(R)-2-Ferrocenyl-4-hydroxy­methyl-4,5-dihydro-1,3-oxazole

Todd, M.H.; Motevalli, M.; El-Fayyoumy, S.; Richards, C.

doi:10.1107/S1600536806006982

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 4| April 2006| Pages m719-m720

https://doi.org/10.1107/S1600536806006982

(R)-2-Ferrocenyl-4-hydroxymethyl-4,5-dihydro-1,3-oxazole

Matthew H. Todd,^a ^* Majid Motevalli,^b Shaimaa El-Fayyoumy ^b and Chris Richards ^b

^aSchool of Chemistry, University of Sydney, NSW 2006, Australia, and ^bSchool of Biological and Chemical Sciences, Queen Mary University of London, Mile End Road, London E1 4NS, England
^*Correspondence e-mail: m.todd@chem.usyd.edu.au

(Received 3 February 2006; accepted 27 February 2006; online 8 March 2006)

The title compound, [Fe(C₅H₅)(C₉H₁₀NO₂)], was prepared from ferrocenecarboxylic acid and serine. In the crystal structure, molecules are arranged in chains with an intermolecular hydrogen bond between hydroxy groups and N atoms.

Comment

A series of serine-derived oxazoles has been shown to be effective in asymmetric alkylation reactions, and hence their crystal structures are of interest (Jones & Richards, 2004 ). As representatives of the general amino alcohol class of ligands for these reactions, we have an interest in understanding their non-linear catalytic characteristics. A single-crystal X-ray structure has been reported for a related compound, viz. (4S)-4-(1-hydroxy-1-methylethyl)-2-ferrocenyl-4,5-dihydro-1,3-oxazole monohydrate (Chesney et al., 1998 ).

The structure of the title compound, (I) (Fig. 1), reveals that the two cyclopentadienyl rings of ferrocene deviate by only four degrees from a fully eclipsed conformation. The torsion angle C1—C1c—C2c—C11 (where C1c and C2c are the cycopentadiene ring centroids) is −3.5 (6)°. The oxazoline ring is almost coplanar with the cyclopentadienyl ring to which it is attached [interplanar angle = 9.2 (5)° and C2—C1—C6—O1 = −6.3 (10)°], the O rather than the N atom being slightly closer to iron. The oxazoline hydroxymethyl substituent is oriented away from the iron-cyclopentadienyl group of ferrocene. Significantly, the opposite rotamer, with respect to rotation about the ferrocene-oxazoline C—C σ-bond, was observed in the structure reported by Chesney et al. (1998). This contains a larger 1-hydroxy-1-methylethyloxazoline substituent, and in both cases the hydroxy group is oriented over the oxazoline ring; in the present structure, N1—C8—C9—O2 = −73.7 (7)°.

Figure 1
The molecular structure of (I)

. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
The polymeric assembly of (I)

, involving hydrogen-bonded (dashed lines) oxazole groups.

Experimental

LiAlH₄ (68 mg, 1.797 mmol, 1.1 equivalent) was added to a solution of (S)-4-carbomethoxy-2-ferrocenyl-1,3-oxazoline (513 mg, 1.634 mmol) in diethyl ether (15 ml) cooled to 273 K. After stirring for 15 min, ethyl acetate (25 ml) was added followed by water (38 ml), and the organic layer was then separated, dried (MgSO₄), filtered and concentrated in vacuo to give the crude alcohol as an orange solid. The crude solid was recrystallized from dichloromethane and hexane (ca 1:1) to give the pure oxazoline [434 mg, 93%; m.p. 390–392 K (literature 390–392 K]. ¹H NMR (CDCl₃): δ 3.59 (1H, dd, J = 11.4, 3.7 Hz, OCHH) and 3.86 (1H, dd, J = 11.4, 3.2 Hz OCHH), 4.16 (5H, s, Cp), 4.18–4.40 (5H, m, OCH₂ + CHN + Cp × 2), 4.72 (2H, m, Cp).

