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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1297–m1298.
Published online 2009 October 3. doi:  10.1107/S1600536809037982
PMCID: PMC2970952

cis-Bis[(1-adamantylmeth­yl)amine-κN]­dichloridoplatinum(II) N,N-dimethyl­formamide solvate

Abstract

The asymmetric unit of the title compound {systematic name: cis-dichloridobis[(3,7-dimethylbicyclo­[3.3.1]non-1-ylmeth­yl)­amine-κN]platinum(II) N,N-dimethyl­formamide solvate}, [PtCl2(C11H19N)2]·C3H7NO, consists of two metrically similar Pt complexes and two dimethyl­formamide solvent mol­ecules. Each PtII center is coordinated by the amine groups of two (1-adamantylmeth­yl)amine ligands and two Cl atoms in a cis-square-planar arrangement. The PtII centers lie slightly outside [0.031 (4) and 0.038 (4) Å] the coordination planes. The N—Pt—N and Cl—Pt—Cl angles [92.1 (4)–92.30 (11)°] are slightly more open than the N—Pt—Cl angles [87.3 (3)–88.3 (3)°]. N—H(...)O and N—H(...)Cl inter­molecular hydrogen bonds are observed, forming two discrete pairs of complexes and solvent mol­ecules.

Related literature

For the anti­viral and anti­tumor activity of Pt complexes with polycyclic cages such as adamantamine, see: Hay et al. (1985 [triangle]); Ho et al. (1972 [triangle]); Widell et al. (1986 [triangle]). The synthesis and spectroscopic characterization of the title compound is described by Rochon et al. (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1297-scheme1.jpg

Experimental

Crystal data

  • [PtCl2(C11H19N)2]·C3H7NO
  • M r = 669.63
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1297-efi1.jpg
  • a = 12.299 (3) Å
  • b = 14.035 (4) Å
  • c = 15.644 (4) Å
  • α = 81.137 (3)°
  • β = 82.323 (3)°
  • γ = 89.292 (3)°
  • V = 2644.3 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.53 mm−1
  • T = 200 K
  • 0.35 × 0.29 × 0.23 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.151, T max = 0.281
  • 26513 measured reflections
  • 9285 independent reflections
  • 5724 reflections with I > 2σ(I)
  • R int = 0.099

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.152
  • S = 0.97
  • 9285 reflections
  • 581 parameters
  • H-atom parameters constrained
  • Δρmax = 7.80 e Å−3
  • Δρmin = −2.82 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: 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 publCIF (Westrip, 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/S1600536809037982/hy2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037982/hy2221Isup2.hkl

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

Acknowledgments

The authors are grateful to the Natural Sciences and Engineering Research Council of Canada for financial support.

supplementary crystallographic information

Comment

Cisplatin [cis-Pt(NH3)2Cl2] is now a well known antitumor drug, but it has numerous side effects and resistance to the drug is an important problem. Replacement of the NH3 ligand by an amine more compatible to the human system might possibly surmount some of these problems. One such amine is the polycyclic cage molecule adamantanamine, which has been demonstrated to exhibit both antiviral (Hay et al., 1985; Widell et al., 1986) and antitumor activity (Ho et al., 1972). The synthesis and the spectroscopic study of PtII compounds with adamantanamine derivatives have been reported (Rochon et al., 1993).

In the title compound (one of the Pt complex is shown in Fig. 1), the Pt metal center exhibits a cis square-planar geometry formed by two amine groups from (1-adamantylmethyl)amine and two Cl atoms. The Pt centers are slightly outside [0.031 (4) and 0.038 (4) Å] the N2Cl2 planes. The bulky adamantane cycles slightly open the N—Pt—N angles [92.1 (4)°] compared to the N—Pt—Cl angles [87.3 (3)–88.3 (3)°]. However, the Cl—Pt—Cl angles are also opened to the same extent [92.17 (11)–92.30 (11)°]. The Pt—N [2.026 (9)–2.056 (9) Å] and Pt—Cl [2.304 (3)–2.312 (3) Å] are normal as well as all other bond distances and angles.

The asymmetric unit of the title compound is described as two crystallographically independent Pt complexes and two dimethylformamide (DMF) solvent molecules linked by N—H···O hydrogen bonds (Fig. 2) between the amine groups and the O atoms from the DMF molecules. N—H···Cl hydrogen bonds between the amine groups and Cl atoms from symmetry equivalent complexes are also observed, forming discrete pairs of complexes and solvent molecules (Fig. 3).

Experimental

One mmol of K2[PtCl4] and 2 mmol of (1-adamantylmethyl)amine were heated in a DMF solution at 80°C for 3 h. The solution was concentrated, cooled to 0°C and the KCl was filtered off. The mixture was evaporated to dryness and the residue washed with ether, acetone and then with water. After drying, the residue was washed with ether and dried. Yield 68%, dec. 195–225°C, ν(Pt—Cl) IR 341, 325, Raman 334, 325 cm-1, 195Pt NMR -2213 p.p.m. The crystals were recrystalized in DMF for crystallographic studies.

Refinement

H atoms were placed at calculated positions (C—H = 0.95–1.00 Å, N—H = 0.92 Å) and were allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N) for the CH, CH2 and NH2 groups and Uiso(H) = 1.5Ueq(C) for the CH3 groups. The highest residual electron density was found 1.0 Å from Pt2.

Figures

Fig. 1.
A view of one of the crystallographically independent molecules of the title compound. Displacement ellipsoids are shown at the 50% probability level.
Fig. 2.
A view of the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms not participating in hydrogen bonds have been omitted for clarity.
Fig. 3.
The hydrogen bonding pattern in the title compound. H atoms not participating in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y+1, -z+2.]

