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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1341–m1342.
Published online 2010 September 30. doi:  10.1107/S1600536810038134
PMCID: PMC2983250

Chlorido{N 2,N 6-dibenzyl-N 2,N 6-bis­[(diphenyl­phosphan­yl)meth­yl]pyridine-2,6-diamine}­methyl­platinum(II)

Abstract

In the title mononuclear complex, [Pt(CH3)Cl(C45H41N3P2)], the pyridine-2,6-diamine ligand can be viewed as a centrosymmetric motif having two pendant N-benzyl-N-[(diphenyl­phosphan­yl)meth­yl] arms, the two P atoms of which chelate to the PtII ion, forming a ten-membered metallocycle. A distorted square-planar coordination geometry around the PtII atom is completed by a methyl ligand and a chloride ion. The packing between the mononuclear units is achieved through C—H(...)π inter­actions, which link the mol­ecules into chains along the c axis.

Related literature

For coordination complexes with hemilabile tridentate ligands with PXP (X = C, N, O, S, and As) donor sets, see: Ainscough et al. (2004 [triangle]); Song et al. (2002 [triangle]); Kunz et al. (2010 [triangle]); Wang et al. (2010 [triangle]); Zhang & Cheng (1996 [triangle]). For a coordination complex of the 2,6-bis­(N-benzyl-N-diphenyl­phosphinomethyl­amino)­pyri­dine ligand, see: Li et al. (2005 [triangle]). For C—H(benzene)(...)π inter­actions, see: Umezawa et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1341-scheme1.jpg

Experimental

Crystal data

  • [Pt(CH3)Cl(C45H41N3P2)]
  • M r = 931.32
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1341-efi1.jpg
  • a = 15.3515 (9) Å
  • b = 15.9294 (10) Å
  • c = 16.5197 (10) Å
  • V = 4039.7 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.66 mm−1
  • T = 293 K
  • 0.32 × 0.24 × 0.16 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.640, T max = 1.000
  • 21886 measured reflections
  • 7108 independent reflections
  • 6498 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.050
  • S = 0.97
  • 7108 reflections
  • 479 parameters
  • H-atom parameters constrained
  • Δρmax = 0.74 e Å−3
  • Δρmin = −0.38 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3125 Friedel pairs
  • Flack parameter: −0.010 (4)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2007 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038134/bq2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038134/bq2234Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Science and Technology program, Beijing Municipal Education Commission.

supplementary crystallographic information

Comment

The hemilabile tridentate ligands with PXP (X = C, N, O, S, and As) donor sets have attracted particular attention for their coordinative extensibility and structural diversity with transition metals (Ainscough et al., 2004; Song, et al., 2002; Kunz et al., 2010; Wang, et al., 2010), as well as the catalytic property of their metal complexes (Zhang et al., 1996).

In the present context, we report a new complex of 2,6-bis(N-benzyl-N-diphenylphosphinomethylamino)pyridine ligand (abbreviated as L), namely Pt(L)MeCl, (I). In the title complex, two phosphine atoms of the pendant diphenylphosinomethylamino arms bond to the square-planar coordinated PtII ion at the cis sites, generating a 10-membered ring similar to that of the reported Pt(L)Cl2.CH2Cl2 (Li et al., 2005), as shown in Fig. 1. The mononuclear units are arranged along the c direction and interconnect through C-H(methylene)..π and C—H(benzene)···π interactions (Umezawa et al., 1998) to form a chain. As shown in Fig. 2, the C5i—Hi···Cg1 contact exhibits a C5i···centroid distance of 3.812 (2) Å and a C5i—Hi···centroid angle of 146°, while the C26ii—H(methylene) interaction has a C26ii···centroid separation of 3.807 (2) Å and a C26ii—Hii···centroid angle of 147° [Cg1 presents ring of C15-C20 (benzene), symmetry codes: i -x + 1.5, -y + 1, z + 0.5; ii -x + 1.5, -y + 1, z - 0.5].

