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Acta Cryst. (2010). E66, m22    [ doi:10.1107/S1600536809051903 ]

An orthorhombic polymorph of 1-[(ferrocenyl)(hydroxy)methyl]-1,2-dicarba-closo-dodecaborane

H. Chen, J. Miao, P. Zhu, D. Wang and Y. Nie

Abstract top

An orthorhombic polymorph of the title compound, [Fe(C5H5)(C8H17B10O)] or C13H22B10FeO, is described here in addition to the known monoclinic polymorph [Crundwell et al. (1999). Acta Cryst. C55, IUC9900087]. The asymmetric unit contains four independent molecules with Ccage-Ccage distances of 1.636 (16)-1.700 (16) Å, and with the methylhydroxy groups disordered over two positions in each molecule [occupancy ratios 0.80 (2):0.20 (2), 0.59 (3):0.41 (3), 0.60 (2):0.40 (2) and 0.793 (17):0.207 (17)].

Comment top

In 1999 Crundwell et al. reported an interesting compound having an o-carboranyl and a ferrocenyl moieties tethered through a hydroxymethyl group, from the reaction of o-carborane and ferrocenecarboxaldehyde mediated by tetrabutylammonium fluoride. We have recently studied a similar reaction of dilithiocarborane with ferrocenecarboxaldehyde in the hope of obtaining a novel species that have two ferrocenyl groups linking to the carborane cage via a single carbon atom. It turned out that the reaction occurred only at one cage carbon yielding after recrystallization a new polymorph of the known compound (Crundwell et al., 1999)

The title compound (I) crystallizes in the orthorhombic Pca21 space group (cf. that of Crundwell et al. in the monoclinic P21/c space group) with the normal geometric parameters comparable with those observed in related structures of carboranyl alcohols (Tsuji, 2004; Terrasson et al., 2008; Shen et al., 2006).

There are four crystallographically independent molecules in the asymmetric unit, and all the hydroxyl groups are disordered over two positions with different occupancy for each oxygen atom. These molecules have the same constitution and very similar geometric parameters, only some subtle differences are found within the carborane cage. The Ccage—Ccage distances in the present structure vary in the range 1.636 (16)–1.700 (16) Å, while that of Crundwell et al. has been reported to be 1.658 (3) Å.

Related literature top

For the crystal structure of the monoclinic polymorph, see Crundwell et al. (1999). For the crystal structures of related carboranyl alcohols, see: Tsuji (2004); Terrasson et al. (2008); Shen et al. (2006).

Experimental top

Under argon a portion of n-BuLi (2.2 M, 0.23 ml, 0.5 mmol) was added dropwise to a solution of o-carborane (36 mg, 0.25 mmol) in diethylether (20 ml) cooled with ice-bath. The resulting suspension was stirred at ambient temperature for 0.5 h, cooled to 253 K, to which ferrocenecarboxaldehyde (106 mg, 0.5 mmol) was added. The reaction mixture was warmed up to ambient temperature and stirred for 2 h. After quenching with HCl (10%) the mixture was filtered to remove small amount of black stuff and extracted with ether. The organic phases were combined and dried (MgSO4) to give a yellow solid, which was purified with preparative TLC (eluent: CH2Cl2/ petroleum ether (b.p. 333–363 K) (1:1, V/V). A yellow band at Rf = 0.51 was collected and identified to be the title compound (34 mg, 38%). Yellow crystals were grown from a dichloromethane/n-hexane solution at ambient temperature. m.p. 464–465 K. IR (KBr): v = 3552 (w), 3082 (w), 2896 (w), 2585 (s) cm-1.

Refinement top

All H-atoms were positioned geometrically (C—H 0.93-0.98 Å; B—H 1.1 Å; O—H 0.82 Å), and refined using a riding model, with Uiso=1.2Ueq of the parent atom.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of one independent molecule of (I) showing the atomic numbering and 25% probability displacement ellipsoids. Only major parts of the disordered atoms are shown for clarity.
1-[(ferrocenyl)(hydroxy)methyl]- 1,2-dicarba-closo-dodecaborane top
Crystal data top
[Fe(C5H5)(C8H17B10O)]Dx = 1.344 Mg m−3
Mr = 358.26Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 3704 reflections
a = 27.051 (2) Åθ = 2.6–25.3°
b = 8.9682 (7) ŵ = 0.85 mm−1
c = 29.191 (3) ÅT = 298 K
V = 7081.8 (11) Å3Yellow, block
Z = 160.25 × 0.14 × 0.07 mm
F(000) = 2944
Data collection top
Bruker SMART CCD area-detector
diffractometer		12025 independent reflections
Radiation source: fine-focus sealed tube5629 reflections with I > 2σ(I)
graphiteRint = 0.115
phi and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −32→32
Tmin = 0.816, Tmax = 0.943k = −10→9
35277 measured reflectionsl = −34→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)] = 0.075H-atom parameters constrained
wR(F2) = 0.181 w = 1/[σ2(Fo2) + (0.0599P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
12025 reflectionsΔρmax = 1.12 e Å−3
942 parametersΔρmin = −0.45 e Å−3
1 restraintAbsolute structure: Flack (1983), 5617 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (3)
Crystal data top
[Fe(C5H5)(C8H17B10O)]V = 7081.8 (11) Å3
Mr = 358.26Z = 16
Orthorhombic, Pca21Mo Kα radiation
a = 27.051 (2) ŵ = 0.85 mm−1
b = 8.9682 (7) ÅT = 298 K
c = 29.191 (3) Å0.25 × 0.14 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		12025 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		5629 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.943Rint = 0.115
35277 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.181Δρmax = 1.12 e Å−3
S = 1.03Δρmin = −0.45 e Å−3
12025 reflectionsAbsolute structure: Flack (1983), 5617 Friedel pairs
942 parametersFlack parameter: 0.02 (3)
1 restraint
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.

