fac-(2,2′-Bi­pyridine)(1,1′-di­chloro­ferrocen-2-yl)tri­methyl­platinum(IV)

Blake, A.J.; Osborne, A.G.; Hollands, R.E.

doi:10.1107/S1600536801010170

fac-(2,2'-Bipyridine)(1,1'-dichloroferrocen-2-yl)trimethylplatinum(IV)

A. J. Blake, A. G. Osborne and R. E. Hollands

Reaction of 2-lithio-1,1'-dichloroferrocene (LiCl₂Fc) with [PtI(CH₃)₃(bipy)], where bipy is 2,2'-bipyridine, results in the formation of fac-[Pt(CH₃)₃(Cl₂Fc)(bipy)], i.e. fac-[Pt(CH₃)₃(C₁₀H₇Cl₂Fe)(C₁₀H₈N₂)]. The three methyl groups of the octahedral metal complex are in the fac configuration, with Pt-C bond lengths of 2.072 (11), 2.082 (11) and 2.092 (11) Å, together with a Pt-C(Cl₂Fc) distance of 2.146 (11) Å. In one of the two independent molecules in the asymmetric unit, the C atoms of the cyclopentadienyl rings are in an eclipsed conformation, while in the other, they are staggered by 26.7°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010170/cf6086sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010170/cf6086Isup2.hkl Contains datablock I

CCDC reference: 170748

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.019 Å
Disorder in main residue
R factor = 0.061
wR factor = 0.168
Data-to-parameter ratio = 16.9

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
          Tmin and Tmax reported:      0.166     0.670
          Tmin and Tmax expected:      0.158     0.712
          RR =      1.118
          Please check that your absorption correction is appropriate.

PLAT_301  Alert C Main Residue Disorder ........................       3.00 Perc.

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C6   -C7      1.555   1.555

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C6   -C10     1.555   1.555

PLAT_741  Alert C Bond    Calc   1.420(19), Rep     1.42000 ....    Missing s.u.
                     C7   -C8      1.555   1.555

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C8   -C9      1.555   1.555

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C9   -C10     1.555   1.555

PLAT_741  Alert C Bond    Calc   1.420(17), Rep     1.42000 ....    Missing s.u.
                     C6'  -C7'     1.555   1.555

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C6'  -C10'    1.555   1.555

PLAT_741  Alert C Bond    Calc   1.421(18), Rep     1.42000 ....    Missing s.u.
                     C7'  -C8'     1.555   1.555

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C8'  -C9'     1.555   1.555

PLAT_741  Alert C Bond    Calc     1.42(2), Rep     1.42000 ....    Missing s.u.
                     C9'  -C10'    1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(11), Rep      108.00 ....    Missing s.u.
                     C7   -C6   -C10     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(11), Rep      108.00 ....    Missing s.u.
                     C8   -C7   -C6      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(11), Rep      108.00 ....    Missing s.u.
                     C9   -C8   -C7      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(12), Rep      108.00 ....    Missing s.u.
                     C10  -C9   -C8      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(12), Rep      108.00 ....    Missing s.u.
                     C9   -C10  -C6      1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(11), Rep      108.00 ....    Missing s.u.
                     C7'  -C6'  -C10'    1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(11), Rep      108.00 ....    Missing s.u.
                     C8'  -C7'  -C6'     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   107.9(11), Rep      108.00 ....    Missing s.u.
                     C7'  -C8'  -C9'     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.0(12), Rep      108.00 ....    Missing s.u.
                     C10' -C9'  -C8'     1.555   1.555   1.555

PLAT_742  Alert C Angle   Calc   108.1(12), Rep      108.00 ....    Missing s.u.
                     C9'  -C10' -C6'     1.555   1.555   1.555

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      1.062
          Tmax scaled      0.712 Tmin scaled      0.176


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 22 Alert Level C = Please check

Comment top

The title compound, (I), was prepared during an investigation into the stability and reactivity of Pt^IV compounds with four Pt—C σ-bonds. The structure of (I) (Fig. 1) shows that the three methyl groups are in the fac orientation and hence the ferrocenyl unit is trans to a methyl group. For one of the independent molecules, the Pt—C_methyl distances are 2.072 (11), 2.082 (11) and 2.092 (11) Å, whilst the Pt—C(Cl₂Fc) distance of 2.146 (11) Å lies trans to the longest Pt—C_methyl distance. The principal distortions from regular octahedral geometry at Pt arise from the small bite angle [N1—Pt—N2 77.1 (3)°] of bipy and the angle C3M—Pt—N2 of 99.4 (5)°.

In one of the independent molecules, the C atoms of the cyclopentadienyl rings are in an eclipsed conformation, with a twist of only 0.5°, while in the other, they are staggered by 26.7°. The Fe centre lies 1.634 (5) Å out of the C1–C5 plane and 1.610 (9) Å from the C6–C10 plane, with a centroid–Fe–centroid angle of 177.8°; the corresponding values for Fe' in the second molecule are 1.657 (5) Å, 1.653 (9) Å and 173.1°.

