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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): m1013.
Published online 2008 July 9. doi:  10.1107/S1600536808020473
PMCID: PMC2961937

Chlorido[6-phenyl-4-(p-tol­yl)-2,2′-bipyridyl-κ2 N,N′]platinum(II)

Abstract

The asymmetric unit of the title compound, [Pt(C23H17N2)Cl], contains two independent mol­ecules with distinct dihedral angles between the central pyridyl and methylbenzene rings [7.77 (2) and 24.07 (2)°]. Short inter­molecular distances [3.582 (6) and 3.600 (6) Å] between the outer pyridine and the PtNC3 and PtN2C2 rings, respectively, indicate the existence of π–π inter­actions, which link the mol­ecules into stacks along the a axis. The crystal structure is further stabilized by weak C—H(...)π inter­actions.

Related literature

For related literature, see: Allen et al. (1987 [triangle]); Catalano et al. (2000 [triangle]); Kubicki et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1013-scheme1.jpg

Experimental

Crystal data

  • [Pt(C23H17N2)Cl]
  • M r = 551.92
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1013-efi1.jpg
  • a = 7.379 (5) Å
  • b = 18.066 (5) Å
  • c = 14.222 (5) Å
  • β = 102.551 (5)°
  • V = 1850.6 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 7.74 mm−1
  • T = 298 (2) K
  • 0.50 × 0.30 × 0.20 mm

Data collection

  • Bruker APEX area-dectector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.113, T max = 0.307 (expected range = 0.078–0.213)
  • 14983 measured reflections
  • 8028 independent reflections
  • 6615 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.110
  • S = 0.72
  • 8028 reflections
  • 489 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 1.91 e Å−3
  • Δρmin = −0.65 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 3598 Friedel pairs
  • Flack parameter: 0.001 (11)

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected interatomic distances (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020473/cv2424sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020473/cv2424Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Professor W.-T. Yu of Shan Dong University for his kind assistance with the X-ray structure determination.

supplementary crystallographic information

Comment

Recently, the bonding interaction between the closed-shell metal atoms or ions is gaining increasing attention, and while there exist numerous examples of fluorophenyl and cyanate platinum(II) centers aggregating with s2 ions such as Tl(I) or Pb(II) and d10 ions such as Au(I) or Ag(I)(Catalano et al., 2000), there are few reports of similar association in the case of alkyl platinum(II) complexes. As a part of our ongoing investigation on platinum complexes, the title compound (I) has been prepared and its crystal structure is presented here.

There are two crystallographically independent molecules in the asymmetric unit of (I) (Fig. 1). Each molecule contains a Pt atom coordinated in a distorted square-planar configuration with two Pt-N, one Pt-C and one Pt-Cl bonds (Table 1). Bond lengths and angles in the two molecules are similar and in a argreement with the values reported in the literature (Allen et al., 1987). The dihedral angles formed by the C17—C22 and C40—C45 benzene rings with N1/C6—C10 and N3/C29—C33 are 24.07 (2)°, 7.77 (2)°, respectively. The crystal packing of the structure exhibits π-π interactions proved by short intermolecular Cg1···Cg2 and Cg1···Cg3 distances of 3.582 (6) and 3.600 (6) Å, respectively; Cg1, Cg2 and Cg3 are centroids of N4/C24—C28, Pt1/N1/C10/C11/C16 and Pt1/N1/N2/C5/C6 rings, respectively (Table 1), which link the molecules into stacks along a axis. The crystal structure is further stabilized by the weak C—H···π interactions (Kubicki et al., 2002; Table 2).

Experimental

For the preparation of 3,6-diimidazolyl-9-ethylcarbazole, A mixture of 4-(p-tolyl)-6-phenyl-2,2'-bipyridine (96.72 mg, 0.30 mmol) and K2PtCl4 (124.58 mg, 0.30 mmol) were heated at 363 K with CH3CN (10 ml) as solvent for 18 h. The mixture was cooled to room temperature. Then it was filtered and concentrated, the re-crystallization from DMF produced red single crystals (38.90 mg, Yield 83.88%).

Refinement

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 - 0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). The highest residual peak [1.91 e Å-3] is situated 0.11 Å at atom H30.

Figures

Fig. 1.
: The content of asymmetric unit of the title compound showing the atomic numbering and 50% probability displacement ellipsoids.

