(η6-N,N-Diethyl­aniline)(η4-1,2,3,4-tetra­methyl­cyclo­buta­diene)­cobalt(I) hexa­fluoro­phosphate

Kennedy, A.R.; Pauson, P.L.

doi:10.1107/S1600536805000863

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 2| February 2005| Pages m302-m303

https://doi.org/10.1107/S1600536805000863

(η⁶-N,N-Diethylaniline)(η⁴-1,2,3,4-tetramethylcyclobutadiene)cobalt(I) hexafluorophosphate

Alan R. Kennedy ^a ^* and Peter L. Pauson ^a

^aDepartment of Pure and Applied Chemistry, University of Strathclyde, Glasgow G1 1XL, Scotland
^*Correspondence e-mail: a.r.kennedy@strath.ac.uk

(Received 6 January 2005; accepted 10 January 2005; online 15 January 2005)

The title isocobaltocenium salt, [Co(C₈H₁₂)(C₁₀H₁₅N)]PF₆, is shown to exist as discrete monomers with near equivalent C—C bonds in the cyclobutadiene ring.

Comment

Isocobaltocenes are the series of compounds in which, in place of two cyclopentadienyl residues, the cobalt is π-bonded to one cyclobutadiene and one benzene ring. Species with bulky cyclobutadiene ring substituents have been known since the work of Maitlis & Efraty (1965 ) and have been widely crystallographically characterized. However, despite synthetic protocols being well known (Cook et al., 1987 ), the only known structures of tetramethylcyclobutadiene-based isocobaltocenes are two species with unusual substituted boratabenzenes (Herberich et al., 2002 ).

Reported here is the structure of (I), a tetramethylcyclobutadiene isocobaltocenium salt with a simple N,N-diethylaniline group as its arene component (Fig. 1). The centroid of the cyclobutadiene group lies further from Co1 than the centroid of the benzene ring (1.705 versus 1.592 Å) and this distance is also slightly longer than those found for the boratabenzene species (range 1.686–1.702 Å; Herberich et al., 2002). However, it falls into the middle of the range found for nine general Co–tetramethylcyclobutadiene complexes found in a search of the Cambridge Structural Database (Version 5, with updates to December 2004; Allen, 2002 ). The cyclobutadiene ring C—C distances show only slight signs of alternate single- and double-bond nature (Table 1), indicating a high degree of aromaticity. The Co atom is placed over the centre of the cyclobutadiene ring but is displaced away from the amine-substituted C1 atom of the benzene ring. No strong intermolecular contacts were observed.

Figure 1
The molecular structure of the cation of (I

), shown with 50% probability displacement ellipsoids. H atoms and disordered fragments have been omitted for clarity.

Experimental

The title compound was prepared according to the method of Cook et al. (1987).

Crystal data

[Co(C₈H₁₂)(C₁₀H₁₅N)]PF₆
M_r = 461.31
Monoclinic, P2₁/c
a = 8.4201 (2) Å
b = 16.2404 (3) Å
c = 15.1960 (4) Å
β = 103.844 (1)°
V = 2017.63 (8) Å³
Z = 4
D_x = 1.519 Mg m⁻³
Mo Kα radiation
Cell parameters from 21 381 reflections
θ = 3.0–27.5°
μ = 0.99 mm⁻¹
T = 120 (2) K
Cut block, yellow
0.12 × 0.10 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
φ and ω scans
21 381 measured reflections
4587 independent reflections
3068 reflections with I > 2σ(I)
R_int = 0.078
θ_max = 27.5°
h = −10 → 10
k = −21 → 21
l = −17 → 19

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.141
S = 1.03
4587 reflections
273 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0681P)² + 0.6904P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—C14	1.973 (3)
Co1—C11	1.987 (3)
Co1—C13	1.992 (3)
Co1—C12	2.004 (3)
Co1—C3	2.077 (3)
Co1—C5	2.088 (4)
Co1—C4	2.101 (3)
Co1—C2	2.109 (3)
Co1—C6	2.126 (3)
Co1—C1	2.241 (3)
C11—C14	1.447 (5)
C11—C12	1.450 (4)
C12—C13	1.442 (4)
C13—C14	1.452 (5)

C14—C11—C12	90.0 (3)
C13—C12—C11	90.1 (3)
C12—C13—C14	90.1 (3)
C11—C14—C13	89.8 (3)

H atoms were included in the riding-model approximation with C—H distances: CH₃ 0.98, CH₂ 0.99 and CH 0.95 Å, and with U_iso(H) = 1.2U_eq(C) and 1.5U_eq(C_methyl). The PF₆⁻ anion is rotationally disordered about the F3—P1—F4 axis. After several trial calculations, the remaining four F atoms were refined over 12 sites with set occupancies. The largest remaining electron-density peaks all occur near to the PF₆⁻ anion. The C10 methyl group was refined as disordered over two sites with occupancies refined [0.52 (2):0.48 (2)]. The occupancies of atoms F1, F2, F5 and F6 were set at 0.5 and the occupancies of atoms F7–F12 were set at 0.25.