In both molecules, the cyclopentadienyl rings are inclined at 4.8 (13)°. In one molecule, the disordered chlorines are twisted about the line connecting the ring centroids by 79.2 and 123.4°; in the other, the corresponding values are 82.9 and 116.2°. This is in contrast to the reported structures of other Cl₂Fc complexes (Hollands et al., 1985; Blake et al., 2001) where the chlorines are eclipsed.

Experimental top

A solution of n-butyl lithium (1.10 mmol) in hexane was added to a stirred solution of 1,1'-dichloroferrocene (0.29 g, 1.13 mmol) (Kovar et al., 1970) in tetrahydrofuran (25 ml). After 1 h, the solution was cooled to 195 K and [PtIMe₃(bipy)] (0.50 g, 0.96 mmol) (Lile & Menzies, 1949) was added. The mixture was allowed to warm slowly to ambient temperature and was then heated under reflux for 3 h. The cooled solution was poured into benzene (50 ml), washed with water (3 x 100 ml), dried over MgSO₄ and filtered. Removal of the solvent under vacuum produced a dark-brown oil that was purified by dry-column chromatography on alumina. Hexane eluted 1,1'-dichloroferrocene (0.17 g) and then benzene eluted the title compound which was subsequently crystallized from CH₂Cl₂/hexane to produce orange–red crystals (yield 0.067 g, 11%)

Computing details top

Data collection: local program; cell refinement: local program; data reduction: local program; program(s) used to solve structure: SHELX76 (Sheldrick, 1976); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PLATON.

Figures top

Fig. 1. A view of one of the two independent molecules of the title compound in the asymmetric unit, showing the atom-numbering scheme. Only the major [0.602 (14)] component of the disorder of the chlorine substituent on the C₅H₄Cl ring is shown. Displacement ellipsoids are drawn at the 20% probability level.

(I) top

Crystal data top

[Pt(CH₃)₃(C₁₀H₇Cl₂Fe)(C₁₀H₈N₂)]	F(000) = 2512
M_r = 650.28	D_x = 1.915 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 20.137 (4) Å	Cell parameters from 17 reflections
b = 10.572 (5) Å	θ = 9.5–21.0°
c = 21.810 (6) Å	µ = 7.09 mm⁻¹
β = 103.71 (1)°	T = 295 K
V = 4511 (3) Å³	Plate, orange
Z = 8	0.28 × 0.28 × 0.05 mm

Data collection top

Stoe Stadi-2 two-circle diffractometer	5558 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.009
Graphite monochromator	θ_max = 25.0°, θ_min = 2.8°
ω scans	h = −23→23
Absorption correction: ψ scan local program	k = 0→12
T_min = 0.166, T_max = 0.670	l = 0→25
7797 measured reflections	3 standard reflections every 360 min
7797 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: constr
wR(F²) = 0.168	See text
S = 1.08	w = 1/[σ²(F_o²) + (0.098P)²] where P = (F_o² + 2F_c²)/3
7797 reflections	(Δ/σ)_max = 0.005
461 parameters	Δρ_max = 2.43 e Å⁻³
200 restraints	Δρ_min = −1.13 e Å⁻³

Crystal data top

[Pt(CH₃)₃(C₁₀H₇Cl₂Fe)(C₁₀H₈N₂)]	V = 4511 (3) Å³
M_r = 650.28	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 20.137 (4) Å	µ = 7.09 mm⁻¹
b = 10.572 (5) Å	T = 295 K
c = 21.810 (6) Å	0.28 × 0.28 × 0.05 mm
β = 103.71 (1)°

Data collection top

Stoe Stadi-2 two-circle diffractometer	5558 reflections with I > 2σ(I)
Absorption correction: ψ scan local program	R_int = 0.009
T_min = 0.166, T_max = 0.670	3 standard reflections every 360 min
7797 measured reflections	intensity decay: none
7797 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	200 restraints
wR(F²) = 0.168	See text
S = 1.08	Δρ_max = 2.43 e Å⁻³
7797 reflections	Δρ_min = −1.13 e Å⁻³
461 parameters