Crystal data

[Pt(C23H17N2)Cl]Z = 4
Mr = 551.92F000 = 1056
Monoclinic, P21Dx = 1.981 Mg m3
a = 7.379 (5) ÅMo Kα radiation λ = 0.71069 Å
b = 18.066 (5) ŵ = 7.74 mm1
c = 14.222 (5) ÅT = 298 (2) K
β = 102.551 (5)ºNeedle, red
V = 1850.6 (15) Å30.50 × 0.30 × 0.20 mm

Data collection

Bruker APEX area-dectector diffractometer8028 independent reflections
Radiation source: fine-focus sealed tube6615 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 298(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2002)h = −9→9
Tmin = 0.113, Tmax = 0.307k = −23→23
14983 measured reflectionsl = −18→18

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038  w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max = 0.001
S = 0.72Δρmax = 1.91 e Å3
8028 reflectionsΔρmin = −0.65 e Å3
489 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 3598 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.001 (11)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
C190.7020 (18)0.2281 (9)0.3338 (8)0.071 (3)
H190.73830.27340.36280.085*
N30.0093 (11)0.0772 (4)0.1479 (6)0.0455 (18)
Pt2−0.09764 (5)−0.01160 (2)0.08126 (2)0.04713 (11)
Pt10.35781 (5)0.143731 (18)−0.25831 (2)0.04136 (10)
Cl2−0.2212 (5)−0.11757 (18)0.0028 (2)0.0741 (8)
Cl10.2643 (5)0.1428 (2)−0.42342 (17)0.0687 (7)
N10.4326 (9)0.1481 (5)−0.1195 (5)0.0391 (14)
C440.2848 (18)0.3505 (7)0.4362 (7)0.061 (3)
H440.27390.35800.49940.074*
C39−0.0498 (14)−0.0514 (6)0.2157 (7)0.052 (2)
C80.5388 (12)0.1543 (6)0.0788 (6)0.044 (2)
C27−0.0172 (14)0.1830 (6)−0.0774 (7)0.048 (2)
H270.03470.2287−0.05690.057*
C170.5989 (13)0.1582 (5)0.1879 (6)0.044 (2)
C400.2257 (12)0.2733 (5)0.2945 (6)0.0400 (19)
C330.0607 (13)0.0765 (5)0.2432 (7)0.044 (2)
C90.4583 (13)0.0905 (5)0.0326 (7)0.045 (2)
H90.44100.04930.06890.054*
C450.2185 (16)0.2857 (6)0.3890 (7)0.050 (2)
H450.16780.24960.42220.060*
C310.1507 (13)0.2049 (5)0.2432 (6)0.041 (2)
C410.3111 (14)0.3287 (6)0.2493 (6)0.047 (2)
H410.32260.32170.18610.056*
C120.2565 (16)−0.0365 (6)−0.0924 (9)0.058 (3)
H120.2838−0.0446−0.02620.069*
C100.4033 (12)0.0878 (5)−0.0677 (7)0.0404 (19)
C420.3768 (16)0.3918 (6)0.2959 (8)0.056 (3)
H420.42990.42750.26330.067*
C430.3675 (18)0.4046 (6)0.3900 (8)0.061 (3)
N4−0.1077 (11)0.0607 (5)−0.0380 (6)0.0500 (19)
C320.1347 (12)0.1397 (6)0.2932 (6)0.0457 (19)
H320.17360.13840.35990.055*
C290.0292 (12)0.1399 (7)0.0952 (5)0.0416 (18)
C25−0.1501 (16)0.0992 (8)−0.2003 (8)0.064 (3)
H25−0.18930.0876−0.26530.077*
N20.4760 (11)0.2509 (5)−0.2403 (5)0.0440 (17)
C160.2736 (12)0.0437 (5)−0.2302 (7)0.0411 (19)
C210.637 (2)0.1009 (9)0.3453 (9)0.081 (4)
