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Acta Cryst. (2011). E67, m741    [ doi:10.1107/S1600536811016588 ]

Dibenzyl ferrocene-1,1'-dicarboxylate

B. O. Patrick, C. Rock and A. S. Abd-El-Aziz

Abstract top

In the title compound, [Fe(C13H11O2)2], there are markedly different orientations of the two phenylmethoxycarbonyl substituents [O-C-C-C torsion angles = 84.5 (3) and 139.6 (2)°]. These orientations are mediated by a number of intermolecular C-H...O interactions, which result in a one-dimensional hydrogen-bonded network of molecules.

Comment top

Ferrocene has well defined redox properties and has successfully been incorporated into larger compounds in order to take advantage of these properties (Abd-El-Aziz et al., 2007). The monoester of the title compound was reported as a classic example of a ferroecene ester (Hur et al., 2010).

The stucture of the title compound is presented in Fig. 1. While the molecule posesses internal inversion symmetry, this symmetry is broken in the solid state. The two benzyl cyclopentadienylcarboxylate groups stack almost perfectly eclipsed. However, there is a significant difference between the orientation of the two benzyl substituents, as denoted by the O2—C7—C8—C9 and O4—C20—C21—C22 torsion angles [84.5 (3) and 139.6 (2)°, respectively]. Of the two torsion angles described above, the former resembles most closely that of the monoester, with a torsion angle of 82.4° (Hur et al., 2010). These different orientations are mediated by a variety of intermolecular C—H···O interactions. These interactions ultimately form a one-dimensional hydrogen-bonded network of molecules; details have been given in Table 1 and Figure 2.

Related literature top

For properties of ferrocene-incorporated compounds, see: Abd-El-Aziz et al. (2007). For the crystal structure of a ferroecene ester, see: Hur et al. (2010). For related literature [on what subject?], see: Khrustalev et al. (2006).

Experimental top

The title compound was formed during attempts to incorporate ferrocene along with free arenes into larger dendrimers and polymers. 1,1'-Ddicarboxylic acid ferrocene (4 mmol), benzyl alcohol (4 mmol), N,N'-dicyclohexylcarbodiimide(DCC) (4.4 mmol) and dimethylaminopyride (DMAP) (4.4 mmol) were combined in 50 mL of dimethylformamide (DMF) and stirred under an atmosphere of nitrogen for 15 h. The mixture was then cooled to 269 K for 30 minutes before gravity filtration. The filtrate was washed with 1.2 M HCl and deionized water consecutively. The solution was then dried using MgSO4 and the solvent removed in vacuo. The di-substituted form was separated from the mono-substituted (i.e., monoester) form using a silica gel column, using ethyl acetate as the eluent. Red crystals of the product were grown using ethyl acetate.

Refinement top

All hydrogen atoms were placed in calculated positions, riding on C atoms with Uiso(H) = 1.2Ueq(C). The Cp and phenyl H atoms were placed at C—H = 0.95 Å and methylene H atoms at C—H = 0.99 Å. The absolute stereochemistry was determined on the basis of the refined Flack x-parameter, with x = 0.02 (1) (Flack, 1983) using 2280 Friedel pairs of reflections which were not merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atomic labels and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. One-dimensional C—H···O hydrogen bonded network formed by the title compound.
Dibenzyl ferrocene-1,1'-dicarboxylate top
Crystal data top
[Fe(C13H11O2)2]F(000) = 944
Mr = 454.29Dx = 1.518 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2a2Cell parameters from 3257 reflections
a = 13.1120 (14) Åθ = 3.2–26.1°
b = 5.9366 (6) ŵ = 0.79 mm−1
c = 25.538 (3) ÅT = 100 K
V = 1987.9 (4) Å3Irregular, orange
Z = 40.15 × 0.05 × 0.05 mm
Data collection top
Bruker X8 APEXII
diffractometer		4726 independent reflections
Radiation source: fine-focus sealed tube3820 reflections with I > 2σ(I)
graphiteRint = 0.050
area detector scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −14→17
Tmin = 0.830, Tmax = 0.961k = −7→7
16738 measured reflectionsl = −33→33
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0277P)2 + 0.1317P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.002
4726 reflectionsΔρmax = 0.31 e Å−3
280 parametersΔρmin = −0.33 e Å−3
1 restraintAbsolute structure: Flack (1983), 2280 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.016 (14)
Crystal data top
[Fe(C13H11O2)2]V = 1987.9 (4) Å3
Mr = 454.29Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 13.1120 (14) ŵ = 0.79 mm−1
b = 5.9366 (6) ÅT = 100 K
c = 25.538 (3) Å0.15 × 0.05 × 0.05 mm
Data collection top
Bruker X8 APEXII
diffractometer		3820 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		Rint = 0.050
Tmin = 0.830, Tmax = 0.961θmax = 28.0°
16738 measured reflectionsStandard reflections: 0
4726 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.070Δρmax = 0.31 e Å−3
S = 1.02Δρmin = −0.33 e Å−3
4726 reflectionsAbsolute structure: Flack (1983), 2280 Friedel pairs
280 parametersFlack parameter: 0.016 (14)
1 restraint
Special details top

