Crystal structure of ruthenocenecarbo­nitrile

Strehler, F.; Korb, M.; Lang, H.

doi:10.1107/S205698901500540X

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Volume 71| Part 4| April 2015| Pages 398-401

doi:10.1107/S205698901500540X

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Crystal structure of ruthenocenecarbonitrile

Frank Strehler,^a Marcus Korb ^a and Heinrich Lang ^a ^*

^aTechnische Universität Chemnitz, Fakultät für Naturwissenschaften, Institut für Chemie, Anorganische Chemie, D-09107 Chemnitz, Germany
^*Correspondence e-mail: heinrich.lang@chemie.tu-chemnitz.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 20 January 2015; accepted 16 March 2015; online 21 March 2015)

The molecular structure of ruthenocenecarbonitrile, [Ru(η⁵-C₅H₄C≡N)(η⁵-C₅H₅)], exhibits point group symmetry m, with the mirror plane bisecting the molecule through the C≡N substituent. The Ru^II atom is slightly shifted from the η⁵-C₅H₄ centroid towards the C≡N substituent. In the crystal, molecules are arranged in columns parallel to [100]. One-dimensional intermolecular π–π interactions [3.363 (3) Å] between the C≡N carbon atom and one carbon of the cyclopentadienyl ring of the overlaying molecule are present.

Keywords: crystal structure; ruthenocene; ruthenocenecarbonitrile; sandwich compound; nitrile.

CCDC reference: 1054219

1. Chemical context

The nitrile group is isoelectronic with the acetylid function (Bonniard et al., 2011 ), which has already been investigated in electron-transfer studies (see, for example, Lang et al., 2006 ; Poppitz et al., 2014 ; Speck et al., 2012 ; Hildebrandt & Lang, 2013 ; Miesel et al., 2013 ). Coordination of, for example, ferrocenecarbonitrile towards transition metals M will allow investigation of the electronic properties of —C≡N—M— or —C≡N—M—N≡C— bridging units. A synthesis for ferrocenecarbonitrile has already been described in 1957 (Graham et al., 1957 ); however, only one example of an application in electrochemical studies has been described by Dowling et al. (1981 ). This prompted us to synthesize ferrocenecarbonitrile transition metal complexes to investigate the electronic properties of the —C≡N—M—N≡C— bridging units (Strehler et al. 2013 , 2014 ). In a continuation of this work, we present herein the synthesis and crystal structure of the related ruthenocenecarbonitrile, (I). The synthesis of this compound was realized by treatment of formylruthenocene with hydroxylamine hydrochloride, zinc oxide and potassium iodide in acetonitrile, which is similar to a procedure already described for the synthesis of ferrocenecarbonitrile (Kivrak & Zora, 2007 ).

2. Structural commentary

The title compound contains one half-molecule in the asymmetric unit with a mirror plane bisecting the molecule through atoms C1, C2, C5, N1 and Ru1 (Fig. 1). The Ru1–centroid distance to the C≡N-substituted cyclopentadienyl ring is slightly increased [1.8179 (1) Å] compared to the unsubstituted C₅H₅ unit [1.8157 (1) Å]. Both cyclopentadienyl rings adopt an ideally eclipsed conformation and are virtually oriented parallel towards each other, which is expressed by the bond angle at the Ru^II between the two centroids (= D), with D(C₅H₄)—Ru1—D(C₅H₅) = 178.87 (1)°. However, the Ru^II atom is slightly shifted from the centre of the C₅ ring to the nitrile-bonded C2 atom, which can be explained best by the significantly different Ru—C bond lengths (Table 1) and also the Ru—D—C angles, which should ideally be 90° (Table 1). This is in accordance with the shift in the ferrocenedicarbonitrile structure (Altmannshofer et al., 2008 ). The C≡N substituent itself is bent away from the metal atom in (I), with a maximum shift for N1 [0.047 (4) Å].