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)
Pt	0.68055 (2)	0.29385 (4)	0.007239 (18)	0.06363 (16)
C1M	0.7152 (6)	0.3079 (11)	−0.0757 (6)	0.076 (3)
H1M	0.6929	0.3776	−0.1004	0.114*
H2M	0.7049	0.2310	−0.0994	0.114*
H3M	0.7637	0.3214	−0.0651	0.114*
C2M	0.7829 (6)	0.3034 (16)	0.0553 (7)	0.105 (4)
H4M	0.8062	0.3637	0.0349	0.157*
H5M	0.8037	0.2217	0.0550	0.157*
H6M	0.7861	0.3293	0.0981	0.157*
C3M	0.6970 (7)	0.1010 (11)	0.0023 (7)	0.094 (4)
H7M	0.6678	0.0677	−0.0356	0.140*
H8M	0.6870	0.0601	0.0383	0.140*
H9M	0.7439	0.0860	0.0018	0.140*
N1	0.6590 (4)	0.4910 (8)	0.0061 (4)	0.0655 (18)
N2	0.5776 (4)	0.3049 (9)	−0.0520 (4)	0.071 (2)
C11	0.6995 (7)	0.5852 (12)	0.0345 (6)	0.081 (3)
H11	0.7447	0.5642	0.0529	0.097*
C12	0.6821 (9)	0.7032 (13)	0.0391 (6)	0.099 (4)
H12	0.7123	0.7582	0.0651	0.119*
C13	0.6215 (10)	0.7457 (14)	0.0067 (9)	0.113 (5)
H13	0.6099	0.8309	0.0061	0.136*
C14	0.5750 (7)	0.6513 (13)	−0.0274 (8)	0.104 (4)
H14	0.5314	0.6744	−0.0499	0.125*
C15	0.5956 (5)	0.5283 (10)	−0.0263 (5)	0.070 (2)
C16	0.5508 (5)	0.4217 (10)	−0.0593 (5)	0.070 (2)
C17	0.4874 (5)	0.4451 (13)	−0.1019 (5)	0.077 (3)
H17	0.4709	0.5274	−0.1081	0.092*
C18	0.4521 (6)	0.3523 (14)	−0.1325 (6)	0.088 (3)
H18	0.4098	0.3672	−0.1599	0.106*
C19	0.4795 (6)	0.2265 (14)	−0.1233 (5)	0.086 (3)
H19	0.4562	0.1574	−0.1445	0.104*
C20	0.5417 (6)	0.2136 (11)	−0.0817 (5)	0.074 (3)
H20	0.5593	0.1322	−0.0743	0.089*
Fe	0.67931 (9)	0.18472 (18)	0.17953 (8)	0.0844 (5)
C1	0.5951 (5)	0.2037 (10)	0.1086 (5)	0.076 (2)
C2	0.6477 (5)	0.2792 (9)	0.0937 (5)	0.0664 (19)
C3	0.6676 (5)	0.3672 (11)	0.1456 (4)	0.072 (2)
H3	0.7012	0.4290	0.1493	0.087*
C4	0.6275 (6)	0.3440 (12)	0.1905 (6)	0.090 (3)
H4	0.6304	0.3879	0.2280	0.109*
C5	0.5817 (6)	0.2410 (13)	0.1674 (5)	0.085 (3)
H5	0.5497	0.2058	0.1870	0.102*
Cl1	0.54818 (17)	0.0851 (3)	0.06319 (16)	0.0922 (9)
C6	0.7074 (7)	0.0017 (12)	0.1862 (6)	0.127 (5)*
C7	0.7624 (7)	0.0735 (13)	0.1740 (6)	0.135 (6)*
C8	0.7813 (6)	0.1654 (12)	0.2225 (7)	0.130 (6)*
C9	0.7379 (8)	0.1505 (13)	0.2647 (6)	0.132 (6)*
C10	0.6922 (6)	0.0493 (14)	0.2423 (7)	0.141 (6)*
H6	0.6816	−0.0756	0.1579	0.169*
H7	0.7858	0.0604	0.1348	0.169*
H8	0.8215	0.2346	0.2266	0.169*
H9	0.7393	0.2063	0.3065	0.169*	0.602 (14)
H10	0.6528	0.0146	0.2640	0.169*	0.398 (14)
Cl2A	0.7013 (8)	0.1820 (16)	0.3307 (8)	0.163 (7)*	0.398 (14)
Cl2B	0.6461 (5)	0.0158 (10)	0.2913 (5)	0.159 (4)*	0.602 (14)
Pt'	0.45932 (2)	0.72749 (6)	0.34009 (2)	0.0880 (2)
C1M'	0.5481 (8)	0.760 (2)	0.3123 (8)	0.127 (5)
H1M'	0.5819	0.7937	0.3470	0.190*
H2M'	0.5396	0.8191	0.2780	0.190*
H3M'	0.5644	0.6817	0.2988	0.190*
C2M'	0.4135 (7)	0.7133 (17)	0.2456 (6)	0.106 (4)
