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Acta Cryst. (2008). E64, m1630    [ doi:10.1107/S1600536808039524 ]

4-Ferrocenylphenol

V. O. Nyamori and M. D. Bala

Abstract top

The title compound, [Fe(C5H5)(C11H9O)], is of interest as a precursor to the synthesis of cheap ferrocene-based liquid crystals. The -OH substituent only results in weak C-H...O weak interactions between one of cyclopentadienyl (Cp) ring H atoms and the O atom of a neighbouring molecule with a distance of 3.308 (3) Å between the donor and acceptor atoms. The interplanar angle between the Cp and benzene rings is 13.0 (4)°. There are also weak O-H...[pi] and C-H...[pi] interactions involving the unsubstituted Cp and the benzene ring, respectively.

Comment top

The synthesis of arylferrocenes especially compounds prepared by the reaction of para-substituted anilines via diazonium reactions to yield phenylferrocenes has evoked the interest of material scientists (Togni & Hayashi, 1995). For example, arylferrocenes have been established as precursors in the synthesis of ferrocenomesogens especially those with ferrocenyl moiety incorporated as a terminal group (Imrie et al., 2002). These class of compounds are most readily prepared by cross-coupling reactions, e.g. of iodoferrocene (Imrie et al., 2003) with arylboronic (Tsukazaki et al., 1996) and organotin compounds (Lin et al., 1995). Alternative cross-coupling reagents include aryl halides with tin (Guillaneux & Kagan, 1995), zinc (Foxman & Rosenblum, 1993) and ferrocenylboronic acids (Knapp & Rehahn, 1993). In this paper we report the synthesis of 4-hydroxyphenylferrocene using 4-aminophenol which was obtained via diazonium reaction.

The title compound (I) (Fig. 1) is a precursor prepared as part of a study to develop starting materials from cheaper sources for the development of new ionic liquid and liquid crystal materials (Nyamori & Bala, 2008a; 2008b). Due to the –OH subtituent on the benzyl ring it was thought that the property of (I) will be dominated by intra- or intermolecular hydrogen bonding, but analysis revealed no classical hydrogen bonds. Hence, the high melting point of 162 oC may be attributed to a concerted contribution from all molecular contacts within the crystal of (I) (Table 1: Cg(1) is the centroid of the unsubstituted Cp and Cg(3) the centroid of the benzene ring).

In the crystal of (I), the two cp rings are marginally tilted towards each other with a tilt angle between the planes of the two rings of 0.41 (5)°, while the interplanar angle between the cp and the phenyl ring is 13.0 (4)°.

Related literature top

For general background, see: Togni & Hayashi (1995); Imrie et al. (2002). For related structures, see: Imrie et al. (2003); Nyamori & Bala (2008a,b). For related syntheses, see: Guillaneux & Kagan (1995); Foxman & Rosenblum (1993); Tsukazaki et al. (1996); Lin et al. (1995); Knapp & Rehahn, (1993). Cg1 and Cg3 are the centroids of the unsubstituted Cp and the benzene rings, respectively.

Experimental top

In an excess of 2M hydrochloric acid at 5 °C was dissolved 4-aminophenol (12.00 g, 0.11 mol) followed by slow addition of sodium nitrite (8.00 g, 0.11 mol) in cold water (20 cm3) also at 5 °C. The solution was left to stir at this temperature for 30 min and the resultant solution was filtered. The filtrate was immediately added to a cold thoroughly stirred solution of ferrocene (18.00 g, 0.10 mol) in diethyl ether (500 cm3). Stirring was continued at 5 °C for 8 h. The ether layer was then separated, washed with water (3 x 100 cm3) and dried over anhydrous sodium sulfate. The solution was concentrated and the residue was passed through a column of alumina. Dichloromethane: hexane (1:1) eluted unreacted ferrocene. Further elution of the column with diethyl ether yielded 4-ferrocenylphenol (5.22 g, 32%) as yellow crystals recrystallized from hexane, mp 162 oC.

