Literature DB >> 21578064

cis-Bis[(1-adamantylmeth-yl)amine-κN]-dichloridoplatinum(II) N,N-dimethyl-formamide solvate.

Fernande D Rochon1, Christian Tessier.   

Abstract

The asymmetric unit of the title compound {systematic name: cis-dichloridobis[(3,7-dimethylbicyclo-[3.3.1]non-1-ylmeth-yl)-amine-κN]platinum(II) N,N-dimethyl-formamide solvate}, [PtCl(2)(C(11)H(19)N)(2)]·C(3)H(7)NO, consists of two metrically similar Pt complexes and two dimethyl-formamide solvent mol-ecules. Each Pt(II) center is coordinated by the amine groups of two (1-adamantylmeth-yl)amine ligands and two Cl atoms in a cis-square-planar arrangement. The Pt(II) 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 inter-molecular hydrogen bonds are observed, forming two discrete pairs of complexes and solvent mol-ecules.

Entities:  

Year:  2009        PMID: 21578064      PMCID: PMC2970952          DOI: 10.1107/S1600536809037982

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

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

Experimental

Crystal data

[PtCl2(C11H19N)2]·C3H7NO M = 669.63 Triclinic, 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 ▶) 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 ▶); cell refinement: 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 publCIF (Westrip, 2009 ▶). 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
[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
Bruker SMART APEXII CCD diffractometer9285 independent reflections
Radiation source: normal-focus sealed tube5724 reflections with I > 2σ(I)
graphiteRint = 0.099
φ 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 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
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*
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)
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)
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
Table 1

Selected bond lengths (Å)

Pt1—N112.040 (9)
Pt1—N122.026 (9)
Pt1—Cl112.304 (3)
Pt1—Cl122.312 (3)
Pt2—N212.048 (8)
Pt2—N222.056 (9)
Pt2—Cl212.307 (3)
Pt2—Cl222.306 (3)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—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) ; (ii) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Influence of twenty potentially antiviral substances on in vitro multiplication of hepatitis A virus.

Authors:  A Widell; B G Hansson; B Oberg; E Nordenfelt
Journal:  Antiviral Res       Date:  1986-03       Impact factor: 5.970

3.  5-(1-Adamantyl) pyrimidines as inhibitors of folate metabolism.

Authors:  Y K Ho; M T Hakala; S F Zakrzewski
Journal:  Cancer Res       Date:  1972-05       Impact factor: 12.701

4.  The molecular basis of the specific anti-influenza action of amantadine.

Authors:  A J Hay; A J Wolstenholme; J J Skehel; M H Smith
Journal:  EMBO J       Date:  1985-11       Impact factor: 11.598

  4 in total
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1.  Solvent inclusion in the crystal structure of bis-[(adamantan-1-yl)methanaminium chloride] 1,4-dioxane hemisolvate monohydrate explained using the computed crystal energy landscape.

Authors:  Sharmarke Mohamed
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-08-26
  1 in total

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