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

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

doi:10.1107/S1600536809051903

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m22

doi:10.1107/S1600536809051903

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

Hongwei Chen,^a Jinling Miao,^a Peihua Zhu,^a Daqi Wang ^b and Yong Nie ^a ^*

^aSchool of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: chm_niey@ujn.edu.cn

(Received 20 November 2009; accepted 2 December 2009; online 9 December 2009)

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 C_cage–C_cage 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)].

Related literature

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

Crystal data

[Fe(C₅H₅)(C₈H₁₇B₁₀O)]
M_r = 358.26
Orthorhombic, P c a 2₁
a = 27.051 (2) Å
b = 8.9682 (7) Å
c = 29.191 (3) Å
V = 7081.8 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 298 K
0.25 × 0.14 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.816, T_max = 0.943
35277 measured reflections
12025 independent reflections
5629 reflections with I > 2σ(I)
R_int = 0.115

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.181
S = 1.03
12025 reflections
942 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −0.45 e Å⁻³
Absolute structure: Flack (1983 ), 5617 Friedel pairs
Flack parameter: 0.02 (3)

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051903/cv2664sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051903/cv2664Isup2.hkl

checkCIF report

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 C_cage—C_cage 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.

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

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)]	D_x = 1.344 Mg m⁻³
M_r = 358.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 3704 reflections
a = 27.051 (2) Å	θ = 2.6–25.3°
b = 8.9682 (7) Å	µ = 0.85 mm⁻¹
c = 29.191 (3) Å	T = 298 K
V = 7081.8 (11) Å³	Yellow, block
Z = 16	0.25 × 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 tube	5629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.115
phi and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −32→32
T_min = 0.816, T_max = 0.943	k = −10→9
35277 measured reflections	l = −34→33

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.181	w = 1/[σ²(F_o²) + (0.0599P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
12025 reflections	Δρ_max = 1.12 e Å⁻³
942 parameters	Δρ_min = −0.45 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 5617 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