FTIR: νmax(KBr/cm-1) 3515, 3091, 1901, 1607, 1525, 1454, 1434, 1264, 1210, 1176, 1102, 1027, 998, 885, 839, 816, 665, 620; 1H-NMR: δH(CDCl3) 7.38(2H, d, J 8.5, ArH), 6.79(2H, d, J 8.1, ArH), 4.87(1H, s,OH), 4.58(2H, t, J 1.9, C5H4), 4.28(2H, t, J 1.9, C5H4), 4.05(5H, s, C5H5); 13C-NMR: δC(CDCl3) 154.25, 131.88, 127.76, 115.70, 86.192, 69.87, 68.89, 66.51; EI–MS 70 eV m/z (%): 280(39%), 277(M+, 81%), 276(100%), 220(10%), 213(39%); Found: M+, 278.0388 for C16H14FeO, requires M, 278.0392.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). Hydrogen atom attached to oxygen was freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title complex with the atom labelling scheme. Ellipsoids are drawn at the 50% probability level.
4-Ferrocenylphenol top
Crystal data top
[Fe(C5H5)(C11H9O)]F(000) = 1152
Mr = 278.12Dx = 1.51 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 946 reflections
a = 9.950 (2) Åθ = 3.9–27.6°
b = 7.9205 (17) ŵ = 1.22 mm−1
c = 31.046 (6) ÅT = 173 K
V = 2446.8 (9) Å3Plate, orange
Z = 80.42 × 0.22 × 0.07 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2214 reflections with I > 2σ(I)
φ and ω scansRint = 0.051
Absorption correction: integration
(XPREP; Bruker, 2005)		θmax = 28.3°, θmin = 2.4°
Tmin = 0.750, Tmax = 0.929h = −13→8
14324 measured reflectionsk = −9→10
3039 independent reflectionsl = −41→41
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0424P)2 + 0.544P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.31 e Å−3
3039 reflectionsΔρmin = −0.42 e Å−3
164 parameters
Crystal data top
[Fe(C5H5)(C11H9O)]V = 2446.8 (9) Å3
Mr = 278.12Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.950 (2) ŵ = 1.22 mm−1
b = 7.9205 (17) ÅT = 173 K
c = 31.046 (6) Å0.42 × 0.22 × 0.07 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3039 independent reflections
Absorption correction: integration
(XPREP; Bruker, 2005)		2214 reflections with I > 2σ(I)
Tmin = 0.750, Tmax = 0.929Rint = 0.051
14324 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.084Δρmax = 0.31 e Å−3
S = 1.02Δρmin = −0.42 e Å−3
3039 reflectionsAbsolute structure: ?
164 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1−0.1342 (2)0.1001 (3)0.11907 (7)0.0408 (6)
