[(1,2,5,6-η)-Cyclo­octa-1,5-diene]bis­(4-methyl­phen­yl)platinum(II)

Wang, Z.-W.; Liu, R.; Liu, H.-Y.; Wan, C.-Q.

doi:10.1107/S1600536810049664

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m37

https://doi.org/10.1107/S1600536810049664

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[(1,2,5,6-η)-Cycloocta-1,5-diene]bis(4-methylphenyl)platinum(II)

Zhi-Wei Wang,^a Ran Liu,^a Hong-Yu Liu ^a and Chong-Qing Wan ^a ^*

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: wanchqing@yahoo.com.cn

(Received 20 November 2010; accepted 28 November 2010; online 4 December 2010)

In the mononuclear title complex, [Pt(C₇H₇)₂(C₈H₁₂)], the Pt^II ion exhibits a square-planar coordination geometry defined by two methylphenyl ligands and the mid-points of the two π-coordinated double bonds of cycloocta-1,5-diene. The two methylphenyl groups have a cis relationship with a C—Pt—C bond angle of 88.54 (18)° and a dihedral angle between the mean planes of the benzene rings of 83.87 (1)°. Each complex molecule links to four symmetry-related ones through intermolecular C—H⋯π interactions, forming a layer almost parallel to the bc plane.

Related literature

For general background to Pt^II complexes with cycloocta-1,5-diene, see: Goel et al. (1982); Syed et al. (1984 ). For the structures of analogous Pt^II complexes, see: Deacon et al. (1993 ); Debaerdemaeker et al. (1987 , 1991 ); Roviello et al. (2006 ). For C—H⋯π interactions, see: Umezawa et al. (1998 ). For the preparation, see: Chaudhury & Puddephatt (1975 ).

Experimental

Crystal data

[Pt(C₇H₇)₂(C₈H₁₂)]
M_r = 485.52
Monoclinic, C 2/c
a = 25.029 (13) Å
b = 8.172 (4) Å
c = 19.674 (10) Å
β = 118.417 (8)°
V = 3539 (3) Å³
Z = 8
Mo Kα radiation
μ = 7.93 mm⁻¹
T = 293 K
0.36 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.584, T_max = 1.000
8906 measured reflections
3113 independent reflections
2884 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.061
S = 1.11
3113 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 2.74 e Å⁻³
Δρ_min = −0.99 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯Cg1ⁱ	0.96	2.93	3.615 (4)	129
C20—H20B⋯Cg1ⁱⁱ	0.96	2.85	3.749 (5)	155
C21—H21A⋯Cg2ⁱⁱ	0.97	2.83	3.411 (4)	119
C8—H8C⋯Cg2ⁱⁱⁱ	0.96	2.85	3.509 (2)	126
Symmetry codes: (i) $[x, -y+2, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810049664/zq2077sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049664/zq2077Isup2.hkl

checkCIF report

Comment top

The Pt^II complexes with cycloocta-1,5-diene (COD) are versatile precursors in inorganic synthesis (Goel et al., 1982; Syed et al., 1984). Herein, we report the structure of the bis-aryl complex [(COD)Pt(C₇H₇)₂]. In the crystal structure of the title complex, the center Pt^II adopts a square-planer coordination geometry with two methylphenyl groups depositing in a cis relationship, and the cycloocta-1,5-diene bonding to the ion with a 1,2,5,6-η⁴-coordination mode (Fig. 1). The Pt1—C5 and Pt1—C12 bond lengths equal 2.028 (4) Å, while the distances from the Pt^II to the doubly-bonded C atoms lie within the range of 2.256 (4)–2.279 (4) Å, all of which are comparable to that of similar complexes. The two methylphenyl groups site in a cis relationship with a C5—Pt1—C12 bond angle of 88.54 (18)° and a dihedral angle between the two benzene rings of 83.87 (1)°. Each of such mononuclear complex moiety links four symmetry-related ones through two types of intermolecular C—H···π interactions [C—H(methylene)···π and C—H(methyl)···π] to form a layer almost parallel to the bc plane, as shown in Fig. 2. The C···centroid distances vary from 3.411 (4) to 3.749 (5) Å, and C—H···centroid bond angles lie within the range of 119–155° (Umezawa et al. 1998).