H210.62830.05920.38230.097*
C37−0.0303 (18)−0.1362 (7)0.3487 (9)0.066 (3)
H37−0.0465−0.18390.36990.079*
C38−0.0821 (19)−0.1205 (7)0.2512 (8)0.064 (3)
H38−0.1395−0.15700.20890.077*
C340.0295 (14)0.0036 (5)0.2848 (7)0.046 (2)
C300.0987 (12)0.2031 (5)0.1427 (6)0.0403 (19)
H300.11150.24550.10760.048*
C460.436 (2)0.4749 (8)0.4407 (10)0.088 (4)
H46A0.44400.51250.39410.131*
H46B0.55620.46690.48140.131*
H46C0.35100.49050.47930.131*
C110.3080 (12)0.0276 (6)−0.1299 (7)0.044 (2)
C60.5122 (13)0.2106 (5)−0.0761 (7)0.044 (2)
C180.6581 (17)0.2241 (7)0.2346 (8)0.059 (3)
H180.66820.26630.19850.070*
C28−0.0335 (13)0.1287 (5)−0.0092 (6)0.045 (2)
C220.594 (2)0.0974 (8)0.2454 (8)0.074 (4)
H220.56080.05190.21610.089*
C70.5620 (15)0.2149 (6)0.0231 (7)0.047 (2)
H70.61120.25870.05260.057*
C24−0.1648 (14)0.0476 (7)−0.1329 (7)0.056 (3)
H24−0.21610.0018−0.15300.068*
C130.1620 (16)−0.0893 (6)−0.1555 (9)0.062 (3)
H130.1259−0.1337−0.13200.074*
C40.6150 (16)0.3362 (6)−0.1195 (8)0.057 (2)
H40.65260.3487−0.05480.068*
C350.0742 (16)−0.0126 (7)0.3828 (8)0.060 (2)
H350.12430.02380.42710.072*
C50.5346 (14)0.2690 (5)−0.1462 (7)0.045 (2)
C140.1223 (16)−0.0757 (7)−0.2530 (10)0.062 (3)
H140.0578−0.1111−0.29480.075*
C150.1765 (14)−0.0102 (8)−0.2903 (8)0.056 (2)
H150.1472−0.0024−0.35660.067*
C20.5799 (19)0.3664 (7)−0.2857 (9)0.068 (3)
H20.59290.3992−0.33420.082*
C10.5009 (15)0.2984 (7)−0.3080 (8)0.057 (3)
H10.46330.2850−0.37240.069*
C26−0.0770 (16)0.1693 (7)−0.1738 (7)0.063 (3)
H26−0.06940.2052−0.21970.075*
C30.6396 (17)0.3855 (7)−0.1910 (9)0.065 (3)
H30.69620.4311−0.17440.078*
C200.6946 (17)0.1699 (9)0.3895 (7)0.071 (4)
C360.044 (2)−0.0835 (7)0.4141 (9)0.069 (3)
H360.0738−0.09480.47940.082*
C230.744 (2)0.1739 (10)0.5006 (9)0.086 (4)
H23A0.84540.14080.52490.129*
H23B0.63830.15970.52540.129*
H23C0.77980.22350.52050.129*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C190.077 (8)0.085 (9)0.050 (6)−0.004 (7)0.013 (6)−0.018 (6)
N30.051 (4)0.042 (4)0.038 (4)0.008 (4)−0.003 (3)−0.003 (3)
Pt20.0528 (2)0.04704 (19)0.04067 (19)0.00263 (18)0.00828 (15)−0.00699 (16)
Pt10.04689 (18)0.03779 (16)0.03740 (17)0.00176 (16)0.00475 (13)0.00092 (15)
Cl20.102 (2)0.0613 (17)0.0567 (16)−0.0187 (17)0.0123 (16)−0.0182 (14)
Cl10.0953 (19)0.0648 (14)0.0393 (11)−0.0045 (19)−0.0002 (12)0.0015 (14)
N10.045 (3)0.035 (3)0.037 (3)0.009 (4)0.008 (3)−0.003 (4)
C440.084 (8)0.059 (7)0.037 (5)−0.006 (6)0.005 (5)−0.004 (5)
C390.056 (6)0.055 (6)0.048 (5)0.000 (5)0.016 (5)−0.009 (5)
C80.039 (4)0.055 (6)0.038 (4)0.015 (4)0.010 (3)0.000 (4)
C270.055 (6)0.047 (5)0.039 (5)0.012 (5)0.009 (4)0.003 (4)