H1−0.15860.14890.14590.049*
C2−0.1895 (2)0.1413 (3)0.07829 (8)0.0354 (5)
H2−0.25750.22280.07290.042*
C3−0.1253 (2)0.0396 (3)0.04727 (7)0.0347 (5)
H3−0.14260.04010.01720.042*
C4−0.0312 (2)−0.0627 (3)0.06860 (9)0.0380 (6)
H40.0263−0.14310.05540.046*
C5−0.0366 (2)−0.0263 (3)0.11265 (9)0.0420 (6)
H50.0163−0.07780.13450.05*
C60.10992 (19)0.3807 (2)0.10912 (6)0.0210 (4)
C70.0405 (2)0.4386 (2)0.07116 (6)0.0250 (4)
H7−0.02810.5220.07040.03*
C80.0926 (2)0.3492 (2)0.03499 (6)0.0263 (4)
H80.0650.36290.00590.032*
C90.1930 (2)0.2361 (3)0.04994 (7)0.0267 (4)
H90.24410.16080.03260.032*
C100.20381 (19)0.2549 (2)0.09535 (7)0.0237 (4)
H100.26340.19410.11350.028*
C110.09297 (19)0.4446 (2)0.15359 (6)0.0218 (4)
C12−0.0132 (2)0.5527 (3)0.16436 (7)0.0281 (4)
H12−0.07890.57910.14320.034*
C13−0.0248 (2)0.6219 (3)0.20519 (7)0.0332 (5)
H13−0.09750.69530.21170.04*
C140.0701 (3)0.5840 (3)0.23658 (7)0.0339 (5)
C150.1749 (2)0.4741 (3)0.22686 (7)0.0322 (5)
H150.2390.44580.24840.039*
C160.1861 (2)0.4061 (3)0.18597 (6)0.0266 (4)
H160.25840.33170.17970.032*
O10.0663 (2)0.6509 (3)0.27745 (5)0.0519 (5)
H1A−0.00330.70990.28030.078*
Fe10.01267 (3)0.18508 (3)0.078786 (8)0.02002 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0393 (14)0.0524 (15)0.0306 (12)−0.0248 (12)0.0100 (10)−0.0062 (11)
C20.0181 (10)0.0312 (11)0.0567 (16)−0.0031 (8)−0.0022 (10)0.0064 (10)
C30.0340 (12)0.0417 (13)0.0286 (11)−0.0154 (10)−0.0044 (9)−0.0013 (10)
C40.0294 (12)0.0196 (10)0.0650 (17)−0.0067 (9)0.0036 (11)−0.0031 (10)
C50.0360 (13)0.0390 (14)0.0511 (15)−0.0137 (10)−0.0123 (11)0.0252 (12)
C60.0207 (10)0.0187 (9)0.0236 (10)−0.0036 (7)0.0012 (8)0.0020 (7)
C70.0273 (11)0.0198 (9)0.0278 (11)−0.0011 (8)0.0005 (8)0.0027 (8)
C80.0334 (12)0.0248 (10)0.0207 (10)−0.0065 (8)0.0018 (8)0.0026 (8)
C90.0237 (10)0.0268 (10)0.0295 (11)−0.0047 (8)0.0069 (9)−0.0064 (8)
C100.0192 (10)0.0218 (10)0.0303 (10)−0.0020 (8)−0.0016 (8)−0.0009 (8)
C110.0234 (10)0.0190 (9)0.0230 (10)−0.0025 (8)0.0012 (8)0.0009 (7)
C120.0285 (11)0.0295 (11)0.0262 (10)0.0035 (9)−0.0027 (8)0.0009 (8)
C130.0378 (13)0.0323 (11)0.0294 (11)0.0078 (10)0.0053 (10)−0.0026 (9)
C140.0487 (14)0.0327 (12)0.0202 (10)−0.0010 (10)0.0032 (10)−0.0029 (8)
C150.0369 (12)0.0348 (12)0.0249 (11)−0.0015 (10)−0.0052 (9)0.0032 (9)