Experimental. Data were scaled in point group 222 in order to keep all Friedel pairs unmerged. In total 97% of all Friedel pairs were measured.

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 (Å2) top
xyzUiso*/Ueq
C10.01829 (18)0.0437 (4)0.19218 (9)0.0126 (5)
H10.0185−0.07910.21600.015*
C20.0484 (2)0.0360 (4)0.13853 (10)0.0147 (5)
H20.0730−0.09280.12040.018*
C30.03515 (19)0.2546 (5)0.11696 (10)0.0168 (5)
H30.04820.29640.08170.020*
C4−0.0009 (2)0.3998 (5)0.15699 (9)0.0137 (6)
H4−0.01490.55600.15340.016*
C5−0.01225 (18)0.2695 (4)0.20357 (10)0.0130 (5)
C6−0.04033 (19)0.3471 (4)0.25657 (10)0.0132 (5)
C7−0.0510 (2)0.6662 (4)0.31290 (10)0.0148 (5)
H7A−0.09990.57140.33260.018*
H7B−0.07960.82010.31030.018*
C80.0496 (2)0.6733 (4)0.34143 (9)0.0145 (6)
C90.1152 (2)0.8552 (5)0.33434 (10)0.0175 (6)
H90.09480.97710.31260.021*
C100.2096 (2)0.8607 (5)0.35846 (11)0.0229 (7)
H100.25360.98580.35330.027*
C110.2400 (2)0.6838 (5)0.39020 (11)0.0250 (7)
H110.30500.68660.40660.030*
C120.1750 (2)0.5026 (5)0.39792 (11)0.0259 (7)
H120.19520.38190.42000.031*
C130.0805 (2)0.4967 (5)0.37356 (10)0.0197 (6)
H130.03660.37150.37880.024*
C140.22644 (18)0.5344 (4)0.19765 (9)0.0130 (5)
H140.20710.68860.19710.016*
C150.21971 (19)0.3869 (4)0.24127 (10)0.0149 (5)
H150.19520.42520.27510.018*
C160.2561 (2)0.1719 (4)0.22540 (10)0.0156 (5)
H160.26010.04170.24690.019*
C170.28541 (17)0.1843 (4)0.17215 (11)0.0137 (5)
H170.31220.06450.15170.016*
C180.26740 (19)0.4098 (4)0.15472 (9)0.0126 (5)
C190.29004 (18)0.4912 (4)0.10128 (10)0.0128 (5)
C200.2863 (2)0.8194 (5)0.04625 (10)0.0188 (6)
H20A0.32730.71670.02410.023*
H20B0.32690.95720.05270.023*
C210.1895 (2)0.8802 (5)0.01829 (10)0.0146 (6)
C220.1823 (2)1.0860 (5)−0.00775 (10)0.0204 (6)
H220.23761.1893−0.00640.025*
C230.0947 (2)1.1407 (5)−0.03571 (11)0.0250 (6)
H230.09121.2792−0.05430.030*
C240.0130 (2)0.9952 (5)−0.03662 (11)0.0264 (7)
H24−0.04721.0347−0.05510.032*
C250.0187 (2)0.7918 (5)−0.01058 (10)0.0257 (7)
H25−0.03750.6910−0.01130.031*
C260.1066 (2)0.7348 (5)0.01658 (11)0.0216 (6)
H260.11010.59430.03430.026*
O1−0.06304 (14)0.2228 (3)0.29215 (7)0.0176 (4)
O2−0.03591 (13)0.5731 (3)0.26035 (6)0.0134 (4)
O30.32897 (14)0.3805 (3)0.06757 (7)0.0185 (4)