H4M'	0.3776	0.6515	0.2395	0.158*
H5M'	0.4468	0.6879	0.2230	0.158*
H6M'	0.3947	0.7938	0.2302	0.158*
C3M'	0.4371 (8)	0.9110 (15)	0.3314 (6)	0.104 (3)
H7M'	0.3958	0.9269	0.3448	0.156*
H8M'	0.4309	0.9358	0.2881	0.156*
H9M'	0.4738	0.9589	0.3572	0.156*
N1'	0.4932 (5)	0.5349 (11)	0.3532 (5)	0.087 (2)
N2'	0.5192 (5)	0.7267 (10)	0.4384 (5)	0.084 (2)
C11'	0.4802 (7)	0.4382 (19)	0.3114 (7)	0.117 (5)
H11'	0.4518	0.4536	0.2718	0.140*
C12'	0.5070 (8)	0.316 (2)	0.3243 (9)	0.134 (6)
H12'	0.4966	0.2503	0.2954	0.161*
C13'	0.5472 (8)	0.3033 (18)	0.3792 (9)	0.124 (5)
H13'	0.5664	0.2235	0.3884	0.149*
C14'	0.5650 (7)	0.3893 (15)	0.4248 (7)	0.097 (3)
H14'	0.5943	0.3707	0.4636	0.116*
C15'	0.5366 (5)	0.5094 (13)	0.4103 (5)	0.076 (2)
C16'	0.5501 (5)	0.6143 (12)	0.4535 (5)	0.076 (2)
C17'	0.5875 (6)	0.6012 (13)	0.5173 (6)	0.086 (3)
H17'	0.6038	0.5218	0.5320	0.103*
C18'	0.5997 (6)	0.6998 (13)	0.5566 (6)	0.091 (4)
H18'	0.6255	0.6896	0.5977	0.110*
C19'	0.5740 (6)	0.8156 (14)	0.5359 (6)	0.093 (4)
H19'	0.5836	0.8872	0.5612	0.112*
C20'	0.5315 (6)	0.8211 (13)	0.4730 (6)	0.089 (3)
H20'	0.5124	0.8983	0.4577	0.106*
Fe'	0.26270 (9)	0.71797 (17)	0.33344 (9)	0.0835 (5)
C1'	0.3353 (5)	0.7243 (11)	0.4155 (5)	0.082 (3)
C2'	0.3684 (5)	0.6817 (11)	0.3673 (4)	0.072 (2)
C3'	0.3281 (5)	0.5658 (11)	0.3449 (5)	0.071 (2)
H3'	0.3352	0.5124	0.3132	0.085*
C4'	0.2781 (6)	0.5495 (11)	0.3784 (5)	0.079 (3)
H4'	0.2465	0.4838	0.3725	0.094*
C5'	0.2827 (6)	0.6455 (12)	0.4215 (5)	0.084 (3)
H5'	0.2550	0.6556	0.4498	0.101*
Cl1'	0.35999 (19)	0.8612 (3)	0.46205 (17)	0.1004 (10)
C6'	0.2352 (7)	0.8947 (10)	0.3011 (6)	0.118 (5)*
C7'	0.2382 (6)	0.8093 (12)	0.2516 (6)	0.132 (6)*
C8'	0.1894 (7)	0.7121 (10)	0.2513 (6)	0.110 (5)*
C9'	0.1563 (7)	0.7375 (14)	0.3007 (7)	0.145 (7)*
C10'	0.1846 (8)	0.8503 (14)	0.3314 (6)	0.157 (7)*
H6'	0.2660	0.9786	0.3135	0.188*
H7'	0.2717	0.8169	0.2197	0.188*
H8'	0.1793	0.6329	0.2192	0.188*
H9'	0.1165	0.6809	0.3127	0.188*	0.335 (14)
H10'	0.1701	0.8946	0.3710	0.188*	0.665 (14)
Cl4A	0.0970 (4)	0.6382 (9)	0.3249 (4)	0.145 (4)*	0.665 (14)
Cl4B	0.1075 (8)	0.7991 (17)	0.3418 (8)	0.146 (7)*	0.335 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt	0.0565 (2)	0.0696 (3)	0.0586 (2)	0.00896 (18)	0.00129 (17)	0.00170 (18)
C1M	0.074 (6)	0.080 (6)	0.080 (6)	0.003 (5)	0.030 (5)	−0.001 (5)
C2M	0.045 (5)	0.156 (11)	0.099 (8)	0.019 (6)	−0.010 (5)	0.018 (8)
C3M	0.103 (8)	0.064 (5)	0.121 (10)	0.035 (5)	0.039 (7)	0.023 (5)
N1	0.069 (4)	0.064 (4)	0.061 (5)	0.015 (3)	0.011 (4)	0.008 (3)
N2	0.048 (4)	0.080 (4)	0.073 (5)	0.010 (3)	−0.007 (3)	0.012 (4)
C11	0.083 (7)	0.079 (5)	0.076 (7)	0.002 (5)	0.007 (6)	−0.005 (6)
