[6-(Hy­droxy­meth­yl)pyridin-2-yl]methyl ferrocene-1-carboxyl­ate

Auzias, M.; Süss-Fink, G.; Therrien, B.

doi:10.1107/S1600536811043972

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1618

doi:10.1107/S1600536811043972

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[6-(Hydroxymethyl)pyridin-2-yl]methyl ferrocene-1-carboxylate

Mathieu Auzias,^a Georg Süss-Fink ^a and Bruno Therrien ^a ^*

^aInstitut de Chimie, Université de Neuchâtel, Avenue de Bellevaux 51, CH-2000 Neuchâtel, Switzerland
^*Correspondence e-mail: bruno.therrien@unine.ch

(Received 20 October 2011; accepted 23 October 2011; online 29 October 2011)

The crystal structure of the title ferrocene derivative, [Fe(C₅H₅)(C₁₃H₁₂NO₃)], shows strong intermolecular O—H⋯N hydrogen bonds between the alcohol function and the pyridine group of a neighbouring molecule, while the pyridine function forms another hydrogen bond with the alcohol function of another neighbouring molecule, resulting in the formation of chains along the a-axis direction.

Related literature

For analogous pyridinoferrocene derivatives and the synthesis of the title compound, see: Izumi et al. (1984 , 1988 ). For a review on ferrocene derivatives as anticancer agents, see: Hillard & Jaouen (2011 ). For related structures, see: Auzias et al. (2008 , 2009 ).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₃H₁₂NO₃)]
M_r = 351.18
Tetragonal, P 4₁ 2₁ 2
a = 7.5477 (3) Å
c = 53.351 (4) Å
V = 3039.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 173 K
0.17 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
13026 measured reflections
2808 independent reflections
2092 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.083
S = 0.86
2808 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.57 e Å⁻³
Absolute structure: Flack (1983 ), 1024 Friedel pairs
Flack parameter: 0.02 (3)

Data collection: SMART (Bruker, 1999 ); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043972/ff2038sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043972/ff2038Isup2.hkl

checkCIF report

Comment top

Ferrocene derivatives are known to exert antiproliferative effects on cancers (Hillard & Jaouen, 2011) and, in this paper, the molecular structure of a ferrocene derivative, {6-(hydroxymethyl)pyridin-2-yl}methyl ferrocene-1-carboxylate, is presented. However, a biological evaluation was not possible due to the low water-solubility of the compound.

The title compound is obtained following a previsouly published procedure (Izumi et al., 1984; Izumi et al., 1988) using ferrocenoyl chloride and 2,6-pyridinedimethanol in the presence of triethylamine. After purification, the compound crystallizes in the tetragonal space group P 4₁2₁2 with eight molecules per unit cell. These molecules are pilled along the c axis (c = 53.351 (4) Å). In the solid state, the ferrocene adopts an eclipsed conformation, and the pyridyl substituent is positionned perpendicular to the plane of the η⁵-C₅H₄COOCH₂– moiety. Otherwise, the metrical parameters are normal and compare well to those of analogous functionalized-ferrocenyl molecules (Auzias et al., 2008; Auzias et al., 2009).

In the crystal packing, the pyridyl and the alcohol functions are involved in strong H-bonded interactions with two neighbouring symmetry-related molecules: The N—O separation being 2.827 (4) Å with the O—H···N angle being 159 (6)°.

Related literature top

For analogous pyridinoferrocene derivatives and the synthesis of the title compound; see: Izumi et al. (1984, 1988). For a review on ferrocene derivatives as anticancer agents, see: Hillard & Jaouen (2011). For related structures, see: Auzias et al. (2008, 2009).

Experimental top

Crystals suitable for X-ray diffraction analysis were obtained, after days, by slow diffusion of diethyl ether into a chloroform solution of the title complex.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART and SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (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 {6-(hydroxymethyl)pyridin-2-yl}methyl ferrocene-1-carboxylate. Displacement ellipsoids are drawn at the 50% probability level.