O40.26322 (14)0.7100 (3)0.09598 (7)0.0167 (4)
Fe10.13475 (2)0.26824 (5)0.179289 (17)0.01072 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0091 (12)0.0132 (12)0.0156 (14)−0.0014 (10)−0.0005 (9)0.0005 (9)
C20.0097 (12)0.0179 (13)0.0164 (12)−0.0032 (11)−0.0006 (10)−0.0038 (11)
C30.0120 (13)0.0238 (15)0.0146 (12)−0.0039 (11)−0.0016 (10)0.0022 (11)
C40.0067 (12)0.0147 (14)0.0197 (13)0.0005 (11)−0.0050 (10)0.0016 (11)
C50.0048 (12)0.0162 (13)0.0181 (11)−0.0022 (11)0.0001 (9)0.0017 (11)
C60.0068 (13)0.0137 (13)0.0191 (13)0.0003 (10)−0.0008 (10)0.0005 (10)
C70.0137 (14)0.0154 (13)0.0155 (12)0.0018 (11)0.0033 (11)−0.0017 (10)
C80.0134 (14)0.0171 (14)0.0129 (12)0.0038 (11)0.0035 (10)−0.0016 (10)
C90.0182 (16)0.0181 (15)0.0161 (13)0.0011 (12)0.0020 (11)−0.0007 (11)
C100.0183 (16)0.0288 (17)0.0214 (14)−0.0038 (13)−0.0006 (12)−0.0048 (13)
C110.0182 (16)0.0400 (18)0.0168 (13)0.0038 (13)−0.0043 (11)−0.0096 (12)
C120.0310 (18)0.0289 (17)0.0178 (14)0.0087 (14)−0.0054 (12)0.0031 (12)
C130.0241 (16)0.0191 (15)0.0160 (13)0.0009 (12)−0.0006 (11)0.0022 (11)
C140.0074 (12)0.0140 (12)0.0175 (12)−0.0022 (10)−0.0033 (9)−0.0019 (10)
C150.0112 (13)0.0197 (14)0.0140 (12)−0.0008 (11)−0.0016 (10)−0.0021 (10)
C160.0125 (13)0.0168 (13)0.0175 (13)−0.0035 (11)−0.0039 (11)0.0024 (10)
C170.0068 (11)0.0141 (12)0.0202 (15)−0.0002 (8)0.0001 (11)−0.0016 (11)
C180.0065 (12)0.0145 (13)0.0170 (12)−0.0012 (11)−0.0001 (10)−0.0005 (10)
C190.0070 (12)0.0140 (13)0.0172 (12)−0.0039 (11)−0.0028 (10)0.0020 (10)
C200.0187 (15)0.0198 (15)0.0181 (13)−0.0028 (12)0.0053 (11)0.0057 (11)
C210.0163 (15)0.0163 (14)0.0112 (12)−0.0005 (12)0.0027 (11)−0.0027 (11)
C220.0270 (16)0.0180 (14)0.0163 (13)−0.0035 (12)−0.0021 (12)0.0033 (11)
C230.0338 (18)0.0241 (15)0.0171 (14)0.0017 (14)−0.0042 (13)0.0030 (11)
C240.0221 (16)0.0402 (18)0.0170 (13)0.0047 (14)−0.0032 (12)−0.0011 (13)
C250.0230 (15)0.0371 (18)0.0169 (14)−0.0096 (14)0.0016 (12)−0.0005 (13)
C260.0276 (16)0.0201 (15)0.0171 (13)−0.0064 (13)0.0019 (11)0.0046 (12)
O10.0211 (10)0.0130 (9)0.0187 (9)0.0000 (8)0.0052 (7)0.0016 (8)
O20.0140 (9)0.0107 (9)0.0155 (9)0.0006 (7)0.0019 (7)0.0006 (7)
O30.0195 (11)0.0174 (10)0.0185 (9)0.0003 (8)0.0044 (8)−0.0026 (8)