Crystal data

[PtCl2(C11H19N)2]·C3H7NOZ = 4
Mr = 669.63F(000) = 1344
Triclinic, P1Dx = 1.682 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.299 (3) ÅCell parameters from 6035 reflections
b = 14.035 (4) Åθ = 2.2–26.3°
c = 15.644 (4) ŵ = 5.53 mm1
α = 81.137 (3)°T = 200 K
β = 82.323 (3)°Block, yellow
γ = 89.292 (3)°0.35 × 0.29 × 0.23 mm
V = 2644.3 (12) Å3

Data collection

Bruker SMART APEXII CCD diffractometer9285 independent reflections
Radiation source: normal-focus sealed tube5724 reflections with I > 2σ(I)
graphiteRint = 0.099
[var phi] and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −14→14
Tmin = 0.151, Tmax = 0.281k = −16→16
26513 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0732P)2]
9285 reflections(Δ/σ)max = 0.001
581 parametersΔρmax = 7.80 e Å3
0 restraintsΔρmin = −2.82 e Å3
0 constraints

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

xyzUiso*/Ueq
Pt11.00670 (3)0.12043 (3)0.99942 (3)0.02177 (15)
Pt20.50836 (3)0.38164 (3)0.99668 (3)0.02119 (15)
Cl111.1120 (2)0.0882 (2)1.1116 (2)0.0311 (7)
Cl121.1596 (2)0.1589 (2)0.8970 (2)0.0313 (7)
Cl210.6257 (2)0.3401 (2)1.0995 (2)0.0306 (7)
Cl220.6520 (2)0.4151 (2)0.8854 (2)0.0308 (7)
N110.8725 (7)0.0841 (7)1.0899 (6)0.028 (2)
H11A0.81250.08351.06060.034*
H11B0.88180.02201.11680.034*
N120.9139 (7)0.1428 (6)0.9006 (6)0.024 (2)
H12A0.93340.09710.86510.029*
H12B0.84210.13020.92470.029*
N210.3800 (7)0.3594 (7)1.0955 (6)0.025 (2)
H21A0.38610.40461.13150.030*
H21B0.31650.37281.07100.030*
N220.4049 (7)0.4215 (7)0.9047 (6)0.025 (2)
H22A0.33530.42610.93360.030*
H22B0.42550.48220.87640.030*
C110.8455 (9)0.1455 (8)1.1597 (8)0.026 (3)
H11C0.80830.20421.13470.031*
H11D0.91510.16641.17670.031*
C120.7745 (8)0.0994 (8)1.2407 (8)0.027 (3)
C130.8333 (10)0.0124 (9)1.2863 (9)0.037 (3)
H13A0.8459−0.03711.24740.044*
H13B0.90560.03321.29850.044*
C140.7644 (11)−0.0307 (9)1.3717 (9)0.040 (3)
H140.8035−0.08701.40080.048*
C150.6534 (11)−0.0633 (10)1.3540 (10)0.046 (4)
H15A0.6093−0.09201.40950.055*
H15B0.6633−0.11301.31510.055*
C160.5936 (10)0.0243 (10)1.3106 (9)0.042 (4)
H160.52080.00301.29830.050*
C170.6638 (9)0.0671 (9)1.2227 (8)0.033 (3)
H17A0.67390.01771.18350.040*
H17B0.62540.12271.19340.040*
C180.7575 (9)0.1732 (9)1.3017 (8)0.029 (3)
H18A0.71900.22951.27370.035*
H18B0.82990.19571.31220.035*
C190.7469 (11)0.0470 (10)1.4320 (8)0.042 (3)
H19A0.70210.01981.48750.050*
H19B0.81880.06701.44550.050*
C1100.5759 (10)0.1016 (10)1.3705 (9)0.042 (3)
H11E0.52990.07531.42570.051*
H11F0.53820.15791.34170.051*
C1110.6906 (10)0.1326 (10)1.3894 (9)0.037 (3)
H1110.68180.18321.42840.044*
C1120.9164 (8)0.2395 (8)0.8425 (7)0.025 (3)
H11G0.99350.26250.82880.030*
H11H0.87490.28600.87550.030*
C1130.8697 (9)0.2402 (8)0.7573 (8)0.028 (3)
C1140.7502 (8)0.2058 (8)0.7745 (8)0.026 (3)
H11I0.70630.24720.81170.031*
H11J0.74570.13870.80570.031*
C1150.7041 (10)0.2106 (9)0.6873 (9)0.033 (3)
H1150.62590.18810.69910.040*
C1160.7692 (11)0.1466 (10)0.6313 (9)0.046 (4)
H11K0.73880.14960.57550.055*
H11L0.76370.07910.66130.055*
C1170.8906 (11)0.1789 (10)0.6129 (9)0.046 (4)
H1170.93430.13580.57630.055*
C1180.9350 (9)0.1754 (9)0.7006 (8)0.034 (3)
H11M0.93130.10820.73160.040*
H11N1.01290.19610.68980.040*
C1190.8761 (9)0.3426 (9)0.7076 (8)0.033 (3)
H11O0.83440.38620.74380.040*
H11P0.95360.36470.69600.040*
C1200.7092 (10)0.3150 (9)0.6396 (9)0.039 (3)
H12C0.66550.35730.67600.046*
H12D0.67850.31850.58380.046*
C1210.8971 (10)0.2848 (10)0.5652 (9)0.042 (3)
H12E0.97450.30720.55350.051*
