Dichlorido{[2-(diphenyl­phosphino)phenyl­imino­meth­yl]ferrocene-κ2N,P}platinum(II) dichloro­methane hemisolvate

Xie, Y.; Wei, Y.; Hu, J.-G.; Zhao, J.-S.; Jiang, F.-X.

doi:10.1107/S1600536808043493

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m138

doi:10.1107/S1600536808043493

Open

access

Dichlorido{[2-(diphenylphosphino)phenyliminomethyl]ferrocene-κ²N,P}platinum(II) dichloromethane hemisolvate

Yu Xie,^a ^* Ya Wei,^a Jin-Gang Hu,^a Jin-Sheng Zhao ^a,^b and Feng-Xing Jiang ^a

^aKey Laboratory of Nondestructive Testing of the Ministry of Education, Nanchang Hangkong University, Nanchang 330063, People's Republic of China, and ^bDepartment of Chemistry, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: xieyu_121@163.com

(Received 26 November 2008; accepted 20 December 2008; online 8 January 2009)

In the title compound, [FePt(C₅H₅)(C₂₄H₁₉NP)Cl₂]·0.5CH₂Cl₂, the Pt^II atom adopts a distorted square-planar geometry defined by one P atom and one N atom from the bidentate [2-(diphenylphosphino)phenyliminomethyl]ferrocene ligand and two Cl atoms. Two disordered dichloromethane solvent molecules are each 0.25-occupied on a twofold rotation axis.

Related literature

For general background, see: Cullen & Woolins (1981 ); Farrell et al. (2002 ); Gul et al. (2002 ); Wu et al. (2001 ). For the ligand synthesis, see: Gong et al. (2006 ); Zhang et al. (2006 ).

Experimental

Crystal data

[FePt(C₅H₅)(C₂₄H₁₉NP)Cl₂]·0.5CH₂Cl₂
M_r = 781.75
Orthorhombic, P 2₁ 2₁ 2
a = 19.5045 (11) Å
b = 12.0182 (7) Å
c = 12.9800 (8) Å
V = 3042.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 5.40 mm⁻¹
T = 293 (2) K
0.3 × 0.1 × 0.1 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.532, T_max = 0.588
19964 measured reflections
5902 independent reflections
4954 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.04
5902 reflections
345 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.93 e Å⁻³
Absolute structure: Flack (1983 ), 856 Friedel pairs
Flack parameter: 0.002 (11)

Table 1
Selected bond lengths (Å)

Pt—N	2.031 (3)
Pt—P	2.2089 (10)
Pt—Cl1	2.2996 (13)
Pt—Cl2	2.3673 (11)

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043493/hy2171sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043493/hy2171Isup2.hkl

checkCIF report

Comment top

Ferrocene derivatives containing heteroatoms with good donor abilities have attracted great interest during the last few years in organometallic chemistry, since the coordination of a metal to these heteroatoms produces polymetallic molecules (Cullen & Woolins, 1981). Some examples showing the utility of these polymetallic compounds in homogeneous catalysis (Farrell et al., 2002; Wu et al., 2001) or for the design of new materials with outstanding properties (Gul et al., 2002) have been described. Here we report a new bimetallic platinum(II) complex with a ferrocenyliminophosphine ligand.

In the title compound, the Pt^II atom adopts a distorted square planar geometry, defined by one P atom and one N atom from the bidentate ferrocenyliminophosphine ligand (L) and two Cl atoms (Fig. 1), with N—Pt—Cl1 = 176.29 (9)° and P—Pt—Cl2 = 170.19 (4)°. The difference between the Pt—Cl bond lengths [2.2996 (13) and 2.3673 (11) Å] (Table 1) reflects the stronger trans influence of the tertiary phosphine compared with the imino group. The ligand L adopts a five-membered chelating ring. The benzene ring and the cyclopentadienyl ring are trans, with respect to the C11—N double bond.

Related literature top

For general background, see: Cullen & Woolins (1981); Farrell et al. (2002); Gul et al. (2002); Wu et al. (2001). For the ligand synthesis, see: Gong et al. (2006); Zhang et al. (2006).