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1988 ); cell refinement: DENZO and COLLECT; data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805000863/cv6448sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805000863/cv6448Isup2.hkl

Computing details top

Data collection: DENZO and COLLECT (Otwinowski & Minor, 1997; Hooft, 1988); cell refinement: DENZO and COLLECT; data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(η⁶-N,N-Diethylaniline)(η⁴-1,2,3,4-tetramethylcyclobutadiene)cobalt(I) hexafluorophosphate top

Crystal data top

[Co(C₈H₁₂)(C₁₀H₁₅N)]PF₆	F(000) = 952
M_r = 461.31	D_x = 1.519 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4201 (2) Å	Cell parameters from 21381 reflections
b = 16.2404 (3) Å	θ = 3.0–27.5°
c = 15.1960 (4) Å	µ = 0.99 mm⁻¹
β = 103.844 (1)°	T = 120 K
V = 2017.63 (8) Å³	Cut block, yellow
Z = 4	0.12 × 0.10 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	3068 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.078
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
φ and ω scans	h = −10→10
21381 measured reflections	k = −21→21
4587 independent reflections	l = −17→19

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0681P)² + 0.6904P] where P = (F_o² + 2F_c²)/3
4587 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.78 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	Occ. (<1)
Co1	0.44977 (5)	0.14989 (2)	0.68037 (3)	0.02448 (16)
P1	0.07791 (11)	−0.09763 (5)	0.76435 (7)	0.0360 (2)
F1	0.0804 (8)	−0.1934 (4)	0.7872 (5)	0.065 (2)	0.50
F2	0.0287 (7)	−0.0740 (4)	0.8545 (4)	0.0581 (16)*	0.50
F3	0.2675 (3)	−0.10062 (16)	0.81208 (16)	0.0621 (7)
F4	−0.1109 (3)	−0.09398 (17)	0.7176 (2)	0.0812 (9)
F5	0.1390 (9)	−0.1072 (5)	0.6680 (5)	0.057 (2)	0.50
F6	0.0897 (8)	−0.0010 (4)	0.7584 (5)	0.071 (2)*	0.50
F7	0.0865 (7)	−0.0158 (4)	0.8326 (4)	0.0219 (14)*	0.25
F8	0.1053 (8)	−0.0390 (5)	0.6877 (5)	0.0245 (15)*	0.25
F9	0.0087 (12)	−0.1080 (8)	0.8508 (6)	0.044 (2)*	0.25
F10	0.0699 (10)	−0.1755 (6)	0.7049 (7)	0.036 (2)*	0.25
F11	0.0515 (16)	−0.1946 (9)	0.7480 (10)	0.040 (3)*	0.25
F12	0.0552 (10)	−0.1542 (6)	0.8531 (6)	0.0355 (18)*	0.25
F13	0.123 (2)	−0.1303 (11)	0.6776 (13)	0.058 (5)*	0.25
F14	0.0764 (12)	−0.0062 (6)	0.7203 (8)	0.042 (2)*	0.25
N1	0.7040 (4)	0.11021 (18)	0.8825 (2)	0.0429 (8)
C1	0.5745 (4)	0.14937 (18)	0.8282 (2)	0.0329 (8)
C2	0.5938 (5)	0.22397 (19)	0.7831 (2)	0.0374 (8)
H2	0.7007	0.2445	0.7865	0.045*
C3	0.4575 (5)	0.2681 (2)	0.7334 (2)	0.0412 (9)
H3	0.4735	0.3195	0.7070	0.049*
C4	0.2990 (5)	0.2371 (2)	0.7224 (2)	0.0431 (9)
H4	0.2069	0.2676	0.6904	0.052*
C5	0.2796 (5)	0.1602 (2)	0.7596 (2)	0.0425 (9)
H5	0.1730	0.1375	0.7512	0.051*
C6	0.4145 (4)	0.1157 (2)	0.8094 (2)	0.0322 (7)
H6	0.3983	0.0622	0.8308	0.039*
C7	0.6824 (5)	0.0478 (2)	0.9488 (2)	0.0472 (10)
H7A	0.5771	0.0578	0.9652	0.057*
H7B	0.7710	0.0540	1.0044	0.057*
C8	0.6839 (5)	−0.0384 (2)	0.9146 (3)	0.0526 (10)
H8A	0.5876	−0.0473	0.8646	0.079*
H8B	0.6819	−0.0771	0.9637	0.079*
H8C	0.7833	−0.0473	0.8929	0.079*
C9	0.8713 (5)	0.1362 (3)	0.8877 (3)	0.0701 (15)