[Fe(C₅H₅)(C₈H₁₇B₁₀O)]	V = 7081.8 (11) Å³
M_r = 358.26	Z = 16
Orthorhombic, Pca2₁	Mo Kα radiation
a = 27.051 (2) Å	µ = 0.85 mm⁻¹
b = 8.9682 (7) Å	T = 298 K
c = 29.191 (3) Å	0.25 × 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)
T_min = 0.816, T_max = 0.943	R_int = 0.115
35277 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.181	Δρ_max = 1.12 e Å⁻³
S = 1.03	Δρ_min = −0.45 e Å⁻³
12025 reflections	Absolute structure: Flack (1983), 5617 Friedel pairs
942 parameters	Absolute structure 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.02406 (6)	0.5567 (2)	0.22116 (6)	0.0499 (5)
Fe2	0.24220 (6)	0.43970 (18)	0.47382 (5)	0.0470 (4)
Fe3	0.37998 (6)	0.94455 (19)	0.34605 (5)	0.0458 (4)
Fe4	0.40150 (6)	0.93997 (19)	0.09112 (4)	0.0451 (4)
O1	0.1333 (3)	0.6277 (13)	0.2864 (4)	0.078 (5)	0.80 (2)
H1	0.1623	0.6514	0.2896	0.116*	0.80 (2)
O2	0.3554 (5)	0.342 (2)	0.5263 (7)	0.076 (8)	0.59 (3)
H2	0.3728	0.3236	0.5487	0.115*	0.59 (3)
O3	0.2684 (5)	0.8410 (17)	0.2913 (5)	0.072 (6)	0.60 (2)
H3	0.2408	0.8042	0.2892	0.109*	0.60 (2)
O4	0.5111 (3)	0.8624 (11)	0.0271 (3)	0.069 (4)	0.793 (17)
H4	0.5398	0.8343	0.0251	0.103*	0.793 (17)
O1'	0.1373 (15)	0.729 (5)	0.2444 (18)	0.08 (2)	0.20 (2)
H1'	0.1635	0.7621	0.2543	0.116*	0.20 (2)
O2'	0.3530 (7)	0.241 (3)	0.4882 (9)	0.076 (11)	0.41 (3)
H2'	0.3740	0.1755	0.4909	0.115*	0.41 (3)
O3'	0.2719 (7)	0.728 (2)	0.3309 (8)	0.072 (10)	0.40 (2)
H3'	0.2456	0.6908	0.3226	0.108*	0.40 (2)
O4'	0.5154 (13)	0.746 (4)	0.0740 (13)	0.069 (16)	0.207 (17)
H4'	0.5427	0.7271	0.0632	0.103*	0.207 (17)
B1	0.1600 (5)	0.9955 (16)	0.2925 (5)	0.060 (4)
H1A	0.1840	0.9835	0.2622	0.072*
B2	0.1619 (5)	0.8823 (15)	0.3371 (5)	0.051 (4)
H2A	0.1884	0.7893	0.3357	0.061*
B3	0.1070 (5)	0.8518 (16)	0.3630 (4)	0.052 (4)
H3A	0.0971	0.7441	0.3785	0.063*
B4	0.0629 (5)	0.9635 (15)	0.3349 (4)	0.051 (4)
H4A	0.0237	0.9325	0.3323	0.061*
B5	0.0821 (5)	1.1460 (15)	0.3405 (5)	0.051 (4)
H5	0.0551	1.2377	0.3407	0.061*
B6	0.1416 (5)	1.1706 (17)	0.3159 (5)	0.060 (4)
H6	0.1526	1.2783	0.3010	0.072*
B7	0.1836 (4)	1.0591 (13)	0.3436 (4)	0.038 (3)
H7	0.2228	1.0913	0.3461	0.046*
B8	0.1517 (6)	0.9647 (18)	0.3890 (6)	0.060 (5)
H8	0.1702	0.9339	0.4213	0.072*
B9	0.0871 (7)	1.0227 (18)	0.3850 (6)	0.059 (5)
H9	0.0628	1.0318	0.4151	0.071*
B10	0.1363 (6)	1.1474 (16)	0.3759 (5)	0.057 (4)
H10	0.1445	1.2367	0.4006	0.068*
B11	0.3273 (5)	0.1532 (19)	0.6143 (5)	0.065 (4)
H11	0.3195	0.2648	0.6281	0.078*
B12	0.3791 (5)	0.1062 (18)	0.5876 (6)	0.063 (5)
H12	0.4075	0.1929	0.5829	0.076*
B13	0.3733 (6)	−0.0116 (19)	0.5468 (6)	0.064 (5)
H13	0.3966	−0.0077	0.5160	0.077*
B14	0.3114 (5)	−0.0589 (17)	0.5443 (5)	0.066 (4)
H14	0.2930	−0.0887	0.5120	0.079*
B15	0.2950 (6)	−0.1456 (18)	0.5955 (5)	0.069 (5)
H15	0.2661	−0.2317	0.5962	0.083*
B16	0.3056 (7)	−0.0143 (19)	0.6427 (6)	0.069 (5)
H16	0.2840	−0.0171	0.6746	0.083*
B17	0.3695 (7)	0.037 (2)	0.6398 (6)	0.073 (6)
H17	0.3902	0.0745	0.6701	0.087*
B18	0.3959 (5)	−0.0737 (18)	0.5999 (5)	0.061 (4)
H18	0.4337	−0.1158	0.6048	0.074*
B19	0.3545 (6)	−0.1780 (18)	0.5721 (5)	0.072 (5)
H19	0.3647	−0.2876	0.5582	0.086*
B20	0.3502 (6)	−0.1441 (18)	0.6307 (5)	0.063 (4)
H20	0.3568	−0.2317	0.6564	0.076*