C12	0.152 (11)	0.084 (6)	0.059 (7)	0.004 (7)	0.018 (7)	−0.012 (6)
C13	0.142 (11)	0.071 (6)	0.136 (13)	0.032 (6)	0.053 (9)	−0.008 (7)
C14	0.092 (8)	0.082 (6)	0.140 (12)	0.028 (6)	0.028 (7)	0.029 (7)
C15	0.050 (5)	0.071 (4)	0.090 (7)	0.011 (4)	0.020 (4)	0.027 (5)
C16	0.053 (5)	0.077 (5)	0.074 (6)	0.021 (4)	0.006 (4)	0.020 (5)
C17	0.060 (5)	0.105 (7)	0.062 (6)	0.023 (5)	0.007 (4)	0.018 (5)
C18	0.053 (6)	0.121 (8)	0.082 (7)	0.000 (5)	−0.001 (5)	0.041 (7)
C19	0.078 (7)	0.111 (7)	0.059 (6)	−0.011 (6)	−0.006 (5)	0.005 (6)
C20	0.067 (6)	0.086 (6)	0.059 (6)	−0.006 (5)	−0.007 (4)	0.009 (5)
Fe	0.0804 (11)	0.0912 (11)	0.0725 (10)	0.0238 (9)	0.0001 (8)	0.0180 (9)
C1	0.065 (5)	0.085 (6)	0.075 (5)	0.011 (4)	0.010 (4)	0.015 (4)
C2	0.067 (5)	0.065 (5)	0.065 (4)	0.014 (4)	0.011 (4)	0.009 (3)
C3	0.067 (5)	0.090 (5)	0.053 (5)	0.023 (4)	0.001 (4)	0.010 (4)
C4	0.112 (9)	0.089 (7)	0.074 (6)	0.019 (5)	0.030 (6)	0.006 (5)
C5	0.065 (5)	0.131 (9)	0.052 (5)	0.010 (5)	0.000 (4)	0.020 (5)
Cl1	0.095 (2)	0.0784 (18)	0.098 (2)	−0.0099 (15)	0.0115 (17)	0.0028 (16)
Pt'	0.0651 (3)	0.1270 (5)	0.0626 (3)	−0.0068 (3)	−0.0037 (2)	0.0177 (3)
C1M'	0.091 (7)	0.179 (13)	0.110 (9)	−0.029 (8)	0.024 (7)	0.024 (11)
C2M'	0.086 (7)	0.178 (13)	0.053 (5)	0.033 (8)	0.015 (5)	0.012 (6)
C3M'	0.126 (10)	0.124 (6)	0.062 (6)	−0.017 (6)	0.022 (7)	0.039 (6)
N1'	0.060 (5)	0.122 (5)	0.072 (5)	0.002 (5)	0.002 (4)	−0.008 (4)
N2'	0.068 (5)	0.095 (5)	0.075 (5)	−0.019 (5)	−0.010 (4)	0.008 (4)
C11'	0.083 (8)	0.177 (10)	0.081 (8)	0.034 (9)	−0.001 (6)	−0.039 (8)
C12'	0.092 (10)	0.176 (11)	0.118 (10)	0.048 (10)	−0.007 (8)	−0.074 (11)
C13'	0.090 (10)	0.134 (10)	0.132 (12)	0.022 (9)	−0.009 (8)	−0.032 (8)
C14'	0.088 (8)	0.114 (7)	0.080 (7)	0.006 (7)	0.005 (6)	−0.003 (6)
C15'	0.033 (4)	0.114 (6)	0.072 (6)	0.001 (5)	−0.004 (4)	0.001 (5)
C16'	0.064 (6)	0.088 (5)	0.069 (5)	−0.018 (5)	0.002 (5)	0.018 (4)
C17'	0.069 (7)	0.099 (7)	0.074 (6)	−0.014 (6)	−0.013 (5)	0.004 (5)
C18'	0.056 (6)	0.101 (7)	0.092 (7)	−0.007 (6)	−0.029 (6)	0.005 (6)
C19'	0.074 (7)	0.103 (7)	0.083 (7)	−0.008 (6)	−0.018 (6)	−0.015 (6)
C20'	0.077 (7)	0.092 (7)	0.082 (7)	−0.007 (6)	−0.011 (6)	0.012 (5)
Fe'	0.0687 (9)	0.0794 (10)	0.0883 (11)	0.0097 (8)	−0.0097 (8)	0.0059 (9)
C1'	0.054 (5)	0.098 (7)	0.084 (6)	0.007 (4)	−0.004 (3)	−0.023 (6)
C2'	0.061 (4)	0.097 (6)	0.049 (5)	0.000 (4)	−0.002 (3)	0.001 (4)
C3'	0.057 (5)	0.090 (6)	0.058 (5)	0.009 (4)	0.001 (4)	−0.005 (4)
C4'	0.096 (7)	0.083 (5)	0.057 (6)	−0.013 (5)	0.017 (5)	0.008 (4)
C5'	0.080 (7)	0.097 (7)	0.074 (5)	0.005 (5)	0.016 (5)	−0.001 (4)
Cl1'	0.103 (2)	0.088 (2)	0.099 (2)	0.0040 (18)	−0.0003 (18)	−0.0217 (18)