H9A	0.8831	0.1581	0.8289	0.084*
H9B	0.9489	0.0900	0.9063	0.084*
C10A	0.9020 (11)	0.2107 (5)	0.9677 (6)	0.040 (3)*	0.518 (17)
H10A	1.0149	0.2306	0.9787	0.060*	0.518 (17)
H10B	0.8823	0.1883	1.0241	0.060*	0.518 (17)
H10C	0.8264	0.2564	0.9468	0.060*	0.518 (17)
C10B	0.9617 (14)	0.1965 (6)	0.9370 (7)	0.052 (3)*	0.482 (17)
H10D	0.9046	0.2492	0.9233	0.078*	0.482 (17)
H10E	1.0682	0.1997	0.9216	0.078*	0.482 (17)
H10F	0.9780	0.1842	1.0017	0.078*	0.482 (17)
C11	0.3432 (4)	0.09746 (18)	0.5630 (2)	0.0323 (8)
C12	0.4799 (4)	0.04821 (17)	0.61148 (19)	0.0253 (7)
C13	0.5916 (4)	0.1125 (2)	0.6003 (2)	0.0353 (8)
C14	0.4550 (5)	0.16211 (19)	0.5519 (2)	0.0359 (8)
C15	0.1647 (5)	0.0810 (3)	0.5277 (3)	0.0552 (11)
H15A	0.1036	0.1326	0.5260	0.083*
H15B	0.1281	0.0417	0.5676	0.083*
H15C	0.1453	0.0580	0.4665	0.083*
C16	0.4987 (4)	−0.03750 (19)	0.6468 (2)	0.0348 (8)
H16A	0.5008	−0.0756	0.5971	0.052*
H16B	0.4064	−0.0512	0.6731	0.052*
H16C	0.6011	−0.0422	0.6935	0.052*
C17	0.7718 (5)	0.1187 (3)	0.6168 (4)	0.0657 (13)
H17A	0.8231	0.0851	0.6695	0.099*
H17B	0.8051	0.1763	0.6284	0.099*
H17C	0.8065	0.0989	0.5634	0.099*
C18	0.4395 (7)	0.2401 (2)	0.4985 (3)	0.0679 (14)
H18A	0.4331	0.2272	0.4347	0.102*
H18B	0.5351	0.2750	0.5222	0.102*
H18C	0.3401	0.2692	0.5035	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0316 (3)	0.0195 (2)	0.0230 (2)	0.00180 (17)	0.00793 (18)	−0.00229 (16)
P1	0.0291 (5)	0.0295 (5)	0.0451 (6)	−0.0006 (4)	0.0001 (4)	0.0083 (4)
F1	0.060 (4)	0.038 (3)	0.093 (6)	0.003 (2)	0.007 (4)	0.042 (4)
F3	0.0297 (12)	0.0898 (19)	0.0587 (15)	0.0015 (11)	−0.0057 (11)	0.0010 (13)
F4	0.0309 (13)	0.0776 (19)	0.118 (2)	−0.0047 (12)	−0.0167 (14)	0.0332 (16)
F5	0.063 (4)	0.065 (5)	0.043 (3)	−0.024 (3)	0.012 (2)	0.013 (3)
N1	0.0461 (19)	0.0327 (16)	0.0421 (18)	−0.0054 (14)	−0.0047 (14)	0.0082 (13)
C1	0.048 (2)	0.0233 (16)	0.0258 (17)	0.0008 (14)	0.0063 (16)	−0.0028 (13)
C2	0.050 (2)	0.0251 (17)	0.0321 (19)	−0.0023 (15)	0.0005 (16)	−0.0072 (14)
C3	0.065 (3)	0.0208 (17)	0.0325 (19)	0.0105 (16)	0.0012 (18)	−0.0089 (14)
C4	0.050 (2)	0.046 (2)	0.0326 (19)	0.0235 (18)	0.0097 (17)	−0.0055 (16)
C5	0.042 (2)	0.060 (3)	0.0295 (18)	0.0087 (18)	0.0166 (17)	−0.0041 (17)
C6	0.041 (2)	0.0339 (18)	0.0238 (16)	0.0020 (15)	0.0119 (15)	−0.0035 (14)
C7	0.063 (3)	0.039 (2)	0.034 (2)	0.0015 (18)	0.0016 (19)	0.0028 (16)
C8	0.063 (3)	0.037 (2)	0.061 (3)	0.0005 (19)	0.023 (2)	0.0026 (19)
C9	0.045 (2)	0.058 (3)	0.089 (4)	−0.014 (2)	−0.021 (2)	0.036 (2)
C11	0.049 (2)	0.0237 (16)	0.0220 (16)	0.0082 (14)	0.0035 (15)	−0.0035 (12)
C12	0.0363 (18)	0.0211 (15)	0.0195 (15)	0.0015 (13)	0.0085 (13)	−0.0038 (12)
C13	0.048 (2)	0.0247 (17)	0.041 (2)	0.0015 (15)	0.0252 (17)	−0.0052 (14)
C14	0.060 (2)	0.0248 (17)	0.0295 (18)	0.0075 (15)	0.0231 (17)	0.0033 (13)
C15	0.052 (3)	0.050 (2)	0.052 (2)	0.0150 (19)	−0.012 (2)	−0.0141 (19)
C16	0.050 (2)	0.0230 (16)	0.0336 (18)	0.0058 (15)	0.0149 (16)	0.0013 (14)
C17	0.052 (3)	0.045 (2)	0.114 (4)	−0.005 (2)	0.047 (3)	−0.018 (3)
C18	0.131 (4)	0.033 (2)	0.058 (3)	0.019 (2)	0.059 (3)	0.0158 (19)