Crystal data

[Fe(C₅H₅)(C₉H₁₀NO₂)]
M_r = 285.12
Monoclinic, P 2₁
a = 5.808 (4) Å
b = 7.557 (3) Å
c = 13.716 (8) Å
β = 92.39 (6)°
V = 601.5 (6) Å³
Z = 2
D_x = 1.574 Mg m⁻³
Mo Kα radiation
Cell parameters from 25 reflections
θ = 9.9–13.2°
μ = 1.25 mm⁻¹
T = 160 (2) K
Prism, orange
0.30 × 0.13 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
ω/2θ scans
Absorption correction: ψ scan(North et al., 1968 )T_min = 0.706, T_max = 0.912
1305 measured reflections
1137 independent reflections
877 reflections with I > 2σ(I)
R_int = 0.033
θ_max = 25.0°
h = −1 → 6
k = 0 → 8
l = −16 → 16
2 standard reflections every 100 reflections intensity decay: 5%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.079
S = 1.03
1137 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0336P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 171 Friedel Pairs
Flack parameter: 0.01 (4)

Table 1
Selected torsion angles (°)

C2—C1—C6—O1	−6.3 (10)
N1—C8—C9—O2	−73.7 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H20⋯N1ⁱ	0.87 (7)	2.02 (8)	2.877 (7)	165 (7)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

H atoms were treated as riding atoms [C—H = 0.95 and 0.99 Å; U_iso(H) = 1.2U_eq(C)]), except for H20, which was refined freely with an isotropic displacement parameter.

Data collection: CAD-4/PC (Enraf–Nonius, 1994 ); cell refinement: CAD-4/PC; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806006982/sj6194sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806006982/sj6194Isup2.hkl

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1994); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(R)-2-Ferrocenyl-4-hydroxymethyl-4,5-dihydrooxazole top

Crystal data top

[Fe(C₅H₅)(C₉H₁₀NO₂)]	F(000) = 296
M_r = 285.12	D_x = 1.574 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 5.808 (4) Å	θ = 9.9–13.2°
b = 7.557 (3) Å	µ = 1.25 mm⁻¹
c = 13.716 (8) Å	T = 160 K
β = 92.39 (6)°	Prism, orange
V = 601.5 (6) Å³	0.30 × 0.13 × 0.08 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	877 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.0°, θ_min = 3.1°
non–profiled ω/2θ scans	h = −1→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.706, T_max = 0.912	l = −16→16
1305 measured reflections	2 standard reflections every 100 reflections
1137 independent reflections	intensity decay: 5%

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0336P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1137 reflections	Δρ_max = 0.54 e Å⁻³
168 parameters	Δρ_min = −0.37 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 171 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (4)