Experimental

The 2,6-bis(N-benzyl-N-diphenylphosphinomethylamino)pyridine (L) was synthesized through the procedure as the literature (Li et al., 2005). The solid of Pt(COD)MeCl (0.210 g, 0.60 mmol) was added to the solution of L (0.411 g, 0.6 mmol) in CH2Cl2 (30 ml) and the mixture was stirred for one hour at room temperature. The yellow solvent was removed under vacuum and the title complex was obtained as a yellow powder, the block like crystals of which were obtained after four days by recrystallization from CH2Cl2/n-hexane (0.447 g, 80% yield).

Refinement

The hydrogen atoms were placed in idealized positions and allowed to ride on the relevant carbon atoms, with C—H = 0.93, 0.97 and 0.96 Å for aryl, methylene and methyl hydrogens, respectively. Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The atom-numbering scheme of the title complex I.Displacement ellipsoids are drawn at the 30% probability level and H atoms are omitted for clarity.
Fig. 2.
The C—H(benzene)···π interactions between the mononuclear Pt(L)MeCl units arranged along the c direction. The red-dashed lines indicate the C—H···π interactions, while the ...

Crystal data

[Pt(CH3)Cl(C45H41N3P2)]Z = 4
Mr = 931.32F(000) = 1864
Orthorhombic, P212121Dx = 1.531 Mg m3
Hall symbol: P 2ac 2abMo Kα radiation, λ = 0.71073 Å
a = 15.3515 (9) ŵ = 3.66 mm1
b = 15.9294 (10) ÅT = 293 K
c = 16.5197 (10) ÅBlock, colorless
V = 4039.7 (4) Å30.32 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer7108 independent reflections
Radiation source: fine-focus sealed tube6498 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −15→18
Tmin = 0.640, Tmax = 1.000k = −18→18
21886 measured reflectionsl = −17→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.050w = 1/[σ2(Fo2) + (0.P)2] P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.003
7108 reflectionsΔρmax = 0.74 e Å3
479 parametersΔρmin = −0.38 e Å3
0 restraintsAbsolute structure: Flack (1983), 3125 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.010 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Pt10.442088 (10)0.536151 (10)0.964197 (10)0.03462 (5)
Cl10.33715 (9)0.50166 (8)1.06371 (8)0.0633 (4)
P10.54103 (7)0.57645 (7)0.87509 (7)0.0328 (3)
P20.47428 (6)0.39415 (6)0.96383 (8)0.0344 (2)
N10.5395 (2)0.4046 (2)1.1248 (2)0.0444 (9)
N20.62990 (18)0.47138 (19)1.03402 (19)0.0340 (7)
N30.7081 (2)0.5456 (2)0.93740 (19)0.0386 (9)
C10.4996 (3)0.5651 (2)0.7722 (3)0.0371 (10)
C20.4096 (3)0.5615 (3)0.7627 (3)0.0513 (13)
H20.37390.56670.80790.062*
C30.3728 (3)0.5505 (4)0.6874 (3)0.0627 (15)
H30.31250.54830.68210.075*
C40.4240 (4)0.5428 (4)0.6211 (3)0.0686 (14)
H40.39900.53480.57040.082*
C50.5120 (4)0.5466 (4)0.6290 (3)0.0693 (15)
H50.54690.54180.58320.083*
C60.5504 (3)0.5576 (3)0.7034 (3)0.0568 (13)
H60.61080.56000.70750.068*
C70.5844 (3)0.6819 (2)0.8848 (3)0.0397 (10)
C80.6100 (3)0.7296 (3)0.8197 (3)0.0525 (12)
H80.59690.71230.76740.063*
C90.6558 (4)0.8044 (3)0.8325 (4)0.0717 (17)
H90.67390.83650.78860.086*