Experimental top

The ligand L was prepared by literature method (Gong et al., 2006; Zhang et al., 2006). The title compound was prepared by reacting equal molar K₂PtCl₄ and L in CH₂Cl₂ (yield 83%). Brown needle crystals suitable for X-ray analysis were obtained by vapor diffusion of diethyl ether into a solution of the title compound in CH₂Cl₂. Analysis calculated for C_29.5H₂₅Cl₃FeNPPt: C 45.32, H 3.22, N 1.79%; found: C 45.61, H 3.33, N 1.70%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms and disordered dichloromethane solvent molecules have been omitted for clarity.

Dichlorido{[2-(diphenylphosphino)phenyliminomethyl]ferrocene- κ²N,P}platinum(II) dichloromethane hemisolvate top

Crystal data top

[FePt(C₅H₅)(C₂₄H₁₉NP)Cl₂]·0.5CH₂Cl₂	F(000) = 1516
M_r = 781.75	D_x = 1.707 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 892 reflections
a = 19.5045 (11) Å	θ = 3.2–25.8°
b = 12.0182 (7) Å	µ = 5.40 mm⁻¹
c = 12.9800 (8) Å	T = 293 K
V = 3042.6 (3) Å³	Needle, brown–yellow
Z = 4	0.3 × 0.1 × 0.1 mm

Data collection top

Siemens SMART CCD diffractometer	5902 independent reflections
Radiation source: fine-focus sealed tube	4954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→24
T_min = 0.532, T_max = 0.588	k = −14→14
19964 measured reflections	l = −16→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.024
5902 reflections	Δρ_max = 1.18 e Å⁻³
345 parameters	Δρ_min = −0.93 e Å⁻³
24 restraints	Absolute structure: Flack (1983), 856 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.002 (11)

Crystal data top

[FePt(C₅H₅)(C₂₄H₁₉NP)Cl₂]·0.5CH₂Cl₂	V = 3042.6 (3) Å³
M_r = 781.75	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 19.5045 (11) Å	µ = 5.40 mm⁻¹
b = 12.0182 (7) Å	T = 293 K
c = 12.9800 (8) Å	0.3 × 0.1 × 0.1 mm