Related literature top

For general background to Pt^II complexes with cycloocta-1,5-diene, see: Goel et al. (1982); Syed et al. (1984). For the structures of analogous Pt^II complexes, see: Deacon et al. (1993); Debaerdemaeker et al. (1987, 1991); Roviello et al. (2006). For C—H···π interactions, see: Umezawa et al. (1998). For the preparation, see: Chaudhury & Puddephatt (1975).

Experimental top

The title complex was obtained following a reaction procedure from literature (Chaudhury et al., 1975). Reaction of aryl Grignard reagents (C₆H₄-4-CH₃)MgBr (0.195 g, 1 mmol) with (COD)PtCl₂ (0.086 g, 0.8 mmol) in ether formed the title compound as a white powder, crystals of which were obtained after four days by recrystallization from CH₂Cl₂/n-hexane, yield: 0.233 g (60%).

Structure description top

For general background to Pt^II complexes with cycloocta-1,5-diene, see: Goel et al. (1982); Syed et al. (1984). For the structures of analogous Pt^II complexes, see: Deacon et al. (1993); Debaerdemaeker et al. (1987, 1991); Roviello et al. (2006). For C—H···π interactions, see: Umezawa et al. (1998). For the preparation, see: Chaudhury & Puddephatt (1975).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The atom-numbering scheme of the title complex. Displacement ellipsoids are drawn at the 30% probability level and H atoms are omitted for clarity.
	Fig. 2. The C—H(methyl)···π and C—H(methylene)···π interactions between the mononuclear units, forming a layer in the bc plane. The Cg1 and Cg2 are the centroids of the C9—C10—C11—C12—C13—C14 and C2—C3—C4—C5—C6—C7 rings, respectively. Symmetry codes: (i) x, -y + 2, z - 1/2; (ii) x, y + 1, z; (iii) x, -y + 2, z + 1/2.

[(1,2,5,6-η)-Cycloocta-1,5-diene]bis(4-methylphenyl)platinum(II) top

Crystal data top

[Pt(C₇H₇)₂(C₈H₁₂)]	Z = 8
M_r = 485.52	F(000) = 1888
Monoclinic, C2/c	D_x = 1.823 Mg m⁻³
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.029 (13) Å	µ = 7.93 mm⁻¹
b = 8.172 (4) Å	T = 293 K
c = 19.674 (10) Å	Block, colourless
β = 118.417 (8)°	0.36 × 0.30 × 0.20 mm
V = 3539 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3113 independent reflections
Radiation source: fine-focus sealed tube	2884 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −29→17
T_min = 0.584, T_max = 1.000	k = −9→9
8906 measured reflections	l = −20→23

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0308P)² + 23.1984P] P = (F_o² + 2F_c²)/3
3113 reflections	(Δ/σ)_max = 0.004
208 parameters	Δρ_max = 2.74 e Å⁻³
0 restraints	Δρ_min = −0.99 e Å⁻³