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*/UeqOcc. (<1)
Fe10.02406 (6)0.5567 (2)0.22116 (6)0.0499 (5)
Fe20.24220 (6)0.43970 (18)0.47382 (5)0.0470 (4)
Fe30.37998 (6)0.94455 (19)0.34605 (5)0.0458 (4)
Fe40.40150 (6)0.93997 (19)0.09112 (4)0.0451 (4)
O10.1333 (3)0.6277 (13)0.2864 (4)0.078 (5)0.80 (2)
H10.16230.65140.28960.116*0.80 (2)
O20.3554 (5)0.342 (2)0.5263 (7)0.076 (8)0.59 (3)
H20.37280.32360.54870.115*0.59 (3)
O30.2684 (5)0.8410 (17)0.2913 (5)0.072 (6)0.60 (2)
H30.24080.80420.28920.109*0.60 (2)
O40.5111 (3)0.8624 (11)0.0271 (3)0.069 (4)0.793 (17)
H40.53980.83430.02510.103*0.793 (17)
O1'0.1373 (15)0.729 (5)0.2444 (18)0.08 (2)0.20 (2)
H1'0.16350.76210.25430.116*0.20 (2)
O2'0.3530 (7)0.241 (3)0.4882 (9)0.076 (11)0.41 (3)
H2'0.37400.17550.49090.115*0.41 (3)
O3'0.2719 (7)0.728 (2)0.3309 (8)0.072 (10)0.40 (2)
H3'0.24560.69080.32260.108*0.40 (2)
O4'0.5154 (13)0.746 (4)0.0740 (13)0.069 (16)0.207 (17)
H4'0.54270.72710.06320.103*0.207 (17)
B10.1600 (5)0.9955 (16)0.2925 (5)0.060 (4)
H1A0.18400.98350.26220.072*
B20.1619 (5)0.8823 (15)0.3371 (5)0.051 (4)
H2A0.18840.78930.33570.061*
B30.1070 (5)0.8518 (16)0.3630 (4)0.052 (4)
H3A0.09710.74410.37850.063*
B40.0629 (5)0.9635 (15)0.3349 (4)0.051 (4)
H4A0.02370.93250.33230.061*
B50.0821 (5)1.1460 (15)0.3405 (5)0.051 (4)
H50.05511.23770.34070.061*
B60.1416 (5)1.1706 (17)0.3159 (5)0.060 (4)
H60.15261.27830.30100.072*
B70.1836 (4)1.0591 (13)0.3436 (4)0.038 (3)
H70.22281.09130.34610.046*
B80.1517 (6)0.9647 (18)0.3890 (6)0.060 (5)
H80.17020.93390.42130.072*
B90.0871 (7)1.0227 (18)0.3850 (6)0.059 (5)
H90.06281.03180.41510.071*
B100.1363 (6)1.1474 (16)0.3759 (5)0.057 (4)
H100.14451.23670.40060.068*
B110.3273 (5)0.1532 (19)0.6143 (5)0.065 (4)
H110.31950.26480.62810.078*
B120.3791 (5)0.1062 (18)0.5876 (6)0.063 (5)
H120.40750.19290.58290.076*
B130.3733 (6)−0.0116 (19)0.5468 (6)0.064 (5)
H130.3966−0.00770.51600.077*
B140.3114 (5)−0.0589 (17)0.5443 (5)0.066 (4)
H140.2930−0.08870.51200.079*
B150.2950 (6)−0.1456 (18)0.5955 (5)0.069 (5)
H150.2661−0.23170.59620.083*
B160.3056 (7)−0.0143 (19)0.6427 (6)0.069 (5)
H160.2840−0.01710.67460.083*
B170.3695 (7)0.037 (2)0.6398 (6)0.073 (6)
H170.39020.07450.67010.087*
B180.3959 (5)−0.0737 (18)0.5999 (5)0.061 (4)
H180.4337−0.11580.60480.074*
B190.3545 (6)−0.1780 (18)0.5721 (5)0.072 (5)
H190.3647−0.28760.55820.086*
B200.3502 (6)−0.1441 (18)0.6307 (5)0.063 (4)
H200.3568−0.23170.65640.076*
B210.3462 (5)0.5429 (15)0.2318 (4)0.054 (4)
H210.38450.58320.23520.065*
B220.3012 (5)0.6486 (16)0.2047 (4)0.051 (4)
H220.30950.75930.19040.061*
B230.2456 (5)0.6038 (15)0.2302 (4)0.049 (4)
H230.21670.68980.23250.058*
B240.2548 (6)0.4790 (17)0.2725 (5)0.060 (4)
H240.23180.47930.30360.072*
B250.3321 (5)0.3534 (14)0.2237 (5)0.057 (3)
H250.36100.26770.22120.068*