C100.6739 (4)0.8304 (3)0.9096 (5)0.0745 (18)
H100.70400.88030.91800.089*
C110.6482 (3)0.7836 (3)0.9737 (4)0.0709 (16)
H110.66130.80151.02590.085*
C120.6028 (3)0.7101 (3)0.9627 (3)0.0506 (11)
H120.58440.67911.00720.061*
C130.6476 (2)0.5207 (3)0.8754 (2)0.0387 (10)
H13A0.63660.46100.88110.046*
H13B0.67510.52910.82310.046*
C140.7841 (3)0.5946 (3)0.9142 (3)0.0430 (11)
H14A0.79080.64080.95190.052*
H14B0.77420.61840.86090.052*
C150.8671 (3)0.5450 (3)0.9125 (2)0.0427 (10)
C160.9462 (3)0.5834 (3)0.9267 (3)0.0582 (12)
H160.94730.63990.94080.070*
C171.0234 (3)0.5404 (5)0.9205 (3)0.0762 (16)
H171.07610.56740.93030.091*
C181.0216 (4)0.4565 (6)0.8994 (4)0.087 (2)
H181.07360.42690.89430.104*
C190.9465 (5)0.4176 (4)0.8865 (3)0.0764 (17)
H190.94610.36080.87350.092*
C200.8677 (3)0.4615 (4)0.8924 (3)0.0580 (12)
H200.81540.43370.88270.070*
C210.6965 (2)0.5226 (2)1.0174 (2)0.0369 (10)
C220.7514 (3)0.5538 (3)1.0782 (3)0.0425 (11)
H220.79950.58681.06560.051*
C230.7319 (3)0.5341 (3)1.1561 (3)0.0480 (11)
H230.76770.55381.19740.058*
C240.6610 (3)0.4863 (3)1.1754 (3)0.0462 (12)
H240.64660.47521.22900.055*
C250.6110 (3)0.4545 (3)1.1117 (2)0.0370 (9)
C260.4923 (3)0.4046 (3)1.2028 (3)0.0496 (12)
H26A0.43240.42121.19330.060*
H26B0.51850.44611.23820.060*
C270.4930 (3)0.3215 (3)1.2446 (3)0.0458 (12)
C280.5690 (4)0.2808 (3)1.2634 (3)0.0626 (14)
H280.62210.30461.24890.075*
C290.5676 (5)0.2044 (4)1.3036 (3)0.0746 (16)
H290.61990.17741.31510.089*
C300.4926 (6)0.1689 (4)1.3263 (4)0.086 (2)
H300.49270.11781.35350.104*
C310.4153 (5)0.2087 (4)1.3089 (4)0.090 (2)
H310.36280.18471.32490.108*
C320.4153 (4)0.2852 (3)1.2672 (3)0.0660 (15)
H320.36290.31151.25480.079*
C330.5016 (3)0.3507 (3)1.0645 (3)0.0434 (11)
H33A0.44860.32741.08720.052*
H33B0.54140.30421.05610.052*
C340.3790 (3)0.3301 (3)0.9376 (3)0.0412 (11)
C350.3074 (3)0.3654 (3)0.9016 (3)0.0549 (13)
H350.30560.42320.89360.066*
C360.2383 (3)0.3169 (4)0.8772 (4)0.0724 (16)
H360.19050.34140.85210.087*
C370.2406 (4)0.2315 (4)0.8903 (4)0.0698 (16)
H370.19360.19840.87470.084*
C380.3104 (4)0.1956 (3)0.9257 (3)0.0635 (15)
H380.31160.13790.93440.076*
C390.3789 (3)0.2437 (3)0.9485 (3)0.0508 (12)
H390.42710.21820.97220.061*
C400.5494 (3)0.3437 (2)0.8929 (3)0.0371 (10)
C410.5277 (3)0.3486 (3)0.8112 (3)0.0501 (12)
H410.47610.37430.79520.060*
C420.5840 (4)0.3148 (3)0.7537 (3)0.0637 (15)
H420.56960.31830.69910.076*
C430.6587 (4)0.2773 (4)0.7757 (5)0.0791 (19)
H430.69550.25530.73640.095*
C440.6806 (4)0.2714 (3)0.8551 (5)0.0746 (18)
H440.73230.24500.87000.089*
C450.6265 (3)0.3044 (3)0.9140 (3)0.0541 (13)
H450.64200.30020.96830.065*
C460.3910 (2)0.66327 (19)0.9668 (3)0.0264 (8)
H46A0.40090.68741.01930.040*
H46B0.32960.66210.95580.040*
H46C0.41990.69650.92640.040*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pt10.03517 (8)0.03335 (7)0.03532 (8)0.00224 (8)0.00569 (8)0.00014 (9)
Cl10.0630 (8)0.0570 (6)0.0698 (9)0.0094 (6)0.0314 (7)0.0093 (6)
P10.0343 (7)0.0330 (5)0.0310 (6)−0.0013 (4)0.0000 (5)0.0017 (5)
P20.0359 (5)0.0318 (5)0.0354 (6)−0.0028 (4)0.0006 (6)−0.0013 (6)