Crystal data top

[Pt(C₇H₇)₂(C₈H₁₂)]	V = 3539 (3) Å³
M_r = 485.52	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.029 (13) Å	µ = 7.93 mm⁻¹
b = 8.172 (4) Å	T = 293 K
c = 19.674 (10) Å	0.36 × 0.30 × 0.20 mm
β = 118.417 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3113 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2884 reflections with I > 2σ(I)
T_min = 0.584, T_max = 1.000	R_int = 0.023
8906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0308P)² + 23.1984P] P = (F_o² + 2F_c²)/3
3113 reflections	Δρ_max = 2.74 e Å⁻³
208 parameters	Δρ_min = −0.99 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
Pt1	0.625760 (7)	0.723387 (19)	0.445111 (9)	0.00847 (8)
C5	0.6352 (2)	0.8997 (5)	0.5226 (2)	0.0123 (9)
C12	0.6322 (2)	0.9000 (5)	0.3769 (2)	0.0119 (9)
C15	0.5845 (2)	0.5524 (5)	0.4975 (2)	0.0118 (9)
H15A	0.5749	0.6041	0.5353	0.014*
C19	0.6452 (2)	0.5268 (5)	0.3793 (2)	0.0110 (9)
H19A	0.6613	0.5682	0.3458	0.013*
C18	0.5828 (2)	0.5402 (5)	0.3479 (2)	0.0137 (9)
H18A	0.5628	0.5894	0.2962	0.016*
C9	0.6352 (2)	1.1307 (5)	0.2696 (2)	0.0126 (9)
C11	0.6864 (2)	0.9413 (5)	0.3760 (2)	0.0106 (9)
H11A	0.7225	0.8924	0.4116	0.013*
C8	0.6356 (2)	1.2543 (6)	0.2132 (3)	0.0172 (10)
H8A	0.6763	1.2668	0.2210	0.026*
H8B	0.6212	1.3575	0.2213	0.026*
H8C	0.6096	1.2174	0.1614	0.026*
C21	0.6671 (2)	0.3611 (5)	0.5002 (2)	0.0139 (9)
H21A	0.6357	0.2780	0.4800	0.017*
H21B	0.7020	0.3150	0.5446	0.017*
C20	0.6854 (2)	0.4039 (5)	0.4380 (3)	0.0148 (9)
H20A	0.7266	0.4459	0.4633	0.018*
H20B	0.6854	0.3042	0.4112	0.018*
C6	0.5846 (2)	0.9915 (5)	0.5136 (3)	0.0136 (9)
H6A	0.5472	0.9738	0.4703	0.016*
C7	0.5889 (2)	1.1085 (5)	0.5680 (3)	0.0162 (10)
H7A	0.5545	1.1665	0.5601	0.019*
C1	0.6475 (3)	1.2679 (6)	0.6911 (3)	0.0246 (12)
H1A	0.6883	1.2740	0.7328	0.037*
H1B	0.6205	1.2389	0.7112	0.037*
H1C	0.6358	1.3723	0.6659	0.037*
C13	0.5800 (2)	0.9798 (6)	0.3221 (3)	0.0153 (9)
H13A	0.5431	0.9575	0.3207	0.018*
C17	0.5429 (2)	0.4230 (6)	0.3636 (2)	0.0144 (9)
H17A	0.5622	0.3163	0.3757	0.017*
H17B	0.5044	0.4120	0.3168	0.017*
C14	0.5813 (2)	1.0902 (5)	0.2700 (3)	0.0154 (9)
H14A	0.5452	1.1389	0.2342	0.019*
C22	0.6441 (2)	0.5074 (5)	0.5265 (2)	0.0133 (9)
H22A	0.6694	0.5349	0.5812	0.016*
C4	0.6897 (2)	0.9310 (5)	0.5893 (2)	0.0136 (9)
H4A	0.7241	0.8714	0.5984	0.016*
C10	0.6876 (2)	1.0531 (5)	0.3235 (2)	0.0134 (9)
H10A	0.7244	1.0763	0.3246	0.016*
C2	0.6439 (2)	1.1394 (6)	0.6337 (3)	0.0181 (10)
C16	0.5305 (2)	0.4754 (6)	0.4297 (3)	0.0152 (9)
H16A	0.4972	0.5528	0.4098	0.018*
H16B	0.5179	0.3801	0.4478	0.018*
C3	0.6939 (2)	1.0492 (6)	0.6427 (2)	0.0158 (9)
H3A	0.7314	1.0683	0.6857	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01211 (11)	0.00610 (11)	0.00793 (11)	−0.00017 (6)	0.00537 (8)	−0.00012 (6)
C5	0.019 (2)	0.009 (2)	0.012 (2)	−0.0001 (18)	0.0095 (19)	0.0006 (17)
C12	0.015 (2)	0.009 (2)	0.009 (2)	0.0004 (17)	0.0042 (18)	−0.0013 (17)
C15	0.021 (2)	0.007 (2)	0.011 (2)	−0.0015 (18)	0.0101 (19)	0.0012 (16)
C19	0.021 (2)	0.004 (2)	0.011 (2)	−0.0019 (17)	0.0103 (19)	−0.0031 (16)
C18	0.022 (3)	0.009 (2)	0.009 (2)	−0.0033 (18)	0.0059 (19)	−0.0051 (16)
C9	0.023 (2)	0.007 (2)	0.0093 (19)	−0.0021 (18)	0.0085 (19)	−0.0019 (16)
C11	0.013 (2)	0.006 (2)	0.010 (2)	0.0017 (17)	0.0036 (18)	0.0008 (16)
C8	0.028 (3)	0.011 (2)	0.016 (2)	0.0040 (19)	0.014 (2)	0.0011 (18)
C21	0.018 (2)	0.010 (2)	0.013 (2)	0.0005 (18)	0.0080 (19)	0.0011 (17)
C20	0.021 (2)	0.009 (2)	0.016 (2)	0.0010 (18)	0.010 (2)	−0.0024 (17)
C6	0.018 (2)	0.007 (2)	0.016 (2)	0.0005 (17)	0.0080 (19)	0.0019 (17)
C7	0.024 (3)	0.009 (2)	0.022 (2)	0.0046 (19)	0.016 (2)	0.0041 (18)
C1	0.041 (3)	0.011 (2)	0.023 (3)	0.002 (2)	0.017 (3)	−0.0013 (19)
C13	0.016 (2)	0.016 (2)	0.015 (2)	−0.0010 (18)	0.0082 (19)	0.0001 (18)
C17	0.014 (2)	0.014 (2)	0.013 (2)	−0.0039 (18)	0.0046 (18)	−0.0045 (17)
C14	0.018 (2)	0.013 (2)	0.012 (2)	0.0049 (18)	0.0049 (19)	0.0042 (18)
C22	0.020 (2)	0.011 (2)	0.010 (2)	−0.0017 (18)	0.0079 (19)	0.0001 (17)
C4	0.017 (2)	0.011 (2)	0.014 (2)	0.0019 (18)	0.0085 (19)	0.0035 (17)
C10	0.016 (2)	0.012 (2)	0.014 (2)	−0.0029 (18)	0.0085 (19)	−0.0013 (17)
C2	0.035 (3)	0.011 (2)	0.014 (2)	0.000 (2)	0.017 (2)	0.0016 (18)
C16	0.014 (2)	0.014 (2)	0.018 (2)	−0.0009 (18)	0.0069 (19)	−0.0024 (18)
C3	0.021 (2)	0.014 (2)	0.009 (2)	−0.0057 (19)	0.0044 (19)	−0.0007 (18)