Table 1
Selected bond lengths (Å) and angles (°) for the clarification of the shift of the Ru1 atom towards the C≡N substituent in (I)

D is the centroid of the C₅H₄ or C₅H₅ ring.

	C2	C3	C4	C5	C6	C7
Ru1—C	2.1650 (18)	2.1886 (13)	2.2013 (12)	2.1779 (18)	2.1847 (13)	2.1879 (12)
C—D—Ru1	88.90 (8)	89.63 (6)	90.93 (6)	89.75 (9)	89.95 (6)	90.16 (6)

Figure 1
The molecular structure of (I)

, with displacement ellipsoids drawn at the 50% probability level. All H atoms have been omitted for clarity. [Symmetry code: (A) x, −y + $[{1\over 2}]$ , z.]

3. Supramolecular features

The packing of (I) consists of a layer-type structure parallel to (010) with the direction of the C≡N function aligned parallel to [10 $[\overline{1}]$ ], alternating between adjacent layers. A further order is observed by a columnar arrangement of slightly tilted molecules parallel to [100]. Weak intermolecular π–π interactions within the sum of the van der Waals radii (Σ = 3.4 Å; Bondi, 1964 ) are present between C5 and the C1′ atom [3.363 (3) Å] of the overlying molecule in the same layer (Fig. 2).

Figure 2
Intermolecular π–π interactions (blue) between C5 and C1′ in the crystal structure of (I)

. All H atoms have been omitted for clarity. [Symmetry code: (′) x − 1, y, z.]

4. Database survey

The ruthenocene backbone is hardly described in the literature. Reported derivatives contain sp (ethynyl) (Sato et al., 1997 ; Packheiser et al., 2008 ; Jakob et al., 2008 , 2009a ), sp² (Sato et al., 1998 , 2004 ; Jakob et al., 2009b ) and sp³ (Sokolov et al., 2010 ; Barlow et al., 2001 ) carbon substituents or a carboxylic acid moiety (Zhang & Coppens, 2001 ) and its respective Ru^II complex (Wyman et al., 2005 ). They all exhibit similar Ru—D distances (1.795–1.823 Å) as compared to (I) [1.8179 (1)–1.8157 (1) Å] or unsubstituted ruthenocene (1.794–1.816 Å) (Ma & Coppens, 2003 ; Borissova et al., 2008 ; Seiler & Dunitz, 1980 ).

Comparison of the C—C [1.431 (3) Å] and the C≡N distances [1.148 (3) Å] with the respective ferrocene carbonitrile derivatives (C≡N = 1.133–1.150; C—C = 1.428–1.433 Å; Altmannshofer et al., 2008; Dayaker et al., 2010 ; Bell et al., 1996 ; Nemykin et al., 2007 ; Erben et al., 2007 ) reveals no significant influence of the central metal atom on the electronic properties of the substituent.

5. Synthesis and crystallization

Formylruthenocene was prepared according to a published procedure (Mueller-Westerhoff et al., 1993 ). Synthesis of ruthenocenecarbonitrile, (I): formylruthenocene (2.27 g, 8.8 mmol), hydroxylamine hydrochloride (0.96 g, 13.8 mmol), zinc oxide (0.86 g, 10.6 mmol) and potassium iodide (1.76 g, 10.6 mmol) were suspended in 120 ml of dry acetonitrile. The mixture was stirred for 4 h at precisely 368 K. After cooling the reaction mixture to ambient temperature, 18 ml of an aqueous Na₂S₂O₃ (5%) solution were added in a single portion, and stirring was continued for additional 20 min. Solid particles were removed by filtration and the filtrate was extracted with ethyl acetate (3 × 50 ml). The combined organic layers were dried over MgSO₄. All volatiles were removed under reduced pressure and the crude product was purified by flash chromatography on aluminum oxide using dichloromethane as eluent. Greenish crystals of (I) were obtained by slow evaporation of a saturated dichloromethane solution containing (I) at ambient temperature (yield: 820 mg, 3.3 mmol, 38% based on formylruthenocene). IR (KBr, cm⁻¹): ν = 2226 (m, C≡N), 2854 (s), 2925 (s), 3082 (m, C—H). ¹H NMR (500.3 MHz, CDCl₃, 298 K): δ 4.69 (s, 5H, C₅H₅), 4.70 (pt, 2H, J_H,H = 1.8 Hz), 4.70 (pt, 2H, J_H,H = 1.8 Hz). ¹³C{¹H} NMR (125.7 MHz, CDCl₃, 298 K): δ = 55.3 (C_i-C₅H₄), 72.4 (C₅H₄), 72.9 (C₅H₅), 73.5 (C₅H₄), 119.4 (CN). HRMS (ESI–TOF, M⁺): C₁₁H₉NRu: m/z = 256.9792 (calc. 256.9776).