O40.0194 (10)0.0157 (10)0.0150 (9)0.0029 (8)0.0036 (7)0.0024 (7)
Fe10.00747 (14)0.01212 (15)0.01259 (13)−0.00068 (14)−0.00029 (19)0.0001 (2)
Geometric parameters (Å, °) top
C1—C21.426 (4)C14—C151.419 (3)
C1—C51.429 (3)C14—C181.427 (3)
C1—Fe12.053 (2)C14—Fe12.040 (2)
C1—H10.9500C14—H140.9500
C2—C31.420 (4)C15—C161.422 (4)
C2—Fe12.066 (2)C15—Fe12.060 (2)
C2—H20.9500C15—H150.9500
C3—C41.418 (4)C16—C171.415 (4)
C3—Fe12.061 (2)C16—Fe12.061 (3)
C3—H30.9500C16—H160.9500
C4—C51.427 (3)C17—C181.431 (3)
C4—Fe12.024 (3)C17—Fe12.046 (2)
C4—H40.9500C17—H170.9500
C5—C61.476 (3)C18—C191.478 (3)
C5—Fe12.025 (2)C18—Fe12.031 (2)
C6—O11.208 (3)C19—O31.197 (3)
C6—O21.346 (3)C19—O41.353 (3)
C7—O21.465 (3)C20—O41.458 (3)
C7—C81.508 (4)C20—C211.501 (4)
C7—H7A0.9900C20—H20A0.9900
C7—H7B0.9900C20—H20B0.9900
C8—C131.391 (3)C21—C261.389 (4)
C8—C91.392 (4)C21—C221.394 (4)
C9—C101.383 (4)C22—C231.391 (4)
C9—H90.9500C22—H220.9500
C10—C111.385 (4)C23—C241.376 (4)
C10—H100.9500C23—H230.9500
C11—C121.386 (4)C24—C251.380 (4)
C11—H110.9500C24—H240.9500
C12—C131.387 (4)C25—C261.386 (4)
C12—H120.9500C25—H250.9500
C13—H130.9500C26—H260.9500
C2—C1—C5107.7 (2)C14—C18—C17107.9 (2)
C2—C1—Fe170.20 (14)C14—C18—C19128.0 (2)
C5—C1—Fe168.42 (14)C17—C18—C19124.1 (2)
C2—C1—H1126.2C14—C18—Fe169.81 (14)
C5—C1—H1126.2C17—C18—Fe169.99 (13)
Fe1—C1—H1126.8C19—C18—Fe1126.34 (18)
C3—C2—C1108.0 (2)O3—C19—O4124.5 (2)
C3—C2—Fe169.67 (14)O3—C19—C18124.8 (2)
C1—C2—Fe169.28 (15)O4—C19—C18110.7 (2)
C3—C2—H2126.0O4—C20—C21110.2 (2)
C1—C2—H2126.0O4—C20—H20A109.6
Fe1—C2—H2126.6C21—C20—H20A109.6
C4—C3—C2108.5 (2)O4—C20—H20B109.6
C4—C3—Fe168.30 (14)C21—C20—H20B109.6
C2—C3—Fe170.06 (14)H20A—C20—H20B108.1
C4—C3—H3125.8C26—C21—C22118.5 (3)
C2—C3—H3125.8C26—C21—C20121.9 (2)
Fe1—C3—H3127.4C22—C21—C20119.6 (2)
C3—C4—C5107.8 (2)C23—C22—C21120.3 (3)
C3—C4—Fe171.08 (15)C23—C22—H22119.8
C5—C4—Fe169.40 (14)C21—C22—H22119.8
C3—C4—H4126.1C24—C23—C22120.3 (3)
C5—C4—H4126.1C24—C23—H23119.8
Fe1—C4—H4125.0C22—C23—H23119.8
C4—C5—C1108.0 (2)C23—C24—C25119.9 (3)
C4—C5—C6128.4 (2)C23—C24—H24120.0
C1—C5—C6123.3 (2)C25—C24—H24120.0
C4—C5—Fe169.33 (14)C24—C25—C26120.0 (3)
C1—C5—Fe170.57 (14)C24—C25—H25120.0
C6—C5—Fe1121.29 (17)C26—C25—H25120.0