H12F0.86830.28860.50870.051*
C1220.8302 (10)0.3481 (9)0.6220 (9)0.036 (3)
H1220.83470.41630.59160.043*
C210.3643 (9)0.2604 (8)1.1537 (7)0.025 (3)
H21C0.33350.21471.12080.030*
H21D0.43690.23591.16720.030*
C220.2910 (9)0.2626 (8)1.2367 (8)0.027 (3)
C230.2776 (9)0.1592 (8)1.2867 (9)0.033 (3)
H23A0.24480.11771.25100.040*
H23B0.35060.13301.29730.040*
C240.2043 (10)0.1579 (10)1.3739 (9)0.036 (3)
H240.19730.09021.40550.043*
C250.0903 (10)0.1947 (9)1.3549 (9)0.041 (3)
H25A0.05920.15291.31850.049*
H25B0.04030.19211.41030.049*
C260.0996 (10)0.2980 (9)1.3072 (9)0.036 (3)
H260.02540.32231.29550.044*
C270.1764 (9)0.3021 (9)1.2207 (8)0.034 (3)
H27A0.18370.36961.19080.041*
H27B0.14440.26341.18230.041*
C280.3380 (10)0.3259 (9)1.2930 (8)0.037 (3)
H28A0.34570.39281.26150.045*
H28B0.41190.30271.30400.045*
C290.2507 (12)0.2204 (10)1.4295 (9)0.050 (4)
H29A0.32280.19521.44370.059*
H29B0.20100.21951.48490.059*
C2100.1496 (14)0.3623 (11)1.3623 (11)0.061 (5)
H21E0.10130.36231.41830.073*
H21F0.15580.42931.33110.073*
C2110.2644 (12)0.3252 (10)1.3804 (8)0.042 (3)
H2110.29710.36701.41680.050*
C2120.3992 (9)0.3588 (9)0.8380 (8)0.031 (3)
H21G0.35330.30190.86500.037*
H21H0.47410.33540.82110.037*
C2130.3545 (8)0.4031 (8)0.7564 (8)0.026 (3)
C2140.3578 (9)0.3252 (9)0.6998 (8)0.031 (3)
H21I0.31220.26970.73100.037*
H21J0.43410.30280.68790.037*
C2150.3149 (10)0.3628 (9)0.6132 (8)0.032 (3)
H2150.31870.31020.57650.039*
C2160.3852 (10)0.4487 (9)0.5644 (8)0.037 (3)
H21K0.46240.42860.55190.044*
H21L0.35820.47280.50820.044*
C2170.3781 (10)0.5276 (9)0.6210 (8)0.035 (3)
H2170.42340.58410.58960.042*
C2180.4229 (9)0.4896 (9)0.7074 (8)0.032 (3)
H21M0.50040.47030.69490.038*
H21N0.42010.54130.74410.038*
C2190.2345 (9)0.4343 (9)0.7761 (8)0.030 (3)
H21O0.23010.48620.81270.036*
H21P0.18940.37900.80850.036*
C2200.1947 (9)0.3931 (10)0.6334 (8)0.037 (3)
H22C0.16450.41560.57830.045*
H22D0.15030.33720.66540.045*
C2210.2589 (11)0.5595 (10)0.6414 (9)0.044 (4)
H22E0.25520.60980.67960.053*
H22F0.23020.58680.58670.053*
C2220.1897 (10)0.4717 (10)0.6873 (8)0.036 (3)
H2220.11160.49190.69980.044*
O10.1953 (6)0.4012 (6)1.0075 (6)0.038 (2)
N10.0234 (8)0.4174 (7)1.0768 (8)0.039 (3)
C10.0970 (10)0.3779 (10)1.0247 (10)0.045 (4)
H10.07290.32710.99780.054*
C3−0.0896 (10)0.3810 (10)1.0928 (12)0.059 (5)
H3A−0.09460.32471.06330.088*
H3B−0.13850.43151.07010.088*
H3C−0.11120.36221.15570.088*
C40.0489 (10)0.4994 (9)1.1196 (10)0.043 (3)
H4A0.12430.52171.09820.064*
H4B0.04160.47891.18290.064*
H4C−0.00210.55211.10620.064*
O20.6969 (6)0.1013 (6)0.9856 (6)0.035 (2)
N20.5460 (7)0.0836 (7)0.9195 (7)0.030 (2)
C20.6048 (9)0.1270 (9)0.9700 (8)0.029 (3)
H20.57320.18030.99480.035*
C50.4361 (9)0.1158 (9)0.9092 (10)0.041 (4)
H5A0.41650.16660.94480.061*
H5B0.38470.06150.92810.061*
H5C0.43230.14120.84770.061*
C60.5893 (9)0.0038 (8)0.8775 (9)0.036 (3)
H6A0.6606−0.01470.89620.055*
H6B0.59840.02310.81410.055*
H6C0.5384−0.05110.89390.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pt10.0202 (2)0.0212 (3)0.0250 (3)0.00066 (18)−0.00497 (19)−0.0053 (2)
Pt20.0207 (2)0.0200 (3)0.0230 (3)0.00236 (18)−0.00192 (19)−0.0046 (2)
Cl110.0281 (15)0.0326 (18)0.0365 (19)0.0051 (12)−0.0141 (13)−0.0093 (15)
Cl120.0241 (14)0.0338 (18)0.0350 (19)0.0010 (12)−0.0014 (12)−0.0045 (14)
Cl210.0255 (14)0.0323 (18)0.0346 (19)0.0047 (12)−0.0092 (13)−0.0031 (14)
Cl220.0259 (14)0.0320 (18)0.0324 (18)0.0024 (12)0.0055 (12)−0.0066 (14)
N110.028 (5)0.028 (6)0.030 (6)−0.001 (4)−0.006 (4)−0.008 (5)
