4)
C2—C3—Fe1—C4	−119.37 (19)	C23—C24—Fe2—C30	−162.15 (15)
C4—C3—Fe1—C5	37.47 (13)	C25—C24—Fe2—C30	78.02 (17)
C2—C3—Fe1—C5	−81.90 (13)	C23—C24—Fe2—C22	37.61 (13)
C4—C3—Fe1—C9	−82.37 (16)	C25—C24—Fe2—C22	−82.22 (14)
C2—C3—Fe1—C9	158.26 (13)	C25—C24—Fe2—C23	−119.82 (19)
C4—C3—Fe1—C2	119.37 (19)	C23—C24—Fe2—C25	119.82 (19)
C4—C3—Fe1—C10	−51.0 (3)	C23—C24—Fe2—C21	81.72 (14)
C2—C3—Fe1—C10	−170.36 (18)	C25—C24—Fe2—C21	−38.10 (13)
C4—C3—Fe1—C1	81.49 (14)	C22—C21—Fe2—C28	41.0 (4)
C2—C3—Fe1—C1	−37.88 (12)	C25—C21—Fe2—C28	160.3 (4)
C3—C2—Fe1—C7	−124.39 (15)	C31—C21—Fe2—C28	−79.0 (4)
C1—C2—Fe1—C7	116.53 (13)	C22—C21—Fe2—C27	75.1 (2)
C3—C2—Fe1—C8	−81.11 (16)	C25—C21—Fe2—C27	−165.54 (19)
C1—C2—Fe1—C8	159.81 (13)	C31—C21—Fe2—C27	−44.9 (3)
C3—C2—Fe1—C6	−165.15 (14)	C22—C21—Fe2—C29	−166.7 (2)
C1—C2—Fe1—C6	75.77 (15)	C25—C21—Fe2—C29	−47.3 (3)
C3—C2—Fe1—C4	37.43 (14)	C31—C21—Fe2—C29	73.4 (3)
C1—C2—Fe1—C4	−81.66 (13)	C22—C21—Fe2—C26	117.50 (17)
C3—C2—Fe1—C5	81.26 (14)	C25—C21—Fe2—C26	−123.15 (17)
C1—C2—Fe1—C5	−37.83 (11)	C31—C21—Fe2—C26	−2.5 (2)
C3—C2—Fe1—C9	−47.5 (3)	C22—C21—Fe2—C30	159.31 (15)
C1—C2—Fe1—C9	−166.59 (18)	C25—C21—Fe2—C30	−81.33 (16)
C1—C2—Fe1—C3	−119.09 (17)	C31—C21—Fe2—C30	39.3 (2)
C3—C2—Fe1—C10	164.1 (3)	C25—C21—Fe2—C22	119.35 (16)
C1—C2—Fe1—C10	45.0 (3)	C31—C21—Fe2—C22	−120.0 (2)
C3—C2—Fe1—C1	119.09 (17)	C22—C21—Fe2—C23	−37.91 (12)
C6—C10—Fe1—C7	−37.76 (14)	C25—C21—Fe2—C23	81.44 (13)
C9—C10—Fe1—C7	81.98 (16)	C31—C21—Fe2—C23	−157.9 (2)
C6—C10—Fe1—C8	−82.27 (16)	C22—C21—Fe2—C25	−119.35 (16)
C9—C10—Fe1—C8	37.47 (15)	C31—C21—Fe2—C25	120.7 (2)
C9—C10—Fe1—C6	119.7 (2)	C22—C21—Fe2—C24	−81.52 (13)
C6—C10—Fe1—C4	159.63 (14)	C25—C21—Fe2—C24	37.84 (12)
C9—C10—Fe1—C4	−80.64 (16)	C31—C21—Fe2—C24	158.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg2^i	0.93	3.10	3.874 (2)	142
C29—H29···Cg1^ii	0.93	3.12	3.889 (3)	141

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1.