B21	0.3462 (5)	0.5429 (15)	0.2318 (4)	0.054 (4)
H21	0.3845	0.5832	0.2352	0.065*
B22	0.3012 (5)	0.6486 (16)	0.2047 (4)	0.051 (4)
H22	0.3095	0.7593	0.1904	0.061*
B23	0.2456 (5)	0.6038 (15)	0.2302 (4)	0.049 (4)
H23	0.2167	0.6898	0.2325	0.058*
B24	0.2548 (6)	0.4790 (17)	0.2725 (5)	0.060 (4)
H24	0.2318	0.4793	0.3036	0.072*
B25	0.3321 (5)	0.3534 (14)	0.2237 (5)	0.057 (3)
H25	0.3610	0.2677	0.2212	0.068*
B26	0.3224 (6)	0.4866 (17)	0.1801 (5)	0.056 (4)
H26	0.3453	0.4897	0.1490	0.068*
B27	0.2572 (6)	0.5254 (18)	0.1781 (5)	0.055 (5)
H27	0.2371	0.5529	0.1465	0.066*
B28	0.2296 (5)	0.4210 (16)	0.2242 (6)	0.059 (4)
H28	0.1912	0.3815	0.2232	0.071*
B29	0.2773 (5)	0.3167 (18)	0.2495 (5)	0.064 (4)
H29	0.2707	0.2058	0.2644	0.077*
B30	0.2779 (5)	0.3421 (16)	0.1903 (5)	0.060 (4)
H30	0.2711	0.2512	0.1657	0.071*
B31	0.4803 (5)	0.6450 (16)	−0.0499 (4)	0.046 (3)
H31	0.4686	0.7517	−0.0650	0.055*
B32	0.4394 (5)	0.5353 (15)	−0.0195 (5)	0.053 (4)
H32	0.4008	0.5710	−0.0149	0.063*
B33	0.4709 (5)	0.4354 (15)	0.0232 (5)	0.046 (3)
H33	0.4524	0.4052	0.0554	0.055*
B34	0.5342 (5)	0.4931 (17)	0.0201 (5)	0.046 (4)
H34	0.5578	0.5035	0.0506	0.056*
B35	0.5585 (5)	0.4340 (15)	−0.0310 (5)	0.053 (4)
H35	0.5978	0.4035	−0.0338	0.063*
B36	0.5261 (6)	0.5250 (18)	−0.0765 (5)	0.052 (4)
H36	0.5441	0.5532	−0.1092	0.062*
B37	0.4638 (5)	0.4738 (18)	−0.0729 (5)	0.046 (4)
H37	0.4405	0.4670	−0.1037	0.055*
B38	0.4578 (5)	0.3433 (15)	−0.0269 (5)	0.048 (3)
H38	0.4310	0.2512	−0.0281	0.058*
B39	0.5153 (5)	0.3209 (16)	−0.0009 (4)	0.051 (4)
H39	0.5259	0.2155	0.0157	0.062*
B40	0.5120 (5)	0.3421 (15)	−0.0624 (4)	0.049 (4)
H40	0.5207	0.2508	−0.0862	0.058*
C1	0.1115 (4)	0.8805 (13)	0.3052 (4)	0.046 (3)
C2	0.0972 (4)	1.0492 (14)	0.2886 (4)	0.067 (4)
H2B	0.0803	1.0736	0.2551	0.080*
C3	0.1063 (4)	0.7509 (13)	0.2709 (4)	0.059 (3)
H3B	0.1200	0.7827	0.2414	0.070*	0.80 (2)
H3'B	0.1144	0.6706	0.2923	0.070*	0.20 (2)
C4	0.0537 (4)	0.7096 (13)	0.2640 (4)	0.052 (3)
C5	0.0237 (5)	0.6067 (16)	0.2896 (5)	0.074 (4)
H5A	0.0338	0.5441	0.3132	0.089*
C6	−0.0245 (5)	0.6211 (17)	0.2709 (5)	0.081 (4)
H6A	−0.0519	0.5681	0.2812	0.097*
C7	−0.0255 (5)	0.7227 (15)	0.2361 (5)	0.080 (4)
H7A	−0.0528	0.7501	0.2187	0.096*
C8	0.0222 (4)	0.7769 (14)	0.2321 (4)	0.068 (4)
H8A	0.0321	0.8486	0.2110	0.082*
C9	0.0625 (6)	0.3699 (17)	0.2050 (5)	0.086 (5)
H9A	0.0852	0.3195	0.2232	0.103*
C10	0.0120 (7)	0.3459 (17)	0.2046 (6)	0.094 (6)
H10A	−0.0056	0.2799	0.2230	0.112*
C11	−0.0072 (7)	0.442 (2)	0.1708 (6)	0.097 (6)
H11A	−0.0400	0.4505	0.1615	0.116*
C12	0.0340 (8)	0.5224 (19)	0.1541 (6)	0.090 (5)
H12A	0.0332	0.5962	0.1318	0.107*
C13	0.0733 (7)	0.4752 (19)	0.1755 (6)	0.078 (5)
H13A	0.1050	0.5116	0.1704	0.093*
C14	0.3298 (4)	0.1115 (14)	0.5573 (4)	0.056 (3)
C15	0.2808 (4)	0.0463 (14)	0.5878 (4)	0.070 (3)
H15A	0.2427	0.0874	0.5848	0.084*
C16	0.3235 (4)	0.2333 (15)	0.5206 (5)	0.068 (4)
H16A	0.3312	0.1870	0.4910	0.081*	0.59 (3)
H16'	0.3368	0.3166	0.5385	0.081*	0.41 (3)
C17	0.2703 (4)	0.2884 (12)	0.5177 (4)	0.046 (3)
C18	0.2486 (5)	0.4058 (15)	0.5425 (4)	0.067 (4)
H18A	0.2642	0.4685	0.5634	0.081*
C19	0.1984 (4)	0.4093 (15)	0.5294 (4)	0.067 (4)
H19A	0.1751	0.4755	0.5410	0.080*