[6-(Hydroxymethyl)pyridin-2-yl]methyl ferrocene-1-carboxylate top

Crystal data top

[Fe(C₅H₅)(C₁₃H₁₂NO₃)]	D_x = 1.535 Mg m⁻³
M_r = 351.18	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 9687 reflections
Hall symbol: P 4abw 2nw	θ = 1.5–26.0°
a = 7.5477 (3) Å	µ = 1.01 mm⁻¹
c = 53.351 (4) Å	T = 173 K
V = 3039.3 (3) Å³	Block, orange
Z = 8	0.17 × 0.14 × 0.12 mm
F(000) = 1456

Data collection top

Bruker SMART CCD diffractometer	2092 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 25.6°, θ_min = 1.5°
Detector resolution: 0 pixels mm^-1	h = −9→8
ω scans	k = −9→9
13026 measured reflections	l = −64→64
2808 independent reflections

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0458P)²] where P = (F_o² + 2F_c²)/3
S = 0.86	(Δ/σ)_max < 0.001
2808 reflections	Δρ_max = 0.24 e Å⁻³
212 parameters	Δρ_min = −0.57 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1024 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

[Fe(C₅H₅)(C₁₃H₁₂NO₃)]	Z = 8
M_r = 351.18	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 1.01 mm⁻¹
a = 7.5477 (3) Å	T = 173 K
c = 53.351 (4) Å	0.17 × 0.14 × 0.12 mm
V = 3039.3 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2092 reflections with I > 2σ(I)
13026 measured reflections	R_int = 0.072
2808 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	Δρ_max = 0.24 e Å⁻³
S = 0.86	Δρ_min = −0.57 e Å⁻³
2808 reflections	Absolute structure: Flack (1983), 1024 Friedel pairs
212 parameters	Absolute structure parameter: 0.02 (3)
0 restraints

Special details top

Experimental. A crystal was mounted at 173 K on a Bruker SMART CCD PLATFORM using Mo Kα graphite monochromated radiation. Image plate distance 70 mm, ϕ oscillation scans 0 - 200°, step Δϕ = 0.5°, 3 minutes per frame.