B260.3224 (6)0.4866 (17)0.1801 (5)0.056 (4)
H260.34530.48970.14900.068*
B270.2572 (6)0.5254 (18)0.1781 (5)0.055 (5)
H270.23710.55290.14650.066*
B280.2296 (5)0.4210 (16)0.2242 (6)0.059 (4)
H280.19120.38150.22320.071*
B290.2773 (5)0.3167 (18)0.2495 (5)0.064 (4)
H290.27070.20580.26440.077*
B300.2779 (5)0.3421 (16)0.1903 (5)0.060 (4)
H300.27110.25120.16570.071*
B310.4803 (5)0.6450 (16)−0.0499 (4)0.046 (3)
H310.46860.7517−0.06500.055*
B320.4394 (5)0.5353 (15)−0.0195 (5)0.053 (4)
H320.40080.5710−0.01490.063*
B330.4709 (5)0.4354 (15)0.0232 (5)0.046 (3)
H330.45240.40520.05540.055*
B340.5342 (5)0.4931 (17)0.0201 (5)0.046 (4)
H340.55780.50350.05060.056*
B350.5585 (5)0.4340 (15)−0.0310 (5)0.053 (4)
H350.59780.4035−0.03380.063*
B360.5261 (6)0.5250 (18)−0.0765 (5)0.052 (4)
H360.54410.5532−0.10920.062*
B370.4638 (5)0.4738 (18)−0.0729 (5)0.046 (4)
H370.44050.4670−0.10370.055*
B380.4578 (5)0.3433 (15)−0.0269 (5)0.048 (3)
H380.43100.2512−0.02810.058*
B390.5153 (5)0.3209 (16)−0.0009 (4)0.051 (4)
H390.52590.21550.01570.062*
B400.5120 (5)0.3421 (15)−0.0624 (4)0.049 (4)
H400.52070.2508−0.08620.058*
C10.1115 (4)0.8805 (13)0.3052 (4)0.046 (3)
C20.0972 (4)1.0492 (14)0.2886 (4)0.067 (4)
H2B0.08031.07360.25510.080*
C30.1063 (4)0.7509 (13)0.2709 (4)0.059 (3)
H3B0.12000.78270.24140.070*0.80 (2)
H3'B0.11440.67060.29230.070*0.20 (2)
C40.0537 (4)0.7096 (13)0.2640 (4)0.052 (3)
C50.0237 (5)0.6067 (16)0.2896 (5)0.074 (4)
H5A0.03380.54410.31320.089*
C6−0.0245 (5)0.6211 (17)0.2709 (5)0.081 (4)
H6A−0.05190.56810.28120.097*
C7−0.0255 (5)0.7227 (15)0.2361 (5)0.080 (4)
H7A−0.05280.75010.21870.096*
C80.0222 (4)0.7769 (14)0.2321 (4)0.068 (4)
H8A0.03210.84860.21100.082*
C90.0625 (6)0.3699 (17)0.2050 (5)0.086 (5)
H9A0.08520.31950.22320.103*
C100.0120 (7)0.3459 (17)0.2046 (6)0.094 (6)
H10A−0.00560.27990.22300.112*
C11−0.0072 (7)0.442 (2)0.1708 (6)0.097 (6)
H11A−0.04000.45050.16150.116*
C120.0340 (8)0.5224 (19)0.1541 (6)0.090 (5)
H12A0.03320.59620.13180.107*
C130.0733 (7)0.4752 (19)0.1755 (6)0.078 (5)
H13A0.10500.51160.17040.093*
C140.3298 (4)0.1115 (14)0.5573 (4)0.056 (3)
C150.2808 (4)0.0463 (14)0.5878 (4)0.070 (3)
H15A0.24270.08740.58480.084*
C160.3235 (4)0.2333 (15)0.5206 (5)0.068 (4)
H16A0.33120.18700.49100.081*0.59 (3)
H16'0.33680.31660.53850.081*0.41 (3)
C170.2703 (4)0.2884 (12)0.5177 (4)0.046 (3)
C180.2486 (5)0.4058 (15)0.5425 (4)0.067 (4)
H18A0.26420.46850.56340.081*
C190.1984 (4)0.4093 (15)0.5294 (4)0.067 (4)
H19A0.17510.47550.54100.080*
C200.1885 (4)0.2999 (15)0.4968 (4)0.068 (4)
H20A0.15840.28160.48250.081*
C210.2328 (4)0.2234 (13)0.4898 (3)0.058 (3)
H21A0.23720.14280.47020.069*
C220.2819 (6)0.6162 (17)0.4530 (5)0.075 (4)
H22A0.30530.66380.47110.090*
C230.2919 (6)0.4956 (16)0.4239 (5)0.067 (5)
H23A0.32260.45270.41860.080*
C240.2489 (6)0.4538 (17)0.4052 (4)0.069 (4)
