[η5-(Phenyl­ethyn­yl)cyclo­penta­dien­yl](η4-tetra­phenyl­cyclo­butadiene)cobalt(I)

Courtney, D.; Manning, A.R.; McAdam, C.J.; Simpson, J.

doi:10.1107/S1600536811016928

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m742-m743

doi:10.1107/S1600536811016928

Open

access

[η⁵-(Phenylethynyl)cyclopentadienyl](η⁴-tetraphenylcyclobutadiene)cobalt(I)

Donagh Courtney,^a Anthony R. Manning,^a C. John McAdam ^b and Jim Simpson ^b ^*

^aSchool of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: jsimpson@alkali.otago.ac.nz

(Received 4 May 2011; accepted 4 May 2011; online 14 May 2011)

In the title compound, [Co(C₁₃H₉)(C₂₈H₂₀)], the Co atom is sandwiched between cyclopentadienyl and cyclobutadienyl rings that are inclined at a dihedral angle of 2.6 (3)°. The four phenyl rings are tilted with respect to the cyclobutadienyl plane so that the C₄Ph₄ unit constitutes a four-bladed propeller. The phenyl ring of the phenyl-alkyne substituent is inclined to the cyclopentadienyl ring at an angle of 34.92 (18)°. The crystal structure is stabilized solely by C—H⋯π interactions which generate a three-dimensional network.

Related literature

For the synthesis, see: Stephens & Castro (1963 ). For related structures, see: Classen et al. (2002 ); Cuffe et al. (2005 ); Kjaergaard et al. (2008 ); Zora et al. (2006 ). For recent applications of [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄R)] compounds, see: O'Donohue et al. (2011a ,b ); Nguyen et al. (2008 ).

Experimental

Crystal data

[Co(C₁₃H₉)(C₂₈H₂₀)]
M_r = 580.57
Monoclinic, P 2₁ /c
a = 11.2685 (5) Å
b = 14.9167 (7) Å
c = 16.8122 (8) Å
β = 97.937 (3)°
V = 2798.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 91 K
0.46 × 0.34 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.829, T_max = 1.000
25140 measured reflections
3651 independent reflections
3130 reflections with I > 2σ(I)
R_int = 0.050
θ_max = 22.6°

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.06
3651 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C17–C22 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32⋯Cg1ⁱ	0.95	2.66	3.460 (4)	142
C14—H14⋯Cg2ⁱⁱ	0.95	2.86	3.674 (4)	144
C28—H28⋯Cg2ⁱⁱⁱ	0.95	2.93	3.578 (4)	127
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ) and TITAN (Hunter & Simpson, 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN; molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016928/cv5089sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016928/cv5089Isup2.hkl

checkCIF report

Comment top

Recent interest in [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄R] type compounds has focused on their applications in asymmetric synthesis and catalysis, and as components of molecular machines (Nguyen et al., 2008; O'Donohue et al., 2011a). Despite this attention, comparison with its isoelectronic ferrocene cousin reveals relatively few crystallographically characterized examples. Alkyne derivatives in particular are limited to five structures (Classen et al., 2002). We present here data for the archetypal derivative [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄—C≡ C-Aryl)], Aryl = phenyl.

Bond lengths and angles within the [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄–} fragment are close to those reported in other examples (Classen et al., 2002; Kjaergaard et al., 2008; O'Donohue et al., 2011a,b). The distances between the cyclopentadienyl (Cp) and cyclobutadienyl (Cb) rings and the cobalt atom are 1.6759 (17) Å and 1.6990 (17) Å respectively and the angle between these planes is 2.6 (3)°. The four phenyl rings are tilted in an alternating 20.1/41.9/25.0/46.0° pattern with respect to the Cb plane so that the C₄Ph₄ unit constitutes a four-bladed propeller. The C≡C length of 1.207 (6) Å is similar to those observed for [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄–] butadiynes (Classen et al., 2002) but is slightly longer than its ferrocenyl analogue Fc—C≡ C-Ph, 1.192 (3) (Zora et al., 2006) and other simple ferrocenyl ethynylaryl compounds (Cuffe et al., 2005). The alkyne phenyl group is tilted 34.92 (18)° with respect to the Cp plane in marked contrast to the angle of 89.06 (13)° observed for Fc—C≡C-phenyl (Zora et al., 2006).