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	0.16190 (7)	0.78987 (6)	0.032064 (10)	0.03038 (14)
O2	−0.0794 (3)	0.8358 (3)	0.09355 (4)	0.0367 (6)
O1	−0.2404 (3)	0.9840 (3)	0.06481 (6)	0.0436 (7)
C11	−0.0980 (5)	0.9287 (5)	0.07208 (7)	0.0323 (8)
C7	0.1223 (5)	0.5232 (5)	0.03604 (7)	0.0393 (9)
H7	0.1192	0.4606	0.0510	0.047*
C1	0.0706 (5)	0.9566 (4)	0.05913 (7)	0.0307 (8)
C5	0.0887 (5)	1.0483 (5)	0.03606 (7)	0.0335 (8)
H5	−0.0017	1.1044	0.0273	0.040*
C9	0.2208 (5)	0.6541 (5)	−0.00017 (8)	0.0432 (10)
H9	0.2945	0.6926	−0.0130	0.052*
C4	0.2692 (5)	1.0391 (5)	0.02876 (8)	0.0375 (9)
H4	0.3180	1.0894	0.0144	0.045*
N1	−0.5056 (4)	0.6281 (4)	0.10764 (5)	0.0300 (7)
C13	−0.3422 (4)	0.6468 (4)	0.09774 (6)	0.0304 (8)
C14	−0.6050 (5)	0.4895 (5)	0.10050 (6)	0.0318 (9)
C17	−0.2723 (5)	0.5255 (5)	0.08130 (7)	0.0365 (9)
H17	−0.1574	0.5386	0.0753	0.044*
C10	0.0354 (5)	0.6827 (5)	0.00140 (7)	0.0400 (9)
H10	−0.0344	0.7431	−0.0101	0.048*
C2	0.2408 (5)	0.8887 (5)	0.06595 (7)	0.0318 (8)
H2	0.2673	0.8227	0.0802	0.038*
C16	−0.3757 (5)	0.3827 (5)	0.07373 (7)	0.0381 (10)
H16	−0.3321	0.3007	0.0623	0.046*
C15	−0.5450 (5)	0.3646 (5)	0.08355 (7)	0.0361 (9)
H15	−0.6167	0.2702	0.0788	0.043*
C3	0.3618 (5)	0.9408 (5)	0.04698 (8)	0.0379 (9)
H3	0.4821	0.9145	0.0466	0.046*
C8	0.2748 (6)	0.5564 (5)	0.02136 (8)	0.0426 (10)
H8	0.3897	0.5207	0.0251	0.051*
C19	−0.7864 (5)	0.4814 (5)	0.11208 (8)	0.0399 (10)
H19A	−0.7748	0.4622	0.1300	0.048*
H19B	−0.8458	0.5939	0.1096	0.048*
C6	−0.0237 (5)	0.6013 (5)	0.02401 (7)	0.0385 (9)
H6	−0.1398	0.6001	0.0298	0.046*
C12	−0.2403 (5)	0.8036 (5)	0.10734 (7)	0.0418 (9)
H12A	−0.3148	0.9081	0.1064	0.050*
H12B	−0.2110	0.7842	0.1248	0.050*
O3	−0.8909 (4)	0.3441 (4)	0.10162 (6)	0.0475 (7)
H3O	−0.935 (8)	0.248 (8)	0.1126 (13)	0.14 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0306 (3)	0.0287 (3)	0.0318 (2)	0.0000 (2)	−0.0007 (2)	−0.0016 (2)
O2	0.0287 (13)	0.0459 (16)	0.0356 (14)	−0.0041 (12)	0.0036 (11)	0.0020 (13)
O1	0.0284 (16)	0.0444 (16)	0.0581 (18)	0.0058 (12)	−0.0066 (13)	0.0012 (14)
C11	0.033 (2)	0.029 (2)	0.035 (2)	−0.0008 (16)	−0.0008 (16)	−0.0083 (16)
C7	0.050 (3)	0.034 (2)	0.034 (2)	0.0004 (17)	0.0023 (18)	−0.0036 (17)
C1	0.025 (2)	0.031 (2)	0.036 (2)	−0.0003 (14)	−0.0020 (15)	−0.0020 (16)
C5	0.034 (2)	0.031 (2)	0.035 (2)	−0.0041 (15)	−0.0046 (16)	0.0000 (16)
C9	0.051 (3)	0.038 (2)	0.040 (2)	−0.001 (2)	0.0090 (18)	−0.0070 (19)
C4	0.035 (2)	0.038 (2)	0.039 (2)	−0.0072 (16)	−0.0006 (17)	0.0016 (17)
N1	0.0288 (17)	0.0290 (18)	0.0323 (16)	0.0008 (13)	0.0012 (13)	0.0023 (13)
C13	0.0292 (19)	0.0329 (19)	0.0293 (17)	0.0014 (17)	0.0016 (14)	−0.0011 (14)
C14	0.032 (2)	0.031 (2)	0.033 (2)	−0.0004 (15)	−0.0016 (15)	0.0056 (16)
C17	0.036 (2)	0.039 (2)	0.034 (2)	0.0064 (17)	0.0060 (17)	−0.0020 (17)
C10	0.046 (3)	0.040 (2)	0.034 (2)	−0.0031 (18)	−0.0052 (17)	−0.0045 (19)
C2	0.032 (2)	0.035 (2)	0.0285 (18)	−0.0001 (15)	−0.0023 (15)	−0.0006 (15)
C16	0.047 (3)	0.030 (2)	0.038 (2)	0.0062 (17)	0.0044 (18)	0.0002 (16)
C15	0.047 (2)	0.028 (2)	0.033 (2)	−0.0003 (18)	−0.0017 (17)	0.0027 (16)
C3	0.028 (2)	0.041 (2)	0.045 (2)	−0.0030 (18)	0.0017 (17)	−0.0012 (17)
C8	0.044 (2)	0.042 (2)	0.041 (2)	0.0041 (19)	0.0026 (19)	−0.0038 (18)
C19	0.042 (2)	0.036 (2)	0.042 (2)	−0.0028 (18)	0.0048 (19)	0.0052 (17)
C6	0.041 (2)	0.037 (2)	0.037 (2)	0.0010 (17)	−0.0001 (18)	−0.0021 (17)
C12	0.036 (2)	0.051 (3)	0.039 (2)	−0.0074 (17)	0.0099 (16)	−0.0056 (19)
O3	0.0446 (17)	0.0500 (18)	0.0478 (17)	−0.0159 (14)	−0.0041 (13)	0.0078 (15)