N10.063 (3)0.044 (2)0.0255 (19)−0.0086 (18)0.0047 (17)−0.0020 (16)
N20.0392 (17)0.0321 (16)0.0306 (17)−0.0007 (15)−0.0022 (16)0.002 (2)
N30.0324 (18)0.046 (2)0.037 (2)−0.0084 (17)0.0007 (14)0.0068 (18)
C10.048 (3)0.033 (2)0.031 (2)−0.0003 (19)−0.005 (2)0.0005 (18)
C20.047 (3)0.058 (3)0.049 (3)−0.001 (2)−0.001 (2)−0.001 (2)
C30.048 (3)0.080 (4)0.060 (3)−0.005 (3)−0.016 (3)−0.011 (3)
C40.078 (4)0.084 (4)0.044 (3)−0.002 (3)−0.016 (3)−0.007 (3)
C50.080 (4)0.095 (4)0.033 (3)−0.006 (4)0.002 (3)−0.008 (3)
C60.053 (3)0.080 (4)0.037 (3)−0.003 (3)0.001 (3)0.002 (2)
C70.038 (3)0.033 (2)0.047 (3)−0.0015 (18)0.001 (2)−0.001 (2)
C80.057 (3)0.046 (3)0.054 (3)−0.006 (2)−0.004 (3)0.008 (2)
C90.066 (4)0.047 (3)0.102 (5)−0.012 (3)0.002 (4)0.027 (3)
C100.063 (4)0.044 (3)0.117 (6)−0.016 (3)−0.016 (4)−0.006 (3)
C110.076 (4)0.051 (3)0.085 (4)−0.005 (3)−0.016 (4)−0.017 (3)
C120.054 (3)0.042 (2)0.055 (3)−0.002 (2)−0.002 (3)−0.007 (3)
C130.040 (2)0.041 (3)0.036 (2)−0.0030 (19)0.0029 (19)0.005 (2)
C140.039 (2)0.044 (3)0.046 (3)−0.005 (2)0.000 (2)0.007 (2)
C150.041 (2)0.056 (3)0.032 (2)−0.003 (2)0.0002 (18)0.009 (2)
C160.048 (3)0.073 (3)0.053 (3)−0.013 (3)−0.001 (3)0.011 (2)
C170.042 (3)0.115 (5)0.072 (4)0.007 (4)0.001 (3)0.018 (4)
C180.061 (4)0.135 (7)0.065 (4)0.044 (5)0.016 (3)0.018 (5)
C190.096 (5)0.080 (4)0.054 (3)0.035 (4)0.016 (4)0.004 (3)
C200.065 (3)0.060 (3)0.049 (3)0.006 (3)−0.004 (2)0.002 (3)
C210.038 (2)0.029 (2)0.044 (3)0.0050 (18)−0.0004 (18)−0.0015 (19)
C220.040 (2)0.041 (3)0.046 (3)−0.0045 (19)−0.008 (2)−0.004 (2)
C230.051 (3)0.046 (2)0.048 (3)0.005 (3)−0.015 (2)−0.008 (3)
C240.062 (3)0.045 (3)0.032 (2)0.004 (2)−0.007 (2)−0.003 (2)
C250.045 (2)0.030 (2)0.035 (2)0.003 (2)−0.0004 (19)−0.001 (2)
C260.062 (3)0.051 (3)0.036 (3)−0.002 (2)0.013 (2)0.001 (2)
C270.062 (3)0.048 (3)0.027 (2)−0.012 (2)0.008 (2)0.002 (2)
C280.069 (4)0.065 (3)0.054 (3)0.000 (3)0.008 (3)0.005 (3)
C290.104 (5)0.070 (4)0.049 (3)0.013 (4)0.003 (4)0.011 (3)
C300.148 (7)0.061 (4)0.051 (4)−0.014 (4)0.000 (4)0.019 (3)
C310.107 (6)0.079 (4)0.084 (5)−0.041 (4)0.015 (4)0.018 (4)
C320.070 (4)0.073 (4)0.054 (3)−0.014 (3)−0.002 (3)0.007 (3)
C330.053 (3)0.037 (2)0.040 (3)−0.012 (2)−0.001 (2)0.004 (2)
C340.034 (2)0.048 (3)0.042 (3)−0.004 (2)0.008 (2)−0.006 (2)
C350.043 (3)0.050 (3)0.071 (4)−0.003 (2)−0.006 (3)−0.006 (3)
C360.039 (3)0.085 (4)0.094 (5)−0.004 (3)−0.008 (3)−0.014 (4)
C370.055 (4)0.078 (4)0.077 (4)−0.034 (3)0.008 (3)−0.020 (3)
C380.070 (4)0.052 (3)0.068 (4)−0.022 (3)0.002 (3)−0.008 (3)
C390.046 (3)0.041 (2)0.066 (4)−0.009 (2)−0.009 (2)0.001 (2)
C400.034 (2)0.034 (2)0.043 (3)−0.001 (2)0.000 (2)−0.0075 (19)
C410.048 (3)0.050 (3)0.052 (3)−0.014 (2)0.008 (2)−0.010 (2)
C420.066 (4)0.070 (3)0.055 (3)−0.020 (3)0.016 (3)−0.022 (3)
C430.066 (4)0.071 (4)0.100 (5)−0.009 (3)0.030 (4)−0.039 (4)
C440.050 (3)0.061 (4)0.112 (6)0.013 (3)0.012 (4)−0.019 (4)
C450.048 (3)0.049 (3)0.065 (3)0.003 (2)−0.001 (3)−0.004 (3)
C460.0311 (19)0.0184 (16)0.030 (2)0.0069 (14)0.011 (2)−0.0014 (18)