Geometric parameters (Å, º) top

Co1—C14	1.973 (3)	C7—C8	1.495 (5)
Co1—C11	1.987 (3)	C7—H7A	0.9900
Co1—C13	1.992 (3)	C7—H7B	0.9900
Co1—C12	2.004 (3)	C8—H8A	0.9800
Co1—C3	2.077 (3)	C8—H8B	0.9800
Co1—C5	2.088 (4)	C8—H8C	0.9800
Co1—C4	2.101 (3)	C9—C10B	1.352 (9)
Co1—C2	2.109 (3)	C9—C10A	1.691 (10)
Co1—C6	2.126 (3)	C9—H9A	0.9900
Co1—C1	2.241 (3)	C9—H9B	0.9900
P1—F10	1.546 (8)	C10A—H10A	0.9800
P1—F13	1.548 (19)	C10A—H10B	0.9800
P1—F8	1.564 (7)	C10A—H10C	0.9800
P1—F9	1.568 (9)	C10B—H10D	0.9800
P1—F2	1.571 (6)	C10B—H10E	0.9800
P1—F6	1.576 (6)	C10B—H10F	0.9800
P1—F4	1.579 (2)	C11—C14	1.447 (5)
P1—F3	1.588 (2)	C11—C12	1.450 (4)
P1—F1	1.592 (5)	C11—C15	1.494 (5)
P1—F11	1.602 (14)	C12—C13	1.442 (4)
P1—F14	1.627 (9)	C12—C16	1.487 (4)
P1—F5	1.671 (7)	C13—C14	1.452 (5)
N1—C1	1.358 (4)	C13—C17	1.481 (5)
N1—C9	1.454 (5)	C14—C18	1.493 (4)
N1—C7	1.470 (4)	C15—H15A	0.9800
C1—C6	1.417 (5)	C15—H15B	0.9800
C1—C2	1.420 (4)	C15—H15C	0.9800
C2—C3	1.409 (5)	C16—H16A	0.9800
C2—H2	0.9500	C16—H16B	0.9800
C3—C4	1.399 (5)	C16—H16C	0.9800
C3—H3	0.9500	C17—H17A	0.9800
C4—C5	1.397 (5)	C17—H17B	0.9800
C4—H4	0.9500	C17—H17C	0.9800
C5—C6	1.405 (5)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800