H24A0.24420.37430.38530.083*
C250.2126 (6)0.5510 (19)0.4210 (5)0.077 (4)
H25A0.17950.54710.41260.092*
C260.2327 (7)0.6546 (17)0.4511 (5)0.082 (5)
H26A0.21670.73170.46630.098*
C270.2975 (3)0.6116 (12)0.2615 (3)0.043 (3)
C280.3172 (4)0.4385 (14)0.2755 (4)0.070 (4)
H28A0.33600.41200.30790.084*
C290.3023 (4)0.7313 (14)0.2967 (4)0.063 (3)
H29A0.29490.68420.32620.075*0.60 (2)
H29'0.28740.81280.27910.075*0.40 (2)
C300.3527 (4)0.7936 (12)0.3009 (3)0.048 (3)
C310.3920 (4)0.7303 (13)0.3276 (4)0.057 (3)
H31A0.39050.64780.34680.068*
C320.4326 (5)0.8194 (15)0.3183 (4)0.066 (4)
H32A0.46360.80440.33130.080*
C330.4222 (5)0.9325 (15)0.2879 (4)0.068 (4)
H33A0.44371.00540.27700.082*
C340.3726 (4)0.9135 (13)0.2771 (4)0.055 (3)
H34A0.35510.97290.25660.066*
C350.3725 (6)0.9481 (16)0.4157 (4)0.071 (4)
H35A0.37700.86740.43530.086*
C360.4102 (6)1.0491 (19)0.4019 (5)0.079 (5)
H36A0.44321.04850.41080.094*
C370.3855 (6)1.1561 (15)0.3701 (5)0.076 (4)
H37A0.40071.23360.35430.091*
C380.3345 (5)1.1179 (14)0.3685 (4)0.062 (4)
H38A0.30981.16860.35260.074*
C390.3282 (6)0.9884 (17)0.3955 (5)0.071 (5)
H39A0.29850.93760.39930.085*
C400.4872 (4)0.6142 (12)0.0076 (3)0.037 (3)
C410.5375 (3)0.6109 (12)−0.0249 (4)0.044 (3)
H410.56440.7027−0.02410.053*
C420.4819 (4)0.7461 (13)0.0409 (4)0.049 (3)
H420.49390.71310.07090.059*0.793 (17)
H42'0.49350.82810.02150.059*0.207 (17)
C430.4296 (4)0.7875 (11)0.0462 (3)0.041 (2)
C440.4042 (4)0.9010 (14)0.0229 (4)0.057 (3)
H440.41800.96240.00060.068*
C450.3567 (5)0.9086 (15)0.0374 (4)0.066 (4)
H450.33330.97780.02780.079*
C460.3491 (5)0.7979 (14)0.0684 (4)0.068 (4)
H460.31900.77530.08220.082*
C470.3939 (4)0.7229 (12)0.0764 (4)0.053 (3)
H470.39930.64610.09720.064*
C480.4458 (6)1.1224 (15)0.1078 (5)0.075 (4)
H480.46811.17340.08940.090*
C490.3928 (6)1.1530 (16)0.1136 (5)0.081 (5)
H490.37481.22720.09890.097*
C500.3733 (6)1.0434 (18)0.1474 (5)0.077 (5)
H500.34091.03540.15780.092*
C510.4129 (6)0.9562 (16)0.1602 (4)0.069 (4)
H510.41100.88030.18180.083*
C520.4555 (6)0.9945 (16)0.1372 (5)0.069 (4)
H520.48580.94630.14000.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0616 (11)0.0438 (10)0.0442 (9)−0.0073 (9)−0.0085 (8)−0.0061 (10)
Fe20.0522 (10)0.0455 (9)0.0431 (9)0.0043 (9)−0.0062 (8)0.0038 (10)
Fe30.0526 (9)0.0439 (10)0.0407 (9)−0.0038 (9)−0.0082 (7)−0.0036 (10)
Fe40.0505 (10)0.0439 (11)0.0409 (9)0.0075 (8)0.0093 (8)−0.0048 (10)
O10.051 (6)0.077 (9)0.105 (11)0.014 (6)−0.020 (5)−0.029 (8)
O20.050 (9)0.078 (13)0.102 (15)−0.013 (8)−0.009 (8)0.039 (12)
O30.047 (8)0.072 (11)0.097 (12)0.002 (7)−0.008 (7)−0.031 (9)
O40.048 (6)0.071 (8)0.087 (8)−0.014 (5)0.019 (5)−0.030 (6)
O1'0.05 (3)0.08 (3)0.11 (4)0.01 (2)−0.02 (2)−0.03 (3)
O2'0.050 (13)0.078 (18)0.10 (2)−0.013 (11)−0.009 (12)0.039 (17)
O3'0.047 (12)0.072 (17)0.097 (19)0.002 (10)−0.008 (11)−0.031 (14)