Special details top

Experimental. Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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
C1	0.6839 (10)	0.0630 (10)	0.6919 (4)	0.0169 (15)
C2	0.8278 (11)	−0.0481 (10)	0.7527 (5)	0.0192 (15)
H2	0.9815	−0.0823	0.7409	0.023*
C3	0.7001 (17)	−0.0974 (13)	0.8332 (7)	0.031 (3)
H3	0.7536	−0.1708	0.8857	0.037*
C4	0.4774 (12)	−0.0190 (11)	0.8232 (5)	0.0254 (16)
H4	0.3566	−0.0303	0.8674	0.030*
C5	0.4693 (10)	0.0788 (9)	0.7353 (4)	0.0177 (15)
H5	0.3407	0.1441	0.7097	0.021*
C6	0.7433 (9)	0.1413 (10)	0.5996 (4)	0.0171 (18)
C7	0.9844 (10)	0.2045 (11)	0.4816 (4)	0.0221 (18)
H7A	1.0478	0.1224	0.4333	0.026*
H7B	1.0858	0.3095	0.4879	0.026*
C8	0.7372 (10)	0.2586 (10)	0.4514 (4)	0.0208 (15)
H8	0.7314	0.3880	0.4362	0.025*
C9	0.6402 (11)	0.1529 (12)	0.3645 (4)	0.0231 (16)
H9A	0.4704	0.1659	0.3605	0.028*
H9B	0.7012	0.2020	0.3039	0.028*
C10	1.0133 (12)	0.3030 (13)	0.8785 (7)	0.047 (3)
H10	1.1679	0.2662	0.8708	0.056*
C11	0.8812 (19)	0.4114 (13)	0.8152 (6)	0.052 (3)
H11	0.9322	0.4623	0.7566	0.063*
C12	0.664 (2)	0.4326 (15)	0.8517 (9)	0.052 (3)
H12	0.5396	0.4982	0.8227	0.063*
C13	0.6638 (14)	0.3415 (15)	0.9372 (7)	0.053 (3)
H13	0.5367	0.3357	0.9785	0.064*
C14	0.8715 (16)	0.2591 (12)	0.9560 (6)	0.043 (2)
H14	0.9120	0.1866	1.0106	0.052*
Fe1	0.72777 (14)	0.1715 (2)	0.82749 (6)	0.0192 (2)
N1	0.6050 (8)	0.2214 (7)	0.5395 (3)	0.0196 (14)
O1	0.9634 (7)	0.1180 (6)	0.5750 (3)	0.0209 (11)
O2	0.6970 (8)	−0.0304 (7)	0.3711 (4)	0.0269 (11)
H20	0.610 (11)	−0.094 (11)	0.408 (5)	0.04 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.016 (3)	0.019 (4)	0.015 (3)	0.001 (3)	−0.004 (3)	−0.002 (3)
C2	0.018 (3)	0.017 (4)	0.023 (4)	0.005 (3)	0.001 (3)	−0.006 (3)
C3	0.049 (7)	0.015 (5)	0.029 (5)	0.003 (4)	0.005 (5)	0.011 (4)
C4	0.026 (4)	0.028 (4)	0.022 (4)	−0.001 (3)	0.000 (3)	0.003 (3)
C5	0.018 (3)	0.018 (4)	0.017 (3)	−0.001 (3)	0.002 (3)	−0.002 (3)
C6	0.016 (3)	0.021 (5)	0.014 (3)	−0.002 (3)	0.001 (2)	−0.005 (3)
C7	0.021 (3)	0.024 (5)	0.022 (3)	0.000 (3)	0.001 (3)	0.005 (3)
C8	0.023 (4)	0.017 (3)	0.022 (4)	0.002 (3)	−0.002 (3)	0.000 (3)
C9	0.031 (3)	0.020 (4)	0.018 (3)	−0.004 (4)	0.000 (2)	0.004 (4)
C10	0.013 (4)	0.053 (6)	0.075 (7)	−0.003 (4)	0.003 (4)	−0.046 (5)
C11	0.086 (8)	0.044 (6)	0.028 (5)	−0.032 (6)	0.015 (6)	−0.006 (4)
C12	0.060 (7)	0.043 (7)	0.051 (7)	0.011 (6)	−0.027 (6)	−0.029 (6)
C13	0.034 (5)	0.079 (8)	0.047 (6)	−0.016 (5)	0.014 (4)	−0.040 (6)
C14	0.069 (6)	0.036 (5)	0.024 (4)	−0.010 (5)	−0.025 (4)	−0.002 (4)
Fe1	0.0192 (4)	0.0216 (4)	0.0165 (4)	0.0002 (7)	−0.0009 (3)	−0.0051 (7)
N1	0.021 (3)	0.019 (4)	0.019 (3)	0.002 (2)	0.004 (2)	0.000 (2)
O1	0.020 (2)	0.025 (3)	0.019 (2)	0.0050 (18)	0.0040 (19)	0.0033 (18)
O2	0.030 (3)	0.020 (3)	0.031 (3)	−0.009 (2)	0.006 (2)	0.002 (2)