Geometric parameters (Å, º) top

Pt—C1M	2.092 (11)	Pt'—C1M'	2.049 (15)
Pt—C2M	2.082 (11)	Pt'—C2M'	2.054 (12)
Pt—C3M	2.072 (11)	Pt'—C3M'	1.990 (16)
Pt—N1	2.128 (8)	Pt'—N1'	2.145 (12)
Pt—N2	2.170 (8)	Pt'—N2'	2.196 (10)
Pt—C2	2.146 (11)	Pt'—C2'	2.110 (11)
C1M—H1M	0.96	C1M'—H1M'	0.96
C1M—H2M	0.96	C1M'—H2M'	0.96
C1M—H3M	0.96	C1M'—H3M'	0.96
C2M—H4M	0.96	C2M'—H4M'	0.96
C2M—H5M	0.96	C2M'—H5M'	0.96
C2M—H6M	0.96	C2M'—H6M'	0.96
C3M—H7M	0.96	C3M'—H7M'	0.96
C3M—H8M	0.96	C3M'—H8M'	0.96
C3M—H9M	0.96	C3M'—H9M'	0.96
N1—C11	1.343 (15)	N1'—C11'	1.354 (18)
N1—C15	1.363 (12)	N1'—C15'	1.367 (13)
N2—C20	1.286 (14)	N2'—C20'	1.241 (17)
N2—C16	1.342 (13)	N2'—C16'	1.345 (16)
C11—C12	1.306 (18)	C11'—C12'	1.40 (3)
C11—H11	0.93	C11'—H11'	0.93
C12—C13	1.33 (2)	C12'—C13'	1.28 (2)
C12—H12	0.93	C12'—H12'	0.93
C13—C14	1.45 (2)	C13'—C14'	1.33 (2)
C13—H13	0.93	C13'—H13'	0.93
C14—C15	1.363 (17)	C14'—C15'	1.398 (19)
C14—H14	0.93	C14'—H14'	0.93
C15—C16	1.515 (16)	C15'—C16'	1.439 (17)
C16—C17	1.411 (14)	C16'—C17'	1.423 (15)
C17—C18	1.300 (18)	C17'—C18'	1.334 (18)
C17—H17	0.93	C17'—H17'	0.93
C18—C19	1.44 (2)	C18'—C19'	1.363 (18)
C18—H18	0.93	C18'—H18'	0.93
C19—C20	1.368 (15)	C19'—C20'	1.436 (16)
C19—H19	0.93	C19'—H19'	0.93
C20—H20	0.93	C20'—H20'	0.93
Fe—C1	2.017 (10)	Fe'—C1'	2.026 (10)
Fe—C2	2.085 (9)	Fe'—C2'	2.117 (10)
Fe—C3	2.059 (11)	Fe'—C3'	2.056 (10)
Fe—C4	2.025 (11)	Fe'—C4'	2.021 (10)
Fe—C5	2.011 (11)	Fe'—C5'	2.018 (11)
Fe—C6	2.011 (14)	Fe'—C6'	2.027 (13)
Fe—C7	2.072 (13)	Fe'—C7'	1.986 (13)
Fe—C8	2.055 (13)	Fe'—C8'	2.034 (13)
Fe—C9	1.983 (14)	Fe'—C9'	2.102 (14)
Fe—C10	1.955 (14)	Fe'—C10'	2.098 (14)
C1—C2	1.424 (16)	C1'—C5'	1.378 (17)
C1—C5	1.429 (17)	C1'—C2'	1.444 (16)
C1—Cl1	1.732 (13)	C1'—Cl1'	1.770 (12)
C2—C3	1.448 (15)	C2'—C3'	1.487 (16)
C3—C4	1.430 (16)	C3'—C4'	1.387 (15)
C3—H3	0.93	C3'—H3'	0.93
C4—C5	1.438 (19)	C4'—C5'	1.372 (17)
C4—H4	0.93	C4'—H4'	0.93
C5—H5	0.93	C5'—H5'	0.93
C6—C7	1.42	C6'—C7'	1.42
C6—C10	1.42	C6'—C10'	1.42
C7—C8	1.42	C7'—C8'	1.42
C7—H7	1.08	C7'—H7'	1.08
C8—C9	1.42	C8'—C9'	1.42
C8—H8	1.08	C8'—H8'	1.08
C9—C10	1.42	C9'—C10'	1.42
C9—Cl2A	1.798 (19)	C9'—Cl4A	1.762 (13)
C9—H9	1.08	C9'—H9'	1.08
C10—Cl2B	1.614 (14)	C10'—Cl4B	1.71 (2)
C10—H10	1.08	C10'—H10'	1.08