Geometric parameters (Å, °)

Pt1—C462.172 (3)C18—H180.9300
Pt1—P12.2105 (11)C19—C201.400 (7)
Pt1—P22.3153 (10)C19—H190.9300
Pt1—Cl12.3663 (12)C20—H200.9300
P1—C71.814 (4)C21—C221.402 (6)
P1—C11.824 (4)C22—C231.358 (6)
P1—C131.862 (4)C22—H220.9300
P2—C401.830 (4)C23—C241.366 (6)
P2—C341.836 (4)C23—H230.9300
P2—C331.850 (4)C24—C251.397 (6)
N1—C251.373 (5)C24—H240.9300
N1—C331.438 (5)C26—C271.493 (6)
N1—C261.478 (5)C26—H26A0.9700
N2—C211.336 (5)C26—H26B0.9700
N2—C251.343 (5)C27—C281.370 (7)
N3—C211.383 (5)C27—C321.377 (7)
N3—C131.439 (5)C28—C291.386 (7)
N3—C141.455 (5)C28—H280.9300
C1—C61.384 (6)C29—C301.336 (9)
C1—C21.390 (6)C29—H290.9300
C2—C31.378 (6)C30—C311.377 (9)
C2—H20.9300C30—H300.9300
C3—C41.354 (7)C31—C321.400 (8)
C3—H30.9300C31—H310.9300
C4—C51.359 (7)C32—H320.9300
C4—H40.9300C33—H33A0.9700
C5—C61.374 (6)C33—H33B0.9700
C5—H50.9300C34—C351.370 (6)
C6—H60.9300C34—C391.387 (6)
C7—C81.375 (6)C35—C361.373 (7)
C7—C121.390 (7)C35—H350.9300
C8—C91.400 (7)C36—C371.377 (8)
C8—H80.9300C36—H360.9300
C9—C101.368 (8)C37—C381.349 (8)
C9—H90.9300C37—H370.9300
C10—C111.353 (8)C38—C391.354 (6)
C10—H100.9300C38—H380.9300
C11—C121.376 (6)C39—H390.9300
C11—H110.9300C40—C451.384 (6)
C12—H120.9300C40—C411.392 (6)
C13—H13A0.9700C41—C421.393 (7)
C13—H13B0.9700C41—H410.9300
C14—C151.499 (6)C42—C431.343 (8)
C14—H14A0.9700C42—H420.9300
C14—H14B0.9700C43—C441.358 (8)
C15—C201.371 (7)C43—H430.9300
C15—C161.380 (6)C44—C451.384 (7)
C16—C171.371 (7)C44—H440.9300
C16—H160.9300C45—H450.9300
C17—C181.382 (10)C46—H46A0.9600
C17—H170.9300C46—H46B0.9600
C18—C191.327 (9)C46—H46C0.9600
C46—Pt1—P189.45 (10)C15—C20—H20119.8
C46—Pt1—P2171.11 (9)C19—C20—H20119.8
P1—Pt1—P297.77 (4)N2—C21—N3117.2 (4)
C46—Pt1—Cl187.54 (10)N2—C21—C22121.9 (4)
P1—Pt1—Cl1176.26 (4)N3—C21—C22120.8 (4)
P2—Pt1—Cl185.43 (4)C23—C22—C21117.7 (4)
C7—P1—C1107.6 (2)C23—C22—H22121.2
C7—P1—C1396.84 (18)C21—C22—H22121.2
C1—P1—C13105.16 (19)C22—C23—C24121.7 (4)
C7—P1—Pt1117.51 (15)C22—C23—H23119.1