Geometric parameters (Å, º) top

C1—C5	1.408 (8)	C8—C9	1.523 (9)
C1—C2	1.429 (9)	C8—H8	1.0000
C1—C6	1.452 (8)	C9—O2	1.426 (10)
C1—Fe1	2.039 (6)	C9—H9A	0.9900
C2—C3	1.407 (11)	C9—H9B	0.9900
C2—Fe1	2.048 (7)	C10—C11	1.398 (13)
C2—H2	0.9500	C10—C14	1.412 (12)
C3—C4	1.425 (11)	C10—Fe1	2.032 (7)
C3—Fe1	2.040 (11)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.385 (15)
C4—C5	1.413 (9)	C11—Fe1	2.030 (9)
C4—Fe1	2.045 (8)	C11—H11	0.9500
C4—H4	0.9500	C12—C13	1.360 (14)
C5—Fe1	2.046 (6)	C12—Fe1	2.037 (12)
C5—H5	0.9500	C12—H12	0.9500
C6—N1	1.279 (7)	C13—C14	1.372 (12)
C6—O1	1.347 (7)	C13—Fe1	2.025 (9)
C7—O1	1.447 (7)	C13—H13	0.9500
C7—C8	1.533 (8)	C14—Fe1	2.029 (7)
C7—H7A	0.9900	C14—H14	0.9500
C7—H7B	0.9900	O2—H20	0.88 (7)
C8—N1	1.485 (8)