C3M—Pt—C2M	85.6 (6)	C1M'—Pt'—C2M'	86.0 (6)
C3M—Pt—C1M	86.2 (5)	C3M'—Pt'—C2'	93.4 (5)
C2M—Pt—C1M	86.5 (5)	C1M'—Pt'—C2'	176.3 (7)
C3M—Pt—N1	176.1 (5)	C2M'—Pt'—C2'	93.0 (5)
C2M—Pt—N1	97.7 (5)	C3M'—Pt'—N1'	174.5 (5)
C1M—Pt—N1	91.7 (4)	C1M'—Pt'—N1'	85.7 (6)
C3M—Pt—C2	93.5 (4)	C2M'—Pt'—N1'	96.8 (6)
C2M—Pt—C2	92.1 (5)	C2'—Pt'—N1'	90.8 (4)
C1M—Pt—C2	178.5 (4)	C3M'—Pt'—N2'	98.9 (5)
N1—Pt—C2	88.6 (3)	C1M'—Pt'—N2'	88.5 (6)
C3M—Pt—N2	99.4 (5)	C2M'—Pt'—N2'	172.3 (5)
C2M—Pt—N2	171.6 (5)	C2'—Pt'—N2'	92.1 (4)
C1M—Pt—N2	87.1 (4)	N1'—Pt'—N2'	77.4 (4)
N1—Pt—N2	77.1 (3)	Pt'—C1M'—H1M'	109.5
C2—Pt—N2	94.4 (4)	Pt'—C1M'—H2M'	109.5
Pt—C1M—H1M	109.5	H1M'—C1M'—H2M'	109.5
Pt—C1M—H2M	109.5	Pt'—C1M'—H3M'	109.5
H1M—C1M—H2M	109.5	H1M'—C1M'—H3M'	109.5
Pt—C1M—H3M	109.5	H2M'—C1M'—H3M'	109.5
H1M—C1M—H3M	109.5	Pt'—C2M'—H4M'	109.5
H2M—C1M—H3M	109.5	Pt'—C2M'—H5M'	109.5
Pt—C2M—H4M	109.5	H4M'—C2M'—H5M'	109.5
Pt—C2M—H5M	109.5	Pt'—C2M'—H6M'	109.5
H4M—C2M—H5M	109.5	H4M'—C2M'—H6M'	109.5
Pt—C2M—H6M	109.5	H5M'—C2M'—H6M'	109.5
H4M—C2M—H6M	109.5	Pt'—C3M'—H7M'	109.5
H5M—C2M—H6M	109.5	Pt'—C3M'—H8M'	109.5
Pt—C3M—H7M	109.5	H7M'—C3M'—H8M'	109.5
Pt—C3M—H8M	109.5	Pt'—C3M'—H9M'	109.5
H7M—C3M—H8M	109.5	H7M'—C3M'—H9M'	109.5
Pt—C3M—H9M	109.5	H8M'—C3M'—H9M'	109.5
H7M—C3M—H9M	109.5	C11'—N1'—C15'	116.4 (12)
H8M—C3M—H9M	109.5	C11'—N1'—Pt'	128.5 (9)
C11—N1—C15	114.7 (9)	C15'—N1'—Pt'	115.0 (8)
C11—N1—Pt	128.4 (7)	C20'—N2'—C16'	123.1 (11)
C15—N1—Pt	116.9 (7)	C20'—N2'—Pt'	125.1 (9)
C20—N2—C16	117.9 (9)	C16'—N2'—Pt'	111.0 (8)
C20—N2—Pt	127.2 (8)	N1'—C11'—C12'	123.8 (13)
C16—N2—Pt	114.9 (7)	N1'—C11'—H11'	118.1
C12—C11—N1	126.8 (13)	C12'—C11'—H11'	118.1
C12—C11—H11	116.6	C13'—C12'—C11'	114.5 (15)
N1—C11—H11	116.6	C13'—C12'—H12'	122.8
C11—C12—C13	120.6 (15)	C11'—C12'—H12'	122.8
C11—C12—H12	119.7	C12'—C13'—C14'	128.4 (18)
C13—C12—H12	119.7	C12'—C13'—H13'	115.8
C12—C13—C14	116.1 (13)	C14'—C13'—H13'	115.8
C12—C13—H13	122.0	C13'—C14'—C15'	115.3 (13)
C14—C13—H13	122.0	C13'—C14'—H14'	122.3
C15—C14—C13	119.4 (13)	C15'—C14'—H14'	122.3
C15—C14—H14	120.3	N1'—C15'—C14'	121.6 (12)
C13—C14—H14	120.3	N1'—C15'—C16'	115.2 (11)
N1—C15—C14	122.0 (12)	C14'—C15'—C16'	123.2 (10)
N1—C15—C16	114.2 (9)	N2'—C16'—C17'	115.7 (12)
C14—C15—C16	123.9 (10)	N2'—C16'—C15'	121.0 (10)
N2—C16—C17	121.1 (11)	C17'—C16'—C15'	122.6 (11)
N2—C16—C15	116.8 (8)	C18'—C17'—C16'	121.7 (12)
C17—C16—C15	121.7 (10)	C18'—C17'—H17'	119.2
C18—C17—C16	120.3 (12)	C16'—C17'—H17'	119.2
C18—C17—H17	119.8	C17'—C18'—C19'	119.5 (11)
C16—C17—H17	119.8	C17'—C18'—H18'	120.3
C17—C18—C19	118.8 (10)	C19'—C18'—H18'	120.3
C17—C18—H18	120.6	C18'—C19'—C20'	116.4 (12)