Geometric parameters (Å, º) top

Pt1—C5	2.028 (4)	C21—C20	1.538 (6)
Pt1—C12	2.028 (4)	C21—H21A	0.9700
Pt1—C15	2.256 (4)	C21—H21B	0.9700
Pt1—C19	2.257 (4)	C20—H20A	0.9700
Pt1—C18	2.258 (4)	C20—H20B	0.9700
Pt1—C22	2.279 (4)	C6—C7	1.399 (6)
C5—C4	1.394 (6)	C6—H6A	0.9300
C5—C6	1.409 (6)	C7—C2	1.392 (7)
C12—C13	1.399 (6)	C7—H7A	0.9300
C12—C11	1.405 (6)	C1—C2	1.514 (7)
C15—C22	1.369 (7)	C1—H1A	0.9600
C15—C16	1.511 (6)	C1—H1B	0.9600
C15—H15A	0.9800	C1—H1C	0.9600
C19—C18	1.383 (6)	C13—C14	1.376 (6)
C19—C20	1.500 (6)	C13—H13A	0.9300
C19—H19A	0.9800	C17—C16	1.535 (6)
C18—C17	1.517 (6)	C17—H17A	0.9700
C18—H18A	0.9800	C17—H17B	0.9700
C9—C10	1.387 (6)	C14—H14A	0.9300
C9—C14	1.393 (7)	C22—H22A	0.9800
C9—C8	1.504 (6)	C4—C3	1.393 (6)
C11—C10	1.390 (6)	C4—H4A	0.9300
C11—H11A	0.9300	C10—H10A	0.9300
C8—H8A	0.9600	C2—C3	1.389 (7)
C8—H8B	0.9600	C16—H16A	0.9700
C8—H8C	0.9600	C16—H16B	0.9700
C21—C22	1.521 (6)	C3—H3A	0.9300

