2-(4-Ferrocenylphen­yl)-4,4,5,5-tetra­methyl-1,3,2-dioxaborolane

Boyd, P.D.W.; Paauwe, J.D.

doi:10.1107/S1600536808035228

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1494

doi:10.1107/S1600536808035228

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2-(4-Ferrocenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Peter D. W. Boyd ^a ^* and J. D. Paauwe ^a

^aDepartment of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand
^*Correspondence e-mail: pdw.boyd@auckland.ac.nz

(Received 23 October 2008; accepted 28 October 2008; online 8 November 2008)

In the title compound,, [Fe(C₅H₅)(C₁₇H₂₀BO₂)], the two near parallel cyclopentadienyl rings of the ferrocene group are eclipsed. The benzene ring is tilted with respect to the attached cyclopentadiene ring by 17.0 (1)° and by 24.2 (1)° with respect to the dioxaborolane ring. The molecules assemble in the crystal via C—H⋯π interactions between the cyclopentadienyl H atoms and the benzene and cyclopentadienyl rings of neighbouring molecules.

Related literature

For the related tris(4-ferrocenylphenyl)boroxine benzene solvate, see: Makarov et al. (2004 ). For other related structures, see: Anderson et al. (2003 ); Nyamori & Bala (2008 ). For related literature, see: Leclerc et al. (2003 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₇H₂₀BO₂)]
M_r = 388.08
Monoclinic, P 2₁ /c
a = 12.4439 (3) Å
b = 12.9832 (3) Å
c = 13.0728 (3) Å
β = 117.126 (1)°
V = 1879.75 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 89 (2) K
0.37 × 0.37 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.717, T_max = 0.849
23134 measured reflections
4442 independent reflections
3984 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.03
4442 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯C12ⁱ	0.93	2.86	3.6302 (19)	141
C5—H5⋯C6ⁱⁱ	0.93	2.62	3.538 (2)	168
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035228/hg2435sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035228/hg2435Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was prepared from the reaction of lithiated 4-bromophenylferrocene with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxoborolane in tetrahydrofuran. Unlike the related tris(4-ferrocenylphenyl)boroxine benzene solvate (Makarov et al. (2004), the 2-(4-ferrocenyl-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is monomeric (Fig. 1). The two cyclopentadienyl rings are nearly eclipsed, average torsion angle 2.1 (1)°, with a small tilt of the two planes (C1—C5 and C6—C10) of 3.5 (1)°. The distances of the iron atom to the ring centroids were 1.6514 (2)Å and 1.6475 (2) Å respectively. The phenyl ring is tilted by 17.0 (1)° with respect to the (C6—C10) plane. This value is slightly higher than that observed in similar structures (Anderson et al. (2003), Nyamori and Bala (2008)). The dioxaborolane ring is in a half-chair conformation, with an O1—C17—C18—O2 torsion angle of 24.2 (1)°. The BO₂ group is rotated away from the plane of the phenyl ring system by 11.1 (2)°, and the angle between the dioxaborolane ring and the phenylplane is 9.9 (1)°. The molecules pack in the crystal, (Fig. 2), with C—H···π interactions between cyclopentadienyl hydrogen atoms and the phenyl and cyclopentadienyl rings of neighbouring molecules, Table 1.

Related literature top

For the related tris(4-ferrocenylphenyl)boroxine benzene

solvate, see: Makarov et al. (2004). For other related structures, see: Anderson et al. (2003); Nyamori & Bala (2008). For related literature, see: Leclerc et al. (2003).