N120.019 (5)0.021 (5)0.031 (6)0.000 (4)0.000 (4)−0.003 (4)
N210.026 (5)0.024 (6)0.024 (6)0.004 (4)0.001 (4)−0.002 (4)
N220.022 (5)0.032 (6)0.022 (6)0.002 (4)0.003 (4)−0.007 (5)
C110.028 (6)0.024 (7)0.026 (7)0.004 (5)−0.006 (5)−0.003 (5)
C120.024 (6)0.023 (7)0.032 (8)0.008 (5)−0.005 (5)0.003 (5)
C130.039 (7)0.034 (8)0.037 (8)0.010 (6)−0.006 (6)−0.002 (6)
C140.063 (9)0.023 (7)0.033 (8)0.019 (6)−0.009 (7)−0.003 (6)
C150.064 (10)0.036 (9)0.036 (9)−0.005 (7)−0.005 (7)−0.001 (7)
C160.041 (8)0.040 (9)0.046 (9)−0.010 (6)−0.006 (7)−0.011 (7)
C170.038 (7)0.040 (8)0.024 (7)−0.003 (6)−0.006 (6)−0.014 (6)
C180.025 (6)0.033 (7)0.032 (8)0.000 (5)−0.008 (5)−0.007 (6)
C190.050 (8)0.060 (10)0.016 (7)0.003 (7)−0.005 (6)−0.011 (7)
C1100.044 (8)0.056 (10)0.026 (8)0.000 (7)−0.004 (6)−0.003 (7)
C1110.038 (7)0.035 (8)0.038 (9)0.008 (6)−0.007 (6)−0.008 (6)
C1120.019 (5)0.030 (7)0.026 (7)0.006 (5)0.000 (5)−0.005 (5)
C1130.023 (6)0.033 (7)0.026 (7)0.004 (5)−0.001 (5)−0.003 (6)
C1140.022 (6)0.029 (7)0.028 (7)−0.002 (5)−0.002 (5)−0.007 (5)
C1150.034 (7)0.034 (8)0.035 (8)0.000 (5)−0.009 (6)−0.012 (6)
C1160.066 (10)0.046 (9)0.031 (9)−0.002 (7)−0.018 (7)−0.013 (7)
C1170.051 (8)0.054 (10)0.033 (9)0.021 (7)−0.003 (6)−0.012 (7)
C1180.033 (7)0.041 (8)0.025 (7)0.004 (6)0.002 (5)−0.003 (6)
C1190.023 (6)0.038 (8)0.033 (8)0.001 (5)−0.003 (5)0.007 (6)
C1200.044 (8)0.049 (9)0.026 (8)0.016 (6)−0.018 (6)−0.002 (6)
C1210.042 (7)0.059 (10)0.023 (8)0.009 (6)−0.002 (6)0.000 (7)
C1220.038 (7)0.030 (8)0.035 (8)0.005 (6)−0.003 (6)0.005 (6)
C210.028 (6)0.026 (7)0.022 (7)−0.003 (5)−0.008 (5)−0.001 (5)
C220.030 (6)0.024 (7)0.027 (7)−0.004 (5)−0.009 (5)−0.002 (5)
C230.031 (6)0.024 (7)0.046 (9)−0.005 (5)−0.020 (6)0.001 (6)
C240.038 (7)0.035 (8)0.032 (8)−0.005 (6)−0.008 (6)0.008 (6)
C250.048 (8)0.039 (8)0.028 (8)−0.006 (6)0.010 (6)0.004 (6)
C260.039 (7)0.032 (8)0.036 (8)0.004 (6)0.002 (6)−0.002 (6)
C270.032 (7)0.043 (8)0.025 (7)0.004 (6)−0.005 (5)0.001 (6)
C280.053 (8)0.032 (8)0.029 (8)−0.011 (6)−0.010 (6)−0.009 (6)
C290.072 (10)0.047 (9)0.030 (9)−0.017 (8)−0.017 (7)0.002 (7)
C2100.100 (13)0.033 (9)0.043 (10)−0.003 (8)0.015 (9)−0.003 (8)
C2110.067 (9)0.042 (9)0.017 (7)−0.010 (7)−0.003 (6)−0.008 (6)
C2120.029 (6)0.032 (7)0.031 (8)0.001 (5)−0.002 (5)−0.009 (6)
C2130.022 (6)0.031 (7)0.027 (7)−0.003 (5)−0.006 (5)−0.002 (6)
C2140.019 (6)0.042 (8)0.032 (8)0.003 (5)−0.004 (5)−0.006 (6)
C2150.039 (7)0.033 (8)0.028 (8)−0.011 (6)−0.001 (6)−0.015 (6)
C2160.038 (7)0.051 (9)0.020 (7)−0.010 (6)0.003 (5)−0.006 (6)
C2170.047 (8)0.044 (8)0.010 (7)−0.009 (6)0.003 (5)0.004 (6)
C2180.031 (6)0.030 (7)0.037 (8)−0.012 (5)0.001 (5)−0.016 (6)
C2190.025 (6)0.042 (8)0.026 (7)−0.003 (5)0.001 (5)−0.013 (6)
C2200.032 (7)0.055 (9)0.025 (8)−0.002 (6)−0.009 (5)−0.001 (7)
C2210.063 (9)0.039 (9)0.031 (8)0.009 (7)−0.015 (7)0.001 (7)
C2220.032 (7)0.050 (9)0.027 (8)0.015 (6)−0.010 (6)−0.001 (7)
O10.022 (4)0.051 (6)0.038 (6)0.001 (4)−0.001 (4)0.002 (4)
N10.037 (6)0.023 (6)0.060 (8)0.007 (5)−0.009 (5)−0.015 (6)
C10.042 (8)0.035 (8)0.060 (11)0.000 (6)−0.009 (7)−0.015 (7)
C30.024 (7)0.040 (9)0.113 (15)0.002 (6)0.002 (8)−0.026 (9)
C40.045 (8)0.031 (8)0.057 (10)0.000 (6)−0.012 (7)−0.017 (7)
O20.021 (4)0.047 (6)0.037 (6)−0.001 (4)−0.007 (4)−0.002 (4)
N20.022 (5)0.026 (6)0.044 (7)0.001 (4)−0.004 (4)−0.013 (5)
C20.031 (7)0.028 (7)0.029 (8)0.001 (5)0.001 (5)−0.008 (6)
C50.024 (6)0.035 (8)0.062 (10)0.000 (5)−0.010 (6)−0.002 (7)
C60.036 (7)0.026 (7)0.048 (9)−0.004 (5)−0.004 (6)−0.010 (6)