C5—Pt1—C12	88.54 (18)	H21A—C21—H21B	107.7
C5—Pt1—C15	90.66 (17)	C19—C20—C21	114.9 (4)
C12—Pt1—C15	160.11 (17)	C19—C20—H20A	108.5
C5—Pt1—C19	163.18 (18)	C21—C20—H20A	108.5
C12—Pt1—C19	91.14 (17)	C19—C20—H20B	108.5
C15—Pt1—C19	95.26 (16)	C21—C20—H20B	108.5
C5—Pt1—C18	161.08 (18)	H20A—C20—H20B	107.5
C12—Pt1—C18	93.84 (17)	C7—C6—C5	122.0 (4)
C15—Pt1—C18	80.76 (16)	C7—C6—H6A	119.0
C19—Pt1—C18	35.68 (16)	C5—C6—H6A	119.0
C5—Pt1—C22	96.28 (17)	C2—C7—C6	121.1 (4)
C12—Pt1—C22	164.40 (17)	C2—C7—H7A	119.4
C15—Pt1—C22	35.13 (16)	C6—C7—H7A	119.4
C19—Pt1—C22	79.97 (16)	C2—C1—H1A	109.5
C18—Pt1—C22	86.41 (16)	C2—C1—H1B	109.5
C4—C5—C6	116.0 (4)	H1A—C1—H1B	109.5
C4—C5—Pt1	123.3 (3)	C2—C1—H1C	109.5
C6—C5—Pt1	120.6 (3)	H1A—C1—H1C	109.5
C13—C12—C11	115.5 (4)	H1B—C1—H1C	109.5
C13—C12—Pt1	120.2 (3)	C14—C13—C12	122.4 (4)
C11—C12—Pt1	124.1 (3)	C14—C13—H13A	118.8
C22—C15—C16	126.5 (4)	C12—C13—H13A	118.8
C22—C15—Pt1	73.4 (3)	C18—C17—C16	114.5 (4)
C16—C15—Pt1	105.5 (3)	C18—C17—H17A	108.6
C22—C15—H15A	114.2	C16—C17—H17A	108.6
C16—C15—H15A	114.2	C18—C17—H17B	108.6
Pt1—C15—H15A	114.2	C16—C17—H17B	108.6
C18—C19—C20	126.7 (4)	H17A—C17—H17B	107.6
C18—C19—Pt1	72.2 (2)	C13—C14—C9	121.7 (4)
C20—C19—Pt1	106.5 (3)	C13—C14—H14A	119.2
C18—C19—H19A	114.2	C9—C14—H14A	119.2
C20—C19—H19A	114.2	C15—C22—C21	125.7 (4)
Pt1—C19—H19A	114.2	C15—C22—Pt1	71.5 (3)
C19—C18—C17	124.9 (4)	C21—C22—Pt1	110.6 (3)
C19—C18—Pt1	72.1 (2)	C15—C22—H22A	113.7
C17—C18—Pt1	109.8 (3)	C21—C22—H22A	113.7
C19—C18—H18A	114.1	Pt1—C22—H22A	113.7
C17—C18—H18A	114.1	C3—C4—C5	121.8 (4)
Pt1—C18—H18A	114.1	C3—C4—H4A	119.1
C10—C9—C14	117.0 (4)	C5—C4—H4A	119.1
C10—C9—C8	122.3 (4)	C9—C10—C11	121.4 (4)
C14—C9—C8	120.7 (4)	C9—C10—H10A	119.3
C10—C11—C12	122.0 (4)	C11—C10—H10A	119.3
C10—C11—H11A	119.0	C3—C2—C7	117.1 (4)
C12—C11—H11A	119.0	C3—C2—C1	122.9 (5)
C9—C8—H8A	109.5	C7—C2—C1	120.0 (5)
C9—C8—H8B	109.5	C15—C16—C17	114.0 (4)
H8A—C8—H8B	109.5	C15—C16—H16A	108.7
C9—C8—H8C	109.5	C17—C16—H16A	108.7
H8A—C8—H8C	109.5	C15—C16—H16B	108.7
H8B—C8—H8C	109.5	C17—C16—H16B	108.7
C22—C21—C20	113.4 (4)	H16A—C16—H16B	107.6
C22—C21—H21A	108.9	C2—C3—C4	122.1 (4)
C20—C21—H21A	108.9	C2—C3—H3A	119.0
C22—C21—H21B	108.9	C4—C3—H3A	119.0
C20—C21—H21B	108.9