Experimental top

To a solution of 4-bromophenyl ferrocene (0.2 g, 0.59 mmol) in dry THF (10 mL) stirred at -78°C under nitrogen was added dropwise a solution of n-BuLi 2.5M in hexane (0.51 ml, 0.88 mmol).The mixture was then stirred at -78 °C for 20 minutes. Then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxoborolane (0.18 ml, 0.88 mmol) was added, the stirring was kept at -78°C for 2 h and the mixture allowed to warm to -35 C and stir for 1 h and then warmed to room temperature. The reaction mixture was then poured into water and extracted with diethyl ether (2 x 25 ml). The combined organic layers were washed with brine and dried with Na₂SO₄. The solvent removed under reduced pressure and purified by column chromatography (SiO₂, Hexane/DCM =2/1) to give the pure compound 2-(4-ferrocenyl-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.052 g, 0.129 mmol, 23%) as an orange solid. FAB-MS (C₂₂H₂₅¹⁰BFeO₂) 387.13293 (C₂₂H₂₅¹¹BFeO₂) 388.12934. ¹H NMR (CDCl₃, 300 MHz) δ 1.36 (CH₃, s 12H), 4.02 (CpH, s, 5H), 4.33 (CpH, t, J=1.84, 2H), 4.68 (CpH, t, J =1.85 2H), 7.46 (ArH, d, J=8.3 2H), 7.72 (ArH, d, J=8.3 2H) p.p.m..

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2008).

Figures top

	Fig. 1. Structure of (I) showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I) showing C—H..π interactions between adjacent molecules. [Symmetry codes: x,y,z and 1 - x,1 - y,1 - z]

2-(4-Ferrocenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane top

Crystal data top

[Fe(C₅H₅)(C₁₇H₂₀BO₂)]	F(000) = 816
M_r = 388.08	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9781 reflections
a = 12.4439 (3) Å	θ = 1.8–27.8°
b = 12.9832 (3) Å	µ = 0.82 mm⁻¹
c = 13.0728 (3) Å	T = 89 K
β = 117.126 (1)°	Block, orange
V = 1879.75 (8) Å³	0.37 × 0.37 × 0.2 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4442 independent reflections
Radiation source: fine-focus sealed tube	3984 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.8°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→14
T_min = 0.717, T_max = 0.849	k = 0→17
23134 measured reflections	l = 0→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0491P)² + 1.0943P] where P = (F_o² + 2F_c²)/3
4442 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₁₇H₂₀BO₂)]	V = 1879.75 (8) Å³
M_r = 388.08	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4439 (3) Å	µ = 0.82 mm⁻¹
b = 12.9832 (3) Å	T = 89 K
c = 13.0728 (3) Å	0.37 × 0.37 × 0.2 mm
β = 117.126 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4442 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3984 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.849	R_int = 0.027
23134 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	Δρ_max = 0.86 e Å⁻³
4442 reflections	Δρ_min = −0.31 e Å⁻³
239 parameters