6. Refinement

C-bonded H atoms were placed in calculated positions and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C) and a C—H distance of 0.93 Å. Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Ru(C₅H₅)(C₆H₄N)]
M_r	256.26
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	110
a, b, c (Å)	7.2023 (2), 8.6802 (2), 7.2922 (1)
β (°)	106.497 (2)
V (Å³)	437.12 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.74
Crystal size (mm)	0.38 × 0.30 × 0.30

Data collection
Diffractometer	Oxford Gemini S CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ )
T_min, T_max	0.849, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	27710, 900, 877
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.012, 0.032, 1.05
No. of reflections	900
No. of parameters	67
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.39
Computer programs: CrysAlis CCD and CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction, Abingdon, England.]$ ), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1054219

Crystal structure: contains datablock I. DOI: 10.1107/S205698901500540X/wm5119sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500540X/wm5119Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Ruthenocenecarbonitrile top

Crystal data top

[Ru(C₅H₅)(C₆H₄N)]	F(000) = 252
M_r = 256.26	D_x = 1.947 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 7.2023 (2) Å	Cell parameters from 26762 reflections
b = 8.6802 (2) Å	θ = 3.5–28.7°
c = 7.2922 (1) Å	µ = 1.74 mm⁻¹
β = 106.497 (2)°	T = 110 K
V = 437.12 (2) Å³	Block, yellow green
Z = 2	0.38 × 0.30 × 0.30 mm

Data collection top

Oxford Gemini S CCD diffractometer	900 independent reflections
Radiation source: fine-focus sealed tube	877 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 26.0°, θ_min = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −8→8
T_min = 0.849, T_max = 1.000	k = −10→10
27710 measured reflections	l = −8→8

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)] = 0.012	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.032	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0218P)² + 0.1909P] where P = (F_o² + 2F_c²)/3
900 reflections	(Δ/σ)_max < 0.001
67 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

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
C1	−0.4152 (3)	0.2500	−0.0364 (3)	0.0162 (4)
C2	−0.3084 (3)	0.2500	0.1617 (3)	0.0142 (4)
C3	−0.24721 (18)	0.11497 (16)	0.27791 (19)	0.0142 (3)
H3C	−0.2679	0.0130	0.2382	0.017*
C4	−0.14854 (18)	0.16776 (15)	0.46603 (18)	0.0145 (3)
H4C	−0.0935	0.1053	0.5710	0.017*
C5	0.1429 (3)	0.2500	0.0334 (3)	0.0185 (4)
H5C	0.0744	0.2500	−0.0957	0.022*
C6	0.20428 (19)	0.11674 (17)	0.1491 (2)	0.0175 (3)
H6C	0.1832	0.0149	0.1089	0.021*
C7	0.30392 (17)	0.16746 (16)	0.33757 (19)	0.0158 (3)
H7C	0.3591	0.1045	0.4420	0.019*
N1	−0.5024 (2)	0.2500	−0.1949 (3)	0.0244 (4)
Ru1	0.00474 (2)	0.2500	0.26311 (2)	0.00953 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0120 (8)	0.0168 (9)	0.0198 (10)	0.000	0.0045 (7)	0.000
C2	0.0093 (8)	0.0168 (9)	0.0170 (9)	0.000	0.0044 (7)	0.000
C3	0.0111 (6)	0.0148 (7)	0.0182 (6)	−0.0022 (5)	0.0065 (5)	−0.0003 (5)
C4	0.0145 (6)	0.0163 (7)	0.0146 (6)	0.0003 (5)	0.0072 (5)	0.0029 (5)
C5	0.0155 (9)	0.0283 (11)	0.0145 (9)	0.000	0.0087 (7)	0.000
C6	0.0143 (6)	0.0190 (7)	0.0222 (7)	0.0005 (5)	0.0101 (5)	−0.0047 (6)
C7	0.0098 (6)	0.0191 (7)	0.0193 (6)	0.0033 (5)	0.0054 (5)	0.0029 (5)
N1	0.0222 (9)	0.0274 (10)	0.0208 (9)	0.000	0.0015 (7)	0.000
Ru1	0.00850 (10)	0.00992 (10)	0.01040 (10)	0.000	0.00305 (6)	0.000