Geometric parameters (Å, º) top

Fe1—C1	2.035 (3)	C4—H4	0.9300
Fe1—C5	2.038 (4)	N1—C14	1.342 (4)
Fe1—C8	2.039 (4)	N1—C13	1.349 (4)
Fe1—C6	2.042 (4)	C13—C17	1.373 (5)
Fe1—C2	2.045 (3)	C13—C12	1.502 (5)
Fe1—C7	2.046 (4)	C14—C15	1.382 (5)
Fe1—C9	2.051 (4)	C14—C19	1.504 (5)
Fe1—C3	2.051 (4)	C17—C16	1.390 (5)
Fe1—C4	2.056 (3)	C17—H17	0.9300
Fe1—C10	2.060 (4)	C10—C6	1.425 (5)
O2—C11	1.350 (4)	C10—H10	0.9300
O2—C12	1.440 (4)	C2—C3	1.419 (5)
O1—C11	1.217 (4)	C2—H2	0.9300
C11—C1	1.464 (5)	C16—C15	1.388 (5)
C7—C6	1.404 (5)	C16—H16	0.9300
C7—C8	1.414 (5)	C15—H15	0.9300
C7—H7	0.9300	C3—H3	0.9300
C1—C5	1.419 (5)	C8—H8	0.9300
C1—C2	1.430 (5)	C19—O3	1.416 (4)
C5—C4	1.418 (5)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C9—C10	1.418 (5)	C6—H6	0.9300
C9—C8	1.425 (6)	C12—H12A	0.9700
C9—H9	0.9300	C12—H12B	0.9700
C4—C3	1.408 (5)	O3—H3O	0.99 (6)