Data collection top

Siemens SMART CCD diffractometer	5902 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4954 reflections with I > 2σ(I)
T_min = 0.532, T_max = 0.588	R_int = 0.058
19964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 1.18 e Å⁻³
S = 1.04	Δρ_min = −0.93 e Å⁻³
5902 reflections	Absolute structure: Flack (1983), 856 Friedel pairs
345 parameters	Absolute structure parameter: 0.002 (11)
24 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt	0.270357 (7)	0.911967 (14)	0.143789 (12)	0.03558 (4)
Fe	0.34183 (3)	0.52770 (6)	0.19921 (5)	0.04447 (19)
Cl1	0.32009 (6)	1.06905 (11)	0.21198 (10)	0.0568 (4)
Cl2	0.35362 (5)	0.90898 (12)	0.01112 (9)	0.0538 (3)
Cl3	0.4874 (2)	0.8826 (5)	0.3249 (4)	0.167 (2)	0.50
Cl4	0.06774 (11)	0.54821 (19)	0.23620 (19)	0.0506 (7)	0.50
P	0.17978 (5)	0.91268 (11)	0.24594 (8)	0.0378 (3)
N	0.22282 (15)	0.7723 (3)	0.0921 (2)	0.0337 (9)
C1	0.3477 (4)	0.3728 (6)	0.2664 (5)	0.097 (3)
H1A	0.3771	0.3110	0.2447	0.117*
C2	0.3629 (4)	0.4509 (6)	0.3371 (4)	0.096 (3)
H2A	0.4066	0.4563	0.3742	0.115*
C3	0.3087 (4)	0.5257 (7)	0.3468 (5)	0.102 (2)
H3A	0.3067	0.5896	0.3936	0.123*
C4	0.2585 (4)	0.4921 (8)	0.2825 (6)	0.112 (2)
H4A	0.2137	0.5282	0.2749	0.135*
C5	0.2797 (4)	0.3974 (6)	0.2289 (6)	0.110 (3)
H5A	0.2530	0.3543	0.1789	0.132*
C6	0.3711 (2)	0.6848 (4)	0.1581 (3)	0.0451 (13)
H6A	0.3666	0.7517	0.2007	0.054*
C7	0.3221 (2)	0.6444 (4)	0.0886 (3)	0.0402 (12)
C8	0.3478 (2)	0.5451 (4)	0.0462 (3)	0.0442 (13)
H8A	0.3246	0.4984	−0.0050	0.053*
C9	0.4145 (2)	0.5275 (4)	0.0860 (4)	0.0482 (13)
H9A	0.4452	0.4658	0.0686	0.058*
C10	0.4278 (2)	0.6129 (4)	0.1561 (4)	0.0539 (15)
H10A	0.4696	0.6210	0.1973	0.065*
C11	0.25027 (18)	0.6757 (4)	0.0722 (3)	0.0360 (11)
H11A	0.2215	0.6215	0.0449	0.043*
C12	0.1890 (2)	0.8272 (4)	0.3601 (4)	0.0516 (13)
C13	0.1388 (3)	0.7539 (5)	0.3915 (4)	0.0752 (19)
H13A	0.0985	0.7462	0.3539	0.090*
C14	0.1495 (4)	0.6915 (6)	0.4806 (4)	0.090 (2)
H14A	0.1174	0.6392	0.5022	0.108*
C15	0.2068 (3)	0.7088 (6)	0.5338 (5)	0.092 (2)
H15A	0.2139	0.6660	0.5925	0.111*
C16	0.2540 (3)	0.7823 (6)	0.5090 (5)	0.0902 (19)
H16A	0.2923	0.7946	0.5502	0.108*
C17	0.2437 (3)	0.8398 (6)	0.4191 (4)	0.086 (2)
H17A	0.2770	0.8904	0.3985	0.104*
C18	0.1426 (2)	1.0435 (4)	0.2854 (3)	0.0443 (13)
C19	0.1014 (3)	1.0460 (5)	0.3785 (4)	0.0586 (16)
H19A	0.0966	0.9831	0.4195	0.070*
C20	0.0699 (3)	1.1442 (5)	0.4040 (5)	0.0793 (19)
H20A	0.0416	1.1462	0.4617	0.095*
C21	0.0784 (3)	1.2379 (4)	0.3481 (5)	0.0659 (17)
H21A	0.0579	1.3039	0.3693	0.079*
C22	0.1165 (3)	1.2358 (5)	0.2618 (5)	0.0641 (17)
H22A	0.1198	1.2999	0.2219	0.077*
C23	0.1507 (2)	1.1413 (4)	0.2307 (4)	0.0505 (14)
H23A	0.1792	1.1434	0.1732	0.061*
C24	0.1200 (2)	0.8442 (4)	0.1607 (3)	0.0378 (11)
C25	0.0481 (2)	0.8598 (4)	0.1615 (3)	0.0404 (12)
H25A	0.0273	0.9038	0.2115	0.049*
C26	0.0092 (2)	0.8074 (4)	0.0854 (4)	0.0536 (15)
H26A	−0.0381	0.8164	0.0841	0.064*
C27	0.0420 (2)	0.7399 (4)	0.0095 (3)	0.0506 (14)
H27A	0.0159	0.7044	−0.0406	0.061*