(II) (Phenylethynyl)ferrocene

Crystal data

[Fe(C5H5)(C13H9)]	F(000) = 592
Mr = 286.14	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10424 reflections
a = 8.7368 (9) Å	θ = 1.9–27.9°
b = 10.6296 (15) Å	µ = 1.10 mm^−1
c = 15.1113 (16) Å	T = 296 K
β = 105.327 (8)°	Plate, red
V = 1353.5 (3) Å^3	0.62 × 0.51 × 0.14 mm
Z = 4

Data collection

Stoe IPDS 2 diffractometer	2650 independent reflections
Radiation source: fine-focus sealed tube	1865 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
w scan	θmax = 26.0°, θmin = 2.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −8→10
Tmin = 0.583, Tmax = 0.848	k = −12→13
7479 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.036P)^2] where P = (Fo^2 + 2Fc^2)/3
2650 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.8896 (3)	0.33485 (19)	0.37962 (13)	0.0522 (5)
C2	0.8274 (3)	0.2171 (2)	0.34068 (13)	0.0577 (5)
H2	0.7407	0.2062	0.2901	0.069*
C3	0.9205 (3)	0.1200 (2)	0.39231 (15)	0.0645 (6)
H3	0.9057	0.0341	0.3818	0.077*
C4	1.0398 (3)	0.1766 (2)	0.46243 (15)	0.0660 (6)
H4	1.1178	0.1340	0.5059	0.079*
C5	1.0214 (3)	0.3082 (2)	0.45583 (14)	0.0587 (5)
H5	1.0841	0.3672	0.4944	0.070*
C6	0.6545 (4)	0.3274 (3)	0.51408 (19)	0.0841 (8)
H6	0.6173	0.4064	0.4921	0.101*
C7	0.5918 (3)	0.2107 (3)	0.47678 (19)	0.0846 (8)
H7	0.5055	0.1992	0.4261	0.102*
C8	0.6834 (4)	0.1147 (3)	0.5301 (2)	0.0808 (7)
H8	0.6689	0.0286	0.5205	0.097*
C9	0.7992 (3)	0.1719 (3)	0.59944 (16)	0.0769 (7)
H9	0.8753	0.1301	0.6446	0.092*
C10	0.7828 (4)	0.3028 (3)	0.59019 (18)	0.0794 (7)
H10	0.8457	0.3626	0.6278	0.095*
C11	0.8314 (3)	0.4571 (2)	0.34863 (13)	0.0558 (5)
C12	0.7863 (3)	0.5603 (2)	0.32363 (14)	0.0564 (5)
C13	0.7305 (2)	0.68504 (18)	0.29474 (13)	0.0509 (5)
C14	0.6196 (3)	0.7447 (2)	0.33065 (16)	0.0651 (6)
H14	0.5808	0.7046	0.3749	0.078*
C15	0.5664 (3)	0.8634 (2)	0.30094 (18)	0.0748 (7)
H15	0.4908	0.9025	0.3248	0.090*
C16	0.6238 (3)	0.9243 (2)	0.23672 (19)	0.0766 (7)
H16	0.5875	1.0044	0.2170	0.092*
C17	0.7343 (3)	0.8668 (2)	0.20194 (18)	0.0759 (7)
H17	0.7739	0.9084	0.1586	0.091*