Geometric parameters (Å, º) top

C1—N1	1.148 (3)	C5—Ru1	2.1780 (18)
C1—C2	1.431 (3)	C5—H5C	0.9300
C2—C3ⁱ	1.4401 (17)	C6—C7	1.4274 (19)
C2—C3	1.4401 (17)	C6—Ru1	2.1848 (13)
C2—Ru1	2.1649 (18)	C6—H6C	0.9300
C3—C4	1.4294 (18)	C7—C7ⁱ	1.433 (3)
C3—Ru1	2.1885 (13)	C7—Ru1	2.1878 (12)
C3—H3C	0.9300	C7—H7C	0.9300
C4—C4ⁱ	1.428 (3)	Ru1—C6ⁱ	2.1848 (13)
C4—Ru1	2.2013 (12)	Ru1—C7ⁱ	2.1878 (12)
C4—H4C	0.9300	Ru1—C3ⁱ	2.1885 (13)
C5—C6ⁱ	1.4262 (18)	Ru1—C4ⁱ	2.2013 (12)
C5—C6	1.4262 (18)

N1—C1—C2	179.4 (2)	C5—Ru1—C6	38.16 (5)
C1—C2—C3ⁱ	125.52 (8)	C6ⁱ—Ru1—C6	63.94 (8)
C1—C2—C3	125.52 (8)	C2—Ru1—C7ⁱ	160.38 (4)
C3ⁱ—C2—C3	108.96 (16)	C5—Ru1—C7ⁱ	63.77 (6)
C1—C2—Ru1	123.64 (13)	C6ⁱ—Ru1—C7ⁱ	38.11 (5)
C3ⁱ—C2—Ru1	71.57 (8)	C6—Ru1—C7ⁱ	63.89 (5)
C3—C2—Ru1	71.57 (8)	C2—Ru1—C7	160.38 (4)
C4—C3—C2	106.82 (12)	C5—Ru1—C7	63.77 (6)
C4—C3—Ru1	71.48 (7)	C6ⁱ—Ru1—C7	63.89 (5)
C2—C3—Ru1	69.80 (9)	C6—Ru1—C7	38.11 (5)
C4—C3—H3C	126.6	C7ⁱ—Ru1—C7	38.23 (7)
C2—C3—H3C	126.6	C2—Ru1—C3ⁱ	38.63 (4)
Ru1—C3—H3C	123.8	C5—Ru1—C3ⁱ	127.17 (5)
C4ⁱ—C4—C3	108.70 (8)	C6ⁱ—Ru1—C3ⁱ	112.30 (6)
C4ⁱ—C4—Ru1	71.08 (3)	C6—Ru1—C3ⁱ	161.19 (5)
C3—C4—Ru1	70.51 (7)	C7ⁱ—Ru1—C3ⁱ	125.76 (5)
C4ⁱ—C4—H4C	125.7	C7—Ru1—C3ⁱ	159.25 (5)
C3—C4—H4C	125.7	C2—Ru1—C3	38.63 (4)
Ru1—C4—H4C	124.4	C5—Ru1—C3	127.17 (5)
C6ⁱ—C5—C6	108.40 (17)	C6ⁱ—Ru1—C3	161.18 (5)
C6ⁱ—C5—Ru1	71.18 (9)	C6—Ru1—C3	112.30 (6)
C6—C5—Ru1	71.18 (9)	C7ⁱ—Ru1—C3	159.25 (5)
C6ⁱ—C5—H5C	125.8	C7—Ru1—C3	125.76 (5)
C6—C5—H5C	125.8	C3ⁱ—Ru1—C3	64.76 (7)
Ru1—C5—H5C	123.5	C2—Ru1—C4ⁱ	63.69 (6)