C20	0.1885 (4)	0.2999 (15)	0.4968 (4)	0.068 (4)
H20A	0.1584	0.2816	0.4825	0.081*
C21	0.2328 (4)	0.2234 (13)	0.4898 (3)	0.058 (3)
H21A	0.2372	0.1428	0.4702	0.069*
C22	0.2819 (6)	0.6162 (17)	0.4530 (5)	0.075 (4)
H22A	0.3053	0.6638	0.4711	0.090*
C23	0.2919 (6)	0.4956 (16)	0.4239 (5)	0.067 (5)
H23A	0.3226	0.4527	0.4186	0.080*
C24	0.2489 (6)	0.4538 (17)	0.4052 (4)	0.069 (4)
H24A	0.2442	0.3743	0.3853	0.083*
C25	0.2126 (6)	0.5510 (19)	0.4210 (5)	0.077 (4)
H25A	0.1795	0.5471	0.4126	0.092*
C26	0.2327 (7)	0.6546 (17)	0.4511 (5)	0.082 (5)
H26A	0.2167	0.7317	0.4663	0.098*
C27	0.2975 (3)	0.6116 (12)	0.2615 (3)	0.043 (3)
C28	0.3172 (4)	0.4385 (14)	0.2755 (4)	0.070 (4)
H28A	0.3360	0.4120	0.3079	0.084*
C29	0.3023 (4)	0.7313 (14)	0.2967 (4)	0.063 (3)
H29A	0.2949	0.6842	0.3262	0.075*	0.60 (2)
H29'	0.2874	0.8128	0.2791	0.075*	0.40 (2)
C30	0.3527 (4)	0.7936 (12)	0.3009 (3)	0.048 (3)
C31	0.3920 (4)	0.7303 (13)	0.3276 (4)	0.057 (3)
H31A	0.3905	0.6478	0.3468	0.068*
C32	0.4326 (5)	0.8194 (15)	0.3183 (4)	0.066 (4)
H32A	0.4636	0.8044	0.3313	0.080*
C33	0.4222 (5)	0.9325 (15)	0.2879 (4)	0.068 (4)
H33A	0.4437	1.0054	0.2770	0.082*
C34	0.3726 (4)	0.9135 (13)	0.2771 (4)	0.055 (3)
H34A	0.3551	0.9729	0.2566	0.066*
C35	0.3725 (6)	0.9481 (16)	0.4157 (4)	0.071 (4)
H35A	0.3770	0.8674	0.4353	0.086*
C36	0.4102 (6)	1.0491 (19)	0.4019 (5)	0.079 (5)
H36A	0.4432	1.0485	0.4108	0.094*
C37	0.3855 (6)	1.1561 (15)	0.3701 (5)	0.076 (4)
H37A	0.4007	1.2336	0.3543	0.091*
C38	0.3345 (5)	1.1179 (14)	0.3685 (4)	0.062 (4)
H38A	0.3098	1.1686	0.3526	0.074*
C39	0.3282 (6)	0.9884 (17)	0.3955 (5)	0.071 (5)
H39A	0.2985	0.9376	0.3993	0.085*
C40	0.4872 (4)	0.6142 (12)	0.0076 (3)	0.037 (3)
C41	0.5375 (3)	0.6109 (12)	−0.0249 (4)	0.044 (3)
H41	0.5644	0.7027	−0.0241	0.053*
C42	0.4819 (4)	0.7461 (13)	0.0409 (4)	0.049 (3)
H42	0.4939	0.7131	0.0709	0.059*	0.793 (17)
H42'	0.4935	0.8281	0.0215	0.059*	0.207 (17)
C43	0.4296 (4)	0.7875 (11)	0.0462 (3)	0.041 (2)
C44	0.4042 (4)	0.9010 (14)	0.0229 (4)	0.057 (3)
H44	0.4180	0.9624	0.0006	0.068*
C45	0.3567 (5)	0.9086 (15)	0.0374 (4)	0.066 (4)
H45	0.3333	0.9778	0.0278	0.079*
C46	0.3491 (5)	0.7979 (14)	0.0684 (4)	0.068 (4)
H46	0.3190	0.7753	0.0822	0.082*
C47	0.3939 (4)	0.7229 (12)	0.0764 (4)	0.053 (3)
H47	0.3993	0.6461	0.0972	0.064*
C48	0.4458 (6)	1.1224 (15)	0.1078 (5)	0.075 (4)
H48	0.4681	1.1734	0.0894	0.090*
C49	0.3928 (6)	1.1530 (16)	0.1136 (5)	0.081 (5)
H49	0.3748	1.2272	0.0989	0.097*
C50	0.3733 (6)	1.0434 (18)	0.1474 (5)	0.077 (5)
H50	0.3409	1.0354	0.1578	0.092*
C51	0.4129 (6)	0.9562 (16)	0.1602 (4)	0.069 (4)
H51	0.4110	0.8803	0.1818	0.083*
C52	0.4555 (6)	0.9945 (16)	0.1372 (5)	0.069 (4)
H52	0.4858	0.9463	0.1400	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0616 (11)	0.0438 (10)	0.0442 (9)	−0.0073 (9)	−0.0085 (8)	−0.0061 (10)
Fe2	0.0522 (10)	0.0455 (9)	0.0431 (9)	0.0043 (9)	−0.0062 (8)	0.0038 (10)
Fe3	0.0526 (9)	0.0439 (10)	0.0407 (9)	−0.0038 (9)	−0.0082 (7)	−0.0036 (10)
Fe4	0.0505 (10)	0.0439 (11)	0.0409 (9)	0.0075 (8)	0.0093 (8)	−0.0048 (10)
O1	0.051 (6)	0.077 (9)	0.105 (11)	0.014 (6)	−0.020 (5)	−0.029 (8)
O2	0.050 (9)	0.078 (13)	0.102 (15)	−0.013 (8)	−0.009 (8)	0.039 (12)
O3	0.047 (8)	0.072 (11)	0.097 (12)	0.002 (7)	−0.008 (7)	−0.031 (9)