C18	0.7881 (3)	0.74820 (19)	0.22991 (15)	0.0619 (6)
H18	0.8634	0.7101	0.2053	0.074*
Fe1	0.82136 (4)	0.22731 (3)	0.474237 (18)	0.05270 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0622 (14)	0.0480 (11)	0.0498 (10)	0.0001 (10)	0.0206 (9)	0.0036 (8)
C2	0.0732 (14)	0.0535 (12)	0.0490 (10)	−0.0020 (12)	0.0206 (10)	−0.0017 (9)
C3	0.0890 (18)	0.0484 (13)	0.0649 (13)	0.0071 (12)	0.0360 (13)	0.0025 (10)
C4	0.0679 (16)	0.0693 (14)	0.0662 (13)	0.0171 (12)	0.0272 (12)	0.0153 (11)
C5	0.0601 (14)	0.0606 (14)	0.0567 (11)	−0.0014 (10)	0.0179 (10)	0.0026 (9)
C6	0.096 (2)	0.0771 (18)	0.097 (2)	0.0256 (17)	0.0565 (19)	0.0176 (15)
C7	0.0605 (16)	0.115 (2)	0.0830 (17)	0.0018 (17)	0.0264 (13)	0.0081 (17)
C8	0.0891 (19)	0.0741 (17)	0.0937 (17)	−0.0076 (16)	0.0495 (16)	0.0083 (15)
C9	0.0833 (19)	0.0956 (19)	0.0604 (14)	0.0137 (15)	0.0343 (13)	0.0204 (13)
C10	0.098 (2)	0.084 (2)	0.0689 (15)	0.0014 (15)	0.0451 (14)	−0.0090 (13)
C11	0.0629 (14)	0.0550 (13)	0.0513 (11)	−0.0054 (11)	0.0184 (10)	−0.0004 (9)
C12	0.0611 (14)	0.0512 (13)	0.0560 (11)	−0.0026 (10)	0.0142 (10)	0.0025 (9)
C13	0.0521 (12)	0.0448 (11)	0.0552 (10)	−0.0045 (9)	0.0130 (9)	−0.0008 (8)
C14	0.0635 (14)	0.0637 (16)	0.0735 (14)	−0.0040 (11)	0.0276 (11)	−0.0024 (10)
C15	0.0619 (16)	0.0673 (16)	0.0972 (17)	0.0089 (12)	0.0245 (14)	−0.0157 (13)
C16	0.0738 (18)	0.0492 (14)	0.1017 (19)	0.0044 (12)	0.0145 (15)	0.0025 (12)
C17	0.0841 (19)	0.0600 (15)	0.0890 (16)	0.0036 (13)	0.0325 (15)	0.0196 (12)
C18	0.0635 (15)	0.0557 (15)	0.0726 (13)	0.0063 (11)	0.0288 (11)	0.0069 (9)
Fe1	0.06105 (19)	0.05138 (17)	0.04986 (16)	0.00331 (16)	0.02204 (12)	0.00424 (13)

Geometric parameters (Å, º)

C1—C5	1.425 (3)	C8—C9	1.390 (4)
C1—C2	1.428 (3)	C8—Fe1	2.034 (2)
C1—C11	1.429 (3)	C8—H8	0.9300
C1—Fe1	2.0390 (19)	C9—C10	1.402 (4)
C2—C3	1.414 (3)	C9—Fe1	2.039 (2)
C2—Fe1	2.0358 (19)	C9—H9	0.9300
C2—H2	0.9300	C10—Fe1	2.035 (2)
C3—C4	1.409 (3)	C10—H10	0.9300
C3—Fe1	2.038 (2)	C11—C12	1.192 (3)
C3—H3	0.9300	C12—C13	1.440 (3)
C4—C5	1.408 (3)	C13—C14	1.384 (3)
C4—Fe1	2.036 (2)	C13—C18	1.387 (3)
C4—H4	0.9300	C14—C15	1.378 (3)