O1—C6—O2124.4 (2)C25—C26—C21120.9 (3)
O1—C6—C5124.1 (2)C25—C26—H26119.5
O2—C6—C5111.5 (2)C21—C26—H26119.5
O2—C7—C8109.6 (2)C6—O2—C7115.83 (19)
O2—C7—H7A109.8C19—O4—C20117.4 (2)
C8—C7—H7A109.8C4—Fe1—C541.27 (10)
O2—C7—H7B109.8C4—Fe1—C18120.38 (10)
C8—C7—H7B109.8C5—Fe1—C18155.26 (10)
H7A—C7—H7B108.2C4—Fe1—C14106.47 (10)
C13—C8—C9118.8 (3)C5—Fe1—C14119.19 (10)
C13—C8—C7121.2 (2)C18—Fe1—C1441.05 (9)
C9—C8—C7120.0 (2)C4—Fe1—C17156.55 (10)
C10—C9—C8120.9 (3)C5—Fe1—C17161.36 (10)
C10—C9—H9119.6C18—Fe1—C1741.09 (10)
C8—C9—H9119.6C14—Fe1—C1768.91 (10)
C9—C10—C11120.0 (3)C4—Fe1—C169.04 (10)
C9—C10—H10120.0C5—Fe1—C141.01 (10)
C11—C10—H10120.0C18—Fe1—C1162.74 (10)
C10—C11—C12119.7 (3)C14—Fe1—C1154.70 (10)
C10—C11—H11120.2C17—Fe1—C1125.05 (10)
C12—C11—H11120.2C4—Fe1—C15124.01 (11)
C11—C12—C13120.3 (3)C5—Fe1—C15106.15 (10)
C11—C12—H12119.8C18—Fe1—C1568.45 (10)
C13—C12—H12119.8C14—Fe1—C1540.51 (10)
C12—C13—C8120.3 (3)C17—Fe1—C1568.26 (10)
C12—C13—H13119.8C1—Fe1—C15120.07 (10)
C8—C13—H13119.8C4—Fe1—C16161.16 (10)
C15—C14—C18107.9 (2)C5—Fe1—C16124.14 (10)
C15—C14—Fe170.49 (14)C18—Fe1—C1668.29 (10)
C18—C14—Fe169.14 (14)C14—Fe1—C1668.19 (10)
C15—C14—H14126.1C17—Fe1—C1640.31 (10)
C18—C14—H14126.1C1—Fe1—C16107.61 (10)
Fe1—C14—H14125.9C15—Fe1—C1640.38 (10)
C14—C15—C16108.0 (2)C4—Fe1—C340.62 (10)
C14—C15—Fe169.00 (14)C5—Fe1—C368.50 (10)
C16—C15—Fe169.85 (14)C18—Fe1—C3108.69 (10)
C14—C15—H15126.0C14—Fe1—C3125.56 (10)
C16—C15—H15126.0C17—Fe1—C3122.25 (10)
Fe1—C15—H15126.7C1—Fe1—C368.09 (10)
C17—C16—C15108.6 (2)C15—Fe1—C3161.78 (11)
C17—C16—Fe169.26 (14)C16—Fe1—C3156.92 (11)
C15—C16—Fe169.77 (15)C4—Fe1—C268.54 (11)
C17—C16—H16125.7C5—Fe1—C268.59 (10)
C15—C16—H16125.7C18—Fe1—C2126.16 (10)
Fe1—C16—H16126.8C14—Fe1—C2162.92 (10)
C16—C17—C18107.6 (2)C17—Fe1—C2108.77 (10)
C16—C17—Fe170.42 (14)C1—Fe1—C240.52 (10)
C18—C17—Fe168.92 (13)C15—Fe1—C2155.79 (10)
C16—C17—H17126.2C16—Fe1—C2121.74 (10)
C18—C17—H17126.2C3—Fe1—C240.27 (10)
Fe1—C17—H17126.0
C5—C1—C2—C3−0.8 (3)C14—C18—Fe1—C1−160.7 (3)
Fe1—C1—C2—C3−59.10 (17)C17—C18—Fe1—C1−41.8 (4)
C5—C1—C2—Fe158.34 (17)C19—C18—Fe1—C176.4 (4)
C1—C2—C3—C41.3 (3)C14—C18—Fe1—C15−37.69 (14)
Fe1—C2—C3—C4−57.60 (18)C17—C18—Fe1—C1581.20 (15)
C1—C2—C3—Fe158.85 (17)C19—C18—Fe1—C15−160.6 (3)