In the crystal structure C–H···π interactions (Table 1) involving contacts from the C29···C33 Cp ring to Cg1, the centroid of the C11···C16 ring, and the C11···C16 phenyl ring to Cg2, the centroid of the C17···C22 ring, link the molecules into chains along the c axis (Fig. 2). An additional C28–H28···Cg2 contact generates a three-dimensional network structure (Fig. 3).

Related literature top

For the synthesis, see: Stephens & Castro (1963). For related structures, see: Classen et al. (2002); Cuffe et al. (2005); Kjaergaard et al. (2008); Zora et al. (2006). For recent applications of [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄R)] compounds, see: O'Donohue et al. (2011a,b); Nguyen et al. (2008).

Experimental top

The title compound was prepared by the Castro-Stephens coupling (Stephens & Castro, 1963) of [Co(η⁴-C₄Ph₄)(η⁵-C₅H₄–C≡C–H)] and an equimolar amount of iodobenzene by stirring with 2.5 mol% CuI in N₂ degassed triethylamine for 16 hrs. Solvent was removed under vacuum and the residue chromatographed on silica with a CH₂Cl₂ eluent. X-ray quality crystals were grown from CH₂Cl₂ layered with hexane.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 and SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of I showing the atom numbering with ellipsoids drawn at the 50% probability level.
	Fig. 2. C–H···π interactions (dotted lines) in the structure of I.
	Fig. 3. Crystal packing for I viewed down the a axis.

[η⁵-(Phenylethynyl)cyclopentadienyl](η⁴-tetraphenylcyclobutadiene) cobalt(I) top

Crystal data top

[Co(C₁₃H₉)(C₂₈H₂₀)]	F(000) = 1208
M_r = 580.57	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5542 reflections
a = 11.2685 (5) Å	θ = 2.3–22.4°
b = 14.9167 (7) Å	µ = 0.64 mm⁻¹
c = 16.8122 (8) Å	T = 91 K
β = 97.937 (3)°	Irregular fragment, orange
V = 2798.9 (2) Å³	0.46 × 0.34 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3651 independent reflections
Radiation source: fine-focus sealed tube	3130 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 22.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −12→12
T_min = 0.829, T_max = 1.000	k = −16→16
25140 measured reflections	l = −16→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0693P)² + 4.4297P] where P = (F_o² + 2F_c²)/3
3651 reflections	(Δ/σ)_max < 0.001
379 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Co(C₁₃H₉)(C₂₈H₂₀)]	V = 2798.9 (2) Å³
M_r = 580.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2685 (5) Å	µ = 0.64 mm⁻¹
b = 14.9167 (7) Å	T = 91 K
c = 16.8122 (8) Å	0.46 × 0.34 × 0.13 mm
β = 97.937 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3651 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3130 reflections with I > 2σ(I)
T_min = 0.829, T_max = 1.000	R_int = 0.050
25140 measured reflections	θ_max = 22.6°

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.06	Δρ_max = 1.05 e Å⁻³
3651 reflections	Δρ_min = −0.48 e Å⁻³
379 parameters

Special details top

Experimental. IR ν/cm^-1 ν(C≡C) 2214 (ATR). ¹H NMR (CDCl₃): δ 7.5 (8H, m, Cb-o-Ph), 7.42 (2H, m, C₂-m-Ph), 7.27 (1H, m, C₂-p-Ph), 7.2 (12H, m, Cb-m/p-Ph), 7.14 (2H, m, C₂-o-Ph), 4.82 (2H, t, α-Cp), 4.65 (2H, t, β-Cp). ¹³C NMR (CDCl₃): δ 135.6 (Cb-ipso-Ph), 131.4 (C₂-o-Ph), 128.9 (C₂-m-Ph & Cb-o-Ph), 128.1 (Cb-m-Ph), 127.6 (C₂-p-Ph), 126.4 (Cb-p-Ph), 123.7 (C₂-ipso-Ph), 87.8 (C≡CPh), 85.7 (α-Cp), 85.2 (C≡CPh), 84.9 (β-Cp), 79.2 (ipso-Cp), 76.2 (C₄Ph₄). UV-Vis, λ_max/nm (ε/dm³mol^-1cm^-1) (CH₂Cl₂): 269 (44 000), 300 (sh, 30 000), 330 (sh, 24 000) 385 (sh, 4800).