C14—Co1—C11	42.86 (14)	C1—C6—H6	119.4
C14—Co1—C13	42.95 (14)	Co1—C6—H6	128.2
C11—Co1—C13	61.91 (15)	N1—C7—C8	113.3 (3)
C14—Co1—C12	61.99 (12)	N1—C7—H7A	108.9
C11—Co1—C12	42.62 (12)	C8—C7—H7A	108.9
C13—Co1—C12	42.29 (13)	N1—C7—H7B	108.9
C14—Co1—C3	106.54 (13)	C8—C7—H7B	108.9
C11—Co1—C3	135.23 (13)	H7A—C7—H7B	107.7
C13—Co1—C3	123.42 (15)	C7—C8—H8A	109.5
C12—Co1—C3	165.54 (14)	C7—C8—H8B	109.5
C14—Co1—C5	138.04 (16)	H8A—C8—H8B	109.5
C11—Co1—C5	109.11 (15)	C7—C8—H8C	109.5
C13—Co1—C5	166.19 (14)	H8A—C8—H8C	109.5
C12—Co1—C5	123.91 (14)	H8B—C8—H8C	109.5
C3—Co1—C5	70.38 (15)	C10B—C9—N1	130.6 (8)
C14—Co1—C4	113.03 (14)	C10B—C9—C10A	27.7 (5)
C11—Co1—C4	112.70 (14)	N1—C9—C10A	103.1 (5)
C13—Co1—C4	152.28 (15)	C10B—C9—H9A	94.3
C12—Co1—C4	151.15 (15)	N1—C9—H9A	111.1
C3—Co1—C4	39.11 (15)	C10A—C9—H9A	111.1
C5—Co1—C4	38.95 (14)	C10B—C9—H9B	98.3
C14—Co1—C2	122.01 (15)	N1—C9—H9B	111.1
C11—Co1—C2	164.86 (14)	C10A—C9—H9B	111.1
C13—Co1—C2	107.67 (15)	H9A—C9—H9B	109.1
C12—Co1—C2	137.26 (13)	C9—C10A—H10A	109.5
C3—Co1—C2	39.33 (13)	C9—C10A—H10B	109.5
C5—Co1—C2	83.08 (15)	C9—C10A—H10C	109.5
C4—Co1—C2	70.89 (15)	C9—C10B—H10D	109.5
C14—Co1—C6	168.49 (14)	C9—C10B—H10E	109.5
C11—Co1—C6	125.70 (14)	H10D—C10B—H10E	109.5
C13—Co1—C6	136.05 (14)	C9—C10B—H10F	109.5
C12—Co1—C6	109.27 (12)	H10D—C10B—H10F	109.5
C3—Co1—C6	83.21 (14)	H10E—C10B—H10F	109.5
C5—Co1—C6	38.94 (13)	C14—C11—C12	90.0 (3)
C4—Co1—C6	70.59 (14)	C14—C11—C15	135.6 (3)
C2—Co1—C6	69.42 (13)	C12—C11—C15	133.8 (3)
C14—Co1—C1	151.21 (15)	C14—C11—Co1	68.08 (18)
C11—Co1—C1	154.34 (12)	C12—C11—Co1	69.32 (17)
C13—Co1—C1	113.93 (14)	C15—C11—Co1	126.7 (3)
C12—Co1—C1	115.67 (12)	C13—C12—C11	90.1 (3)
C3—Co1—C1	69.56 (12)	C13—C12—C16	134.8 (3)
C5—Co1—C1	69.11 (14)	C11—C12—C16	134.6 (3)
C4—Co1—C1	82.52 (13)	C13—C12—Co1	68.44 (16)
C2—Co1—C1	37.96 (12)	C11—C12—Co1	68.06 (16)
C6—Co1—C1	37.76 (12)	C16—C12—Co1	126.8 (2)
C1—N1—C9	121.6 (3)	C12—C13—C14	90.1 (3)
C1—N1—C7	121.7 (3)	C12—C13—C17	134.4 (3)
C9—N1—C7	116.1 (3)	C14—C13—C17	134.7 (3)
N1—C1—C6	121.9 (3)	C12—C13—Co1	69.27 (17)
N1—C1—C2	121.6 (3)	C14—C13—Co1	67.82 (18)
C6—C1—C2	116.4 (3)	C17—C13—Co1	128.0 (3)
N1—C1—Co1	136.6 (2)	C11—C14—C13	89.8 (3)
C6—C1—Co1	66.71 (18)	C11—C14—C18	134.8 (4)
C2—C1—Co1	65.99 (18)	C13—C14—C18	134.6 (4)
C3—C2—C1	121.3 (3)	C11—C14—Co1	69.06 (17)
C3—C2—Co1	69.09 (18)	C13—C14—Co1	69.23 (18)
C1—C2—Co1	76.05 (19)	C18—C14—Co1	127.1 (2)
C3—C2—H2	119.3	C11—C15—H15A	109.5
C1—C2—H2	119.3	C11—C15—H15B	109.5
Co1—C2—H2	127.6	H15A—C15—H15B	109.5
C4—C3—C2	120.8 (3)	C11—C15—H15C	109.5
C4—C3—Co1	71.3 (2)	H15A—C15—H15C	109.5
C2—C3—Co1	71.57 (18)	H15B—C15—H15C	109.5
C4—C3—H3	119.6	C12—C16—H16A	109.5
C2—C3—H3	119.6	C12—C16—H16B	109.5
Co1—C3—H3	130.1	H16A—C16—H16B	109.5
C5—C4—C3	118.4 (3)	C12—C16—H16C	109.5
C5—C4—Co1	70.0 (2)	H16A—C16—H16C	109.5
C3—C4—Co1	69.54 (19)	H16B—C16—H16C	109.5
C5—C4—H4	120.8	C13—C17—H17A	109.5
C3—C4—H4	120.8	C13—C17—H17B	109.5
Co1—C4—H4	132.4	H17A—C17—H17B	109.5
C4—C5—C6	121.3 (4)	C13—C17—H17C	109.5
C4—C5—Co1	71.0 (2)	H17A—C17—H17C	109.5
C6—C5—Co1	72.0 (2)	H17B—C17—H17C	109.5
C4—C5—H5	119.4	C14—C18—H18A	109.5
C6—C5—H5	119.4	C14—C18—H18B	109.5
Co1—C5—H5	130.3	H18A—C18—H18B	109.5
C5—C6—C1	121.2 (3)	C14—C18—H18C	109.5
C5—C6—Co1	69.07 (19)	H18A—C18—H18C	109.5
C1—C6—Co1	75.53 (19)	H18B—C18—H18C	109.5
C5—C6—H6	119.4