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
Fe1	0.244744 (18)	0.661122 (14)	0.209954 (16)	0.01545 (8)
O2	0.36539 (9)	1.21833 (8)	−0.03562 (9)	0.0207 (2)
O1	0.16554 (9)	1.19391 (8)	−0.16076 (9)	0.0195 (2)
C11	0.26427 (12)	0.89643 (10)	0.14427 (11)	0.0157 (3)
C14	0.26540 (13)	1.05937 (10)	0.00034 (12)	0.0167 (3)
C18	0.33635 (13)	1.29767 (11)	−0.12386 (12)	0.0187 (3)
C2	0.16209 (14)	0.52057 (11)	0.16048 (14)	0.0231 (3)
H2	0.1105	0.4901	0.1854	0.028*
C16	0.37235 (12)	0.94523 (10)	0.16343 (12)	0.0178 (3)
H16	0.4447	0.9239	0.2241	0.021*
C7	0.15815 (13)	0.78484 (11)	0.23606 (12)	0.0186 (3)
H7	0.0789	0.8050	0.1895	0.022*
C13	0.15859 (13)	1.00753 (10)	−0.02096 (12)	0.0172 (3)
H13	0.0868	1.0269	−0.0836	0.021*
C8	0.26304 (13)	0.81901 (11)	0.22597 (12)	0.0167 (3)
C9	0.36571 (13)	0.76831 (11)	0.31467 (12)	0.0187 (3)
H9	0.4454	0.7758	0.3281	0.022*
C6	0.19744 (14)	0.71467 (11)	0.33018 (12)	0.0209 (3)
H6	0.1480	0.6811	0.3556	0.025*
B1	0.26500 (15)	1.15783 (11)	−0.06779 (14)	0.0174 (3)
C15	0.37260 (13)	1.02504 (11)	0.09282 (12)	0.0184 (3)
H15	0.4453	1.0564	0.1071	0.022*
C5	0.23381 (15)	0.61510 (11)	0.05503 (13)	0.0243 (3)
H5	0.2370	0.6572	−0.0011	0.029*
C21	0.39377 (14)	1.39832 (11)	−0.06503 (13)	0.0238 (3)
H21A	0.3680	1.4143	−0.0079	0.036*
H21B	0.3695	1.4526	−0.1210	0.036*
H21C	0.4801	1.3916	−0.0290	0.036*
C4	0.33403 (14)	0.56821 (11)	0.14749 (13)	0.0226 (3)
H4	0.4144	0.5745	0.1628	0.027*
C10	0.32509 (14)	0.70475 (11)	0.37867 (12)	0.0208 (3)
H10	0.3735	0.6639	0.4413	0.025*
C12	0.15769 (12)	0.92783 (10)	0.04947 (12)	0.0169 (3)
H12	0.0854	0.8949	0.0335	0.020*
C17	0.19486 (13)	1.29760 (11)	−0.18488 (13)	0.0201 (3)
C22	0.39120 (14)	1.26270 (11)	−0.20117 (14)	0.0235 (3)
H22A	0.4761	1.2510	−0.1555	0.035*
H22B	0.3790	1.3150	−0.2573	0.035*
H22C	0.3530	1.2000	−0.2395	0.035*
C3	0.29014 (14)	0.50988 (11)	0.21282 (14)	0.0228 (3)
H3	0.3369	0.4715	0.2783	0.027*
C20	0.14060 (15)	1.37292 (13)	−0.13159 (16)	0.0294 (3)
H20A	0.0554	1.3605	−0.1625	0.044*
H20B	0.1539	1.4422	−0.1489	0.044*
H20C	0.1783	1.3635	−0.0498	0.044*
C19	0.13736 (16)	1.31085 (15)	−0.31429 (14)	0.0312 (4)