C5—Fe1	2.031 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.367 (4)
C6—C10	1.402 (4)	C15—H15	0.9300
C6—C7	1.412 (4)	C16—C17	1.360 (4)
C6—Fe1	2.021 (3)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.372 (3)
C7—C8	1.411 (4)	C17—H17	0.9300
C7—Fe1	2.024 (3)	C18—H18	0.9300
C7—H7	0.9300
C5—C1—C2	107.25 (18)	C14—C13—C12	121.28 (19)
C5—C1—C11	126.0 (2)	C18—C13—C12	120.20 (19)
C2—C1—C11	126.77 (19)	C15—C14—C13	120.2 (2)
C5—C1—Fe1	69.21 (11)	C15—C14—H14	119.9
C2—C1—Fe1	69.37 (11)	C13—C14—H14	119.9
C11—C1—Fe1	126.52 (15)	C16—C15—C14	120.6 (2)
C3—C2—C1	108.16 (18)	C16—C15—H15	119.7
C3—C2—Fe1	69.75 (11)	C14—C15—H15	119.7
C1—C2—Fe1	69.61 (11)	C17—C16—C15	119.5 (2)
C3—C2—H2	125.9	C17—C16—H16	120.2
C1—C2—H2	125.9	C15—C16—H16	120.2
Fe1—C2—H2	126.3	C16—C17—C18	120.9 (2)
C4—C3—C2	107.84 (19)	C16—C17—H17	119.5
C4—C3—Fe1	69.69 (13)	C18—C17—H17	119.5
C2—C3—Fe1	69.61 (12)	C17—C18—C13	120.2 (2)
C4—C3—H3	126.1	C17—C18—H18	119.9
C2—C3—H3	126.1	C13—C18—H18	119.9
Fe1—C3—H3	126.2	C6—Fe1—C7	40.86 (12)
C5—C4—C3	108.8 (2)	C6—Fe1—C5	122.19 (11)
C5—C4—Fe1	69.57 (13)	C7—Fe1—C5	158.78 (11)
C3—C4—Fe1	69.83 (14)	C6—Fe1—C8	68.46 (12)
C5—C4—H4	125.6	C7—Fe1—C8	40.68 (11)
C3—C4—H4	125.6	C5—Fe1—C8	158.68 (11)
Fe1—C4—H4	126.6	C6—Fe1—C10	40.45 (11)
C4—C5—C1	107.9 (2)	C7—Fe1—C10	68.13 (12)
C4—C5—Fe1	69.91 (13)	C5—Fe1—C10	107.18 (10)
C1—C5—Fe1	69.80 (12)	C8—Fe1—C10	67.90 (11)
C4—C5—H5	126.0	C6—Fe1—C4	158.82 (12)
C1—C5—H5	126.0	C7—Fe1—C4	159.25 (12)
Fe1—C5—H5	125.8	C5—Fe1—C4	40.52 (9)
C10—C6—C7	107.8 (2)	C8—Fe1—C4	123.54 (11)
C10—C6—Fe1	70.30 (14)	C10—Fe1—C4	123.54 (11)
C7—C6—Fe1	69.69 (15)	C6—Fe1—C2	122.23 (10)
C10—C6—H6	126.1	C7—Fe1—C2	107.45 (10)
C7—C6—H6	126.1	C5—Fe1—C2	68.78 (9)
Fe1—C6—H6	125.5	C8—Fe1—C2	123.61 (11)
C8—C7—C6	107.8 (2)	C10—Fe1—C2	158.18 (10)
C8—C7—Fe1	70.03 (15)	C4—Fe1—C2	68.18 (9)
C6—C7—Fe1	69.45 (15)	C6—Fe1—C3	158.73 (12)
C8—C7—H7	126.1	C7—Fe1—C3	123.05 (12)
C6—C7—H7	126.1	C5—Fe1—C3	68.54 (9)
Fe1—C7—H7	126.0	C8—Fe1—C3	108.44 (10)
C9—C8—C7	107.7 (3)	C10—Fe1—C3	159.70 (11)
C9—C8—Fe1	70.24 (14)	C4—Fe1—C3	40.48 (9)
C7—C8—Fe1	69.29 (15)	C2—Fe1—C3	40.64 (8)