C1—Fe1—C5	40.77 (13)	C8—C9—Fe1	69.2 (2)
C1—Fe1—C8	150.96 (15)	C10—C9—H9	125.9
C5—Fe1—C8	165.83 (15)	C8—C9—H9	125.9
C1—Fe1—C6	110.37 (15)	Fe1—C9—H9	126.3
C5—Fe1—C6	120.19 (15)	C3—C4—C5	108.2 (4)
C8—Fe1—C6	67.99 (16)	C3—C4—Fe1	69.8 (2)
C1—Fe1—C2	41.02 (13)	C5—C4—Fe1	69.07 (19)
C5—Fe1—C2	68.73 (14)	C3—C4—H4	125.9
C8—Fe1—C2	116.19 (16)	C5—C4—H4	125.9
C6—Fe1—C2	129.80 (14)	Fe1—C4—H4	126.9
C1—Fe1—C7	119.02 (14)	C14—N1—C13	118.7 (3)
C5—Fe1—C7	152.99 (14)	N1—C13—C17	122.1 (3)
C8—Fe1—C7	40.51 (14)	N1—C13—C12	114.6 (3)
C6—Fe1—C7	40.19 (15)	C17—C13—C12	123.1 (3)
C2—Fe1—C7	108.06 (15)	N1—C14—C15	122.3 (3)
C1—Fe1—C9	167.76 (15)	N1—C14—C19	115.1 (3)
C5—Fe1—C9	128.65 (16)	C15—C14—C19	122.6 (3)
C8—Fe1—C9	40.78 (15)	C13—C17—C16	119.1 (4)
C6—Fe1—C9	67.92 (15)	C13—C17—H17	120.4
C2—Fe1—C9	149.40 (15)	C16—C17—H17	120.4
C7—Fe1—C9	68.11 (15)	C9—C10—C6	107.1 (4)
C1—Fe1—C3	68.30 (15)	C9—C10—Fe1	69.5 (2)
C5—Fe1—C3	68.11 (14)	C6—C10—Fe1	69.0 (2)
C8—Fe1—C3	106.35 (16)	C9—C10—H10	126.5
C6—Fe1—C3	166.67 (15)	C6—C10—H10	126.5
C2—Fe1—C3	40.54 (14)	Fe1—C10—H10	126.6
C7—Fe1—C3	127.87 (15)	C3—C2—C1	107.3 (3)
C9—Fe1—C3	116.32 (15)	C3—C2—Fe1	70.0 (2)
C1—Fe1—C4	68.18 (15)	C1—C2—Fe1	69.1 (2)
C5—Fe1—C4	40.54 (14)	C3—C2—H2	126.4
C8—Fe1—C4	127.05 (15)	C1—C2—H2	126.4
C6—Fe1—C4	152.84 (16)	Fe1—C2—H2	126.1
C2—Fe1—C4	68.10 (15)	C15—C16—C17	118.9 (4)
C7—Fe1—C4	165.19 (15)	C15—C16—H16	120.5
C9—Fe1—C4	107.45 (16)	C17—C16—H16	120.5
C3—Fe1—C4	40.10 (15)	C14—C15—C16	118.8 (3)
C1—Fe1—C10	130.51 (16)	C14—C15—H15	120.6
C5—Fe1—C10	109.47 (16)	C16—C15—H15	120.6
C8—Fe1—C10	68.39 (17)	C4—C3—C2	108.6 (3)
C6—Fe1—C10	40.65 (14)	C4—C3—Fe1	70.1 (2)
C2—Fe1—C10	168.74 (14)	C2—C3—Fe1	69.5 (2)
C7—Fe1—C10	68.17 (16)	C4—C3—H3	125.7
C9—Fe1—C10	40.37 (15)	C2—C3—H3	125.7
C3—Fe1—C10	150.13 (16)	Fe1—C3—H3	126.3
C4—Fe1—C10	118.30 (16)	C7—C8—C9	107.8 (4)
C11—O2—C12	115.7 (3)	C7—C8—Fe1	70.0 (2)
O1—C11—O2	122.7 (3)	C9—C8—Fe1	70.0 (2)
O1—C11—C1	124.6 (4)	C7—C8—H8	126.1
O2—C11—C1	112.6 (3)	C9—C8—H8	126.1
C6—C7—C8	108.1 (3)	Fe1—C8—H8	125.4
C6—C7—Fe1	69.8 (2)	O3—C19—C14	112.0 (3)
C8—C7—Fe1	69.5 (2)	O3—C19—H19A	109.2
C6—C7—H7	125.9	C14—C19—H19A	109.2
C8—C7—H7	125.9	O3—C19—H19B	109.2
Fe1—C7—H7	126.4	C14—C19—H19B	109.2
C5—C1—C2	108.0 (3)	H19A—C19—H19B	107.9
C5—C1—C11	124.3 (3)	C7—C6—C10	108.8 (4)
C2—C1—C11	127.6 (3)	C7—C6—Fe1	70.0 (2)
C5—C1—Fe1	69.7 (2)	C10—C6—Fe1	70.3 (2)
C2—C1—Fe1	69.8 (2)	C7—C6—H6	125.6
C11—C1—Fe1	122.7 (2)	C10—C6—H6	125.6
C4—C5—C1	107.9 (3)	Fe1—C6—H6	125.6
C4—C5—Fe1	70.4 (2)	O2—C12—C13	113.0 (3)
C1—C5—Fe1	69.5 (2)	O2—C12—H12A	109.0
C4—C5—H5	126.1	C13—C12—H12A	109.0
C1—C5—H5	126.1	O2—C12—H12B	109.0
Fe1—C5—H5	125.6	C13—C12—H12B	109.0
C10—C9—C8	108.2 (4)	H12A—C12—H12B	107.8
C10—C9—Fe1	70.2 (2)	C19—O3—H3O	119 (4)