C12—Pt1—C5—C4	−100.7 (4)	C12—Pt1—C18—C17	−151.9 (3)
C15—Pt1—C5—C4	99.1 (4)	C15—Pt1—C18—C17	8.8 (3)
C19—Pt1—C5—C4	−11.6 (8)	C19—Pt1—C18—C17	121.5 (4)
C18—Pt1—C5—C4	161.7 (4)	C22—Pt1—C18—C17	43.7 (3)
C22—Pt1—C5—C4	64.4 (4)	C13—C12—C11—C10	−0.6 (6)
C12—Pt1—C5—C6	83.4 (4)	Pt1—C12—C11—C10	174.2 (3)
C15—Pt1—C5—C6	−76.7 (4)	C18—C19—C20—C21	−37.3 (6)
C19—Pt1—C5—C6	172.5 (4)	Pt1—C19—C20—C21	42.5 (4)
C18—Pt1—C5—C6	−14.2 (7)	C22—C21—C20—C19	−38.0 (5)
C22—Pt1—C5—C6	−111.5 (4)	C4—C5—C6—C7	0.7 (6)
C5—Pt1—C12—C13	−89.5 (4)	Pt1—C5—C6—C7	176.9 (3)
C15—Pt1—C12—C13	−1.6 (7)	C5—C6—C7—C2	0.1 (7)
C19—Pt1—C12—C13	107.3 (4)	C11—C12—C13—C14	0.7 (6)
C18—Pt1—C12—C13	71.7 (4)	Pt1—C12—C13—C14	−174.3 (3)
C22—Pt1—C12—C13	162.1 (5)	C19—C18—C17—C16	93.6 (5)
C5—Pt1—C12—C11	95.9 (4)	Pt1—C18—C17—C16	12.0 (5)
C15—Pt1—C12—C11	−176.2 (4)	C12—C13—C14—C9	−0.9 (7)
C19—Pt1—C12—C11	−67.3 (4)	C10—C9—C14—C13	0.8 (6)
C18—Pt1—C12—C11	−102.9 (4)	C8—C9—C14—C13	−178.7 (4)
C22—Pt1—C12—C11	−12.5 (8)	C16—C15—C22—C21	−5.3 (7)
C5—Pt1—C15—C22	−100.0 (3)	Pt1—C15—C22—C21	−102.5 (4)
C12—Pt1—C15—C22	172.5 (4)	C16—C15—C22—Pt1	97.2 (4)
C19—Pt1—C15—C22	64.2 (3)	C20—C21—C22—C15	94.0 (5)
C18—Pt1—C15—C22	96.9 (3)	C20—C21—C22—Pt1	12.4 (5)
C5—Pt1—C15—C16	135.8 (3)	C5—Pt1—C22—C15	82.2 (3)
C12—Pt1—C15—C16	48.3 (6)	C12—Pt1—C22—C15	−170.5 (5)
C19—Pt1—C15—C16	−60.0 (3)	C19—Pt1—C22—C15	−114.4 (3)
C18—Pt1—C15—C16	−27.3 (3)	C18—Pt1—C22—C15	−79.0 (3)
C22—Pt1—C15—C16	−124.2 (4)	C5—Pt1—C22—C21	−155.7 (3)
C5—Pt1—C19—C18	176.3 (5)	C12—Pt1—C22—C21	−48.4 (7)
C12—Pt1—C19—C18	−95.0 (3)	C15—Pt1—C22—C21	122.1 (4)
C15—Pt1—C19—C18	66.1 (3)	C19—Pt1—C22—C21	7.7 (3)
C22—Pt1—C19—C18	97.9 (3)	C18—Pt1—C22—C21	43.1 (3)
C5—Pt1—C19—C20	52.3 (7)	C6—C5—C4—C3	−1.6 (6)
C12—Pt1—C19—C20	141.0 (3)	Pt1—C5—C4—C3	−177.6 (3)
C15—Pt1—C19—C20	−57.9 (3)	C14—C9—C10—C11	−0.7 (6)
C18—Pt1—C19—C20	−124.0 (4)	C8—C9—C10—C11	178.9 (4)
C22—Pt1—C19—C20	−26.1 (3)	C12—C11—C10—C9	0.6 (7)
C20—C19—C18—C17	−4.5 (7)	C6—C7—C2—C3	−0.1 (6)
Pt1—C19—C18—C17	−102.1 (4)	C6—C7—C2—C1	179.4 (4)
C20—C19—C18—Pt1	97.6 (4)	C22—C15—C16—C17	−37.5 (6)
C5—Pt1—C18—C19	−176.7 (4)	Pt1—C15—C16—C17	43.0 (4)
C12—Pt1—C18—C19	86.6 (3)	C18—C17—C16—C15	−38.4 (5)
C15—Pt1—C18—C19	−112.7 (3)	C7—C2—C3—C4	−0.8 (7)
C22—Pt1—C18—C19	−77.8 (3)	C1—C2—C3—C4	179.7 (4)
C5—Pt1—C18—C17	−55.2 (6)	C5—C4—C3—C2	1.7 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9–C14 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···Cg1ⁱ	0.96	2.93	3.615 (4)	129
C20—H20B···Cg1ⁱⁱ	0.96	2.85	3.749 (5)	155
C21—H21A···Cg2ⁱⁱ	0.97	2.83	3.411 (4)	119
C8—H8C···Cg2ⁱⁱⁱ	0.96	2.85	3.509 (2)	126