O4'0.05 (2)0.07 (3)0.09 (3)−0.014 (19)0.02 (2)−0.03 (2)
B10.054 (9)0.058 (10)0.067 (10)−0.021 (8)0.013 (8)−0.012 (8)
B20.045 (8)0.049 (8)0.059 (9)−0.005 (7)−0.008 (7)−0.020 (7)
B30.057 (9)0.049 (9)0.051 (8)−0.006 (7)0.006 (7)−0.004 (7)
B40.043 (7)0.053 (9)0.057 (8)−0.012 (7)0.001 (6)−0.010 (7)
B50.055 (8)0.040 (8)0.058 (9)−0.008 (7)−0.002 (7)−0.015 (7)
B60.062 (9)0.054 (10)0.066 (10)−0.017 (8)0.001 (8)−0.012 (8)
B70.037 (6)0.031 (7)0.046 (7)−0.021 (6)0.007 (6)−0.010 (7)
B80.063 (11)0.063 (11)0.055 (9)0.001 (9)−0.009 (8)−0.007 (8)
B90.057 (11)0.056 (11)0.063 (10)−0.003 (8)0.010 (9)−0.012 (8)
B100.061 (10)0.053 (10)0.055 (9)−0.008 (8)0.003 (7)−0.013 (7)
B110.066 (10)0.065 (11)0.065 (10)0.009 (9)−0.003 (8)0.010 (8)
B120.056 (10)0.068 (12)0.066 (10)0.011 (7)0.008 (8)0.018 (10)
B130.062 (10)0.069 (11)0.061 (10)0.020 (8)−0.005 (8)0.018 (9)
B140.065 (9)0.065 (11)0.067 (10)0.011 (8)−0.008 (7)0.004 (9)
B150.066 (10)0.059 (10)0.082 (12)0.005 (8)−0.006 (9)0.021 (9)
B160.068 (11)0.082 (13)0.059 (10)0.019 (9)0.004 (8)0.020 (9)
B170.070 (12)0.079 (14)0.069 (12)0.009 (10)−0.016 (9)0.008 (10)
B180.050 (8)0.068 (11)0.066 (10)0.023 (8)−0.008 (8)0.011 (8)
B190.073 (10)0.064 (11)0.078 (11)0.022 (9)−0.008 (9)0.004 (9)
B200.063 (10)0.063 (11)0.063 (10)0.012 (9)−0.007 (8)0.027 (8)
B210.046 (7)0.061 (9)0.054 (9)0.001 (7)0.002 (6)−0.012 (7)
B220.051 (9)0.048 (9)0.055 (9)−0.016 (7)0.002 (7)0.000 (7)
B230.034 (7)0.054 (9)0.057 (10)−0.005 (7)−0.005 (6)−0.017 (7)
B240.049 (9)0.072 (12)0.059 (9)−0.018 (8)0.003 (7)−0.009 (8)
B250.046 (7)0.056 (8)0.069 (9)−0.005 (7)−0.007 (7)−0.013 (8)
B260.048 (9)0.070 (11)0.052 (8)−0.013 (7)0.009 (7)−0.016 (7)
B270.056 (10)0.061 (12)0.048 (9)0.002 (8)−0.016 (7)−0.002 (8)
B280.051 (9)0.066 (10)0.061 (9)−0.012 (8)−0.008 (7)0.001 (9)
B290.061 (9)0.063 (11)0.069 (10)−0.010 (8)−0.016 (8)0.009 (8)
B300.053 (9)0.055 (10)0.071 (10)−0.001 (8)−0.007 (7)−0.011 (8)
B310.049 (8)0.044 (9)0.045 (8)0.004 (7)−0.002 (7)0.002 (7)
B320.048 (8)0.048 (9)0.063 (9)−0.003 (7)0.005 (7)−0.009 (8)
B330.048 (8)0.043 (9)0.045 (7)0.002 (7)0.003 (6)−0.003 (7)
B340.043 (8)0.049 (9)0.047 (9)0.009 (6)−0.004 (6)−0.009 (7)
B350.043 (7)0.055 (9)0.060 (9)0.002 (7)−0.001 (7)−0.012 (8)
B360.056 (10)0.049 (11)0.050 (9)−0.009 (7)0.012 (7)−0.011 (7)
B370.045 (9)0.048 (11)0.044 (8)0.005 (7)−0.005 (6)−0.008 (7)
B380.051 (8)0.040 (8)0.053 (8)−0.007 (6)0.007 (7)−0.011 (7)
B390.054 (9)0.047 (9)0.053 (8)0.013 (7)0.000 (7)−0.006 (7)
B400.053 (9)0.045 (9)0.048 (8)0.005 (7)0.002 (6)−0.010 (6)
C10.037 (6)0.048 (7)0.052 (7)−0.004 (6)0.001 (5)−0.012 (6)
C20.072 (9)0.061 (9)0.067 (8)−0.011 (7)−0.002 (6)−0.004 (7)
C30.044 (7)0.060 (9)0.072 (8)−0.004 (6)0.004 (7)−0.020 (7)
C40.046 (7)0.057 (8)0.054 (7)−0.005 (6)−0.003 (6)−0.005 (6)