C160.0265 (11)0.0255 (11)0.0278 (11)0.0015 (8)−0.0005 (9)0.0025 (8)
O10.0721 (14)0.0599 (12)0.0237 (8)0.0148 (10)−0.0012 (9)−0.0124 (8)
Fe10.01885 (16)0.01960 (15)0.02160 (15)−0.00114 (11)−0.00087 (11)0.00129 (11)
Geometric parameters (Å, °) top
C1—C51.409 (4)C7—H70.95
C1—C21.419 (3)C8—C91.420 (3)
C1—Fe12.038 (2)C8—Fe12.0425 (19)
C1—H10.95C8—H80.95
C2—C31.409 (3)C9—C101.422 (3)
C2—Fe12.041 (2)C9—Fe12.046 (2)
C2—H20.95C9—H90.95
C3—C41.404 (3)C10—Fe12.046 (2)
C3—Fe12.042 (2)C10—H100.95
C3—H30.95C11—C121.400 (3)
C4—C51.399 (4)C11—C161.401 (3)
C4—Fe12.036 (2)C12—C131.386 (3)
C4—H40.95C12—H120.95
C5—Fe12.037 (2)C13—C141.390 (3)
C5—H50.95C13—H130.95
C6—C101.431 (3)C14—O11.376 (2)
C6—C71.441 (3)C14—C151.392 (3)
C6—C111.480 (3)C15—C161.384 (3)
C6—Fe12.0550 (19)C15—H150.95
C7—C81.425 (3)C16—H160.95
C7—Fe12.041 (2)O1—H1A0.84
C5—C1—C2107.7 (2)C16—C11—C6121.30 (18)
C5—C1—Fe169.74 (13)C13—C12—C11121.55 (19)
C2—C1—Fe169.79 (12)C13—C12—H12119.2
C5—C1—H1126.1C11—C12—H12119.2
C2—C1—H1126.1C12—C13—C14119.9 (2)
Fe1—C1—H1125.9C12—C13—H13120
C3—C2—C1107.6 (2)C14—C13—H13120
C3—C2—Fe169.83 (12)O1—C14—C13123.0 (2)
C1—C2—Fe169.51 (12)O1—C14—C15117.5 (2)
C3—C2—H2126.2C13—C14—C15119.50 (19)
C1—C2—H2126.2C16—C15—C14120.2 (2)
Fe1—C2—H2126C16—C15—H15119.9
C4—C3—C2108.1 (2)C14—C15—H15119.9
C4—C3—Fe169.63 (12)C15—C16—C11121.37 (19)
C2—C3—Fe169.80 (12)C15—C16—H16119.3
C4—C3—H3126C11—C16—H16119.3
C2—C3—H3126C14—O1—H1A109.5
Fe1—C3—H3126.2C4—Fe1—C540.17 (10)
C5—C4—C3108.5 (2)C4—Fe1—C167.84 (10)
C5—C4—Fe169.96 (13)C5—Fe1—C140.45 (10)
C3—C4—Fe170.11 (13)C4—Fe1—C7163.72 (9)
C5—C4—H4125.8C5—Fe1—C7154.33 (10)
C3—C4—H4125.8C1—Fe1—C7119.58 (10)
Fe1—C4—H4125.7C4—Fe1—C267.88 (9)
C4—C5—C1108.1 (2)C5—Fe1—C268.10 (9)
C4—C5—Fe169.86 (13)C1—Fe1—C240.70 (9)
C1—C5—Fe169.81 (13)C7—Fe1—C2107.46 (9)
C4—C5—H5125.9C4—Fe1—C340.27 (9)
C1—C5—H5125.9C5—Fe1—C367.76 (10)
Fe1—C5—H5126C1—Fe1—C368.01 (9)
C10—C6—C7106.89 (17)C7—Fe1—C3126.24 (9)
C10—C6—C11126.23 (17)C2—Fe1—C340.37 (9)
C7—C6—C11126.81 (18)C4—Fe1—C8126.43 (10)
C10—C6—Fe169.26 (11)C5—Fe1—C8163.85 (10)
C7—C6—Fe168.89 (11)C1—Fe1—C8153.91 (10)
C11—C6—Fe1129.17 (13)C7—Fe1—C840.86 (8)
C8—C7—C6108.17 (18)C2—Fe1—C8119.13 (9)
C8—C7—Fe169.62 (11)C3—Fe1—C8107.58 (9)