C5—C1—C2	108.0 (5)	C11—C12—Fe1	69.8 (6)
C5—C1—C6	125.5 (5)	C13—C12—H12	126.7
C2—C1—C6	126.4 (6)	C11—C12—H12	126.7
C5—C1—Fe1	70.1 (3)	Fe1—C12—H12	125.2
C2—C1—Fe1	69.9 (4)	C12—C13—C14	111.0 (9)
C6—C1—Fe1	127.3 (5)	C12—C13—Fe1	70.9 (6)
C3—C2—C1	107.4 (6)	C14—C13—Fe1	70.4 (5)
C3—C2—Fe1	69.6 (5)	C12—C13—H13	124.5
C1—C2—Fe1	69.2 (4)	C14—C13—H13	124.5
C3—C2—H2	126.3	Fe1—C13—H13	125.8
C1—C2—H2	126.3	C13—C14—C10	106.8 (8)
Fe1—C2—H2	126.5	C13—C14—Fe1	70.1 (4)
C2—C3—C4	108.7 (7)	C10—C14—Fe1	69.8 (4)
C2—C3—Fe1	70.2 (5)	C13—C14—H14	126.6
C4—C3—Fe1	69.8 (5)	C10—C14—H14	126.6
C2—C3—H3	125.7	Fe1—C14—H14	125.2
C4—C3—H3	125.7	C13—Fe1—C11	65.8 (4)
Fe1—C3—H3	126.0	C13—Fe1—C14	39.6 (3)
C5—C4—C3	107.3 (6)	C11—Fe1—C14	67.3 (4)
C5—C4—Fe1	69.8 (4)	C13—Fe1—C10	66.8 (3)
C3—C4—Fe1	69.4 (5)	C11—Fe1—C10	40.3 (4)
C5—C4—H4	126.3	C14—Fe1—C10	40.7 (3)
C3—C4—H4	126.3	C13—Fe1—C12	39.1 (4)
Fe1—C4—H4	126.0	C11—Fe1—C12	39.8 (4)
C1—C5—C4	108.5 (6)	C14—Fe1—C12	67.2 (4)
C1—C5—Fe1	69.6 (3)	C10—Fe1—C12	67.8 (4)
C4—C5—Fe1	69.8 (4)	C13—Fe1—C1	156.0 (4)
C1—C5—H5	125.7	C11—Fe1—C1	108.8 (3)
C4—C5—H5	125.7	C14—Fe1—C1	162.7 (3)
Fe1—C5—H5	126.5	C10—Fe1—C1	125.4 (3)
N1—C6—O1	118.5 (5)	C12—Fe1—C1	121.4 (4)
N1—C6—C1	126.1 (5)	C13—Fe1—C3	125.9 (4)
O1—C6—C1	115.3 (5)	C11—Fe1—C3	158.1 (4)
O1—C7—C8	104.3 (5)	C14—Fe1—C3	108.8 (4)
O1—C7—H7A	110.9	C10—Fe1—C3	122.6 (4)
C8—C7—H7A	110.9	C12—Fe1—C3	160.6 (4)
O1—C7—H7B	110.9	C1—Fe1—C3	68.1 (3)
C8—C7—H7B	110.9	C13—Fe1—C5	121.6 (3)
H7A—C7—H7B	108.9	C11—Fe1—C5	124.6 (4)
N1—C8—C9	110.5 (5)	C14—Fe1—C5	156.0 (3)
N1—C8—C7	103.9 (5)	C10—Fe1—C5	161.3 (3)
C9—C8—C7	112.6 (6)	C12—Fe1—C5	107.4 (4)
N1—C8—H8	109.9	C1—Fe1—C5	40.3 (2)
C9—C8—H8	109.9	C3—Fe1—C5	68.0 (3)
C7—C8—H8	109.9	C13—Fe1—C4	108.4 (3)
O2—C9—C8	112.5 (5)	C11—Fe1—C4	160.1 (4)
O2—C9—H9A	109.1	C14—Fe1—C4	121.4 (3)
C8—C9—H9A	109.1	C10—Fe1—C4	157.4 (4)
O2—C9—H9B	109.1	C12—Fe1—C4	123.6 (4)
C8—C9—H9B	109.1	C1—Fe1—C4	68.2 (3)
H9A—C9—H9B	107.8	C3—Fe1—C4	40.8 (3)
C11—C10—C14	106.4 (7)	C5—Fe1—C4	40.4 (2)
C11—C10—Fe1	69.8 (5)	C13—Fe1—C2	162.0 (4)
C14—C10—Fe1	69.6 (4)	C11—Fe1—C2	123.2 (3)
C11—C10—H10	126.8	C14—Fe1—C2	125.8 (3)
C14—C10—H10	126.8	C10—Fe1—C2	108.9 (3)
Fe1—C10—H10	125.5	C12—Fe1—C2	157.5 (4)
C12—C11—C10	109.2 (9)	C1—Fe1—C2	40.9 (3)
C12—C11—Fe1	70.4 (6)	C3—Fe1—C2	40.2 (3)
C10—C11—Fe1	70.0 (5)	C5—Fe1—C2	68.2 (3)
C12—C11—H11	125.4	C4—Fe1—C2	68.4 (3)
C10—C11—H11	125.4	C6—N1—C8	106.4 (5)
Fe1—C11—H11	125.8	C6—O1—C7	106.2 (4)
C13—C12—C11	106.7 (10)	C9—O2—H20	116 (5)
C13—C12—Fe1	69.9 (6)