C2—C3—C4—C5−1.3 (3)C14—C18—Fe1—C16−81.28 (15)
Fe1—C3—C4—C5−59.93 (17)C17—C18—Fe1—C1637.61 (15)
C2—C3—C4—Fe158.68 (18)C19—C18—Fe1—C16155.8 (3)
C3—C4—C5—C10.8 (3)C14—C18—Fe1—C3123.13 (15)
Fe1—C4—C5—C1−60.23 (17)C17—C18—Fe1—C3−117.98 (15)
C3—C4—C5—C6175.2 (2)C19—C18—Fe1—C30.2 (3)
Fe1—C4—C5—C6114.2 (3)C14—C18—Fe1—C2164.50 (14)
C3—C4—C5—Fe161.00 (18)C17—C18—Fe1—C2−76.62 (18)
C2—C1—C5—C40.0 (3)C19—C18—Fe1—C241.5 (3)
Fe1—C1—C5—C459.45 (16)C15—C14—Fe1—C4123.50 (15)
C2—C1—C5—C6−174.7 (2)C18—C14—Fe1—C4−117.61 (15)
Fe1—C1—C5—C6−115.3 (2)C15—C14—Fe1—C580.60 (17)
C2—C1—C5—Fe1−59.45 (17)C18—C14—Fe1—C5−160.51 (14)
C4—C5—C6—O1168.6 (2)C15—C14—Fe1—C18−118.9 (2)
C1—C5—C6—O1−17.8 (4)C15—C14—Fe1—C17−80.81 (16)
Fe1—C5—C6—O1−104.0 (3)C18—C14—Fe1—C1738.08 (14)
C4—C5—C6—O2−12.4 (4)C15—C14—Fe1—C147.8 (3)
C1—C5—C6—O2161.2 (2)C18—C14—Fe1—C1166.7 (2)
Fe1—C5—C6—O275.0 (2)C18—C14—Fe1—C15118.9 (2)
O2—C7—C8—C13−93.1 (3)C15—C14—Fe1—C16−37.36 (15)
O2—C7—C8—C984.5 (3)C18—C14—Fe1—C1681.54 (15)
C13—C8—C9—C100.3 (4)C15—C14—Fe1—C3163.89 (15)
C7—C8—C9—C10−177.3 (2)C18—C14—Fe1—C3−77.21 (17)
C8—C9—C10—C11−0.1 (4)C15—C14—Fe1—C2−166.2 (3)
C9—C10—C11—C12−0.5 (4)C18—C14—Fe1—C2−47.3 (4)
C10—C11—C12—C130.8 (4)C16—C17—Fe1—C4163.5 (2)
C11—C12—C13—C8−0.5 (4)C18—C17—Fe1—C444.7 (3)
C9—C8—C13—C12−0.1 (4)C16—C17—Fe1—C5−38.7 (4)
C7—C8—C13—C12177.6 (2)C18—C17—Fe1—C5−157.5 (3)
C18—C14—C15—C16−0.1 (3)C16—C17—Fe1—C18118.8 (2)
Fe1—C14—C15—C1659.15 (18)C16—C17—Fe1—C1480.74 (16)
C18—C14—C15—Fe1−59.27 (16)C18—C17—Fe1—C14−38.04 (14)
C14—C15—C16—C17−0.1 (3)C16—C17—Fe1—C1−75.20 (18)
Fe1—C15—C16—C1758.55 (17)C18—C17—Fe1—C1166.02 (13)
C14—C15—C16—Fe1−58.62 (17)C16—C17—Fe1—C1537.09 (15)
C15—C16—C17—C180.2 (3)C18—C17—Fe1—C15−81.70 (15)
Fe1—C16—C17—C1859.10 (16)C18—C17—Fe1—C16−118.8 (2)
C15—C16—C17—Fe1−58.86 (18)C16—C17—Fe1—C3−159.67 (15)
C15—C14—C18—C170.3 (3)C18—C17—Fe1—C381.54 (16)
Fe1—C14—C18—C17−59.85 (16)C16—C17—Fe1—C2−117.27 (16)
C15—C14—C18—C19−179.0 (2)C18—C17—Fe1—C2123.94 (15)
Fe1—C14—C18—C19120.9 (3)C2—C1—Fe1—C481.09 (16)
C15—C14—C18—Fe160.12 (17)C5—C1—Fe1—C4−38.19 (15)
C16—C17—C18—C14−0.3 (3)C2—C1—Fe1—C5119.3 (2)
Fe1—C17—C18—C1459.74 (16)C2—C1—Fe1—C18−45.2 (4)
C16—C17—C18—C19179.0 (2)C5—C1—Fe1—C18−164.5 (3)