Geometric parameters (Å, °)

Pt1—N112.040 (9)C21—H21C0.9900
Pt1—N122.026 (9)C21—H21D0.9900
Pt1—Cl112.304 (3)C22—C281.512 (16)
Pt1—Cl122.312 (3)C22—C231.539 (16)
Pt2—N212.048 (8)C22—C271.545 (15)
Pt2—N222.056 (9)C23—C241.529 (17)
Pt2—Cl212.307 (3)C23—H23A0.9900
Pt2—Cl222.306 (3)C23—H23B0.9900
N11—C111.493 (14)C24—C291.494 (18)
N11—H11A0.9200C24—C251.539 (17)
N11—H11B0.9200C24—H241.0000
N12—C1121.511 (14)C25—C261.524 (17)
N12—H12A0.9200C25—H25A0.9900
N12—H12B0.9200C25—H25B0.9900
N21—C211.538 (14)C26—C2101.53 (2)
N21—H21A0.9200C26—C271.537 (16)
N21—H21B0.9200C26—H261.0000
N22—C2121.474 (15)C27—H27A0.9900
N22—H22A0.9200C27—H27B0.9900
N22—H22B0.9200C28—C2111.535 (17)
C11—C121.501 (15)C28—H28A0.9900
C11—H11C0.9900C28—H28B0.9900
C11—H11D0.9900C29—C2111.551 (18)
C12—C181.509 (16)C29—H29A0.9900
C12—C171.515 (15)C29—H29B0.9900
C12—C131.540 (16)C210—C2111.55 (2)
C13—C141.526 (17)C210—H21E0.9900
C13—H13A0.9900C210—H21F0.9900
C13—H13B0.9900C211—H2111.0000
C14—C151.518 (18)C212—C2131.501 (16)
C14—C191.544 (17)C212—H21G0.9900
C14—H141.0000C212—H21H0.9900
C15—C161.540 (19)C213—C2141.506 (16)
C15—H15A0.9900C213—C2181.528 (15)
C15—H15B0.9900C213—C2191.540 (14)
C16—C1101.534 (18)C214—C2151.535 (17)
C16—C171.561 (17)C214—H21I0.9900
C16—H161.0000C214—H21J0.9900
C17—H17A0.9900C215—C2161.534 (16)
C17—H17B0.9900C215—C2201.538 (16)
C18—C1111.535 (17)C215—H2151.0000
C18—H18A0.9900C216—C2171.515 (17)
C18—H18B0.9900C216—H21K0.9900
C19—C1111.491 (18)C216—H21L0.9900
C19—H19A0.9900C217—C2211.534 (17)
C19—H19B0.9900C217—C2181.545 (17)
C110—C1111.560 (17)C217—H2171.0000
C110—H11E0.9900C218—H21M0.9900
C110—H11F0.9900C218—H21N0.9900
C111—H1111.0000C219—C2221.575 (16)
C112—C1131.519 (16)C219—H21O0.9900
C112—H11G0.9900C219—H21P0.9900
C112—H11H0.9900C220—C2221.484 (18)
C113—C1181.517 (16)C220—H22C0.9900
C113—C1191.523 (16)C220—H22D0.9900
C113—C1141.528 (14)C221—C2221.532 (17)
C114—C1151.538 (16)C221—H22E0.9900
C114—H11I0.9900C221—H22F0.9900
C114—H11J0.9900C222—H2221.0000
C115—C1161.501 (17)O1—C11.239 (14)
C115—C1201.536 (17)N1—C11.312 (16)
C115—H1151.0000N1—C31.463 (15)
C116—C1171.542 (18)N1—C41.474 (15)
C116—H11K0.9900C1—H10.9500
C116—H11L0.9900C3—H3A0.9800
C117—C1181.536 (18)C3—H3B0.9800
C117—C1211.555 (19)C3—H3C0.9800
C117—H1171.0000C4—H4A0.9800
C118—H11M0.9900C4—H4B0.9800
C118—H11N0.9900C4—H4C0.9800
C119—C1221.512 (18)O2—C21.229 (13)
C119—H11O0.9900N2—C21.354 (14)
C119—H11P0.9900N2—C51.441 (14)
C120—C1221.541 (16)N2—C61.445 (14)
C120—H12C0.9900C2—H20.9500
C120—H12D0.9900C5—H5A0.9800
C121—C1221.513 (17)C5—H5B0.9800
C121—H12E0.9900C5—H5C0.9800
C121—H12F0.9900C6—H6A0.9800
C122—H1221.0000C6—H6B0.9800
C21—C221.483 (15)C6—H6C0.9800
N12—Pt1—N1192.1 (4)C22—C21—N21113.5 (9)
N12—Pt1—Cl11177.6 (3)C22—C21—H21C108.9
N11—Pt1—Cl1187.5 (3)N21—C21—H21C108.9
N12—Pt1—Cl1288.2 (3)C22—C21—H21D108.9
N11—Pt1—Cl12179.0 (3)N21—C21—H21D108.9
Cl11—Pt1—Cl1292.17 (11)H21C—C21—H21D107.7
N21—Pt2—N2292.1 (4)C21—C22—C28111.4 (9)
N21—Pt2—Cl22177.0 (3)C21—C22—C23108.5 (10)
N22—Pt2—Cl2287.3 (3)C28—C22—C23109.0 (10)
N21—Pt2—Cl2188.3 (3)C21—C22—C27111.8 (10)
N22—Pt2—Cl21178.8 (3)C28—C22—C27107.4 (10)
Cl22—Pt2—Cl2192.30 (11)C23—C22—C27108.7 (9)
C11—N11—Pt1118.1 (7)C24—C23—C22110.6 (10)
C11—N11—H11A107.8C24—C23—H23A109.5
Pt1—N11—H11A107.8C22—C23—H23A109.5
C11—N11—H11B107.8C24—C23—H23B109.5
Pt1—N11—H11B107.8C22—C23—H23B109.5
H11A—N11—H11B107.1H23A—C23—H23B108.1