C5—C1—C2—C3	−0.7 (8)	C13—C12—Fe1—C14	−36.0 (5)
C6—C1—C2—C3	−178.6 (7)	C11—C12—Fe1—C14	81.4 (6)
Fe1—C1—C2—C3	59.3 (5)	C13—C12—Fe1—C10	−80.2 (6)
C5—C1—C2—Fe1	−60.0 (4)	C11—C12—Fe1—C10	37.2 (6)
C6—C1—C2—Fe1	122.1 (7)	C13—C12—Fe1—C1	160.9 (5)
C1—C2—C3—C4	0.3 (9)	C11—C12—Fe1—C1	−81.7 (7)
Fe1—C2—C3—C4	59.4 (6)	C13—C12—Fe1—C3	45.9 (11)
C1—C2—C3—Fe1	−59.1 (5)	C11—C12—Fe1—C3	163.3 (8)
C2—C3—C4—C5	0.2 (9)	C13—C12—Fe1—C5	119.0 (6)
Fe1—C3—C4—C5	59.8 (5)	C11—C12—Fe1—C5	−123.6 (6)
C2—C3—C4—Fe1	−59.6 (6)	C13—C12—Fe1—C4	77.6 (7)
C2—C1—C5—C4	0.8 (7)	C11—C12—Fe1—C4	−165.1 (5)
C6—C1—C5—C4	178.7 (6)	C13—C12—Fe1—C2	−166.0 (7)
Fe1—C1—C5—C4	−59.0 (5)	C11—C12—Fe1—C2	−48.6 (12)
C2—C1—C5—Fe1	59.8 (4)	C5—C1—Fe1—C13	−49.2 (9)
C6—C1—C5—Fe1	−122.2 (7)	C2—C1—Fe1—C13	−168.1 (8)
C3—C4—C5—C1	−0.6 (8)	C6—C1—Fe1—C13	70.8 (10)
Fe1—C4—C5—C1	58.9 (4)	C5—C1—Fe1—C11	−121.8 (5)
C3—C4—C5—Fe1	−59.5 (5)	C2—C1—Fe1—C11	119.3 (5)
C5—C1—C6—N1	−7.2 (11)	C6—C1—Fe1—C11	−1.7 (7)
C2—C1—C6—N1	170.3 (7)	C5—C1—Fe1—C14	164.3 (12)
Fe1—C1—C6—N1	−98.3 (7)	C2—C1—Fe1—C14	45.4 (14)
C5—C1—C6—O1	176.1 (6)	C6—C1—Fe1—C14	−75.6 (14)
C2—C1—C6—O1	−6.3 (10)	C5—C1—Fe1—C10	−163.4 (5)
Fe1—C1—C6—O1	85.1 (7)	C2—C1—Fe1—C10	77.7 (6)
O1—C7—C8—N1	8.7 (6)	C6—C1—Fe1—C10	−43.4 (7)
O1—C7—C8—C9	−110.9 (6)	C5—C1—Fe1—C12	−79.7 (6)
N1—C8—C9—O2	−73.7 (7)	C2—C1—Fe1—C12	161.4 (6)
C7—C8—C9—O2	41.9 (7)	C6—C1—Fe1—C12	40.3 (7)
C14—C10—C11—C12	−0.6 (10)	C5—C1—Fe1—C3	81.3 (4)
Fe1—C10—C11—C12	59.7 (7)	C2—C1—Fe1—C3	−37.6 (4)
C14—C10—C11—Fe1	−60.2 (5)	C6—C1—Fe1—C3	−158.6 (6)
C10—C11—C12—C13	1.1 (11)	C2—C1—Fe1—C5	−118.9 (5)
Fe1—C11—C12—C13	60.6 (7)	C6—C1—Fe1—C5	120.1 (7)
C10—C11—C12—Fe1	−59.4 (6)	C5—C1—Fe1—C4	37.2 (4)
C11—C12—C13—C14	−1.3 (11)	C2—C1—Fe1—C4	−81.7 (4)
Fe1—C12—C13—C14	59.1 (7)	C6—C1—Fe1—C4	157.3 (6)
C11—C12—C13—Fe1	−60.5 (7)	C5—C1—Fe1—C2	118.9 (5)
C12—C13—C14—C10	1.0 (10)	C6—C1—Fe1—C2	−121.0 (7)
Fe1—C13—C14—C10	60.4 (5)	C2—C3—Fe1—C13	−164.3 (4)