C9—C8—H8	126.1	C6—Fe1—C1	106.36 (10)
C7—C8—H8	126.1	C7—Fe1—C1	122.50 (10)
Fe1—C8—H8	125.9	C5—Fe1—C1	40.99 (8)
C8—C9—C10	108.9 (2)	C8—Fe1—C1	159.43 (11)
C8—C9—Fe1	69.84 (14)	C10—Fe1—C1	121.91 (10)
C10—C9—Fe1	69.70 (13)	C4—Fe1—C1	68.43 (9)
C8—C9—H9	125.5	C2—Fe1—C1	41.02 (8)
C10—C9—H9	125.5	C3—Fe1—C1	68.75 (8)
Fe1—C9—H9	126.5	C6—Fe1—C9	67.84 (11)
C9—C10—C6	107.8 (3)	C7—Fe1—C9	67.65 (11)
C9—C10—Fe1	70.03 (13)	C5—Fe1—C9	123.04 (10)
C6—C10—Fe1	69.25 (14)	C8—Fe1—C9	39.92 (10)
C9—C10—H10	126.1	C10—Fe1—C9	40.27 (11)
C6—C10—H10	126.1	C4—Fe1—C9	109.01 (10)
Fe1—C10—H10	126.2	C2—Fe1—C9	159.76 (11)
C12—C11—C1	178.5 (3)	C3—Fe1—C9	124.19 (10)
C11—C12—C13	179.0 (2)	C1—Fe1—C9	158.39 (11)
C14—C13—C18	118.52 (19)
C5—C1—C2—C3	−0.2 (2)	C9—C10—Fe1—C6	119.0 (3)
C11—C1—C2—C3	179.9 (2)	C9—C10—Fe1—C7	80.78 (19)
Fe1—C1—C2—C3	−59.30 (15)	C6—C10—Fe1—C7	−38.24 (17)
C5—C1—C2—Fe1	59.07 (14)	C9—C10—Fe1—C5	−121.19 (17)
C11—C1—C2—Fe1	−120.8 (2)	C6—C10—Fe1—C5	119.78 (17)
C1—C2—C3—C4	−0.2 (2)	C9—C10—Fe1—C8	36.75 (16)
Fe1—C2—C3—C4	−59.43 (15)	C6—C10—Fe1—C8	−82.28 (19)
C1—C2—C3—Fe1	59.21 (14)	C9—C10—Fe1—C4	−79.75 (19)
C2—C3—C4—C5	0.6 (3)	C6—C10—Fe1—C4	161.22 (16)
Fe1—C3—C4—C5	−58.79 (15)	C9—C10—Fe1—C2	163.1 (2)
C2—C3—C4—Fe1	59.38 (15)	C6—C10—Fe1—C2	44.1 (4)
C3—C4—C5—C1	−0.7 (2)	C9—C10—Fe1—C3	−46.7 (4)
Fe1—C4—C5—C1	−59.69 (15)	C6—C10—Fe1—C3	−165.7 (3)
C3—C4—C5—Fe1	58.96 (16)	C9—C10—Fe1—C1	−163.62 (16)
C2—C1—C5—C4	0.6 (2)	C6—C10—Fe1—C1	77.36 (19)
C11—C1—C5—C4	−179.51 (19)	C6—C10—Fe1—C9	−119.0 (3)
Fe1—C1—C5—C4	59.76 (15)	C5—C4—Fe1—C6	−41.4 (3)
C2—C1—C5—Fe1	−59.17 (14)	C3—C4—Fe1—C6	−161.6 (2)
C11—C1—C5—Fe1	120.7 (2)	C5—C4—Fe1—C7	164.1 (3)
C10—C6—C7—C8	−0.5 (3)	C3—C4—Fe1—C7	43.8 (3)
Fe1—C6—C7—C8	59.75 (18)	C3—C4—Fe1—C5	−120.24 (17)
C10—C6—C7—Fe1	−60.25 (17)	C5—C4—Fe1—C8	−160.83 (14)
C6—C7—C8—C9	0.6 (3)	C3—C4—Fe1—C8	78.93 (16)
Fe1—C7—C8—C9	60.00 (18)	C5—C4—Fe1—C10	−76.70 (16)
C6—C7—C8—Fe1	−59.39 (18)	C3—C4—Fe1—C10	163.06 (13)
C7—C8—C9—C10	−0.5 (3)	C5—C4—Fe1—C2	82.43 (13)
Fe1—C8—C9—C10	58.91 (17)	C3—C4—Fe1—C2	−37.81 (12)
