Acta Crystallographica Section E
Acta Crystallographica
Section E CRYSTALLOGRAPHIC COMMUNICATIONS

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

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

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)].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809051903/cv2664sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809051903/cv2664Isup2.hkl Contains datablock I

CCDC reference: 766650

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.018 Å
Disorder in main residue
R factor = 0.075
wR factor = 0.181
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT312_ALERT_2_A Strange C-O-H Geometry (C-O .LT. 1.25 Ang) .....        O1'

Author Response: The oxygen atom is disordered over two sites with occupancy of 0.8 and 0.2 respectively.

PLAT415_ALERT_2_A Short Inter D-H..H-X       H2A    ..  H3'     ..       1.82 Ang.

Author Response: The oxygen atom is disordered over two sites with occupancy of 0.60 and 0.40 respectively.


PLAT415_ALERT_2_A Short Inter D-H..H-X       H12    ..  H4'     ..       1.63 Ang.

Author Response: The oxygen atom is disordered over two sites with occupancy of 0.60 and 0.40 respectively.


PLAT415_ALERT_2_A Short Inter D-H..H-X       H23    ..  H1'     ..       1.70 Ang.

Author Response: The oxygen atom is disordered over two sites with occupancy of 0.60 and 0.40 respectively.



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on  C-C Bonds (x 1000) Ang ..         18
PLAT414_ALERT_2_B Short Intra D-H..H-X       H2     ..  H12     ..       1.80 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H2A    ..  H3      ..       1.97 Ang.

Author Response: The oxygen atom is disordered over two sites with occupancy of 0.60 and 0.40 respectively.


PLAT415_ALERT_2_B Short Inter D-H..H-X       H41    ..  H2'     ..       2.04 Ang.

Author Response: The oxygen atom is disordered over two sites with occupancy of 0.60 and 0.40 respectively.



Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            block
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.51
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         B7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe4
PLAT367_ALERT_2_C Long?  C(sp?)-C(sp?) Bond  C1     -   C2     ...       1.63 Ang.
PLAT367_ALERT_2_C Long?  C(sp?)-C(sp?) Bond  C14    -   C15    ...       1.70 Ang.
PLAT367_ALERT_2_C Long?  C(sp?)-C(sp?) Bond  C27    -   C28    ...       1.69 Ang.
PLAT367_ALERT_2_C Long?  C(sp?)-C(sp?) Bond  C40    -   C41    ...       1.66 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H2A     ..       1.96 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H13    ..  H2'     ..       1.90 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H4     ..  H41     ..       1.97 Ang.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT234_ALERT_4_C Large Hirshfeld Difference B1     --  B7      ..       0.15 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference B2     --  B7      ..       0.15 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference B7     --  B8      ..       0.19 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C17    --  C18     ..       0.17 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.02
           From the CIF: _reflns_number_total              12025
           Count of symmetry unique reflns         6398
           Completeness (_total/calc)            187.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      5627
           Fraction of Friedel pairs measured     0.879
           Are heavy atom types Z>Si present        yes
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................       4.00 Perc.
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C1
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C2
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C14
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C15
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C27
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C28
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C40
PLAT343_ALERT_2_G Check sp?     Angle Range in Main Residue for ..        C41
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.55
PLAT917_ALERT_2_G The FCF is likely NOT based on a BASF/TWIN Flack          !
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1379
            C12 -FE1 -C5  -C6    143.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1387
            C12 -FE1 -C5  -C4     27.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1401
            C13 -FE1 -C6  -C7   -176.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1409
            C13 -FE1 -C6  -C5     62.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1421
            C9  -FE1 -C7  -C6     70.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1428
            C9  -FE1 -C7  -C8   -172.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1462
            C7  -FE1 -C9  -C13   121.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1470
            C7  -FE1 -C9  -C10     1.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1518
            C5  -FE1 -C12 -C13    51.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1526
            C5  -FE1 -C12 -C11   169.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1539
            C6  -FE1 -C13 -C12   133.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1547
            C6  -FE1 -C13 -C9     11.00  7.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1775
            C23 -FE2 -C19 -C20  -172.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1783
            C23 -FE2 -C19 -C18   -50.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1851
            C19 -FE2 -C23 -C24  -148.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #       1859
            C19 -FE2 -C23 -C22   -29.00  4.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      39.10 Deg.
              C3   -O1   -H3'B    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      43.40 Deg.
              C29  -O3   -H29'    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      38.60 Deg.
              C42  -O4   -H42'    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      35.70 Deg.
              O1'  -C3   -H3B     1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      25.20 Deg.
              O1   -C3   -H3'B    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      38.10 Deg.
              O2'  -C16  -H16A    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      29.00 Deg.
              O2   -C16  -H16'    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      35.10 Deg.
              O3'  -C29  -H29A    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      28.20 Deg.
              O3   -C29  -H29'    1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      28.50 Deg.
              O4'  -C42  -H42     1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      22.00 Deg.
              O4   -C42  -H42'    1.555   1.555   1.555
PLAT792_ALERT_1_G The Model has Chirality at C3      (Verify) ....          R
PLAT792_ALERT_1_G The Model has Chirality at C42     (Verify) ....          R

   4 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  23 ALERT level C = Check and explain
  42 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  32 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  34 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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

[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)]	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).

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