C50.076 (10)0.080 (11)0.067 (9)−0.013 (8)0.001 (7)−0.013 (8)
C60.063 (9)0.095 (12)0.085 (10)−0.032 (8)0.005 (8)−0.023 (9)
C70.069 (9)0.081 (10)0.090 (11)−0.001 (8)−0.011 (8)−0.019 (8)
C80.069 (8)0.067 (9)0.068 (9)−0.005 (7)−0.005 (7)−0.017 (7)
C90.100 (14)0.072 (11)0.086 (12)0.001 (9)−0.006 (9)−0.017 (9)
C100.118 (16)0.067 (12)0.095 (14)−0.030 (11)0.023 (12)−0.017 (9)
C110.086 (13)0.111 (16)0.093 (12)−0.003 (12)−0.023 (11)−0.049 (12)
C120.121 (15)0.085 (13)0.063 (11)0.000 (11)0.010 (10)−0.011 (9)
C130.076 (11)0.080 (13)0.076 (11)−0.012 (9)0.023 (9)−0.015 (9)
C140.050 (7)0.059 (9)0.058 (8)0.007 (6)−0.003 (6)0.014 (6)
C150.061 (7)0.075 (9)0.074 (8)0.006 (7)0.000 (7)0.019 (8)
C160.055 (8)0.078 (10)0.070 (9)−0.001 (7)0.005 (7)0.028 (8)
C170.041 (6)0.052 (8)0.045 (6)0.012 (6)0.007 (5)0.011 (6)
C180.076 (9)0.074 (10)0.052 (8)0.010 (7)−0.006 (6)0.012 (7)
C190.061 (9)0.079 (10)0.061 (8)0.028 (7)0.015 (7)0.012 (7)
C200.045 (7)0.088 (10)0.070 (9)0.003 (7)−0.018 (6)0.013 (8)
C210.060 (7)0.062 (8)0.051 (7)−0.005 (7)−0.003 (6)0.011 (6)
C220.082 (11)0.070 (11)0.073 (10)−0.011 (9)−0.007 (8)0.014 (9)
C230.068 (11)0.069 (12)0.064 (10)0.002 (8)0.008 (8)0.020 (8)
C240.085 (11)0.078 (11)0.045 (8)−0.005 (9)0.000 (7)0.025 (7)
C250.069 (10)0.086 (11)0.075 (9)0.002 (10)−0.020 (8)0.029 (9)
C260.099 (13)0.061 (11)0.085 (12)0.017 (10)0.004 (10)0.018 (9)
C270.033 (6)0.051 (7)0.044 (6)−0.006 (5)0.001 (5)−0.016 (5)
C280.066 (8)0.073 (9)0.071 (8)−0.008 (7)−0.013 (6)0.002 (8)
C290.050 (7)0.074 (10)0.065 (8)−0.010 (7)0.004 (7)−0.025 (7)
C300.046 (7)0.054 (8)0.044 (6)−0.006 (6)−0.006 (5)−0.012 (5)
C310.063 (8)0.055 (8)0.052 (7)0.004 (7)−0.016 (6)−0.007 (6)
C320.053 (8)0.082 (10)0.064 (9)−0.001 (8)−0.003 (6)−0.015 (8)
C330.075 (10)0.073 (10)0.057 (8)−0.027 (8)0.004 (7)−0.008 (7)
C340.063 (8)0.061 (9)0.040 (7)−0.007 (7)−0.013 (6)−0.001 (6)
C350.099 (11)0.073 (10)0.042 (7)0.003 (9)−0.006 (7)−0.017 (7)
C360.082 (10)0.084 (11)0.070 (9)0.002 (10)−0.030 (8)−0.027 (9)
C370.095 (11)0.053 (9)0.081 (10)−0.013 (8)−0.001 (9)−0.015 (8)
C380.070 (9)0.046 (8)0.068 (8)0.012 (7)−0.009 (7)−0.015 (7)
C390.077 (11)0.069 (11)0.066 (9)−0.001 (8)0.005 (8)−0.025 (7)
C400.036 (6)0.038 (7)0.036 (6)0.001 (5)0.007 (5)−0.008 (5)
C410.038 (6)0.044 (7)0.051 (6)−0.001 (5)0.005 (5)−0.012 (6)
C420.043 (6)0.054 (8)0.050 (6)0.004 (6)0.000 (6)−0.016 (6)
C430.044 (6)0.044 (7)0.034 (6)0.002 (5)0.008 (5)−0.007 (5)
C440.063 (8)0.067 (9)0.041 (7)0.010 (7)0.003 (6)−0.003 (6)
C450.065 (9)0.078 (11)0.055 (8)0.027 (8)−0.015 (7)−0.012 (7)
C460.051 (7)0.079 (10)0.073 (9)0.006 (7)0.010 (6)−0.022 (8)
C470.055 (7)0.049 (8)0.054 (7)0.001 (6)0.015 (5)−0.006 (6)
C480.088 (11)0.060 (10)0.077 (9)−0.017 (8)−0.002 (8)−0.016 (8)
C490.106 (13)0.052 (10)0.084 (11)0.023 (9)−0.008 (10)−0.021 (8)
C500.079 (11)0.079 (12)0.073 (10)−0.001 (10)0.028 (8)−0.028 (9)