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	0.6521 (3)	0.2050 (2)	1.0157 (2)	0.0227 (8)
C2	0.5229 (3)	0.2125 (2)	1.0222 (2)	0.0230 (8)
C3	0.4966 (3)	0.1499 (2)	0.9545 (2)	0.0237 (8)
C4	0.6247 (3)	0.1436 (2)	0.9479 (2)	0.0236 (8)
Co1	0.56188 (4)	0.26618 (3)	0.92077 (3)	0.0238 (2)
C5	0.7628 (3)	0.2358 (2)	1.0628 (2)	0.0255 (9)
C6	0.8710 (3)	0.2326 (2)	1.0314 (2)	0.0300 (9)
H6	0.8719	0.2138	0.9775	0.036*
C7	0.9761 (4)	0.2564 (3)	1.0777 (3)	0.0369 (10)
H7	1.0495	0.2522	1.0561	0.044*
C8	0.9763 (4)	0.2865 (3)	1.1556 (3)	0.0394 (10)
H8	1.0496	0.3022	1.1875	0.047*
C9	0.8702 (3)	0.2934 (3)	1.1867 (2)	0.0362 (10)
H9	0.8696	0.3164	1.2393	0.043*
C10	0.7642 (3)	0.2669 (2)	1.1414 (2)	0.0300 (9)
H10	0.6915	0.2700	1.1639	0.036*
C11	0.4524 (3)	0.2540 (2)	1.0794 (2)	0.0221 (8)
C12	0.4748 (3)	0.3418 (2)	1.1069 (2)	0.0254 (8)
H12	0.5361	0.3759	1.0876	0.030*
C13	0.4084 (3)	0.3795 (2)	1.1618 (2)	0.0281 (9)
H13	0.4254	0.4389	1.1805	0.034*
C14	0.3184 (3)	0.3316 (3)	1.1894 (2)	0.0287 (9)
H14	0.2728	0.3577	1.2269	0.034*
C15	0.2945 (3)	0.2448 (3)	1.1621 (2)	0.0269 (9)
H15	0.2318	0.2117	1.1807	0.032*
C16	0.3611 (3)	0.2061 (2)	1.1083 (2)	0.0221 (8)
H16	0.3446	0.1463	1.0907	0.027*
C17	0.3896 (3)	0.1023 (2)	0.9165 (2)	0.0232 (8)
C18	0.4002 (4)	0.0193 (2)	0.8804 (2)	0.0311 (9)
H18	0.4771	−0.0069	0.8810	0.037*
C19	0.2997 (4)	−0.0253 (3)	0.8438 (2)	0.0380 (10)
H19	0.3085	−0.0812	0.8182	0.046*
C20	0.1878 (4)	0.0102 (3)	0.8439 (2)	0.0387 (11)
H20	0.1192	−0.0214	0.8193	0.046*
C21	0.1748 (3)	0.0917 (3)	0.8796 (2)	0.0350 (10)
H21	0.0971	0.1165	0.8798	0.042*
C22	0.2753 (3)	0.1382 (3)	0.9157 (2)	0.0295 (9)
H22	0.2659	0.1948	0.9399	0.035*
C23	0.6966 (3)	0.0865 (2)	0.9016 (2)	0.0252 (8)
C24	0.6679 (3)	0.0760 (3)	0.8189 (2)	0.0321 (9)
H24	0.6005	0.1066	0.7913	0.038*
C25	0.7359 (4)	0.0216 (3)	0.7764 (3)	0.0392 (10)
H25	0.7150	0.0150	0.7200	0.047*
C26	0.8343 (4)	−0.0232 (3)	0.8155 (3)	0.0421 (11)
H26	0.8820	−0.0597	0.7862	0.050*
C27	0.8628 (4)	−0.0144 (3)	0.8978 (3)	0.0387 (10)
H27	0.9296	−0.0458	0.9252	0.046*