C1—P1—Pt1110.60 (15)C24—C23—H23119.1
C13—P1—Pt1117.62 (13)C23—C24—C25117.6 (4)
C40—P2—C3496.12 (19)C23—C24—H24121.2
C40—P2—C33105.6 (2)C25—C24—H24121.2
C34—P2—C33100.7 (2)N2—C25—N1116.1 (3)
C40—P2—Pt1124.42 (14)N2—C25—C24121.9 (4)
C34—P2—Pt1111.95 (14)N1—C25—C24122.0 (4)
C33—P2—Pt1114.30 (15)N1—C26—C27113.6 (4)
C25—N1—C33124.0 (3)N1—C26—H26A108.9
C25—N1—C26122.0 (3)C27—C26—H26A108.9
C33—N1—C26114.0 (4)N1—C26—H26B108.9
C21—N2—C25119.0 (3)C27—C26—H26B108.9
C21—N3—C13121.6 (3)H26A—C26—H26B107.7
C21—N3—C14119.9 (3)C28—C27—C32118.6 (5)
C13—N3—C14118.6 (3)C28—C27—C26122.0 (5)
C6—C1—C2117.7 (4)C32—C27—C26119.4 (5)
C6—C1—P1125.2 (4)C27—C28—C29120.7 (6)
C2—C1—P1117.1 (4)C27—C28—H28119.7
C3—C2—C1120.9 (5)C29—C28—H28119.7
C3—C2—H2119.5C30—C29—C28121.3 (7)
C1—C2—H2119.5C30—C29—H29119.3
C4—C3—C2120.3 (5)C28—C29—H29119.3
C4—C3—H3119.9C29—C30—C31119.3 (6)
C2—C3—H3119.9C29—C30—H30120.4
C3—C4—C5119.7 (5)C31—C30—H30120.4
C3—C4—H4120.2C30—C31—C32120.2 (6)
C5—C4—H4120.2C30—C31—H31119.9
C4—C5—C6121.3 (5)C32—C31—H31119.9
C4—C5—H5119.4C27—C32—C31119.9 (6)
C6—C5—H5119.4C27—C32—H32120.0
C5—C6—C1120.2 (5)C31—C32—H32120.0
C5—C6—H6119.9N1—C33—P2119.4 (3)
C1—C6—H6119.9N1—C33—H33A107.5
C8—C7—C12119.2 (4)P2—C33—H33A107.5
C8—C7—P1123.2 (4)N1—C33—H33B107.5
C12—C7—P1117.1 (3)P2—C33—H33B107.5
C7—C8—C9119.7 (5)H33A—C33—H33B107.0
C7—C8—H8120.1C35—C34—C39117.6 (4)
C9—C8—H8120.1C35—C34—P2120.9 (3)
C10—C9—C8120.0 (6)C39—C34—P2121.4 (3)
C10—C9—H9120.0C34—C35—C36121.0 (5)
C8—C9—H9120.0C34—C35—H35119.5
C11—C10—C9120.2 (5)C36—C35—H35119.5
C11—C10—H10119.9C35—C36—C37119.4 (5)
C9—C10—H10119.9C35—C36—H36120.3
C10—C11—C12120.9 (6)C37—C36—H36120.3
C10—C11—H11119.6C38—C37—C36120.5 (5)
C12—C11—H11119.6C38—C37—H37119.8
C11—C12—C7120.0 (5)C36—C37—H37119.8
C11—C12—H12120.0C37—C38—C39119.8 (5)
C7—C12—H12120.0C37—C38—H38120.1
N3—C13—P1115.9 (3)C39—C38—H38120.1
N3—C13—H13A108.3C38—C39—C34121.7 (5)
P1—C13—H13A108.3C38—C39—H39119.1
N3—C13—H13B108.3C34—C39—H39119.1
P1—C13—H13B108.3C45—C40—C41118.3 (4)