C510.090 (10)0.071 (10)0.047 (8)0.000 (9)0.006 (8)−0.015 (7)
C520.076 (10)0.066 (10)0.064 (9)0.007 (7)0.005 (8)−0.016 (7)
Geometric parameters (Å) top
Fe1—C101.978 (15)B24—H241.1000
Fe1—C111.984 (15)B25—B291.695 (19)
Fe1—C121.999 (15)B25—C281.740 (18)
Fe1—C82.001 (12)B25—B301.763 (19)
Fe1—C42.020 (11)B25—B261.76 (2)
Fe1—C132.022 (15)B25—H251.1000
Fe1—C92.028 (15)B26—B301.79 (2)
Fe1—C62.042 (13)B26—B271.80 (2)
Fe1—C52.046 (14)B26—H261.1000
Fe1—C72.051 (13)B27—B301.77 (2)
Fe2—C252.004 (13)B27—B281.80 (2)
Fe2—C222.006 (13)B27—H271.1000
Fe2—C212.012 (11)B28—B291.76 (2)
Fe2—C172.014 (10)B28—B301.79 (2)
Fe2—C242.015 (13)B28—H281.1000
Fe2—C192.028 (11)B29—C281.712 (18)
Fe2—C202.032 (12)B29—B301.745 (18)
Fe2—C182.036 (13)B29—H291.1000
Fe2—C232.044 (15)B30—H301.1000
Fe2—C262.054 (14)B31—C401.712 (15)
Fe3—C321.985 (12)B31—B321.726 (18)
Fe3—C312.022 (11)B31—B371.73 (2)
Fe3—C302.027 (10)B31—C411.738 (16)
Fe3—C372.029 (13)B31—B361.82 (2)
Fe3—C342.043 (11)B31—H311.1000
Fe3—C352.044 (13)B32—C401.675 (17)
Fe3—C332.050 (12)B32—B331.756 (19)
Fe3—C392.051 (14)B32—B371.78 (2)
Fe3—C362.051 (13)B32—B381.806 (18)
Fe3—C382.088 (12)B32—H321.1000
Fe4—C452.001 (12)B33—B381.717 (18)
Fe4—C472.004 (11)B33—C401.725 (16)
Fe4—C462.019 (12)B33—B391.729 (18)
Fe4—C442.024 (12)B33—B341.789 (18)
Fe4—C492.034 (14)B33—H331.1000
Fe4—C502.035 (14)B34—C411.687 (18)
Fe4—C432.042 (9)B34—C401.710 (17)
Fe4—C512.045 (13)B34—B351.714 (19)
Fe4—C522.046 (15)B34—B391.74 (2)
Fe4—C482.085 (13)B34—H341.1000
O1—C31.400 (15)B35—C411.695 (16)
O1—H10.8200B35—B401.760 (17)
O1—H3'B0.6617B35—B391.778 (19)
O2—C161.31 (2)B35—B361.79 (2)
O2—H20.8200B35—H351.1000
O2—H16'0.6567B36—C411.721 (18)
O3—C291.354 (16)B36—B401.73 (2)
O3—H30.8200B36—B371.75 (2)
O3—H29'0.6750B36—H361.1000
O4—C421.369 (13)B37—B401.786 (19)
O4—H40.8200B37—B381.79 (2)
O4—H42'0.5889B37—H371.1000
O1'—C31.15 (5)B38—B391.742 (18)
O1'—H1'0.8200B38—B401.794 (18)
O2'—C161.24 (2)B38—H381.1000
O2'—H2'0.8200B39—B401.806 (17)
O3'—C291.29 (2)B39—H391.1000
O3'—H3'0.8200B40—H401.1000
O4'—C421.33 (4)C1—C31.543 (14)
O4'—H4'0.8200C1—C21.636 (16)
B1—B21.65 (2)C2—H2B1.1000
B1—C11.710 (17)C3—C41.484 (14)
B1—B71.720 (19)C3—H3B0.9800
B1—C21.771 (19)C3—H3'B0.9800
B1—B61.78 (2)C4—C81.398 (15)
B1—H1A1.1000C4—C51.436 (16)
B2—C11.650 (16)C5—C61.420 (16)
B2—B31.687 (19)C5—H5A0.9300
B2—B71.701 (16)C6—C71.365 (17)
B2—B81.71 (2)C6—H6A0.9300
B2—H2A1.1000C7—C81.385 (15)
B3—C11.709 (17)C7—H7A0.9300
B3—B91.75 (2)C8—H8A0.9300
B3—B81.75 (2)C9—C131.311 (18)
B3—B41.762 (18)C9—C101.38 (2)
B3—H3A1.1000C9—H9A0.9300
B4—B91.690 (19)C10—C111.41 (2)
B4—B51.725 (17)C10—H10A0.9300
B4—C11.741 (16)C11—C121.42 (2)
B4—C21.810 (17)C11—H11A0.9300
B4—H4A1.1000C12—C131.30 (2)
B5—B91.71 (2)C12—H12A0.9300
B5—B61.777 (18)C13—H13A0.9300
B5—B101.79 (2)C14—C161.539 (15)