C112—N12—Pt1120.2 (7)C29—C24—C23111.2 (10)
C112—N12—H12A107.3C29—C24—C25109.7 (12)
Pt1—N12—H12A107.3C23—C24—C25108.2 (10)
C112—N12—H12B107.3C29—C24—H24109.2
Pt1—N12—H12B107.3C23—C24—H24109.2
H12A—N12—H12B106.9C25—C24—H24109.2
C21—N21—Pt2119.8 (7)C26—C25—C24109.8 (10)
C21—N21—H21A107.4C26—C25—H25A109.7
Pt2—N21—H21A107.4C24—C25—H25A109.7
C21—N21—H21B107.4C26—C25—H25B109.7
Pt2—N21—H21B107.4C24—C25—H25B109.7
H21A—N21—H21B106.9H25A—C25—H25B108.2
C212—N22—Pt2117.7 (7)C25—C26—C210109.8 (12)
C212—N22—H22A107.9C25—C26—C27109.8 (10)
Pt2—N22—H22A107.9C210—C26—C27107.5 (11)
C212—N22—H22B107.9C25—C26—H26109.9
Pt2—N22—H22B107.9C210—C26—H26109.9
H22A—N22—H22B107.2C27—C26—H26109.9
N11—C11—C12116.0 (9)C26—C27—C22111.0 (10)
N11—C11—H11C108.3C26—C27—H27A109.4
C12—C11—H11C108.3C22—C27—H27A109.4
N11—C11—H11D108.3C26—C27—H27B109.4
C12—C11—H11D108.3C22—C27—H27B109.4
H11C—C11—H11D107.4H27A—C27—H27B108.0
C11—C12—C18107.2 (9)C22—C28—C211111.4 (10)
C11—C12—C17112.9 (10)C22—C28—H28A109.3
C18—C12—C17109.1 (9)C211—C28—H28A109.3
C11—C12—C13110.3 (9)C22—C28—H28B109.3
C18—C12—C13107.9 (10)C211—C28—H28B109.3
C17—C12—C13109.3 (10)H28A—C28—H28B108.0
C14—C13—C12110.3 (10)C24—C29—C211109.8 (11)
C14—C13—H13A109.6C24—C29—H29A109.7
C12—C13—H13A109.6C211—C29—H29A109.7
C14—C13—H13B109.6C24—C29—H29B109.7
C12—C13—H13B109.6C211—C29—H29B109.7
H13A—C13—H13B108.1H29A—C29—H29B108.2
C15—C14—C13110.2 (12)C26—C210—C211110.1 (12)
C15—C14—C19109.0 (11)C26—C210—H21E109.6
C13—C14—C19108.9 (11)C211—C210—H21E109.6
C15—C14—H14109.6C26—C210—H21F109.6
C13—C14—H14109.6C211—C210—H21F109.6
C19—C14—H14109.6H21E—C210—H21F108.2
C14—C15—C16108.9 (11)C28—C211—C210108.8 (11)
C14—C15—H15A109.9C28—C211—C29109.6 (11)
C16—C15—H15A109.9C210—C211—C29107.8 (11)
C14—C15—H15B109.9C28—C211—H211110.2
C16—C15—H15B109.9C210—C211—H211110.2
H15A—C15—H15B108.3C29—C211—H211110.2
C110—C16—C15110.8 (12)N22—C212—C213116.6 (10)
C110—C16—C17109.7 (10)N22—C212—H21G108.1
C15—C16—C17108.9 (11)C213—C212—H21G108.1
C110—C16—H16109.1N22—C212—H21H108.1
C15—C16—H16109.1C213—C212—H21H108.1
C17—C16—H16109.1H21G—C212—H21H107.3
C12—C17—C16109.5 (10)C212—C213—C214106.1 (10)
C12—C17—H17A109.8C212—C213—C218112.3 (9)
C16—C17—H17A109.8C214—C213—C218109.4 (10)
C12—C17—H17B109.8C212—C213—C219111.5 (10)
C16—C17—H17B109.8C214—C213—C219108.3 (9)
H17A—C17—H17B108.2C218—C213—C219109.2 (10)
C12—C18—C111112.2 (10)C213—C214—C215110.8 (10)
C12—C18—H18A109.2C213—C214—H21I109.5
C111—C18—H18A109.2C215—C214—H21I109.5
C12—C18—H18B109.2C213—C214—H21J109.5
C111—C18—H18B109.2C215—C214—H21J109.5
H18A—C18—H18B107.9H21I—C214—H21J108.1
C111—C19—C14110.7 (11)C216—C215—C214109.8 (10)
C111—C19—H19A109.5C216—C215—C220110.6 (11)
C14—C19—H19A109.5C214—C215—C220108.4 (10)
C111—C19—H19B109.5C216—C215—H215109.4
C14—C19—H19B109.5C214—C215—H215109.4
H19A—C19—H19B108.1C220—C215—H215109.4
C16—C110—C111108.0 (11)C217—C216—C215108.5 (10)
C16—C110—H11E110.1C217—C216—H21K110.0
C111—C110—H11E110.1C215—C216—H21K110.0
C16—C110—H11F110.1C217—C216—H21L110.0
C111—C110—H11F110.1C215—C216—H21L110.0
H11E—C110—H11F108.4H21K—C216—H21L108.4
C19—C111—C18109.8 (10)C216—C217—C221110.8 (11)
C19—C111—C110109.5 (11)C216—C217—C218109.3 (11)
C18—C111—C110107.6 (11)C221—C217—C218109.1 (10)
C19—C111—H111110.0C216—C217—H217109.2
C18—C111—H111110.0C221—C217—H217109.2
C110—C111—H111110.0C218—C217—H217109.2
N12—C112—C113115.3 (9)C213—C218—C217109.9 (9)