C7—C8—C9—Fe1	−59.40 (18)	C5—C4—Fe1—C3	120.24 (17)
C8—C9—C10—C6	0.2 (3)	C5—C4—Fe1—C1	38.12 (12)
Fe1—C9—C10—C6	59.17 (17)	C3—C4—Fe1—C1	−82.11 (13)
C8—C9—C10—Fe1	−59.00 (18)	C5—C4—Fe1—C9	−118.98 (14)
C7—C6—C10—C9	0.2 (3)	C3—C4—Fe1—C9	120.78 (15)
Fe1—C6—C10—C9	−59.67 (17)	C3—C2—Fe1—C6	−163.12 (16)
C7—C6—C10—Fe1	59.87 (17)	C1—C2—Fe1—C6	77.44 (17)
C18—C13—C14—C15	1.1 (3)	C3—C2—Fe1—C7	−120.77 (16)
C12—C13—C14—C15	−179.1 (2)	C1—C2—Fe1—C7	119.79 (15)
C13—C14—C15—C16	−0.8 (4)	C3—C2—Fe1—C5	81.37 (15)
C14—C15—C16—C17	0.1 (4)	C1—C2—Fe1—C5	−38.07 (13)
C15—C16—C17—C18	0.5 (4)	C3—C2—Fe1—C8	−78.98 (18)
C16—C17—C18—C13	−0.2 (4)	C1—C2—Fe1—C8	161.58 (14)
C14—C13—C18—C17	−0.6 (3)	C3—C2—Fe1—C10	164.6 (3)
C12—C13—C18—C17	179.6 (2)	C1—C2—Fe1—C10	45.2 (3)
C10—C6—Fe1—C7	118.6 (2)	C3—C2—Fe1—C4	37.67 (14)
C10—C6—Fe1—C5	−78.45 (18)	C1—C2—Fe1—C4	−81.77 (14)
C7—C6—Fe1—C5	162.96 (14)	C1—C2—Fe1—C3	−119.44 (19)
C10—C6—Fe1—C8	80.76 (18)	C3—C2—Fe1—C1	119.44 (19)
C7—C6—Fe1—C8	−37.82 (16)	C3—C2—Fe1—C9	−48.2 (3)
C7—C6—Fe1—C10	−118.6 (2)	C1—C2—Fe1—C9	−167.7 (3)
C10—C6—Fe1—C4	−47.9 (3)	C4—C3—Fe1—C6	161.7 (3)
C7—C6—Fe1—C4	−166.5 (2)	C2—C3—Fe1—C6	42.6 (3)
C10—C6—Fe1—C2	−162.20 (15)	C4—C3—Fe1—C7	−162.97 (15)
C7—C6—Fe1—C2	79.22 (18)	C2—C3—Fe1—C7	77.94 (17)
C10—C6—Fe1—C3	166.4 (2)	C4—C3—Fe1—C5	37.10 (13)
C7—C6—Fe1—C3	47.8 (3)	C2—C3—Fe1—C5	−81.99 (14)
C10—C6—Fe1—C1	−120.32 (16)	C4—C3—Fe1—C8	−120.43 (15)
C7—C6—Fe1—C1	121.10 (16)	C2—C3—Fe1—C8	120.49 (15)
C10—C6—Fe1—C9	37.61 (17)	C4—C3—Fe1—C10	−44.4 (3)
C7—C6—Fe1—C9	−80.98 (17)	C2—C3—Fe1—C10	−163.5 (3)
C8—C7—Fe1—C6	−119.0 (2)	C2—C3—Fe1—C4	−119.09 (19)
C8—C7—Fe1—C5	−162.2 (2)	C4—C3—Fe1—C2	119.09 (19)
C6—C7—Fe1—C5	−43.3 (3)	C4—C3—Fe1—C1	81.26 (14)
C6—C7—Fe1—C8	119.0 (2)	C2—C3—Fe1—C1	−37.83 (13)
C8—C7—Fe1—C10	−81.08 (18)	C4—C3—Fe1—C9	−79.09 (17)
C6—C7—Fe1—C10	37.87 (15)	C2—C3—Fe1—C9	161.83 (15)
C8—C7—Fe1—C4	47.3 (4)	C5—C1—Fe1—C6	120.57 (15)
C6—C7—Fe1—C4	166.3 (2)	C2—C1—Fe1—C6	−120.62 (15)
C8—C7—Fe1—C2	121.63 (17)	C11—C1—Fe1—C6	0.5 (2)
C6—C7—Fe1—C2	−119.42 (16)	C5—C1—Fe1—C7	162.18 (14)
C8—C7—Fe1—C3	79.75 (19)	C2—C1—Fe1—C7	−79.01 (17)