B5—C21.795 (18)C14—C151.700 (16)
B5—H51.1000C15—H15A1.1000
B6—B71.715 (19)C16—C171.525 (15)
B6—B101.770 (18)C16—H16A0.9800
B6—C21.808 (17)C16—H16'0.9800
B6—H61.1000C17—C181.407 (15)
B7—B101.778 (18)C17—C211.424 (14)
B7—B81.80 (2)C18—C191.411 (15)
B7—H71.1000C18—H18A0.9300
B8—B101.73 (2)C19—C201.393 (15)
B8—B91.83 (2)C19—H19A0.9300
B8—H81.1000C20—C211.396 (14)
B9—B101.76 (2)C20—H20A0.9300
B9—H91.1000C21—H21A0.9300
B10—H101.1000C22—C261.375 (17)
B11—B121.66 (2)C22—C231.401 (18)
B11—C141.706 (18)C22—H22A0.9300
B11—B171.72 (2)C23—C241.337 (19)
B11—C151.759 (19)C23—H23A0.9300
B11—B161.81 (2)C24—C251.392 (18)
B11—H111.1000C24—H24A0.9300
B12—B131.60 (2)C25—C261.388 (18)
B12—C141.601 (18)C25—H25A0.9300
B12—B171.66 (2)C26—H26A0.9300
B12—B181.71 (2)C27—C291.493 (13)
B12—H121.1000C27—C281.692 (15)
B13—C141.642 (19)C28—H28A1.1000
B13—B141.73 (2)C29—C301.479 (13)
B13—B191.74 (2)C29—H29A0.9800
B13—B181.76 (2)C29—H29'0.9800
B13—H131.1000C30—C341.390 (14)
B14—C141.652 (19)C30—C311.434 (13)
B14—B151.74 (2)C31—C321.385 (15)
B14—B191.78 (2)C31—H31A0.9300
B14—C151.784 (19)C32—C331.378 (16)
B14—H141.1000C32—H32A0.9300
B15—B191.77 (2)C33—C341.389 (16)
B15—C151.777 (18)C33—H33A0.9300
B15—B201.81 (2)C34—H34A0.9300
B15—B161.84 (2)C35—C391.383 (18)
B15—H151.1000C35—C361.421 (19)
B16—B201.71 (2)C35—H35A0.9300
B16—B171.79 (3)C36—C371.493 (18)
B16—C151.820 (19)C36—H36A0.9300
B16—H161.1000C37—C381.424 (15)
B17—B181.69 (2)C37—H37A0.9300
B17—B201.73 (2)C38—C391.415 (17)
B17—H171.1000C38—H38A0.9300
B18—B201.65 (2)C39—H39A0.9300
B18—B191.67 (2)C40—C421.537 (13)
B18—H181.1000C40—C411.657 (13)
B19—B201.74 (2)C41—H411.1000
B19—H191.1000C42—C431.469 (13)
B20—H201.1000C42—H420.9800
B21—C271.694 (15)C42—H42'0.9800
B21—B261.717 (19)C43—C441.405 (14)
B21—B221.736 (18)C43—C471.430 (13)
B21—B251.758 (17)C44—C451.355 (15)
B21—C281.766 (17)C44—H440.9300
B21—H211.1000C45—C461.360 (15)
B22—C271.694 (17)C45—H450.9300
B22—B261.719 (19)C46—C471.407 (15)
B22—B231.726 (17)C46—H460.9300
B22—B271.798 (19)C47—H470.9300
B22—H221.1000C48—C521.457 (17)
B23—C271.675 (15)C48—C491.468 (18)
B23—B241.68 (2)C48—H480.9300
B23—B281.704 (19)C49—C501.489 (19)
B23—B271.705 (19)C49—H490.9300
B23—H231.1000C50—C511.377 (18)
B24—B281.65 (2)C50—H500.9300
B24—C271.688 (17)C51—C521.379 (18)
B24—B291.71 (2)C51—H510.9300
B24—C281.728 (19)C52—H520.9300
Acknowledgements top

This work was supported by the University of Jinan (grant No. B0605), the Key Subject Research Foundation of Shandong Province (grant No. XTD 0704), the NSFC (grant No. 20702020) and the SRF for ROCS, SEM (grant No. SQT0804).

references
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Shen, H., Chan, H.-S. & Xie, Z.-W. (2006). Organometallics, 25, 2617–2625.

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