C12—C13—C14—Fe1	−59.4 (7)	C4—C3—Fe1—C13	76.0 (6)
C11—C10—C14—C13	−0.2 (9)	C2—C3—Fe1—C11	−48.0 (12)
Fe1—C10—C14—C13	−60.6 (6)	C4—C3—Fe1—C11	−167.7 (8)
C11—C10—C14—Fe1	60.4 (5)	C2—C3—Fe1—C14	−123.7 (5)
C12—C13—Fe1—C11	38.6 (6)	C4—C3—Fe1—C14	116.6 (5)
C14—C13—Fe1—C11	−83.1 (6)	C2—C3—Fe1—C10	−80.8 (6)
C12—C13—Fe1—C14	121.7 (9)	C4—C3—Fe1—C10	159.5 (4)
C12—C13—Fe1—C10	82.7 (7)	C2—C3—Fe1—C12	161.7 (9)
C14—C13—Fe1—C10	−39.0 (5)	C4—C3—Fe1—C12	42.0 (10)
C14—C13—Fe1—C12	−121.7 (9)	C2—C3—Fe1—C1	38.2 (4)
C12—C13—Fe1—C1	−43.3 (11)	C4—C3—Fe1—C1	−81.5 (5)
C14—C13—Fe1—C1	−165.0 (7)	C2—C3—Fe1—C5	81.8 (5)
C12—C13—Fe1—C3	−162.9 (5)	C4—C3—Fe1—C5	−37.9 (4)
C14—C13—Fe1—C3	75.4 (7)	C2—C3—Fe1—C4	119.7 (7)
C12—C13—Fe1—C5	−78.5 (7)	C4—C3—Fe1—C2	−119.7 (7)
C14—C13—Fe1—C5	159.8 (5)	C1—C5—Fe1—C13	158.8 (5)
C12—C13—Fe1—C4	−120.9 (7)	C4—C5—Fe1—C13	−81.3 (6)
C14—C13—Fe1—C4	117.3 (6)	C1—C5—Fe1—C11	78.0 (5)
C12—C13—Fe1—C2	162.5 (10)	C4—C5—Fe1—C11	−162.1 (5)
C14—C13—Fe1—C2	40.8 (13)	C1—C5—Fe1—C14	−168.6 (9)
C12—C11—Fe1—C13	−37.9 (6)	C4—C5—Fe1—C14	−48.7 (10)
C10—C11—Fe1—C13	82.1 (5)	C1—C5—Fe1—C10	46.5 (12)
C12—C11—Fe1—C14	−81.2 (7)	C4—C5—Fe1—C10	166.5 (11)
C10—C11—Fe1—C14	38.9 (5)	C1—C5—Fe1—C12	118.4 (6)
C12—C11—Fe1—C10	−120.1 (8)	C4—C5—Fe1—C12	−121.7 (6)
C10—C11—Fe1—C12	120.1 (8)	C4—C5—Fe1—C1	119.9 (6)
C12—C11—Fe1—C1	116.9 (6)	C1—C5—Fe1—C3	−81.7 (4)
C10—C11—Fe1—C1	−123.1 (5)	C4—C5—Fe1—C3	38.3 (4)
C12—C11—Fe1—C3	−165.1 (8)	C1—C5—Fe1—C4	−119.9 (6)
C10—C11—Fe1—C3	−45.1 (12)	C1—C5—Fe1—C2	−38.1 (4)
C12—C11—Fe1—C5	74.9 (7)	C4—C5—Fe1—C2	81.8 (4)
C10—C11—Fe1—C5	−165.0 (4)	C5—C4—Fe1—C13	117.5 (5)
C12—C11—Fe1—C4	39.1 (12)	C3—C4—Fe1—C13	−124.0 (6)
C10—C11—Fe1—C4	159.1 (8)	C5—C4—Fe1—C11	48.0 (11)
C12—C11—Fe1—C2	159.9 (6)	C3—C4—Fe1—C11	166.5 (9)
C10—C11—Fe1—C2	−80.0 (6)	C5—C4—Fe1—C14	159.0 (5)
C10—C14—Fe1—C13	−117.4 (8)	C3—C4—Fe1—C14	−82.5 (6)
C13—C14—Fe1—C11	78.9 (6)	C5—C4—Fe1—C10	−168.8 (8)