C28	0.7945 (3)	0.0398 (2)	0.9404 (2)	0.0301 (9)
H28	0.8147	0.0452	0.9969	0.036*
C29	0.6216 (4)	0.3951 (2)	0.9078 (2)	0.0335 (10)
C30	0.4945 (3)	0.3952 (2)	0.9017 (2)	0.0298 (9)
H30	0.4484	0.4271	0.9356	0.036*
C31	0.4490 (3)	0.3399 (3)	0.8368 (2)	0.0323 (9)
H31	0.3667	0.3281	0.8194	0.039*
C32	0.5459 (3)	0.3053 (3)	0.8023 (2)	0.0298 (9)
H32	0.5399	0.2662	0.7573	0.036*
C33	0.6523 (3)	0.3376 (2)	0.8449 (2)	0.0303 (9)
H33	0.7310	0.3241	0.8344	0.036*
C34	0.7017 (4)	0.4436 (3)	0.9644 (3)	0.0388 (10)
C35	0.7710 (4)	0.4866 (3)	1.0105 (3)	0.0410 (11)
C36	0.8551 (4)	0.5366 (3)	1.0640 (3)	0.0411 (11)
C37	0.8290 (4)	0.6205 (3)	1.0890 (3)	0.0480 (12)
H37	0.7542	0.6475	1.0698	0.058*
C38	0.9135 (4)	0.6667 (3)	1.1432 (3)	0.0476 (12)
H38	0.8948	0.7245	1.1617	0.057*
C39	1.0170 (4)	0.6311 (3)	1.1682 (2)	0.0413 (11)
H39	1.0727	0.6637	1.2048	0.050*
C40	1.0488 (4)	0.5471 (3)	1.1432 (3)	0.0474 (12)
H40	1.1256	0.5227	1.1615	0.057*
C41	0.9665 (4)	0.4998 (3)	1.0913 (3)	0.0438 (11)
H41	0.9861	0.4417	1.0740	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.026 (2)	0.0215 (19)	0.0215 (19)	0.0007 (15)	0.0054 (15)	0.0031 (15)
C2	0.0230 (19)	0.0213 (19)	0.025 (2)	−0.0014 (15)	0.0043 (16)	0.0013 (16)
C3	0.027 (2)	0.0217 (19)	0.0235 (19)	0.0017 (16)	0.0083 (16)	0.0021 (16)
C4	0.028 (2)	0.0210 (19)	0.0219 (19)	0.0008 (16)	0.0028 (15)	0.0031 (16)
Co1	0.0257 (3)	0.0224 (3)	0.0237 (3)	0.0001 (2)	0.0054 (2)	0.0023 (2)
C5	0.025 (2)	0.023 (2)	0.029 (2)	0.0011 (16)	0.0044 (17)	0.0046 (16)
C6	0.025 (2)	0.035 (2)	0.031 (2)	0.0000 (17)	0.0060 (18)	0.0002 (17)
C7	0.022 (2)	0.046 (3)	0.042 (3)	0.0044 (18)	0.0057 (19)	−0.001 (2)
C8	0.024 (2)	0.047 (3)	0.044 (3)	−0.0002 (19)	−0.0071 (19)	0.004 (2)
C9	0.035 (2)	0.040 (2)	0.032 (2)	0.0029 (19)	−0.0012 (19)	0.0007 (19)
C10	0.026 (2)	0.030 (2)	0.033 (2)	0.0017 (17)	0.0046 (18)	0.0046 (17)
C11	0.0200 (19)	0.027 (2)	0.018 (2)	0.0014 (15)	−0.0005 (15)	0.0005 (15)
C12	0.026 (2)	0.026 (2)	0.023 (2)	−0.0035 (16)	0.0019 (16)	0.0022 (16)