C9—N1—C1—C6	167.8 (4)	C7—N1—C9—C10B	−88.3 (7)
C7—N1—C1—C6	−21.4 (5)	C1—N1—C9—C10A	86.2 (5)
C9—N1—C1—C2	−8.5 (5)	C7—N1—C9—C10A	−85.1 (4)
C7—N1—C1—C2	162.3 (3)	C13—Co1—C11—C14	−49.9 (2)
C9—N1—C1—Co1	79.0 (5)	C12—Co1—C11—C14	−98.7 (3)
C7—N1—C1—Co1	−110.2 (4)	C3—Co1—C11—C14	60.5 (3)
C14—Co1—C1—N1	−54.3 (5)	C5—Co1—C11—C14	141.6 (2)
C11—Co1—C1—N1	51.5 (5)	C4—Co1—C11—C14	99.9 (2)
C13—Co1—C1—N1	−23.0 (4)	C2—Co1—C11—C14	−0.8 (6)
C12—Co1—C1—N1	23.7 (4)	C6—Co1—C11—C14	−178.28 (18)
C3—Co1—C1—N1	−141.6 (4)	C1—Co1—C11—C14	−137.1 (3)
C5—Co1—C1—N1	142.4 (4)	C14—Co1—C11—C12	98.7 (3)
C4—Co1—C1—N1	−179.8 (4)	C13—Co1—C11—C12	48.83 (19)
C2—Co1—C1—N1	−111.4 (4)	C3—Co1—C11—C12	159.2 (2)
C6—Co1—C1—N1	112.4 (4)	C5—Co1—C11—C12	−119.7 (2)
C14—Co1—C1—C6	−166.7 (2)	C4—Co1—C11—C12	−161.35 (19)
C11—Co1—C1—C6	−60.9 (4)	C2—Co1—C11—C12	97.9 (5)
C13—Co1—C1—C6	−135.5 (2)	C6—Co1—C11—C12	−79.6 (2)
C12—Co1—C1—C6	−88.7 (2)	C1—Co1—C11—C12	−38.3 (4)
C3—Co1—C1—C6	106.0 (2)	C14—Co1—C11—C15	−131.4 (4)
C5—Co1—C1—C6	29.9 (2)	C13—Co1—C11—C15	178.7 (3)
C4—Co1—C1—C6	67.8 (2)	C12—Co1—C11—C15	129.9 (4)
C2—Co1—C1—C6	136.2 (3)	C3—Co1—C11—C15	−70.9 (4)
C14—Co1—C1—C2	57.1 (3)	C5—Co1—C11—C15	10.2 (3)
C11—Co1—C1—C2	162.9 (3)	C4—Co1—C11—C15	−31.5 (3)
C13—Co1—C1—C2	88.3 (2)	C2—Co1—C11—C15	−132.3 (5)
C12—Co1—C1—C2	135.1 (2)	C6—Co1—C11—C15	50.3 (3)
C3—Co1—C1—C2	−30.2 (2)	C1—Co1—C11—C15	91.5 (4)
C5—Co1—C1—C2	−106.2 (2)	C14—C11—C12—C13	−0.1 (2)
C4—Co1—C1—C2	−68.4 (2)	C15—C11—C12—C13	171.8 (4)
C6—Co1—C1—C2	−136.2 (3)	Co1—C11—C12—C13	−66.62 (17)
N1—C1—C2—C3	−174.3 (3)	C14—C11—C12—C16	−172.9 (3)
C6—C1—C2—C3	9.2 (4)	C15—C11—C12—C16	−1.0 (6)
Co1—C1—C2—C3	54.4 (3)	Co1—C11—C12—C16	120.6 (4)
N1—C1—C2—Co1	131.3 (3)	C14—C11—C12—Co1	66.49 (17)
C6—C1—C2—Co1	−45.2 (3)	C15—C11—C12—Co1	−121.6 (4)
C14—Co1—C2—C3	76.5 (3)	C14—Co1—C12—C13	49.7 (2)
C11—Co1—C2—C3	77.2 (6)	C11—Co1—C12—C13	99.3 (3)
C13—Co1—C2—C3	121.6 (2)	C3—Co1—C12—C13	10.1 (6)
C12—Co1—C2—C3	158.5 (2)	C5—Co1—C12—C13	−179.2 (2)
C5—Co1—C2—C3	−67.3 (2)	C4—Co1—C12—C13	137.0 (3)
C4—Co1—C2—C3	−29.2 (2)	C2—Co1—C12—C13	−58.3 (3)
C6—Co1—C2—C3	−105.0 (2)	C6—Co1—C12—C13	−138.5 (2)
C1—Co1—C2—C3	−132.0 (3)	C1—Co1—C12—C13	−98.1 (2)
C14—Co1—C2—C1	−151.5 (2)	C14—Co1—C12—C11	−49.6 (2)
C11—Co1—C2—C1	−150.8 (5)	C13—Co1—C12—C11	−99.3 (3)
C13—Co1—C2—C1	−106.5 (2)	C3—Co1—C12—C11	−89.1 (6)
C12—Co1—C2—C1	−69.5 (3)	C5—Co1—C12—C11	81.5 (2)