C19—C18—H18	120.6	C18'—C19'—H19'	121.8
C20—C19—C18	116.5 (12)	C20'—C19'—H19'	121.8
C20—C19—H19	121.8	N2'—C20'—C19'	122.5 (13)
C18—C19—H19	121.8	N2'—C20'—H20'	118.8
N2—C20—C19	125.2 (12)	C19'—C20'—H20'	118.8
N2—C20—H20	117.4	C5'—C1'—C2'	112.2 (11)
C19—C20—H20	117.4	C5'—C1'—Cl1'	123.9 (10)
C2—C1—C5	111.1 (11)	C2'—C1'—Cl1'	123.8 (9)
C2—C1—Cl1	127.6 (9)	C1'—C2'—C3'	100.7 (9)
C5—C1—Cl1	121.3 (10)	C1'—C2'—Pt'	135.6 (8)
C1—C2—C3	105.4 (10)	C3'—C2'—Pt'	122.6 (8)
C1—C2—Pt	129.9 (8)	C4'—C3'—C2'	109.7 (10)
C3—C2—Pt	123.7 (8)	C4'—C3'—H3'	125.2
C4—C3—C2	109.1 (11)	C2'—C3'—H3'	125.2
C4—C3—H3	125.4	C5'—C4'—C3'	109.3 (11)
C2—C3—H3	125.4	C5'—C4'—H4'	125.4
C3—C4—C5	108.1 (11)	C3'—C4'—H4'	125.4
C3—C4—H4	126.0	C4'—C5'—C1'	108.1 (11)
C5—C4—H4	126.0	C4'—C5'—H5'	126.0
C1—C5—C4	106.3 (11)	C1'—C5'—H5'	126.0
C1—C5—H5	126.8	C7'—C6'—C10'	108.0
C4—C5—H5	126.8	C8'—C7'—C6'	108.0
C7—C6—C10	108.0	C8'—C7'—H7'	126.0
C8—C7—C6	108.0	C6'—C7'—H7'	126.0
C8—C7—H7	126.0	C7'—C8'—C9'	108.0
C6—C7—H7	126.0	C7'—C8'—H8'	126.0
C9—C8—C7	108.0	C9'—C8'—H8'	126.0
C9—C8—H8	126.0	C10'—C9'—C8'	108.0
C7—C8—H8	126.0	C10'—C9'—Cl4A	125.7 (10)
C10—C9—C8	108.0	C8'—C9'—Cl4A	126.0 (10)
C10—C9—H9	126.0	C10'—C9'—H9'	126.0
C8—C9—H9	126.0	C8'—C9'—H9'	126.0
C9—C10—C6	108.0	C9'—C10'—C6'	108.0
C9—C10—Cl2B	111.4 (10)	C9'—C10'—H6'	131.0
C9—C10—H10	126.0	C9'—C10'—H10'	126.0
C6—C10—H10	126.0	C6'—C10'—H10'	126.0
C3M'—Pt'—C1M'	90.1 (7)	H6'—C10'—H10'	103.0
C3M'—Pt'—C2M'	86.5 (6)

Experimental details

Crystal data
Chemical formula	[Pt(CH₃)₃(C₁₀H₇Cl₂Fe)(C₁₀H₈N₂)]
M_r	650.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	20.137 (4), 10.572 (5), 21.810 (6)
β (°)	103.71 (1)
V (Å³)	4511 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	7.09
Crystal size (mm)	0.28 × 0.28 × 0.05

Data collection
Diffractometer	Stoe Stadi-2 two-circle diffractometer
Absorption correction	ψ scan local program
T_min, T_max	0.166, 0.670
No. of measured, independent and observed [I > 2σ(I)] reflections	7797, 7797, 5558
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.168, 1.08
No. of reflections	7797
No. of parameters	461
No. of restraints	200
H-atom treatment	See text
Δρ_max, Δρ_min (e Å⁻³)	2.43, −1.13

Computer programs: local program, SHELX76 (Sheldrick, 1976), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 and PLATON.

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fac-(2,2'-Bi­pyridine)(1,1'-di­chloro­ferrocen-2-yl)tri­methyl­platinum(IV)

Supporting information

Key indicators

checkCIF results

fac-(2,2'-Bipyridine)(1,1'-dichloroferrocen-2-yl)trimethylplatinum(IV)