O4	0.048 (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)
B1	0.054 (9)	0.058 (10)	0.067 (10)	−0.021 (8)	0.013 (8)	−0.012 (8)
B2	0.045 (8)	0.049 (8)	0.059 (9)	−0.005 (7)	−0.008 (7)	−0.020 (7)
B3	0.057 (9)	0.049 (9)	0.051 (8)	−0.006 (7)	0.006 (7)	−0.004 (7)
B4	0.043 (7)	0.053 (9)	0.057 (8)	−0.012 (7)	0.001 (6)	−0.010 (7)
B5	0.055 (8)	0.040 (8)	0.058 (9)	−0.008 (7)	−0.002 (7)	−0.015 (7)
B6	0.062 (9)	0.054 (10)	0.066 (10)	−0.017 (8)	0.001 (8)	−0.012 (8)
B7	0.037 (6)	0.031 (7)	0.046 (7)	−0.021 (6)	0.007 (6)	−0.010 (7)
B8	0.063 (11)	0.063 (11)	0.055 (9)	0.001 (9)	−0.009 (8)	−0.007 (8)
B9	0.057 (11)	0.056 (11)	0.063 (10)	−0.003 (8)	0.010 (9)	−0.012 (8)
B10	0.061 (10)	0.053 (10)	0.055 (9)	−0.008 (8)	0.003 (7)	−0.013 (7)
B11	0.066 (10)	0.065 (11)	0.065 (10)	0.009 (9)	−0.003 (8)	0.010 (8)
B12	0.056 (10)	0.068 (12)	0.066 (10)	0.011 (7)	0.008 (8)	0.018 (10)
B13	0.062 (10)	0.069 (11)	0.061 (10)	0.020 (8)	−0.005 (8)	0.018 (9)
B14	0.065 (9)	0.065 (11)	0.067 (10)	0.011 (8)	−0.008 (7)	0.004 (9)
B15	0.066 (10)	0.059 (10)	0.082 (12)	0.005 (8)	−0.006 (9)	0.021 (9)
B16	0.068 (11)	0.082 (13)	0.059 (10)	0.019 (9)	0.004 (8)	0.020 (9)
B17	0.070 (12)	0.079 (14)	0.069 (12)	0.009 (10)	−0.016 (9)	0.008 (10)
B18	0.050 (8)	0.068 (11)	0.066 (10)	0.023 (8)	−0.008 (8)	0.011 (8)
B19	0.073 (10)	0.064 (11)	0.078 (11)	0.022 (9)	−0.008 (9)	0.004 (9)
B20	0.063 (10)	0.063 (11)	0.063 (10)	0.012 (9)	−0.007 (8)	0.027 (8)
B21	0.046 (7)	0.061 (9)	0.054 (9)	0.001 (7)	0.002 (6)	−0.012 (7)
B22	0.051 (9)	0.048 (9)	0.055 (9)	−0.016 (7)	0.002 (7)	0.000 (7)
B23	0.034 (7)	0.054 (9)	0.057 (10)	−0.005 (7)	−0.005 (6)	−0.017 (7)
B24	0.049 (9)	0.072 (12)	0.059 (9)	−0.018 (8)	0.003 (7)	−0.009 (8)
B25	0.046 (7)	0.056 (8)	0.069 (9)	−0.005 (7)	−0.007 (7)	−0.013 (8)
B26	0.048 (9)	0.070 (11)	0.052 (8)	−0.013 (7)	0.009 (7)	−0.016 (7)
B27	0.056 (10)	0.061 (12)	0.048 (9)	0.002 (8)	−0.016 (7)	−0.002 (8)
B28	0.051 (9)	0.066 (10)	0.061 (9)	−0.012 (8)	−0.008 (7)	0.001 (9)
B29	0.061 (9)	0.063 (11)	0.069 (10)	−0.010 (8)	−0.016 (8)	0.009 (8)
B30	0.053 (9)	0.055 (10)	0.071 (10)	−0.001 (8)	−0.007 (7)	−0.011 (8)
B31	0.049 (8)	0.044 (9)	0.045 (8)	0.004 (7)	−0.002 (7)	0.002 (7)
B32	0.048 (8)	0.048 (9)	0.063 (9)	−0.003 (7)	0.005 (7)	−0.009 (8)
B33	0.048 (8)	0.043 (9)	0.045 (7)	0.002 (7)	0.003 (6)	−0.003 (7)
B34	0.043 (8)	0.049 (9)	0.047 (9)	0.009 (6)	−0.004 (6)	−0.009 (7)
B35	0.043 (7)	0.055 (9)	0.060 (9)	0.002 (7)	−0.001 (7)	−0.012 (8)
B36	0.056 (10)	0.049 (11)	0.050 (9)	−0.009 (7)	0.012 (7)	−0.011 (7)
B37	0.045 (9)	0.048 (11)	0.044 (8)	0.005 (7)	−0.005 (6)	−0.008 (7)
B38	0.051 (8)	0.040 (8)	0.053 (8)	−0.007 (6)	0.007 (7)	−0.011 (7)
B39	0.054 (9)	0.047 (9)	0.053 (8)	0.013 (7)	0.000 (7)	−0.006 (7)
B40	0.053 (9)	0.045 (9)	0.048 (8)	0.005 (7)	0.002 (6)	−0.010 (6)
C1	0.037 (6)	0.048 (7)	0.052 (7)	−0.004 (6)	0.001 (5)	−0.012 (6)
C2	0.072 (9)	0.061 (9)	0.067 (8)	−0.011 (7)	−0.002 (6)	−0.004 (7)
C3	0.044 (7)	0.060 (9)	0.072 (8)	−0.004 (6)	0.004 (7)	−0.020 (7)
C4	0.046 (7)	0.057 (8)	0.054 (7)	−0.005 (6)	−0.003 (6)	−0.005 (6)
C5	0.076 (10)	0.080 (11)	0.067 (9)	−0.013 (8)	0.001 (7)	−0.013 (8)