C170.048 (5)0.049 (6)0.035 (4)0.008 (4)0.008 (3)−0.005 (4)
C400.048 (5)0.033 (4)0.039 (4)0.007 (4)0.010 (4)0.005 (4)
C330.044 (5)0.041 (5)0.043 (5)0.005 (4)0.005 (4)0.002 (4)
C90.046 (5)0.040 (5)0.049 (5)0.001 (4)0.012 (4)0.004 (4)
C450.073 (6)0.040 (5)0.035 (5)0.010 (5)0.007 (4)0.003 (4)
C310.049 (5)0.038 (5)0.036 (4)0.006 (4)0.010 (4)−0.001 (4)
C410.067 (6)0.044 (5)0.031 (4)0.007 (5)0.014 (4)0.003 (4)
C120.068 (7)0.049 (6)0.056 (6)0.001 (5)0.012 (5)0.010 (5)
C100.041 (5)0.037 (4)0.042 (5)0.008 (4)0.006 (4)−0.003 (4)
C420.067 (6)0.045 (5)0.053 (6)0.005 (5)0.005 (5)0.001 (5)
C430.080 (8)0.047 (5)0.044 (6)0.003 (6)−0.011 (5)0.003 (5)
N40.044 (4)0.058 (5)0.041 (4)0.001 (4)−0.005 (3)−0.006 (4)
C320.052 (5)0.055 (5)0.030 (4)0.008 (5)0.008 (3)0.003 (5)
C290.048 (4)0.051 (5)0.027 (3)0.010 (5)0.009 (3)0.005 (4)
C250.067 (7)0.091 (9)0.035 (5)0.014 (7)0.012 (5)−0.010 (6)
N20.049 (4)0.046 (4)0.035 (4)−0.005 (4)0.003 (3)0.005 (3)
C160.040 (4)0.035 (4)0.045 (5)0.004 (4)0.003 (4)0.000 (4)
C210.119 (12)0.073 (9)0.048 (7)−0.011 (8)0.015 (7)0.010 (6)
C370.082 (8)0.055 (6)0.060 (7)−0.013 (6)0.015 (6)0.007 (5)
C380.077 (7)0.053 (6)0.056 (7)−0.010 (6)0.002 (6)0.006 (5)
C340.056 (5)0.035 (5)0.047 (5)0.010 (4)0.015 (4)0.000 (4)
C300.042 (5)0.041 (5)0.037 (4)0.005 (4)0.007 (4)−0.001 (4)
C460.127 (12)0.060 (8)0.070 (8)−0.016 (8)0.010 (8)−0.007 (6)
C110.033 (4)0.044 (5)0.052 (5)0.002 (4)0.005 (4)−0.001 (4)
C60.041 (5)0.043 (5)0.045 (5)0.000 (4)0.006 (4)0.000 (4)
C180.067 (7)0.060 (6)0.050 (6)−0.005 (6)0.015 (5)0.007 (5)
C280.054 (5)0.051 (6)0.031 (4)0.020 (4)0.011 (4)−0.002 (4)
C220.108 (10)0.066 (8)0.044 (6)−0.007 (8)0.007 (6)−0.003 (5)
C70.060 (6)0.041 (5)0.041 (5)0.001 (4)0.010 (4)−0.006 (4)
C240.050 (5)0.072 (7)0.042 (5)−0.002 (5)0.000 (4)−0.016 (5)
C130.063 (7)0.041 (5)0.078 (8)−0.009 (5)0.005 (6)−0.002 (5)
C40.076 (7)0.041 (5)0.053 (6)0.000 (5)0.014 (5)0.001 (5)
C350.077 (7)0.045 (5)0.054 (5)0.001 (6)0.006 (5)0.005 (5)
C50.052 (5)0.042 (5)0.040 (5)0.002 (4)0.008 (4)−0.004 (4)
C140.058 (6)0.047 (6)0.082 (9)−0.008 (5)0.013 (6)−0.016 (6)
C150.053 (5)0.056 (6)0.053 (5)−0.010 (6)0.000 (4)−0.006 (6)
C20.084 (8)0.060 (7)0.064 (7)−0.003 (7)0.025 (6)0.018 (6)
C10.061 (6)0.055 (6)0.054 (6)−0.005 (5)0.011 (5)0.019 (5)
C260.066 (7)0.081 (8)0.039 (5)0.017 (6)0.006 (5)0.003 (5)
C30.069 (7)0.048 (6)0.076 (8)−0.017 (6)0.011 (6)−0.005 (6)
C200.069 (7)0.111 (11)0.030 (5)0.006 (7)0.007 (5)0.006 (6)
C360.093 (8)0.063 (7)0.055 (7)0.001 (7)0.026 (6)0.017 (6)
C230.105 (10)0.105 (11)0.048 (7)0.000 (9)0.016 (7)−0.010 (7)