C28	0.1120 (2)	0.7269 (4)	0.0100 (3)	0.0410 (12)
H28A	0.1336	0.6825	−0.0389	0.049*
C29	0.14973 (19)	0.7811 (3)	0.0845 (3)	0.0372 (11)
C30	0.5000	1.0000	0.2754 (18)	0.104 (8)	0.50
H30A	0.5386	0.9885	0.2308	0.125*	0.50
C31	0.0000	0.5000	0.1697 (9)	0.051 (4)	0.50
H31A	−0.0159	0.5590	0.1260	0.061*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt	0.03605 (6)	0.03424 (7)	0.03646 (7)	0.00216 (7)	−0.00032 (7)	0.00005 (8)
Fe	0.0432 (3)	0.0405 (4)	0.0497 (4)	0.0021 (3)	0.0018 (3)	−0.0005 (3)
Cl1	0.0584 (6)	0.0514 (7)	0.0608 (7)	−0.0109 (6)	0.0017 (5)	−0.0103 (6)
Cl2	0.0508 (5)	0.0506 (6)	0.0598 (6)	0.0014 (6)	0.0200 (5)	0.0055 (6)
Cl3	0.131 (3)	0.146 (5)	0.223 (5)	−0.030 (3)	−0.087 (3)	0.041 (4)
Cl4	0.0373 (10)	0.0439 (13)	0.0706 (14)	−0.0113 (9)	−0.0071 (10)	−0.0009 (11)
P	0.0425 (5)	0.0380 (6)	0.0329 (5)	0.0046 (6)	0.0017 (4)	0.0009 (5)
N	0.0341 (15)	0.0340 (17)	0.0331 (15)	0.0043 (15)	0.0016 (14)	−0.0008 (14)
C1	0.132 (5)	0.060 (4)	0.100 (5)	−0.006 (4)	0.029 (4)	0.016 (3)
C2	0.119 (5)	0.115 (6)	0.054 (3)	−0.001 (4)	0.009 (3)	0.029 (3)
C3	0.124 (4)	0.104 (4)	0.078 (3)	0.008 (3)	0.032 (3)	−0.005 (3)
C4	0.097 (4)	0.117 (4)	0.123 (4)	0.006 (3)	0.030 (3)	0.021 (4)
C5	0.123 (5)	0.113 (5)	0.095 (5)	−0.060 (5)	−0.009 (4)	0.023 (4)
C6	0.046 (2)	0.038 (2)	0.051 (3)	−0.004 (2)	−0.010 (2)	−0.004 (2)
C7	0.051 (2)	0.031 (2)	0.039 (2)	0.009 (2)	0.001 (2)	−0.0032 (19)
C8	0.038 (2)	0.045 (3)	0.049 (2)	0.004 (2)	−0.0016 (19)	−0.003 (2)
C9	0.036 (2)	0.042 (3)	0.066 (3)	0.005 (2)	0.002 (2)	−0.006 (2)
C10	0.0300 (18)	0.065 (3)	0.067 (3)	0.004 (2)	−0.006 (2)	−0.011 (3)
C11	0.0337 (19)	0.044 (2)	0.0302 (19)	0.0036 (17)	−0.0006 (16)	0.0032 (19)
C12	0.063 (2)	0.047 (3)	0.044 (2)	0.020 (2)	0.016 (2)	−0.005 (2)
C13	0.095 (4)	0.068 (4)	0.063 (3)	0.015 (3)	0.018 (3)	0.018 (3)
C14	0.129 (5)	0.075 (4)	0.067 (3)	0.004 (4)	0.045 (3)	0.023 (3)
C15	0.121 (4)	0.087 (4)	0.069 (3)	0.035 (3)	0.006 (3)	0.011 (3)
C16	0.093 (3)	0.095 (4)	0.083 (3)	0.028 (3)	−0.014 (3)	0.018 (3)
C17	0.108 (4)	0.114 (5)	0.037 (2)	0.045 (4)	−0.034 (3)	−0.007 (3)
C18	0.040 (2)	0.049 (3)	0.044 (2)	0.013 (2)	−0.0078 (19)	−0.007 (2)
C19	0.065 (3)	0.058 (3)	0.053 (3)	−0.002 (3)	0.011 (2)	−0.011 (2)
C20	0.070 (3)	0.093 (4)	0.075 (3)	0.038 (3)	0.015 (3)	−0.029 (3)
C21	0.071 (3)	0.037 (3)	0.090 (4)	0.016 (2)	−0.010 (3)	−0.006 (3)
C22	0.064 (3)	0.042 (3)	0.085 (4)	0.010 (3)	−0.007 (3)	−0.017 (3)
C23	0.052 (2)	0.048 (3)	0.051 (3)	−0.003 (2)	−0.007 (2)	0.002 (2)
C24	0.048 (2)	0.039 (2)	0.026 (2)	0.0119 (19)	0.0011 (18)	0.0000 (18)
C25	0.0375 (19)	0.042 (2)	0.042 (2)	−0.0011 (19)	0.0028 (18)	0.003 (2)
C26	0.039 (2)	0.056 (3)	0.065 (3)	0.005 (2)	−0.004 (2)	0.017 (3)
C27	0.047 (2)	0.051 (3)	0.054 (3)	0.003 (2)	−0.018 (2)	0.001 (2)
C28	0.040 (2)	0.028 (2)	0.055 (3)	0.0042 (19)	0.003 (2)	−0.0047 (19)
C29	0.0346 (18)	0.029 (2)	0.048 (2)	0.0037 (18)	0.0009 (18)	0.0088 (19)
C30	0.017 (6)	0.121 (17)	0.174 (19)	0.001 (8)	0.000	0.000
C31	0.093 (9)	0.020 (6)	0.040 (7)	−0.019 (7)	0.000	0.000