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

Experimental details

Crystal data
Chemical formula	[Pt(C₇H₇)₂(C₈H₁₂)]
M_r	485.52
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	25.029 (13), 8.172 (4), 19.674 (10)
β (°)	118.417 (8)
V (Å³)	3539 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	7.93
Crystal size (mm)	0.36 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.584, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8906, 3113, 2884
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.061, 1.11
No. of reflections	3113
No. of parameters	208
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0308P)² + 23.1984P] P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.74, −0.99

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C9–C14 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···Cg1ⁱ	0.96	2.93	3.615 (4)	129
C20—H20B···Cg1ⁱⁱ	0.96	2.85	3.749 (5)	155
C21—H21A···Cg2ⁱⁱ	0.97	2.83	3.411 (4)	119
C8—H8C···Cg2ⁱⁱⁱ	0.96	2.85	3.509 (2)	126

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

Acknowledgements

The authors are grateful for financial support from the Technology Program, Beijing Municipal Education Commission (Ref. No. 09530410099).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chaudhury, N. & Puddephatt, R. J. (1975). J. Organomet. Chem. 84, 105–115. CrossRef CAS Web of Science Google Scholar
Deacon, G. B., Hilderbrand, E. A. & Tiekink, E. R. T. (1993). Z. Kristallogr. 205, 340–342. CrossRef CAS Web of Science Google Scholar
Debaerdemaeker, T., Hohenadel, R. & Brune, H.-A. (1991). J. Organomet. Chem. 410, 127–275. CSD CrossRef Web of Science Google Scholar
Debaerdemaeker, T., Stapp, B. & Brune, H. A. (1987). Acta Cryst. C43, 473–476. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Goel, A. B., Goel, S. & van der Veer, D. (1982). Inorg. Chim. Acta, 65, L205–L206. CSD CrossRef CAS Web of Science Google Scholar
Roviello, G., Ruffo, F. & Tuzi, A. (2006). Acta Cryst. E62, m1416–m1418. Web of Science CSD CrossRef IUCr Journals 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
Syed, A., Stevens, E. D. & Cruz, S. G. (1984). Inorg. Chem. 23, 3673–3674. CSD CrossRef CAS Web of Science Google Scholar
Umezawa, Y., Tsuboyama, S., Honda, K., Uzawa, J. & Nishio, M. (1998). Bull. Chem. Soc. Jpn, 71, 1202–1213. Web of Science CrossRef Google Scholar

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