Geometric parameters (Å, °)

C19—C201.32 (2)C32—H320.9300
C19—C181.379 (16)C29—C301.369 (14)
C19—H190.9300C29—C281.470 (11)
N3—C331.325 (12)C25—C241.358 (18)
N3—C291.384 (14)C25—C261.397 (18)
N3—Pt21.941 (8)C25—H250.9300
Pt2—C392.001 (11)N2—C11.333 (13)
Pt2—N42.130 (9)N2—C51.354 (12)
Pt2—Cl22.302 (3)C16—C151.388 (14)
Pt1—N11.932 (7)C16—C111.422 (14)
Pt1—C161.981 (9)C21—C221.388 (17)
Pt1—N22.116 (8)C21—C201.42 (2)
Pt1—Cl12.299 (3)C21—H210.9300
N1—C61.357 (13)C37—C361.360 (18)
N1—C101.358 (13)C37—C381.384 (16)
C44—C451.385 (15)C37—H370.9300
C44—C431.390 (17)C38—H380.9300
C44—H440.9300C34—C351.391 (14)
C39—C381.387 (17)C30—H300.9300
C39—C341.432 (14)C46—H46A0.9600
C8—C71.384 (14)C46—H46B0.9600
C8—C91.394 (14)C46—H46C0.9600
C8—C171.520 (12)C6—C71.381 (13)
C27—C261.368 (14)C6—C51.486 (14)
C27—C281.403 (14)C18—H180.9300
C27—H270.9300C22—H220.9300
C17—C221.374 (16)C7—H70.9300
C17—C181.388 (16)C24—H240.9300
C40—C451.375 (13)C13—C141.375 (17)
C40—C411.410 (13)C13—H130.9300
C40—C311.480 (13)C4—C51.368 (14)
C33—C321.393 (15)C4—C31.393 (16)
C33—C341.482 (13)C4—H40.9300
C9—C101.396 (13)C35—C361.390 (17)
C9—H90.9300C35—H350.9300
C45—H450.9300C14—C151.391 (18)
C31—C321.395 (14)C14—H140.9300
C31—C301.397 (13)C15—H150.9300
C41—C421.354 (15)C2—C31.367 (19)
C41—H410.9300C2—C11.367 (18)
C12—C111.364 (15)C2—H20.9300
C12—C131.390 (16)C1—H10.9300
C12—H120.9300C26—H260.9300
C10—C111.480 (14)C3—H30.9300
C42—C431.374 (16)C20—C231.544 (15)
C42—H420.9300C36—H360.9300
C43—C461.493 (17)C23—H23A0.9600
N4—C241.344 (13)C23—H23B0.9600
N4—C281.370 (13)C23—H23C0.9600
Cg1···Cg2i3.582 (6)Cg1···Cg33.600 (6)
C20—C19—C18122.7 (13)C22—C21—C20118.3 (12)
C20—C19—H19118.7C22—C21—H21120.9
C18—C19—H19118.7C20—C21—H21120.9
C33—N3—C29121.4 (8)C36—C37—C38121.6 (11)
C33—N3—Pt2119.2 (7)C36—C37—H37119.2
C29—N3—Pt2119.4 (6)C38—C37—H37119.2
N3—Pt2—C3982.1 (4)C37—C38—C39121.1 (11)
N3—Pt2—N479.8 (3)C37—C38—H38119.4
C39—Pt2—N4161.8 (4)C39—C38—H38119.4
N3—Pt2—Cl2179.3 (2)C35—C34—C39121.0 (9)
C39—Pt2—Cl297.7 (3)C35—C34—C33124.3 (9)
N4—Pt2—Cl2100.5 (2)C39—C34—C33114.7 (9)
N1—Pt1—C1682.2 (4)C29—C30—C31121.0 (9)
N1—Pt1—N279.6 (3)C29—C30—H30119.5
C16—Pt1—N2161.8 (3)C31—C30—H30119.5
N1—Pt1—Cl1177.9 (3)C43—C46—H46A109.5
C16—Pt1—Cl199.3 (3)C43—C46—H46B109.5
N2—Pt1—Cl198.9 (2)H46A—C46—H46B109.5
C6—N1—C10121.6 (7)C43—C46—H46C109.5
C6—N1—Pt1119.9 (6)H46A—C46—H46C109.5
C10—N1—Pt1118.5 (6)H46B—C46—H46C109.5
C45—C44—C43120.7 (10)C12—C11—C16124.1 (9)
C45—C44—H44119.7C12—C11—C10121.8 (9)
C43—C44—H44119.7C16—C11—C10114.1 (8)
C38—C39—C34116.9 (10)N1—C6—C7120.4 (9)
C38—C39—Pt2131.6 (8)N1—C6—C5112.7 (8)
C34—C39—Pt2111.6 (8)C7—C6—C5126.9 (9)
C7—C8—C9118.6 (8)C19—C18—C17120.9 (12)
C7—C8—C17120.2 (9)C19—C18—H18119.6