C6—C7—Fe169.92 (11)C4—Fe1—C9108.10 (9)
C8—C7—H7125.9C5—Fe1—C9126.82 (10)
C6—C7—H7125.9C1—Fe1—C9164.34 (10)
Fe1—C7—H7126.1C7—Fe1—C968.65 (8)
C9—C8—C7108.17 (18)C2—Fe1—C9153.46 (9)
C9—C8—Fe169.80 (11)C3—Fe1—C9119.42 (9)
C7—C8—Fe169.52 (11)C8—Fe1—C940.65 (8)
C9—C8—H8125.9C4—Fe1—C10119.95 (9)
C7—C8—H8125.9C5—Fe1—C10108.43 (9)
Fe1—C8—H8126.3C1—Fe1—C10126.98 (9)
C8—C9—C10108.12 (17)C7—Fe1—C1068.71 (8)
C8—C9—Fe169.55 (12)C2—Fe1—C10164.51 (9)
C10—C9—Fe169.69 (11)C3—Fe1—C10153.85 (9)
C8—C9—H9125.9C8—Fe1—C1068.49 (8)
C10—C9—H9125.9C9—Fe1—C1040.66 (8)
Fe1—C9—H9126.4C4—Fe1—C6154.05 (9)
C9—C10—C6108.65 (17)C5—Fe1—C6119.77 (9)
C9—C10—Fe169.65 (11)C1—Fe1—C6107.79 (9)
C6—C10—Fe169.90 (11)C7—Fe1—C641.19 (8)
C9—C10—H10125.7C2—Fe1—C6126.55 (9)
C6—C10—H10125.7C3—Fe1—C6164.07 (9)
Fe1—C10—H10126.4C8—Fe1—C669.01 (8)
C12—C11—C16117.44 (18)C9—Fe1—C668.82 (8)
C12—C11—C6121.19 (17)C10—Fe1—C640.84 (8)
C5—C1—C2—C30.0 (2)C6—C7—Fe1—C9−81.82 (13)
Fe1—C1—C2—C359.70 (15)C8—C7—Fe1—C1081.31 (13)
C5—C1—C2—Fe1−59.65 (15)C6—C7—Fe1—C10−38.02 (12)
C1—C2—C3—C4−0.2 (2)C8—C7—Fe1—C6119.33 (18)
Fe1—C2—C3—C459.31 (15)C3—C2—Fe1—C4−37.48 (14)
C1—C2—C3—Fe1−59.50 (15)C1—C2—Fe1—C481.26 (16)
C2—C3—C4—C50.3 (2)C3—C2—Fe1—C5−80.96 (15)
Fe1—C3—C4—C559.67 (15)C1—C2—Fe1—C537.78 (15)
C2—C3—C4—Fe1−59.42 (15)C3—C2—Fe1—C1−118.7 (2)
C3—C4—C5—C1−0.2 (2)C3—C2—Fe1—C7125.93 (14)
Fe1—C4—C5—C159.54 (15)C1—C2—Fe1—C7−115.34 (14)
C3—C4—C5—Fe1−59.76 (15)C1—C2—Fe1—C3118.7 (2)
C2—C1—C5—C40.1 (2)C3—C2—Fe1—C883.02 (15)
Fe1—C1—C5—C4−59.58 (15)C1—C2—Fe1—C8−158.25 (14)
C2—C1—C5—Fe159.68 (15)C3—C2—Fe1—C948.9 (2)
C10—C6—C7—C8−0.3 (2)C1—C2—Fe1—C9167.63 (18)
C11—C6—C7—C8176.84 (18)C3—C2—Fe1—C10−160.9 (3)
Fe1—C6—C7—C8−59.33 (14)C1—C2—Fe1—C10−42.2 (4)
C10—C6—C7—Fe159.07 (13)C3—C2—Fe1—C6167.43 (13)
C11—C6—C7—Fe1−123.83 (19)C1—C2—Fe1—C6−73.83 (16)
C6—C7—C8—C90.2 (2)C2—C3—Fe1—C4119.3 (2)
Fe1—C7—C8—C9−59.30 (14)C4—C3—Fe1—C5−37.40 (14)
C6—C7—C8—Fe159.52 (14)C2—C3—Fe1—C581.89 (15)
C7—C8—C9—C10−0.1 (2)C4—C3—Fe1—C1−81.22 (16)
Fe1—C8—C9—C10−59.22 (14)C2—C3—Fe1—C138.08 (14)
C7—C8—C9—Fe159.13 (14)C4—C3—Fe1—C7167.43 (14)
C8—C9—C10—C6−0.1 (2)C2—C3—Fe1—C7−73.28 (16)
Fe1—C9—C10—C6−59.20 (13)C4—C3—Fe1—C2−119.3 (2)
C8—C9—C10—Fe159.13 (14)C4—C3—Fe1—C8126.14 (14)