Fe1—C17—C18—C19−121.0 (2)C2—C1—Fe1—C14165.4 (2)
C16—C17—C18—Fe1−60.05 (16)C5—C1—Fe1—C1446.1 (3)
C14—C18—C19—O3176.3 (2)C2—C1—Fe1—C17−77.55 (18)
C17—C18—C19—O3−2.8 (4)C5—C1—Fe1—C17163.17 (14)
Fe1—C18—C19—O3−91.9 (3)C2—C1—Fe1—C15−160.85 (15)
C14—C18—C19—O4−2.1 (4)C5—C1—Fe1—C1579.87 (17)
C17—C18—C19—O4178.8 (2)C2—C1—Fe1—C16−118.56 (16)
Fe1—C18—C19—O489.7 (2)C5—C1—Fe1—C16122.15 (15)
O4—C20—C21—C26−41.8 (3)C2—C1—Fe1—C337.32 (15)
O4—C20—C21—C22139.6 (2)C5—C1—Fe1—C3−81.97 (15)
C26—C21—C22—C23−1.4 (4)C5—C1—Fe1—C2−119.3 (2)
C20—C21—C22—C23177.3 (3)C14—C15—Fe1—C4−74.74 (17)
C21—C22—C23—C242.0 (4)C16—C15—Fe1—C4165.68 (15)
C22—C23—C24—C25−1.3 (4)C14—C15—Fe1—C5−116.27 (15)
C23—C24—C25—C260.2 (4)C16—C15—Fe1—C5124.14 (15)
C24—C25—C26—C210.3 (4)C14—C15—Fe1—C1838.18 (14)
C22—C21—C26—C250.3 (4)C16—C15—Fe1—C18−81.40 (16)
C20—C21—C26—C25−178.4 (3)C16—C15—Fe1—C14−119.6 (2)
O1—C6—O2—C75.8 (4)C14—C15—Fe1—C1782.55 (16)
C5—C6—O2—C7−173.27 (19)C16—C15—Fe1—C17−37.03 (15)
C8—C7—O2—C686.9 (3)C14—C15—Fe1—C1−158.54 (14)
O3—C19—O4—C20−1.9 (4)C16—C15—Fe1—C181.88 (17)
C18—C19—O4—C20176.5 (2)C14—C15—Fe1—C16119.6 (2)
C21—C20—O4—C19114.0 (2)C14—C15—Fe1—C3−46.2 (4)
C3—C4—Fe1—C5−118.3 (2)C16—C15—Fe1—C3−165.8 (3)
C3—C4—Fe1—C1883.51 (17)C14—C15—Fe1—C2170.1 (2)
C5—C4—Fe1—C18−158.14 (14)C16—C15—Fe1—C250.6 (3)
C3—C4—Fe1—C14125.93 (15)C17—C16—Fe1—C4−159.6 (3)
C5—C4—Fe1—C14−115.72 (14)C15—C16—Fe1—C4−39.4 (4)
C3—C4—Fe1—C1751.1 (3)C17—C16—Fe1—C5166.02 (14)
C5—C4—Fe1—C17169.4 (2)C15—C16—Fe1—C5−73.83 (18)
C3—C4—Fe1—C1−80.39 (16)C17—C16—Fe1—C18−38.32 (14)
C5—C4—Fe1—C137.96 (14)C15—C16—Fe1—C1881.83 (16)
C3—C4—Fe1—C15166.73 (15)C17—C16—Fe1—C14−82.68 (15)
C5—C4—Fe1—C15−74.92 (17)C15—C16—Fe1—C1437.47 (15)
C3—C4—Fe1—C16−163.5 (3)C15—C16—Fe1—C17120.1 (2)
C5—C4—Fe1—C16−45.2 (4)C17—C16—Fe1—C1123.86 (15)
C5—C4—Fe1—C3118.3 (2)C15—C16—Fe1—C1−115.99 (15)
C3—C4—Fe1—C2−36.78 (15)C17—C16—Fe1—C15−120.1 (2)
C5—C4—Fe1—C281.57 (16)C17—C16—Fe1—C348.5 (3)
C1—C5—Fe1—C4118.9 (2)C15—C16—Fe1—C3168.7 (2)
C6—C5—Fe1—C4−123.2 (3)C17—C16—Fe1—C281.71 (17)
C4—C5—Fe1—C1850.1 (3)C15—C16—Fe1—C2−158.14 (15)
C1—C5—Fe1—C18169.1 (2)C2—C3—Fe1—C4−120.5 (2)
C6—C5—Fe1—C18−73.1 (3)C4—C3—Fe1—C538.61 (14)
C4—C5—Fe1—C1481.72 (16)C2—C3—Fe1—C5−81.84 (16)