C13	0.035 (2)	0.024 (2)	0.024 (2)	0.0007 (17)	−0.0012 (17)	−0.0035 (16)
C14	0.029 (2)	0.036 (2)	0.021 (2)	0.0077 (18)	0.0047 (16)	−0.0025 (17)
C15	0.022 (2)	0.037 (2)	0.023 (2)	−0.0005 (16)	0.0046 (16)	0.0013 (17)
C16	0.0212 (19)	0.0227 (19)	0.0213 (19)	−0.0012 (15)	−0.0008 (15)	−0.0011 (15)
C17	0.030 (2)	0.024 (2)	0.0172 (18)	−0.0031 (16)	0.0054 (15)	0.0032 (16)
C18	0.037 (2)	0.028 (2)	0.030 (2)	−0.0048 (18)	0.0114 (18)	0.0021 (18)
C19	0.056 (3)	0.029 (2)	0.029 (2)	−0.019 (2)	0.008 (2)	−0.0058 (18)
C20	0.040 (3)	0.051 (3)	0.025 (2)	−0.023 (2)	0.0027 (18)	−0.0011 (19)
C21	0.024 (2)	0.051 (3)	0.028 (2)	−0.0068 (19)	−0.0016 (17)	0.004 (2)
C22	0.034 (2)	0.032 (2)	0.022 (2)	0.0005 (18)	0.0035 (16)	0.0023 (17)
C23	0.026 (2)	0.0194 (19)	0.032 (2)	−0.0026 (16)	0.0102 (17)	0.0023 (16)
C24	0.036 (2)	0.033 (2)	0.028 (2)	−0.0001 (18)	0.0074 (18)	−0.0001 (18)
C25	0.053 (3)	0.036 (2)	0.032 (2)	−0.008 (2)	0.017 (2)	−0.0084 (19)
C26	0.041 (3)	0.030 (2)	0.062 (3)	−0.009 (2)	0.033 (2)	−0.013 (2)
C27	0.028 (2)	0.028 (2)	0.061 (3)	−0.0002 (18)	0.012 (2)	−0.003 (2)
C28	0.032 (2)	0.027 (2)	0.032 (2)	−0.0004 (17)	0.0075 (18)	−0.0010 (17)
C29	0.043 (2)	0.021 (2)	0.033 (2)	−0.0109 (18)	−0.0080 (19)	0.0093 (18)
C30	0.033 (2)	0.023 (2)	0.033 (2)	0.0036 (17)	0.0048 (17)	0.0052 (17)
C31	0.036 (2)	0.030 (2)	0.029 (2)	0.0023 (18)	−0.0026 (18)	0.0074 (17)
C32	0.039 (2)	0.027 (2)	0.023 (2)	0.0005 (18)	0.0045 (18)	0.0047 (17)
C33	0.033 (2)	0.032 (2)	0.027 (2)	−0.0016 (18)	0.0084 (17)	0.0062 (17)
C34	0.046 (3)	0.031 (2)	0.040 (3)	−0.001 (2)	0.007 (2)	0.005 (2)
C35	0.043 (3)	0.036 (2)	0.043 (3)	−0.006 (2)	0.003 (2)	−0.002 (2)
C36	0.045 (3)	0.043 (3)	0.037 (2)	−0.012 (2)	0.013 (2)	−0.005 (2)
C37	0.046 (3)	0.041 (3)	0.058 (3)	−0.004 (2)	0.010 (2)	−0.007 (2)
C38	0.057 (3)	0.040 (3)	0.046 (3)	−0.017 (2)	0.011 (2)	−0.012 (2)
C39	0.045 (3)	0.045 (3)	0.036 (2)	−0.018 (2)	0.014 (2)	−0.012 (2)
C40	0.045 (3)	0.055 (3)	0.040 (3)	−0.008 (2)	0.001 (2)	−0.001 (2)
C41	0.051 (3)	0.042 (3)	0.037 (3)	−0.003 (2)	0.002 (2)	0.003 (2)