H19A	0.1653	1.2574	−0.3471	0.047*
H19B	0.1593	1.3768	−0.3324	0.047*
H19C	0.0511	1.3068	−0.3453	0.047*
C1	0.12727 (14)	0.58627 (12)	0.06311 (13)	0.0249 (3)
H1	0.0489	0.6067	0.0136	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02072 (12)	0.00975 (11)	0.01600 (12)	−0.00098 (7)	0.00849 (9)	0.00033 (7)
O2	0.0219 (5)	0.0155 (5)	0.0231 (5)	−0.0012 (4)	0.0087 (4)	0.0059 (4)
O1	0.0234 (5)	0.0134 (5)	0.0205 (5)	−0.0019 (4)	0.0090 (4)	0.0031 (4)
C11	0.0225 (6)	0.0095 (5)	0.0171 (6)	−0.0009 (5)	0.0106 (5)	−0.0026 (5)
C14	0.0228 (7)	0.0119 (6)	0.0174 (6)	0.0003 (5)	0.0110 (5)	−0.0002 (5)
C18	0.0234 (7)	0.0130 (6)	0.0206 (7)	0.0000 (5)	0.0107 (6)	0.0037 (5)
C2	0.0296 (8)	0.0134 (6)	0.0292 (8)	−0.0063 (6)	0.0159 (6)	−0.0055 (6)
C16	0.0196 (6)	0.0135 (6)	0.0192 (6)	0.0003 (5)	0.0078 (5)	−0.0001 (5)
C7	0.0243 (7)	0.0137 (6)	0.0202 (7)	−0.0002 (5)	0.0122 (6)	−0.0005 (5)
C13	0.0214 (7)	0.0144 (6)	0.0155 (6)	0.0007 (5)	0.0080 (5)	−0.0011 (5)
C8	0.0235 (7)	0.0105 (6)	0.0170 (6)	−0.0017 (5)	0.0099 (5)	−0.0018 (5)
C9	0.0232 (7)	0.0140 (6)	0.0176 (6)	−0.0024 (5)	0.0081 (6)	−0.0015 (5)
C6	0.0310 (8)	0.0147 (6)	0.0214 (7)	−0.0024 (5)	0.0158 (6)	0.0000 (5)
B1	0.0228 (8)	0.0131 (7)	0.0182 (7)	−0.0004 (5)	0.0111 (6)	−0.0004 (5)
C15	0.0207 (6)	0.0142 (6)	0.0215 (7)	−0.0014 (5)	0.0106 (6)	−0.0008 (5)
C5	0.0386 (9)	0.0156 (7)	0.0207 (7)	−0.0018 (6)	0.0153 (6)	−0.0020 (5)
C21	0.0284 (7)	0.0160 (7)	0.0263 (7)	−0.0033 (6)	0.0118 (6)	0.0005 (6)
C4	0.0291 (7)	0.0154 (6)	0.0273 (7)	−0.0018 (6)	0.0165 (6)	−0.0046 (6)
C10	0.0305 (8)	0.0149 (6)	0.0153 (6)	−0.0012 (5)	0.0090 (6)	0.0011 (5)
C12	0.0210 (6)	0.0127 (6)	0.0185 (6)	−0.0031 (5)	0.0102 (5)	−0.0032 (5)
C17	0.0246 (7)	0.0128 (6)	0.0241 (7)	0.0002 (5)	0.0122 (6)	0.0038 (5)
C22	0.0303 (8)	0.0157 (6)	0.0308 (8)	−0.0003 (6)	0.0193 (7)	0.0017 (6)
C3	0.0316 (8)	0.0103 (6)	0.0272 (7)	0.0015 (5)	0.0140 (6)	0.0007 (5)
C20	0.0302 (8)	0.0184 (7)	0.0438 (10)	0.0026 (6)	0.0205 (8)	−0.0005 (7)
C19	0.0293 (8)	0.0348 (9)	0.0256 (8)	0.0004 (7)	0.0090 (7)	0.0131 (7)
C1	0.0274 (8)	0.0194 (7)	0.0216 (7)	−0.0019 (6)	0.0057 (6)	−0.0056 (6)