C7—C6—C10—C90.2 (2)C2—C3—Fe1—C8−114.56 (14)
C11—C6—C10—C9−176.92 (17)C4—C3—Fe1—C983.45 (16)
Fe1—C6—C10—C959.04 (13)C2—C3—Fe1—C9−157.26 (13)
C7—C6—C10—Fe1−58.84 (13)C4—C3—Fe1—C1049.3 (3)
C11—C6—C10—Fe1124.04 (19)C2—C3—Fe1—C10168.58 (18)
C10—C6—C11—C12−172.01 (19)C4—C3—Fe1—C6−158.9 (3)
C7—C6—C11—C1211.4 (3)C2—C3—Fe1—C6−39.6 (4)
Fe1—C6—C11—C12−80.3 (2)C9—C8—Fe1—C4−74.51 (15)
C10—C6—C11—C1611.2 (3)C7—C8—Fe1—C4166.01 (12)
C7—C6—C11—C16−165.41 (19)C9—C8—Fe1—C5−44.4 (4)
Fe1—C6—C11—C16102.9 (2)C7—C8—Fe1—C5−163.9 (3)
C16—C11—C12—C131.3 (3)C9—C8—Fe1—C1169.29 (18)
C6—C11—C12—C13−175.68 (19)C7—C8—Fe1—C149.8 (2)
C11—C12—C13—C14−0.3 (3)C9—C8—Fe1—C7119.48 (17)
C12—C13—C14—O1178.6 (2)C9—C8—Fe1—C2−157.37 (12)
C12—C13—C14—C15−1.1 (3)C7—C8—Fe1—C283.15 (14)
O1—C14—C15—C16−178.4 (2)C9—C8—Fe1—C3−114.96 (13)
C13—C14—C15—C161.3 (3)C7—C8—Fe1—C3125.56 (13)
C14—C15—C16—C11−0.3 (3)C7—C8—Fe1—C9−119.48 (17)
C12—C11—C16—C15−1.0 (3)C9—C8—Fe1—C1037.57 (12)
C6—C11—C16—C15175.96 (19)C7—C8—Fe1—C10−81.91 (13)
C3—C4—Fe1—C5119.37 (19)C9—C8—Fe1—C681.54 (12)
C5—C4—Fe1—C1−37.69 (14)C7—C8—Fe1—C6−37.94 (12)
C3—C4—Fe1—C181.68 (15)C8—C9—Fe1—C4125.35 (13)
C5—C4—Fe1—C7−158.1 (3)C10—C9—Fe1—C4−115.18 (13)
C3—C4—Fe1—C7−38.8 (4)C8—C9—Fe1—C5165.92 (13)
C5—C4—Fe1—C2−81.80 (15)C10—C9—Fe1—C5−74.61 (15)
C3—C4—Fe1—C237.57 (13)C8—C9—Fe1—C1−162.4 (3)
C5—C4—Fe1—C3−119.37 (19)C10—C9—Fe1—C1−42.9 (4)
C5—C4—Fe1—C8167.52 (13)C8—C9—Fe1—C7−37.69 (12)
C3—C4—Fe1—C8−73.11 (16)C10—C9—Fe1—C781.77 (12)
C5—C4—Fe1—C9126.18 (14)C8—C9—Fe1—C248.8 (2)
C3—C4—Fe1—C9−114.44 (14)C10—C9—Fe1—C2168.24 (17)
C5—C4—Fe1—C1083.30 (15)C8—C9—Fe1—C382.85 (14)
C3—C4—Fe1—C10−157.33 (13)C10—C9—Fe1—C3−157.68 (12)
C5—C4—Fe1—C647.6 (3)C10—C9—Fe1—C8119.47 (16)
C3—C4—Fe1—C6166.92 (17)C8—C9—Fe1—C10−119.47 (16)
C1—C5—Fe1—C4−119.21 (19)C8—C9—Fe1—C6−82.04 (12)
C4—C5—Fe1—C1119.21 (19)C10—C9—Fe1—C637.43 (11)
C4—C5—Fe1—C7166.05 (18)C9—C10—Fe1—C483.08 (15)
C1—C5—Fe1—C746.8 (3)C6—C10—Fe1—C4−156.99 (13)
C4—C5—Fe1—C281.20 (14)C9—C10—Fe1—C5125.56 (14)
C1—C5—Fe1—C2−38.01 (14)C6—C10—Fe1—C5−114.51 (14)
C4—C5—Fe1—C337.48 (13)C9—C10—Fe1—C1166.69 (13)
C1—C5—Fe1—C3−81.73 (15)C6—C10—Fe1—C1−73.37 (15)
C4—C5—Fe1—C8−38.7 (4)C9—C10—Fe1—C7−81.60 (13)
C1—C5—Fe1—C8−157.9 (3)C6—C10—Fe1—C738.34 (11)