Geometric parameters (Å, º) top

C1—C5	1.456 (5)	C18—H18	0.9500
C1—C4	1.462 (5)	C19—C20	1.368 (6)
C1—C2	1.478 (5)	C19—H19	0.9500
C1—Co1	1.991 (3)	C20—C21	1.373 (6)
C2—C11	1.467 (5)	C20—H20	0.9500
C2—C3	1.470 (5)	C21—C22	1.393 (5)
C2—Co1	1.987 (3)	C21—H21	0.9500
C3—C4	1.466 (5)	C22—H22	0.9500
C3—C17	1.468 (5)	C23—C28	1.389 (5)
C3—Co1	1.997 (3)	C23—C24	1.392 (5)
C4—C23	1.471 (5)	C24—C25	1.382 (6)
C4—Co1	1.991 (3)	C24—H24	0.9500
Co1—C33	2.039 (4)	C25—C26	1.382 (6)
Co1—C32	2.059 (4)	C25—H25	0.9500
Co1—C29	2.059 (4)	C26—C27	1.382 (6)
Co1—C30	2.078 (4)	C26—H26	0.9500
Co1—C31	2.079 (4)	C27—C28	1.383 (6)
C5—C6	1.395 (5)	C27—H27	0.9500
C5—C10	1.398 (5)	C28—H28	0.9500
C6—C7	1.371 (6)	C29—C34	1.416 (6)
C6—H6	0.9500	C29—C30	1.422 (6)
C7—C8	1.384 (6)	C29—C33	1.439 (6)
C7—H7	0.9500	C30—C31	1.407 (5)
C8—C9	1.374 (6)	C30—H30	0.9500
C8—H8	0.9500	C31—C32	1.404 (5)
C9—C10	1.382 (5)	C31—H31	0.9500
C9—H9	0.9500	C32—C33	1.396 (5)
C10—H10	0.9500	C32—H32	0.9500
C11—C16	1.394 (5)	C33—H33	0.9500
C11—C12	1.400 (5)	C34—C35	1.207 (6)
C12—C13	1.386 (5)	C35—C36	1.424 (6)
C12—H12	0.9500	C36—C37	1.366 (6)
C13—C14	1.372 (5)	C36—C41	1.388 (6)
C13—H13	0.9500	C37—C38	1.404 (6)
C14—C15	1.388 (5)	C37—H37	0.9500
C14—H14	0.9500	C38—C39	1.297 (6)
C15—C16	1.380 (5)	C38—H38	0.9500
C15—H15	0.9500	C39—C40	1.383 (6)
C16—H16	0.9500	C39—H39	0.9500
C17—C18	1.390 (5)	C40—C41	1.377 (6)
C17—C22	1.393 (5)	C40—H40	0.9500
C18—C19	1.382 (6)	C41—H41	0.9500