C12—O2—C11—O1	0.8 (5)	C8—C9—C10—Fe1	58.9 (3)
C12—O2—C11—C1	179.9 (3)	C1—Fe1—C10—C9	168.4 (2)
C1—Fe1—C7—C6	87.7 (2)	C5—Fe1—C10—C9	127.4 (2)
C5—Fe1—C7—C6	52.7 (4)	C8—Fe1—C10—C9	−37.7 (2)
C8—Fe1—C7—C6	−119.4 (3)	C6—Fe1—C10—C9	−118.6 (4)
C2—Fe1—C7—C6	131.1 (2)	C2—Fe1—C10—C9	−153.9 (7)
C9—Fe1—C7—C6	−81.3 (2)	C7—Fe1—C10—C9	−81.4 (3)
C3—Fe1—C7—C6	171.7 (2)	C3—Fe1—C10—C9	47.6 (4)
C4—Fe1—C7—C6	−156.5 (6)	C4—Fe1—C10—C9	83.8 (3)
C10—Fe1—C7—C6	−37.6 (2)	C1—Fe1—C10—C6	−73.0 (3)
C1—Fe1—C7—C8	−152.9 (2)	C5—Fe1—C10—C6	−114.0 (2)
C5—Fe1—C7—C8	172.1 (3)	C8—Fe1—C10—C6	80.9 (3)
C6—Fe1—C7—C8	119.4 (3)	C2—Fe1—C10—C6	−35.2 (9)
C2—Fe1—C7—C8	−109.5 (2)	C7—Fe1—C10—C6	37.2 (2)
C9—Fe1—C7—C8	38.2 (2)	C9—Fe1—C10—C6	118.6 (4)
C3—Fe1—C7—C8	−68.8 (3)	C3—Fe1—C10—C6	166.3 (3)
C4—Fe1—C7—C8	−37.0 (7)	C4—Fe1—C10—C6	−157.5 (2)
C10—Fe1—C7—C8	81.8 (3)	C5—C1—C2—C3	0.3 (4)
O1—C11—C1—C5	−1.6 (6)	C11—C1—C2—C3	176.2 (3)
O2—C11—C1—C5	179.3 (3)	Fe1—C1—C2—C3	59.8 (2)
O1—C11—C1—C2	−176.8 (4)	C5—C1—C2—Fe1	−59.5 (2)
O2—C11—C1—C2	4.1 (5)	C11—C1—C2—Fe1	116.3 (3)
O1—C11—C1—Fe1	−88.2 (4)	C1—Fe1—C2—C3	−118.5 (3)
O2—C11—C1—Fe1	92.8 (3)	C5—Fe1—C2—C3	−80.8 (2)
C8—Fe1—C1—C5	165.9 (3)	C8—Fe1—C2—C3	84.7 (3)
C6—Fe1—C1—C5	−113.0 (2)	C6—Fe1—C2—C3	167.0 (2)
C2—Fe1—C1—C5	119.1 (3)	C7—Fe1—C2—C3	127.7 (2)
C7—Fe1—C1—C5	−156.5 (2)	C9—Fe1—C2—C3	50.4 (4)
C9—Fe1—C1—C5	−33.4 (8)	C4—Fe1—C2—C3	−37.0 (2)
C3—Fe1—C1—C5	81.2 (2)	C10—Fe1—C2—C3	−163.7 (7)
C4—Fe1—C1—C5	37.9 (2)	C5—Fe1—C2—C1	37.74 (19)
C10—Fe1—C1—C5	−71.4 (3)	C8—Fe1—C2—C1	−156.8 (2)
C5—Fe1—C1—C2	−119.1 (3)	C6—Fe1—C2—C1	−74.5 (3)
C8—Fe1—C1—C2	46.8 (4)	C7—Fe1—C2—C1	−113.7 (2)
C6—Fe1—C1—C2	127.9 (2)	C9—Fe1—C2—C1	168.9 (3)
C7—Fe1—C1—C2	84.4 (2)	C3—Fe1—C2—C1	118.5 (3)
C9—Fe1—C1—C2	−152.5 (7)	C4—Fe1—C2—C1	81.5 (2)
C3—Fe1—C1—C2	−37.9 (2)	C10—Fe1—C2—C1	−45.2 (9)
C4—Fe1—C1—C2	−81.3 (2)	C13—C17—C16—C15	−1.7 (6)
C10—Fe1—C1—C2	169.5 (2)	N1—C14—C15—C16	0.4 (5)
C5—Fe1—C1—C11	118.5 (4)	C19—C14—C15—C16	179.8 (3)
C8—Fe1—C1—C11	−75.6 (4)	C17—C16—C15—C14	0.1 (6)
C6—Fe1—C1—C11	5.5 (3)	C5—C4—C3—C2	−0.5 (4)
C2—Fe1—C1—C11	−122.4 (4)	Fe1—C4—C3—C2	−59.0 (3)
C7—Fe1—C1—C11	−38.0 (4)	C5—C4—C3—Fe1	58.5 (2)