C10—C14—Fe1—C11	−38.5 (5)	C3—C4—Fe1—C10	−50.3 (10)
C13—C14—Fe1—C10	117.4 (8)	C5—C4—Fe1—C12	77.0 (6)
C13—C14—Fe1—C12	35.6 (6)	C3—C4—Fe1—C12	−164.5 (5)
C10—C14—Fe1—C12	−81.8 (6)	C5—C4—Fe1—C1	−37.2 (4)
C13—C14—Fe1—C1	159.3 (12)	C3—C4—Fe1—C1	81.3 (5)
C10—C14—Fe1—C1	41.9 (14)	C5—C4—Fe1—C3	−118.5 (6)
C13—C14—Fe1—C3	−124.1 (6)	C3—C4—Fe1—C5	118.5 (6)
C10—C14—Fe1—C3	118.5 (6)	C5—C4—Fe1—C2	−81.4 (4)
C13—C14—Fe1—C5	−46.1 (11)	C3—C4—Fe1—C2	37.1 (4)
C10—C14—Fe1—C5	−163.6 (9)	C3—C2—Fe1—C13	45.4 (12)
C13—C14—Fe1—C4	−80.9 (7)	C1—C2—Fe1—C13	164.3 (9)
C10—C14—Fe1—C4	161.7 (5)	C3—C2—Fe1—C11	160.7 (6)
C13—C14—Fe1—C2	−165.6 (6)	C1—C2—Fe1—C11	−80.4 (5)
C10—C14—Fe1—C2	77.0 (6)	C3—C2—Fe1—C14	76.3 (6)
C11—C10—Fe1—C13	−79.3 (6)	C1—C2—Fe1—C14	−164.9 (4)
C14—C10—Fe1—C13	37.9 (5)	C3—C2—Fe1—C10	118.4 (6)
C14—C10—Fe1—C11	117.3 (7)	C1—C2—Fe1—C10	−122.7 (5)
C11—C10—Fe1—C14	−117.3 (7)	C3—C2—Fe1—C12	−164.2 (8)
C11—C10—Fe1—C12	−36.8 (6)	C1—C2—Fe1—C12	−45.3 (11)
C14—C10—Fe1—C12	80.5 (6)	C3—C2—Fe1—C1	−118.9 (6)
C11—C10—Fe1—C1	76.8 (6)	C1—C2—Fe1—C3	118.9 (6)
C14—C10—Fe1—C1	−165.9 (5)	C3—C2—Fe1—C5	−81.3 (5)
C11—C10—Fe1—C3	161.8 (5)	C1—C2—Fe1—C5	37.6 (4)
C14—C10—Fe1—C3	−80.9 (6)	C3—C2—Fe1—C4	−37.6 (5)
C11—C10—Fe1—C5	41.6 (13)	C1—C2—Fe1—C4	81.3 (4)
C14—C10—Fe1—C5	158.9 (10)	O1—C6—N1—C8	3.2 (7)
C11—C10—Fe1—C4	−161.6 (8)	C1—C6—N1—C8	−173.4 (7)
C14—C10—Fe1—C4	−44.3 (10)	C9—C8—N1—C6	113.6 (6)
C11—C10—Fe1—C2	119.4 (5)	C7—C8—N1—C6	−7.3 (6)
C14—C10—Fe1—C2	−123.3 (5)	N1—C6—O1—C7	2.7 (8)
C11—C12—Fe1—C13	117.4 (9)	C1—C6—O1—C7	179.7 (6)
C13—C12—Fe1—C11	−117.4 (9)	C8—C7—O1—C6	−7.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H20···N1ⁱ	0.87 (7)	2.02 (8)	2.877 (7)	165 (7)

Symmetry code: (i) −x+1, y−1/2, −z+1.

Acknowledgements

The authors thank Queen Mary University of London for financial support.

References

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