Geometric parameters (Å, º) top

Pt—N	2.031 (3)	C9—H9A	0.9800
Pt—P	2.2089 (10)	C10—H10A	0.9800
Pt—Cl1	2.2996 (13)	C11—H11A	0.9300
Pt—Cl2	2.3673 (11)	C12—C17	1.323 (7)
Fe—C1	2.059 (7)	C12—C13	1.379 (8)
Fe—C2	2.055 (6)	C13—C14	1.394 (8)
Fe—C3	2.022 (7)	C13—H13A	0.9300
Fe—C4	1.998 (8)	C14—C15	1.330 (9)
Fe—C5	2.017 (7)	C14—H14A	0.9300
Fe—C6	2.043 (5)	C15—C16	1.317 (10)
Fe—C7	2.044 (4)	C15—H15A	0.9300
Fe—C8	2.000 (5)	C16—C17	1.371 (9)
Fe—C9	2.041 (5)	C16—H16A	0.9300
Fe—C10	2.042 (5)	C17—H17A	0.9300
Cl3—C30	1.570 (11)	C18—C23	1.382 (7)
Cl4—C31	1.681 (6)	C18—C19	1.451 (6)
P—C18	1.806 (5)	C19—C20	1.371 (8)
P—C24	1.806 (4)	C19—H19A	0.9300
P—C12	1.812 (5)	C20—C21	1.350 (8)
N—C11	1.304 (5)	C20—H20A	0.9300
N—C29	1.433 (5)	C21—C22	1.345 (8)
C1—C2	1.346 (10)	C21—H21A	0.9300
C1—C5	1.443 (10)	C22—C23	1.378 (7)
C1—H1A	0.9800	C22—H22A	0.9300
C2—C3	1.393 (10)	C23—H23A	0.9300
C2—H2A	0.9800	C24—C29	1.375 (6)
C3—C4	1.348 (11)	C24—C25	1.413 (6)
C3—H3A	0.9800	C25—C26	1.397 (6)
C4—C5	1.396 (11)	C25—H25A	0.9300
C4—H4A	0.9800	C26—C27	1.427 (7)
C5—H5A	0.9800	C26—H26A	0.9300
C6—C7	1.401 (6)	C27—C28	1.375 (6)
C6—C10	1.404 (6)	C27—H27A	0.9300
C6—H6A	0.9800	C28—C29	1.378 (6)
C7—C8	1.407 (6)	C28—H28A	0.9300
C7—C11	1.466 (6)	C30—Cl3ⁱ	1.570 (11)
C8—C9	1.415 (6)	C30—H30A	0.9600
C8—H8A	0.9800	C31—Cl4ⁱⁱ	1.681 (6)
C9—C10	1.396 (7)	C31—H31A	0.9600