C9—Fe1—C1—C11	85.1 (8)	C1—C2—C3—C4	0.1 (4)
C3—Fe1—C1—C11	−160.3 (3)	Fe1—C2—C3—C4	59.4 (3)
C4—Fe1—C1—C11	156.3 (3)	C1—C2—C3—Fe1	−59.3 (2)
C10—Fe1—C1—C11	47.1 (4)	C1—Fe1—C3—C4	−81.5 (2)
C2—C1—C5—C4	−0.6 (4)	C5—Fe1—C3—C4	−37.4 (2)
C11—C1—C5—C4	−176.7 (3)	C8—Fe1—C3—C4	128.8 (2)
Fe1—C1—C5—C4	−60.2 (3)	C6—Fe1—C3—C4	−168.3 (6)
C2—C1—C5—Fe1	59.6 (2)	C2—Fe1—C3—C4	−119.8 (3)
C11—C1—C5—Fe1	−116.4 (3)	C7—Fe1—C3—C4	167.9 (2)
C1—Fe1—C5—C4	118.7 (3)	C9—Fe1—C3—C4	86.1 (3)
C8—Fe1—C5—C4	−32.4 (7)	C10—Fe1—C3—C4	53.8 (4)
C6—Fe1—C5—C4	−154.6 (2)	C1—Fe1—C3—C2	38.4 (2)
C2—Fe1—C5—C4	80.8 (2)	C5—Fe1—C3—C2	82.4 (2)
C7—Fe1—C5—C4	169.0 (3)	C8—Fe1—C3—C2	−111.4 (2)
C9—Fe1—C5—C4	−69.9 (3)	C6—Fe1—C3—C2	−48.5 (7)
C3—Fe1—C5—C4	37.0 (2)	C7—Fe1—C3—C2	−72.2 (3)
C10—Fe1—C5—C4	−111.1 (2)	C9—Fe1—C3—C2	−154.1 (2)
C8—Fe1—C5—C1	−151.1 (6)	C4—Fe1—C3—C2	119.8 (3)
C6—Fe1—C5—C1	86.7 (2)	C10—Fe1—C3—C2	173.7 (3)
C2—Fe1—C5—C1	−38.0 (2)	C6—C7—C8—C9	−0.8 (4)
C7—Fe1—C5—C1	50.2 (4)	Fe1—C7—C8—C9	−60.1 (3)
C9—Fe1—C5—C1	171.4 (2)	C6—C7—C8—Fe1	59.3 (3)
C3—Fe1—C5—C1	−81.7 (2)	C10—C9—C8—C7	0.6 (4)
C4—Fe1—C5—C1	−118.7 (3)	Fe1—C9—C8—C7	60.1 (3)
C10—Fe1—C5—C1	130.2 (2)	C10—C9—C8—Fe1	−59.5 (3)
C1—Fe1—C9—C10	−46.3 (8)	C1—Fe1—C8—C7	55.3 (4)
C5—Fe1—C9—C10	−73.6 (3)	C5—Fe1—C8—C7	−165.3 (6)
C8—Fe1—C9—C10	119.5 (3)	C6—Fe1—C8—C7	−37.3 (2)
C6—Fe1—C9—C10	38.1 (2)	C2—Fe1—C8—C7	87.5 (2)
C2—Fe1—C9—C10	170.3 (3)	C9—Fe1—C8—C7	−118.6 (3)
C7—Fe1—C9—C10	81.6 (2)	C3—Fe1—C8—C7	129.9 (2)
C3—Fe1—C9—C10	−155.8 (2)	C4—Fe1—C8—C7	168.9 (2)
C4—Fe1—C9—C10	−113.4 (2)	C10—Fe1—C8—C7	−81.3 (2)
C1—Fe1—C9—C8	−165.8 (6)	C1—Fe1—C8—C9	173.8 (3)
C5—Fe1—C9—C8	166.8 (2)	C5—Fe1—C8—C9	−46.7 (7)
C6—Fe1—C9—C8	−81.4 (2)	C6—Fe1—C8—C9	81.3 (2)
C2—Fe1—C9—C8	50.7 (4)	C2—Fe1—C8—C9	−154.0 (2)
C7—Fe1—C9—C8	−37.9 (2)	C7—Fe1—C8—C9	118.6 (3)
C3—Fe1—C9—C8	84.7 (3)	C3—Fe1—C8—C9	−111.5 (2)
C4—Fe1—C9—C8	127.0 (2)	C4—Fe1—C8—C9	−72.6 (3)
C10—Fe1—C9—C8	−119.5 (3)	C10—Fe1—C8—C9	37.3 (2)
C1—C5—C4—C3	0.7 (4)	N1—C14—C19—O3	173.3 (3)
Fe1—C5—C4—C3	−58.9 (3)	C15—C14—C19—O3	−6.2 (5)
C1—C5—C4—Fe1	59.7 (2)	C8—C7—C6—C10	0.7 (4)
C1—Fe1—C4—C3	81.8 (3)	Fe1—C7—C6—C10	59.9 (3)