C6—C7—Fe1—C3	−161.30 (15)	C11—C1—Fe1—C7	42.1 (2)
C8—C7—Fe1—C1	164.11 (15)	C2—C1—Fe1—C5	118.81 (18)
C6—C7—Fe1—C1	−76.94 (18)	C11—C1—Fe1—C5	−120.1 (2)
C8—C7—Fe1—C9	−37.46 (16)	C5—C1—Fe1—C8	−167.3 (3)
C6—C7—Fe1—C9	81.49 (17)	C2—C1—Fe1—C8	−48.5 (3)
C4—C5—Fe1—C6	163.60 (14)	C11—C1—Fe1—C8	72.6 (3)
C1—C5—Fe1—C6	−77.47 (16)	C5—C1—Fe1—C10	79.28 (16)
C4—C5—Fe1—C7	−164.4 (3)	C2—C1—Fe1—C10	−161.91 (15)
C1—C5—Fe1—C7	−45.5 (3)	C11—C1—Fe1—C10	−40.8 (2)
C4—C5—Fe1—C8	48.8 (3)	C5—C1—Fe1—C4	−37.70 (13)
C1—C5—Fe1—C8	167.7 (3)	C2—C1—Fe1—C4	81.11 (14)
C4—C5—Fe1—C10	121.89 (15)	C11—C1—Fe1—C4	−157.7 (2)
C1—C5—Fe1—C10	−119.18 (14)	C5—C1—Fe1—C2	−118.81 (18)
C1—C5—Fe1—C4	118.93 (18)	C11—C1—Fe1—C2	121.1 (2)
C4—C5—Fe1—C2	−80.83 (13)	C5—C1—Fe1—C3	−81.32 (14)
C1—C5—Fe1—C2	38.09 (12)	C2—C1—Fe1—C3	37.48 (13)
C4—C5—Fe1—C3	−37.06 (12)	C11—C1—Fe1—C3	158.6 (2)
C1—C5—Fe1—C3	81.87 (13)	C5—C1—Fe1—C9	49.6 (3)
C4—C5—Fe1—C1	−118.93 (18)	C2—C1—Fe1—C9	168.4 (3)
C4—C5—Fe1—C9	80.62 (16)	C11—C1—Fe1—C9	−70.4 (3)
C1—C5—Fe1—C9	−160.45 (14)	C8—C9—Fe1—C6	82.47 (19)
C9—C8—Fe1—C6	−80.78 (18)	C10—C9—Fe1—C6	−37.78 (18)
C7—C8—Fe1—C6	37.98 (16)	C8—C9—Fe1—C7	38.16 (17)
C9—C8—Fe1—C7	−118.8 (2)	C10—C9—Fe1—C7	−82.09 (19)
C9—C8—Fe1—C5	43.5 (3)	C8—C9—Fe1—C5	−162.62 (16)
C7—C8—Fe1—C5	162.3 (2)	C10—C9—Fe1—C5	77.13 (19)
C9—C8—Fe1—C10	−37.06 (17)	C10—C9—Fe1—C8	−120.2 (2)
C7—C8—Fe1—C10	81.70 (19)	C8—C9—Fe1—C10	120.2 (2)
C9—C8—Fe1—C4	79.44 (19)	C8—C9—Fe1—C4	−119.93 (17)
C7—C8—Fe1—C4	−161.79 (17)	C10—C9—Fe1—C4	119.83 (18)
C9—C8—Fe1—C2	164.00 (15)	C8—C9—Fe1—C2	−41.6 (4)
C7—C8—Fe1—C2	−77.2 (2)	C10—C9—Fe1—C2	−161.8 (3)
C9—C8—Fe1—C3	121.63 (17)	C8—C9—Fe1—C3	−77.53 (19)
C7—C8—Fe1—C3	−119.60 (18)	C10—C9—Fe1—C3	162.22 (17)
C9—C8—Fe1—C1	−159.8 (2)	C8—C9—Fe1—C1	160.8 (2)
C7—C8—Fe1—C1	−41.1 (4)	C10—C9—Fe1—C1	40.5 (4)
C7—C8—Fe1—C9	118.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg3^i	0.93	3.13	3.927 (3)	145
C14—H14···Cg2^ii	0.93	3.14	3.817 (3)	131
C15—H15···Cg2^ii	0.93	3.25	3.870 (3)	126
C18—H18···Cg1^iii	0.93	2.72	3.535 (3)	147

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, y+1/2, −z+1/2.