C4—C5—Fe1—C9−73.42 (16)C9—C10—Fe1—C2−160.1 (3)
C1—C5—Fe1—C9167.37 (13)C6—C10—Fe1—C2−40.1 (4)
C4—C5—Fe1—C10−114.89 (14)C9—C10—Fe1—C348.6 (2)
C1—C5—Fe1—C10125.90 (14)C6—C10—Fe1—C3168.58 (18)
C4—C5—Fe1—C6−158.16 (13)C9—C10—Fe1—C8−37.57 (12)
C1—C5—Fe1—C682.62 (15)C6—C10—Fe1—C882.37 (12)
C5—C1—Fe1—C437.44 (14)C6—C10—Fe1—C9119.93 (16)
C2—C1—Fe1—C4−81.38 (15)C9—C10—Fe1—C6−119.93 (16)
C2—C1—Fe1—C5−118.8 (2)C10—C6—Fe1—C450.7 (2)
C5—C1—Fe1—C7−158.69 (14)C7—C6—Fe1—C4169.36 (19)
C2—C1—Fe1—C782.48 (15)C11—C6—Fe1—C4−69.7 (3)
C5—C1—Fe1—C2118.8 (2)C10—C6—Fe1—C583.99 (15)
C5—C1—Fe1—C381.05 (15)C7—C6—Fe1—C5−157.38 (13)
C2—C1—Fe1—C3−37.77 (14)C11—C6—Fe1—C5−36.5 (2)
C5—C1—Fe1—C8166.23 (18)C10—C6—Fe1—C1126.50 (13)
C2—C1—Fe1—C847.4 (3)C7—C6—Fe1—C1−114.87 (13)
C5—C1—Fe1—C9−40.4 (4)C11—C6—Fe1—C16.1 (2)
C2—C1—Fe1—C9−159.2 (3)C10—C6—Fe1—C7−118.63 (16)
C5—C1—Fe1—C10−74.15 (17)C11—C6—Fe1—C7120.9 (2)
C2—C1—Fe1—C10167.03 (12)C10—C6—Fe1—C2167.63 (13)
C5—C1—Fe1—C6−115.30 (14)C7—C6—Fe1—C2−73.74 (15)
C2—C1—Fe1—C6125.87 (14)C11—C6—Fe1—C247.2 (2)
C8—C7—Fe1—C4−43.9 (4)C10—C6—Fe1—C3−161.5 (3)
C6—C7—Fe1—C4−163.3 (3)C7—C6—Fe1—C3−42.8 (3)
C8—C7—Fe1—C5169.75 (19)C11—C6—Fe1—C378.1 (4)
C6—C7—Fe1—C550.4 (3)C10—C6—Fe1—C8−80.98 (13)
C8—C7—Fe1—C1−157.28 (13)C7—C6—Fe1—C837.65 (12)
C6—C7—Fe1—C183.39 (14)C11—C6—Fe1—C8158.6 (2)
C8—C7—Fe1—C2−114.61 (13)C10—C6—Fe1—C9−37.27 (12)
C6—C7—Fe1—C2126.06 (13)C7—C6—Fe1—C981.36 (13)
C8—C7—Fe1—C3−74.04 (15)C11—C6—Fe1—C9−157.7 (2)
C6—C7—Fe1—C3166.62 (12)C7—C6—Fe1—C10118.63 (16)
C6—C7—Fe1—C8−119.33 (18)C11—C6—Fe1—C10−120.4 (2)
C8—C7—Fe1—C937.51 (12)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.553.308 (3)137
O1—H1A···Cg3ii0.842.663.281 (2)141
C2—H2···Cg1iii0.952.903.766 (2)155
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x−1, −y−1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.553.308 (3)137
O1—H1A···Cg3ii0.842.663.281 (2)141
C2—H2···Cg1iii0.952.903.766 (2)155
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) x−1, −y−1/2, z−1/2.
Acknowledgements top

We thank Dr Manuel Fernandez for data collection, and the University of KwaZulu-Natal and the NRF for financial support.

references
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