C6	0.063 (9)	0.095 (12)	0.085 (10)	−0.032 (8)	0.005 (8)	−0.023 (9)
C7	0.069 (9)	0.081 (10)	0.090 (11)	−0.001 (8)	−0.011 (8)	−0.019 (8)
C8	0.069 (8)	0.067 (9)	0.068 (9)	−0.005 (7)	−0.005 (7)	−0.017 (7)
C9	0.100 (14)	0.072 (11)	0.086 (12)	0.001 (9)	−0.006 (9)	−0.017 (9)
C10	0.118 (16)	0.067 (12)	0.095 (14)	−0.030 (11)	0.023 (12)	−0.017 (9)
C11	0.086 (13)	0.111 (16)	0.093 (12)	−0.003 (12)	−0.023 (11)	−0.049 (12)
C12	0.121 (15)	0.085 (13)	0.063 (11)	0.000 (11)	0.010 (10)	−0.011 (9)
C13	0.076 (11)	0.080 (13)	0.076 (11)	−0.012 (9)	0.023 (9)	−0.015 (9)
C14	0.050 (7)	0.059 (9)	0.058 (8)	0.007 (6)	−0.003 (6)	0.014 (6)
C15	0.061 (7)	0.075 (9)	0.074 (8)	0.006 (7)	0.000 (7)	0.019 (8)
C16	0.055 (8)	0.078 (10)	0.070 (9)	−0.001 (7)	0.005 (7)	0.028 (8)
C17	0.041 (6)	0.052 (8)	0.045 (6)	0.012 (6)	0.007 (5)	0.011 (6)
C18	0.076 (9)	0.074 (10)	0.052 (8)	0.010 (7)	−0.006 (6)	0.012 (7)
C19	0.061 (9)	0.079 (10)	0.061 (8)	0.028 (7)	0.015 (7)	0.012 (7)
C20	0.045 (7)	0.088 (10)	0.070 (9)	0.003 (7)	−0.018 (6)	0.013 (8)
C21	0.060 (7)	0.062 (8)	0.051 (7)	−0.005 (7)	−0.003 (6)	0.011 (6)
C22	0.082 (11)	0.070 (11)	0.073 (10)	−0.011 (9)	−0.007 (8)	0.014 (9)
C23	0.068 (11)	0.069 (12)	0.064 (10)	0.002 (8)	0.008 (8)	0.020 (8)
C24	0.085 (11)	0.078 (11)	0.045 (8)	−0.005 (9)	0.000 (7)	0.025 (7)
C25	0.069 (10)	0.086 (11)	0.075 (9)	0.002 (10)	−0.020 (8)	0.029 (9)
C26	0.099 (13)	0.061 (11)	0.085 (12)	0.017 (10)	0.004 (10)	0.018 (9)
C27	0.033 (6)	0.051 (7)	0.044 (6)	−0.006 (5)	0.001 (5)	−0.016 (5)
C28	0.066 (8)	0.073 (9)	0.071 (8)	−0.008 (7)	−0.013 (6)	0.002 (8)
C29	0.050 (7)	0.074 (10)	0.065 (8)	−0.010 (7)	0.004 (7)	−0.025 (7)
C30	0.046 (7)	0.054 (8)	0.044 (6)	−0.006 (6)	−0.006 (5)	−0.012 (5)
C31	0.063 (8)	0.055 (8)	0.052 (7)	0.004 (7)	−0.016 (6)	−0.007 (6)
C32	0.053 (8)	0.082 (10)	0.064 (9)	−0.001 (8)	−0.003 (6)	−0.015 (8)
C33	0.075 (10)	0.073 (10)	0.057 (8)	−0.027 (8)	0.004 (7)	−0.008 (7)
C34	0.063 (8)	0.061 (9)	0.040 (7)	−0.007 (7)	−0.013 (6)	−0.001 (6)
C35	0.099 (11)	0.073 (10)	0.042 (7)	0.003 (9)	−0.006 (7)	−0.017 (7)
C36	0.082 (10)	0.084 (11)	0.070 (9)	0.002 (10)	−0.030 (8)	−0.027 (9)
C37	0.095 (11)	0.053 (9)	0.081 (10)	−0.013 (8)	−0.001 (9)	−0.015 (8)
C38	0.070 (9)	0.046 (8)	0.068 (8)	0.012 (7)	−0.009 (7)	−0.015 (7)
C39	0.077 (11)	0.069 (11)	0.066 (9)	−0.001 (8)	0.005 (8)	−0.025 (7)
C40	0.036 (6)	0.038 (7)	0.036 (6)	0.001 (5)	0.007 (5)	−0.008 (5)
C41	0.038 (6)	0.044 (7)	0.051 (6)	−0.001 (5)	0.005 (5)	−0.012 (6)
C42	0.043 (6)	0.054 (8)	0.050 (6)	0.004 (6)	0.000 (6)	−0.016 (6)
C43	0.044 (6)	0.044 (7)	0.034 (6)	0.002 (5)	0.008 (5)	−0.007 (5)
C44	0.063 (8)	0.067 (9)	0.041 (7)	0.010 (7)	0.003 (6)	−0.003 (6)
C45	0.065 (9)	0.078 (11)	0.055 (8)	0.027 (8)	−0.015 (7)	−0.012 (7)
C46	0.051 (7)	0.079 (10)	0.073 (9)	0.006 (7)	0.010 (6)	−0.022 (8)
C47	0.055 (7)	0.049 (8)	0.054 (7)	0.001 (6)	0.015 (5)	−0.006 (6)
C48	0.088 (11)	0.060 (10)	0.077 (9)	−0.017 (8)	−0.002 (8)	−0.016 (8)
C49	0.106 (13)	0.052 (10)	0.084 (11)	0.023 (9)	−0.008 (10)	−0.021 (8)
C50	0.079 (11)	0.079 (12)	0.073 (10)	−0.001 (10)	0.028 (8)	−0.028 (9)
C51	0.090 (10)	0.071 (10)	0.047 (8)	0.000 (9)	0.006 (8)	−0.015 (7)
C52	0.076 (10)	0.066 (10)	0.064 (9)	0.007 (7)	0.005 (8)	−0.016 (7)