H13A—C13—H13B107.4C45—C40—P2125.2 (4)
N3—C14—C15113.8 (3)C41—C40—P2116.5 (3)
N3—C14—H14A108.8C40—C41—C42119.5 (5)
C15—C14—H14A108.8C40—C41—H41120.3
N3—C14—H14B108.8C42—C41—H41120.3
C15—C14—H14B108.8C43—C42—C41121.1 (6)
H14A—C14—H14B107.7C43—C42—H42119.5
C20—C15—C16117.7 (4)C41—C42—H42119.5
C20—C15—C14121.4 (4)C42—C43—C44120.3 (6)
C16—C15—C14120.7 (5)C42—C43—H43119.8
C17—C16—C15121.8 (5)C44—C43—H43119.8
C17—C16—H16119.1C43—C44—C45120.3 (6)
C15—C16—H16119.1C43—C44—H44119.9
C16—C17—C18119.0 (6)C45—C44—H44119.9
C16—C17—H17120.5C40—C45—C44120.5 (5)
C18—C17—H17120.5C40—C45—H45119.7
C19—C18—C17120.6 (6)C44—C45—H45119.7
C19—C18—H18119.7Pt1—C46—H46A109.5
C17—C18—H18119.7Pt1—C46—H46B109.5
C18—C19—C20120.5 (6)H46A—C46—H46B109.5
C18—C19—H19119.8Pt1—C46—H46C109.5
C20—C19—H19119.8H46A—C46—H46C109.5
C15—C20—C19120.4 (5)H46B—C46—H46C109.5
C46—Pt1—P1—C734.8 (2)C14—N3—C21—N2−174.1 (3)
P2—Pt1—P1—C7−150.40 (16)C13—N3—C21—C22−174.0 (4)
C46—Pt1—P1—C1−89.30 (18)C14—N3—C21—C227.4 (6)
P2—Pt1—P1—C185.50 (14)N2—C21—C22—C23−3.8 (6)
C46—Pt1—P1—C13149.89 (18)N3—C21—C22—C23174.7 (4)
P2—Pt1—P1—C13−35.31 (15)C21—C22—C23—C24−0.5 (7)
P1—Pt1—P2—C40−8.50 (19)C22—C23—C24—C253.0 (7)
Cl1—Pt1—P2—C40173.44 (18)C21—N2—C25—N1177.0 (3)
P1—Pt1—P2—C34−123.05 (15)C21—N2—C25—C24−2.6 (6)
Cl1—Pt1—P2—C3458.88 (15)C33—N1—C25—N219.7 (5)
P1—Pt1—P2—C33123.31 (17)C26—N1—C25—N2−158.0 (4)
Cl1—Pt1—P2—C33−54.75 (17)C33—N1—C25—C24−160.7 (4)
C7—P1—C1—C672.9 (4)C26—N1—C25—C2421.6 (6)
C13—P1—C1—C6−29.6 (4)C23—C24—C25—N2−1.5 (6)
Pt1—P1—C1—C6−157.6 (4)C23—C24—C25—N1178.9 (4)
C7—P1—C1—C2−108.8 (4)C25—N1—C26—C27−118.3 (5)
C13—P1—C1—C2148.7 (3)C33—N1—C26—C2763.9 (5)
Pt1—P1—C1—C220.8 (4)N1—C26—C27—C2856.3 (6)
C6—C1—C2—C30.4 (7)N1—C26—C27—C32−125.6 (5)
P1—C1—C2—C3−178.1 (4)C32—C27—C28—C290.6 (8)
C1—C2—C3—C40.1 (8)C26—C27—C28—C29178.7 (4)
C2—C3—C4—C5−0.5 (9)C27—C28—C29—C30−1.0 (8)
C3—C4—C5—C60.5 (10)C28—C29—C30—C310.3 (10)
C4—C5—C6—C1−0.1 (9)C29—C30—C31—C320.7 (10)
C2—C1—C6—C5−0.4 (7)C28—C27—C32—C310.4 (8)