N—Pt—P	80.59 (9)	C10—C6—Fe	69.9 (3)
N—Pt—Cl1	176.29 (9)	C7—C6—H6A	125.9
P—Pt—Cl1	95.92 (4)	C10—C6—H6A	125.9
N—Pt—Cl2	93.46 (9)	Fe—C6—H6A	125.9
P—Pt—Cl2	170.19 (4)	C6—C7—C8	107.6 (4)
Cl1—Pt—Cl2	90.17 (4)	C6—C7—C11	131.0 (4)
C4—Fe—C8	127.4 (3)	C8—C7—C11	120.1 (4)
C4—Fe—C5	40.7 (3)	C6—C7—Fe	69.9 (3)
C8—Fe—C5	107.8 (3)	C8—C7—Fe	68.0 (3)
C4—Fe—C3	39.2 (3)	C11—C7—Fe	117.3 (3)
C8—Fe—C3	163.9 (2)	C7—C8—C9	108.2 (4)
C5—Fe—C3	67.5 (3)	C7—C8—Fe	71.3 (3)
C4—Fe—C9	162.5 (3)	C9—C8—Fe	71.1 (3)
C8—Fe—C9	40.96 (18)	C7—C8—H8A	125.9
C5—Fe—C9	123.6 (3)	C9—C8—H8A	125.9
C3—Fe—C9	154.7 (2)	Fe—C8—H8A	125.9
C4—Fe—C10	157.4 (3)	C10—C9—C8	107.4 (4)
C8—Fe—C10	68.14 (19)	C10—C9—Fe	70.1 (3)
C5—Fe—C10	159.2 (3)	C8—C9—Fe	68.0 (3)
C3—Fe—C10	121.9 (3)	C10—C9—H9A	126.3
C9—Fe—C10	39.98 (19)	C8—C9—H9A	126.3
C4—Fe—C6	124.5 (3)	Fe—C9—H9A	126.3
C8—Fe—C6	68.16 (18)	C9—C10—C6	108.6 (4)
C5—Fe—C6	159.2 (2)	C9—C10—Fe	70.0 (3)
C3—Fe—C6	110.3 (3)	C6—C10—Fe	69.9 (3)
C9—Fe—C6	67.63 (19)	C9—C10—H10A	125.7
C10—Fe—C6	40.19 (18)	C6—C10—H10A	125.7
C4—Fe—C7	111.9 (3)	Fe—C10—H10A	125.7
C8—Fe—C7	40.71 (18)	N—C11—C7	126.3 (4)
C5—Fe—C7	123.6 (2)	N—C11—H11A	116.9
C3—Fe—C7	127.8 (3)	C7—C11—H11A	116.9
C9—Fe—C7	68.04 (18)	C17—C12—C13	118.3 (5)
C10—Fe—C7	67.55 (18)	C17—C12—P	119.3 (4)
C6—Fe—C7	40.09 (17)	C13—C12—P	122.3 (4)
C4—Fe—C2	66.2 (3)	C12—C13—C14	118.9 (6)
C8—Fe—C2	154.1 (2)	C12—C13—H13A	120.6
C5—Fe—C2	66.8 (3)	C14—C13—H13A	120.6
C3—Fe—C2	40.0 (3)	C15—C14—C13	118.2 (6)
C9—Fe—C2	119.2 (2)	C15—C14—H14A	120.9
C10—Fe—C2	107.4 (3)	C13—C14—H14A	120.9
C6—Fe—C2	125.9 (2)	C16—C15—C14	124.5 (7)
C7—Fe—C2	163.2 (2)	C16—C15—H15A	117.8
C4—Fe—C1	67.8 (3)	C14—C15—H15A	117.8
C8—Fe—C1	120.8 (2)	C15—C16—C17	116.3 (6)
C5—Fe—C1	41.5 (3)	C15—C16—H16A	121.8
C3—Fe—C1	66.8 (3)	C17—C16—H16A	121.8
C9—Fe—C1	105.4 (2)	C12—C17—C16	123.7 (6)
C10—Fe—C1	121.6 (3)	C12—C17—H17A	118.2
C6—Fe—C1	158.5 (2)	C16—C17—H17A	118.2
C7—Fe—C1	158.2 (2)	C23—C18—C19	118.3 (4)
C2—Fe—C1	38.2 (3)	C23—C18—P	123.3 (3)
C18—P—C24	108.1 (2)	C19—C18—P	118.4 (4)
C18—P—C12	107.6 (2)	C20—C19—C18	117.9 (5)
C24—P—C12	107.9 (2)	C20—C19—H19A	121.1
C18—P—Pt	119.65 (15)	C18—C19—H19A	121.1
C24—P—Pt	98.46 (13)	C21—C20—C19	122.2 (5)
C12—P—Pt	114.18 (15)	C21—C20—H20A	118.9
C11—N—C29	117.4 (3)	C19—C20—H20A	118.9
C11—N—Pt	127.8 (3)	C22—C21—C20	120.0 (5)
C29—N—Pt	114.6 (2)	C22—C21—H21A	120.0
C2—C1—C5	106.8 (7)	C20—C21—H21A	120.0
C2—C1—Fe	70.7 (4)	C21—C22—C23	121.8 (5)
C5—C1—Fe	67.7 (4)	C21—C22—H22A	119.1
C2—C1—H1A	126.6	C23—C22—H22A	119.1
C5—C1—H1A	126.6	C22—C23—C18	119.6 (5)
Fe—C1—H1A	126.6	C22—C23—H23A	120.2
C1—C2—C3	110.1 (7)	C18—C23—H23A	120.2
C1—C2—Fe	71.1 (4)	C29—C24—C25	119.8 (4)
C3—C2—Fe	68.7 (4)	C29—C24—P	114.8 (3)
C1—C2—H2A	124.9	C25—C24—P	125.1 (3)
C3—C2—H2A	124.9	C26—C25—C24	118.3 (4)
Fe—C2—H2A	124.9	C26—C25—H25A	120.9
C4—C3—C2	107.6 (7)	C24—C25—H25A	120.9
C4—C3—Fe	69.5 (4)	C25—C26—C27	120.1 (4)
C2—C3—Fe	71.3 (4)	C25—C26—H26A	120.0
C4—C3—H3A	126.2	C27—C26—H26A	120.0
C2—C3—H3A	126.2	C28—C27—C26	120.4 (4)
Fe—C3—H3A	126.2	C28—C27—H27A	119.8
C3—C4—C5	109.7 (7)	C26—C27—H27A	119.8
C3—C4—Fe	71.3 (5)	C27—C28—C29	118.7 (4)
C5—C4—Fe	70.4 (4)	C27—C28—H28A	120.7
C3—C4—H4A	125.1	C29—C28—H28A	120.7
C5—C4—H4A	125.1	C24—C29—C28	122.7 (4)
Fe—C4—H4A	125.1	C24—C29—N	114.3 (4)
C4—C5—C1	105.7 (7)	C28—C29—N	123.0 (4)
C4—C5—Fe	68.9 (5)	Cl3ⁱ—C30—Cl3	131.7 (16)
C1—C5—Fe	70.8 (4)	Cl3ⁱ—C30—H30A	104.6
C4—C5—H5A	127.1	Cl3—C30—H30A	104.0
C1—C5—H5A	127.1	Cl4—C31—Cl4ⁱⁱ	118.2 (7)
Fe—C5—H5A	127.1	Cl4—C31—H31A	107.6
C7—C6—C10	108.2 (4)	Cl4ⁱⁱ—C31—H31A	107.7
C7—C6—Fe	70.0 (3)