C9—C8—C17121.3 (9)C17—C18—H18119.6
C26—C27—C28120.6 (11)N4—C28—C27120.5 (8)
C26—C27—H27119.7N4—C28—C29116.3 (9)
C28—C27—H27119.7C27—C28—C29123.2 (10)
C22—C17—C18116.6 (9)C17—C22—C21122.8 (12)
C22—C17—C8122.1 (9)C17—C22—H22118.6
C18—C17—C8121.3 (9)C21—C22—H22118.6
C45—C40—C41116.5 (9)C6—C7—C8120.0 (9)
C45—C40—C31121.9 (9)C6—C7—H7120.0
C41—C40—C31121.6 (8)C8—C7—H7120.0
N3—C33—C32120.5 (9)N4—C24—C25122.1 (11)
N3—C33—C34112.5 (8)N4—C24—H24118.9
C32—C33—C34127.0 (9)C25—C24—H24118.9
C8—C9—C10120.6 (9)C14—C13—C12119.7 (11)
C8—C9—H9119.7C14—C13—H13120.1
C10—C9—H9119.7C12—C13—H13120.1
C40—C45—C44121.7 (10)C5—C4—C3118.9 (10)
C40—C45—H45119.1C5—C4—H4120.6
C44—C45—H45119.1C3—C4—H4120.6
C32—C31—C30117.8 (8)C36—C35—C34119.7 (11)
C32—C31—C40121.2 (8)C36—C35—H35120.2
C30—C31—C40120.9 (8)C34—C35—H35120.2
C42—C41—C40121.4 (9)N2—C5—C4120.9 (9)
C42—C41—H41119.3N2—C5—C6115.7 (8)
C40—C41—H41119.3C4—C5—C6123.3 (9)
C11—C12—C13118.3 (11)C13—C14—C15121.4 (10)
C11—C12—H12120.9C13—C14—H14119.3
C13—C12—H12120.9C15—C14—H14119.3
N1—C10—C9118.8 (8)C16—C15—C14120.9 (10)
N1—C10—C11112.1 (8)C16—C15—H15119.5
C9—C10—C11129.1 (9)C14—C15—H15119.5
C41—C42—C43122.0 (11)C3—C2—C1119.1 (11)
C41—C42—H42119.0C3—C2—H2120.5
C43—C42—H42119.0C1—C2—H2120.5
C42—C43—C44117.5 (10)N2—C1—C2122.0 (11)
C42—C43—C46122.1 (12)N2—C1—H1119.0
C44—C43—C46120.4 (11)C2—C1—H1119.0
C24—N4—C28118.4 (9)C27—C26—C25117.1 (11)
C24—N4—Pt2129.8 (8)C27—C26—H26121.4
C28—N4—Pt2111.6 (6)C25—C26—H26121.4
C33—C32—C31120.0 (8)C2—C3—C4119.5 (11)
C33—C32—H32120.0C2—C3—H3120.3
C31—C32—H32120.0C4—C3—H3120.3
C30—C29—N3119.2 (7)C19—C20—C21118.7 (10)
C30—C29—C28128.0 (10)C19—C20—C23122.9 (13)
N3—C29—C28112.8 (9)C21—C20—C23118.4 (12)
C24—C25—C26121.1 (10)C37—C36—C35119.6 (11)
C24—C25—H25119.4C37—C36—H36120.2
C26—C25—H25119.4C35—C36—H36120.2
C1—N2—C5119.6 (9)C20—C23—H23A109.5
C1—N2—Pt1128.3 (7)C20—C23—H23B109.5
C5—N2—Pt1112.1 (6)H23A—C23—H23B109.5
C15—C16—C11115.5 (9)C20—C23—H23C109.5
C15—C16—Pt1131.2 (8)H23A—C23—H23C109.5
C11—C16—Pt1113.1 (7)H23B—C23—H23C109.5

Symmetry codes: (i) x+1, y, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···Cg4ii0.932.873.650 (14)142
C14—H14···Cg5iii0.932.713.445 (14)136

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2424).

References

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  • Catalano, V. J., Benett, B. L., Yson, R. L. & Noll, B. C. (2000). J. Am. Chem. Soc.122, 10056–10057.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  • Kubicki, M., Borowiak, T., Dutkiewicz, G., Souhassou, M., Jelsch, C. & Lecomte, C. (2002). J. Phys. Chem. B, 106, 3706–3714.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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