C5—Fe1—C4—C3	119.9 (3)	C8—C7—C6—Fe1	−59.1 (3)
C8—Fe1—C4—C3	−69.6 (3)	C9—C10—C6—C7	−0.4 (4)
C6—Fe1—C4—C3	174.1 (3)	Fe1—C10—C6—C7	−59.7 (3)
C2—Fe1—C4—C3	37.4 (2)	C9—C10—C6—Fe1	59.3 (3)
C7—Fe1—C4—C3	−40.3 (7)	C1—Fe1—C6—C7	−111.3 (2)
C9—Fe1—C4—C3	−110.4 (2)	C5—Fe1—C6—C7	−155.3 (2)
C10—Fe1—C4—C3	−152.8 (2)	C8—Fe1—C6—C7	37.6 (2)
C1—Fe1—C4—C5	−38.1 (2)	C2—Fe1—C6—C7	−68.8 (3)
C8—Fe1—C4—C5	170.5 (2)	C9—Fe1—C6—C7	81.8 (2)
C6—Fe1—C4—C5	54.3 (5)	C3—Fe1—C6—C7	−29.5 (8)
C2—Fe1—C4—C5	−82.4 (2)	C4—Fe1—C6—C7	167.1 (3)
C7—Fe1—C4—C5	−160.1 (5)	C10—Fe1—C6—C7	119.6 (3)
C9—Fe1—C4—C5	129.8 (2)	C1—Fe1—C6—C10	129.1 (2)
C3—Fe1—C4—C5	−119.9 (3)	C5—Fe1—C6—C10	85.1 (3)
C10—Fe1—C4—C5	87.3 (3)	C8—Fe1—C6—C10	−82.0 (3)
C14—N1—C13—C17	−2.3 (5)	C2—Fe1—C6—C10	171.6 (2)
C14—N1—C13—C12	−178.8 (3)	C7—Fe1—C6—C10	−119.6 (3)
C13—N1—C14—C15	0.6 (5)	C9—Fe1—C6—C10	−37.8 (2)
C13—N1—C14—C19	−178.8 (3)	C3—Fe1—C6—C10	−149.1 (6)
N1—C13—C17—C16	2.8 (5)	C4—Fe1—C6—C10	47.5 (5)
C12—C13—C17—C16	179.0 (4)	C11—O2—C12—C13	82.9 (4)
C8—C9—C10—C6	−0.1 (4)	N1—C13—C12—O2	−170.6 (3)
Fe1—C9—C10—C6	−59.0 (3)	C17—C13—C12—O2	13.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1ⁱ	0.99 (6)	1.88 (7)	2.827 (4)	159 (6)

Symmetry code: (i) −x−3/2, y−1/2, −z+1/4.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₁₃H₁₂NO₃)]
M_r	351.18
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	173
a, c (Å)	7.5477 (3), 53.351 (4)
V (Å³)	3039.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.17 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13026, 2808, 2092
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.083, 0.86
No. of reflections	2808
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.57
Absolute structure	Flack (1983), 1024 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: SMART (Bruker, 1999), SMART and SAINT (Bruker, 1999), SAINT (Bruker, 1999), SIR97 (Altomare et al., 1999), SHELXTL (Sheldrick, 2008).

Acknowledgements

A generous loan [gift?] of ruthenium chloride hydrate from the Johnson Matthey Technology Centre is gratefully acknowledged.

References

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