Geometric parameters (Å, º) top

Fe1—C6	2.0357 (14)	C13—C12	1.3885 (19)
Fe1—C3	2.0388 (14)	C13—H13	0.9300
Fe1—C10	2.0431 (14)	C8—C9	1.435 (2)
Fe1—C4	2.0454 (15)	C9—C10	1.4220 (19)
Fe1—C7	2.0477 (14)	C9—H9	0.9300
Fe1—C2	2.0492 (14)	C6—C10	1.422 (2)
Fe1—C9	2.0488 (14)	C6—H6	0.9300
Fe1—C1	2.0512 (15)	C15—H15	0.9300
Fe1—C5	2.0558 (15)	C5—C4	1.419 (2)
Fe1—C8	2.0626 (14)	C5—C1	1.427 (2)
O2—B1	1.3695 (19)	C5—H5	0.9300
O2—C18	1.4636 (16)	C21—H21A	0.9600
O1—B1	1.3626 (19)	C21—H21B	0.9600
O1—C17	1.4663 (16)	C21—H21C	0.9600
C11—C12	1.4007 (19)	C4—C3	1.424 (2)
C11—C16	1.4020 (19)	C4—H4	0.9300
C11—C8	1.4718 (18)	C10—H10	0.9300
C14—C13	1.3998 (19)	C12—H12	0.9300
C14—C15	1.403 (2)	C17—C19	1.516 (2)
C14—B1	1.557 (2)	C17—C20	1.525 (2)
C18—C21	1.519 (2)	C22—H22A	0.9600
C18—C22	1.524 (2)	C22—H22B	0.9600
C18—C17	1.567 (2)	C22—H22C	0.9600
C2—C3	1.426 (2)	C3—H3	0.9300
C2—C1	1.426 (2)	C20—H20A	0.9600
C2—H2	0.9300	C20—H20B	0.9600
C16—C15	1.3887 (19)	C20—H20C	0.9600
C16—H16	0.9300	C19—H19A	0.9600
C7—C6	1.426 (2)	C19—H19B	0.9600
C7—C8	1.4405 (19)	C19—H19C	0.9600
C7—H7	0.9300	C1—H1	0.9300