C3—Co1—C2—C1	132.0 (3)	C4—Co1—C12—C11	37.7 (3)
C5—Co1—C2—C1	64.6 (2)	C2—Co1—C12—C11	−157.6 (2)
C4—Co1—C2—C1	102.7 (2)	C6—Co1—C12—C11	122.2 (2)
C6—Co1—C2—C1	26.9 (2)	C1—Co1—C12—C11	162.65 (19)
C1—C2—C3—C4	−3.9 (5)	C14—Co1—C12—C16	−179.7 (3)
Co1—C2—C3—C4	53.8 (3)	C11—Co1—C12—C16	−130.1 (4)
C1—C2—C3—Co1	−57.7 (3)	C13—Co1—C12—C16	130.6 (4)
C14—Co1—C3—C4	106.4 (2)	C3—Co1—C12—C16	140.7 (5)
C11—Co1—C3—C4	68.2 (3)	C5—Co1—C12—C16	−48.6 (3)
C13—Co1—C3—C4	150.4 (2)	C4—Co1—C12—C16	−92.5 (4)
C12—Co1—C3—C4	142.2 (5)	C2—Co1—C12—C16	72.3 (3)
C5—Co1—C3—C4	−29.5 (2)	C6—Co1—C12—C16	−7.9 (3)
C2—Co1—C3—C4	−133.0 (3)	C1—Co1—C12—C16	32.5 (3)
C6—Co1—C3—C4	−67.4 (2)	C11—C12—C13—C14	0.1 (2)
C1—Co1—C3—C4	−103.8 (2)	C16—C12—C13—C14	172.9 (3)
C14—Co1—C3—C2	−120.7 (2)	Co1—C12—C13—C14	−66.15 (17)
C11—Co1—C3—C2	−158.8 (2)	C11—C12—C13—C17	−170.4 (4)
C13—Co1—C3—C2	−76.6 (3)	C16—C12—C13—C17	2.4 (7)
C12—Co1—C3—C2	−84.8 (6)	Co1—C12—C13—C17	123.4 (4)
C5—Co1—C3—C2	103.5 (2)	C11—C12—C13—Co1	66.27 (17)
C4—Co1—C3—C2	133.0 (3)	C16—C12—C13—Co1	−121.0 (4)
C6—Co1—C3—C2	65.6 (2)	C14—Co1—C13—C12	−99.0 (3)
C1—Co1—C3—C2	29.2 (2)	C11—Co1—C13—C12	−49.25 (18)
C2—C3—C4—C5	−1.9 (5)	C3—Co1—C13—C12	−176.98 (18)
Co1—C3—C4—C5	52.0 (3)	C5—Co1—C13—C12	2.7 (7)
C2—C3—C4—Co1	−53.9 (3)	C4—Co1—C13—C12	−134.9 (3)
C14—Co1—C4—C5	139.4 (2)	C2—Co1—C13—C12	142.69 (18)
C11—Co1—C4—C5	92.7 (2)	C6—Co1—C13—C12	64.3 (3)
C13—Co1—C4—C5	165.2 (3)	C1—Co1—C13—C12	102.51 (19)
C12—Co1—C4—C5	66.0 (3)	C11—Co1—C13—C14	49.8 (2)
C3—Co1—C4—C5	−132.4 (3)	C12—Co1—C13—C14	99.0 (3)
C2—Co1—C4—C5	−103.1 (2)	C3—Co1—C13—C14	−78.0 (2)
C6—Co1—C4—C5	−28.9 (2)	C5—Co1—C13—C14	101.7 (6)
C1—Co1—C4—C5	−65.8 (2)	C4—Co1—C13—C14	−35.9 (4)
C14—Co1—C4—C3	−88.1 (2)	C2—Co1—C13—C14	−118.3 (2)
C11—Co1—C4—C3	−134.9 (2)	C6—Co1—C13—C14	163.3 (2)
C13—Co1—C4—C3	−62.4 (4)	C1—Co1—C13—C14	−158.49 (19)
C12—Co1—C4—C3	−161.5 (2)	C14—Co1—C13—C17	130.1 (4)
C5—Co1—C4—C3	132.4 (3)	C11—Co1—C13—C17	179.9 (4)
C2—Co1—C4—C3	29.4 (2)	C12—Co1—C13—C17	−130.9 (4)
C6—Co1—C4—C3	103.6 (2)	C3—Co1—C13—C17	52.2 (4)
C1—Co1—C4—C3	66.6 (2)	C5—Co1—C13—C17	−128.2 (6)
C3—C4—C5—C6	1.9 (5)	C4—Co1—C13—C17	94.2 (5)
Co1—C4—C5—C6	53.7 (3)	C2—Co1—C13—C17	11.8 (4)
C3—C4—C5—Co1	−51.8 (3)	C6—Co1—C13—C17	−66.6 (4)
C14—Co1—C5—C4	−63.6 (3)	C1—Co1—C13—C17	−28.4 (4)
C11—Co1—C5—C4	−102.8 (2)	C12—C11—C14—C13	0.1 (2)