C5—C1—C4	133.9 (3)	C16—C15—H15	119.7
C5—C1—C2	135.6 (3)	C14—C15—H15	119.7
C4—C1—C2	90.0 (3)	C15—C16—C11	120.5 (3)
C5—C1—Co1	126.6 (2)	C15—C16—H16	119.7
C4—C1—Co1	68.44 (19)	C11—C16—H16	119.7
C2—C1—Co1	68.01 (19)	C18—C17—C22	118.2 (3)
C11—C2—C3	134.9 (3)	C18—C17—C3	120.4 (3)
C11—C2—C1	135.1 (3)	C22—C17—C3	121.4 (3)
C3—C2—C1	89.5 (3)	C19—C18—C17	120.6 (4)
C11—C2—Co1	126.7 (2)	C19—C18—H18	119.7
C3—C2—Co1	68.71 (19)	C17—C18—H18	119.7
C1—C2—Co1	68.35 (19)	C20—C19—C18	120.8 (4)
C4—C3—C17	134.0 (3)	C20—C19—H19	119.6
C4—C3—C2	90.2 (3)	C18—C19—H19	119.6
C17—C3—C2	135.3 (3)	C19—C20—C21	119.8 (4)
C4—C3—Co1	68.21 (19)	C19—C20—H20	120.1
C17—C3—Co1	127.5 (2)	C21—C20—H20	120.1
C2—C3—Co1	67.98 (19)	C20—C21—C22	120.1 (4)
C1—C4—C3	90.3 (3)	C20—C21—H21	120.0
C1—C4—C23	134.7 (3)	C22—C21—H21	120.0
C3—C4—C23	134.2 (3)	C17—C22—C21	120.5 (4)
C1—C4—Co1	68.49 (19)	C17—C22—H22	119.7
C3—C4—Co1	68.65 (19)	C21—C22—H22	119.7
C23—C4—Co1	127.9 (2)	C28—C23—C24	118.2 (3)
C2—Co1—C4	63.05 (14)	C28—C23—C4	120.1 (3)
C2—Co1—C1	43.63 (14)	C24—C23—C4	121.7 (3)
C4—Co1—C1	43.07 (14)	C25—C24—C23	121.0 (4)
C2—Co1—C3	43.31 (14)	C25—C24—H24	119.5
C4—Co1—C3	43.14 (14)	C23—C24—H24	119.5
C1—Co1—C3	62.71 (14)	C24—C25—C26	120.2 (4)
C2—Co1—C33	159.37 (15)	C24—C25—H25	119.9
C4—Co1—C33	115.52 (15)	C26—C25—H25	119.9
C1—Co1—C33	119.79 (15)	C25—C26—C27	119.4 (4)
C3—Co1—C33	150.13 (15)	C25—C26—H26	120.3
C2—Co1—C32	160.72 (15)	C27—C26—H26	120.3
C4—Co1—C32	117.56 (15)	C26—C27—C28	120.3 (4)
C1—Co1—C32	150.69 (15)	C26—C27—H27	119.9
C3—Co1—C32	122.29 (15)	C28—C27—H27	119.9
C33—Co1—C32	39.82 (15)	C27—C28—C23	120.9 (4)
C2—Co1—C29	125.57 (15)	C27—C28—H28	119.6
C4—Co1—C29	140.44 (15)	C23—C28—H28	119.6
C1—Co1—C29	112.01 (15)	C34—C29—C30	126.1 (4)
C3—Co1—C29	168.57 (15)	C34—C29—C33	127.0 (4)
C33—Co1—C29	41.11 (16)	C30—C29—C33	106.9 (3)
C32—Co1—C29	67.61 (15)	C34—C29—Co1	126.3 (3)
C2—Co1—C30	112.71 (15)	C30—C29—Co1	70.6 (2)
C4—Co1—C30	175.54 (15)	C33—C29—Co1	68.7 (2)
C1—Co1—C30	133.08 (15)	C31—C30—C29	108.1 (3)
C3—Co1—C30	135.03 (15)	C31—C30—Co1	70.3 (2)
C33—Co1—C30	67.86 (15)	C29—C30—Co1	69.2 (2)
C32—Co1—C30	66.89 (15)	C31—C30—H30	126.0
C29—Co1—C30	40.20 (15)	C29—C30—H30	126.0
C2—Co1—C31	127.49 (15)	Co1—C30—H30	126.1
C4—Co1—C31	143.75 (15)	C32—C31—C30	108.4 (3)
C1—Co1—C31	169.44 (15)	C32—C31—Co1	69.4 (2)
C3—Co1—C31	115.96 (15)	C30—C31—Co1	70.2 (2)
C33—Co1—C31	67.09 (15)	C32—C31—H31	125.8
C32—Co1—C31	39.65 (15)	C30—C31—H31	125.8
C29—Co1—C31	67.17 (15)	Co1—C31—H31	126.2
C30—Co1—C31	39.56 (15)	C33—C32—C31	108.8 (3)
C6—C5—C10	118.2 (3)	C33—C32—Co1	69.3 (2)
C6—C5—C1	120.7 (3)	C31—C32—Co1	70.9 (2)
C10—C5—C1	121.0 (3)	C33—C32—H32	125.6
C7—C6—C5	120.5 (4)	C31—C32—H32	125.6
C7—C6—H6	119.8	Co1—C32—H32	125.7
C5—C6—H6	119.8	C32—C33—C29	107.9 (3)
C6—C7—C8	120.7 (4)	C32—C33—Co1	70.9 (2)
C6—C7—H7	119.7	C29—C33—Co1	70.2 (2)
C8—C7—H7	119.7	C32—C33—H33	126.1
C9—C8—C7	119.8 (4)	C29—C33—H33	126.1
C9—C8—H8	120.1	Co1—C33—H33	124.5
C7—C8—H8	120.1	C35—C34—C29	177.7 (4)
C8—C9—C10	120.0 (4)	C34—C35—C36	178.6 (5)
C8—C9—H9	120.0	C37—C36—C41	118.9 (4)
C10—C9—H9	120.0	C37—C36—C35	121.4 (4)
C9—C10—C5	120.8 (4)	C41—C36—C35	119.7 (4)
C9—C10—H10	119.6	C36—C37—C38	119.6 (4)
C5—C10—H10	119.6	C36—C37—H37	120.2
C16—C11—C12	118.2 (3)	C38—C37—H37	120.2
C16—C11—C2	120.3 (3)	C39—C38—C37	120.5 (4)
C12—C11—C2	121.4 (3)	C39—C38—H38	119.7
C13—C12—C11	120.7 (3)	C37—C38—H38	119.7
C13—C12—H12	119.6	C38—C39—C40	122.1 (4)
C11—C12—H12	119.6	C38—C39—H39	119.0
C14—C13—C12	120.4 (3)	C40—C39—H39	119.0
C14—C13—H13	119.8	C41—C40—C39	118.4 (4)
C12—C13—H13	119.8	C41—C40—H40	120.8
C13—C14—C15	119.5 (3)	C39—C40—H40	120.8
C13—C14—H14	120.2	C40—C41—C36	120.4 (4)
C15—C14—H14	120.2	C40—C41—H41	119.8
C16—C15—C14	120.6 (3)	C36—C41—H41	119.8