Bond lengths (Å) top

Fe1—C10	1.978 (15)	B24—H24	1.1000
Fe1—C11	1.984 (15)	B25—B29	1.695 (19)
Fe1—C12	1.999 (15)	B25—C28	1.740 (18)
Fe1—C8	2.001 (12)	B25—B30	1.763 (19)
Fe1—C4	2.020 (11)	B25—B26	1.76 (2)
Fe1—C13	2.022 (15)	B25—H25	1.1000
Fe1—C9	2.028 (15)	B26—B30	1.79 (2)
Fe1—C6	2.042 (13)	B26—B27	1.80 (2)
Fe1—C5	2.046 (14)	B26—H26	1.1000
Fe1—C7	2.051 (13)	B27—B30	1.77 (2)
Fe2—C25	2.004 (13)	B27—B28	1.80 (2)
Fe2—C22	2.006 (13)	B27—H27	1.1000
Fe2—C21	2.012 (11)	B28—B29	1.76 (2)
Fe2—C17	2.014 (10)	B28—B30	1.79 (2)
Fe2—C24	2.015 (13)	B28—H28	1.1000
Fe2—C19	2.028 (11)	B29—C28	1.712 (18)
Fe2—C20	2.032 (12)	B29—B30	1.745 (18)
Fe2—C18	2.036 (13)	B29—H29	1.1000
Fe2—C23	2.044 (15)	B30—H30	1.1000
Fe2—C26	2.054 (14)	B31—C40	1.712 (15)
Fe3—C32	1.985 (12)	B31—B32	1.726 (18)
Fe3—C31	2.022 (11)	B31—B37	1.73 (2)
Fe3—C30	2.027 (10)	B31—C41	1.738 (16)
Fe3—C37	2.029 (13)	B31—B36	1.82 (2)
Fe3—C34	2.043 (11)	B31—H31	1.1000
Fe3—C35	2.044 (13)	B32—C40	1.675 (17)
Fe3—C33	2.050 (12)	B32—B33	1.756 (19)
Fe3—C39	2.051 (14)	B32—B37	1.78 (2)
Fe3—C36	2.051 (13)	B32—B38	1.806 (18)
Fe3—C38	2.088 (12)	B32—H32	1.1000
Fe4—C45	2.001 (12)	B33—B38	1.717 (18)
Fe4—C47	2.004 (11)	B33—C40	1.725 (16)
Fe4—C46	2.019 (12)	B33—B39	1.729 (18)
Fe4—C44	2.024 (12)	B33—B34	1.789 (18)
Fe4—C49	2.034 (14)	B33—H33	1.1000
Fe4—C50	2.035 (14)	B34—C41	1.687 (18)
Fe4—C43	2.042 (9)	B34—C40	1.710 (17)
Fe4—C51	2.045 (13)	B34—B35	1.714 (19)
Fe4—C52	2.046 (15)	B34—B39	1.74 (2)
Fe4—C48	2.085 (13)	B34—H34	1.1000
O1—C3	1.400 (15)	B35—C41	1.695 (16)
O1—H1	0.8200	B35—B40	1.760 (17)
O1—H3'B	0.6617	B35—B39	1.778 (19)
O2—C16	1.31 (2)	B35—B36	1.79 (2)
O2—H2	0.8200	B35—H35	1.1000
O2—H16'	0.6567	B36—C41	1.721 (18)
O3—C29	1.354 (16)	B36—B40	1.73 (2)
O3—H3	0.8200	B36—B37	1.75 (2)
O3—H29'	0.6750	B36—H36	1.1000
O4—C42	1.369 (13)	B37—B40	1.786 (19)
O4—H4	0.8200	B37—B38	1.79 (2)
O4—H42'	0.5889	B37—H37	1.1000
O1'—C3	1.15 (5)	B38—B39	1.742 (18)
O1'—H1'	0.8200	B38—B40	1.794 (18)
O2'—C16	1.24 (2)	B38—H38	1.1000
O2'—H2'	0.8200	B39—B40	1.806 (17)
O3'—C29	1.29 (2)	B39—H39	1.1000
O3'—H3'	0.8200	B40—H40	1.1000
O4'—C42	1.33 (4)	C1—C3	1.543 (14)
O4'—H4'	0.8200	C1—C2	1.636 (16)
B1—B2	1.65 (2)	C2—H2B	1.1000
B1—C1	1.710 (17)	C3—C4	1.484 (14)
B1—B7	1.720 (19)	C3—H3B	0.9800
B1—C2	1.771 (19)	C3—H3'B	0.9800
B1—B6	1.78 (2)	C4—C8	1.398 (15)
B1—H1A	1.1000	C4—C5	1.436 (16)
B2—C1	1.650 (16)	C5—C6	1.420 (16)
B2—B3	1.687 (19)	C5—H5A	0.9300
B2—B7	1.701 (16)	C6—C7	1.365 (17)
B2—B8	1.71 (2)	C6—H6A	0.9300
B2—H2A	1.1000	C7—C8	1.385 (15)
B3—C1	1.709 (17)	C7—H7A	0.9300
B3—B9	1.75 (2)	C8—H8A	0.9300
B3—B8	1.75 (2)	C9—C13	1.311 (18)
B3—B4	1.762 (18)	C9—C10	1.38 (2)
B3—H3A	1.1000	C9—H9A	0.9300
B4—B9	1.690 (19)	C10—C11	1.41 (2)
B4—B5	1.725 (17)	C10—H10A	0.9300
B4—C1	1.741 (16)	C11—C12	1.42 (2)
B4—C2	1.810 (17)	C11—H11A	0.9300
B4—H4A	1.1000	C12—C13	1.30 (2)
B5—B9	1.71 (2)	C12—H12A	0.9300
B5—B6	1.777 (18)	C13—H13A	0.9300
B5—B10	1.79 (2)	C14—C16	1.539 (15)
B5—C2	1.795 (18)	C14—C15	1.700 (16)
B5—H5	1.1000	C15—H15A	1.1000
B6—B7	1.715 (19)	C16—C17	1.525 (15)
B6—B10	1.770 (18)	C16—H16A	0.9800
B6—C2	1.808 (17)	C16—H16'	0.9800
B6—H6	1.1000	C17—C18	1.407 (15)
B7—B10	1.778 (18)	C17—C21	1.424 (14)
B7—B8	1.80 (2)	C18—C19	1.411 (15)
B7—H7	1.1000	C18—H18A	0.9300
B8—B10	1.73 (2)	C19—C20	1.393 (15)
B8—B9	1.83 (2)	C19—H19A	0.9300
B8—H8	1.1000	C20—C21	1.396 (14)