C6—Fe1—C3	119.34 (6)	C11—C8—Fe1	129.97 (9)
C6—Fe1—C10	40.82 (6)	C10—C9—C8	108.51 (13)
C3—Fe1—C10	104.60 (6)	C10—C9—Fe1	69.45 (8)
C6—Fe1—C4	155.59 (6)	C8—C9—Fe1	70.09 (8)
C3—Fe1—C4	40.80 (6)	C10—C9—H9	125.7
C10—Fe1—C4	120.46 (6)	C8—C9—H9	125.7
C6—Fe1—C7	40.89 (6)	Fe1—C9—H9	126.3
C3—Fe1—C7	156.19 (6)	C10—C6—C7	108.43 (12)
C10—Fe1—C7	68.79 (6)	C10—C6—Fe1	69.87 (8)
C4—Fe1—C7	162.19 (6)	C7—C6—Fe1	70.01 (8)
C6—Fe1—C2	105.52 (6)	C10—C6—H6	125.8
C3—Fe1—C2	40.82 (6)	C7—C6—H6	125.8
C10—Fe1—C2	121.05 (6)	Fe1—C6—H6	125.9
C4—Fe1—C2	68.57 (6)	O1—B1—O2	114.03 (12)
C7—Fe1—C2	121.64 (6)	O1—B1—C14	123.86 (13)
C6—Fe1—C9	68.60 (6)	O2—B1—C14	122.06 (13)
C3—Fe1—C9	121.93 (6)	C16—C15—C14	121.35 (13)
C10—Fe1—C9	40.67 (5)	C16—C15—H15	119.3
C4—Fe1—C9	107.46 (6)	C14—C15—H15	119.3
C7—Fe1—C9	68.77 (6)	C4—C5—C1	108.05 (13)
C2—Fe1—C9	157.80 (6)	C4—C5—Fe1	69.37 (8)
C6—Fe1—C1	123.42 (6)	C1—C5—Fe1	69.50 (9)
C3—Fe1—C1	68.54 (6)	C4—C5—H5	126.0
C10—Fe1—C1	158.56 (6)	C1—C5—H5	126.0
C4—Fe1—C1	68.41 (6)	Fe1—C5—H5	126.7
C7—Fe1—C1	108.84 (6)	C18—C21—H21A	109.5
C2—Fe1—C1	40.69 (6)	C18—C21—H21B	109.5
C9—Fe1—C1	160.07 (6)	H21A—C21—H21B	109.5
C6—Fe1—C5	161.33 (7)	C18—C21—H21C	109.5
C3—Fe1—C5	68.38 (6)	H21A—C21—H21C	109.5
C10—Fe1—C5	157.54 (7)	H21B—C21—H21C	109.5
C4—Fe1—C5	40.47 (6)	C5—C4—C3	108.11 (13)
C7—Fe1—C5	126.07 (6)	C5—C4—Fe1	70.16 (9)
C2—Fe1—C5	68.40 (6)	C3—C4—Fe1	69.36 (8)
C9—Fe1—C5	123.65 (6)	C5—C4—H4	125.9
C1—Fe1—C5	40.67 (6)	C3—C4—H4	125.9
C6—Fe1—C8	68.88 (5)	Fe1—C4—H4	126.1
C3—Fe1—C8	159.79 (6)	C9—C10—C6	108.03 (12)
C10—Fe1—C8	68.77 (5)	C9—C10—Fe1	69.88 (8)
C4—Fe1—C8	124.87 (6)	C6—C10—Fe1	69.31 (8)
C7—Fe1—C8	41.03 (5)	C9—C10—H10	126.0
C2—Fe1—C8	158.96 (6)	C6—C10—H10	126.0
C9—Fe1—C8	40.85 (6)	Fe1—C10—H10	126.4
C1—Fe1—C8	124.36 (6)	C13—C12—C11	120.85 (13)
C5—Fe1—C8	110.09 (6)	C13—C12—H12	119.6
B1—O2—C18	107.39 (11)	C11—C12—H12	119.6
B1—O1—C17	107.07 (11)	O1—C17—C19	107.88 (12)
C12—C11—C16	118.08 (12)	O1—C17—C20	106.56 (12)
C12—C11—C8	121.46 (12)	C19—C17—C20	110.78 (14)
C16—C11—C8	120.36 (13)	O1—C17—C18	102.89 (11)
C13—C14—C15	117.52 (12)	C19—C17—C18	114.64 (12)
C13—C14—B1	121.73 (13)	C20—C17—C18	113.31 (12)
C15—C14—B1	120.50 (13)	C18—C22—H22A	109.5
O2—C18—C21	108.44 (11)	C18—C22—H22B	109.5
O2—C18—C22	106.79 (11)	H22A—C22—H22B	109.5
C21—C18—C22	110.03 (12)	C18—C22—H22C	109.5
O2—C18—C17	102.54 (10)	H22A—C22—H22C	109.5
C21—C18—C17	114.71 (12)	H22B—C22—H22C	109.5
C22—C18—C17	113.65 (12)	C4—C3—C2	108.11 (13)
C3—C2—C1	107.76 (13)	C4—C3—Fe1	69.85 (8)
C3—C2—Fe1	69.20 (8)	C2—C3—Fe1	69.98 (8)
C1—C2—Fe1	69.73 (8)	C4—C3—H3	125.9
C3—C2—H2	126.1	C2—C3—H3	125.9
C1—C2—H2	126.1	Fe1—C3—H3	125.8
Fe1—C2—H2	126.5	C17—C20—H20A	109.5
C15—C16—C11	120.74 (13)	C17—C20—H20B	109.5
C15—C16—H16	119.6	H20A—C20—H20B	109.5
C11—C16—H16	119.6	C17—C20—H20C	109.5
C6—C7—C8	107.89 (13)	H20A—C20—H20C	109.5
C6—C7—Fe1	69.10 (8)	H20B—C20—H20C	109.5
C8—C7—Fe1	70.04 (8)	C17—C19—H19A	109.5
C6—C7—H7	126.1	C17—C19—H19B	109.5
C8—C7—H7	126.1	H19A—C19—H19B	109.5
Fe1—C7—H7	126.4	C17—C19—H19C	109.5
C12—C13—C14	121.36 (13)	H19A—C19—H19C	109.5
C12—C13—H13	119.3	H19B—C19—H19C	109.5
C14—C13—H13	119.3	C2—C1—C5	107.97 (14)
C9—C8—C7	107.14 (12)	C2—C1—Fe1	69.58 (8)
C9—C8—C11	126.85 (12)	C5—C1—Fe1	69.84 (9)
C7—C8—C11	125.90 (13)	C2—C1—H1	126.0
C9—C8—Fe1	69.06 (8)	C5—C1—H1	126.0
C7—C8—Fe1	68.93 (8)	Fe1—C1—H1	126.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···C12ⁱ	0.93	2.86	3.6302 (19)	141
C5—H5···C6ⁱⁱ	0.93	2.62	3.538 (2)	168

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₇H₂₀BO₂)]
M_r	388.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	89
a, b, c (Å)	12.4439 (3), 12.9832 (3), 13.0728 (3)
β (°)	117.126 (1)
V (Å³)	1879.75 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.37 × 0.37 × 0.2

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.717, 0.849
No. of measured, independent and observed [I > 2σ(I)] reflections	23134, 4442, 3984
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.04
No. of reflections	4442
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.31

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···C12ⁱ	0.93	2.86	3.6302 (19)	141.4
C5—H5···C6ⁱⁱ	0.93	2.62	3.538 (2)	167.6

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

We thank Tania Groutso for help with the data collection.

References

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