C1—C5—Fe1—C14−159.36 (14)C4—C3—Fe1—C18−115.19 (16)
C6—C5—Fe1—C14−41.5 (2)C2—C3—Fe1—C18124.36 (16)
C4—C5—Fe1—C17−166.8 (3)C4—C3—Fe1—C14−72.65 (18)
C1—C5—Fe1—C17−47.9 (4)C2—C3—Fe1—C14166.89 (15)
C6—C5—Fe1—C1770.0 (4)C4—C3—Fe1—C17−158.53 (15)
C4—C5—Fe1—C1−118.9 (2)C2—C3—Fe1—C1781.02 (17)
C6—C5—Fe1—C1117.9 (3)C4—C3—Fe1—C182.91 (16)
C4—C5—Fe1—C15123.56 (15)C2—C3—Fe1—C1−37.55 (15)
C1—C5—Fe1—C15−117.51 (15)C4—C3—Fe1—C15−37.5 (4)
C6—C5—Fe1—C150.4 (2)C2—C3—Fe1—C15−157.9 (3)
C4—C5—Fe1—C16163.94 (15)C4—C3—Fe1—C16166.5 (2)
C1—C5—Fe1—C16−77.14 (17)C2—C3—Fe1—C1646.0 (3)
C6—C5—Fe1—C1640.7 (2)C4—C3—Fe1—C2120.5 (2)
C4—C5—Fe1—C3−38.01 (15)C3—C2—Fe1—C437.09 (15)
C1—C5—Fe1—C380.91 (15)C1—C2—Fe1—C4−82.43 (16)
C6—C5—Fe1—C3−161.2 (2)C3—C2—Fe1—C581.59 (16)
C4—C5—Fe1—C2−81.43 (16)C1—C2—Fe1—C5−37.93 (14)
C1—C5—Fe1—C237.50 (14)C3—C2—Fe1—C18−75.60 (18)
C6—C5—Fe1—C2155.4 (2)C1—C2—Fe1—C18164.88 (15)
C14—C18—Fe1—C480.06 (16)C3—C2—Fe1—C14−38.9 (4)
C17—C18—Fe1—C4−161.05 (15)C1—C2—Fe1—C14−158.4 (3)
C19—C18—Fe1—C4−42.9 (3)C3—C2—Fe1—C17−118.08 (16)
C14—C18—Fe1—C544.1 (3)C1—C2—Fe1—C17122.40 (15)
C17—C18—Fe1—C5163.0 (2)C3—C2—Fe1—C1119.5 (2)
C19—C18—Fe1—C5−78.8 (3)C3—C2—Fe1—C15163.3 (2)
C17—C18—Fe1—C14118.9 (2)C1—C2—Fe1—C1543.8 (3)
C19—C18—Fe1—C14−123.0 (3)C3—C2—Fe1—C16−160.62 (14)
C14—C18—Fe1—C17−118.9 (2)C1—C2—Fe1—C1679.86 (18)
C19—C18—Fe1—C17118.2 (3)C1—C2—Fe1—C3−119.5 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.952.463.368 (3)160
C7—H7B···O1ii0.992.443.350 (3)152
C9—H9···O1ii0.952.593.374 (3)141
C20—H20A···O30.992.282.716 (3)106
C20—H20B···O3ii0.992.543.421 (3)148
C22—H22···O3ii0.952.513.233 (3)133
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.952.463.368 (3)160
C7—H7B···O1ii0.992.443.350 (3)152
C9—H9···O1ii0.952.593.374 (3)141
C20—H20B···O3ii0.992.543.421 (3)148
C22—H22···O3ii0.952.513.233 (3)133
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.
Acknowledgements top

Financial support provided by the Natural Sciences Engineering and Research Council of Canada (NSERC), the Canada Foundation for Innovation and the University of British Columbia Okanagan is gratefully acknowledged.

references
References top

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