B9—B10	1.76 (2)	C20—H20A	0.9300
B9—H9	1.1000	C21—H21A	0.9300
B10—H10	1.1000	C22—C26	1.375 (17)
B11—B12	1.66 (2)	C22—C23	1.401 (18)
B11—C14	1.706 (18)	C22—H22A	0.9300
B11—B17	1.72 (2)	C23—C24	1.337 (19)
B11—C15	1.759 (19)	C23—H23A	0.9300
B11—B16	1.81 (2)	C24—C25	1.392 (18)
B11—H11	1.1000	C24—H24A	0.9300
B12—B13	1.60 (2)	C25—C26	1.388 (18)
B12—C14	1.601 (18)	C25—H25A	0.9300
B12—B17	1.66 (2)	C26—H26A	0.9300
B12—B18	1.71 (2)	C27—C29	1.493 (13)
B12—H12	1.1000	C27—C28	1.692 (15)
B13—C14	1.642 (19)	C28—H28A	1.1000
B13—B14	1.73 (2)	C29—C30	1.479 (13)
B13—B19	1.74 (2)	C29—H29A	0.9800
B13—B18	1.76 (2)	C29—H29'	0.9800
B13—H13	1.1000	C30—C34	1.390 (14)
B14—C14	1.652 (19)	C30—C31	1.434 (13)
B14—B15	1.74 (2)	C31—C32	1.385 (15)
B14—B19	1.78 (2)	C31—H31A	0.9300
B14—C15	1.784 (19)	C32—C33	1.378 (16)
B14—H14	1.1000	C32—H32A	0.9300
B15—B19	1.77 (2)	C33—C34	1.389 (16)
B15—C15	1.777 (18)	C33—H33A	0.9300
B15—B20	1.81 (2)	C34—H34A	0.9300
B15—B16	1.84 (2)	C35—C39	1.383 (18)
B15—H15	1.1000	C35—C36	1.421 (19)
B16—B20	1.71 (2)	C35—H35A	0.9300
B16—B17	1.79 (3)	C36—C37	1.493 (18)
B16—C15	1.820 (19)	C36—H36A	0.9300
B16—H16	1.1000	C37—C38	1.424 (15)
B17—B18	1.69 (2)	C37—H37A	0.9300
B17—B20	1.73 (2)	C38—C39	1.415 (17)
B17—H17	1.1000	C38—H38A	0.9300
B18—B20	1.65 (2)	C39—H39A	0.9300
B18—B19	1.67 (2)	C40—C42	1.537 (13)
B18—H18	1.1000	C40—C41	1.657 (13)
B19—B20	1.74 (2)	C41—H41	1.1000
B19—H19	1.1000	C42—C43	1.469 (13)
B20—H20	1.1000	C42—H42	0.9800
B21—C27	1.694 (15)	C42—H42'	0.9800
B21—B26	1.717 (19)	C43—C44	1.405 (14)
B21—B22	1.736 (18)	C43—C47	1.430 (13)
B21—B25	1.758 (17)	C44—C45	1.355 (15)
B21—C28	1.766 (17)	C44—H44	0.9300
B21—H21	1.1000	C45—C46	1.360 (15)
B22—C27	1.694 (17)	C45—H45	0.9300
B22—B26	1.719 (19)	C46—C47	1.407 (15)
B22—B23	1.726 (17)	C46—H46	0.9300
B22—B27	1.798 (19)	C47—H47	0.9300
B22—H22	1.1000	C48—C52	1.457 (17)
B23—C27	1.675 (15)	C48—C49	1.468 (18)
B23—B24	1.68 (2)	C48—H48	0.9300
B23—B28	1.704 (19)	C49—C50	1.489 (19)
B23—B27	1.705 (19)	C49—H49	0.9300
B23—H23	1.1000	C50—C51	1.377 (18)
B24—B28	1.65 (2)	C50—H50	0.9300
B24—C27	1.688 (17)	C51—C52	1.379 (18)
B24—B29	1.71 (2)	C51—H51	0.9300
B24—C28	1.728 (19)	C52—H52	0.9300

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₈H₁₇B₁₀O)]
M_r	358.26
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	27.051 (2), 8.9682 (7), 29.191 (3)
V (Å³)	7081.8 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.25 × 0.14 × 0.07

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.816, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	35277, 12025, 5629
R_int	0.115
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.181, 1.03
No. of reflections	12025
No. of parameters	942
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.45
Absolute structure	Flack (1983), 5617 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Crundwell, G., Arellanes, C., Gomez, F. & Kantardjieff, K. (1999). Acta Cryst. C55, IUC9900087. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, H., Chan, H.-S. & Xie, Z.-W. (2006). Organometallics, 25, 2617–2625. Web of Science CSD CrossRef CAS Google Scholar
Terrasson, V., Planas, J. G., Prim, D., Viñas, C., Teixidor, F., Light, M. E. & Hursthouse, M. B. (2008). J. Org. Chem. 73, 9140–9143. Web of Science CSD CrossRef PubMed CAS Google Scholar
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