C13—Co1—C5—C4	−150.1 (6)	C15—C11—C14—C13	−171.5 (4)
C12—Co1—C5—C4	−147.9 (2)	Co1—C11—C14—C13	67.76 (18)
C3—Co1—C5—C4	29.6 (2)	C12—C11—C14—C18	170.3 (4)
C2—Co1—C5—C4	68.0 (2)	C15—C11—C14—C18	−1.3 (7)
C6—Co1—C5—C4	133.6 (3)	Co1—C11—C14—C18	−122.0 (4)
C1—Co1—C5—C4	104.5 (2)	C12—C11—C14—Co1	−67.63 (17)
C14—Co1—C5—C6	162.8 (2)	C15—C11—C14—Co1	120.7 (4)
C11—Co1—C5—C6	123.6 (2)	C12—C13—C14—C11	−0.1 (2)
C13—Co1—C5—C6	76.3 (6)	C17—C13—C14—C11	170.3 (4)
C12—Co1—C5—C6	78.5 (2)	Co1—C13—C14—C11	−67.60 (18)
C3—Co1—C5—C6	−104.0 (2)	C12—C13—C14—C18	−170.4 (4)
C4—Co1—C5—C6	−133.6 (3)	C17—C13—C14—C18	0.1 (7)
C2—Co1—C5—C6	−65.6 (2)	Co1—C13—C14—C18	122.1 (4)
C1—Co1—C5—C6	−29.1 (2)	C12—C13—C14—Co1	67.48 (17)
C4—C5—C6—C1	3.8 (5)	C17—C13—C14—Co1	−122.1 (4)
Co1—C5—C6—C1	57.0 (3)	C13—Co1—C14—C11	98.1 (2)
C4—C5—C6—Co1	−53.3 (3)	C12—Co1—C14—C11	49.30 (19)
N1—C1—C6—C5	174.4 (3)	C3—Co1—C14—C11	−140.2 (2)
C2—C1—C6—C5	−9.1 (4)	C5—Co1—C14—C11	−61.4 (3)
Co1—C1—C6—C5	−54.0 (3)	C4—Co1—C14—C11	−99.1 (2)
N1—C1—C6—Co1	−131.6 (3)	C2—Co1—C14—C11	179.74 (18)
C2—C1—C6—Co1	44.9 (3)	C6—Co1—C14—C11	7.0 (8)
C14—Co1—C6—C5	−81.5 (7)	C1—Co1—C14—C11	142.2 (2)
C11—Co1—C6—C5	−75.6 (3)	C11—Co1—C14—C13	−98.1 (2)
C13—Co1—C6—C5	−160.5 (2)	C12—Co1—C14—C13	−48.84 (19)
C12—Co1—C6—C5	−120.5 (2)	C3—Co1—C14—C13	121.6 (2)
C3—Co1—C6—C5	67.0 (2)	C5—Co1—C14—C13	−159.5 (2)
C4—Co1—C6—C5	28.9 (2)	C4—Co1—C14—C13	162.7 (2)
C2—Co1—C6—C5	105.1 (2)	C2—Co1—C14—C13	81.6 (2)
C1—Co1—C6—C5	132.1 (3)	C6—Co1—C14—C13	−91.1 (7)
C14—Co1—C6—C1	146.4 (6)	C1—Co1—C14—C13	44.1 (3)
C11—Co1—C6—C1	152.22 (19)	C11—Co1—C14—C18	131.0 (5)
C13—Co1—C6—C1	67.4 (3)	C13—Co1—C14—C18	−130.9 (5)
C12—Co1—C6—C1	107.4 (2)	C12—Co1—C14—C18	−179.7 (5)
C3—Co1—C6—C1	−65.1 (2)	C3—Co1—C14—C18	−9.2 (4)
C5—Co1—C6—C1	−132.1 (3)	C5—Co1—C14—C18	69.6 (5)
C4—Co1—C6—C1	−103.3 (2)	C4—Co1—C14—C18	31.9 (4)
C2—Co1—C6—C1	−27.07 (19)	C2—Co1—C14—C18	−49.3 (4)
C1—N1—C7—C8	96.8 (4)	C6—Co1—C14—C18	138.0 (6)
C9—N1—C7—C8	−92.0 (4)	C1—Co1—C14—C18	−86.8 (5)
C1—N1—C9—C10B	82.9 (7)

Acknowledgements

Thanks are due to the EPSRC X-ray Crystallography Service at the University of Southampton for data collection.

References

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Volume 61| Part 2| February 2005| Pages m302-m303

https://doi.org/10.1107/S1600536805000863

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