P1—C1—C6—C5177.9 (4)C26—C27—C32—C31−177.8 (5)
C1—P1—C7—C8−21.8 (4)C30—C31—C32—C27−1.0 (9)
C13—P1—C7—C886.5 (4)C25—N1—C33—P2−51.3 (5)
Pt1—P1—C7—C8−147.4 (3)C26—N1—C33—P2126.5 (4)
C1—P1—C7—C12166.9 (3)C40—P2—C33—N1112.4 (4)
C13—P1—C7—C12−84.7 (4)C34—P2—C33—N1−148.1 (4)
Pt1—P1—C7—C1241.4 (4)Pt1—P2—C33—N1−27.9 (4)
C12—C7—C8—C91.5 (7)C40—P2—C34—C35−114.5 (4)
P1—C7—C8—C9−169.5 (4)C33—P2—C34—C35138.4 (4)
C7—C8—C9—C10−0.9 (8)Pt1—P2—C34—C3516.6 (4)
C8—C9—C10—C110.4 (9)C40—P2—C34—C3961.3 (4)
C9—C10—C11—C12−0.7 (9)C33—P2—C34—C39−45.8 (4)
C10—C11—C12—C71.4 (8)Pt1—P2—C34—C39−167.7 (3)
C8—C7—C12—C11−1.8 (7)C39—C34—C35—C36−0.1 (8)
P1—C7—C12—C11169.8 (4)P2—C34—C35—C36175.8 (4)
C21—N3—C13—P173.8 (5)C34—C35—C36—C371.0 (9)
C14—N3—C13—P1−107.6 (4)C35—C36—C37—C38−1.0 (9)
C7—P1—C13—N347.1 (3)C36—C37—C38—C390.0 (9)
C1—P1—C13—N3157.5 (3)C37—C38—C39—C340.9 (8)
Pt1—P1—C13—N3−78.9 (3)C35—C34—C39—C38−0.8 (7)
C21—N3—C14—C1574.5 (5)P2—C34—C39—C38−176.8 (4)
C13—N3—C14—C15−104.2 (4)C34—P2—C40—C45−121.8 (4)
N3—C14—C15—C2032.0 (6)C33—P2—C40—C45−18.9 (4)
N3—C14—C15—C16−151.7 (4)Pt1—P2—C40—C45116.2 (4)
C20—C15—C16—C170.6 (6)C34—P2—C40—C4160.7 (4)
C14—C15—C16—C17−175.9 (5)C33—P2—C40—C41163.6 (3)
C15—C16—C17—C180.0 (8)Pt1—P2—C40—C41−61.2 (4)
C16—C17—C18—C19−1.0 (9)C45—C40—C41—C42−0.5 (6)
C17—C18—C19—C201.3 (9)P2—C40—C41—C42177.2 (3)
C16—C15—C20—C19−0.2 (6)C40—C41—C42—C430.2 (7)
C14—C15—C20—C19176.2 (4)C41—C42—C43—C440.3 (9)
C18—C19—C20—C15−0.7 (8)C42—C43—C44—C45−0.4 (9)
C25—N2—C21—N3−173.3 (4)C41—C40—C45—C440.3 (7)
C25—N2—C21—C225.2 (5)P2—C40—C45—C44−177.1 (4)
C13—N3—C21—N24.5 (6)C43—C44—C45—C400.1 (8)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C15–C20 benzene ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg1i0.933.003.812 (2)146
C26—H26B···Cg1ii0.972.963.807 (2)147

Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+3/2, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2234).

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