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C11–C16 and C17–C22 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···Cg1ⁱ	0.95	2.66	3.460 (4)	142
C14—H14···Cg2ⁱⁱ	0.95	2.86	3.674 (4)	144
C28—H28···Cg2ⁱⁱⁱ	0.95	2.93	3.578 (4)	127

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₃H₉)(C₂₈H₂₀)]
M_r	580.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	91
a, b, c (Å)	11.2685 (5), 14.9167 (7), 16.8122 (8)
β (°)	97.937 (3)
V (Å³)	2798.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.46 × 0.34 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.829, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	25140, 3651, 3130
R_int	0.050
θ_max (°)	22.6
(sin θ/λ)_max (Å⁻¹)	0.540

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.06
No. of reflections	3651
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.48

Computer programs: APEX2 (Bruker, 2006), APEX2 and SAINT (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999), SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C11–C16 and C17–C22 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···Cg1ⁱ	0.95	2.66	3.460 (4)	142
C14—H14···Cg2ⁱⁱ	0.95	2.86	3.674 (4)	144
C28—H28···Cg2ⁱⁱⁱ	0.95	2.93	3.578 (4)	127

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

Acknowledgements

The authors thank the New Economy Research Fund (grant No. UOO-X0808) for support of this work and the University of Otago for the purchase of the diffractometer.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Classen, J., Gleiter, R. & Rominger, F. (2002). Eur. J. Inorg. Chem. pp. 2040–2046. CrossRef Google Scholar
Cuffe, L., Hudson, R. D. A., Gallagher, J. F., Jennings, S., McAdam, C. J., Connelly, R. B. T., Manning, A. R., Robinson, B. H. & Simpson, J. (2005). Organometallics, 24, 2051–2060. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand. Google Scholar
Kjaergaard, H. G., McAdam, C. J., Manning, A. R., Mueller-Bunz, H., O'Donohue, P., Ortin, Y., Robinson, B. H. & Simpson, J. (2008). Inorg. Chim. Acta, 361, 1616–1623. CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nguyen, H. V., Yeamine, M. R., Amin, J., Motevalli, M. & Richards, C. J. (2008). J. Organomet. Chem. 693, 3668–3676. CrossRef CAS Google Scholar
O'Donohue, P., McAdam, C. J., Courtney, D., Ortin, Y., Müller-Bunz, H., Manning, A. R., McGlinchey, M. J. & Simpson, J. (2011a). J. Organomet. Chem. 696, 1496–1509. CAS Google Scholar
O'Donohue, P., McAdam, C. J., Courtney, D., Ortin, Y., Müller-Bunz, H., Manning, A. R., McGlinchey, M. J. & Simpson, J. (2011b). J. Organomet. Chem. 696, 1510–1527. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stephens, R. D. & Castro, C. E. (1963). J. Org. Chem. 28, 3313–3315. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zora, M., Açıkgöz, C., Tumay, T. A., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327–m330. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m742-m743

doi:10.1107/S1600536811016928

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)