N12—C112—H11G108.5C213—C218—H21M109.7
C113—C112—H11G108.5C217—C218—H21M109.7
N12—C112—H11H108.5C213—C218—H21N109.7
C113—C112—H11H108.5C217—C218—H21N109.7
H11G—C112—H11H107.5H21M—C218—H21N108.2
C118—C113—C112111.1 (10)C213—C219—C222108.9 (9)
C118—C113—C119108.2 (10)C213—C219—H21O109.9
C112—C113—C119108.8 (10)C222—C219—H21O109.9
C118—C113—C114108.6 (10)C213—C219—H21P109.9
C112—C113—C114110.8 (9)C222—C219—H21P109.9
C119—C113—C114109.4 (9)H21O—C219—H21P108.3
C113—C114—C115109.6 (10)C222—C220—C215109.1 (10)
C113—C114—H11I109.8C222—C220—H22C109.9
C115—C114—H11I109.8C215—C220—H22C109.9
C113—C114—H11J109.8C222—C220—H22D109.9
C115—C114—H11J109.8C215—C220—H22D109.9
H11I—C114—H11J108.2H22C—C220—H22D108.3
C116—C115—C120109.7 (11)C222—C221—C217108.7 (11)
C116—C115—C114109.9 (10)C222—C221—H22E109.9
C120—C115—C114109.8 (10)C217—C221—H22E109.9
C116—C115—H115109.1C222—C221—H22F109.9
C120—C115—H115109.1C217—C221—H22F109.9
C114—C115—H115109.1H22E—C221—H22F108.3
C115—C116—C117110.3 (11)C220—C222—C221112.0 (11)
C115—C116—H11K109.6C220—C222—C219109.6 (10)
C117—C116—H11K109.6C221—C222—C219108.0 (10)
C115—C116—H11L109.6C220—C222—H222109.1
C117—C116—H11L109.6C221—C222—H222109.1
H11K—C116—H11L108.1C219—C222—H222109.1
C118—C117—C116108.5 (11)C1—N1—C3119.7 (11)
C118—C117—C121108.7 (12)C1—N1—C4122.7 (11)
C116—C117—C121108.6 (11)C3—N1—C4117.6 (11)
C118—C117—H117110.3O1—C1—N1125.5 (13)
C116—C117—H117110.3O1—C1—H1117.2
C121—C117—H117110.3N1—C1—H1117.2
C113—C118—C117111.2 (10)N1—C3—H3A109.5
C113—C118—H11M109.4N1—C3—H3B109.5
C117—C118—H11M109.4H3A—C3—H3B109.5
C113—C118—H11N109.4N1—C3—H3C109.5
C117—C118—H11N109.4H3A—C3—H3C109.5
H11M—C118—H11N108.0H3B—C3—H3C109.5
C122—C119—C113111.3 (11)N1—C4—H4A109.5
C122—C119—H11O109.4N1—C4—H4B109.5
C113—C119—H11O109.4H4A—C4—H4B109.5
C122—C119—H11P109.4N1—C4—H4C109.5
C113—C119—H11P109.4H4A—C4—H4C109.5
H11O—C119—H11P108.0H4B—C4—H4C109.5
C115—C120—C122108.3 (10)C2—N2—C5119.3 (10)
C115—C120—H12C110.0C2—N2—C6121.7 (10)
C122—C120—H12C110.0C5—N2—C6119.0 (10)
C115—C120—H12D110.0O2—C2—N2123.5 (11)
C122—C120—H12D110.0O2—C2—H2118.2
H12C—C120—H12D108.4N2—C2—H2118.2
C122—C121—C117109.1 (10)N2—C5—H5A109.5
C122—C121—H12E109.9N2—C5—H5B109.5
C117—C121—H12E109.9H5A—C5—H5B109.5
C122—C121—H12F109.9N2—C5—H5C109.5
C117—C121—H12F109.9H5A—C5—H5C109.5
H12E—C121—H12F108.3H5B—C5—H5C109.5
C119—C122—C121109.3 (11)N2—C6—H6A109.5
C119—C122—C120109.6 (10)N2—C6—H6B109.5
C121—C122—C120110.4 (11)H6A—C6—H6B109.5
C119—C122—H122109.2N2—C6—H6C109.5
C121—C122—H122109.2H6A—C6—H6C109.5
C120—C122—H122109.2H6B—C6—H6C109.5
N12—Pt1—N11—C11−118.0 (8)C115—C120—C122—C119−59.8 (14)
Cl11—Pt1—N11—C1164.4 (8)C115—C120—C122—C12160.7 (14)
N11—Pt1—N12—C112122.5 (8)Pt2—N21—C21—C22162.7 (7)
Cl12—Pt1—N12—C112−58.5 (7)N21—C21—C22—C28−62.7 (13)
N22—Pt2—N21—C21123.0 (8)N21—C21—C22—C23177.4 (9)
Cl21—Pt2—N21—C21−58.1 (8)N21—C21—C22—C2757.5 (12)
N21—Pt2—N22—C212−114.7 (8)C21—C22—C23—C24178.9 (10)
Cl22—Pt2—N22—C21268.2 (7)C28—C22—C23—C2457.5 (12)
Pt1—N11—C11—C12−159.0 (8)C27—C22—C23—C24−59.3 (13)
N11—C11—C12—C18−179.9 (9)C22—C23—C24—C29−58.8 (14)
N11—C11—C12—C17−59.8 (13)C22—C23—C24—C2561.7 (13)
N11—C11—C12—C1362.8 (13)C29—C24—C25—C2659.9 (14)
C11—C12—C13—C14176.4 (11)C23—C24—C25—C26−61.6 (14)
C18—C12—C13—C1459.6 (13)C24—C25—C26—C210−58.2 (14)
C17—C12—C13—C14−58.9 (14)C24—C25—C26—C2759.8 (14)
C12—C13—C14—C1559.4 (14)C25—C26—C27—C22−57.7 (14)