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

Experimental details

Crystal data
Chemical formula	[FePt(C₅H₅)(C₂₄H₁₉NP)Cl₂]·0.5CH₂Cl₂
M_r	781.75
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	19.5045 (11), 12.0182 (7), 12.9800 (8)
V (Å³)	3042.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.40
Crystal size (mm)	0.3 × 0.1 × 0.1

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.532, 0.588
No. of measured, independent and observed [I > 2σ(I)] reflections	19964, 5902, 4954
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.04
No. of reflections	5902
No. of parameters	345
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.93
Absolute structure	Flack (1983), 856 Friedel pairs
Absolute structure parameter	0.002 (11)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Pt—N	2.031 (3)	Pt—Cl1	2.2996 (13)
Pt—P	2.2089 (10)	Pt—Cl2	2.3673 (11)

Acknowledgements

The authors thank Jiangxi Provincial Department of Education (2007168) and the Natural Science Foundation of Jiangxi Province (0620071) for financial support for this work. In addition, the Materials Chemistry Department of Nanchang Hangkong University is acknowledged.

References

Cullen, W. R. & Woolins, J. D. (1981). Coord. Chem. Rev. 39, 1–47. CrossRef CAS Web of Science Google Scholar
Farrell, A., Goddard, R. & Guiry, P. J. (2002). J. Org. Chem. 67, 4209–4217. Web of Science CSD CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gong, J. F., Wang, D. W., Zhang, Y. H., Zhu, Y. & Wu, Y. J. (2006). Inorg. Chim. Acta, 359, 2115–2119. Web of Science CrossRef CAS Google Scholar
Gul, N., Nelson, J. H., Willis, A. C. & Ross, A. D. (2002). Organometallics, 21, 2041–2045. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Wu, Y., Hou, J., Cui, X. & Yuan, R. (2001). J. Organomet. Chem. 637–639, 793–798. Web of Science CrossRef CAS Google Scholar
Zhang, X.-L., Kuang, R.-Y., Cao, Q.-Y. & Luo, L.-T. (2006). Acta Cryst. E62, m2491–m2492. Web of Science CSD CrossRef 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.