C5—C6—C7	107.83 (13)	C5—Ru1—C4ⁱ	160.55 (4)
C5—C6—Ru1	70.66 (9)	C6ⁱ—Ru1—C4ⁱ	126.43 (5)
C7—C6—Ru1	71.06 (7)	C6—Ru1—C4ⁱ	159.58 (5)
C5—C6—H6C	126.1	C7ⁱ—Ru1—C4ⁱ	111.94 (5)
C7—C6—H6C	126.1	C7—Ru1—C4ⁱ	125.87 (5)
Ru1—C6—H6C	123.8	C3ⁱ—Ru1—C4ⁱ	38.01 (5)
C6—C7—C7ⁱ	107.97 (8)	C3—Ru1—C4ⁱ	63.86 (5)
C6—C7—Ru1	70.83 (7)	C2—Ru1—C4	63.69 (6)
C7ⁱ—C7—Ru1	70.88 (4)	C5—Ru1—C4	160.55 (4)
C6—C7—H7C	126.0	C6ⁱ—Ru1—C4	159.58 (5)
C7ⁱ—C7—H7C	126.0	C6—Ru1—C4	126.42 (5)
Ru1—C7—H7C	123.9	C7ⁱ—Ru1—C4	125.87 (5)
C2—Ru1—C5	113.36 (7)	C7—Ru1—C4	111.94 (5)
C2—Ru1—C6ⁱ	127.17 (5)	C3ⁱ—Ru1—C4	63.86 (5)
C5—Ru1—C6ⁱ	38.16 (5)	C3—Ru1—C4	38.01 (5)
C2—Ru1—C6	127.17 (5)	C4ⁱ—Ru1—C4	37.84 (7)

C1—C2—C3—C4	−179.04 (16)	C2—C3—C4—Ru1	−61.20 (10)
C3ⁱ—C2—C3—C4	0.13 (19)	C6ⁱ—C5—C6—C7	0.1 (2)
Ru1—C2—C3—C4	62.30 (9)	Ru1—C5—C6—C7	−61.69 (9)
C1—C2—C3—Ru1	118.66 (18)	C6ⁱ—C5—C6—Ru1	61.79 (12)
C3ⁱ—C2—C3—Ru1	−62.17 (12)	C5—C6—C7—C7ⁱ	−0.06 (12)
C2—C3—C4—C4ⁱ	−0.08 (12)	Ru1—C6—C7—C7ⁱ	−61.50 (4)
Ru1—C3—C4—C4ⁱ	61.12 (4)	C5—C6—C7—Ru1	61.44 (10)

Symmetry code: (i) x, −y+1/2, z.

Selected bond lengths (Å) and angles (°) for the clarification of the shift of the Ru1 atom towards the C≡N substituent in (I). top

D is the centroid of the C₅H₄ or C₅H₅ ring.

	C2	C3	C4	C5	C6	C7
Ru1—C	2.1650 (18)	2.1886 (13)	2.2013 (12)	2.1779 (18)	2.1847 (13)	2.1879 (12)
C—D—Ru1	88.90 (8)	89.63 (6)	90.93 (6)	89.75 (9)	89.95 (6)	90.16 (6)

Acknowledgements

MK is grateful to the Fonds der Chemischen Industrie for a Chemiefonds fellowship.

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