C12—C13—C14—C19−60.0 (14)C210—C26—C27—C2261.8 (14)
C13—C14—C15—C16−60.2 (14)C21—C22—C27—C26176.5 (10)
C19—C14—C15—C1659.2 (14)C28—C22—C27—C26−61.0 (13)
C14—C15—C16—C110−60.4 (14)C23—C22—C27—C2656.8 (13)
C14—C15—C16—C1760.4 (14)C21—C22—C28—C211−177.8 (11)
C11—C12—C17—C16−177.5 (10)C23—C22—C28—C211−58.1 (14)
C18—C12—C17—C16−58.4 (13)C27—C22—C28—C21159.4 (13)
C13—C12—C17—C1659.4 (13)C23—C24—C29—C21158.1 (15)
C110—C16—C17—C1260.7 (14)C25—C24—C29—C211−61.5 (14)
C15—C16—C17—C12−60.7 (13)C25—C26—C210—C21159.1 (14)
C11—C12—C18—C111−177.0 (10)C27—C26—C210—C211−60.3 (14)
C17—C12—C18—C11160.4 (13)C22—C28—C211—C210−59.5 (14)
C13—C12—C18—C111−58.2 (12)C22—C28—C211—C2958.2 (15)
C15—C14—C19—C111−61.1 (14)C26—C210—C211—C2859.4 (14)
C13—C14—C19—C11159.1 (14)C26—C210—C211—C29−59.4 (14)
C15—C16—C110—C11159.1 (14)C24—C29—C211—C28−57.2 (15)
C17—C16—C110—C111−61.2 (14)C24—C29—C211—C21061.1 (15)
C14—C19—C111—C18−57.2 (14)Pt2—N22—C212—C213−160.5 (7)
C14—C19—C111—C11060.8 (14)N22—C212—C213—C214179.9 (9)
C12—C18—C111—C1958.2 (14)N22—C212—C213—C21860.4 (13)
C12—C18—C111—C110−60.9 (13)N22—C212—C213—C219−62.5 (13)
C16—C110—C111—C19−59.2 (14)C212—C213—C214—C215−179.3 (9)
C16—C110—C111—C1860.1 (14)C218—C213—C214—C215−58.0 (12)
Pt1—N12—C112—C113163.9 (7)C219—C213—C214—C21560.9 (12)
N12—C112—C113—C118−62.2 (12)C213—C214—C215—C21659.3 (12)
N12—C112—C113—C119178.8 (8)C213—C214—C215—C220−61.6 (12)
N12—C112—C113—C11458.6 (12)C214—C215—C216—C217−60.1 (13)
C118—C113—C114—C115−59.7 (12)C220—C215—C216—C21759.4 (13)
C112—C113—C114—C115178.1 (10)C215—C216—C217—C221−59.4 (14)
C119—C113—C114—C11558.2 (13)C215—C216—C217—C21860.9 (13)
C113—C114—C115—C11660.4 (13)C212—C213—C218—C217176.0 (10)
C113—C114—C115—C120−60.4 (13)C214—C213—C218—C21758.5 (12)
C120—C115—C116—C11761.2 (14)C219—C213—C218—C217−59.8 (12)
C114—C115—C116—C117−59.7 (14)C216—C217—C218—C213−60.7 (12)
C115—C116—C117—C11858.3 (15)C221—C217—C218—C21360.6 (13)
C115—C116—C117—C121−59.7 (15)C212—C213—C219—C222−175.1 (10)
C112—C113—C118—C117−177.8 (10)C214—C213—C219—C222−58.8 (12)
C119—C113—C118—C117−58.5 (13)C218—C213—C219—C22260.2 (12)
C114—C113—C118—C11760.1 (13)C216—C215—C220—C222−59.0 (14)
C116—C117—C118—C113−58.9 (14)C214—C215—C220—C22261.3 (13)
C121—C117—C118—C11359.0 (13)C216—C217—C221—C22258.2 (14)
C118—C113—C119—C12259.5 (12)C218—C217—C221—C222−62.2 (13)
C112—C113—C119—C122−179.7 (9)C215—C220—C222—C22158.5 (14)
C114—C113—C119—C122−58.6 (13)C215—C220—C222—C219−61.3 (13)
C116—C115—C120—C122−60.4 (13)C217—C221—C222—C220−58.2 (14)
C114—C115—C120—C12260.5 (13)C217—C221—C222—C21962.6 (13)
C118—C117—C121—C122−59.1 (13)C213—C219—C222—C22060.5 (13)
C116—C117—C121—C12258.8 (15)C213—C219—C222—C221−61.8 (13)
C113—C119—C122—C121−61.4 (13)C3—N1—C1—O1−178.5 (14)
C113—C119—C122—C12059.7 (13)C4—N1—C1—O13(2)
C117—C121—C122—C11960.3 (14)C5—N2—C2—O2176.5 (11)
C117—C121—C122—C120−60.4 (14)C6—N2—C2—O2−1.7 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N11—H11A···O20.921.952.863 (13)170
N11—H11B···Cl12i0.922.643.409 (10)141
N12—H12A···Cl11i0.922.633.299 (9)131
N12—H12B···O20.921.932.843 (11)175
N21—H21A···Cl22ii0.922.553.238 (10)132
N21—H21B···O10.921.912.821 (12)173
N22—H22A···O10.921.942.843 (11)165
N22—H22B···Cl21ii0.922.643.354 (10)136

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2221).

References

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